#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:26:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180429 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/98/7209814.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7209814
loop_
_publ_author_name
'Yates, Jane L. R.'
'Sparkes, Hazel A.'
_publ_section_title
;
 4-Bromo-trans-cinnamic acid: structural characterisation and
 crystallographic investigation into the solid state [2 + 2] cycloaddition
 reaction and temperature induced phase transition
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              3547
_journal_paper_doi               10.1039/c3ce40300a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C9 H7 Br O2'
_chemical_formula_sum            'C9 H7 Br O2'
_chemical_formula_weight         227.06
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.5710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8994(4)
_cell_length_b                   3.8566(2)
_cell_length_c                   31.2021(19)
_cell_measurement_reflns_used    3210
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      56.560
_cell_measurement_theta_min      5.222
_cell_volume                     830.19(8)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.054 (Bruker, 1999)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 6K CCD Detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            4802
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    4.901
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.095
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0449P)²+1.0312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                1538
_reflns_number_total             1689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40300a.txt
_cod_data_source_block           120K
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7209814
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.38975(4) 0.52376(7) 0.211457(10) 0.02024(15) Uani 1 1 d .
O1 O 1.4072(4) -0.0604(6) 0.04972(8) 0.0254(5) Uani 1 1 d .
O2 O 1.2830(3) 0.2310(7) -0.00627(7) 0.0279(5) Uani 1 1 d .
H2 H 1.3865 0.1632 -0.0175 0.034 Uiso 1 1 calc R
C1 C 0.7452(5) 0.3876(8) 0.10684(10) 0.0193(6) Uani 1 1 d .
H1 H 0.7396 0.4401 0.0771 0.023 Uiso 1 1 calc R
C2 C 0.5892(5) 0.4713(8) 0.13259(11) 0.0203(7) Uani 1 1 d .
H2A H 0.4769 0.5785 0.1207 0.024 Uiso 1 1 calc R
C3 C 0.5999(4) 0.3962(8) 0.17579(10) 0.0168(6) Uani 1 1 d .
C4 C 0.7604(4) 0.2345(8) 0.19391(10) 0.0182(6) Uani 1 1 d .
H4 H 0.7647 0.1827 0.2237 0.022 Uiso 1 1 calc R
C5 C 0.9147(4) 0.1498(8) 0.16772(10) 0.0175(6) Uani 1 1 d .
H5 H 1.0250 0.0373 0.1798 0.021 Uiso 1 1 calc R
C6 C 0.9107(4) 0.2270(7) 0.12395(10) 0.0158(6) Uani 1 1 d .
C7 C 1.0778(4) 0.1377(8) 0.09762(10) 0.0183(6) Uani 1 1 d .
H7 H 1.1782 0.0071 0.1110 0.022 Uiso 1 1 calc R
C8 C 1.1024(5) 0.2224(8) 0.05657(10) 0.0200(6) Uani 1 1 d .
H8 H 1.0040 0.3520 0.0423 0.024 Uiso 1 1 calc R
C9 C 1.2759(5) 0.1231(8) 0.03259(10) 0.0197(6) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 '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
C9 O2 H2 109.5
C2 C1 C6 121.1(3)
C2 C1 H1 119.5
C6 C1 H1 119.5
C3 C2 C1 118.8(3)
C3 C2 H2A 120.6
C1 C2 H2A 120.6
C2 C3 C4 121.8(3)
C2 C3 Br1 118.9(2)
C4 C3 Br1 119.2(2)
C3 C4 C5 118.7(3)
C3 C4 H4 120.7
C5 C4 H4 120.7
C4 C5 C6 121.2(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C1 118.4(3)
C5 C6 C7 119.4(3)
C1 C6 C7 122.3(3)
C8 C7 C6 126.2(3)
C8 C7 H7 116.9
C6 C7 H7 116.9
C7 C8 C9 122.5(3)
C7 C8 H8 118.7
C9 C8 H8 118.7
O1 C9 O2 123.2(3)
O1 C9 C8 121.0(3)
O2 C9 C8 115.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.901(3)
O1 C9 1.264(4)
O2 C9 1.283(4)
O2 H2 0.8400
C1 C2 1.388(5)
C1 C6 1.400(4)
C1 H1 0.9500
C2 C3 1.380(5)
C2 H2A 0.9500
C3 C4 1.387(4)
C4 C5 1.387(4)
C4 H4 0.9500
C5 C6 1.398(4)
C5 H5 0.9500
C6 C7 1.463(4)
C7 C8 1.334(4)
C7 H7 0.9500
C8 C9 1.469(4)
C8 H8 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84 1.80 2.626(3) 169.7 3_855
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 0.5(5)
C1 C2 C3 C4 -1.1(5)
C1 C2 C3 Br1 178.1(2)
C2 C3 C4 C5 0.6(5)
Br1 C3 C4 C5 -178.5(2)
C3 C4 C5 C6 0.5(4)
C4 C5 C6 C1 -1.0(4)
C4 C5 C6 C7 179.1(3)
C2 C1 C6 C5 0.5(5)
C2 C1 C6 C7 -179.6(3)
C5 C6 C7 C8 -173.5(3)
C1 C6 C7 C8 6.6(5)
C6 C7 C8 C9 179.7(3)
C7 C8 C9 O1 2.7(5)
C7 C8 C9 O2 -178.0(3)
