data_02sot097
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Phil Gale
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C32 H25 N3 O3'
_chemical_formula_weight          499.55
 
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                    8.8334(2)
_cell_length_b                    15.6053(4)
_cell_length_c                    19.0971(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  102.4470(10)
_cell_angle_gamma                 90.00
_cell_volume                      2570.62(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     7988
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.07
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.291
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1048
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type    Multi-scans
_exptl_absorpt_correction_T_min   0.9834
_exptl_absorpt_correction_T_max   0.9941
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
?
;
 
_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   graphite
_diffrn_measurement_device_type   'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method        'φ and ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  '9.091 pixels mm^1^'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             8697
_diffrn_reflns_av_R_equivalents   0.0390
_diffrn_reflns_av_sigmaI/netI     0.0669
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.10
_diffrn_reflns_theta_max          25.02
_reflns_number_total              4541
_reflns_number_gt                 3130
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO (Otwinowski and MInor, 1997)'
_computing_data_reduction         'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.0602P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        none
_refine_ls_number_reflns          4541
_refine_ls_number_parameters      344
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0763
_refine_ls_R_factor_gt            0.0435
_refine_ls_wR_factor_ref          0.1127
_refine_ls_wR_factor_gt           0.0987
_refine_ls_goodness_of_fit_ref    0.965
_refine_ls_restrained_S_all       0.965
_refine_ls_shift/su_max           0.028
_refine_ls_shift/su_mean          0.001
 
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
N1 N 0.60314(16) 0.61896(9) 0.04076(8) 0.0226(4) Uani 1 1 d . . .
H1 H 0.6785 0.6079 0.0186 0.027 Uiso 1 1 calc R . .
N2 N 0.88733(16) 0.40806(9) -0.06134(8) 0.0220(4) Uani 1 1 d . . .
H2 H 0.7932 0.4293 -0.0671 0.026 Uiso 1 1 calc R . .
O1 O 0.45349(13) 0.55590(8) 0.11092(7) 0.0248(3) Uani 1 1 d . . .
O2 O 0.75958(12) 0.47474(7) 0.03910(7) 0.0205(3) Uani 1 1 d . . .
O3 O 1.08921(13) 0.35626(8) 0.02453(7) 0.0263(3) Uani 1 1 d . . .
C1 C 0.4414(2) 0.73605(12) 0.07184(11) 0.0283(5) Uani 1 1 d . . .
H1A H 0.4156 0.7033 0.1095 0.034 Uiso 1 1 calc R . .
C2 C 0.3855(2) 0.81930(13) 0.05858(12) 0.0336(5) Uani 1 1 d . . .
H2A H 0.3202 0.8429 0.0872 0.040 Uiso 1 1 calc R . .
C3 C 0.4235(2) 0.86800(13) 0.00459(12) 0.0336(5) Uani 1 1 d . . .
H3 H 0.3845 0.9246 -0.0040 0.040 Uiso 1 1 calc R . .
C4 C 0.5190(2) 0.83375(13) -0.03705(12) 0.0321(5) Uani 1 1 d . . .
H4 H 0.5469 0.8673 -0.0738 0.039 Uiso 1 1 calc R . .
C5 C 0.5739(2) 0.75061(12) -0.02522(11) 0.0272(5) Uani 1 1 d . . .
H5 H 0.6381 0.7271 -0.0544 0.033 Uiso 1 1 calc R . .
C6 C 0.53529(19) 0.70163(11) 0.02915(10) 0.0230(4) Uani 1 1 d . . .
C7 C 0.56537(18) 0.55492(11) 0.08204(10) 0.0204(4) Uani 1 1 d . . .
C8 C 0.67314(18) 0.48110(11) 0.09063(10) 0.0192(4) Uani 1 1 d . . .
C9 C 0.71826(18) 0.42042(11) 0.14264(10) 0.0192(4) Uani 1 1 d . . .
C10 C 0.84354(18) 0.37379(11) 0.12226(10) 0.0186(4) Uani 1 1 d . . .
C11 C 0.86343(18) 0.40884(11) 0.05951(10) 0.0194(4) Uani 1 1 d . . .
C12 C 0.95881(19) 0.38777(11) 0.00656(10) 0.0205(4) Uani 1 1 d . . .
C13 C 0.94631(18) 0.39910(11) -0.12427(10) 0.0205(4) Uani 1 1 d . . .
C14 C 0.89131(19) 0.45630(11) -0.17975(10) 0.0224(4) Uani 1 1 d . . .
H14 H 0.8210 0.5002 -0.1734 0.027 Uiso 1 1 calc R . .
C15 C 0.9383(2) 0.44970(12) -0.24404(11) 0.0260(5) Uani 1 1 d . . .
H15 H 0.8992 0.4884 -0.2820 0.031 Uiso 1 1 calc R . .
C16 C 1.0425(2) 0.38644(13) -0.25285(11) 0.0287(5) Uani 1 1 d . . .
H16 H 1.0763 0.3822 -0.2967 0.034 Uiso 1 1 calc R . .
C17 C 1.0971(2) 0.32953(13) -0.19782(11) 0.0286(5) Uani 1 1 d . . .
H17 H 1.1687 0.2863 -0.2041 0.034 Uiso 1 1 calc R . .
C18 C 1.04879(18) 0.33479(12) -0.13369(11) 0.0247(5) Uani 1 1 d . . .
H18 H 1.0854 0.2948 -0.0964 0.030 Uiso 1 1 calc R . .
C19 C 0.66355(19) 0.40976(11) 0.21036(10) 0.0203(4) Uani 1 1 d . . .
C20 C 0.5062(2) 0.40712(11) 0.21148(11) 0.0248(4) Uani 1 1 d . . .
H20 H 0.4310 0.4086 0.1677 0.030 Uiso 1 1 calc R . .
C21 C 0.4589(2) 0.40234(12) 0.27607(11) 0.0287(5) Uani 1 1 d . . .
H21 H 0.3515 0.4008 0.2763 0.034 Uiso 1 1 calc R . .
C22 C 0.5672(2) 0.39975(13) 0.33984(12) 0.0333(5) Uani 1 1 d . . .
H22 H 0.5343 0.3980 0.3840 0.040 Uiso 1 1 calc R . .
C23 C 0.7242(2) 0.39963(13) 0.33980(11) 0.0315(5) Uani 1 1 d . . .
H23 H 0.7988 0.3964 0.3838 0.038 Uiso 1 1 calc R . .
C24 C 0.7718(2) 0.40426(12) 0.27541(11) 0.0249(5) Uani 1 1 d . . .
H24 H 0.8794 0.4037 0.2754 0.030 Uiso 1 1 calc R . .
C25 C 0.92432(18) 0.29872(11) 0.16070(10) 0.0195(4) Uani 1 1 d . . .
C26 C 0.8380(2) 0.22920(12) 0.17608(11) 0.0271(5) Uani 1 1 d . . .
H26 H 0.7281 0.2305 0.1618 0.033 Uiso 1 1 calc R . .
C27 C 0.9105(2) 0.15816(13) 0.21193(12) 0.0324(5) Uani 1 1 d . . .
H27 H 0.8505 0.1106 0.2212 0.039 Uiso 1 1 calc R . .
C28 C 1.0690(2) 0.15647(13) 0.23404(11) 0.0300(5) Uani 1 1 d . . .
H28 H 1.1184 0.1080 0.2592 0.036 Uiso 1 1 calc R . .
C29 C 1.1573(2) 0.22504(12) 0.21988(11) 0.0305(5) Uani 1 1 d . . .
H29 H 1.2669 0.2236 0.2355 0.037 Uiso 1 1 calc R . .
C30 C 1.08567(19) 0.29574(12) 0.18295(11) 0.0261(5) Uani 1 1 d . . .
H30 H 1.1466 0.3424 0.1727 0.031 Uiso 1 1 calc R . .
C32 C 0.0284(3) 0.14085(13) 0.03913(12) 0.0428(6) Uani 1 1 d . . .
H32A H -0.0543 0.1257 -0.0021 0.064 Uiso 1 1 calc R . .
H32B H 0.0916 0.1870 0.0256 0.064 Uiso 1 1 calc R . .
H32C H -0.0176 0.1601 0.0788 0.064 Uiso 1 1 calc R . .
C33 C 0.1252(2) 0.06641(14) 0.06150(12) 0.0323(5) Uani 1 1 d . . .
N3 N 0.2004(2) 0.00759(13) 0.07888(11) 0.0471(5) 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
N1 C7 1.358(2) . ?
N1 C6 1.420(2) . ?
N2 C12 1.352(2) . ?
N2 C13 1.416(2) . ?
O1 C7 1.231(2) . ?
O2 C8 1.373(2) . ?
O2 C11 1.377(2) . ?
O3 C12 1.231(2) . ?
C1 C6 1.390(3) . ?
C1 C2 1.393(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.390(3) . ?
C7 C8 1.481(2) . ?
C8 C9 1.368(3) . ?
C9 C10 1.446(2) . ?
C9 C19 1.484(3) . ?
C10 C11 1.363(3) . ?
C10 C25 1.481(2) . ?
C11 C12 1.486(2) . ?
C13 C18 1.389(2) . ?
C13 C14 1.390(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.384(3) . ?
C19 C20 1.395(2) . ?
C19 C24 1.398(3) . ?
C20 C21 1.387(3) . ?
C21 C22 1.378(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.385(3) . ?
C25 C26 1.393(2) . ?
C25 C30 1.398(2) . ?
C26 C27 1.385(3) . ?
C27 C28 1.373(3) . ?
C28 C29 1.385(3) . ?
C29 C30 1.387(3) . ?
C32 C33 1.451(3) . ?
C33 N3 1.140(3) . ?
 
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
C7 N1 C6 127.66(15) . . ?
C12 N2 C13 127.57(15) . . ?
C8 O2 C11 106.89(14) . . ?
C6 C1 C2 119.10(19) . . ?
C3 C2 C1 121.07(19) . . ?
C2 C3 C4 119.52(18) . . ?
C3 C4 C5 120.2(2) . . ?
C4 C5 C6 120.17(18) . . ?
C5 C6 C1 119.94(17) . . ?
C5 C6 N1 116.94(16) . . ?
C1 C6 N1 123.01(17) . . ?
O1 C7 N1 124.90(16) . . ?
O1 C7 C8 121.26(16) . . ?
N1 C7 C8 113.84(15) . . ?
C9 C8 O2 110.51(14) . . ?
C9 C8 C7 134.32(17) . . ?
O2 C8 C7 114.86(15) . . ?
C8 C9 C10 105.84(16) . . ?
C8 C9 C19 127.70(16) . . ?
C10 C9 C19 126.15(16) . . ?
C11 C10 C9 106.61(15) . . ?
C11 C10 C25 127.85(15) . . ?
C9 C10 C25 125.40(16) . . ?
C10 C11 O2 110.14(15) . . ?
C10 C11 C12 135.17(16) . . ?
O2 C11 C12 114.42(15) . . ?
O3 C12 N2 125.20(17) . . ?
O3 C12 C11 122.16(17) . . ?
N2 C12 C11 112.63(15) . . ?
C18 C13 C14 119.71(17) . . ?
C18 C13 N2 123.40(17) . . ?
C14 C13 N2 116.82(16) . . ?
C15 C14 C13 120.44(17) . . ?
C14 C15 C16 119.73(19) . . ?
C17 C16 C15 119.90(19) . . ?
C16 C17 C18 120.76(18) . . ?
C17 C18 C13 119.44(18) . . ?
C20 C19 C24 118.54(17) . . ?
C20 C19 C9 121.95(17) . . ?
C24 C19 C9 119.49(15) . . ?
C21 C20 C19 120.50(18) . . ?
C22 C21 C20 120.15(18) . . ?
C21 C22 C23 120.24(19) . . ?
C24 C23 C22 119.70(19) . . ?
C23 C24 C19 120.79(17) . . ?
C26 C25 C30 118.61(16) . . ?
C26 C25 C10 119.54(14) . . ?
C30 C25 C10 121.85(16) . . ?
C27 C26 C25 120.75(16) . . ?
C28 C27 C26 119.98(18) . . ?
C27 C28 C29 120.34(17) . . ?
C28 C29 C30 119.98(16) . . ?
C29 C30 C25 120.33(17) . . ?
N3 C33 C32 179.5(3) . . ?
 
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
N2 H2 O1  0.88 2.17 3.0079(18) 158.6 3_665
N1 H1 O3  0.88 2.43 3.2481(19) 153.9 3_765
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.209
_refine_diff_density_min   -0.256
_refine_diff_density_rms    0.049
