# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5061a
_database_code_depnum_ccdc_archive 'CCDC 1028008'

_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;
_audit_creation_date             2014-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C35 H23 Cl2 N2'
_chemical_formula_sum            'C35 H24 Cl2 N2'
_chemical_formula_weight         543.46
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 'x+1/4, -y+1/4, z+1/4'
4 '-x+1/4, y+1/4, z+1/4'
5 'x, y+1/2, z+1/2'
6 '-x, -y+1/2, z+1/2'
7 'x+1/4, -y+3/4, z+3/4'
8 '-x+1/4, y+3/4, z+3/4'
9 'x+1/2, y, z+1/2'
10 '-x+1/2, -y, z+1/2'
11 'x+3/4, -y+1/4, z+3/4'
12 '-x+3/4, y+1/4, z+3/4'
13 'x+1/2, y+1/2, z'
14 '-x+1/2, -y+1/2, z'
15 'x+3/4, -y+3/4, z+1/4'
16 '-x+3/4, y+3/4, z+1/4'

_cell_length_a                   21.2603(17)
_cell_length_b                   42.109(4)
_cell_length_c                   5.7891(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5182.7(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1370
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      2.72
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.8369
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7385
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2009
_reflns_number_total             2251
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(12)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.227
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0688P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1441
_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. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H12A(0.5) H12B(0.5)
 Fixed U13: C12(0)
 Fixed U23: C12(0)
 Fixed Uiso: H3(0.028) H5(0.046) H6(0.045) H9A(0.033) H9B(0.033) H10(0.034)
 H12A(0.043) H12B(0.043) H14(0.044) H15(0.054) H16(0.051) H17(0.054) H18(0.045)
 Fixed X: H3(0.1305) H5(-0.0203) H6(-0.0836) H9A(-0.1151) H9B(-0.1026)
 H10(0.0858) C12(0) H12A(0.015) H12B(-0.015) H14(0.1607) H15(0.2685)
 H16(0.3168) H17(0.257) H18(0.1487)
 Fixed Y: H3(0.0986) H5(0.1275) H6(0.0941) H9A(0.0112) H9B(0.0309) H10(0.0221)
 C12(0) H12A(-0.0173) H12B(0.0173) H14(0.0289) H15(0.0242) H16(0.0454)
 H17(0.0694) H18(0.0736)
 Fixed Z: H3(0.3558) H5(-0.0068) H6(0.1967) H9A(0.6989) H9B(0.9279)
 H10(1.0188) H12A(1.1785) H12B(1.1785) H14(0.3489) H15(0.3991) H16(0.719)
 H17(1.0013) H18(0.9573)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.10704(5) 0.14241(3) 0.0016(2) 0.0383(3) Uani 1 1 d . . .
N1 N -0.05668(15) 0.05611(8) 0.5222(7) 0.0278(8) Uani 1 1 d . . .
C1 C 0.07343(18) 0.05401(9) 0.6186(7) 0.0217(9) Uani 1 1 d . . .
C2 C 0.04977(17) 0.07562(9) 0.4507(7) 0.0230(9) Uani 1 1 d . . .
C3 C 0.08710(19) 0.09721(10) 0.3257(7) 0.0235(9) Uani 1 1 d . . .
H3 H 0.1305 0.0986 0.3558 0.028 Uiso 1 1 calc R . .
C4 C 0.06060(19) 0.11594(11) 0.1620(8) 0.0308(10) Uani 1 1 d . . .
C5 C -0.0033(2) 0.11465(11) 0.1107(9) 0.0380(12) Uani 1 1 d . . .
H5 H -0.0203 0.1275 -0.0068 0.046 Uiso 1 1 calc R . .
C6 C -0.04044(19) 0.09491(11) 0.2307(10) 0.0377(12) Uani 1 1 d . . .
H6 H -0.0836 0.0941 0.1967 0.045 Uiso 1 1 calc R . .
C7 C -0.01606(18) 0.07542(9) 0.4064(7) 0.0251(9) Uani 1 1 d . . .
C8 C -0.03411(17) 0.03754(9) 0.6840(7) 0.0239(9) Uani 1 1 d . . .
C9 C -0.0825(2) 0.01786(10) 0.8086(8) 0.0279(10) Uani 1 1 d . . .
H9A H -0.1151 0.0112 0.6989 0.033 Uiso 1 1 calc R . .
H9B H -0.1026 0.0309 0.9279 0.033 Uiso 1 1 calc R . .
C10 C 0.0534(2) 0.01179(10) 0.9218(7) 0.0281(10) Uani 1 1 d . . .
H10 H 0.0858 0.0221 1.0188 0.034 Uiso 1 1 calc R . .
C11 C 0.03132(17) 0.03537(9) 0.7411(7) 0.0231(8) Uani 1 1 d . . .
C12 C 0.0000 0.0000 1.0796(10) 0.0358(16) Uani 1 2 d S . .
H12A H 0.0150 -0.0173 1.1785 0.043 Uiso 0.50 1 calc PR . .
H12B H -0.0150 0.0173 1.1785 0.043 Uiso 0.50 1 calc PR . .
C13 C 0.14376(17) 0.05150(10) 0.6495(7) 0.0234(9) Uani 1 1 d . . .
C14 C 0.17976(19) 0.03705(12) 0.4827(9) 0.0368(11) Uani 1 1 d . . .
H14 H 0.1607 0.0289 0.3489 0.044 Uiso 1 1 calc R . .
C15 C 0.2443(2) 0.03454(13) 0.5121(9) 0.0453(13) Uani 1 1 d . . .
H15 H 0.2685 0.0242 0.3991 0.054 Uiso 1 1 calc R . .
C16 C 0.2729(2) 0.04683(12) 0.7024(9) 0.0428(13) Uani 1 1 d . . .
H16 H 0.3168 0.0454 0.7190 0.051 Uiso 1 1 calc R . .
C17 C 0.2375(2) 0.06117(13) 0.8686(9) 0.0453(13) Uani 1 1 d . . .
H17 H 0.2570 0.0694 1.0013 0.054 Uiso 1 1 calc R . .
C18 C 0.1728(2) 0.06362(12) 0.8424(8) 0.0379(12) Uani 1 1 d . . .
H18 H 0.1487 0.0736 0.9573 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
Cl1 C4 1.755(4) . ?
N1 C7 1.363(5) . ?
N1 C8 1.311(5) . ?
C1 C2 1.423(6) . ?
C1 C11 1.386(6) . ?
C1 C13 1.510(5) . ?
C2 C3 1.407(6) . ?
C2 C7 1.423(5) . ?
C3 C4 1.356(6) . ?
C4 C5 1.392(6) . ?
C5 C6 1.340(7) . ?
C6 C7 1.406(6) . ?
C8 C9 1.505(6) . ?
C8 C11 1.433(5) . ?
C9 C10 1.540(6) 2 ?
C10 C9 1.540(6) 2 ?
C10 C11 1.516(6) . ?
C10 C12 1.539(5) . ?
C12 C10 1.539(5) 2 ?
C13 C14 1.374(6) . ?
C13 C18 1.374(6) . ?
C14 C15 1.386(6) . ?
C15 C16 1.360(7) . ?
C16 C17 1.362(7) . ?
C17 C18 1.389(6) . ?

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
C8 N1 C7 118.4(3) . . ?
C2 C1 C13 118.4(3) . . ?
C11 C1 C2 118.9(3) . . ?
C11 C1 C13 122.6(4) . . ?
C3 C2 C1 124.4(3) . . ?
C3 C2 C7 117.8(4) . . ?
C7 C2 C1 117.8(4) . . ?
C4 C3 C2 120.1(4) . . ?
C3 C4 Cl1 120.4(3) . . ?
C3 C4 C5 122.2(4) . . ?
C5 C4 Cl1 117.5(4) . . ?
C6 C5 C4 119.2(5) . . ?
C5 C6 C7 121.3(4) . . ?
N1 C7 C2 122.5(4) . . ?
N1 C7 C6 118.1(4) . . ?
C6 C7 C2 119.3(4) . . ?
N1 C8 C9 114.9(3) . . ?
N1 C8 C11 123.9(4) . . ?
C11 C8 C9 121.2(4) . . ?
C8 C9 C10 112.0(3) . 2 ?
C11 C10 C9 111.2(4) . 2 ?
C11 C10 C12 113.2(3) . . ?
C12 C10 C9 106.7(3) . 2 ?
C1 C11 C8 118.2(4) . . ?
C1 C11 C10 121.6(3) . . ?
C8 C11 C10 120.1(4) . . ?
C10 C12 C10 107.2(5) 2 . ?
C14 C13 C1 120.0(4) . . ?
C18 C13 C1 121.0(4) . . ?
C18 C13 C14 119.0(4) . . ?
C13 C14 C15 119.9(4) . . ?
C16 C15 C14 120.8(5) . . ?
C15 C16 C17 119.6(4) . . ?
C16 C17 C18 120.2(4) . . ?
C13 C18 C17 120.4(4) . . ?
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5032
_database_code_depnum_ccdc_archive 'CCDC 1028009'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H28 Cl2 N2 O'
_chemical_formula_weight         575.50

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'
Cl Cl 0.1484 0.1585 '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   P2(1)/c

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

_cell_length_a                   10.3943(5)
_cell_length_b                   17.4818(10)
_cell_length_c                   15.6814(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.6860(10)
_cell_angle_gamma                90.00
_cell_volume                     2823.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3715
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.35

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_correction_T_min  0.9065
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19838
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6500
_reflns_number_gt                5239
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0576P)²+1.2474P] 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       ?
_refine_ls_number_reflns         6500
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
Cl1 Cl 0.67181(6) 1.19544(3) 0.46634(4) 0.04352(17) Uani 1 1 d . . .
Cl2 Cl 0.16124(8) 0.47432(4) 0.62456(5) 0.0630(2) Uani 1 1 d . . .
N1 N 0.37402(15) 0.92420(10) 0.33946(11) 0.0276(4) Uani 1 1 d . . .
N2 N 0.56952(17) 0.65128(10) 0.48951(11) 0.0322(4) Uani 1 1 d . . .
C1 C 0.64692(18) 0.91355(11) 0.36036(12) 0.0246(4) Uani 1 1 d . . .
C2 C 0.58571(19) 0.98275(11) 0.38176(12) 0.0246(4) Uani 1 1 d . . .
C3 C 0.6547(2) 1.04926(12) 0.41203(12) 0.0285(4) Uani 1 1 d . . .
H3 H 0.7459 1.0499 0.4184 0.034 Uiso 1 1 calc R . .
C4 C 0.5877(2) 1.11241(12) 0.43194(12) 0.0301(4) Uani 1 1 d . . .
C5 C 0.4523(2) 1.11388(12) 0.42449(13) 0.0325(5) Uani 1 1 d . . .
H5 H 0.4089 1.1578 0.4402 0.039 Uiso 1 1 calc R . .
C6 C 0.3842(2) 1.05091(12) 0.39413(13) 0.0312(5) Uani 1 1 d . . .
H6 H 0.2931 1.0518 0.3881 0.037 Uiso 1 1 calc R . .
C7 C 0.44846(19) 0.98416(11) 0.37140(12) 0.0262(4) Uani 1 1 d . . .
C8 C 0.43294(18) 0.86193(12) 0.31776(12) 0.0266(4) Uani 1 1 d . . .
C9 C 0.34447(19) 0.80043(12) 0.27538(14) 0.0309(4) Uani 1 1 d . . .
H9A H 0.3133 0.8162 0.2162 0.037 Uiso 1 1 calc R . .
H9B H 0.2688 0.7960 0.3062 0.037 Uiso 1 1 calc R . .
C10 C 0.4086(2) 0.72190(12) 0.27321(13) 0.0295(4) Uani 1 1 d . . .
H10 H 0.3531 0.6891 0.2319 0.035 Uiso 1 1 calc R . .
C11 C 0.42569(19) 0.68280(11) 0.36030(12) 0.0257(4) Uani 1 1 d . . .
C12 C 0.32350(19) 0.64575(11) 0.39077(13) 0.0267(4) Uani 1 1 d . . .
C13 C 0.3459(2) 0.60702(11) 0.47111(13) 0.0292(4) Uani 1 1 d . . .
C14 C 0.2489(2) 0.56433(13) 0.50567(15) 0.0364(5) Uani 1 1 d . . .
H14 H 0.1642 0.5617 0.4761 0.044 Uiso 1 1 calc R . .
C15 C 0.2793(3) 0.52722(13) 0.58178(16) 0.0420(6) Uani 1 1 d . . .
C16 C 0.4044(3) 0.52931(14) 0.62792(15) 0.0450(6) Uani 1 1 d . . .
H16 H 0.4231 0.5023 0.6799 0.054 Uiso 1 1 calc R . .
C17 C 0.4983(3) 0.57064(14) 0.59686(14) 0.0411(5) Uani 1 1 d . . .
H17 H 0.5820 0.5728 0.6281 0.049 Uiso 1 1 calc R . .
C18 C 0.4717(2) 0.61058(12) 0.51800(13) 0.0316(5) Uani 1 1 d . . .
C19 C 0.54715(19) 0.68513(11) 0.41378(13) 0.0269(4) Uani 1 1 d . . .
C20 C 0.66249(19) 0.72617(12) 0.38588(14) 0.0310(5) Uani 1 1 d . . .
H20A H 0.7265 0.6880 0.3735 0.037 Uiso 1 1 calc R . .
H20B H 0.7028 0.7577 0.4338 0.037 Uiso 1 1 calc R . .
C21 C 0.62968(19) 0.77727(11) 0.30656(13) 0.0276(4) Uani 1 1 d . . .
H21 H 0.7110 0.7881 0.2823 0.033 Uiso 1 1 calc R . .
C22 C 0.57066(18) 0.85281(11) 0.32870(12) 0.0255(4) Uani 1 1 d . . .
C23 C 0.5397(2) 0.73243(12) 0.24019(13) 0.0316(5) Uani 1 1 d . . .
H23A H 0.5778 0.6824 0.2306 0.038 Uiso 1 1 calc R . .
H23B H 0.5276 0.7601 0.1854 0.038 Uiso 1 1 calc R . .
C24 C 0.79202(18) 0.90880(11) 0.37241(13) 0.0266(4) Uani 1 1 d . . .
C25 C 0.8610(2) 0.89699(14) 0.45306(15) 0.0388(5) Uani 1 1 d . . .
H25 H 0.8162 0.8907 0.5008 0.047 Uiso 1 1 calc R . .
C26 C 0.9952(2) 0.89439(16) 0.46432(16) 0.0454(6) Uani 1 1 d . . .
H26 H 1.0407 0.8857 0.5194 0.055 Uiso 1 1 calc R . .
C27 C 1.0624(2) 0.90436(13) 0.39539(17) 0.0402(6) Uani 1 1 d . . .
H27 H 1.1537 0.9039 0.4034 0.048 Uiso 1 1 calc R . .
C28 C 0.9957(2) 0.91492(14) 0.31499(17) 0.0423(6) Uani 1 1 d . . .
H28 H 1.0414 0.9213 0.2676 0.051 Uiso 1 1 calc R . .
C29 C 0.8611(2) 0.91633(13) 0.30280(15) 0.0356(5) Uani 1 1 d . . .
H29 H 0.8162 0.9224 0.2471 0.043 Uiso 1 1 calc R . .
C30 C 0.19060(19) 0.64867(11) 0.34198(13) 0.0287(4) Uani 1 1 d . . .
C31 C 0.1006(2) 0.69989(13) 0.36674(17) 0.0402(5) Uani 1 1 d . . .
H31 H 0.1219 0.7289 0.4171 0.048 Uiso 1 1 calc R . .
C32 C -0.0190(2) 0.70882(15) 0.3189(2) 0.0523(7) Uani 1 1 d . . .
H32 H -0.0780 0.7447 0.3360 0.063 Uiso 1 1 calc R . .
C33 C -0.0531(2) 0.66589(17) 0.24635(19) 0.0531(7) Uani 1 1 d . . .
H33 H -0.1347 0.6725 0.2133 0.064 Uiso 1 1 calc R . .
C34 C 0.0334(2) 0.61271(16) 0.22213(16) 0.0484(6) Uani 1 1 d . . .
H34 H 0.0097 0.5821 0.1733 0.058 Uiso 1 1 calc R . .
C35 C 0.1543(2) 0.60433(14) 0.26931(15) 0.0385(5) Uani 1 1 d . . .
H35 H 0.2127 0.5682 0.2521 0.046 Uiso 1 1 calc R . .
C1S C 0.9022(3) 0.6776(3) 0.5848(2) 0.0868(12) Uani 1 1 d . . .
H1S1 H 0.9112 0.6993 0.5290 0.130 Uiso 1 1 calc R . .
H1S2 H 0.9046 0.6222 0.5813 0.130 Uiso 1 1 calc R . .
H1S3 H 0.9728 0.6952 0.6269 0.130 Uiso 1 1 calc R . .
O1S O 0.7835(2) 0.70056(18) 0.60962(15) 0.0880(9) Uani 1 1 d . . .
H1S H 0.722(4) 0.681(2) 0.569(3) 0.113(15) 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
Cl1 C4 1.742(2) . ?
Cl2 C15 1.741(2) . ?
N1 C8 1.316(3) . ?
N1 C7 1.358(3) . ?
N2 C19 1.319(3) . ?
N2 C18 1.364(3) . ?
C1 C22 1.377(3) . ?
C1 C2 1.428(3) . ?
C1 C24 1.497(3) . ?
C2 C7 1.414(3) . ?
C2 C3 1.414(3) . ?
C3 C4 1.364(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.360(3) . ?
C6 C7 1.413(3) . ?
C8 C22 1.428(3) . ?
C8 C9 1.510(3) . ?
C9 C10 1.529(3) . ?
C10 C11 1.516(3) . ?
C10 C23 1.532(3) . ?
C11 C12 1.383(3) . ?
C11 C19 1.420(3) . ?
C12 C13 1.422(3) . ?
C12 C30 1.488(3) . ?
C13 C18 1.414(3) . ?
C13 C14 1.419(3) . ?
C14 C15 1.358(3) . ?
C15 C16 1.402(4) . ?
C16 C17 1.356(4) . ?
C17 C18 1.415(3) . ?
C19 C20 1.511(3) . ?
C20 C21 1.532(3) . ?
C21 C22 1.516(3) . ?
C21 C23 1.521(3) . ?
C24 C25 1.383(3) . ?
C24 C29 1.391(3) . ?
C25 C26 1.383(3) . ?
C26 C27 1.375(3) . ?
C27 C28 1.368(4) . ?
C28 C29 1.387(3) . ?
C30 C31 1.388(3) . ?
C30 C35 1.388(3) . ?
C31 C32 1.373(3) . ?
C32 C33 1.369(4) . ?
C33 C34 1.381(4) . ?
C34 C35 1.378(3) . ?
C1S O1S 1.401(4) . ?

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
C8 N1 C7 118.16(17) . . ?
C19 N2 C18 118.65(18) . . ?
C22 C1 C2 119.01(17) . . ?
C22 C1 C24 121.62(17) . . ?
C2 C1 C24 119.37(17) . . ?
C7 C2 C3 118.86(18) . . ?
C7 C2 C1 117.52(18) . . ?
C3 C2 C1 123.61(18) . . ?
C4 C3 C2 119.39(19) . . ?
C3 C4 C5 122.4(2) . . ?
C3 C4 Cl1 119.67(17) . . ?
C5 C4 Cl1 117.95(16) . . ?
C6 C5 C4 119.05(19) . . ?
C5 C6 C7 121.0(2) . . ?
N1 C7 C6 117.72(18) . . ?
N1 C7 C2 123.03(18) . . ?
C6 C7 C2 119.24(19) . . ?
N1 C8 C22 123.72(18) . . ?
N1 C8 C9 115.20(17) . . ?
C22 C8 C9 121.01(18) . . ?
C8 C9 C10 114.04(16) . . ?
C11 C10 C9 112.56(17) . . ?
C11 C10 C23 110.89(17) . . ?
C9 C10 C23 108.05(17) . . ?
C12 C11 C19 118.22(18) . . ?
C12 C11 C10 121.31(18) . . ?
C19 C11 C10 120.45(17) . . ?
C11 C12 C13 119.14(19) . . ?
C11 C12 C30 120.64(18) . . ?
C13 C12 C30 120.18(18) . . ?
C18 C13 C14 118.67(19) . . ?
C18 C13 C12 118.06(19) . . ?
C14 C13 C12 123.3(2) . . ?
C15 C14 C13 119.6(2) . . ?
C14 C15 C16 122.1(2) . . ?
C14 C15 Cl2 120.0(2) . . ?
C16 C15 Cl2 117.91(18) . . ?
C17 C16 C15 119.4(2) . . ?
C16 C17 C18 120.8(2) . . ?
N2 C18 C13 122.06(19) . . ?
N2 C18 C17 118.5(2) . . ?
C13 C18 C17 119.5(2) . . ?
N2 C19 C11 123.68(19) . . ?
N2 C19 C20 114.99(18) . . ?
C11 C19 C20 121.32(18) . . ?
C19 C20 C21 114.38(17) . . ?
C22 C21 C23 112.02(17) . . ?
C22 C21 C20 112.02(16) . . ?
C23 C21 C20 107.75(17) . . ?
C1 C22 C8 118.47(18) . . ?
C1 C22 C21 121.54(17) . . ?
C8 C22 C21 119.99(17) . . ?
C21 C23 C10 108.91(16) . . ?
C25 C24 C29 118.21(19) . . ?
C25 C24 C1 120.94(18) . . ?
C29 C24 C1 120.85(18) . . ?
C26 C25 C24 120.8(2) . . ?
C27 C26 C25 120.4(2) . . ?
C28 C27 C26 119.6(2) . . ?
C27 C28 C29 120.5(2) . . ?
C28 C29 C24 120.5(2) . . ?
C31 C30 C35 118.1(2) . . ?
C31 C30 C12 119.52(19) . . ?
C35 C30 C12 122.35(19) . . ?
C32 C31 C30 121.0(2) . . ?
C33 C32 C31 120.4(3) . . ?
C32 C33 C34 119.5(2) . . ?
C35 C34 C33 120.3(2) . . ?
C34 C35 C30 120.7(2) . . ?

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
O1S H1S N2 0.91(4) 1.95(4) 2.849(3) 170(4) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5069
_database_code_depnum_ccdc_archive 'CCDC 1028010'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H30 Cl2 N2 O'
_chemical_formula_weight         589.53

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'
Cl Cl 0.1484 0.1585 '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   P2(1)/c

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

_cell_length_a                   10.4238(6)
_cell_length_b                   17.4861(10)
_cell_length_c                   15.9174(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.410(2)
_cell_angle_gamma                90.00
_cell_volume                     2870.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1789
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      29.83

_exptl_crystal_description       'Thin Plate'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15135
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         24.00
_reflns_number_total             4497
_reflns_number_gt                3394
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0580P)²+3.0805P] 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       ?
_refine_ls_number_reflns         4497
_refine_ls_number_parameters     381
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0926
_refine_ls_wR_factor_ref         0.1856
_refine_ls_wR_factor_gt          0.1737
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_restrained_S_all      1.234
_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
Cl1 Cl 0.82521(18) -0.02395(9) 0.37140(10) 0.0612(5) Uani 1 1 d . . .
Cl2 Cl 0.33114(14) 0.69577(7) 0.53680(9) 0.0399(4) Uani 1 1 d . . .
N1 N 0.4248(4) 0.1527(2) 0.5092(2) 0.0271(10) Uani 1 1 d . . .
N2 N 0.6258(4) 0.4224(2) 0.6593(2) 0.0221(9) Uani 1 1 d . . .
C1 C 0.6718(5) 0.1437(3) 0.6068(3) 0.0230(11) Uani 1 1 d . . .
C2 C 0.6466(5) 0.1060(3) 0.5273(3) 0.0241(12) Uani 1 1 d . . .
C3 C 0.7409(5) 0.0634(3) 0.4917(3) 0.0320(13) Uani 1 1 d . . .
H3 H 0.8259 0.0597 0.5208 0.038 Uiso 1 1 calc R . .
C4 C 0.7089(6) 0.0281(3) 0.4159(4) 0.0399(15) Uani 1 1 d . . .
C5 C 0.5852(6) 0.0324(3) 0.3694(3) 0.0424(16) Uani 1 1 d . . .
H5 H 0.5661 0.0075 0.3167 0.051 Uiso 1 1 calc R . .
C6 C 0.4925(6) 0.0731(3) 0.4013(3) 0.0406(15) Uani 1 1 d . . .
H6 H 0.4084 0.0757 0.3707 0.049 Uiso 1 1 calc R . .
C7 C 0.5209(5) 0.1116(3) 0.4796(3) 0.0284(12) Uani 1 1 d . . .
C8 C 0.4493(5) 0.1852(3) 0.5843(3) 0.0223(11) Uani 1 1 d . . .
C9 C 0.3358(5) 0.2264(3) 0.6122(3) 0.0280(12) Uani 1 1 d . . .
H9A H 0.2716 0.1884 0.6239 0.034 Uiso 1 1 calc R . .
H9B H 0.2952 0.2584 0.5652 0.034 Uiso 1 1 calc R . .
C10 C 0.3696(4) 0.2770(3) 0.6910(3) 0.0237(11) Uani 1 1 d . . .
H10 H 0.2891 0.2877 0.7150 0.028 Uiso 1 1 calc R . .
C11 C 0.4288(4) 0.3523(3) 0.6694(3) 0.0191(11) Uani 1 1 d . . .
C12 C 0.3538(4) 0.4127(3) 0.6373(3) 0.0199(11) Uani 1 1 d . . .
C13 C 0.4156(4) 0.4819(3) 0.6174(3) 0.0196(11) Uani 1 1 d . . .
C14 C 0.3483(5) 0.5489(3) 0.5883(3) 0.0252(12) Uani 1 1 d . . .
H14 H 0.2573 0.5498 0.5817 0.030 Uiso 1 1 calc R . .
C15 C 0.4141(5) 0.6119(3) 0.5698(3) 0.0247(12) Uani 1 1 d . . .
C16 C 0.5492(5) 0.6130(3) 0.5780(3) 0.0281(12) Uani 1 1 d . . .
H16 H 0.5931 0.6569 0.5633 0.034 Uiso 1 1 calc R . .
C17 C 0.6161(5) 0.5497(3) 0.6072(3) 0.0260(12) Uani 1 1 d . . .
H17 H 0.7072 0.5504 0.6138 0.031 Uiso 1 1 calc R . .
C18 C 0.5523(5) 0.4827(3) 0.6281(3) 0.0229(11) Uani 1 1 d . . .
C19 C 0.5669(5) 0.3605(3) 0.6804(3) 0.0226(11) Uani 1 1 d . . .
C20 C 0.6551(5) 0.2985(3) 0.7220(3) 0.0277(12) Uani 1 1 d . . .
H20A H 0.6873 0.3138 0.7805 0.033 Uiso 1 1 calc R . .
H20B H 0.7301 0.2939 0.6917 0.033 Uiso 1 1 calc R . .
C21 C 0.5899(5) 0.2203(3) 0.7233(3) 0.0249(12) Uani 1 1 d . . .
H21 H 0.6452 0.1871 0.7640 0.030 Uiso 1 1 calc R . .
C22 C 0.5710(5) 0.1814(3) 0.6368(3) 0.0213(11) Uani 1 1 d . . .
C23 C 0.4606(5) 0.2318(3) 0.7556(3) 0.0276(12) Uani 1 1 d . . .
H23A H 0.4221 0.1820 0.7651 0.033 Uiso 1 1 calc R . .
H23B H 0.4745 0.2593 0.8098 0.033 Uiso 1 1 calc R . .
C24 C 0.8055(5) 0.1457(3) 0.6543(3) 0.0252(12) Uani 1 1 d . . .
C25 C 0.8952(5) 0.1966(3) 0.6299(3) 0.0334(13) Uani 1 1 d . . .
H25 H 0.8724 0.2268 0.5812 0.040 Uiso 1 1 calc R . .
C26 C 1.0171(5) 0.2036(3) 0.6759(4) 0.0426(15) Uani 1 1 d . . .
H26 H 1.0760 0.2391 0.6590 0.051 Uiso 1 1 calc R . .
C27 C 1.0527(6) 0.1595(4) 0.7456(4) 0.0440(15) Uani 1 1 d . . .
H27 H 1.1358 0.1647 0.7771 0.053 Uiso 1 1 calc R . .
C28 C 0.9664(6) 0.1069(4) 0.7703(4) 0.0445(16) Uani 1 1 d . . .
H28 H 0.9915 0.0756 0.8178 0.053 Uiso 1 1 calc R . .
C29 C 0.8434(5) 0.1006(3) 0.7249(3) 0.0353(14) Uani 1 1 d . . .
H29 H 0.7847 0.0651 0.7422 0.042 Uiso 1 1 calc R . .
C30 C 0.2086(4) 0.4086(3) 0.6244(3) 0.0219(11) Uani 1 1 d . . .
C31 C 0.1396(5) 0.3995(3) 0.5438(3) 0.0328(13) Uani 1 1 d . . .
H31 H 0.1845 0.3952 0.4970 0.039 Uiso 1 1 calc R . .
C32 C 0.0067(5) 0.3967(3) 0.5314(4) 0.0396(14) Uani 1 1 d . . .
H32 H -0.0383 0.3893 0.4764 0.048 Uiso 1 1 calc R . .
C33 C -0.0613(5) 0.4046(3) 0.5986(4) 0.0319(13) Uani 1 1 d . . .
H33 H -0.1525 0.4045 0.5895 0.038 Uiso 1 1 calc R . .
C34 C 0.0050(5) 0.4125(3) 0.6789(4) 0.0360(14) Uani 1 1 d . . .
H34 H -0.0410 0.4168 0.7253 0.043 Uiso 1 1 calc R . .
C35 C 0.1386(5) 0.4144(3) 0.6925(3) 0.0294(12) Uani 1 1 d . . .
H35 H 0.1829 0.4197 0.7480 0.035 Uiso 1 1 calc R . .
O1S O 0.2074(5) 0.1992(4) 0.3894(3) 0.100(2) Uani 1 1 d D . .
H1S H 0.2758 0.1897 0.4213 0.151 Uiso 1 1 calc R . .
C1S C -0.0183(10) 0.1969(6) 0.3988(7) 0.133(4) Uani 1 1 d DU . .
H1S1 H -0.0108 0.2431 0.4329 0.200 Uiso 1 1 calc R . .
H1S2 H -0.0899 0.1662 0.4127 0.200 Uiso 1 1 calc R . .
H1S3 H -0.0341 0.2104 0.3391 0.200 Uiso 1 1 calc R . .
C2S C 0.1002(7) 0.1537(6) 0.4161(6) 0.124(4) Uani 1 1 d DU . .
H2S1 H 0.0912 0.1052 0.3848 0.149 Uiso 1 1 calc R . .
H2S2 H 0.1193 0.1422 0.4769 0.149 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
Cl1 C4 1.746(6) . ?
Cl2 C15 1.744(5) . ?
N1 C8 1.315(6) . ?
N1 C7 1.371(6) . ?
N2 C19 1.312(6) . ?
N2 C18 1.353(6) . ?
C1 C22 1.384(6) . ?
C1 C2 1.416(7) . ?
C1 C24 1.486(7) . ?
C2 C3 1.417(7) . ?
C2 C7 1.419(7) . ?
C3 C4 1.353(7) . ?
C4 C5 1.392(8) . ?
C5 C6 1.356(8) . ?
C6 C7 1.409(7) . ?
C8 C22 1.415(7) . ?
C8 C9 1.507(7) . ?
C9 C10 1.533(7) . ?
C10 C23 1.515(6) . ?
C10 C11 1.516(6) . ?
C11 C12 1.368(6) . ?
C11 C19 1.431(6) . ?
C12 C13 1.428(6) . ?
C12 C30 1.499(6) . ?
C13 C14 1.408(6) . ?
C13 C18 1.411(6) . ?
C14 C15 1.353(7) . ?
C15 C16 1.396(7) . ?
C16 C17 1.354(7) . ?
C17 C18 1.411(7) . ?
C19 C20 1.511(7) . ?
C20 C21 1.528(7) . ?
C21 C22 1.522(6) . ?
C21 C23 1.524(6) . ?
C24 C29 1.383(7) . ?
C24 C25 1.387(7) . ?
C25 C26 1.376(7) . ?
C26 C27 1.358(8) . ?
C27 C28 1.382(8) . ?
C28 C29 1.381(8) . ?
C30 C31 1.384(7) . ?
C30 C35 1.396(7) . ?
C31 C32 1.371(7) . ?
C32 C33 1.374(7) . ?
C33 C34 1.369(7) . ?
C34 C35 1.378(7) . ?
O1S C2S 1.483(8) . ?
C1S C2S 1.440(8) . ?

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
C8 N1 C7 119.0(4) . . ?
C19 N2 C18 118.3(4) . . ?
C22 C1 C2 118.6(4) . . ?
C22 C1 C24 121.0(4) . . ?
C2 C1 C24 120.3(4) . . ?
C1 C2 C3 123.6(5) . . ?
C1 C2 C7 118.9(4) . . ?
C3 C2 C7 117.5(5) . . ?
C4 C3 C2 120.2(5) . . ?
C3 C4 C5 122.5(5) . . ?
C3 C4 Cl1 120.3(5) . . ?
C5 C4 Cl1 117.2(4) . . ?
C6 C5 C4 119.0(5) . . ?
C5 C6 C7 120.8(6) . . ?
N1 C7 C6 119.0(5) . . ?
N1 C7 C2 121.0(4) . . ?
C6 C7 C2 119.9(5) . . ?
N1 C8 C22 123.7(4) . . ?
N1 C8 C9 114.7(4) . . ?
C22 C8 C9 121.5(4) . . ?
C8 C9 C10 114.9(4) . . ?
C23 C10 C11 111.9(4) . . ?
C23 C10 C9 107.5(4) . . ?
C11 C10 C9 111.5(4) . . ?
C12 C11 C19 118.5(4) . . ?
C12 C11 C10 121.7(4) . . ?
C19 C11 C10 119.7(4) . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 C30 121.7(4) . . ?
C13 C12 C30 119.3(4) . . ?
C14 C13 C18 118.5(4) . . ?
C14 C13 C12 124.0(4) . . ?
C18 C13 C12 117.5(4) . . ?
C15 C14 C13 120.4(5) . . ?
C14 C15 C16 121.8(5) . . ?
C14 C15 Cl2 120.4(4) . . ?
C16 C15 Cl2 117.8(4) . . ?
C17 C16 C15 118.9(5) . . ?
C16 C17 C18 121.6(5) . . ?
N2 C18 C17 118.2(4) . . ?
N2 C18 C13 123.0(4) . . ?
C17 C18 C13 118.8(5) . . ?
N2 C19 C11 123.5(4) . . ?
N2 C19 C20 115.2(4) . . ?
C11 C19 C20 121.2(4) . . ?
C19 C20 C21 113.9(4) . . ?
C22 C21 C23 111.1(4) . . ?
C22 C21 C20 112.7(4) . . ?
C23 C21 C20 107.7(4) . . ?
C1 C22 C8 118.6(4) . . ?
C1 C22 C21 121.4(4) . . ?
C8 C22 C21 120.0(4) . . ?
C10 C23 C21 109.7(4) . . ?
C29 C24 C25 118.0(5) . . ?
C29 C24 C1 122.4(5) . . ?
C25 C24 C1 119.5(4) . . ?
C26 C25 C24 121.1(5) . . ?
C27 C26 C25 120.3(6) . . ?
C26 C27 C28 119.9(5) . . ?
C29 C28 C27 119.9(5) . . ?
C28 C29 C24 120.8(5) . . ?
C31 C30 C35 117.9(4) . . ?
C31 C30 C12 120.7(4) . . ?
C35 C30 C12 121.4(4) . . ?
C32 C31 C30 121.0(5) . . ?
C31 C32 C33 120.6(5) . . ?
C34 C33 C32 119.3(5) . . ?
C33 C34 C35 120.6(5) . . ?
C34 C35 C30 120.5(5) . . ?
C1S C2S O1S 108.9(8) . . ?

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
O1S H1S N1 0.83 2.04 2.859(6) 169.9 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5048
_database_code_depnum_ccdc_archive 'CCDC 1028011'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H28 Cl2 N2 O2'
_chemical_formula_weight         603.51

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'
Cl Cl 0.1484 0.1585 '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   P2(1)/c

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

_cell_length_a                   10.4620(5)
_cell_length_b                   17.5011(8)
_cell_length_c                   15.8272(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.5300(10)
_cell_angle_gamma                90.00
_cell_volume                     2884.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7305
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.51

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_correction_T_min  0.9018
_exptl_absorpt_correction_T_max  0.9250
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37577
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6637
_reflns_number_gt                5616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0823P)²+0.7077P] 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       ?
_refine_ls_number_reflns         6637
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.003
_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
Cl1 Cl 1.16967(4) 1.19601(2) 0.46078(3) 0.05024(14) Uani 1 1 d . . .
Cl2 Cl 0.66800(6) 0.47543(3) 0.63054(4) 0.07025(18) Uani 1 1 d . . .
N1 N 0.88463(11) 0.92192(7) 0.34155(8) 0.0333(3) Uani 1 1 d . . .
N2 N 1.07828(13) 0.64870(7) 0.49028(8) 0.0383(3) Uani 1 1 d . . .
C1 C 1.15542(13) 0.91269(8) 0.36151(9) 0.0300(3) Uani 1 1 d . . .
C2 C 1.09195(13) 0.98164(8) 0.38195(9) 0.0297(3) Uani 1 1 d . . .
C3 C 1.15833(14) 1.04902(8) 0.41067(9) 0.0329(3) Uani 1 1 d . . .
H3 H 1.2486 1.0501 0.4169 0.039 Uiso 1 1 calc R . .
C4 C 1.08955(15) 1.11211(8) 0.42907(9) 0.0348(3) Uani 1 1 d . . .
C5 C 0.95504(16) 1.11322(9) 0.42217(10) 0.0380(3) Uani 1 1 d . . .
H5 H 0.9107 1.1572 0.4370 0.046 Uiso 1 1 calc R . .
C6 C 0.88958(15) 1.04941(9) 0.39349(10) 0.0371(3) Uani 1 1 d . . .
H6 H 0.7993 1.0498 0.3877 0.045 Uiso 1 1 calc R . .
C7 C 0.95616(13) 0.98261(8) 0.37228(9) 0.0309(3) Uani 1 1 d . . .
C8 C 0.94533(13) 0.85976(8) 0.32064(9) 0.0310(3) Uani 1 1 d . . .
C9 C 0.86025(14) 0.79767(9) 0.28012(10) 0.0367(3) Uani 1 1 d . . .
H9A H 0.8313 0.8128 0.2218 0.044 Uiso 1 1 calc R . .
H9B H 0.7841 0.7930 0.3112 0.044 Uiso 1 1 calc R . .
C10 C 0.92581(14) 0.71965(8) 0.27831(9) 0.0340(3) Uani 1 1 d . . .
H10 H 0.8728 0.6863 0.2383 0.041 Uiso 1 1 calc R . .
C11 C 0.93957(14) 0.68117(8) 0.36473(9) 0.0319(3) Uani 1 1 d . . .
C12 C 0.83740(14) 0.64407(8) 0.39619(9) 0.0332(3) Uani 1 1 d . . .
C13 C 0.85699(15) 0.60549(8) 0.47562(10) 0.0363(3) Uani 1 1 d . . .
C14 C 0.75935(17) 0.56326(9) 0.51077(11) 0.0429(4) Uani 1 1 d . . .
H14 H 0.6765 0.5602 0.4822 0.051 Uiso 1 1 calc R . .
C15 C 0.7871(2) 0.52711(9) 0.58651(12) 0.0500(4) Uani 1 1 d . . .
C16 C 0.9096(2) 0.52919(10) 0.63108(12) 0.0544(5) Uani 1 1 d . . .
H16 H 0.9258 0.5032 0.6830 0.065 Uiso 1 1 calc R . .
C17 C 1.0048(2) 0.56936(10) 0.59833(11) 0.0491(4) Uani 1 1 d . . .
H17 H 1.0872 0.5710 0.6278 0.059 Uiso 1 1 calc R . .
C18 C 0.98055(16) 0.60867(8) 0.52030(10) 0.0382(3) Uani 1 1 d . . .
C19 C 1.05867(14) 0.68354(8) 0.41596(10) 0.0333(3) Uani 1 1 d . . .
C20 C 1.17309(14) 0.72545(9) 0.38768(11) 0.0372(3) Uani 1 1 d . . .
H20A H 1.2383 0.6879 0.3755 0.045 Uiso 1 1 calc R . .
H20B H 1.2100 0.7575 0.4346 0.045 Uiso 1 1 calc R . .
C21 C 1.14307(14) 0.77592(8) 0.30927(10) 0.0338(3) Uani 1 1 d . . .
H21 H 1.2245 0.7871 0.2847 0.041 Uiso 1 1 calc R . .
C22 C 1.08154(13) 0.85133(8) 0.33095(9) 0.0304(3) Uani 1 1 d . . .
C23 C 1.05638(15) 0.73067(9) 0.24432(10) 0.0379(3) Uani 1 1 d . . .
H23A H 1.0951 0.6809 0.2345 0.045 Uiso 1 1 calc R . .
H23B H 1.0459 0.7584 0.1903 0.045 Uiso 1 1 calc R . .
C24 C 1.29884(13) 0.90877(8) 0.37409(10) 0.0323(3) Uani 1 1 d . . .
C25 C 1.36043(15) 0.89641(10) 0.45437(11) 0.0418(4) Uani 1 1 d . . .
H25 H 1.3115 0.8894 0.5006 0.050 Uiso 1 1 calc R . .
C26 C 1.49401(16) 0.89428(11) 0.46744(12) 0.0492(4) Uani 1 1 d . . .
H26 H 1.5345 0.8851 0.5221 0.059 Uiso 1 1 calc R . .
C27 C 1.56680(15) 0.90560(10) 0.40061(13) 0.0476(4) Uani 1 1 d . . .
H27 H 1.6569 0.9058 0.4097 0.057 Uiso 1 1 calc R . .
C28 C 1.50684(17) 0.91660(10) 0.32058(13) 0.0502(4) Uani 1 1 d . . .
H28 H 1.5563 0.9234 0.2746 0.060 Uiso 1 1 calc R . .
C29 C 1.37307(16) 0.91783(9) 0.30671(11) 0.0419(4) Uani 1 1 d . . .
H29 H 1.3331 0.9248 0.2515 0.050 Uiso 1 1 calc R . .
C30 C 0.70644(14) 0.64700(8) 0.35022(10) 0.0350(3) Uani 1 1 d . . .
C31 C 0.61726(16) 0.69810(9) 0.37745(12) 0.0440(4) Uani 1 1 d . . .
H31 H 0.6393 0.7282 0.4259 0.053 Uiso 1 1 calc R . .
C32 C 0.49652(17) 0.70523(10) 0.33421(14) 0.0517(4) Uani 1 1 d . . .
H32 H 0.4374 0.7403 0.3530 0.062 Uiso 1 1 calc R . .
C33 C 0.46326(18) 0.66117(11) 0.26411(13) 0.0536(5) Uani 1 1 d . . .
H33 H 0.3813 0.6661 0.2346 0.064 Uiso 1 1 calc R . .
C34 C 0.54970(19) 0.60949(12) 0.23658(13) 0.0536(5) Uani 1 1 d . . .
H34 H 0.5261 0.5790 0.1887 0.064 Uiso 1 1 calc R . .
C35 C 0.67185(17) 0.60235(10) 0.27936(11) 0.0441(4) Uani 1 1 d . . .
H35 H 0.7307 0.5673 0.2602 0.053 Uiso 1 1 calc R . .
O1S O 1.31243(15) 0.75977(10) 0.59512(11) 0.0732(5) Uani 1 1 d . . .
O2S O 1.31887(16) 0.63615(9) 0.56664(11) 0.0660(4) Uani 1 1 d . . .
H2S H 1.228(3) 0.644(2) 0.545(2) 0.115(11) Uiso 1 1 d . . .
C1S C 1.5144(2) 0.69429(15) 0.61484(16) 0.0683(6) Uani 1 1 d . . .
H1SA H 1.5412 0.6419 0.6074 0.102 Uiso 1 1 calc R . .
H1SB H 1.5347 0.7093 0.6736 0.102 Uiso 1 1 calc R . .
H1SC H 1.5592 0.7275 0.5784 0.102 Uiso 1 1 calc R . .
C2S C 1.3723(2) 0.70078(12) 0.59169(12) 0.0526(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7406(15) . ?
Cl2 C15 1.7386(18) . ?
N1 C8 1.3178(19) . ?
N1 C7 1.3618(19) . ?
N2 C19 1.323(2) . ?
N2 C18 1.362(2) . ?
C1 C22 1.3829(19) . ?
C1 C2 1.4293(19) . ?
C1 C24 1.4961(19) . ?
C2 C7 1.414(2) . ?
C2 C3 1.421(2) . ?
C3 C4 1.365(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.365(2) . ?
C6 C7 1.418(2) . ?
C8 C22 1.4263(19) . ?
C8 C9 1.508(2) . ?
C9 C10 1.530(2) . ?
C10 C11 1.519(2) . ?
C10 C23 1.528(2) . ?
C11 C12 1.384(2) . ?
C11 C19 1.420(2) . ?
C12 C13 1.424(2) . ?
C12 C30 1.489(2) . ?
C13 C18 1.413(2) . ?
C13 C14 1.417(2) . ?
C14 C15 1.362(3) . ?
C15 C16 1.403(3) . ?
C16 C17 1.362(3) . ?
C17 C18 1.415(2) . ?
C19 C20 1.508(2) . ?
C20 C21 1.531(2) . ?
C21 C22 1.5220(19) . ?
C21 C23 1.525(2) . ?
C24 C25 1.385(2) . ?
C24 C29 1.387(2) . ?
C25 C26 1.393(2) . ?
C26 C27 1.376(3) . ?
C27 C28 1.372(3) . ?
C28 C29 1.396(2) . ?
C30 C35 1.386(2) . ?
C30 C31 1.391(2) . ?
C31 C32 1.383(3) . ?
C32 C33 1.368(3) . ?
C33 C34 1.379(3) . ?
C34 C35 1.393(3) . ?
O1S C2S 1.212(2) . ?
O2S C2S 1.306(3) . ?
C1S C2S 1.501(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
C8 N1 C7 118.16(12) . . ?
C19 N2 C18 119.32(14) . . ?
C22 C1 C2 118.59(13) . . ?
C22 C1 C24 122.04(12) . . ?
C2 C1 C24 119.37(12) . . ?
C7 C2 C3 118.65(13) . . ?
C7 C2 C1 117.99(12) . . ?
C3 C2 C1 123.35(13) . . ?
C4 C3 C2 119.24(13) . . ?
C3 C4 C5 122.75(14) . . ?
C3 C4 Cl1 119.67(12) . . ?
C5 C4 Cl1 117.57(11) . . ?
C6 C5 C4 118.86(14) . . ?
C5 C6 C7 120.75(14) . . ?
N1 C7 C2 122.75(13) . . ?
N1 C7 C6 117.52(13) . . ?
C2 C7 C6 119.71(13) . . ?
N1 C8 C22 123.85(13) . . ?
N1 C8 C9 115.00(12) . . ?
C22 C8 C9 121.09(13) . . ?
C8 C9 C10 113.82(12) . . ?
C11 C10 C23 111.26(13) . . ?
C11 C10 C9 112.50(12) . . ?
C23 C10 C9 108.16(12) . . ?
C12 C11 C19 118.30(14) . . ?
C12 C11 C10 121.50(13) . . ?
C19 C11 C10 120.19(13) . . ?
C11 C12 C13 119.31(14) . . ?
C11 C12 C30 120.96(13) . . ?
C13 C12 C30 119.67(13) . . ?
C18 C13 C14 118.89(15) . . ?
C18 C13 C12 118.02(14) . . ?
C14 C13 C12 123.08(15) . . ?
C15 C14 C13 119.17(17) . . ?
C14 C15 C16 122.50(17) . . ?
C14 C15 Cl2 119.64(16) . . ?
C16 C15 Cl2 117.86(14) . . ?
C17 C16 C15 119.25(17) . . ?
C16 C17 C18 120.44(19) . . ?
N2 C18 C13 121.79(14) . . ?
N2 C18 C17 118.47(16) . . ?
C13 C18 C17 119.74(16) . . ?
N2 C19 C11 123.11(14) . . ?
N2 C19 C20 115.37(13) . . ?
C11 C19 C20 121.51(13) . . ?
C19 C20 C21 114.48(12) . . ?
C22 C21 C23 111.42(12) . . ?
C22 C21 C20 112.07(12) . . ?
C23 C21 C20 108.00(12) . . ?
C1 C22 C8 118.57(13) . . ?
C1 C22 C21 121.19(12) . . ?
C8 C22 C21 120.23(12) . . ?
C21 C23 C10 108.78(12) . . ?
C25 C24 C29 118.53(14) . . ?
C25 C24 C1 120.07(13) . . ?
C29 C24 C1 121.39(14) . . ?
C24 C25 C26 120.77(16) . . ?
C27 C26 C25 120.23(17) . . ?
C28 C27 C26 119.49(15) . . ?
C27 C28 C29 120.65(16) . . ?
C24 C29 C28 120.29(16) . . ?
C35 C30 C31 118.86(15) . . ?
C35 C30 C12 122.16(14) . . ?
C31 C30 C12 118.95(14) . . ?
C32 C31 C30 120.85(17) . . ?
C33 C32 C31 119.95(18) . . ?
C32 C33 C34 120.17(17) . . ?
C33 C34 C35 120.27(18) . . ?
C30 C35 C34 119.90(17) . . ?
O1S C2S O2S 122.91(19) . . ?
O1S C2S C1S 123.9(2) . . ?
O2S C2S C1S 113.17(18) . . ?

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
O2S H2S N2 0.98(3) 1.72(4) 2.694(2) 169(3) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.061
