# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_bb818a
_database_code_depnum_ccdc_archive 'CCDC 1864170'
_audit_update_record             
;
2018-08-27 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2018-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H23 Cl N2 O3'
_chemical_formula_sum            'C16 H23 Cl N2 O3'
_chemical_formula_weight         326.81
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.6148(2)
_cell_length_b                   5.07730(10)
_cell_length_c                   15.8871(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.929(2)
_cell_angle_gamma                90
_cell_volume                     827.33(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3483
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.34
_cell_measurement_theta_min      5.76
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.487
_exptl_absorpt_coefficient_mu    2.164
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0840 before and 0.0696 after correction. The Ratio of minimum to maximum transmission is 0.8337. 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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of methanol and hexanes  by slow evaporation'
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.021
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9843
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.393
_diffrn_reflns_theta_min         4.310
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                2684
_reflns_number_total             3116
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1011 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.010
_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)+(0.0333P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0850
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the Hydrogen atom on the nitrogen atom which was found 
by difference Fourier methods and refined isotropically.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C9(H9), C10(H10), C12(H12)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.10456(9) 0.74221(18) 0.18474(5) 0.0375(2) Uani 1 1 d . . . . .
O1 O 0.4349(3) 0.0007(5) 0.22668(17) 0.0342(6) Uani 1 1 d . . . . .
O2 O 0.8549(3) 0.4266(6) 0.04185(17) 0.0399(6) Uani 1 1 d . . . . .
O3 O 0.2851(3) 1.0018(5) 0.46142(17) 0.0331(6) Uani 1 1 d . . . . .
N1 N 0.3793(3) 0.4290(6) 0.22240(19) 0.0275(6) Uani 1 1 d . . . . .
H1 H 0.401(4) 0.580(9) 0.216(2) 0.029(10) Uiso 1 1 d . . . . .
N2 N 0.2346(3) 0.5717(5) 0.43951(19) 0.0257(6) Uani 1 1 d . . . . .
H2 H 0.246(3) 0.426(8) 0.457(2) 0.016(9) Uiso 1 1 d . . . . .
C00I C 0.6665(4) 0.1367(7) 0.1767(2) 0.0300(7) Uani 1 1 d . . . . .
H00I H 0.673915 -0.009080 0.215170 0.036 Uiso 1 1 calc R . . . .
C1 C 0.2801(3) 0.3786(6) 0.2683(2) 0.0278(7) Uani 1 1 d . . . . .
H1A H 0.320366 0.291263 0.324462 0.033 Uiso 1 1 calc R . . . .
H1B H 0.213601 0.258162 0.233246 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2151(3) 0.6325(6) 0.2850(2) 0.0266(7) Uani 1 1 d . . . . .
H2A H 0.284325 0.769391 0.303948 0.032 Uiso 1 1 calc R . . . .
C3 C 0.1401(3) 0.6106(6) 0.3552(2) 0.0244(7) Uani 1 1 d . . . . .
H3 H 0.094975 0.782411 0.357440 0.029 Uiso 1 1 calc R . . . .
C4 C 0.0371(3) 0.3933(6) 0.3395(2) 0.0289(7) Uani 1 1 d . . . . .
H4A H -0.007268 0.385963 0.276547 0.035 Uiso 1 1 calc R . . . .
H4B H 0.080679 0.221750 0.356210 0.035 Uiso 1 1 calc R . . . .
C5 C -0.0648(4) 0.4354(7) 0.3908(2) 0.0332(8) Uani 1 1 d . . . . .
H5A H -0.112854 0.268756 0.391633 0.040 Uiso 1 1 calc R . . . .
H5B H -0.019888 0.480795 0.451727 0.040 Uiso 1 1 calc R . . . .
C6 C -0.1610(4) 0.6503(8) 0.3532(3) 0.0442(10) Uani 1 1 d . . . . .
H6A H -0.212114 0.598476 0.294972 0.066 Uiso 1 1 calc GR . . . .
H6B H -0.113747 0.813733 0.349073 0.066 Uiso 1 1 calc GR . . . .
H6C H -0.219473 0.678428 0.391026 0.066 Uiso 1 1 calc GR . . . .
C7 C 0.4529(3) 0.2299(7) 0.20554(19) 0.0260(6) Uani 1 1 d . . . . .
C8 C 0.5559(3) 0.2953(6) 0.1611(2) 0.0258(7) Uani 1 1 d . . . . .
C9 C 0.5463(4) 0.5050(7) 0.1033(2) 0.0283(7) Uani 1 1 d . . . . .
H9 H 0.471935 0.616451 0.092287 0.034 Uiso 1 1 calc R . . . .
C10 C 0.6436(4) 0.5533(7) 0.0615(2) 0.0306(8) Uani 1 1 d . . . . .
H10 H 0.634915 0.694976 0.021374 0.037 Uiso 1 1 calc R . . . .
C11 C 0.7540(3) 0.3945(8) 0.0784(2) 0.0304(8) Uani 1 1 d . . . . .
C12 C 0.7652(3) 0.1873(7) 0.1374(2) 0.0324(8) Uani 1 1 d . . . . .
H12 H 0.841348 0.080679 0.150548 0.039 Uiso 1 1 calc R . . . .
C13 C 0.8511(4) 0.6456(8) -0.0151(3) 0.0430(10) Uani 1 1 d . . . . .
H13A H 0.779733 0.621723 -0.067710 0.065 Uiso 1 1 calc GR . . . .
H13B H 0.934020 0.657323 -0.031350 0.065 Uiso 1 1 calc GR . . . .
H13C H 0.837071 0.808006 0.014495 0.065 Uiso 1 1 calc GR . . . .
C14 C 0.3018(3) 0.7705(7) 0.4856(2) 0.0257(7) Uani 1 1 d . . . . .
C15 C 0.4004(4) 0.6946(8) 0.5685(2) 0.0372(9) Uani 1 1 d . . . . .
H15A H 0.488528 0.713187 0.560489 0.056 Uiso 1 1 calc GR . . . .
H15B H 0.386076 0.511273 0.582955 0.056 Uiso 1 1 calc GR . . . .
H15C H 0.390886 0.809830 0.615927 0.056 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.806(3) . ?
O1 C7 1.240(4) . ?
O2 C11 1.353(5) . ?
O2 C13 1.428(5) . ?
O3 C14 1.234(4) . ?
N1 H1 0.81(4) . ?
N1 C1 1.449(4) . ?
N1 C7 1.346(4) . ?
N2 H2 0.79(4) . ?
N2 C3 1.466(4) . ?
N2 C14 1.340(4) . ?
C00I H00I 0.9500 . ?
C00I C8 1.392(5) . ?
C00I C12 1.375(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.518(4) . ?
C2 H2A 1.0000 . ?
C2 C3 1.532(5) . ?
C3 H3 1.0000 . ?
C3 C4 1.528(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.528(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.508(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.484(5) . ?
C8 C9 1.393(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(5) . ?
C11 C12 1.394(5) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.506(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C13 118.0(3) . . ?
C1 N1 H1 120(3) . . ?
C7 N1 H1 119(3) . . ?
C7 N1 C1 120.1(3) . . ?
C3 N2 H2 117(3) . . ?
C14 N2 H2 120(3) . . ?
C14 N2 C3 122.7(3) . . ?
C8 C00I H00I 119.4 . . ?
C12 C00I H00I 119.4 . . ?
C12 C00I C8 121.2(3) . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
N1 C1 C2 111.1(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
Cl1 C2 H2A 108.1 . . ?
C1 C2 Cl1 109.2(2) . . ?
C1 C2 H2A 108.1 . . ?
C1 C2 C3 114.3(3) . . ?
C3 C2 Cl1 108.8(2) . . ?
C3 C2 H2A 108.1 . . ?
N2 C3 C2 108.2(3) . . ?
N2 C3 H3 107.8 . . ?
N2 C3 C4 110.2(3) . . ?
C2 C3 H3 107.8 . . ?
C4 C3 C2 114.7(3) . . ?
C4 C3 H3 107.8 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.8(3) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.9(3) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 N1 120.9(3) . . ?
O1 C7 C8 121.5(3) . . ?
N1 C7 C8 117.6(3) . . ?
C00I C8 C7 118.5(3) . . ?
C00I C8 C9 118.3(3) . . ?
C9 C8 C7 123.1(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
O2 C11 C10 124.7(3) . . ?
O2 C11 C12 116.1(3) . . ?
C10 C11 C12 119.3(3) . . ?
C00I C12 C11 120.2(3) . . ?
C00I C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 N2 122.2(3) . . ?
O3 C14 C15 121.8(3) . . ?
N2 C14 C15 115.9(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.81(4) 2.17(4) 2.959(4) 165(4) 1_565 yes
N2 H2 O3 0.79(4) 2.19(4) 2.947(4) 161(3) 1_545 yes

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'From NMR tube'
_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_bb319t
_database_code_depnum_ccdc_archive 'CCDC 1909607'
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 Br Cl N2 O2'
_chemical_formula_sum            'C15 H20 Br Cl N2 O2'
_chemical_formula_weight         375.69
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   4.9505(2)
_cell_length_b                   8.5820(3)
_cell_length_c                   19.9420(6)
_cell_angle_alpha                88.027(2)
_cell_angle_beta                 85.435(2)
_cell_angle_gamma                89.121(2)
_cell_volume                     843.98(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6368
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.60
_cell_measurement_theta_min      4.45
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.370
_exptl_absorpt_coefficient_mu    4.824
_exptl_absorpt_correction_T_max  0.1048
_exptl_absorpt_correction_T_min  0.0183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1005 before and 0.0740 after correction. The Ratio of minimum to maximum transmission is 0.1746. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19825
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.126
_diffrn_reflns_theta_min         2.224
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.976
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                5104
_reflns_number_total             6030
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 2087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6030
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.050
_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)+(0.0593P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the hydrogen atom on the non-carbon atom(s) which was found by difference Fourier methods and refined isotropically.'
_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.a Ternary CH refined with riding coordinates:
 C2A(H2AA), C3A(H3A), C2B(H2BA), C3B(H3B)
2.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C1B(H1BA,H1BB), C4B(H4BA,
 H4BB), C5B(H5BA,H5BB)
2.c Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N2A(H2A), C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A), N1B(H1B),
 N2B(H2B), C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B)
2.d Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C8A(H8AA,H8AB,H8AC), C6B(H6BA,H6BB,H6BC), C8B(H8BA,H8BB,
 H8BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1A Br 0.35939(16) 0.09911(9) 0.29425(5) 0.0762(3) Uani 1 1 d . . . . .
Cl1A Cl 0.2171(4) -0.0613(2) 0.73819(11) 0.0674(5) Uani 1 1 d . . . . .
O1A O 0.6360(10) 0.1729(7) 0.6213(3) 0.0631(13) Uani 1 1 d . . . . .
O2A O 0.3446(11) 0.3957(7) 0.8485(3) 0.0671(15) Uani 1 1 d . . . . .
N1A N 0.1857(12) 0.2181(8) 0.6361(3) 0.0576(15) Uani 1 1 d . . . . .
H1A H 0.032837 0.224635 0.616353 0.069 Uiso 1 1 calc R . . . .
N2A N -0.0796(12) 0.3111(7) 0.8389(3) 0.0550(14) Uani 1 1 d . . . . .
H2A H -0.252043 0.337533 0.839039 0.066 Uiso 1 1 calc R . . . .
C1A C 0.1800(16) 0.2456(10) 0.7072(5) 0.0595(19) Uani 1 1 d . . . . .
H1AA H 0.092297 0.348047 0.716080 0.071 Uiso 1 1 calc R . . . .
H1AB H 0.368403 0.250197 0.720226 0.071 Uiso 1 1 calc R . . . .
C2A C 0.0303(15) 0.1215(10) 0.7502(4) 0.0531(18) Uani 1 1 d . . . . .
H2AA H -0.154633 0.110421 0.734205 0.064 Uiso 1 1 calc R . . . .
C3A C 0.0022(16) 0.1499(10) 0.8259(4) 0.0562(17) Uani 1 1 d . . . . .
H3A H 0.184039 0.131708 0.843534 0.067 Uiso 1 1 calc R . . . .
C4A C -0.1945(17) 0.0366(10) 0.8630(4) 0.0631(19) Uani 1 1 d . . . . .
H4AA H -0.373859 0.051226 0.844868 0.076 Uiso 1 1 calc R . . . .
H4AB H -0.131447 -0.070936 0.853435 0.076 Uiso 1 1 calc R . . . .
C5A C -0.229(2) 0.0528(14) 0.9383(5) 0.082(3) Uani 1 1 d . . . . .
H5AA H -0.305168 0.157512 0.948192 0.098 Uiso 1 1 calc R . . . .
H5AB H -0.048417 0.045154 0.956345 0.098 Uiso 1 1 calc R . . . .
C6A C -0.411(3) -0.0690(15) 0.9740(6) 0.096(3) Uani 1 1 d . . . . .
H6AA H -0.585528 -0.068304 0.953919 0.144 Uiso 1 1 calc GR . . . .
H6AB H -0.440975 -0.045403 1.021818 0.144 Uiso 1 1 calc GR . . . .
H6AC H -0.325278 -0.172149 0.969563 0.144 Uiso 1 1 calc GR . . . .
C7A C 0.1027(16) 0.4207(10) 0.8506(4) 0.0575(17) Uani 1 1 d . . . . .
C8A C -0.016(2) 0.5792(11) 0.8669(5) 0.069(2) Uani 1 1 d . . . . .
H8AA H 0.042745 0.611058 0.910102 0.103 Uiso 1 1 calc GR . . . .
H8AB H -0.214710 0.574204 0.869862 0.103 Uiso 1 1 calc GR . . . .
H8AC H 0.045224 0.655297 0.831441 0.103 Uiso 1 1 calc GR . . . .
C9A C 0.4139(14) 0.1833(9) 0.5990(4) 0.0545(17) Uani 1 1 d . . . . .
C10A C 0.3858(15) 0.1646(9) 0.5245(4) 0.0528(17) Uani 1 1 d . . . . .
C11A C 0.5724(17) 0.0679(10) 0.4899(5) 0.0632(19) Uani 1 1 d . . . . .
H11A H 0.707486 0.014624 0.513482 0.076 Uiso 1 1 calc R . . . .
C12A C 0.5634(18) 0.0487(10) 0.4221(4) 0.065(2) Uani 1 1 d . . . . .
H12A H 0.689519 -0.018649 0.398744 0.078 Uiso 1 1 calc R . . . .
C13A C 0.3683(19) 0.1287(11) 0.3884(4) 0.063(2) Uani 1 1 d . . . . .
C14A C 0.1846(17) 0.2286(11) 0.4207(5) 0.066(2) Uani 1 1 d . . . . .
H14A H 0.055111 0.285169 0.396528 0.079 Uiso 1 1 calc R . . . .
C15A C 0.1939(16) 0.2443(11) 0.4893(5) 0.0639(19) Uani 1 1 d . . . . .
H15A H 0.066330 0.310876 0.512634 0.077 Uiso 1 1 calc R . . . .
Br1B Br -0.36242(16) 0.60416(9) 0.70598(5) 0.0751(3) Uani 1 1 d . . . . .
Cl1B Cl -0.2103(4) 0.4199(2) 0.26421(12) 0.0683(5) Uani 1 1 d . . . . .
O1B O 0.2211(11) 0.7116(7) 0.3836(3) 0.0659(14) Uani 1 1 d . . . . .
O2B O -0.3353(11) 0.8850(7) 0.1494(3) 0.0663(14) Uani 1 1 d . . . . .
N1B N -0.2122(12) 0.6862(8) 0.3618(3) 0.0560(15) Uani 1 1 d . . . . .
H1B H -0.377132 0.661509 0.377925 0.067 Uiso 1 1 calc R . . . .
N2B N 0.0899(12) 0.7959(8) 0.1598(3) 0.0554(15) Uani 1 1 d . . . . .
H2B H 0.262218 0.820411 0.158720 0.066 Uiso 1 1 calc R . . . .
C1B C -0.1630(16) 0.7247(10) 0.2910(5) 0.0594(19) Uani 1 1 d . . . . .
H1BA H -0.054306 0.820816 0.285611 0.071 Uiso 1 1 calc R . . . .
H1BB H -0.338853 0.747368 0.272097 0.071 Uiso 1 1 calc R . . . .
C2B C -0.0158(17) 0.5971(10) 0.2506(5) 0.058(2) Uani 1 1 d . . . . .
H2BA H 0.168439 0.579389 0.266834 0.069 Uiso 1 1 calc R . . . .
C3B C 0.0116(15) 0.6346(10) 0.1743(4) 0.0547(17) Uani 1 1 d . . . . .
H3B H -0.169298 0.619558 0.156641 0.066 Uiso 1 1 calc R . . . .
C4B C 0.2149(17) 0.5232(11) 0.1381(5) 0.065(2) Uani 1 1 d . . . . .
H4BA H 0.395345 0.537642 0.154880 0.078 Uiso 1 1 calc R . . . .
H4BB H 0.159514 0.414572 0.149665 0.078 Uiso 1 1 calc R . . . .
C5B C 0.239(2) 0.5458(14) 0.0621(5) 0.084(3) Uani 1 1 d . . . . .
H5BA H 0.310725 0.651087 0.050165 0.100 Uiso 1 1 calc R . . . .
H5BB H 0.056742 0.540120 0.045439 0.100 Uiso 1 1 calc R . . . .
C6B C 0.424(3) 0.4248(15) 0.0269(6) 0.098(4) Uani 1 1 d . . . . .
H6BA H 0.433220 0.445460 -0.021827 0.147 Uiso 1 1 calc GR . . . .
H6BB H 0.351886 0.320402 0.037441 0.147 Uiso 1 1 calc GR . . . .
H6BC H 0.606316 0.430949 0.042593 0.147 Uiso 1 1 calc GR . . . .
C7B C -0.0932(16) 0.9078(10) 0.1482(4) 0.0585(18) Uani 1 1 d . . . . .
C8B C 0.019(2) 1.0688(11) 0.1326(5) 0.066(2) Uani 1 1 d . . . . .
H8BA H -0.049837 1.110667 0.090771 0.100 Uiso 1 1 calc GR . . . .
H8BB H 0.216962 1.062854 0.127349 0.100 Uiso 1 1 calc GR . . . .
H8BC H -0.038782 1.137256 0.169537 0.100 Uiso 1 1 calc GR . . . .
C9B C -0.0149(14) 0.6869(9) 0.4033(4) 0.0531(16) Uani 1 1 d . . . . .
C10B C -0.1016(14) 0.6638(9) 0.4768(4) 0.0549(16) Uani 1 1 d . . . . .
C11B C 0.0373(16) 0.7380(10) 0.5240(4) 0.0630(19) Uani 1 1 d . . . . .
H11B H 0.187996 0.800702 0.508841 0.076 Uiso 1 1 calc R . . . .
C12B C -0.0352(18) 0.7241(11) 0.5916(4) 0.0649(19) Uani 1 1 d . . . . .
H12B H 0.061193 0.777283 0.622981 0.078 Uiso 1 1 calc R . . . .
C13B C -0.2545(18) 0.6299(10) 0.6131(4) 0.0607(19) Uani 1 1 d . . . . .
C14B C -0.3954(17) 0.5530(10) 0.5677(5) 0.0626(19) Uani 1 1 d . . . . .
H14B H -0.542712 0.487987 0.583011 0.075 Uiso 1 1 calc R . . . .
C15B C -0.3209(16) 0.5713(10) 0.4997(4) 0.0603(19) Uani 1 1 d . . . . .
H15B H -0.420221 0.520274 0.468157 0.072 Uiso 1 1 calc R . . . .


_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
Br1A C13A 1.908(8) . ?
Cl1A C2A 1.822(8) . ?
O1A C9A 1.219(9) . ?
O2A C7A 1.211(10) . ?
N1A H1A 0.8800 . ?
N1A C1A 1.444(11) . ?
N1A C9A 1.336(10) . ?
N2A H2A 0.8800 . ?
N2A C3A 1.461(11) . ?
N2A C7A 1.352(10) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.510(11) . ?
C2A H2AA 1.0000 . ?
C2A C3A 1.533(12) . ?
C3A H3A 1.0000 . ?
C3A C4A 1.519(11) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.507(14) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.514(15) . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C7A C8A 1.510(13) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A C10A 1.516(11) . ?
C10A C11A 1.390(12) . ?
C10A C15A 1.385(12) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.372(13) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.381(13) . ?
C13A C14A 1.378(13) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.384(13) . ?
C15A H15A 0.9500 . ?
Br1B C13B 1.893(8) . ?
Cl1B C2B 1.814(8) . ?
O1B C9B 1.222(9) . ?
O2B C7B 1.216(9) . ?
N1B H1B 0.8800 . ?
N1B C1B 1.440(11) . ?
N1B C9B 1.330(10) . ?
N2B H2B 0.8800 . ?
N2B C3B 1.456(10) . ?
N2B C7B 1.337(11) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.524(13) . ?
C2B H2BA 1.0000 . ?
C2B C3B 1.539(12) . ?
C3B H3B 1.0000 . ?
C3B C4B 1.534(12) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.516(14) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C6B 1.525(16) . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C6B H6BC 0.9800 . ?
C7B C8B 1.509(12) . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C9B C10B 1.502(11) . ?
C10B C11B 1.385(11) . ?
C10B C15B 1.392(11) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.369(12) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.395(12) . ?
C13B C14B 1.377(13) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.381(12) . ?
C15B H15B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A H1A 118.7 . . ?
C9A N1A H1A 118.7 . . ?
C9A N1A C1A 122.6(6) . . ?
C3A N2A H2A 119.1 . . ?
C7A N2A H2A 119.1 . . ?
C7A N2A C3A 121.8(7) . . ?
N1A C1A H1AA 109.0 . . ?
N1A C1A H1AB 109.0 . . ?
N1A C1A C2A 113.1(7) . . ?
H1AA C1A H1AB 107.8 . . ?
C2A C1A H1AA 109.0 . . ?
C2A C1A H1AB 109.0 . . ?
Cl1A C2A H2AA 108.8 . . ?
C1A C2A Cl1A 107.4(6) . . ?
C1A C2A H2AA 108.8 . . ?
C1A C2A C3A 115.4(7) . . ?
C3A C2A Cl1A 107.4(6) . . ?
C3A C2A H2AA 108.8 . . ?
N2A C3A C2A 111.0(7) . . ?
N2A C3A H3A 107.8 . . ?
N2A C3A C4A 110.9(7) . . ?
C2A C3A H3A 107.8 . . ?
C4A C3A C2A 111.3(7) . . ?
C4A C3A H3A 107.8 . . ?
C3A C4A H4AA 108.5 . . ?
C3A C4A H4AB 108.5 . . ?
H4AA C4A H4AB 107.5 . . ?
C5A C4A C3A 115.0(8) . . ?
C5A C4A H4AA 108.5 . . ?
C5A C4A H4AB 108.5 . . ?
C4A C5A H5AA 108.9 . . ?
C4A C5A H5AB 108.9 . . ?
C4A C5A C6A 113.6(10) . . ?
H5AA C5A H5AB 107.7 . . ?
C6A C5A H5AA 108.9 . . ?
C6A C5A H5AB 108.9 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
O2A C7A N2A 123.3(8) . . ?
O2A C7A C8A 121.5(8) . . ?
N2A C7A C8A 115.1(7) . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
O1A C9A N1A 123.8(8) . . ?
O1A C9A C10A 120.4(7) . . ?
N1A C9A C10A 115.8(6) . . ?
C11A C10A C9A 117.5(7) . . ?
C15A C10A C9A 123.4(8) . . ?
C15A C10A C11A 119.0(8) . . ?
C10A C11A H11A 119.7 . . ?
C12A C11A C10A 120.7(8) . . ?
C12A C11A H11A 119.7 . . ?
C11A C12A H12A 120.5 . . ?
C11A C12A C13A 119.0(8) . . ?
C13A C12A H12A 120.5 . . ?
C12A C13A Br1A 118.1(7) . . ?
C14A C13A Br1A 119.9(7) . . ?
C14A C13A C12A 122.0(8) . . ?
C13A C14A H14A 120.9 . . ?
C13A C14A C15A 118.1(8) . . ?
C15A C14A H14A 120.9 . . ?
C10A C15A H15A 119.4 . . ?
C14A C15A C10A 121.2(9) . . ?
C14A C15A H15A 119.4 . . ?
C1B N1B H1B 119.1 . . ?
C9B N1B H1B 119.1 . . ?
C9B N1B C1B 121.8(6) . . ?
C3B N2B H2B 119.1 . . ?
C7B N2B H2B 119.1 . . ?
C7B N2B C3B 121.7(6) . . ?
N1B C1B H1BA 108.7 . . ?
N1B C1B H1BB 108.7 . . ?
N1B C1B C2B 114.2(7) . . ?
H1BA C1B H1BB 107.6 . . ?
C2B C1B H1BA 108.7 . . ?
C2B C1B H1BB 108.7 . . ?
Cl1B C2B H2BA 109.3 . . ?
C1B C2B Cl1B 108.0(6) . . ?
C1B C2B H2BA 109.3 . . ?
C1B C2B C3B 113.3(7) . . ?
C3B C2B Cl1B 107.5(6) . . ?
C3B C2B H2BA 109.3 . . ?
N2B C3B C2B 111.3(7) . . ?
N2B C3B H3B 108.0 . . ?
N2B C3B C4B 110.4(6) . . ?
C2B C3B H3B 108.0 . . ?
C4B C3B C2B 111.0(7) . . ?
C4B C3B H3B 108.0 . . ?
C3B C4B H4BA 108.7 . . ?
C3B C4B H4BB 108.7 . . ?
H4BA C4B H4BB 107.6 . . ?
C5B C4B C3B 114.1(8) . . ?
C5B C4B H4BA 108.7 . . ?
C5B C4B H4BB 108.7 . . ?
C4B C5B H5BA 109.0 . . ?
C4B C5B H5BB 109.0 . . ?
C4B C5B C6B 113.0(10) . . ?
H5BA C5B H5BB 107.8 . . ?
C6B C5B H5BA 109.0 . . ?
C6B C5B H5BB 109.0 . . ?
C5B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
C5B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
O2B C7B N2B 123.6(8) . . ?
O2B C7B C8B 120.6(8) . . ?
N2B C7B C8B 115.8(7) . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
O1B C9B N1B 122.5(7) . . ?
O1B C9B C10B 121.6(7) . . ?
N1B C9B C10B 115.9(6) . . ?
C11B C10B C9B 119.5(7) . . ?
C11B C10B C15B 118.3(8) . . ?
C15B C10B C9B 122.2(7) . . ?
C10B C11B H11B 118.9 . . ?
C12B C11B C10B 122.3(7) . . ?
C12B C11B H11B 118.9 . . ?
C11B C12B H12B 120.9 . . ?
C11B C12B C13B 118.2(8) . . ?
C13B C12B H12B 120.9 . . ?
C12B C13B Br1B 120.3(7) . . ?
C14B C13B Br1B 118.7(7) . . ?
C14B C13B C12B 121.1(8) . . ?
C13B C14B H14B 120.2 . . ?
C13B C14B C15B 119.5(8) . . ?
C15B C14B H14B 120.2 . . ?
C10B C15B H15B 119.7 . . ?
C14B C15B C10B 120.6(8) . . ?
C14B C15B H15B 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1A 0.88 2.01 2.794(8) 147.1 1_455 yes
N1B H1B O1B 0.88 2.02 2.811(8) 148.4 1_455 yes

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
Br1A C13A C14A C15A 178.6(6) . . . . ?
Cl1A C2A C3A N2A 164.9(5) . . . . ?
Cl1A C2A C3A C4A -71.1(7) . . . . ?
O1A C9A C10A C11A 29.9(11) . . . . ?
O1A C9A C10A C15A -146.8(8) . . . . ?
N1A C1A C2A Cl1A 64.0(8) . . . . ?
N1A C1A C2A C3A -176.3(7) . . . . ?
N1A C9A C10A C11A -153.1(7) . . . . ?
N1A C9A C10A C15A 30.2(10) . . . . ?
N2A C3A C4A C5A -57.7(10) . . . . ?
C1A N1A C9A O1A -0.7(12) . . . . ?
C1A N1A C9A C10A -177.6(7) . . . . ?
C1A C2A C3A N2A 45.3(9) . . . . ?
C1A C2A C3A C4A 169.3(7) . . . . ?
C2A C3A C4A C5A 178.3(8) . . . . ?
C3A N2A C7A O2A 3.2(12) . . . . ?
C3A N2A C7A C8A -176.7(7) . . . . ?
C3A C4A C5A C6A -176.0(9) . . . . ?
C7A N2A C3A C2A -97.9(8) . . . . ?
C7A N2A C3A C4A 137.9(7) . . . . ?
C9A N1A C1A C2A -112.7(8) . . . . ?
C9A C10A C11A C12A -178.3(7) . . . . ?
C9A C10A C15A C14A 177.0(7) . . . . ?
C10A C11A C12A C13A 0.9(12) . . . . ?
C11A C10A C15A C14A 0.3(12) . . . . ?
C11A C12A C13A Br1A -179.7(6) . . . . ?
C11A C12A C13A C14A 0.8(13) . . . . ?
C12A C13A C14A C15A -1.9(13) . . . . ?
C13A C14A C15A C10A 1.4(13) . . . . ?
C15A C10A C11A C12A -1.4(12) . . . . ?
Br1B C13B C14B C15B 179.5(6) . . . . ?
Cl1B C2B C3B N2B 162.6(5) . . . . ?
Cl1B C2B C3B C4B -74.0(7) . . . . ?
O1B C9B C10B C11B 30.4(12) . . . . ?
O1B C9B C10B C15B -150.5(8) . . . . ?
N1B C1B C2B Cl1B 55.9(8) . . . . ?
N1B C1B C2B C3B 174.8(6) . . . . ?
N1B C9B C10B C11B -146.6(8) . . . . ?
N1B C9B C10B C15B 32.5(11) . . . . ?
N2B C3B C4B C5B -59.9(10) . . . . ?
C1B N1B C9B O1B -4.2(12) . . . . ?
C1B N1B C9B C10B 172.8(7) . . . . ?
C1B C2B C3B N2B 43.4(9) . . . . ?
C1B C2B C3B C4B 166.9(7) . . . . ?
C2B C3B C4B C5B 176.2(8) . . . . ?
C3B N2B C7B O2B 0.8(12) . . . . ?
C3B N2B C7B C8B -178.9(7) . . . . ?
C3B C4B C5B C6B -175.1(9) . . . . ?
C7B N2B C3B C2B -96.9(8) . . . . ?
C7B N2B C3B C4B 139.3(8) . . . . ?
C9B N1B C1B C2B 74.8(9) . . . . ?
C9B C10B C11B C12B 178.6(8) . . . . ?
C9B C10B C15B C14B -179.8(7) . . . . ?
C10B C11B C12B C13B 0.9(14) . . . . ?
C11B C10B C15B C14B -0.7(13) . . . . ?
C11B C12B C13B Br1B 179.3(7) . . . . ?
C11B C12B C13B C14B -0.2(13) . . . . ?
C12B C13B C14B C15B -0.9(13) . . . . ?
C13B C14B C15B C10B 1.4(13) . . . . ?
C15B C10B C11B C12B -0.5(13) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with paratone oil'
_olex2_submission_original_sample_id 42
_olex2_submission_special_instructions 'No special instructions were received'
