data_2008src0845

#Dr. E. McDonald

#ADDSYM detects a possible pseudo-symmetry and the molecules are
#similar, but it appears the rotation of an aromatic ring breaks
#the symmetry.
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C23 H20 N2 O6'
_chemical_formula_weight          420.41
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    P21/n
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    21.5955(7)
_cell_length_b                    9.5241(3)
_cell_length_c                    30.6167(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  107.4310(10)
_cell_angle_gamma                 90.00
_cell_volume                      6008.0(3)
_cell_formula_units_Z             12
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     13783
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        'Cut Block'
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.09
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.394
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2640
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9838
_exptl_absorpt_correction_T_max   0.9909
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Parameter refinement on 36537 reflections reduced R(int) from 0.0801 to 0.0430
Ratio of minimum to maximum apparent transmission: 0.929860
The given Tmin and Tmax were generated using the SHELX SIZE command
;


_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type   'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             52032
_diffrn_reflns_av_R_equivalents   0.0509
_diffrn_reflns_av_sigmaI/netI     0.0555
_diffrn_reflns_limit_h_min        -27
_diffrn_reflns_limit_h_max        27
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -38
_diffrn_reflns_limit_l_max        39
_diffrn_reflns_theta_min          2.91
_diffrn_reflns_theta_max          27.48
_reflns_number_total              13704
_reflns_number_gt                 8793
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0218P)²+12.5958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          13704
_refine_ls_number_parameters      844
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1262
_refine_ls_R_factor_gt            0.0795
_refine_ls_wR_factor_ref          0.1653
_refine_ls_wR_factor_gt           0.1414
_refine_ls_goodness_of_fit_ref    1.068
_refine_ls_restrained_S_all       1.068
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.96335(13) -0.0167(3) 0.32274(10) 0.0196(6) Uani 1 1 d . . .
C2 C 1.06047(13) -0.0837(3) 0.37608(10) 0.0187(6) Uani 1 1 d . . .
C3 C 1.06589(12) -0.1324(3) 0.33019(9) 0.0175(6) Uani 1 1 d . . .
H3 H 1.0765 -0.2347 0.3304 0.021 Uiso 1 1 calc R . .
C4 C 0.99953(13) -0.0986(3) 0.29559(9) 0.0175(6) Uani 1 1 d . . .
H4 H 0.9756 -0.1839 0.2804 0.021 Uiso 1 1 calc R . .
C5 C 1.01928(13) 0.0018(3) 0.26181(9) 0.0180(6) Uani 1 1 d . . .
C6 C 1.05481(13) -0.0951(3) 0.23670(10) 0.0191(6) Uani 1 1 d . . .
C7 C 1.11213(13) -0.0408(3) 0.31044(9) 0.0180(6) Uani 1 1 d . . .
C8 C 0.96843(13) 0.0996(3) 0.23283(10) 0.0199(6) Uani 1 1 d . . .
C9 C 0.86976(14) 0.1086(3) 0.17284(11) 0.0288(7) Uani 1 1 d . . .
H9A H 0.8459 0.1587 0.1907 0.043 Uiso 1 1 calc R . .
H9B H 0.8400 0.0463 0.1508 0.043 Uiso 1 1 calc R . .
H9C H 0.8886 0.1766 0.1564 0.043 Uiso 1 1 calc R . .
C10 C 1.17691(13) 0.0034(3) 0.34108(10) 0.0233(6) Uani 1 1 d . . .
H10A H 1.1987 0.0620 0.3239 0.035 Uiso 1 1 calc R . .
H10B H 1.2034 -0.0799 0.3526 0.035 Uiso 1 1 calc R . .
H10C H 1.1712 0.0572 0.3669 0.035 Uiso 1 1 calc R . .
C11 C 0.97760(13) 0.0413(3) 0.40489(9) 0.0186(6) Uani 1 1 d . . .
C12 C 0.91406(14) 0.0143(3) 0.40421(11) 0.0236(6) Uani 1 1 d . . .
H12 H 0.8863 -0.0413 0.3806 0.028 Uiso 1 1 calc R . .
C13 C 0.89208(15) 0.0702(3) 0.43866(11) 0.0281(7) Uani 1 1 d . . .
H13 H 0.8483 0.0560 0.4380 0.034 Uiso 1 1 calc R . .
C14 C 0.93356(15) 0.1469(3) 0.47415(11) 0.0276(7) Uani 1 1 d . . .
H14 H 0.9187 0.1810 0.4984 0.033 Uiso 1 1 calc R . .
C15 C 0.99649(15) 0.1734(3) 0.47412(11) 0.0257(7) Uani 1 1 d . . .
H15 H 1.0246 0.2268 0.4982 0.031 Uiso 1 1 calc R . .
C16 C 1.01881(14) 0.1223(3) 0.43887(10) 0.0226(6) Uani 1 1 d . . .
H16 H 1.0616 0.1427 0.4382 0.027 Uiso 1 1 calc R . .
C17 C 1.15578(13) -0.2314(3) 0.26578(10) 0.0203(6) Uani 1 1 d . . .
H17A H 1.1323 -0.2935 0.2402 0.024 Uiso 1 1 calc R . .
H17B H 1.1642 -0.2860 0.2945 0.024 Uiso 1 1 calc R . .
C18 C 1.22047(13) -0.1911(3) 0.25921(10) 0.0199(6) Uani 1 1 d . . .
C19 C 1.27811(14) -0.2342(3) 0.29065(11) 0.0289(7) Uani 1 1 d . . .
H19 H 1.2769 -0.2825 0.3175 0.035 Uiso 1 1 calc R . .
C20 C 1.33766(15) -0.2076(4) 0.28341(13) 0.0374(8) Uani 1 1 d . . .
H20 H 1.3768 -0.2372 0.3053 0.045 Uiso 1 1 calc R . .
C21 C 1.33950(15) -0.1380(3) 0.24436(12) 0.0335(8) Uani 1 1 d . . .
H21 H 1.3800 -0.1206 0.2391 0.040 Uiso 1 1 calc R . .
C22 C 1.28279(16) -0.0937(4) 0.21303(12) 0.0353(8) Uani 1 1 d . . .
H22 H 1.2842 -0.0456 0.1862 0.042 Uiso 1 1 calc R . .
C23 C 1.22346(15) -0.1192(3) 0.22057(11) 0.0306(7) Uani 1 1 d . . .
H23 H 1.1846 -0.0869 0.1990 0.037 Uiso 1 1 calc R . .
N1 N 1.00070(11) -0.0168(2) 0.36910(8) 0.0183(5) Uani 1 1 d . . .
N2 N 1.11373(11) -0.1121(2) 0.26783(8) 0.0187(5) Uani 1 1 d . . .
O1 O 0.91184(9) 0.0414(2) 0.30717(7) 0.0275(5) Uani 1 1 d . . .
O2 O 1.10029(10) -0.1011(2) 0.41293(7) 0.0251(5) Uani 1 1 d . . .
O3 O 1.07191(9) 0.07767(19) 0.29204(6) 0.0192(4) Uani 1 1 d . . .
O4 O 1.03324(9) -0.1516(2) 0.19964(7) 0.0239(5) Uani 1 1 d . . .
O5 O 0.97082(10) 0.2254(2) 0.23599(7) 0.0253(5) Uani 1 1 d . . .
O6 O 0.92145(9) 0.0256(2) 0.20358(7) 0.0236(5) Uani 1 1 d . . .
C31 C 0.37215(13) 0.0138(3) 0.00875(10) 0.0195(6) Uani 1 1 d . . .
C32 C 0.27697(13) 0.0910(3) -0.04437(10) 0.0195(6) Uani 1 1 d . . .
C33 C 0.27213(13) 0.1406(3) 0.00161(9) 0.0179(6) Uani 1 1 d . . .
H33 H 0.2639 0.2439 0.0018 0.022 Uiso 1 1 calc R . .
C34 C 0.33783(13) 0.0994(3) 0.03631(9) 0.0181(6) Uani 1 1 d . . .
H34 H 0.3636 0.1820 0.0520 0.022 Uiso 1 1 calc R . .
C35 C 0.31513(13) 0.0014(3) 0.06945(9) 0.0177(6) Uani 1 1 d . . .
C36 C 0.28138(13) 0.1017(3) 0.09455(10) 0.0189(6) Uani 1 1 d . . .
C37 C 0.22382(13) 0.0546(3) 0.02041(10) 0.0189(6) Uani 1 1 d . . .
C38 C 0.36351(13) -0.1009(3) 0.09858(9) 0.0194(6) Uani 1 1 d . . .
C39 C 0.45988(15) -0.1182(3) 0.16021(11) 0.0301(7) Uani 1 1 d . . .
H39A H 0.4381 -0.1835 0.1755 0.045 Uiso 1 1 calc R . .
H39B H 0.4897 -0.0584 0.1831 0.045 Uiso 1 1 calc R . .
H39C H 0.4844 -0.1715 0.1435 0.045 Uiso 1 1 calc R . .
C40 C 0.15763(13) 0.0178(3) -0.01076(10) 0.0232(6) Uani 1 1 d . . .
H40A H 0.1621 -0.0366 -0.0368 0.035 Uiso 1 1 calc R . .
H40B H 0.1334 0.1042 -0.0219 0.035 Uiso 1 1 calc R . .
H40C H 0.1343 -0.0380 0.0061 0.035 Uiso 1 1 calc R . .
C41 C 0.35801(13) -0.0408(3) -0.07336(9) 0.0183(6) Uani 1 1 d . . .
C42 C 0.31568(14) -0.1157(3) -0.10827(10) 0.0217(6) Uani 1 1 d . . .
H42 H 0.2724 -0.1321 -0.1081 0.026 Uiso 1 1 calc R . .
C43 C 0.33720(15) -0.1672(3) -0.14383(10) 0.0241(6) Uani 1 1 d . . .
H43 H 0.3081 -0.2161 -0.1686 0.029 Uiso 1 1 calc R . .
C44 C 0.40109(15) -0.1468(3) -0.14283(11) 0.0259(7) Uani 1 1 d . . .
H44 H 0.4158 -0.1819 -0.1670 0.031 Uiso 1 1 calc R . .
C45 C 0.44386(15) -0.0754(3) -0.10673(11) 0.0276(7) Uani 1 1 d . . .
H45 H 0.4879 -0.0641 -0.1058 0.033 Uiso 1 1 calc R . .
C46 C 0.42224(14) -0.0207(3) -0.07198(10) 0.0246(6) Uani 1 1 d . . .
H46 H 0.4510 0.0300 -0.0475 0.029 Uiso 1 1 calc R . .
C47 C 0.18119(14) 0.2417(3) 0.06727(10) 0.0218(6) Uani 1 1 d . . .
H47A H 0.1647 0.2885 0.0371 0.026 Uiso 1 1 calc R . .
H47B H 0.2069 0.3115 0.0893 0.026 Uiso 1 1 calc R . .
C48 C 0.12386(13) 0.1966(3) 0.08279(10) 0.0206(6) Uani 1 1 d . . .
C49 C 0.07193(15) 0.2883(4) 0.07609(11) 0.0322(7) Uani 1 1 d . . .
H49 H 0.0723 0.3755 0.0611 0.039 Uiso 1 1 calc R . .
C50 C 0.01946(16) 0.2530(4) 0.09123(13) 0.0439(10) Uani 1 1 d . . .
H50 H -0.0164 0.3153 0.0859 0.053 Uiso 1 1 calc R . .
C51 C 0.01900(16) 0.1281(4) 0.11392(13) 0.0432(10) Uani 1 1 d . . .
H51 H -0.0168 0.1046 0.1245 0.052 Uiso 1 1 calc R . .
C52 C 0.07088(16) 0.0378(4) 0.12110(12) 0.0358(8) Uani 1 1 d . . .
H52 H 0.0711 -0.0478 0.1371 0.043 Uiso 1 1 calc R . .
C53 C 0.12291(14) 0.0705(3) 0.10519(10) 0.0260(7) Uani 1 1 d . . .
H53 H 0.1580 0.0064 0.1097 0.031 Uiso 1 1 calc R . .
N31 N 0.33577(11) 0.0190(2) -0.03728(8) 0.0183(5) Uani 1 1 d . . .
N32 N 0.22381(11) 0.1267(2) 0.06337(8) 0.0189(5) Uani 1 1 d . . .
O31 O 0.42226(9) -0.0497(2) 0.02448(7) 0.0269(5) Uani 1 1 d . . .
O32 O 0.23797(9) 0.1122(2) -0.08136(7) 0.0244(5) Uani 1 1 d . . .
O33 O 0.26104(9) -0.06841(19) 0.03856(6) 0.0184(4) Uani 1 1 d . . .
O34 O 0.30283(10) 0.1524(2) 0.13270(7) 0.0233(4) Uani 1 1 d . . .
O35 O 0.35734(10) -0.2258(2) 0.09582(7) 0.0252(5) Uani 1 1 d . . .
O36 O 0.41153(9) -0.0309(2) 0.12816(7) 0.0233(4) Uani 1 1 d . . .
C61 C 0.79173(13) 0.5056(3) 0.15625(10) 0.0194(6) Uani 1 1 d . . .
C62 C 0.88618(13) 0.5857(3) 0.20959(10) 0.0187(6) Uani 1 1 d . . .
C63 C 0.89154(13) 0.6307(3) 0.16330(9) 0.0180(6) Uani 1 1 d . . .
H63 H 0.9005 0.7335 0.1622 0.022 Uiso 1 1 calc R . .
C64 C 0.82663(13) 0.5889(3) 0.12860(9) 0.0181(6) Uani 1 1 d . . .
H64 H 0.8011 0.6709 0.1122 0.022 Uiso 1 1 calc R . .
C65 C 0.84933(13) 0.4877(3) 0.09635(9) 0.0170(6) Uani 1 1 d . . .
C66 C 0.88497(13) 0.5827(3) 0.07112(9) 0.0169(5) Uani 1 1 d . . .
C67 C 0.94049(13) 0.5390(3) 0.14634(9) 0.0178(6) Uani 1 1 d . . .
C68 C 0.80027(13) 0.3863(3) 0.06730(9) 0.0185(6) Uani 1 1 d . . .
C69 C 0.70277(14) 0.3729(3) 0.00647(11) 0.0283(7) Uani 1 1 d . . .
H69A H 0.7236 0.3057 -0.0089 0.043 Uiso 1 1 calc R . .
H69B H 0.6735 0.4338 -0.0164 0.043 Uiso 1 1 calc R . .
H69C H 0.6779 0.3218 0.0234 0.043 Uiso 1 1 calc R . .
C70 C 1.00450(13) 0.5020(3) 0.17966(10) 0.0217(6) Uani 1 1 d . . .
H70A H 0.9975 0.4435 0.2041 0.033 Uiso 1 1 calc R . .
H70B H 1.0274 0.5881 0.1929 0.033 Uiso 1 1 calc R . .
H70C H 1.0306 0.4501 0.1638 0.033 Uiso 1 1 calc R . .
C71 C 0.80666(13) 0.4497(3) 0.23853(10) 0.0203(6) Uani 1 1 d . . .
C72 C 0.85017(14) 0.3740(3) 0.27299(10) 0.0216(6) Uani 1 1 d . . .
H72 H 0.8935 0.3597 0.2725 0.026 Uiso 1 1 calc R . .
C73 C 0.82939(15) 0.3193(3) 0.30833(11) 0.0256(7) Uani 1 1 d . . .
H73 H 0.8589 0.2690 0.3325 0.031 Uiso 1 1 calc R . .
C74 C 0.76557(15) 0.3378(3) 0.30840(11) 0.0268(7) Uani 1 1 d . . .
H74 H 0.7517 0.3010 0.3327 0.032 Uiso 1 1 calc R . .
C75 C 0.72217(15) 0.4102(3) 0.27282(11) 0.0274(7) Uani 1 1 d . . .
H75 H 0.6782 0.4198 0.2723 0.033 Uiso 1 1 calc R . .
C76 C 0.74265(14) 0.4687(3) 0.23793(10) 0.0236(6) Uani 1 1 d . . .
H76 H 0.7134 0.5207 0.2141 0.028 Uiso 1 1 calc R . .
C77 C 0.98478(13) 0.7241(3) 0.10007(10) 0.0197(6) Uani 1 1 d . . .
H77A H 0.9990 0.7715 0.1302 0.024 Uiso 1 1 calc R . .
H77B H 0.9585 0.7921 0.0776 0.024 Uiso 1 1 calc R . .
C78 C 1.04420(14) 0.6864(3) 0.08616(10) 0.0221(6) Uani 1 1 d . . .
C79 C 1.04052(17) 0.6800(4) 0.04016(12) 0.0360(8) Uani 1 1 d . . .
H79 H 0.9999 0.6929 0.0174 0.043 Uiso 1 1 calc R . .
C80 C 1.0959(2) 0.6549(4) 0.02722(15) 0.0530(11) Uani 1 1 d . . .
H80 H 1.0930 0.6498 -0.0043 0.064 Uiso 1 1 calc R . .
C81 C 1.1547(2) 0.6373(4) 0.05980(18) 0.0598(13) Uani 1 1 d . . .
H81 H 1.1925 0.6205 0.0508 0.072 Uiso 1 1 calc R . .
C82 C 1.15922(18) 0.6440(5) 0.10530(17) 0.0564(12) Uani 1 1 d . . .
H82 H 1.2001 0.6325 0.1278 0.068 Uiso 1 1 calc R . .
C83 C 1.10382(15) 0.6676(4) 0.11841(13) 0.0379(8) Uani 1 1 d . . .
H83 H 1.1070 0.6708 0.1500 0.045 Uiso 1 1 calc R . .
N61 N 0.82776(11) 0.5113(2) 0.20224(8) 0.0186(5) Uani 1 1 d . . .
N62 N 0.94346(10) 0.6043(2) 0.10312(8) 0.0171(5) Uani 1 1 d . . .
O61 O 0.74157(9) 0.4423(2) 0.14086(7) 0.0269(5) Uani 1 1 d . . .
O62 O 0.92473(9) 0.6092(2) 0.24644(7) 0.0251(5) Uani 1 1 d . . .
O63 O 0.90209(9) 0.41673(19) 0.12852(6) 0.0177(4) Uani 1 1 d . . .
O64 O 0.86480(9) 0.6327(2) 0.03298(7) 0.0232(4) Uani 1 1 d . . .
O65 O 0.80567(10) 0.2607(2) 0.06953(7) 0.0256(5) Uani 1 1 d . . .
O66 O 0.75229(9) 0.4582(2) 0.03823(7) 0.0215(4) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 O1 1.205(3) . ?
C1 N1 1.407(3) . ?
C1 C4 1.516(4) . ?
C2 O2 1.208(3) . ?
C2 N1 1.397(3) . ?
C2 C3 1.517(4) . ?
C3 C4 1.539(4) . ?
C3 C7 1.576(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.559(4) . ?
C4 H4 1.0000 . ?
C5 O3 1.428(3) . ?
C5 C8 1.509(4) . ?
C5 C6 1.544(4) . ?
C6 O4 1.215(3) . ?
C6 N2 1.352(3) . ?
C7 O3 1.433(3) . ?
C7 N2 1.480(3) . ?
C7 C10 1.493(4) . ?
C8 O5 1.202(3) . ?
C8 O6 1.336(3) . ?
C9 O6 1.459(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.384(4) . ?
C11 C12 1.390(4) . ?
C11 N1 1.443(3) . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N2 1.468(3) . ?
C17 C18 1.519(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C23 1.386(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.392(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C31 O31 1.207(3) . ?
C31 N31 1.394(4) . ?
C31 C34 1.517(4) . ?
C32 O32 1.209(3) . ?
C32 N31 1.402(3) . ?
C32 C33 1.518(4) . ?
C33 C34 1.547(4) . ?
C33 C37 1.565(4) . ?
C33 H33 1.0000 . ?
C34 C35 1.562(4) . ?
C34 H34 1.0000 . ?
C35 O33 1.428(3) . ?
C35 C38 1.509(4) . ?
C35 C36 1.540(4) . ?
C36 O34 1.220(3) . ?
C36 N32 1.342(4) . ?
C37 O33 1.435(3) . ?
C37 N32 1.484(3) . ?
C37 C40 1.503(4) . ?
C38 O35 1.197(3) . ?
C38 O36 1.333(3) . ?
C39 O36 1.460(3) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.379(4) . ?
C41 C46 1.388(4) . ?
C41 N31 1.447(3) . ?
C42 C43 1.394(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.385(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.388(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.385(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 N32 1.458(3) . ?
C47 C48 1.515(4) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C53 1.386(4) . ?
C48 C49 1.387(4) . ?
C49 C50 1.388(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.379(6) . ?
C50 H50 0.9500 . ?
C51 C52 1.377(5) . ?
C51 H51 0.9500 . ?
C52 C53 1.387(4) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C61 O61 1.206(3) . ?
C61 N61 1.391(4) . ?
C61 C64 1.515(4) . ?
C62 O62 1.206(3) . ?
C62 N61 1.405(3) . ?
C62 C63 1.518(4) . ?
C63 C64 1.536(4) . ?
C63 C67 1.574(4) . ?
C63 H63 1.0000 . ?
C64 C65 1.560(4) . ?
C64 H64 1.0000 . ?
C65 O63 1.432(3) . ?
C65 C68 1.510(4) . ?
C65 C66 1.538(4) . ?
C66 O64 1.215(3) . ?
C66 N62 1.363(3) . ?
C67 O63 1.439(3) . ?
C67 N62 1.481(3) . ?
C67 C70 1.494(4) . ?
C68 O65 1.201(3) . ?
C68 O66 1.335(3) . ?
C69 O66 1.458(3) . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C70 H70A 0.9800 . ?
C70 H70B 0.9800 . ?
C70 H70C 0.9800 . ?
C71 C72 1.387(4) . ?
C71 C76 1.389(4) . ?
C71 N61 1.445(3) . ?
C72 C73 1.391(4) . ?
C72 H72 0.9500 . ?
C73 C74 1.390(4) . ?
C73 H73 0.9500 . ?
C74 C75 1.389(4) . ?
C74 H74 0.9500 . ?
C75 C76 1.389(4) . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
C77 N62 1.469(3) . ?
C77 C78 1.511(4) . ?
C77 H77A 0.9900 . ?
C77 H77B 0.9900 . ?
C78 C83 1.380(4) . ?
C78 C79 1.388(4) . ?
C79 C80 1.389(5) . ?
C79 H79 0.9500 . ?
C80 C81 1.370(6) . ?
C80 H80 0.9500 . ?
C81 C82 1.368(6) . ?
C81 H81 0.9500 . ?
C82 C83 1.390(5) . ?
C82 H82 0.9500 . ?
C83 H83 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O1 C1 N1 125.6(3) . . ?
O1 C1 C4 125.8(3) . . ?
N1 C1 C4 108.6(2) . . ?
O2 C2 N1 124.9(3) . . ?
O2 C2 C3 126.3(2) . . ?
N1 C2 C3 108.8(2) . . ?
C2 C3 C4 105.0(2) . . ?
C2 C3 C7 114.8(2) . . ?
C4 C3 C7 100.8(2) . . ?
C2 C3 H3 111.8 . . ?
C4 C3 H3 111.8 . . ?
C7 C3 H3 111.8 . . ?
C1 C4 C3 104.9(2) . . ?
C1 C4 C5 109.7(2) . . ?
C3 C4 C5 101.6(2) . . ?
C1 C4 H4 113.3 . . ?
C3 C4 H4 113.3 . . ?
C5 C4 H4 113.3 . . ?
O3 C5 C8 111.5(2) . . ?
O3 C5 C6 102.0(2) . . ?
C8 C5 C6 117.3(2) . . ?
O3 C5 C4 101.7(2) . . ?
C8 C5 C4 118.2(2) . . ?
C6 C5 C4 103.8(2) . . ?
O4 C6 N2 128.5(3) . . ?
O4 C6 C5 128.4(2) . . ?
N2 C6 C5 102.9(2) . . ?
O3 C7 N2 100.7(2) . . ?
O3 C7 C10 111.6(2) . . ?
N2 C7 C10 114.7(2) . . ?
O3 C7 C3 102.0(2) . . ?
N2 C7 C3 105.6(2) . . ?
C10 C7 C3 119.8(2) . . ?
O5 C8 O6 125.9(3) . . ?
O5 C8 C5 124.2(3) . . ?
O6 C8 C5 109.9(2) . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.6(3) . . ?
C16 C11 N1 119.6(2) . . ?
C12 C11 N1 118.8(3) . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 118.9(3) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
N2 C17 C18 114.5(2) . . ?
N2 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
N2 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C23 C18 C19 118.5(3) . . ?
C23 C18 C17 121.2(3) . . ?
C19 C18 C17 120.2(3) . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 120.6(3) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C2 N1 C1 112.3(2) . . ?
C2 N1 C11 124.9(2) . . ?
C1 N1 C11 122.8(2) . . ?
C6 N2 C17 121.7(2) . . ?
C6 N2 C7 107.5(2) . . ?
C17 N2 C7 124.8(2) . . ?
C5 O3 C7 97.31(19) . . ?
C8 O6 C9 115.3(2) . . ?
O31 C31 N31 126.0(3) . . ?
O31 C31 C34 125.2(3) . . ?
N31 C31 C34 108.8(2) . . ?
O32 C32 N31 124.8(3) . . ?
O32 C32 C33 126.5(2) . . ?
N31 C32 C33 108.6(2) . . ?
C32 C33 C34 104.7(2) . . ?
C32 C33 C37 114.6(2) . . ?
C34 C33 C37 101.0(2) . . ?
C32 C33 H33 111.9 . . ?
C34 C33 H33 111.9 . . ?
C37 C33 H33 111.9 . . ?
C31 C34 C33 104.8(2) . . ?
C31 C34 C35 109.9(2) . . ?
C33 C34 C35 101.3(2) . . ?
C31 C34 H34 113.3 . . ?
C33 C34 H34 113.3 . . ?
C35 C34 H34 113.3 . . ?
O33 C35 C38 112.0(2) . . ?
O33 C35 C36 101.8(2) . . ?
C38 C35 C36 116.9(2) . . ?
O33 C35 C34 101.6(2) . . ?
C38 C35 C34 118.3(2) . . ?
C36 C35 C34 103.9(2) . . ?
O34 C36 N32 128.0(3) . . ?
O34 C36 C35 128.5(3) . . ?
N32 C36 C35 103.4(2) . . ?
O33 C37 N32 100.6(2) . . ?
O33 C37 C40 111.8(2) . . ?
N32 C37 C40 114.7(2) . . ?
O33 C37 C33 102.2(2) . . ?
N32 C37 C33 105.1(2) . . ?
C40 C37 C33 120.0(2) . . ?
O35 C38 O36 126.3(3) . . ?
O35 C38 C35 123.8(3) . . ?
O36 C38 C35 109.8(2) . . ?
O36 C39 H39A 109.5 . . ?
O36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C46 121.3(3) . . ?
C42 C41 N31 120.1(2) . . ?
C46 C41 N31 118.7(2) . . ?
C41 C42 C43 119.2(3) . . ?
C41 C42 H42 120.4 . . ?
C43 C42 H42 120.4 . . ?
C44 C43 C42 119.8(3) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C45 120.5(3) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C46 C45 C44 119.9(3) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C41 119.2(3) . . ?
C45 C46 H46 120.4 . . ?
C41 C46 H46 120.4 . . ?
N32 C47 C48 114.1(2) . . ?
N32 C47 H47A 108.7 . . ?
C48 C47 H47A 108.7 . . ?
N32 C47 H47B 108.7 . . ?
C48 C47 H47B 108.7 . . ?
H47A C47 H47B 107.6 . . ?
C53 C48 C49 119.2(3) . . ?
C53 C48 C47 122.4(3) . . ?
C49 C48 C47 118.4(3) . . ?
C48 C49 C50 120.2(3) . . ?
C48 C49 H49 119.9 . . ?
C50 C49 H49 119.9 . . ?
C51 C50 C49 120.5(3) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 H50 119.8 . . ?
C52 C51 C50 119.4(3) . . ?
C52 C51 H51 120.3 . . ?
C50 C51 H51 120.3 . . ?
C51 C52 C53 120.6(3) . . ?
C51 C52 H52 119.7 . . ?
C53 C52 H52 119.7 . . ?
C48 C53 C52 120.1(3) . . ?
C48 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C31 N31 C32 112.6(2) . . ?
C31 N31 C41 122.9(2) . . ?
C32 N31 C41 124.5(2) . . ?
C36 N32 C47 123.2(2) . . ?
C36 N32 C37 107.6(2) . . ?
C47 N32 C37 126.0(2) . . ?
C35 O33 C37 97.39(19) . . ?
C38 O36 C39 115.2(2) . . ?
O61 C61 N61 125.4(3) . . ?
O61 C61 C64 125.6(3) . . ?
N61 C61 C64 108.9(2) . . ?
O62 C62 N61 125.4(3) . . ?
O62 C62 C63 126.6(2) . . ?
N61 C62 C63 108.0(2) . . ?
C62 C63 C64 105.3(2) . . ?
C62 C63 C67 113.4(2) . . ?
C64 C63 C67 101.1(2) . . ?
C62 C63 H63 112.1 . . ?
C64 C63 H63 112.1 . . ?
C67 C63 H63 112.1 . . ?
C61 C64 C63 104.7(2) . . ?
C61 C64 C65 109.5(2) . . ?
C63 C64 C65 101.7(2) . . ?
C61 C64 H64 113.4 . . ?
C63 C64 H64 113.4 . . ?
C65 C64 H64 113.4 . . ?
O63 C65 C68 112.1(2) . . ?
O63 C65 C66 102.0(2) . . ?
C68 C65 C66 116.7(2) . . ?
O63 C65 C64 101.1(2) . . ?
C68 C65 C64 118.0(2) . . ?
C66 C65 C64 104.7(2) . . ?
O64 C66 N62 128.3(3) . . ?
O64 C66 C65 128.7(2) . . ?
N62 C66 C65 102.9(2) . . ?
O63 C67 N62 100.1(2) . . ?
O63 C67 C70 112.2(2) . . ?
N62 C67 C70 115.5(2) . . ?
O63 C67 C63 101.9(2) . . ?
N62 C67 C63 106.0(2) . . ?
C70 C67 C63 118.8(2) . . ?
O65 C68 O66 126.2(3) . . ?
O65 C68 C65 124.3(3) . . ?
O66 C68 C65 109.4(2) . . ?
O66 C69 H69A 109.5 . . ?
O66 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
O66 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C67 C70 H70A 109.5 . . ?
C67 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
C67 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C72 C71 C76 121.5(3) . . ?
C72 C71 N61 119.9(2) . . ?
C76 C71 N61 118.6(3) . . ?
C71 C72 C73 118.9(3) . . ?
C71 C72 H72 120.5 . . ?
C73 C72 H72 120.5 . . ?
C74 C73 C72 120.3(3) . . ?
C74 C73 H73 119.8 . . ?
C72 C73 H73 119.8 . . ?
C75 C74 C73 119.9(3) . . ?
C75 C74 H74 120.1 . . ?
C73 C74 H74 120.1 . . ?
C74 C75 C76 120.4(3) . . ?
C74 C75 H75 119.8 . . ?
C76 C75 H75 119.8 . . ?
C71 C76 C75 118.9(3) . . ?
C71 C76 H76 120.6 . . ?
C75 C76 H76 120.6 . . ?
N62 C77 C78 114.6(2) . . ?
N62 C77 H77A 108.6 . . ?
C78 C77 H77A 108.6 . . ?
N62 C77 H77B 108.6 . . ?
C78 C77 H77B 108.6 . . ?
H77A C77 H77B 107.6 . . ?
C83 C78 C79 118.6(3) . . ?
C83 C78 C77 121.2(3) . . ?
C79 C78 C77 120.1(3) . . ?
C78 C79 C80 120.3(4) . . ?
C78 C79 H79 119.8 . . ?
C80 C79 H79 119.8 . . ?
C81 C80 C79 120.2(4) . . ?
C81 C80 H80 119.9 . . ?
C79 C80 H80 119.9 . . ?
C82 C81 C80 120.2(3) . . ?
C82 C81 H81 119.9 . . ?
C80 C81 H81 119.9 . . ?
C81 C82 C83 119.8(4) . . ?
C81 C82 H82 120.1 . . ?
C83 C82 H82 120.1 . . ?
C78 C83 C82 120.9(4) . . ?
C78 C83 H83 119.5 . . ?
C82 C83 H83 119.5 . . ?
C61 N61 C62 112.6(2) . . ?
C61 N61 C71 123.6(2) . . ?
C62 N61 C71 123.8(2) . . ?
C66 N62 C77 121.4(2) . . ?
C66 N62 C67 107.5(2) . . ?
C77 N62 C67 125.0(2) . . ?
C65 O63 C67 97.37(19) . . ?
C68 O66 C69 115.3(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.331
_refine_diff_density_min   -0.271
_refine_diff_density_rms    0.060
