# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 1833962'
_audit_update_record             
;
2018-03-31 deposited with the CCDC.
2018-08-07 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         'C31 H25 Cl N2 O3'
_chemical_formula_sum            'C31 H25 Cl N2 O3'
_chemical_formula_weight         508.98

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      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                   13.114(2)
_cell_length_b                   22.015(4)
_cell_length_c                   9.2346(16)
_cell_angle_alpha                90
_cell_angle_beta                 105.660(5)
_cell_angle_gamma                90
_cell_volume                     2567.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5850
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      23.73

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26039
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5894
_reflns_number_gt                2966
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+0.8433P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0140(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5894
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1589
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1742
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
C1 C -0.2353(2) 0.35069(14) 0.4260(3) 0.0655(8) Uani 1 1 d . . . . .
C2 C -0.3392(3) 0.36311(19) 0.3463(4) 0.0947(12) Uani 1 1 d . . . . .
H2 H -0.3807 0.3902 0.3829 0.114 Uiso 1 1 calc R U . . .
C3 C -0.3779(3) 0.3341(2) 0.2126(5) 0.1177(16) Uani 1 1 d . . . . .
H3 H -0.4470 0.3418 0.1567 0.141 Uiso 1 1 calc R U . . .
C4 C -0.3171(3) 0.2934(2) 0.1575(5) 0.1230(17) Uani 1 1 d . . . . .
H4 H -0.3465 0.2740 0.0663 0.148 Uiso 1 1 calc R U . . .
C5 C -0.2146(3) 0.28110(19) 0.2345(4) 0.1058(14) Uani 1 1 d . . . . .
H5 H -0.1743 0.2539 0.1962 0.127 Uiso 1 1 calc R U . . .
C6 C -0.1715(2) 0.31031(14) 0.3724(4) 0.0693(9) Uani 1 1 d . . . . .
C7 C -0.0708(2) 0.30993(12) 0.4803(3) 0.0579(7) Uani 1 1 d . . . . .
C8 C -0.07691(19) 0.34810(11) 0.5931(3) 0.0478(7) Uani 1 1 d . . . . .
C9 C 0.0269(2) 0.27460(16) 0.4884(4) 0.0818(11) Uani 1 1 d . . . . .
H9A H 0.0210 0.2348 0.5306 0.098 Uiso 1 1 calc R U . . .
H9B H 0.0348 0.2690 0.3878 0.098 Uiso 1 1 calc R U . . .
C10 C 0.1216(2) 0.30608(14) 0.5824(3) 0.0637(8) Uani 1 1 d . . . . .
H10A H 0.1806 0.2779 0.6075 0.076 Uiso 1 1 calc R U . . .
H10B H 0.1404 0.3393 0.5254 0.076 Uiso 1 1 calc R U . . .
C11 C 0.00916(19) 0.35617(10) 0.7264(3) 0.0422(6) Uani 1 1 d . . . . .
C12 C 0.02258(19) 0.37933(10) 0.8706(3) 0.0436(6) Uani 1 1 d . . . . .
C13 C -0.0641(2) 0.40711(12) 0.9171(3) 0.0554(7) Uani 1 1 d . . . . .
C14 C -0.1299(3) 0.4425(2) 1.1176(4) 0.1152(16) Uani 1 1 d . . . . .
H14A H -0.1597 0.4764 1.0531 0.138 Uiso 1 1 calc R U . . .
H14B H -0.1863 0.4138 1.1160 0.138 Uiso 1 1 calc R U . . .
C15 C -0.0843(4) 0.4636(2) 1.2690(5) 0.1183(15) Uani 1 1 d . . . . .
H15A H -0.0509 0.4302 1.3308 0.177 Uiso 1 1 calc R U . . .
H15B H -0.1390 0.4802 1.3085 0.177 Uiso 1 1 calc R U . . .
H15C H -0.0325 0.4944 1.2687 0.177 Uiso 1 1 calc R U . . .
C16 C 0.2902(2) 0.34076(11) 1.1509(3) 0.0516(7) Uani 1 1 d . . . . .
C17 C 0.3568(2) 0.34417(13) 1.2950(4) 0.0642(8) Uani 1 1 d . . . . .
H17 H 0.4171 0.3200 1.3219 0.077 Uiso 1 1 calc R U . . .
C18 C 0.3345(3) 0.38301(15) 1.3983(4) 0.0731(9) Uani 1 1 d . . . . .
H18 H 0.3778 0.3846 1.4962 0.088 Uiso 1 1 calc R U . . .
C19 C 0.2470(3) 0.41941(13) 1.3540(3) 0.0651(8) Uani 1 1 d . . . . .
C20 C 0.1793(2) 0.41673(12) 1.2119(3) 0.0547(7) Uani 1 1 d . . . . .
H20 H 0.1211 0.4426 1.1856 0.066 Uiso 1 1 calc R U . . .
C21 C 0.1973(2) 0.37566(11) 1.1071(3) 0.0459(6) Uani 1 1 d . . . . .
C22 C 0.13011(19) 0.36617(10) 0.9537(3) 0.0425(6) Uani 1 1 d . . . . .
C23 C 0.17516(18) 0.33615(10) 0.8573(3) 0.0428(6) Uani 1 1 d . . . . .
C24 C 0.28661(19) 0.31391(11) 0.8968(3) 0.0483(7) Uani 1 1 d . . . . .
H24 H 0.2877 0.2761 0.8411 0.058 Uiso 1 1 calc R U . . .
C25 C 0.36532(18) 0.35703(11) 0.8585(3) 0.0459(6) Uani 1 1 d . . . . .
C26 C 0.4523(2) 0.33511(14) 0.8189(3) 0.0616(8) Uani 1 1 d . . . . .
H26 H 0.4615 0.2934 0.8129 0.074 Uiso 1 1 calc R U . . .
C27 C 0.5259(2) 0.37407(16) 0.7880(4) 0.0700(9) Uani 1 1 d . . . . .
H27 H 0.5839 0.3582 0.7612 0.084 Uiso 1 1 calc R U . . .
C28 C 0.5153(2) 0.43604(15) 0.7960(3) 0.0646(8) Uani 1 1 d . . . . .
C29 C 0.5934(3) 0.47864(18) 0.7569(5) 0.1036(13) Uani 1 1 d . . . . .
H29A H 0.5859 0.5184 0.7957 0.155 Uiso 1 1 calc R U . . .
H29B H 0.5803 0.4807 0.6496 0.155 Uiso 1 1 calc R U . . .
H29C H 0.6640 0.4640 0.8006 0.155 Uiso 1 1 calc R U . . .
C30 C 0.4285(2) 0.45719(13) 0.8353(3) 0.0657(8) Uani 1 1 d . . . . .
H30 H 0.4195 0.4989 0.8415 0.079 Uiso 1 1 calc R U . . .
C31 C 0.3539(2) 0.41899(12) 0.8662(3) 0.0582(8) Uani 1 1 d . . . . .
H31 H 0.2956 0.4351 0.8922 0.070 Uiso 1 1 calc R U . . .
Cl1 Cl 0.22041(9) 0.47092(5) 1.48087(10) 0.1039(4) Uani 1 1 d . . . . .
N1 N -0.17655(17) 0.37309(11) 0.5607(3) 0.0614(7) Uani 1 1 d . . . . .
H1 H -0.1983 0.3986 0.6161 0.074 Uiso 1 1 calc R U . . .
N2 N 0.10320(15) 0.32991(8) 0.7208(2) 0.0425(5) Uani 1 1 d . . . . .
O1 O -0.14529(19) 0.42482(13) 0.8337(3) 0.1008(9) Uani 1 1 d . . . . .
O2 O -0.04686(16) 0.41316(11) 1.0630(2) 0.0823(7) Uani 1 1 d . . . . .
O3 O 0.31673(14) 0.29909(8) 1.0559(2) 0.0566(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.366(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.361(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.423(4) . ?
C7 C8 1.357(4) . ?
C7 C9 1.483(4) . ?
C8 N1 1.374(3) . ?
C8 C11 1.439(4) . ?
C9 C10 1.481(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.461(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.375(3) . ?
C11 C12 1.392(3) . ?
C12 C22 1.441(3) . ?
C12 C13 1.455(4) . ?
C13 O1 1.198(3) . ?
C13 O2 1.311(3) . ?
C14 C15 1.441(5) . ?
C14 O2 1.468(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O3 1.377(3) . ?
C16 C17 1.382(4) . ?
C16 C21 1.405(4) . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(4) . ?
C19 Cl1 1.732(3) . ?
C20 C21 1.390(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.467(4) . ?
C22 C23 1.365(3) . ?
C23 N2 1.362(3) . ?
C23 C24 1.490(3) . ?
C24 O3 1.451(3) . ?
C24 C25 1.513(3) . ?
C24 H24 0.9800 . ?
C25 C26 1.376(4) . ?
C25 C31 1.376(4) . ?
C26 C27 1.377(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.375(4) . ?
C27 H27 0.9300 . ?
C28 C30 1.367(4) . ?
C28 C29 1.503(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.377(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 130.0(3) . . ?
N1 C1 C6 107.9(2) . . ?
C2 C1 C6 122.1(3) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.7(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 106.7(3) . . ?
C5 C6 C7 134.7(3) . . ?
C8 C7 C6 107.3(2) . . ?
C8 C7 C9 121.0(2) . . ?
C6 C7 C9 131.6(3) . . ?
C7 C8 N1 109.3(2) . . ?
C7 C8 C11 122.5(2) . . ?
N1 C8 C11 128.1(2) . . ?
C10 C9 C7 111.1(2) . . ?
C10 C9 H9A 109.4 . . ?
C7 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C7 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C9 111.7(2) . . ?
N2 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C12 107.9(2) . . ?
N2 C11 C8 114.9(2) . . ?
C12 C11 C8 137.0(2) . . ?
C11 C12 C22 106.8(2) . . ?
C11 C12 C13 122.0(2) . . ?
C22 C12 C13 131.1(2) . . ?
O1 C13 O2 120.3(3) . . ?
O1 C13 C12 125.2(3) . . ?
O2 C13 C12 114.5(2) . . ?
C15 C14 O2 108.8(3) . . ?
C15 C14 H14A 109.9 . . ?
O2 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
O2 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 C17 116.5(3) . . ?
O3 C16 C21 122.0(2) . . ?
C17 C16 C21 121.4(3) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 118.5(3) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C20 122.3(3) . . ?
C18 C19 Cl1 119.2(2) . . ?
C20 C19 Cl1 118.6(3) . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 116.9(2) . . ?
C20 C21 C22 126.5(2) . . ?
C16 C21 C22 116.6(2) . . ?
C23 C22 C12 106.5(2) . . ?
C23 C22 C21 116.5(2) . . ?
C12 C22 C21 137.0(2) . . ?
N2 C23 C22 109.8(2) . . ?
N2 C23 C24 125.6(2) . . ?
C22 C23 C24 124.6(2) . . ?
O3 C24 C23 107.6(2) . . ?
O3 C24 C25 111.18(19) . . ?
C23 C24 C25 115.0(2) . . ?
O3 C24 H24 107.6 . . ?
C23 C24 H24 107.6 . . ?
C25 C24 H24 107.6 . . ?
C26 C25 C31 118.1(2) . . ?
C26 C25 C24 120.6(2) . . ?
C31 C25 C24 121.3(2) . . ?
C25 C26 C27 120.9(3) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C28 C27 C26 121.4(3) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C30 C28 C27 117.1(3) . . ?
C30 C28 C29 121.5(3) . . ?
C27 C28 C29 121.4(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 C31 122.4(3) . . ?
C28 C30 H30 118.8 . . ?
C31 C30 H30 118.8 . . ?
C25 C31 C30 120.1(3) . . ?
C25 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C1 N1 C8 108.9(2) . . ?
C1 N1 H1 125.6 . . ?
C8 N1 H1 125.6 . . ?
C23 N2 C11 109.1(2) . . ?
C23 N2 C10 127.5(2) . . ?
C11 N2 C10 123.0(2) . . ?
C13 O2 C14 117.3(2) . . ?
C16 O3 C24 116.64(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
N1 H1 O1 0.86 2.02 2.695(3) 134.2 .

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1833965'
_audit_update_record             
;
2018-03-31 deposited with the CCDC.
2018-08-07 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         'C27 H28 N2 O3'
_chemical_formula_sum            'C27 H28 N2 O3'
_chemical_formula_weight         428.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   7.9309(8)
_cell_length_b                   8.1886(8)
_cell_length_c                   18.5826(19)
_cell_angle_alpha                96.559(3)
_cell_angle_beta                 100.627(4)
_cell_angle_gamma                98.478(3)
_cell_volume                     1160.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6608
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18192
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.254
_diffrn_reflns_theta_max         27.609
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5359
_reflns_number_gt                3465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.2369P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5359
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.6402(2) 0.5332(2) 0.69566(10) 0.0457(4) Uani 1 1 d . . . . .
C2 C 0.5817(3) 0.6646(2) 0.73216(12) 0.0584(5) Uani 1 1 d . . . . .
H2 H 0.5462 0.7505 0.7077 0.070 Uiso 1 1 calc R U . . .
C3 C 0.5781(3) 0.6633(3) 0.80547(13) 0.0711(6) Uani 1 1 d . . . . .
H3 H 0.5395 0.7500 0.8310 0.085 Uiso 1 1 calc R U . . .
C4 C 0.6310(3) 0.5349(3) 0.84290(12) 0.0690(6) Uani 1 1 d . . . . .
C5 C 0.7027(5) 0.4478(4) 0.96108(14) 0.1101(10) Uani 1 1 d . . . . .
H5A H 0.6460 0.3344 0.9442 0.165 Uiso 1 1 calc R U . . .
H5B H 0.6939 0.4785 1.0115 0.165 Uiso 1 1 calc R U . . .
H5C H 0.8232 0.4583 0.9580 0.165 Uiso 1 1 calc R U . . .
C6 C 0.6848(3) 0.4019(3) 0.80683(11) 0.0589(5) Uani 1 1 d . . . . .
H6 H 0.7183 0.3160 0.8318 0.071 Uiso 1 1 calc R U . . .
C7 C 0.6879(2) 0.3990(2) 0.73149(10) 0.0464(4) Uani 1 1 d . . . . .
C8 C 0.7300(2) 0.2829(2) 0.67690(10) 0.0444(4) Uani 1 1 d . . . . .
C9 C 0.7099(2) 0.35066(19) 0.61254(9) 0.0414(4) Uani 1 1 d . . . . .
C10 C 0.7856(3) 0.1161(2) 0.67950(10) 0.0508(5) Uani 1 1 d . . . . .
H10A H 0.7382 0.0616 0.7169 0.061 Uiso 1 1 calc R U . . .
H10B H 0.9116 0.1309 0.6928 0.061 Uiso 1 1 calc R U . . .
C11 C 0.7216(3) 0.0085(2) 0.60480(10) 0.0511(5) Uani 1 1 d . . . . .
H11A H 0.7808 -0.0870 0.6031 0.061 Uiso 1 1 calc R U . . .
H11B H 0.5978 -0.0326 0.5980 0.061 Uiso 1 1 calc R U . . .
C12 C 0.7399(2) 0.26726(19) 0.54465(9) 0.0400(4) Uani 1 1 d . . . . .
C13 C 0.7610(2) 0.30776(19) 0.47588(9) 0.0399(4) Uani 1 1 d . . . . .
C14 C 0.7601(2) 0.4748(2) 0.45521(9) 0.0425(4) Uani 1 1 d . . . . .
C15 C 0.7910(3) 0.6370(2) 0.35982(12) 0.0644(6) Uani 1 1 d . . . . .
H15A H 0.6830 0.6753 0.3617 0.097 Uiso 1 1 calc R U . . .
H15B H 0.8064 0.6232 0.3096 0.097 Uiso 1 1 calc R U . . .
H15C H 0.8855 0.7174 0.3897 0.097 Uiso 1 1 calc R U . . .
C16 C 0.7775(2) 0.0373(2) 0.47723(10) 0.0471(4) Uani 1 1 d . . . . .
H16 H 0.7875 -0.0732 0.4637 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7845(2) 0.1583(2) 0.43248(9) 0.0420(4) Uani 1 1 d . . . . .
C18 C 0.8040(2) 0.12621(19) 0.35457(9) 0.0412(4) Uani 1 1 d . . . . .
C19 C 0.9319(2) 0.2179(2) 0.32630(10) 0.0496(4) Uani 1 1 d . . . . .
H19 H 1.0106 0.3044 0.3571 0.060 Uiso 1 1 calc R U . . .
C20 C 0.9442(3) 0.1827(2) 0.25351(11) 0.0567(5) Uani 1 1 d . . . . .
H20 H 1.0313 0.2467 0.2364 0.068 Uiso 1 1 calc R U . . .
C21 C 0.8313(3) 0.0551(3) 0.20468(10) 0.0558(5) Uani 1 1 d . . . . .
C22 C 0.8475(4) 0.0186(4) 0.12416(12) 0.0803(7) Uani 1 1 d . . . . .
C23 C 1.0120(8) -0.0503(9) 0.1208(2) 0.151(3) Uani 0.744(4) 1 d . . P A 1
H23A H 1.0056 -0.1543 0.1402 0.226 Uiso 0.744(4) 1 calc R U P A 1
H23B H 1.1100 0.0276 0.1498 0.226 Uiso 0.744(4) 1 calc R U P A 1
H23C H 1.0254 -0.0680 0.0704 0.226 Uiso 0.744(4) 1 calc R U P A 1
C24 C 0.8681(9) 0.1882(6) 0.0920(2) 0.140(2) Uani 0.744(4) 1 d . . P A 1
H24A H 0.9669 0.2636 0.1218 0.211 Uiso 0.744(4) 1 calc R U P A 1
H24B H 0.7650 0.2364 0.0925 0.211 Uiso 0.744(4) 1 calc R U P A 1
H24C H 0.8849 0.1682 0.0421 0.211 Uiso 0.744(4) 1 calc R U P A 1
C25 C 0.6887(7) -0.0891(9) 0.0759(2) 0.136(2) Uani 0.744(4) 1 d . . P A 1
H25A H 0.6942 -0.0865 0.0249 0.204 Uiso 0.744(4) 1 calc R U P A 1
H25B H 0.5866 -0.0482 0.0857 0.204 Uiso 0.744(4) 1 calc R U P A 1
H25C H 0.6835 -0.2018 0.0863 0.204 Uiso 0.744(4) 1 calc R U P A 1
C23' C 1.008(2) 0.108(3) 0.1082(7) 0.151(3) Uani 0.256(4) 1 d . . P A 2
H23D H 1.0080 0.0827 0.0565 0.226 Uiso 0.256(4) 1 calc R U P A 2
H23E H 1.1070 0.0751 0.1369 0.226 Uiso 0.256(4) 1 calc R U P A 2
H23F H 1.0130 0.2264 0.1207 0.226 Uiso 0.256(4) 1 calc R U P A 2
C24' C 0.687(3) 0.042(2) 0.0749(8) 0.140(2) Uani 0.256(4) 1 d . . P A 2
H24D H 0.6604 0.1500 0.0896 0.211 Uiso 0.256(4) 1 calc R U P A 2
H24E H 0.5922 -0.0428 0.0782 0.211 Uiso 0.256(4) 1 calc R U P A 2
H24F H 0.7034 0.0338 0.0248 0.211 Uiso 0.256(4) 1 calc R U P A 2
C25' C 0.863(2) -0.181(2) 0.1112(6) 0.136(2) Uani 0.256(4) 1 d . . P A 2
H25D H 0.8973 -0.2071 0.0649 0.204 Uiso 0.256(4) 1 calc R U P A 2
H25E H 0.7522 -0.2474 0.1103 0.204 Uiso 0.256(4) 1 calc R U P A 2
H25F H 0.9485 -0.2040 0.1507 0.204 Uiso 0.256(4) 1 calc R U P A 2
C26 C 0.7069(3) -0.0378(2) 0.23348(11) 0.0554(5) Uani 1 1 d . . . . .
H26 H 0.6304 -0.1263 0.2029 0.066 Uiso 1 1 calc R U . . .
C27 C 0.6928(2) -0.0031(2) 0.30649(10) 0.0469(4) Uani 1 1 d . . . . .
H27 H 0.6066 -0.0681 0.3237 0.056 Uiso 1 1 calc R U . . .
N1 N 0.65549(19) 0.50165(17) 0.62318(8) 0.0450(4) Uani 1 1 d . . . . .
H1 H 0.6346 0.5655 0.5901 0.054 Uiso 1 1 calc R U . . .
N2 N 0.75358(19) 0.10274(16) 0.54473(8) 0.0445(4) Uani 1 1 d . . . . .
O1 O 0.6224(3) 0.5533(3) 0.91673(9) 0.1040(7) Uani 1 1 d . . . . .
O2 O 0.73582(19) 0.59600(15) 0.49338(7) 0.0596(4) Uani 1 1 d . . . . .
O3 O 0.7881(2) 0.48066(15) 0.38729(7) 0.0601(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.373(2) . ?
C1 C2 1.389(3) . ?
C1 C7 1.411(2) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.376(3) . ?
C4 O1 1.378(3) . ?
C5 O1 1.401(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.402(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.429(2) . ?
C8 C9 1.368(2) . ?
C8 C10 1.498(2) . ?
C9 N1 1.374(2) . ?
C9 C12 1.441(2) . ?
C10 C11 1.513(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.466(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.3676(19) . ?
C12 C13 1.390(2) . ?
C13 C17 1.442(2) . ?
C13 C14 1.463(2) . ?
C14 O2 1.213(2) . ?
C14 O3 1.326(2) . ?
C15 O3 1.430(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N2 1.364(2) . ?
C16 C17 1.366(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.482(2) . ?
C18 C27 1.384(2) . ?
C18 C19 1.390(2) . ?
C19 C20 1.375(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9300 . ?
C21 C26 1.381(3) . ?
C21 C22 1.525(3) . ?
C22 C23' 1.469(19) . ?
C22 C24' 1.477(19) . ?
C22 C25 1.498(5) . ?
C22 C23 1.504(5) . ?
C22 C24 1.572(5) . ?
C22 C25' 1.649(18) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C23' H23D 0.9600 . ?
C23' H23E 0.9600 . ?
C23' H23F 0.9600 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
C25' H25D 0.9600 . ?
C25' H25E 0.9600 . ?
C25' H25F 0.9600 . ?
C26 C27 1.382(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 130.15(17) . . ?
N1 C1 C7 108.13(15) . . ?
C2 C1 C7 121.66(17) . . ?
C3 C2 C1 117.65(19) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.73(19) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C6 C4 O1 124.2(2) . . ?
C6 C4 C3 121.12(19) . . ?
O1 C4 C3 114.63(19) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 118.40(19) . . ?
C4 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C1 119.36(17) . . ?
C6 C7 C8 133.99(17) . . ?
C1 C7 C8 106.65(15) . . ?
C9 C8 C7 106.68(15) . . ?
C9 C8 C10 120.64(15) . . ?
C7 C8 C10 132.68(16) . . ?
C8 C9 N1 110.23(15) . . ?
C8 C9 C12 122.49(15) . . ?
N1 C9 C12 127.26(15) . . ?
C8 C10 C11 109.94(14) . . ?
C8 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
C8 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N2 C11 C10 111.20(14) . . ?
N2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C13 107.57(14) . . ?
N2 C12 C9 115.01(14) . . ?
C13 C12 C9 137.42(14) . . ?
C12 C13 C17 107.36(14) . . ?
C12 C13 C14 123.90(15) . . ?
C17 C13 C14 128.73(15) . . ?
O2 C14 O3 122.17(15) . . ?
O2 C14 C13 126.14(16) . . ?
O3 C14 C13 111.68(14) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 109.86(14) . . ?
N2 C16 H16 125.1 . . ?
C17 C16 H16 125.1 . . ?
C16 C17 C13 105.81(15) . . ?
C16 C17 C18 123.23(15) . . ?
C13 C17 C18 130.89(15) . . ?
C27 C18 C19 116.88(16) . . ?
C27 C18 C17 119.62(15) . . ?
C19 C18 C17 123.49(16) . . ?
C20 C19 C18 121.10(17) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 122.31(18) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C26 C21 C20 116.32(17) . . ?
C26 C21 C22 122.3(2) . . ?
C20 C21 C22 121.32(19) . . ?
C23' C22 C24' 113.8(9) . . ?
C25 C22 C23 113.2(4) . . ?
C23' C22 C21 113.8(6) . . ?
C24' C22 C21 109.7(6) . . ?
C25 C22 C21 113.1(3) . . ?
C23 C22 C21 109.4(2) . . ?
C25 C22 C24 105.9(4) . . ?
C23 C22 C24 106.5(4) . . ?
C21 C22 C24 108.4(2) . . ?
C23' C22 C25' 105.6(9) . . ?
C24' C22 C25' 108.2(9) . . ?
C21 C22 C25' 105.1(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C23' H23D 109.5 . . ?
C22 C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22 C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C22 C24' H24D 109.5 . . ?
C22 C24' H24E 109.5 . . ?
H24D C24' H24E 109.5 . . ?
C22 C24' H24F 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C22 C25' H25D 109.5 . . ?
C22 C25' H25E 109.5 . . ?
H25D C25' H25E 109.5 . . ?
C22 C25' H25F 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
C21 C26 C27 121.85(18) . . ?
C21 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C18 121.52(17) . . ?
C26 C27 H27 119.2 . . ?
C18 C27 H27 119.2 . . ?
C1 N1 C9 108.30(14) . . ?
C1 N1 H1 125.8 . . ?
C9 N1 H1 125.8 . . ?
C16 N2 C12 109.37(14) . . ?
C16 N2 C11 125.94(14) . . ?
C12 N2 C11 124.14(14) . . ?
C4 O1 C5 117.9(2) . . ?
C14 O3 C15 117.71(14) . . ?

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
N1 H1 O2 0.86 2.12 2.7691(19) 131.4 .

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_2e
_database_code_depnum_ccdc_archive 'CCDC 1833966'
_audit_update_record             
;
2018-03-31 deposited with the CCDC.
2018-08-07 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         'C24 H22 N2 O2'
_chemical_formula_sum            'C24 H22 N2 O2'
_chemical_formula_weight         370.43

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.5245(8)
_cell_length_b                   9.0785(9)
_cell_length_c                   25.005(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1935.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5448
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      22.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22351
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.387
_diffrn_reflns_theta_max         27.749
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4459
_reflns_number_gt                2447
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.1621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4459
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
C1 C 0.6343(4) 0.5988(4) 0.00773(13) 0.0592(9) Uani 1 1 d . . . . .
C2 C 0.6786(5) 0.7363(4) -0.01137(15) 0.0763(11) Uani 1 1 d . . . . .
H2 H 0.7430 0.7985 0.0084 0.092 Uiso 1 1 calc R U . . .
C3 C 0.6229(6) 0.7766(5) -0.06094(17) 0.0913(14) Uani 1 1 d . . . . .
H3 H 0.6483 0.8688 -0.0746 0.110 Uiso 1 1 calc R U . . .
C4 C 0.5297(7) 0.6825(5) -0.09107(17) 0.0950(14) Uani 1 1 d . . . . .
H4 H 0.4953 0.7132 -0.1246 0.114 Uiso 1 1 calc R U . . .
C5 C 0.4870(5) 0.5466(5) -0.07298(15) 0.0776(11) Uani 1 1 d . . . . .
H5 H 0.4244 0.4850 -0.0937 0.093 Uiso 1 1 calc R U . . .
C6 C 0.5398(4) 0.5019(4) -0.02231(13) 0.0592(9) Uani 1 1 d . . . . .
C7 C 0.5220(4) 0.3714(4) 0.00887(13) 0.0565(8) Uani 1 1 d . . . . .
C8 C 0.6004(4) 0.3937(4) 0.05586(12) 0.0511(8) Uani 1 1 d . . . . .
C9 C 0.4417(5) 0.2283(4) -0.00100(16) 0.0758(11) Uani 1 1 d . . . . .
H9A H 0.3311 0.2392 0.0072 0.091 Uiso 1 1 calc R U . . .
H9B H 0.4504 0.2042 -0.0387 0.091 Uiso 1 1 calc R U . . .
C10 C 0.5036(6) 0.1084(5) 0.02977(14) 0.0883(13) Uani 1 1 d . . . . .
H10A H 0.5927 0.0673 0.0108 0.106 Uiso 1 1 calc R U . . .
H10B H 0.4242 0.0322 0.0321 0.106 Uiso 1 1 calc R U . . .
C11 C 0.6121(4) 0.2832(4) 0.09679(13) 0.0517(8) Uani 1 1 d . . . . .
C12 C 0.6639(4) 0.2753(4) 0.14950(13) 0.0512(8) Uani 1 1 d . . . . .
C13 C 0.7282(4) 0.4014(4) 0.17901(16) 0.0607(9) Uani 1 1 d . . . . .
C14 C 0.7949(5) 0.4917(5) 0.26433(17) 0.0907(14) Uani 1 1 d . . . . .
H14A H 0.8870 0.5361 0.2493 0.136 Uiso 1 1 calc R U . . .
H14B H 0.8185 0.4550 0.2994 0.136 Uiso 1 1 calc R U . . .
H14C H 0.7128 0.5638 0.2667 0.136 Uiso 1 1 calc R U . . .
C15 C 0.6075(4) 0.0979(4) 0.26804(14) 0.0650(10) Uani 1 1 d . . . . .
H15 H 0.5333 0.1729 0.2688 0.078 Uiso 1 1 calc R U . . .
C16 C 0.6479(5) 0.0265(5) 0.31527(15) 0.0729(11) Uani 1 1 d . . . . .
H16 H 0.5993 0.0541 0.3470 0.088 Uiso 1 1 calc R U . . .
C17 C 0.7579(5) -0.0839(4) 0.31611(16) 0.0731(11) Uani 1 1 d . . . . .
C18 C 0.8044(6) -0.1634(5) 0.36652(17) 0.1057(16) Uani 1 1 d . . . . .
H18A H 0.7745 -0.2651 0.3639 0.158 Uiso 1 1 calc R U . . .
H18B H 0.7523 -0.1192 0.3966 0.158 Uiso 1 1 calc R U . . .
H18C H 0.9159 -0.1565 0.3713 0.158 Uiso 1 1 calc R U . . .
C19 C 0.8265(5) -0.1232(5) 0.26839(18) 0.0836(12) Uani 1 1 d . . . . .
H19 H 0.9016 -0.1976 0.2680 0.100 Uiso 1 1 calc R U . . .
C20 C 0.7860(5) -0.0542(4) 0.22094(17) 0.0772(12) Uani 1 1 d . . . . .
H20 H 0.8331 -0.0843 0.1892 0.093 Uiso 1 1 calc R U . . .
C21 C 0.6768(4) 0.0586(4) 0.21978(14) 0.0589(9) Uani 1 1 d . . . . .
C22 C 0.6360(4) 0.1278(4) 0.16791(13) 0.0568(9) Uani 1 1 d . . . . .
C23 C 0.5690(4) 0.0524(4) 0.12634(14) 0.0627(9) Uani 1 1 d . . . . .
C24 C 0.5161(6) -0.1046(4) 0.12345(16) 0.0928(14) Uani 1 1 d . . . . .
H24A H 0.5158 -0.1464 0.1587 0.139 Uiso 1 1 calc R U . . .
H24B H 0.5864 -0.1593 0.1010 0.139 Uiso 1 1 calc R U . . .
H24C H 0.4121 -0.1086 0.1088 0.139 Uiso 1 1 calc R U . . .
N1 N 0.6697(4) 0.5306(3) 0.05520(12) 0.0618(8) Uani 1 1 d . . . . .
H1 H 0.7259 0.5674 0.0804 0.074 Uiso 1 1 calc R U . . .
N2 N 0.5531(3) 0.1468(3) 0.08345(10) 0.0590(8) Uani 1 1 d . . . . .
O1 O 0.7641(3) 0.5192(3) 0.15982(11) 0.0791(8) Uani 1 1 d . . . . .
O2 O 0.7446(3) 0.3724(3) 0.23094(10) 0.0765(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.372(4) . ?
C1 C2 1.389(5) . ?
C1 C6 1.410(5) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.427(5) . ?
C7 C8 1.367(4) . ?
C7 C9 1.489(5) . ?
C8 N1 1.376(4) . ?
C8 C11 1.436(4) . ?
C9 C10 1.433(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.449(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.378(4) . ?
C11 C12 1.392(5) . ?
C12 C22 1.436(5) . ?
C12 C13 1.468(5) . ?
C13 O1 1.212(4) . ?
C13 O2 1.332(4) . ?
C14 O2 1.433(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C21 1.390(5) . ?
C15 C16 1.391(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(6) . ?
C16 H16 0.9300 . ?
C17 C19 1.376(6) . ?
C17 C18 1.505(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.385(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.483(5) . ?
C22 C23 1.369(4) . ?
C23 N2 1.379(4) . ?
C23 C24 1.496(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 130.0(3) . . ?
N1 C1 C6 107.7(3) . . ?
C2 C1 C6 122.2(3) . . ?
C3 C2 C1 117.0(4) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 122.0(4) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 118.3(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 134.3(3) . . ?
C1 C6 C7 106.8(3) . . ?
C8 C7 C6 107.1(3) . . ?
C8 C7 C9 119.8(3) . . ?
C6 C7 C9 133.1(3) . . ?
C7 C8 N1 109.5(3) . . ?
C7 C8 C11 122.9(3) . . ?
N1 C8 C11 127.5(3) . . ?
C10 C9 C7 113.8(3) . . ?
C10 C9 H9A 108.8 . . ?
C7 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C7 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 N2 115.0(3) . . ?
C9 C10 H10A 108.5 . . ?
N2 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
N2 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 C12 107.4(3) . . ?
N2 C11 C8 115.5(3) . . ?
C12 C11 C8 137.1(3) . . ?
C11 C12 C22 107.4(3) . . ?
C11 C12 C13 123.6(3) . . ?
C22 C12 C13 128.9(3) . . ?
O1 C13 O2 122.3(3) . . ?
O1 C13 C12 125.7(3) . . ?
O2 C13 C12 112.0(3) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C15 C16 120.8(4) . . ?
C21 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 121.5(4) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C19 117.8(4) . . ?
C16 C17 C18 122.8(4) . . ?
C19 C17 C18 119.4(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C20 121.3(4) . . ?
C17 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C15 117.2(3) . . ?
C20 C21 C22 119.3(3) . . ?
C15 C21 C22 123.4(3) . . ?
C23 C22 C12 107.0(3) . . ?
C23 C22 C21 123.4(3) . . ?
C12 C22 C21 129.5(3) . . ?
C22 C23 N2 108.7(3) . . ?
C22 C23 C24 129.7(4) . . ?
N2 C23 C24 121.6(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C8 108.9(3) . . ?
C1 N1 H1 125.6 . . ?
C8 N1 H1 125.6 . . ?
C11 N2 C23 109.5(3) . . ?
C11 N2 C10 123.1(3) . . ?
C23 N2 C10 126.8(3) . . ?
C13 O2 C14 116.8(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
N1 H1 O1 0.86 2.06 2.739(4) 135.5 .

_refine_diff_density_max         0.125
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_1i
_database_code_depnum_ccdc_archive 'CCDC 1833964'
_audit_update_record             
;
2018-03-31 deposited with the CCDC.
2018-08-07 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         'C31 H25 Br N2 O4'
_chemical_formula_sum            'C31 H25 Br N2 O4'
_chemical_formula_weight         569.44

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                   15.3274(14)
_cell_length_b                   10.9875(10)
_cell_length_c                   15.7022(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.769(3)
_cell_angle_gamma                90
_cell_volume                     2531.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7156
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.665
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.717
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25557
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.296
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5827
_reflns_number_gt                3612
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.5630P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5827
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.05868(2) 1.22736(3) 0.27808(2) 0.05649(12) Uani 1 1 d . . . . .
C1 C 0.68980(15) 1.0417(2) 0.72372(14) 0.0343(6) Uani 1 1 d . . . . .
C2 C 0.77127(16) 1.1074(2) 0.74371(16) 0.0420(6) Uani 1 1 d . . . . .
H2 H 0.7769 1.1776 0.7126 0.050 Uiso 1 1 calc R U . . .
C3 C 0.84265(17) 1.0636(2) 0.81158(16) 0.0449(6) Uani 1 1 d . . . . .
H3 H 0.8978 1.1053 0.8267 0.054 Uiso 1 1 calc R U . . .
C4 C 0.83471(17) 0.9589(3) 0.85816(15) 0.0449(7) Uani 1 1 d . . . . .
C5 C 0.9086(2) 0.8333(3) 0.98178(19) 0.0678(9) Uani 1 1 d . . . . .
H5A H 0.8638 0.8514 1.0119 0.102 Uiso 1 1 calc R U . . .
H5B H 0.9671 0.8230 1.0247 0.102 Uiso 1 1 calc R U . . .
H5C H 0.8920 0.7596 0.9481 0.102 Uiso 1 1 calc R U . . .
C6 C 0.75549(16) 0.8921(2) 0.83847(16) 0.0430(6) Uani 1 1 d . . . . .
H6 H 0.7512 0.8215 0.8698 0.052 Uiso 1 1 calc R U . . .
C7 C 0.68063(15) 0.9346(2) 0.76878(15) 0.0359(6) Uani 1 1 d . . . . .
C8 C 0.58993(16) 0.8907(2) 0.72902(15) 0.0378(6) Uani 1 1 d . . . . .
C9 C 0.54857(15) 0.9725(2) 0.66382(14) 0.0329(5) Uani 1 1 d . . . . .
C10 C 0.53719(17) 0.7853(2) 0.74913(17) 0.0467(7) Uani 1 1 d . . . . .
H10A H 0.5105 0.8077 0.7959 0.056 Uiso 1 1 calc R U . . .
H10B H 0.5780 0.7171 0.7700 0.056 Uiso 1 1 calc R U . . .
C11 C 0.46263(18) 0.7481(2) 0.66702(18) 0.0454(7) Uani 1 1 d . . . . .
H11A H 0.4893 0.7034 0.6274 0.055 Uiso 1 1 calc R U . . .
H11B H 0.4205 0.6942 0.6842 0.055 Uiso 1 1 calc R U . . .
C12 C 0.45468(15) 0.9612(2) 0.61110(14) 0.0310(5) Uani 1 1 d . . . . .
C13 C 0.39005(14) 1.0368(2) 0.55489(14) 0.0302(5) Uani 1 1 d . . . . .
C14 C 0.40972(15) 1.1611(2) 0.53467(14) 0.0315(5) Uani 1 1 d . . . . .
C15 C 0.35037(19) 1.3560(2) 0.4900(2) 0.0625(8) Uani 1 1 d . . . . .
H15A H 0.3954 1.3960 0.5370 0.094 Uiso 1 1 calc R U . . .
H15B H 0.2940 1.4001 0.4773 0.094 Uiso 1 1 calc R U . . .
H15C H 0.3707 1.3533 0.4376 0.094 Uiso 1 1 calc R U . . .
C16 C 0.32643(17) 0.6683(2) 0.43945(17) 0.0426(6) Uani 1 1 d . . . . .
H16 H 0.3809 0.7054 0.4703 0.051 Uiso 1 1 calc R U . . .
C17 C 0.32253(18) 0.6002(2) 0.36434(18) 0.0478(7) Uani 1 1 d . . . . .
H17 H 0.3746 0.5931 0.3456 0.057 Uiso 1 1 calc R U . . .
C18 C 0.24390(19) 0.5428(2) 0.31669(16) 0.0448(6) Uani 1 1 d . . . . .
C19 C 0.2408(2) 0.4681(3) 0.23526(19) 0.0691(9) Uani 1 1 d . . . . .
H19A H 0.3006 0.4644 0.2274 0.104 Uiso 1 1 calc R U . . .
H19B H 0.1994 0.5051 0.1839 0.104 Uiso 1 1 calc R U . . .
H19C H 0.2203 0.3873 0.2426 0.104 Uiso 1 1 calc R U . . .
C20 C 0.16795(17) 0.5553(2) 0.34767(17) 0.0467(7) Uani 1 1 d . . . . .
H20 H 0.1138 0.5170 0.3173 0.056 Uiso 1 1 calc R U . . .
C21 C 0.17107(16) 0.6234(2) 0.42246(17) 0.0426(6) Uani 1 1 d . . . . .
H21 H 0.1192 0.6299 0.4416 0.051 Uiso 1 1 calc R U . . .
C22 C 0.25030(16) 0.6820(2) 0.46926(15) 0.0350(6) Uani 1 1 d . . . . .
C23 C 0.25364(16) 0.7588(2) 0.55064(17) 0.0385(6) Uani 1 1 d . . . . .
H23 H 0.2674 0.7054 0.6028 0.046 Uiso 1 1 calc R U . . .
C24 C 0.32412(15) 0.8575(2) 0.56723(15) 0.0340(5) Uani 1 1 d . . . . .
C25 C 0.30656(15) 0.9685(2) 0.52720(14) 0.0318(5) Uani 1 1 d . . . . .
C26 C 0.21350(14) 0.9921(2) 0.47027(14) 0.0331(5) Uani 1 1 d . . . . .
C27 C 0.18631(15) 1.0841(2) 0.40746(14) 0.0348(6) Uani 1 1 d . . . . .
H27 H 0.2295 1.1361 0.3961 0.042 Uiso 1 1 calc R U . . .
C28 C 0.09536(16) 1.0986(2) 0.36182(15) 0.0400(6) Uani 1 1 d . . . . .
C29 C 0.02981(17) 1.0227(3) 0.37608(18) 0.0526(7) Uani 1 1 d . . . . .
H29 H -0.0314 1.0353 0.3464 0.063 Uiso 1 1 calc R U . . .
C30 C 0.05621(17) 0.9279(3) 0.43497(19) 0.0516(7) Uani 1 1 d . . . . .
H30 H 0.0127 0.8744 0.4439 0.062 Uiso 1 1 calc R U . . .
C31 C 0.14618(16) 0.9115(2) 0.48067(16) 0.0377(6) Uani 1 1 d . . . . .
N1 N 0.60811(12) 1.06385(17) 0.66030(12) 0.0362(5) Uani 1 1 d . . . . .
H1 H 0.5965 1.1249 0.6245 0.043 Uiso 1 1 calc R U . . .
N2 N 0.41262(12) 0.85311(17) 0.61964(12) 0.0347(5) Uani 1 1 d . . . . .
O1 O 0.91286(12) 0.9293(2) 0.92420(12) 0.0628(6) Uani 1 1 d . . . . .
O2 O 0.48389(11) 1.19977(15) 0.53535(12) 0.0465(5) Uani 1 1 d . . . . .
O3 O 0.33681(11) 1.23382(14) 0.51699(12) 0.0432(4) Uani 1 1 d . . . . .
O4 O 0.16710(11) 0.81683(16) 0.54155(11) 0.0427(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C28 1.903(3) . ?
C1 N1 1.378(3) . ?
C1 C2 1.398(3) . ?
C1 C7 1.401(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.376(3) . ?
C4 O1 1.378(3) . ?
C5 O1 1.403(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.417(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.433(3) . ?
C8 C9 1.372(3) . ?
C8 C10 1.498(3) . ?
C9 N1 1.369(3) . ?
C9 C12 1.444(3) . ?
C10 C11 1.512(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.464(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.376(3) . ?
C12 C13 1.395(3) . ?
C13 C25 1.438(3) . ?
C13 C14 1.453(3) . ?
C14 O2 1.211(3) . ?
C14 O3 1.336(3) . ?
C15 O3 1.441(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.383(4) . ?
C16 C22 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C18 C20 1.392(4) . ?
C18 C19 1.508(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.520(3) . ?
C23 O4 1.441(3) . ?
C23 C24 1.499(3) . ?
C23 H23 0.9800 . ?
C24 C25 1.364(3) . ?
C24 N2 1.369(3) . ?
C25 C26 1.471(3) . ?
C26 C27 1.390(3) . ?
C26 C31 1.405(3) . ?
C27 C28 1.380(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.373(4) . ?
C29 C30 1.375(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.370(3) . ?
C30 H30 0.9300 . ?
C31 O4 1.386(3) . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 129.6(2) . . ?
N1 C1 C7 108.1(2) . . ?
C2 C1 C7 122.3(2) . . ?
C3 C2 C1 116.9(2) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C6 C4 O1 124.2(2) . . ?
C6 C4 C3 122.0(2) . . ?
O1 C4 C3 113.8(2) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 117.6(2) . . ?
C4 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C1 C7 C6 119.3(2) . . ?
C1 C7 C8 106.8(2) . . ?
C6 C7 C8 133.9(2) . . ?
C9 C8 C7 106.6(2) . . ?
C9 C8 C10 120.2(2) . . ?
C7 C8 C10 133.1(2) . . ?
N1 C9 C8 109.91(19) . . ?
N1 C9 C12 127.3(2) . . ?
C8 C9 C12 122.8(2) . . ?
C8 C10 C11 110.5(2) . . ?
C8 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 112.1(2) . . ?
N2 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 C13 107.98(18) . . ?
N2 C12 C9 115.85(19) . . ?
C13 C12 C9 136.0(2) . . ?
C12 C13 C25 106.72(19) . . ?
C12 C13 C14 122.9(2) . . ?
C25 C13 C14 130.3(2) . . ?
O2 C14 O3 121.3(2) . . ?
O2 C14 C13 125.5(2) . . ?
O3 C14 C13 113.2(2) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C22 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
C22 C16 H16 119.6 . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C20 117.0(2) . . ?
C17 C18 C19 121.3(3) . . ?
C20 C18 C19 121.6(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C18 121.6(2) . . ?
C21 C20 H20 119.2 . . ?
C18 C20 H20 119.2 . . ?
C20 C21 C22 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C16 117.8(2) . . ?
C21 C22 C23 121.1(2) . . ?
C16 C22 C23 121.1(2) . . ?
O4 C23 C24 107.07(19) . . ?
O4 C23 C22 110.84(19) . . ?
C24 C23 C22 113.3(2) . . ?
O4 C23 H23 108.5 . . ?
C24 C23 H23 108.5 . . ?
C22 C23 H23 108.5 . . ?
C25 C24 N2 109.7(2) . . ?
C25 C24 C23 122.0(2) . . ?
N2 C24 C23 128.2(2) . . ?
C24 C25 C13 106.71(19) . . ?
C24 C25 C26 117.7(2) . . ?
C13 C25 C26 135.5(2) . . ?
C27 C26 C31 117.5(2) . . ?
C27 C26 C25 126.8(2) . . ?
C31 C26 C25 115.7(2) . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 121.5(2) . . ?
C29 C28 Br1 118.69(18) . . ?
C27 C28 Br1 119.81(19) . . ?
C28 C29 C30 118.9(2) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.6 . . ?
C31 C30 C29 120.6(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 O4 117.2(2) . . ?
C30 C31 C26 121.2(2) . . ?
O4 C31 C26 121.4(2) . . ?
C9 N1 C1 108.57(19) . . ?
C9 N1 H1 125.7 . . ?
C1 N1 H1 125.7 . . ?
C24 N2 C12 108.79(18) . . ?
C24 N2 C11 127.98(19) . . ?
C12 N2 C11 122.57(19) . . ?
C4 O1 C5 118.1(2) . . ?
C14 O3 C15 115.80(19) . . ?
C31 O4 C23 115.05(17) . . ?

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
N1 H1 O2 0.86 2.05 2.748(2) 137.1 .

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.413
_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_1h
_database_code_depnum_ccdc_archive 'CCDC 1833963'
_audit_update_record             
;
2018-03-31 deposited with the CCDC.
2018-08-07 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         'C31 H25 Cl N2 O4'
_chemical_formula_sum            'C31 H25 Cl N2 O4'
_chemical_formula_weight         524.98

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   15.2082(10)
_cell_length_b                   10.9099(6)
_cell_length_c                   15.7373(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.780(2)
_cell_angle_gamma                90
_cell_volume                     2500.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5513
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.80

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26214
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5735
_reflns_number_gt                3007
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.2166P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5735
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
C1 C 0.69213(14) 0.53986(19) 0.72401(13) 0.0372(5) Uani 1 1 d . . . . .
C2 C 0.77406(15) 0.6048(2) 0.74397(15) 0.0439(6) Uani 1 1 d . . . . .
H2 H 0.7799 0.6754 0.7130 0.053 Uiso 1 1 calc R U . . .
C3 C 0.84602(15) 0.5608(2) 0.81109(15) 0.0483(6) Uani 1 1 d . . . . .
H3 H 0.9017 0.6026 0.8260 0.058 Uiso 1 1 calc R U . . .
C4 C 0.83756(15) 0.4549(2) 0.85759(15) 0.0475(6) Uani 1 1 d . . . . .
C5 C 0.91016(17) 0.3301(3) 0.98173(17) 0.0710(8) Uani 1 1 d . . . . .
H5A H 0.8663 0.3527 1.0123 0.107 Uiso 1 1 calc R U . . .
H5B H 0.9691 0.3178 1.0241 0.107 Uiso 1 1 calc R U . . .
H5C H 0.8908 0.2556 0.9492 0.107 Uiso 1 1 calc R U . . .
C6 C 0.75742(15) 0.3889(2) 0.83768(15) 0.0465(6) Uani 1 1 d . . . . .
H6 H 0.7528 0.3178 0.8687 0.056 Uiso 1 1 calc R U . . .
C7 C 0.68207(14) 0.43229(19) 0.76867(14) 0.0388(5) Uani 1 1 d . . . . .
C8 C 0.59030(14) 0.38922(19) 0.72880(14) 0.0400(5) Uani 1 1 d . . . . .
C9 C 0.54919(14) 0.47221(18) 0.66377(13) 0.0353(5) Uani 1 1 d . . . . .
C10 C 0.53650(15) 0.2841(2) 0.74830(15) 0.0497(6) Uani 1 1 d . . . . .
H10A H 0.5092 0.3073 0.7946 0.060 Uiso 1 1 calc R U . . .
H10B H 0.5772 0.2153 0.7696 0.060 Uiso 1 1 calc R U . . .
C11 C 0.46158(15) 0.2465(2) 0.66596(15) 0.0477(6) Uani 1 1 d . . . . .
H11A H 0.4886 0.2020 0.6264 0.057 Uiso 1 1 calc R U . . .
H11B H 0.4189 0.1922 0.6826 0.057 Uiso 1 1 calc R U . . .
C12 C 0.45495(14) 0.46217(18) 0.61095(13) 0.0344(5) Uani 1 1 d . . . . .
C13 C 0.39032(13) 0.53916(17) 0.55521(13) 0.0319(5) Uani 1 1 d . . . . .
C14 C 0.41078(15) 0.66411(19) 0.53629(13) 0.0343(5) Uani 1 1 d . . . . .
C15 C 0.35228(18) 0.8621(2) 0.49503(19) 0.0673(8) Uani 1 1 d . . . . .
H15A H 0.3987 0.9006 0.5422 0.101 Uiso 1 1 calc R U . . .
H15B H 0.2959 0.9072 0.4840 0.101 Uiso 1 1 calc R U . . .
H15C H 0.3718 0.8609 0.4422 0.101 Uiso 1 1 calc R U . . .
C16 C 0.16727(15) 0.1235(2) 0.42277(16) 0.0473(6) Uani 1 1 d . . . . .
H16 H 0.1150 0.1305 0.4418 0.057 Uiso 1 1 calc R U . . .
C17 C 0.16443(16) 0.0540(2) 0.34878(16) 0.0500(6) Uani 1 1 d . . . . .
H17 H 0.1100 0.0146 0.3190 0.060 Uiso 1 1 calc R U . . .
C18 C 0.24035(17) 0.0413(2) 0.31748(15) 0.0476(6) Uani 1 1 d . . . . .
C19 C 0.23757(18) -0.0356(3) 0.23661(17) 0.0750(8) Uani 1 1 d . . . . .
H19A H 0.1968 0.0016 0.1848 0.112 Uiso 1 1 calc R U . . .
H19B H 0.2160 -0.1164 0.2441 0.112 Uiso 1 1 calc R U . . .
H19C H 0.2981 -0.0407 0.2297 0.112 Uiso 1 1 calc R U . . .
C20 C 0.31954(16) 0.0998(2) 0.36384(17) 0.0508(6) Uani 1 1 d . . . . .
H20 H 0.3717 0.0928 0.3447 0.061 Uiso 1 1 calc R U . . .
C21 C 0.32341(15) 0.1693(2) 0.43863(16) 0.0454(6) Uani 1 1 d . . . . .
H21 H 0.3782 0.2072 0.4689 0.054 Uiso 1 1 calc R U . . .
C22 C 0.24713(14) 0.18310(18) 0.46900(14) 0.0378(5) Uani 1 1 d . . . . .
C23 C 0.25076(14) 0.26075(19) 0.54970(15) 0.0415(6) Uani 1 1 d . . . . .
H23 H 0.2637 0.2072 0.6018 0.050 Uiso 1 1 calc R U . . .
C24 C 0.32269(14) 0.35922(19) 0.56668(14) 0.0378(5) Uani 1 1 d . . . . .
C25 C 0.30570(13) 0.47170(18) 0.52727(13) 0.0340(5) Uani 1 1 d . . . . .
C26 C 0.21293(13) 0.49633(19) 0.47004(13) 0.0361(5) Uani 1 1 d . . . . .
C27 C 0.18714(14) 0.5899(2) 0.40744(14) 0.0405(6) Uani 1 1 d . . . . .
H27 H 0.2316 0.6417 0.3972 0.049 Uiso 1 1 calc R U . . .
C28 C 0.09585(15) 0.6061(2) 0.36055(14) 0.0454(6) Uani 1 1 d . . . . .
C29 C 0.02920(16) 0.5307(2) 0.37316(17) 0.0592(7) Uani 1 1 d . . . . .
H29 H -0.0322 0.5441 0.3425 0.071 Uiso 1 1 calc R U . . .
C30 C 0.05388(16) 0.4346(2) 0.43180(18) 0.0581(7) Uani 1 1 d . . . . .
H30 H 0.0090 0.3814 0.4395 0.070 Uiso 1 1 calc R U . . .
C31 C 0.14406(15) 0.4165(2) 0.47900(15) 0.0425(6) Uani 1 1 d . . . . .
Cl1 Cl 0.06473(4) 0.72553(6) 0.28460(4) 0.0656(2) Uani 1 1 d . . . . .
N1 N 0.60989(11) 0.56345(15) 0.66054(11) 0.0396(4) Uani 1 1 d . . . . .
H1 H 0.5987 0.6251 0.6250 0.047 Uiso 1 1 calc R U . . .
N2 N 0.41164(11) 0.35363(15) 0.61934(11) 0.0376(4) Uani 1 1 d . . . . .
O1 O 0.91635(10) 0.42344(17) 0.92292(11) 0.0676(5) Uani 1 1 d . . . . .
O2 O 0.48553(10) 0.70281(13) 0.53683(10) 0.0501(4) Uani 1 1 d . . . . .
O3 O 0.33800(10) 0.73807(13) 0.52016(10) 0.0472(4) Uani 1 1 d . . . . .
O4 O 0.16368(10) 0.32075(13) 0.53961(10) 0.0473(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.381(2) . ?
C1 C2 1.388(3) . ?
C1 C7 1.399(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.371(3) . ?
C4 O1 1.378(3) . ?
C5 O1 1.398(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.413(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.434(3) . ?
C8 C9 1.374(3) . ?
C8 C10 1.491(3) . ?
C9 N1 1.369(2) . ?
C9 C12 1.438(3) . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.469(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.380(2) . ?
C12 C13 1.394(3) . ?
C13 C25 1.437(3) . ?
C13 C14 1.448(3) . ?
C14 O2 1.210(2) . ?
C14 O3 1.334(2) . ?
C15 O3 1.443(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.380(3) . ?
C16 C22 1.384(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9300 . ?
C18 C20 1.373(3) . ?
C18 C19 1.515(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.514(3) . ?
C23 O4 1.444(2) . ?
C23 C24 1.501(3) . ?
C23 H23 0.9800 . ?
C24 C25 1.365(3) . ?
C24 N2 1.369(3) . ?
C25 C26 1.463(3) . ?
C26 C27 1.394(3) . ?
C26 C31 1.400(3) . ?
C27 C28 1.383(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.364(3) . ?
C28 Cl1 1.739(2) . ?
C29 C30 1.375(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(3) . ?
C30 H30 0.9300 . ?
C31 O4 1.388(3) . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 129.4(2) . . ?
N1 C1 C7 108.20(18) . . ?
C2 C1 C7 122.38(19) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C6 C4 O1 124.3(2) . . ?
C6 C4 C3 121.7(2) . . ?
O1 C4 C3 114.0(2) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 118.0(2) . . ?
C4 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C1 C7 C6 119.0(2) . . ?
C1 C7 C8 106.79(18) . . ?
C6 C7 C8 134.2(2) . . ?
C9 C8 C7 106.62(18) . . ?
C9 C8 C10 120.08(19) . . ?
C7 C8 C10 133.2(2) . . ?
N1 C9 C8 109.89(18) . . ?
N1 C9 C12 127.17(18) . . ?
C8 C9 C12 122.91(19) . . ?
C8 C10 C11 110.74(19) . . ?
C8 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 111.38(18) . . ?
N2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C13 107.94(17) . . ?
N2 C12 C9 115.70(18) . . ?
C13 C12 C9 136.18(19) . . ?
C12 C13 C25 106.88(17) . . ?
C12 C13 C14 122.84(18) . . ?
C25 C13 C14 130.24(18) . . ?
O2 C14 O3 121.10(19) . . ?
O2 C14 C13 125.74(19) . . ?
O3 C14 C13 113.13(18) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C22 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C22 C16 H16 119.7 . . ?
C16 C17 C18 121.9(2) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C20 C18 C17 117.2(2) . . ?
C20 C18 C19 120.8(2) . . ?
C17 C18 C19 122.0(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 121.4(2) . . ?
C18 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 121.2(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C16 C22 C21 117.6(2) . . ?
C16 C22 C23 121.2(2) . . ?
C21 C22 C23 121.27(19) . . ?
O4 C23 C24 107.04(17) . . ?
O4 C23 C22 110.55(17) . . ?
C24 C23 C22 113.45(18) . . ?
O4 C23 H23 108.6 . . ?
C24 C23 H23 108.6 . . ?
C22 C23 H23 108.6 . . ?
C25 C24 N2 109.85(18) . . ?
C25 C24 C23 121.98(19) . . ?
N2 C24 C23 128.17(19) . . ?
C24 C25 C13 106.62(17) . . ?
C24 C25 C26 117.85(18) . . ?
C13 C25 C26 135.53(18) . . ?
C27 C26 C31 117.42(19) . . ?
C27 C26 C25 126.46(19) . . ?
C31 C26 C25 116.11(19) . . ?
C28 C27 C26 120.3(2) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 121.3(2) . . ?
C29 C28 Cl1 119.06(18) . . ?
C27 C28 Cl1 119.65(18) . . ?
C28 C29 C30 119.1(2) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C31 C30 C29 120.6(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 O4 117.6(2) . . ?
C30 C31 C26 121.0(2) . . ?
O4 C31 C26 121.25(19) . . ?
C9 N1 C1 108.50(17) . . ?
C9 N1 H1 125.7 . . ?
C1 N1 H1 125.7 . . ?
C24 N2 C12 108.63(16) . . ?
C24 N2 C11 128.02(17) . . ?
C12 N2 C11 122.55(17) . . ?
C4 O1 C5 117.72(19) . . ?
C14 O3 C15 115.91(17) . . ?
C31 O4 C23 115.16(15) . . ?

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
N1 H1 O2 0.86 2.06 2.748(2) 137.0 .

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_1p
_database_code_depnum_ccdc_archive 'CCDC 1836518'
_audit_update_record             
;
2018-04-12 deposited with the CCDC.
2018-08-07 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         'C30 H22 Br Cl N2 O4'
_chemical_formula_sum            'C30 H22 Br Cl N2 O4'
_chemical_formula_weight         589.85

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      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                   14.2605(5)
_cell_length_b                   13.5158(5)
_cell_length_c                   14.5519(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.1110(9)
_cell_angle_gamma                90
_cell_volume                     2539.68(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.765
_shelx_estimated_absorpt_T_min   0.657
_shelx_estimated_absorpt_T_max   0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28830
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.577
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5836
_reflns_number_gt                3824
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0771P)²+1.2270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5836
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1499
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Br1 Br 0.21124(3) -0.07912(4) 1.04070(3) 0.07853(19) Uani 1 1 d . . . . .
C1 C -0.24195(19) 0.1176(2) 0.2970(2) 0.0352(6) Uani 1 1 d . . . . .
C2 C -0.3373(2) 0.0820(2) 0.2274(2) 0.0428(7) Uani 1 1 d . . . . .
H2 H -0.3696 0.0294 0.2436 0.051 Uiso 1 1 calc R U . . .
C3 C -0.3819(2) 0.1270(2) 0.1345(2) 0.0459(7) Uani 1 1 d . . . . .
H3 H -0.4451 0.1037 0.0863 0.055 Uiso 1 1 calc R U . . .
C4 C -0.3346(2) 0.2072(2) 0.1104(2) 0.0493(7) Uani 1 1 d . . . . .
C5 C -0.3417(3) 0.3192(3) -0.0190(3) 0.0776(12) Uani 1 1 d . . . . .
H5A H -0.3248 0.3742 0.0269 0.116 Uiso 1 1 calc R U . . .
H5B H -0.3883 0.3406 -0.0858 0.116 Uiso 1 1 calc R U . . .
H5C H -0.2796 0.2937 -0.0206 0.116 Uiso 1 1 calc R U . . .
C6 C -0.2405(2) 0.2430(2) 0.1781(2) 0.0508(8) Uani 1 1 d . . . . .
H6 H -0.2093 0.2960 0.1612 0.061 Uiso 1 1 calc R U . . .
C7 C -0.1925(2) 0.1974(2) 0.2738(2) 0.0401(6) Uani 1 1 d . . . . .
C8 C -0.09740(19) 0.2129(2) 0.3616(2) 0.0410(6) Uani 1 1 d . . . . .
C9 C -0.09327(18) 0.14477(19) 0.43292(19) 0.0346(6) Uani 1 1 d . . . . .
C10 C -0.0149(2) 0.2885(3) 0.3847(3) 0.0654(10) Uani 1 1 d . . . . .
H10A H -0.0037 0.3004 0.3243 0.078 Uiso 1 1 calc R U . . .
H10B H -0.0377 0.3501 0.4028 0.078 Uiso 1 1 calc R U . . .
C11 C 0.0820(2) 0.2586(3) 0.4669(3) 0.0666(10) Uani 1 1 d . . . . .
H11A H 0.1225 0.3175 0.4962 0.080 Uiso 1 1 calc R U . . .
H11B H 0.1203 0.2192 0.4386 0.080 Uiso 1 1 calc R U . . .
C12 C -0.00925(18) 0.14035(19) 0.53303(19) 0.0351(6) Uani 1 1 d . . . . .
C13 C 0.01057(18) 0.09318(19) 0.6246(2) 0.0334(6) Uani 1 1 d . . . . .
C14 C -0.06420(19) 0.0281(2) 0.6379(2) 0.0372(6) Uani 1 1 d . . . . .
C15 C -0.1142(3) -0.0494(3) 0.7559(3) 0.0749(11) Uani 1 1 d . . . . .
H15A H -0.1849 -0.0290 0.7190 0.112 Uiso 1 1 calc R U . . .
H15B H -0.0964 -0.0482 0.8274 0.112 Uiso 1 1 calc R U . . .
H15C H -0.1058 -0.1153 0.7360 0.112 Uiso 1 1 calc R U . . .
C16 C 0.3210(2) 0.1341(2) 0.6011(2) 0.0433(7) Uani 1 1 d . . . . .
H16 H 0.2553 0.1325 0.5476 0.052 Uiso 1 1 calc R U . . .
C17 C 0.4004(2) 0.0829(2) 0.5927(2) 0.0496(7) Uani 1 1 d . . . . .
H17 H 0.3891 0.0481 0.5338 0.060 Uiso 1 1 calc R U . . .
C18 C 0.4968(2) 0.0839(3) 0.6728(3) 0.0546(8) Uani 1 1 d . . . . .
C19 C 0.5151(2) 0.1383(3) 0.7576(3) 0.0685(10) Uani 1 1 d . . . . .
H19 H 0.5812 0.1403 0.8102 0.082 Uiso 1 1 calc R U . . .
C20 C 0.4356(2) 0.1902(3) 0.7654(3) 0.0590(9) Uani 1 1 d . . . . .
H20 H 0.4483 0.2271 0.8234 0.071 Uiso 1 1 calc R U . . .
C21 C 0.33649(19) 0.1879(2) 0.6868(2) 0.0392(6) Uani 1 1 d . . . . .
C22 C 0.2488(2) 0.2434(2) 0.6967(2) 0.0425(7) Uani 1 1 d . . . . .
H22 H 0.2427 0.3084 0.6649 0.051 Uiso 1 1 calc R U . . .
C23 C 0.14522(19) 0.1924(2) 0.6468(2) 0.0387(6) Uani 1 1 d . . . . .
C24 C 0.11078(19) 0.1272(2) 0.6972(2) 0.0363(6) Uani 1 1 d . . . . .
C25 C 0.17806(19) 0.1084(2) 0.8040(2) 0.0388(6) Uani 1 1 d . . . . .
C26 C 0.1703(2) 0.0293(2) 0.8619(2) 0.0443(7) Uani 1 1 d . . . . .
H26 H 0.1205 -0.0193 0.8318 0.053 Uiso 1 1 calc R U . . .
C27 C 0.2365(2) 0.0229(3) 0.9641(2) 0.0504(8) Uani 1 1 d . . . . .
C28 C 0.3152(2) 0.0893(3) 1.0107(2) 0.0574(9) Uani 1 1 d . . . . .
H28 H 0.3597 0.0829 1.0791 0.069 Uiso 1 1 calc R U . . .
C29 C 0.3270(2) 0.1661(3) 0.9536(2) 0.0537(8) Uani 1 1 d . . . . .
H29 H 0.3806 0.2113 0.9835 0.064 Uiso 1 1 calc R U . . .
C30 C 0.2592(2) 0.1760(2) 0.8519(2) 0.0426(7) Uani 1 1 d . . . . .
Cl1 Cl 0.59517(8) 0.01133(10) 0.66695(9) 0.0926(4) Uani 1 1 d . . . . .
N1 N -0.18050(16) 0.08635(16) 0.39392(17) 0.0377(5) Uani 1 1 d . . . . .
H1 H -0.1942 0.0383 0.4250 0.045 Uiso 1 1 calc R U . . .
N2 N 0.07326(15) 0.20201(17) 0.54806(17) 0.0382(5) Uani 1 1 d . . . . .
O1 O -0.38956(17) 0.24416(19) 0.01396(16) 0.0690(7) Uani 1 1 d . . . . .
O2 O -0.13682(16) -0.01211(17) 0.57058(15) 0.0598(6) Uani 1 1 d . . . . .
O3 O -0.04737(16) 0.01718(17) 0.73409(15) 0.0534(6) Uani 1 1 d . . . . .
O4 O 0.27032(14) 0.25842(15) 0.80133(15) 0.0479(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C27 1.901(3) . ?
C1 N1 1.374(3) . ?
C1 C2 1.391(4) . ?
C1 C7 1.406(4) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.372(4) . ?
C4 O1 1.378(3) . ?
C5 O1 1.415(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.407(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.429(4) . ?
C8 C9 1.370(4) . ?
C8 C10 1.486(4) . ?
C9 N1 1.376(3) . ?
C9 C12 1.442(3) . ?
C10 C11 1.450(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.457(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.382(3) . ?
C12 C13 1.394(4) . ?
C13 C24 1.445(3) . ?
C13 C14 1.457(4) . ?
C14 O2 1.210(3) . ?
C14 O3 1.325(3) . ?
C15 O3 1.441(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.377(4) . ?
C16 C21 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(5) . ?
C18 Cl1 1.743(3) . ?
C19 C20 1.378(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.517(4) . ?
C22 O4 1.434(4) . ?
C22 C23 1.507(4) . ?
C22 H22 0.9800 . ?
C23 C24 1.365(4) . ?
C23 N2 1.372(3) . ?
C24 C25 1.461(4) . ?
C25 C26 1.394(4) . ?
C25 C30 1.405(4) . ?
C26 C27 1.385(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.371(5) . ?
C28 C29 1.383(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.389(4) . ?
C29 H29 0.9300 . ?
C30 O4 1.382(4) . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 129.9(2) . . ?
N1 C1 C7 108.4(2) . . ?
C2 C1 C7 121.7(2) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C6 C4 O1 124.4(3) . . ?
C6 C4 C3 121.4(3) . . ?
O1 C4 C3 114.2(2) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 118.3(3) . . ?
C4 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C1 C7 C6 119.3(2) . . ?
C1 C7 C8 106.3(2) . . ?
C6 C7 C8 134.3(3) . . ?
C9 C8 C7 107.3(2) . . ?
C9 C8 C10 121.0(2) . . ?
C7 C8 C10 131.5(3) . . ?
C8 C9 N1 109.4(2) . . ?
C8 C9 C12 122.9(2) . . ?
N1 C9 C12 127.7(2) . . ?
C11 C10 C8 112.4(3) . . ?
C11 C10 H10A 109.1 . . ?
C8 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C8 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 N2 115.8(3) . . ?
C10 C11 H11A 108.3 . . ?
N2 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
N2 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
N2 C12 C13 108.1(2) . . ?
N2 C12 C9 114.9(2) . . ?
C13 C12 C9 136.8(2) . . ?
C12 C13 C24 106.9(2) . . ?
C12 C13 C14 122.7(2) . . ?
C24 C13 C14 130.3(2) . . ?
O2 C14 O3 120.9(3) . . ?
O2 C14 C13 125.9(3) . . ?
O3 C14 C13 113.1(2) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C21 C16 H16 119.2 . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 Cl1 119.9(3) . . ?
C17 C18 Cl1 119.3(3) . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 118.2(3) . . ?
C16 C21 C22 121.6(2) . . ?
C20 C21 C22 120.2(3) . . ?
O4 C22 C23 107.5(2) . . ?
O4 C22 C21 110.9(2) . . ?
C23 C22 C21 114.1(2) . . ?
O4 C22 H22 108.1 . . ?
C23 C22 H22 108.1 . . ?
C21 C22 H22 108.1 . . ?
C24 C23 N2 110.1(2) . . ?
C24 C23 C22 122.6(2) . . ?
N2 C23 C22 127.3(2) . . ?
C23 C24 C13 106.4(2) . . ?
C23 C24 C25 117.4(2) . . ?
C13 C24 C25 136.2(3) . . ?
C26 C25 C30 117.3(3) . . ?
C26 C25 C24 126.3(2) . . ?
C30 C25 C24 116.4(3) . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 122.1(3) . . ?
C28 C27 Br1 120.3(2) . . ?
C26 C27 Br1 117.6(3) . . ?
C27 C28 C29 118.4(3) . . ?
C27 C28 H28 120.8 . . ?
C29 C28 H28 120.8 . . ?
C28 C29 C30 120.4(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
O4 C30 C29 117.4(3) . . ?
O4 C30 C25 121.1(2) . . ?
C29 C30 C25 121.3(3) . . ?
C1 N1 C9 108.6(2) . . ?
C1 N1 H1 125.7 . . ?
C9 N1 H1 125.7 . . ?
C23 N2 C12 108.5(2) . . ?
C23 N2 C11 128.0(2) . . ?
C12 N2 C11 123.3(2) . . ?
C4 O1 C5 117.2(2) . . ?
C14 O3 C15 117.5(2) . . ?
C30 O4 C22 115.5(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
N1 H1 O2 0.86 2.04 2.722(3) 136.0 .

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.074

