#------------------------------------------------------------------------------
#$Date: 2018-07-14 05:03:57 +0300 (Sat, 14 Jul 2018) $
#$Revision: 209026 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/11/2021178.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021178
loop_
_publ_author_name
'Khoj, Manal A.'
'Hughes, Colan E.'
'Harris, Kenneth D. M.'
'Kariuki, Benson M.'
_publ_section_title
;
 Polymorphic phase transformations of 3-chloro-trans-cinnamic acid
 and its solid solution with 3-bromo-trans-cinnamic acid
;
_journal_coeditor_code           KU3223
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618009269
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H7 Br0.43 Cl0.57 O2'
_chemical_formula_moiety         'C9 H7 Br0.43 Cl0.57 O2'
_chemical_formula_sum            'C9 H7 Br0.43 Cl0.57 O2'
_chemical_formula_weight         201.49
_chemical_name_systematic
;
3-(3-Chloro/bromophenyl)prop-2-enoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.871(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3957(8)
_cell_length_b                   4.9381(2)
_cell_length_c                   14.2102(12)
_cell_measurement_reflns_used    1154
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.2860
_cell_measurement_theta_min      6.2410
_cell_volume                     866.68(10)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type
'Agilent SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2874
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.921
_diffrn_reflns_theta_min         6.252
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.627
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       needle
_exptl_crystal_F_000             405
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1670
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0580P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                1306
_reflns_number_total             1670
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ku3223sup1.cif
_cod_data_source_block           I
_cod_database_code               2021178
_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.
;
_shelx_estimated_absorpt_t_min   0.348
_shelx_estimated_absorpt_t_max   0.808
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.67233(18) -0.6465(4) 0.23649(16) 0.0493(5) Uani d 1
C C2 0.62396(18) -0.5315(5) 0.31173(16) 0.0528(5) Uani d 1
H H2 0.555859 -0.589481 0.325993 0.063 Uiso calc 1
C C3 0.6770(2) -0.3315(5) 0.36513(16) 0.0557(6) Uani d 1
C C4 0.7783(2) -0.2403(5) 0.34630(19) 0.0610(6) Uani d 1
H H4 0.813206 -0.105848 0.383226 0.073 Uiso calc 1
C C5 0.8267(2) -0.3534(5) 0.27113(19) 0.0629(6) Uani d 1
H H5 0.894935 -0.294524 0.257509 0.075 Uiso calc 1
C C6 0.77456(18) -0.5532(5) 0.21618(17) 0.0552(6) Uani d 1
H H6 0.807542 -0.625904 0.165490 0.066 Uiso calc 1
C C7 0.61382(18) -0.8594(4) 0.18165(17) 0.0510(5) Uani d 1
H H7 0.546210 -0.906212 0.200428 0.061 Uiso calc 1
C C8 0.64617(17) -0.9925(5) 0.10857(15) 0.0513(5) Uani d 1
H H8 0.712007 -0.946555 0.085987 0.062 Uiso calc 1
C C9 0.58153(17) -1.2110(4) 0.06175(16) 0.0471(5) Uani d 1
O O1 0.62133(13) -1.3381(3) -0.00454(13) 0.0589(4) Uani d 1
O O2 0.48893(13) -1.2659(4) 0.08900(13) 0.0594(5) Uani d 1
Cl Cl1 0.6164(7) -0.170(2) 0.4567(5) 0.0732(12) Uani d 0.575(4)
Br Br1 0.6053(4) -0.1842(12) 0.4661(2) 0.0710(7) Uani d 0.425(4)
H H1O 0.438(4) -1.450(11) 0.045(3) 0.145(16) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.7(2)
C2 C1 C7 118.4(2)
C6 C1 C7 122.8(2)
C3 C2 C1 120.0(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 121.7(2)
C2 C3 Cl1 121.5(4)
C4 C3 Cl1 116.7(4)
C2 C3 Br1 117.3(3)
C4 C3 Br1 120.9(3)
Cl1 C3 Br1 4.9(6)
C3 C4 C5 118.6(2)
C3 C4 H4 120.7
C5 C4 H4 120.7
C6 C5 C4 120.6(2)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 120.4(2)
C5 C6 H6 119.8
C1 C6 H6 119.8
C8 C7 C1 127.4(2)
C8 C7 H7 116.3
C1 C7 H7 116.3
C7 C8 C9 122.11(19)
C7 C8 H8 118.9
C9 C8 H8 118.9
O1 C9 O2 122.7(2)
O1 C9 C8 117.97(18)
O2 C9 C8 119.37(19)
C9 O2 H1O 115.5(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.391(3)
C1 C6 1.401(3)
C1 C7 1.464(3)
C2 C3 1.378(3)
C2 H2 0.9300
C3 C4 1.381(4)
C3 Cl1 1.7504(10)
C3 Br1 1.896(4)
C4 C5 1.387(4)
C4 H4 0.9300
C5 C6 1.384(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.320(3)
C7 H7 0.9300
C8 C9 1.469(3)
C8 H8 0.9300
C9 O1 1.266(3)
C9 O2 1.271(3)
O2 H1O 1.24(5)
