# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_79p
_database_code_depnum_ccdc_archive 'CCDC 1941104'
loop_
_audit_author_name
_audit_author_address
'Ying Yeung Yeung'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Br2'
_chemical_formula_weight         368.11

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.2066(5)
_cell_length_b                   16.0484(10)
_cell_length_c                   5.6011(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.525(2)
_cell_angle_gamma                90
_cell_volume                     725.27(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    93
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    5.569
_shelx_estimated_absorpt_T_min   0.214
_shelx_estimated_absorpt_T_max   0.402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2968
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10259
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1306
_reflns_number_gt                1199
_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       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_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)+(0.0310P)²+0.4079P] 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         1306
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.001
_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 0.42463(3) 0.33292(2) 0.08093(5) 0.04436(13) Uani 1 1 d . . . . .
C1 C 0.4702(3) 0.47835(14) 0.3788(4) 0.0327(5) Uani 1 1 d . . . . .
H1A H 0.350022 0.478361 0.342771 0.039 Uiso 1 1 calc R U . . .
H1B H 0.509633 0.508709 0.250755 0.039 Uiso 1 1 calc R U . . .
C2 C 0.5330(3) 0.38938(14) 0.3854(4) 0.0316(5) Uani 1 1 d . . . . .
H2A H 0.497266 0.361056 0.522072 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7181(3) 0.38054(14) 0.4161(4) 0.0311(5) Uani 1 1 d . . . . .
C4 C 0.8030(4) 0.33860(16) 0.6152(5) 0.0435(6) Uani 1 1 d . . . . .
H4A H 0.744970 0.313720 0.724163 0.052 Uiso 1 1 calc R U . . .
C5 C 0.9742(4) 0.33327(18) 0.6542(7) 0.0557(8) Uani 1 1 d . . . . .
H5A H 1.030926 0.305618 0.790256 0.067 Uiso 1 1 calc R U . . .
C6 C 1.0603(4) 0.3689(2) 0.4913(6) 0.0542(8) Uani 1 1 d . . . . .
H6A H 1.175251 0.365154 0.516974 0.065 Uiso 1 1 calc R U . . .
C7 C 0.9774(4) 0.4097(2) 0.2928(6) 0.0570(8) Uani 1 1 d . . . . .
H7A H 1.035965 0.433087 0.182185 0.068 Uiso 1 1 calc R U . . .
C8 C 0.8071(3) 0.41656(18) 0.2546(5) 0.0460(7) Uani 1 1 d . . . . .
H8A H 0.751597 0.445456 0.120076 0.055 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0468(2) 0.04047(18) 0.0421(2) -0.00966(11) -0.00175(13) -0.00325(11)
C1 0.0311(12) 0.0323(12) 0.0336(13) -0.0013(10) 0.0027(10) 0.0023(10)
C2 0.0333(12) 0.0303(12) 0.0307(12) -0.0011(9) 0.0041(10) -0.0016(10)
C3 0.0326(12) 0.0280(11) 0.0324(12) -0.0037(9) 0.0050(10) 0.0019(9)
C4 0.0465(16) 0.0408(14) 0.0423(16) 0.0063(11) 0.0054(13) 0.0012(12)
C5 0.0449(16) 0.0570(19) 0.0580(19) 0.0092(14) -0.0096(15) 0.0094(14)
C6 0.0323(14) 0.0602(18) 0.069(2) -0.0045(17) 0.0052(14) 0.0036(13)
C7 0.0415(16) 0.075(2) 0.0572(19) 0.0037(16) 0.0173(14) -0.0055(15)
C8 0.0409(15) 0.0573(17) 0.0396(15) 0.0090(13) 0.0067(12) 0.0024(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.992(2) . ?
C1 C2 1.516(3) . ?
C1 C1 1.524(5) 3_666 ?
C2 C3 1.504(3) . ?
C3 C4 1.378(4) . ?
C3 C8 1.388(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.377(5) . ?
C6 C7 1.360(5) . ?
C7 C8 1.379(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
C2 C1 C1 110.8(2) . 3_666 ?
C3 C2 C1 115.05(19) . . ?
C3 C2 Br1 109.80(16) . . ?
C1 C2 Br1 108.10(16) . . ?
C4 C3 C8 118.8(2) . . ?
C4 C3 C2 119.3(2) . . ?
C8 C3 C2 121.8(2) . . ?
C3 C4 C5 120.4(3) . . ?
C6 C5 C4 119.9(3) . . ?
C7 C6 C5 120.1(3) . . ?
C6 C7 C8 120.4(3) . . ?
C7 C8 C3 120.3(3) . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.058

_shelx_res_file                  
;
TITL P_a.res in P2(1)/c
    p.res
    created by SHELXL-2018/3 at 11:20:50 on 17-Jun-2019
CELL  0.71073   8.2066  16.0484   5.6011   90.000  100.525   90.000
ZERR  2.000   0.0005   0.0010   0.0003    0.000    0.002    0.000
LATT 1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C  H  Br
UNIT 32 32 4
rem C16 H16 Br2
rem d8venture block colourless
omit -3 50.5
size 0.40 0.30 0.20
L.S. 10
acta
FMAP 2
PLAN 20
TEMP 23
WGHT    0.031000    0.407900
FVAR       0.94774
BR1   3    0.424634    0.332920    0.080932    11.00000    0.04677    0.04047 =
         0.04211   -0.00966   -0.00175   -0.00325
C1    1    0.470213    0.478347    0.378765    11.00000    0.03109    0.03228 =
         0.03357   -0.00132    0.00266    0.00229
AFIX  23
H1A   2    0.350022    0.478361    0.342771    11.00000   -1.20000
H1B   2    0.509633    0.508709    0.250755    11.00000   -1.20000
AFIX   0
C2    1    0.533012    0.389380    0.385437    11.00000    0.03325    0.03026 =
         0.03067   -0.00109    0.00407   -0.00162
AFIX  13
H2A   2    0.497266    0.361056    0.522072    11.00000   -1.20000
AFIX   0
C3    1    0.718070    0.380543    0.416122    11.00000    0.03265    0.02797 =
         0.03236   -0.00371    0.00497    0.00195
C4    1    0.803021    0.338605    0.615231    11.00000    0.04651    0.04083 =
         0.04226    0.00626    0.00539    0.00122
AFIX  43
H4A   2    0.744970    0.313720    0.724163    11.00000   -1.20000
AFIX   0
C5    1    0.974174    0.333266    0.654197    11.00000    0.04490    0.05702 =
         0.05797    0.00919   -0.00962    0.00940
AFIX  43
H5A   2    1.030926    0.305618    0.790256    11.00000   -1.20000
AFIX   0
C6    1    1.060288    0.368933    0.491299    11.00000    0.03226    0.06017 =
         0.06856   -0.00454    0.00515    0.00359
AFIX  43
H6A   2    1.175251    0.365154    0.516974    11.00000   -1.20000
AFIX   0
C7    1    0.977408    0.409693    0.292848    11.00000    0.04151    0.07526 =
         0.05725    0.00368    0.01731   -0.00545
AFIX  43
H7A   2    1.035965    0.433087    0.182185    11.00000   -1.20000
AFIX   0
C8    1    0.807067    0.416563    0.254633    11.00000    0.04090    0.05732 =
         0.03959    0.00901    0.00670    0.00235
AFIX  43
H8A   2    0.751597    0.445456    0.120076    11.00000   -1.20000

AFIX   0
HKLF 4




REM  P_a.res in P2(1)/c
REM wR2 = 0.064876, GooF = S = 1.16562, Restrained GooF = 1.16562 for all data
REM R1 = 0.023051 for 1199 Fo > 4sig(Fo) and 0.025801 for all 1306 data
REM 82 parameters refined using 0 restraints

END

WGHT      0.0295      0.4742

REM Highest difference peak  0.298,  deepest hole -0.402,  1-sigma level  0.058
Q1    1   0.3763  0.3819  0.0380  11.00000  0.05    0.30
Q2    1   0.5393  0.5406  0.1809  11.00000  0.05    0.27
Q3    1   0.5049  0.4390  0.3738  11.00000  0.05    0.26
Q4    1   0.6331  0.3813  0.4002  11.00000  0.05    0.24
Q5    1   0.4807  0.3811 -0.0833  11.00000  0.05    0.23
Q6    1   0.3955  0.3152  0.2197  11.00000  0.05    0.21
Q7    1   0.7567  0.3836  0.5424  11.00000  0.05    0.19
Q8    1   0.7587  0.4220  0.3858  11.00000  0.05    0.18
Q9    1   0.4003  0.4776  0.3776  11.00000  0.05    0.18
Q10   1   0.9963  0.3643  0.3466  11.00000  0.05    0.16
Q11   1   0.5629  0.3199  0.8431  11.00000  0.05    0.15
Q12   1   0.5562  0.4444  0.2502  11.00000  0.05    0.14
Q13   1   0.4742  0.3535  0.4180  11.00000  0.05    0.14
Q14   1   1.0170  0.3405  0.5339  11.00000  0.05    0.14
Q15   1   0.7239  0.5375  0.3201  11.00000  0.05    0.13
Q16   1   0.3812  0.3850  0.2446  11.00000  0.05    0.13
Q17   1   0.2141  0.4997  0.5144  11.00000  0.05    0.12
Q18   1   1.1233  0.3366  0.4057  11.00000  0.05    0.12
Q19   1   1.0311  0.4817  0.2255  11.00000  0.05    0.12
Q20   1   1.2064  0.3416  0.4211  11.00000  0.05    0.12
;
_shelx_res_checksum              26161
