# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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. 
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data_cdz
_database_code_depnum_ccdc_archive 'CCDC 1514780'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_audit_creation_date             2015-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Br N3 O5, C H2 Cl2'
_chemical_formula_sum            'C23 H22 Br Cl2 N3 O5'
_chemical_formula_weight         571.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.593(4)
_cell_length_b                   15.307(7)
_cell_length_c                   16.705(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.785(8)
_cell_angle_gamma                90
_cell_volume                     2448(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3209
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      22.791
_cell_measurement_theta_min      2.382
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.937
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0837 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.7955.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14118
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        23.188
_diffrn_reflns_theta_max         23.188
_diffrn_reflns_theta_min         1.806
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2567
_reflns_number_total             3436
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0665P)²+1.3275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: H22C(0.65) H22D(0.65) H22A(0.35) H22B(0.35) Cl1A(0.35) Cl2A(0.35)
 Cl1B(0.65) Cl2B(0.65)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C22(H22C,H22D), C22(H22A,H22B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.97738(4) 0.23154(4) 0.54969(3) 0.0793(2) Uani 1 1 d . . . . .
O1 O 0.2653(3) 0.19056(19) 0.72595(16) 0.0598(7) Uani 1 1 d . . . . .
O2 O 0.2963(3) 0.00173(19) 0.44368(18) 0.0733(9) Uani 1 1 d . . . . .
O3 O 0.1948(3) 0.11554(17) 0.38160(16) 0.0665(8) Uani 1 1 d . . . . .
O4 O 0.4058(3) 0.36840(15) 0.65160(15) 0.0484(6) Uani 1 1 d . . . . .
O5 O 0.5090(3) 0.35743(18) 0.44760(15) 0.0603(7) Uani 1 1 d . . . . .
N1 N 0.4999(3) 0.19674(19) 0.76091(16) 0.0440(7) Uani 1 1 d . . . . .
N2 N 0.3685(3) 0.25618(17) 0.56867(16) 0.0354(7) Uani 1 1 d . . . . .
N3 N 0.3107(3) 0.22102(18) 0.49842(16) 0.0366(7) Uani 1 1 d . . . . .
C00V C 0.5959(4) 0.3668(3) 0.3822(3) 0.0702(13) Uani 1 1 d . . . . .
H00A H 0.5407 0.3560 0.3317 0.105 Uiso 1 1 calc GR . . . .
H00B H 0.6728 0.3246 0.3880 0.105 Uiso 1 1 calc GR . . . .
H00C H 0.6340 0.4262 0.3820 0.105 Uiso 1 1 calc GR . . . .
C1 C 0.8303(4) 0.2199(2) 0.6191(2) 0.0471(9) Uani 1 1 d . . . . .
C2 C 0.6940(4) 0.2129(2) 0.5864(2) 0.0425(9) Uani 1 1 d . . . . .
H2 H 0.6729 0.2139 0.5300 0.051 Uiso 1 1 calc R . . . .
C3 C 0.5920(3) 0.2043(2) 0.63860(19) 0.0349(8) Uani 1 1 d . . . . .
C4 C 0.6236(4) 0.2041(2) 0.7207(2) 0.0399(8) Uani 1 1 d . . . . .
C5 C 0.7583(4) 0.2117(2) 0.7523(2) 0.0502(10) Uani 1 1 d . . . . .
H5 H 0.7794 0.2119 0.8087 0.060 Uiso 1 1 calc R . . . .
C6 C 0.8623(4) 0.2190(3) 0.6998(2) 0.0543(10) Uani 1 1 d . . . . .
H6 H 0.9570 0.2234 0.7199 0.065 Uiso 1 1 calc R . . . .
C7 C 0.4367(3) 0.1914(2) 0.62334(19) 0.0360(8) Uani 1 1 d . . . . .
C8 C 0.3860(4) 0.1945(2) 0.7088(2) 0.0418(8) Uani 1 1 d . . . . .
C9 C 0.4957(5) 0.1950(3) 0.8474(2) 0.0642(12) Uani 1 1 d . . . . .
H9A H 0.5545 0.1473 0.8694 0.096 Uiso 1 1 calc GR . . . .
H9B H 0.3993 0.1860 0.8617 0.096 Uiso 1 1 calc GR . . . .
H9C H 0.5305 0.2507 0.8698 0.096 Uiso 1 1 calc GR . . . .
C10 C 0.3938(4) 0.1058(2) 0.5804(2) 0.0451(9) Uani 1 1 d . . . . .
H10A H 0.4762 0.0691 0.5711 0.054 Uiso 1 1 calc R . . . .
H10B H 0.3278 0.0718 0.6113 0.054 Uiso 1 1 calc R . . . .
C11 C 0.3251(3) 0.1384(2) 0.50323(19) 0.0364(8) Uani 1 1 d . . . . .
C12 C 0.2711(4) 0.0777(3) 0.4400(2) 0.0472(9) Uani 1 1 d . . . . .
C13 C 0.1327(6) 0.0591(3) 0.3194(3) 0.0889(17) Uani 1 1 d . . . . .
H13A H 0.2015 0.0144 0.3053 0.107 Uiso 1 1 calc R . . . .
H13B H 0.1077 0.0941 0.2707 0.107 Uiso 1 1 calc R . . . .
C14 C 0.0060(6) 0.0156(4) 0.3463(4) 0.112(2) Uani 1 1 d . . . . .
H14A H -0.0599 0.0598 0.3630 0.167 Uiso 1 1 calc GR . . . .
H14B H 0.0320 -0.0231 0.3915 0.167 Uiso 1 1 calc GR . . . .
H14C H -0.0380 -0.0188 0.3020 0.167 Uiso 1 1 calc GR . . . .
C15 C 0.3678(3) 0.3433(2) 0.5844(2) 0.0353(8) Uani 1 1 d . . . . .
C16 C 0.3220(3) 0.4036(2) 0.5183(2) 0.0382(8) Uani 1 1 d . . . . .
C17 C 0.3993(4) 0.4123(2) 0.4515(2) 0.0450(9) Uani 1 1 d . . . . .
C18 C 0.3639(5) 0.4773(3) 0.3960(2) 0.0603(11) Uani 1 1 d . . . . .
H18 H 0.4163 0.4842 0.3501 0.072 Uiso 1 1 calc R . . . .
C19 C 0.2536(5) 0.5316(3) 0.4073(3) 0.0689(13) Uani 1 1 d . . . . .
H19 H 0.2311 0.5766 0.3694 0.083 Uiso 1 1 calc R . . . .
C20 C 0.1760(5) 0.5222(3) 0.4714(3) 0.0669(12) Uani 1 1 d . . . . .
H20 H 0.0976 0.5589 0.4774 0.080 Uiso 1 1 calc R . . . .
C21 C 0.2111(4) 0.4592(2) 0.5277(2) 0.0516(10) Uani 1 1 d . . . . .
H21 H 0.1584 0.4538 0.5736 0.062 Uiso 1 1 calc R . . . .
C22 C 0.1484(6) 0.3880(4) 0.7710(4) 0.1007(18) Uani 1 1 d . . . . .
H22C H 0.2402 0.4097 0.7559 0.121 Uiso 0.65 1 calc R . P A 2
H22D H 0.1319 0.3303 0.7452 0.121 Uiso 0.65 1 calc R . P A 2
H22A H 0.2512 0.3903 0.7807 0.121 Uiso 0.35 1 calc R . P B 1
H22B H 0.1274 0.3430 0.7293 0.121 Uiso 0.35 1 calc R . P B 1
Cl1A Cl 0.0816(10) 0.3540(6) 0.8555(5) 0.120(3) Uani 0.35 1 d . . P C 1
Cl2A Cl 0.0950(9) 0.4843(5) 0.7336(4) 0.115(2) Uani 0.35 1 d . U P C 1
Cl1B Cl 0.1521(5) 0.3754(2) 0.8768(2) 0.1080(12) Uani 0.65 1 d . . P C 2
Cl2B Cl 0.0216(4) 0.4585(3) 0.7367(3) 0.1132(13) Uani 0.65 1 d . . P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.893(4) . ?
O1 C8 1.213(4) . ?
O2 C12 1.188(4) . ?
O3 C12 1.315(4) . ?
O3 C13 1.449(5) . ?
O4 C15 1.220(4) . ?
O5 C00V 1.425(4) . ?
O5 C17 1.351(4) . ?
N1 C4 1.406(4) . ?
N1 C8 1.352(5) . ?
N1 C9 1.449(5) . ?
N2 N3 1.374(4) . ?
N2 C7 1.471(4) . ?
N2 C15 1.360(4) . ?
N3 C11 1.274(4) . ?
C00V H00A 0.9800 . ?
C00V H00B 0.9800 . ?
C00V H00C 0.9800 . ?
C1 C2 1.387(5) . ?
C1 C6 1.362(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.360(5) . ?
C3 C4 1.386(5) . ?
C3 C7 1.508(5) . ?
C4 C5 1.368(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.539(5) . ?
C7 C10 1.538(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.495(5) . ?
C11 C12 1.475(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.482(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.482(5) . ?
C16 C17 1.386(5) . ?
C16 C21 1.379(5) . ?
C17 C18 1.388(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.368(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.352(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(6) . ?
C21 H21 0.9500 . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 Cl1A 1.671(11) . ?
C22 Cl2A 1.669(9) . ?
C22 Cl1B 1.776(7) . ?
C22 Cl2B 1.697(7) . ?

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
C12 O3 C13 116.9(3) . . ?
C17 O5 C00V 118.2(3) . . ?
C4 N1 C9 123.9(3) . . ?
C8 N1 C4 111.5(3) . . ?
C8 N1 C9 124.6(3) . . ?
N3 N2 C7 113.8(2) . . ?
C15 N2 N3 122.8(3) . . ?
C15 N2 C7 123.3(3) . . ?
C11 N3 N2 107.4(3) . . ?
O5 C00V H00A 109.5 . . ?
O5 C00V H00B 109.5 . . ?
O5 C00V H00C 109.5 . . ?
H00A C00V H00B 109.5 . . ?
H00A C00V H00C 109.5 . . ?
H00B C00V H00C 109.5 . . ?
C2 C1 Br1 119.2(3) . . ?
C6 C1 Br1 118.6(3) . . ?
C6 C1 C2 122.3(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 C7 130.5(3) . . ?
C4 C3 C7 108.5(3) . . ?
C3 C4 N1 109.7(3) . . ?
C5 C4 N1 128.9(3) . . ?
C5 C4 C3 121.4(3) . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.9(3) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N2 C7 C3 114.2(3) . . ?
N2 C7 C8 113.6(3) . . ?
N2 C7 C10 101.0(3) . . ?
C3 C7 C8 102.0(3) . . ?
C3 C7 C10 114.9(3) . . ?
C10 C7 C8 111.6(3) . . ?
O1 C8 N1 126.4(3) . . ?
O1 C8 C7 125.6(3) . . ?
N1 C8 C7 107.9(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 111.4 . . ?
C7 C10 H10B 111.4 . . ?
H10A C10 H10B 109.3 . . ?
C11 C10 C7 101.9(3) . . ?
C11 C10 H10A 111.4 . . ?
C11 C10 H10B 111.4 . . ?
N3 C11 C10 115.2(3) . . ?
N3 C11 C12 123.3(3) . . ?
C12 C11 C10 121.4(3) . . ?
O2 C12 O3 124.8(3) . . ?
O2 C12 C11 121.3(3) . . ?
O3 C12 C11 113.9(3) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 C14 110.9(4) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 N2 118.8(3) . . ?
O4 C15 C16 123.1(3) . . ?
N2 C15 C16 118.2(3) . . ?
C17 C16 C15 120.7(3) . . ?
C21 C16 C15 119.5(3) . . ?
C21 C16 C17 119.4(3) . . ?
O5 C17 C16 116.1(3) . . ?
O5 C17 C18 124.8(3) . . ?
C16 C17 C18 119.1(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.1(4) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.6(4) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(4) . . ?
C20 C21 H21 119.6 . . ?
H22C C22 H22D 107.9 . . ?
H22A C22 H22B 107.2 . . ?
Cl1A C22 H22A 107.9 . . ?
Cl1A C22 H22B 107.9 . . ?
Cl2A C22 H22A 107.9 . . ?
Cl2A C22 H22B 107.9 . . ?
Cl2A C22 Cl1A 117.8(5) . . ?
Cl1B C22 H22C 109.3 . . ?
Cl1B C22 H22D 109.3 . . ?
Cl2B C22 H22C 109.3 . . ?
Cl2B C22 H22D 109.3 . . ?
Cl2B C22 Cl1B 111.8(4) . . ?

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
Br1 C1 C2 C3 179.8(3) . . . . ?
Br1 C1 C6 C5 179.2(3) . . . . ?
O4 C15 C16 C17 113.6(4) . . . . ?
O4 C15 C16 C21 -58.6(5) . . . . ?
O5 C17 C18 C19 -177.5(4) . . . . ?
N1 C4 C5 C6 -179.3(4) . . . . ?
N2 N3 C11 C10 1.3(4) . . . . ?
N2 N3 C11 C12 177.7(3) . . . . ?
N2 C7 C8 O1 53.3(5) . . . . ?
N2 C7 C8 N1 -130.6(3) . . . . ?
N2 C7 C10 C11 7.4(3) . . . . ?
N2 C15 C16 C17 -65.7(4) . . . . ?
N2 C15 C16 C21 122.2(3) . . . . ?
N3 N2 C7 C3 116.2(3) . . . . ?
N3 N2 C7 C8 -127.3(3) . . . . ?
N3 N2 C7 C10 -7.7(3) . . . . ?
N3 N2 C15 O4 171.3(3) . . . . ?
N3 N2 C15 C16 -9.4(4) . . . . ?
N3 C11 C12 O2 173.9(4) . . . . ?
N3 C11 C12 O3 -6.3(5) . . . . ?
C00V O5 C17 C16 -176.8(3) . . . . ?
C00V O5 C17 C18 0.4(5) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C2 C3 C7 -177.0(3) . . . . ?
C2 C1 C6 C5 -0.6(6) . . . . ?
C2 C3 C4 N1 178.5(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C2 C3 C7 N2 -52.7(5) . . . . ?
C2 C3 C7 C8 -175.7(3) . . . . ?
C2 C3 C7 C10 63.4(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C3 C7 C8 O1 176.8(3) . . . . ?
C3 C7 C8 N1 -7.1(3) . . . . ?
C3 C7 C10 C11 -116.0(3) . . . . ?
C4 N1 C8 O1 -178.1(4) . . . . ?
C4 N1 C8 C7 5.8(4) . . . . ?
C4 C3 C7 N2 129.1(3) . . . . ?
C4 C3 C7 C8 6.1(3) . . . . ?
C4 C3 C7 C10 -114.8(3) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
C7 N2 N3 C11 4.4(4) . . . . ?
C7 N2 C15 O4 -11.7(4) . . . . ?
C7 N2 C15 C16 167.6(3) . . . . ?
C7 C3 C4 N1 -3.1(4) . . . . ?
C7 C3 C4 C5 177.8(3) . . . . ?
C7 C10 C11 N3 -6.0(4) . . . . ?
C7 C10 C11 C12 177.6(3) . . . . ?
C8 N1 C4 C3 -1.8(4) . . . . ?
C8 N1 C4 C5 177.2(4) . . . . ?
C8 C7 C10 C11 128.5(3) . . . . ?
C9 N1 C4 C3 -179.7(3) . . . . ?
C9 N1 C4 C5 -0.6(6) . . . . ?
C9 N1 C8 O1 -0.3(6) . . . . ?
C9 N1 C8 C7 -176.4(3) . . . . ?
C10 C7 C8 O1 -60.1(5) . . . . ?
C10 C7 C8 N1 116.0(3) . . . . ?
C10 C11 C12 O2 -10.0(5) . . . . ?
C10 C11 C12 O3 169.9(3) . . . . ?
C12 O3 C13 C14 79.1(6) . . . . ?
C13 O3 C12 O2 2.8(6) . . . . ?
C13 O3 C12 C11 -177.1(4) . . . . ?
C15 N2 N3 C11 -178.3(3) . . . . ?
C15 N2 C7 C3 -61.1(4) . . . . ?
C15 N2 C7 C8 55.4(4) . . . . ?
C15 N2 C7 C10 175.0(3) . . . . ?
C15 C16 C17 O5 5.8(5) . . . . ?
C15 C16 C17 C18 -171.6(3) . . . . ?
C15 C16 C21 C20 172.9(4) . . . . ?
C16 C17 C18 C19 -0.3(6) . . . . ?
C17 C16 C21 C20 0.6(5) . . . . ?
C17 C18 C19 C20 -1.1(6) . . . . ?
C18 C19 C20 C21 2.3(7) . . . . ?
C19 C20 C21 C16 -2.0(6) . . . . ?
C21 C16 C17 O5 178.0(3) . . . . ?
C21 C16 C17 C18 0.6(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_170110a_0m
_database_code_depnum_ccdc_archive 'CCDC 1526815'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT341_mo_170110a_0m       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01806 Ang.  
RESPONSE: The data were collected at room temperature, which caused the
relatively low bond precision. 
;
# end Validation Reply Form

_audit_creation_date             2017-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H16 Br N3 O3, C H Cl3'
_chemical_formula_sum            'C20 H17 Br Cl3 N3 O3'
_chemical_formula_weight         533.62
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.299(8)
_cell_length_b                   11.774(15)
_cell_length_c                   14.904(19)
_cell_angle_alpha                99.608(16)
_cell_angle_beta                 94.163(15)
_cell_angle_gamma                96.363(16)
_cell_volume                     1078(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    935
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.35
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.802
_exptl_absorpt_coefficient_mu    2.305
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_correction_T_min  0.8022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_unetI/netI     0.1679
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7173
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.392
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1905
_reflns_number_total             3798
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.199
_refine_ls_extinction_coef       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2000
_refine_ls_R_factor_gt           0.1125
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1400P)²+9.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2823
_refine_ls_wR_factor_ref         0.3492
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
3.a Ternary CH refined with riding coordinates:
 C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17), N3(H3A)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.2111(2) 0.53036(15) 0.15335(11) 0.0630(7) Uani 1 1 d . . . . .
C1 C 0.0960(17) 0.6908(11) 0.2658(8) 0.034(3) Uani 1 1 d . . . . .
H1 H 0.0101 0.6785 0.3124 0.040 Uiso 1 1 calc R . . . .
C2 C 0.0431(18) 0.6358(10) 0.1818(9) 0.035(3) Uani 1 1 d . . . . .
C3 C 0.170(2) 0.6503(12) 0.1119(9) 0.045(3) Uani 1 1 d . . . . .
H3 H 0.1296 0.6074 0.0537 0.054 Uiso 1 1 calc R . . . .
C4 C 0.354(2) 0.7272(12) 0.1273(8) 0.044(3) Uani 1 1 d . . . . .
H4 H 0.4403 0.7398 0.0810 0.053 Uiso 1 1 calc R . . . .
C5 C 0.4006(18) 0.7829(11) 0.2135(7) 0.035(3) Uani 1 1 d . . . . .
C6 C 0.2816(18) 0.7671(11) 0.2833(8) 0.038(3) Uani 1 1 d . . . . .
C7 C 0.3776(16) 0.8467(10) 0.3696(7) 0.028(3) Uani 1 1 d . . . . .
C8 C 0.5882(18) 0.8966(10) 0.3391(8) 0.033(3) Uani 1 1 d . . . . .
C9 C 0.2466(17) 0.9457(11) 0.3983(9) 0.040(3) Uani 1 1 d . . . . .
H9A H 0.1023 0.9135 0.4066 0.048 Uiso 1 1 calc R . . . .
H9B H 0.3101 0.9903 0.4566 0.048 Uiso 1 1 calc R . . . .
C10 C 0.2357(18) 1.0229(13) 0.3314(10) 0.042(3) Uani 1 1 d . . . . .
C11 C 0.744(2) 0.8996(13) 0.1908(10) 0.050(4) Uani 1 1 d . . . . .
H11A H 0.8075 0.8335 0.1630 0.076 Uiso 1 1 calc GR . . . .
H11B H 0.8530 0.9545 0.2280 0.076 Uiso 1 1 calc GR . . . .
H11C H 0.6798 0.9353 0.1440 0.076 Uiso 1 1 calc GR . . . .
C12 C 0.570(2) 0.7219(12) 0.4516(8) 0.042(3) Uani 1 1 d . . . . .
C13 C 0.5900(19) 0.6711(11) 0.5308(8) 0.038(3) Uani 1 1 d . . . . .
C14 C 0.757(2) 0.5979(14) 0.5290(11) 0.061(4) Uani 1 1 d . . . . .
H14 H 0.8404 0.5886 0.4799 0.073 Uiso 1 1 calc R . . . .
C15 C 0.791(3) 0.5433(17) 0.5996(11) 0.074(5) Uani 1 1 d . U . . .
H15 H 0.9061 0.5005 0.6006 0.089 Uiso 1 1 calc R . . . .
C16 C 0.664(2) 0.5474(14) 0.6699(10) 0.055(4) Uani 1 1 d . . . . .
H16 H 0.6844 0.5032 0.7154 0.066 Uiso 1 1 calc R . . . .
C17 C 0.514(3) 0.6149(13) 0.6717(10) 0.057(4) Uani 1 1 d . . . . .
H17 H 0.4305 0.6211 0.7209 0.068 Uiso 1 1 calc R . . . .
C18 C 0.4724(19) 0.6782(11) 0.6030(8) 0.037(3) Uani 1 1 d . . . . .
C19 C 0.211(3) 0.7739(16) 0.6838(10) 0.071(5) Uani 1 1 d . . . . .
H19A H 0.1280 0.7056 0.6960 0.106 Uiso 1 1 calc GR . . . .
H19B H 0.1181 0.8314 0.6757 0.106 Uiso 1 1 calc GR . . . .
H19C H 0.3167 0.8040 0.7343 0.106 Uiso 1 1 calc GR . . . .
C20 C 0.231(2) 0.2109(14) 0.1124(12) 0.066(4) Uani 1 1 d . . . . .
H20 H 0.2463 0.2211 0.1793 0.079 Uiso 1 1 calc R . . . .
Cl1 Cl 0.3923(12) 0.1129(7) 0.0695(4) 0.132(3) Uani 1 1 d . . . . .
Cl2 Cl -0.0322(10) 0.1634(8) 0.0729(6) 0.154(3) Uani 1 1 d . . . . .
Cl3 Cl 0.2979(10) 0.3428(5) 0.0798(4) 0.108(2) Uani 1 1 d . . . . .
N1 N 0.5815(15) 0.8625(10) 0.2472(7) 0.042(3) Uani 1 1 d . . . . .
N2 N 0.2333(19) 1.0762(11) 0.2817(9) 0.057(3) Uani 1 1 d . . . . .
N3 N 0.4139(14) 0.7937(10) 0.4462(6) 0.040(3) Uani 1 1 d . . . . .
H3A H 0.3359 0.8065 0.4910 0.048 Uiso 1 1 calc R . . . .
O1 O 0.7234(12) 0.9674(8) 0.3845(6) 0.046(2) Uani 1 1 d . . . . .
O2 O 0.6806(15) 0.7084(10) 0.3893(6) 0.059(3) Uani 1 1 d . . . . .
O3 O 0.3141(14) 0.7452(10) 0.6037(6) 0.057(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 C2 1.890(11) . ?
C1 H1 0.9300 . ?
C1 C2 1.311(16) . ?
C1 C6 1.373(16) . ?
C2 C3 1.378(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.337(16) . ?
C5 C6 1.352(17) . ?
C5 N1 1.398(15) . ?
C6 C7 1.503(16) . ?
C7 C8 1.522(16) . ?
C7 C9 1.523(17) . ?
C7 N3 1.406(14) . ?
C8 N1 1.357(15) . ?
C8 O1 1.203(13) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.46(2) . ?
C10 N2 1.048(16) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 N1 1.448(17) . ?
C12 C13 1.414(17) . ?
C12 N3 1.375(15) . ?
C12 O2 1.198(15) . ?
C13 C14 1.431(18) . ?
C13 C18 1.346(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.34(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.36(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.30(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(18) . ?
C18 O3 1.338(15) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 O3 1.410(17) . ?
C20 H20 0.9800 . ?
C20 Cl1 1.696(17) . ?
C20 Cl2 1.720(16) . ?
C20 Cl3 1.720(18) . ?
N3 H3A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.9 . . ?
C2 C1 C6 118.2(11) . . ?
C6 C1 H1 120.9 . . ?
C1 C2 Br1 120.2(9) . . ?
C1 C2 C3 122.2(11) . . ?
C3 C2 Br1 117.6(9) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.7(12) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 122.3 . . ?
C5 C4 C3 115.3(13) . . ?
C5 C4 H4 122.3 . . ?
C4 C5 C6 124.7(12) . . ?
C4 C5 N1 126.4(11) . . ?
C6 C5 N1 108.8(10) . . ?
C1 C6 C7 130.8(11) . . ?
C5 C6 C1 118.8(11) . . ?
C5 C6 C7 110.3(10) . . ?
C6 C7 C8 100.9(9) . . ?
C6 C7 C9 113.0(9) . . ?
C8 C7 C9 108.7(9) . . ?
N3 C7 C6 115.9(10) . . ?
N3 C7 C8 111.0(9) . . ?
N3 C7 C9 107.1(10) . . ?
N1 C8 C7 107.7(10) . . ?
O1 C8 C7 126.6(11) . . ?
O1 C8 N1 124.8(12) . . ?
C7 C9 H9A 109.1 . . ?
C7 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C7 112.6(11) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
N2 C10 C9 177.2(17) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
N3 C12 C13 117.2(12) . . ?
O2 C12 C13 125.4(12) . . ?
O2 C12 N3 117.5(12) . . ?
C12 C13 C14 112.4(12) . . ?
C18 C13 C12 130.0(12) . . ?
C18 C13 C14 117.5(12) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.4(15) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 118.4 . . ?
C14 C15 C16 123.2(15) . . ?
C16 C15 H15 118.4 . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.0(14) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 H17 118.7 . . ?
C16 C17 C18 122.6(14) . . ?
C18 C17 H17 118.7 . . ?
C13 C18 C17 120.1(12) . . ?
O3 C18 C13 117.3(11) . . ?
O3 C18 C17 122.6(12) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
Cl1 C20 H20 109.2 . . ?
Cl1 C20 Cl2 110.4(10) . . ?
Cl1 C20 Cl3 111.1(11) . . ?
Cl2 C20 H20 109.2 . . ?
Cl2 C20 Cl3 107.7(9) . . ?
Cl3 C20 H20 109.2 . . ?
C5 N1 C11 123.6(10) . . ?
C8 N1 C5 111.5(10) . . ?
C8 N1 C11 124.9(11) . . ?
C7 N3 H3A 119.1 . . ?
C12 N3 C7 121.9(10) . . ?
C12 N3 H3A 119.1 . . ?
C18 O3 C19 120.2(11) . . ?

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
Br1 C2 C3 C4 178.6(10) . . . . ?
C1 C2 C3 C4 -3(2) . . . . ?
C1 C6 C7 C8 176.0(13) . . . . ?
C1 C6 C7 C9 -68.1(17) . . . . ?
C1 C6 C7 N3 56.1(17) . . . . ?
C2 C1 C6 C5 0.5(19) . . . . ?
C2 C1 C6 C7 176.2(12) . . . . ?
C2 C3 C4 C5 1.5(19) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C3 C4 C5 N1 178.0(12) . . . . ?
C4 C5 C6 C1 -2(2) . . . . ?
C4 C5 C6 C7 -178.1(12) . . . . ?
C4 C5 N1 C8 -175.5(12) . . . . ?
C4 C5 N1 C11 2(2) . . . . ?
C5 C6 C7 C8 -8.0(13) . . . . ?
C5 C6 C7 C9 107.9(12) . . . . ?
C5 C6 C7 N3 -128.0(11) . . . . ?
C6 C1 C2 Br1 -179.7(9) . . . . ?
C6 C1 C2 C3 1.5(19) . . . . ?
C6 C5 N1 C8 2.3(15) . . . . ?
C6 C5 N1 C11 180.0(12) . . . . ?
C6 C7 C8 N1 9.1(12) . . . . ?
C6 C7 C8 O1 178.9(12) . . . . ?
C6 C7 C9 C10 -63.1(13) . . . . ?
C6 C7 N3 C12 69.9(14) . . . . ?
C7 C8 N1 C5 -7.5(13) . . . . ?
C7 C8 N1 C11 174.8(11) . . . . ?
C8 C7 C9 C10 48.0(12) . . . . ?
C8 C7 N3 C12 -44.4(15) . . . . ?
C9 C7 C8 N1 -109.9(11) . . . . ?
C9 C7 C8 O1 59.9(15) . . . . ?
C9 C7 N3 C12 -163.0(10) . . . . ?
C12 C13 C14 C15 -179.2(15) . . . . ?
C12 C13 C18 C17 176.3(14) . . . . ?
C12 C13 C18 O3 -2(2) . . . . ?
C13 C12 N3 C7 -178.6(11) . . . . ?
C13 C14 C15 C16 5(3) . . . . ?
C13 C18 O3 C19 -168.3(13) . . . . ?
C14 C13 C18 C17 -0.7(19) . . . . ?
C14 C13 C18 O3 -179.0(12) . . . . ?
C14 C15 C16 C17 -5(3) . . . . ?
C15 C16 C17 C18 3(2) . . . . ?
C16 C17 C18 C13 0(2) . . . . ?
C16 C17 C18 O3 178.2(14) . . . . ?
C17 C18 O3 C19 13(2) . . . . ?
C18 C13 C14 C15 -2(2) . . . . ?
N1 C5 C6 C1 -179.4(11) . . . . ?
N1 C5 C6 C7 4.1(14) . . . . ?
N3 C7 C8 N1 132.5(10) . . . . ?
N3 C7 C8 O1 -57.7(16) . . . . ?
N3 C7 C9 C10 168.0(9) . . . . ?
N3 C12 C13 C14 179.8(12) . . . . ?
N3 C12 C13 C18 3(2) . . . . ?
O1 C8 N1 C5 -177.5(11) . . . . ?
O1 C8 N1 C11 5(2) . . . . ?
O2 C12 C13 C14 -1(2) . . . . ?
O2 C12 C13 C18 -178.2(14) . . . . ?
O2 C12 N3 C7 2.1(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
