# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 1904039'
loop_
_audit_author_name
_audit_author_address
'Chao Chen'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 Br O'
_chemical_formula_sum            'C13 H15 Br O'
_chemical_formula_weight         267.16

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5578(11)
_cell_length_b                   7.5212(16)
_cell_length_c                   15.993(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.303(11)
_cell_angle_gamma                90
_cell_volume                     1205.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    8197
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      68.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   0.4065
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.406
_shelx_estimated_absorpt_T_min   0.418
_shelx_estimated_absorpt_T_max   0.473
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10799
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.457
_diffrn_reflns_theta_max         68.387
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2199
_reflns_number_gt                2025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1225P)²+0.9861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2199
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1968
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.19115(5) 0.68212(8) 0.45522(3) 0.0790(3) Uani 1 1 d . . . . .
C1 C 0.3856(4) 0.6664(4) 0.6284(2) 0.0441(8) Uani 1 1 d . . . . .
O1 O 0.5302(3) 0.7286(4) 0.53903(19) 0.0592(7) Uani 1 1 d . . . . .
C3 C 0.4150(6) 0.9578(6) 0.6968(3) 0.0704(12) Uani 1 1 d . . . . .
H3A H 0.477636 0.928488 0.753881 0.085 Uiso 1 1 calc R U . . .
H3B H 0.371991 1.069819 0.701023 0.085 Uiso 1 1 calc R U . . .
C2 C 0.3120(5) 0.8093(5) 0.6636(3) 0.0589(10) Uani 1 1 d . . . . .
H2A H 0.234672 0.852438 0.617264 0.071 Uiso 1 1 calc R U . . .
H2B H 0.283042 0.762730 0.711200 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4851(5) 0.9663(5) 0.6260(3) 0.0694(12) Uani 1 1 d . . . . .
H4A H 0.440374 1.049852 0.580018 0.083 Uiso 1 1 calc R U . . .
H4B H 0.577380 1.002512 0.651592 0.083 Uiso 1 1 calc R U . . .
C5 C 0.4764(4) 0.7801(5) 0.5899(3) 0.0492(8) Uani 1 1 d . . . . .
C7 C 0.1922(3) 0.4139(6) 0.5876(2) 0.0535(9) Uani 1 1 d . . . . .
H7A H 0.146230 0.338053 0.539369 0.080 Uiso 1 1 calc R U . . .
H7B H 0.128693 0.486630 0.603595 0.080 Uiso 1 1 calc R U . . .
H7C H 0.240442 0.342479 0.637114 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2974(3) 0.5420(5) 0.5581(2) 0.0513(8) Uani 1 1 d . . . . .
H6 H 0.356575 0.464220 0.538123 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5758(4) 0.4452(5) 0.6814(3) 0.0531(8) Uani 1 1 d . . . . .
H9 H 0.585868 0.451425 0.625715 0.064 Uiso 1 1 calc R U . . .
C8 C 0.4779(3) 0.5481(4) 0.7007(2) 0.0442(7) Uani 1 1 d . . . . .
C10 C 0.6577(5) 0.3345(6) 0.7446(3) 0.0655(11) Uani 1 1 d . . . . .
H10 H 0.723233 0.268088 0.731402 0.079 Uiso 1 1 calc R U . . .
C11 C 0.6428(5) 0.3217(6) 0.8274(4) 0.0728(13) Uani 1 1 d . . . . .
H11 H 0.697106 0.245705 0.869468 0.087 Uiso 1 1 calc R U . . .
C12 C 0.5482(5) 0.4212(7) 0.8467(3) 0.0744(12) Uani 1 1 d . . . . .
H12 H 0.538967 0.413823 0.902500 0.089 Uiso 1 1 calc R U . . .
C13 C 0.4650(4) 0.5337(6) 0.7846(3) 0.0606(10) Uani 1 1 d . . . . .
H13 H 0.400383 0.599824 0.798993 0.073 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
Br1 C6 1.979(4) . ?
C1 C6 1.533(5) . ?
C1 C2 1.533(5) . ?
C1 C8 1.539(5) . ?
C1 C5 1.549(5) . ?
O1 C5 1.195(5) . ?
C3 C2 1.533(7) . ?
C3 C4 1.535(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C5 1.507(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 C6 1.647(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6 0.9800 . ?
C9 C10 1.384(6) . ?
C9 C8 1.402(5) . ?
C9 H9 0.9300 . ?
C8 C13 1.394(5) . ?
C10 C11 1.385(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 115.8(3) . . ?
C6 C1 C8 107.1(3) . . ?
C2 C1 C8 113.8(3) . . ?
C6 C1 C5 110.8(3) . . ?
C2 C1 C5 101.9(3) . . ?
C8 C1 C5 107.0(3) . . ?
C2 C3 C4 103.3(4) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C3 C2 C1 104.5(3) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C5 C4 C3 104.9(3) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.8 . . ?
O1 C5 C4 125.3(4) . . ?
O1 C5 C1 125.3(3) . . ?
C4 C5 C1 109.4(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C6 C7 117.1(3) . . ?
C1 C6 Br1 109.9(3) . . ?
C7 C6 Br1 107.0(2) . . ?
C1 C6 H6 107.5 . . ?
C7 C6 H6 107.5 . . ?
Br1 C6 H6 107.5 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C13 C8 C9 118.1(3) . . ?
C13 C8 C1 122.5(3) . . ?
C9 C8 C1 119.3(3) . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.3(5) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?

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
C4 C3 C2 C1 40.5(4) . . . . ?
C6 C1 C2 C3 -155.1(3) . . . . ?
C8 C1 C2 C3 80.0(4) . . . . ?
C5 C1 C2 C3 -34.8(4) . . . . ?
C2 C3 C4 C5 -29.3(5) . . . . ?
C3 C4 C5 O1 -172.7(4) . . . . ?
C3 C4 C5 C1 7.8(5) . . . . ?
C6 C1 C5 O1 -39.0(5) . . . . ?
C2 C1 C5 O1 -162.8(4) . . . . ?
C8 C1 C5 O1 77.5(5) . . . . ?
C6 C1 C5 C4 140.5(4) . . . . ?
C2 C1 C5 C4 16.7(4) . . . . ?
C8 C1 C5 C4 -103.1(4) . . . . ?
C2 C1 C6 C7 -63.4(4) . . . . ?
C8 C1 C6 C7 64.8(4) . . . . ?
C5 C1 C6 C7 -178.8(3) . . . . ?
C2 C1 C6 Br1 58.9(4) . . . . ?
C8 C1 C6 Br1 -172.9(2) . . . . ?
C5 C1 C6 Br1 -56.5(3) . . . . ?
C10 C9 C8 C13 -0.7(6) . . . . ?
C10 C9 C8 C1 -178.3(4) . . . . ?
C6 C1 C8 C13 -110.3(4) . . . . ?
C2 C1 C8 C13 19.0(5) . . . . ?
C5 C1 C8 C13 130.8(4) . . . . ?
C6 C1 C8 C9 67.2(4) . . . . ?
C2 C1 C8 C9 -163.4(3) . . . . ?
C5 C1 C8 C9 -51.6(4) . . . . ?
C8 C9 C10 C11 0.9(6) . . . . ?
C9 C10 C11 C12 -1.0(7) . . . . ?
C10 C11 C12 C13 0.8(7) . . . . ?
C11 C12 C13 C8 -0.6(7) . . . . ?
C9 C8 C13 C12 0.5(6) . . . . ?
C1 C8 C13 C12 178.1(4) . . . . ?

_refine_diff_density_max         1.002
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.088



