# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2019

####################################################################### 
# 
# 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_r10018
_database_code_depnum_ccdc_archive 'CCDC 1867907'
loop_
_audit_author_name
_audit_author_address
'Nigam Rath'
;University of Missouri- St. Louis
United States of America
;
_audit_update_record             
;
2018-09-14 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H11 N), C6 H4 Br1.25 Cl0.75 O2'
_chemical_formula_sum            'C32 H26 Br1.25 Cl0.75 N2 O2'
_chemical_formula_weight         597.02

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.9120(17)
_cell_length_b                   10.9997(17)
_cell_length_c                   11.6021(18)
_cell_angle_alpha                91.680(8)
_cell_angle_beta                 97.459(8)
_cell_angle_gamma                91.733(8)
_cell_volume                     1379.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1689
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      19.16

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             609
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.594
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    1.957
_shelx_estimated_absorpt_T_min   0.389
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3447
_exptl_absorpt_correction_T_max  0.4901
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            11536
_diffrn_reflns_av_unetI/netI     0.1263
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.771
_diffrn_reflns_theta_max         25.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4891
_reflns_number_gt                2146
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4891
_refine_ls_number_parameters     364
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_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
O1 O 0.2034(3) 1.0011(3) 0.1463(3) 0.0741(9) Uani 1 1 d . . . . .
H1A H 0.177544 0.978597 0.079329 0.111 Uiso 1 1 calc R U . . .
O2 O 0.5508(3) 0.7707(3) 0.0686(3) 0.0798(10) Uani 1 1 d . . . . .
H2A H 0.509502 0.762062 0.004428 0.120 Uiso 1 1 calc R U . . .
C27 C 0.3103(4) 0.9475(4) 0.1806(4) 0.0546(12) Uani 1 1 d . . . . .
C28 C 0.3576(4) 0.9546(3) 0.2975(3) 0.0508(11) Uani 1 1 d D . . . .
C29 C 0.4667(4) 0.9003(3) 0.3360(4) 0.0529(12) Uani 1 1 d . . . . .
H29 H 0.497907 0.905547 0.414516 0.063 Uiso 1 1 calc R U . . .
C30 C 0.5295(4) 0.8386(3) 0.2591(4) 0.0539(12) Uani 1 1 d D . . . .
C31 C 0.4851(4) 0.8306(4) 0.1419(4) 0.0566(12) Uani 1 1 d . . . . .
C32 C 0.3762(4) 0.8864(4) 0.1032(4) 0.0609(13) Uani 1 1 d . . . . .
H32 H 0.346621 0.883026 0.024276 0.073 Uiso 1 1 calc R U . . .
Br1 Br 0.2700(6) 1.0432(6) 0.3999(5) 0.0633(9) Uani 0.618(3) 1 d D . P A 1
Br2 Br 0.6748(2) 0.76010(18) 0.31330(19) 0.0616(5) Uani 0.618(3) 1 d D . P A 1
Cl1 Cl 0.293(2) 1.031(2) 0.4054(19) 0.062(4) Uani 0.382(3) 1 d D . P A 2
Cl2 Cl 0.6617(12) 0.7624(11) 0.3066(11) 0.144(6) Uani 0.382(3) 1 d D . P A 2
N1 N 0.1193(4) 0.9447(4) -0.0769(4) 0.0729(12) Uani 1 1 d . . . . .
C1 C 0.1563(5) 1.0072(5) -0.1609(5) 0.0859(16) Uani 1 1 d . . . . .
H1 H 0.201354 1.079647 -0.141328 0.103 Uiso 1 1 calc R U . . .
C2 C 0.1324(5) 0.9721(5) -0.2757(4) 0.0868(16) Uani 1 1 d . . . . .
H2 H 0.161113 1.020884 -0.331382 0.104 Uiso 1 1 calc R U . . .
C3 C 0.0675(4) 0.8672(5) -0.3098(4) 0.0629(13) Uani 1 1 d . . . . .
C4 C 0.0238(4) 0.8035(4) -0.2242(5) 0.0790(15) Uani 1 1 d . . . . .
H4 H -0.024657 0.732725 -0.241920 0.095 Uiso 1 1 calc R U . . .
C5 C 0.0527(5) 0.8458(5) -0.1103(5) 0.0877(17) Uani 1 1 d . . . . .
H5 H 0.022471 0.800592 -0.052964 0.105 Uiso 1 1 calc R U . . .
C6 C 0.0489(4) 0.8294(5) -0.4341(4) 0.0792(15) Uani 1 1 d . . . . .
H6 H 0.079306 0.883300 -0.484685 0.095 Uiso 1 1 calc R U . . .
C7 C -0.0040(4) 0.7314(4) -0.4805(4) 0.0739(15) Uani 1 1 d . . . . .
H7 H -0.040919 0.681266 -0.430853 0.089 Uiso 1 1 calc R U . . .
C8 C -0.0138(4) 0.6881(5) -0.6019(4) 0.0648(13) Uani 1 1 d . . . . .
C9 C 0.0370(4) 0.7527(5) -0.6855(5) 0.0823(16) Uani 1 1 d . . . . .
H9 H 0.077549 0.827326 -0.665156 0.099 Uiso 1 1 calc R U . . .
C10 C 0.0283(5) 0.7085(6) -0.7975(5) 0.108(2) Uani 1 1 d . . . . .
H10 H 0.063717 0.752647 -0.852619 0.129 Uiso 1 1 calc R U . . .
C11 C -0.0324(5) 0.5991(6) -0.8292(5) 0.103(2) Uani 1 1 d . . . . .
H11 H -0.038332 0.569250 -0.905621 0.124 Uiso 1 1 calc R U . . .
C12 C -0.0834(5) 0.5354(5) -0.7493(6) 0.0952(18) Uani 1 1 d . . . . .
H12 H -0.125227 0.461582 -0.770781 0.114 Uiso 1 1 calc R U . . .
C13 C -0.0739(4) 0.5792(5) -0.6348(5) 0.0785(15) Uani 1 1 d . . . . .
H13 H -0.108720 0.534078 -0.580027 0.094 Uiso 1 1 calc R U . . .
N2 N 0.4321(3) 0.7317(4) -0.1460(3) 0.0658(11) Uani 1 1 d . . . . .
C14 C 0.4170(4) 0.8139(5) -0.2270(5) 0.0757(15) Uani 1 1 d . . . . .
H14 H 0.428201 0.895575 -0.203842 0.091 Uiso 1 1 calc R U . . .
C15 C 0.3856(4) 0.7857(4) -0.3435(4) 0.0709(14) Uani 1 1 d . . . . .
H15 H 0.374302 0.847689 -0.396189 0.085 Uiso 1 1 calc R U . . .
C16 C 0.3707(4) 0.6659(4) -0.3826(4) 0.0592(13) Uani 1 1 d . . . . .
C17 C 0.3861(4) 0.5811(4) -0.2978(4) 0.0676(14) Uani 1 1 d . . . . .
H17 H 0.376163 0.498750 -0.318448 0.081 Uiso 1 1 calc R U . . .
C18 C 0.4156(4) 0.6165(5) -0.1838(4) 0.0695(14) Uani 1 1 d . . . . .
H18 H 0.424910 0.556206 -0.129114 0.083 Uiso 1 1 calc R U . . .
C19 C 0.3407(4) 0.6364(4) -0.5076(4) 0.0693(14) Uani 1 1 d . . . . .
H19 H 0.325899 0.701479 -0.556335 0.083 Uiso 1 1 calc R U . . .
C20 C 0.3329(4) 0.5285(4) -0.5564(4) 0.0643(13) Uani 1 1 d . . . . .
H20 H 0.344609 0.464655 -0.505835 0.077 Uiso 1 1 calc R U . . .
C21 C 0.3083(4) 0.4932(4) -0.6798(4) 0.0606(13) Uani 1 1 d . . . . .
C22 C 0.3075(4) 0.5757(4) -0.7679(4) 0.0742(14) Uani 1 1 d . . . . .
H22 H 0.319442 0.658319 -0.748761 0.089 Uiso 1 1 calc R U . . .
C23 C 0.2892(4) 0.5377(5) -0.8834(4) 0.0842(16) Uani 1 1 d . . . . .
H23 H 0.288983 0.594267 -0.941371 0.101 Uiso 1 1 calc R U . . .
C24 C 0.2714(4) 0.4162(6) -0.9124(5) 0.0882(18) Uani 1 1 d . . . . .
H24 H 0.260184 0.390233 -0.990156 0.106 Uiso 1 1 calc R U . . .
C25 C 0.2700(4) 0.3333(5) -0.8274(6) 0.0886(18) Uani 1 1 d . . . . .
H25 H 0.256058 0.251082 -0.847500 0.106 Uiso 1 1 calc R U . . .
C26 C 0.2893(4) 0.3707(4) -0.7114(5) 0.0745(15) Uani 1 1 d . . . . .
H26 H 0.289502 0.313321 -0.654036 0.089 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
O1 C27 1.342(4) . ?
O1 H1A 0.8200 . ?
O2 C31 1.351(4) . ?
O2 H2A 0.8200 . ?
C27 C28 1.387(5) . ?
C27 C32 1.392(5) . ?
C28 C29 1.375(5) . ?
C28 Cl1 1.722(15) . ?
C28 Br1 1.887(6) . ?
C29 C30 1.370(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.383(5) . ?
C30 Cl2 1.727(13) . ?
C30 Br2 1.874(5) . ?
C31 C32 1.382(5) . ?
C32 H32 0.9300 . ?
N1 C1 1.308(5) . ?
N1 C5 1.310(6) . ?
C1 C2 1.366(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(6) . ?
C3 C6 1.475(6) . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.278(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.462(6) . ?
C7 H7 0.9300 . ?
C8 C13 1.368(6) . ?
C8 C9 1.382(6) . ?
C9 C10 1.365(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.345(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N2 C14 1.322(5) . ?
N2 C18 1.328(5) . ?
C14 C15 1.374(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 C19 1.469(6) . ?
C17 C18 1.363(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.296(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.461(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(6) . ?
C21 C26 1.388(5) . ?
C22 C23 1.380(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.364(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(6) . ?
C25 H25 0.9300 . ?
C26 H26 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
C27 O1 H1A 109.5 . . ?
C31 O2 H2A 109.5 . . ?
O1 C27 C28 118.7(4) . . ?
O1 C27 C32 122.6(4) . . ?
C28 C27 C32 118.7(4) . . ?
C29 C28 C27 120.4(4) . . ?
C29 C28 Cl1 113.9(10) . . ?
C27 C28 Cl1 125.7(10) . . ?
C29 C28 Br1 121.7(4) . . ?
C27 C28 Br1 117.9(4) . . ?
C30 C29 C28 120.3(4) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.7(4) . . ?
C29 C30 Cl2 121.1(6) . . ?
C31 C30 Cl2 118.1(5) . . ?
C29 C30 Br2 119.9(4) . . ?
C31 C30 Br2 119.3(3) . . ?
O2 C31 C32 122.1(4) . . ?
O2 C31 C30 119.0(4) . . ?
C32 C31 C30 118.9(4) . . ?
C31 C32 C27 121.0(4) . . ?
C31 C32 H32 119.5 . . ?
C27 C32 H32 119.5 . . ?
C1 N1 C5 115.2(4) . . ?
N1 C1 C2 123.7(5) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 116.2(5) . . ?
C2 C3 C6 119.4(5) . . ?
C4 C3 C6 124.4(5) . . ?
C3 C4 C5 118.8(5) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 125.1(5) . . ?
N1 C5 H5 117.5 . . ?
C4 C5 H5 117.5 . . ?
C7 C6 C3 127.8(5) . . ?
C7 C6 H6 116.1 . . ?
C3 C6 H6 116.1 . . ?
C6 C7 C8 128.3(5) . . ?
C6 C7 H7 115.9 . . ?
C8 C7 H7 115.9 . . ?
C13 C8 C9 118.1(5) . . ?
C13 C8 C7 119.5(5) . . ?
C9 C8 C7 122.3(5) . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.3(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.7(6) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.3(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 120.7(5) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C14 N2 C18 115.7(4) . . ?
N2 C14 C15 123.8(5) . . ?
N2 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C14 C15 C16 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 115.4(4) . . ?
C17 C16 C19 124.6(4) . . ?
C15 C16 C19 120.0(5) . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
N2 C18 C17 124.0(4) . . ?
N2 C18 H18 118.0 . . ?
C17 C18 H18 118.0 . . ?
C20 C19 C16 126.3(5) . . ?
C20 C19 H19 116.9 . . ?
C16 C19 H19 116.9 . . ?
C19 C20 C21 129.1(5) . . ?
C19 C20 H20 115.5 . . ?
C21 C20 H20 115.5 . . ?
C22 C21 C26 117.9(4) . . ?
C22 C21 C20 123.2(4) . . ?
C26 C21 C20 118.8(5) . . ?
C23 C22 C21 121.2(5) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 119.8(5) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.1(5) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.4(5) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.6(5) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 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
O1 C27 C28 C29 179.7(4) . . . . ?
C32 C27 C28 C29 -1.0(6) . . . . ?
O1 C27 C28 Cl1 -2.0(13) . . . . ?
C32 C27 C28 Cl1 177.3(12) . . . . ?
O1 C27 C28 Br1 -1.7(6) . . . . ?
C32 C27 C28 Br1 177.6(4) . . . . ?
C27 C28 C29 C30 -0.1(6) . . . . ?
Cl1 C28 C29 C30 -178.7(11) . . . . ?
Br1 C28 C29 C30 -178.7(4) . . . . ?
C28 C29 C30 C31 0.5(6) . . . . ?
C28 C29 C30 Cl2 -176.2(6) . . . . ?
C28 C29 C30 Br2 -177.7(3) . . . . ?
C29 C30 C31 O2 178.9(4) . . . . ?
Cl2 C30 C31 O2 -4.2(7) . . . . ?
Br2 C30 C31 O2 -2.8(6) . . . . ?
C29 C30 C31 C32 0.2(6) . . . . ?
Cl2 C30 C31 C32 177.1(6) . . . . ?
Br2 C30 C31 C32 178.5(3) . . . . ?
O2 C31 C32 C27 180.0(4) . . . . ?
C30 C31 C32 C27 -1.4(6) . . . . ?
O1 C27 C32 C31 -178.9(4) . . . . ?
C28 C27 C32 C31 1.8(6) . . . . ?
C5 N1 C1 C2 -2.3(7) . . . . ?
N1 C1 C2 C3 -0.2(8) . . . . ?
C1 C2 C3 C4 2.9(7) . . . . ?
C1 C2 C3 C6 -177.0(4) . . . . ?
C2 C3 C4 C5 -3.0(7) . . . . ?
C6 C3 C4 C5 176.9(4) . . . . ?
C1 N1 C5 C4 2.1(7) . . . . ?
C3 C4 C5 N1 0.5(8) . . . . ?
C2 C3 C6 C7 176.3(5) . . . . ?
C4 C3 C6 C7 -3.6(8) . . . . ?
C3 C6 C7 C8 -174.3(4) . . . . ?
C6 C7 C8 C13 179.5(5) . . . . ?
C6 C7 C8 C9 0.2(8) . . . . ?
C13 C8 C9 C10 -0.6(7) . . . . ?
C7 C8 C9 C10 178.6(4) . . . . ?
C8 C9 C10 C11 0.7(8) . . . . ?
C9 C10 C11 C12 -0.1(9) . . . . ?
C10 C11 C12 C13 -0.6(9) . . . . ?
C9 C8 C13 C12 -0.1(7) . . . . ?
C7 C8 C13 C12 -179.3(4) . . . . ?
C11 C12 C13 C8 0.6(8) . . . . ?
C18 N2 C14 C15 0.4(7) . . . . ?
N2 C14 C15 C16 -1.5(7) . . . . ?
C14 C15 C16 C17 1.7(6) . . . . ?
C14 C15 C16 C19 -178.2(4) . . . . ?
C15 C16 C17 C18 -0.9(6) . . . . ?
C19 C16 C17 C18 179.0(4) . . . . ?
C14 N2 C18 C17 0.5(7) . . . . ?
C16 C17 C18 N2 -0.2(7) . . . . ?
C17 C16 C19 C20 -5.1(7) . . . . ?
C15 C16 C19 C20 174.8(4) . . . . ?
C16 C19 C20 C21 -177.4(4) . . . . ?
C19 C20 C21 C22 10.2(7) . . . . ?
C19 C20 C21 C26 -172.3(5) . . . . ?
C26 C21 C22 C23 -0.4(7) . . . . ?
C20 C21 C22 C23 177.1(4) . . . . ?
C21 C22 C23 C24 0.1(7) . . . . ?
C22 C23 C24 C25 0.9(8) . . . . ?
C23 C24 C25 C26 -1.4(8) . . . . ?
C24 C25 C26 C21 1.0(7) . . . . ?
C22 C21 C26 C25 -0.1(7) . . . . ?
C20 C21 C26 C25 -177.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#C29 H29 Br1  0.93 3.13 3.940(8) 146.8 2_676 
#C29 H29 Cl1  0.93 2.94 3.76(3) 148.3 2_676 
#C1 H1 Br2  0.93 3.11 3.728(7) 125.5 2_675 
#C2 H2 Br2  0.93 2.94 3.637(6) 132.5 2_675 
O1 H1A N1 0.82 1.86 2.681(5) 174.0 .
O2 H2A N2 0.82 1.85 2.670(5) 173.0 .
C17 H17 Br2 0.93 2.89 3.787(5) 162.9 2_665
#C17 H17 Cl2  0.93 2.90 3.796(13) 162.2 2_665 

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_r9418
_database_code_depnum_ccdc_archive 'CCDC 1867910'
loop_
_audit_author_name
_audit_author_address
'Nigam Rath'
;University of Missouri- St. Louis
United States of America
;
_audit_update_record             
;
2018-09-14 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2, C6 H4 Br0.8 Cl1.2 O2'
_chemical_formula_sum            'C32 H26 Br0.80 Cl1.20 N2 O2'
_chemical_formula_weight         577.01

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   18.9449(8)
_cell_length_b                   9.4629(4)
_cell_length_c                   14.4914(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2597.93(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8510
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             1186
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.196
_exptl_absorpt_coefficient_mu    1.432
_shelx_estimated_absorpt_T_min   0.701
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_T_max  0.7563
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            24687
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         27.164
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5653
_reflns_number_gt                5032
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.984

_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0111P)²+0.0398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2091 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.016(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5653
_refine_ls_number_parameters     364
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1 O 0.54075(11) 0.2456(2) 0.81223(15) 0.0210(5) Uani 1 1 d . . . . .
H1A H 0.504116 0.210891 0.788699 0.031 Uiso 1 1 calc R U . . .
O2 O 0.64353(11) 0.0927(2) 0.52675(15) 0.0223(5) Uani 1 1 d . . . . .
H2A H 0.601574 0.102666 0.509170 0.033 Uiso 1 1 calc R U . . .
C27 C 0.59742(16) 0.2105(3) 0.7601(2) 0.0167(7) Uani 1 1 d . . . . .
C28 C 0.66469(17) 0.2178(3) 0.7983(2) 0.0173(7) Uani 1 1 d D . . . .
C29 C 0.72364(15) 0.1815(3) 0.7468(2) 0.0191(7) Uani 1 1 d . . . . .
H29 H 0.769338 0.186208 0.773610 0.023 Uiso 1 1 calc R U . . .
C30 C 0.71563(15) 0.1385(3) 0.6565(2) 0.0181(7) Uani 1 1 d D . . . .
C31 C 0.64928(17) 0.1338(3) 0.6154(2) 0.0177(7) Uani 1 1 d . . . . .
C32 C 0.59101(16) 0.1688(3) 0.6692(2) 0.0179(7) Uani 1 1 d . . . . .
H32 H 0.545287 0.163816 0.642444 0.021 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6807(5) 0.2785(9) 0.9150(5) 0.0272(17) Uani 0.597(2) 1 d D . P A 1
Cl2 Cl 0.7947(4) 0.0924(8) 0.5901(5) 0.0204(13) Uani 0.597(2) 1 d D . P A 1
Br1 Br 0.6761(3) 0.2782(5) 0.9202(3) 0.0172(7) Uani 0.403(2) 1 d D . P A 2
Br2 Br 0.7927(2) 0.0834(6) 0.5850(3) 0.0268(10) Uani 0.403(2) 1 d D . P A 2
N1 N 0.51330(14) 0.1550(3) 0.46025(18) 0.0221(6) Uani 1 1 d . . . . .
N2 N 0.08424(13) 0.6300(3) 0.24728(19) 0.0224(6) Uani 1 1 d . . . . .
C1 C 0.49625(17) 0.2922(4) 0.4645(2) 0.0245(8) Uani 1 1 d . . . . .
H1 H 0.526549 0.354112 0.497582 0.029 Uiso 1 1 calc R U . . .
C2 C 0.43700(16) 0.3480(3) 0.4233(2) 0.0224(7) Uani 1 1 d . . . . .
H2 H 0.427448 0.446314 0.427857 0.027 Uiso 1 1 calc R U . . .
C3 C 0.39122(16) 0.2604(3) 0.3750(2) 0.0160(7) Uani 1 1 d . . . . .
C4 C 0.40879(17) 0.1190(3) 0.3718(2) 0.0250(8) Uani 1 1 d . . . . .
H4 H 0.378983 0.054446 0.340158 0.030 Uiso 1 1 calc R U . . .
C5 C 0.46900(17) 0.0711(3) 0.4139(2) 0.0272(8) Uani 1 1 d . . . . .
H5 H 0.479770 -0.026745 0.410017 0.033 Uiso 1 1 calc R U . . .
C6 C 0.32545(15) 0.3192(3) 0.3316(2) 0.0158(7) Uani 1 1 d . . . . .
H6 H 0.300603 0.380777 0.377345 0.019 Uiso 1 1 calc R U . . .
C7 C 0.27127(16) 0.2190(3) 0.28587(19) 0.0150(7) Uani 1 1 d . . . . .
H7 H 0.299332 0.143111 0.254850 0.018 Uiso 1 1 calc R U . . .
C8 C 0.21533(15) 0.1455(3) 0.3400(2) 0.0162(7) Uani 1 1 d . . . . .
C9 C 0.22634(16) 0.1097(3) 0.4318(2) 0.0226(7) Uani 1 1 d . . . . .
H9 H 0.266191 0.146340 0.463623 0.027 Uiso 1 1 calc R U . . .
C10 C 0.17986(18) 0.0212(4) 0.4775(2) 0.0280(8) Uani 1 1 d . . . . .
H10 H 0.188138 -0.002841 0.540183 0.034 Uiso 1 1 calc R U . . .
C11 C 0.12181(16) -0.0322(4) 0.4326(2) 0.0267(8) Uani 1 1 d . . . . .
H11 H 0.090837 -0.095483 0.463427 0.032 Uiso 1 1 calc R U . . .
C12 C 0.10878(17) 0.0067(4) 0.3423(2) 0.0267(8) Uani 1 1 d . . . . .
H12 H 0.068068 -0.027909 0.311352 0.032 Uiso 1 1 calc R U . . .
C13 C 0.15511(17) 0.0962(4) 0.2967(2) 0.0221(7) Uani 1 1 d . . . . .
H13 H 0.145367 0.123903 0.235017 0.026 Uiso 1 1 calc R U . . .
C14 C 0.10607(17) 0.5854(4) 0.1642(2) 0.0258(8) Uani 1 1 d . . . . .
H14 H 0.082604 0.621303 0.111229 0.031 Uiso 1 1 calc R U . . .
C15 C 0.16038(16) 0.4907(4) 0.1509(2) 0.0213(7) Uani 1 1 d . . . . .
H15 H 0.173380 0.463531 0.090086 0.026 Uiso 1 1 calc R U . . .
C16 C 0.19624(15) 0.4349(3) 0.2265(2) 0.0165(7) Uani 1 1 d . . . . .
C17 C 0.17445(16) 0.4814(4) 0.3128(2) 0.0212(7) Uani 1 1 d . . . . .
H17 H 0.196936 0.446930 0.366954 0.025 Uiso 1 1 calc R U . . .
C18 C 0.12034(16) 0.5772(3) 0.3197(2) 0.0215(7) Uani 1 1 d . . . . .
H18 H 0.107388 0.608437 0.379624 0.026 Uiso 1 1 calc R U . . .
C19 C 0.25720(15) 0.3345(3) 0.2109(2) 0.0158(7) Uani 1 1 d . . . . .
H19 H 0.256831 0.293858 0.147167 0.019 Uiso 1 1 calc R U . . .
C20 C 0.33068(15) 0.3993(3) 0.2363(2) 0.0161(7) Uani 1 1 d . . . . .
H20 H 0.328061 0.504114 0.244291 0.019 Uiso 1 1 calc R U . . .
C21 C 0.39282(16) 0.3563(3) 0.1784(2) 0.0153(7) Uani 1 1 d . . . . .
C22 C 0.45234(16) 0.4440(3) 0.1778(2) 0.0200(7) Uani 1 1 d . . . . .
H22 H 0.451250 0.530680 0.210860 0.024 Uiso 1 1 calc R U . . .
C23 C 0.51264(17) 0.4068(4) 0.1299(2) 0.0247(8) Uani 1 1 d . . . . .
H23 H 0.552138 0.468694 0.129894 0.030 Uiso 1 1 calc R U . . .
C24 C 0.51613(17) 0.2813(3) 0.0823(3) 0.0257(7) Uani 1 1 d . . . . .
H24 H 0.557785 0.255469 0.049933 0.031 Uiso 1 1 calc R U . . .
C25 C 0.45765(16) 0.1932(3) 0.0825(2) 0.0254(7) Uani 1 1 d . . . . .
H25 H 0.459383 0.105780 0.050294 0.030 Uiso 1 1 calc R U . . .
C26 C 0.39676(17) 0.2314(3) 0.1290(2) 0.0207(7) Uani 1 1 d . . . . .
H26 H 0.356885 0.170560 0.127094 0.025 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
O1 C27 1.354(4) . ?
O1 H1A 0.8400 . ?
O2 C31 1.346(4) . ?
O2 H2A 0.8400 . ?
C27 C32 1.382(4) . ?
C27 C28 1.391(4) . ?
C28 C29 1.386(4) . ?
C28 Cl1 1.811(8) . ?
C28 Br1 1.869(5) . ?
C29 C30 1.379(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.392(4) . ?
C30 Cl2 1.833(7) . ?
C30 Br2 1.865(5) . ?
C31 C32 1.391(4) . ?
C32 H32 0.9500 . ?
N1 C5 1.336(4) . ?
N1 C1 1.340(4) . ?
N2 C14 1.341(4) . ?
N2 C18 1.349(4) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 C6 1.502(4) . ?
C4 C5 1.371(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.547(4) . ?
C6 C20 1.579(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.490(4) . ?
C7 C19 1.564(4) . ?
C7 H7 1.0000 . ?
C8 C13 1.383(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(4) . ?
C16 C19 1.513(4) . ?
C17 C18 1.372(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.565(4) . ?
C19 H19 1.0000 . ?
C20 C21 1.502(4) . ?
C20 H20 1.0000 . ?
C21 C26 1.384(4) . ?
C21 C22 1.400(4) . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9500 . ?
C26 H26 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
C27 O1 H1A 109.5 . . ?
C31 O2 H2A 109.5 . . ?
O1 C27 C32 122.2(3) . . ?
O1 C27 C28 119.5(3) . . ?
C32 C27 C28 118.3(3) . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 Cl1 116.5(4) . . ?
C27 C28 Cl1 122.7(4) . . ?
C29 C28 Br1 119.4(3) . . ?
C27 C28 Br1 119.8(3) . . ?
C30 C29 C28 119.7(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 121.0(3) . . ?
C29 C30 Cl2 118.6(3) . . ?
C31 C30 Cl2 120.3(3) . . ?
C29 C30 Br2 121.6(3) . . ?
C31 C30 Br2 117.4(3) . . ?
O2 C31 C32 122.6(3) . . ?
O2 C31 C30 119.4(3) . . ?
C32 C31 C30 117.9(3) . . ?
C27 C32 C31 122.2(3) . . ?
C27 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C5 N1 C1 116.6(3) . . ?
C14 N2 C18 115.2(3) . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 116.5(3) . . ?
C4 C3 C6 123.0(3) . . ?
C2 C3 C6 120.5(3) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N1 C5 C4 123.4(3) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C3 C6 C7 120.2(3) . . ?
C3 C6 C20 119.5(2) . . ?
C7 C6 C20 87.7(2) . . ?
C3 C6 H6 109.2 . . ?
C7 C6 H6 109.2 . . ?
C20 C6 H6 109.2 . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 C19 124.8(3) . . ?
C6 C7 C19 89.0(2) . . ?
C8 C7 H7 106.3 . . ?
C6 C7 H7 106.3 . . ?
C19 C7 H7 106.3 . . ?
C13 C8 C9 118.4(3) . . ?
C13 C8 C7 120.4(3) . . ?
C9 C8 C7 120.7(3) . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 120.8(3) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N2 C14 C15 124.1(3) . . ?
N2 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 116.4(3) . . ?
C17 C16 C19 124.1(3) . . ?
C15 C16 C19 119.5(3) . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
N2 C18 C17 124.6(3) . . ?
N2 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
C16 C19 C7 117.7(3) . . ?
C16 C19 C20 113.4(2) . . ?
C7 C19 C20 87.6(2) . . ?
C16 C19 H19 112.0 . . ?
C7 C19 H19 112.0 . . ?
C20 C19 H19 112.0 . . ?
C21 C20 C19 117.4(2) . . ?
C21 C20 C6 114.1(2) . . ?
C19 C20 C6 87.8(2) . . ?
C21 C20 H20 111.8 . . ?
C19 C20 H20 111.8 . . ?
C6 C20 H20 111.8 . . ?
C26 C21 C22 117.4(3) . . ?
C26 C21 C20 124.2(3) . . ?
C22 C21 C20 118.3(3) . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 118.7(3) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C21 C26 C25 121.3(3) . . ?
C21 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?

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
O1 C27 C28 C29 179.5(3) . . . . ?
C32 C27 C28 C29 -1.2(5) . . . . ?
O1 C27 C28 Cl1 -2.1(5) . . . . ?
C32 C27 C28 Cl1 177.2(4) . . . . ?
O1 C27 C28 Br1 -0.9(4) . . . . ?
C32 C27 C28 Br1 178.4(3) . . . . ?
C27 C28 C29 C30 0.4(5) . . . . ?
Cl1 C28 C29 C30 -178.1(4) . . . . ?
Br1 C28 C29 C30 -179.3(3) . . . . ?
C28 C29 C30 C31 1.4(5) . . . . ?
C28 C29 C30 Cl2 179.5(4) . . . . ?
C28 C29 C30 Br2 -178.2(3) . . . . ?
C29 C30 C31 O2 179.3(3) . . . . ?
Cl2 C30 C31 O2 1.3(5) . . . . ?
Br2 C30 C31 O2 -1.0(4) . . . . ?
C29 C30 C31 C32 -2.4(5) . . . . ?
Cl2 C30 C31 C32 179.5(3) . . . . ?
Br2 C30 C31 C32 177.3(3) . . . . ?
O1 C27 C32 C31 179.5(3) . . . . ?
C28 C27 C32 C31 0.2(5) . . . . ?
O2 C31 C32 C27 179.8(3) . . . . ?
C30 C31 C32 C27 1.6(5) . . . . ?
C5 N1 C1 C2 -0.7(5) . . . . ?
N1 C1 C2 C3 0.5(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C6 178.5(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C6 C3 C4 C5 -179.0(3) . . . . ?
C1 N1 C5 C4 0.2(5) . . . . ?
C3 C4 C5 N1 0.5(5) . . . . ?
C4 C3 C6 C7 4.0(4) . . . . ?
C2 C3 C6 C7 -174.3(3) . . . . ?
C4 C3 C6 C20 -102.1(4) . . . . ?
C2 C3 C6 C20 79.6(4) . . . . ?
C3 C6 C7 C8 84.5(4) . . . . ?
C20 C6 C7 C8 -152.4(3) . . . . ?
C3 C6 C7 C19 -144.0(3) . . . . ?
C20 C6 C7 C19 -20.9(2) . . . . ?
C6 C7 C8 C13 158.5(3) . . . . ?
C19 C7 C8 C13 44.2(4) . . . . ?
C6 C7 C8 C9 -29.6(4) . . . . ?
C19 C7 C8 C9 -143.9(3) . . . . ?
C13 C8 C9 C10 3.1(5) . . . . ?
C7 C8 C9 C10 -169.0(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 -2.1(5) . . . . ?
C10 C11 C12 C13 1.7(5) . . . . ?
C9 C8 C13 C12 -3.5(5) . . . . ?
C7 C8 C13 C12 168.6(3) . . . . ?
C11 C12 C13 C8 1.2(5) . . . . ?
C18 N2 C14 C15 1.1(5) . . . . ?
N2 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C14 C15 C16 C19 -178.2(3) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C19 C16 C17 C18 177.3(3) . . . . ?
C14 N2 C18 C17 -1.9(5) . . . . ?
C16 C17 C18 N2 1.4(5) . . . . ?
C17 C16 C19 C7 33.0(4) . . . . ?
C15 C16 C19 C7 -149.7(3) . . . . ?
C17 C16 C19 C20 -67.2(4) . . . . ?
C15 C16 C19 C20 110.1(3) . . . . ?
C8 C7 C19 C16 35.2(4) . . . . ?
C6 C7 C19 C16 -94.2(3) . . . . ?
C8 C7 C19 C20 150.6(3) . . . . ?
C6 C7 C19 C20 21.1(2) . . . . ?
C16 C19 C20 C21 -145.2(3) . . . . ?
C7 C19 C20 C21 95.5(3) . . . . ?
C16 C19 C20 C6 98.7(3) . . . . ?
C7 C19 C20 C6 -20.7(2) . . . . ?
C3 C6 C20 C21 25.5(4) . . . . ?
C7 C6 C20 C21 -98.2(3) . . . . ?
C3 C6 C20 C19 144.7(3) . . . . ?
C7 C6 C20 C19 20.9(2) . . . . ?
C19 C20 C21 C26 -24.8(4) . . . . ?
C6 C20 C21 C26 75.9(4) . . . . ?
C19 C20 C21 C22 158.8(3) . . . . ?
C6 C20 C21 C22 -100.5(3) . . . . ?
C26 C21 C22 C23 -0.2(4) . . . . ?
C20 C21 C22 C23 176.5(3) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
C22 C23 C24 C25 0.6(5) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C22 C21 C26 C25 1.3(5) . . . . ?
C20 C21 C26 C25 -175.2(3) . . . . ?
C24 C25 C26 C21 -1.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N2 0.84 1.94 2.773(3) 174.1 4_545
O2 H2A N1 0.84 1.88 2.714(3) 169.9 .
C5 H5 O1 0.95 2.54 3.345(4) 142.7 2_654
C17 H17 O2 0.95 2.55 3.232(4) 128.4 3_455

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_r10118
_database_code_depnum_ccdc_archive 'CCDC 1867909'
loop_
_audit_author_name
_audit_author_address
'Nigam Rath'
;University of Missouri- St. Louis
United States of America
;
_audit_update_record             
;
2018-09-14 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H11 N), C6 H4 Br0.65 Cl1.35 O2'
_chemical_formula_sum            'C32 H26 Br0.65 Cl1.35 N2 O2'
_chemical_formula_weight         570.35

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.9822(13)
_cell_length_b                   10.9866(13)
_cell_length_c                   11.6040(13)
_cell_angle_alpha                98.151(3)
_cell_angle_beta                 90.796(3)
_cell_angle_gamma                91.779(4)
_cell_volume                     1385.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5978
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.75

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             587
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    1.141
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            20026
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.773
_diffrn_reflns_theta_max         26.689
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5670
_reflns_number_gt                3763
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.1542P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5670
_refine_ls_number_parameters     346
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O1 O 0.99970(14) 0.20362(13) 1.14544(12) 0.0718(4) Uani 1 1 d . . . . .
H1A H 0.982640 0.180853 1.076579 0.108 Uiso 1 1 calc R U . . .
O2 O 0.76952(16) 0.55182(14) 1.07475(13) 0.0796(5) Uani 1 1 d . . . . .
H2A H 0.764166 0.512725 1.009113 0.119 Uiso 1 1 calc R U . . .
C27 C 0.94659(17) 0.31067(18) 1.18069(17) 0.0538(5) Uani 1 1 d . . . . .
C28 C 0.95339(16) 0.35847(18) 1.29891(16) 0.0513(5) Uani 1 1 d D . . . .
C29 C 0.89890(16) 0.46721(18) 1.33926(16) 0.0534(5) Uani 1 1 d . . . . .
H29 H 0.903888 0.497921 1.418153 0.064 Uiso 1 1 calc R U . . .
C30 C 0.83746(16) 0.53063(17) 1.26451(17) 0.0538(5) Uani 1 1 d D . . . .
C31 C 0.82992(18) 0.48647(18) 1.14543(17) 0.0567(5) Uani 1 1 d . . . . .
C32 C 0.88580(18) 0.37737(19) 1.10622(17) 0.0594(5) Uani 1 1 d . . . . .
H32 H 0.882427 0.347772 1.027037 0.071 Uiso 1 1 calc R U . . .
Cl1 Cl 1.0355(3) 0.2784(3) 1.3970(3) 0.1068(18) Uani 0.665(2) 1 d D . P A 1
Cl2 Cl 0.7642(3) 0.6677(3) 1.3169(3) 0.1110(18) Uani 0.665(2) 1 d D . P A 1
Br1 Br 1.03813(15) 0.27489(16) 1.39950(15) 0.0483(4) Uani 0.335(2) 1 d D . P A
2
Br2 Br 0.76200(14) 0.67377(16) 1.31915(16) 0.0505(4) Uani 0.335(2) 1 d D . P A
2
N1 N 0.9461(2) 0.11937(17) 0.92099(16) 0.0741(6) Uani 1 1 d . . . . .
C1 C 0.8465(3) 0.0509(2) 0.8876(2) 0.0865(8) Uani 1 1 d . . . . .
H1 H 0.801908 0.019180 0.944738 0.104 Uiso 1 1 calc R U . . .
C2 C 0.8051(2) 0.0237(2) 0.7742(2) 0.0789(7) Uani 1 1 d . . . . .
H2 H 0.733924 -0.023813 0.756657 0.095 Uiso 1 1 calc R U . . .
C3 C 0.8693(2) 0.06712(19) 0.68706(18) 0.0631(6) Uani 1 1 d . . . . .
C4 C 0.9740(2) 0.1336(2) 0.7213(2) 0.0842(7) Uani 1 1 d . . . . .
H4 H 1.022527 0.162994 0.665579 0.101 Uiso 1 1 calc R U . . .
C5 C 1.0086(2) 0.1576(2) 0.8362(2) 0.0846(7) Uani 1 1 d . . . . .
H5 H 1.080405 0.203490 0.855500 0.102 Uiso 1 1 calc R U . . .
C6 C 0.8308(2) 0.0487(2) 0.56367(19) 0.0741(7) Uani 1 1 d . . . . .
H6 H 0.884334 0.079249 0.512488 0.089 Uiso 1 1 calc R U . . .
C7 C 0.7320(2) -0.00445(19) 0.5180(2) 0.0698(6) Uani 1 1 d . . . . .
H7 H 0.681454 -0.040963 0.567847 0.084 Uiso 1 1 calc R U . . .
C8 C 0.6897(2) -0.01420(18) 0.39621(19) 0.0639(6) Uani 1 1 d . . . . .
C9 C 0.5802(2) -0.0745(2) 0.3638(2) 0.0793(7) Uani 1 1 d . . . . .
H9 H 0.535449 -0.109664 0.418803 0.095 Uiso 1 1 calc R U . . .
C10 C 0.5353(3) -0.0836(2) 0.2504(3) 0.0976(9) Uani 1 1 d . . . . .
H10 H 0.461504 -0.125188 0.229391 0.117 Uiso 1 1 calc R U . . .
C11 C 0.6004(3) -0.0312(3) 0.1700(3) 0.1060(10) Uani 1 1 d . . . . .
H11 H 0.570547 -0.036083 0.094080 0.127 Uiso 1 1 calc R U . . .
C12 C 0.7091(3) 0.0284(3) 0.2007(2) 0.1028(9) Uani 1 1 d . . . . .
H12 H 0.753338 0.063480 0.145366 0.123 Uiso 1 1 calc R U . . .
C13 C 0.7535(2) 0.0370(2) 0.3121(2) 0.0805(7) Uani 1 1 d . . . . .
H13 H 0.827904 0.077933 0.331663 0.097 Uiso 1 1 calc R U . . .
N2 N 0.73127(18) 0.43264(16) 0.85720(16) 0.0657(5) Uani 1 1 d . . . . .
C14 C 0.6149(2) 0.41667(19) 0.8213(2) 0.0674(6) Uani 1 1 d . . . . .
H14 H 0.554661 0.426456 0.877144 0.081 Uiso 1 1 calc R U . . .
C15 C 0.57940(19) 0.38672(18) 0.70703(18) 0.0610(4) Uani 1 1 d . . . . .
H15 H 0.496958 0.377832 0.687138 0.073 Uiso 1 1 calc R U . . .
C16 C 0.66571(19) 0.36960(18) 0.62088(19) 0.0610(4) Uani 1 1 d . . . . .
C17 C 0.7854(2) 0.3856(2) 0.6590(2) 0.0705(6) Uani 1 1 d . . . . .
H17 H 0.847626 0.375164 0.605262 0.085 Uiso 1 1 calc R U . . .
C18 C 0.8139(2) 0.4167(2) 0.7749(2) 0.0720(6) Uani 1 1 d . . . . .
H18 H 0.895656 0.427265 0.797046 0.086 Uiso 1 1 calc R U . . .
C19 C 0.63551(19) 0.34055(19) 0.49602(19) 0.0641(4) Uani 1 1 d . . . . .
H19 H 0.700271 0.325508 0.445750 0.077 Uiso 1 1 calc R U . . .
C20 C 0.52609(19) 0.33385(18) 0.44887(19) 0.0641(4) Uani 1 1 d . . . . .
H20 H 0.462102 0.346239 0.500427 0.077 Uiso 1 1 calc R U . . .
C21 C 0.4917(2) 0.30923(19) 0.32487(19) 0.0656(4) Uani 1 1 d . . . . .
C22 C 0.3690(2) 0.2914(2) 0.2944(2) 0.0741(7) Uani 1 1 d . . . . .
H22 H 0.311329 0.292281 0.352453 0.089 Uiso 1 1 calc R U . . .
C23 C 0.3317(3) 0.2725(2) 0.1792(3) 0.0870(8) Uani 1 1 d . . . . .
H23 H 0.249274 0.260799 0.160109 0.104 Uiso 1 1 calc R U . . .
C24 C 0.4152(3) 0.2707(2) 0.0930(2) 0.0889(8) Uani 1 1 d . . . . .
H24 H 0.389766 0.257250 0.015363 0.107 Uiso 1 1 calc R U . . .
C25 C 0.5367(3) 0.2888(2) 0.1212(2) 0.0841(7) Uani 1 1 d . . . . .
H25 H 0.593667 0.288740 0.062568 0.101 Uiso 1 1 calc R U . . .
C26 C 0.5746(2) 0.30719(19) 0.23638(19) 0.0656(4) Uani 1 1 d . . . . .
H26 H 0.657261 0.318372 0.254688 0.079 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
O1 C27 1.343(2) . ?
O1 H1A 0.8200 . ?
O2 C31 1.345(2) . ?
O2 H2A 0.8200 . ?
C27 C32 1.387(3) . ?
C27 C28 1.398(3) . ?
C28 C29 1.378(3) . ?
C28 Cl1 1.785(4) . ?
C28 Br1 1.844(3) . ?
C29 C30 1.370(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.399(3) . ?
C30 Cl2 1.764(4) . ?
C30 Br2 1.837(3) . ?
C31 C32 1.385(3) . ?
C32 H32 0.9300 . ?
N1 C5 1.317(3) . ?
N1 C1 1.329(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(3) . ?
C3 C6 1.472(3) . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.287(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.469(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(3) . ?
C8 C13 1.382(3) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.361(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N2 C18 1.323(3) . ?
N2 C14 1.338(3) . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(3) . ?
C16 C19 1.470(3) . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.309(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.468(3) . ?
C20 H20 0.9300 . ?
C21 C26 1.380(3) . ?
C21 C22 1.389(3) . ?
C22 C23 1.378(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.380(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
C27 O1 H1A 109.5 . . ?
C31 O2 H2A 109.5 . . ?
O1 C27 C32 123.72(17) . . ?
O1 C27 C28 118.42(18) . . ?
C32 C27 C28 117.86(19) . . ?
C29 C28 C27 120.44(18) . . ?
C29 C28 Cl1 120.20(18) . . ?
C27 C28 Cl1 119.35(19) . . ?
C29 C28 Br1 120.58(15) . . ?
C27 C28 Br1 118.97(16) . . ?
C30 C29 C28 120.78(18) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 120.44(18) . . ?
C29 C30 Cl2 120.7(2) . . ?
C31 C30 Cl2 118.8(2) . . ?
C29 C30 Br2 120.64(16) . . ?
C31 C30 Br2 118.92(17) . . ?
O2 C31 C32 123.29(18) . . ?
O2 C31 C30 118.66(19) . . ?
C32 C31 C30 118.04(18) . . ?
C31 C32 C27 122.42(18) . . ?
C31 C32 H32 118.8 . . ?
C27 C32 H32 118.8 . . ?
C5 N1 C1 115.3(2) . . ?
N1 C1 C2 124.4(2) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 115.8(2) . . ?
C4 C3 C6 119.9(2) . . ?
C2 C3 C6 124.4(2) . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N1 C5 C4 123.8(2) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C7 C6 C3 127.9(2) . . ?
C7 C6 H6 116.1 . . ?
C3 C6 H6 116.1 . . ?
C6 C7 C8 127.6(2) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 H7 116.2 . . ?
C9 C8 C13 117.8(2) . . ?
C9 C8 C7 119.1(2) . . ?
C13 C8 C7 123.1(2) . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 121.1(2) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C18 N2 C14 116.11(19) . . ?
N2 C14 C15 123.7(2) . . ?
N2 C14 H14 118.2 . . ?
C15 C14 H14 118.2 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 115.5(2) . . ?
C17 C16 C19 120.7(2) . . ?
C15 C16 C19 123.80(19) . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
N2 C18 C17 123.6(2) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C20 C19 C16 126.2(2) . . ?
C20 C19 H19 116.9 . . ?
C16 C19 H19 116.9 . . ?
C19 C20 C21 128.2(2) . . ?
C19 C20 H20 115.9 . . ?
C21 C20 H20 115.9 . . ?
C26 C21 C22 118.0(2) . . ?
C26 C21 C20 123.42(19) . . ?
C22 C21 C20 118.6(2) . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.9(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C27 C28 C29 -179.16(17) . . . . ?
C32 C27 C28 C29 1.3(3) . . . . ?
O1 C27 C28 Cl1 1.8(3) . . . . ?
C32 C27 C28 Cl1 -177.8(2) . . . . ?
O1 C27 C28 Br1 1.7(3) . . . . ?
C32 C27 C28 Br1 -177.89(16) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
Cl1 C28 C29 C30 178.85(19) . . . . ?
Br1 C28 C29 C30 178.97(15) . . . . ?
C28 C29 C30 C31 -0.6(3) . . . . ?
C28 C29 C30 Cl2 178.27(18) . . . . ?
C28 C29 C30 Br2 178.61(15) . . . . ?
C29 C30 C31 O2 -179.54(18) . . . . ?
Cl2 C30 C31 O2 1.6(3) . . . . ?
Br2 C30 C31 O2 1.3(3) . . . . ?
C29 C30 C31 C32 0.2(3) . . . . ?
Cl2 C30 C31 C32 -178.7(2) . . . . ?
Br2 C30 C31 C32 -179.00(16) . . . . ?
O2 C31 C32 C27 -179.3(2) . . . . ?
C30 C31 C32 C27 1.0(3) . . . . ?
O1 C27 C32 C31 178.78(19) . . . . ?
C28 C27 C32 C31 -1.7(3) . . . . ?
C5 N1 C1 C2 -2.7(4) . . . . ?
N1 C1 C2 C3 1.0(4) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C6 -177.1(2) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C6 C3 C4 C5 176.5(2) . . . . ?
C1 N1 C5 C4 2.1(4) . . . . ?
C3 C4 C5 N1 0.3(4) . . . . ?
C4 C3 C6 C7 -175.4(3) . . . . ?
C2 C3 C6 C7 3.1(4) . . . . ?
C3 C6 C7 C8 174.9(2) . . . . ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C6 C7 C8 C13 -1.1(4) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
C7 C8 C9 C10 178.6(2) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C8 0.0(4) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
C7 C8 C13 C12 -178.2(2) . . . . ?
C18 N2 C14 C15 -0.6(3) . . . . ?
N2 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C14 C15 C16 C19 -178.33(19) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C19 C16 C17 C18 177.8(2) . . . . ?
C14 N2 C18 C17 -0.1(3) . . . . ?
C16 C17 C18 N2 0.4(4) . . . . ?
C17 C16 C19 C20 -173.7(2) . . . . ?
C15 C16 C19 C20 4.1(3) . . . . ?
C16 C19 C20 C21 177.8(2) . . . . ?
C19 C20 C21 C26 -10.1(4) . . . . ?
C19 C20 C21 C22 172.3(2) . . . . ?
C26 C21 C22 C23 -0.1(3) . . . . ?
C20 C21 C22 C23 177.6(2) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C23 C24 C25 C26 0.8(4) . . . . ?
C24 C25 C26 C21 -0.8(4) . . . . ?
C22 C21 C26 C25 0.4(3) . . . . ?
C20 C21 C26 C25 -177.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N1 0.82 1.87 2.688(2) 176.5 .
O2 H2A N2 0.82 1.88 2.695(2) 172.3 .
#C29 H29 Br1  0.93 3.08 3.883(2) 145.8 2_768 
#C4 H4 Cl2  0.93 2.93 3.626(4) 132.6 2_767 
#C5 H5 Br2  0.93 3.11 3.717(3) 124.8 2_767 
#C15 H15 Cl2  0.93 2.89 3.803(4) 165.6 2_667 

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_r7918
_database_code_depnum_ccdc_archive 'CCDC 1867908'
loop_
_audit_author_name
_audit_author_address
'Nigam Rath'
;University of Missouri- St. Louis
United States of America
;
_audit_update_record             
;
2018-09-14 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H11 N), C6 H4 Br Cl O2'
_chemical_formula_sum            'C32 H26 Br Cl N2 O2'
_chemical_formula_weight         585.91

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.9647(8)
_cell_length_b                   11.0160(8)
_cell_length_c                   11.6107(10)
_cell_angle_alpha                91.273(4)
_cell_angle_beta                 97.696(4)
_cell_angle_gamma                91.769(4)
_cell_volume                     1388.64(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    4620
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      23.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.223
_exptl_absorpt_coefficient_mu    1.608
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_T_max  0.6292
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            15123
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.770
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6367
_reflns_number_gt                4135
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+0.1048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6367
_refine_ls_number_parameters     364
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O1 O 0.20340(13) 1.00002(14) 1.14617(12) 0.0741(4) Uani 1 1 d . . . . .
H1A H 0.1841 0.9882 1.0760 0.111 Uiso 1 1 calc R U . . .
O2 O 0.55116(14) 0.77009(15) 1.07118(13) 0.0816(5) Uani 1 1 d . . . . .
H2A H 0.5119 0.7652 1.0059 0.122 Uiso 1 1 calc R U . . .
C27 C 0.31045(18) 0.94703(16) 1.18061(16) 0.0553(5) Uani 1 1 d . . . . .
C28 C 0.35806(17) 0.95389(15) 1.29809(15) 0.0524(5) Uani 1 1 d D . . . .
C29 C 0.46698(17) 0.89959(14) 1.33737(15) 0.0535(5) Uani 1 1 d . . . . .
H29 H 0.4978 0.9048 1.4160 0.064 Uiso 1 1 calc R U . . .
C30 C 0.53039(17) 0.83788(15) 1.26141(17) 0.0538(5) Uani 1 1 d D . . . .
C31 C 0.48596(18) 0.83058(16) 1.14354(17) 0.0573(5) Uani 1 1 d . . . . .
C32 C 0.37688(18) 0.88583(17) 1.10496(16) 0.0601(5) Uani 1 1 d . . . . .
H32 H 0.3471 0.8819 1.0261 0.072 Uiso 1 1 calc R U . . .
Br1 Br 0.27404(11) 1.04024(9) 1.40093(10) 0.0551(3) Uani 0.502(2) 1 d D . P A 1
Br2 Br 0.67382(9) 0.76082(7) 1.31531(8) 0.0559(2) Uani 0.502(2) 1 d D . P A 1
Cl1 Cl 0.2799(4) 1.0365(4) 1.3980(4) 0.117(2) Uani 0.498(2) 1 d D . P A 2
Cl2 Cl 0.6673(4) 0.7640(3) 1.3120(4) 0.140(2) Uani 0.498(2) 1 d D . P A 2
N1 N 0.11935(17) 0.94517(18) 0.92208(16) 0.0756(5) Uani 1 1 d . . . . .
C1 C 0.1568(2) 1.0081(2) 0.8380(2) 0.0848(7) Uani 1 1 d . . . . .
H1 H 0.2022 1.0800 0.8576 0.102 Uiso 1 1 calc R U . . .
C2 C 0.1327(2) 0.9735(2) 0.7230(2) 0.0860(7) Uani 1 1 d . . . . .
H2 H 0.1614 1.0222 0.6673 0.103 Uiso 1 1 calc R U . . .
C3 C 0.06673(19) 0.86813(19) 0.68888(18) 0.0653(5) Uani 1 1 d . . . . .
C4 C 0.0245(2) 0.8039(2) 0.7759(2) 0.0791(7) Uani 1 1 d . . . . .
H4 H -0.0223 0.7324 0.7584 0.095 Uiso 1 1 calc R U . . .
C5 C 0.0514(2) 0.8454(2) 0.8893(2) 0.0886(7) Uani 1 1 d . . . . .
H5 H 0.0202 0.8008 0.9465 0.106 Uiso 1 1 calc R U . . .
C6 C 0.0487(2) 0.8302(2) 0.56526(19) 0.0760(6) Uani 1 1 d . . . . .
H6 H 0.0789 0.8839 0.5144 0.091 Uiso 1 1 calc R U . . .
C7 C -0.00404(19) 0.7314(2) 0.51921(19) 0.0707(6) Uani 1 1 d . . . . .
H7 H -0.0402 0.6807 0.5689 0.085 Uiso 1 1 calc R U . . .
C8 C -0.01373(18) 0.68933(19) 0.39700(18) 0.0650(5) Uani 1 1 d . . . . .
C9 C 0.0367(2) 0.7535(2) 0.3135(2) 0.0817(7) Uani 1 1 d . . . . .
H9 H 0.0771 0.8280 0.3333 0.098 Uiso 1 1 calc R U . . .
C10 C 0.0279(3) 0.7088(3) 0.2015(2) 0.1060(9) Uani 1 1 d . . . . .
H10 H 0.0628 0.7532 0.1463 0.127 Uiso 1 1 calc R U . . .
C11 C -0.0312(3) 0.6005(3) 0.1701(3) 0.1083(10) Uani 1 1 d . . . . .
H11 H -0.0361 0.5705 0.0940 0.130 Uiso 1 1 calc R U . . .
C12 C -0.0830(2) 0.5361(3) 0.2507(3) 0.0986(9) Uani 1 1 d . . . . .
H12 H -0.1247 0.4626 0.2293 0.118 Uiso 1 1 calc R U . . .
C13 C -0.0742(2) 0.5796(2) 0.3646(2) 0.0804(7) Uani 1 1 d . . . . .
H13 H -0.1092 0.5346 0.4195 0.096 Uiso 1 1 calc R U . . .
N2 N 0.43221(16) 0.73191(16) 0.85474(15) 0.0672(5) Uani 1 1 d . . . . .
C14 C 0.4166(2) 0.81432(19) 0.7731(2) 0.0727(6) Uani 1 1 d . . . . .
H14 H 0.4271 0.8958 0.7959 0.087 Uiso 1 1 calc R U . . .
C15 C 0.3858(2) 0.78632(18) 0.65693(19) 0.0724(6) Uani 1 1 d . . . . .
H15 H 0.3755 0.8483 0.6037 0.087 Uiso 1 1 calc R U . . .
C16 C 0.37000(17) 0.66647(17) 0.61855(17) 0.0587(5) Uani 1 1 d . . . . .
C17 C 0.38589(19) 0.58062(17) 0.70368(19) 0.0663(6) Uani 1 1 d . . . . .
H17 H 0.3760 0.4984 0.6833 0.080 Uiso 1 1 calc R U . . .
C18 C 0.41615(19) 0.61603(19) 0.81822(19) 0.0698(6) Uani 1 1 d . . . . .
H18 H 0.4260 0.5560 0.8735 0.084 Uiso 1 1 calc R U . . .
C19 C 0.34097(19) 0.63627(18) 0.49394(18) 0.0661(6) Uani 1 1 d . . . . .
H19 H 0.3270 0.7009 0.4442 0.079 Uiso 1 1 calc R U . . .
C20 C 0.33277(18) 0.52667(18) 0.44586(18) 0.0649(6) Uani 1 1 d . . . . .
H20 H 0.3435 0.4628 0.4969 0.078 Uiso 1 1 calc R U . . .
C21 C 0.30890(17) 0.49238(17) 0.32205(18) 0.0605(5) Uani 1 1 d . . . . .
C22 C 0.3077(2) 0.5749(2) 0.23457(19) 0.0735(6) Uani 1 1 d . . . . .
H22 H 0.3193 0.6573 0.2535 0.088 Uiso 1 1 calc R U . . .
C23 C 0.2895(2) 0.5370(2) 0.1191(2) 0.0877(7) Uani 1 1 d . . . . .
H23 H 0.2899 0.5938 0.0611 0.105 Uiso 1 1 calc R U . . .
C24 C 0.2709(2) 0.4158(3) 0.0898(2) 0.0916(8) Uani 1 1 d . . . . .
H24 H 0.2583 0.3904 0.0121 0.110 Uiso 1 1 calc R U . . .
C25 C 0.2710(2) 0.3328(2) 0.1754(3) 0.0879(8) Uani 1 1 d . . . . .
H25 H 0.2584 0.2506 0.1559 0.105 Uiso 1 1 calc R U . . .
C26 C 0.2897(2) 0.37018(19) 0.2909(2) 0.0770(6) Uani 1 1 d . . . . .
H26 H 0.2895 0.3129 0.3485 0.092 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
O1 C27 1.344(2) . ?
O1 H1A 0.8200 . ?
O2 C31 1.351(2) . ?
O2 H2A 0.8200 . ?
C27 C32 1.390(3) . ?
C27 C28 1.393(2) . ?
C28 C29 1.379(2) . ?
C28 Cl1 1.782(5) . ?
C28 Br1 1.865(2) . ?
C29 C30 1.375(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.390(2) . ?
C30 Cl2 1.767(4) . ?
C30 Br2 1.851(2) . ?
C31 C32 1.384(3) . ?
C32 H32 0.9300 . ?
N1 C1 1.312(3) . ?
N1 C5 1.328(3) . ?
C1 C2 1.369(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 C6 1.472(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.287(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.472(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(3) . ?
C8 C13 1.381(3) . ?
C9 C10 1.370(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N2 C14 1.325(3) . ?
N2 C18 1.335(2) . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 C19 1.468(3) . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.314(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.465(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(3) . ?
C21 C26 1.388(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
C27 O1 H1A 109.5 . . ?
C31 O2 H2A 109.5 . . ?
O1 C27 C32 123.42(17) . . ?
O1 C27 C28 118.57(17) . . ?
C32 C27 C28 118.01(18) . . ?
C29 C28 C27 120.47(17) . . ?
C29 C28 Cl1 119.6(2) . . ?
C27 C28 Cl1 119.9(2) . . ?
C29 C28 Br1 120.49(14) . . ?
C27 C28 Br1 119.02(15) . . ?
C30 C29 C28 120.64(17) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 120.24(17) . . ?
C29 C30 Cl2 120.8(2) . . ?
C31 C30 Cl2 119.0(2) . . ?
C29 C30 Br2 120.45(14) . . ?
C31 C30 Br2 119.30(15) . . ?
O2 C31 C32 122.66(17) . . ?
O2 C31 C30 118.68(18) . . ?
C32 C31 C30 118.66(17) . . ?
C31 C32 C27 121.97(18) . . ?
C31 C32 H32 119.0 . . ?
C27 C32 H32 119.0 . . ?
C1 N1 C5 115.88(19) . . ?
N1 C1 C2 123.5(2) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 120.9(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 115.8(2) . . ?
C4 C3 C6 124.7(2) . . ?
C2 C3 C6 119.4(2) . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 124.0(2) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C7 C6 C3 127.7(2) . . ?
C7 C6 H6 116.2 . . ?
C3 C6 H6 116.2 . . ?
C6 C7 C8 127.6(2) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 H7 116.2 . . ?
C9 C8 C13 118.3(2) . . ?
C9 C8 C7 123.0(2) . . ?
C13 C8 C7 118.7(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 120.2(2) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C14 N2 C18 116.13(18) . . ?
N2 C14 C15 123.79(19) . . ?
N2 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 115.87(19) . . ?
C17 C16 C19 123.74(18) . . ?
C15 C16 C19 120.38(19) . . ?
C18 C17 C16 120.29(18) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N2 C18 C17 123.6(2) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C20 C19 C16 126.3(2) . . ?
C20 C19 H19 116.9 . . ?
C16 C19 H19 116.9 . . ?
C19 C20 C21 128.2(2) . . ?
C19 C20 H20 115.9 . . ?
C21 C20 H20 115.9 . . ?
C22 C21 C26 118.1(2) . . ?
C22 C21 C20 123.38(18) . . ?
C26 C21 C20 118.5(2) . . ?
C21 C22 C23 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.6(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.8(2) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 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
O1 C27 C28 C29 179.27(16) . . . . ?
C32 C27 C28 C29 -1.0(3) . . . . ?
O1 C27 C28 Cl1 -2.3(3) . . . . ?
C32 C27 C28 Cl1 177.5(2) . . . . ?
O1 C27 C28 Br1 -2.0(2) . . . . ?
C32 C27 C28 Br1 177.78(14) . . . . ?
C27 C28 C29 C30 0.0(3) . . . . ?
Cl1 C28 C29 C30 -178.4(2) . . . . ?
Br1 C28 C29 C30 -178.72(13) . . . . ?
C28 C29 C30 C31 0.7(3) . . . . ?
C28 C29 C30 Cl2 -177.9(2) . . . . ?
C28 C29 C30 Br2 -177.95(13) . . . . ?
C29 C30 C31 O2 179.44(17) . . . . ?
Cl2 C30 C31 O2 -1.9(3) . . . . ?
Br2 C30 C31 O2 -1.9(2) . . . . ?
C29 C30 C31 C32 -0.4(3) . . . . ?
Cl2 C30 C31 C32 178.2(2) . . . . ?
Br2 C30 C31 C32 178.27(14) . . . . ?
O2 C31 C32 C27 179.56(18) . . . . ?
C30 C31 C32 C27 -0.6(3) . . . . ?
O1 C27 C32 C31 -178.97(18) . . . . ?
C28 C27 C32 C31 1.3(3) . . . . ?
C5 N1 C1 C2 -2.2(4) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 2.0(4) . . . . ?
C1 C2 C3 C6 -176.5(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C6 C3 C4 C5 177.1(2) . . . . ?
C1 N1 C5 C4 3.0(4) . . . . ?
C3 C4 C5 N1 -1.3(4) . . . . ?
C4 C3 C6 C7 -2.7(4) . . . . ?
C2 C3 C6 C7 175.6(2) . . . . ?
C3 C6 C7 C8 -174.9(2) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C6 C7 C8 C13 179.8(2) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C10 178.3(2) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
C7 C8 C13 C12 -178.8(2) . . . . ?
C11 C12 C13 C8 0.7(4) . . . . ?
C18 N2 C14 C15 -0.1(3) . . . . ?
N2 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C14 C15 C16 C19 -178.0(2) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C19 C16 C17 C18 178.26(19) . . . . ?
C14 N2 C18 C17 0.4(3) . . . . ?
C16 C17 C18 N2 -0.1(3) . . . . ?
C17 C16 C19 C20 -3.9(3) . . . . ?
C15 C16 C19 C20 174.6(2) . . . . ?
C16 C19 C20 C21 -177.37(19) . . . . ?
C19 C20 C21 C22 9.2(4) . . . . ?
C19 C20 C21 C26 -172.6(2) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?
C20 C21 C22 C23 177.4(2) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C20 C21 C26 C25 -177.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#C29 H29 Br1  0.93 3.09 3.901(2) 146.3 2_678 
#C1 H1 Br2  0.93 3.11 3.728(3) 125.2 2_677 
#C2 H2 Br2  0.93 2.94 3.632(2) 132.6 2_677 
O1 H1A N1 0.82 1.88 2.690(2) 170.8 .
O2 H2A N2 0.82 1.88 2.690(2) 171.7 .
C17 H17 Br2 0.93 2.89 3.794(2) 163.9 2_667

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.037

