#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/92/1529279.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_1529279
loop_
_publ_author_name
'Itoh, Takahito'
'Nomura, Shinji'
'Nakasho, Hirofumi'
'Uno, Takahiro'
'Kubo, Masataka'
'Tohnai, Norimitsu'
'Miyata, Mikiji'
_publ_section_title
;
 Halogen Bond Effect for Single-Crystal-to-Single-Crystal Transformation:
 Topochemical Polymerization of Substituted Quinodimethane
;
_journal_issue                   15
_journal_name_full               Macromolecules
_journal_page_first              5450
_journal_paper_doi               10.1021/acs.macromol.5b01078
_journal_volume                  48
_journal_year                    2015
_chemical_formula_sum            'C10 H10 Br2 O4'
_chemical_formula_weight         353.99
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                98.28(2)
_cell_angle_beta                 103.43(2)
_cell_angle_gamma                106.30(2)
_cell_formula_units_Z            2
_cell_length_a                   6.795(2)
_cell_length_b                   8.051(2)
_cell_length_c                   11.928(3)
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    93.2
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.9
_cell_volume                     593.7(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9056
_diffrn_measured_fraction_theta_max 0.9056
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5419
_diffrn_reflns_av_R_equivalents  0.129
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5060
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_exptl_absorpt_coefficient_mu    8.672
_exptl_absorpt_correction_T_max  0.648
_exptl_absorpt_correction_T_min  0.285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         2.45
_refine_diff_density_min         -2.09
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.322
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1956
_refine_ls_R_factor_gt           0.1324
_refine_ls_shift/su_max          0.0007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2992
_reflns_number_gt                784
_reflns_number_total             1956
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ma5b01078_si_002.cif
_cod_data_source_block           Br
_cod_depositor_comments
'Adding full bibliography for 1529278--1529279.cif.'
_cod_original_cell_volume        593.8(3)
_cod_original_sg_symbol_H-M      'P -1         '
_cod_original_formula_sum        'C10 H10 Br2 O4 '
_cod_database_code               1529279
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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_calc_flag
Br(1) Br -0.1213(5) 0.6927(4) 0.6217(2) 0.076(1) Uani 1.00 d
Br(2) Br -0.6605(7) 0.8597(6) 0.3467(3) 0.123(2) Uani 1.00 d
O(1) O -0.487(2) 0.347(2) 0.171(1) 0.046(5) Uani 1.00 d
O(2) O -0.274(2) 0.624(2) 0.261(1) 0.041(4) Uani 1.00 d
O(3) O -0.211(2) 0.879(2) 0.076(1) 0.051(5) Uani 1.00 d
O(4) O -0.531(2) 0.785(2) 0.112(1) 0.043(4) Uani 1.00 d
C(2) C -0.275(3) 0.582(3) 0.379(2) 0.042(7) Uani 1.00 d
C(3) C -0.406(4) 0.491(3) 0.163(2) 0.056(8) Uani 1.00 d
C(4) C -0.391(3) 0.551(3) 0.047(2) 0.038(6) Uani 1.00 d
C(5) C -0.352(3) 0.764(3) 0.079(2) 0.040(6) Uani 1.00 d
C(6) C -0.086(3) 0.418(3) 0.080(2) 0.040(6) Uani 1.00 d
C(7) C -0.184(2) 0.528(3) 0.023(2) 0.034(5) Uani 1.00 d
C(8) C -0.092(3) 0.613(3) -0.057(2) 0.037(6) Uani 1.00 d
C(9) C -0.138(4) 0.751(3) 0.465(2) 0.061(8) Uani 1.00 d
C(10) C -0.501(3) 0.965(3) 0.161(2) 0.043(6) Uani 1.00 d
C(11) C -0.696(4) 0.951(3) 0.204(2) 0.067(9) Uani 1.00 d
H(1) H -0.1502 0.6731 -0.1345 0.0948 Uiso 1.00 calc
H(2) H -0.4165 0.5441 0.3872 0.0516 Uiso 1.00 calc
H(3) H -0.2148 0.4881 0.3911 0.0516 Uiso 1.00 calc
H(4) H -0.2006 0.8459 0.4570 0.0712 Uiso 1.00 calc
H(5) H 0.0026 0.7953 0.4543 0.0712 Uiso 1.00 calc
H(6) H -0.3716 1.0207 0.2262 0.0523 Uiso 1.00 calc
H(7) H -0.4923 1.0407 0.1041 0.0523 Uiso 1.00 calc
H(8) H -0.8221 0.8768 0.1438 0.0793 Uiso 1.00 calc
H(9) H -0.7154 1.0685 0.2208 0.0793 Uiso 1.00 calc
H(10) H -0.2540 0.3346 0.0971 0.0948 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Br Br -0.676 1.280
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(2) O(2) C(3) 115(1) 1_555 1_555 yes
C(5) O(4) C(10) 112(1) 1_555 1_555 yes
O(2) C(2) C(9) 103(1) 1_555 1_555 yes
O(1) C(3) O(2) 121(1) 1_555 1_555 yes
O(1) C(3) C(4) 126(1) 1_555 1_555 yes
O(2) C(3) C(4) 110(1) 1_555 1_555 yes
C(3) C(4) C(4) 107(1) 1_555 2_465 yes
C(3) C(4) C(5) 104(1) 1_555 1_555 yes
C(3) C(4) C(7) 107(1) 1_555 1_555 yes
C(4) C(4) C(5) 111(1) 2_465 1_555 yes
C(4) C(4) C(7) 118(2) 2_465 1_555 yes
C(5) C(4) C(7) 106(1) 1_555 1_555 yes
O(3) C(5) O(4) 124(1) 1_555 1_555 yes
O(3) C(5) C(4) 128(1) 1_555 1_555 yes
O(4) C(5) C(4) 107(1) 1_555 1_555 yes
C(7) C(6) C(8) 121(1) 1_555 2_565 yes
C(4) C(7) C(6) 119(1) 1_555 1_555 yes
C(4) C(7) C(8) 121(1) 1_555 1_555 yes
C(6) C(7) C(8) 118(1) 1_555 1_555 yes
C(6) C(8) C(7) 119(1) 2_565 1_555 yes
Br(1) C(9) C(2) 104(1) 1_555 1_555 yes
O(4) C(10) C(11) 102(1) 1_555 1_555 yes
Br(2) C(11) C(10) 108(1) 1_555 1_555 yes
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
Br(1) C(9) 1.98(2) . yes
Br(2) C(11) 1.94(2) . yes
O(1) C(3) 1.16(2) . yes
O(2) C(2) 1.49(2) . yes
O(2) C(3) 1.39(2) . yes
O(3) C(5) 1.14(2) . yes
O(4) C(5) 1.40(2) . yes
O(4) C(10) 1.42(2) . yes
C(2) C(9) 1.49(3) . yes
C(3) C(4) 1.54(3) . yes
C(4) C(4) 1.55(3) 2_465 yes
C(4) C(5) 1.63(3) . yes
C(4) C(7) 1.56(3) . yes
C(6) C(7) 1.42(2) . yes
C(6) C(8) 1.38(2) 2_565 yes
C(7) C(8) 1.41(2) . yes
C(10) C(11) 1.51(3) . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) C(10) 3.03(2) 1_545
O(1) C(11) 3.23(3) 1_545
O(3) C(11) 3.32(3) 1_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br(1) C(9) C(2) O(2) -176(1) 1_555 1_555 1_555 1_555 yes
Br(2) C(11) C(10) O(4) 74(1) 1_555 1_555 1_555 1_555 yes
O(1) C(3) O(2) C(2) -10(3) 1_555 1_555 1_555 1_555 yes
O(1) C(3) C(4) C(4) 39(3) 1_555 1_555 1_555 2_465 yes
O(1) C(3) C(4) C(5) 158(2) 1_555 1_555 1_555 1_555 yes
O(1) C(3) C(4) C(7) -88(2) 1_555 1_555 1_555 1_555 yes
O(2) C(3) C(4) C(4) -151(2) 1_555 1_555 1_555 2_465 yes
O(2) C(3) C(4) C(5) -33(2) 1_555 1_555 1_555 1_555 yes
O(2) C(3) C(4) C(7) 80(2) 1_555 1_555 1_555 1_555 yes
O(3) C(5) O(4) C(10) -10(2) 1_555 1_555 1_555 1_555 yes
O(3) C(5) C(4) C(3) 119(2) 1_555 1_555 1_555 1_555 yes
O(3) C(5) C(4) C(4) -124(2) 1_555 1_555 1_555 2_465 yes
O(3) C(5) C(4) C(7) 5(2) 1_555 1_555 1_555 1_555 yes
O(4) C(5) C(4) C(3) -61(1) 1_555 1_555 1_555 1_555 yes
O(4) C(5) C(4) C(4) 54(2) 1_555 1_555 1_555 2_465 yes
O(4) C(5) C(4) C(7) -174(1) 1_555 1_555 1_555 1_555 yes
C(2) O(2) C(3) C(4) 179(1) 1_555 1_555 1_555 1_555 yes
C(3) O(2) C(2) C(9) -174(1) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(4) C(3) 180.0 1_555 1_555 2_465 2_465 yes
C(3) C(4) C(4) C(5) -65(2) 1_555 1_555 2_465 2_465 yes
C(3) C(4) C(4) C(7) 58(2) 1_555 1_555 2_465 2_465 yes
C(3) C(4) C(7) C(6) 17(2) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(7) C(8) -162(1) 1_555 1_555 1_555 1_555 yes
C(4) C(4) C(7) C(6) 103(2) 1_555 2_465 2_465 2_465 yes
C(4) C(4) C(7) C(8) -75(2) 1_555 2_465 2_465 2_465 yes
C(4) C(5) O(4) C(10) 170(1) 1_555 1_555 1_555 1_555 yes
C(4) C(7) C(6) C(8) 176(1) 1_555 1_555 1_555 2_565 yes
C(4) C(7) C(8) C(6) -176(1) 1_555 1_555 1_555 2_565 yes
C(5) O(4) C(10) C(11) -172(1) 1_555 1_555 1_555 1_555 yes
C(5) C(4) C(4) C(5) 180.0 1_555 1_555 2_465 2_465 yes
C(5) C(4) C(4) C(7) -55(2) 1_555 1_555 2_465 2_465 yes
C(5) C(4) C(7) C(6) 129(1) 1_555 1_555 1_555 1_555 yes
C(5) C(4) C(7) C(8) -50(2) 1_555 1_555 1_555 1_555 yes
C(7) C(4) C(4) C(7) -180.0 1_555 1_555 2_465 2_465 yes
