# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_zz
_audit_block_doi                 10.5517/ccdc.csd.cc248w1c
_database_code_depnum_ccdc_archive 'CCDC 1974732'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_audit_creation_date             2019-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 Br N O2'
_chemical_formula_sum            'C17 H16 Br N O2'
_chemical_formula_weight         346.22
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.7754(7)
_cell_length_b                   8.5582(4)
_cell_length_c                   11.6197(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.1620(10)
_cell_angle_gamma                90
_cell_volume                     1498.91(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4434
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.383
_cell_measurement_theta_min      2.703
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.810
_exptl_absorpt_coefficient_mu    2.746
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1178 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.6716. 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    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15168
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_min         2.703
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_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                2379
_reflns_number_total             3036
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.335
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.042
_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)+(0.0273P)²+1.1195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0784
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C14(H14), C13(H13), C9(H9), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
Br1 Br 0.54564(2) 0.76171(4) 0.33083(3) 0.03097(11) Uani 1 1 d . . . . .
O2 O 0.24076(13) 0.4707(2) 0.24474(16) 0.0255(5) Uani 1 1 d . . . . .
H2 H 0.248830 0.471586 0.176446 0.038 Uiso 1 1 calc GR . . . .
O1 O 0.26543(13) 0.0141(2) 0.52853(16) 0.0258(5) Uani 1 1 d . . . . .
N1 N 0.24527(15) 0.2323(2) 0.41060(19) 0.0199(5) Uani 1 1 d . . . . .
H1 H 0.250964 0.268954 0.342513 0.024 Uiso 1 1 calc R . . . .
C16 C 0.38062(18) 0.6046(3) 0.2911(2) 0.0194(6) Uani 1 1 d . . . . .
H16 H 0.380774 0.599280 0.209494 0.023 Uiso 1 1 calc R . . . .
C15 C 0.45000(18) 0.6740(3) 0.3774(2) 0.0199(6) Uani 1 1 d . . . . .
C14 C 0.45178(19) 0.6841(3) 0.4968(2) 0.0221(6) Uani 1 1 d . . . . .
H14 H 0.500474 0.730802 0.555201 0.027 Uiso 1 1 calc R . . . .
C17 C 0.31060(18) 0.5427(3) 0.3262(2) 0.0188(6) Uani 1 1 d . . . . .
C12 C 0.30880(18) 0.5520(3) 0.4459(2) 0.0191(6) Uani 1 1 d . . . . .
C10 C 0.27333(18) 0.0848(3) 0.4394(2) 0.0203(6) Uani 1 1 d . . . . .
C7 C 0.20729(18) 0.3357(3) 0.4783(2) 0.0183(6) Uani 1 1 d . . . . .
C13 C 0.38081(18) 0.6243(3) 0.5286(2) 0.0211(6) Uani 1 1 d . . . . .
H13 H 0.380799 0.632584 0.610087 0.025 Uiso 1 1 calc R . . . .
C9 C 0.19603(19) 0.5950(3) 0.5534(2) 0.0227(6) Uani 1 1 d . . . . .
H9 H 0.212066 0.702357 0.559763 0.027 Uiso 1 1 calc R . . . .
C8 C 0.23470(18) 0.4928(3) 0.4895(2) 0.0191(6) Uani 1 1 d . . . . .
C5 C 0.11006(18) 0.3844(3) 0.5986(2) 0.0236(6) Uani 1 1 d . . . . .
C6 C 0.14510(18) 0.2817(3) 0.5320(2) 0.0210(6) Uani 1 1 d . . . . .
H6 H 0.126688 0.175586 0.523283 0.025 Uiso 1 1 calc R . . . .
C4 C 0.13414(19) 0.5400(3) 0.6077(2) 0.0243(6) Uani 1 1 d . . . . .
C11 C 0.3190(2) 0.0106(3) 0.3571(2) 0.0274(7) Uani 1 1 d . . . . .
H11A H 0.383253 0.010531 0.395940 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.305597 0.069925 0.281720 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.298111 -0.097123 0.339847 0.041 Uiso 1 1 calc GR . . . .
C1 C 0.0450(2) 0.3493(3) 0.6673(3) 0.0295(7) Uani 1 1 d . . . . .
H1A H 0.067965 0.266255 0.727851 0.035 Uiso 1 1 calc R . . . .
H1B H -0.012770 0.315575 0.612187 0.035 Uiso 1 1 calc R . . . .
C3 C 0.0863(2) 0.6288(4) 0.6828(3) 0.0332(7) Uani 1 1 d . . . . .
H3A H 0.045036 0.706835 0.633253 0.040 Uiso 1 1 calc R . . . .
H3B H 0.129012 0.682881 0.750888 0.040 Uiso 1 1 calc R . . . .
C2 C 0.0359(3) 0.5031(4) 0.7279(4) 0.0522(11) Uani 1 1 d . . . . .
H2A H 0.060298 0.492423 0.816414 0.063 Uiso 1 1 calc R . . . .
H2B H -0.027493 0.532118 0.708732 0.063 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
Br1 C15 1.901(3) . ?
O2 C17 1.369(3) . ?
O1 C10 1.237(3) . ?
N1 C10 1.346(3) . ?
N1 C7 1.428(3) . ?
C16 C15 1.382(4) . ?
C16 C17 1.390(4) . ?
C15 C14 1.382(4) . ?
C14 C13 1.376(4) . ?
C17 C12 1.402(3) . ?
C12 C13 1.397(4) . ?
C12 C8 1.493(4) . ?
C10 C11 1.498(4) . ?
C7 C8 1.406(4) . ?
C7 C6 1.388(4) . ?
C9 C8 1.399(4) . ?
C9 C4 1.391(4) . ?
C5 C6 1.389(4) . ?
C5 C4 1.380(4) . ?
C5 C1 1.504(4) . ?
C4 C3 1.515(4) . ?
C1 C2 1.520(4) . ?
C3 C2 1.520(4) . ?

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
C10 N1 C7 127.2(2) . . ?
C15 C16 C17 118.6(2) . . ?
C16 C15 Br1 119.2(2) . . ?
C16 C15 C14 122.2(2) . . ?
C14 C15 Br1 118.6(2) . . ?
C13 C14 C15 117.9(3) . . ?
O2 C17 C16 121.1(2) . . ?
O2 C17 C12 117.6(2) . . ?
C16 C17 C12 121.3(2) . . ?
C17 C12 C8 124.4(2) . . ?
C13 C12 C17 117.2(2) . . ?
C13 C12 C8 118.4(2) . . ?
O1 C10 N1 124.1(2) . . ?
O1 C10 C11 120.9(2) . . ?
N1 C10 C11 115.0(2) . . ?
C8 C7 N1 118.5(2) . . ?
C6 C7 N1 120.5(2) . . ?
C6 C7 C8 121.0(2) . . ?
C14 C13 C12 122.8(2) . . ?
C4 C9 C8 120.2(2) . . ?
C7 C8 C12 122.9(2) . . ?
C9 C8 C12 118.4(2) . . ?
C9 C8 C7 118.5(2) . . ?
C6 C5 C1 127.9(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 C1 111.6(2) . . ?
C7 C6 C5 119.4(2) . . ?
C9 C4 C3 128.8(3) . . ?
C5 C4 C9 120.4(2) . . ?
C5 C4 C3 110.8(2) . . ?
C5 C1 C2 104.2(2) . . ?
C4 C3 C2 104.1(2) . . ?
C1 C2 C3 108.8(2) . . ?

_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_220191293lxj_0m
_audit_block_doi                 10.5517/ccdc.csd.cc248w2d
_database_code_depnum_ccdc_archive 'CCDC 1974733'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Br N O3'
_chemical_formula_sum            'C20 H14 Br N O3'
_chemical_formula_weight         396.23
_chemical_absolute_configuration .
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.2743(5)
_cell_length_b                   15.4368(16)
_cell_length_c                   24.939(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1645.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.512
_cell_measurement_theta_min      2.370
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    2.517
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1429 before and 0.0772 after correction. The Ratio of minimum to maximum transmission is 0.6511. 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    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.1007
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7712
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.506
_diffrn_reflns_theta_min         2.639
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                2289
_reflns_number_total             3328
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.405
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 
;
 Flack x determined using 668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.194(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      0.997
_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)+(0.0487P)²+0.2479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1169
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C17(H17), C19(H19), C11(H11), C20(H20), C12(H12), C5(H5), C4(H4),
 C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Br1 Br 0.5354(2) 0.01814(5) 0.67719(3) 0.0368(3) Uani 1 1 d . . . . .
O3 O 0.3930(13) 0.5933(3) 0.5734(2) 0.0266(13) Uani 1 1 d . . . . .
O1 O -0.0278(14) 0.2776(3) 0.5844(2) 0.0288(12) Uani 1 1 d . . . . .
H1 H -0.018341 0.242086 0.558901 0.043 Uiso 1 1 calc GR . . . .
O2 O 0.5291(15) 0.3403(3) 0.4927(2) 0.0365(14) Uani 1 1 d . . . . .
N1 N 0.4814(17) 0.4056(3) 0.5718(2) 0.0249(14) Uani 1 1 d . . . . .
H1A H 0.660143 0.382247 0.581692 0.030 Uiso 1 1 calc R . . . .
C18 C 0.4122(15) 0.1363(4) 0.6736(3) 0.0221(16) Uani 1 1 d . . . . .
C9 C 0.3098(18) 0.4499(5) 0.6120(3) 0.0228(18) Uani 1 1 d . . . . .
C17 C 0.2349(17) 0.1628(4) 0.6305(3) 0.0214(17) Uani 1 1 d . . . . .
H17 H 0.166324 0.122046 0.604465 0.026 Uiso 1 1 calc R . . . .
C8 C 0.2721(17) 0.5384(5) 0.6125(3) 0.0231(18) Uani 1 1 d . . . . .
C19 C 0.513(2) 0.1940(4) 0.7125(3) 0.0263(16) Uani 1 1 d . . . . .
H19 H 0.633311 0.174684 0.742169 0.032 Uiso 1 1 calc R . . . .
C11 C 0.036(2) 0.4497(4) 0.6978(3) 0.0261(18) Uani 1 1 d . . . . .
H11 H -0.039449 0.418590 0.728077 0.031 Uiso 1 1 calc R . . . .
C7 C 0.107(2) 0.5840(5) 0.6522(3) 0.026(2) Uani 1 1 d . . . . .
C20 C 0.4329(19) 0.2799(4) 0.7070(3) 0.0267(18) Uani 1 1 d . . . . .
H20 H 0.498349 0.319882 0.733734 0.032 Uiso 1 1 calc R . . . .
C16 C 0.1579(16) 0.2495(5) 0.6255(3) 0.0238(18) Uani 1 1 d . . . . .
C10 C 0.1940(17) 0.4044(4) 0.6573(3) 0.0221(19) Uani 1 1 d . . . . .
C15 C 0.2586(16) 0.3102(4) 0.6635(3) 0.0203(18) Uani 1 1 d . . . . .
C12 C -0.0143(19) 0.5384(4) 0.6952(3) 0.0261(17) Uani 1 1 d . . . . .
H12 H -0.129874 0.567274 0.722345 0.031 Uiso 1 1 calc R . . . .
C14 C 0.3974(18) 0.3956(5) 0.5196(3) 0.028(2) Uani 1 1 d . . . . .
C1 C 0.3048(19) 0.6757(5) 0.5897(3) 0.0287(19) Uani 1 1 d . . . . .
C5 C 0.023(2) 0.7523(5) 0.6582(3) 0.038(2) Uani 1 1 d . . . . .
H5 H -0.094467 0.752861 0.690498 0.045 Uiso 1 1 calc R . . . .
C6 C 0.1280(19) 0.6748(5) 0.6367(4) 0.034(2) Uani 1 1 d . . . . .
C4 C 0.091(2) 0.8282(5) 0.6320(4) 0.043(2) Uani 1 1 d . . . . .
H4 H 0.015921 0.881497 0.645990 0.051 Uiso 1 1 calc R . . . .
C3 C 0.271(2) 0.8283(6) 0.5846(4) 0.044(2) Uani 1 1 d . . . . .
H3 H 0.318841 0.881679 0.567509 0.052 Uiso 1 1 calc R . . . .
C2 C 0.380(2) 0.7512(5) 0.5624(4) 0.036(2) Uani 1 1 d . . . . .
H2 H 0.500240 0.750312 0.530357 0.043 Uiso 1 1 calc R . . . .
C13 C 0.163(2) 0.4555(5) 0.4959(3) 0.038(2) Uani 1 1 d . . . . .
H13A H 0.268637 0.508045 0.483243 0.057 Uiso 1 1 calc GR . . . .
H13B H 0.007509 0.470933 0.523081 0.057 Uiso 1 1 calc GR . . . .
H13C H 0.059091 0.426974 0.465643 0.057 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
Br1 C18 1.901(6) . ?
O3 C8 1.392(9) . ?
O3 C1 1.387(8) . ?
O1 H1 0.8400 . ?
O1 C16 1.368(8) . ?
O2 C14 1.223(9) . ?
N1 H1A 0.8800 . ?
N1 C9 1.417(9) . ?
N1 C14 1.360(9) . ?
C18 C17 1.377(10) . ?
C18 C19 1.385(10) . ?
C9 C8 1.376(10) . ?
C9 C10 1.419(11) . ?
C17 H17 0.9500 . ?
C17 C16 1.384(10) . ?
C8 C7 1.404(10) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(9) . ?
C11 H11 0.9500 . ?
C11 C10 1.402(10) . ?
C11 C12 1.388(9) . ?
C7 C12 1.384(10) . ?
C7 C6 1.457(10) . ?
C20 H20 0.9500 . ?
C20 C15 1.398(10) . ?
C16 C15 1.400(10) . ?
C10 C15 1.488(9) . ?
C12 H12 0.9500 . ?
C14 C13 1.485(11) . ?
C1 C6 1.395(12) . ?
C1 C2 1.387(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(10) . ?
C5 C4 1.373(11) . ?
C4 H4 0.9500 . ?
C4 C3 1.411(13) . ?
C3 H3 0.9500 . ?
C3 C2 1.392(12) . ?
C2 H2 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C1 O3 C8 104.6(6) . . ?
C16 O1 H1 109.5 . . ?
C9 N1 H1A 116.7 . . ?
C14 N1 H1A 116.7 . . ?
C14 N1 C9 126.5(7) . . ?
C17 C18 Br1 118.3(6) . . ?
C17 C18 C19 121.8(6) . . ?
C19 C18 Br1 119.8(6) . . ?
N1 C9 C10 120.3(6) . . ?
C8 C9 N1 123.1(7) . . ?
C8 C9 C10 116.3(7) . . ?
C18 C17 H17 120.4 . . ?
C18 C17 C16 119.2(7) . . ?
C16 C17 H17 120.4 . . ?
O3 C8 C7 112.0(6) . . ?
C9 C8 O3 123.7(7) . . ?
C9 C8 C7 124.3(7) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.2(7) . . ?
C20 C19 H19 120.9 . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C12 C11 C10 122.1(7) . . ?
C8 C7 C6 105.4(7) . . ?
C12 C7 C8 118.6(7) . . ?
C12 C7 C6 135.8(7) . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C15 122.1(7) . . ?
C15 C20 H20 118.9 . . ?
O1 C16 C17 120.7(7) . . ?
O1 C16 C15 118.3(7) . . ?
C17 C16 C15 120.9(7) . . ?
C9 C10 C15 120.0(7) . . ?
C11 C10 C9 119.7(6) . . ?
C11 C10 C15 120.1(7) . . ?
C20 C15 C16 117.7(6) . . ?
C20 C15 C10 120.4(6) . . ?
C16 C15 C10 121.8(7) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 C11 118.8(7) . . ?
C7 C12 H12 120.6 . . ?
O2 C14 N1 118.9(7) . . ?
O2 C14 C13 121.7(8) . . ?
N1 C14 C13 119.3(7) . . ?
O3 C1 C6 112.6(7) . . ?
O3 C1 C2 124.3(8) . . ?
C2 C1 C6 123.1(8) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(8) . . ?
C1 C6 C7 105.3(7) . . ?
C5 C6 C7 135.1(8) . . ?
C5 C6 C1 119.5(8) . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.0(8) . . ?
C3 C4 H4 119.5 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 121.0(8) . . ?
C2 C3 H3 119.5 . . ?
C1 C2 C3 116.5(9) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_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_zz_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc248w3f
_database_code_depnum_ccdc_archive 'CCDC 1974734'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_audit_creation_date             2019-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 Br N O2'
_chemical_formula_sum            'C18 H18 Br N O2'
_chemical_formula_weight         360.24
_chemical_absolute_configuration .
_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'
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.5591(3)
_cell_length_b                   7.9650(2)
_cell_length_c                   17.2106(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1584.55(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7062
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.367
_cell_measurement_theta_min      2.557
_shelx_estimated_absorpt_T_max   0.819
_shelx_estimated_absorpt_T_min   0.638
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0955 before and 0.0747 after correction. The Ratio of minimum to maximum transmission is 0.7362. 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    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17118
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.385
_diffrn_reflns_theta_min         2.367
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                2726
_reflns_number_total             3027
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.667
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1070 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.047
_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)+(0.0250P)²+1.0224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0722
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C8(H8), C9(H9), C2(H2), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Br1 Br 0.84585(4) 0.05963(6) 0.22384(4) 0.03517(15) Uani 1 1 d . . . . .
O1 O 0.8247(2) 0.2675(4) 0.51115(19) 0.0252(7) Uani 1 1 d . . . . .
H1 H 0.895909 0.271128 0.501522 0.038 Uiso 1 1 calc GR . . . .
O2 O 0.5442(3) 0.7098(4) 0.4744(2) 0.0348(8) Uani 1 1 d . . . . .
N1 N 0.6654(3) 0.5148(4) 0.5258(2) 0.0206(7) Uani 1 1 d . . . . .
H1A H 0.738516 0.493305 0.536097 0.025 Uiso 1 1 calc R . . . .
C1 C 0.7644(4) 0.1061(5) 0.3174(3) 0.0245(10) Uani 1 1 d . . . . .
C18 C 0.6428(3) 0.6532(5) 0.4838(3) 0.0219(9) Uani 1 1 d . . . . .
C10 C 0.4279(4) 0.3304(6) 0.6446(3) 0.0262(10) Uani 1 1 d . . . . .
C12 C 0.5816(3) 0.3994(5) 0.5554(3) 0.0196(9) Uani 1 1 d . . . . .
C8 C 0.4948(4) 0.1270(6) 0.5513(3) 0.0231(9) Uani 1 1 d . . . . .
H8 H 0.489719 0.017313 0.529820 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7671(3) 0.2090(5) 0.4478(2) 0.0201(9) Uani 1 1 d . . . . .
C9 C 0.4213(4) 0.1722(6) 0.6112(3) 0.0263(10) Uani 1 1 d . . . . .
H9 H 0.365648 0.094018 0.629658 0.032 Uiso 1 1 calc R . . . .
C2 C 0.8253(4) 0.1693(5) 0.3796(3) 0.0228(9) Uani 1 1 d . . . . .
H2 H 0.906570 0.185640 0.375910 0.027 Uiso 1 1 calc R . . . .
C6 C 0.6458(4) 0.0783(5) 0.3210(3) 0.0257(10) Uani 1 1 d . . . . .
H6 H 0.605161 0.030759 0.278332 0.031 Uiso 1 1 calc R . . . .
C11 C 0.5104(4) 0.4455(5) 0.6171(3) 0.0225(9) Uani 1 1 d . . . . .
C13 C 0.5233(4) 0.6091(6) 0.6606(3) 0.0297(11) Uani 1 1 d . . . . .
H13A H 0.459678 0.686454 0.646358 0.036 Uiso 1 1 calc R . . . .
H13B H 0.597606 0.663103 0.646795 0.036 Uiso 1 1 calc R . . . .
C7 C 0.5759(3) 0.2394(5) 0.5218(3) 0.0197(8) Uani 1 1 d . . . . .
C5 C 0.5893(4) 0.1221(5) 0.3885(3) 0.0230(9) Uani 1 1 d . . . . .
H5 H 0.508093 0.105249 0.391456 0.028 Uiso 1 1 calc R . . . .
C17 C 0.7456(4) 0.7350(6) 0.4467(3) 0.0310(11) Uani 1 1 d . . . . .
H17A H 0.738996 0.726750 0.390088 0.046 Uiso 1 1 calc GR . . . .
H17B H 0.816326 0.678215 0.463873 0.046 Uiso 1 1 calc GR . . . .
H17C H 0.748612 0.853416 0.461978 0.046 Uiso 1 1 calc GR . . . .
C4 C 0.6460(3) 0.1901(5) 0.4528(3) 0.0203(9) Uani 1 1 d . . . . .
C16 C 0.5198(5) 0.5732(7) 0.7473(3) 0.0422(15) Uani 1 1 d . . . . .
H16A H 0.588649 0.506186 0.761710 0.051 Uiso 1 1 calc R . . . .
H16B H 0.523681 0.680799 0.776013 0.051 Uiso 1 1 calc R . . . .
C14 C 0.3535(4) 0.3837(8) 0.7115(4) 0.0453(15) Uani 1 1 d . . . . .
H14A H 0.288991 0.452301 0.691001 0.054 Uiso 1 1 calc R . . . .
H14B H 0.319463 0.281931 0.735337 0.054 Uiso 1 1 calc R . . . .
C15 C 0.4118(7) 0.4791(11) 0.7720(5) 0.088(3) Uani 1 1 d . . . . .
H15A H 0.432964 0.401009 0.814441 0.105 Uiso 1 1 calc R . . . .
H15B H 0.356135 0.561271 0.793642 0.105 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
Br1 C1 1.902(4) . ?
O1 H1 0.8400 . ?
O1 C3 1.361(5) . ?
O2 C18 1.237(5) . ?
N1 H1A 0.8800 . ?
N1 C18 1.344(6) . ?
N1 C12 1.429(5) . ?
C1 C2 1.377(6) . ?
C1 C6 1.389(6) . ?
C18 C17 1.497(6) . ?
C10 C9 1.388(6) . ?
C10 C11 1.405(6) . ?
C10 C14 1.497(7) . ?
C12 C11 1.393(6) . ?
C12 C7 1.401(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(6) . ?
C8 C7 1.392(6) . ?
C3 C2 1.389(6) . ?
C3 C4 1.410(6) . ?
C9 H9 0.9500 . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.379(6) . ?
C11 C13 1.510(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C16 1.520(8) . ?
C7 C4 1.490(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.395(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.517(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.455(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C3 O1 H1 109.5 . . ?
C18 N1 H1A 117.0 . . ?
C18 N1 C12 126.0(3) . . ?
C12 N1 H1A 117.0 . . ?
C2 C1 Br1 118.4(3) . . ?
C2 C1 C6 122.0(4) . . ?
C6 C1 Br1 119.6(3) . . ?
O2 C18 N1 123.3(4) . . ?
O2 C18 C17 121.1(4) . . ?
N1 C18 C17 115.6(4) . . ?
C9 C10 C11 119.3(4) . . ?
C9 C10 C14 123.0(4) . . ?
C11 C10 C14 117.7(4) . . ?
C11 C12 N1 120.2(4) . . ?
C11 C12 C7 121.8(4) . . ?
C7 C12 N1 118.0(4) . . ?
C9 C8 H8 119.4 . . ?
C9 C8 C7 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
O1 C3 C2 121.2(4) . . ?
O1 C3 C4 118.2(4) . . ?
C2 C3 C4 120.6(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C1 C2 C3 119.4(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C1 C6 H6 121.2 . . ?
C5 C6 C1 117.6(4) . . ?
C5 C6 H6 121.2 . . ?
C10 C11 C13 117.5(4) . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 C13 123.2(4) . . ?
C11 C13 H13A 109.9 . . ?
C11 C13 H13B 109.9 . . ?
C11 C13 C16 108.8(4) . . ?
H13A C13 H13B 108.3 . . ?
C16 C13 H13A 109.9 . . ?
C16 C13 H13B 109.9 . . ?
C12 C7 C4 122.9(4) . . ?
C8 C7 C12 117.8(4) . . ?
C8 C7 C4 119.1(4) . . ?
C6 C5 H5 118.5 . . ?
C6 C5 C4 123.0(4) . . ?
C4 C5 H5 118.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C4 C7 124.1(4) . . ?
C5 C4 C3 117.3(4) . . ?
C5 C4 C7 118.7(4) . . ?
C13 C16 H16A 109.0 . . ?
C13 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C15 C16 C13 113.0(6) . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C10 C14 H14A 108.4 . . ?
C10 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C10 115.6(5) . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C16 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C14 C15 C16 116.0(6) . . ?
C14 C15 H15A 108.3 . . ?
C14 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?

_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_220191300_0m
_audit_block_doi                 10.5517/ccdc.csd.cc248w4g
_database_code_depnum_ccdc_archive 'CCDC 1974735'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_audit_creation_date             2019-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Br N O2'
_chemical_formula_sum            'C18 H14 Br N O2'
_chemical_formula_weight         356.21
_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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.3242(3)
_cell_length_b                   12.6129(3)
_cell_length_c                   28.2407(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2965.06(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6203
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.055
_cell_measurement_theta_min      2.841
_shelx_estimated_absorpt_T_max   0.808
_shelx_estimated_absorpt_T_min   0.665
_exptl_absorpt_coefficient_mu    2.779
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0912 before and 0.0599 after correction. The Ratio of minimum to maximum transmission is 0.8035. 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    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            32027
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.841
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_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                2230
_reflns_number_total             3030
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.383
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²+4.1331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C16(H16), C13(H13), C15(H15), C9(H9), C10(H10), C5(H5), C2(H2),
 C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Br1 Br 0.31984(4) 0.89019(2) 0.21217(2) 0.03085(11) Uani 1 1 d . . . . .
O1 O 0.5266(3) 0.79763(15) 0.38150(7) 0.0248(5) Uani 1 1 d . . . . .
H1 H 0.545500 0.862820 0.379090 0.037 Uiso 1 1 calc GR . . . .
O2 O 0.9285(3) 0.50916(15) 0.36668(8) 0.0282(5) Uani 1 1 d . . . . .
N1 N 0.7446(3) 0.63309(18) 0.38759(8) 0.0208(5) Uani 1 1 d . . . . .
H1A H 0.727571 0.701427 0.391363 0.025 Uiso 1 1 calc R . . . .
C7 C 0.6143(3) 0.5629(2) 0.39750(10) 0.0201(6) Uani 1 1 d . . . . .
C16 C 0.3748(3) 0.6161(2) 0.29155(10) 0.0228(6) Uani 1 1 d . . . . .
H16 H 0.356089 0.542389 0.287414 0.027 Uiso 1 1 calc R . . . .
C14 C 0.3625(3) 0.7917(2) 0.26175(11) 0.0239(7) Uani 1 1 d . . . . .
C12 C 0.4646(3) 0.7605(2) 0.33941(10) 0.0215(6) Uani 1 1 d . . . . .
C17 C 0.8914(4) 0.6029(2) 0.37295(10) 0.0209(6) Uani 1 1 d . . . . .
C11 C 0.4421(3) 0.6509(2) 0.33418(10) 0.0198(6) Uani 1 1 d . . . . .
C6 C 0.6321(3) 0.4870(2) 0.43442(10) 0.0218(6) Uani 1 1 d . . . . .
C8 C 0.4729(3) 0.5725(2) 0.37264(10) 0.0207(6) Uani 1 1 d . . . . .
C13 C 0.4254(3) 0.8305(2) 0.30329(10) 0.0226(7) Uani 1 1 d . . . . .
H13 H 0.441896 0.904498 0.307244 0.027 Uiso 1 1 calc R . . . .
C15 C 0.3343(4) 0.6844(2) 0.25520(11) 0.0254(7) Uani 1 1 d . . . . .
H15 H 0.288656 0.658569 0.226606 0.030 Uiso 1 1 calc R . . . .
C9 C 0.3454(4) 0.5007(2) 0.38334(11) 0.0244(7) Uani 1 1 d . . . . .
H9 H 0.248043 0.505155 0.365915 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5022(4) 0.4176(2) 0.44487(11) 0.0237(7) Uani 1 1 d . . . . .
C10 C 0.3598(4) 0.4263(2) 0.41778(11) 0.0258(7) Uani 1 1 d . . . . .
H10 H 0.272930 0.379378 0.423796 0.031 Uiso 1 1 calc R . . . .
C18 C 1.0113(4) 0.6901(2) 0.36545(11) 0.0284(7) Uani 1 1 d . . . . .
H18A H 1.097004 0.684241 0.389105 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.957825 0.758894 0.368696 0.043 Uiso 1 1 calc GR . . . .
H18C H 1.057510 0.683983 0.333646 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.7723(4) 0.4800(2) 0.46318(11) 0.0279(7) Uani 1 1 d . . . . .
H5 H 0.860342 0.526073 0.457344 0.034 Uiso 1 1 calc R . . . .
C2 C 0.5166(4) 0.3442(2) 0.48225(12) 0.0295(7) Uani 1 1 d . . . . .
H2 H 0.429888 0.297630 0.488959 0.035 Uiso 1 1 calc R . . . .
C4 C 0.7813(4) 0.4075(3) 0.49911(12) 0.0325(8) Uani 1 1 d . . . . .
H4 H 0.876232 0.403465 0.517708 0.039 Uiso 1 1 calc R . . . .
C3 C 0.6526(4) 0.3390(2) 0.50894(12) 0.0329(8) Uani 1 1 d . . . . .
H3 H 0.660423 0.289216 0.534086 0.039 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
Br1 C14 1.905(3) . ?
O1 H1 0.8400 . ?
O1 C12 1.378(3) . ?
O2 C17 1.235(3) . ?
N1 H1A 0.8800 . ?
N1 C7 1.428(4) . ?
N1 C17 1.344(4) . ?
C7 C6 1.423(4) . ?
C7 C8 1.376(4) . ?
C16 H16 0.9500 . ?
C16 C11 1.399(4) . ?
C16 C15 1.381(4) . ?
C14 C13 1.375(4) . ?
C14 C15 1.386(4) . ?
C12 C11 1.402(4) . ?
C12 C13 1.388(4) . ?
C17 C18 1.500(4) . ?
C11 C8 1.492(4) . ?
C6 C1 1.422(4) . ?
C6 C5 1.424(4) . ?
C8 C9 1.427(4) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.357(4) . ?
C1 C10 1.415(4) . ?
C1 C2 1.409(4) . ?
C10 H10 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.368(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.362(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.404(5) . ?
C3 H3 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
C12 O1 H1 109.5 . . ?
C7 N1 H1A 117.4 . . ?
C17 N1 H1A 117.4 . . ?
C17 N1 C7 125.1(2) . . ?
C6 C7 N1 118.8(3) . . ?
C8 C7 N1 119.7(3) . . ?
C8 C7 C6 121.5(3) . . ?
C11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C15 C16 C11 122.8(3) . . ?
C13 C14 Br1 117.8(2) . . ?
C13 C14 C15 121.7(3) . . ?
C15 C14 Br1 120.5(2) . . ?
O1 C12 C11 118.4(3) . . ?
O1 C12 C13 120.3(2) . . ?
C13 C12 C11 121.2(3) . . ?
O2 C17 N1 122.8(3) . . ?
O2 C17 C18 121.0(3) . . ?
N1 C17 C18 116.2(2) . . ?
C16 C11 C12 117.0(3) . . ?
C16 C11 C8 119.2(2) . . ?
C12 C11 C8 123.7(3) . . ?
C7 C6 C5 123.0(3) . . ?
C1 C6 C7 119.1(3) . . ?
C1 C6 C5 117.8(3) . . ?
C7 C8 C11 125.3(3) . . ?
C7 C8 C9 118.2(3) . . ?
C9 C8 C11 116.6(3) . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.2 . . ?
C10 C1 C6 118.5(3) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C10 121.8(3) . . ?
C9 C10 C1 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C1 C10 H10 119.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
