# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_dm15081_0m
_database_code_depnum_ccdc_archive 'CCDC 1045751'
_audit_update_record             
;
2015-01-27 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;
_audit_creation_date             2015-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H13 N O S'
_chemical_formula_sum            'C17 H13 N O S'
_chemical_formula_weight         279.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   6.9438(5)
_cell_length_b                   16.2467(11)
_cell_length_c                   24.2648(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2737.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6188
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.914
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0685 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.8961.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.524
_diffrn_reflns_theta_min         1.678
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                3334
_reflns_number_total             4175
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+0.9311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1146
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S1 S 0.91616(5) 0.21059(2) 0.28990(2) 0.02089(10) Uani 1 1 d . . . . .
O1 O 0.85784(16) 0.36169(6) 0.26442(4) 0.0258(2) Uani 1 1 d . . . . .
N1 N 0.95286(16) 0.12866(6) 0.19379(5) 0.0201(2) Uani 1 1 d . . . . .
C1 C 0.89049(18) 0.29501(7) 0.24372(5) 0.0187(2) Uani 1 1 d . . . . .
C2 C 0.91306(17) 0.27907(7) 0.18486(5) 0.0166(2) Uani 1 1 d . . . . .
C3 C 0.93946(17) 0.20154(7) 0.16403(5) 0.0171(2) Uani 1 1 d . . . . .
C4 C 0.94259(18) 0.12588(7) 0.24663(6) 0.0200(2) Uani 1 1 d . . . . .
C5 C 0.9512(2) 0.04518(9) 0.27626(6) 0.0277(3) Uani 1 1 d . . . . .
H5A H 0.9773 0.0010 0.2498 0.042 Uiso 1 1 calc GR . . . .
H5B H 0.8277 0.0348 0.2946 0.042 Uiso 1 1 calc GR . . . .
H5C H 1.0541 0.0468 0.3039 0.042 Uiso 1 1 calc GR . . . .
C6 C 0.95279(19) 0.18518(7) 0.10385(5) 0.0186(2) Uani 1 1 d . . . . .
C7 C 1.1044(2) 0.13794(8) 0.08350(6) 0.0230(3) Uani 1 1 d . . . . .
H7 H 1.2019 0.1188 0.1078 0.028 Uiso 1 1 calc R . . . .
C8 C 1.1135(2) 0.11865(9) 0.02780(6) 0.0268(3) Uani 1 1 d . . . . .
H8 H 1.2189 0.0877 0.0139 0.032 Uiso 1 1 calc R . . . .
C9 C 0.9692(2) 0.14456(9) -0.00759(6) 0.0272(3) Uani 1 1 d . . . . .
H9 H 0.9747 0.1306 -0.0456 0.033 Uiso 1 1 calc R . . . .
C10 C 0.8171(2) 0.19069(9) 0.01234(6) 0.0275(3) Uani 1 1 d . . . . .
H10 H 0.7178 0.2081 -0.0119 0.033 Uiso 1 1 calc R . . . .
C11 C 0.8094(2) 0.21165(8) 0.06794(6) 0.0233(3) Uani 1 1 d . . . . .
H11 H 0.7058 0.2441 0.0814 0.028 Uiso 1 1 calc R . . . .
C12 C 0.90791(19) 0.35338(7) 0.14909(5) 0.0186(2) Uani 1 1 d . . . . .
C13 C 1.0697(2) 0.37572(8) 0.11873(6) 0.0233(3) Uani 1 1 d . . . . .
H13 H 1.1839 0.3437 0.1212 0.028 Uiso 1 1 calc R . . . .
C14 C 1.0649(2) 0.44465(9) 0.08473(6) 0.0301(3) Uani 1 1 d . . . . .
H14 H 1.1755 0.4594 0.0639 0.036 Uiso 1 1 calc R . . . .
C15 C 0.8995(3) 0.49163(9) 0.08124(6) 0.0325(4) Uani 1 1 d . . . . .
H15 H 0.8959 0.5384 0.0578 0.039 Uiso 1 1 calc R . . . .
C16 C 0.7388(2) 0.47043(8) 0.11191(6) 0.0296(3) Uani 1 1 d . . . . .
H16 H 0.6254 0.5030 0.1096 0.036 Uiso 1 1 calc R . . . .
C17 C 0.7427(2) 0.40176(8) 0.14606(6) 0.0238(3) Uani 1 1 d . . . . .
H17 H 0.6326 0.3878 0.1673 0.029 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7800(13) . ?
S1 C4 1.7406(13) . ?
O1 C1 1.2155(15) . ?
N1 C3 1.3901(15) . ?
N1 C4 1.2849(17) . ?
C1 C2 1.4600(18) . ?
C2 C3 1.3695(17) . ?
C2 C12 1.4874(17) . ?
C3 C6 1.4872(17) . ?
C4 C5 1.4964(18) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.3932(18) . ?
C6 C11 1.3912(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3890(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3926(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3913(18) . ?
C12 C17 1.3923(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3913(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3899(19) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C1 103.90(6) . . ?
C4 N1 C3 123.00(11) . . ?
O1 C1 S1 116.45(10) . . ?
O1 C1 C2 125.61(12) . . ?
C2 C1 S1 117.93(9) . . ?
C1 C2 C12 115.11(10) . . ?
C3 C2 C1 122.58(11) . . ?
C3 C2 C12 122.31(11) . . ?
N1 C3 C6 110.72(10) . . ?
C2 C3 N1 126.92(12) . . ?
C2 C3 C6 122.34(11) . . ?
N1 C4 S1 125.44(10) . . ?
N1 C4 C5 120.52(12) . . ?
C5 C4 S1 114.03(10) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C3 119.56(11) . . ?
C11 C6 C3 121.01(12) . . ?
C11 C6 C7 119.29(12) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.23(13) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.11(13) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.04(13) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.07(13) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 120.24(13) . . ?
C6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C2 120.08(11) . . ?
C13 C12 C17 119.33(12) . . ?
C17 C12 C2 120.58(12) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.32(13) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.03(14) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.97(13) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.29(13) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.05(14) . . ?
C16 C17 H17 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 4.65(16) . . . . ?
S1 C1 C2 C12 -174.57(9) . . . . ?
O1 C1 C2 C3 -176.38(13) . . . . ?
O1 C1 C2 C12 4.40(18) . . . . ?
N1 C3 C6 C7 -51.14(15) . . . . ?
N1 C3 C6 C11 124.52(13) . . . . ?
C1 S1 C4 N1 4.04(13) . . . . ?
C1 S1 C4 C5 -175.36(10) . . . . ?
C1 C2 C3 N1 -1.4(2) . . . . ?
C1 C2 C3 C6 176.94(11) . . . . ?
C1 C2 C12 C13 116.18(13) . . . . ?
C1 C2 C12 C17 -63.10(15) . . . . ?
C2 C3 C6 C7 130.24(13) . . . . ?
C2 C3 C6 C11 -54.10(18) . . . . ?
C2 C12 C13 C14 179.29(12) . . . . ?
C2 C12 C17 C16 -179.13(12) . . . . ?
C3 N1 C4 S1 -1.49(18) . . . . ?
C3 N1 C4 C5 177.87(12) . . . . ?
C3 C2 C12 C13 -63.04(17) . . . . ?
C3 C2 C12 C17 117.68(14) . . . . ?
C3 C6 C7 C8 176.75(12) . . . . ?
C3 C6 C11 C10 -175.35(12) . . . . ?
C4 S1 C1 O1 175.67(10) . . . . ?
C4 S1 C1 C2 -5.27(11) . . . . ?
C4 N1 C3 C2 -0.4(2) . . . . ?
C4 N1 C3 C6 -178.98(12) . . . . ?
C6 C7 C8 C9 -1.7(2) . . . . ?
C7 C6 C11 C10 0.3(2) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C6 -1.0(2) . . . . ?
C11 C6 C7 C8 1.02(19) . . . . ?
C12 C2 C3 N1 177.72(12) . . . . ?
C12 C2 C3 C6 -3.89(18) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C12 C17 C16 1.59(19) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C12 -0.7(2) . . . . ?
C17 C12 C13 C14 -1.43(19) . . . . ?

_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_cd17095
_database_code_depnum_ccdc_archive 'CCDC 1535814'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 Br N O2'
_chemical_formula_weight         404.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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

_cell_length_a                   17.425(3)
_cell_length_b                   7.1016(12)
_cell_length_c                   29.618(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.008(4)
_cell_angle_gamma                90
_cell_volume                     3523.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3252
_cell_measurement_theta_min      4.864
_cell_measurement_theta_max      45.807

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.349
_shelx_estimated_absorpt_T_min   0.651
_shelx_estimated_absorpt_T_max   0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4800
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19639
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.216
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6559
_reflns_number_gt                4175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6559
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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_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 1.45948(2) 0.65607(5) 0.10225(2) 0.06460(16) Uani 1 1 d . . . . .
Br2 Br 0.05226(2) 0.13517(5) 0.15484(2) 0.06157(15) Uani 1 1 d . . . . .
N1 N 1.06609(14) 0.6508(3) 0.10370(8) 0.0409(6) Uani 1 1 d . . . . .
N2 N 0.44192(14) 0.1321(3) 0.14592(8) 0.0348(6) Uani 1 1 d . . . . .
O1 O 0.94582(16) 0.8145(6) -0.02467(9) 0.1176(14) Uani 1 1 d . . . . .
O2 O 1.05850(13) 0.7385(4) 0.02723(7) 0.0676(7) Uani 1 1 d . . . . .
O3 O 0.56518(13) -0.0743(4) 0.27005(8) 0.0598(7) Uani 1 1 d . . . . .
O4 O 0.45137(12) 0.0030(3) 0.21969(7) 0.0435(5) Uani 1 1 d . . . . .
C1 C 0.9767(2) 0.7668(6) 0.01504(13) 0.0660(11) Uani 1 1 d . . . . .
C2 C 0.93820(18) 0.7319(5) 0.05144(10) 0.0446(8) Uani 1 1 d . . . . .
C3 C 0.98382(18) 0.6615(4) 0.09298(10) 0.0397(8) Uani 1 1 d . . . . .
C4 C 1.09932(19) 0.6910(4) 0.07136(11) 0.0426(8) Uani 1 1 d . . . . .
C5 C 1.18513(18) 0.6874(4) 0.07861(10) 0.0390(7) Uani 1 1 d . . . . .
C6 C 1.23397(18) 0.6050(4) 0.11882(11) 0.0438(8) Uani 1 1 d . . . . .
H6 H 1.2113 0.5540 0.1411 0.053 Uiso 1 1 calc R U . . .
C7 C 1.3151(2) 0.5974(4) 0.12629(11) 0.0471(8) Uani 1 1 d . . . . .
H7 H 1.3475 0.5424 0.1534 0.057 Uiso 1 1 calc R U . . .
C8 C 1.34811(19) 0.6724(4) 0.09303(12) 0.0444(8) Uani 1 1 d . . . . .
C9 C 1.3018(2) 0.7563(5) 0.05316(12) 0.0514(9) Uani 1 1 d . . . . .
H9 H 1.3250 0.8082 0.0313 0.062 Uiso 1 1 calc R U . . .
C10 C 1.2205(2) 0.7627(5) 0.04586(11) 0.0503(9) Uani 1 1 d . . . . .
H10 H 1.1887 0.8182 0.0187 0.060 Uiso 1 1 calc R U . . .
C11 C 0.85219(18) 0.7779(5) 0.04198(10) 0.0443(8) Uani 1 1 d . . . . .
C12 C 0.79530(19) 0.7044(5) 0.00346(11) 0.0489(8) Uani 1 1 d . . . . .
H12 H 0.8111 0.6266 -0.0176 0.059 Uiso 1 1 calc R U . . .
C13 C 0.71581(19) 0.7461(5) -0.00369(12) 0.0541(9) Uani 1 1 d . . . . .
H13 H 0.6780 0.6933 -0.0290 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6918(2) 0.8652(5) 0.02640(12) 0.0556(10) Uani 1 1 d . . . . .
H14 H 0.6380 0.8936 0.0215 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7480(2) 0.9414(5) 0.06363(12) 0.0592(10) Uani 1 1 d . . . . .
H15 H 0.7323 1.0233 0.0839 0.071 Uiso 1 1 calc R U . . .
C16 C 0.8270(2) 0.8982(5) 0.07129(11) 0.0531(9) Uani 1 1 d . . . . .
H16 H 0.8644 0.9513 0.0968 0.064 Uiso 1 1 calc R U . . .
C17 C 0.95037(17) 0.5862(4) 0.13073(10) 0.0392(7) Uani 1 1 d . . . . .
C18 C 0.88840(19) 0.4580(5) 0.12003(12) 0.0511(9) Uani 1 1 d . . . . .
H18 H 0.8638 0.4275 0.0889 0.061 Uiso 1 1 calc R U . . .
C19 C 0.8629(2) 0.3752(5) 0.15545(14) 0.0597(10) Uani 1 1 d . . . . .
H19 H 0.8218 0.2873 0.1483 0.072 Uiso 1 1 calc R U . . .
C20 C 0.8987(2) 0.4235(5) 0.20148(13) 0.0597(10) Uani 1 1 d . . . . .
H20 H 0.8817 0.3675 0.2254 0.072 Uiso 1 1 calc R U . . .
C21 C 0.9587(2) 0.5521(5) 0.21217(12) 0.0527(9) Uani 1 1 d . . . . .
H21 H 0.9815 0.5865 0.2433 0.063 Uiso 1 1 calc R U . . .
C22 C 0.98555(19) 0.6316(4) 0.17712(11) 0.0448(8) Uani 1 1 d . . . . .
H22 H 1.0278 0.7166 0.1847 0.054 Uiso 1 1 calc R U . . .
C23 C 0.53364(18) -0.0124(4) 0.23158(11) 0.0417(8) Uani 1 1 d . . . . .
C24 C 0.57128(17) 0.0455(4) 0.19603(10) 0.0362(7) Uani 1 1 d . . . . .
C25 C 0.52425(17) 0.1213(4) 0.15531(10) 0.0333(7) Uani 1 1 d . . . . .
C26 C 0.40994(17) 0.0752(4) 0.17753(10) 0.0348(7) Uani 1 1 d . . . . .
C27 C 0.32445(17) 0.0849(4) 0.17238(10) 0.0333(7) Uani 1 1 d . . . . .
C28 C 0.27199(18) 0.1199(4) 0.12897(10) 0.0403(8) Uani 1 1 d . . . . .
H28 H 0.2916 0.1356 0.1030 0.048 Uiso 1 1 calc R U . . .
C29 C 0.19122(19) 0.1320(4) 0.12341(11) 0.0447(8) Uani 1 1 d . . . . .
H29 H 0.1563 0.1549 0.0940 0.054 Uiso 1 1 calc R U . . .
C30 C 0.16299(18) 0.1098(4) 0.16181(12) 0.0408(8) Uani 1 1 d . . . . .
C31 C 0.21335(19) 0.0739(5) 0.20548(12) 0.0490(8) Uani 1 1 d . . . . .
H31 H 0.1931 0.0580 0.2312 0.059 Uiso 1 1 calc R U . . .
C32 C 0.29380(19) 0.0618(5) 0.21076(11) 0.0450(8) Uani 1 1 d . . . . .
H32 H 0.3283 0.0379 0.2403 0.054 Uiso 1 1 calc R U . . .
C33 C 0.65808(17) 0.0110(4) 0.20613(10) 0.0379(7) Uani 1 1 d . . . . .
C34 C 0.71108(19) 0.0840(5) 0.24644(11) 0.0488(8) Uani 1 1 d . . . . .
H34 H 0.6924 0.1564 0.2673 0.059 Uiso 1 1 calc R U . . .
C35 C 0.7917(2) 0.0478(6) 0.25509(12) 0.0589(10) Uani 1 1 d . . . . .
H35 H 0.8272 0.0983 0.2818 0.071 Uiso 1 1 calc R U . . .
C36 C 0.8205(2) -0.0600(6) 0.22544(13) 0.0605(10) Uani 1 1 d . . . . .
H36 H 0.8750 -0.0832 0.2319 0.073 Uiso 1 1 calc R U . . .
C37 C 0.7686(2) -0.1345(5) 0.18589(13) 0.0588(10) Uani 1 1 d . . . . .
H37 H 0.7878 -0.2088 0.1655 0.071 Uiso 1 1 calc R U . . .
C38 C 0.68817(19) -0.0990(5) 0.17646(11) 0.0489(9) Uani 1 1 d . . . . .
H38 H 0.6534 -0.1499 0.1496 0.059 Uiso 1 1 calc R U . . .
C39 C 0.55464(16) 0.2030(4) 0.11751(10) 0.0351(7) Uani 1 1 d . . . . .
C40 C 0.61929(18) 0.3243(4) 0.12758(11) 0.0458(8) Uani 1 1 d . . . . .
H40 H 0.6474 0.3472 0.1587 0.055 Uiso 1 1 calc R U . . .
C41 C 0.6425(2) 0.4121(5) 0.09167(13) 0.0539(9) Uani 1 1 d . . . . .
H41 H 0.6853 0.4955 0.0987 0.065 Uiso 1 1 calc R U . . .
C42 C 0.6025(2) 0.3762(5) 0.04586(13) 0.0559(10) Uani 1 1 d . . . . .
H42 H 0.6182 0.4347 0.0218 0.067 Uiso 1 1 calc R U . . .
C43 C 0.5392(2) 0.2539(5) 0.03548(11) 0.0517(9) Uani 1 1 d . . . . .
H43 H 0.5128 0.2274 0.0043 0.062 Uiso 1 1 calc R U . . .
C44 C 0.51459(18) 0.1706(4) 0.07084(10) 0.0435(8) Uani 1 1 d . . . . .
H44 H 0.4704 0.0912 0.0634 0.052 Uiso 1 1 calc R 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
Br1 C8 1.887(3) . ?
Br2 C30 1.892(3) . ?
N1 C4 1.280(4) . ?
N1 C3 1.382(4) . ?
N2 C26 1.280(3) . ?
N2 C25 1.386(4) . ?
O1 C1 1.199(4) . ?
O2 C4 1.347(3) . ?
O2 C1 1.385(4) . ?
O3 C23 1.203(3) . ?
O4 C26 1.359(3) . ?
O4 C23 1.383(3) . ?
C1 C2 1.440(4) . ?
C2 C3 1.362(4) . ?
C2 C11 1.483(4) . ?
C3 C17 1.495(4) . ?
C4 C5 1.451(4) . ?
C5 C6 1.388(4) . ?
C5 C10 1.392(4) . ?
C6 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(4) . ?
C9 C10 1.372(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.373(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.379(4) . ?
C17 C18 1.381(4) . ?
C18 C19 1.379(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.358(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.445(4) . ?
C24 C25 1.368(4) . ?
C24 C33 1.479(4) . ?
C25 C39 1.482(4) . ?
C26 C27 1.457(4) . ?
C27 C28 1.379(4) . ?
C27 C32 1.393(4) . ?
C28 C29 1.374(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.367(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.372(4) . ?
C31 C32 1.370(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C38 1.383(4) . ?
C33 C34 1.393(4) . ?
C34 C35 1.381(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.361(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.373(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.375(4) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C40 1.384(4) . ?
C39 C44 1.385(4) . ?
C40 C41 1.386(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.368(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.370(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.371(4) . ?
C43 H43 0.9300 . ?
C44 H44 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
C4 N1 C3 118.1(3) . . ?
C26 N2 C25 118.1(2) . . ?
C4 O2 C1 121.3(3) . . ?
C26 O4 C23 121.0(2) . . ?
O1 C1 O2 116.6(3) . . ?
O1 C1 C2 127.4(3) . . ?
O2 C1 C2 116.0(3) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 C11 124.0(3) . . ?
C1 C2 C11 118.4(3) . . ?
C2 C3 N1 122.5(3) . . ?
C2 C3 C17 123.8(3) . . ?
N1 C3 C17 113.7(2) . . ?
N1 C4 O2 123.7(3) . . ?
N1 C4 C5 123.1(3) . . ?
O2 C4 C5 113.3(3) . . ?
C6 C5 C10 118.4(3) . . ?
C6 C5 C4 119.8(3) . . ?
C10 C5 C4 121.8(3) . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.0(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 Br1 119.3(3) . . ?
C7 C8 Br1 119.2(3) . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C16 C11 C12 118.2(3) . . ?
C16 C11 C2 120.0(3) . . ?
C12 C11 C2 121.8(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C22 C17 C18 119.2(3) . . ?
C22 C17 C3 120.2(3) . . ?
C18 C17 C3 120.4(3) . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
O3 C23 O4 116.2(3) . . ?
O3 C23 C24 127.8(3) . . ?
O4 C23 C24 116.0(3) . . ?
C25 C24 C23 118.2(3) . . ?
C25 C24 C33 125.0(3) . . ?
C23 C24 C33 116.7(3) . . ?
C24 C25 N2 122.3(3) . . ?
C24 C25 C39 124.6(3) . . ?
N2 C25 C39 113.1(2) . . ?
N2 C26 O4 124.3(3) . . ?
N2 C26 C27 123.2(3) . . ?
O4 C26 C27 112.5(3) . . ?
C28 C27 C32 118.5(3) . . ?
C28 C27 C26 120.1(3) . . ?
C32 C27 C26 121.4(3) . . ?
C29 C28 C27 121.1(3) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C30 C29 C28 119.0(3) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C29 C30 C31 121.5(3) . . ?
C29 C30 Br2 119.2(2) . . ?
C31 C30 Br2 119.2(2) . . ?
C32 C31 C30 119.2(3) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C31 C32 C27 120.7(3) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C38 C33 C34 118.5(3) . . ?
C38 C33 C24 120.7(3) . . ?
C34 C33 C24 120.7(3) . . ?
C35 C34 C33 119.3(3) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C36 C35 C34 121.5(3) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C37 119.6(3) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C36 C37 C38 119.8(3) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C37 C38 C33 121.2(3) . . ?
C37 C38 H38 119.4 . . ?
C33 C38 H38 119.4 . . ?
C40 C39 C44 118.3(3) . . ?
C40 C39 C25 121.3(3) . . ?
C44 C39 C25 120.1(3) . . ?
C39 C40 C41 120.4(3) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C42 C41 C40 120.1(3) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 120.0(3) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C44 C43 C42 120.3(3) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C39 120.9(3) . . ?
C43 C44 H44 119.6 . . ?
C39 C44 H44 119.6 . . ?

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
C4 O2 C1 O1 177.7(4) . . . . ?
C4 O2 C1 C2 -3.4(5) . . . . ?
O1 C1 C2 C3 174.0(4) . . . . ?
O2 C1 C2 C3 -4.8(5) . . . . ?
O1 C1 C2 C11 -7.2(7) . . . . ?
O2 C1 C2 C11 174.0(3) . . . . ?
C1 C2 C3 N1 10.3(5) . . . . ?
C11 C2 C3 N1 -168.4(3) . . . . ?
C1 C2 C3 C17 -168.7(3) . . . . ?
C11 C2 C3 C17 12.6(5) . . . . ?
C4 N1 C3 C2 -7.2(4) . . . . ?
C4 N1 C3 C17 171.8(3) . . . . ?
C3 N1 C4 O2 -1.7(5) . . . . ?
C3 N1 C4 C5 179.1(3) . . . . ?
C1 O2 C4 N1 7.0(5) . . . . ?
C1 O2 C4 C5 -173.7(3) . . . . ?
N1 C4 C5 C6 12.4(5) . . . . ?
O2 C4 C5 C6 -166.9(3) . . . . ?
N1 C4 C5 C10 -168.5(3) . . . . ?
O2 C4 C5 C10 12.2(4) . . . . ?
C10 C5 C6 C7 0.0(5) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C6 C7 C8 Br1 -178.2(2) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
Br1 C8 C9 C10 178.0(3) . . . . ?
C8 C9 C10 C5 0.8(5) . . . . ?
C6 C5 C10 C9 -0.2(5) . . . . ?
C4 C5 C10 C9 -179.3(3) . . . . ?
C3 C2 C11 C16 54.9(5) . . . . ?
C1 C2 C11 C16 -123.9(4) . . . . ?
C3 C2 C11 C12 -126.1(4) . . . . ?
C1 C2 C11 C12 55.2(5) . . . . ?
C16 C11 C12 C13 -2.6(5) . . . . ?
C2 C11 C12 C13 178.4(3) . . . . ?
C11 C12 C13 C14 1.9(5) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 C11 0.0(6) . . . . ?
C12 C11 C16 C15 1.6(5) . . . . ?
C2 C11 C16 C15 -179.3(3) . . . . ?
C2 C3 C17 C22 -136.6(3) . . . . ?
N1 C3 C17 C22 44.3(4) . . . . ?
C2 C3 C17 C18 48.9(4) . . . . ?
N1 C3 C17 C18 -130.1(3) . . . . ?
C22 C17 C18 C19 -0.8(5) . . . . ?
C3 C17 C18 C19 173.7(3) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 C22 -1.8(5) . . . . ?
C20 C21 C22 C17 2.1(5) . . . . ?
C18 C17 C22 C21 -0.8(4) . . . . ?
C3 C17 C22 C21 -175.3(3) . . . . ?
C26 O4 C23 O3 178.5(3) . . . . ?
C26 O4 C23 C24 -2.3(4) . . . . ?
O3 C23 C24 C25 -176.7(3) . . . . ?
O4 C23 C24 C25 4.2(4) . . . . ?
O3 C23 C24 C33 5.5(5) . . . . ?
O4 C23 C24 C33 -173.6(3) . . . . ?
C23 C24 C25 N2 -4.5(4) . . . . ?
C33 C24 C25 N2 173.1(3) . . . . ?
C23 C24 C25 C39 174.2(3) . . . . ?
C33 C24 C25 C39 -8.2(5) . . . . ?
C26 N2 C25 C24 2.7(4) . . . . ?
C26 N2 C25 C39 -176.1(3) . . . . ?
C25 N2 C26 O4 -0.6(4) . . . . ?
C25 N2 C26 C27 178.0(3) . . . . ?
C23 O4 C26 N2 0.6(4) . . . . ?
C23 O4 C26 C27 -178.2(2) . . . . ?
N2 C26 C27 C28 13.7(4) . . . . ?
O4 C26 C27 C28 -167.5(2) . . . . ?
N2 C26 C27 C32 -165.5(3) . . . . ?
O4 C26 C27 C32 13.3(4) . . . . ?
C32 C27 C28 C29 0.0(4) . . . . ?
C26 C27 C28 C29 -179.2(3) . . . . ?
C27 C28 C29 C30 0.4(4) . . . . ?
C28 C29 C30 C31 -0.7(5) . . . . ?
C28 C29 C30 Br2 177.8(2) . . . . ?
C29 C30 C31 C32 0.6(5) . . . . ?
Br2 C30 C31 C32 -177.9(3) . . . . ?
C30 C31 C32 C27 -0.2(5) . . . . ?
C28 C27 C32 C31 -0.1(5) . . . . ?
C26 C27 C32 C31 179.1(3) . . . . ?
C25 C24 C33 C38 -56.2(4) . . . . ?
C23 C24 C33 C38 121.4(3) . . . . ?
C25 C24 C33 C34 125.7(3) . . . . ?
C23 C24 C33 C34 -56.7(4) . . . . ?
C38 C33 C34 C35 1.2(5) . . . . ?
C24 C33 C34 C35 179.4(3) . . . . ?
C33 C34 C35 C36 -1.0(5) . . . . ?
C34 C35 C36 C37 0.2(6) . . . . ?
C35 C36 C37 C38 0.3(5) . . . . ?
C36 C37 C38 C33 0.0(5) . . . . ?
C34 C33 C38 C37 -0.8(5) . . . . ?
C24 C33 C38 C37 -179.0(3) . . . . ?
C24 C25 C39 C40 -45.3(4) . . . . ?
N2 C25 C39 C40 133.5(3) . . . . ?
C24 C25 C39 C44 139.8(3) . . . . ?
N2 C25 C39 C44 -41.4(4) . . . . ?
C44 C39 C40 C41 0.6(4) . . . . ?
C25 C39 C40 C41 -174.3(3) . . . . ?
C39 C40 C41 C42 -1.3(5) . . . . ?
C40 C41 C42 C43 0.3(5) . . . . ?
C41 C42 C43 C44 1.5(5) . . . . ?
C42 C43 C44 C39 -2.2(5) . . . . ?
C40 C39 C44 C43 1.1(4) . . . . ?
C25 C39 C44 C43 176.1(3) . . . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v17405
_database_code_depnum_ccdc_archive 'CCDC 1576769'
_audit_update_record             
;
2017-09-27 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Br N O2'
_chemical_formula_weight         356.21

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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

_cell_length_a                   15.2706(5)
_cell_length_b                   18.9516(6)
_cell_length_c                   11.5233(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.0310(10)
_cell_angle_gamma                90
_cell_volume                     3220.77(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      4.516
_cell_measurement_theta_max      48.620

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.558
_shelx_estimated_absorpt_T_min   0.629
_shelx_estimated_absorpt_T_max   0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5907
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69652
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5982
_reflns_number_gt                3687
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+5.2812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5982
_refine_ls_number_parameters     419
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.008
_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_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 0.26384(3) 0.42217(3) 0.19588(5) 0.0914(2) Uani 1 1 d . . . . .
Br2 Br 0.23145(5) 0.25851(4) 0.50521(7) 0.1452(4) Uani 1 1 d . . . . .
O1 O 0.76934(19) 0.33502(18) 0.7555(3) 0.0745(9) Uani 1 1 d . . . . .
O2 O 0.67150(16) 0.38515(14) 0.6032(2) 0.0524(7) Uani 1 1 d . . . . .
O3 O 0.7886(2) 0.19864(16) 0.9572(3) 0.0642(8) Uani 1 1 d . . . . .
O4 O 0.65375(18) 0.24559(14) 0.8822(2) 0.0572(7) Uani 1 1 d . . . . .
N1 N 0.7108(2) 0.47493(18) 0.4898(3) 0.0576(9) Uani 1 1 d . . . . .
N2 N 0.6137(2) 0.3566(2) 0.9355(4) 0.0789(12) Uani 1 1 d . . . . .
C1 C 0.7593(3) 0.3788(2) 0.6782(3) 0.0507(10) Uani 1 1 d . . . . .
C2 C 0.8256(2) 0.4260(2) 0.6529(3) 0.0464(9) Uani 1 1 d . . . . .
C3 C 0.7993(3) 0.4720(2) 0.5616(4) 0.0546(10) Uani 1 1 d . . . . .
C4 C 0.6533(3) 0.4320(2) 0.5118(3) 0.0498(9) Uani 1 1 d . . . . .
C5 C 0.5585(2) 0.4298(2) 0.4393(3) 0.0501(9) Uani 1 1 d . . . . .
C6 C 0.4981(3) 0.3798(2) 0.4581(4) 0.0625(11) Uani 1 1 d . . . . .
H6 H 0.5165 0.3471 0.5197 0.075 Uiso 1 1 calc R U . . .
C7 C 0.4102(3) 0.3780(3) 0.3859(4) 0.0698(13) Uani 1 1 d . . . . .
H7 H 0.3698 0.3439 0.3984 0.084 Uiso 1 1 calc R U . . .
C8 C 0.3834(3) 0.4264(3) 0.2962(4) 0.0612(11) Uani 1 1 d . . . . .
C9 C 0.4415(3) 0.4779(3) 0.2771(4) 0.0673(12) Uani 1 1 d . . . . .
H9 H 0.4220 0.5112 0.2167 0.081 Uiso 1 1 calc R U . . .
C10 C 0.5292(3) 0.4793(2) 0.3491(4) 0.0629(11) Uani 1 1 d . . . . .
H10 H 0.5691 0.5139 0.3369 0.075 Uiso 1 1 calc R U . . .
C11 C 0.9204(2) 0.4197(2) 0.7287(3) 0.0471(9) Uani 1 1 d . . . . .
C12 C 0.9720(3) 0.3610(2) 0.7207(4) 0.0617(11) Uani 1 1 d . . . . .
H12 H 0.9468 0.3242 0.6695 0.074 Uiso 1 1 calc R U . . .
C13 C 1.0610(3) 0.3568(3) 0.7886(5) 0.0738(13) Uani 1 1 d . . . . .
H13 H 1.0954 0.3172 0.7823 0.089 Uiso 1 1 calc R U . . .
C14 C 1.0991(3) 0.4104(3) 0.8650(4) 0.0679(13) Uani 1 1 d . . . . .
H14 H 1.1591 0.4073 0.9097 0.082 Uiso 1 1 calc R U . . .
C15 C 1.0486(3) 0.4681(3) 0.8754(4) 0.0678(12) Uani 1 1 d . . . . .
H15 H 1.0740 0.5043 0.9279 0.081 Uiso 1 1 calc R U . . .
C16 C 0.9598(3) 0.4732(2) 0.8079(4) 0.0626(11) Uani 1 1 d . . . . .
H16 H 0.9258 0.5128 0.8154 0.075 Uiso 1 1 calc R U . . .
C17 C 0.8611(3) 0.5236(3) 0.5234(5) 0.0792(15) Uani 1 1 d . . . . .
H17A H 0.8355 0.5706 0.5200 0.095 Uiso 1 1 calc R U . . .
H17B H 0.9194 0.5239 0.5824 0.095 Uiso 1 1 calc R U . . .
C18 C 0.8736(4) 0.5056(5) 0.4092(6) 0.147(3) Uani 1 1 d . . . . .
H18A H 0.8994 0.4592 0.4127 0.221 Uiso 1 1 calc R U . . .
H18B H 0.9137 0.5391 0.3873 0.221 Uiso 1 1 calc R U . . .
H18C H 0.8161 0.5063 0.3504 0.221 Uiso 1 1 calc R U . . .
C19 C 0.7418(3) 0.2490(2) 0.9569(3) 0.0512(10) Uani 1 1 d . . . . .
C20 C 0.7636(3) 0.3132(2) 1.0259(3) 0.0529(10) Uani 1 1 d . . . . .
C21 C 0.6999(3) 0.3634(2) 1.0143(4) 0.0703(13) Uani 1 1 d D . . . .
C22 C 0.5964(3) 0.3006(2) 0.8744(4) 0.0608(11) Uani 1 1 d . . . . .
C23 C 0.5088(3) 0.2893(3) 0.7843(4) 0.0676(12) Uani 1 1 d . . . . .
C24 C 0.4377(3) 0.3347(3) 0.7819(5) 0.0902(17) Uani 1 1 d . . . . .
H24 H 0.4455 0.3718 0.8366 0.108 Uiso 1 1 calc R U . . .
C25 C 0.3546(4) 0.3258(3) 0.6988(6) 0.103(2) Uani 1 1 d . . . . .
H25 H 0.3068 0.3564 0.6977 0.124 Uiso 1 1 calc R U . . .
C26 C 0.3441(4) 0.2719(3) 0.6192(5) 0.0941(19) Uani 1 1 d . . . . .
C27 C 0.4135(4) 0.2264(3) 0.6189(5) 0.0946(18) Uani 1 1 d . . . . .
H27 H 0.4051 0.1899 0.5631 0.114 Uiso 1 1 calc R U . . .
C28 C 0.4970(4) 0.2350(3) 0.7027(4) 0.0818(15) Uani 1 1 d . . . . .
H28 H 0.5444 0.2040 0.7034 0.098 Uiso 1 1 calc R U . . .
C29 C 0.8587(3) 0.3196(2) 1.1021(3) 0.0519(10) Uani 1 1 d . . . . .
C30 C 0.9295(3) 0.3227(2) 1.0480(4) 0.0621(11) Uani 1 1 d . . . . .
H30 H 0.9178 0.3208 0.9647 0.074 Uiso 1 1 calc R U . . .
C31 C 1.0176(3) 0.3286(2) 1.1177(5) 0.0713(13) Uani 1 1 d . . . . .
H31 H 1.0650 0.3311 1.0809 0.086 Uiso 1 1 calc R U . . .
C32 C 1.0360(3) 0.3308(2) 1.2403(5) 0.0725(13) Uani 1 1 d . . . . .
H32 H 1.0956 0.3345 1.2866 0.087 Uiso 1 1 calc R U . . .
C33 C 0.9666(3) 0.3276(2) 1.2943(4) 0.0715(13) Uani 1 1 d . . . . .
H33 H 0.9790 0.3294 1.3777 0.086 Uiso 1 1 calc R U . . .
C34 C 0.8774(3) 0.3217(2) 1.2261(4) 0.0623(11) Uani 1 1 d . . . . .
H34 H 0.8305 0.3192 1.2637 0.075 Uiso 1 1 calc R U . . .
C35 C 0.7169(10) 0.4302(5) 1.0839(13) 0.108(3) Uani 0.7 1 d D U P A 1
H35A H 0.7495 0.4174 1.1651 0.130 Uiso 0.7 1 calc R U P A 1
H35B H 0.7588 0.4573 1.0511 0.130 Uiso 0.7 1 calc R U P A 1
C36 C 0.6467(8) 0.4782(7) 1.0948(13) 0.111(3) Uani 0.5 1 d D U P A 1
H36A H 0.6281 0.5061 1.0230 0.166 Uiso 0.5 1 calc R U P A 1
H36B H 0.6692 0.5087 1.1625 0.166 Uiso 0.5 1 calc R U P A 1
H36C H 0.5958 0.4520 1.1062 0.166 Uiso 0.5 1 calc R U P A 1
C35' C 0.709(3) 0.4410(11) 1.058(3) 0.108(3) Uani 0.3 1 d D U P A 2
H35C H 0.7720 0.4545 1.0892 0.129 Uiso 0.3 1 calc R U P A 2
H35D H 0.6796 0.4733 0.9948 0.129 Uiso 0.3 1 calc R U P A 2
C36' C 0.6596(8) 0.4384(7) 1.1587(12) 0.106(3) Uani 0.5 1 d D U P A 2
H36D H 0.5955 0.4345 1.1237 0.158 Uiso 0.5 1 calc R U P A 2
H36E H 0.6721 0.4807 1.2057 0.158 Uiso 0.5 1 calc R U P A 2
H36F H 0.6803 0.3983 1.2092 0.158 Uiso 0.5 1 calc R U P A 2


_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 C8 1.892(4) . ?
Br2 C26 1.891(5) . ?
O1 C1 1.198(4) . ?
O2 C4 1.350(4) . ?
O2 C1 1.399(4) . ?
O3 C19 1.193(5) . ?
O4 C22 1.349(5) . ?
O4 C19 1.397(4) . ?
N1 C4 1.270(5) . ?
N1 C3 1.390(5) . ?
N2 C22 1.264(5) . ?
N2 C21 1.398(5) . ?
C1 C2 1.437(5) . ?
C2 C3 1.345(5) . ?
C2 C11 1.489(5) . ?
C3 C17 1.502(6) . ?
C4 C5 1.473(5) . ?
C5 C6 1.378(5) . ?
C5 C10 1.385(6) . ?
C6 C7 1.384(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.363(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(6) . ?
C9 C10 1.381(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.379(6) . ?
C11 C16 1.392(5) . ?
C12 C13 1.384(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.419(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.444(6) . ?
C20 C21 1.341(6) . ?
C20 C29 1.495(5) . ?
C21 C35 1.486(10) . ?
C21 C35' 1.551(19) . ?
C22 C23 1.480(6) . ?
C23 C28 1.375(7) . ?
C23 C24 1.381(7) . ?
C24 C25 1.387(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.355(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(8) . ?
C27 C28 1.394(7) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.382(6) . ?
C29 C34 1.383(5) . ?
C30 C31 1.382(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.367(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.363(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.389(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.437(14) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C35' C36' 1.54(2) . ?
C35' H35C 0.9700 . ?
C35' H35D 0.9700 . ?
C36' H36D 0.9600 . ?
C36' H36E 0.9600 . ?
C36' H36F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C1 120.6(3) . . ?
C22 O4 C19 120.6(3) . . ?
C4 N1 C3 118.1(3) . . ?
C22 N2 C21 117.7(4) . . ?
O1 C1 O2 115.9(3) . . ?
O1 C1 C2 128.4(4) . . ?
O2 C1 C2 115.7(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C11 124.0(3) . . ?
C1 C2 C11 117.4(3) . . ?
C2 C3 N1 122.6(4) . . ?
C2 C3 C17 124.5(4) . . ?
N1 C3 C17 112.8(3) . . ?
N1 C4 O2 124.3(3) . . ?
N1 C4 C5 122.3(4) . . ?
O2 C4 C5 113.4(3) . . ?
C6 C5 C10 119.0(4) . . ?
C6 C5 C4 122.0(4) . . ?
C10 C5 C4 119.0(4) . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 119.5(4) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 121.3(4) . . ?
C7 C8 Br1 119.2(3) . . ?
C9 C8 Br1 119.5(4) . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C5 120.7(4) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C12 C11 C16 118.3(4) . . ?
C12 C11 C2 120.7(3) . . ?
C16 C11 C2 120.9(4) . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.7(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C18 C17 C3 111.1(5) . . ?
C18 C17 H17A 109.4 . . ?
C3 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C3 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O4 116.4(4) . . ?
O3 C19 C20 128.3(4) . . ?
O4 C19 C20 115.3(4) . . ?
C21 C20 C19 119.0(4) . . ?
C21 C20 C29 124.8(4) . . ?
C19 C20 C29 116.2(4) . . ?
C20 C21 N2 122.4(4) . . ?
C20 C21 C35 122.0(7) . . ?
N2 C21 C35 115.6(7) . . ?
C20 C21 C35' 129.7(16) . . ?
N2 C21 C35' 106.8(17) . . ?
N2 C22 O4 125.0(4) . . ?
N2 C22 C23 122.1(4) . . ?
O4 C22 C23 112.8(4) . . ?
C28 C23 C24 119.3(4) . . ?
C28 C23 C22 121.5(5) . . ?
C24 C23 C22 119.2(5) . . ?
C23 C24 C25 120.8(6) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 119.1(6) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C27 121.4(5) . . ?
C25 C26 Br2 119.9(5) . . ?
C27 C26 Br2 118.7(5) . . ?
C26 C27 C28 119.6(6) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C23 C28 C27 119.7(5) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C30 C29 C34 119.3(4) . . ?
C30 C29 C20 119.5(4) . . ?
C34 C29 C20 121.2(4) . . ?
C29 C30 C31 119.9(4) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C32 C31 C30 120.7(5) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C33 C32 C31 119.7(4) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 120.6(4) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C29 C34 C33 119.7(4) . . ?
C29 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C36 C35 C21 123.9(13) . . ?
C36 C35 H35A 106.4 . . ?
C21 C35 H35A 106.4 . . ?
C36 C35 H35B 106.4 . . ?
C21 C35 H35B 106.4 . . ?
H35A C35 H35B 106.4 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C36' C35' C21 101.3(14) . . ?
C36' C35' H35C 111.5 . . ?
C21 C35' H35C 111.5 . . ?
C36' C35' H35D 111.5 . . ?
C21 C35' H35D 111.5 . . ?
H35C C35' H35D 109.3 . . ?
C35' C36' H36D 109.5 . . ?
C35' C36' H36E 109.5 . . ?
H36D C36' H36E 109.5 . . ?
C35' C36' H36F 109.5 . . ?
H36D C36' H36F 109.5 . . ?
H36E C36' H36F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O2 C1 O1 -178.7(4) . . . . ?
C4 O2 C1 C2 1.6(5) . . . . ?
O1 C1 C2 C3 -179.3(4) . . . . ?
O2 C1 C2 C3 0.2(5) . . . . ?
O1 C1 C2 C11 2.0(7) . . . . ?
O2 C1 C2 C11 -178.4(3) . . . . ?
C1 C2 C3 N1 -0.9(6) . . . . ?
C11 C2 C3 N1 177.7(4) . . . . ?
C1 C2 C3 C17 -179.0(4) . . . . ?
C11 C2 C3 C17 -0.4(7) . . . . ?
C4 N1 C3 C2 -0.4(6) . . . . ?
C4 N1 C3 C17 177.9(4) . . . . ?
C3 N1 C4 O2 2.5(6) . . . . ?
C3 N1 C4 C5 -178.6(4) . . . . ?
C1 O2 C4 N1 -3.1(6) . . . . ?
C1 O2 C4 C5 177.8(3) . . . . ?
N1 C4 C5 C6 175.2(4) . . . . ?
O2 C4 C5 C6 -5.7(6) . . . . ?
N1 C4 C5 C10 -4.5(6) . . . . ?
O2 C4 C5 C10 174.6(4) . . . . ?
C10 C5 C6 C7 1.7(7) . . . . ?
C4 C5 C6 C7 -178.0(4) . . . . ?
C5 C6 C7 C8 -0.5(7) . . . . ?
C6 C7 C8 C9 -1.0(7) . . . . ?
C6 C7 C8 Br1 178.7(3) . . . . ?
C7 C8 C9 C10 1.3(7) . . . . ?
Br1 C8 C9 C10 -178.4(3) . . . . ?
C8 C9 C10 C5 -0.1(7) . . . . ?
C6 C5 C10 C9 -1.4(7) . . . . ?
C4 C5 C10 C9 178.3(4) . . . . ?
C3 C2 C11 C12 -110.0(5) . . . . ?
C1 C2 C11 C12 68.5(5) . . . . ?
C3 C2 C11 C16 68.9(6) . . . . ?
C1 C2 C11 C16 -112.5(4) . . . . ?
C16 C11 C12 C13 -1.2(6) . . . . ?
C2 C11 C12 C13 177.8(4) . . . . ?
C11 C12 C13 C14 0.4(7) . . . . ?
C12 C13 C14 C15 0.6(7) . . . . ?
C13 C14 C15 C16 -0.9(7) . . . . ?
C14 C15 C16 C11 0.0(7) . . . . ?
C12 C11 C16 C15 1.0(6) . . . . ?
C2 C11 C16 C15 -178.0(4) . . . . ?
C2 C3 C17 C18 111.5(6) . . . . ?
N1 C3 C17 C18 -66.8(6) . . . . ?
C22 O4 C19 O3 -178.9(4) . . . . ?
C22 O4 C19 C20 2.2(5) . . . . ?
O3 C19 C20 C21 -178.4(4) . . . . ?
O4 C19 C20 C21 0.3(6) . . . . ?
O3 C19 C20 C29 4.1(6) . . . . ?
O4 C19 C20 C29 -177.2(3) . . . . ?
C19 C20 C21 N2 -1.7(7) . . . . ?
C29 C20 C21 N2 175.6(4) . . . . ?
C19 C20 C21 C35 178.9(7) . . . . ?
C29 C20 C21 C35 -3.8(10) . . . . ?
C19 C20 C21 C35' -167.9(14) . . . . ?
C29 C20 C21 C35' 9.3(15) . . . . ?
C22 N2 C21 C20 0.5(8) . . . . ?
C22 N2 C21 C35 179.9(7) . . . . ?
C22 N2 C21 C35' 169.5(10) . . . . ?
C21 N2 C22 O4 2.2(7) . . . . ?
C21 N2 C22 C23 -177.1(4) . . . . ?
C19 O4 C22 N2 -3.7(6) . . . . ?
C19 O4 C22 C23 175.7(3) . . . . ?
N2 C22 C23 C28 167.3(5) . . . . ?
O4 C22 C23 C28 -12.2(6) . . . . ?
N2 C22 C23 C24 -12.4(7) . . . . ?
O4 C22 C23 C24 168.1(4) . . . . ?
C28 C23 C24 C25 0.4(8) . . . . ?
C22 C23 C24 C25 -179.9(5) . . . . ?
C23 C24 C25 C26 -0.2(9) . . . . ?
C24 C25 C26 C27 -0.2(9) . . . . ?
C24 C25 C26 Br2 179.9(4) . . . . ?
C25 C26 C27 C28 0.5(9) . . . . ?
Br2 C26 C27 C28 -179.6(4) . . . . ?
C24 C23 C28 C27 0.0(7) . . . . ?
C22 C23 C28 C27 -179.7(5) . . . . ?
C26 C27 C28 C23 -0.4(8) . . . . ?
C21 C20 C29 C30 -112.7(5) . . . . ?
C19 C20 C29 C30 64.6(5) . . . . ?
C21 C20 C29 C34 68.0(6) . . . . ?
C19 C20 C29 C34 -114.6(4) . . . . ?
C34 C29 C30 C31 -0.7(7) . . . . ?
C20 C29 C30 C31 -180.0(4) . . . . ?
C29 C30 C31 C32 0.5(7) . . . . ?
C30 C31 C32 C33 -0.3(7) . . . . ?
C31 C32 C33 C34 0.3(7) . . . . ?
C30 C29 C34 C33 0.7(6) . . . . ?
C20 C29 C34 C33 179.9(4) . . . . ?
C32 C33 C34 C29 -0.5(7) . . . . ?
C20 C21 C35 C36 -166.0(12) . . . . ?
N2 C21 C35 C36 14.6(17) . . . . ?
C35' C21 C35 C36 64(7) . . . . ?
C20 C21 C35' C36' -110.3(19) . . . . ?
N2 C21 C35' C36' 82(2) . . . . ?
C35 C21 C35' C36' -52(6) . . . . ?

_refine_diff_density_max         0.879
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4



