# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Michael Coogan'
_publ_contact_author_email       COOGANMP@CF.AC.UK

_publ_section_title              
;
Stereostructural Behaviour Of N-N Atropisomers: Two
Conglomerate Crystallisations And A Crystallisation-Induced
Deracemisation.
;
_publ_author_address             'Cardiff University CF10 3AT'
_publ_contact_author             'coogan, michael peter'
loop_
_publ_author_name
'Michael Coogan'
'Richard J. Arthur'
'Meritxell Casadesus'
'M Francesconi'
'Robert Haigh'
;
D.Headspith
;
'Rebecca Laye'

# Attachment 'stereostructural_studies_of_N-N_atropisomers.cif'

data_C14H14N4O2
_database_code_depnum_ccdc_archive 'CCDC 702071'

_audit_creation_method           SHELXL-97
_publ_section_abstract           
;
Structural properties of NN atropisomers are discussed
;
_chemical_name_systematic        
;
1,2-bis-(2-aminobenzoyl)hydrazine
;
_chemical_name_common            1,2-bis-(2-aminobenzoyl)hydrazine
_chemical_melting_point          212
_chemical_formula_moiety         'C14 H14 N4 O2'
_chemical_formula_sum            'C14 H14 N4 O2'
_chemical_formula_weight         270.29
_chemical_absolute_configuration unk

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.1158(3)
_cell_length_b                   9.9478(4)
_cell_length_c                   13.7725(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1248.92(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11218
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11134
_diffrn_reflns_av_R_equivalents  0.1509
_diffrn_reflns_av_sigmaI/netI    0.0900
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.44
_reflns_number_total             1643
_reflns_number_gt                1094
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1000P)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     SHELXL
_refine_ls_extinction_coef       0.034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         1643
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_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
O1 O 0.8639(3) 0.0636(3) 0.62669(17) 0.0329(7) Uani 1 1 d . . .
N2 N 1.0015(3) 0.2508(3) 0.63664(19) 0.0269(7) Uani 1 1 d . . .
C3 C 1.1943(4) 0.0614(4) 0.3422(2) 0.0264(8) Uani 1 1 d . . .
C4 C 0.9039(4) 0.1545(4) 0.7855(2) 0.0248(8) Uani 1 1 d . . .
C5 C 1.0460(4) 0.2631(4) 0.3296(2) 0.0251(8) Uani 1 1 d . . .
H5 H 0.9995 0.3377 0.3596 0.030 Uiso 1 1 calc R . .
N6 N 1.0149(4) 0.2488(3) 0.5363(2) 0.0281(7) Uani 1 1 d . . .
C7 C 0.9367(4) 0.2736(4) 0.9390(3) 0.0305(9) Uani 1 1 d . . .
H7 H 0.9767 0.3468 0.9746 0.037 Uiso 1 1 calc R . .
C10 C 1.1814(4) 0.0467(4) 0.2415(2) 0.0313(9) Uani 1 1 d . . .
H10 H 1.2265 -0.0279 0.2104 0.038 Uiso 1 1 calc R . .
C11 C 0.7973(4) 0.0684(4) 0.9338(2) 0.0313(9) Uani 1 1 d . . .
H11 H 0.7414 0.0020 0.9668 0.038 Uiso 1 1 calc R . .
C12 C 1.0360(4) 0.2476(4) 0.2302(2) 0.0291(9) Uani 1 1 d . . .
H12 H 0.9831 0.3106 0.1920 0.035 Uiso 1 1 calc R . .
C14 C 0.9598(4) 0.2630(4) 0.8398(2) 0.0265(9) Uani 1 1 d . . .
H14 H 1.0148 0.3308 0.8076 0.032 Uiso 1 1 calc R . .
C15 C 1.1227(4) 0.1714(3) 0.3866(2) 0.0244(8) Uani 1 1 d . . .
C16 C 0.9213(4) 0.1498(4) 0.6781(2) 0.0250(8) Uani 1 1 d . . .
C17 C 0.8211(4) 0.0567(4) 0.8340(2) 0.0245(8) Uani 1 1 d . . .
C18 C 0.8546(4) 0.1761(4) 0.9852(2) 0.0324(9) Uani 1 1 d . . .
H18 H 0.8372 0.1829 1.0530 0.039 Uiso 1 1 calc R . .
C19 C 1.1049(4) 0.1380(4) 0.1869(2) 0.0320(9) Uani 1 1 d . . .
H19 H 1.0988 0.1264 0.1186 0.038 Uiso 1 1 calc R . .
C20 C 1.1309(4) 0.1873(3) 0.4943(2) 0.0251(8) Uani 1 1 d . . .
O2 O 1.2364(3) 0.1502(3) 0.54398(17) 0.0330(7) Uani 1 1 d . . .
N4 N 0.7645(4) -0.0573(3) 0.7873(2) 0.0305(8) Uani 1 1 d . . .
N3 N 1.2681(4) -0.0350(4) 0.3948(3) 0.0363(9) Uani 1 1 d . . .
H1 H 0.936(4) 0.269(4) 0.503(3) 0.024(10) Uiso 1 1 d . . .
H4 H 1.296(4) -0.015(4) 0.453(3) 0.035(12) Uiso 1 1 d . . .
H6 H 1.070(5) 0.295(4) 0.672(3) 0.047(13) Uiso 1 1 d . . .
H8 H 1.325(5) -0.087(5) 0.358(3) 0.048(13) Uiso 1 1 d . . .
H2 H 0.688(5) -0.099(4) 0.818(2) 0.031(11) Uiso 1 1 d . . .
H3 H 0.761(5) -0.041(4) 0.719(3) 0.044(12) Uiso 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
O1 C16 1.229(4) . ?
N2 C16 1.367(5) . ?
N2 N6 1.387(4) . ?
N2 H6 0.91(4) . ?
C3 N3 1.377(5) . ?
C3 C10 1.400(5) . ?
C3 C15 1.414(5) . ?
C4 C17 1.402(5) . ?
C4 C14 1.409(5) . ?
C4 C16 1.489(4) . ?
C5 C12 1.381(5) . ?
C5 C15 1.392(5) . ?
C5 H5 0.9500 . ?
N6 C20 1.352(5) . ?
N6 H1 0.88(4) . ?
C7 C18 1.380(5) . ?
C7 C14 1.386(5) . ?
C7 H7 0.9500 . ?
C10 C19 1.370(5) . ?
C10 H10 0.9500 . ?
C11 C18 1.386(5) . ?
C11 C17 1.396(5) . ?
C11 H11 0.9500 . ?
C12 C19 1.392(5) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.494(4) . ?
C17 N4 1.402(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O2 1.236(4) . ?
N4 H2 0.91(4) . ?
N4 H3 0.96(4) . ?
N3 H4 0.87(4) . ?
N3 H8 0.89(5) . ?

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
C16 N2 N6 116.9(3) . . ?
C16 N2 H6 120(3) . . ?
N6 N2 H6 119(3) . . ?
N3 C3 C10 119.3(3) . . ?
N3 C3 C15 122.5(3) . . ?
C10 C3 C15 118.1(3) . . ?
C17 C4 C14 118.3(3) . . ?
C17 C4 C16 120.7(3) . . ?
C14 C4 C16 120.9(3) . . ?
C12 C5 C15 121.3(3) . . ?
C12 C5 H5 119.3 . . ?
C15 C5 H5 119.3 . . ?
C20 N6 N2 120.1(3) . . ?
C20 N6 H1 121(2) . . ?
N2 N6 H1 117(2) . . ?
C18 C7 C14 118.9(3) . . ?
C18 C7 H7 120.6 . . ?
C14 C7 H7 120.6 . . ?
C19 C10 C3 121.2(4) . . ?
C19 C10 H10 119.4 . . ?
C3 C10 H10 119.4 . . ?
C18 C11 C17 120.6(3) . . ?
C18 C11 H11 119.7 . . ?
C17 C11 H11 119.7 . . ?
C5 C12 C19 118.8(3) . . ?
C5 C12 H12 120.6 . . ?
C19 C12 H12 120.6 . . ?
C7 C14 C4 121.8(3) . . ?
C7 C14 H14 119.1 . . ?
C4 C14 H14 119.1 . . ?
C5 C15 C3 119.7(3) . . ?
C5 C15 C20 121.1(3) . . ?
C3 C15 C20 119.3(3) . . ?
O1 C16 N2 120.0(3) . . ?
O1 C16 C4 123.3(3) . . ?
N2 C16 C4 116.7(3) . . ?
C11 C17 N4 117.6(3) . . ?
C11 C17 C4 119.7(3) . . ?
N4 C17 C4 122.7(3) . . ?
C7 C18 C11 120.8(3) . . ?
C7 C18 H18 119.6 . . ?
C11 C18 H18 119.6 . . ?
C10 C19 C12 120.9(3) . . ?
C10 C19 H19 119.5 . . ?
C12 C19 H19 119.5 . . ?
O2 C20 N6 120.5(3) . . ?
O2 C20 C15 123.8(3) . . ?
N6 C20 C15 115.7(3) . . ?
C17 N4 H2 116(2) . . ?
C17 N4 H3 109(2) . . ?
H2 N4 H3 120(4) . . ?
C3 N3 H4 118(3) . . ?
C3 N3 H8 113(3) . . ?
H4 N3 H8 119(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N2 N6 C20 -92.8(4) . . . . ?
N3 C3 C10 C19 177.9(4) . . . . ?
C15 C3 C10 C19 1.7(5) . . . . ?
C15 C5 C12 C19 -0.2(5) . . . . ?
C18 C7 C14 C4 -1.1(5) . . . . ?
C17 C4 C14 C7 1.0(5) . . . . ?
C16 C4 C14 C7 175.8(3) . . . . ?
C12 C5 C15 C3 1.2(5) . . . . ?
C12 C5 C15 C20 -178.9(3) . . . . ?
N3 C3 C15 C5 -177.9(3) . . . . ?
C10 C3 C15 C5 -1.9(5) . . . . ?
N3 C3 C15 C20 2.2(5) . . . . ?
C10 C3 C15 C20 178.2(3) . . . . ?
N6 N2 C16 O1 -0.7(5) . . . . ?
N6 N2 C16 C4 -178.4(3) . . . . ?
C17 C4 C16 O1 1.1(5) . . . . ?
C14 C4 C16 O1 -173.6(3) . . . . ?
C17 C4 C16 N2 178.8(3) . . . . ?
C14 C4 C16 N2 4.0(5) . . . . ?
C18 C11 C17 N4 177.7(3) . . . . ?
C18 C11 C17 C4 0.1(5) . . . . ?
C14 C4 C17 C11 -0.5(5) . . . . ?
C16 C4 C17 C11 -175.4(3) . . . . ?
C14 C4 C17 N4 -177.9(3) . . . . ?
C16 C4 C17 N4 7.2(5) . . . . ?
C14 C7 C18 C11 0.7(6) . . . . ?
C17 C11 C18 C7 -0.2(6) . . . . ?
C3 C10 C19 C12 -0.8(6) . . . . ?
C5 C12 C19 C10 0.0(5) . . . . ?
N2 N6 C20 O2 -10.8(5) . . . . ?
N2 N6 C20 C15 170.4(3) . . . . ?
C5 C15 C20 O2 -149.2(3) . . . . ?
C3 C15 C20 O2 30.7(5) . . . . ?
C5 C15 C20 N6 29.5(5) . . . . ?
C3 C15 C20 N6 -150.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.067

#===END

data_C18H14N4OS
_database_code_depnum_ccdc_archive 'CCDC 702072'

_audit_creation_method           SHELXL-97
_publ_section_abstract           
;
Structural properties of NN atropisomers are discussed
;
_chemical_name_systematic        
;
2,2'-Dimethyl-3,3'-biquinazoline-4-thio-4'-one
;
_chemical_name_common            
2,2'-Dimethyl-3,3'-biquinazoline-4-thio-4'-one
_chemical_melting_point          173
_chemical_formula_moiety         'C18 H14 N4 O S'
_chemical_formula_sum            'C18 H14 N4 O S'
_chemical_formula_weight         334.39
_chemical_absolute_configuration ad

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'
S S 0.1246 0.1234 '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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.054(2)
_cell_length_b                   10.367(3)
_cell_length_c                   9.995(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.174(11)
_cell_angle_gamma                90.00
_cell_volume                     792.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13511
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex2 Kappa '
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15758
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         29.57
_reflns_number_total             4295
_reflns_number_gt                3800
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex version 2.1'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_number_reflns         4295
_refine_ls_number_parameters     219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
S1 S 0.33939(7) 0.12908(7) 0.25035(6) 0.02937(16) Uani 1 1 d . . .
C21 C 0.5473(3) 0.1378(2) 0.2591(2) 0.0202(4) Uani 1 1 d . . .
N4 N 0.9033(2) 0.17519(18) 0.2633(2) 0.0211(4) Uani 1 1 d . . .
C6 C 0.1198(3) 0.6284(2) 0.0710(2) 0.0240(4) Uani 1 1 d . . .
H6 H 0.0334 0.6272 -0.0162 0.029 Uiso 1 1 calc R . .
N3 N 0.2507(2) 0.44143(19) 0.00227(19) 0.0226(4) Uani 1 1 d . . .
C1 C 0.5071(3) 0.4343(2) 0.2774(2) 0.0196(4) Uani 1 1 d . . .
N2 N 0.5001(2) 0.35041(17) 0.16456(18) 0.0194(4) Uani 1 1 d . . .
C3 C 0.3709(3) 0.3546(2) 0.0333(2) 0.0207(4) Uani 1 1 d . . .
C7 C 0.1200(3) 0.7243(2) 0.1680(3) 0.0275(5) Uani 1 1 d . . .
H7 H 0.0344 0.7880 0.1445 0.033 Uiso 1 1 calc R . .
C5 C 0.2499(3) 0.5335(2) 0.1045(2) 0.0201(4) Uani 1 1 d . . .
C8 C 0.3821(3) 0.2555(2) -0.0732(2) 0.0286(5) Uani 1 1 d . . .
H8A H 0.2875 0.2679 -0.1587 0.043 Uiso 1 1 calc R . .
H8B H 0.3748 0.1707 -0.0369 0.043 Uiso 1 1 calc R . .
H8C H 0.4913 0.2647 -0.0921 0.043 Uiso 1 1 calc R . .
O1 O 0.6208(2) 0.41909(16) 0.39415(15) 0.0244(3) Uani 1 1 d . . .
C12 C 0.9484(3) -0.1276(2) 0.4590(3) 0.0288(5) Uani 1 1 d . . .
H12 H 1.0365 -0.1850 0.5046 0.035 Uiso 1 1 calc R . .
C14 C 0.6446(3) -0.0659(2) 0.3930(2) 0.0238(5) Uani 1 1 d . . .
H14 H 0.5311 -0.0812 0.3938 0.029 Uiso 1 1 calc R . .
C11 C 0.9870(3) -0.0204(2) 0.3916(2) 0.0263(5) Uani 1 1 d . . .
H11 H 1.1008 -0.0061 0.3910 0.032 Uiso 1 1 calc R . .
C13 C 0.7754(3) -0.1498(2) 0.4586(2) 0.0285(5) Uani 1 1 d . . .
H13 H 0.7502 -0.2223 0.5034 0.034 Uiso 1 1 calc R . .
C16 C 0.3752(3) 0.6314(2) 0.3379(2) 0.0226(4) Uani 1 1 d . . .
H16 H 0.4585 0.6315 0.4265 0.027 Uiso 1 1 calc R . .
C17 C 0.2479(3) 0.7266(2) 0.3013(3) 0.0267(5) Uani 1 1 d . . .
H17 H 0.2471 0.7919 0.3648 0.032 Uiso 1 1 calc R . .
C15 C 0.3769(3) 0.5344(2) 0.2390(2) 0.0202(4) Uani 1 1 d . . .
C19 C 0.6819(3) 0.0443(2) 0.3240(2) 0.0194(4) Uani 1 1 d . . .
C18 C 0.8544(3) 0.0663(2) 0.3244(2) 0.0203(4) Uani 1 1 d . . .
N1 N 0.6102(2) 0.24283(17) 0.20154(19) 0.0188(4) Uani 1 1 d . . .
C22 C 0.7848(3) 0.2603(2) 0.2075(2) 0.0193(4) Uani 1 1 d . . .
C4 C 0.8335(3) 0.3822(2) 0.1492(3) 0.0266(5) Uani 1 1 d . . .
H4A H 0.8279 0.4531 0.2095 0.040 Uiso 1 1 calc R . .
H4B H 0.7537 0.3971 0.0567 0.040 Uiso 1 1 calc R . .
H4C H 0.9502 0.3748 0.1440 0.040 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
S1 C21 1.652(2) . ?
C21 N1 1.398(3) . ?
C21 C19 1.448(3) . ?
N4 C22 1.292(3) . ?
N4 C18 1.397(3) . ?
C6 C7 1.389(4) . ?
C6 C5 1.400(3) . ?
C6 H6 0.9300 . ?
N3 C3 1.287(3) . ?
N3 C5 1.400(3) . ?
C1 O1 1.249(2) . ?
C1 N2 1.411(3) . ?
C1 C15 1.440(3) . ?
N2 C3 1.398(3) . ?
N2 N1 1.401(2) . ?
C3 C8 1.503(3) . ?
C7 C17 1.408(3) . ?
C7 H7 0.9300 . ?
C5 C15 1.412(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C12 C11 1.384(3) . ?
C12 C13 1.411(4) . ?
C12 H12 0.9300 . ?
C14 C13 1.366(3) . ?
C14 C19 1.414(3) . ?
C14 H14 0.9300 . ?
C11 C18 1.397(3) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C16 C17 1.387(3) . ?
C16 C15 1.413(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C18 1.407(3) . ?
N1 C22 1.401(3) . ?
C22 C4 1.495(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
N1 C21 C19 112.91(18) . . ?
N1 C21 S1 120.82(16) . . ?
C19 C21 S1 126.27(17) . . ?
C22 N4 C18 118.01(19) . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C3 N3 C5 118.37(19) . . ?
O1 C1 N2 120.28(19) . . ?
O1 C1 C15 126.9(2) . . ?
N2 C1 C15 112.78(18) . . ?
C3 N2 N1 119.80(17) . . ?
C3 N2 C1 124.27(17) . . ?
N1 N2 C1 114.55(17) . . ?
N3 C3 N2 122.14(19) . . ?
N3 C3 C8 120.9(2) . . ?
N2 C3 C8 116.88(19) . . ?
C6 C7 C17 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
C17 C7 H7 119.5 . . ?
N3 C5 C6 118.5(2) . . ?
N3 C5 C15 122.18(19) . . ?
C6 C5 C15 119.3(2) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C14 C19 119.9(2) . . ?
C13 C14 H14 120.0 . . ?
C19 C14 H14 120.0 . . ?
C12 C11 C18 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C18 C11 H11 120.1 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C7 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C7 C17 H17 120.0 . . ?
C5 C15 C16 120.6(2) . . ?
C5 C15 C1 119.97(19) . . ?
C16 C15 C1 119.47(19) . . ?
C18 C19 C14 119.3(2) . . ?
C18 C19 C21 119.54(19) . . ?
C14 C19 C21 121.1(2) . . ?
C11 C18 N4 116.9(2) . . ?
C11 C18 C19 120.2(2) . . ?
N4 C18 C19 122.87(19) . . ?
C21 N1 N2 116.63(17) . . ?
C21 N1 C22 124.81(18) . . ?
N2 N1 C22 116.91(17) . . ?
N4 C22 N1 121.79(19) . . ?
N4 C22 C4 119.9(2) . . ?
N1 C22 C4 118.33(19) . . ?
C22 C4 H4A 109.5 . . ?
C22 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C22 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N2 C3 175.5(2) . . . . ?
C15 C1 N2 C3 -6.2(3) . . . . ?
O1 C1 N2 N1 9.0(3) . . . . ?
C15 C1 N2 N1 -172.68(17) . . . . ?
C5 N3 C3 N2 -0.6(3) . . . . ?
C5 N3 C3 C8 -178.1(2) . . . . ?
N1 N2 C3 N3 169.6(2) . . . . ?
C1 N2 C3 N3 3.7(3) . . . . ?
N1 N2 C3 C8 -12.8(3) . . . . ?
C1 N2 C3 C8 -178.6(2) . . . . ?
C5 C6 C7 C17 -1.1(3) . . . . ?
C3 N3 C5 C6 179.8(2) . . . . ?
C3 N3 C5 C15 0.6(3) . . . . ?
C7 C6 C5 N3 -177.22(19) . . . . ?
C7 C6 C5 C15 2.0(3) . . . . ?
C13 C12 C11 C18 0.6(4) . . . . ?
C19 C14 C13 C12 0.3(4) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C15 C16 C17 C7 1.4(3) . . . . ?
C6 C7 C17 C16 -0.6(3) . . . . ?
N3 C5 C15 C16 177.92(19) . . . . ?
C6 C5 C15 C16 -1.2(3) . . . . ?
N3 C5 C15 C1 -3.5(3) . . . . ?
C6 C5 C15 C1 177.3(2) . . . . ?
C17 C16 C15 C5 -0.4(3) . . . . ?
C17 C16 C15 C1 -179.0(2) . . . . ?
O1 C1 C15 C5 -176.0(2) . . . . ?
N2 C1 C15 C5 5.9(3) . . . . ?
O1 C1 C15 C16 2.6(3) . . . . ?
N2 C1 C15 C16 -175.55(18) . . . . ?
C13 C14 C19 C18 -0.2(3) . . . . ?
C13 C14 C19 C21 -177.3(2) . . . . ?
N1 C21 C19 C18 0.3(3) . . . . ?
S1 C21 C19 C18 -179.24(17) . . . . ?
N1 C21 C19 C14 177.35(19) . . . . ?
S1 C21 C19 C14 -2.2(3) . . . . ?
C12 C11 C18 N4 177.4(2) . . . . ?
C12 C11 C18 C19 -0.5(3) . . . . ?
C22 N4 C18 C11 -176.2(2) . . . . ?
C22 N4 C18 C19 1.7(3) . . . . ?
C14 C19 C18 C11 0.3(3) . . . . ?
C21 C19 C18 C11 177.4(2) . . . . ?
C14 C19 C18 N4 -177.5(2) . . . . ?
C21 C19 C18 N4 -0.4(3) . . . . ?
C19 C21 N1 N2 -166.42(17) . . . . ?
S1 C21 N1 N2 13.2(3) . . . . ?
C19 C21 N1 C22 -1.6(3) . . . . ?
S1 C21 N1 C22 178.05(16) . . . . ?
C3 N2 N1 C21 -84.7(2) . . . . ?
C1 N2 N1 C21 82.5(2) . . . . ?
C3 N2 N1 C22 109.3(2) . . . . ?
C1 N2 N1 C22 -83.6(2) . . . . ?
C18 N4 C22 N1 -2.9(3) . . . . ?
C18 N4 C22 C4 176.13(19) . . . . ?
C21 N1 C22 N4 3.0(3) . . . . ?
N2 N1 C22 N4 167.8(2) . . . . ?
C21 N1 C22 C4 -176.0(2) . . . . ?
N2 N1 C22 C4 -11.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.073

#===END

data_C28H18N4O2
_database_code_depnum_ccdc_archive 'CCDC 702073'

_audit_creation_method           'WinGX-Routine XCAD4'
_publ_section_abstract           
;
Structural properties of NN atropisomers are discussed
;
_chemical_name_systematic        
;
2,2'-Diphenyl-3,3-biquinazoline-4,4-dione
;
_chemical_name_common            2,2'-Diphenyl-3,3-biquinazoline-4,4-dione
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 N4 O2'
_chemical_formula_sum            'C28 H18 N4 O2'
_chemical_formula_weight         442.46

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.979(3)
_cell_length_b                   14.653(3)
_cell_length_c                   18.466(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4323.6(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4483
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      25.3

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_correction_T_min  0.7451
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3899
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3899
_reflns_number_gt                2174
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_restrained_S_all      0.852
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

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
O1 O 0.09219(10) 0.85543(11) 0.25956(9) 0.0373(4) Uani 1 1 d . . .
O2 O 0.14516(10) 0.64935(12) 0.26261(9) 0.0390(5) Uani 1 1 d . . .
N1 N 0.07768(10) 0.75862(12) 0.16348(9) 0.0258(4) Uani 1 1 d . . .
N2 N -0.04857(12) 0.73706(12) 0.10108(11) 0.0353(5) Uani 1 1 d . . .
N3 N 0.16432(10) 0.74296(12) 0.16572(9) 0.0247(4) Uani 1 1 d . . .
N4 N 0.29490(12) 0.76659(13) 0.11051(12) 0.0374(5) Uani 1 1 d . . .
C1 C 0.02883(13) 0.71586(15) 0.11054(12) 0.0281(5) Uani 1 1 d . . .
C2 C -0.08553(14) 0.79950(16) 0.14836(14) 0.0331(6) Uani 1 1 d . . .
C3 C -0.17034(15) 0.82037(17) 0.13883(17) 0.0469(7) Uani 1 1 d . . .
H3 H -0.2005 0.7945 0.0995 0.056 Uiso 1 1 calc R . .
C4 C -0.20994(16) 0.87826(17) 0.18633(16) 0.0487(7) Uani 1 1 d . . .
H4 H -0.2676 0.8918 0.1796 0.058 Uiso 1 1 calc R . .
C5 C -0.16737(15) 0.91708(17) 0.24364(16) 0.0432(7) Uani 1 1 d . . .
H5 H -0.1956 0.9568 0.2762 0.052 Uiso 1 1 calc R . .
C6 C -0.08409(14) 0.89792(16) 0.25323(14) 0.0377(6) Uani 1 1 d . . .
H6 H -0.0545 0.9246 0.2925 0.045 Uiso 1 1 calc R . .
C7 C -0.04254(13) 0.83935(15) 0.20560(12) 0.0292(5) Uani 1 1 d . . .
C8 C 0.04634(14) 0.82067(15) 0.21488(12) 0.0276(5) Uani 1 1 d . . .
C9 C 0.06669(14) 0.64508(15) 0.06413(12) 0.0284(5) Uani 1 1 d . . .
C10 C 0.05744(17) 0.65155(18) -0.01050(13) 0.0436(7) Uani 1 1 d . . .
H10 H 0.0309 0.7035 -0.0310 0.052 Uiso 1 1 calc R . .
C11 C 0.08678(17) 0.5826(2) -0.05536(14) 0.0501(7) Uani 1 1 d . . .
H11 H 0.0818 0.5884 -0.1064 0.060 Uiso 1 1 calc R . .
C12 C 0.12302(16) 0.5060(2) -0.02606(15) 0.0486(7) Uani 1 1 d . . .
H12 H 0.1423 0.4585 -0.0568 0.058 Uiso 1 1 calc R . .
C13 C 0.13135(15) 0.49822(17) 0.04784(14) 0.0413(6) Uani 1 1 d . . .
H13 H 0.1559 0.4450 0.0681 0.050 Uiso 1 1 calc R . .
C14 C 0.10427(14) 0.56739(16) 0.09256(13) 0.0325(6) Uani 1 1 d . . .
H14 H 0.1114 0.5619 0.1435 0.039 Uiso 1 1 calc R . .
C15 C 0.21618(14) 0.78580(15) 0.11478(12) 0.0296(5) Uani 1 1 d . . .
C16 C 0.32897(14) 0.70514(15) 0.15975(14) 0.0350(6) Uani 1 1 d . . .
C17 C 0.41464(15) 0.68380(18) 0.15412(18) 0.0511(8) Uani 1 1 d . . .
H17 H 0.4478 0.7106 0.1171 0.061 Uiso 1 1 calc R . .
C18 C 0.45015(16) 0.62363(18) 0.20277(18) 0.0548(8) Uani 1 1 d . . .
H18 H 0.5078 0.6087 0.1985 0.066 Uiso 1 1 calc R . .
C19 C 0.40352(16) 0.58477(17) 0.25746(17) 0.0468(7) Uani 1 1 d . . .
H19 H 0.4290 0.5439 0.2907 0.056 Uiso 1 1 calc R . .
C20 C 0.32056(15) 0.60539(16) 0.26358(14) 0.0379(6) Uani 1 1 d . . .
H20 H 0.2884 0.5790 0.3015 0.045 Uiso 1 1 calc R . .
C21 C 0.28255(13) 0.66492(15) 0.21471(13) 0.0304(6) Uani 1 1 d . . .
C22 C 0.19316(13) 0.68331(15) 0.21954(12) 0.0274(5) Uani 1 1 d . . .
C23 C 0.17822(14) 0.85087(15) 0.06293(12) 0.0320(6) Uani 1 1 d . . .
C24 C 0.18588(18) 0.83221(19) -0.01028(14) 0.0472(7) Uani 1 1 d . . .
H24 H 0.2131 0.7779 -0.0255 0.057 Uiso 1 1 calc R . .
C25 C 0.1543(2) 0.8918(2) -0.06126(16) 0.0614(9) Uani 1 1 d . . .
H25 H 0.1592 0.8781 -0.1114 0.074 Uiso 1 1 calc R . .
C26 C 0.11608(19) 0.9706(2) -0.03960(17) 0.0607(9) Uani 1 1 d . . .
H26 H 0.0944 1.0116 -0.0748 0.073 Uiso 1 1 calc R . .
C27 C 0.10885(18) 0.9909(2) 0.03282(16) 0.0554(8) Uani 1 1 d . . .
H27 H 0.0828 1.0461 0.0476 0.066 Uiso 1 1 calc R . .
C28 C 0.13939(15) 0.93094(16) 0.08414(13) 0.0373(6) Uani 1 1 d . . .
H28 H 0.1337 0.9447 0.1342 0.045 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
O1 C8 1.215(3) . ?
O2 C22 1.212(3) . ?
N1 C1 1.399(3) . ?
N1 N3 1.404(2) . ?
N1 C8 1.407(3) . ?
N2 C1 1.287(3) . ?
N2 C2 1.396(3) . ?
N3 C22 1.401(3) . ?
N3 C15 1.402(3) . ?
N4 C15 1.291(3) . ?
N4 C16 1.391(3) . ?
C1 C9 1.475(3) . ?
C2 C7 1.389(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.457(3) . ?
C9 C10 1.389(3) . ?
C9 C14 1.390(3) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C23 1.481(3) . ?
C16 C21 1.388(3) . ?
C16 C17 1.408(3) . ?
C17 C18 1.381(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.364(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.456(3) . ?
C23 C28 1.384(3) . ?
C23 C24 1.385(3) . ?
C24 C25 1.380(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.366(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.375(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(3) . ?
C27 H27 0.9500 . ?
C28 H28 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
C1 N1 N3 119.85(17) . . ?
C1 N1 C8 124.22(18) . . ?
N3 N1 C8 115.89(17) . . ?
C1 N2 C2 118.7(2) . . ?
C22 N3 C15 124.10(18) . . ?
C22 N3 N1 116.56(17) . . ?
C15 N3 N1 119.33(17) . . ?
C15 N4 C16 118.9(2) . . ?
N2 C1 N1 121.5(2) . . ?
N2 C1 C9 119.0(2) . . ?
N1 C1 C9 119.47(19) . . ?
C7 C2 N2 122.8(2) . . ?
C7 C2 C3 118.8(2) . . ?
N2 C2 C3 118.3(2) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.2(2) . . ?
C2 C7 C8 119.5(2) . . ?
C6 C7 C8 120.3(2) . . ?
O1 C8 N1 121.0(2) . . ?
O1 C8 C7 126.1(2) . . ?
N1 C8 C7 112.91(19) . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C1 119.0(2) . . ?
C14 C9 C1 122.2(2) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
N4 C15 N3 121.3(2) . . ?
N4 C15 C23 120.0(2) . . ?
N3 C15 C23 118.68(19) . . ?
C21 C16 N4 122.9(2) . . ?
C21 C16 C17 118.6(2) . . ?
N4 C16 C17 118.4(2) . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 120.4(2) . . ?
C16 C21 C22 119.4(2) . . ?
C20 C21 C22 120.2(2) . . ?
O2 C22 N3 120.9(2) . . ?
O2 C22 C21 125.8(2) . . ?
N3 C22 C21 113.2(2) . . ?
C28 C23 C24 118.9(2) . . ?
C28 C23 C15 123.1(2) . . ?
C24 C23 C15 117.9(2) . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C28 120.0(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C23 120.2(2) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N3 C22 -103.2(2) . . . . ?
C8 N1 N3 C22 79.0(2) . . . . ?
C1 N1 N3 C15 76.0(2) . . . . ?
C8 N1 N3 C15 -101.8(2) . . . . ?
C2 N2 C1 N1 -4.6(3) . . . . ?
C2 N2 C1 C9 175.7(2) . . . . ?
N3 N1 C1 N2 -171.3(2) . . . . ?
C8 N1 C1 N2 6.3(3) . . . . ?
N3 N1 C1 C9 8.5(3) . . . . ?
C8 N1 C1 C9 -173.93(19) . . . . ?
C1 N2 C2 C7 -0.5(3) . . . . ?
C1 N2 C2 C3 -178.4(2) . . . . ?
C7 C2 C3 C4 -1.0(4) . . . . ?
N2 C2 C3 C4 177.0(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
N2 C2 C7 C6 -176.8(2) . . . . ?
C3 C2 C7 C6 1.0(4) . . . . ?
N2 C2 C7 C8 4.1(3) . . . . ?
C3 C2 C7 C8 -178.0(2) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
C5 C6 C7 C8 178.6(2) . . . . ?
C1 N1 C8 O1 179.9(2) . . . . ?
N3 N1 C8 O1 -2.4(3) . . . . ?
C1 N1 C8 C7 -2.5(3) . . . . ?
N3 N1 C8 C7 175.22(18) . . . . ?
C2 C7 C8 O1 175.0(2) . . . . ?
C6 C7 C8 O1 -4.1(4) . . . . ?
C2 C7 C8 N1 -2.5(3) . . . . ?
C6 C7 C8 N1 178.5(2) . . . . ?
N2 C1 C9 C10 50.3(3) . . . . ?
N1 C1 C9 C10 -129.4(2) . . . . ?
N2 C1 C9 C14 -123.2(2) . . . . ?
N1 C1 C9 C14 57.0(3) . . . . ?
C14 C9 C10 C11 -1.3(4) . . . . ?
C1 C9 C10 C11 -175.1(2) . . . . ?
C9 C10 C11 C12 2.0(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C9 1.3(4) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C1 C9 C14 C13 173.3(2) . . . . ?
C16 N4 C15 N3 -2.9(3) . . . . ?
C16 N4 C15 C23 -179.9(2) . . . . ?
C22 N3 C15 N4 5.9(3) . . . . ?
N1 N3 C15 N4 -173.3(2) . . . . ?
C22 N3 C15 C23 -177.08(19) . . . . ?
N1 N3 C15 C23 3.7(3) . . . . ?
C15 N4 C16 C21 -1.6(3) . . . . ?
C15 N4 C16 C17 179.3(2) . . . . ?
C21 C16 C17 C18 0.2(4) . . . . ?
N4 C16 C17 C18 179.4(2) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
N4 C16 C21 C20 -178.5(2) . . . . ?
C17 C16 C21 C20 0.6(3) . . . . ?
N4 C16 C21 C22 3.4(3) . . . . ?
C17 C16 C21 C22 -177.5(2) . . . . ?
C19 C20 C21 C16 -1.0(3) . . . . ?
C19 C20 C21 C22 177.1(2) . . . . ?
C15 N3 C22 O2 179.0(2) . . . . ?
N1 N3 C22 O2 -1.8(3) . . . . ?
C15 N3 C22 C21 -3.8(3) . . . . ?
N1 N3 C22 C21 175.36(18) . . . . ?
C16 C21 C22 O2 176.4(2) . . . . ?
C20 C21 C22 O2 -1.8(4) . . . . ?
C16 C21 C22 N3 -0.6(3) . . . . ?
C20 C21 C22 N3 -178.8(2) . . . . ?
N4 C15 C23 C28 -120.3(3) . . . . ?
N3 C15 C23 C28 62.6(3) . . . . ?
N4 C15 C23 C24 56.5(3) . . . . ?
N3 C15 C23 C24 -120.6(2) . . . . ?
C28 C23 C24 C25 -0.9(4) . . . . ?
C15 C23 C24 C25 -177.8(2) . . . . ?
C23 C24 C25 C26 0.8(4) . . . . ?
C24 C25 C26 C27 0.0(5) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C26 C27 C28 C23 0.8(4) . . . . ?
C24 C23 C28 C27 0.1(4) . . . . ?
C15 C23 C28 C27 176.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038

#===END

data_C34H28N2O8
_database_code_depnum_ccdc_archive 'CCDC 702074'

_audit_creation_method           SHELXL-97
_publ_section_abstract           
;
Structural properties of NN atropisomers are discussed
;
_chemical_name_systematic        
;
(S,S)-1,2-bis-
(2-benzoyloxypropanoyl)-1,2-dibenzoylhydrazine
;
_chemical_name_common            
(S,S)-1,2-bis-(2-benzoyloxypropanoyl)-1,2-dibenzoylhydrazine
_chemical_melting_point          173
_chemical_formula_moiety         'C34 H28 N2 O8'
_chemical_formula_sum            'C34 H28 N2 O8'
_chemical_formula_weight         592.58
_chemical_absolute_configuration syn

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           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.362(2)
_cell_length_b                   10.943(2)
_cell_length_c                   25.892(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2935.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3115
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      25.3

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_correction_T_min  0.7224
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3021
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.32
_reflns_number_total             3021
_reflns_number_gt                2241
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0895P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(19)
_refine_ls_number_reflns         3021
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
O1 O 0.0774(3) 0.5372(3) -0.08707(11) 0.0318(8) Uani 1 1 d . . .
O2 O 0.0568(3) 0.5063(3) 0.01341(11) 0.0255(7) Uani 1 1 d . . .
O3 O 0.2713(3) 0.5332(3) 0.01033(15) 0.0458(9) Uani 1 1 d . . .
O4 O 0.0990(3) 0.8705(3) -0.02028(11) 0.0290(7) Uani 1 1 d . . .
O5 O -0.1562(3) 0.6933(3) -0.12491(11) 0.0325(8) Uani 1 1 d . . .
O6 O -0.2221(3) 0.6463(3) -0.22522(11) 0.0303(7) Uani 1 1 d . . .
O7 O -0.1937(3) 0.8489(3) -0.23237(12) 0.0357(8) Uani 1 1 d . . .
O8 O 0.1429(3) 0.7699(4) -0.22085(11) 0.0444(9) Uani 1 1 d . . .
N1 N 0.0711(3) 0.7439(3) -0.08850(12) 0.0215(7) Uani 1 1 d . . .
N2 N 0.0551(3) 0.7309(3) -0.14231(12) 0.0217(8) Uani 1 1 d . . .
C1 C 0.0679(4) 0.6298(4) -0.06225(16) 0.0239(9) Uani 1 1 d . . .
C2 C 0.0399(4) 0.6297(4) -0.00451(15) 0.0219(9) Uani 1 1 d . . .
H2 H 0.0984 0.6873 0.0143 0.026 Uiso 1 1 calc R . .
C3 C -0.1005(4) 0.6619(4) 0.00450(16) 0.0270(10) Uani 1 1 d . . .
H3A H -0.1153 0.7474 -0.0050 0.041 Uiso 1 1 calc R . .
H3B H -0.1217 0.6501 0.0410 0.041 Uiso 1 1 calc R . .
H3C H -0.1553 0.6089 -0.0167 0.041 Uiso 1 1 calc R . .
C4 C 0.1800(4) 0.4684(4) 0.01886(16) 0.0260(10) Uani 1 1 d . . .
C5 C 0.1877(4) 0.3384(4) 0.03521(16) 0.0266(10) Uani 1 1 d . . .
C6 C 0.0785(4) 0.2645(4) 0.03592(16) 0.0303(10) Uani 1 1 d . . .
H6 H -0.0033 0.2976 0.0270 0.036 Uiso 1 1 calc R . .
C7 C 0.0892(5) 0.1419(4) 0.04967(17) 0.0344(11) Uani 1 1 d . . .
H7 H 0.0149 0.0912 0.0501 0.041 Uiso 1 1 calc R . .
C8 C 0.2085(5) 0.0942(4) 0.06278(17) 0.0340(12) Uani 1 1 d . . .
H8 H 0.2159 0.0105 0.0721 0.041 Uiso 1 1 calc R . .
C9 C 0.3169(5) 0.1680(4) 0.06235(17) 0.0326(11) Uani 1 1 d . . .
H9 H 0.3985 0.1355 0.0718 0.039 Uiso 1 1 calc R . .
C10 C 0.3060(5) 0.2901(4) 0.04797(16) 0.0289(10) Uani 1 1 d . . .
H10 H 0.3808 0.3403 0.0470 0.035 Uiso 1 1 calc R . .
C11 C 0.0770(4) 0.8618(4) -0.06604(15) 0.0231(9) Uani 1 1 d . . .
C12 C 0.0675(4) 0.9722(4) -0.09924(16) 0.0253(9) Uani 1 1 d . . .
C13 C -0.0302(5) 0.9899(4) -0.13637(16) 0.0309(10) Uani 1 1 d . . .
H13 H -0.0915 0.9275 -0.1433 0.037 Uiso 1 1 calc R . .
C14 C -0.0350(6) 1.1004(5) -0.16265(17) 0.0414(13) Uani 1 1 d . . .
H14 H -0.1002 1.1136 -0.1878 0.050 Uiso 1 1 calc R . .
C15 C 0.0539(6) 1.1915(4) -0.15261(19) 0.0464(14) Uani 1 1 d . . .
H15 H 0.0504 1.2657 -0.1716 0.056 Uiso 1 1 calc R . .
C16 C 0.1472(6) 1.1759(4) -0.1155(2) 0.0477(14) Uani 1 1 d . . .
H16 H 0.2063 1.2399 -0.1081 0.057 Uiso 1 1 calc R . .
C17 C 0.1548(5) 1.0658(4) -0.08866(18) 0.0339(11) Uani 1 1 d . . .
H17 H 0.2195 1.0545 -0.0631 0.041 Uiso 1 1 calc R . .
C18 C -0.0720(4) 0.6927(4) -0.15671(16) 0.0240(9) Uani 1 1 d . . .
C19 C -0.0887(4) 0.6375(4) -0.20991(16) 0.0269(10) Uani 1 1 d . . .
H19 H -0.0321 0.6802 -0.2355 0.032 Uiso 1 1 calc R . .
C20 C -0.0550(5) 0.5030(5) -0.2072(2) 0.0420(13) Uani 1 1 d . . .
H20A H -0.1101 0.4628 -0.1815 0.063 Uiso 1 1 calc R . .
H20B H 0.0357 0.4938 -0.1972 0.063 Uiso 1 1 calc R . .
H20C H -0.0689 0.4654 -0.2411 0.063 Uiso 1 1 calc R . .
C21 C -0.2602(4) 0.7596(4) -0.23913(15) 0.0252(9) Uani 1 1 d . . .
C22 C -0.3900(4) 0.7605(4) -0.26419(14) 0.0268(10) Uani 1 1 d . . .
C23 C -0.4260(5) 0.8654(4) -0.29049(16) 0.0340(11) Uani 1 1 d . . .
H23 H -0.3695 0.9336 -0.2924 0.041 Uiso 1 1 calc R . .
C24 C -0.5473(5) 0.8688(4) -0.31420(17) 0.0373(11) Uani 1 1 d . . .
H24 H -0.5739 0.9401 -0.3322 0.045 Uiso 1 1 calc R . .
C25 C -0.6276(5) 0.7699(5) -0.31165(17) 0.0366(12) Uani 1 1 d . . .
H25 H -0.7092 0.7728 -0.3283 0.044 Uiso 1 1 calc R . .
C26 C -0.5916(5) 0.6657(4) -0.28517(17) 0.0332(11) Uani 1 1 d . . .
H26 H -0.6489 0.5982 -0.2829 0.040 Uiso 1 1 calc R . .
C27 C -0.4716(4) 0.6605(4) -0.26195(15) 0.0292(10) Uani 1 1 d . . .
H27 H -0.4451 0.5884 -0.2445 0.035 Uiso 1 1 calc R . .
C28 C 0.1605(4) 0.7547(4) -0.17508(15) 0.0270(9) Uani 1 1 d . . .
C29 C 0.2924(4) 0.7643(4) -0.15223(15) 0.0245(9) Uani 1 1 d . . .
C30 C 0.3619(4) 0.8681(5) -0.16378(16) 0.0331(11) Uani 1 1 d . . .
H30 H 0.3225 0.9326 -0.1826 0.040 Uiso 1 1 calc R . .
C31 C 0.4886(5) 0.8786(5) -0.14809(17) 0.0399(12) Uani 1 1 d . . .
H31 H 0.5355 0.9516 -0.1548 0.048 Uiso 1 1 calc R . .
C32 C 0.5474(4) 0.7822(5) -0.12244(18) 0.0420(13) Uani 1 1 d . . .
H32 H 0.6353 0.7881 -0.1123 0.050 Uiso 1 1 calc R . .
C33 C 0.4784(5) 0.6785(5) -0.11179(18) 0.0398(13) Uani 1 1 d . . .
H33 H 0.5193 0.6126 -0.0944 0.048 Uiso 1 1 calc R . .
C34 C 0.3484(5) 0.6680(4) -0.12608(16) 0.0316(11) Uani 1 1 d . . .
H34 H 0.3002 0.5966 -0.1180 0.038 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
O1 C1 1.204(5) . ?
O2 C4 1.349(5) . ?
O2 C2 1.439(5) . ?
O3 C4 1.203(5) . ?
O4 C11 1.210(5) . ?
O5 C18 1.200(5) . ?
O6 C21 1.350(5) . ?
O6 C19 1.441(5) . ?
O7 C21 1.209(5) . ?
O8 C28 1.210(5) . ?
N1 N2 1.410(4) . ?
N1 C11 1.417(5) . ?
N1 C1 1.422(5) . ?
N2 C28 1.408(5) . ?
N2 C18 1.431(5) . ?
C1 C2 1.523(6) . ?
C2 C3 1.514(6) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.486(6) . ?
C5 C10 1.375(6) . ?
C5 C6 1.391(6) . ?
C6 C7 1.392(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.486(6) . ?
C12 C17 1.393(6) . ?
C12 C13 1.410(6) . ?
C13 C14 1.388(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.514(6) . ?
C19 C20 1.514(7) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.494(6) . ?
C22 C27 1.383(6) . ?
C22 C23 1.386(6) . ?
C23 C24 1.399(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.367(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.493(6) . ?
C29 C30 1.378(6) . ?
C29 C34 1.380(6) . ?
C30 C31 1.379(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.388(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.369(7) . ?
C32 H32 0.9500 . ?
C33 C34 1.402(7) . ?
C33 H33 0.9500 . ?
C34 H34 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
C4 O2 C2 115.9(3) . . ?
C21 O6 C19 114.5(3) . . ?
N2 N1 C11 120.1(3) . . ?
N2 N1 C1 112.4(3) . . ?
C11 N1 C1 127.2(3) . . ?
C28 N2 N1 119.0(3) . . ?
C28 N2 C18 127.7(3) . . ?
N1 N2 C18 113.3(3) . . ?
O1 C1 N1 118.8(3) . . ?
O1 C1 C2 122.6(4) . . ?
N1 C1 C2 118.3(3) . . ?
O2 C2 C3 106.6(3) . . ?
O2 C2 C1 107.1(3) . . ?
C3 C2 C1 109.5(3) . . ?
O2 C2 H2 111.1 . . ?
C3 C2 H2 111.1 . . ?
C1 C2 H2 111.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O3 C4 O2 123.0(4) . . ?
O3 C4 C5 125.0(4) . . ?
O2 C4 C5 112.0(4) . . ?
C10 C5 C6 119.9(4) . . ?
C10 C5 C4 119.0(4) . . ?
C6 C5 C4 121.1(4) . . ?
C5 C6 C7 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.8(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C5 C10 C9 120.4(5) . . ?
C5 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
O4 C11 N1 118.8(4) . . ?
O4 C11 C12 121.0(4) . . ?
N1 C11 C12 120.0(3) . . ?
C17 C12 C13 119.9(4) . . ?
C17 C12 C11 116.2(4) . . ?
C13 C12 C11 123.6(4) . . ?
C14 C13 C12 118.7(5) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.7(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.1(5) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
O5 C18 N2 119.2(4) . . ?
O5 C18 C19 122.9(4) . . ?
N2 C18 C19 117.3(4) . . ?
O6 C19 C18 109.5(3) . . ?
O6 C19 C20 107.4(4) . . ?
C18 C19 C20 108.6(4) . . ?
O6 C19 H19 110.4 . . ?
C18 C19 H19 110.4 . . ?
C20 C19 H19 110.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C21 O6 122.6(4) . . ?
O7 C21 C22 124.8(4) . . ?
O6 C21 C22 112.7(4) . . ?
C27 C22 C23 120.7(4) . . ?
C27 C22 C21 121.8(4) . . ?
C23 C22 C21 117.5(4) . . ?
C22 C23 C24 118.7(5) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.9(4) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C27 119.5(5) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C26 C27 C22 119.9(4) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
O8 C28 N2 119.9(4) . . ?
O8 C28 C29 121.1(4) . . ?
N2 C28 C29 119.0(3) . . ?
C30 C29 C34 121.1(4) . . ?
C30 C29 C28 116.7(4) . . ?
C34 C29 C28 121.7(4) . . ?
C29 C30 C31 120.2(5) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 119.7(5) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C33 C32 C31 119.8(4) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 121.1(5) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C29 C34 C33 118.1(5) . . ?
C29 C34 H34 121.0 . . ?
C33 C34 H34 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 N2 C28 74.8(5) . . . . ?
C1 N1 N2 C28 -110.5(4) . . . . ?
C11 N1 N2 C18 -105.7(4) . . . . ?
C1 N1 N2 C18 69.0(4) . . . . ?
N2 N1 C1 O1 14.0(6) . . . . ?
C11 N1 C1 O1 -171.8(4) . . . . ?
N2 N1 C1 C2 -160.3(3) . . . . ?
C11 N1 C1 C2 13.9(6) . . . . ?
C4 O2 C2 C3 -166.7(3) . . . . ?
C4 O2 C2 C1 76.1(4) . . . . ?
O1 C1 C2 O2 12.4(6) . . . . ?
N1 C1 C2 O2 -173.5(3) . . . . ?
O1 C1 C2 C3 -102.8(5) . . . . ?
N1 C1 C2 C3 71.3(5) . . . . ?
C2 O2 C4 O3 1.3(6) . . . . ?
C2 O2 C4 C5 -177.4(3) . . . . ?
O3 C4 C5 C10 8.5(7) . . . . ?
O2 C4 C5 C10 -172.9(4) . . . . ?
O3 C4 C5 C6 -169.1(5) . . . . ?
O2 C4 C5 C6 9.5(6) . . . . ?
C10 C5 C6 C7 0.2(7) . . . . ?
C4 C5 C6 C7 177.8(4) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C6 C7 C8 C9 0.1(7) . . . . ?
C7 C8 C9 C10 -0.9(7) . . . . ?
C6 C5 C10 C9 -1.0(6) . . . . ?
C4 C5 C10 C9 -178.6(4) . . . . ?
C8 C9 C10 C5 1.3(7) . . . . ?
N2 N1 C11 O4 -175.4(4) . . . . ?
C1 N1 C11 O4 10.8(6) . . . . ?
N2 N1 C11 C12 -0.6(6) . . . . ?
C1 N1 C11 C12 -174.4(4) . . . . ?
O4 C11 C12 C17 38.8(6) . . . . ?
N1 C11 C12 C17 -135.9(4) . . . . ?
O4 C11 C12 C13 -135.2(5) . . . . ?
N1 C11 C12 C13 50.1(6) . . . . ?
C17 C12 C13 C14 1.6(6) . . . . ?
C11 C12 C13 C14 175.4(4) . . . . ?
C12 C13 C14 C15 -0.2(7) . . . . ?
C13 C14 C15 C16 -1.6(8) . . . . ?
C14 C15 C16 C17 1.9(8) . . . . ?
C15 C16 C17 C12 -0.4(8) . . . . ?
C13 C12 C17 C16 -1.3(7) . . . . ?
C11 C12 C17 C16 -175.6(4) . . . . ?
C28 N2 C18 O5 -169.3(4) . . . . ?
N1 N2 C18 O5 11.3(5) . . . . ?
C28 N2 C18 C19 18.6(6) . . . . ?
N1 N2 C18 C19 -160.9(4) . . . . ?
C21 O6 C19 C18 74.6(4) . . . . ?
C21 O6 C19 C20 -167.7(4) . . . . ?
O5 C18 C19 O6 29.3(6) . . . . ?
N2 C18 C19 O6 -158.9(3) . . . . ?
O5 C18 C19 C20 -87.7(5) . . . . ?
N2 C18 C19 C20 84.1(5) . . . . ?
C19 O6 C21 O7 -10.0(6) . . . . ?
C19 O6 C21 C22 168.9(3) . . . . ?
O7 C21 C22 C27 -167.3(4) . . . . ?
O6 C21 C22 C27 13.8(5) . . . . ?
O7 C21 C22 C23 13.3(6) . . . . ?
O6 C21 C22 C23 -165.5(4) . . . . ?
C27 C22 C23 C24 0.8(6) . . . . ?
C21 C22 C23 C24 -179.8(4) . . . . ?
C22 C23 C24 C25 -0.5(7) . . . . ?
C23 C24 C25 C26 0.9(7) . . . . ?
C24 C25 C26 C27 -1.5(7) . . . . ?
C25 C26 C27 C22 1.7(6) . . . . ?
C23 C22 C27 C26 -1.4(6) . . . . ?
C21 C22 C27 C26 179.2(4) . . . . ?
N1 N2 C28 O8 -164.2(4) . . . . ?
C18 N2 C28 O8 16.3(7) . . . . ?
N1 N2 C28 C29 14.1(6) . . . . ?
C18 N2 C28 C29 -165.3(4) . . . . ?
O8 C28 C29 C30 51.2(6) . . . . ?
N2 C28 C29 C30 -127.1(4) . . . . ?
O8 C28 C29 C34 -121.1(5) . . . . ?
N2 C28 C29 C34 60.6(6) . . . . ?
C34 C29 C30 C31 -1.7(6) . . . . ?
C28 C29 C30 C31 -174.1(4) . . . . ?
C29 C30 C31 C32 2.6(7) . . . . ?
C30 C31 C32 C33 -1.6(7) . . . . ?
C31 C32 C33 C34 -0.4(7) . . . . ?
C30 C29 C34 C33 -0.3(6) . . . . ?
C28 C29 C34 C33 171.7(4) . . . . ?
C32 C33 C34 C29 1.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.32
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.093

#===END


