# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_mo_2016065_0m
_database_code_depnum_ccdc_archive 'CCDC 1588636'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 Cl N O'
_chemical_formula_weight         307.76

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   '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                   7.0958(5)
_cell_length_b                   24.4284(17)
_cell_length_c                   9.0306(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.453(3)
_cell_angle_gamma                90.00
_cell_volume                     1484.87(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8937
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6718
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'

_exptl_special_details           
; 
SADABS; Bruker, 2008
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12870
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3377
_reflns_number_gt                3098
_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)+(0.0450P)²+0.5560P] 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         3377
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.86075(4) 0.231720(11) 1.04372(4) 0.02827(10) Uani 1 1 d . . .
O1 O 0.14793(12) 0.36291(3) 0.74080(9) 0.02103(18) Uani 1 1 d . . .
H1 H 0.1728 0.3882 0.6867 0.032 Uiso 1 1 calc R . .
N1 N 0.22047(13) 0.44327(4) 0.55899(10) 0.01659(19) Uani 1 1 d . . .
C13 C 0.26287(15) 0.49514(4) 0.60962(12) 0.0172(2) Uani 1 1 d . . .
C14 C 0.31649(16) 0.33380(4) 0.80958(12) 0.0180(2) Uani 1 1 d . . .
C12 C 0.27231(15) 0.53903(4) 0.50747(13) 0.0190(2) Uani 1 1 d . . .
C5 C 0.23880(16) 0.52671(5) 0.35065(13) 0.0199(2) Uani 1 1 d . . .
H5 H 0.2423 0.5551 0.2796 0.024 Uiso 1 1 calc R . .
C10 C 0.19182(15) 0.43181(4) 0.40722(12) 0.0165(2) Uani 1 1 d . . .
C11 C 0.20027(15) 0.47322(5) 0.29732(12) 0.0179(2) Uani 1 1 d . . .
C19 C 0.49972(17) 0.34783(5) 0.79374(12) 0.0198(2) Uani 1 1 d . . .
H19 H 0.5096 0.3789 0.7333 0.024 Uiso 1 1 calc R . .
C9 C 0.29834(17) 0.50661(5) 0.77117(13) 0.0224(2) Uani 1 1 d . . .
H9 H 0.2927 0.4779 0.8406 0.027 Uiso 1 1 calc R . .
C4 C 0.16857(17) 0.45766(5) 0.13893(13) 0.0230(2) Uani 1 1 d . . .
H4 H 0.1745 0.4846 0.0648 0.028 Uiso 1 1 calc R . .
C1 C 0.15107(17) 0.37678(5) 0.35490(13) 0.0212(2) Uani 1 1 d . . .
H1A H 0.1441 0.3489 0.4264 0.025 Uiso 1 1 calc R . .
C3 C 0.13006(18) 0.40482(6) 0.09295(13) 0.0266(3) Uani 1 1 d . . .
H3 H 0.1084 0.3951 -0.0130 0.032 Uiso 1 1 calc R . .
C18 C 0.66799(17) 0.31673(5) 0.86582(13) 0.0220(2) Uani 1 1 d . . .
H18 H 0.7925 0.3263 0.8545 0.026 Uiso 1 1 calc R . .
C2 C 0.12208(18) 0.36400(5) 0.20236(14) 0.0262(3) Uani 1 1 d . . .
H2 H 0.0961 0.3271 0.1688 0.031 Uiso 1 1 calc R . .
C17 C 0.65194(17) 0.27189(5) 0.95388(13) 0.0211(2) Uani 1 1 d . . .
C15 C 0.30353(18) 0.28857(5) 0.89911(14) 0.0253(3) Uani 1 1 d . . .
H15 H 0.1793 0.2788 0.9106 0.030 Uiso 1 1 calc R . .
C16 C 0.47132(19) 0.25763(5) 0.97184(15) 0.0271(3) Uani 1 1 d . . .
H16 H 0.4625 0.2269 1.0336 0.033 Uiso 1 1 calc R . .
C6 C 0.31573(18) 0.59297(5) 0.57035(16) 0.0258(3) Uani 1 1 d . . .
H6 H 0.3219 0.6225 0.5037 0.031 Uiso 1 1 calc R . .
C8 C 0.34022(18) 0.55858(5) 0.82609(14) 0.0278(3) Uani 1 1 d . . .
H8 H 0.3644 0.5657 0.9339 0.033 Uiso 1 1 calc R . .
C7 C 0.34827(18) 0.60229(5) 0.72460(16) 0.0295(3) Uani 1 1 d . . .
H7 H 0.3766 0.6383 0.7650 0.035 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
Cl2 C17 1.7480(11) . ?
O1 C14 1.3608(13) . ?
O1 H1 0.8400 . ?
N1 C13 1.3485(14) . ?
N1 C10 1.3497(13) . ?
C13 C9 1.4274(15) . ?
C13 C12 1.4296(16) . ?
C14 C15 1.3892(16) . ?
C14 C19 1.3951(16) . ?
C12 C5 1.3926(16) . ?
C12 C6 1.4294(16) . ?
C5 C11 1.3895(16) . ?
C5 H5 0.9500 . ?
C10 C1 1.4238(15) . ?
C10 C11 1.4316(15) . ?
C11 C4 1.4273(15) . ?
C19 C18 1.3909(16) . ?
C19 H19 0.9500 . ?
C9 C8 1.3613(17) . ?
C9 H9 0.9500 . ?
C4 C3 1.3569(18) . ?
C4 H4 0.9500 . ?
C1 C2 1.3632(16) . ?
C1 H1A 0.9500 . ?
C3 C2 1.4175(18) . ?
C3 H3 0.9500 . ?
C18 C17 1.3793(16) . ?
C18 H18 0.9500 . ?
C2 H2 0.9500 . ?
C17 C16 1.3863(17) . ?
C15 C16 1.3875(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C6 C7 1.3572(19) . ?
C6 H6 0.9500 . ?
C8 C7 1.420(2) . ?
C8 H8 0.9500 . ?
C7 H7 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
C14 O1 H1 109.5 . . ?
C13 N1 C10 119.00(9) . . ?
N1 C13 C9 118.63(10) . . ?
N1 C13 C12 122.47(10) . . ?
C9 C13 C12 118.90(10) . . ?
O1 C14 C15 118.08(10) . . ?
O1 C14 C19 122.53(10) . . ?
C15 C14 C19 119.38(10) . . ?
C5 C12 C6 123.31(11) . . ?
C5 C12 C13 117.80(10) . . ?
C6 C12 C13 118.90(11) . . ?
C11 C5 C12 120.48(10) . . ?
C11 C5 H5 119.8 . . ?
C12 C5 H5 119.8 . . ?
N1 C10 C1 118.83(10) . . ?
N1 C10 C11 122.12(10) . . ?
C1 C10 C11 119.05(10) . . ?
C5 C11 C4 123.30(10) . . ?
C5 C11 C10 118.09(10) . . ?
C4 C11 C10 118.61(10) . . ?
C18 C19 C14 120.50(10) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C8 C9 C13 120.19(11) . . ?
C8 C9 H9 119.9 . . ?
C13 C9 H9 119.9 . . ?
C3 C4 C11 120.83(11) . . ?
C3 C4 H4 119.6 . . ?
C11 C4 H4 119.6 . . ?
C2 C1 C10 120.10(11) . . ?
C2 C1 H1A 120.0 . . ?
C10 C1 H1A 120.0 . . ?
C4 C3 C2 120.30(11) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C17 C18 C19 119.23(11) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C1 C2 C3 121.11(11) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C18 C17 C16 121.00(11) . . ?
C18 C17 Cl2 120.06(9) . . ?
C16 C17 Cl2 118.94(9) . . ?
C16 C15 C14 120.25(11) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.62(11) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C7 C6 C12 120.50(12) . . ?
C7 C6 H6 119.7 . . ?
C12 C6 H6 119.7 . . ?
C9 C8 C7 120.99(11) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C6 C7 C8 120.52(11) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?

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
C10 N1 C13 C9 -178.30(10) . . . . ?
C10 N1 C13 C12 2.12(15) . . . . ?
N1 C13 C12 C5 -0.94(16) . . . . ?
C9 C13 C12 C5 179.47(10) . . . . ?
N1 C13 C12 C6 179.20(10) . . . . ?
C9 C13 C12 C6 -0.39(16) . . . . ?
C6 C12 C5 C11 179.00(10) . . . . ?
C13 C12 C5 C11 -0.84(16) . . . . ?
C13 N1 C10 C1 178.74(10) . . . . ?
C13 N1 C10 C11 -1.53(15) . . . . ?
C12 C5 C11 C4 -178.72(10) . . . . ?
C12 C5 C11 C10 1.38(16) . . . . ?
N1 C10 C11 C5 -0.19(15) . . . . ?
C1 C10 C11 C5 179.53(10) . . . . ?
N1 C10 C11 C4 179.90(9) . . . . ?
C1 C10 C11 C4 -0.37(15) . . . . ?
O1 C14 C19 C18 -179.79(10) . . . . ?
C15 C14 C19 C18 0.44(17) . . . . ?
N1 C13 C9 C8 -179.55(10) . . . . ?
C12 C13 C9 C8 0.05(17) . . . . ?
C5 C11 C4 C3 -179.52(11) . . . . ?
C10 C11 C4 C3 0.37(16) . . . . ?
N1 C10 C1 C2 -179.81(10) . . . . ?
C11 C10 C1 C2 0.46(16) . . . . ?
C11 C4 C3 C2 -0.45(17) . . . . ?
C14 C19 C18 C17 -0.28(17) . . . . ?
C10 C1 C2 C3 -0.53(18) . . . . ?
C4 C3 C2 C1 0.53(18) . . . . ?
C19 C18 C17 C16 -0.24(18) . . . . ?
C19 C18 C17 Cl2 179.26(8) . . . . ?
O1 C14 C15 C16 -179.87(11) . . . . ?
C19 C14 C15 C16 -0.10(18) . . . . ?
C18 C17 C16 C15 0.59(19) . . . . ?
Cl2 C17 C16 C15 -178.92(10) . . . . ?
C14 C15 C16 C17 -0.42(19) . . . . ?
C5 C12 C6 C7 -179.57(11) . . . . ?
C13 C12 C6 C7 0.28(17) . . . . ?
C13 C9 C8 C7 0.40(18) . . . . ?
C12 C6 C7 C8 0.17(18) . . . . ?
C9 C8 C7 C6 -0.52(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_mo_2016050_0m
_database_code_depnum_ccdc_archive 'CCDC 1588640'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 I N O'
_chemical_formula_weight         399.21

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_cell_measurement_reflns_used    5223
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.25
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                   7.3010(3)
_cell_length_b                   25.9817(10)
_cell_length_c                   9.1022(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.488(2)
_cell_angle_gamma                90.00
_cell_volume                     1606.61(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    1.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13402
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         26.58
_reflns_number_total             3348
_reflns_number_gt                2775
_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)+(0.0180P)²+1.4546P] 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         3348
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0592
_refine_ls_wR_factor_gt          0.0549
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
I1 I 0.89337(3) 0.770217(7) 1.05336(3) 0.04659(8) Uani 1 1 d . . .
O1 O 0.1670(3) 0.62714(8) 0.7519(2) 0.0388(5) Uani 1 1 d . . .
H1 H 0.1876 0.6052 0.6950 0.058 Uiso 1 1 calc R . .
N1 N 0.2264(3) 0.55236(8) 0.5659(2) 0.0290(5) Uani 1 1 d . . .
C13 C 0.1983(3) 0.56309(10) 0.4141(3) 0.0292(5) Uani 1 1 d . . .
C17 C 0.6551(4) 0.71992(10) 0.9560(3) 0.0332(6) Uani 1 1 d . . .
C15 C 0.5056(4) 0.64743(10) 0.7938(3) 0.0324(6) Uani 1 1 d . . .
H15 H 0.5136 0.6201 0.7304 0.039 Uiso 1 1 calc R . .
C14 C 0.3318(4) 0.65624(10) 0.8189(3) 0.0304(6) Uani 1 1 d . . .
C10 C 0.2643(3) 0.50338(10) 0.6166(3) 0.0305(6) Uani 1 1 d . . .
C12 C 0.2036(4) 0.52438(10) 0.3040(3) 0.0325(6) Uani 1 1 d . . .
C16 C 0.6667(4) 0.67897(10) 0.8627(3) 0.0336(6) Uani 1 1 d . . .
H16 H 0.7831 0.6727 0.8462 0.040 Uiso 1 1 calc R . .
C9 C 0.1601(4) 0.61485(11) 0.3605(3) 0.0382(6) Uani 1 1 d . . .
H9 H 0.1557 0.6406 0.4302 0.046 Uiso 1 1 calc R . .
C6 C 0.1721(4) 0.53925(13) 0.1464(3) 0.0422(7) Uani 1 1 d . . .
H6 H 0.1761 0.5145 0.0739 0.051 Uiso 1 1 calc R . .
C1 C 0.2976(4) 0.49212(12) 0.7780(3) 0.0400(7) Uani 1 1 d . . .
H1A H 0.2937 0.5184 0.8461 0.048 Uiso 1 1 calc R . .
C5 C 0.2397(4) 0.47410(11) 0.3588(3) 0.0361(6) Uani 1 1 d . . .
H5 H 0.2424 0.4480 0.2897 0.043 Uiso 1 1 calc R . .
C18 C 0.4831(4) 0.72851(11) 0.9835(3) 0.0397(6) Uani 1 1 d . . .
H18 H 0.4760 0.7556 1.0478 0.048 Uiso 1 1 calc R . .
C19 C 0.3222(4) 0.69689(11) 0.9154(3) 0.0379(6) Uani 1 1 d . . .
H19 H 0.2070 0.7028 0.9341 0.046 Uiso 1 1 calc R . .
C11 C 0.2718(4) 0.46216(10) 0.5150(3) 0.0344(6) Uani 1 1 d . . .
C7 C 0.1364(4) 0.58881(14) 0.1005(3) 0.0491(8) Uani 1 1 d . . .
H7 H 0.1159 0.5979 -0.0032 0.059 Uiso 1 1 calc R . .
C8 C 0.1302(4) 0.62691(13) 0.2088(4) 0.0478(7) Uani 1 1 d . . .
H8 H 0.1051 0.6609 0.1755 0.057 Uiso 1 1 calc R . .
C4 C 0.3107(4) 0.41142(11) 0.5781(4) 0.0484(8) Uani 1 1 d . . .
H4 H 0.3150 0.3842 0.5130 0.058 Uiso 1 1 calc R . .
C3 C 0.3416(4) 0.40238(13) 0.7316(5) 0.0558(9) Uani 1 1 d . . .
H3 H 0.3674 0.3691 0.7713 0.067 Uiso 1 1 calc R . .
C2 C 0.3348(4) 0.44318(13) 0.8321(4) 0.0511(8) Uani 1 1 d . . .
H2 H 0.3563 0.4363 0.9374 0.061 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
I1 C17 2.095(3) . ?
O1 C14 1.361(3) . ?
O1 H1 0.8200 . ?
N1 C10 1.347(3) . ?
N1 C13 1.349(3) . ?
C13 C9 1.423(4) . ?
C13 C12 1.430(3) . ?
C17 C16 1.383(4) . ?
C17 C18 1.386(4) . ?
C15 C16 1.381(4) . ?
C15 C14 1.388(3) . ?
C15 H15 0.9300 . ?
C14 C19 1.392(4) . ?
C10 C11 1.429(4) . ?
C10 C1 1.429(4) . ?
C12 C5 1.388(4) . ?
C12 C6 1.421(4) . ?
C16 H16 0.9300 . ?
C9 C8 1.353(4) . ?
C9 H9 0.9300 . ?
C6 C7 1.349(4) . ?
C6 H6 0.9300 . ?
C1 C2 1.355(4) . ?
C1 H1A 0.9300 . ?
C5 C11 1.389(4) . ?
C5 H5 0.9300 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C11 C4 1.425(4) . ?
C7 C8 1.410(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C4 C3 1.352(5) . ?
C4 H4 0.9300 . ?
C3 C2 1.413(5) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?

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
C14 O1 H1 109.5 . . ?
C10 N1 C13 118.8(2) . . ?
N1 C13 C9 118.9(2) . . ?
N1 C13 C12 122.6(2) . . ?
C9 C13 C12 118.5(2) . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 I1 120.78(19) . . ?
C18 C17 I1 119.36(19) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O1 C14 C15 123.1(2) . . ?
O1 C14 C19 117.7(2) . . ?
C15 C14 C19 119.3(2) . . ?
N1 C10 C11 122.5(2) . . ?
N1 C10 C1 118.8(2) . . ?
C11 C10 C1 118.7(2) . . ?
C5 C12 C6 123.9(2) . . ?
C5 C12 C13 117.4(2) . . ?
C6 C12 C13 118.7(3) . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C8 C9 C13 120.5(3) . . ?
C8 C9 H9 119.8 . . ?
C13 C9 H9 119.8 . . ?
C7 C6 C12 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
C12 C6 H6 119.5 . . ?
C2 C1 C10 120.1(3) . . ?
C2 C1 H1A 119.9 . . ?
C10 C1 H1A 119.9 . . ?
C12 C5 C11 121.1(2) . . ?
C12 C5 H5 119.5 . . ?
C11 C5 H5 119.5 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C5 C11 C4 123.6(3) . . ?
C5 C11 C10 117.6(2) . . ?
C4 C11 C10 118.8(3) . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C3 C4 C11 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C11 C4 H4 119.6 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C1 C2 C3 121.2(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 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
C10 N1 C13 C9 -179.4(2) . . . . ?
C10 N1 C13 C12 1.1(3) . . . . ?
C16 C15 C14 O1 178.7(2) . . . . ?
C16 C15 C14 C19 -0.6(4) . . . . ?
C13 N1 C10 C11 -1.3(3) . . . . ?
C13 N1 C10 C1 178.9(2) . . . . ?
N1 C13 C12 C5 -0.1(4) . . . . ?
C9 C13 C12 C5 -179.6(2) . . . . ?
N1 C13 C12 C6 179.9(2) . . . . ?
C9 C13 C12 C6 0.5(3) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C18 C17 C16 C15 1.6(4) . . . . ?
I1 C17 C16 C15 -177.26(19) . . . . ?
N1 C13 C9 C8 -179.6(2) . . . . ?
C12 C13 C9 C8 -0.2(4) . . . . ?
C5 C12 C6 C7 179.6(3) . . . . ?
C13 C12 C6 C7 -0.4(4) . . . . ?
N1 C10 C1 C2 179.6(2) . . . . ?
C11 C10 C1 C2 -0.2(4) . . . . ?
C6 C12 C5 C11 179.2(2) . . . . ?
C13 C12 C5 C11 -0.8(4) . . . . ?
C16 C17 C18 C19 -1.2(4) . . . . ?
I1 C17 C18 C19 177.6(2) . . . . ?
C17 C18 C19 C14 0.0(4) . . . . ?
O1 C14 C19 C18 -178.4(2) . . . . ?
C15 C14 C19 C18 0.9(4) . . . . ?
C12 C5 C11 C4 -179.6(2) . . . . ?
C12 C5 C11 C10 0.7(4) . . . . ?
N1 C10 C11 C5 0.4(4) . . . . ?
C1 C10 C11 C5 -179.8(2) . . . . ?
N1 C10 C11 C4 -179.3(2) . . . . ?
C1 C10 C11 C4 0.5(4) . . . . ?
C12 C6 C7 C8 0.1(4) . . . . ?
C13 C9 C8 C7 -0.2(4) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C5 C11 C4 C3 179.7(3) . . . . ?
C10 C11 C4 C3 -0.5(4) . . . . ?
C11 C4 C3 C2 0.3(4) . . . . ?
C10 C1 C2 C3 0.0(4) . . . . ?
C4 C3 C2 C1 0.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_mo_2016039_0m
_database_code_depnum_ccdc_archive 'CCDC 1588638'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 Br N O'
_chemical_formula_weight         352.22

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   '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                   7.1573(4)
_cell_length_b                   24.8433(14)
_cell_length_c                   9.0381(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.491(3)
_cell_angle_gamma                90.00
_cell_volume                     1524.11(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7556
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.41


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    2.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12989
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.43
_reflns_number_total             3459
_reflns_number_gt                3046
_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)+(0.0493P)²+0.5861P] 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       0.0105(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3459
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.86583(3) 0.230093(7) 1.05403(2) 0.02399(10) Uani 1 1 d . . .
O1 O 0.1476(2) 0.36489(5) 0.74117(16) 0.0198(3) Uani 1 1 d . . .
H1 H 0.1728 0.3890 0.6885 0.030 Uiso 1 1 calc R . .
N1 N 0.2202(2) 0.44401(6) 0.55975(18) 0.0152(3) Uani 1 1 d . . .
C13 C 0.2632(3) 0.49480(7) 0.6121(2) 0.0153(4) Uani 1 1 d . . .
C14 C 0.3140(3) 0.33619(7) 0.8116(2) 0.0160(4) Uani 1 1 d . . .
C18 C 0.6610(3) 0.31824(8) 0.8687(2) 0.0192(4) Uani 1 1 d . . .
H18 H 0.7823 0.3269 0.8575 0.023 Uiso 1 1 calc R . .
C10 C 0.1918(3) 0.43308(7) 0.4081(2) 0.0149(4) Uani 1 1 d . . .
C19 C 0.4963(3) 0.34916(8) 0.7958(2) 0.0179(4) Uani 1 1 d . . .
H19 H 0.5074 0.3787 0.7360 0.022 Uiso 1 1 calc R . .
C11 C 0.2012(3) 0.47430(8) 0.2994(2) 0.0164(4) Uani 1 1 d . . .
C12 C 0.2746(3) 0.53825(7) 0.5112(2) 0.0177(4) Uani 1 1 d . . .
C5 C 0.2417(3) 0.52657(8) 0.3547(2) 0.0186(4) Uani 1 1 d . . .
H5 H 0.2468 0.5540 0.2863 0.022 Uiso 1 1 calc R . .
C17 C 0.6440(3) 0.27448(7) 0.9580(2) 0.0188(4) Uani 1 1 d . . .
C9 C 0.2980(3) 0.50570(9) 0.7734(2) 0.0214(4) Uani 1 1 d . . .
H9 H 0.2916 0.4779 0.8406 0.026 Uiso 1 1 calc R . .
C4 C 0.1688(3) 0.45937(9) 0.1405(2) 0.0226(4) Uani 1 1 d . . .
H4 H 0.1748 0.4855 0.0685 0.027 Uiso 1 1 calc R . .
C16 C 0.4640(3) 0.26135(8) 0.9761(3) 0.0238(4) Uani 1 1 d . . .
H16 H 0.4538 0.2320 1.0368 0.029 Uiso 1 1 calc R . .
C15 C 0.2994(3) 0.29240(8) 0.9029(2) 0.0222(4) Uani 1 1 d . . .
H15 H 0.1786 0.2838 0.9150 0.027 Uiso 1 1 calc R . .
C1 C 0.1502(3) 0.37923(8) 0.3540(2) 0.0204(4) Uani 1 1 d . . .
H1A H 0.1427 0.3522 0.4231 0.025 Uiso 1 1 calc R . .
C3 C 0.1294(3) 0.40777(9) 0.0933(2) 0.0262(5) Uani 1 1 d . . .
H3 H 0.1074 0.3988 -0.0107 0.031 Uiso 1 1 calc R . .
C8 C 0.3405(3) 0.55656(9) 0.8297(3) 0.0276(5) Uani 1 1 d . . .
H8 H 0.3629 0.5631 0.9352 0.033 Uiso 1 1 calc R . .
C6 C 0.3201(3) 0.59100(8) 0.5761(3) 0.0250(4) Uani 1 1 d . . .
H6 H 0.3284 0.6195 0.5119 0.030 Uiso 1 1 calc R . .
C2 C 0.1214(3) 0.36717(9) 0.2016(3) 0.0263(5) Uani 1 1 d . . .
H2 H 0.0960 0.3318 0.1677 0.032 Uiso 1 1 calc R . .
C7 C 0.3511(3) 0.59989(9) 0.7296(3) 0.0295(5) Uani 1 1 d . . .
H7 H 0.3796 0.6345 0.7700 0.035 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
Br1 C17 1.9018(19) . ?
O1 C14 1.361(2) . ?
O1 H1 0.8200 . ?
N1 C13 1.348(2) . ?
N1 C10 1.347(2) . ?
C13 C9 1.425(3) . ?
C13 C12 1.432(3) . ?
C14 C15 1.389(3) . ?
C14 C19 1.395(3) . ?
C18 C17 1.383(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9300 . ?
C10 C1 1.423(3) . ?
C10 C11 1.436(3) . ?
C19 H19 0.9300 . ?
C11 C5 1.389(3) . ?
C11 C4 1.429(3) . ?
C12 C5 1.388(3) . ?
C12 C6 1.431(3) . ?
C5 H5 0.9300 . ?
C17 C16 1.387(3) . ?
C9 C8 1.360(3) . ?
C9 H9 0.9300 . ?
C4 C3 1.352(3) . ?
C4 H4 0.9300 . ?
C16 C15 1.388(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C1 C2 1.360(3) . ?
C1 H1A 0.9300 . ?
C3 C2 1.419(3) . ?
C3 H3 0.9300 . ?
C8 C7 1.423(3) . ?
C8 H8 0.9300 . ?
C6 C7 1.352(3) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?

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
C14 O1 H1 109.5 . . ?
C13 N1 C10 119.30(16) . . ?
N1 C13 C9 118.89(17) . . ?
N1 C13 C12 122.31(17) . . ?
C9 C13 C12 118.80(17) . . ?
O1 C14 C15 117.95(17) . . ?
O1 C14 C19 122.66(17) . . ?
C15 C14 C19 119.39(18) . . ?
C17 C18 C19 119.59(18) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
N1 C10 C1 119.12(17) . . ?
N1 C10 C11 121.86(17) . . ?
C1 C10 C11 119.02(17) . . ?
C18 C19 C14 120.38(17) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C5 C11 C4 123.59(18) . . ?
C5 C11 C10 118.04(17) . . ?
C4 C11 C10 118.36(18) . . ?
C5 C12 C6 123.53(18) . . ?
C5 C12 C13 117.75(17) . . ?
C6 C12 C13 118.71(18) . . ?
C12 C5 C11 120.72(17) . . ?
C12 C5 H5 119.6 . . ?
C11 C5 H5 119.6 . . ?
C18 C17 C16 120.73(18) . . ?
C18 C17 Br1 120.45(14) . . ?
C16 C17 Br1 118.80(14) . . ?
C8 C9 C13 120.3(2) . . ?
C8 C9 H9 119.8 . . ?
C13 C9 H9 119.8 . . ?
C3 C4 C11 120.92(18) . . ?
C3 C4 H4 119.5 . . ?
C11 C4 H4 119.5 . . ?
C15 C16 C17 119.50(18) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C15 C14 120.40(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C2 C1 C10 120.22(18) . . ?
C2 C1 H1A 119.9 . . ?
C10 C1 H1A 119.9 . . ?
C4 C3 C2 120.45(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C7 C6 C12 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C12 C6 H6 119.6 . . ?
C1 C2 C3 121.02(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C6 C7 C8 120.25(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 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
C10 N1 C13 C9 -178.39(17) . . . . ?
C10 N1 C13 C12 1.8(3) . . . . ?
C13 N1 C10 C1 178.79(17) . . . . ?
C13 N1 C10 C11 -1.6(3) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?
O1 C14 C19 C18 -179.29(17) . . . . ?
C15 C14 C19 C18 0.9(3) . . . . ?
N1 C10 C11 C5 0.3(3) . . . . ?
C1 C10 C11 C5 179.91(18) . . . . ?
N1 C10 C11 C4 -179.81(17) . . . . ?
C1 C10 C11 C4 -0.2(3) . . . . ?
N1 C13 C12 C5 -0.7(3) . . . . ?
C9 C13 C12 C5 179.50(18) . . . . ?
N1 C13 C12 C6 179.67(18) . . . . ?
C9 C13 C12 C6 -0.2(3) . . . . ?
C6 C12 C5 C11 178.97(19) . . . . ?
C13 C12 C5 C11 -0.7(3) . . . . ?
C4 C11 C5 C12 -179.06(18) . . . . ?
C10 C11 C5 C12 0.9(3) . . . . ?
C19 C18 C17 C16 -0.3(3) . . . . ?
C19 C18 C17 Br1 178.08(14) . . . . ?
N1 C13 C9 C8 -179.59(18) . . . . ?
C12 C13 C9 C8 0.2(3) . . . . ?
C5 C11 C4 C3 -179.8(2) . . . . ?
C10 C11 C4 C3 0.3(3) . . . . ?
C18 C17 C16 C15 0.3(3) . . . . ?
Br1 C17 C16 C15 -178.08(16) . . . . ?
C17 C16 C15 C14 0.2(3) . . . . ?
O1 C14 C15 C16 179.30(19) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?
N1 C10 C1 C2 -179.87(18) . . . . ?
C11 C10 C1 C2 0.5(3) . . . . ?
C11 C4 C3 C2 -0.6(3) . . . . ?
C13 C9 C8 C7 0.0(3) . . . . ?
C5 C12 C6 C7 -179.8(2) . . . . ?
C13 C12 C6 C7 -0.2(3) . . . . ?
C10 C1 C2 C3 -0.9(3) . . . . ?
C4 C3 C2 C1 0.9(3) . . . . ?
C12 C6 C7 C8 0.5(3) . . . . ?
C9 C8 C7 C6 -0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_mo_2016417_0m
_database_code_depnum_ccdc_archive 'CCDC 1588637'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
_audit_creation_date             2017-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 Cl O, 2(C13 H9 N)'
_chemical_formula_sum            'C32 H23 Cl N2 O'
_chemical_formula_weight         486.97
_chemical_absolute_configuration .
_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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.8719(4)
_cell_length_b                   14.5519(4)
_cell_length_c                   14.2914(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.4000(10)
_cell_angle_gamma                90
_cell_volume                     2418.17(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0777 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.9336. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14308
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.577
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                7286
_reflns_number_total             8184
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2986 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         8184
_refine_ls_number_restraints     1233
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.2180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1104
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C56, C64
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C56 \\sim C64: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9),
 C15(H15), C16(H16), C18(H18), C19(H19), C34(H34), C35(H35), C37(H37), C38(H38),
  C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44),
  C45(H45), C46(H46), C47(H47), C52(H52), C53(H53), C54(H54), C55(H55),
 C56(H56), C57(H57), C58(H58), C59(H59), C60(H60)
5.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.11735(8) 0.66014(8) 0.07397(7) 0.0437(3) Uani 1 1 d . U . . .
O1 O 0.8318(2) 0.94887(19) 0.1331(2) 0.0409(6) Uani 1 1 d . U . . .
H1A H 0.7936 0.9286 0.1638 0.061 Uiso 1 1 calc GR . . . .
N1 N 0.6936(2) 0.88186(19) 0.2191(2) 0.0253(6) Uani 1 1 d . U . . .
C1 C 0.5317(3) 0.8872(3) 0.0544(3) 0.0331(8) Uani 1 1 d . U . . .
H1 H 0.5779 0.9150 0.0254 0.040 Uiso 1 1 calc R . . . .
C2 C 0.4192(3) 0.8712(3) -0.0060(3) 0.0413(9) Uani 1 1 d . U . . .
H2 H 0.3870 0.8888 -0.0768 0.050 Uiso 1 1 calc R . . . .
C3 C 0.3487(3) 0.8285(3) 0.0346(3) 0.0440(10) Uani 1 1 d . U . . .
H3 H 0.2700 0.8170 -0.0093 0.053 Uiso 1 1 calc R . . . .
C4 C 0.3924(3) 0.8040(3) 0.1354(3) 0.0337(8) Uani 1 1 d . U . . .
H4 H 0.3439 0.7759 0.1618 0.040 Uiso 1 1 calc R . . . .
C5 C 0.5626(3) 0.7949(2) 0.3067(3) 0.0281(7) Uani 1 1 d . U . . .
H5 H 0.5181 0.7652 0.3363 0.034 Uiso 1 1 calc R . . . .
C6 C 0.7350(3) 0.7895(3) 0.4748(3) 0.0378(9) Uani 1 1 d . U . . .
H6 H 0.6942 0.7585 0.5072 0.045 Uiso 1 1 calc R . . . .
C7 C 0.8468(4) 0.8111(3) 0.5303(3) 0.0446(10) Uani 1 1 d . U . . .
H7 H 0.8839 0.7955 0.6017 0.054 Uiso 1 1 calc R . . . .
C8 C 0.9093(3) 0.8567(3) 0.4836(3) 0.0452(10) Uani 1 1 d . U . . .
H8 H 0.9877 0.8719 0.5243 0.054 Uiso 1 1 calc R . . . .
C9 C 0.8594(3) 0.8791(3) 0.3817(3) 0.0358(8) Uani 1 1 d . U . . .
H9 H 0.9030 0.9089 0.3513 0.043 Uiso 1 1 calc R . . . .
C10 C 0.5814(3) 0.8629(2) 0.1608(2) 0.0244(7) Uani 1 1 d . U . . .
C11 C 0.5110(3) 0.8198(2) 0.2028(3) 0.0253(7) Uani 1 1 d . U . . .
C12 C 0.6777(3) 0.8128(2) 0.3678(2) 0.0271(7) Uani 1 1 d . U . . .
C13 C 0.7415(3) 0.8579(2) 0.3203(2) 0.0255(7) Uani 1 1 d . U . . .
C14 C 0.8954(3) 0.8799(3) 0.1202(2) 0.0295(8) Uani 1 1 d . U . . .
C15 C 0.9737(3) 0.9020(3) 0.0799(2) 0.0322(8) Uani 1 1 d . U . . .
H15 H 0.9809 0.9638 0.0623 0.039 Uiso 1 1 calc R . . . .
C16 C 1.0405(3) 0.8345(3) 0.0654(2) 0.0326(8) Uani 1 1 d . U . . .
H16 H 1.0936 0.8498 0.0379 0.039 Uiso 1 1 calc R . . . .
C17 C 1.0301(3) 0.7446(3) 0.0910(2) 0.0315(8) Uani 1 1 d . U . . .
C18 C 0.9519(3) 0.7213(3) 0.1296(3) 0.0326(8) Uani 1 1 d . U . . .
H18 H 0.9442 0.6591 0.1458 0.039 Uiso 1 1 calc R . . . .
C19 C 0.8848(3) 0.7888(3) 0.1444(2) 0.0303(8) Uani 1 1 d . U . . .
H19 H 0.8313 0.7729 0.1712 0.036 Uiso 1 1 calc R . . . .
Cl2 Cl 1.02704(7) 0.45734(8) 0.16825(7) 0.0408(2) Uani 1 1 d . U . . .
O2 O 0.7498(2) 0.19624(19) 0.2790(2) 0.0440(7) Uani 1 1 d . U . . .
H2A H 0.7107 0.2240 0.3044 0.066 Uiso 1 1 calc GR . . . .
C33 C 0.8134(3) 0.2585(3) 0.2537(3) 0.0331(8) Uani 1 1 d . U . . .
C34 C 0.8846(3) 0.2256(3) 0.2113(3) 0.0334(8) Uani 1 1 d . U . . .
H34 H 0.8879 0.1615 0.2003 0.040 Uiso 1 1 calc R . . . .
C35 C 0.9512(3) 0.2859(3) 0.1848(2) 0.0318(8) Uani 1 1 d . U . . .
H35 H 1.0005 0.2634 0.1561 0.038 Uiso 1 1 calc R . . . .
C36 C 0.9449(3) 0.3790(3) 0.2004(2) 0.0308(8) Uani 1 1 d . U . . .
C37 C 0.8737(3) 0.4127(3) 0.2425(3) 0.0335(8) Uani 1 1 d . U . . .
H37 H 0.8696 0.4769 0.2524 0.040 Uiso 1 1 calc R . . . .
C38 C 0.8089(3) 0.3524(3) 0.2698(3) 0.0324(8) Uani 1 1 d . U . . .
H38 H 0.7609 0.3750 0.2998 0.039 Uiso 1 1 calc R . . . .
N2 N 0.6212(2) 0.28980(19) 0.3610(2) 0.0262(6) Uani 1 1 d . U . . .
C20 C 0.4646(3) 0.2855(2) 0.1925(3) 0.0317(8) Uani 1 1 d . U . . .
H20 H 0.5138 0.2594 0.1656 0.038 Uiso 1 1 calc R . . . .
C21 C 0.3527(3) 0.3019(3) 0.1283(3) 0.0372(9) Uani 1 1 d . U . . .
H21 H 0.3242 0.2868 0.0569 0.045 Uiso 1 1 calc R . . . .
C22 C 0.2774(3) 0.3414(3) 0.1666(3) 0.0384(9) Uani 1 1 d . U . . .
H22 H 0.1993 0.3526 0.1207 0.046 Uiso 1 1 calc R . . . .
C23 C 0.3167(3) 0.3631(3) 0.2679(3) 0.0330(8) Uani 1 1 d . U . . .
H23 H 0.2656 0.3893 0.2926 0.040 Uiso 1 1 calc R . . . .
C24 C 0.4786(3) 0.3707(2) 0.4419(3) 0.0269(7) Uani 1 1 d . U . . .
H24 H 0.4303 0.3975 0.4694 0.032 Uiso 1 1 calc R . . . .
C25 C 0.6462(3) 0.3803(2) 0.6132(3) 0.0332(8) Uani 1 1 d . U . . .
H25 H 0.6010 0.4082 0.6433 0.040 Uiso 1 1 calc R . . . .
C26 C 0.7598(3) 0.3644(3) 0.6721(3) 0.0422(9) Uani 1 1 d . U . . .
H26 H 0.7937 0.3811 0.7433 0.051 Uiso 1 1 calc R . . . .
C27 C 0.8278(3) 0.3234(3) 0.6281(3) 0.0429(10) Uani 1 1 d . U . . .
H27 H 0.9071 0.3129 0.6704 0.052 Uiso 1 1 calc R . . . .
C28 C 0.7823(3) 0.2984(3) 0.5261(3) 0.0337(8) Uani 1 1 d . U . . .
H28 H 0.8298 0.2713 0.4980 0.040 Uiso 1 1 calc R . . . .
C29 C 0.5086(3) 0.3072(2) 0.2994(2) 0.0246(7) Uani 1 1 d . U . . .
C30 C 0.4336(3) 0.3472(2) 0.3383(2) 0.0245(7) Uani 1 1 d . U . . .
C31 C 0.5944(3) 0.3551(2) 0.5063(2) 0.0255(7) Uani 1 1 d . U . . .
C32 C 0.6635(3) 0.3133(2) 0.4623(2) 0.0253(7) Uani 1 1 d . U . . .
N3 N 0.7646(3) 0.6321(2) 0.2498(3) 0.0364(7) Uani 1 1 d . U . . .
C39 C 0.5961(4) 0.6345(3) 0.0891(3) 0.0433(10) Uani 1 1 d . U . . .
H39 H 0.6392 0.6629 0.0573 0.052 Uiso 1 1 calc R . . . .
C40 C 0.4833(4) 0.6172(3) 0.0320(3) 0.0485(10) Uani 1 1 d . U . . .
H40 H 0.4483 0.6334 -0.0393 0.058 Uiso 1 1 calc R . . . .
C41 C 0.4159(4) 0.5747(3) 0.0776(3) 0.0472(10) Uani 1 1 d . U . . .
H41 H 0.3364 0.5633 0.0371 0.057 Uiso 1 1 calc R . . . .
C42 C 0.4662(3) 0.5508(3) 0.1788(3) 0.0397(9) Uani 1 1 d . U . . .
H42 H 0.4213 0.5218 0.2085 0.048 Uiso 1 1 calc R . . . .
C43 C 0.6407(3) 0.5457(2) 0.3463(3) 0.0332(8) Uani 1 1 d . U . . .
H43 H 0.5991 0.5159 0.3787 0.040 Uiso 1 1 calc R . . . .
C44 C 0.8174(3) 0.5461(3) 0.5111(3) 0.0397(9) Uani 1 1 d . U . . .
H44 H 0.7788 0.5173 0.5469 0.048 Uiso 1 1 calc R . . . .
C45 C 0.9305(3) 0.5673(3) 0.5630(3) 0.0471(10) Uani 1 1 d . U . . .
H45 H 0.9700 0.5536 0.6348 0.057 Uiso 1 1 calc R . . . .
C46 C 0.9899(4) 0.6094(3) 0.5119(4) 0.0482(10) Uani 1 1 d . U . . .
H46 H 1.0692 0.6235 0.5493 0.058 Uiso 1 1 calc R . . . .
C47 C 0.9348(3) 0.6303(3) 0.4092(4) 0.0441(9) Uani 1 1 d . U . . .
H47 H 0.9762 0.6588 0.3757 0.053 Uiso 1 1 calc R . . . .
C48 C 0.6516(3) 0.6113(2) 0.1953(3) 0.0342(8) Uani 1 1 d . U . . .
C49 C 0.5854(3) 0.5681(2) 0.2422(3) 0.0327(8) Uani 1 1 d . U . . .
C50 C 0.7553(3) 0.5662(2) 0.4034(3) 0.0345(8) Uani 1 1 d . U . . .
C51 C 0.8159(3) 0.6098(2) 0.3514(3) 0.0340(8) Uani 1 1 d . U . . .
N4 N 0.5243(3) 0.0538(2) 0.2993(3) 0.0508(9) Uani 1 1 d . U . . .
C52 C 0.2309(3) 0.1236(3) 0.2619(3) 0.0449(10) Uani 1 1 d . U . . .
H52 H 0.1930 0.1476 0.3009 0.054 Uiso 1 1 calc R . . . .
C53 C 0.1696(4) 0.1061(3) 0.1594(4) 0.0529(11) Uani 1 1 d . U . . .
H53 H 0.0893 0.1181 0.1274 0.064 Uiso 1 1 calc R . . . .
C54 C 0.2240(4) 0.0703(3) 0.0997(3) 0.0560(12) Uani 1 1 d . U . . .
H54 H 0.1795 0.0577 0.0283 0.067 Uiso 1 1 calc R . . . .
C55 C 0.3387(4) 0.0538(3) 0.1429(3) 0.0450(10) Uani 1 1 d . U . . .
H55 H 0.3742 0.0310 0.1014 0.054 Uiso 1 1 calc R . . . .
C56 C 0.4088(2) 0.1221(2) 0.4137(2) 0.0183(6) Uani 1 1 d . U . . .
H56 H 0.3704 0.1467 0.4520 0.022 Uiso 1 1 calc R . . . .
C57 C 0.7040(3) 0.0502(3) 0.4628(3) 0.0361(8) Uani 1 1 d . U . . .
H57 H 0.7467 0.0286 0.4271 0.043 Uiso 1 1 calc R . . . .
C58 C 0.7578(3) 0.0627(3) 0.5659(3) 0.0407(9) Uani 1 1 d . U . . .
H58 H 0.8373 0.0487 0.6023 0.049 Uiso 1 1 calc R . . . .
C59 C 0.6959(3) 0.0971(3) 0.6206(3) 0.0399(9) Uani 1 1 d . U . . .
H59 H 0.7346 0.1066 0.6933 0.048 Uiso 1 1 calc R . . . .
C60 C 0.5821(3) 0.1163(2) 0.5697(3) 0.0336(8) Uani 1 1 d . U . . .
H60 H 0.5421 0.1393 0.6073 0.040 Uiso 1 1 calc R . . . .
C61 C 0.3515(3) 0.1061(2) 0.3118(3) 0.0328(8) Uani 1 1 d . U . . .
C62 C 0.4066(3) 0.0706(2) 0.2508(3) 0.0333(8) Uani 1 1 d . U . . .
C63 C 0.5847(3) 0.0686(2) 0.4061(3) 0.0282(7) Uani 1 1 d . U . . .
C64 C 0.5214(3) 0.1025(2) 0.4604(3) 0.0286(7) Uani 1 1 d . U . . .


_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 C17 1.751(4) . ?
O1 H1A 0.8400 . ?
O1 C14 1.357(4) . ?
N1 C10 1.350(4) . ?
N1 C13 1.352(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.350(5) . ?
C1 C10 1.418(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.413(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.350(5) . ?
C4 H4 0.9500 . ?
C4 C11 1.432(5) . ?
C5 H5 0.9500 . ?
C5 C11 1.389(5) . ?
C5 C12 1.384(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.349(6) . ?
C6 C12 1.424(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.411(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.356(5) . ?
C9 H9 0.9500 . ?
C9 C13 1.424(4) . ?
C10 C11 1.429(5) . ?
C12 C13 1.430(5) . ?
C14 C15 1.396(5) . ?
C14 C19 1.391(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(5) . ?
C17 C18 1.380(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(5) . ?
C19 H19 0.9500 . ?
Cl2 C36 1.746(4) . ?
O2 H2A 0.8400 . ?
O2 C33 1.369(5) . ?
C33 C34 1.383(5) . ?
C33 C38 1.391(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.388(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.380(5) . ?
C36 C37 1.383(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.378(5) . ?
C38 H38 0.9500 . ?
N2 C29 1.358(4) . ?
N2 C32 1.354(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.357(5) . ?
C20 C29 1.418(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.422(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.351(5) . ?
C23 H23 0.9500 . ?
C23 C30 1.426(4) . ?
C24 H24 0.9500 . ?
C24 C30 1.382(5) . ?
C24 C31 1.395(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.358(5) . ?
C25 C31 1.428(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.410(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.367(5) . ?
C28 H28 0.9500 . ?
C28 C32 1.421(5) . ?
C29 C30 1.429(5) . ?
C31 C32 1.427(5) . ?
N3 C48 1.358(5) . ?
N3 C51 1.351(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.350(6) . ?
C39 C48 1.413(6) . ?
C40 H40 0.9500 . ?
C40 C41 1.430(6) . ?
C41 H41 0.9500 . ?
C41 C42 1.352(6) . ?
C42 H42 0.9500 . ?
C42 C49 1.431(5) . ?
C43 H43 0.9500 . ?
C43 C49 1.384(5) . ?
C43 C50 1.378(5) . ?
C44 H44 0.9500 . ?
C44 C45 1.356(5) . ?
C44 C50 1.427(5) . ?
C45 H45 0.9500 . ?
C45 C46 1.405(6) . ?
C46 H46 0.9500 . ?
C46 C47 1.363(6) . ?
C47 H47 0.9500 . ?
C47 C51 1.425(5) . ?
C48 C49 1.435(5) . ?
C50 C51 1.435(5) . ?
N4 C62 1.391(5) . ?
N4 C63 1.402(5) . ?
C52 H52 0.9500 . ?
C52 C53 1.357(6) . ?
C52 C61 1.426(5) . ?
C53 H53 0.9500 . ?
C53 C54 1.415(7) . ?
C54 H54 0.9500 . ?
C54 C55 1.355(6) . ?
C55 H55 0.9500 . ?
C55 C62 1.429(5) . ?
C56 H56 0.9500 . ?
C56 C61 1.341(5) . ?
C56 C64 1.341(4) . ?
C57 H57 0.9500 . ?
C57 C58 1.344(5) . ?
C57 C63 1.421(5) . ?
C58 H58 0.9500 . ?
C58 C59 1.425(6) . ?
C59 H59 0.9500 . ?
C59 C60 1.355(5) . ?
C60 H60 0.9500 . ?
C60 C64 1.430(5) . ?
C61 C62 1.435(5) . ?
C63 C64 1.433(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
C14 O1 H1A 109.5 . . ?
C10 N1 C13 118.9(3) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C10 120.6(4) . . ?
C10 C1 H1 119.7 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C11 120.8(4) . . ?
C11 C4 H4 119.6 . . ?
C11 C5 H5 119.4 . . ?
C12 C5 H5 119.4 . . ?
C12 C5 C11 121.2(3) . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C12 120.4(4) . . ?
C12 C6 H6 119.8 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C13 119.9(4) . . ?
C13 C9 H9 120.0 . . ?
N1 C10 C1 118.8(3) . . ?
N1 C10 C11 122.2(3) . . ?
C1 C10 C11 118.9(3) . . ?
C5 C11 C4 124.1(3) . . ?
C5 C11 C10 117.7(3) . . ?
C10 C11 C4 118.2(3) . . ?
C5 C12 C6 123.6(3) . . ?
C5 C12 C13 117.6(3) . . ?
C6 C12 C13 118.7(3) . . ?
N1 C13 C9 118.7(3) . . ?
N1 C13 C12 122.4(3) . . ?
C9 C13 C12 119.0(3) . . ?
O1 C14 C15 118.1(3) . . ?
O1 C14 C19 122.8(3) . . ?
C19 C14 C15 119.1(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 Cl1 119.1(3) . . ?
C18 C17 Cl1 120.3(3) . . ?
C18 C17 C16 120.6(3) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C33 O2 H2A 109.5 . . ?
O2 C33 C34 118.1(3) . . ?
O2 C33 C38 122.3(3) . . ?
C34 C33 C38 119.6(4) . . ?
C33 C34 H34 119.9 . . ?
C33 C34 C35 120.2(3) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.3 . . ?
C36 C35 C34 119.4(3) . . ?
C36 C35 H35 120.3 . . ?
C35 C36 Cl2 120.9(3) . . ?
C35 C36 C37 121.0(4) . . ?
C37 C36 Cl2 118.1(3) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 C36 119.4(3) . . ?
C38 C37 H37 120.3 . . ?
C33 C38 H38 119.8 . . ?
C37 C38 C33 120.4(3) . . ?
C37 C38 H38 119.8 . . ?
C32 N2 C29 118.4(3) . . ?
C21 C20 H20 119.7 . . ?
C21 C20 C29 120.5(3) . . ?
C29 C20 H20 119.7 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C30 121.0(3) . . ?
C30 C23 H23 119.5 . . ?
C30 C24 H24 119.9 . . ?
C30 C24 C31 120.3(3) . . ?
C31 C24 H24 119.9 . . ?
C26 C25 H25 119.9 . . ?
C26 C25 C31 120.3(4) . . ?
C31 C25 H25 119.9 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.3(3) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.6(3) . . ?
C28 C27 H27 119.2 . . ?
C27 C28 H28 120.2 . . ?
C27 C28 C32 119.6(4) . . ?
C32 C28 H28 120.2 . . ?
N2 C29 C20 118.7(3) . . ?
N2 C29 C30 122.3(3) . . ?
C20 C29 C30 119.0(3) . . ?
C23 C30 C29 118.5(3) . . ?
C24 C30 C23 123.1(3) . . ?
C24 C30 C29 118.4(3) . . ?
C24 C31 C25 122.7(3) . . ?
C24 C31 C32 118.1(3) . . ?
C32 C31 C25 119.2(3) . . ?
N2 C32 C28 118.5(3) . . ?
N2 C32 C31 122.5(3) . . ?
C28 C32 C31 119.0(3) . . ?
C51 N3 C48 118.2(3) . . ?
C40 C39 H39 119.3 . . ?
C40 C39 C48 121.5(4) . . ?
C48 C39 H39 119.3 . . ?
C39 C40 H40 119.7 . . ?
C39 C40 C41 120.7(4) . . ?
C41 C40 H40 119.7 . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.6(4) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 119.2 . . ?
C41 C42 C49 121.6(4) . . ?
C49 C42 H42 119.2 . . ?
C49 C43 H43 119.6 . . ?
C50 C43 H43 119.6 . . ?
C50 C43 C49 120.8(3) . . ?
C45 C44 H44 119.4 . . ?
C45 C44 C50 121.1(4) . . ?
C50 C44 H44 119.4 . . ?
C44 C45 H45 119.7 . . ?
C44 C45 C46 120.7(4) . . ?
C46 C45 H45 119.7 . . ?
C45 C46 H46 119.7 . . ?
C47 C46 C45 120.7(4) . . ?
C47 C46 H46 119.7 . . ?
C46 C47 H47 119.7 . . ?
C46 C47 C51 120.7(4) . . ?
C51 C47 H47 119.7 . . ?
N3 C48 C39 119.1(3) . . ?
N3 C48 C49 122.3(3) . . ?
C39 C48 C49 118.6(4) . . ?
C42 C49 C48 118.1(3) . . ?
C43 C49 C42 123.8(3) . . ?
C43 C49 C48 118.0(3) . . ?
C43 C50 C44 123.8(3) . . ?
C43 C50 C51 118.0(3) . . ?
C44 C50 C51 118.1(3) . . ?
N3 C51 C47 118.7(3) . . ?
N3 C51 C50 122.6(3) . . ?
C47 C51 C50 118.7(4) . . ?
C62 N4 C63 119.5(3) . . ?
C53 C52 H52 119.7 . . ?
C53 C52 C61 120.7(4) . . ?
C61 C52 H52 119.7 . . ?
C52 C53 H53 119.6 . . ?
C52 C53 C54 120.7(4) . . ?
C54 C53 H53 119.6 . . ?
C53 C54 H54 119.5 . . ?
C55 C54 C53 121.0(4) . . ?
C55 C54 H54 119.5 . . ?
C54 C55 H55 119.9 . . ?
C54 C55 C62 120.2(4) . . ?
C62 C55 H55 119.9 . . ?
C61 C56 H56 120.8 . . ?
C64 C56 H56 120.8 . . ?
C64 C56 C61 118.4(3) . . ?
C58 C57 H57 119.3 . . ?
C58 C57 C63 121.5(3) . . ?
C63 C57 H57 119.3 . . ?
C57 C58 H58 119.9 . . ?
C57 C58 C59 120.1(3) . . ?
C59 C58 H58 119.9 . . ?
C58 C59 H59 119.7 . . ?
C60 C59 C58 120.5(3) . . ?
C60 C59 H59 119.7 . . ?
C59 C60 H60 119.5 . . ?
C59 C60 C64 121.1(3) . . ?
C64 C60 H60 119.5 . . ?
C52 C61 C62 118.4(3) . . ?
C56 C61 C52 119.0(3) . . ?
C56 C61 C62 122.6(3) . . ?
N4 C62 C55 122.6(4) . . ?
N4 C62 C61 118.5(3) . . ?
C55 C62 C61 119.0(3) . . ?
N4 C63 C57 123.5(3) . . ?
N4 C63 C64 117.6(3) . . ?
C57 C63 C64 118.9(3) . . ?
C56 C64 C60 118.8(3) . . ?
C56 C64 C63 123.3(3) . . ?
C60 C64 C63 117.9(3) . . ?

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
Cl1 C17 C18 C19 178.9(2) . . . . ?
O1 C14 C15 C16 179.9(3) . . . . ?
O1 C14 C19 C18 179.9(3) . . . . ?
N1 C10 C11 C4 178.9(3) . . . . ?
N1 C10 C11 C5 -1.8(5) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C1 C10 C11 C4 -0.8(5) . . . . ?
C1 C10 C11 C5 178.6(3) . . . . ?
C2 C1 C10 N1 -178.6(3) . . . . ?
C2 C1 C10 C11 1.0(5) . . . . ?
C2 C3 C4 C11 -0.6(6) . . . . ?
C3 C4 C11 C5 -178.7(3) . . . . ?
C3 C4 C11 C10 0.6(5) . . . . ?
C5 C12 C13 N1 -1.0(5) . . . . ?
C5 C12 C13 C9 178.6(3) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C6 C12 C13 N1 179.6(3) . . . . ?
C6 C12 C13 C9 -0.8(5) . . . . ?
C7 C6 C12 C5 -178.3(3) . . . . ?
C7 C6 C12 C13 1.1(5) . . . . ?
C7 C8 C9 C13 1.0(6) . . . . ?
C8 C9 C13 N1 179.4(3) . . . . ?
C8 C9 C13 C12 -0.2(5) . . . . ?
C10 N1 C13 C9 -179.2(3) . . . . ?
C10 N1 C13 C12 0.4(5) . . . . ?
C10 C1 C2 C3 -1.1(6) . . . . ?
C11 C5 C12 C6 179.5(3) . . . . ?
C11 C5 C12 C13 0.2(5) . . . . ?
C12 C5 C11 C4 -179.6(3) . . . . ?
C12 C5 C11 C10 1.1(5) . . . . ?
C12 C6 C7 C8 -0.3(6) . . . . ?
C13 N1 C10 C1 -179.3(3) . . . . ?
C13 N1 C10 C11 1.1(5) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C14 C19 C18 0.6(5) . . . . ?
C15 C16 C17 Cl1 -179.0(2) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C16 C17 C18 C19 -1.2(5) . . . . ?
C17 C18 C19 C14 0.3(5) . . . . ?
C19 C14 C15 C16 -0.8(5) . . . . ?
Cl2 C36 C37 C38 -179.2(2) . . . . ?
O2 C33 C34 C35 -179.7(3) . . . . ?
O2 C33 C38 C37 -179.5(3) . . . . ?
C33 C34 C35 C36 -0.5(5) . . . . ?
C34 C33 C38 C37 0.9(5) . . . . ?
C34 C35 C36 Cl2 180.0(2) . . . . ?
C34 C35 C36 C37 0.3(5) . . . . ?
C35 C36 C37 C38 0.5(5) . . . . ?
C36 C37 C38 C33 -1.1(5) . . . . ?
C38 C33 C34 C35 -0.1(5) . . . . ?
N2 C29 C30 C23 179.9(3) . . . . ?
N2 C29 C30 C24 1.5(5) . . . . ?
C20 C21 C22 C23 -0.1(6) . . . . ?
C20 C29 C30 C23 0.5(5) . . . . ?
C20 C29 C30 C24 -177.9(3) . . . . ?
C21 C20 C29 N2 -179.9(3) . . . . ?
C21 C20 C29 C30 -0.5(5) . . . . ?
C21 C22 C23 C30 0.1(6) . . . . ?
C22 C23 C30 C24 178.0(3) . . . . ?
C22 C23 C30 C29 -0.3(5) . . . . ?
C24 C31 C32 N2 1.1(5) . . . . ?
C24 C31 C32 C28 178.8(3) . . . . ?
C25 C26 C27 C28 -0.1(6) . . . . ?
C25 C31 C32 N2 -178.2(3) . . . . ?
C25 C31 C32 C28 -0.5(5) . . . . ?
C26 C25 C31 C24 -179.3(3) . . . . ?
C26 C25 C31 C32 0.0(5) . . . . ?
C26 C27 C28 C32 -0.4(6) . . . . ?
C27 C28 C32 N2 178.5(3) . . . . ?
C27 C28 C32 C31 0.7(5) . . . . ?
C29 N2 C32 C28 -177.6(3) . . . . ?
C29 N2 C32 C31 0.1(5) . . . . ?
C29 C20 C21 C22 0.3(6) . . . . ?
C30 C24 C31 C25 178.3(3) . . . . ?
C30 C24 C31 C32 -1.0(5) . . . . ?
C31 C24 C30 C23 -178.6(3) . . . . ?
C31 C24 C30 C29 -0.2(5) . . . . ?
C31 C25 C26 C27 0.3(6) . . . . ?
C32 N2 C29 C20 178.0(3) . . . . ?
C32 N2 C29 C30 -1.4(5) . . . . ?
N3 C48 C49 C42 178.7(3) . . . . ?
N3 C48 C49 C43 -1.3(5) . . . . ?
C39 C40 C41 C42 -0.7(6) . . . . ?
C39 C48 C49 C42 -0.1(5) . . . . ?
C39 C48 C49 C43 180.0(3) . . . . ?
C40 C39 C48 N3 -178.5(3) . . . . ?
C40 C39 C48 C49 0.3(6) . . . . ?
C40 C41 C42 C49 0.9(6) . . . . ?
C41 C42 C49 C43 179.5(4) . . . . ?
C41 C42 C49 C48 -0.5(6) . . . . ?
C43 C50 C51 N3 0.7(5) . . . . ?
C43 C50 C51 C47 -179.2(3) . . . . ?
C44 C45 C46 C47 0.4(6) . . . . ?
C44 C50 C51 N3 -179.7(3) . . . . ?
C44 C50 C51 C47 0.5(5) . . . . ?
C45 C44 C50 C43 179.5(4) . . . . ?
C45 C44 C50 C51 -0.1(6) . . . . ?
C45 C46 C47 C51 0.0(6) . . . . ?
C46 C47 C51 N3 179.7(3) . . . . ?
C46 C47 C51 C50 -0.4(6) . . . . ?
C48 N3 C51 C47 179.3(3) . . . . ?
C48 N3 C51 C50 -0.6(5) . . . . ?
C48 C39 C40 C41 0.1(6) . . . . ?
C49 C43 C50 C44 179.3(3) . . . . ?
C49 C43 C50 C51 -1.1(5) . . . . ?
C50 C43 C49 C42 -178.6(3) . . . . ?
C50 C43 C49 C48 1.4(5) . . . . ?
C50 C44 C45 C46 -0.3(6) . . . . ?
C51 N3 C48 C39 179.6(3) . . . . ?
C51 N3 C48 C49 0.9(5) . . . . ?
N4 C63 C64 C56 -1.2(5) . . . . ?
N4 C63 C64 C60 179.0(3) . . . . ?
C52 C53 C54 C55 -1.0(7) . . . . ?
C52 C61 C62 N4 179.8(3) . . . . ?
C52 C61 C62 C55 -0.3(5) . . . . ?
C53 C52 C61 C56 -178.4(4) . . . . ?
C53 C52 C61 C62 0.6(6) . . . . ?
C53 C54 C55 C62 1.3(6) . . . . ?
C54 C55 C62 N4 179.2(4) . . . . ?
C54 C55 C62 C61 -0.7(6) . . . . ?
C56 C61 C62 N4 -1.2(5) . . . . ?
C56 C61 C62 C55 178.8(3) . . . . ?
C57 C58 C59 C60 0.9(6) . . . . ?
C57 C63 C64 C56 179.8(3) . . . . ?
C57 C63 C64 C60 0.0(5) . . . . ?
C58 C57 C63 N4 -178.0(3) . . . . ?
C58 C57 C63 C64 1.0(6) . . . . ?
C58 C59 C60 C64 0.1(6) . . . . ?
C59 C60 C64 C56 179.7(3) . . . . ?
C59 C60 C64 C63 -0.5(5) . . . . ?
C61 C52 C53 C54 0.0(7) . . . . ?
C61 C56 C64 C60 -177.8(3) . . . . ?
C61 C56 C64 C63 2.4(5) . . . . ?
C62 N4 C63 C57 177.7(3) . . . . ?
C62 N4 C63 C64 -1.3(5) . . . . ?
C63 N4 C62 C55 -177.6(3) . . . . ?
C63 N4 C62 C61 2.4(5) . . . . ?
C63 C57 C58 C59 -1.4(6) . . . . ?
C64 C56 C61 C52 177.8(3) . . . . ?
C64 C56 C61 C62 -1.2(5) . . . . ?

_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/access/V1 
# 
# Audit and citation data items may have 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_mm
_database_code_depnum_ccdc_archive 'CCDC 1588639'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
_audit_creation_date             2016-08-31
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 Br O, 2(C13 H9 N)'
_chemical_formula_sum            'C32 H23 Br N2 O'
_chemical_formula_weight         531.43
_chemical_absolute_configuration .
_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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.0192(2)
_cell_length_b                   14.6232(3)
_cell_length_c                   14.2369(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.2880(10)
_cell_angle_gamma                90
_cell_volume                     2450.72(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6871
_cell_measurement_temperature    170
_cell_measurement_theta_max      22.07
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.706
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0810 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.8888.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0932
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35552
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.572
_diffrn_reflns_theta_min         1.582
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7934
_reflns_number_total             11088
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.001(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     666
_refine_ls_number_reflns         11088
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0166P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0796
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.001(9) -0.001(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Riding coordinates:
 O1(H1A), O2(H2A)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C34(H34), C35(H35), C37(H37),
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C44(H44), C45(H45), C46(H46),
  C47(H47), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
 C27(H27), C28(H28), C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8),
 C9(H9), C52(H52), C53(H53), C54(H54), C55(H55), C57(H57), C58(H58), C59(H59),
 C60(H60)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.12466(4) 0.40597(4) 0.57540(4) 0.03789(15) Uani 1 1 d . . . . .
O1 O 0.8314(3) 0.6983(3) 0.6368(3) 0.0407(9) Uani 1 1 d . . . . .
H1A H 0.7926 0.6778 0.6646 0.061 Uiso 1 1 d R . . . .
C14 C 0.8941(4) 0.6294(4) 0.6224(4) 0.0301(12) Uani 1 1 d . . . . .
C15 C 0.8852(4) 0.5384(4) 0.6468(4) 0.0313(13) Uani 1 1 d . . . . .
H15 H 0.8330 0.5219 0.6743 0.038 Uiso 1 1 calc R . . . .
C16 C 0.9515(4) 0.4721(4) 0.6313(4) 0.0303(13) Uani 1 1 d . . . . .
H16 H 0.9440 0.4100 0.6469 0.036 Uiso 1 1 calc R . . . .
C17 C 1.0283(4) 0.4958(4) 0.5934(3) 0.0273(12) Uani 1 1 d . . . . .
C18 C 1.0383(4) 0.5861(4) 0.5688(4) 0.0316(13) Uani 1 1 d . . . . .
H18 H 1.0912 0.6023 0.5419 0.038 Uiso 1 1 calc R . . . .
C19 C 0.9714(4) 0.6521(4) 0.5834(4) 0.0320(13) Uani 1 1 d . . . . .
H19 H 0.9785 0.7140 0.5667 0.038 Uiso 1 1 calc R . . . .
Br2 Br 1.02528(4) 0.20916(4) 0.67136(4) 0.03681(15) Uani 1 1 d . . . . .
O2 O 0.7411(3) -0.0610(2) 0.7770(3) 0.0419(10) Uani 1 1 d . . . . .
H2A H 0.7076 -0.0352 0.8069 0.063 Uiso 1 1 d R . . . .
C33 C 0.8046(4) 0.0011(4) 0.7532(4) 0.0313(13) Uani 1 1 d . . . . .
C34 C 0.7985(4) 0.0944(4) 0.7690(4) 0.0347(14) Uani 1 1 d . . . . .
H34 H 0.7489 0.1166 0.7970 0.042 Uiso 1 1 calc R . . . .
C35 C 0.8643(4) 0.1547(4) 0.7440(4) 0.0320(13) Uani 1 1 d . . . . .
H35 H 0.8601 0.2184 0.7549 0.038 Uiso 1 1 calc R . . . .
C36 C 0.9355(4) 0.1228(4) 0.7033(4) 0.0283(12) Uani 1 1 d . . . . .
C37 C 0.9416(4) 0.0305(4) 0.6860(4) 0.0298(13) Uani 1 1 d . . . . .
H37 H 0.9907 0.0088 0.6572 0.036 Uiso 1 1 calc R . . . .
C38 C 0.8755(4) -0.0303(4) 0.7110(4) 0.0322(13) Uani 1 1 d . . . . .
H38 H 0.8790 -0.0938 0.6989 0.039 Uiso 1 1 calc R . . . .
N3 N 0.7662(4) 0.3801(3) 0.7513(4) 0.0387(12) Uani 1 1 d . . . . .
C39 C 0.5990(5) 0.3830(4) 0.5913(5) 0.0457(16) Uani 1 1 d . . . . .
H39 H 0.6408 0.4115 0.5586 0.055 Uiso 1 1 calc R . . . .
C40 C 0.4866(6) 0.3653(4) 0.5348(5) 0.0497(16) Uani 1 1 d . . . . .
H40 H 0.4510 0.3821 0.4636 0.060 Uiso 1 1 calc R . . . .
C41 C 0.4219(5) 0.3220(4) 0.5807(5) 0.0468(16) Uani 1 1 d . . . . .
H41 H 0.3433 0.3107 0.5406 0.056 Uiso 1 1 calc R . . . .
C42 C 0.4724(5) 0.2969(4) 0.6819(5) 0.0392(14) Uani 1 1 d . . . . .
H42 H 0.4288 0.2668 0.7117 0.047 Uiso 1 1 calc R . . . .
C43 C 0.6458(5) 0.2922(4) 0.8491(5) 0.0354(14) Uani 1 1 d . . . . .
H43 H 0.607(4) 0.260(4) 0.884(4) 0.047(17) Uiso 1 1 d . . . . .
C44 C 0.8220(5) 0.2913(4) 1.0126(5) 0.0419(15) Uani 1 1 d . . . . .
H44 H 0.7845 0.2612 1.0483 0.050 Uiso 1 1 calc R . . . .
C45 C 0.9342(5) 0.3128(4) 1.0647(5) 0.0499(16) Uani 1 1 d . . . . .
H45 H 0.9740 0.2986 1.1365 0.060 Uiso 1 1 calc R . . . .
C46 C 0.9910(5) 0.3562(4) 1.0123(5) 0.0507(17) Uani 1 1 d . . . . .
H46 H 1.0695 0.3703 1.0489 0.061 Uiso 1 1 calc R . . . .
C47 C 0.9356(5) 0.3781(4) 0.9101(5) 0.0467(16) Uani 1 1 d . . . . .
H47 H 0.9756 0.4075 0.8762 0.056 Uiso 1 1 calc R . . . .
C48 C 0.6554(5) 0.3596(3) 0.6991(4) 0.0368(14) Uani 1 1 d . . . . .
C49 C 0.5908(5) 0.3147(3) 0.7452(4) 0.0322(13) Uani 1 1 d . . . . .
C50 C 0.7605(5) 0.3131(3) 0.9060(4) 0.0355(13) Uani 1 1 d . . . . .
C51 C 0.8167(5) 0.3573(4) 0.8527(5) 0.0389(14) Uani 1 1 d . . . . .
N2 N 0.6169(3) 0.0342(3) 0.8610(3) 0.0257(10) Uani 1 1 d . . . . .
C20 C 0.4621(4) 0.0310(3) 0.6919(4) 0.0314(13) Uani 1 1 d . . . . .
H20 H 0.5099 0.0037 0.6647 0.038 Uiso 1 1 calc R . . . .
C21 C 0.3514(5) 0.0493(4) 0.6281(4) 0.0360(14) Uani 1 1 d . . . . .
H21 H 0.3231 0.0353 0.5562 0.043 Uiso 1 1 calc R . . . .
C22 C 0.2786(4) 0.0880(4) 0.6658(4) 0.0361(13) Uani 1 1 d . . . . .
H22 H 0.2014 0.0988 0.6197 0.043 Uiso 1 1 calc R . . . .
C23 C 0.3168(4) 0.1105(3) 0.7681(4) 0.0325(13) Uani 1 1 d . . . . .
H23 H 0.2665 0.1371 0.7929 0.039 Uiso 1 1 calc R . . . .
C24 C 0.4779(4) 0.1175(3) 0.9425(4) 0.0256(12) Uani 1 1 d . . . . .
H24 H 0.427(3) 0.148(3) 0.969(3) 0.016(12) Uiso 1 1 d . . . . .
C25 C 0.6435(4) 0.1266(3) 1.1129(4) 0.0327(13) Uani 1 1 d . . . . .
H25 H 0.5991 0.1548 1.1432 0.039 Uiso 1 1 calc R . . . .
C26 C 0.7556(5) 0.1110(4) 1.1720(4) 0.0412(15) Uani 1 1 d . . . . .
H26 H 0.7893 0.1284 1.2431 0.049 Uiso 1 1 calc R . . . .
C27 C 0.8217(5) 0.0691(4) 1.1280(4) 0.0402(15) Uani 1 1 d . . . . .
H27 H 0.9000 0.0585 1.1702 0.048 Uiso 1 1 calc R . . . .
C28 C 0.7765(4) 0.0432(3) 1.0264(4) 0.0349(13) Uani 1 1 d . . . . .
H28 H 0.8230 0.0150 0.9983 0.042 Uiso 1 1 calc R . . . .
C29 C 0.5061(4) 0.0530(3) 0.7998(4) 0.0228(11) Uani 1 1 d . . . . .
C30 C 0.4326(4) 0.0939(3) 0.8377(4) 0.0243(11) Uani 1 1 d . . . . .
C31 C 0.5915(4) 0.1013(3) 1.0064(4) 0.0245(11) Uani 1 1 d . . . . .
C32 C 0.6585(4) 0.0589(3) 0.9623(4) 0.0258(12) Uani 1 1 d . . . . .
N1 N 0.6957(3) 0.6290(3) 0.7224(3) 0.0259(10) Uani 1 1 d . . . . .
C1 C 0.8589(4) 0.6247(4) 0.8857(4) 0.0367(13) Uani 1 1 d . . . . .
H1 H 0.9024 0.6549 0.8558 0.044 Uiso 1 1 calc R . . . .
C2 C 0.9077(5) 0.6013(4) 0.9880(4) 0.0459(16) Uani 1 1 d . . . . .
H2 H 0.9852 0.6160 1.0292 0.055 Uiso 1 1 calc R . . . .
C3 C 0.8457(5) 0.5558(4) 1.0340(4) 0.0499(18) Uani 1 1 d . . . . .
H3 H 0.8820 0.5403 1.1056 0.060 Uiso 1 1 calc R . . . .
C4 C 0.7352(5) 0.5339(4) 0.9780(4) 0.0377(14) Uani 1 1 d . . . . .
H4 H 0.6949 0.5019 1.0099 0.045 Uiso 1 1 calc R . . . .
C5 C 0.5654(5) 0.5412(3) 0.8093(4) 0.0269(12) Uani 1 1 d . . . . .
H5 H 0.526(4) 0.515(3) 0.837(3) 0.029(15) Uiso 1 1 d . . . . .
C6 C 0.3980(4) 0.5518(4) 0.6385(4) 0.0362(14) Uani 1 1 d . . . . .
H6 H 0.3502 0.5235 0.6651 0.043 Uiso 1 1 calc R . . . .
C7 C 0.3547(5) 0.5777(4) 0.5373(4) 0.0431(16) Uani 1 1 d . . . . .
H7 H 0.2767 0.5670 0.4935 0.052 Uiso 1 1 calc R . . . .
C8 C 0.4235(5) 0.6199(4) 0.4965(4) 0.0429(15) Uani 1 1 d . . . . .
H8 H 0.3919 0.6373 0.4254 0.052 Uiso 1 1 calc R . . . .
C9 C 0.5354(4) 0.6361(3) 0.5580(4) 0.0338(13) Uani 1 1 d . . . . .
H9 H 0.5811 0.6650 0.5295 0.041 Uiso 1 1 calc R . . . .
C10 C 0.7419(4) 0.6039(3) 0.8235(4) 0.0280(12) Uani 1 1 d . . . . .
C11 C 0.6792(4) 0.5587(3) 0.8711(4) 0.0268(12) Uani 1 1 d . . . . .
C12 C 0.5146(4) 0.5671(3) 0.7049(4) 0.0258(12) Uani 1 1 d . . . . .
C13 C 0.5844(4) 0.6102(3) 0.6642(4) 0.0240(11) Uani 1 1 d . . . . .
N4 N 0.5937(3) 0.3673(3) 0.0870(3) 0.0316(10) Uani 1 1 d . . . . .
C52 C 0.4199(5) 0.3609(3) -0.0670(4) 0.0337(13) Uani 1 1 d . . . . .
H52 H 0.4582 0.3836 -0.1060 0.040 Uiso 1 1 calc R . . . .
C53 C 0.3072(5) 0.3413(4) -0.1160(4) 0.0414(15) Uani 1 1 d . . . . .
H53 H 0.2678 0.3491 -0.1890 0.050 Uiso 1 1 calc R . . . .
C54 C 0.2480(5) 0.3094(4) -0.0592(4) 0.0410(15) Uani 1 1 d . . . . .
H54 H 0.1691 0.2967 -0.0942 0.049 Uiso 1 1 calc R . . . .
C55 C 0.3028(4) 0.2970(4) 0.0443(4) 0.0351(13) Uani 1 1 d . . . . .
H55 H 0.2617 0.2760 0.0814 0.042 Uiso 1 1 calc R . . . .
C56 C 0.4822(5) 0.3016(4) 0.2047(4) 0.0335(14) Uani 1 1 d . . . . .
H56 H 0.446(4) 0.285(3) 0.246(4) 0.030(14) Uiso 1 1 d . . . . .
C57 C 0.6663(5) 0.3020(4) 0.3598(4) 0.0480(17) Uani 1 1 d . . . . .
H57 H 0.6325 0.2789 0.4023 0.058 Uiso 1 1 calc R . . . .
C58 C 0.7804(6) 0.3194(4) 0.4017(5) 0.060(2) Uani 1 1 d . . . . .
H58 H 0.8257 0.3076 0.4733 0.072 Uiso 1 1 calc R . . . .
C59 C 0.8310(5) 0.3542(4) 0.3405(5) 0.0569(19) Uani 1 1 d . . . . .
H59 H 0.9103 0.3665 0.3714 0.068 Uiso 1 1 calc R . . . .
C60 C 0.7694(5) 0.3710(4) 0.2375(5) 0.0441(15) Uani 1 1 d . . . . .
H60 H 0.8055 0.3953 0.1973 0.053 Uiso 1 1 calc R . . . .
C61 C 0.4813(4) 0.3479(3) 0.0422(4) 0.0273(12) Uani 1 1 d . . . . .
C62 C 0.4214(4) 0.3149(3) 0.0990(4) 0.0291(12) Uani 1 1 d . . . . .
C63 C 0.5983(5) 0.3186(3) 0.2527(4) 0.0348(13) Uani 1 1 d . . . . .
C64 C 0.6509(4) 0.3522(3) 0.1902(4) 0.0326(13) 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
Br1 C17 1.907(5) . ?
O1 H1A 0.8202 . ?
O1 C14 1.367(6) . ?
C14 C15 1.392(7) . ?
C14 C19 1.381(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.368(6) . ?
C17 C18 1.387(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.374(7) . ?
C19 H19 0.9500 . ?
Br2 C36 1.903(5) . ?
O2 H2A 0.8200 . ?
O2 C33 1.365(6) . ?
C33 C34 1.390(8) . ?
C33 C38 1.378(7) . ?
C34 H34 0.9500 . ?
C34 C35 1.378(7) . ?
C35 H35 0.9500 . ?
C35 C36 1.368(6) . ?
C36 C37 1.381(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.384(7) . ?
C38 H38 0.9500 . ?
N3 C48 1.344(7) . ?
N3 C51 1.348(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.360(8) . ?
C39 C48 1.431(8) . ?
C40 H40 0.9500 . ?
C40 C41 1.416(8) . ?
C41 H41 0.9500 . ?
C41 C42 1.354(8) . ?
C42 H42 0.9500 . ?
C42 C49 1.438(7) . ?
C43 H43 0.97(5) . ?
C43 C49 1.380(7) . ?
C43 C50 1.395(7) . ?
C44 H44 0.9500 . ?
C44 C45 1.363(7) . ?
C44 C50 1.417(8) . ?
C45 H45 0.9500 . ?
C45 C46 1.407(8) . ?
C46 H46 0.9500 . ?
C46 C47 1.357(8) . ?
C47 H47 0.9500 . ?
C47 C51 1.442(8) . ?
C48 C49 1.429(7) . ?
C50 C51 1.416(7) . ?
N2 C29 1.357(6) . ?
N2 C32 1.354(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.362(7) . ?
C20 C29 1.429(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.394(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.362(7) . ?
C23 H23 0.9500 . ?
C23 C30 1.428(6) . ?
C24 H24 1.00(4) . ?
C24 C30 1.393(6) . ?
C24 C31 1.386(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.358(7) . ?
C25 C31 1.421(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.402(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.362(7) . ?
C28 H28 0.9500 . ?
C28 C32 1.431(6) . ?
C29 C30 1.416(6) . ?
C31 C32 1.417(6) . ?
N1 C10 1.353(6) . ?
N1 C13 1.355(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.361(7) . ?
C1 C10 1.431(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.404(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.353(7) . ?
C4 H4 0.9500 . ?
C4 C11 1.425(7) . ?
C5 H5 0.86(4) . ?
C5 C11 1.386(7) . ?
C5 C12 1.396(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.359(7) . ?
C6 C12 1.422(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.362(7) . ?
C9 H9 0.9500 . ?
C9 C13 1.419(6) . ?
C10 C11 1.426(7) . ?
C12 C13 1.417(6) . ?
N4 C61 1.353(6) . ?
N4 C64 1.351(6) . ?
C52 H52 0.9500 . ?
C52 C53 1.360(7) . ?
C52 C61 1.425(6) . ?
C53 H53 0.9500 . ?
C53 C54 1.413(7) . ?
C54 H54 0.9500 . ?
C54 C55 1.346(7) . ?
C55 H55 0.9500 . ?
C55 C62 1.425(7) . ?
C56 H56 0.93(5) . ?
C56 C62 1.382(7) . ?
C56 C63 1.390(7) . ?
C57 H57 0.9500 . ?
C57 C58 1.368(8) . ?
C57 C63 1.419(7) . ?
C58 H58 0.9500 . ?
C58 C59 1.395(9) . ?
C59 H59 0.9500 . ?
C59 C60 1.359(8) . ?
C60 H60 0.9500 . ?
C60 C64 1.423(7) . ?
C61 C62 1.426(7) . ?
C63 C64 1.422(7) . ?

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
C14 O1 H1A 109.4 . . ?
O1 C14 C15 123.3(5) . . ?
O1 C14 C19 117.8(5) . . ?
C19 C14 C15 118.9(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(5) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(5) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 Br1 120.8(4) . . ?
C16 C17 C18 120.3(5) . . ?
C18 C17 Br1 119.0(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(5) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C33 O2 H2A 109.6 . . ?
O2 C33 C34 122.1(5) . . ?
O2 C33 C38 118.4(5) . . ?
C38 C33 C34 119.5(5) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.2(5) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0(5) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 Br2 118.1(4) . . ?
C35 C36 C37 120.6(5) . . ?
C37 C36 Br2 121.2(4) . . ?
C36 C37 H37 120.3 . . ?
C36 C37 C38 119.5(5) . . ?
C38 C37 H37 120.3 . . ?
C33 C38 C37 120.3(5) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C48 N3 C51 117.0(5) . . ?
C40 C39 H39 119.4 . . ?
C40 C39 C48 121.2(5) . . ?
C48 C39 H39 119.4 . . ?
C39 C40 H40 119.5 . . ?
C39 C40 C41 120.9(6) . . ?
C41 C40 H40 119.5 . . ?
C40 C41 H41 120.1 . . ?
C42 C41 C40 119.9(6) . . ?
C42 C41 H41 120.1 . . ?
C41 C42 H42 119.3 . . ?
C41 C42 C49 121.4(5) . . ?
C49 C42 H42 119.3 . . ?
C49 C43 H43 121(3) . . ?
C49 C43 C50 120.5(5) . . ?
C50 C43 H43 118(3) . . ?
C45 C44 H44 119.5 . . ?
C45 C44 C50 121.0(5) . . ?
C50 C44 H44 119.5 . . ?
C44 C45 H45 120.0 . . ?
C44 C45 C46 120.0(6) . . ?
C46 C45 H45 120.0 . . ?
C45 C46 H46 119.5 . . ?
C47 C46 C45 121.1(6) . . ?
C47 C46 H46 119.5 . . ?
C46 C47 H47 119.7 . . ?
C46 C47 C51 120.5(6) . . ?
C51 C47 H47 119.7 . . ?
N3 C48 C39 118.5(5) . . ?
N3 C48 C49 123.5(5) . . ?
C49 C48 C39 118.0(5) . . ?
C43 C49 C42 123.7(5) . . ?
C43 C49 C48 117.7(5) . . ?
C48 C49 C42 118.6(5) . . ?
C43 C50 C44 123.2(5) . . ?
C43 C50 C51 117.3(5) . . ?
C51 C50 C44 119.5(5) . . ?
N3 C51 C47 118.0(5) . . ?
N3 C51 C50 124.1(5) . . ?
C50 C51 C47 117.9(5) . . ?
C32 N2 C29 117.5(4) . . ?
C21 C20 H20 120.1 . . ?
C21 C20 C29 119.8(5) . . ?
C29 C20 H20 120.1 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.5(5) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(5) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C30 119.7(5) . . ?
C30 C23 H23 120.1 . . ?
C30 C24 H24 118(2) . . ?
C31 C24 H24 121(2) . . ?
C31 C24 C30 120.3(5) . . ?
C26 C25 H25 119.5 . . ?
C26 C25 C31 120.9(5) . . ?
C31 C25 H25 119.5 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 119.9(5) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.1 . . ?
C28 C27 C26 121.8(5) . . ?
C28 C27 H27 119.1 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C32 119.4(5) . . ?
C32 C28 H28 120.3 . . ?
N2 C29 C20 118.2(4) . . ?
N2 C29 C30 123.2(4) . . ?
C30 C29 C20 118.6(4) . . ?
C24 C30 C23 122.6(5) . . ?
C24 C30 C29 117.8(4) . . ?
C29 C30 C23 119.5(4) . . ?
C24 C31 C25 123.0(5) . . ?
C24 C31 C32 118.1(4) . . ?
C32 C31 C25 119.0(4) . . ?
N2 C32 C28 117.9(5) . . ?
N2 C32 C31 123.1(4) . . ?
C31 C32 C28 118.9(5) . . ?
C10 N1 C13 117.9(4) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C10 119.7(5) . . ?
C10 C1 H1 120.1 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.3(5) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C11 119.9(5) . . ?
C11 C4 H4 120.0 . . ?
C11 C5 H5 118(3) . . ?
C11 C5 C12 121.2(5) . . ?
C12 C5 H5 121(3) . . ?
C7 C6 H6 119.9 . . ?
C7 C6 C12 120.2(5) . . ?
C12 C6 H6 119.9 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C13 120.6(5) . . ?
C13 C9 H9 119.7 . . ?
N1 C10 C1 118.2(5) . . ?
N1 C10 C11 123.2(4) . . ?
C11 C10 C1 118.6(5) . . ?
C4 C11 C10 119.4(5) . . ?
C5 C11 C4 123.4(5) . . ?
C5 C11 C10 117.2(5) . . ?
C5 C12 C6 123.4(5) . . ?
C5 C12 C13 117.5(5) . . ?
C13 C12 C6 119.1(5) . . ?
N1 C13 C9 118.2(4) . . ?
N1 C13 C12 123.1(4) . . ?
C12 C13 C9 118.7(4) . . ?
C64 N4 C61 117.4(4) . . ?
C53 C52 H52 119.6 . . ?
C53 C52 C61 120.7(5) . . ?
C61 C52 H52 119.6 . . ?
C52 C53 H53 119.7 . . ?
C52 C53 C54 120.6(5) . . ?
C54 C53 H53 119.7 . . ?
C53 C54 H54 119.8 . . ?
C55 C54 C53 120.4(5) . . ?
C55 C54 H54 119.8 . . ?
C54 C55 H55 119.4 . . ?
C54 C55 C62 121.2(5) . . ?
C62 C55 H55 119.4 . . ?
C62 C56 H56 121(3) . . ?
C62 C56 C63 120.5(5) . . ?
C63 C56 H56 118(3) . . ?
C58 C57 H57 120.0 . . ?
C58 C57 C63 120.0(6) . . ?
C63 C57 H57 120.0 . . ?
C57 C58 H58 119.7 . . ?
C57 C58 C59 120.6(6) . . ?
C59 C58 H58 119.7 . . ?
C58 C59 H59 119.3 . . ?
C60 C59 C58 121.5(6) . . ?
C60 C59 H59 119.3 . . ?
C59 C60 H60 120.1 . . ?
C59 C60 C64 119.8(6) . . ?
C64 C60 H60 120.1 . . ?
N4 C61 C52 118.4(5) . . ?
N4 C61 C62 123.2(4) . . ?
C52 C61 C62 118.4(5) . . ?
C55 C62 C61 118.6(5) . . ?
C56 C62 C55 123.5(5) . . ?
C56 C62 C61 117.8(5) . . ?
C56 C63 C57 123.1(5) . . ?
C56 C63 C64 117.8(5) . . ?
C57 C63 C64 119.0(5) . . ?
N4 C64 C60 117.8(5) . . ?
N4 C64 C63 123.2(5) . . ?
C63 C64 C60 119.0(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
Br1 C17 C18 C19 -178.5(4) . . . . ?
O1 C14 C15 C16 -179.4(4) . . . . ?
O1 C14 C19 C18 178.9(4) . . . . ?
C14 C15 C16 C17 1.2(7) . . . . ?
C15 C14 C19 C18 0.2(7) . . . . ?
C15 C16 C17 Br1 178.0(4) . . . . ?
C15 C16 C17 C18 -1.1(7) . . . . ?
C16 C17 C18 C19 0.6(7) . . . . ?
C17 C18 C19 C14 -0.1(7) . . . . ?
C19 C14 C15 C16 -0.7(7) . . . . ?
Br2 C36 C37 C38 179.6(3) . . . . ?
O2 C33 C34 C35 179.9(4) . . . . ?
O2 C33 C38 C37 -179.8(4) . . . . ?
C33 C34 C35 C36 0.1(7) . . . . ?
C34 C33 C38 C37 1.1(7) . . . . ?
C34 C35 C36 Br2 -179.5(4) . . . . ?
C34 C35 C36 C37 0.7(7) . . . . ?
C35 C36 C37 C38 -0.6(7) . . . . ?
C36 C37 C38 C33 -0.3(7) . . . . ?
C38 C33 C34 C35 -1.0(8) . . . . ?
N3 C48 C49 C42 179.5(5) . . . . ?
N3 C48 C49 C43 0.4(8) . . . . ?
C39 C40 C41 C42 -0.8(8) . . . . ?
C39 C48 C49 C42 -1.1(7) . . . . ?
C39 C48 C49 C43 179.8(5) . . . . ?
C40 C39 C48 N3 -179.0(5) . . . . ?
C40 C39 C48 C49 1.6(8) . . . . ?
C40 C41 C42 C49 1.3(8) . . . . ?
C41 C42 C49 C43 178.7(5) . . . . ?
C41 C42 C49 C48 -0.3(8) . . . . ?
C43 C50 C51 N3 0.1(8) . . . . ?
C43 C50 C51 C47 -179.1(5) . . . . ?
C44 C45 C46 C47 0.8(9) . . . . ?
C44 C50 C51 N3 179.4(5) . . . . ?
C44 C50 C51 C47 0.1(7) . . . . ?
C45 C44 C50 C43 179.7(5) . . . . ?
C45 C44 C50 C51 0.5(8) . . . . ?
C45 C46 C47 C51 -0.1(9) . . . . ?
C46 C47 C51 N3 -179.6(5) . . . . ?
C46 C47 C51 C50 -0.3(8) . . . . ?
C48 N3 C51 C47 179.6(4) . . . . ?
C48 N3 C51 C50 0.4(7) . . . . ?
C48 C39 C40 C41 -0.7(8) . . . . ?
C49 C43 C50 C44 -179.6(5) . . . . ?
C49 C43 C50 C51 -0.4(8) . . . . ?
C50 C43 C49 C42 -178.9(5) . . . . ?
C50 C43 C49 C48 0.1(8) . . . . ?
C50 C44 C45 C46 -1.0(9) . . . . ?
C51 N3 C48 C39 179.9(5) . . . . ?
C51 N3 C48 C49 -0.7(7) . . . . ?
N2 C29 C30 C23 -179.4(4) . . . . ?
N2 C29 C30 C24 1.4(7) . . . . ?
C20 C21 C22 C23 1.3(8) . . . . ?
C20 C29 C30 C23 1.2(7) . . . . ?
C20 C29 C30 C24 -178.1(4) . . . . ?
C21 C20 C29 N2 -179.7(5) . . . . ?
C21 C20 C29 C30 -0.2(7) . . . . ?
C21 C22 C23 C30 -0.3(8) . . . . ?
C22 C23 C30 C24 178.3(5) . . . . ?
C22 C23 C30 C29 -0.9(7) . . . . ?
C24 C31 C32 N2 0.5(7) . . . . ?
C24 C31 C32 C28 178.8(5) . . . . ?
C25 C26 C27 C28 0.0(8) . . . . ?
C25 C31 C32 N2 -178.5(4) . . . . ?
C25 C31 C32 C28 -0.2(7) . . . . ?
C26 C25 C31 C24 -178.7(5) . . . . ?
C26 C25 C31 C32 0.3(7) . . . . ?
C26 C27 C28 C32 0.0(8) . . . . ?
C27 C28 C32 N2 178.5(5) . . . . ?
C27 C28 C32 C31 0.1(7) . . . . ?
C29 N2 C32 C28 -177.2(4) . . . . ?
C29 N2 C32 C31 1.1(7) . . . . ?
C29 C20 C21 C22 -1.0(8) . . . . ?
C30 C24 C31 C25 177.8(5) . . . . ?
C30 C24 C31 C32 -1.2(7) . . . . ?
C31 C24 C30 C23 -178.9(5) . . . . ?
C31 C24 C30 C29 0.3(7) . . . . ?
C31 C25 C26 C27 -0.2(8) . . . . ?
C32 N2 C29 C20 177.4(4) . . . . ?
C32 N2 C29 C30 -2.1(7) . . . . ?
N1 C10 C11 C4 179.3(5) . . . . ?
N1 C10 C11 C5 -0.5(7) . . . . ?
C1 C2 C3 C4 0.0(9) . . . . ?
C1 C10 C11 C4 -1.5(7) . . . . ?
C1 C10 C11 C5 178.6(5) . . . . ?
C2 C1 C10 N1 179.3(5) . . . . ?
C2 C1 C10 C11 0.1(7) . . . . ?
C2 C3 C4 C11 -1.4(8) . . . . ?
C3 C4 C11 C5 -178.0(5) . . . . ?
C3 C4 C11 C10 2.2(8) . . . . ?
C5 C12 C13 N1 -1.7(7) . . . . ?
C5 C12 C13 C9 179.2(5) . . . . ?
C6 C7 C8 C9 -0.2(9) . . . . ?
C6 C12 C13 N1 178.6(5) . . . . ?
C6 C12 C13 C9 -0.5(7) . . . . ?
C7 C6 C12 C5 -179.1(5) . . . . ?
C7 C6 C12 C13 0.6(8) . . . . ?
C7 C8 C9 C13 0.3(8) . . . . ?
C8 C9 C13 N1 -179.1(5) . . . . ?
C8 C9 C13 C12 0.0(7) . . . . ?
C10 N1 C13 C9 -179.8(4) . . . . ?
C10 N1 C13 C12 1.1(7) . . . . ?
C10 C1 C2 C3 0.7(8) . . . . ?
C11 C5 C12 C6 -179.1(5) . . . . ?
C11 C5 C12 C13 1.2(7) . . . . ?
C12 C5 C11 C4 180.0(5) . . . . ?
C12 C5 C11 C10 -0.1(7) . . . . ?
C12 C6 C7 C8 -0.2(8) . . . . ?
C13 N1 C10 C1 -179.1(4) . . . . ?
C13 N1 C10 C11 0.1(7) . . . . ?
N4 C61 C62 C55 179.7(5) . . . . ?
N4 C61 C62 C56 -0.6(7) . . . . ?
C52 C53 C54 C55 -0.8(8) . . . . ?
C52 C61 C62 C55 -0.4(7) . . . . ?
C52 C61 C62 C56 179.3(5) . . . . ?
C53 C52 C61 N4 179.1(5) . . . . ?
C53 C52 C61 C62 -0.8(7) . . . . ?
C53 C54 C55 C62 -0.5(8) . . . . ?
C54 C55 C62 C56 -178.6(5) . . . . ?
C54 C55 C62 C61 1.0(8) . . . . ?
C56 C63 C64 N4 -0.8(8) . . . . ?
C56 C63 C64 C60 179.4(5) . . . . ?
C57 C58 C59 C60 -0.7(9) . . . . ?
C57 C63 C64 N4 177.9(5) . . . . ?
C57 C63 C64 C60 -1.9(7) . . . . ?
C58 C57 C63 C56 179.3(5) . . . . ?
C58 C57 C63 C64 0.7(8) . . . . ?
C58 C59 C60 C64 -0.5(9) . . . . ?
C59 C60 C64 N4 -177.9(5) . . . . ?
C59 C60 C64 C63 1.9(8) . . . . ?
C61 N4 C64 C60 179.0(4) . . . . ?
C61 N4 C64 C63 -0.8(7) . . . . ?
C61 C52 C53 C54 1.4(8) . . . . ?
C62 C56 C63 C57 -176.9(5) . . . . ?
C62 C56 C63 C64 1.7(8) . . . . ?
C63 C56 C62 C55 178.6(5) . . . . ?
C63 C56 C62 C61 -1.1(8) . . . . ?
C63 C57 C58 C59 0.6(9) . . . . ?
C64 N4 C61 C52 -178.4(4) . . . . ?
C64 N4 C61 C62 1.5(7) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.001(9)
2 -0.001(9)

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_zz
_database_code_depnum_ccdc_archive 'CCDC 1588641'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
_audit_creation_date             2016-09-01
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5215)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 I O, 2(C13 H9 N)'
_chemical_formula_sum            'C32 H23 I N2 O'
_chemical_formula_weight         578.42
_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'
I I -0.4742 1.8119 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.8528(6)
_cell_length_b                   10.1405(4)
_cell_length_c                   28.1824(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5102.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8207
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.061
_cell_measurement_theta_min      2.281
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.283
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0754 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.8745.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            42912
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.728
_diffrn_reflns_theta_min         1.841
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4564
_reflns_number_total             5941
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+2.3930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0698
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.78711(2) 0.81226(2) 0.38322(2) 0.02726(6) Uani 1 1 d . . . . .
O1 O 0.43808(10) 0.79446(16) 0.37739(7) 0.0320(4) Uani 1 1 d . . . . .
H1A H 0.4224 0.7168 0.3745 0.048 Uiso 1 1 calc GR . . . .
N1 N 0.36286(11) 0.56370(18) 0.36641(7) 0.0265(4) Uani 1 1 d . . . . .
C1 C 0.36540(16) 0.5091(2) 0.44877(9) 0.0356(6) Uani 1 1 d . . . . .
H1 H 0.4090 0.5616 0.4529 0.043 Uiso 1 1 calc R . . . .
C2 C 0.33512(18) 0.4446(3) 0.48638(10) 0.0446(7) Uani 1 1 d . . . . .
H2 H 0.3577 0.4526 0.5168 0.054 Uiso 1 1 calc R . . . .
C3 C 0.27000(18) 0.3651(3) 0.48093(11) 0.0482(8) Uani 1 1 d . . . . .
H3 H 0.2494 0.3210 0.5077 0.058 Uiso 1 1 calc R . . . .
C4 C 0.23728(17) 0.3519(3) 0.43813(11) 0.0417(7) Uani 1 1 d . . . . .
H4 H 0.1938 0.2987 0.4350 0.050 Uiso 1 1 calc R . . . .
C5 C 0.23550(14) 0.4058(2) 0.35260(10) 0.0314(5) Uani 1 1 d . . . . .
H5 H 0.1921 0.3532 0.3480 0.038 Uiso 1 1 calc R . . . .
C6 C 0.23781(15) 0.4660(3) 0.26709(10) 0.0368(6) Uani 1 1 d . . . . .
H6 H 0.1949 0.4134 0.2608 0.044 Uiso 1 1 calc R . . . .
C7 C 0.27028(16) 0.5346(3) 0.23129(10) 0.0388(6) Uani 1 1 d . . . . .
H7 H 0.2498 0.5304 0.2002 0.047 Uiso 1 1 calc R . . . .
C8 C 0.33429(16) 0.6120(2) 0.24014(9) 0.0372(6) Uani 1 1 d . . . . .
H8 H 0.3567 0.6591 0.2147 0.045 Uiso 1 1 calc R . . . .
C9 C 0.36479(15) 0.6208(2) 0.28416(9) 0.0313(5) Uani 1 1 d . . . . .
H9 H 0.4081 0.6735 0.2892 0.038 Uiso 1 1 calc R . . . .
C10 C 0.33170(14) 0.4982(2) 0.40282(9) 0.0266(5) Uani 1 1 d . . . . .
C11 C 0.26704(14) 0.4166(2) 0.39771(9) 0.0294(5) Uani 1 1 d . . . . .
C12 C 0.26735(13) 0.4720(2) 0.31424(9) 0.0275(5) Uani 1 1 d . . . . .
C13 C 0.33191(13) 0.5513(2) 0.32279(8) 0.0257(5) Uani 1 1 d . . . . .
C14 C 0.51402(13) 0.7942(2) 0.37838(8) 0.0235(5) Uani 1 1 d . . . . .
C15 C 0.55547(14) 0.6786(2) 0.38112(8) 0.0264(5) Uani 1 1 d . . . . .
H15 H 0.5308 0.5957 0.3822 0.032 Uiso 1 1 calc R . . . .
C16 C 0.63266(14) 0.6845(2) 0.38232(8) 0.0276(5) Uani 1 1 d . . . . .
H16 H 0.6610 0.6054 0.3838 0.033 Uiso 1 1 calc R . . . .
C17 C 0.66899(13) 0.8049(2) 0.38138(8) 0.0229(5) Uani 1 1 d . . . . .
C18 C 0.62826(13) 0.9204(2) 0.37912(8) 0.0246(5) Uani 1 1 d . . . . .
H18 H 0.6532 1.0031 0.3787 0.030 Uiso 1 1 calc R . . . .
C19 C 0.55107(14) 0.9150(2) 0.37747(8) 0.0273(5) Uani 1 1 d . . . . .
H19 H 0.5230 0.9944 0.3757 0.033 Uiso 1 1 calc R . . . .
N2 N 0.53519(11) 0.32610(19) 0.37881(7) 0.0277(4) Uani 1 1 d . . . . .
C20 C 0.53823(15) 0.2654(3) 0.46050(9) 0.0337(6) Uani 1 1 d . . . . .
H20 H 0.5841 0.3117 0.4643 0.040 Uiso 1 1 calc R . . . .
C21 C 0.50730(16) 0.2015(3) 0.49807(10) 0.0390(6) Uani 1 1 d . . . . .
H21 H 0.5322 0.2030 0.5278 0.047 Uiso 1 1 calc R . . . .
C22 C 0.43893(17) 0.1331(3) 0.49370(10) 0.0409(7) Uani 1 1 d . . . . .
H22 H 0.4182 0.0897 0.5205 0.049 Uiso 1 1 calc R . . . .
C23 C 0.40246(15) 0.1286(3) 0.45148(10) 0.0361(6) Uani 1 1 d . . . . .
H23 H 0.3563 0.0827 0.4490 0.043 Uiso 1 1 calc R . . . .
C24 C 0.39988(14) 0.1882(2) 0.36621(9) 0.0293(5) Uani 1 1 d . . . . .
H24 H 0.3539 0.1424 0.3621 0.035 Uiso 1 1 calc R . . . .
C25 C 0.40220(15) 0.2489(3) 0.28125(9) 0.0358(6) Uani 1 1 d . . . . .
H25 H 0.3570 0.2021 0.2755 0.043 Uiso 1 1 calc R . . . .
C26 C 0.43601(17) 0.3130(3) 0.24519(9) 0.0394(6) Uani 1 1 d . . . . .
H26 H 0.4149 0.3102 0.2143 0.047 Uiso 1 1 calc R . . . .
C27 C 0.50326(16) 0.3849(3) 0.25339(9) 0.0406(7) Uani 1 1 d . . . . .
H27 H 0.5262 0.4309 0.2279 0.049 Uiso 1 1 calc R . . . .
C28 C 0.53500(15) 0.3887(3) 0.29710(9) 0.0348(6) Uani 1 1 d . . . . .
H28 H 0.5800 0.4368 0.3019 0.042 Uiso 1 1 calc R . . . .
C29 C 0.50206(13) 0.2630(2) 0.41535(8) 0.0257(5) Uani 1 1 d . . . . .
C30 C 0.43331(13) 0.1928(2) 0.41062(9) 0.0273(5) Uani 1 1 d . . . . .
C31 C 0.43324(13) 0.2501(2) 0.32788(8) 0.0270(5) Uani 1 1 d . . . . .
C32 C 0.50117(13) 0.3209(2) 0.33598(8) 0.0265(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C17 2.111(2) . ?
O1 H1A 0.8400 . ?
O1 C14 1.356(3) . ?
N1 C10 1.343(3) . ?
N1 C13 1.354(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.358(4) . ?
C1 C10 1.432(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.423(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.347(4) . ?
C4 H4 0.9500 . ?
C4 C11 1.418(4) . ?
C5 H5 0.9500 . ?
C5 C11 1.395(4) . ?
C5 C12 1.394(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.355(4) . ?
C6 C12 1.431(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.409(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.358(4) . ?
C9 H9 0.9500 . ?
C9 C13 1.424(3) . ?
C10 C11 1.428(3) . ?
C12 C13 1.426(3) . ?
C14 C15 1.388(3) . ?
C14 C19 1.392(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 C18 1.380(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(3) . ?
C19 H19 0.9500 . ?
N2 C29 1.349(3) . ?
N2 C32 1.352(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.358(4) . ?
C20 C29 1.427(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.410(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.357(4) . ?
C23 H23 0.9500 . ?
C23 C30 1.433(3) . ?
C24 H24 0.9500 . ?
C24 C30 1.387(3) . ?
C24 C31 1.384(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.349(4) . ?
C25 C31 1.426(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.424(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.356(4) . ?
C28 H28 0.9500 . ?
C28 C32 1.428(3) . ?
C29 C30 1.425(3) . ?
C31 C32 1.428(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
C14 O1 H1A 109.5 . . ?
C10 N1 C13 118.6(2) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C10 120.1(3) . . ?
C10 C1 H1 120.0 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C11 120.7(3) . . ?
C11 C4 H4 119.6 . . ?
C11 C5 H5 119.8 . . ?
C12 C5 H5 119.8 . . ?
C12 C5 C11 120.3(2) . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C12 120.8(2) . . ?
C12 C6 H6 119.6 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C13 120.0(2) . . ?
C13 C9 H9 120.0 . . ?
N1 C10 C1 118.6(2) . . ?
N1 C10 C11 123.0(2) . . ?
C11 C10 C1 118.4(2) . . ?
C4 C11 C10 119.3(2) . . ?
C5 C11 C4 123.0(2) . . ?
C5 C11 C10 117.6(2) . . ?
C5 C12 C6 123.3(2) . . ?
C5 C12 C13 118.1(2) . . ?
C13 C12 C6 118.6(2) . . ?
N1 C13 C9 118.7(2) . . ?
N1 C13 C12 122.4(2) . . ?
C9 C13 C12 118.9(2) . . ?
O1 C14 C15 122.4(2) . . ?
O1 C14 C19 118.2(2) . . ?
C15 C14 C19 119.4(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 I1 119.98(17) . . ?
C18 C17 I1 119.83(16) . . ?
C18 C17 C16 120.2(2) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C29 N2 C32 117.8(2) . . ?
C21 C20 H20 119.9 . . ?
C21 C20 C29 120.2(3) . . ?
C29 C20 H20 119.9 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C30 120.3(3) . . ?
C30 C23 H23 119.8 . . ?
C30 C24 H24 119.9 . . ?
C31 C24 H24 119.9 . . ?
C31 C24 C30 120.2(2) . . ?
C26 C25 H25 119.5 . . ?
C26 C25 C31 121.1(3) . . ?
C31 C25 H25 119.5 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.1(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 120.9(3) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C32 120.5(3) . . ?
C32 C28 H28 119.8 . . ?
N2 C29 C20 118.3(2) . . ?
N2 C29 C30 122.9(2) . . ?
C30 C29 C20 118.8(2) . . ?
C24 C30 C23 123.0(2) . . ?
C24 C30 C29 118.2(2) . . ?
C29 C30 C23 118.9(2) . . ?
C24 C31 C25 123.2(2) . . ?
C24 C31 C32 117.9(2) . . ?
C25 C31 C32 118.8(2) . . ?
N2 C32 C28 118.4(2) . . ?
N2 C32 C31 123.0(2) . . ?
C31 C32 C28 118.6(2) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
