 
data_ssf1327
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Methylmalonic acid and 1,1,3,3-tetramethylbutylamine
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H23 N O4'
_chemical_formula_weight          233.30
 
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            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    11.189(7)
_cell_length_b                    11.208(6)
_cell_length_c                    21.906(13)
_cell_angle_alpha                 84.512(7)
_cell_angle_beta                  85.814(7)
_cell_angle_gamma                 89.942(7)
_cell_volume                      2727(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     975
_cell_measurement_theta_min       2.75
_cell_measurement_theta_max       21.07
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.04
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.136
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1024
_exptl_absorpt_coefficient_mu     0.085
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   0.9966
_exptl_absorpt_correction_T_max   0.9991
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.6905
_diffrn_radiation_type            synchrotron
_diffrn_radiation_source          'Daresbury SRS station 9.8'
_diffrn_radiation_monochromator   'silicon 111'
_diffrn_measurement_device_type   'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method        'fine-slice ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         5
_diffrn_reflns_number             14900
_diffrn_reflns_av_R_equivalents   0.0668
_diffrn_reflns_av_sigmaI/netI     0.0859
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          21.34
_reflns_number_total              6612
_reflns_number_gt                 4985
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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)+(0.1225P)²+10.9513P] 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      SHELXL
_refine_ls_extinction_coef        0.076(6)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          6612
_refine_ls_number_parameters      610
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1253
_refine_ls_R_factor_gt            0.0988
_refine_ls_wR_factor_ref          0.2717
_refine_ls_wR_factor_gt           0.2520
_refine_ls_goodness_of_fit_ref    1.050
_refine_ls_restrained_S_all       1.050
_refine_ls_shift/su_max           0.000
_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 0.3460(7) 1.7753(7) 0.0030(4) 0.038(2) Uani 1 1 d . . .
C2 C 0.3797(7) 1.6687(7) 0.0460(4) 0.039(2) Uani 1 1 d . . .
C3 C 0.3784(8) 1.4571(8) 0.0633(5) 0.048(2) Uani 1 1 d . . .
H3A H 0.4596 1.4643 0.0766 0.072 Uiso 1 1 calc R . .
H3B H 0.3745 1.3883 0.0390 0.072 Uiso 1 1 calc R . .
H3C H 0.3212 1.4454 0.0994 0.072 Uiso 1 1 calc R . .
O1A O 0.4056(5) 1.8697(5) 0.0084(2) 0.0394(14) Uani 1 1 d . . .
O1B O 0.2644(5) 1.7639(5) -0.0316(2) 0.0398(14) Uani 1 1 d . . .
O2A O 0.3494(5) 1.5637(5) 0.0266(3) 0.0383(14) Uani 1 1 d . . .
O2B O 0.4290(6) 1.6747(5) 0.0938(3) 0.0575(18) Uani 1 1 d . . .
C21 C 0.4358(9) 1.1886(8) 0.1858(5) 0.057(3) Uani 1 1 d . . .
H21A H 0.4450 1.2339 0.1451 0.086 Uiso 1 1 calc R . .
H21B H 0.4937 1.2182 0.2123 0.086 Uiso 1 1 calc R . .
H21C H 0.3544 1.1989 0.2040 0.086 Uiso 1 1 calc R . .
C22 C 0.4584(7) 1.0550(7) 0.1792(4) 0.037(2) Uani 1 1 d . . .
C23 C 0.5911(7) 1.0456(7) 0.1566(4) 0.0327(19) Uani 1 1 d . . .
H23A H 0.6061 1.1107 0.1231 0.039 Uiso 1 1 calc R . .
H23B H 0.6377 1.0663 0.1909 0.039 Uiso 1 1 calc R . .
C24 C 0.6493(7) 0.9339(7) 0.1334(3) 0.0312(18) Uani 1 1 d . . .
C26 C 0.4329(8) 0.9880(9) 0.2437(4) 0.053(2) Uani 1 1 d . . .
H26A H 0.3535 1.0102 0.2608 0.079 Uiso 1 1 calc R . .
H26B H 0.4938 1.0098 0.2707 0.079 Uiso 1 1 calc R . .
H26C H 0.4351 0.9013 0.2406 0.079 Uiso 1 1 calc R . .
C27 C 0.3736(8) 1.0142(10) 0.1340(5) 0.061(3) Uani 1 1 d . . .
H27A H 0.3924 1.0574 0.0934 0.092 Uiso 1 1 calc R . .
H27B H 0.2908 1.0309 0.1483 0.092 Uiso 1 1 calc R . .
H27C H 0.3830 0.9279 0.1312 0.092 Uiso 1 1 calc R . .
C28 C 0.7858(7) 0.9550(8) 0.1257(4) 0.036(2) Uani 1 1 d . . .
H28A H 0.8160 0.9641 0.1659 0.054 Uiso 1 1 calc R . .
H28B H 0.8036 1.0279 0.0981 0.054 Uiso 1 1 calc R . .
H28C H 0.8248 0.8864 0.1082 0.054 Uiso 1 1 calc R . .
C29 C 0.6218(7) 0.8167(7) 0.1722(4) 0.037(2) Uani 1 1 d . . .
H29A H 0.6417 0.8240 0.2145 0.056 Uiso 1 1 calc R . .
H29B H 0.6696 0.7525 0.1553 0.056 Uiso 1 1 calc R . .
H29C H 0.5364 0.7976 0.1719 0.056 Uiso 1 1 calc R . .
N25 N 0.6130(5) 0.9164(6) 0.0691(3) 0.0307(15) Uani 1 1 d . . .
H25A H 0.6631 0.8630 0.0518 0.046 Uiso 1 1 calc R . .
H25B H 0.6176 0.9878 0.0454 0.046 Uiso 1 1 calc R . .
H25C H 0.5364 0.8880 0.0716 0.046 Uiso 1 1 calc R . .
C31 C 0.7207(7) 0.6601(7) 0.4908(3) 0.0292(18) Uani 1 1 d . . .
C32 C 0.8325(7) 0.6276(7) 0.4512(4) 0.037(2) Uani 1 1 d . . .
C33 C 1.0437(7) 0.6251(7) 0.4419(4) 0.041(2) Uani 1 1 d . . .
H33A H 1.0418 0.5386 0.4383 0.061 Uiso 1 1 calc R . .
H33B H 1.1113 0.6443 0.4654 0.061 Uiso 1 1 calc R . .
H33C H 1.0530 0.6683 0.4008 0.061 Uiso 1 1 calc R . .
O31A O 0.6246(5) 0.6100(5) 0.4795(2) 0.0373(14) Uani 1 1 d . . .
O31B O 0.7323(5) 0.7325(5) 0.5297(3) 0.0403(14) Uani 1 1 d . . .
O32A O 0.8305(6) 0.5767(7) 0.4051(3) 0.066(2) Uani 1 1 d . . .
O32B O 0.9328(4) 0.6607(5) 0.4734(2) 0.0364(14) Uani 1 1 d . . .
C41 C 0.6631(10) 0.4071(9) 0.7136(5) 0.062(3) Uani 1 1 d . . .
H41A H 0.7315 0.4626 0.7062 0.093 Uiso 1 1 calc R . .
H41B H 0.6912 0.3248 0.7109 0.093 Uiso 1 1 calc R . .
H41C H 0.6244 0.4142 0.7547 0.093 Uiso 1 1 calc R . .
C42 C 0.5711(7) 0.4386(7) 0.6642(4) 0.037(2) Uani 1 1 d . . .
C43 C 0.5496(7) 0.5729(7) 0.6607(4) 0.039(2) Uani 1 1 d . . .
H43A H 0.6220 0.6109 0.6384 0.047 Uiso 1 1 calc R . .
H43B H 0.5490 0.5949 0.7034 0.047 Uiso 1 1 calc R . .
C44 C 0.4433(7) 0.6368(7) 0.6330(3) 0.0308(18) Uani 1 1 d . . .
C46 C 0.4584(9) 0.3611(8) 0.6844(4) 0.052(2) Uani 1 1 d . . .
H46A H 0.4226 0.3844 0.7236 0.078 Uiso 1 1 calc R . .
H46B H 0.4809 0.2764 0.6893 0.078 Uiso 1 1 calc R . .
H46C H 0.4002 0.3732 0.6531 0.078 Uiso 1 1 calc R . .
C47 C 0.6279(8) 0.3985(7) 0.6032(4) 0.044(2) Uani 1 1 d . . .
H47A H 0.5680 0.4028 0.5726 0.066 Uiso 1 1 calc R . .
H47B H 0.6563 0.3159 0.6101 0.066 Uiso 1 1 calc R . .
H47C H 0.6956 0.4514 0.5882 0.066 Uiso 1 1 calc R . .
C48 C 0.3241(7) 0.6123(8) 0.6695(4) 0.041(2) Uani 1 1 d . . .
H48A H 0.3326 0.6232 0.7128 0.062 Uiso 1 1 calc R . .
H48B H 0.2985 0.5299 0.6658 0.062 Uiso 1 1 calc R . .
H48C H 0.2640 0.6682 0.6533 0.062 Uiso 1 1 calc R . .
C49 C 0.4703(7) 0.7723(6) 0.6272(4) 0.0349(19) Uani 1 1 d . . .
H49A H 0.4003 0.8165 0.6130 0.052 Uiso 1 1 calc R . .
H49B H 0.5392 0.7902 0.5974 0.052 Uiso 1 1 calc R . .
H49C H 0.4886 0.7965 0.6673 0.052 Uiso 1 1 calc R . .
N45 N 0.4260(5) 0.6096(5) 0.5677(3) 0.0303(16) Uani 1 1 d . . .
H45A H 0.4975 0.6163 0.5450 0.07(3) Uiso 1 1 calc R . .
H45B H 0.3731 0.6625 0.5508 0.03(2) Uiso 1 1 calc R . .
H45C H 0.3969 0.5337 0.5681 0.03(2) Uiso 1 1 calc R . .
C51 C 0.3301(7) 0.8983(7) 0.4551(4) 0.0346(19) Uani 1 1 d . . .
C52 C 0.2229(7) 0.8488(7) 0.4994(4) 0.0318(19) Uani 1 1 d . . .
C53 C 0.5405(7) 0.8984(8) 0.4359(4) 0.045(2) Uani 1 1 d . . .
H53A H 0.5394 0.8667 0.3958 0.068 Uiso 1 1 calc R . .
H53B H 0.6123 0.8699 0.4558 0.068 Uiso 1 1 calc R . .
H53C H 0.5416 0.9862 0.4302 0.068 Uiso 1 1 calc R . .
O51A O 0.4339(4) 0.8574(4) 0.4744(2) 0.0346(13) Uani 1 1 d . . .
O51B O 0.3187(5) 0.9638(6) 0.4087(3) 0.0513(16) Uani 1 1 d . . .
O52A O 0.1302(5) 0.9095(5) 0.4936(2) 0.0391(14) Uani 1 1 d . . .
O52B O 0.2380(5) 0.7569(5) 0.5334(3) 0.0394(14) Uani 1 1 d . . .
C61 C 0.9834(9) 0.3485(10) 0.7845(5) 0.063(3) Uani 1 1 d . . .
H61A H 1.0395 0.2828 0.7926 0.094 Uiso 1 1 calc R . .
H61B H 1.0035 0.3891 0.7434 0.094 Uiso 1 1 calc R . .
H61C H 0.9015 0.3165 0.7867 0.094 Uiso 1 1 calc R . .
C62 C 0.9920(7) 0.4386(7) 0.8329(4) 0.036(2) Uani 1 1 d . . .
C63 C 1.1272(7) 0.4640(7) 0.8366(4) 0.039(2) Uani 1 1 d . . .
H63A H 1.1603 0.3904 0.8576 0.047 Uiso 1 1 calc R . .
H63B H 1.1630 0.4700 0.7938 0.047 Uiso 1 1 calc R . .
C64 C 1.1803(7) 0.5699(7) 0.8665(3) 0.0311(18) Uani 1 1 d . . .
C66 C 0.9197(8) 0.5495(9) 0.8144(4) 0.052(2) Uani 1 1 d . . .
H66A H 0.9557 0.5897 0.7758 0.078 Uiso 1 1 calc R . .
H66B H 0.9196 0.6043 0.8467 0.078 Uiso 1 1 calc R . .
H66C H 0.8371 0.5259 0.8090 0.078 Uiso 1 1 calc R . .
C67 C 0.9359(8) 0.3792(8) 0.8944(4) 0.052(2) Uani 1 1 d . . .
H67A H 0.8577 0.3448 0.8881 0.078 Uiso 1 1 calc R . .
H67B H 0.9255 0.4393 0.9240 0.078 Uiso 1 1 calc R . .
H67C H 0.9886 0.3155 0.9102 0.078 Uiso 1 1 calc R . .
C68 C 1.1616(8) 0.6932(7) 0.8313(4) 0.041(2) Uani 1 1 d . . .
H68A H 1.2070 0.7542 0.8492 0.061 Uiso 1 1 calc R . .
H68B H 1.0762 0.7132 0.8343 0.061 Uiso 1 1 calc R . .
H68C H 1.1896 0.6908 0.7880 0.061 Uiso 1 1 calc R . .
C69 C 1.3135(7) 0.5447(7) 0.8700(4) 0.038(2) Uani 1 1 d . . .
H69A H 1.3510 0.6090 0.8893 0.057 Uiso 1 1 calc R . .
H69B H 1.3511 0.5407 0.8284 0.057 Uiso 1 1 calc R . .
H69C H 1.3241 0.4680 0.8945 0.057 Uiso 1 1 calc R . .
N65 N 1.1312(5) 0.5770(6) 0.9318(3) 0.0322(16) Uani 1 1 d . . .
H65A H 1.1724 0.6336 0.9489 0.048 Uiso 1 1 calc R . .
H65B H 1.1391 0.5046 0.9537 0.048 Uiso 1 1 calc R . .
H65C H 1.0523 0.5970 0.9323 0.048 Uiso 1 1 calc R . .
C71 C -0.1138(7) 0.8337(7) 0.9512(4) 0.0335(19) Uani 1 1 d . . .
C72 C -0.1610(7) 0.7181(7) 0.9909(4) 0.0320(19) Uani 1 1 d . . .
C73 C -0.1076(7) 1.0457(7) 0.9428(4) 0.042(2) Uani 1 1 d . . .
H73A H -0.0200 1.0436 0.9375 0.062 Uiso 1 1 calc R . .
H73B H -0.1323 1.1114 0.9674 0.062 Uiso 1 1 calc R . .
H73C H -0.1406 1.0584 0.9025 0.062 Uiso 1 1 calc R . .
O71A O -0.1525(5) 0.9319(4) 0.9746(2) 0.0354(14) Uani 1 1 d . . .
O71B O -0.0527(7) 0.8323(6) 0.9056(3) 0.073(2) Uani 1 1 d . . .
O72A O -0.2428(5) 0.7296(5) 1.0300(3) 0.0410(14) Uani 1 1 d . . .
O72B O -0.1052(5) 0.6253(5) 0.9798(2) 0.0366(14) Uani 1 1 d . . .
C81 C -0.0113(9) 0.9910(9) 0.7438(4) 0.054(2) Uani 1 1 d . . .
H81A H 0.0032 1.0692 0.7585 0.081 Uiso 1 1 calc R . .
H81B H 0.0167 0.9274 0.7732 0.081 Uiso 1 1 calc R . .
H81C H -0.0972 0.9806 0.7399 0.081 Uiso 1 1 calc R . .
C82 C 0.0575(8) 0.9842(7) 0.6804(4) 0.043(2) Uani 1 1 d . . .
C83 C 0.0505(7) 0.8577(7) 0.6584(4) 0.0325(19) Uani 1 1 d . . .
H83A H 0.1160 0.8539 0.6258 0.039 Uiso 1 1 calc R . .
H83B H 0.0722 0.8011 0.6934 0.039 Uiso 1 1 calc R . .
C84 C -0.0605(7) 0.8038(7) 0.6339(4) 0.0343(19) Uani 1 1 d . . .
C86 C 0.1917(8) 1.0028(9) 0.6898(5) 0.055(3) Uani 1 1 d . . .
H86A H 0.2392 0.9970 0.6508 0.083 Uiso 1 1 calc R . .
H86B H 0.2175 0.9410 0.7207 0.083 Uiso 1 1 calc R . .
H86C H 0.2034 1.0822 0.7038 0.083 Uiso 1 1 calc R . .
C87 C 0.0164(11) 1.0800(8) 0.6347(5) 0.068(3) Uani 1 1 d . . .
H87A H 0.0533 1.0682 0.5938 0.102 Uiso 1 1 calc R . .
H87B H 0.0398 1.1586 0.6462 0.102 Uiso 1 1 calc R . .
H87C H -0.0710 1.0760 0.6342 0.102 Uiso 1 1 calc R . .
C88 C -0.1772(7) 0.8157(7) 0.6738(4) 0.036(2) Uani 1 1 d . . .
H88A H -0.1982 0.9006 0.6740 0.054 Uiso 1 1 calc R . .
H88B H -0.1665 0.7816 0.7159 0.054 Uiso 1 1 calc R . .
H88C H -0.2416 0.7725 0.6571 0.054 Uiso 1 1 calc R . .
C89 C -0.0358(8) 0.6724(7) 0.6263(4) 0.038(2) Uani 1 1 d . . .
H89A H -0.0191 0.6307 0.6661 0.056 Uiso 1 1 calc R . .
H89B H 0.0337 0.6660 0.5969 0.056 Uiso 1 1 calc R . .
H89C H -0.1060 0.6360 0.6111 0.056 Uiso 1 1 calc R . .
N85 N -0.0794(5) 0.8631(6) 0.5700(3) 0.0312(15) Uani 1 1 d . . .
H85A H -0.1117 0.9370 0.5731 0.047 Uiso 1 1 calc R . .
H85B H -0.1301 0.8173 0.5513 0.047 Uiso 1 1 calc R . .
H85C H -0.0078 0.8703 0.5474 0.047 Uiso 1 1 calc R . .
 
 
_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 O1B 1.243(10) . ?
C1 O1A 1.271(10) . ?
C1 C2 1.514(12) . ?
C2 O2B 1.226(10) . ?
C2 O2A 1.341(10) . ?
C3 O2A 1.426(10) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C21 C22 1.537(12) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.521(12) . ?
C22 C23 1.537(11) . ?
C22 C26 1.544(12) . ?
C23 C24 1.524(11) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C29 1.514(11) . ?
C24 N25 1.525(10) . ?
C24 C28 1.540(10) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
N25 H25A 0.9100 . ?
N25 H25B 0.9100 . ?
N25 H25C 0.9100 . ?
C31 O31B 1.245(9) . ?
C31 O31A 1.265(9) . ?
C31 C32 1.532(11) . ?
C32 O32A 1.207(10) . ?
C32 O32B 1.322(9) . ?
C33 O32B 1.449(10) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C41 C42 1.564(12) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.520(12) . ?
C42 C47 1.544(12) . ?
C42 C46 1.546(12) . ?
C43 C44 1.521(11) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C48 1.515(11) . ?
C44 N45 1.517(9) . ?
C44 C49 1.541(11) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
N45 H45A 0.9100 . ?
N45 H45B 0.9100 . ?
N45 H45C 0.9100 . ?
C51 O51B 1.210(10) . ?
C51 O51A 1.331(10) . ?
C51 C52 1.555(11) . ?
C52 O52B 1.232(9) . ?
C52 O52A 1.247(9) . ?
C53 O51A 1.458(10) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C61 C62 1.540(12) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C62 C66 1.520(12) . ?
C62 C67 1.535(12) . ?
C62 C63 1.549(11) . ?
C63 C64 1.548(11) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 N65 1.504(10) . ?
C64 C69 1.523(11) . ?
C64 C68 1.538(11) . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
N65 H65A 0.9100 . ?
N65 H65B 0.9100 . ?
N65 H65C 0.9100 . ?
C71 O71B 1.169(10) . ?
C71 O71A 1.317(9) . ?
C71 C72 1.560(11) . ?
C72 O72A 1.222(9) . ?
C72 O72B 1.248(9) . ?
C73 O71A 1.464(9) . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?
C81 C82 1.545(13) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C82 C87 1.492(13) . ?
C82 C83 1.545(11) . ?
C82 C86 1.547(12) . ?
C83 C84 1.536(11) . ?
C83 H83A 0.9900 . ?
C83 H83B 0.9900 . ?
C84 N85 1.518(10) . ?
C84 C89 1.520(11) . ?
C84 C88 1.530(11) . ?
C86 H86A 0.9800 . ?
C86 H86B 0.9800 . ?
C86 H86C 0.9800 . ?
C87 H87A 0.9800 . ?
C87 H87B 0.9800 . ?
C87 H87C 0.9800 . ?
C88 H88A 0.9800 . ?
C88 H88B 0.9800 . ?
C88 H88C 0.9800 . ?
C89 H89A 0.9800 . ?
C89 H89B 0.9800 . ?
C89 H89C 0.9800 . ?
N85 H85A 0.9100 . ?
N85 H85B 0.9100 . ?
N85 H85C 0.9100 . ?
 
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
O1B C1 O1A 127.3(8) . . ?
O1B C1 C2 119.1(7) . . ?
O1A C1 C2 113.6(7) . . ?
O2B C2 O2A 122.2(8) . . ?
O2B C2 C1 125.1(8) . . ?
O2A C2 C1 112.7(7) . . ?
O2A C3 H3A 109.5 . . ?
O2A C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O2A C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 O2A C3 117.4(7) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 113.0(7) . . ?
C27 C22 C21 108.2(8) . . ?
C23 C22 C21 106.0(7) . . ?
C27 C22 C26 111.2(8) . . ?
C23 C22 C26 111.2(7) . . ?
C21 C22 C26 106.8(7) . . ?
C24 C23 C22 124.8(6) . . ?
C24 C23 H23A 106.1 . . ?
C22 C23 H23A 106.1 . . ?
C24 C23 H23B 106.1 . . ?
C22 C23 H23B 106.1 . . ?
H23A C23 H23B 106.3 . . ?
C29 C24 C23 116.4(6) . . ?
C29 C24 N25 106.3(6) . . ?
C23 C24 N25 110.8(6) . . ?
C29 C24 C28 109.7(6) . . ?
C23 C24 C28 108.0(6) . . ?
N25 C24 C28 105.1(6) . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 N25 H25A 109.5 . . ?
C24 N25 H25B 109.5 . . ?
H25A N25 H25B 109.5 . . ?
C24 N25 H25C 109.5 . . ?
H25A N25 H25C 109.5 . . ?
H25B N25 H25C 109.5 . . ?
O31B C31 O31A 126.7(7) . . ?
O31B C31 C32 118.1(6) . . ?
O31A C31 C32 115.2(7) . . ?
O32A C32 O32B 123.1(7) . . ?
O32A C32 C31 124.4(7) . . ?
O32B C32 C31 112.4(7) . . ?
O32B C33 H33A 109.5 . . ?
O32B C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O32B C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 O32B C33 116.5(6) . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C47 112.4(7) . . ?
C43 C42 C46 114.4(7) . . ?
C47 C42 C46 108.7(7) . . ?
C43 C42 C41 107.9(7) . . ?
C47 C42 C41 106.5(7) . . ?
C46 C42 C41 106.5(7) . . ?
C42 C43 C44 125.2(7) . . ?
C42 C43 H43A 106.0 . . ?
C44 C43 H43A 106.0 . . ?
C42 C43 H43B 106.0 . . ?
C44 C43 H43B 106.0 . . ?
H43A C43 H43B 106.3 . . ?
C48 C44 N45 106.6(6) . . ?
C48 C44 C43 114.8(7) . . ?
N45 C44 C43 113.8(6) . . ?
C48 C44 C49 109.4(6) . . ?
N45 C44 C49 104.2(6) . . ?
C43 C44 C49 107.5(6) . . ?
C42 C46 H46A 109.5 . . ?
C42 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C42 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C42 C47 H47A 109.5 . . ?
C42 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C42 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C44 C48 H48A 109.5 . . ?
C44 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C44 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C44 C49 H49A 109.5 . . ?
C44 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C44 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C44 N45 H45A 109.5 . . ?
C44 N45 H45B 109.5 . . ?
H45A N45 H45B 109.5 . . ?
C44 N45 H45C 109.5 . . ?
H45A N45 H45C 109.5 . . ?
H45B N45 H45C 109.5 . . ?
O51B C51 O51A 125.3(7) . . ?
O51B C51 C52 123.5(7) . . ?
O51A C51 C52 111.2(7) . . ?
O52B C52 O52A 129.0(7) . . ?
O52B C52 C51 118.2(7) . . ?
O52A C52 C51 112.8(7) . . ?
O51A C53 H53A 109.5 . . ?
O51A C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
O51A C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 O51A C53 115.6(6) . . ?
C62 C61 H61A 109.5 . . ?
C62 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C62 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C66 C62 C67 108.5(7) . . ?
C66 C62 C61 109.2(7) . . ?
C67 C62 C61 107.6(7) . . ?
C66 C62 C63 113.9(7) . . ?
C67 C62 C63 111.0(7) . . ?
C61 C62 C63 106.5(7) . . ?
C64 C63 C62 125.6(7) . . ?
C64 C63 H63A 105.9 . . ?
C62 C63 H63A 105.9 . . ?
C64 C63 H63B 105.9 . . ?
C62 C63 H63B 105.9 . . ?
H63A C63 H63B 106.3 . . ?
N65 C64 C69 105.6(6) . . ?
N65 C64 C68 107.3(6) . . ?
C69 C64 C68 110.3(6) . . ?
N65 C64 C63 112.9(6) . . ?
C69 C64 C63 106.4(6) . . ?
C68 C64 C63 114.0(7) . . ?
C62 C66 H66A 109.5 . . ?
C62 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C62 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C62 C67 H67A 109.5 . . ?
C62 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C62 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C64 C68 H68A 109.5 . . ?
C64 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C64 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C64 C69 H69A 109.5 . . ?
C64 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C64 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C64 N65 H65A 109.5 . . ?
C64 N65 H65B 109.5 . . ?
H65A N65 H65B 109.5 . . ?
C64 N65 H65C 109.5 . . ?
H65A N65 H65C 109.5 . . ?
H65B N65 H65C 109.5 . . ?
O71B C71 O71A 124.5(7) . . ?
O71B C71 C72 123.4(7) . . ?
O71A C71 C72 112.0(7) . . ?
O72A C72 O72B 128.3(7) . . ?
O72A C72 C71 117.4(7) . . ?
O72B C72 C71 114.2(7) . . ?
O71A C73 H73A 109.5 . . ?
O71A C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
O71A C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
C71 O71A C73 116.5(6) . . ?
C82 C81 H81A 109.5 . . ?
C82 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C82 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C87 C82 C83 112.9(7) . . ?
C87 C82 C81 110.6(8) . . ?
C83 C82 C81 111.8(7) . . ?
C87 C82 C86 109.9(8) . . ?
C83 C82 C86 104.6(7) . . ?
C81 C82 C86 106.6(7) . . ?
C84 C83 C82 125.0(7) . . ?
C84 C83 H83A 106.1 . . ?
C82 C83 H83A 106.1 . . ?
C84 C83 H83B 106.1 . . ?
C82 C83 H83B 106.1 . . ?
H83A C83 H83B 106.3 . . ?
N85 C84 C89 106.2(6) . . ?
N85 C84 C88 107.6(6) . . ?
C89 C84 C88 109.9(7) . . ?
N85 C84 C83 110.0(6) . . ?
C89 C84 C83 108.1(7) . . ?
C88 C84 C83 114.8(6) . . ?
C82 C86 H86A 109.5 . . ?
C82 C86 H86B 109.5 . . ?
H86A C86 H86B 109.5 . . ?
C82 C86 H86C 109.5 . . ?
H86A C86 H86C 109.5 . . ?
H86B C86 H86C 109.5 . . ?
C82 C87 H87A 109.5 . . ?
C82 C87 H87B 109.5 . . ?
H87A C87 H87B 109.5 . . ?
C82 C87 H87C 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
C84 C88 H88A 109.5 . . ?
C84 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C84 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
C84 C89 H89A 109.5 . . ?
C84 C89 H89B 109.5 . . ?
H89A C89 H89B 109.5 . . ?
C84 C89 H89C 109.5 . . ?
H89A C89 H89C 109.5 . . ?
H89B C89 H89C 109.5 . . ?
C84 N85 H85A 109.5 . . ?
C84 N85 H85B 109.5 . . ?
H85A N85 H85B 109.5 . . ?
C84 N85 H85C 109.5 . . ?
H85A N85 H85C 109.5 . . ?
H85B N85 H85C 109.5 . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N45 H45A O31A  0.91 1.95 2.837(8) 163.6 .
N45 H45B O52B  0.91 1.88 2.775(8) 165.4 .
N85 H85C O52A  0.91 1.90 2.800(8) 170.2 .
N25 H25A O72A  0.91 1.91 2.803(9) 168.3 1_654
N25 H25A O71A  0.91 2.64 3.216(8) 122.1 1_654
N25 H25B O1A  0.91 1.92 2.818(8) 168.1 2_685
N25 H25C O1A  0.91 2.11 2.831(8) 135.3 1_545
N45 H45C O31A  0.91 2.02 2.832(8) 147.2 2_666
N65 H65A O1B  0.91 1.89 2.785(8) 168.8 1_646
N65 H65B O72B  0.91 1.98 2.838(8) 157.7 2_667
N65 H65C O72B  0.91 2.02 2.844(8) 149.9 1_655
N85 H85A O52A  0.91 2.17 2.863(8) 132.5 2_576
N85 H85A O51B  0.91 2.59 3.336(9) 139.7 2_576
N85 H85B O31B  0.91 1.92 2.808(8) 164.2 1_455
N85 H85B O32B  0.91 2.62 3.244(8) 126.0 1_455
 
_diffrn_measured_fraction_theta_max    0.989
_diffrn_reflns_theta_full              21.34
_diffrn_measured_fraction_theta_full   0.989
_refine_diff_density_max    0.376
_refine_diff_density_min   -0.298
_refine_diff_density_rms    0.079
