# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_p-BrBA_Room_Temperature
_database_code_depnum_ccdc_archive 'CCDC 1513379'
_audit_update_record             
;
2016-10-29 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 Br O'
_chemical_formula_weight         187.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21'

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

_cell_length_a                   6.0614(5)
_cell_length_b                   4.9572(4)
_cell_length_c                   12.1601(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.523(8)
_cell_angle_gamma                90
_cell_volume                     356.69(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    654
_cell_measurement_theta_min      3.2030
_cell_measurement_theta_max      24.1181
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             184
_exptl_absorpt_coefficient_mu    5.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   
;
 ?   
;

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1556
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.443
_diffrn_reflns_theta_max         28.825
_reflns_number_total             1244
_reflns_number_gt                1000
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_number_reflns         1244
_refine_ls_number_parameters     73
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.85534(12) 0.7204(5) 0.39848(6) 0.0584(4) Uani 1 1 d . . . . .
C1 C 0.6499(8) 0.4728(8) 0.3173(4) 0.044(2) Uani 1 1 d G . . . .
C2 C 0.6755(8) 0.3724(12) 0.2140(4) 0.055(2) Uani 1 1 d G . . . .
H2 H 0.7947 0.4312 0.1833 0.066 Uiso 1 1 calc R U . . .
C3 C 0.5229(10) 0.1841(13) 0.1568(4) 0.054(2) Uani 1 1 d G . . . .
H3 H 0.5400 0.1169 0.0878 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3447(8) 0.0962(12) 0.2029(4) 0.049(2) Uani 1 1 d G . . . .
C5 C 0.3191(7) 0.1966(13) 0.3061(4) 0.051(2) Uani 1 1 d G . . . .
H5 H 0.1998 0.1377 0.3369 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4717(9) 0.3849(11) 0.3633(4) 0.047(2) Uani 1 1 d G . . . .
H6 H 0.4545 0.4521 0.4324 0.057 Uiso 1 1 calc R U . . .
C7 C 0.1808(18) -0.113(2) 0.1452(10) 0.074(3) Uani 1 1 d . . . . .
H7A H 0.2591 -0.2834 0.1461 0.089 Uiso 1 1 calc R U . . .
H7B H 0.0631 -0.1357 0.1872 0.089 Uiso 1 1 calc R U . . .
O1 O 0.0828(16) -0.0480(16) 0.0361(6) 0.075(2) Uani 1 1 d . . . . .
H1 H 0.04(3) 0.08(2) 0.015(14) 0.113 Uiso 1 1 d . 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 0.0554(5) 0.0610(6) 0.0532(5) -0.0011(8) -0.0003(3) -0.0134(6)
C1 0.045(5) 0.047(5) 0.037(4) -0.001(4) 0.000(4) 0.003(4)
C2 0.053(5) 0.068(7) 0.046(5) 0.003(5) 0.015(4) -0.006(5)
C3 0.066(5) 0.054(7) 0.041(4) -0.003(6) 0.009(4) 0.008(6)
C4 0.049(5) 0.038(5) 0.049(5) 0.019(4) -0.013(4) -0.007(4)
C5 0.054(4) 0.048(5) 0.050(4) 0.010(7) 0.010(3) -0.013(6)
C6 0.055(5) 0.055(6) 0.033(4) 0.005(4) 0.010(4) -0.002(5)
C7 0.074(7) 0.062(7) 0.071(7) 0.019(6) -0.020(6) -0.016(6)
O1 0.105(6) 0.048(4) 0.050(4) 0.008(4) -0.033(4) -0.011(5)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.870(4) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 C7 1.499(10) . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.368(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O1 H1 0.71(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.0 . . ?
C2 C1 Br1 121.3(3) . . ?
C6 C1 Br1 118.7(3) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C7 121.5(6) . . ?
C5 C4 C7 118.5(6) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 C4 113.4(8) . . ?
O1 C7 H7A 108.9 . . ?
C4 C7 H7A 108.9 . . ?
O1 C7 H7B 108.9 . . ?
C4 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 O1 H1 127(10) . . ?

_diffrn_measured_fraction_theta_max 0.872
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_p-MeBA_BrBA_50_50
_database_code_depnum_ccdc_archive 'CCDC 1513380'
_audit_update_record             
;
2016-10-29 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT215_p-MeBA_BrBA_50_50   
;
PROBLEM: Disordered C8        has ADP max/min Ratio .....        4.8  
RESPONSE: Data quality scarce and disorder probably affecting, 
even shlightly, the whole molecule.
;
_vrf_PLAT341_p-MeBA_BrBA_50_50   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01771 Ang.  
RESPONSE: Again, this is due to low diffraction and poor data quality. 
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7.50 H8.50 Br0.50 O'
_chemical_formula_weight         154.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

_cell_length_a                   6.044(2)
_cell_length_b                   4.9739(12)
_cell_length_c                   12.231(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.69(4)
_cell_angle_gamma                90
_cell_volume                     357.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      3.8115
_cell_measurement_theta_max      24.3207
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             158
_exptl_absorpt_coefficient_mu    2.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   
;
 ?   
;

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1188
_diffrn_reflns_av_unetI/netI     0.1167
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.429
_diffrn_reflns_theta_max         26.659
_reflns_number_total             904
_reflns_number_gt                589
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1067P)²+0.0216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(4)
_refine_ls_number_reflns         904
_refine_ls_number_parameters     79
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0943
_refine_ls_wR_factor_ref         0.2507
_refine_ls_wR_factor_gt          0.2196
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.138
_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 0.8663(8) 0.2268(18) 0.9009(4) 0.0642(12) Uani 0.5 1 d . . P A 1
C8 C 0.809(5) 0.244(6) 0.873(3) 0.10(3) Uani 0.5 1 d D U P A 2
H8A H 0.9202 0.2066 0.8300 0.154 Uiso 0.5 1 calc R U P A 2
H8B H 0.8854 0.2927 0.9480 0.154 Uiso 0.5 1 calc R U P A 2
H8C H 0.7182 0.0862 0.8743 0.154 Uiso 0.5 1 calc R U P A 2
C7 C 0.193(4) 1.064(5) 0.6469(16) 0.106(8) Uani 1 1 d . . . . .
H7A H 0.0808 1.1049 0.6897 0.128 Uiso 1 1 calc R U . . .
H7B H 0.2811 1.2255 0.6438 0.128 Uiso 1 1 calc R U . . .
O1 O 0.082(3) 0.990(3) 0.5385(11) 0.121(6) Uani 1 1 d . . . . .
H1 H -0.0068 1.1090 0.5098 0.181 Uiso 1 1 calc R U . . .
C1 C 0.6585(17) 0.4716(14) 0.8185(9) 0.066(5) Uani 1 1 d DG U . . .
C2 C 0.484(2) 0.562(2) 0.8656(8) 0.082(6) Uani 1 1 d DG . . A .
H2 H 0.4716 0.4964 0.9351 0.098 Uiso 1 1 calc R U . . .
C3 C 0.3280(16) 0.749(2) 0.8087(10) 0.075(4) Uani 1 1 d G . . A .
H3 H 0.2112 0.8092 0.8402 0.090 Uiso 1 1 calc R U . . .
C4 C 0.3465(17) 0.846(2) 0.7047(9) 0.069(5) Uani 1 1 d DG . . A .
C5 C 0.521(2) 0.756(2) 0.6576(8) 0.075(5) Uani 1 1 d G . . A .
H5 H 0.5334 0.8216 0.5880 0.090 Uiso 1 1 calc R U . . .
C6 C 0.6770(17) 0.569(2) 0.7145(10) 0.077(5) Uani 1 1 d DG . . A .
H6 H 0.7938 0.5088 0.6830 0.093 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 0.054(3) 0.055(2) 0.074(2) -0.001(2) -0.004(2) 0.014(3)
C8 0.04(2) 0.025(16) 0.20(6) 0.01(2) -0.06(2) -0.013(14)
C7 0.12(2) 0.079(15) 0.103(15) 0.007(13) 0.002(14) 0.033(14)
O1 0.167(17) 0.060(8) 0.098(10) -0.001(8) -0.043(9) 0.019(10)
C1 0.055(11) 0.044(9) 0.096(12) 0.014(9) 0.014(10) 0.005(9)
C2 0.071(14) 0.055(12) 0.129(15) -0.013(12) 0.044(12) -0.002(11)
C3 0.057(10) 0.066(11) 0.103(12) -0.006(14) 0.018(9) 0.011(14)
C4 0.065(12) 0.049(9) 0.083(11) -0.016(9) -0.005(9) 0.019(8)
C5 0.073(11) 0.066(12) 0.081(10) 0.002(12) 0.009(9) 0.028(14)
C6 0.057(12) 0.086(12) 0.087(12) -0.018(11) 0.013(10) 0.017(11)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.865(10) . ?
C8 C1 1.506(7) . ?
C7 O1 1.39(2) . ?
C7 C4 1.49(2) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?

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 C7 C4 111.4(16) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 C8 120.0(7) . . ?
C6 C1 C8 119.6(7) . . ?
C2 C1 Br1 117.8(7) . . ?
C6 C1 Br1 122.2(7) . . ?
C1 C2 C3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C7 119.1(12) . . ?
C3 C4 C7 120.7(12) . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.792
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.908
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_p-ClBA_BrBA_50_50
_database_code_depnum_ccdc_archive 'CCDC 1513381'
_audit_update_record             
;
2016-12-03 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 Br0.50 Cl0.50 O'
_chemical_formula_weight         164.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

_cell_length_a                   5.9892(6)
_cell_length_b                   4.9395(5)
_cell_length_c                   12.0858(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.590(10)
_cell_angle_gamma                90
_cell_volume                     348.94(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    928
_cell_measurement_theta_min      3.4029
_cell_measurement_theta_max      25.1008
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             166
_exptl_absorpt_coefficient_mu    3.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   
;
 ?   
;

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1560
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.455
_diffrn_reflns_theta_max         29.234
_reflns_number_total             1206
_reflns_number_gt                954
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_number_reflns         1206
_refine_ls_number_parameters     79
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.006
_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
Cl1 Cl 0.1453(18) 0.740(3) 0.0999(6) 0.043(3) Uani 0.5 1 d D . P A 1
Br1 Br 0.1401(10) 0.7731(16) 0.1022(4) 0.0714(19) Uani 0.5 1 d D . P A 2
C4 C 0.6553(7) 0.1445(6) 0.2957(4) 0.0526(19) Uani 1 1 d G . . . .
C3 C 0.4757(8) 0.2341(9) 0.3422(3) 0.062(2) Uani 1 1 d G . . . .
H3 H 0.4594 0.1683 0.4122 0.075 Uiso 1 1 calc R U . . .
C2 C 0.3206(7) 0.4221(10) 0.2843(4) 0.061(2) Uani 1 1 d G . . . .
H2 H 0.2005 0.4821 0.3154 0.073 Uiso 1 1 calc R U . . .
C1 C 0.3450(7) 0.5204(10) 0.1798(4) 0.0482(17) Uani 1 1 d DG . . . .
C6 C 0.5245(8) 0.4307(10) 0.1333(3) 0.0500(18) Uani 1 1 d G . . . .
H6 H 0.5408 0.4965 0.0634 0.060 Uiso 1 1 calc R U . . .
C5 C 0.6796(6) 0.2428(9) 0.1912(4) 0.0542(16) Uani 1 1 d G . . . .
H5 H 0.7997 0.1828 0.1601 0.065 Uiso 1 1 calc R U . . .
C7 C 0.8196(14) -0.0695(19) 0.3532(7) 0.075(3) Uani 1 1 d . . . . .
H7A H 0.7386 -0.2398 0.3525 0.090 Uiso 1 1 calc R U . . .
H7B H 0.9386 -0.0948 0.3110 0.090 Uiso 1 1 calc R U . . .
O1 O 0.9176(11) -0.0014(12) 0.4626(5) 0.085(2) Uani 1 1 d . . . . .
H1 H 1.0044 -0.1226 0.4916 0.127 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
Cl1 0.053(5) 0.047(6) 0.030(3) -0.002(3) 0.013(3) 0.012(3)
Br1 0.065(3) 0.054(3) 0.089(3) 0.0033(17) 0.004(2) 0.0143(15)
C4 0.053(4) 0.038(4) 0.058(4) -0.012(3) -0.006(3) 0.004(3)
C3 0.079(5) 0.061(6) 0.051(4) -0.002(6) 0.023(4) 0.005(6)
C2 0.056(5) 0.071(5) 0.057(5) 0.008(4) 0.018(4) 0.018(4)
C1 0.052(4) 0.037(4) 0.052(4) -0.008(4) 0.003(3) 0.002(3)
C6 0.056(4) 0.049(4) 0.050(4) -0.002(4) 0.022(4) 0.003(4)
C5 0.054(4) 0.051(4) 0.059(4) -0.005(6) 0.012(3) 0.011(5)
C7 0.090(7) 0.064(6) 0.063(5) -0.006(5) 0.000(5) 0.021(5)
O1 0.113(5) 0.051(3) 0.069(4) -0.007(3) -0.025(3) 0.014(4)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cl1 C1 1.743(9) . ?
Br1 C1 1.855(6) . ?
C4 C3 1.3900 . ?
C4 C5 1.3900 . ?
C4 C7 1.507(8) . ?
C3 C2 1.3900 . ?
C2 C1 1.3900 . ?
C1 C6 1.3900 . ?
C6 C5 1.3900 . ?
C7 O1 1.367(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C4 C5 120.0 . . ?
C3 C4 C7 121.5(5) . . ?
C5 C4 C7 118.5(5) . . ?
C4 C3 C2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C6 C1 C2 120.0 . . ?
C6 C1 Cl1 118.1(4) . . ?
C2 C1 Cl1 121.7(4) . . ?
C6 C1 Br1 119.6(3) . . ?
C2 C1 Br1 120.4(3) . . ?
C1 C6 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
O1 C7 C4 111.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.073
