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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r1518
_database_code_depnum_ccdc_archive 'CCDC 1829784'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-06-08 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 Br2 O2'
_chemical_formula_sum            'C32 H26 Br2 N2 O2'
_chemical_formula_weight         630.37

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      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                   10.9175(2)
_cell_length_b                   11.1262(2)
_cell_length_c                   11.6716(2)
_cell_angle_alpha                92.5040(10)
_cell_angle_beta                 96.8400(10)
_cell_angle_gamma                91.7890(10)
_cell_volume                     1405.37(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    563(2)
_cell_measurement_reflns_used    8559
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      23.53

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.198
_exptl_absorpt_coefficient_mu    2.916
_shelx_estimated_absorpt_T_min   0.345
_shelx_estimated_absorpt_T_max   0.596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6027
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      563(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            33870
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0576
_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       14
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         26.393
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5736
_reflns_number_gt                3671
_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-2013 (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)+(0.0473P)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         5736
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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 0.27472(3) 0.54366(3) 0.40312(2) 0.06177(13) Uani 1 1 d . . . . .
Br2 Br 0.67338(3) 0.25768(3) 0.30622(3) 0.06711(13) Uani 1 1 d . . . . .
O1 O 0.2024(2) 0.5012(2) 0.14681(16) 0.0675(6) Uani 1 1 d . . . . .
H1 H 0.182267 0.487574 0.077408 0.101 Uiso 1 1 calc R U . . .
O2 O 0.5490(2) 0.2717(2) 0.06285(17) 0.0746(7) Uani 1 1 d . . . . .
H2 H 0.507196 0.261874 -0.000264 0.112 Uiso 1 1 calc R U . . .
C28 C 0.3751(3) 0.3874(3) 0.1013(2) 0.0567(8) Uani 1 1 d . . . . .
H28 H 0.345162 0.384061 0.023145 0.068 Uiso 1 1 calc R U . . .
C29 C 0.4841(3) 0.3314(3) 0.1367(2) 0.0539(8) Uani 1 1 d . . . . .
C32 C 0.3576(3) 0.4556(2) 0.2948(2) 0.0480(7) Uani 1 1 d . . . . .
C27 C 0.3092(3) 0.4485(3) 0.1791(2) 0.0505(7) Uani 1 1 d . . . . .
C31 C 0.4657(3) 0.4006(2) 0.3318(2) 0.0471(7) Uani 1 1 d . . . . .
H31 H 0.496622 0.405628 0.409660 0.057 Uiso 1 1 calc R U . . .
C30 C 0.5279(3) 0.3383(2) 0.2541(2) 0.0464(7) Uani 1 1 d . . . . .
N1 N 0.4307(2) 0.2345(3) 0.8481(2) 0.0612(7) Uani 1 1 d . . . . .
C3 C 0.3702(3) 0.1688(3) 0.6120(2) 0.0547(8) Uani 1 1 d . . . . .
C8 C 0.3075(3) -0.0061(3) 0.3149(3) 0.0573(8) Uani 1 1 d . . . . .
C1 C 0.4157(3) 0.3154(3) 0.7679(3) 0.0702(9) Uani 1 1 d . . . . .
H1A H 0.425990 0.396252 0.791884 0.084 Uiso 1 1 calc R U . . .
C6 C 0.3414(3) 0.1377(3) 0.4875(3) 0.0614(9) Uani 1 1 d . . . . .
H6 H 0.329387 0.201596 0.439154 0.074 Uiso 1 1 calc R U . . .
C4 C 0.3853(3) 0.0836(3) 0.6956(3) 0.0606(8) Uani 1 1 d . . . . .
H4 H 0.375310 0.002090 0.673883 0.073 Uiso 1 1 calc R U . . .
C7 C 0.3308(3) 0.0291(3) 0.4378(3) 0.0587(8) Uani 1 1 d . . . . .
H7 H 0.339313 -0.033983 0.487510 0.070 Uiso 1 1 calc R U . . .
C9 C 0.3095(3) 0.0758(3) 0.2285(3) 0.0691(9) Uani 1 1 d . . . . .
H9 H 0.322926 0.157348 0.248586 0.083 Uiso 1 1 calc R U . . .
C5 C 0.4148(3) 0.1190(3) 0.8102(3) 0.0657(9) Uani 1 1 d . . . . .
H5 H 0.424197 0.059838 0.864093 0.079 Uiso 1 1 calc R U . . .
C2 C 0.3862(3) 0.2879(3) 0.6527(3) 0.0666(9) Uani 1 1 d . . . . .
H2A H 0.376769 0.349375 0.601199 0.080 Uiso 1 1 calc R U . . .
N2 N 0.1183(3) 0.4435(3) 0.9244(2) 0.0680(8) Uani 1 1 d . . . . .
C21 C -0.0130(3) 0.1883(3) 0.3975(3) 0.0595(9) Uani 1 1 d . . . . .
C16 C 0.0653(3) 0.3654(3) 0.6909(3) 0.0605(8) Uani 1 1 d . . . . .
C20 C -0.0040(3) 0.2294(3) 0.5199(3) 0.0661(9) Uani 1 1 d . . . . .
H20 H -0.040136 0.178617 0.568591 0.079 Uiso 1 1 calc R U . . .
C14 C 0.1534(3) 0.5062(3) 0.8408(3) 0.0786(10) Uani 1 1 d . . . . .
H14 H 0.197105 0.578749 0.860510 0.094 Uiso 1 1 calc R U . . .
C17 C 0.0247(3) 0.3016(3) 0.7776(3) 0.0733(10) Uani 1 1 d . . . . .
H17 H -0.021864 0.230365 0.759874 0.088 Uiso 1 1 calc R U . . .
C13 C 0.2873(3) -0.1269(3) 0.2808(3) 0.0727(10) Uani 1 1 d . . . . .
H13 H 0.285698 -0.183644 0.336828 0.087 Uiso 1 1 calc R U . . .
C22 C 0.0371(3) 0.2526(3) 0.3148(3) 0.0775(10) Uani 1 1 d . . . . .
H22 H 0.077173 0.326816 0.335239 0.093 Uiso 1 1 calc R U . . .
C19 C 0.0480(3) 0.3274(3) 0.5673(3) 0.0712(10) Uani 1 1 d . . . . .
H19 H 0.078440 0.380907 0.517566 0.085 Uiso 1 1 calc R U . . .
C18 C 0.0528(4) 0.3428(4) 0.8916(3) 0.0798(11) Uani 1 1 d . . . . .
H18 H 0.024156 0.297231 0.948510 0.096 Uiso 1 1 calc R U . . .
C25 C -0.0815(4) 0.0359(4) 0.2505(4) 0.0925(13) Uani 1 1 d . . . . .
H25 H -0.122253 -0.037608 0.228500 0.111 Uiso 1 1 calc R U . . .
C26 C -0.0728(3) 0.0796(3) 0.3643(3) 0.0739(10) Uani 1 1 d . . . . .
H26 H -0.107792 0.035125 0.418587 0.089 Uiso 1 1 calc R U . . .
C11 C 0.2729(3) -0.0822(4) 0.0825(3) 0.0882(12) Uani 1 1 d . . . . .
H11 H 0.262520 -0.107399 0.004759 0.106 Uiso 1 1 calc R U . . .
C15 C 0.1296(4) 0.4714(3) 0.7266(3) 0.0824(11) Uani 1 1 d . . . . .
H15 H 0.157356 0.520362 0.671712 0.099 Uiso 1 1 calc R U . . .
C23 C 0.0283(4) 0.2079(4) 0.2032(3) 0.0990(14) Uani 1 1 d . . . . .
H23 H 0.063196 0.252082 0.148706 0.119 Uiso 1 1 calc R U . . .
C10 C 0.2919(3) 0.0381(4) 0.1142(3) 0.0834(11) Uani 1 1 d . . . . .
H10 H 0.292741 0.094336 0.057645 0.100 Uiso 1 1 calc R U . . .
C12 C 0.2695(3) -0.1646(4) 0.1657(4) 0.0862(12) Uani 1 1 d . . . . .
H12 H 0.255211 -0.245850 0.144712 0.103 Uiso 1 1 calc R U . . .
C24 C -0.0299(4) 0.1011(5) 0.1704(3) 0.0991(15) Uani 1 1 d . . . . .
H24 H -0.034959 0.071976 0.094023 0.119 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 C32 1.896(3) . ?
Br2 C30 1.899(3) . ?
O1 C27 1.343(3) . ?
O1 H1 0.8200 . ?
O2 C29 1.345(3) . ?
O2 H2 0.8200 . ?
C28 C29 1.389(4) . ?
C28 C27 1.391(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.394(4) . ?
C32 C31 1.379(4) . ?
C32 C27 1.389(4) . ?
C31 C30 1.373(4) . ?
C31 H31 0.9300 . ?
N1 C1 1.327(4) . ?
N1 C5 1.339(4) . ?
C3 C2 1.387(4) . ?
C3 C4 1.389(4) . ?
C3 C6 1.473(4) . ?
C8 C13 1.388(4) . ?
C8 C9 1.390(4) . ?
C8 C7 1.460(4) . ?
C1 C2 1.364(4) . ?
C1 H1A 0.9300 . ?
C6 C7 1.313(4) . ?
C6 H6 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C2 H2A 0.9300 . ?
N2 C14 1.311(4) . ?
N2 C18 1.327(4) . ?
C21 C26 1.374(5) . ?
C21 C22 1.381(4) . ?
C21 C20 1.472(4) . ?
C16 C17 1.369(4) . ?
C16 C15 1.376(5) . ?
C16 C19 1.474(4) . ?
C20 C19 1.285(4) . ?
C20 H20 0.9300 . ?
C14 C15 1.364(4) . ?
C14 H14 0.9300 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C13 C12 1.380(5) . ?
C13 H13 0.9300 . ?
C22 C23 1.365(4) . ?
C22 H22 0.9300 . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C25 C24 1.370(6) . ?
C25 C26 1.386(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C11 C12 1.367(5) . ?
C11 C10 1.376(5) . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
C23 C24 1.348(6) . ?
C23 H23 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C24 H24 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 H1 109.5 . . ?
C29 O2 H2 109.5 . . ?
C29 C28 C27 122.0(3) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
O2 C29 C28 122.9(2) . . ?
O2 C29 C30 119.0(3) . . ?
C28 C29 C30 118.1(3) . . ?
C31 C32 C27 120.8(3) . . ?
C31 C32 Br1 119.6(2) . . ?
C27 C32 Br1 119.5(2) . . ?
O1 C27 C32 119.1(3) . . ?
O1 C27 C28 122.9(2) . . ?
C32 C27 C28 118.0(3) . . ?
C30 C31 C32 120.3(2) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C30 C29 120.7(3) . . ?
C31 C30 Br2 120.1(2) . . ?
C29 C30 Br2 119.2(2) . . ?
C1 N1 C5 116.0(3) . . ?
C2 C3 C4 115.6(3) . . ?
C2 C3 C6 120.9(3) . . ?
C4 C3 C6 123.4(3) . . ?
C13 C8 C9 117.4(3) . . ?
C13 C8 C7 119.5(3) . . ?
C9 C8 C7 123.0(3) . . ?
N1 C1 C2 124.4(3) . . ?
N1 C1 H1A 117.8 . . ?
C2 C1 H1A 117.8 . . ?
C7 C6 C3 126.8(3) . . ?
C7 C6 H6 116.6 . . ?
C3 C6 H6 116.6 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C7 C8 128.8(3) . . ?
C6 C7 H7 115.6 . . ?
C8 C7 H7 115.6 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
N1 C5 C4 123.3(3) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C14 N2 C18 115.7(3) . . ?
C26 C21 C22 118.4(3) . . ?
C26 C21 C20 118.3(3) . . ?
C22 C21 C20 123.3(3) . . ?
C17 C16 C15 115.0(3) . . ?
C17 C16 C19 125.3(3) . . ?
C15 C16 C19 119.6(3) . . ?
C19 C20 C21 127.5(3) . . ?
C19 C20 H20 116.3 . . ?
C21 C20 H20 116.3 . . ?
N2 C14 C15 123.9(3) . . ?
N2 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C12 C13 C8 121.5(4) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
C23 C22 C21 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C20 C19 C16 127.9(3) . . ?
C20 C19 H19 116.1 . . ?
C16 C19 H19 116.1 . . ?
N2 C18 C17 123.8(3) . . ?
N2 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 120.4(4) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C24 C23 C22 121.4(4) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C23 C24 C25 119.4(4) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?

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
C27 C28 C29 O2 179.9(3) . . . . ?
C27 C28 C29 C30 -0.5(5) . . . . ?
C31 C32 C27 O1 178.7(3) . . . . ?
Br1 C32 C27 O1 -2.1(4) . . . . ?
C31 C32 C27 C28 -1.9(4) . . . . ?
Br1 C32 C27 C28 177.3(2) . . . . ?
C29 C28 C27 O1 -178.7(3) . . . . ?
C29 C28 C27 C32 2.0(5) . . . . ?
C27 C32 C31 C30 0.4(4) . . . . ?
Br1 C32 C31 C30 -178.8(2) . . . . ?
C32 C31 C30 C29 1.0(4) . . . . ?
C32 C31 C30 Br2 -177.6(2) . . . . ?
O2 C29 C30 C31 178.6(3) . . . . ?
C28 C29 C30 C31 -1.0(4) . . . . ?
O2 C29 C30 Br2 -2.7(4) . . . . ?
C28 C29 C30 Br2 177.7(2) . . . . ?
C5 N1 C1 C2 -0.2(5) . . . . ?
C2 C3 C6 C7 176.0(4) . . . . ?
C4 C3 C6 C7 -2.9(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C6 C3 C4 C5 178.6(3) . . . . ?
C3 C6 C7 C8 -177.2(3) . . . . ?
C13 C8 C7 C6 -173.6(3) . . . . ?
C9 C8 C7 C6 9.2(5) . . . . ?
C13 C8 C9 C10 0.1(5) . . . . ?
C7 C8 C9 C10 177.4(3) . . . . ?
C1 N1 C5 C4 0.3(5) . . . . ?
C3 C4 C5 N1 -0.1(5) . . . . ?
N1 C1 C2 C3 -0.2(6) . . . . ?
C4 C3 C2 C1 0.5(5) . . . . ?
C6 C3 C2 C1 -178.5(3) . . . . ?
C26 C21 C20 C19 179.9(4) . . . . ?
C22 C21 C20 C19 0.8(6) . . . . ?
C18 N2 C14 C15 -2.1(6) . . . . ?
C15 C16 C17 C18 -2.2(5) . . . . ?
C19 C16 C17 C18 176.1(3) . . . . ?
C9 C8 C13 C12 -0.2(5) . . . . ?
C7 C8 C13 C12 -177.5(3) . . . . ?
C26 C21 C22 C23 -0.8(5) . . . . ?
C20 C21 C22 C23 178.3(3) . . . . ?
C21 C20 C19 C16 -175.2(3) . . . . ?
C17 C16 C19 C20 -1.7(6) . . . . ?
C15 C16 C19 C20 176.5(4) . . . . ?
C14 N2 C18 C17 2.0(6) . . . . ?
C16 C17 C18 N2 0.2(6) . . . . ?
C22 C21 C26 C25 0.5(5) . . . . ?
C20 C21 C26 C25 -178.7(3) . . . . ?
C24 C25 C26 C21 0.1(6) . . . . ?
N2 C14 C15 C16 0.1(6) . . . . ?
C17 C16 C15 C14 2.1(5) . . . . ?
C19 C16 C15 C14 -176.3(4) . . . . ?
C21 C22 C23 C24 0.5(6) . . . . ?
C8 C9 C10 C11 -0.6(6) . . . . ?
C12 C11 C10 C9 1.2(6) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
C8 C13 C12 C11 0.7(6) . . . . ?
C22 C23 C24 C25 0.1(7) . . . . ?
C26 C25 C24 C23 -0.4(6) . . . . ?

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 H1 N2 0.82 1.88 2.691(3) 172.2 1_554
O2 H2 N1 0.82 1.87 2.688(3) 172.6 1_554
#C31 H31 Br1  0.93 3.14 3.953(3) 147.7 2_666 
#C4 H4 Br2  0.93 2.95 3.829(3) 159.0 2_656 
#C15 H15 Br2  0.93 3.02 3.708(4) 132.0 2_666 

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_r18117
_database_code_depnum_ccdc_archive 'CCDC 1829786'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-06-08 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 Cl2 O2'
_chemical_formula_sum            'C32 H26 Cl2 N2 O2'
_chemical_formula_weight         541.45

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'

_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                   10.9020(5)
_cell_length_b                   11.0152(5)
_cell_length_c                   11.5729(5)
_cell_angle_alpha                80.9869(12)
_cell_angle_beta                 89.8172(12)
_cell_angle_gamma                88.0995(14)
_cell_volume                     1371.85(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    5553
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.196
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8288
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(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            16806
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0257
_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       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.869
_diffrn_reflns_theta_max         25.722
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5187
_reflns_number_gt                3711
_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-2013 (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)+(0.0430P)²+0.2611P] 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         5187
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23397(5) 0.66716(5) 0.17397(5) 0.07031(17) Uani 1 1 d . . . . .
Cl2 Cl -0.03039(5) 0.28033(5) 0.10521(4) 0.06852(17) Uani 1 1 d . . . . .
O1 O 0.00113(13) 0.20454(13) 0.35605(11) 0.0692(4) Uani 1 1 d . . . . .
H1A H 0.015403 0.183513 0.425976 0.104 Uiso 1 1 calc R U . . .
O2 O 0.23093(15) 0.55294(13) 0.41860(12) 0.0747(4) Uani 1 1 d . . . . .
H2A H 0.233516 0.515411 0.485636 0.112 Uiso 1 1 calc R U . . .
C27 C 0.05446(16) 0.31146(17) 0.31846(15) 0.0516(4) Uani 1 1 d . . . . .
C28 C 0.11500(17) 0.37809(17) 0.39141(15) 0.0557(5) Uani 1 1 d . . . . .
H28 H 0.118423 0.348394 0.471152 0.067 Uiso 1 1 calc R U . . .
C29 C 0.17052(16) 0.48723(17) 0.34969(16) 0.0535(5) Uani 1 1 d . . . . .
C30 C 0.16300(15) 0.53160(17) 0.23000(15) 0.0516(4) Uani 1 1 d . . . . .
C31 C 0.10171(15) 0.46807(17) 0.15645(15) 0.0513(5) Uani 1 1 d . . . . .
H31 H 0.096585 0.498832 0.076995 0.062 Uiso 1 1 calc R U . . .
C32 C 0.04793(15) 0.35941(17) 0.19946(14) 0.0502(4) Uani 1 1 d . . . . .
N1 N 0.05202(19) 0.12032(16) 0.58226(14) 0.0707(5) Uani 1 1 d . . . . .
C1 C 0.1508(3) 0.0496(2) 0.61529(19) 0.0827(7) Uani 1 1 d . . . . .
H1 H 0.194716 0.016553 0.557908 0.099 Uiso 1 1 calc R U . . .
C2 C 0.1924(2) 0.0221(2) 0.72877(18) 0.0751(6) Uani 1 1 d . . . . .
H2 H 0.263205 -0.026647 0.746106 0.090 Uiso 1 1 calc R U . . .
C3 C 0.12864(19) 0.06722(18) 0.81630(16) 0.0593(5) Uani 1 1 d . . . . .
C4 C 0.0242(2) 0.1365(2) 0.78238(18) 0.0778(6) Uani 1 1 d . . . . .
H4 H -0.023997 0.167171 0.838361 0.093 Uiso 1 1 calc R U . . .
C5 C -0.0099(2) 0.1608(2) 0.6671(2) 0.0779(6) Uani 1 1 d . . . . .
H5 H -0.080908 0.208750 0.647598 0.093 Uiso 1 1 calc R U . . .
C6 C 0.1675(2) 0.0495(2) 0.93943(17) 0.0700(6) Uani 1 1 d . . . . .
H6 H 0.114458 0.081663 0.990886 0.084 Uiso 1 1 calc R U . . .
C7 C 0.2669(2) -0.00559(19) 0.98483(18) 0.0675(6) Uani 1 1 d . . . . .
H7 H 0.316843 -0.043587 0.934831 0.081 Uiso 1 1 calc R U . . .
C8 C 0.3097(2) -0.01492(17) 1.10588(16) 0.0613(5) Uani 1 1 d . . . . .
C9 C 0.4205(2) -0.0759(2) 1.1375(2) 0.0790(6) Uani 1 1 d . . . . .
H9 H 0.465368 -0.111526 1.082268 0.095 Uiso 1 1 calc R U . . .
C10 C 0.4653(3) -0.0845(2) 1.2501(3) 0.0961(9) Uani 1 1 d . . . . .
H10 H 0.539347 -0.126548 1.270611 0.115 Uiso 1 1 calc R U . . .
C11 C 0.4007(3) -0.0312(3) 1.3311(2) 0.1039(10) Uani 1 1 d . . . . .
H11 H 0.431402 -0.035760 1.406563 0.125 Uiso 1 1 calc R U . . .
C12 C 0.2913(3) 0.0287(3) 1.3015(2) 0.0995(9) Uani 1 1 d . . . . .
H12 H 0.247118 0.064300 1.357171 0.119 Uiso 1 1 calc R U . . .
C13 C 0.2460(2) 0.0367(2) 1.19051(18) 0.0773(6) Uani 1 1 d . . . . .
H13 H 0.171063 0.077585 1.171595 0.093 Uiso 1 1 calc R U . . .
N2 N 0.27033(16) 0.43357(15) -0.36268(14) 0.0618(4) Uani 1 1 d . . . . .
C14 C 0.38703(19) 0.41831(18) -0.32830(17) 0.0628(5) Uani 1 1 d . . . . .
H14 H 0.447659 0.429446 -0.385339 0.075 Uiso 1 1 calc R U . . .
C15 C 0.42316(18) 0.38713(17) -0.21367(17) 0.0593(5) Uani 1 1 d . . . . .
H15 H 0.506184 0.377547 -0.194998 0.071 Uiso 1 1 calc R U . . .
C16 C 0.33560(18) 0.36985(17) -0.12543(16) 0.0542(5) Uani 1 1 d . . . . .
C17 C 0.21512(18) 0.3849(2) -0.16196(17) 0.0654(5) Uani 1 1 d . . . . .
H17 H 0.152320 0.373317 -0.107160 0.078 Uiso 1 1 calc R U . . .
C18 C 0.18692(19) 0.4169(2) -0.27872(18) 0.0676(6) Uani 1 1 d . . . . .
H18 H 0.104590 0.427481 -0.299941 0.081 Uiso 1 1 calc R U . . .
C19 C 0.36561(18) 0.34019(18) -0.00058(17) 0.0606(5) Uani 1 1 d . . . . .
H19 H 0.300315 0.323565 0.050742 0.073 Uiso 1 1 calc R U . . .
C20 C 0.47580(18) 0.33484(17) 0.04569(16) 0.0584(5) Uani 1 1 d . . . . .
H20 H 0.540385 0.348366 -0.006952 0.070 Uiso 1 1 calc R U . . .
C21 C 0.51011(18) 0.31026(16) 0.16983(17) 0.0559(5) Uani 1 1 d . . . . .
C22 C 0.63358(19) 0.29395(19) 0.1990(2) 0.0697(6) Uani 1 1 d . . . . .
H22 H 0.691838 0.296544 0.139865 0.084 Uiso 1 1 calc R U . . .
C23 C 0.6713(2) 0.2739(2) 0.3143(2) 0.0790(7) Uani 1 1 d . . . . .
H23 H 0.754407 0.262729 0.332360 0.095 Uiso 1 1 calc R U . . .
C24 C 0.5862(3) 0.2706(2) 0.4023(2) 0.0825(7) Uani 1 1 d . . . . .
H24 H 0.611471 0.257327 0.480072 0.099 Uiso 1 1 calc R U . . .
C25 C 0.4637(2) 0.2869(2) 0.37518(19) 0.0791(6) Uani 1 1 d . . . . .
H25 H 0.406019 0.284783 0.434784 0.095 Uiso 1 1 calc R U . . .
C26 C 0.4256(2) 0.30627(19) 0.26002(18) 0.0660(5) Uani 1 1 d . . . . .
H26 H 0.342364 0.316798 0.242686 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
Cl1 C30 1.7376(18) . ?
Cl2 C32 1.7409(18) . ?
O1 C27 1.341(2) . ?
O1 H1A 0.8200 . ?
O2 C29 1.345(2) . ?
O2 H2A 0.8200 . ?
C27 C28 1.385(2) . ?
C27 C32 1.397(2) . ?
C28 C29 1.382(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.396(2) . ?
C30 C31 1.372(3) . ?
C31 C32 1.372(2) . ?
C31 H31 0.9300 . ?
N1 C5 1.316(3) . ?
N1 C1 1.329(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 C6 1.470(3) . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.296(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.465(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.382(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N2 C18 1.324(2) . ?
N2 C14 1.332(2) . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(3) . ?
C16 C19 1.466(2) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.313(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.467(3) . ?
C20 H20 0.9300 . ?
C21 C26 1.386(3) . ?
C21 C22 1.388(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(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 . . ?
C29 O2 H2A 109.5 . . ?
O1 C27 C28 123.59(15) . . ?
O1 C27 C32 118.54(16) . . ?
C28 C27 C32 117.86(17) . . ?
C29 C28 C27 122.20(16) . . ?
C29 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
O2 C29 C28 123.30(16) . . ?
O2 C29 C30 118.46(17) . . ?
C28 C29 C30 118.24(16) . . ?
C31 C30 C29 120.51(17) . . ?
C31 C30 Cl1 119.94(14) . . ?
C29 C30 Cl1 119.54(14) . . ?
C30 C31 C32 120.36(16) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 120.81(16) . . ?
C31 C32 Cl2 119.84(13) . . ?
C27 C32 Cl2 119.35(14) . . ?
C5 N1 C1 115.64(18) . . ?
N1 C1 C2 124.3(2) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 115.91(19) . . ?
C4 C3 C6 119.60(19) . . ?
C2 C3 C6 124.5(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 123.7(2) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C7 C6 C3 127.7(2) . . ?
C7 C6 H6 116.1 . . ?
C3 C6 H6 116.1 . . ?
C6 C7 C8 127.5(2) . . ?
C6 C7 H7 116.3 . . ?
C8 C7 H7 116.3 . . ?
C13 C8 C9 117.8(2) . . ?
C13 C8 C7 123.2(2) . . ?
C9 C8 C7 119.0(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
C18 N2 C14 116.12(17) . . ?
N2 C14 C15 123.90(19) . . ?
N2 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C14 C15 C16 120.01(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 115.65(17) . . ?
C17 C16 C19 120.52(18) . . ?
C15 C16 C19 123.82(17) . . ?
C18 C17 C16 120.59(19) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
N2 C18 C17 123.73(19) . . ?
N2 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
C20 C19 C16 126.24(19) . . ?
C20 C19 H19 116.9 . . ?
C16 C19 H19 116.9 . . ?
C19 C20 C21 128.30(19) . . ?
C19 C20 H20 115.9 . . ?
C21 C20 H20 115.9 . . ?
C26 C21 C22 118.02(19) . . ?
C26 C21 C20 123.34(18) . . ?
C22 C21 C20 118.60(19) . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.4(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 179.09(18) . . . . ?
C32 C27 C28 C29 -1.5(3) . . . . ?
C27 C28 C29 O2 -179.30(18) . . . . ?
C27 C28 C29 C30 1.0(3) . . . . ?
O2 C29 C30 C31 -179.61(17) . . . . ?
C28 C29 C30 C31 0.1(3) . . . . ?
O2 C29 C30 Cl1 1.4(2) . . . . ?
C28 C29 C30 Cl1 -178.89(14) . . . . ?
C29 C30 C31 C32 -0.6(3) . . . . ?
Cl1 C30 C31 C32 178.42(13) . . . . ?
C30 C31 C32 C27 0.0(3) . . . . ?
C30 C31 C32 Cl2 179.59(13) . . . . ?
O1 C27 C32 C31 -179.55(17) . . . . ?
C28 C27 C32 C31 1.1(3) . . . . ?
O1 C27 C32 Cl2 0.9(2) . . . . ?
C28 C27 C32 Cl2 -178.54(14) . . . . ?
C5 N1 C1 C2 -2.7(4) . . . . ?
N1 C1 C2 C3 1.3(4) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 C6 -176.7(2) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C6 C3 C4 C5 175.9(2) . . . . ?
C1 N1 C5 C4 1.7(3) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C4 C3 C6 C7 -175.0(2) . . . . ?
C2 C3 C6 C7 2.7(4) . . . . ?
C3 C6 C7 C8 174.96(19) . . . . ?
C6 C7 C8 C13 -0.1(3) . . . . ?
C6 C7 C8 C9 -178.6(2) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C10 178.7(2) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C8 -0.2(4) . . . . ?
C9 C8 C13 C12 0.5(3) . . . . ?
C7 C8 C13 C12 -178.1(2) . . . . ?
C18 N2 C14 C15 0.0(3) . . . . ?
N2 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C14 C15 C16 C19 -178.06(18) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C19 C16 C17 C18 177.73(19) . . . . ?
C14 N2 C18 C17 -0.4(3) . . . . ?
C16 C17 C18 N2 1.0(3) . . . . ?
C17 C16 C19 C20 -173.3(2) . . . . ?
C15 C16 C19 C20 5.4(3) . . . . ?
C16 C19 C20 C21 177.46(18) . . . . ?
C19 C20 C21 C26 -9.9(3) . . . . ?
C19 C20 C21 C22 172.2(2) . . . . ?
C26 C21 C22 C23 0.2(3) . . . . ?
C20 C21 C22 C23 178.21(19) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
C20 C21 C26 C25 -177.78(19) . . . . ?

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 2.690(2) 174.4 .
O2 H2A N2 0.82 1.88 2.692(2) 169.6 1_556
#C4 H4 Cl1  0.93 2.87 3.576(2) 133.7 2_566 
#C15 H15 Cl1  0.93 2.86 3.784(2) 170.4 2_665 

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_r20117
_database_code_depnum_ccdc_archive 'CCDC 1829787'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-06-08 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 Cl2 O2'
_chemical_formula_sum            'C32 H26 Cl2 N2 O2'
_chemical_formula_weight         541.45

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'

_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                   18.9319(13)
_cell_length_b                   9.4899(6)
_cell_length_c                   14.4526(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2596.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3414
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      25.65

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.226
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7818
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            32881
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         30.527
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7913
_reflns_number_gt                5977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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-2013 (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+0.6503P] 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 2149 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7913
_refine_ls_number_parameters     345
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20962(4) 0.09083(11) 0.23257(6) 0.0299(2) Uani 1 1 d . . . . .
Cl2 Cl 0.32496(5) 0.27357(10) 0.55321(6) 0.0278(2) Uani 1 1 d . . . . .
O1 O 0.45972(13) 0.2455(3) 0.45192(17) 0.0228(6) Uani 1 1 d . . . . .
H1A H 0.495651 0.216632 0.426541 0.034 Uiso 1 1 calc R U . . .
O2 O 0.35513(13) 0.0914(3) 0.16667(16) 0.0249(6) Uani 1 1 d . . . . .
H2A H 0.395459 0.104933 0.147981 0.037 Uiso 1 1 calc R U . . .
C27 C 0.40247(18) 0.2098(4) 0.4004(2) 0.0177(7) Uani 1 1 d . . . . .
C28 C 0.40878(18) 0.1678(4) 0.3090(2) 0.0200(7) Uani 1 1 d . . . . .
H28 H 0.453517 0.163102 0.282595 0.024 Uiso 1 1 calc R U . . .
C29 C 0.35025(18) 0.1323(4) 0.2553(2) 0.0190(7) Uani 1 1 d . . . . .
C30 C 0.28343(17) 0.1375(4) 0.2972(2) 0.0193(7) Uani 1 1 d . . . . .
C31 C 0.27625(18) 0.1809(4) 0.3884(2) 0.0209(7) Uani 1 1 d . . . . .
H31 H 0.231690 0.185285 0.415311 0.025 Uiso 1 1 calc R U . . .
C32 C 0.33524(18) 0.2176(4) 0.4391(2) 0.0188(7) Uani 1 1 d . . . . .
N1 N 0.08490(15) 0.3691(3) 0.3862(2) 0.0241(7) Uani 1 1 d . . . . .
N2 N 0.51510(16) 0.8439(4) 0.5996(2) 0.0246(7) Uani 1 1 d . . . . .
C1 C 0.12115(19) 0.4182(4) 0.4593(3) 0.0252(8) Uani 1 1 d . . . . .
H1 H 0.108638 0.385890 0.517754 0.030 Uiso 1 1 calc R U . . .
C2 C 0.17631(18) 0.5147(4) 0.4527(3) 0.0262(8) Uani 1 1 d . . . . .
H2 H 0.198971 0.546786 0.505763 0.031 Uiso 1 1 calc R U . . .
C3 C 0.19723(17) 0.5626(4) 0.3656(2) 0.0187(7) Uani 1 1 d . . . . .
C4 C 0.16113(19) 0.5087(4) 0.2905(2) 0.0261(8) Uani 1 1 d . . . . .
H4 H 0.173763 0.535504 0.230839 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1064(2) 0.4151(5) 0.3038(3) 0.0297(9) Uani 1 1 d . . . . .
H5 H 0.082905 0.381846 0.251737 0.036 Uiso 1 1 calc R U . . .
C6 C 0.39390(18) 0.6433(4) 0.3179(2) 0.0186(7) Uani 1 1 d . . . . .
C7 C 0.45349(19) 0.5550(4) 0.3166(2) 0.0232(8) Uani 1 1 d . . . . .
H7 H 0.452628 0.470336 0.348968 0.028 Uiso 1 1 calc R U . . .
C8 C 0.51372(19) 0.5927(4) 0.2673(3) 0.0280(9) Uani 1 1 d . . . . .
H8 H 0.552411 0.532306 0.266270 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5165(2) 0.7176(4) 0.2205(3) 0.0301(9) Uani 1 1 d . . . . .
H9 H 0.557191 0.743447 0.188644 0.036 Uiso 1 1 calc R U . . .
C10 C 0.4586(2) 0.8047(4) 0.2210(3) 0.0297(9) Uani 1 1 d . . . . .
H10 H 0.460367 0.890035 0.189436 0.036 Uiso 1 1 calc R U . . .
C11 C 0.39785(19) 0.7674(4) 0.2675(3) 0.0237(8) Uani 1 1 d . . . . .
H11 H 0.358757 0.826575 0.265039 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4967(2) 0.7082(4) 0.6054(3) 0.0291(9) Uani 1 1 d . . . . .
H12 H 0.525797 0.647994 0.638969 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4373(2) 0.6523(4) 0.5647(3) 0.0266(8) Uani 1 1 d . . . . .
H13 H 0.427345 0.556796 0.570578 0.032 Uiso 1 1 calc R U . . .
C14 C 0.39217(18) 0.7394(4) 0.5148(2) 0.0187(7) Uani 1 1 d . . . . .
C15 C 0.4098(2) 0.8788(4) 0.5102(3) 0.0315(10) Uani 1 1 d . . . . .
H15 H 0.380716 0.941041 0.478168 0.038 Uiso 1 1 calc R U . . .
C16 C 0.4703(2) 0.9284(4) 0.5525(3) 0.0333(9) Uani 1 1 d . . . . .
H16 H 0.480632 1.024013 0.548512 0.040 Uiso 1 1 calc R U . . .
C17 C 0.21531(17) 0.8522(4) 0.4803(2) 0.0187(7) Uani 1 1 d . . . . .
C18 C 0.22647(19) 0.8884(4) 0.5722(2) 0.0244(8) Uani 1 1 d . . . . .
H18 H 0.265633 0.853284 0.603468 0.029 Uiso 1 1 calc R U . . .
C19 C 0.1798(2) 0.9762(5) 0.6173(3) 0.0334(10) Uani 1 1 d . . . . .
H19 H 0.187697 0.999326 0.679003 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1221(2) 1.0296(4) 0.5727(3) 0.0325(10) Uani 1 1 d . . . . .
H20 H 0.091898 1.091401 0.603107 0.039 Uiso 1 1 calc R U . . .
C21 C 0.1090(2) 0.9910(4) 0.4818(3) 0.0306(9) Uani 1 1 d . . . . .
H21 H 0.069170 1.025046 0.451466 0.037 Uiso 1 1 calc R U . . .
C22 C 0.15539(18) 0.9012(4) 0.4359(2) 0.0236(8) Uani 1 1 d . . . . .
H22 H 0.146100 0.874057 0.375283 0.028 Uiso 1 1 calc R U . . .
C23 C 0.25803(18) 0.6633(4) 0.3500(2) 0.0186(7) Uani 1 1 d . . . . .
H23 H 0.257788 0.702915 0.287364 0.022 Uiso 1 1 calc R U . . .
C24 C 0.33147(17) 0.5992(4) 0.3761(2) 0.0191(7) Uani 1 1 d . . . . .
H24 H 0.329180 0.496737 0.384051 0.023 Uiso 1 1 calc R U . . .
C25 C 0.32624(18) 0.6797(4) 0.4714(2) 0.0187(7) Uani 1 1 d . . . . .
H25 H 0.301963 0.619727 0.516509 0.022 Uiso 1 1 calc R U . . .
C26 C 0.27222(18) 0.7785(4) 0.4254(2) 0.0174(7) Uani 1 1 d . . . . .
H26 H 0.299632 0.852777 0.394959 0.021 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
Cl1 C30 1.739(3) . ?
Cl2 C32 1.743(3) . ?
O1 C27 1.358(4) . ?
O1 H1A 0.8200 . ?
O2 C29 1.342(4) . ?
O2 H2A 0.8200 . ?
C27 C28 1.385(5) . ?
C27 C32 1.392(5) . ?
C28 C29 1.394(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.404(5) . ?
C30 C31 1.386(5) . ?
C31 C32 1.381(5) . ?
C31 H31 0.9300 . ?
N1 C5 1.332(5) . ?
N1 C1 1.343(5) . ?
N2 C12 1.337(5) . ?
N2 C16 1.350(5) . ?
C1 C2 1.392(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 C23 1.513(5) . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C11 1.386(5) . ?
C6 C7 1.405(5) . ?
C6 C24 1.510(5) . ?
C7 C8 1.391(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(5) . ?
C14 C25 1.507(5) . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.384(5) . ?
C17 C18 1.388(5) . ?
C17 C26 1.510(5) . ?
C18 C19 1.378(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.564(5) . ?
C23 C26 1.566(5) . ?
C23 H23 0.9800 . ?
C24 C25 1.578(5) . ?
C24 H24 0.9800 . ?
C25 C26 1.538(5) . ?
C25 H25 0.9800 . ?
C26 H26 0.9800 . ?

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 . . ?
C29 O2 H2A 109.5 . . ?
O1 C27 C28 121.7(3) . . ?
O1 C27 C32 119.7(3) . . ?
C28 C27 C32 118.5(3) . . ?
C27 C28 C29 122.1(3) . . ?
C27 C28 H28 118.9 . . ?
C29 C28 H28 118.9 . . ?
O2 C29 C28 123.1(3) . . ?
O2 C29 C30 119.0(3) . . ?
C28 C29 C30 117.9(3) . . ?
C31 C30 C29 120.6(3) . . ?
C31 C30 Cl1 120.5(3) . . ?
C29 C30 Cl1 118.9(3) . . ?
C32 C31 C30 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.8(3) . . ?
C31 C32 Cl2 119.3(3) . . ?
C27 C32 Cl2 119.9(3) . . ?
C5 N1 C1 115.6(3) . . ?
C12 N2 C16 116.1(3) . . ?
N1 C1 C2 123.9(3) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 116.6(3) . . ?
C4 C3 C23 119.6(3) . . ?
C2 C3 C23 123.8(3) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 124.5(3) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C11 C6 C7 117.1(3) . . ?
C11 C6 C24 124.8(3) . . ?
C7 C6 C24 118.1(3) . . ?
C8 C7 C6 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.3(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 121.3(4) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
N2 C12 C13 123.9(3) . . ?
N2 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 116.8(3) . . ?
C15 C14 C25 123.1(3) . . ?
C13 C14 C25 120.1(3) . . ?
C14 C15 C16 120.7(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
N2 C16 C15 122.8(4) . . ?
N2 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C22 C17 C18 119.0(3) . . ?
C22 C17 C26 119.8(3) . . ?
C18 C17 C26 120.6(3) . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.9(4) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.5(4) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.0(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.1(3) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C3 C23 C24 113.2(3) . . ?
C3 C23 C26 117.9(3) . . ?
C24 C23 C26 87.2(2) . . ?
C3 C23 H23 112.1 . . ?
C24 C23 H23 112.1 . . ?
C26 C23 H23 112.1 . . ?
C6 C24 C23 117.0(3) . . ?
C6 C24 C25 113.7(3) . . ?
C23 C24 C25 88.1(2) . . ?
C6 C24 H24 112.0 . . ?
C23 C24 H24 112.0 . . ?
C25 C24 H24 112.0 . . ?
C14 C25 C26 120.1(3) . . ?
C14 C25 C24 119.5(3) . . ?
C26 C25 C24 87.7(2) . . ?
C14 C25 H25 109.2 . . ?
C26 C25 H25 109.2 . . ?
C24 C25 H25 109.2 . . ?
C17 C26 C25 122.0(3) . . ?
C17 C26 C23 124.5(3) . . ?
C25 C26 C23 89.4(3) . . ?
C17 C26 H26 106.3 . . ?
C25 C26 H26 106.3 . . ?
C23 C26 H26 106.3 . . ?

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 -179.3(3) . . . . ?
C32 C27 C28 C29 -0.5(5) . . . . ?
C27 C28 C29 O2 180.0(3) . . . . ?
C27 C28 C29 C30 -1.3(5) . . . . ?
O2 C29 C30 C31 -179.2(3) . . . . ?
C28 C29 C30 C31 1.9(5) . . . . ?
O2 C29 C30 Cl1 0.0(5) . . . . ?
C28 C29 C30 Cl1 -178.9(3) . . . . ?
C29 C30 C31 C32 -0.9(5) . . . . ?
Cl1 C30 C31 C32 179.9(3) . . . . ?
C30 C31 C32 C27 -0.9(5) . . . . ?
C30 C31 C32 Cl2 179.3(3) . . . . ?
O1 C27 C32 C31 -179.5(3) . . . . ?
C28 C27 C32 C31 1.6(5) . . . . ?
O1 C27 C32 Cl2 0.2(5) . . . . ?
C28 C27 C32 Cl2 -178.7(3) . . . . ?
C5 N1 C1 C2 2.1(6) . . . . ?
N1 C1 C2 C3 -1.4(6) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C23 -177.8(3) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
C23 C3 C4 C5 179.0(4) . . . . ?
C1 N1 C5 C4 -1.0(6) . . . . ?
C3 C4 C5 N1 -0.8(7) . . . . ?
C11 C6 C7 C8 0.7(5) . . . . ?
C24 C6 C7 C8 -177.3(3) . . . . ?
C6 C7 C8 C9 1.1(6) . . . . ?
C7 C8 C9 C10 -1.3(6) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C9 C10 C11 C6 2.2(6) . . . . ?
C7 C6 C11 C10 -2.3(5) . . . . ?
C24 C6 C11 C10 175.6(3) . . . . ?
C16 N2 C12 C13 1.9(6) . . . . ?
N2 C12 C13 C14 -0.6(6) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C12 C13 C14 C25 -178.9(3) . . . . ?
C13 C14 C15 C16 0.9(6) . . . . ?
C25 C14 C15 C16 178.9(4) . . . . ?
C12 N2 C16 C15 -1.8(6) . . . . ?
C14 C15 C16 N2 0.5(7) . . . . ?
C22 C17 C18 C19 -2.4(6) . . . . ?
C26 C17 C18 C19 168.9(4) . . . . ?
C17 C18 C19 C20 -0.3(6) . . . . ?
C18 C19 C20 C21 2.3(6) . . . . ?
C19 C20 C21 C22 -1.6(6) . . . . ?
C18 C17 C22 C21 3.1(6) . . . . ?
C26 C17 C22 C21 -168.3(3) . . . . ?
C20 C21 C22 C17 -1.1(6) . . . . ?
C4 C3 C23 C24 -111.3(4) . . . . ?
C2 C3 C23 C24 65.9(4) . . . . ?
C4 C3 C23 C26 149.1(3) . . . . ?
C2 C3 C23 C26 -33.7(5) . . . . ?
C11 C6 C24 C23 24.2(5) . . . . ?
C7 C6 C24 C23 -158.0(3) . . . . ?
C11 C6 C24 C25 -76.3(4) . . . . ?
C7 C6 C24 C25 101.6(4) . . . . ?
C3 C23 C24 C6 145.5(3) . . . . ?
C26 C23 C24 C6 -95.3(3) . . . . ?
C3 C23 C24 C25 -98.9(3) . . . . ?
C26 C23 C24 C25 20.4(2) . . . . ?
C15 C14 C25 C26 -4.7(5) . . . . ?
C13 C14 C25 C26 173.2(3) . . . . ?
C15 C14 C25 C24 101.2(4) . . . . ?
C13 C14 C25 C24 -80.8(4) . . . . ?
C6 C24 C25 C14 -25.6(4) . . . . ?
C23 C24 C25 C14 -144.4(3) . . . . ?
C6 C24 C25 C26 98.0(3) . . . . ?
C23 C24 C25 C26 -20.8(3) . . . . ?
C22 C17 C26 C25 -158.9(3) . . . . ?
C18 C17 C26 C25 29.9(5) . . . . ?
C22 C17 C26 C23 -44.5(5) . . . . ?
C18 C17 C26 C23 144.3(3) . . . . ?
C14 C25 C26 C17 -84.7(4) . . . . ?
C24 C25 C26 C17 152.1(3) . . . . ?
C14 C25 C26 C23 143.9(3) . . . . ?
C24 C25 C26 C23 20.7(2) . . . . ?
C3 C23 C26 C17 -35.5(5) . . . . ?
C24 C23 C26 C17 -150.4(3) . . . . ?
C3 C23 C26 C25 94.0(3) . . . . ?
C24 C23 C26 C25 -20.9(3) . . . . ?

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 1.96 2.775(4) 170.1 3
O2 H2A N2 0.82 1.90 2.711(4) 173.5 2_664
C2 H2 O2 0.93 2.58 3.232(4) 127.9 4
C16 H16 O1 0.93 2.55 3.348(5) 143.6 1_565

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_r2018
_database_code_depnum_ccdc_archive 'CCDC 1829785'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-06-08 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 Br2 O2'
_chemical_formula_sum            'C32 H26 Br2 N2 O2'
_chemical_formula_weight         630.37

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                   17.251(2)
_cell_length_b                   9.2852(11)
_cell_length_c                   17.340(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.350(3)
_cell_angle_gamma                90
_cell_volume                     2754.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4935
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.80

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    2.975
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2888
_exptl_absorpt_correction_T_max  0.3972
_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            23779
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.369
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5589
_reflns_number_gt                3582
_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-2013 (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)+(0.0600P)²+16.8478P] 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         5589
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.18531(4) 0.70872(8) 0.67835(4) 0.0300(2) Uani 1 1 d . . . . .
Br2 Br 0.30708(4) 0.83203(8) 0.39623(4) 0.0301(2) Uani 1 1 d . . . . .
O1 O 0.3492(3) 0.6001(6) 0.7236(2) 0.0297(12) Uani 1 1 d . . . . .
H1A H 0.396453 0.584729 0.739745 0.045 Uiso 1 1 calc R U . . .
O2 O 0.4552(3) 0.7263(6) 0.4884(3) 0.0321(12) Uani 1 1 d . . . . .
H2A H 0.497243 0.703787 0.515663 0.048 Uiso 1 1 calc R U . . .
C27 C 0.2699(4) 0.7059(7) 0.6186(3) 0.0229(15) Uani 1 1 d . . . . .
C28 C 0.3429(4) 0.6554(8) 0.6508(4) 0.0258(16) Uani 1 1 d . . . . .
C29 C 0.4051(4) 0.6630(8) 0.6079(4) 0.0257(16) Uani 1 1 d . . . . .
H29 H 0.455002 0.629423 0.630328 0.031 Uiso 1 1 calc R U . . .
C30 C 0.3963(4) 0.7194(8) 0.5320(4) 0.0259(16) Uani 1 1 d . . . . .
C31 C 0.3218(4) 0.7649(8) 0.5004(4) 0.0259(16) Uani 1 1 d . . . . .
C32 C 0.2588(4) 0.7596(7) 0.5427(4) 0.0240(16) Uani 1 1 d . . . . .
H32 H 0.208745 0.792113 0.520371 0.029 Uiso 1 1 calc R U . . .
N1 N 0.5029(4) 0.0447(7) 0.7108(3) 0.0347(16) Uani 1 1 d . . . . .
N2 N 0.4012(3) 0.2053(7) 0.9355(3) 0.0276(14) Uani 1 1 d . . . . .
C1 C 0.4528(5) -0.0381(9) 0.7448(4) 0.0353(19) Uani 1 1 d . . . . .
H1 H 0.473279 -0.107900 0.781935 0.042 Uiso 1 1 calc R U . . .
C2 C 0.3731(5) -0.0251(8) 0.7275(4) 0.0332(18) Uani 1 1 d . . . . .
H2 H 0.339196 -0.087674 0.750788 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3425(4) 0.0817(8) 0.6751(4) 0.0291(17) Uani 1 1 d . . . . .
C4 C 0.3935(4) 0.1576(9) 0.6373(4) 0.035(2) Uani 1 1 d . . . . .
H4 H 0.374660 0.224799 0.598032 0.042 Uiso 1 1 calc R U . . .
C5 C 0.4737(5) 0.1360(9) 0.6566(4) 0.037(2) Uani 1 1 d . . . . .
H5 H 0.508621 0.189426 0.629560 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2560(4) 0.1132(8) 0.6667(4) 0.0271(17) Uani 1 1 d . . . . .
H6 H 0.226243 0.034115 0.637029 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2266(4) 0.2613(8) 0.6345(4) 0.0276(17) Uani 1 1 d . . . . .
H7 H 0.270489 0.332399 0.641960 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1751(4) 0.2766(8) 0.7030(3) 0.0240(16) Uani 1 1 d . . . . .
H8 H 0.187772 0.367504 0.732882 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2196(4) 0.1457(8) 0.7442(4) 0.0270(17) Uani 1 1 d . . . . .
H9 H 0.182330 0.067991 0.755121 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2783(4) 0.1734(8) 0.8134(4) 0.0235(15) Uani 1 1 d . . . . .
C11 C 0.3297(4) 0.2908(8) 0.8170(4) 0.0264(17) Uani 1 1 d . . . . .
H11 H 0.323897 0.362302 0.777469 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3886(4) 0.3017(8) 0.8783(4) 0.0294(17) Uani 1 1 d . . . . .
H12 H 0.422228 0.382915 0.879955 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3486(5) 0.1001(9) 0.9356(4) 0.0359(19) Uani 1 1 d . . . . .
H13 H 0.353045 0.036844 0.979032 0.043 Uiso 1 1 calc R U . . .
C14 C 0.2881(4) 0.0775(8) 0.8767(4) 0.0308(18) Uani 1 1 d . . . . .
H14 H 0.253554 -0.001717 0.878791 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1852(4) 0.2732(8) 0.5524(4) 0.0268(17) Uani 1 1 d . . . . .
C16 C 0.1952(5) 0.1707(9) 0.4971(4) 0.0325(18) Uani 1 1 d . . . . .
H16 H 0.230288 0.092875 0.509614 0.039 Uiso 1 1 calc R U . . .
C17 C 0.1539(5) 0.1810(9) 0.4226(4) 0.035(2) Uani 1 1 d . . . . .
H17 H 0.161341 0.109783 0.384904 0.042 Uiso 1 1 calc R U . . .
C18 C 0.1028(5) 0.2923(10) 0.4029(4) 0.039(2) Uani 1 1 d . . . . .
H18 H 0.073771 0.296486 0.352558 0.047 Uiso 1 1 calc R U . . .
C19 C 0.0938(5) 0.3998(9) 0.4581(4) 0.0365(19) Uani 1 1 d . . . . .
H19 H 0.059677 0.478889 0.445003 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1354(4) 0.3891(8) 0.5321(4) 0.0284(17) Uani 1 1 d . . . . .
H20 H 0.129770 0.462020 0.569413 0.034 Uiso 1 1 calc R U . . .
C21 C 0.0886(4) 0.2561(8) 0.6856(4) 0.0272(17) Uani 1 1 d . . . . .
C22 C 0.0552(5) 0.1378(9) 0.6440(4) 0.037(2) Uani 1 1 d . . . . .
H22 H 0.088136 0.065735 0.626825 0.045 Uiso 1 1 calc R U . . .
C23 C -0.0243(5) 0.1238(11) 0.6276(4) 0.044(2) Uani 1 1 d . . . . .
H23 H -0.045817 0.043422 0.598375 0.053 Uiso 1 1 calc R U . . .
C24 C -0.0734(5) 0.2257(12) 0.6531(5) 0.051(3) Uani 1 1 d . . . . .
H24 H -0.128420 0.215459 0.641584 0.061 Uiso 1 1 calc R U . . .
C25 C -0.0420(5) 0.3435(12) 0.6958(5) 0.054(3) Uani 1 1 d . . . . .
H25 H -0.075580 0.412750 0.714517 0.064 Uiso 1 1 calc R U . . .
C26 C 0.0382(5) 0.3595(9) 0.7109(4) 0.0346(19) Uani 1 1 d . . . . .
H26 H 0.059369 0.441529 0.738697 0.042 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 C27 1.895(7) . ?
Br2 C31 1.897(6) . ?
O1 C28 1.354(7) . ?
O1 H1A 0.8400 . ?
O2 C30 1.342(8) . ?
O2 H2A 0.8400 . ?
C27 C28 1.392(10) . ?
C27 C32 1.396(9) . ?
C28 C29 1.384(10) . ?
C29 C30 1.407(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.398(10) . ?
C31 C32 1.387(10) . ?
C32 H32 0.9500 . ?
N1 C5 1.317(10) . ?
N1 C1 1.347(10) . ?
N2 C12 1.333(9) . ?
N2 C13 1.333(10) . ?
C1 C2 1.375(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.359(10) . ?
C3 C6 1.510(10) . ?
C4 C5 1.395(11) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.546(10) . ?
C6 C9 1.582(9) . ?
C6 H6 1.0000 . ?
C7 C15 1.512(9) . ?
C7 C8 1.579(9) . ?
C7 H7 1.0000 . ?
C8 C21 1.495(10) . ?
C8 C9 1.561(10) . ?
C8 H8 1.0000 . ?
C9 C10 1.492(9) . ?
C9 H9 1.0000 . ?
C10 C11 1.401(10) . ?
C10 C14 1.406(9) . ?
C11 C12 1.377(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.381(10) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.377(10) . ?
C15 C20 1.394(10) . ?
C16 C17 1.396(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(9) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.398(11) . ?
C21 C26 1.403(10) . ?
C22 C23 1.371(11) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(11) . ?
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
C28 O1 H1A 109.5 . . ?
C30 O2 H2A 109.5 . . ?
C28 C27 C32 120.4(6) . . ?
C28 C27 Br1 120.3(5) . . ?
C32 C27 Br1 119.2(5) . . ?
O1 C28 C29 123.0(6) . . ?
O1 C28 C27 117.6(6) . . ?
C29 C28 C27 119.4(6) . . ?
C28 C29 C30 121.6(7) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
O2 C30 C31 119.3(6) . . ?
O2 C30 C29 123.1(6) . . ?
C31 C30 C29 117.6(6) . . ?
C32 C31 C30 121.7(6) . . ?
C32 C31 Br2 119.8(5) . . ?
C30 C31 Br2 118.5(5) . . ?
C31 C32 C27 119.3(6) . . ?
C31 C32 H32 120.4 . . ?
C27 C32 H32 120.4 . . ?
C5 N1 C1 118.1(7) . . ?
C12 N2 C13 116.5(6) . . ?
N1 C1 C2 122.3(7) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.1(7) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 117.8(7) . . ?
C4 C3 C6 123.1(7) . . ?
C2 C3 C6 119.0(7) . . ?
C3 C4 C5 119.5(7) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.7(7) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C3 C6 C7 118.8(6) . . ?
C3 C6 C9 116.8(5) . . ?
C7 C6 C9 89.4(5) . . ?
C3 C6 H6 110.1 . . ?
C7 C6 H6 110.1 . . ?
C9 C6 H6 110.1 . . ?
C15 C7 C6 119.9(6) . . ?
C15 C7 C8 117.3(6) . . ?
C6 C7 C8 89.9(5) . . ?
C15 C7 H7 109.4 . . ?
C6 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C21 C8 C9 114.4(6) . . ?
C21 C8 C7 118.7(5) . . ?
C9 C8 C7 89.0(5) . . ?
C21 C8 H8 111.0 . . ?
C9 C8 H8 111.0 . . ?
C7 C8 H8 111.0 . . ?
C10 C9 C8 118.5(6) . . ?
C10 C9 C6 114.4(6) . . ?
C8 C9 C6 89.2(5) . . ?
C10 C9 H9 111.0 . . ?
C8 C9 H9 111.0 . . ?
C6 C9 H9 111.0 . . ?
C11 C10 C14 116.5(6) . . ?
C11 C10 C9 122.0(6) . . ?
C14 C10 C9 121.3(6) . . ?
C12 C11 C10 119.4(6) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
N2 C12 C11 124.0(7) . . ?
N2 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
N2 C13 C14 124.1(7) . . ?
N2 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C13 C14 C10 119.0(7) . . ?
C13 C14 H14 120.5 . . ?
C10 C14 H14 120.5 . . ?
C16 C15 C20 119.0(6) . . ?
C16 C15 C7 121.3(7) . . ?
C20 C15 C7 119.7(6) . . ?
C15 C16 C17 120.2(8) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 121.1(7) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.3(7) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 119.2(8) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C15 121.1(7) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C22 C21 C26 117.8(7) . . ?
C22 C21 C8 122.6(7) . . ?
C26 C21 C8 119.5(7) . . ?
C23 C22 C21 121.2(8) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 120.4(9) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 119.8(8) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 119.8(9) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 120.9(8) . . ?
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
C32 C27 C28 O1 -177.8(6) . . . . ?
Br1 C27 C28 O1 4.3(9) . . . . ?
C32 C27 C28 C29 2.1(10) . . . . ?
Br1 C27 C28 C29 -175.8(5) . . . . ?
O1 C28 C29 C30 179.2(7) . . . . ?
C27 C28 C29 C30 -0.7(10) . . . . ?
C28 C29 C30 O2 -178.9(6) . . . . ?
C28 C29 C30 C31 -1.3(10) . . . . ?
O2 C30 C31 C32 179.7(6) . . . . ?
C29 C30 C31 C32 2.1(10) . . . . ?
O2 C30 C31 Br2 0.9(9) . . . . ?
C29 C30 C31 Br2 -176.7(5) . . . . ?
C30 C31 C32 C27 -0.7(10) . . . . ?
Br2 C31 C32 C27 178.1(5) . . . . ?
C28 C27 C32 C31 -1.4(10) . . . . ?
Br1 C27 C32 C31 176.5(5) . . . . ?
C5 N1 C1 C2 -3.3(10) . . . . ?
N1 C1 C2 C3 -2.6(11) . . . . ?
C1 C2 C3 C4 7.0(10) . . . . ?
C1 C2 C3 C6 -169.5(6) . . . . ?
C2 C3 C4 C5 -5.6(10) . . . . ?
C6 C3 C4 C5 170.7(6) . . . . ?
C1 N1 C5 C4 4.8(11) . . . . ?
C3 C4 C5 N1 -0.3(11) . . . . ?
C4 C3 C6 C7 -18.5(9) . . . . ?
C2 C3 C6 C7 157.8(6) . . . . ?
C4 C3 C6 C9 -123.8(7) . . . . ?
C2 C3 C6 C9 52.4(9) . . . . ?
C3 C6 C7 C15 105.8(7) . . . . ?
C9 C6 C7 C15 -133.7(6) . . . . ?
C3 C6 C7 C8 -132.4(6) . . . . ?
C9 C6 C7 C8 -11.9(5) . . . . ?
C15 C7 C8 C21 18.6(10) . . . . ?
C6 C7 C8 C21 -105.4(7) . . . . ?
C15 C7 C8 C9 136.1(7) . . . . ?
C6 C7 C8 C9 12.0(5) . . . . ?
C21 C8 C9 C10 -132.9(6) . . . . ?
C7 C8 C9 C10 105.9(6) . . . . ?
C21 C8 C9 C6 109.5(6) . . . . ?
C7 C8 C9 C6 -11.7(5) . . . . ?
C3 C6 C9 C10 13.1(9) . . . . ?
C7 C6 C9 C10 -109.2(6) . . . . ?
C3 C6 C9 C8 134.3(7) . . . . ?
C7 C6 C9 C8 12.0(5) . . . . ?
C8 C9 C10 C11 -40.3(9) . . . . ?
C6 C9 C10 C11 62.9(9) . . . . ?
C8 C9 C10 C14 143.7(7) . . . . ?
C6 C9 C10 C14 -113.1(7) . . . . ?
C14 C10 C11 C12 3.7(10) . . . . ?
C9 C10 C11 C12 -172.4(6) . . . . ?
C13 N2 C12 C11 -6.3(11) . . . . ?
C10 C11 C12 N2 0.9(11) . . . . ?
C12 N2 C13 C14 7.2(11) . . . . ?
N2 C13 C14 C10 -2.7(12) . . . . ?
C11 C10 C14 C13 -2.9(10) . . . . ?
C9 C10 C14 C13 173.3(7) . . . . ?
C6 C7 C15 C16 -22.2(10) . . . . ?
C8 C7 C15 C16 -129.3(7) . . . . ?
C6 C7 C15 C20 157.2(7) . . . . ?
C8 C7 C15 C20 50.2(9) . . . . ?
C20 C15 C16 C17 -2.1(11) . . . . ?
C7 C15 C16 C17 177.4(7) . . . . ?
C15 C16 C17 C18 -0.1(11) . . . . ?
C16 C17 C18 C19 2.0(12) . . . . ?
C17 C18 C19 C20 -1.7(12) . . . . ?
C18 C19 C20 C15 -0.5(11) . . . . ?
C16 C15 C20 C19 2.4(11) . . . . ?
C7 C15 C20 C19 -177.1(7) . . . . ?
C9 C8 C21 C22 -53.9(8) . . . . ?
C7 C8 C21 C22 49.2(9) . . . . ?
C9 C8 C21 C26 126.8(6) . . . . ?
C7 C8 C21 C26 -130.1(7) . . . . ?
C26 C21 C22 C23 0.7(10) . . . . ?
C8 C21 C22 C23 -178.6(6) . . . . ?
C21 C22 C23 C24 -1.2(11) . . . . ?
C22 C23 C24 C25 0.1(12) . . . . ?
C23 C24 C25 C26 1.5(12) . . . . ?
C24 C25 C26 C21 -1.9(11) . . . . ?
C22 C21 C26 C25 0.8(10) . . . . ?
C8 C21 C26 C25 -179.9(6) . . . . ?

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 0.84 1.87 2.707(8) 171.9 2_656
O2 H2A N2 0.84 1.85 2.661(7) 163.2 2_656
C5 H5 O2 0.95 2.35 3.203(9) 149.4 3_666
C11 H11 O1 0.95 2.46 3.335(9) 153.4 .
C12 H12 N1 0.95 2.63 3.424(9) 141.3 2_656

_refine_diff_density_max         1.915
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.135

