# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535002'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-chlorobenzoic acid/2-bromo-4-chlorobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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/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                   7.2271(7)
_cell_length_b                   8.9480(7)
_cell_length_c                   12.1887(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.819(9)
_cell_angle_gamma                90
_cell_volume                     758.37(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1979
_cell_measurement_theta_min      2.7960
_cell_measurement_theta_max      27.4960

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.062
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.710
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5398
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1737
_reflns_number_gt                1374
_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    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ', Occupancy Disorder'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²+0.7369P] 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         1737
_refine_ls_number_parameters     107
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.3893(5) 0.1215(3) 0.24133(9) 0.0226(3) Uani 0.752(2) 1 d D . P A 1
Cl1 Cl 0.080(3) -0.3224(8) -0.0497(19) 0.0228(11) Uani 0.752(2) 1 d D . P A 1
Cl2 Cl 0.384(4) 0.131(3) 0.2251(8) 0.0226(3) Uani 0.248(2) 1 d D . P A 2
Br2 Br 0.087(3) -0.3432(10) -0.056(2) 0.0228(11) Uani 0.248(2) 1 d D . P A 2
O1 O 0.4106(4) 0.3598(3) -0.0926(3) 0.0264(8) Uani 1 1 d . . . . .
O2 O 0.4454(5) 0.3694(4) 0.0946(3) 0.0284(8) Uani 1 1 d . . . . .
H2 H 0.486474 0.452666 0.085677 0.043 Uiso 1 1 calc R U . . .
C1 C 0.3962(5) 0.3019(5) -0.0006(4) 0.0138(9) Uani 1 1 d . . . . .
C2 C 0.3164(6) 0.1471(5) -0.0065(4) 0.0155(9) Uani 1 1 d . . . . .
C3 C 0.3072(6) 0.0591(5) 0.0875(3) 0.0174(9) Uani 1 1 d D . . . .
C6 C 0.1763(6) -0.0597(5) -0.1298(4) 0.0194(10) Uani 1 1 d . . . . .
H6 H 0.130396 -0.099592 -0.202690 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2381(6) -0.0848(5) 0.0750(4) 0.0180(9) Uani 1 1 d . . . . .
H4 H 0.234717 -0.142066 0.138077 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2487(6) 0.0831(5) -0.1142(4) 0.0179(10) Uani 1 1 d . . . . .
H7 H 0.252562 0.139004 -0.177857 0.022 Uiso 1 1 calc R U . . .
C5 C 0.1734(6) -0.1424(3) -0.0350(4) 0.0200(10) Uani 1 1 d D . . . .

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 0.0335(4) 0.0187(5) 0.0142(5) 0.0013(6) 0.0044(7) 0.0008(4)
Cl1 0.0233(12) 0.0069(17) 0.039(2) -0.008(2) 0.0093(9) 0.000(2)
Cl2 0.0335(4) 0.0187(5) 0.0142(5) 0.0013(6) 0.0044(7) 0.0008(4)
Br2 0.0233(12) 0.0069(17) 0.039(2) -0.008(2) 0.0093(9) 0.000(2)
O1 0.040(2) 0.0163(19) 0.0223(19) 0.0039(14) 0.0076(15) -0.0043(14)
O2 0.043(2) 0.0171(18) 0.0255(19) -0.0067(15) 0.0099(16) -0.0112(15)
C1 0.012(2) 0.013(2) 0.016(2) 0.0016(18) 0.0035(17) 0.0021(16)
C2 0.015(2) 0.015(2) 0.016(2) 0.0011(18) 0.0038(17) 0.0003(17)
C3 0.019(2) 0.017(2) 0.017(2) -0.0013(18) 0.0049(18) 0.0018(18)
C6 0.020(2) 0.019(3) 0.020(2) -0.0045(19) 0.0058(18) 0.0003(18)
C4 0.017(2) 0.017(2) 0.022(2) 0.0030(19) 0.0088(18) 0.0018(17)
C7 0.015(2) 0.018(2) 0.022(2) 0.0002(19) 0.0068(18) 0.0019(17)
C5 0.016(2) 0.013(2) 0.032(3) 0.000(2) 0.0077(19) 0.0018(17)

_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 C3 1.890(4) . ?
Cl1 C5 1.737(4) . ?
Cl2 C3 1.740(5) . ?
Br2 C5 1.896(5) . ?
O1 C1 1.266(5) . ?
O2 C1 1.269(5) . ?
C1 C2 1.494(6) . ?
C2 C7 1.393(6) . ?
C2 C3 1.407(6) . ?
C3 C4 1.374(6) . ?
C6 C7 1.374(6) . ?
C6 C5 1.377(6) . ?
C4 C5 1.393(6) . ?

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
O1 C1 O2 123.0(4) . . ?
O1 C1 C2 117.4(4) . . ?
O2 C1 C2 119.6(4) . . ?
C7 C2 C3 117.0(4) . . ?
C7 C2 C1 117.3(4) . . ?
C3 C2 C1 125.7(4) . . ?
C4 C3 C2 122.0(4) . . ?
C4 C3 Cl2 117.7(8) . . ?
C2 C3 Cl2 120.3(8) . . ?
C4 C3 Br1 113.2(3) . . ?
C2 C3 Br1 124.8(3) . . ?
C7 C6 C5 118.4(4) . . ?
C3 C4 C5 118.0(4) . . ?
C6 C7 C2 122.4(4) . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 Cl1 120.4(8) . . ?
C4 C5 Cl1 117.5(8) . . ?
C6 C5 Br2 118.5(9) . . ?
C4 C5 Br2 119.4(9) . . ?

_refine_diff_density_max         0.577
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.130

_shelx_res_file                  
;
TITL red in P2(1)/n
    shelx.res
    created by SHELXL-2016/6 at 15:54:50 on 17-Apr-2017
CELL  0.71073   7.2271   8.9480  12.1887   90.000  105.819   90.000
ZERR     4.00   0.0007   0.0007   0.0011    0.000    0.009    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    CL   BR
UNIT  28 16 8 4 4
MERG   2
EADP BR1 CL2
EADP BR2 CL1
DFIX 1.900 0.005 C5 BR2
DFIX 1.900 0.005 C3 BR1
DFIX 1.740 0.005 C3 CL2
DFIX 1.740 0.005 C5 CL1
FMAP   2
PLAN   20
ACTA
LIST   3
L.S.   5
WGHT    0.023500    0.736900
FVAR       2.14301   0.75205
PART    1
BR1   5    0.389317    0.121498    0.241334    21.00000    0.03351    0.01867 =
         0.01423    0.00130    0.00437    0.00075
CL1   4    0.079744   -0.322408   -0.049742    21.00000    0.02329    0.00691 =
         0.03880   -0.00756    0.00927   -0.00048
PART    2
CL2   4    0.383647    0.131099    0.225118   -21.00000    0.03351    0.01867 =
         0.01423    0.00130    0.00437    0.00075
BR2   5    0.087159   -0.343229   -0.055628   -21.00000    0.02329    0.00691 =
         0.03880   -0.00756    0.00927   -0.00048
PART    0
O1    3    0.410557    0.359752   -0.092644    11.00000    0.04014    0.01635 =
         0.02227    0.00388    0.00757   -0.00431
O2    3    0.445378    0.369412    0.094553    11.00000    0.04289    0.01710 =
         0.02554   -0.00672    0.00988   -0.01123
AFIX  83
H2    2    0.486474    0.452666    0.085677    11.00000   -1.50000
AFIX   0
C1    1    0.396161    0.301873   -0.000585    11.00000    0.01225    0.01295 =
         0.01592    0.00162    0.00354    0.00207
C2    1    0.316434    0.147098   -0.006499    11.00000    0.01523    0.01520 =
         0.01573    0.00114    0.00382    0.00028
C3    1    0.307219    0.059079    0.087506    11.00000    0.01876    0.01700 =
         0.01651   -0.00125    0.00494    0.00178
C6    1    0.176301   -0.059740   -0.129848    11.00000    0.01960    0.01872 =
         0.02006   -0.00455    0.00582    0.00034
AFIX  43
H6    2    0.130396   -0.099592   -0.202690    11.00000   -1.20000
AFIX   0
C4    1    0.238134   -0.084831    0.074970    11.00000    0.01748    0.01666 =
         0.02181    0.00299    0.00881    0.00180
AFIX  43
H4    2    0.234717   -0.142066    0.138077    11.00000   -1.20000
AFIX   0
C7    1    0.248670    0.083061   -0.114220    11.00000    0.01453    0.01832 =
         0.02201    0.00024    0.00679    0.00192
AFIX  43
H7    2    0.252562    0.139004   -0.177857    11.00000   -1.20000
AFIX   0
C5    1    0.173399   -0.142416   -0.035023    11.00000    0.01620    0.01293 =
         0.03152    0.00001    0.00767    0.00181
HKLF    4




REM  red in P2(1)/n
REM R1 =  0.0458 for    1374 Fo > 4sig(Fo)  and  0.0618 for all    1737 data
REM    107 parameters refined using      4 restraints

END

WGHT      0.0235      0.7397

REM Highest difference peak  0.577,  deepest hole -0.486,  1-sigma level  0.130
Q1    1   0.2531  0.1455  0.2367  11.00000  0.05    0.58
Q2    1   0.5239  0.1177  0.2419  11.00000  0.05    0.54
Q3    1   0.4810  0.2179  0.2190  11.00000  0.05    0.49
Q4    1   0.4431  0.4525 -0.1000  11.00000  0.05    0.49
Q5    1   0.2793  0.1169 -0.0518  11.00000  0.05    0.48
Q6    1   0.3814 -0.1989 -0.0606  11.00000  0.05    0.43
Q7    1  -0.0814 -0.2137  0.0008  11.00000  0.05    0.42
Q8    1   0.2042 -0.3315 -0.0681  11.00000  0.05    0.42
Q9    1   0.0580 -0.2371 -0.0372  11.00000  0.05    0.42
Q10   1   0.0462 -0.0981 -0.2404  11.00000  0.05    0.41
Q11   1   0.3233 -0.0288 -0.2642  11.00000  0.05    0.40
Q12   1   0.1408  0.0421 -0.1241  11.00000  0.05    0.40
Q13   1  -0.0146 -0.3262 -0.1677  11.00000  0.05    0.40
Q14   1   0.3327 -0.2125  0.0984  11.00000  0.05    0.39
Q15   1   0.3057  0.1248  0.0404  11.00000  0.05    0.39
Q16   1   0.4490  0.4332 -0.1771  11.00000  0.05    0.39
Q17   1  -0.0013 -0.2131  0.0884  11.00000  0.05    0.39
Q18   1   0.1839 -0.1205 -0.2314  11.00000  0.05    0.38
Q19   1  -0.1074 -0.1412 -0.2047  11.00000  0.05    0.38
Q20   1   0.5199  0.0136  0.2385  11.00000  0.05    0.37
;
_shelx_res_checksum              1437

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1534999'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '4-bromo-2-chlorobenzoic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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/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                   7.2738(3)
_cell_length_b                   9.0627(3)
_cell_length_c                   11.7233(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.916(4)
_cell_angle_gamma                90
_cell_volume                     753.25(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2841
_cell_measurement_theta_min      2.8520
_cell_measurement_theta_max      27.4710

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.076
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.749
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5392
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.869
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1728
_reflns_number_gt                1499
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0247P)²+0.0041P] 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         1728
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0586
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.41446(4) 0.16791(3) 0.05834(2) 0.02106(10) Uani 1 1 d . . . . .
Cl1 Cl 0.12211(10) 0.61802(7) -0.23789(5) 0.02288(17) Uani 1 1 d . . . . .
O1 O 0.0782(3) 0.86323(18) 0.08763(15) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.0676(3) 0.8697(2) -0.10351(15) 0.0235(5) Uani 1 1 d . . . . .
H2 H 0.0266 0.9528 -0.0968 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3208(4) 0.3638(3) 0.0348(2) 0.0168(6) Uani 1 1 d . . . . .
C2 C 0.1037(4) 0.8042(3) -0.0017(2) 0.0155(5) Uani 1 1 d . . . . .
C3 C 0.1798(3) 0.6502(3) 0.0024(2) 0.0145(5) Uani 1 1 d . . . . .
C4 C 0.3120(4) 0.4482(3) 0.1319(2) 0.0188(6) Uani 1 1 d . . . . .
H4 H 0.3521 0.4103 0.2071 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2619(4) 0.4185(3) -0.0776(2) 0.0171(6) Uani 1 1 d . . . . .
H5 H 0.2686 0.3603 -0.1419 0.020 Uiso 1 1 calc R U . . .
C6 C 0.1925(3) 0.5617(3) -0.0931(2) 0.0158(5) Uani 1 1 d . . . . .
C7 C 0.2420(4) 0.5900(3) 0.1143(2) 0.0176(6) Uani 1 1 d . . . . .
H7 H 0.2360 0.6476 0.1790 0.021 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 0.02087(15) 0.01147(15) 0.03011(17) 0.00264(11) 0.00412(12) 0.00321(10)
Cl1 0.0379(4) 0.0147(3) 0.0145(3) 0.0009(3) 0.0027(3) 0.0001(3)
O1 0.0329(12) 0.0149(9) 0.0168(9) -0.0011(8) 0.0031(8) 0.0067(8)
O2 0.0357(12) 0.0151(9) 0.0193(10) 0.0028(8) 0.0055(9) 0.0103(9)
C1 0.0143(13) 0.0098(11) 0.0264(14) 0.0012(11) 0.0047(11) 0.0006(10)
C2 0.0159(12) 0.0129(12) 0.0165(13) -0.0007(11) 0.0012(10) -0.0013(10)
C3 0.0133(12) 0.0124(12) 0.0175(13) 0.0007(10) 0.0026(10) -0.0017(10)
C4 0.0197(13) 0.0174(13) 0.0177(13) 0.0031(11) 0.0008(11) -0.0006(11)
C5 0.0184(13) 0.0125(12) 0.0207(13) -0.0045(11) 0.0052(11) -0.0020(11)
C6 0.0159(13) 0.0139(12) 0.0167(12) 0.0003(11) 0.0018(10) -0.0007(10)
C7 0.0187(13) 0.0174(13) 0.0161(12) -0.0026(11) 0.0026(10) -0.0012(11)

_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 1.899(2) . ?
Cl1 C6 1.736(2) . ?
O1 C2 1.227(3) . ?
O2 C2 1.306(3) . ?
C1 C5 1.383(3) . ?
C1 C4 1.385(3) . ?
C2 C3 1.498(3) . ?
C3 C6 1.396(3) . ?
C3 C7 1.399(3) . ?
C4 C7 1.381(3) . ?
C5 C6 1.390(3) . ?

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
C5 C1 C4 121.6(2) . . ?
C5 C1 Br1 119.89(19) . . ?
C4 C1 Br1 118.55(19) . . ?
O1 C2 O2 122.9(2) . . ?
O1 C2 C3 120.3(2) . . ?
O2 C2 C3 116.8(2) . . ?
C6 C3 C7 117.5(2) . . ?
C6 C3 C2 126.8(2) . . ?
C7 C3 C2 115.6(2) . . ?
C7 C4 C1 118.3(2) . . ?
C1 C5 C6 119.0(2) . . ?
C5 C6 C3 121.2(2) . . ?
C5 C6 Cl1 114.91(19) . . ?
C3 C6 Cl1 123.86(19) . . ?
C4 C7 C3 122.3(2) . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.094

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7


TITL red in P2(1)/n
CELL  0.71073   7.2738   9.0627  11.7233   90.000  102.916   90.000
ZERR     4.00   0.0003   0.0003   0.0005    0.000    0.004    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    CL   BR
UNIT  28 16 8 4 4
MERG   2
FMAP   2
PLAN   20
ACTA
LIST   3
L.S.  5
WGHT    0.024700    0.004100
FVAR       4.53257
BR1   5    0.414458    0.167911    0.058342    11.00000    0.02087    0.01147 =
         0.03011    0.00264    0.00412    0.00321
CL1   4    0.122110    0.618015   -0.237892    11.00000    0.03790    0.01469 =
         0.01453    0.00094    0.00266    0.00014
O1    3    0.078155    0.863228    0.087633    11.00000    0.03287    0.01487 =
         0.01681   -0.00110    0.00310    0.00666
O2    3    0.067554    0.869677   -0.103513    11.00000    0.03574    0.01514 =
         0.01934    0.00284    0.00549    0.01031
AFIX  83
H2    2    0.026575    0.952760   -0.096821    11.00000   -1.50000
AFIX   0
C1    1    0.320770    0.363752    0.034776    11.00000    0.01427    0.00985 =
         0.02640    0.00117    0.00466    0.00061
C2    1    0.103716    0.804160   -0.001719    11.00000    0.01589    0.01292 =
         0.01652   -0.00069    0.00115   -0.00134
C3    1    0.179840    0.650172    0.002377    11.00000    0.01326    0.01242 =
         0.01754    0.00070    0.00262   -0.00170
C4    1    0.311957    0.448212    0.131885    11.00000    0.01970    0.01736 =
         0.01769    0.00310    0.00076   -0.00060
AFIX  43
H4    2    0.352141    0.410349    0.207070    11.00000   -1.20000
AFIX   0
C5    1    0.261868    0.418463   -0.077607    11.00000    0.01840    0.01254 =
         0.02069   -0.00453    0.00522   -0.00201
AFIX  43
H5    2    0.268590    0.360250   -0.141879    11.00000   -1.20000
AFIX   0
C6    1    0.192471    0.561726   -0.093107    11.00000    0.01594    0.01394 =
         0.01672    0.00035    0.00182   -0.00073
C7    1    0.242018    0.590018    0.114255    11.00000    0.01866    0.01744 =
         0.01610   -0.00256    0.00260   -0.00124
AFIX  43
H7    2    0.236035    0.647552    0.179014    11.00000   -1.20000
AFIX   0
HKLF    4

REM  red in P2(1)/n
REM R1 =  0.0276 for    1499 Fo > 4sig(Fo)  and  0.0346 for all    1728 data
REM    100 parameters refined using      0 restraints

END

WGHT      0.0246      0.0082

REM Highest difference peak  0.349,  deepest hole -0.440,  1-sigma level  0.094
Q1    1   0.2587  0.3915 -0.0182  11.00000  0.05    0.35
Q2    1   0.2703  0.3920  0.0882  11.00000  0.05    0.34
Q3    1   0.2226  0.6037  0.0543  11.00000  0.05    0.34
Q4    1   0.4513  0.1795 -0.0363  11.00000  0.05    0.33
Q5    1   0.5064  0.3960  0.0336  11.00000  0.05    0.33
Q6    1   0.5318  0.1608  0.1496  11.00000  0.05    0.31
Q7    1   0.0896  0.9678  0.0756  11.00000  0.05    0.31
Q8    1   0.2101  0.6053  0.1352  11.00000  0.05    0.30
Q9    1   0.1963  0.5687 -0.1834  11.00000  0.05    0.30
Q10   1   0.2981  0.9970 -0.0937  11.00000  0.05    0.29
Q11   1   0.1280  0.6320  0.1805  11.00000  0.05    0.29
Q12   1   0.0071  0.8823  0.1059  11.00000  0.05    0.29
Q13   1   0.1162  0.8172  0.1385  11.00000  0.05    0.29
Q14   1   0.2764  0.5762 -0.1741  11.00000  0.05    0.29
Q15   1   0.4020  0.3012  0.0337  11.00000  0.05    0.28
Q16   1   0.4788  0.1115  0.0995  11.00000  0.05    0.28
Q17   1   0.0640  0.5342 -0.2828  11.00000  0.05    0.28
Q18   1   0.1379  0.6020 -0.0537  11.00000  0.05    0.28
Q19   1   0.2450  0.6413 -0.0218  11.00000  0.05    0.27
Q20   1   0.1868  0.4775 -0.0850  11.00000  0.05    0.27
;
_shelx_res_checksum              33197
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535004'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-chlorobenzoic acid/2-bromo-4-chlorobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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/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                   7.2577(3)
_cell_length_b                   9.0397(3)
_cell_length_c                   11.8561(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.904(4)
_cell_angle_gamma                90
_cell_volume                     755.06(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6789
_cell_measurement_theta_min      2.8270
_cell_measurement_theta_max      30.4530

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.071
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.735
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11833
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2307
_reflns_number_gt                2136
_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    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ', Occupancy disorder'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²+0.5425P] 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         2307
_refine_ls_number_parameters     107
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0590
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.186
_refine_ls_shift/su_mean         0.048

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 0.9154(3) 0.83304(10) 0.05721(19) 0.02044(10) Uani 0.7450(12) 1 d D . P
A 1
Cl1 Cl 0.6221(13) 0.3855(8) -0.2354(3) 0.0198(3) Uani 0.7450(12) 1 d D . P A 1
Cl2 Cl 0.910(2) 0.8174(8) 0.0585(14) 0.02044(10) Uani 0.2550(12) 1 d D . P A 2
Br2 Br 0.6152(16) 0.3752(10) -0.2475(4) 0.0198(3) Uani 0.2550(12) 1 d D . P A 2
O1 O 0.5806(2) 0.13700(14) 0.08800(11) 0.0224(3) Uani 1 1 d . . . . .
O2 O 0.5642(2) 0.13028(14) -0.10166(11) 0.0240(3) Uani 1 1 d . . . . .
H2 H 0.523513 0.046974 -0.094831 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6923(2) 0.43862(17) -0.09176(13) 0.0145(3) Uani 1 1 d D . . . .
C5 C 0.8227(2) 0.63767(16) 0.03537(15) 0.0163(3) Uani 1 1 d D . . . .
C4 C 0.7620(2) 0.58259(18) -0.07637(14) 0.0163(3) Uani 1 1 d . . . . .
H4 H 0.767575 0.640814 -0.140129 0.020 Uiso 1 1 calc R U . . .
C6 C 0.8160(2) 0.55355(19) 0.13212(15) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.858062 0.591890 0.206672 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7450(2) 0.41125(18) 0.11487(14) 0.0167(3) Uani 1 1 d . . . . .
H7 H 0.739638 0.354151 0.179251 0.020 Uiso 1 1 calc R U . . .
C1 C 0.6044(2) 0.19603(18) -0.00053(14) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.6808(2) 0.34991(17) 0.00347(14) 0.0141(3) Uani 1 1 d . . . . .

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 0.01969(18) 0.0103(3) 0.03064(14) -0.0031(3) 0.00468(11) -0.0032(2)
Cl1 0.0335(6) 0.0122(8) 0.0114(6) -0.0040(5) 0.0007(8) -0.0003(6)
Cl2 0.01969(18) 0.0103(3) 0.03064(14) -0.0031(3) 0.00468(11) -0.0032(2)
Br2 0.0335(6) 0.0122(8) 0.0114(6) -0.0040(5) 0.0007(8) -0.0003(6)
O1 0.0331(8) 0.0161(6) 0.0169(6) 0.0013(4) 0.0040(5) -0.0062(5)
O2 0.0393(8) 0.0150(6) 0.0184(6) -0.0034(5) 0.0081(5) -0.0101(5)
C3 0.0164(7) 0.0131(7) 0.0138(6) -0.0004(5) 0.0030(6) 0.0015(6)
C5 0.0148(8) 0.0097(6) 0.0241(8) -0.0018(6) 0.0042(6) 0.0001(5)
C4 0.0176(8) 0.0120(7) 0.0199(7) 0.0018(6) 0.0060(6) 0.0011(6)
C6 0.0192(8) 0.0169(7) 0.0172(7) -0.0023(6) 0.0031(6) -0.0012(6)
C7 0.0181(8) 0.0159(7) 0.0155(7) 0.0001(6) 0.0029(6) -0.0010(6)
C1 0.0144(7) 0.0131(6) 0.0155(7) 0.0006(5) 0.0013(5) 0.0006(5)
C2 0.0148(7) 0.0110(6) 0.0163(7) -0.0004(5) 0.0034(6) 0.0008(5)

_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 C5 1.8852(17) . ?
Cl1 C3 1.724(3) . ?
Cl2 C5 1.741(5) . ?
Br2 C3 1.886(4) . ?
O1 C1 1.226(2) . ?
O2 C1 1.307(2) . ?
C3 C4 1.392(2) . ?
C3 C2 1.404(2) . ?
C5 C4 1.384(2) . ?
C5 C6 1.387(2) . ?
C6 C7 1.382(2) . ?
C7 C2 1.405(2) . ?
C1 C2 1.494(2) . ?

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
C4 C3 C2 121.24(14) . . ?
C4 C3 Cl1 113.7(3) . . ?
C2 C3 Cl1 125.1(3) . . ?
C4 C3 Br2 115.2(3) . . ?
C2 C3 Br2 123.6(3) . . ?
C4 C5 C6 121.85(15) . . ?
C4 C5 Cl2 120.4(6) . . ?
C6 C5 Cl2 117.7(6) . . ?
C4 C5 Br1 119.31(14) . . ?
C6 C5 Br1 118.84(14) . . ?
C5 C4 C3 118.93(15) . . ?
C7 C6 C5 118.28(15) . . ?
C6 C7 C2 122.28(15) . . ?
O1 C1 O2 122.77(16) . . ?
O1 C1 C2 120.37(15) . . ?
O2 C1 C2 116.86(14) . . ?
C3 C2 C7 117.41(14) . . ?
C3 C2 C1 126.85(14) . . ?
C7 C2 C1 115.73(14) . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.090

_shelx_res_file                  
;
TITL red in P2(1)/n
    shelx.res
    created by SHELXL-2016/6 at 16:31:01 on 17-Apr-2017
CELL  0.71073   7.2577   9.0397  11.8561   90.000  103.904   90.000
ZERR     4.00   0.0003   0.0003   0.0004    0.000    0.004    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    CL   BR
UNIT  28 16 8 4 4
MERG   2
EADP BR1 CL2
EADP BR2 CL1
DFIX 1.900 0.005 C5 BR1
DFIX 1.900 0.005 C3 BR2
DFIX 1.740 0.005 C3 CL1
DFIX 1.740 0.005 C5 CL2
FMAP   2
PLAN   20
ACTA
LIST   3
L.S.   2
WGHT    0.025400    0.542500
FVAR       5.03499   0.74497
PART    1
BR1   5    0.915365    0.833036    0.057209    21.00000    0.01969    0.01029 =
         0.03064   -0.00313    0.00468   -0.00324
CL1   4    0.622085    0.385535   -0.235356    21.00000    0.03350    0.01223 =
         0.01141   -0.00400    0.00069   -0.00028
PART    2
CL2   4    0.909920    0.817431    0.058492   -21.00000    0.01969    0.01029 =
         0.03064   -0.00313    0.00468   -0.00324
BR2   5    0.615230    0.375176   -0.247518   -21.00000    0.03350    0.01223 =
         0.01141   -0.00400    0.00069   -0.00028
PART    0
O1    3    0.580620    0.136999    0.088001    11.00000    0.03309    0.01614 =
         0.01693    0.00127    0.00402   -0.00624
O2    3    0.564227    0.130276   -0.101658    11.00000    0.03929    0.01498 =
         0.01844   -0.00336    0.00814   -0.01006
AFIX  83
H2    2    0.523513    0.046974   -0.094831    11.00000   -1.50000
AFIX   0
C3    1    0.692285    0.438623   -0.091759    11.00000    0.01641    0.01306 =
         0.01384   -0.00045    0.00300    0.00147
C5    1    0.822743    0.637674    0.035366    11.00000    0.01485    0.00965 =
         0.02413   -0.00184    0.00423    0.00012
C4    1    0.761956    0.582587   -0.076374    11.00000    0.01758    0.01202 =
         0.01991    0.00182    0.00599    0.00107
AFIX  43
H4    2    0.767575    0.640814   -0.140129    11.00000   -1.20000
AFIX   0
C6    1    0.815969    0.553555    0.132121    11.00000    0.01918    0.01694 =
         0.01720   -0.00234    0.00307   -0.00120
AFIX  43
H6    2    0.858062    0.591890    0.206672    11.00000   -1.20000
AFIX   0
C7    1    0.745027    0.411251    0.114872    11.00000    0.01809    0.01587 =
         0.01554    0.00015    0.00291   -0.00099
AFIX  43
H7    2    0.739638    0.354151    0.179251    11.00000   -1.20000
AFIX   0
C1    1    0.604394    0.196031   -0.000527    11.00000    0.01440    0.01308 =
         0.01553    0.00064    0.00133    0.00060
C2    1    0.680797    0.349906    0.003474    11.00000    0.01476    0.01096 =
         0.01632   -0.00041    0.00337    0.00082
HKLF    4




REM  red in P2(1)/n
REM R1 =  0.0243 for    2136 Fo > 4sig(Fo)  and  0.0271 for all    2307 data
REM    107 parameters refined using      4 restraints

END

WGHT      0.0251      0.5227

REM Highest difference peak  0.468,  deepest hole -0.503,  1-sigma level  0.090
Q1    1   0.9086  0.8293 -0.0060  11.00000  0.05    0.47
Q2    1   0.7204  0.5126 -0.0832  11.00000  0.05    0.46
Q3    1   0.8182  0.4640  0.1229  11.00000  0.05    0.43
Q4    1   1.0661  0.7747  0.1183  11.00000  0.05    0.41
Q5    1   0.6449  0.2798  0.0008  11.00000  0.05    0.36
Q6    1   0.7347  0.4995  0.1195  11.00000  0.05    0.36
Q7    1   0.6780  0.3888 -0.0414  11.00000  0.05    0.36
Q8    1   1.0397  0.8214  0.0620  11.00000  0.05    0.35
Q9    1   0.4976  0.3745 -0.2466  11.00000  0.05    0.32
Q10   1   0.6261  0.4702 -0.2426  11.00000  0.05    0.31
Q11   1   0.7835  0.6019  0.0749  11.00000  0.05    0.30
Q12   1   0.7924  0.8297  0.0451  11.00000  0.05    0.29
Q13   1   0.6028  0.7068 -0.2639  11.00000  0.05    0.27
Q14   1   0.3926  0.3041 -0.2448  11.00000  0.05    0.27
Q15   1   0.5751  0.7401 -0.2665  11.00000  0.05    0.27
Q16   1   1.0763  0.8786  0.1144  11.00000  0.05    0.26
Q17   1   0.9745  0.7330  0.0510  11.00000  0.05    0.26
Q18   1   0.8544  0.7119  0.0430  11.00000  0.05    0.26
Q19   1   0.7628  0.6136 -0.0215  11.00000  0.05    0.26
Q20   1   0.3533  0.2340 -0.1038  11.00000  0.05    0.26
;
_shelx_res_checksum              15550

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1534997'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '4-bromo-2chlorobenzoic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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/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                   7.2560(2)
_cell_length_b                   9.0227(2)
_cell_length_c                   11.9855(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.676(3)
_cell_angle_gamma                90
_cell_volume                     759.07(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8766
_cell_measurement_theta_min      2.8300
_cell_measurement_theta_max      27.4450

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.705
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13288
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.861
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1743
_reflns_number_gt                1656
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0240P)²+0.4121P] 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         1743
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_ref         0.0516
_refine_ls_wR_factor_gt          0.0508
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.003
_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 0.9201(6) 0.3349(5) 0.0580(5) 0.0217(4) Uani 0.5178(12) 1 d . . P A 1
Cl1 Cl 0.6345(15) -0.1207(13) -0.2317(9) 0.0201(8) Uani 0.5178(12) 1 d . . P A
1
Cl2 Cl 0.9016(18) 0.3187(13) 0.0505(13) 0.0230(10) Uani 0.4822(12) 1 d . . P A
2
Br2 Br 0.6084(7) -0.1199(6) -0.2458(4) 0.0214(5) Uani 0.4822(12) 1 d . . P A 2
O2 O 0.5832(2) -0.36215(14) 0.08909(11) 0.0264(3) Uani 1 1 d . . . . .
O1 O 0.5620(2) -0.36979(14) -0.09926(11) 0.0281(3) Uani 1 1 d . . . . .
H1 H 0.5211 -0.4530 -0.0918 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8244(2) 0.13938(18) 0.03549(16) 0.0195(3) Uani 1 1 d . . . . .
C6 C 0.8183(2) 0.0556(2) 0.13169(15) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.8612 0.0944 0.2056 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6819(2) -0.14950(18) 0.00452(15) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.7620(2) 0.08306(19) -0.07520(15) 0.0194(3) Uani 1 1 d . . . . .
H4 H 0.7667 0.1410 -0.1386 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7469(2) -0.08697(19) 0.11484(15) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.7417 -0.1435 0.1788 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6922(2) -0.06114(18) -0.09037(14) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.6048(2) -0.30330(18) -0.00011(14) 0.0178(3) Uani 1 1 d . . . . .

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 0.0197(8) 0.0114(8) 0.0329(7) -0.0059(6) 0.0043(6) -0.0055(6)
Cl1 0.027(2) 0.0193(8) 0.0087(16) -0.0001(10) -0.0053(13) 0.0005(12)
Cl2 0.0207(17) 0.0119(19) 0.0342(15) -0.0085(12) 0.0027(12) -0.0097(11)
Br2 0.0298(11) 0.0179(4) 0.0123(10) -0.0007(6) -0.0025(7) 0.0015(6)
O2 0.0389(8) 0.0196(6) 0.0196(6) 0.0024(5) 0.0055(6) -0.0067(6)
O1 0.0455(9) 0.0183(6) 0.0210(7) -0.0039(5) 0.0095(6) -0.0109(6)
C5 0.0178(8) 0.0127(7) 0.0281(9) -0.0023(7) 0.0062(7) 0.0006(6)
C6 0.0212(8) 0.0214(8) 0.0194(8) -0.0036(7) 0.0029(6) -0.0003(7)
C2 0.0170(8) 0.0147(7) 0.0189(8) 0.0004(6) 0.0042(6) 0.0020(6)
C4 0.0209(8) 0.0166(8) 0.0214(8) 0.0028(6) 0.0066(7) 0.0022(6)
C7 0.0209(8) 0.0201(8) 0.0179(8) 0.0016(6) 0.0051(7) 0.0011(6)
C3 0.0189(8) 0.0160(8) 0.0182(8) -0.0011(6) 0.0052(6) 0.0024(6)
C1 0.0188(8) 0.0166(8) 0.0171(8) 0.0005(6) 0.0028(6) 0.0016(6)

_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 C5 1.890(4) . ?
Cl1 C3 1.724(11) . ?
Cl2 C5 1.707(11) . ?
Br2 C3 1.883(5) . ?
O2 C1 1.239(2) . ?
O1 C1 1.297(2) . ?
C5 C4 1.385(2) . ?
C5 C6 1.389(2) . ?
C6 C7 1.382(2) . ?
C2 C7 1.405(2) . ?
C2 C3 1.406(2) . ?
C2 C1 1.492(2) . ?
C4 C3 1.391(2) . ?

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
C4 C5 C6 121.59(16) . . ?
C4 C5 Cl2 117.9(5) . . ?
C6 C5 Cl2 120.5(5) . . ?
C4 C5 Br1 119.9(2) . . ?
C6 C5 Br1 118.5(2) . . ?
C7 C6 C5 118.35(16) . . ?
C7 C2 C3 117.36(15) . . ?
C7 C2 C1 116.23(15) . . ?
C3 C2 C1 126.40(15) . . ?
C5 C4 C3 119.22(16) . . ?
C6 C7 C2 122.37(16) . . ?
C4 C3 C2 121.11(15) . . ?
C4 C3 Cl1 114.2(4) . . ?
C2 C3 Cl1 124.6(4) . . ?
C4 C3 Br2 114.1(2) . . ?
C2 C3 Br2 124.8(2) . . ?
O2 C1 O1 122.64(16) . . ?
O2 C1 C2 119.66(15) . . ?
O1 C1 C2 117.70(15) . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.059

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL red1 in P2(1)/n
CELL  0.71073   7.2560   9.0227  11.9855   90.000  104.676   90.000
ZERR     4.00   0.0002   0.0002   0.0003    0.000    0.003    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    CL   BR
UNIT  28 16 8 4 4
MERG   2
FMAP   2
PLAN   20
ACTA
LIST   3
L.S.   5
WGHT    0.024000    0.412100
FVAR       4.99907   0.51779
PART    1
BR1   5    0.920107    0.334913    0.057962    21.00000    0.01968    0.01136 =
         0.03289   -0.00592    0.00434   -0.00554
CL1   4    0.634481   -0.120688   -0.231662    21.00000    0.02697    0.01926 =
         0.00866   -0.00013   -0.00534    0.00046
PART    2
CL2   4    0.901635    0.318711    0.050496   -21.00000    0.02067    0.01189 =
         0.03421   -0.00852    0.00272   -0.00968
BR2   5    0.608425   -0.119901   -0.245764   -21.00000    0.02976    0.01788 =
         0.01230   -0.00065   -0.00250    0.00147
PART    0
O2    3    0.583218   -0.362150    0.089086    11.00000    0.03891    0.01958 =
         0.01961    0.00235    0.00549   -0.00670
O1    3    0.561973   -0.369787   -0.099263    11.00000    0.04551    0.01835 =
         0.02099   -0.00389    0.00951   -0.01086
AFIX  83
H1    2    0.521125   -0.452970   -0.091847    11.00000   -1.50000
AFIX   0
C5    1    0.824419    0.139379    0.035486    11.00000    0.01783    0.01274 =
         0.02808   -0.00227    0.00621    0.00062
C6    1    0.818322    0.055572    0.131694    11.00000    0.02122    0.02136 =
         0.01936   -0.00358    0.00288   -0.00035
AFIX  43
H6    2    0.861215    0.094406    0.205616    11.00000   -1.20000
AFIX   0
C2    1    0.681896   -0.149501    0.004517    11.00000    0.01702    0.01471 =
         0.01889    0.00039    0.00424    0.00198
C4    1    0.761999    0.083062   -0.075196    11.00000    0.02095    0.01659 =
         0.02144    0.00284    0.00655    0.00224
AFIX  43
H4    2    0.766678    0.140959   -0.138616    11.00000   -1.20000
AFIX   0
C7    1    0.746924   -0.086970    0.114837    11.00000    0.02087    0.02011 =
         0.01792    0.00157    0.00508    0.00106
AFIX  43
H7    2    0.741748   -0.143525    0.178844    11.00000   -1.20000
AFIX   0
C3    1    0.692220   -0.061144   -0.090367    11.00000    0.01890    0.01605 =
         0.01817   -0.00107    0.00523    0.00243
C1    1    0.604787   -0.303303   -0.000113    11.00000    0.01882    0.01659 =
         0.01712    0.00048    0.00276    0.00159
HKLF    4

REM  red1 in P2(1)/n
REM R1 =  0.0198 for    1656 Fo > 4sig(Fo)  and  0.0214 for all    1743 data
REM    119 parameters refined using      0 restraints

END

WGHT      0.0240      0.4124

REM Highest difference peak  0.390,  deepest hole -0.322,  1-sigma level  0.059
Q1    1   0.6478 -0.2209 -0.0033  11.00000  0.05    0.39
Q2    1   0.6867 -0.1156 -0.0398  11.00000  0.05    0.32
Q3    1   0.4902 -0.1330 -0.2351  11.00000  0.05    0.31
Q4    1   0.7183 -0.1154  0.0578  11.00000  0.05    0.30
Q5    1   0.6971  0.0184 -0.0811  11.00000  0.05    0.29
Q6    1   0.8099 -0.0224  0.1162  11.00000  0.05    0.28
Q7    1   0.8121  0.0908  0.0787  11.00000  0.05    0.28
Q8    1   0.6999 -0.1178  0.2349  11.00000  0.05    0.27
Q9    1   0.8579  0.2191  0.0388  11.00000  0.05    0.27
Q10   1   0.7806  0.1146 -0.0223  11.00000  0.05    0.25
Q11   1   0.5026 -0.0451 -0.2642  11.00000  0.05    0.25
Q12   1   0.5542 -0.0170 -0.2718  11.00000  0.05    0.25
Q13   1   0.9717  0.3092  0.1448  11.00000  0.05    0.24
Q14   1   0.8767  0.3337 -0.0275  11.00000  0.05    0.19
Q15   1   0.7739  0.0991 -0.1016  11.00000  0.05    0.18
Q16   1   0.5379 -0.4394  0.0782  11.00000  0.05    0.18
Q17   1   0.6063 -0.4520  0.0978  11.00000  0.05    0.17
Q18   1   0.5758 -0.3278 -0.0482  11.00000  0.05    0.17
Q19   1   0.6485 -0.0767 -0.1382  11.00000  0.05    0.17
Q20   1   0.7288 -0.1870 -0.2346  11.00000  0.05    0.17
;
_shelx_res_checksum              85118
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1534998'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '2-Bromo-4chlorobenzoic acid'
_chemical_name_common            '2-Bromo-4chlorobenzoic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   3.8949(3)
_cell_length_b                   8.2939(3)
_cell_length_c                   11.8408(5)
_cell_angle_alpha                89.014(3)
_cell_angle_beta                 89.991(5)
_cell_angle_gamma                78.651(5)
_cell_volume                     374.97(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2975
_cell_measurement_theta_min      3.0500
_cell_measurement_theta_max      29.9600

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.085
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.774
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5698
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         30.382
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2009
_reflns_number_gt                1827
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0249P)²+0.4110P] 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         2009
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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 0.58049(8) 0.91757(4) 0.33429(3) 0.01927(11) Uani 1 1 d . . . . .
Cl2 Cl 0.8383(2) 0.25881(9) 0.40688(7) 0.02039(18) Uani 1 1 d . . . . .
O2 O 0.2541(7) 0.9644(3) 0.1083(2) 0.0266(6) Uani 1 1 d . . . . .
O1 O 0.0215(7) 0.7781(3) 0.0180(2) 0.0246(5) Uani 1 1 d . . . . .
H1 H -0.0552 0.8580 -0.0228 0.037 Uiso 1 1 calc R U . . .
C3 C 0.5259(8) 0.7110(4) 0.2813(3) 0.0164(6) Uani 1 1 d . . . . .
C4 C 0.6655(8) 0.5785(4) 0.3517(3) 0.0175(6) Uani 1 1 d . . . . .
H4 H 0.7708 0.5955 0.4198 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6460(8) 0.4204(4) 0.3190(3) 0.0182(6) Uani 1 1 d . . . . .
C2 C 0.3611(8) 0.6863(4) 0.1788(3) 0.0167(6) Uani 1 1 d . . . . .
C1 C 0.2097(8) 0.8229(4) 0.1001(3) 0.0187(7) Uani 1 1 d . . . . .
C6 C 0.4892(9) 0.3910(4) 0.2182(3) 0.0182(6) Uani 1 1 d . . . . .
H6 H 0.4807 0.2844 0.1969 0.022 Uiso 1 1 calc R U . . .
C7 C 0.3455(8) 0.5253(4) 0.1500(3) 0.0182(6) Uani 1 1 d . . . . .
H7 H 0.2352 0.5075 0.0830 0.022 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 0.02357(18) 0.01180(16) 0.02241(19) 0.00198(12) -0.00454(13) -0.00361(12)
Cl2 0.0259(4) 0.0120(3) 0.0227(4) 0.0042(3) -0.0061(3) -0.0026(3)
O2 0.0363(14) 0.0187(12) 0.0258(13) 0.0072(10) -0.0101(11) -0.0081(10)
O1 0.0343(14) 0.0182(12) 0.0208(13) 0.0068(9) -0.0079(11) -0.0046(10)
C3 0.0190(15) 0.0108(13) 0.0201(16) 0.0005(12) 0.0026(13) -0.0046(11)
C4 0.0185(15) 0.0168(15) 0.0167(16) -0.0001(12) -0.0014(12) -0.0025(12)
C5 0.0185(15) 0.0157(15) 0.0192(16) 0.0048(12) 0.0038(13) -0.0007(12)
C2 0.0169(14) 0.0164(14) 0.0160(16) 0.0045(12) 0.0012(12) -0.0015(12)
C1 0.0189(15) 0.0198(15) 0.0166(16) 0.0025(12) 0.0013(13) -0.0024(12)
C6 0.0233(16) 0.0118(14) 0.0189(16) 0.0005(12) -0.0008(13) -0.0025(12)
C7 0.0199(15) 0.0185(15) 0.0167(16) 0.0009(12) -0.0006(13) -0.0054(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 C3 1.886(3) . ?
Cl2 C5 1.731(3) . ?
O2 C1 1.225(4) . ?
O1 C1 1.319(4) . ?
C3 C4 1.389(4) . ?
C3 C2 1.410(4) . ?
C4 C5 1.390(4) . ?
C5 C6 1.388(5) . ?
C2 C7 1.396(4) . ?
C2 C1 1.484(4) . ?
C6 C7 1.390(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
C4 C3 C2 120.7(3) . . ?
C4 C3 Br1 114.7(2) . . ?
C2 C3 Br1 124.7(2) . . ?
C3 C4 C5 119.2(3) . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 Cl2 120.6(2) . . ?
C4 C5 Cl2 117.5(3) . . ?
C7 C2 C3 118.1(3) . . ?
C7 C2 C1 118.9(3) . . ?
C3 C2 C1 123.0(3) . . ?
O2 C1 O1 122.1(3) . . ?
O2 C1 C2 124.2(3) . . ?
O1 C1 C2 113.6(3) . . ?
C5 C6 C7 118.1(3) . . ?
C6 C7 C2 122.2(3) . . ?

_refine_diff_density_max         0.629
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.131

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL red in P1
CELL  0.71073   3.8949   8.2939  11.8408   89.014   89.991   78.651
ZERR     2.00   0.0003   0.0003   0.0005    0.003    0.005    0.005
LATT   1
SFAC  C    H    O    CL   BR
UNIT  14 8 4 2 2
MERG   2
FMAP   2
PLAN   20
ACTA
L.S.  10
WGHT    0.024900    0.411000
FVAR       5.65030
BR1   5    0.580489    0.917572    0.334291    11.00000    0.02357    0.01180 =
         0.02241    0.00198   -0.00454   -0.00361
CL2   4    0.838292    0.258811    0.406881    11.00000    0.02590    0.01198 =
         0.02266    0.00424   -0.00607   -0.00257
O2    3    0.254061    0.964400    0.108304    11.00000    0.03625    0.01871 =
         0.02581    0.00724   -0.01008   -0.00812
O1    3    0.021511    0.778110    0.017967    11.00000    0.03429    0.01816 =
         0.02078    0.00681   -0.00792   -0.00463
AFIX  83
H1    2   -0.055204    0.857990   -0.022805    11.00000   -1.50000
AFIX   0
C3    1    0.525915    0.710956    0.281282    11.00000    0.01900    0.01083 =
         0.02010    0.00051    0.00255   -0.00457
C4    1    0.665543    0.578549    0.351666    11.00000    0.01850    0.01684 =
         0.01671   -0.00009   -0.00143   -0.00247
AFIX  43
H4    2    0.770814    0.595504    0.419771    11.00000   -1.20000
AFIX   0
C5    1    0.645962    0.420393    0.319035    11.00000    0.01853    0.01571 =
         0.01919    0.00479    0.00379   -0.00065
C2    1    0.361115    0.686280    0.178793    11.00000    0.01694    0.01639 =
         0.01598    0.00447    0.00124   -0.00148
C1    1    0.209709    0.822899    0.100055    11.00000    0.01889    0.01977 =
         0.01663    0.00250    0.00133   -0.00238
C6    1    0.489222    0.390964    0.218197    11.00000    0.02331    0.01185 =
         0.01889    0.00053   -0.00083   -0.00246
AFIX  43
H6    2    0.480672    0.284418    0.196892    11.00000   -1.20000
AFIX   0
C7    1    0.345460    0.525333    0.150008    11.00000    0.01991    0.01849 =
         0.01670    0.00095   -0.00059   -0.00538
AFIX  43
H7    2    0.235212    0.507473    0.083008    11.00000   -1.20000
AFIX   0
HKLF    4

REM  red in P1
REM R1 =  0.0340 for    1827 Fo > 4sig(Fo)  and  0.0394 for all    2009 data
REM    100 parameters refined using      0 restraints

END

WGHT      0.0247      0.4123

REM Highest difference peak  0.629,  deepest hole -0.592,  1-sigma level  0.131
Q1    1   0.3009  0.9658  0.2948  11.00000  0.05    0.63
Q2    1   0.8798  0.9115  0.3174  11.00000  0.05    0.62
Q3    1   0.8494  0.8438  0.3808  11.00000  0.05    0.58
Q4    1   0.7505  0.8948  0.2745  11.00000  0.05    0.56
Q5    1   0.3205  0.7391  0.1434  11.00000  0.05    0.55
Q6    1   0.4425  0.9422  0.3998  11.00000  0.05    0.53
Q7    1   0.5016  0.2793  0.4195  11.00000  0.05    0.53
Q8    1   0.2813  0.9155  0.3594  11.00000  0.05    0.53
Q9    1   0.4023  1.0600  0.3028  11.00000  0.05    0.52
Q10   1   0.7058  0.9992  0.2780  11.00000  0.05    0.52
Q11   1   0.7182  0.7769  0.3231  11.00000  0.05    0.51
Q12   1   0.7704  0.1254  0.3649  11.00000  0.05    0.49
Q13   1   0.6404  0.4128  0.2650  11.00000  0.05    0.47
Q14   1   0.1126  0.6167  0.0782  11.00000  0.05    0.45
Q15   1   0.5096  0.8377  0.4172  11.00000  0.05    0.45
Q16   1   0.4015  0.9542  0.4923  11.00000  0.05    0.44
Q17   1   0.2806  0.9844  0.1444  11.00000  0.05    0.44
Q18   1   0.5601  0.2266  0.4367  11.00000  0.05    0.43
Q19   1   0.6372  1.0381  0.3856  11.00000  0.05    0.41
Q20   1   0.1005  0.9586  0.1174  11.00000  0.05    0.40
;
_shelx_res_checksum              30259
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535001'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-chlorobenzoic acid/2-bromo-4-chlorobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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/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                   7.2385(4)
_cell_length_b                   8.9976(5)
_cell_length_c                   12.1313(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.406(5)
_cell_angle_gamma                90
_cell_volume                     761.71(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2653
_cell_measurement_theta_min      2.8390
_cell_measurement_theta_max      27.4430

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.053
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.685
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5434
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.856
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1750
_reflns_number_gt                1512
_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    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ', Occupancy disorder'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²] 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         1750
_refine_ls_number_parameters     107
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.8873(5) 0.8778(4) 0.24264(12) 0.02092(19) Uani 0.7146(14) 1 d D . P A
1
Cl1 Cl 0.585(2) 1.3207(7) -0.0567(14) 0.0212(6) Uani 0.7146(14) 1 d D . P A 1
Cl2 Cl 0.888(3) 0.885(3) 0.2309(8) 0.02092(19) Uani 0.2854(14) 1 d D . P A 2
Br2 Br 0.584(2) 1.3396(8) -0.0513(15) 0.0212(6) Uani 0.2854(14) 1 d D . P A 2
O1 O 0.9134(3) 0.6390(2) -0.09059(15) 0.0250(5) Uani 1 1 d . . . . .
O2 O 0.9414(3) 0.6305(2) 0.09636(16) 0.0265(5) Uani 1 1 d . . . . .
H2 H 0.981964 0.547239 0.088235 0.040 Uiso 1 1 calc R U . . .
C1 C 0.8950(3) 0.6973(3) -0.0005(2) 0.0153(6) Uani 1 1 d . . . . .
C2 C 0.8177(4) 0.8513(3) -0.0053(2) 0.0141(6) Uani 1 1 d . . . . .
C3 C 0.8079(3) 0.9397(3) 0.08873(19) 0.0154(6) Uani 1 1 d D . . . .
C4 C 0.6784(4) 1.0585(3) -0.1307(2) 0.0189(6) Uani 1 1 d . . . . .
H4 H 0.634161 1.098170 -0.203772 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6740(4) 1.1413(3) -0.0352(2) 0.0177(6) Uani 1 1 d D . . . .
C6 C 0.7383(4) 1.0843(3) 0.0743(2) 0.0172(6) Uani 1 1 d . . . . .
H6 H 0.734832 1.141955 0.137304 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7500(4) 0.9153(3) -0.1148(2) 0.0174(6) Uani 1 1 d . . . . .
H7 H 0.753697 0.859136 -0.178582 0.021 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 0.0307(2) 0.0178(5) 0.0130(4) 0.0017(4) 0.0036(4) -0.0005(2)
Cl1 0.0207(3) 0.0082(13) 0.0342(12) 0.0016(16) 0.0063(6) 0.0033(14)
Cl2 0.0307(2) 0.0178(5) 0.0130(4) 0.0017(4) 0.0036(4) -0.0005(2)
Br2 0.0207(3) 0.0082(13) 0.0342(12) 0.0016(16) 0.0063(6) 0.0033(14)
O1 0.0360(12) 0.0188(13) 0.0199(10) -0.0031(9) 0.0067(9) 0.0057(9)
O2 0.0411(13) 0.0169(12) 0.0215(10) 0.0048(9) 0.0086(9) 0.0110(10)
C1 0.0133(12) 0.0142(16) 0.0178(13) 0.0004(12) 0.0031(11) -0.0036(12)
C2 0.0117(12) 0.0114(15) 0.0191(13) 0.0010(11) 0.0036(11) -0.0009(11)
C3 0.0155(13) 0.0163(16) 0.0156(12) 0.0021(11) 0.0061(10) -0.0009(12)
C4 0.0174(14) 0.0206(17) 0.0181(13) 0.0023(12) 0.0039(11) -0.0022(13)
C5 0.0121(13) 0.0131(16) 0.0279(14) 0.0015(12) 0.0055(11) 0.0009(12)
C6 0.0165(14) 0.0151(16) 0.0206(13) -0.0038(12) 0.0064(11) -0.0040(12)
C7 0.0185(14) 0.0175(16) 0.0166(13) -0.0038(12) 0.0055(11) -0.0025(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 C3 1.886(3) . ?
Cl1 C5 1.731(4) . ?
Cl2 C3 1.739(5) . ?
Br2 C5 1.892(4) . ?
O1 C1 1.251(3) . ?
O2 C1 1.282(3) . ?
C1 C2 1.490(4) . ?
C2 C3 1.408(3) . ?
C2 C7 1.411(4) . ?
C3 C6 1.389(4) . ?
C4 C7 1.383(4) . ?
C4 C5 1.385(4) . ?
C5 C6 1.384(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
O1 C1 O2 122.7(3) . . ?
O1 C1 C2 118.8(2) . . ?
O2 C1 C2 118.5(2) . . ?
C3 C2 C7 117.0(2) . . ?
C3 C2 C1 126.4(2) . . ?
C7 C2 C1 116.7(2) . . ?
C6 C3 C2 121.4(2) . . ?
C6 C3 Cl2 113.9(9) . . ?
C2 C3 Cl2 124.6(9) . . ?
C6 C3 Br1 114.0(2) . . ?
C2 C3 Br1 124.6(2) . . ?
C7 C4 C5 118.4(2) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 Cl1 120.5(6) . . ?
C4 C5 Cl1 117.7(6) . . ?
C6 C5 Br2 117.9(6) . . ?
C4 C5 Br2 120.3(6) . . ?
C5 C6 C3 119.1(2) . . ?
C4 C7 C2 122.3(2) . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.101

_shelx_res_file                  
;
TITL red in P2(1)/n
    shelx.res
    created by SHELXL-2016/6 at 10:44:20 on 17-Apr-2017
CELL  0.71073   7.2385   8.9976  12.1313   90.000  105.406   90.000
ZERR     4.00   0.0004   0.0005   0.0006    0.000    0.005    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    CL   BR
UNIT  28 16 8 4 4
MERG   2
EADP BR1 CL2
EADP BR2 CL1
DFIX 1.900 0.005 C3 BR1 C5 BR2
DFIX 1.740 0.005 C3 CL2 C5 CL1
FMAP   2
PLAN   20
ACTA
LIST   3
L.S.   2
WGHT    0.023800
FVAR       3.51167   0.71458
PART    1
BR1   5    0.887259    0.877784    0.242644    21.00000    0.03069    0.01779 =
         0.01304    0.00175    0.00364   -0.00052
CL1   4    0.585092    1.320651   -0.056718    21.00000    0.02072    0.00821 =
         0.03421    0.00162    0.00630    0.00333
PART    2
CL2   4    0.887829    0.884701    0.230913   -21.00000    0.03069    0.01779 =
         0.01304    0.00175    0.00364   -0.00052
BR2   5    0.583643    1.339570   -0.051294   -21.00000    0.02072    0.00821 =
         0.03421    0.00162    0.00630    0.00333
PART    0
O1    3    0.913429    0.638988   -0.090592    11.00000    0.03596    0.01882 =
         0.01985   -0.00312    0.00672    0.00567
O2    3    0.941407    0.630493    0.096360    11.00000    0.04113    0.01695 =
         0.02152    0.00483    0.00856    0.01103
AFIX  83
H2    2    0.981964    0.547239    0.088235    11.00000   -1.50000
AFIX   0
C1    1    0.895001    0.697336   -0.000469    11.00000    0.01333    0.01415 =
         0.01781    0.00037    0.00313   -0.00362
C2    1    0.817696    0.851335   -0.005306    11.00000    0.01168    0.01136 =
         0.01911    0.00102    0.00358   -0.00091
C3    1    0.807926    0.939721    0.088728    11.00000    0.01548    0.01631 =
         0.01559    0.00207    0.00613   -0.00094
C4    1    0.678355    1.058457   -0.130714    11.00000    0.01744    0.02059 =
         0.01807    0.00225    0.00391   -0.00223
AFIX  43
H4    2    0.634161    1.098170   -0.203772    11.00000   -1.20000
AFIX   0
C5    1    0.674008    1.141288   -0.035189    11.00000    0.01213    0.01308 =
         0.02789    0.00146    0.00555    0.00085
C6    1    0.738250    1.084275    0.074262    11.00000    0.01654    0.01511 =
         0.02065   -0.00380    0.00637   -0.00395
AFIX  43
H6    2    0.734832    1.141955    0.137304    11.00000   -1.20000
AFIX   0
C7    1    0.750010    0.915255   -0.114824    11.00000    0.01846    0.01750 =
         0.01659   -0.00375    0.00553   -0.00247
AFIX  43
H7    2    0.753697    0.859136   -0.178582    11.00000   -1.20000
AFIX   0
HKLF    4




REM  red in P2(1)/n
REM R1 =  0.0330 for    1512 Fo > 4sig(Fo)  and  0.0411 for all    1750 data
REM    107 parameters refined using      4 restraints

END

WGHT      0.0238      0.0000

REM Highest difference peak  0.410,  deepest hole -0.408,  1-sigma level  0.101
Q1    1   0.8589  0.8125 -0.0647  11.00000  0.05    0.41
Q2    1   0.8130  1.0304  0.0799  11.00000  0.05    0.41
Q3    1   0.8065  0.7647  0.2469  11.00000  0.05    0.37
Q4    1   0.7456  0.9926 -0.0949  11.00000  0.05    0.37
Q5    1   0.7498  1.2609 -0.0186  11.00000  0.05    0.36
Q6    1   0.4137  1.3339 -0.0139  11.00000  0.05    0.35
Q7    1   0.9248  0.9964  0.2028  11.00000  0.05    0.34
Q8    1   0.8027  0.8873  0.0390  11.00000  0.05    0.34
Q9    1   0.8357  0.9142  0.1208  11.00000  0.05    0.33
Q10   1   0.5616  1.0187  0.0250  11.00000  0.05    0.33
Q11   1   1.0844  0.8833  0.3044  11.00000  0.05    0.33
Q12   1   0.8419  0.6205 -0.1207  11.00000  0.05    0.32
Q13   1   0.7589  1.0822  0.1370  11.00000  0.05    0.32
Q14   1   1.0008  0.9631  0.3070  11.00000  0.05    0.32
Q15   1   0.9777  0.5612 -0.0847  11.00000  0.05    0.32
Q16   1   0.5290  1.1258 -0.1176  11.00000  0.05    0.32
Q17   1   0.8220  0.7561  0.0012  11.00000  0.05    0.31
Q18   1   0.9902  0.6058  0.1018  11.00000  0.05    0.31
Q19   1   0.7874  0.8936 -0.0421  11.00000  0.05    0.31
Q20   1   0.7220  0.9398  0.0874  11.00000  0.05    0.31
;
_shelx_res_checksum              14260

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535003'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'2-bromo-4-chlorobenzoic acid/4-bromo-2-chlorobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   3.9007(4)
_cell_length_b                   8.3070(4)
_cell_length_c                   11.9258(12)
_cell_angle_alpha                88.909(6)
_cell_angle_beta                 89.987(8)
_cell_angle_gamma                78.731(6)
_cell_volume                     378.91(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1943
_cell_measurement_theta_min      3.0130
_cell_measurement_theta_max      27.4720

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.064
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.714
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5270
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_av_R_equivalents  0.1228
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         27.445
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1718
_reflns_number_gt                1427
_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    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ', occupancy disorder'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.0228P] 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         1718
_refine_ls_number_parameters     107
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.076
_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 0.5809(13) 0.4162(3) 0.3329(4) 0.0240(3) Uani 0.814(2) 1 d D . P A 1
Cl1 Cl 0.826(3) -0.2409(13) 0.4055(11) 0.0221(9) Uani 0.814(2) 1 d D . P A 1
Cl2 Cl 0.576(15) 0.403(3) 0.324(4) 0.0240(3) Uani 0.186(2) 1 d D . P A 2
Br2 Br 0.873(6) -0.251(2) 0.413(2) 0.0221(9) Uani 0.186(2) 1 d D . P A 2
O1 O 0.0207(10) 0.2773(5) 0.0170(3) 0.0326(9) Uani 1 1 d . . . . .
H1 H -0.056140 0.356548 -0.023972 0.049 Uiso 1 1 calc R U . . .
O2 O 0.2542(10) 0.4646(4) 0.1082(3) 0.0315(9) Uani 1 1 d . . . . .
C3 C 0.5265(12) 0.2100(4) 0.2795(4) 0.0208(10) Uani 1 1 d D . . . .
C4 C 0.6636(12) 0.0779(5) 0.3501(4) 0.0229(11) Uani 1 1 d . . . . .
H4 H 0.765024 0.094821 0.418382 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3609(12) 0.1864(5) 0.1785(4) 0.0220(11) Uani 1 1 d . . . . .
C7 C 0.3457(13) 0.0241(6) 0.1498(4) 0.0248(11) Uani 1 1 d . . . . .
H7 H 0.236865 0.006171 0.083041 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4873(13) -0.1095(6) 0.2175(4) 0.0238(11) Uani 1 1 d . . . . .
H6 H 0.476551 -0.215971 0.197173 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6463(12) -0.0786(5) 0.3170(4) 0.0211(10) Uani 1 1 d D . . . .
C1 C 0.2117(13) 0.3243(6) 0.1001(4) 0.0227(11) Uani 1 1 d . . . . .

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 0.0290(4) 0.0119(5) 0.0301(10) -0.0003(4) -0.0067(6) -0.0011(5)
Cl1 0.022(3) 0.0122(12) 0.0289(17) 0.0039(6) -0.0097(15) 0.0033(14)
Cl2 0.0290(4) 0.0119(5) 0.0301(10) -0.0003(4) -0.0067(6) -0.0011(5)
Br2 0.022(3) 0.0122(12) 0.0289(17) 0.0039(6) -0.0097(15) 0.0033(14)
O1 0.040(2) 0.0260(19) 0.030(2) 0.0073(15) -0.0109(18) -0.0023(16)
O2 0.044(2) 0.0190(17) 0.033(2) 0.0050(15) -0.0118(18) -0.0100(16)
C3 0.017(2) 0.016(2) 0.028(3) -0.0017(18) 0.000(2) -0.0006(18)
C4 0.021(3) 0.020(2) 0.024(3) 0.0015(19) 0.000(2) 0.0041(19)
C2 0.021(3) 0.016(2) 0.026(3) -0.0001(19) -0.004(2) 0.0027(18)
C7 0.025(3) 0.024(2) 0.024(3) -0.002(2) 0.000(2) -0.001(2)
C6 0.023(3) 0.019(2) 0.030(3) -0.0027(19) -0.003(2) -0.0043(19)
C5 0.018(2) 0.020(2) 0.023(2) 0.0021(19) 0.002(2) 0.0009(18)
C1 0.023(3) 0.026(3) 0.018(2) 0.0023(19) 0.001(2) -0.002(2)

_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 C3 1.889(4) . ?
Cl1 C5 1.732(4) . ?
Cl2 C3 1.741(5) . ?
Br2 C5 1.894(5) . ?
O1 C1 1.348(6) . ?
O2 C1 1.214(6) . ?
C3 C4 1.391(6) . ?
C3 C2 1.402(6) . ?
C4 C5 1.380(6) . ?
C2 C7 1.410(7) . ?
C2 C1 1.491(6) . ?
C7 C6 1.384(7) . ?
C6 C5 1.391(7) . ?

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
C4 C3 C2 121.1(4) . . ?
C4 C3 Cl2 116.1(18) . . ?
C2 C3 Cl2 122.9(18) . . ?
C4 C3 Br1 114.3(4) . . ?
C2 C3 Br1 124.6(4) . . ?
C5 C4 C3 118.8(4) . . ?
C3 C2 C7 117.7(4) . . ?
C3 C2 C1 122.8(4) . . ?
C7 C2 C1 119.5(4) . . ?
C6 C7 C2 122.3(5) . . ?
C7 C6 C5 117.5(4) . . ?
C4 C5 C6 122.7(4) . . ?
C4 C5 Cl1 117.8(6) . . ?
C6 C5 Cl1 119.6(6) . . ?
C4 C5 Br2 115.5(9) . . ?
C6 C5 Br2 121.8(9) . . ?
O2 C1 O1 122.5(4) . . ?
O2 C1 C2 124.8(4) . . ?
O1 C1 C2 112.7(4) . . ?

_refine_diff_density_max         1.060
_refine_diff_density_min         -1.877
_refine_diff_density_rms         0.205

_shelx_res_file                  
;
TITL new in P-1
    shelx.res
    created by SHELXL-2016/6 at 16:24:34 on 17-Apr-2017
CELL  0.71073   3.9007   8.3070  11.9258   88.909   89.987   78.731
ZERR     2.00   0.0004   0.0004   0.0012    0.006    0.008    0.006
LATT   1
SFAC  C    H    O    CL   BR
UNIT  14 8 4 2 2
MERG   2
EADP BR1 CL2
EADP BR2 CL1
DFIX 1.900 0.005 C3 BR1
DFIX 1.900 0.005 C5 BR2
DFIX 1.740 0.005 C3 CL2
DFIX 1.740 0.005 C5 CL1
FMAP   2
PLAN   20
ACTA
LIST   3
L.S.   5
WGHT    0.066900    0.022800
FVAR       6.35525   0.81362
PART    1
BR1   5    0.580859    0.416199    0.332873    21.00000    0.02900    0.01185 =
         0.03010   -0.00028   -0.00671   -0.00110
CL1   4    0.826306   -0.240923    0.405504    21.00000    0.02234    0.01225 =
         0.02885    0.00387   -0.00968    0.00328
PART    2
CL2   4    0.576490    0.402500    0.323877   -21.00000    0.02900    0.01185 =
         0.03010   -0.00028   -0.00671   -0.00110
BR2   5    0.873004   -0.250785    0.413253   -21.00000    0.02234    0.01225 =
         0.02885    0.00387   -0.00968    0.00328
PART    0
O1    3    0.020654    0.277319    0.016998    11.00000    0.04025    0.02597 =
         0.02962    0.00727   -0.01092   -0.00233
AFIX  83
H1    2   -0.056140    0.356548   -0.023972    11.00000   -1.50000
AFIX   0
O2    3    0.254168    0.464589    0.108234    11.00000    0.04438    0.01904 =
         0.03257    0.00502   -0.01181   -0.01005
C3    1    0.526510    0.209983    0.279489    11.00000    0.01717    0.01597 =
         0.02811   -0.00170    0.00034   -0.00058
C4    1    0.663607    0.077946    0.350127    11.00000    0.02099    0.02016 =
         0.02427    0.00155   -0.00023    0.00407
AFIX  43
H4    2    0.765024    0.094821    0.418382    11.00000   -1.20000
AFIX   0
C2    1    0.360854    0.186407    0.178452    11.00000    0.02101    0.01586 =
         0.02640   -0.00013   -0.00372    0.00273
C7    1    0.345724    0.024086    0.149759    11.00000    0.02483    0.02438 =
         0.02376   -0.00234    0.00012   -0.00115
AFIX  43
H7    2    0.236865    0.006171    0.083041    11.00000   -1.20000
AFIX   0
C6    1    0.487317   -0.109527    0.217473    11.00000    0.02313    0.01867 =
         0.02978   -0.00269   -0.00324   -0.00430
AFIX  43
H6    2    0.476551   -0.215971    0.197173    11.00000   -1.20000
AFIX   0
C5    1    0.646335   -0.078590    0.317040    11.00000    0.01794    0.02042 =
         0.02304    0.00211    0.00155    0.00092
C1    1    0.211678    0.324349    0.100076    11.00000    0.02283    0.02630 =
         0.01761    0.00229    0.00118   -0.00162
HKLF    4




REM  new in P-1
REM R1 =  0.0601 for    1427 Fo > 4sig(Fo)  and  0.0734 for all    1718 data
REM    107 parameters refined using      4 restraints

END

WGHT      0.0675      0.0228

REM Highest difference peak  1.060,  deepest hole -1.877,  1-sigma level  0.205
Q1    1   0.3886  0.4124  0.3991  11.00000  0.05    1.06
Q2    1   0.7139  0.4039  0.3974  11.00000  0.05    0.94
Q3    1   0.3279  0.3573  0.3275  11.00000  0.05    0.80
Q4    1   0.3921  0.4362  0.2782  11.00000  0.05    0.73
Q5    1   0.7216  0.4195  0.2563  11.00000  0.05    0.71
Q6    1   1.0482 -0.5282  0.4545  11.00000  0.05    0.70
Q7    1   0.8770 -0.2361  0.3316  11.00000  0.05    0.69
Q8    1   0.4814  0.5221  0.4059  11.00000  0.05    0.68
Q9    1   0.6331  0.3284  0.4378  11.00000  0.05    0.67
Q10   1   0.7785 -0.3951  0.4592  11.00000  0.05    0.66
Q11   1   0.8604  0.4668  0.3287  11.00000  0.05    0.65
Q12   1   0.6328  0.4349  0.2424  11.00000  0.05    0.64
Q13   1   0.8215 -0.2103  0.4904  11.00000  0.05    0.58
Q14   1   0.5420  0.1195  0.4933  11.00000  0.05    0.57
Q15   1   0.3434  0.4560  0.3045  11.00000  0.05    0.57
Q16   1   1.1051 -0.3865  0.4536  11.00000  0.05    0.56
Q17   1   0.6870  0.2996  0.2516  11.00000  0.05    0.56
Q18   1   0.2831  0.5217  0.4254  11.00000  0.05    0.55
Q19   1   0.6758 -0.2410  0.4829  11.00000  0.05    0.53
Q20   1  -0.0012  0.3111  0.2351  11.00000  0.05    0.53
;
_shelx_res_checksum              52901

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535000'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-chlobenzoic acid/ 2-bromo-4-chlorobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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/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                   7.2399(3)
_cell_length_b                   9.0087(2)
_cell_length_c                   12.0539(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.036(4)
_cell_angle_gamma                90
_cell_volume                     759.26(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3289
_cell_measurement_theta_min      2.8680
_cell_measurement_theta_max      29.6800

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.703
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5835
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         30.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2007
_reflns_number_gt                1791
_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    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ', Occupancy disorder '
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.3256P] 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         2007
_refine_ls_number_parameters     107
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.8842(4) 0.3789(4) 0.24397(12) 0.0201(2) Uani 0.6151(13) 1 d D . P A 1
Cl1 Cl 0.5793(12) 0.8164(5) -0.0552(10) 0.0195(4) Uani 0.6151(13) 1 d D . P A 1
Cl2 Cl 0.8911(19) 0.3812(15) 0.2314(5) 0.0201(2) Uani 0.3849(13) 1 d D . P A 2
Br2 Br 0.5881(7) 0.8387(3) -0.0550(6) 0.0195(4) Uani 0.3849(13) 1 d D . P A 2
O1 O 0.9151(2) 0.13848(17) -0.08990(13) 0.0244(4) Uani 1 1 d . . . . .
O2 O 0.9398(3) 0.13034(17) 0.09788(14) 0.0268(4) Uani 1 1 d . . . . .
H2 H 0.980465 0.046998 0.090405 0.040 Uiso 1 1 calc R U . . .
C1 C 0.8956(3) 0.1965(2) -0.00029(18) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.6754(3) 0.6398(2) -0.0355(2) 0.0174(4) Uani 1 1 d D . . . .
C2 C 0.8180(3) 0.3512(2) -0.00493(18) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.8077(3) 0.4390(2) 0.08912(16) 0.0154(4) Uani 1 1 d D . . . .
C6 C 0.6802(3) 0.5567(2) -0.13137(19) 0.0184(4) Uani 1 1 d . . . . .
H6 H 0.636494 0.595822 -0.204942 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7379(3) 0.5837(2) 0.07440(19) 0.0169(4) Uani 1 1 d . . . . .
H4 H 0.733492 0.641589 0.137566 0.020 Uiso 1 1 calc R U . . .
C7 C 0.7521(3) 0.4137(2) -0.11431(18) 0.0175(4) Uani 1 1 d . . . . .
H7 H 0.756729 0.357059 -0.178029 0.021 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 0.0315(3) 0.01546(18) 0.0128(4) 0.0010(4) 0.0049(4) -0.00110(18)
Cl1 0.0202(5) 0.0033(8) 0.0345(2) 0.0039(10) 0.0061(3) -0.0007(8)
Cl2 0.0315(3) 0.01546(18) 0.0128(4) 0.0010(4) 0.0049(4) -0.00110(18)
Br2 0.0202(5) 0.0033(8) 0.0345(2) 0.0039(10) 0.0061(3) -0.0007(8)
O1 0.0353(10) 0.0173(7) 0.0199(9) -0.0029(6) 0.0060(7) 0.0057(7)
O2 0.0439(10) 0.0164(7) 0.0204(8) 0.0040(6) 0.0091(8) 0.0108(7)
C1 0.0142(9) 0.0121(8) 0.0184(10) -0.0008(8) 0.0031(8) -0.0021(7)
C5 0.0141(9) 0.0106(8) 0.0275(12) 0.0018(8) 0.0053(8) 0.0007(7)
C2 0.0132(9) 0.0113(8) 0.0191(10) -0.0002(7) 0.0040(8) -0.0015(7)
C3 0.0160(10) 0.0144(9) 0.0157(10) 0.0023(8) 0.0039(8) -0.0026(8)
C6 0.0175(10) 0.0179(9) 0.0196(11) 0.0035(8) 0.0045(8) 0.0004(8)
C4 0.0181(10) 0.0145(9) 0.0194(10) -0.0030(8) 0.0073(8) -0.0005(8)
C7 0.0184(10) 0.0175(9) 0.0173(10) -0.0010(8) 0.0061(8) -0.0003(8)

_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 C3 1.884(2) . ?
Cl1 C5 1.728(4) . ?
Cl2 C3 1.743(5) . ?
Br2 C5 1.895(3) . ?
O1 C1 1.241(2) . ?
O2 C1 1.289(3) . ?
C1 C2 1.498(3) . ?
C5 C4 1.380(3) . ?
C5 C6 1.385(3) . ?
C2 C7 1.399(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.393(3) . ?
C6 C7 1.385(3) . ?

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
O1 C1 O2 123.17(19) . . ?
O1 C1 C2 119.06(18) . . ?
O2 C1 C2 117.77(18) . . ?
C4 C5 C6 122.05(18) . . ?
C4 C5 Cl1 119.3(4) . . ?
C6 C5 Cl1 118.6(4) . . ?
C4 C5 Br2 118.8(3) . . ?
C6 C5 Br2 119.1(3) . . ?
C7 C2 C3 117.29(18) . . ?
C7 C2 C1 116.28(18) . . ?
C3 C2 C1 126.42(19) . . ?
C4 C3 C2 121.31(18) . . ?
C4 C3 Cl2 115.3(5) . . ?
C2 C3 Cl2 123.3(5) . . ?
C4 C3 Br1 113.52(18) . . ?
C2 C3 Br1 125.16(18) . . ?
C5 C6 C7 117.94(19) . . ?
C5 C4 C3 118.86(19) . . ?
C6 C7 C2 122.5(2) . . ?

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.093

_shelx_res_file                  
;
TITL red in P2(1)/n
    shelx.res
    created by SHELXL-2016/6 at 10:27:16 on 17-Apr-2017
CELL  0.71073   7.2399   9.0087  12.0539   90.000  105.036   90.000
ZERR     4.00   0.0003   0.0002   0.0004    0.000    0.004    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    CL   BR
UNIT  28 16 8 4 4
MERG   2
EADP BR1 CL2
EADP BR2 CL1
DFIX 1.900 0.005 C5 BR2
DFIX 1.900 0.005 C3 BR1
DFIX 1.740 0.005 C3 CL2
DFIX 1.740 0.005 C5 CL1
FMAP   2
PLAN   20
ACTA
LIST   3
L.S.   5
WGHT    0.028200    0.325600
FVAR       5.11134   0.61514
PART    1
BR1   5    0.884219    0.378886    0.243970    21.00000    0.03148    0.01546 =
         0.01280    0.00104    0.00490   -0.00110
CL1   4    0.579267    0.816379   -0.055174    21.00000    0.02020    0.00328 =
         0.03449    0.00386    0.00613   -0.00068
PART    2
CL2   4    0.891135    0.381208    0.231353   -21.00000    0.03148    0.01546 =
         0.01280    0.00104    0.00490   -0.00110
BR2   5    0.588105    0.838735   -0.055034   -21.00000    0.02020    0.00328 =
         0.03449    0.00386    0.00613   -0.00068
PART    0
O1    3    0.915054    0.138482   -0.089903    11.00000    0.03529    0.01731 =
         0.01988   -0.00288    0.00600    0.00566
O2    3    0.939774    0.130341    0.097881    11.00000    0.04391    0.01642 =
         0.02038    0.00403    0.00914    0.01080
AFIX  83
H2    2    0.980465    0.046998    0.090405    11.00000   -1.50000
AFIX   0
C1    1    0.895561    0.196521   -0.000289    11.00000    0.01417    0.01212 =
         0.01840   -0.00082    0.00306   -0.00206
C5    1    0.675397    0.639786   -0.035483    11.00000    0.01411    0.01064 =
         0.02745    0.00184    0.00526    0.00070
C2    1    0.817972    0.351161   -0.004927    11.00000    0.01320    0.01127 =
         0.01911   -0.00021    0.00401   -0.00146
C3    1    0.807675    0.439017    0.089115    11.00000    0.01600    0.01444 =
         0.01573    0.00233    0.00394   -0.00264
C6    1    0.680192    0.556750   -0.131369    11.00000    0.01755    0.01786 =
         0.01964    0.00346    0.00448    0.00042
AFIX  43
H6    2    0.636494    0.595822   -0.204942    11.00000   -1.20000
AFIX   0
C4    1    0.737887    0.583739    0.074401    11.00000    0.01807    0.01455 =
         0.01939   -0.00300    0.00727   -0.00054
AFIX  43
H4    2    0.733492    0.641589    0.137566    11.00000   -1.20000
AFIX   0
C7    1    0.752079    0.413713   -0.114312    11.00000    0.01845    0.01752 =
         0.01728   -0.00097    0.00615   -0.00034
AFIX  43
H7    2    0.756729    0.357059   -0.178029    11.00000   -1.20000
AFIX   0
HKLF    4




REM  red in P2(1)/n
REM R1 =  0.0277 for    1791 Fo > 4sig(Fo)  and  0.0330 for all    2007 data
REM    107 parameters refined using      4 restraints

END

WGHT      0.0280      0.3279

REM Highest difference peak  0.381,  deepest hole -0.579,  1-sigma level  0.093
Q1    1   0.8268  0.4118  0.1348  11.00000  0.05    0.38
Q2    1   1.0730  0.2212  0.1991  11.00000  0.05    0.35
Q3    1   0.8657  0.2758  0.0063  11.00000  0.05    0.35
Q4    1   0.7278  0.4900 -0.1149  11.00000  0.05    0.35
Q5    1   0.6547  0.6936 -0.0429  11.00000  0.05    0.33
Q6    1   0.8090  0.2805  0.2762  11.00000  0.05    0.31
Q7    1   0.7543  0.3866 -0.0551  11.00000  0.05    0.30
Q8    1   0.4988  0.7419  0.0028  11.00000  0.05    0.30
Q9    1   0.6702  0.9336  0.0007  11.00000  0.05    0.30
Q10   1   0.8910  0.5883  0.2407  11.00000  0.05    0.29
Q11   1   0.9724  0.2817  0.1929  11.00000  0.05    0.29
Q12   1   0.8223  0.3942  0.0423  11.00000  0.05    0.29
Q13   1   1.0536  0.3631  0.3982  11.00000  0.05    0.28
Q14   1   0.7501  0.8658 -0.0443  11.00000  0.05    0.28
Q15   1   1.0317  0.3807  0.2593  11.00000  0.05    0.28
Q16   1   1.0292  0.2383  0.1170  11.00000  0.05    0.28
Q17   1   1.0229 -0.0413  0.0858  11.00000  0.05    0.28
Q18   1   0.7434  0.6332  0.0206  11.00000  0.05    0.28
Q19   1   0.9131  0.6611  0.0801  11.00000  0.05    0.27
Q20   1   0.6270  0.2038 -0.1086  11.00000  0.05    0.27
;
_shelx_res_checksum              92892

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
