# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_cxy1949_0m
_database_code_depnum_ccdc_archive 'CCDC 2191583'
_audit_update_record             
;
2022-07-20 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26
_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'
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      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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.7082(3)
_cell_length_b                   12.0888(5)
_cell_length_c                   12.3892(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1154.46(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.65
_cell_measurement_theta_min      5.11
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.7083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0827 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9399.
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    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22748
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.724
_diffrn_reflns_theta_min         5.112
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2273
_reflns_number_total             2296
_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 (Bruker, 2018)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 941 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.0120(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.078
_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)+(0.0328P)²+0.3028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0642
_refine_special_details          ?
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C14(H14), C15(H15)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O1 O 0.31203(14) 0.13416(9) 0.29789(9) 0.0155(3) Uani 1 1 d . . . . .
O2 O 0.37602(15) 0.03846(9) 0.15320(9) 0.0181(3) Uani 1 1 d . . . . .
O3 O 0.55115(16) 0.34337(9) 0.45458(9) 0.0159(3) Uani 1 1 d . . . . .
H3 H 0.560623 0.402467 0.419417 0.024 Uiso 1 1 calc R U . . .
C1 C 0.0304(2) 0.46221(14) 0.26055(13) 0.0206(4) Uani 1 1 d . . . . .
H1 H -0.079750 0.492663 0.277985 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0986(2) 0.37642(14) 0.32196(13) 0.0178(3) Uani 1 1 d . . . . .
H2 H 0.034783 0.348195 0.381489 0.021 Uiso 1 1 calc R U . . .
C3 C 0.26017(19) 0.33151(13) 0.29674(12) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.35549(19) 0.37255(12) 0.20911(12) 0.0128(3) Uani 1 1 d . . . . .
C5 C 0.52834(19) 0.32294(12) 0.18560(12) 0.0120(3) Uani 1 1 d . . . . .
C6 C 0.6393(2) 0.36536(13) 0.09241(12) 0.0160(3) Uani 1 1 d . . . . .
H6A H 0.698841 0.434833 0.112802 0.019 Uiso 1 1 calc R U . . .
H6B H 0.566687 0.379513 0.027944 0.019 Uiso 1 1 calc R U . . .
C7 C 0.7719(2) 0.27343(14) 0.06954(13) 0.0183(4) Uani 1 1 d . . . . .
H7A H 0.875652 0.282217 0.115810 0.022 Uiso 1 1 calc R U . . .
H7B H 0.808521 0.274955 -0.007032 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6772(2) 0.16478(13) 0.09567(12) 0.0153(3) Uani 1 1 d . . . . .
H8A H 0.612238 0.137638 0.032039 0.018 Uiso 1 1 calc R U . . .
H8B H 0.760462 0.107046 0.118695 0.018 Uiso 1 1 calc R U . . .
C9 C 0.6233(2) 0.26630(12) 0.27700(12) 0.0130(3) Uani 1 1 d . . . . .
H9 H 0.751717 0.277198 0.280725 0.016 Uiso 1 1 calc R U . . .
C10 C 0.5287(2) 0.25363(13) 0.38221(11) 0.0132(3) Uani 1 1 d . . . . .
H10 H 0.573040 0.185278 0.418356 0.016 Uiso 1 1 calc R U . . .
C11 C 0.3353(2) 0.23704(13) 0.35935(12) 0.0136(3) Uani 1 1 d . . . . .
H11 H 0.272202 0.230405 0.429562 0.016 Uiso 1 1 calc R U . . .
C12 C 0.41027(19) 0.11779(12) 0.20949(12) 0.0130(3) Uani 1 1 d . . . . .
C13 C 0.5550(2) 0.19423(12) 0.18650(13) 0.0127(3) Uani 1 1 d . . . . .
C14 C 0.1240(2) 0.50311(14) 0.17365(14) 0.0197(3) Uani 1 1 d . . . . .
H14 H 0.077417 0.561462 0.131237 0.024 Uiso 1 1 calc R U . . .
C15 C 0.2860(2) 0.45898(13) 0.14825(13) 0.0162(3) Uani 1 1 d . . . . .
H15 H 0.349686 0.488001 0.089014 0.019 Uiso 1 1 calc R U . . .


_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
O1 C11 1.4692(18) . ?
O1 C12 1.3461(19) . ?
O2 C12 1.2149(19) . ?
O3 H3 0.8400 . ?
O3 C10 1.4180(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.390(2) . ?
C1 C14 1.387(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(2) . ?
C3 C4 1.402(2) . ?
C3 C11 1.497(2) . ?
C4 C5 1.490(2) . ?
C4 C15 1.395(2) . ?
C5 C6 1.525(2) . ?
C5 C9 1.512(2) . ?
C5 C13 1.5696(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.536(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.537(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C13 1.510(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.501(2) . ?
C9 C13 1.514(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.531(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.476(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(2) . ?
C15 H15 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 C11 118.51(11) . . ?
C10 O3 H3 109.5 . . ?
C2 C1 H1 120.2 . . ?
C14 C1 H1 120.2 . . ?
C14 C1 C2 119.60(15) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.41(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.27(15) . . ?
C2 C3 C11 121.78(14) . . ?
C4 C3 C11 117.93(13) . . ?
C3 C4 C5 118.54(13) . . ?
C15 C4 C3 118.85(14) . . ?
C15 C4 C5 122.61(14) . . ?
C4 C5 C6 120.92(13) . . ?
C4 C5 C9 117.94(13) . . ?
C4 C5 C13 120.98(13) . . ?
C6 C5 C13 105.38(12) . . ?
C9 C5 C6 116.61(13) . . ?
C9 C5 C13 58.83(9) . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
C5 C6 C7 105.63(12) . . ?
H6A C6 H6B 108.7 . . ?
C7 C6 H6A 110.6 . . ?
C7 C6 H6B 110.6 . . ?
C6 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C6 C7 C8 105.29(12) . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C13 C8 C7 104.57(12) . . ?
C13 C8 H8A 110.8 . . ?
C13 C8 H8B 110.8 . . ?
C5 C9 H9 117.0 . . ?
C5 C9 C13 62.48(9) . . ?
C10 C9 C5 117.49(13) . . ?
C10 C9 H9 117.0 . . ?
C10 C9 C13 114.56(13) . . ?
C13 C9 H9 117.0 . . ?
O3 C10 C9 114.32(13) . . ?
O3 C10 H10 107.9 . . ?
O3 C10 C11 109.64(12) . . ?
C9 C10 H10 107.9 . . ?
C9 C10 C11 108.99(12) . . ?
C11 C10 H10 107.9 . . ?
O1 C11 C3 109.26(12) . . ?
O1 C11 C10 109.02(12) . . ?
O1 C11 H11 108.9 . . ?
C3 C11 C10 111.89(13) . . ?
C3 C11 H11 108.9 . . ?
C10 C11 H11 108.9 . . ?
O1 C12 C13 119.35(13) . . ?
O2 C12 O1 117.44(13) . . ?
O2 C12 C13 123.20(14) . . ?
C8 C13 C5 108.06(13) . . ?
C8 C13 C9 118.07(13) . . ?
C9 C13 C5 58.69(9) . . ?
C12 C13 C5 121.53(13) . . ?
C12 C13 C8 117.89(13) . . ?
C12 C13 C9 118.67(13) . . ?
C1 C14 H14 119.8 . . ?
C1 C14 C15 120.32(15) . . ?
C15 C14 H14 119.8 . . ?
C4 C15 H15 119.7 . . ?
C14 C15 C4 120.55(15) . . ?
C14 C15 H15 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C13 C5 -50.8(2) . . . . ?
O1 C12 C13 C8 171.83(13) . . . . ?
O1 C12 C13 C9 18.2(2) . . . . ?
O2 C12 C13 C5 130.56(16) . . . . ?
O2 C12 C13 C8 -6.8(2) . . . . ?
O2 C12 C13 C9 -160.51(14) . . . . ?
O3 C10 C11 O1 -171.51(11) . . . . ?
O3 C10 C11 C3 67.52(16) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C2 C3 C11 -178.32(14) . . . . ?
C1 C14 C15 C4 0.6(2) . . . . ?
C2 C1 C14 C15 -0.4(2) . . . . ?
C2 C3 C4 C5 179.42(13) . . . . ?
C2 C3 C4 C15 0.2(2) . . . . ?
C2 C3 C11 O1 101.70(16) . . . . ?
C2 C3 C11 C10 -137.46(14) . . . . ?
C3 C4 C5 C6 -179.04(13) . . . . ?
C3 C4 C5 C9 -23.72(19) . . . . ?
C3 C4 C5 C13 44.9(2) . . . . ?
C3 C4 C15 C14 -0.5(2) . . . . ?
C4 C3 C11 O1 -76.68(16) . . . . ?
C4 C3 C11 C10 44.15(18) . . . . ?
C4 C5 C6 C7 -161.58(13) . . . . ?
C4 C5 C9 C10 6.21(19) . . . . ?
C4 C5 C9 C13 111.11(15) . . . . ?
C4 C5 C13 C8 141.61(14) . . . . ?
C4 C5 C13 C9 -106.00(15) . . . . ?
C4 C5 C13 C12 0.6(2) . . . . ?
C5 C4 C15 C14 -179.70(14) . . . . ?
C5 C6 C7 C8 32.47(16) . . . . ?
C5 C9 C10 O3 -89.72(16) . . . . ?
C5 C9 C10 C11 33.35(18) . . . . ?
C5 C9 C13 C8 94.99(15) . . . . ?
C5 C9 C13 C12 -111.40(15) . . . . ?
C6 C5 C9 C10 162.60(13) . . . . ?
C6 C5 C9 C13 -92.50(14) . . . . ?
C6 C5 C13 C8 -0.28(16) . . . . ?
C6 C5 C13 C9 112.12(13) . . . . ?
C6 C5 C13 C12 -141.29(14) . . . . ?
C6 C7 C8 C13 -32.27(16) . . . . ?
C7 C8 C13 C5 20.00(16) . . . . ?
C7 C8 C13 C9 -43.54(17) . . . . ?
C7 C8 C13 C12 162.64(13) . . . . ?
C9 C5 C6 C7 42.78(17) . . . . ?
C9 C5 C13 C8 -112.39(14) . . . . ?
C9 C5 C13 C12 106.60(16) . . . . ?
C9 C10 C11 O1 62.67(16) . . . . ?
C9 C10 C11 C3 -58.29(16) . . . . ?
C10 C9 C13 C5 109.52(15) . . . . ?
C10 C9 C13 C8 -155.49(13) . . . . ?
C10 C9 C13 C12 -1.9(2) . . . . ?
C11 O1 C12 O2 -172.03(13) . . . . ?
C11 O1 C12 C13 9.2(2) . . . . ?
C11 C3 C4 C5 -2.2(2) . . . . ?
C11 C3 C4 C15 178.62(13) . . . . ?
C12 O1 C11 C3 72.53(16) . . . . ?
C12 O1 C11 C10 -50.03(17) . . . . ?
C13 C5 C6 C7 -19.67(16) . . . . ?
C13 C5 C9 C10 -104.90(15) . . . . ?
C13 C9 C10 O3 -160.15(13) . . . . ?
C13 C9 C10 C11 -37.09(18) . . . . ?
C14 C1 C2 C3 0.0(2) . . . . ?
C15 C4 C5 C6 0.1(2) . . . . ?
C15 C4 C5 C9 155.46(14) . . . . ?
C15 C4 C5 C13 -135.94(16) . . . . ?

_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. 
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data_cxy3584_0m
_database_code_depnum_ccdc_archive 'CCDC 2191640'
_audit_update_record             
;
2022-07-20 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-06-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 Br O2'
_chemical_formula_sum            'C15 H13 Br O2'
_chemical_formula_weight         305.16
_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'
O O 0.0492 0.0322 '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'

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

_cell_length_a                   7.0572(6)
_cell_length_b                   10.6743(7)
_cell_length_c                   15.6753(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1180.83(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.03
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.663
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1409 before and 0.0800 after correction.
The Ratio of minimum to maximum transmission is 0.5273.
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    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10210
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.257
_diffrn_reflns_theta_min         5.013
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.11
_diffrn_source_power             0.05550000000000001
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2308
_reflns_number_total             2316
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details 
;
 Flack x determined using 950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.089
_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)+(0.0523P)²+0.1128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0781
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C14(H14)
;
_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 0.81429(4) 0.58522(3) 0.38498(2) 0.02874(15) Uani 1 1 d . . . . .
O1 O 0.3215(3) 0.5814(2) 0.53192(15) 0.0295(5) Uani 1 1 d . . . . .
O2 O 0.1046(4) 0.4386(2) 0.55926(17) 0.0346(6) Uani 1 1 d . . . . .
C1 C 0.2720(5) 0.2318(3) 0.3355(3) 0.0304(7) Uani 1 1 d . . . . .
H1A H 0.397434 0.190463 0.332964 0.037 Uiso 1 1 calc R U . . .
H1B H 0.175647 0.174586 0.311210 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2750(5) 0.3571(3) 0.2870(2) 0.0291(7) Uani 1 1 d . . . . .
H2A H 0.363669 0.352876 0.238116 0.035 Uiso 1 1 calc R U . . .
H2B H 0.146997 0.377763 0.265231 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3402(4) 0.4546(3) 0.3511(2) 0.0260(7) Uani 1 1 d . . . . .
C4 C 0.3106(4) 0.5898(3) 0.3339(2) 0.0273(7) Uani 1 1 d . . . . .
C5 C 0.2263(5) 0.6320(3) 0.2583(3) 0.0298(7) Uani 1 1 d . . . . .
H5 H 0.184389 0.573475 0.216732 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2039(4) 0.7600(4) 0.2443(2) 0.0315(7) Uani 1 1 d . . . . .
H6 H 0.146562 0.788413 0.193034 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2645(5) 0.8461(4) 0.3044(3) 0.0337(8) Uani 1 1 d . . . . .
H7 H 0.246459 0.933102 0.294709 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2212(5) 0.2679(3) 0.4281(2) 0.0296(7) Uani 1 1 d . . . . .
H8A H 0.082194 0.267627 0.436471 0.036 Uiso 1 1 calc R U . . .
H8B H 0.279162 0.208425 0.469012 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3002(5) 0.3972(3) 0.4404(2) 0.0279(7) Uani 1 1 d . . . . .
C10 C 0.5028(4) 0.4184(3) 0.4090(2) 0.0261(6) Uani 1 1 d . . . . .
H10 H 0.578840 0.342892 0.393106 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6023(5) 0.5216(3) 0.4543(2) 0.0264(7) Uani 1 1 d . . . . .
H11 H 0.653175 0.488969 0.509482 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4655(5) 0.6290(3) 0.4727(2) 0.0273(7) Uani 1 1 d . . . . .
H12 H 0.536408 0.698847 0.500807 0.033 Uiso 1 1 calc R U . . .
C13 C 0.3734(4) 0.6773(3) 0.3935(3) 0.0274(7) Uani 1 1 d . . . . .
C14 C 0.3513(5) 0.8055(3) 0.3786(3) 0.0293(7) Uani 1 1 d . . . . .
H14 H 0.395690 0.864642 0.419288 0.035 Uiso 1 1 calc R U . . .
C15 C 0.2327(5) 0.4722(3) 0.5133(2) 0.0289(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.970(3) . ?
O1 C12 1.466(4) . ?
O1 C15 1.356(4) . ?
O2 C15 1.210(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.538(5) . ?
C1 C8 1.545(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.518(5) . ?
C3 C4 1.483(5) . ?
C3 C9 1.554(5) . ?
C3 C10 1.514(5) . ?
C4 C5 1.400(5) . ?
C4 C13 1.394(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(6) . ?
C7 H7 0.9500 . ?
C7 C14 1.384(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.501(5) . ?
C9 C10 1.529(4) . ?
C9 C15 1.475(5) . ?
C10 H10 1.0000 . ?
C10 C11 1.486(5) . ?
C11 H11 1.0000 . ?
C11 C12 1.527(5) . ?
C12 H12 1.0000 . ?
C12 C13 1.493(5) . ?
C13 C14 1.397(5) . ?
C14 H14 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
C15 O1 C12 118.8(3) . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
C2 C1 C8 104.6(3) . . ?
C8 C1 H1A 110.8 . . ?
C8 C1 H1B 110.8 . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 C1 105.8(3) . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C2 C3 C9 105.7(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 C9 121.5(3) . . ?
C4 C3 C10 117.7(3) . . ?
C10 C3 C2 116.9(3) . . ?
C10 C3 C9 59.8(2) . . ?
C5 C4 C3 121.8(3) . . ?
C13 C4 C3 119.0(3) . . ?
C13 C4 C5 119.1(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C14 120.1(3) . . ?
C14 C7 H7 120.0 . . ?
C1 C8 H8A 110.7 . . ?
C1 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C9 C8 C1 105.3(3) . . ?
C9 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
C8 C9 C3 108.3(3) . . ?
C8 C9 C10 116.2(3) . . ?
C10 C9 C3 58.8(2) . . ?
C15 C9 C3 122.9(3) . . ?
C15 C9 C8 118.6(3) . . ?
C15 C9 C10 118.1(3) . . ?
C3 C10 C9 61.4(2) . . ?
C3 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
C11 C10 C3 117.1(3) . . ?
C11 C10 C9 113.5(3) . . ?
C11 C10 H10 117.6 . . ?
Br1 C11 H11 108.9 . . ?
C10 C11 Br1 110.6(2) . . ?
C10 C11 H11 108.9 . . ?
C10 C11 C12 110.4(3) . . ?
C12 C11 Br1 109.0(2) . . ?
C12 C11 H11 108.9 . . ?
O1 C12 C11 107.3(3) . . ?
O1 C12 H12 109.1 . . ?
O1 C12 C13 110.1(3) . . ?
C11 C12 H12 109.1 . . ?
C13 C12 C11 112.1(3) . . ?
C13 C12 H12 109.1 . . ?
C4 C13 C12 117.7(3) . . ?
C4 C13 C14 120.6(3) . . ?
C14 C13 C12 121.7(3) . . ?
C7 C14 C13 119.7(4) . . ?
C7 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O1 C15 C9 118.9(3) . . ?
O2 C15 O1 118.2(3) . . ?
O2 C15 C9 122.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C11 C12 O1 -173.9(2) . . . . ?
Br1 C11 C12 C13 65.0(3) . . . . ?
O1 C12 C13 C4 -76.9(4) . . . . ?
O1 C12 C13 C14 103.5(4) . . . . ?
C1 C2 C3 C4 -163.4(3) . . . . ?
C1 C2 C3 C9 -21.0(4) . . . . ?
C1 C2 C3 C10 42.6(4) . . . . ?
C1 C8 C9 C3 17.4(3) . . . . ?
C1 C8 C9 C10 -46.2(4) . . . . ?
C1 C8 C9 C15 163.7(3) . . . . ?
C2 C1 C8 C9 -30.1(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C2 C3 C4 C13 -179.5(3) . . . . ?
C2 C3 C9 C8 2.2(4) . . . . ?
C2 C3 C9 C10 112.3(3) . . . . ?
C2 C3 C9 C15 -142.4(3) . . . . ?
C2 C3 C10 C9 -93.2(3) . . . . ?
C2 C3 C10 C11 163.4(3) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
C3 C4 C13 C12 -0.8(4) . . . . ?
C3 C4 C13 C14 178.7(3) . . . . ?
C3 C9 C10 C11 109.2(3) . . . . ?
C3 C9 C15 O1 -47.9(5) . . . . ?
C3 C9 C15 O2 134.4(4) . . . . ?
C3 C10 C11 Br1 -89.8(3) . . . . ?
C3 C10 C11 C12 30.9(4) . . . . ?
C4 C3 C9 C8 144.0(3) . . . . ?
C4 C3 C9 C10 -105.9(3) . . . . ?
C4 C3 C9 C15 -0.5(5) . . . . ?
C4 C3 C10 C9 112.1(3) . . . . ?
C4 C3 C10 C11 8.8(4) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C4 C13 C14 C7 0.7(5) . . . . ?
C5 C4 C13 C12 -179.0(3) . . . . ?
C5 C4 C13 C14 0.5(5) . . . . ?
C5 C6 C7 C14 1.2(5) . . . . ?
C6 C7 C14 C13 -1.5(5) . . . . ?
C8 C1 C2 C3 31.8(4) . . . . ?
C8 C9 C10 C3 96.4(3) . . . . ?
C8 C9 C10 C11 -154.4(3) . . . . ?
C8 C9 C15 O1 170.9(3) . . . . ?
C8 C9 C15 O2 -6.8(5) . . . . ?
C9 C3 C4 C5 -137.8(3) . . . . ?
C9 C3 C4 C13 44.1(4) . . . . ?
C9 C3 C10 C11 -103.3(3) . . . . ?
C9 C10 C11 Br1 -158.5(2) . . . . ?
C9 C10 C11 C12 -37.7(4) . . . . ?
C10 C3 C4 C5 152.5(3) . . . . ?
C10 C3 C4 C13 -25.7(4) . . . . ?
C10 C3 C9 C8 -110.1(3) . . . . ?
C10 C3 C9 C15 105.3(4) . . . . ?
C10 C9 C15 O1 21.4(5) . . . . ?
C10 C9 C15 O2 -156.3(3) . . . . ?
C10 C11 C12 O1 64.4(4) . . . . ?
C10 C11 C12 C13 -56.6(4) . . . . ?
C11 C12 C13 C4 42.5(4) . . . . ?
C11 C12 C13 C14 -137.0(3) . . . . ?
C12 O1 C15 O2 -174.6(3) . . . . ?
C12 O1 C15 C9 7.6(4) . . . . ?
C12 C13 C14 C7 -179.8(3) . . . . ?
C13 C4 C5 C6 -0.9(5) . . . . ?
C15 O1 C12 C11 -49.9(4) . . . . ?
C15 O1 C12 C13 72.4(4) . . . . ?
C15 C9 C10 C3 -113.4(3) . . . . ?
C15 C9 C10 C11 -4.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
