# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1848765'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-07-24 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 H30 Br N3 O3'
_chemical_formula_sum            'C30 H30 Br N3 O3'
_chemical_formula_weight         560.48

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5691(18)
_cell_length_b                   12.489(2)
_cell_length_c                   13.082(2)
_cell_angle_alpha                113.373(5)
_cell_angle_beta                 95.324(5)
_cell_angle_gamma                113.736(5)
_cell_volume                     1383.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4682
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      23.52

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.520
_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_T_max  0.738
_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            15004
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             5306
_reflns_number_gt                3204
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0525P)²+0.5460P] 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         5306
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.60893(5) 0.09789(5) 0.66920(4) 0.0590(2) Uani 1 1 d . . . . .
C1 C 0.1943(5) 0.5880(4) 0.9025(4) 0.0587(12) Uani 1 1 d . . . . .
H1 H 0.2932 0.6174 0.9262 0.070 Uiso 1 1 calc R U . . .
C2 C 0.1373(5) 0.6654(5) 0.9684(4) 0.0624(13) Uani 1 1 d . . . . .
H2 H 0.1990 0.7451 1.0355 0.075 Uiso 1 1 calc R U . . .
C3 C -0.0062(4) 0.6272(4) 0.9370(4) 0.0467(10) Uani 1 1 d . . . . .
C4 C -0.0668(5) 0.7102(5) 1.0112(4) 0.0725(14) Uani 1 1 d . . . . .
H4A H -0.0153 0.7499 1.0921 0.109 Uiso 1 1 calc R U . . .
H4B H -0.1677 0.6546 0.9976 0.109 Uiso 1 1 calc R U . . .
H4C H -0.0558 0.7788 0.9910 0.109 Uiso 1 1 calc R U . . .
C5 C -0.0921(5) 0.5106(5) 0.8364(4) 0.0665(13) Uani 1 1 d . . . . .
H5 H -0.1902 0.4836 0.8111 0.080 Uiso 1 1 calc R U . . .
C6 C -0.0371(4) 0.4313(4) 0.7709(4) 0.0590(12) Uani 1 1 d . . . . .
H6 H -0.0991 0.3513 0.7040 0.071 Uiso 1 1 calc R U . . .
C7 C 0.1079(4) 0.4701(4) 0.8041(3) 0.0355(9) Uani 1 1 d . . . . .
C8 C 0.1667(4) 0.3813(4) 0.7376(3) 0.0370(9) Uani 1 1 d . . . . .
H8 H 0.0893 0.2888 0.7008 0.044 Uiso 1 1 calc R U . . .
C9 C 0.2300(4) 0.4073(3) 0.6437(3) 0.0314(8) Uani 1 1 d . . . . .
C10 C 0.2819(4) 0.3057(3) 0.5833(3) 0.0307(8) Uani 1 1 d . . . . .
H10 H 0.3555 0.3443 0.5496 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3491(4) 0.2732(3) 0.6655(3) 0.0317(8) Uani 1 1 d . . . . .
C12 C 0.4269(4) 0.2054(3) 0.6334(3) 0.0378(9) Uani 1 1 d . . . . .
H12 H 0.4307 0.1716 0.5570 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4984(4) 0.1873(4) 0.7125(3) 0.0403(9) Uani 1 1 d . . . . .
C14 C 0.4961(4) 0.2384(4) 0.8267(3) 0.0480(10) Uani 1 1 d . . . . .
H14 H 0.5448 0.2258 0.8803 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4218(5) 0.3077(4) 0.8608(3) 0.0509(11) Uani 1 1 d . . . . .
H15 H 0.4212 0.3435 0.9379 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3478(4) 0.3247(4) 0.7808(3) 0.0387(9) Uani 1 1 d . . . . .
C17 C 0.1200(4) 0.0655(5) 0.4199(3) 0.0445(10) Uani 1 1 d . . . . .
C18 C 0.1439(4) 0.1982(3) 0.4837(3) 0.0336(9) Uani 1 1 d . . . . .
C19 C 0.0598(4) 0.2493(4) 0.4671(3) 0.0368(9) Uani 1 1 d . . . . .
C20 C -0.0780(4) 0.1988(4) 0.3769(3) 0.0467(10) Uani 1 1 d . . . . .
C21 C -0.1964(5) 0.1986(6) 0.4367(5) 0.0967(19) Uani 1 1 d . . . . .
H21A H -0.2080 0.1455 0.4754 0.145 Uiso 1 1 calc R U . . .
H21B H -0.2862 0.1620 0.3792 0.145 Uiso 1 1 calc R U . . .
H21C H -0.1690 0.2880 0.4930 0.145 Uiso 1 1 calc R U . . .
C22 C -0.0504(6) 0.2919(6) 0.3242(5) 0.109(2) Uani 1 1 d . . . . .
H22A H -0.0131 0.3813 0.3854 0.164 Uiso 1 1 calc R U . . .
H22B H -0.1395 0.2658 0.2716 0.164 Uiso 1 1 calc R U . . .
H22C H 0.0189 0.2873 0.2824 0.164 Uiso 1 1 calc R U . . .
C23 C -0.1300(6) 0.0586(5) 0.2826(5) 0.0962(19) Uani 1 1 d . . . . .
H23A H -0.0583 0.0565 0.2431 0.144 Uiso 1 1 calc R U . . .
H23B H -0.2191 0.0289 0.2277 0.144 Uiso 1 1 calc R U . . .
H23C H -0.1459 0.0010 0.3171 0.144 Uiso 1 1 calc R U . . .
C24 C 0.3535(4) 0.5344(4) 0.5081(4) 0.0435(10) Uani 1 1 d . . . . .
C25 C 0.3992(4) 0.5978(3) 0.6351(3) 0.0329(8) Uani 1 1 d . . . . .
C26 C 0.5299(4) 0.7351(4) 0.6902(3) 0.0384(9) Uani 1 1 d . . . . .
C27 C 0.6021(4) 0.8168(4) 0.8201(3) 0.0468(10) Uani 1 1 d . . . . .
C28 C 0.7440(6) 0.9377(5) 0.8440(4) 0.0940(19) Uani 1 1 d . . . . .
H28A H 0.8079 0.9084 0.8093 0.141 Uiso 1 1 calc R U . . .
H28B H 0.7889 0.9931 0.9267 0.141 Uiso 1 1 calc R U . . .
H28C H 0.7240 0.9875 0.8108 0.141 Uiso 1 1 calc R U . . .
C29 C 0.5005(6) 0.8635(6) 0.8757(4) 0.0912(18) Uani 1 1 d . . . . .
H29A H 0.4887 0.9212 0.8490 0.137 Uiso 1 1 calc R U . . .
H29B H 0.5411 0.9108 0.9591 0.137 Uiso 1 1 calc R U . . .
H29C H 0.4079 0.7878 0.8539 0.137 Uiso 1 1 calc R U . . .
C30 C 0.6370(5) 0.7382(4) 0.8711(4) 0.0663(13) Uani 1 1 d . . . . .
H30A H 0.5485 0.6691 0.8666 0.099 Uiso 1 1 calc R U . . .
H30B H 0.6950 0.7966 0.9513 0.099 Uiso 1 1 calc R U . . .
H30C H 0.6894 0.6993 0.8277 0.099 Uiso 1 1 calc R U . . .
N1 N 0.1053(4) -0.0400(4) 0.3744(3) 0.0650(11) Uani 1 1 d . . . . .
N2 N 0.3447(3) 0.5420(3) 0.6951(2) 0.0326(7) Uani 1 1 d . . . . .
N3 N 0.3275(4) 0.4841(4) 0.4091(3) 0.0694(11) Uani 1 1 d . . . . .
O1 O 0.2795(3) 0.3983(3) 0.8224(2) 0.0438(7) Uani 1 1 d . . . . .
O2 O 0.1133(2) 0.3789(2) 0.5530(2) 0.0369(6) Uani 1 1 d . . . . .
O3 O 0.5705(3) 0.7749(3) 0.6229(3) 0.0637(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
Br1 C13 1.898(4) . ?
C1 C7 1.362(5) . ?
C1 C2 1.395(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(5) . ?
C2 H2 0.9300 . ?
C3 C5 1.367(6) . ?
C3 C4 1.509(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.505(5) . ?
C8 O1 1.434(4) . ?
C8 C9 1.536(5) . ?
C8 H8 0.9800 . ?
C9 N2 1.436(4) . ?
C9 O2 1.448(4) . ?
C9 C10 1.543(5) . ?
C10 C11 1.504(5) . ?
C10 C18 1.520(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.384(5) . ?
C11 C16 1.389(5) . ?
C12 C13 1.368(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(5) . ?
C14 C15 1.367(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 O1 1.368(4) . ?
C17 N1 1.145(5) . ?
C17 C18 1.426(6) . ?
C18 C19 1.333(5) . ?
C19 O2 1.380(4) . ?
C19 C20 1.503(5) . ?
C20 C23 1.509(6) . ?
C20 C22 1.520(6) . ?
C20 C21 1.536(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 N3 1.139(5) . ?
C24 C25 1.456(6) . ?
C25 N2 1.275(4) . ?
C25 C26 1.515(5) . ?
C26 O3 1.205(4) . ?
C26 C27 1.506(5) . ?
C27 C30 1.520(6) . ?
C27 C29 1.528(6) . ?
C27 C28 1.531(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 121.3(4) . . ?
C7 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 121.6(4) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C5 117.0(4) . . ?
C2 C3 C4 120.9(4) . . ?
C5 C3 C4 122.1(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 122.0(4) . . ?
C3 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1 C7 C6 117.6(4) . . ?
C1 C7 C8 121.5(3) . . ?
C6 C7 C8 120.8(4) . . ?
O1 C8 C7 106.5(3) . . ?
O1 C8 C9 108.0(3) . . ?
C7 C8 C9 116.6(3) . . ?
O1 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
N2 C9 O2 112.2(3) . . ?
N2 C9 C8 109.9(3) . . ?
O2 C9 C8 108.0(3) . . ?
N2 C9 C10 112.1(3) . . ?
O2 C9 C10 105.0(2) . . ?
C8 C9 C10 109.5(3) . . ?
C11 C10 C18 120.2(3) . . ?
C11 C10 C9 113.3(3) . . ?
C18 C10 C9 99.0(3) . . ?
C11 C10 H10 107.8 . . ?
C18 C10 H10 107.8 . . ?
C9 C10 H10 107.8 . . ?
C12 C11 C16 118.2(3) . . ?
C12 C11 C10 121.6(3) . . ?
C16 C11 C10 119.7(3) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 Br1 120.8(3) . . ?
C14 C13 Br1 118.7(3) . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
O1 C16 C15 116.6(3) . . ?
O1 C16 C11 122.7(3) . . ?
C15 C16 C11 120.6(3) . . ?
N1 C17 C18 176.0(4) . . ?
C19 C18 C17 128.6(3) . . ?
C19 C18 C10 110.1(3) . . ?
C17 C18 C10 121.4(3) . . ?
C18 C19 O2 111.6(3) . . ?
C18 C19 C20 134.9(3) . . ?
O2 C19 C20 113.5(3) . . ?
C19 C20 C23 111.7(3) . . ?
C19 C20 C22 108.4(3) . . ?
C23 C20 C22 110.3(4) . . ?
C19 C20 C21 108.8(3) . . ?
C23 C20 C21 108.0(4) . . ?
C22 C20 C21 109.7(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C25 174.5(4) . . ?
N2 C25 C24 124.8(3) . . ?
N2 C25 C26 122.4(3) . . ?
C24 C25 C26 112.6(3) . . ?
O3 C26 C27 122.5(4) . . ?
O3 C26 C25 115.2(3) . . ?
C27 C26 C25 122.2(3) . . ?
C26 C27 C30 111.8(3) . . ?
C26 C27 C29 107.8(3) . . ?
C30 C27 C29 110.8(4) . . ?
C26 C27 C28 108.5(4) . . ?
C30 C27 C28 108.4(4) . . ?
C29 C27 C28 109.5(4) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 N2 C9 123.2(3) . . ?
C16 O1 C8 116.5(3) . . ?
C19 O2 C9 107.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 C3 -0.5(7) . . . . ?
C1 C2 C3 C5 -1.3(7) . . . . ?
C1 C2 C3 C4 178.2(4) . . . . ?
C2 C3 C5 C6 2.4(7) . . . . ?
C4 C3 C5 C6 -177.1(4) . . . . ?
C3 C5 C6 C7 -1.8(7) . . . . ?
C2 C1 C7 C6 1.1(7) . . . . ?
C2 C1 C7 C8 -175.3(4) . . . . ?
C5 C6 C7 C1 0.0(6) . . . . ?
C5 C6 C7 C8 176.4(4) . . . . ?
C1 C7 C8 O1 32.7(5) . . . . ?
C6 C7 C8 O1 -143.6(4) . . . . ?
C1 C7 C8 C9 -87.9(5) . . . . ?
C6 C7 C8 C9 95.7(4) . . . . ?
O1 C8 C9 N2 -62.2(3) . . . . ?
C7 C8 C9 N2 57.6(4) . . . . ?
O1 C8 C9 O2 175.1(3) . . . . ?
C7 C8 C9 O2 -65.0(4) . . . . ?
O1 C8 C9 C10 61.3(3) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
N2 C9 C10 C11 84.9(3) . . . . ?
O2 C9 C10 C11 -153.1(3) . . . . ?
C8 C9 C10 C11 -37.3(4) . . . . ?
N2 C9 C10 C18 -146.6(3) . . . . ?
O2 C9 C10 C18 -24.5(3) . . . . ?
C8 C9 C10 C18 91.2(3) . . . . ?
C18 C10 C11 C12 76.2(4) . . . . ?
C9 C10 C11 C12 -167.2(3) . . . . ?
C18 C10 C11 C16 -111.1(4) . . . . ?
C9 C10 C11 C16 5.5(5) . . . . ?
C16 C11 C12 C13 1.2(5) . . . . ?
C10 C11 C12 C13 174.0(3) . . . . ?
C11 C12 C13 C14 -1.1(6) . . . . ?
C11 C12 C13 Br1 -178.5(3) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
Br1 C13 C14 C15 177.4(3) . . . . ?
C13 C14 C15 C16 0.9(6) . . . . ?
C14 C15 C16 O1 -178.2(4) . . . . ?
C14 C15 C16 C11 -0.8(6) . . . . ?
C12 C11 C16 O1 177.0(3) . . . . ?
C10 C11 C16 O1 4.1(5) . . . . ?
C12 C11 C16 C15 -0.3(5) . . . . ?
C10 C11 C16 C15 -173.2(3) . . . . ?
C11 C10 C18 C19 143.6(3) . . . . ?
C9 C10 C18 C19 19.9(4) . . . . ?
C11 C10 C18 C17 -38.3(5) . . . . ?
C9 C10 C18 C17 -162.1(3) . . . . ?
C17 C18 C19 O2 174.7(3) . . . . ?
C10 C18 C19 O2 -7.4(4) . . . . ?
C17 C18 C19 C20 -5.6(7) . . . . ?
C10 C18 C19 C20 172.3(4) . . . . ?
C18 C19 C20 C23 -1.5(7) . . . . ?
O2 C19 C20 C23 178.2(4) . . . . ?
C18 C19 C20 C22 -123.2(5) . . . . ?
O2 C19 C20 C22 56.5(5) . . . . ?
C18 C19 C20 C21 117.6(5) . . . . ?
O2 C19 C20 C21 -62.7(5) . . . . ?
N2 C25 C26 O3 179.4(3) . . . . ?
C24 C25 C26 O3 4.6(5) . . . . ?
N2 C25 C26 C27 -1.6(5) . . . . ?
C24 C25 C26 C27 -176.4(3) . . . . ?
O3 C26 C27 C30 -130.3(4) . . . . ?
C25 C26 C27 C30 50.8(5) . . . . ?
O3 C26 C27 C29 107.7(5) . . . . ?
C25 C26 C27 C29 -71.2(5) . . . . ?
O3 C26 C27 C28 -10.7(5) . . . . ?
C25 C26 C27 C28 170.4(4) . . . . ?
C24 C25 N2 C9 0.4(5) . . . . ?
C26 C25 N2 C9 -173.8(3) . . . . ?
O2 C9 N2 C25 -47.2(4) . . . . ?
C8 C9 N2 C25 -167.3(3) . . . . ?
C10 C9 N2 C25 70.7(4) . . . . ?
C15 C16 O1 C8 -160.4(3) . . . . ?
C11 C16 O1 C8 22.2(5) . . . . ?
C7 C8 O1 C16 179.2(3) . . . . ?
C9 C8 O1 C16 -54.7(4) . . . . ?
C18 C19 O2 C9 -9.8(4) . . . . ?
C20 C19 O2 C9 170.4(3) . . . . ?
N2 C9 O2 C19 144.3(3) . . . . ?
C8 C9 O2 C19 -94.4(3) . . . . ?
C10 C9 O2 C19 22.3(3) . . . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1848769'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-07-24 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         'C25 H22 Br N3 O4'
_chemical_formula_sum            'C25 H22 Br N3 O4'
_chemical_formula_weight         508.36

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

_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                   6.8547(15)
_cell_length_b                   15.209(3)
_cell_length_c                   23.124(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.52
_cell_angle_gamma                90
_cell_volume                     2384.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2598
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      19.96

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             1040
_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    1.760
_shelx_estimated_absorpt_T_min   0.677
_shelx_estimated_absorpt_T_max   0.720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            11012
_diffrn_reflns_av_unetI/netI     0.2626
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.228
_diffrn_reflns_theta_max         24.710
_diffrn_reflns_theta_full        24.710
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measured_fraction_theta_full 0.853
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_Laue_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.853
_reflns_number_total             3463
_reflns_number_gt                1240
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0989P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3463
_refine_ls_number_parameters     331
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.2521
_refine_ls_R_factor_gt           0.0833
_refine_ls_wR_factor_ref         0.2262
_refine_ls_wR_factor_gt          0.1701
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_restrained_S_all      0.920
_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 1.66625(15) 0.12422(8) 0.19872(5) 0.0887(5) Uani 1 1 d . . . . .
C1 C 1.1069(12) 0.1874(5) 0.1140(3) 0.043(2) Uani 1 1 d . . . . .
C2 C 1.2941(14) 0.1906(6) 0.1479(3) 0.055(2) Uani 1 1 d . . . . .
H2 H 1.3369 0.2418 0.1677 0.065 Uiso 1 1 calc R U . . .
C3 C 1.4166(13) 0.1164(7) 0.1519(3) 0.057(2) Uani 1 1 d . . . . .
C4 C 1.3566(15) 0.0395(7) 0.1231(4) 0.061(2) Uani 1 1 d . . . . .
H4 H 1.4343 -0.0108 0.1285 0.074 Uiso 1 1 calc R U . . .
C5 C 1.1786(16) 0.0384(6) 0.0859(4) 0.063(3) Uani 1 1 d . . . . .
H5 H 1.1412 -0.0118 0.0642 0.076 Uiso 1 1 calc R U . . .
C6 C 1.0558(14) 0.1108(5) 0.0807(3) 0.048(2) Uani 1 1 d . . . . .
C7 C 0.8416(13) 0.1909(5) 0.0125(3) 0.052(2) Uani 1 1 d . . . . .
H7 H 0.9505 0.2076 -0.0083 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6542(14) 0.1816(5) -0.0300(3) 0.047(2) Uani 1 1 d . . . . .
C9 C 0.5045(15) 0.1262(6) -0.0149(4) 0.067(3) Uani 1 1 d . . . . .
H9 H 0.5251 0.0970 0.0208 0.080 Uiso 1 1 calc R U . . .
C10 C 0.3261(17) 0.1139(7) -0.0520(4) 0.076(3) Uani 1 1 d . . . . .
H10 H 0.2296 0.0778 -0.0404 0.091 Uiso 1 1 calc R U . . .
C11 C 0.2933(18) 0.1544(7) -0.1046(4) 0.081(3) Uani 1 1 d . . . . .
H11 H 0.1752 0.1457 -0.1294 0.097 Uiso 1 1 calc R U . . .
C12 C 0.4367(19) 0.2088(7) -0.1213(4) 0.078(3) Uani 1 1 d . . . . .
H12 H 0.4151 0.2381 -0.1570 0.093 Uiso 1 1 calc R U . . .
C13 C 0.6144(17) 0.2193(5) -0.0837(4) 0.058(3) Uani 1 1 d . . . . .
C14 C 0.8179(13) 0.2596(5) 0.0600(3) 0.044(2) Uani 1 1 d . . . . .
C15 C 0.9562(12) 0.2583(5) 0.1096(3) 0.042(2) Uani 1 1 d . . . . .
C16 C 0.9257(13) 0.3177(5) 0.1539(3) 0.046(2) Uani 1 1 d . . . . .
C17 C 1.0479(16) 0.3050(7) 0.2105(4) 0.071(3) Uani 1 1 d . . . . .
C18 C 0.7742(14) 0.3832(6) 0.1448(4) 0.056(2) Uani 1 1 d . . . . .
C19 C 0.735(3) 0.4547(9) 0.1869(6) 0.129(3) Uani 1 1 d . U . . .
C20 C 0.906(2) 0.4636(8) 0.2423(5) 0.135(3) Uani 1 1 d . U . . .
H20A H 0.8834 0.5154 0.2641 0.203 Uiso 1 1 calc R U . . .
H20B H 1.0319 0.4680 0.2290 0.203 Uiso 1 1 calc R U . . .
H20C H 0.9046 0.4128 0.2668 0.203 Uiso 1 1 calc R U . . .
C21 C 0.551(2) 0.4357(9) 0.2116(6) 0.136(4) Uani 1 1 d . U . . .
H21A H 0.4666 0.4862 0.2068 0.204 Uiso 1 1 calc R U . . .
H21B H 0.5838 0.4221 0.2524 0.204 Uiso 1 1 calc R U . . .
H21C H 0.4850 0.3865 0.1915 0.204 Uiso 1 1 calc R U . . .
C22 C 0.721(3) 0.5433(9) 0.1612(6) 0.142(4) Uani 1 1 d . U . . .
H22A H 0.6043 0.5471 0.1326 0.212 Uiso 1 1 calc R U . . .
H22B H 0.8349 0.5547 0.1428 0.212 Uiso 1 1 calc R U . . .
H22C H 0.7135 0.5860 0.1914 0.212 Uiso 1 1 calc R U . . .
C23 C 0.6496(18) 0.3736(6) 0.0915(4) 0.071(3) Uani 1 1 d . . . . .
O4 O 0.528(4) 0.4428(15) 0.0739(10) 0.070(5) Uani 0.424(19) 1 d . U P A 1
C24 C 0.384(4) 0.4407(18) 0.0139(12) 0.081(6) Uani 0.424(19) 1 d . U P A 1
H24A H 0.3212 0.4974 0.0052 0.097 Uiso 0.424(19) 1 calc R U P A 1
H24B H 0.4522 0.4236 -0.0181 0.097 Uiso 0.424(19) 1 calc R U P A 1
C25 C 0.245(5) 0.377(2) 0.0247(15) 0.084(6) Uani 0.424(19) 1 d . U P A 1
H25A H 0.1850 0.3940 0.0578 0.126 Uiso 0.424(19) 1 calc R U P A 1
H25B H 0.3107 0.3213 0.0325 0.126 Uiso 0.424(19) 1 calc R U P A 1
H25C H 0.1458 0.3713 -0.0090 0.126 Uiso 0.424(19) 1 calc R U P A 1
O4' O 0.457(2) 0.4126(9) 0.0872(7) 0.060(4) Uani 0.576(19) 1 d . U P A 2
C24' C 0.321(3) 0.3913(17) 0.0391(12) 0.082(5) Uani 0.576(19) 1 d . U P A 2
H24C H 0.2753 0.3314 0.0421 0.098 Uiso 0.576(19) 1 calc R U P A 2
H24D H 0.3796 0.3967 0.0035 0.098 Uiso 0.576(19) 1 calc R U P A 2
C25' C 0.155(3) 0.4546(12) 0.0385(8) 0.088(5) Uani 0.576(19) 1 d . U P A 2
H25D H 0.1104 0.4543 0.0760 0.131 Uiso 0.576(19) 1 calc R U P A 2
H25E H 0.0480 0.4375 0.0089 0.131 Uiso 0.576(19) 1 calc R U P A 2
H25F H 0.1983 0.5126 0.0302 0.131 Uiso 0.576(19) 1 calc R U P A 2
N1 N 0.7607(19) 0.2771(7) -0.1041(4) 0.098(3) Uani 1 1 d . . . . .
N2 N 1.1382(17) 0.2859(7) 0.2533(4) 0.106(3) Uani 1 1 d . . . . .
N3 N 0.6663(12) 0.3143(5) 0.0502(3) 0.060(2) Uani 1 1 d . . . . .
O1 O 0.8827(9) 0.1074(3) 0.0411(2) 0.0537(15) Uani 1 1 d . . . . .
O2 O 0.8651(19) 0.3201(6) -0.0721(4) 0.131(3) Uani 1 1 d . . . . .
O3 O 0.772(2) 0.2805(9) -0.1543(5) 0.208(7) 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 C3 1.888(9) . ?
C1 C2 1.402(12) . ?
C1 C6 1.412(11) . ?
C1 C15 1.486(11) . ?
C2 C3 1.401(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(12) . ?
C4 C5 1.384(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(11) . ?
C5 H5 0.9300 . ?
C6 O1 1.387(10) . ?
C7 O1 1.440(9) . ?
C7 C8 1.504(12) . ?
C7 C14 1.542(10) . ?
C7 H7 0.9800 . ?
C8 C13 1.358(11) . ?
C8 C9 1.410(13) . ?
C9 C10 1.398(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.353(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(14) . ?
C12 H12 0.9300 . ?
C13 N1 1.464(14) . ?
C14 N3 1.324(10) . ?
C14 C15 1.376(11) . ?
C15 C16 1.405(10) . ?
C16 C18 1.431(12) . ?
C16 C17 1.458(13) . ?
C17 N2 1.126(13) . ?
C18 C23 1.399(13) . ?
C18 C19 1.510(13) . ?
C19 C22 1.471(19) . ?
C19 C21 1.49(2) . ?
C19 C20 1.61(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N3 1.330(10) . ?
C23 O4 1.37(2) . ?
C23 O4' 1.434(18) . ?
O4 C24 1.58(3) . ?
C24 C25 1.41(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
O4' C24' 1.38(3) . ?
C24' C25' 1.49(3) . ?
C24' H24C 0.9700 . ?
C24' H24D 0.9700 . ?
C25' H25D 0.9600 . ?
C25' H25E 0.9600 . ?
C25' H25F 0.9600 . ?
N1 O2 1.154(12) . ?
N1 O3 1.176(11) . ?

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
C2 C1 C6 117.8(8) . . ?
C2 C1 C15 125.6(7) . . ?
C6 C1 C15 116.6(7) . . ?
C3 C2 C1 119.9(8) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 121.2(9) . . ?
C4 C3 Br1 120.7(7) . . ?
C2 C3 Br1 118.1(7) . . ?
C3 C4 C5 118.9(9) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.0(9) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 O1 118.7(8) . . ?
C5 C6 C1 120.8(9) . . ?
O1 C6 C1 120.6(7) . . ?
O1 C7 C8 107.9(7) . . ?
O1 C7 C14 107.7(6) . . ?
C8 C7 C14 111.1(7) . . ?
O1 C7 H7 110.0 . . ?
C8 C7 H7 110.0 . . ?
C14 C7 H7 110.0 . . ?
C13 C8 C9 115.0(9) . . ?
C13 C8 C7 126.4(8) . . ?
C9 C8 C7 118.5(7) . . ?
C10 C9 C8 122.1(9) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C11 C10 C9 120.3(10) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.6(11) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 119.0(9) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C8 C13 C12 124.1(9) . . ?
C8 C13 N1 119.6(9) . . ?
C12 C13 N1 116.3(8) . . ?
N3 C14 C15 125.3(7) . . ?
N3 C14 C7 117.9(7) . . ?
C15 C14 C7 116.8(8) . . ?
C14 C15 C16 116.1(8) . . ?
C14 C15 C1 117.0(7) . . ?
C16 C15 C1 126.5(7) . . ?
C15 C16 C18 121.6(7) . . ?
C15 C16 C17 116.2(8) . . ?
C18 C16 C17 122.1(7) . . ?
N2 C17 C16 172.6(11) . . ?
C23 C18 C16 113.1(7) . . ?
C23 C18 C19 120.0(10) . . ?
C16 C18 C19 126.8(10) . . ?
C22 C19 C21 108.8(13) . . ?
C22 C19 C18 114.0(11) . . ?
C21 C19 C18 110.3(12) . . ?
C22 C19 C20 104.1(12) . . ?
C21 C19 C20 105.6(11) . . ?
C18 C19 C20 113.5(12) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 O4 115.0(13) . . ?
N3 C23 C18 126.6(10) . . ?
O4 C23 C18 116.7(13) . . ?
N3 C23 O4' 113.9(11) . . ?
C18 C23 O4' 117.0(10) . . ?
C23 O4 C24 121.4(19) . . ?
C25 C24 O4 102(2) . . ?
C25 C24 H24A 111.4 . . ?
O4 C24 H24A 111.4 . . ?
C25 C24 H24B 111.4 . . ?
O4 C24 H24B 111.4 . . ?
H24A C24 H24B 109.2 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24' O4' C23 117.7(15) . . ?
O4' C24' C25' 106.4(18) . . ?
O4' C24' H24C 110.5 . . ?
C25' C24' H24C 110.5 . . ?
O4' C24' H24D 110.5 . . ?
C25' C24' H24D 110.5 . . ?
H24C C24' H24D 108.6 . . ?
C24' C25' H25D 109.5 . . ?
C24' C25' H25E 109.5 . . ?
H25D C25' H25E 109.5 . . ?
C24' C25' H25F 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
O2 N1 O3 119.0(12) . . ?
O2 N1 C13 121.5(9) . . ?
O3 N1 C13 119.5(11) . . ?
C14 N3 C23 116.9(7) . . ?
C6 O1 C7 111.1(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -5.4(10) . . . . ?
C15 C1 C2 C3 174.9(6) . . . . ?
C1 C2 C3 C4 -0.2(11) . . . . ?
C1 C2 C3 Br1 -179.5(5) . . . . ?
C2 C3 C4 C5 5.3(11) . . . . ?
Br1 C3 C4 C5 -175.5(6) . . . . ?
C3 C4 C5 C6 -4.6(12) . . . . ?
C4 C5 C6 O1 177.5(7) . . . . ?
C4 C5 C6 C1 -1.2(11) . . . . ?
C2 C1 C6 C5 6.2(10) . . . . ?
C15 C1 C6 C5 -174.1(6) . . . . ?
C2 C1 C6 O1 -172.5(6) . . . . ?
C15 C1 C6 O1 7.2(9) . . . . ?
O1 C7 C8 C13 -142.7(8) . . . . ?
C14 C7 C8 C13 99.5(9) . . . . ?
O1 C7 C8 C9 34.9(9) . . . . ?
C14 C7 C8 C9 -82.9(9) . . . . ?
C13 C8 C9 C10 -2.1(12) . . . . ?
C7 C8 C9 C10 -179.9(8) . . . . ?
C8 C9 C10 C11 1.1(15) . . . . ?
C9 C10 C11 C12 -0.7(15) . . . . ?
C10 C11 C12 C13 1.4(15) . . . . ?
C9 C8 C13 C12 2.9(12) . . . . ?
C7 C8 C13 C12 -179.5(8) . . . . ?
C9 C8 C13 N1 -179.3(8) . . . . ?
C7 C8 C13 N1 -1.6(13) . . . . ?
C11 C12 C13 C8 -2.6(15) . . . . ?
C11 C12 C13 N1 179.5(8) . . . . ?
O1 C7 C14 N3 -134.1(7) . . . . ?
C8 C7 C14 N3 -16.1(10) . . . . ?
O1 C7 C14 C15 45.4(9) . . . . ?
C8 C7 C14 C15 163.3(7) . . . . ?
N3 C14 C15 C16 3.1(12) . . . . ?
C7 C14 C15 C16 -176.3(7) . . . . ?
N3 C14 C15 C1 175.7(7) . . . . ?
C7 C14 C15 C1 -3.7(10) . . . . ?
C2 C1 C15 C14 156.1(7) . . . . ?
C6 C1 C15 C14 -23.5(9) . . . . ?
C2 C1 C15 C16 -32.2(12) . . . . ?
C6 C1 C15 C16 148.1(7) . . . . ?
C14 C15 C16 C18 -7.8(11) . . . . ?
C1 C15 C16 C18 -179.5(7) . . . . ?
C14 C15 C16 C17 168.3(8) . . . . ?
C1 C15 C16 C17 -3.4(12) . . . . ?
C15 C16 C18 C23 7.6(11) . . . . ?
C17 C16 C18 C23 -168.2(9) . . . . ?
C15 C16 C18 C19 -175.3(11) . . . . ?
C17 C16 C18 C19 8.9(15) . . . . ?
C23 C18 C19 C22 -54.3(18) . . . . ?
C16 C18 C19 C22 128.7(13) . . . . ?
C23 C18 C19 C21 68.5(15) . . . . ?
C16 C18 C19 C21 -108.5(14) . . . . ?
C23 C18 C19 C20 -173.3(11) . . . . ?
C16 C18 C19 C20 9.8(18) . . . . ?
C16 C18 C23 N3 -3.1(14) . . . . ?
C19 C18 C23 N3 179.6(11) . . . . ?
C16 C18 C23 O4 -166.9(13) . . . . ?
C19 C18 C23 O4 15.7(19) . . . . ?
C16 C18 C23 O4' 157.7(10) . . . . ?
C19 C18 C23 O4' -19.7(16) . . . . ?
N3 C23 O4 C24 13(3) . . . . ?
C18 C23 O4 C24 178.7(16) . . . . ?
C23 O4 C24 C25 69(3) . . . . ?
N3 C23 O4' C24' -6(2) . . . . ?
C18 C23 O4' C24' -169.1(17) . . . . ?
C23 O4' C24' C25' -167.7(16) . . . . ?
C8 C13 N1 O2 -32.1(17) . . . . ?
C12 C13 N1 O2 145.9(12) . . . . ?
C8 C13 N1 O3 148.3(13) . . . . ?
C12 C13 N1 O3 -33.6(18) . . . . ?
C15 C14 N3 C23 1.3(12) . . . . ?
C7 C14 N3 C23 -179.3(8) . . . . ?
O4 C23 N3 C14 162.9(14) . . . . ?
C18 C23 N3 C14 -1.2(14) . . . . ?
O4' C23 N3 C14 -162.5(10) . . . . ?
C5 C6 O1 C7 -142.1(7) . . . . ?
C1 C6 O1 C7 36.6(8) . . . . ?
C8 C7 O1 C6 179.3(6) . . . . ?
C14 C7 O1 C6 -60.8(8) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_5f
_database_code_depnum_ccdc_archive 'CCDC 1848772'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-07-24 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         'C25 H16 Br N O2'
_chemical_formula_sum            'C25 H16 Br N O2'
_chemical_formula_weight         442.30

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

_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                   5.3424(18)
_cell_length_b                   19.837(6)
_cell_length_c                   19.534(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.226(10)
_cell_angle_gamma                90
_cell_volume                     2015.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2429
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      19.41

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             896
_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    2.061
_shelx_estimated_absorpt_T_min   0.638
_shelx_estimated_absorpt_T_max   0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_T_max  0.662
_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            17985
_diffrn_reflns_av_unetI/netI     0.1414
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3949
_reflns_number_gt                1354
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0524P)²+2.7711P] 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         3949
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2514
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.1961
_refine_ls_wR_factor_gt          0.1415
_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
Br1 Br 1.4730(2) 1.25310(5) 0.26571(6) 0.1375(5) Uani 1 1 d . . . . .
C1 C 0.2349(16) 0.9044(4) 0.3056(4) 0.094(2) Uani 1 1 d . . . . .
H1 H 0.2411 0.8846 0.2629 0.113 Uiso 1 1 calc R U . . .
C2 C 0.0792(16) 0.8763(4) 0.3458(5) 0.114(3) Uani 1 1 d . . . . .
H2 H -0.0191 0.8384 0.3299 0.137 Uiso 1 1 calc R U . . .
C3 C 0.0707(16) 0.9050(5) 0.4095(5) 0.104(3) Uani 1 1 d . . . . .
H3 H -0.0306 0.8860 0.4374 0.124 Uiso 1 1 calc R U . . .
C4 C 0.2097(16) 0.9606(5) 0.4311(4) 0.103(3) Uani 1 1 d . . . . .
H4 H 0.2043 0.9797 0.4742 0.124 Uiso 1 1 calc R U . . .
C5 C 0.3606(13) 0.9899(4) 0.3905(3) 0.089(2) Uani 1 1 d . . . . .
H5 H 0.4495 1.0295 0.4056 0.107 Uiso 1 1 calc R U . . .
C6 C 0.3806(13) 0.9607(4) 0.3274(3) 0.0687(18) Uani 1 1 d . . . . .
C7 C 0.5377(13) 0.9907(4) 0.2843(3) 0.0651(18) Uani 1 1 d . . . . .
C8 C 0.7129(13) 1.0421(4) 0.2938(3) 0.0625(17) Uani 1 1 d . . . . .
C9 C 0.7845(15) 1.0841(4) 0.3528(4) 0.085(2) Uani 1 1 d . . . . .
C10 C 0.4435(19) 0.8957(6) 0.0429(5) 0.102(3) Uani 1 1 d . . . . .
H10 H 0.3084 0.9258 0.0286 0.122 Uiso 1 1 calc R U . . .
C11 C 0.4160(18) 0.8295(8) 0.0196(4) 0.107(3) Uani 1 1 d . . . . .
H11 H 0.2623 0.8149 -0.0093 0.129 Uiso 1 1 calc R U . . .
C12 C 0.621(3) 0.7857(5) 0.0398(5) 0.091(2) Uani 1 1 d . . . . .
C13 C 0.585(2) 0.7144(5) 0.0125(5) 0.156(4) Uani 1 1 d . . . . .
H13A H 0.7388 0.6995 -0.0003 0.234 Uiso 1 1 calc R U . . .
H13B H 0.4437 0.7128 -0.0279 0.234 Uiso 1 1 calc R U . . .
H13C H 0.5491 0.6854 0.0485 0.234 Uiso 1 1 calc R U . . .
C14 C 0.8411(18) 0.8078(6) 0.0812(5) 0.097(2) Uani 1 1 d . . . . .
H14 H 0.9804 0.7787 0.0940 0.117 Uiso 1 1 calc R U . . .
C15 C 0.8618(17) 0.8730(6) 0.1046(4) 0.101(3) Uani 1 1 d . . . . .
H15 H 1.0153 0.8874 0.1337 0.121 Uiso 1 1 calc R U . . .
C16 C 0.665(2) 0.9169(4) 0.0864(4) 0.085(2) Uani 1 1 d . . . . .
C17 C 0.6924(16) 0.9901(5) 0.1121(3) 0.102(3) Uani 1 1 d . . . . .
H17 H 0.5515 1.0165 0.0835 0.122 Uiso 1 1 calc R U . . .
C18 C 0.6857(15) 0.9986(4) 0.1893(3) 0.081(2) Uani 1 1 d . . . . .
C19 C 0.8103(13) 1.0468(4) 0.2307(3) 0.0658(18) Uani 1 1 d . . . . .
C20 C 0.9897(13) 1.0895(4) 0.2060(3) 0.0708(18) Uani 1 1 d . . . . .
C21 C 1.1175(14) 1.1442(4) 0.2419(4) 0.081(2) Uani 1 1 d . . . . .
H21 H 1.0882 1.1563 0.2854 0.098 Uiso 1 1 calc R U . . .
C22 C 1.2876(15) 1.1806(3) 0.2134(4) 0.090(2) Uani 1 1 d . . . . .
C23 C 1.3247(16) 1.1654(5) 0.1478(5) 0.097(2) Uani 1 1 d . . . . .
H23 H 1.4363 1.1913 0.1284 0.116 Uiso 1 1 calc R U . . .
C24 C 1.1981(16) 1.1125(5) 0.1112(4) 0.094(2) Uani 1 1 d . . . . .
H24 H 1.2223 1.1024 0.0667 0.113 Uiso 1 1 calc R U . . .
C25 C 1.0337(14) 1.0738(4) 0.1401(4) 0.077(2) Uani 1 1 d . . . . .
N1 N 0.8462(15) 1.1185(4) 0.4010(4) 0.126(3) Uani 1 1 d . . . . .
O1 O 0.5200(8) 0.9630(2) 0.2187(2) 0.0871(14) Uani 1 1 d . . . . .
O2 O 0.9312(10) 1.0177(3) 0.1034(2) 0.0895(15) 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 C22 1.905(8) . ?
C1 C6 1.373(9) . ?
C1 C2 1.384(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.342(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(8) . ?
C7 C8 1.367(8) . ?
C7 O1 1.377(7) . ?
C8 C9 1.403(10) . ?
C8 C19 1.447(7) . ?
C9 N1 1.147(9) . ?
C10 C16 1.355(10) . ?
C10 C11 1.385(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(11) . ?
C11 H11 0.9300 . ?
C12 C14 1.340(10) . ?
C12 C13 1.509(12) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.366(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.350(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.531(10) . ?
C17 O2 1.434(8) . ?
C17 C18 1.525(9) . ?
C17 H17 0.9800 . ?
C18 C19 1.329(8) . ?
C18 O1 1.359(7) . ?
C19 C20 1.441(9) . ?
C20 C21 1.384(9) . ?
C20 C25 1.396(8) . ?
C21 C22 1.375(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(9) . ?
C23 C24 1.360(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(9) . ?
C24 H24 0.9300 . ?
C25 O2 1.370(8) . ?

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
C6 C1 C2 121.6(7) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.6(8) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.4(8) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.3(8) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 120.5(7) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.5(7) . . ?
C1 C6 C7 121.2(6) . . ?
C5 C6 C7 121.3(7) . . ?
C8 C7 O1 108.9(5) . . ?
C8 C7 C6 134.3(6) . . ?
O1 C7 C6 116.8(7) . . ?
C7 C8 C9 127.1(6) . . ?
C7 C8 C19 107.5(6) . . ?
C9 C8 C19 125.3(7) . . ?
N1 C9 C8 179.2(8) . . ?
C16 C10 C11 120.8(9) . . ?
C16 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 118.9(8) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C14 C12 C11 119.7(8) . . ?
C14 C12 C13 122.9(12) . . ?
C11 C12 C13 117.4(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 120.3(8) . . ?
C12 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 121.6(9) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C10 118.6(9) . . ?
C15 C16 C17 121.0(11) . . ?
C10 C16 C17 120.3(10) . . ?
O2 C17 C18 107.3(6) . . ?
O2 C17 C16 110.1(6) . . ?
C18 C17 C16 114.0(7) . . ?
O2 C17 H17 108.4 . . ?
C18 C17 H17 108.4 . . ?
C16 C17 H17 108.4 . . ?
C19 C18 O1 113.6(6) . . ?
C19 C18 C17 124.0(7) . . ?
O1 C18 C17 121.7(8) . . ?
C18 C19 C20 119.9(6) . . ?
C18 C19 C8 104.2(6) . . ?
C20 C19 C8 136.0(7) . . ?
C21 C20 C25 118.2(7) . . ?
C21 C20 C19 125.5(6) . . ?
C25 C20 C19 116.3(7) . . ?
C22 C21 C20 120.2(7) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.8(8) . . ?
C23 C22 Br1 119.9(7) . . ?
C21 C22 Br1 119.3(6) . . ?
C24 C23 C22 119.9(8) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.1(7) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
O2 C25 C24 117.0(7) . . ?
O2 C25 C20 122.2(7) . . ?
C24 C25 C20 120.7(8) . . ?
C18 O1 C7 105.8(6) . . ?
C25 O2 C17 120.5(6) . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_4i
_database_code_depnum_ccdc_archive 'CCDC 1848771'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-07-24 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 H20 Br Cl N2 O2'
_chemical_formula_sum            'C24 H20 Br Cl N2 O2'
_chemical_formula_weight         483.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2635(5)
_cell_length_b                   11.3364(6)
_cell_length_c                   11.3467(6)
_cell_angle_alpha                86.529(2)
_cell_angle_beta                 72.466(2)
_cell_angle_gamma                78.713(2)
_cell_volume                     1114.23(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6559
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.74

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             492
_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    1.987
_shelx_estimated_absorpt_T_min   0.647
_shelx_estimated_absorpt_T_max   0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_T_max  0.672
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            17365
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5062
_reflns_number_gt                3291
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0435P)²+0.3062P] 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         5062
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.20280(4) 0.48594(2) 0.87408(3) 0.06633(14) Uani 1 1 d . . . . .
C1 C 0.1525(3) 0.6523(2) 0.8388(2) 0.0419(6) Uani 1 1 d . . . . .
C2 C 0.0521(3) 0.7257(2) 0.9325(2) 0.0496(6) Uani 1 1 d . . . . .
H2 H 0.0098 0.6935 1.0097 0.059 Uiso 1 1 calc R U . . .
C3 C 0.0150(3) 0.8464(2) 0.9110(3) 0.0538(7) Uani 1 1 d . . . . .
H3 H -0.0537 0.8964 0.9735 0.065 Uiso 1 1 calc R U . . .
C4 C 0.0794(3) 0.8935(2) 0.7971(3) 0.0568(7) Uani 1 1 d . . . . .
H4 H 0.0560 0.9757 0.7830 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1786(3) 0.8189(2) 0.7040(2) 0.0502(6) Uani 1 1 d . . . . .
H5 H 0.2204 0.8517 0.6270 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2181(3) 0.6955(2) 0.7220(2) 0.0390(5) Uani 1 1 d . . . . .
C7 C 0.3277(3) 0.6137(2) 0.6195(2) 0.0434(6) Uani 1 1 d . . . . .
H7 H 0.2841 0.5413 0.6212 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3497(3) 0.6671(2) 0.4927(2) 0.0437(6) Uani 1 1 d . . . . .
C9 C 0.4686(3) 0.7262(2) 0.4405(2) 0.0401(6) Uani 1 1 d . . . . .
C10 C 0.5618(3) 0.7451(2) 0.5210(2) 0.0408(6) Uani 1 1 d . . . . .
C11 C 0.6429(3) 0.8386(2) 0.5094(2) 0.0472(6) Uani 1 1 d . . . . .
H11 H 0.6388 0.8968 0.4485 0.057 Uiso 1 1 calc R U . . .
C12 C 0.7289(3) 0.8448(3) 0.5879(3) 0.0534(7) Uani 1 1 d . . . . .
C13 C 0.7381(3) 0.7602(3) 0.6784(3) 0.0588(7) Uani 1 1 d . . . . .
H13 H 0.8009 0.7635 0.7280 0.071 Uiso 1 1 calc R U . . .
C14 C 0.6534(3) 0.6707(3) 0.6949(2) 0.0537(7) Uani 1 1 d . . . . .
H14 H 0.6570 0.6138 0.7570 0.064 Uiso 1 1 calc R U . . .
C15 C 0.5625(3) 0.6651(2) 0.6189(2) 0.0429(6) Uani 1 1 d . . . . .
C16 C 0.6332(4) 0.8043(3) 0.2553(2) 0.0520(7) Uani 1 1 d . . . . .
C17 C 0.4927(3) 0.7600(2) 0.3140(2) 0.0434(6) Uani 1 1 d . . . . .
C18 C 0.3909(3) 0.7431(2) 0.2498(2) 0.0464(6) Uani 1 1 d . . . . .
C19 C 0.4037(3) 0.7762(3) 0.1134(3) 0.0580(8) Uani 1 1 d . . . . .
C20 C 0.2627(4) 0.8741(3) 0.1099(3) 0.0882(12) Uani 1 1 d . . . . .
H20A H 0.2646 0.9450 0.1511 0.132 Uiso 1 1 calc R U . . .
H20B H 0.1697 0.8448 0.1509 0.132 Uiso 1 1 calc R U . . .
H20C H 0.2665 0.8931 0.0256 0.132 Uiso 1 1 calc R U . . .
C21 C 0.4054(4) 0.6626(3) 0.0441(3) 0.0694(9) Uani 1 1 d . . . . .
H21A H 0.4091 0.6831 -0.0400 0.104 Uiso 1 1 calc R U . . .
H21B H 0.3138 0.6309 0.0837 0.104 Uiso 1 1 calc R U . . .
H21C H 0.4943 0.6032 0.0454 0.104 Uiso 1 1 calc R U . . .
C22 C 0.5478(4) 0.8252(3) 0.0416(3) 0.0768(10) Uani 1 1 d . . . . .
H22A H 0.5500 0.8976 0.0801 0.115 Uiso 1 1 calc R U . . .
H22B H 0.5460 0.8423 -0.0420 0.115 Uiso 1 1 calc R U . . .
H22C H 0.6378 0.7664 0.0414 0.115 Uiso 1 1 calc R U . . .
C23 C 0.2655(3) 0.6906(3) 0.3228(3) 0.0540(7) Uani 1 1 d . . . . .
C24 C 0.0300(4) 0.6256(4) 0.3427(4) 0.0973(13) Uani 1 1 d . . . . .
H24A H 0.0676 0.5455 0.3665 0.146 Uiso 1 1 calc R U . . .
H24B H -0.0390 0.6227 0.2950 0.146 Uiso 1 1 calc R U . . .
H24C H -0.0238 0.6733 0.4154 0.146 Uiso 1 1 calc R U . . .
Cl1 Cl 0.82986(11) 0.96252(8) 0.56973(8) 0.0829(3) Uani 1 1 d . . . . .
N1 N 0.7496(4) 0.8339(3) 0.2164(2) 0.0779(8) Uani 1 1 d . . . . .
N2 N 0.2473(2) 0.6500(2) 0.4360(2) 0.0506(5) Uani 1 1 d . . . . .
O1 O 0.47613(18) 0.57621(15) 0.64168(16) 0.0475(4) Uani 1 1 d . . . . .
O2 O 0.1568(2) 0.6782(2) 0.2702(2) 0.0793(7) 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 C1 1.900(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.385(3) . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(3) . ?
C7 O1 1.450(3) . ?
C7 C8 1.498(4) . ?
C7 H7 0.9800 . ?
C8 N2 1.343(3) . ?
C8 C9 1.364(3) . ?
C9 C17 1.426(3) . ?
C9 C10 1.482(3) . ?
C10 C15 1.392(3) . ?
C10 C11 1.393(4) . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(4) . ?
C12 Cl1 1.742(3) . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 O1 1.372(3) . ?
C16 N1 1.143(4) . ?
C16 C17 1.443(4) . ?
C17 C18 1.400(3) . ?
C18 C23 1.422(4) . ?
C18 C19 1.545(4) . ?
C19 C22 1.528(4) . ?
C19 C21 1.544(4) . ?
C19 C20 1.548(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N2 1.310(4) . ?
C23 O2 1.348(3) . ?
C24 O2 1.430(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.5(2) . . ?
C2 C1 Br1 117.85(19) . . ?
C6 C1 Br1 119.60(18) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 116.3(2) . . ?
C1 C6 C7 122.0(2) . . ?
C5 C6 C7 121.7(2) . . ?
O1 C7 C8 109.56(19) . . ?
O1 C7 C6 110.65(19) . . ?
C8 C7 C6 114.17(19) . . ?
O1 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
C6 C7 H7 107.4 . . ?
N2 C8 C9 123.9(2) . . ?
N2 C8 C7 115.3(2) . . ?
C9 C8 C7 120.7(2) . . ?
C8 C9 C17 116.8(2) . . ?
C8 C9 C10 116.2(2) . . ?
C17 C9 C10 127.0(2) . . ?
C15 C10 C11 117.8(2) . . ?
C15 C10 C9 116.7(2) . . ?
C11 C10 C9 125.4(2) . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 121.6(3) . . ?
C13 C12 Cl1 119.7(2) . . ?
C11 C12 Cl1 118.7(2) . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
O1 C15 C14 117.7(2) . . ?
O1 C15 C10 121.1(2) . . ?
C14 C15 C10 121.1(2) . . ?
N1 C16 C17 174.0(3) . . ?
C18 C17 C9 121.5(2) . . ?
C18 C17 C16 122.7(2) . . ?
C9 C17 C16 115.7(2) . . ?
C17 C18 C23 113.5(2) . . ?
C17 C18 C19 126.5(3) . . ?
C23 C18 C19 120.0(2) . . ?
C22 C19 C21 106.5(2) . . ?
C22 C19 C18 115.5(2) . . ?
C21 C19 C18 108.9(2) . . ?
C22 C19 C20 107.2(3) . . ?
C21 C19 C20 110.2(2) . . ?
C18 C19 C20 108.4(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 O2 116.6(3) . . ?
N2 C23 C18 126.1(2) . . ?
O2 C23 C18 117.3(3) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 N2 C8 117.7(2) . . ?
C15 O1 C7 113.32(18) . . ?
C23 O2 C24 117.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(4) . . . . ?
Br1 C1 C2 C3 179.0(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
Br1 C1 C6 C5 -178.51(18) . . . . ?
C2 C1 C6 C7 -179.6(2) . . . . ?
Br1 C1 C6 C7 1.1(3) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C1 C6 C7 O1 -73.2(3) . . . . ?
C5 C6 C7 O1 106.4(3) . . . . ?
C1 C6 C7 C8 162.7(2) . . . . ?
C5 C6 C7 C8 -17.8(3) . . . . ?
O1 C7 C8 N2 147.7(2) . . . . ?
C6 C7 C8 N2 -87.6(3) . . . . ?
O1 C7 C8 C9 -31.0(3) . . . . ?
C6 C7 C8 C9 93.7(3) . . . . ?
N2 C8 C9 C17 -6.7(3) . . . . ?
C7 C8 C9 C17 171.9(2) . . . . ?
N2 C8 C9 C10 175.0(2) . . . . ?
C7 C8 C9 C10 -6.3(3) . . . . ?
C8 C9 C10 C15 24.5(3) . . . . ?
C17 C9 C10 C15 -153.5(2) . . . . ?
C8 C9 C10 C11 -152.8(2) . . . . ?
C17 C9 C10 C11 29.1(4) . . . . ?
C15 C10 C11 C12 4.5(4) . . . . ?
C9 C10 C11 C12 -178.2(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C10 C11 C12 Cl1 179.5(2) . . . . ?
C11 C12 C13 C14 -3.2(4) . . . . ?
Cl1 C12 C13 C14 177.5(2) . . . . ?
C12 C13 C14 C15 1.3(4) . . . . ?
C13 C14 C15 O1 -177.9(2) . . . . ?
C13 C14 C15 C10 3.6(4) . . . . ?
C11 C10 C15 O1 175.1(2) . . . . ?
C9 C10 C15 O1 -2.4(3) . . . . ?
C11 C10 C15 C14 -6.4(4) . . . . ?
C9 C10 C15 C14 176.0(2) . . . . ?
C8 C9 C17 C18 5.6(3) . . . . ?
C10 C9 C17 C18 -176.3(2) . . . . ?
C8 C9 C17 C16 -170.2(2) . . . . ?
C10 C9 C17 C16 7.8(3) . . . . ?
C9 C17 C18 C23 0.2(3) . . . . ?
C16 C17 C18 C23 175.7(2) . . . . ?
C9 C17 C18 C19 179.7(2) . . . . ?
C16 C17 C18 C19 -4.8(4) . . . . ?
C17 C18 C19 C22 3.9(4) . . . . ?
C23 C18 C19 C22 -176.6(2) . . . . ?
C17 C18 C19 C21 123.7(3) . . . . ?
C23 C18 C19 C21 -56.8(3) . . . . ?
C17 C18 C19 C20 -116.3(3) . . . . ?
C23 C18 C19 C20 63.2(3) . . . . ?
C17 C18 C23 N2 -6.0(4) . . . . ?
C19 C18 C23 N2 174.4(2) . . . . ?
C17 C18 C23 O2 175.9(2) . . . . ?
C19 C18 C23 O2 -3.7(4) . . . . ?
O2 C23 N2 C8 -176.5(2) . . . . ?
C18 C23 N2 C8 5.3(4) . . . . ?
C9 C8 N2 C23 1.5(4) . . . . ?
C7 C8 N2 C23 -177.2(2) . . . . ?
C14 C15 O1 C7 144.2(2) . . . . ?
C10 C15 O1 C7 -37.3(3) . . . . ?
C8 C7 O1 C15 52.1(2) . . . . ?
C6 C7 O1 C15 -74.6(2) . . . . ?
N2 C23 O2 C24 1.7(4) . . . . ?
C18 C23 O2 C24 -180.0(3) . . . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_3j
_database_code_depnum_ccdc_archive 'CCDC 1848767'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-07-24 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 H30 Cl N3 O4'
_chemical_formula_sum            'C30 H30 Cl N3 O4'
_chemical_formula_weight         532.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1744(8)
_cell_length_b                   12.6935(11)
_cell_length_c                   13.1360(12)
_cell_angle_alpha                113.581(3)
_cell_angle_beta                 93.921(3)
_cell_angle_gamma                112.484(2)
_cell_volume                     1386.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6732
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.19

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.965
_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            21973
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6397
_reflns_number_gt                3993
_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)+(0.0537P)²+0.5333P] 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         6397
_refine_ls_number_parameters     363
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.058
_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 0.3453(2) 0.81914(19) 0.27908(17) 0.0404(5) Uani 1 1 d . . . . .
C2 C 0.4212(3) 0.8020(2) 0.35847(19) 0.0511(6) Uani 1 1 d . . . . .
H2 H 0.4179 0.8364 0.4349 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5013(3) 0.7341(2) 0.3236(2) 0.0529(6) Uani 1 1 d . . . . .
H3 H 0.5519 0.7218 0.3762 0.063 Uiso 1 1 calc R U . . .
C4 C 0.5062(2) 0.6842(2) 0.2105(2) 0.0457(5) Uani 1 1 d . . . . .
C5 C 0.4340(2) 0.70252(19) 0.13139(18) 0.0405(5) Uani 1 1 d . . . . .
H5 H 0.4401 0.6696 0.0556 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3516(2) 0.77055(18) 0.16523(16) 0.0353(4) Uani 1 1 d . . . . .
C7 C 0.2841(2) 0.80365(18) 0.08351(16) 0.0338(4) Uani 1 1 d . . . . .
H7 H 0.3609 0.8425 0.0507 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2234(2) 0.90040(18) 0.14342(15) 0.0330(4) Uani 1 1 d . . . . .
C9 C 0.1562(2) 0.87296(19) 0.23655(17) 0.0380(5) Uani 1 1 d . . . . .
H9 H 0.0813 0.7831 0.2007 0.046 Uiso 1 1 calc R U . . .
C10 C 0.0871(2) 0.95719(19) 0.30020(17) 0.0372(5) Uani 1 1 d . . . . .
C11 C 0.1630(2) 1.0643(2) 0.40410(19) 0.0508(6) Uani 1 1 d . . . . .
H11 H 0.2605 1.0870 0.4350 0.061 Uiso 1 1 calc R U . . .
C12 C 0.0983(2) 1.1396(2) 0.46445(19) 0.0529(6) Uani 1 1 d . . . . .
H12 H 0.1524 1.2126 0.5344 0.063 Uiso 1 1 calc R U . . .
C13 C -0.0462(2) 1.1058(2) 0.42023(19) 0.0459(5) Uani 1 1 d . . . . .
C14 C -0.0446(3) 1.2835(2) 0.5794(2) 0.0693(8) Uani 1 1 d . . . . .
H14A H 0.0002 1.2637 0.6315 0.104 Uiso 1 1 calc R U . . .
H14B H -0.1117 1.3152 0.6116 0.104 Uiso 1 1 calc R U . . .
H14C H 0.0304 1.3478 0.5671 0.104 Uiso 1 1 calc R U . . .
C15 C -0.1250(3) 0.9973(2) 0.3167(2) 0.0583(6) Uani 1 1 d . . . . .
H15 H -0.2230 0.9738 0.2863 0.070 Uiso 1 1 calc R U . . .
C16 C -0.0591(2) 0.9238(2) 0.25810(19) 0.0534(6) Uani 1 1 d . . . . .
H16 H -0.1139 0.8501 0.1888 0.064 Uiso 1 1 calc R U . . .
C17 C 0.1284(2) 0.5716(2) -0.07821(18) 0.0444(5) Uani 1 1 d . . . . .
C18 C 0.1482(2) 0.69982(19) -0.01474(16) 0.0373(5) Uani 1 1 d . . . . .
C19 C 0.0587(2) 0.74981(19) -0.03046(16) 0.0377(5) Uani 1 1 d . . . . .
C20 C -0.0790(2) 0.7011(2) -0.12127(19) 0.0510(5) Uani 1 1 d . U . . .
C21 C -0.1239(4) 0.5646(4) -0.2152(3) 0.0764(10) Uani 0.779(3) 1 d . U P A 1
H21A H -0.0454 0.5635 -0.2516 0.115 Uiso 0.779(3) 1 calc R U P A 1
H21B H -0.2110 0.5372 -0.2715 0.115 Uiso 0.779(3) 1 calc R U P A 1
H21C H -0.1435 0.5073 -0.1816 0.115 Uiso 0.779(3) 1 calc R U P A 1
C22 C -0.0523(5) 0.7922(4) -0.1734(4) 0.0800(10) Uani 0.779(3) 1 d . U P A 1
H22A H -0.0251 0.8773 -0.1137 0.120 Uiso 0.779(3) 1 calc R U P A 1
H22B H -0.1406 0.7641 -0.2287 0.120 Uiso 0.779(3) 1 calc R U P A 1
H22C H 0.0258 0.7930 -0.2106 0.120 Uiso 0.779(3) 1 calc R U P A 1
C23 C -0.2077(4) 0.6962(4) -0.0641(3) 0.0762(10) Uani 0.779(3) 1 d . U P A 1
H23A H -0.2165 0.6467 -0.0233 0.114 Uiso 0.779(3) 1 calc R U P A 1
H23B H -0.2978 0.6569 -0.1223 0.114 Uiso 0.779(3) 1 calc R U P A 1
H23C H -0.1888 0.7820 -0.0112 0.114 Uiso 0.779(3) 1 calc R U P A 1
C21' C -0.0455(15) 0.6458(14) -0.2429(11) 0.0764(10) Uani 0.221(3) 1 d . U P A
2
H21D H -0.0089 0.5849 -0.2481 0.115 Uiso 0.221(3) 1 calc R U P A 2
H21E H 0.0271 0.7150 -0.2512 0.115 Uiso 0.221(3) 1 calc R U P A 2
H21F H -0.1344 0.6040 -0.3029 0.115 Uiso 0.221(3) 1 calc R U P A 2
C22' C -0.1012(17) 0.8212(14) -0.1113(13) 0.0800(10) Uani 0.221(3) 1 d . U P A
2
H22D H -0.1811 0.7939 -0.1738 0.120 Uiso 0.221(3) 1 calc R U P A 2
H22E H -0.0125 0.8830 -0.1144 0.120 Uiso 0.221(3) 1 calc R U P A 2
H22F H -0.1233 0.8595 -0.0395 0.120 Uiso 0.221(3) 1 calc R U P A 2
C23' C -0.1995(13) 0.6044(15) -0.1077(12) 0.0762(10) Uani 0.221(3) 1 d . U P A
2
H23D H -0.1846 0.5289 -0.1296 0.114 Uiso 0.221(3) 1 calc R U P A 2
H23E H -0.2906 0.5829 -0.1559 0.114 Uiso 0.221(3) 1 calc R U P A 2
H23F H -0.2032 0.6373 -0.0288 0.114 Uiso 0.221(3) 1 calc R U P A 2
C24 C 0.3472(2) 1.0296(2) 0.0101(2) 0.0447(5) Uani 1 1 d . . . . .
C25 C 0.3872(2) 1.08893(18) 0.13622(16) 0.0353(4) Uani 1 1 d . . . . .
C26 C 0.5108(2) 1.2261(2) 0.19171(18) 0.0416(5) Uani 1 1 d . . . . .
C27 C 0.5742(3) 1.3035(2) 0.32028(19) 0.0505(6) Uani 1 1 d . . . . .
C28 C 0.7017(4) 1.4319(3) 0.3470(3) 0.1004(12) Uani 1 1 d . . . . .
H28A H 0.7777 1.4171 0.3133 0.151 Uiso 1 1 calc R U . . .
H28B H 0.7405 1.4835 0.4289 0.151 Uiso 1 1 calc R U . . .
H28C H 0.6672 1.4761 0.3157 0.151 Uiso 1 1 calc R U . . .
C29 C 0.4551(4) 1.3288(3) 0.3762(2) 0.0828(9) Uani 1 1 d . . . . .
H29A H 0.4255 1.3789 0.3499 0.124 Uiso 1 1 calc R U . . .
H29B H 0.4936 1.3751 0.4584 0.124 Uiso 1 1 calc R U . . .
H29C H 0.3715 1.2484 0.3556 0.124 Uiso 1 1 calc R U . . .
C30 C 0.6289(3) 1.2323(3) 0.3680(3) 0.0823(9) Uani 1 1 d . . . . .
H30A H 0.5466 1.1561 0.3586 0.123 Uiso 1 1 calc R U . . .
H30B H 0.6783 1.2870 0.4483 0.123 Uiso 1 1 calc R U . . .
H30C H 0.6961 1.2089 0.3273 0.123 Uiso 1 1 calc R U . . .
Cl1 Cl 0.61058(7) 0.60040(7) 0.16844(6) 0.0681(2) Uani 1 1 d . . . . .
N1 N 0.1144(2) 0.4690(2) -0.12365(19) 0.0650(6) Uani 1 1 d . . . . .
N2 N 0.33460(17) 1.03264(15) 0.19493(13) 0.0351(4) Uani 1 1 d . . . . .
N3 N 0.3271(2) 0.9833(2) -0.08701(19) 0.0691(6) Uani 1 1 d . . . . .
O1 O 0.27098(16) 0.89038(14) 0.32052(11) 0.0448(4) Uani 1 1 d . . . . .
O2 O -0.12223(18) 1.17112(16) 0.47328(14) 0.0642(5) Uani 1 1 d . . . . .
O3 O 0.10616(14) 0.87392(12) 0.05425(11) 0.0379(3) Uani 1 1 d . . . . .
O4 O 0.5525(2) 1.26663(16) 0.12484(14) 0.0681(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 O1 1.368(2) . ?
C1 C6 1.388(3) . ?
C1 C2 1.390(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 Cl1 1.744(2) . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(3) . ?
C7 C18 1.522(3) . ?
C7 C8 1.543(3) . ?
C7 H7 0.9800 . ?
C8 N2 1.445(2) . ?
C8 O3 1.448(2) . ?
C8 C9 1.536(3) . ?
C9 O1 1.435(2) . ?
C9 C10 1.509(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.369(3) . ?
C10 C16 1.385(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 O2 1.369(2) . ?
C13 C15 1.378(3) . ?
C14 O2 1.413(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N1 1.139(3) . ?
C17 C18 1.423(3) . ?
C18 C19 1.340(3) . ?
C19 O3 1.377(2) . ?
C19 C20 1.512(3) . ?
C20 C23' 1.447(14) . ?
C20 C22 1.517(4) . ?
C20 C21 1.530(4) . ?
C20 C23 1.547(4) . ?
C20 C22' 1.581(15) . ?
C20 C21' 1.588(13) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C21' H21D 0.9600 . ?
C21' H21E 0.9600 . ?
C21' H21F 0.9600 . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 0.9600 . ?
C23' H23D 0.9600 . ?
C23' H23E 0.9600 . ?
C23' H23F 0.9600 . ?
C24 N3 1.134(3) . ?
C24 C25 1.468(3) . ?
C25 N2 1.264(2) . ?
C25 C26 1.526(3) . ?
C26 O4 1.209(2) . ?
C26 C27 1.507(3) . ?
C27 C30 1.520(4) . ?
C27 C28 1.525(4) . ?
C27 C29 1.530(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 122.70(17) . . ?
O1 C1 C2 116.49(18) . . ?
C6 C1 C2 120.75(19) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 Cl1 119.74(17) . . ?
C3 C4 Cl1 118.94(17) . . ?
C4 C5 C6 119.75(19) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.79(18) . . ?
C1 C6 C7 120.08(17) . . ?
C5 C6 C7 120.80(17) . . ?
C6 C7 C18 119.91(16) . . ?
C6 C7 C8 112.81(15) . . ?
C18 C7 C8 99.14(15) . . ?
C6 C7 H7 108.1 . . ?
C18 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
N2 C8 O3 111.64(14) . . ?
N2 C8 C9 109.22(15) . . ?
O3 C8 C9 108.35(15) . . ?
N2 C8 C7 112.89(15) . . ?
O3 C8 C7 105.03(14) . . ?
C9 C8 C7 109.55(15) . . ?
O1 C9 C10 107.18(15) . . ?
O1 C9 C8 108.15(15) . . ?
C10 C9 C8 115.80(16) . . ?
O1 C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C8 C9 H9 108.5 . . ?
C11 C10 C16 117.69(19) . . ?
C11 C10 C9 121.65(18) . . ?
C16 C10 C9 120.55(18) . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
O2 C13 C12 124.6(2) . . ?
O2 C13 C15 115.9(2) . . ?
C12 C13 C15 119.50(19) . . ?
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 . . ?
C16 C15 C13 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C13 C15 H15 119.9 . . ?
C15 C16 C10 121.3(2) . . ?
C15 C16 H16 119.3 . . ?
C10 C16 H16 119.3 . . ?
N1 C17 C18 176.4(2) . . ?
C19 C18 C17 127.92(19) . . ?
C19 C18 C7 109.62(17) . . ?
C17 C18 C7 122.44(18) . . ?
C18 C19 O3 111.81(17) . . ?
C18 C19 C20 134.15(19) . . ?
O3 C19 C20 114.02(17) . . ?
C23' C20 C19 108.5(5) . . ?
C19 C20 C22 108.9(2) . . ?
C19 C20 C21 111.9(2) . . ?
C22 C20 C21 110.3(3) . . ?
C19 C20 C23 108.9(2) . . ?
C22 C20 C23 109.8(3) . . ?
C21 C20 C23 107.1(3) . . ?
C23' C20 C22' 115.7(8) . . ?
C19 C20 C22' 107.9(5) . . ?
C23' C20 C21' 112.6(8) . . ?
C19 C20 C21' 107.2(5) . . ?
C22' C20 C21' 104.6(8) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C21' H21D 109.5 . . ?
C20 C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C20 C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C20 C22' H22D 109.5 . . ?
C20 C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
C20 C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
C20 C23' H23D 109.5 . . ?
C20 C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C20 C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
N3 C24 C25 174.3(2) . . ?
N2 C25 C24 125.16(18) . . ?
N2 C25 C26 122.07(18) . . ?
C24 C25 C26 112.61(17) . . ?
O4 C26 C27 123.4(2) . . ?
O4 C26 C25 114.84(19) . . ?
C27 C26 C25 121.74(18) . . ?
C26 C27 C30 110.9(2) . . ?
C26 C27 C28 108.7(2) . . ?
C30 C27 C28 109.7(2) . . ?
C26 C27 C29 109.1(2) . . ?
C30 C27 C29 109.6(2) . . ?
C28 C27 C29 108.9(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 N2 C8 122.81(16) . . ?
C1 O1 C9 115.84(15) . . ?
C13 O2 C14 117.40(18) . . ?
C19 O3 C8 107.84(14) . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1848768'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-07-24 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         'C25 H22 Br2 N2 O2'
_chemical_formula_sum            'C25 H22 Br2 N2 O2'
_chemical_formula_weight         542.26

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                   6.8119(12)
_cell_length_b                   15.187(3)
_cell_length_c                   22.922(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.315(5)
_cell_angle_gamma                90
_cell_volume                     2346.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5477
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      23.82

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.479
_shelx_estimated_absorpt_T_min   0.515
_shelx_estimated_absorpt_T_max   0.543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_T_max  0.499
_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            22889
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         27.664
_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             5425
_reflns_number_gt                2788
_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)+(0.0499P)²+3.8409P] 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         5425
_refine_ls_number_parameters     313
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1449
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.030
_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 -0.66567(8) 0.87479(4) 0.29881(3) 0.0805(3) Uani 1 1 d . . . . .
Br2 Br 0.19081(10) 0.70427(5) 0.61025(3) 0.0954(3) Uani 1 1 d . . . . .
C1 C -0.0613(6) 0.8888(3) 0.41969(17) 0.0423(11) Uani 1 1 d . . . . .
C2 C -0.1826(7) 0.9615(3) 0.4136(2) 0.0536(12) Uani 1 1 d . . . . .
H2 H -0.1447 1.0125 0.4347 0.064 Uiso 1 1 calc R U . . .
C3 C -0.3599(7) 0.9591(3) 0.3762(2) 0.0553(13) Uani 1 1 d . . . . .
H3 H -0.4409 1.0086 0.3710 0.066 Uiso 1 1 calc R U . . .
C4 C -0.4152(6) 0.8820(3) 0.34660(19) 0.0485(12) Uani 1 1 d . . . . .
C5 C -0.2921(7) 0.8097(3) 0.35075(19) 0.0474(11) Uani 1 1 d . . . . .
H5 H -0.3322 0.7587 0.3300 0.057 Uiso 1 1 calc R U . . .
C6 C -0.1069(6) 0.8129(3) 0.38603(17) 0.0407(10) Uani 1 1 d . . . . .
C7 C 0.0451(6) 0.7436(3) 0.39075(17) 0.0382(10) Uani 1 1 d . . . . .
C8 C 0.1798(6) 0.7417(3) 0.44203(17) 0.0387(10) Uani 1 1 d . . . . .
C9 C 0.1585(7) 0.8098(3) 0.48876(17) 0.0429(11) Uani 1 1 d . . . . .
H9 H 0.0511 0.7923 0.5105 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3466(7) 0.8223(3) 0.53134(17) 0.0426(11) Uani 1 1 d . . . . .
C11 C 0.3827(7) 0.7809(3) 0.58511(19) 0.0519(12) Uani 1 1 d . . . . .
C12 C 0.5594(8) 0.7910(3) 0.6225(2) 0.0624(14) Uani 1 1 d . . . . .
H12 H 0.5810 0.7619 0.6585 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7029(8) 0.8451(4) 0.6052(2) 0.0663(15) Uani 1 1 d . . . . .
H13 H 0.8218 0.8532 0.6302 0.080 Uiso 1 1 calc R U . . .
C14 C 0.6736(7) 0.8862(3) 0.5531(2) 0.0550(13) Uani 1 1 d . . . . .
H14 H 0.7731 0.9214 0.5418 0.066 Uiso 1 1 calc R U . . .
C15 C 0.4947(7) 0.8764(3) 0.5156(2) 0.0555(13) Uani 1 1 d . . . . .
H15 H 0.4745 0.9063 0.4798 0.067 Uiso 1 1 calc R U . . .
C16 C -0.0326(8) 0.6991(3) 0.2888(2) 0.0594(14) Uani 1 1 d . . . . .
C17 C 0.0786(7) 0.6825(3) 0.34627(18) 0.0439(11) Uani 1 1 d . . . . .
C18 C 0.2259(7) 0.6188(3) 0.3556(2) 0.0523(12) Uani 1 1 d . . . . .
C19 C 0.2642(11) 0.5473(5) 0.3112(3) 0.0996(16) Uani 1 1 d . U . . .
C20 C 0.2817(13) 0.4582(5) 0.3400(3) 0.125(2) Uani 1 1 d . U . . .
H20A H 0.2802 0.4135 0.3103 0.188 Uiso 1 1 calc R U . . .
H20B H 0.1723 0.4492 0.3614 0.188 Uiso 1 1 calc R U . . .
H20C H 0.4040 0.4548 0.3666 0.188 Uiso 1 1 calc R U . . .
C21 C 0.4548(12) 0.5687(5) 0.2867(3) 0.123(2) Uani 1 1 d . U . . .
H21A H 0.5639 0.5695 0.3183 0.184 Uiso 1 1 calc R U . . .
H21B H 0.4426 0.6254 0.2680 0.184 Uiso 1 1 calc R U . . .
H21C H 0.4779 0.5247 0.2584 0.184 Uiso 1 1 calc R U . . .
C22 C 0.1034(12) 0.5373(5) 0.2585(3) 0.121(2) Uani 1 1 d . U . . .
H22A H 0.1351 0.4887 0.2347 0.181 Uiso 1 1 calc R U . . .
H22B H 0.0949 0.5903 0.2355 0.181 Uiso 1 1 calc R U . . .
H22C H -0.0215 0.5265 0.2719 0.181 Uiso 1 1 calc R U . . .
O2 O 0.5341(18) 0.5878(8) 0.4159(5) 0.061(3) Uani 0.562(14) 1 d . . P A 1
C23 C 0.678(3) 0.6075(14) 0.4680(9) 0.070(5) Uani 0.562(14) 1 d . . P A 1
H23A H 0.6201 0.5981 0.5037 0.084 Uiso 0.562(14) 1 calc R U P A 1
H23B H 0.7220 0.6682 0.4672 0.084 Uiso 0.562(14) 1 calc R U P A 1
C24 C 0.8496(16) 0.5460(8) 0.4660(5) 0.092(5) Uani 0.562(14) 1 d . . P A 1
H24A H 0.8079 0.4866 0.4717 0.138 Uiso 0.562(14) 1 calc R U P A 1
H24B H 0.9558 0.5613 0.4965 0.138 Uiso 0.562(14) 1 calc R U P A 1
H24C H 0.8947 0.5506 0.4283 0.138 Uiso 0.562(14) 1 calc R U P A 1
O2' O 0.473(2) 0.5543(9) 0.4289(7) 0.064(4) Uani 0.438(14) 1 d . . P A 2
C23' C 0.600(2) 0.5642(11) 0.4848(6) 0.062(4) Uani 0.438(14) 1 d . . P A 2
H23C H 0.6596 0.5081 0.4977 0.074 Uiso 0.438(14) 1 calc R U P A 2
H23D H 0.5250 0.5856 0.5147 0.074 Uiso 0.438(14) 1 calc R U P A 2
C24' C 0.755(4) 0.628(2) 0.4753(17) 0.104(11) Uani 0.438(14) 1 d . . P A 2
H24D H 0.8247 0.6072 0.4444 0.156 Uiso 0.438(14) 1 calc R U P A 2
H24E H 0.8468 0.6345 0.5110 0.156 Uiso 0.438(14) 1 calc R U P A 2
H24F H 0.6951 0.6838 0.4643 0.156 Uiso 0.438(14) 1 calc R U P A 2
N1 N -0.1161(8) 0.7210(4) 0.2450(2) 0.0945(18) Uani 1 1 d . . . . .
N2 N 0.3289(6) 0.6859(2) 0.45148(16) 0.0521(10) Uani 1 1 d . . . . .
C25 C 0.3504(8) 0.6272(3) 0.4106(2) 0.0637(14) Uani 1 1 d . . . . .
O1 O 0.1098(4) 0.89315(18) 0.45983(12) 0.0487(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
Br1 C4 1.893(4) . ?
Br2 C11 1.901(5) . ?
C1 C2 1.374(6) . ?
C1 O1 1.378(5) . ?
C1 C6 1.398(6) . ?
C2 C3 1.377(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(6) . ?
C5 C6 1.397(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.469(6) . ?
C7 C8 1.383(5) . ?
C7 C17 1.422(6) . ?
C8 N2 1.316(5) . ?
C8 C9 1.511(6) . ?
C9 O1 1.446(5) . ?
C9 C10 1.506(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.373(6) . ?
C10 C15 1.389(6) . ?
C11 C12 1.381(7) . ?
C12 C13 1.378(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.337(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N1 1.131(6) . ?
C16 C17 1.443(7) . ?
C17 C18 1.387(6) . ?
C18 C25 1.420(7) . ?
C18 C19 1.535(7) . ?
C19 C20 1.503(10) . ?
C19 C22 1.517(9) . ?
C19 C21 1.522(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O2 C25 1.377(13) . ?
O2 C23 1.46(2) . ?
C23 C24 1.50(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O2' C25 1.414(15) . ?
O2' C23' 1.448(19) . ?
C23' C24' 1.47(3) . ?
C23' H23C 0.9700 . ?
C23' H23D 0.9700 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
N2 C25 1.317(6) . ?

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
C2 C1 O1 117.9(4) . . ?
C2 C1 C6 121.6(4) . . ?
O1 C1 C6 120.5(4) . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 Br1 118.9(4) . . ?
C3 C4 Br1 119.6(4) . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 117.2(4) . . ?
C5 C6 C7 125.9(4) . . ?
C1 C6 C7 116.9(4) . . ?
C8 C7 C17 116.1(4) . . ?
C8 C7 C6 116.9(4) . . ?
C17 C7 C6 126.8(4) . . ?
N2 C8 C7 123.7(4) . . ?
N2 C8 C9 118.4(4) . . ?
C7 C8 C9 117.9(4) . . ?
O1 C9 C10 107.7(3) . . ?
O1 C9 C8 108.3(3) . . ?
C10 C9 C8 112.7(4) . . ?
O1 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C11 C10 C15 117.5(4) . . ?
C11 C10 C9 123.3(4) . . ?
C15 C10 C9 119.2(4) . . ?
C10 C11 C12 122.2(5) . . ?
C10 C11 Br2 120.7(4) . . ?
C12 C11 Br2 117.1(4) . . ?
C13 C12 C11 118.7(5) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 120.9(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.3(4) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N1 C16 C17 172.9(6) . . ?
C18 C17 C7 122.2(4) . . ?
C18 C17 C16 122.3(4) . . ?
C7 C17 C16 115.0(4) . . ?
C17 C18 C25 113.6(4) . . ?
C17 C18 C19 125.4(5) . . ?
C25 C18 C19 120.9(5) . . ?
C20 C19 C22 105.2(6) . . ?
C20 C19 C21 109.7(7) . . ?
C22 C19 C21 106.5(6) . . ?
C20 C19 C18 110.9(6) . . ?
C22 C19 C18 115.2(5) . . ?
C21 C19 C18 109.2(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C25 O2 C23 118.6(12) . . ?
O2 C23 C24 106.3(13) . . ?
O2 C23 H23A 110.5 . . ?
C24 C23 H23A 110.5 . . ?
O2 C23 H23B 110.5 . . ?
C24 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
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 . . ?
C25 O2' C23' 115.7(11) . . ?
O2' C23' C24' 106.8(17) . . ?
O2' C23' H23C 110.4 . . ?
C24' C23' H23C 110.4 . . ?
O2' C23' H23D 110.4 . . ?
C24' C23' H23D 110.4 . . ?
H23C C23' H23D 108.6 . . ?
C23' C24' H24D 109.5 . . ?
C23' C24' H24E 109.5 . . ?
H24D C24' H24E 109.5 . . ?
C23' C24' H24F 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C8 N2 C25 118.7(4) . . ?
N2 C25 O2 115.1(6) . . ?
N2 C25 O2' 116.1(8) . . ?
N2 C25 C18 125.4(4) . . ?
O2 C25 C18 117.3(6) . . ?
O2' C25 C18 116.4(7) . . ?
C1 O1 C9 112.4(3) . . ?

_refine_diff_density_max         0.805
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_4f
_database_code_depnum_ccdc_archive 'CCDC 1848770'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-07-24 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 H20 Br N3 O4'
_chemical_formula_sum            'C24 H20 Br N3 O4'
_chemical_formula_weight         494.34

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0719(4)
_cell_length_b                   11.2308(4)
_cell_length_c                   11.5065(4)
_cell_angle_alpha                80.4220(10)
_cell_angle_beta                 76.3630(10)
_cell_angle_gamma                70.8480(10)
_cell_volume                     1071.16(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9148
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             504
_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    1.956
_shelx_estimated_absorpt_T_min   0.651
_shelx_estimated_absorpt_T_max   0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  0.676
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            14647
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4188
_reflns_number_gt                3594
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0275P)²+0.3961P] 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         4188
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.17789(3) 0.41914(2) 0.04558(2) 0.03464(8) Uani 1 1 d . . . . .
C1 C 0.44479(19) 0.36223(15) 0.35742(14) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.3519(2) 0.28525(16) 0.35940(15) 0.0203(4) Uani 1 1 d . . . . .
H2 H 0.3462 0.2214 0.4216 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2677(2) 0.30358(16) 0.26861(16) 0.0217(4) Uani 1 1 d . . . . .
H3 H 0.2031 0.2537 0.2698 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2816(2) 0.39751(16) 0.17632(15) 0.0205(4) Uani 1 1 d . . . . .
C5 C 0.36853(19) 0.47859(15) 0.17587(15) 0.0181(3) Uani 1 1 d . . . . .
H5 H 0.3748 0.5415 0.1128 0.022 Uiso 1 1 calc R U . . .
C6 C 0.44669(19) 0.46555(15) 0.27030(14) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.53876(19) 0.54818(15) 0.28313(14) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.66224(19) 0.49236(15) 0.34371(14) 0.0155(3) Uani 1 1 d . . . . .
C9 C 0.68699(19) 0.35895(15) 0.40163(14) 0.0161(3) Uani 1 1 d . . . . .
H9 H 0.7357 0.3507 0.4712 0.019 Uiso 1 1 calc R U . . .
C10 C 0.79625(18) 0.25787(15) 0.31932(14) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.8334(2) 0.29089(16) 0.19678(15) 0.0203(4) Uani 1 1 d . . . . .
H11 H 0.7947 0.3750 0.1670 0.024 Uiso 1 1 calc R U . . .
C12 C 0.9268(2) 0.20220(17) 0.11677(16) 0.0226(4) Uani 1 1 d . . . . .
H12 H 0.9489 0.2274 0.0350 0.027 Uiso 1 1 calc R U . . .
C13 C 0.9862(2) 0.07737(16) 0.15865(15) 0.0211(4) Uani 1 1 d . . . . .
H13 H 1.0507 0.0183 0.1057 0.025 Uiso 1 1 calc R U . . .
C14 C 0.9497(2) 0.04004(16) 0.28006(15) 0.0190(4) Uani 1 1 d . . . . .
H14 H 0.9880 -0.0444 0.3090 0.023 Uiso 1 1 calc R U . . .
C15 C 0.85576(18) 0.12933(15) 0.35797(14) 0.0153(3) Uani 1 1 d . . . . .
C16 C 0.3687(2) 0.73888(15) 0.19246(15) 0.0189(4) Uani 1 1 d . . . . .
C17 C 0.51070(19) 0.67950(15) 0.24364(14) 0.0153(3) Uani 1 1 d . . . . .
C18 C 0.61025(19) 0.74608(15) 0.25791(14) 0.0153(3) Uani 1 1 d . . . . .
C19 C 0.59178(19) 0.88800(15) 0.22096(14) 0.0173(3) Uani 1 1 d . . . . .
C20 C 0.7350(2) 0.90057(17) 0.12173(16) 0.0242(4) Uani 1 1 d . . . . .
H20A H 0.7374 0.8609 0.0533 0.036 Uiso 1 1 calc R U . . .
H20B H 0.8317 0.8601 0.1516 0.036 Uiso 1 1 calc R U . . .
H20C H 0.7252 0.9886 0.0985 0.036 Uiso 1 1 calc R U . . .
C21 C 0.5827(2) 0.95313(16) 0.33140(16) 0.0216(4) Uani 1 1 d . . . . .
H21A H 0.5741 1.0409 0.3078 0.032 Uiso 1 1 calc R U . . .
H21B H 0.6772 0.9128 0.3641 0.032 Uiso 1 1 calc R U . . .
H21C H 0.4913 0.9463 0.3911 0.032 Uiso 1 1 calc R U . . .
C22 C 0.4420(2) 0.96267(16) 0.17023(16) 0.0230(4) Uani 1 1 d . . . . .
H22A H 0.3493 0.9583 0.2296 0.034 Uiso 1 1 calc R U . . .
H22B H 0.4430 0.9269 0.0997 0.034 Uiso 1 1 calc R U . . .
H22C H 0.4401 1.0495 0.1496 0.034 Uiso 1 1 calc R U . . .
C23 C 0.74110(19) 0.66986(15) 0.31292(14) 0.0173(3) Uani 1 1 d . . . . .
C24 C 0.9786(2) 0.64958(17) 0.38067(18) 0.0268(4) Uani 1 1 d . . . . .
H24A H 0.9374 0.6225 0.4619 0.040 Uiso 1 1 calc R U . . .
H24B H 1.0469 0.6992 0.3807 0.040 Uiso 1 1 calc R U . . .
H24C H 1.0379 0.5768 0.3378 0.040 Uiso 1 1 calc R U . . .
N1 N 0.82175(16) 0.08058(13) 0.48524(13) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.2542(2) 0.77598(15) 0.15479(15) 0.0302(4) Uani 1 1 d . . . . .
N3 N 0.76399(16) 0.55053(13) 0.35719(12) 0.0169(3) Uani 1 1 d . . . . .
O1 O 0.53420(13) 0.33582(10) 0.44524(10) 0.0175(2) Uani 1 1 d . . . . .
O2 O 0.78339(16) 0.15328(12) 0.56311(11) 0.0267(3) Uani 1 1 d . . . . .
O3 O 0.83562(15) -0.03315(11) 0.50849(11) 0.0252(3) Uani 1 1 d . . . . .
O4 O 0.84848(14) 0.72518(11) 0.32293(11) 0.0231(3) 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 C4 1.8982(17) . ?
C1 O1 1.377(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C5 C6 1.395(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.481(2) . ?
C7 C8 1.377(2) . ?
C7 C17 1.425(2) . ?
C8 N3 1.342(2) . ?
C8 C9 1.502(2) . ?
C9 O1 1.4510(19) . ?
C9 C10 1.531(2) . ?
C9 H9 0.9800 . ?
C10 C11 1.387(2) . ?
C10 C15 1.401(2) . ?
C11 C12 1.393(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9300 . ?
C15 N1 1.473(2) . ?
C16 N2 1.144(2) . ?
C16 C17 1.454(2) . ?
C17 C18 1.398(2) . ?
C18 C23 1.432(2) . ?
C18 C19 1.543(2) . ?
C19 C22 1.534(2) . ?
C19 C21 1.542(2) . ?
C19 C20 1.543(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N3 1.319(2) . ?
C23 O4 1.350(2) . ?
C24 O4 1.442(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 O2 1.2250(18) . ?
N1 O3 1.2310(18) . ?

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
O1 C1 C2 117.97(15) . . ?
O1 C1 C6 120.44(14) . . ?
C2 C1 C6 121.58(15) . . ?
C1 C2 C3 119.89(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 118.53(16) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 122.12(16) . . ?
C3 C4 Br1 119.79(13) . . ?
C5 C4 Br1 118.09(13) . . ?
C4 C5 C6 119.78(16) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 117.58(15) . . ?
C5 C6 C7 125.35(15) . . ?
C1 C6 C7 117.00(14) . . ?
C8 C7 C17 116.50(15) . . ?
C8 C7 C6 116.02(14) . . ?
C17 C7 C6 127.44(15) . . ?
N3 C8 C7 124.08(15) . . ?
N3 C8 C9 116.10(14) . . ?
C7 C8 C9 119.81(14) . . ?
O1 C9 C8 109.55(12) . . ?
O1 C9 C10 109.72(12) . . ?
C8 C9 C10 114.04(13) . . ?
O1 C9 H9 107.8 . . ?
C8 C9 H9 107.8 . . ?
C10 C9 H9 107.8 . . ?
C11 C10 C15 116.03(14) . . ?
C11 C10 C9 119.53(15) . . ?
C15 C10 C9 124.32(14) . . ?
C10 C11 C12 122.19(16) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 120.00(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.64(15) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 119.49(16) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 122.61(15) . . ?
C14 C15 N1 115.63(15) . . ?
C10 C15 N1 121.76(14) . . ?
N2 C16 C17 174.17(18) . . ?
C18 C17 C7 121.78(15) . . ?
C18 C17 C16 123.09(14) . . ?
C7 C17 C16 115.08(14) . . ?
C17 C18 C23 113.85(14) . . ?
C17 C18 C19 126.88(14) . . ?
C23 C18 C19 119.26(14) . . ?
C22 C19 C21 106.07(13) . . ?
C22 C19 C20 106.51(14) . . ?
C21 C19 C20 110.78(14) . . ?
C22 C19 C18 115.01(13) . . ?
C21 C19 C18 109.63(13) . . ?
C20 C19 C18 108.78(13) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 O4 117.00(15) . . ?
N3 C23 C18 125.48(15) . . ?
O4 C23 C18 117.50(14) . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 N1 O3 122.80(14) . . ?
O2 N1 C15 119.34(14) . . ?
O3 N1 C15 117.85(13) . . ?
C23 N3 C8 117.87(14) . . ?
C1 O1 C9 112.89(12) . . ?
C23 O4 C24 117.70(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -176.07(14) . . . . ?
C6 C1 C2 C3 5.0(2) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C2 C3 C4 C5 -4.2(3) . . . . ?
C2 C3 C4 Br1 176.37(12) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
Br1 C4 C5 C6 -179.90(12) . . . . ?
C4 C5 C6 C1 5.5(2) . . . . ?
C4 C5 C6 C7 -177.80(15) . . . . ?
O1 C1 C6 C5 172.71(14) . . . . ?
C2 C1 C6 C5 -8.4(2) . . . . ?
O1 C1 C6 C7 -4.3(2) . . . . ?
C2 C1 C6 C7 174.64(14) . . . . ?
C5 C6 C7 C8 -150.81(16) . . . . ?
C1 C6 C7 C8 25.9(2) . . . . ?
C5 C6 C7 C17 31.5(3) . . . . ?
C1 C6 C7 C17 -151.74(15) . . . . ?
C17 C7 C8 N3 -6.4(2) . . . . ?
C6 C7 C8 N3 175.68(14) . . . . ?
C17 C7 C8 C9 172.41(14) . . . . ?
C6 C7 C8 C9 -5.5(2) . . . . ?
N3 C8 C9 O1 145.28(13) . . . . ?
C7 C8 C9 O1 -33.62(19) . . . . ?
N3 C8 C9 C10 -91.32(17) . . . . ?
C7 C8 C9 C10 89.78(17) . . . . ?
O1 C9 C10 C11 109.17(16) . . . . ?
C8 C9 C10 C11 -14.1(2) . . . . ?
O1 C9 C10 C15 -66.67(19) . . . . ?
C8 C9 C10 C15 170.02(15) . . . . ?
C15 C10 C11 C12 -1.1(2) . . . . ?
C9 C10 C11 C12 -177.33(15) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C10 -0.6(2) . . . . ?
C13 C14 C15 N1 179.36(15) . . . . ?
C11 C10 C15 C14 1.7(2) . . . . ?
C9 C10 C15 C14 177.64(15) . . . . ?
C11 C10 C15 N1 -178.32(15) . . . . ?
C9 C10 C15 N1 -2.3(2) . . . . ?
C8 C7 C17 C18 4.5(2) . . . . ?
C6 C7 C17 C18 -177.88(15) . . . . ?
C8 C7 C17 C16 -173.21(14) . . . . ?
C6 C7 C17 C16 4.4(2) . . . . ?
C7 C17 C18 C23 1.0(2) . . . . ?
C16 C17 C18 C23 178.50(14) . . . . ?
C7 C17 C18 C19 -179.06(14) . . . . ?
C16 C17 C18 C19 -1.6(2) . . . . ?
C17 C18 C19 C22 3.8(2) . . . . ?
C23 C18 C19 C22 -176.29(14) . . . . ?
C17 C18 C19 C21 123.17(17) . . . . ?
C23 C18 C19 C21 -56.90(19) . . . . ?
C17 C18 C19 C20 -115.55(17) . . . . ?
C23 C18 C19 C20 64.38(18) . . . . ?
C17 C18 C23 N3 -5.7(2) . . . . ?
C19 C18 C23 N3 174.36(15) . . . . ?
C17 C18 C23 O4 175.87(13) . . . . ?
C19 C18 C23 O4 -4.1(2) . . . . ?
C14 C15 N1 O2 157.95(15) . . . . ?
C10 C15 N1 O2 -22.1(2) . . . . ?
C14 C15 N1 O3 -21.1(2) . . . . ?
C10 C15 N1 O3 158.93(15) . . . . ?
O4 C23 N3 C8 -177.31(13) . . . . ?
C18 C23 N3 C8 4.2(2) . . . . ?
C7 C8 N3 C23 2.3(2) . . . . ?
C9 C8 N3 C23 -176.59(14) . . . . ?
C2 C1 O1 C9 143.88(14) . . . . ?
C6 C1 O1 C9 -37.16(19) . . . . ?
C8 C9 O1 C1 54.43(16) . . . . ?
C10 C9 O1 C1 -71.48(16) . . . . ?
N3 C23 O4 C24 0.1(2) . . . . ?
C18 C23 O4 C24 178.66(14) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 1848766'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-07-24 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         'C29 H28 Cl N3 O3'
_chemical_formula_sum            'C29 H28 Cl N3 O3'
_chemical_formula_weight         501.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9330(7)
_cell_length_b                   12.4636(12)
_cell_length_c                   23.3748(16)
_cell_angle_alpha                93.564(3)
_cell_angle_beta                 97.108(2)
_cell_angle_gamma                113.474(2)
_cell_volume                     2614.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7499
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1056
_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    0.181
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_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            41384
_diffrn_reflns_av_unetI/netI     0.1221
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         27.602
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             12043
_reflns_number_gt                5910
_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)+(0.0440P)²+0.8224P] 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         12043
_refine_ls_number_parameters     661
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1733
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1084
_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 0.8282(3) 0.8821(2) 0.14054(11) 0.0385(6) Uani 1 1 d . . . . .
C2 C 0.8073(3) 0.9639(2) 0.17686(11) 0.0511(8) Uani 1 1 d . . . . .
H2 H 0.8648 0.9912 0.2135 0.061 Uiso 1 1 calc R U . . .
C3 C 0.7014(3) 1.0050(2) 0.15880(12) 0.0516(8) Uani 1 1 d . . . . .
H3 H 0.6863 1.0593 0.1834 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6180(3) 0.9654(2) 0.10414(12) 0.0420(7) Uani 1 1 d . . . . .
C5 C 0.6395(3) 0.8860(2) 0.06731(11) 0.0383(6) Uani 1 1 d . . . . .
H5 H 0.5826 0.8603 0.0305 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7467(3) 0.8436(2) 0.08500(10) 0.0321(6) Uani 1 1 d . . . . .
C7 C 0.7641(3) 0.7514(2) 0.04586(9) 0.0299(6) Uani 1 1 d . . . . .
H7 H 0.6651 0.6899 0.0308 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8583(3) 0.6938(2) 0.07727(9) 0.0307(6) Uani 1 1 d . . . . .
C9 C 0.9868(3) 0.7861(2) 0.12147(10) 0.0337(6) Uani 1 1 d . . . . .
H9 H 1.0477 0.8485 0.1004 0.040 Uiso 1 1 calc R U . . .
C10 C 1.0866(3) 0.7385(2) 0.15462(10) 0.0335(6) Uani 1 1 d . . . . .
C11 C 1.2140(3) 0.7442(2) 0.13492(11) 0.0474(7) Uani 1 1 d . . . . .
H11 H 1.2396 0.7796 0.1017 0.057 Uiso 1 1 calc R U . . .
C12 C 1.3045(3) 0.6977(3) 0.16425(14) 0.0581(8) Uani 1 1 d . . . . .
H12 H 1.3897 0.7010 0.1504 0.070 Uiso 1 1 calc R U . . .
C13 C 1.2684(4) 0.6472(3) 0.21332(14) 0.0599(8) Uani 1 1 d . . . . .
H13 H 1.3287 0.6155 0.2328 0.072 Uiso 1 1 calc R U . . .
C14 C 1.1440(4) 0.6430(3) 0.23408(12) 0.0608(8) Uani 1 1 d . . . . .
H14 H 1.1203 0.6090 0.2678 0.073 Uiso 1 1 calc R U . . .
C15 C 1.0527(3) 0.6891(2) 0.20499(11) 0.0471(7) Uani 1 1 d . . . . .
H15 H 0.9685 0.6867 0.2195 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8360(3) 0.8775(2) -0.03774(11) 0.0375(6) Uani 1 1 d . . . . .
C17 C 0.8476(3) 0.7883(2) -0.00495(9) 0.0298(6) Uani 1 1 d . . . . .
C18 C 0.9273(3) 0.7254(2) -0.01215(10) 0.0314(6) Uani 1 1 d . . . . .
C19 C 1.0168(3) 0.7123(2) -0.05712(10) 0.0386(6) Uani 1 1 d . . . . .
C20 C 0.9682(4) 0.5824(3) -0.07764(15) 0.0913(13) Uani 1 1 d . . . . .
H20A H 0.9855 0.5429 -0.0454 0.137 Uiso 1 1 calc R U . . .
H20B H 1.0242 0.5741 -0.1070 0.137 Uiso 1 1 calc R U . . .
H20C H 0.8642 0.5482 -0.0935 0.137 Uiso 1 1 calc R U . . .
C21 C 0.9987(4) 0.7760(4) -0.10843(14) 0.0989(14) Uani 1 1 d . . . . .
H21A H 0.8967 0.7417 -0.1270 0.148 Uiso 1 1 calc R U . . .
H21B H 1.0607 0.7691 -0.1356 0.148 Uiso 1 1 calc R U . . .
H21C H 1.0272 0.8577 -0.0953 0.148 Uiso 1 1 calc R U . . .
C22 C 1.1801(3) 0.7631(3) -0.03029(15) 0.0873(12) Uani 1 1 d . . . . .
H22A H 1.2107 0.8436 -0.0143 0.131 Uiso 1 1 calc R U . . .
H22B H 1.2384 0.7595 -0.0596 0.131 Uiso 1 1 calc R U . . .
H22C H 1.1943 0.7182 0.0000 0.131 Uiso 1 1 calc R U . . .
C23 C 0.6557(3) 0.4712(2) 0.01328(12) 0.0390(6) Uani 1 1 d . . . . .
C24 C 0.6819(3) 0.4972(2) 0.07682(10) 0.0322(6) Uani 1 1 d . . . . .
C25 C 0.5787(3) 0.3940(2) 0.10445(11) 0.0388(6) Uani 1 1 d . . . . .
C26 C 0.5810(3) 0.3952(2) 0.16912(11) 0.0441(7) Uani 1 1 d . . . . .
C27 C 0.4561(4) 0.2825(3) 0.18092(13) 0.0737(10) Uani 1 1 d . . . . .
H27A H 0.3618 0.2809 0.1644 0.111 Uiso 1 1 calc R U . . .
H27B H 0.4605 0.2806 0.2221 0.111 Uiso 1 1 calc R U . . .
H27C H 0.4675 0.2153 0.1637 0.111 Uiso 1 1 calc R U . . .
C28 C 0.7302(4) 0.3995(3) 0.19749(13) 0.0775(10) Uani 1 1 d . . . . .
H28A H 0.7407 0.3298 0.1833 0.116 Uiso 1 1 calc R U . . .
H28B H 0.7344 0.4036 0.2389 0.116 Uiso 1 1 calc R U . . .
H28C H 0.8093 0.4678 0.1882 0.116 Uiso 1 1 calc R U . . .
C29 C 0.5568(4) 0.5026(3) 0.19336(14) 0.0743(10) Uani 1 1 d . . . . .
H29A H 0.6401 0.5735 0.1895 0.111 Uiso 1 1 calc R U . . .
H29B H 0.5473 0.4985 0.2336 0.111 Uiso 1 1 calc R U . . .
H29C H 0.4677 0.5026 0.1721 0.111 Uiso 1 1 calc R U . . .
C30 C 1.0014(3) 0.2849(2) 0.34819(11) 0.0426(7) Uani 1 1 d . . . . .
C31 C 1.0910(4) 0.3347(3) 0.30767(13) 0.0598(8) Uani 1 1 d . . . . .
H31 H 1.0487 0.3302 0.2693 0.072 Uiso 1 1 calc R U . . .
C32 C 1.2431(4) 0.3911(3) 0.32437(14) 0.0607(9) Uani 1 1 d . . . . .
H32 H 1.3039 0.4239 0.2972 0.073 Uiso 1 1 calc R U . . .
C33 C 1.3043(3) 0.3985(2) 0.38130(14) 0.0492(7) Uani 1 1 d . . . . .
C34 C 1.2165(3) 0.3480(2) 0.42155(12) 0.0404(6) Uani 1 1 d . . . . .
H34 H 1.2596 0.3521 0.4597 0.049 Uiso 1 1 calc R U . . .
C35 C 1.0622(3) 0.2904(2) 0.40516(11) 0.0347(6) Uani 1 1 d . . . . .
C36 C 0.9669(3) 0.2254(2) 0.44790(10) 0.0318(6) Uani 1 1 d . . . . .
H36 H 1.0106 0.1743 0.4649 0.038 Uiso 1 1 calc R U . . .
C37 C 0.8050(3) 0.1467(2) 0.41884(10) 0.0315(6) Uani 1 1 d . . . . .
C38 C 0.7554(3) 0.2081(2) 0.37071(10) 0.0372(6) Uani 1 1 d . . . . .
H38 H 0.7661 0.2854 0.3879 0.045 Uiso 1 1 calc R U . . .
C39 C 0.5978(3) 0.1420(2) 0.33948(10) 0.0359(6) Uani 1 1 d . . . . .
C40 C 0.4856(3) 0.1710(2) 0.35489(12) 0.0510(7) Uani 1 1 d . . . . .
H40 H 0.5071 0.2305 0.3850 0.061 Uiso 1 1 calc R U . . .
C41 C 0.3411(3) 0.1118(3) 0.32571(14) 0.0629(9) Uani 1 1 d . . . . .
H41 H 0.2659 0.1311 0.3367 0.075 Uiso 1 1 calc R U . . .
C42 C 0.3087(3) 0.0252(3) 0.28100(14) 0.0652(9) Uani 1 1 d . . . . .
H42 H 0.2118 -0.0140 0.2613 0.078 Uiso 1 1 calc R U . . .
C43 C 0.4195(4) -0.0039(3) 0.26518(12) 0.0593(8) Uani 1 1 d . . . . .
H43 H 0.3979 -0.0627 0.2346 0.071 Uiso 1 1 calc R U . . .
C44 C 0.5622(3) 0.0535(2) 0.29443(11) 0.0474(7) Uani 1 1 d . . . . .
H44 H 0.6363 0.0325 0.2837 0.057 Uiso 1 1 calc R U . . .
C45 C 1.0486(3) 0.3986(2) 0.52883(11) 0.0382(6) Uani 1 1 d . . . . .
C46 C 0.9361(3) 0.2936(2) 0.49722(10) 0.0311(6) Uani 1 1 d . . . . .
C47 C 0.7955(3) 0.2371(2) 0.50563(10) 0.0320(6) Uani 1 1 d . . . . .
C48 C 0.7038(3) 0.2529(2) 0.54924(10) 0.0386(6) Uani 1 1 d . . . . .
C49 C 0.7970(3) 0.3583(3) 0.59524(12) 0.0605(8) Uani 1 1 d . . . . .
H49A H 0.8787 0.3455 0.6153 0.091 Uiso 1 1 calc R U . . .
H49B H 0.7361 0.3668 0.6225 0.091 Uiso 1 1 calc R U . . .
H49C H 0.8346 0.4286 0.5767 0.091 Uiso 1 1 calc R U . . .
C50 C 0.6429(4) 0.1409(3) 0.57873(14) 0.0769(10) Uani 1 1 d . . . . .
H50A H 0.5841 0.0750 0.5499 0.115 Uiso 1 1 calc R U . . .
H50B H 0.5822 0.1498 0.6060 0.115 Uiso 1 1 calc R U . . .
H50C H 0.7241 0.1276 0.5988 0.115 Uiso 1 1 calc R U . . .
C51 C 0.5751(3) 0.2756(3) 0.51768(13) 0.0676(9) Uani 1 1 d . . . . .
H51A H 0.6139 0.3440 0.4979 0.101 Uiso 1 1 calc R U . . .
H51B H 0.5176 0.2883 0.5454 0.101 Uiso 1 1 calc R U . . .
H51C H 0.5129 0.2085 0.4900 0.101 Uiso 1 1 calc R U . . .
C52 C 0.8148(3) -0.0272(2) 0.49247(12) 0.0380(6) Uani 1 1 d . . . . .
C53 C 0.7950(2) -0.0444(2) 0.42884(10) 0.0312(6) Uani 1 1 d . . . . .
C54 C 0.7933(3) -0.1628(2) 0.40654(10) 0.0336(6) Uani 1 1 d . . . . .
C55 C 0.7965(3) -0.1944(2) 0.34341(10) 0.0379(6) Uani 1 1 d . . . . .
C56 C 0.6445(3) -0.2172(3) 0.30840(12) 0.0608(8) Uani 1 1 d . . . . .
H56A H 0.5686 -0.2827 0.3212 0.091 Uiso 1 1 calc R U . . .
H56B H 0.6452 -0.2346 0.2679 0.091 Uiso 1 1 calc R U . . .
H56C H 0.6245 -0.1483 0.3142 0.091 Uiso 1 1 calc R U . . .
C57 C 0.8215(3) -0.3083(2) 0.33788(12) 0.0582(8) Uani 1 1 d . . . . .
H57A H 0.9165 -0.2948 0.3597 0.087 Uiso 1 1 calc R U . . .
H57B H 0.8193 -0.3318 0.2977 0.087 Uiso 1 1 calc R U . . .
H57C H 0.7445 -0.3695 0.3527 0.087 Uiso 1 1 calc R U . . .
C58 C 0.9228(3) -0.0972(3) 0.32154(11) 0.0564(8) Uani 1 1 d . . . . .
H58A H 0.9020 -0.0284 0.3202 0.085 Uiso 1 1 calc R U . . .
H58B H 0.9315 -0.1239 0.2833 0.085 Uiso 1 1 calc R U . . .
H58C H 1.0143 -0.0782 0.3473 0.085 Uiso 1 1 calc R U . . .
Cl1 Cl 0.48182(8) 1.01646(7) 0.08284(3) 0.0614(2) Uani 1 1 d . . . . .
Cl2 Cl 1.49594(8) 0.47118(7) 0.40221(4) 0.0729(3) Uani 1 1 d . . . . .
N1 N 0.8276(3) 0.9538(2) -0.06084(11) 0.0576(7) Uani 1 1 d . . . . .
N2 N 0.7701(2) 0.59489(17) 0.10538(8) 0.0310(5) Uani 1 1 d . . . . .
N3 N 0.6248(3) 0.4513(2) -0.03606(11) 0.0605(7) Uani 1 1 d . . . . .
N4 N 1.1442(3) 0.4839(2) 0.55176(10) 0.0555(6) Uani 1 1 d . . . . .
N5 N 0.7901(2) 0.03101(17) 0.39600(8) 0.0317(5) Uani 1 1 d . . . . .
N6 N 0.8424(3) -0.0145(2) 0.54179(11) 0.0601(7) Uani 1 1 d . . . . .
O1 O 0.9279(2) 0.83808(15) 0.16281(7) 0.0446(5) Uani 1 1 d . . . . .
O2 O 0.92512(17) 0.65671(13) 0.03252(6) 0.0317(4) Uani 1 1 d . . . . .
O3 O 0.4959(2) 0.30969(18) 0.06995(8) 0.0686(6) Uani 1 1 d . . . . .
O4 O 0.8516(2) 0.22593(16) 0.32769(7) 0.0491(5) Uani 1 1 d . . . . .
O5 O 0.71589(17) 0.14100(13) 0.46379(6) 0.0333(4) Uani 1 1 d . . . . .
O6 O 0.7892(2) -0.22830(15) 0.44294(7) 0.0523(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 O1 1.377(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.387(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 Cl1 1.744(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.502(3) . ?
C7 C17 1.522(3) . ?
C7 C8 1.536(3) . ?
C7 H7 0.9800 . ?
C8 N2 1.450(3) . ?
C8 O2 1.451(3) . ?
C8 C9 1.541(3) . ?
C9 O1 1.434(3) . ?
C9 C10 1.508(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.376(3) . ?
C10 C15 1.379(3) . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N1 1.148(3) . ?
C16 C17 1.423(4) . ?
C17 C18 1.335(3) . ?
C18 O2 1.388(3) . ?
C18 C19 1.499(3) . ?
C19 C21 1.510(4) . ?
C19 C22 1.518(4) . ?
C19 C20 1.519(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N3 1.141(3) . ?
C23 C24 1.468(4) . ?
C24 N2 1.265(3) . ?
C24 C25 1.530(3) . ?
C25 O3 1.213(3) . ?
C25 C26 1.508(3) . ?
C26 C28 1.526(4) . ?
C26 C27 1.527(4) . ?
C26 C29 1.538(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 O4 1.376(3) . ?
C30 C35 1.378(3) . ?
C30 C31 1.384(3) . ?
C31 C32 1.380(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.374(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.371(3) . ?
C33 Cl2 1.739(3) . ?
C34 C35 1.398(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.508(3) . ?
C36 C46 1.523(3) . ?
C36 C37 1.549(3) . ?
C36 H36 0.9800 . ?
C37 O5 1.443(3) . ?
C37 N5 1.450(3) . ?
C37 C38 1.538(3) . ?
C38 O4 1.439(3) . ?
C38 C39 1.509(3) . ?
C38 H38 0.9800 . ?
C39 C44 1.379(3) . ?
C39 C40 1.380(3) . ?
C40 C41 1.386(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.364(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.372(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.371(4) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 N4 1.148(3) . ?
C45 C46 1.421(4) . ?
C46 C47 1.336(3) . ?
C47 O5 1.388(3) . ?
C47 C48 1.502(3) . ?
C48 C50 1.530(4) . ?
C48 C51 1.530(4) . ?
C48 C49 1.532(4) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 N6 1.138(3) . ?
C52 C53 1.467(3) . ?
C53 N5 1.261(3) . ?
C53 C54 1.527(3) . ?
C54 O6 1.209(3) . ?
C54 C55 1.511(3) . ?
C55 C58 1.526(3) . ?
C55 C56 1.535(3) . ?
C55 C57 1.536(3) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 117.1(2) . . ?
O1 C1 C6 122.3(2) . . ?
C2 C1 C6 120.6(2) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 Cl1 120.3(2) . . ?
C3 C4 Cl1 118.8(2) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 C7 121.1(2) . . ?
C5 C6 C7 120.0(2) . . ?
C6 C7 C17 119.08(19) . . ?
C6 C7 C8 112.84(18) . . ?
C17 C7 C8 99.14(17) . . ?
C6 C7 H7 108.4 . . ?
C17 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
N2 C8 O2 111.24(17) . . ?
N2 C8 C7 112.32(19) . . ?
O2 C8 C7 105.15(17) . . ?
N2 C8 C9 110.67(18) . . ?
O2 C8 C9 106.93(18) . . ?
C7 C8 C9 110.27(18) . . ?
O1 C9 C10 107.98(18) . . ?
O1 C9 C8 109.78(19) . . ?
C10 C9 C8 114.50(19) . . ?
O1 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C11 C10 C15 119.0(2) . . ?
C11 C10 C9 120.1(2) . . ?
C15 C10 C9 120.9(2) . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.0(3) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N1 C16 C17 175.5(3) . . ?
C18 C17 C16 128.2(2) . . ?
C18 C17 C7 109.87(19) . . ?
C16 C17 C7 121.9(2) . . ?
C17 C18 O2 111.56(19) . . ?
C17 C18 C19 134.6(2) . . ?
O2 C18 C19 113.79(19) . . ?
C18 C19 C21 111.4(2) . . ?
C18 C19 C22 109.2(2) . . ?
C21 C19 C22 108.8(3) . . ?
C18 C19 C20 109.5(2) . . ?
C21 C19 C20 109.5(3) . . ?
C22 C19 C20 108.3(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 C24 174.6(3) . . ?
N2 C24 C23 125.1(2) . . ?
N2 C24 C25 123.5(2) . . ?
C23 C24 C25 111.2(2) . . ?
O3 C25 C26 122.5(2) . . ?
O3 C25 C24 114.3(2) . . ?
C26 C25 C24 123.1(2) . . ?
C25 C26 C28 108.8(2) . . ?
C25 C26 C27 109.0(2) . . ?
C28 C26 C27 109.2(2) . . ?
C25 C26 C29 109.6(2) . . ?
C28 C26 C29 110.9(3) . . ?
C27 C26 C29 109.3(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O4 C30 C35 122.7(2) . . ?
O4 C30 C31 116.3(2) . . ?
C35 C30 C31 120.9(3) . . ?
C32 C31 C30 119.8(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C33 C32 C31 119.7(3) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C34 C33 C32 120.9(3) . . ?
C34 C33 Cl2 119.7(2) . . ?
C32 C33 Cl2 119.4(2) . . ?
C33 C34 C35 120.0(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 118.8(2) . . ?
C30 C35 C36 120.9(2) . . ?
C34 C35 C36 120.0(2) . . ?
C35 C36 C46 120.13(19) . . ?
C35 C36 C37 112.53(19) . . ?
C46 C36 C37 99.48(18) . . ?
C35 C36 H36 108.0 . . ?
C46 C36 H36 108.0 . . ?
C37 C36 H36 108.0 . . ?
O5 C37 N5 112.09(18) . . ?
O5 C37 C38 107.25(18) . . ?
N5 C37 C38 110.93(18) . . ?
O5 C37 C36 105.16(17) . . ?
N5 C37 C36 111.43(19) . . ?
C38 C37 C36 109.73(19) . . ?
O4 C38 C39 107.22(19) . . ?
O4 C38 C37 108.89(18) . . ?
C39 C38 C37 115.4(2) . . ?
O4 C38 H38 108.4 . . ?
C39 C38 H38 108.4 . . ?
C37 C38 H38 108.4 . . ?
C44 C39 C40 118.3(2) . . ?
C44 C39 C38 121.5(2) . . ?
C40 C39 C38 120.2(2) . . ?
C39 C40 C41 120.4(3) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C42 C41 C40 120.3(3) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C41 C42 C43 119.8(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C42 120.0(3) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C43 C44 C39 121.2(3) . . ?
C43 C44 H44 119.4 . . ?
C39 C44 H44 119.4 . . ?
N4 C45 C46 176.0(3) . . ?
C47 C46 C45 128.3(2) . . ?
C47 C46 C36 109.8(2) . . ?
C45 C46 C36 121.8(2) . . ?
C46 C47 O5 111.8(2) . . ?
C46 C47 C48 135.4(2) . . ?
O5 C47 C48 112.8(2) . . ?
C47 C48 C50 109.2(2) . . ?
C47 C48 C51 108.8(2) . . ?
C50 C48 C51 109.9(2) . . ?
C47 C48 C49 110.9(2) . . ?
C50 C48 C49 109.5(2) . . ?
C51 C48 C49 108.5(2) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N6 C52 C53 173.8(3) . . ?
N5 C53 C52 125.3(2) . . ?
N5 C53 C54 123.1(2) . . ?
C52 C53 C54 111.4(2) . . ?
O6 C54 C55 123.0(2) . . ?
O6 C54 C53 115.1(2) . . ?
C55 C54 C53 121.9(2) . . ?
C54 C55 C58 111.0(2) . . ?
C54 C55 C56 108.1(2) . . ?
C58 C55 C56 111.7(2) . . ?
C54 C55 C57 108.3(2) . . ?
C58 C55 C57 108.7(2) . . ?
C56 C55 C57 109.0(2) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C55 C57 H57A 109.5 . . ?
C55 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C55 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C55 C58 H58A 109.5 . . ?
C55 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C55 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C24 N2 C8 122.0(2) . . ?
C53 N5 C37 121.86(19) . . ?
C1 O1 C9 116.57(17) . . ?
C18 O2 C8 107.42(16) . . ?
C30 O4 C38 115.76(18) . . ?
C47 O5 C37 107.95(17) . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045

