#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:49:47 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257436 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/47/7234796.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_7234796
loop_
_publ_author_name
'Chongboriboon, Nucharee'
'Samakun, Kodchakorn'
'Inprasit, Thitirat'
'Kielar, Filip'
'Dungkaew, Winya'
'Wong, Lawrence W.-Y.'
'Sung, Herman H.-Y.'
'Ninković, Dragan B.'
'Zarić, Snežana D.'
'Chainok, Kittipong'
_publ_section_title
;
 Two-dimensional halogen-bonded organic frameworks based on the
 tetrabromobenzene-1,4-dicarboxylic acid building molecule
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              24
_journal_page_last               34
_journal_paper_doi               10.1039/C9CE01140D
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         '0.5(C16 H4 Br8 O8), 2(C2 H6 O2)'
_chemical_formula_sum            'C12 H14 Br4 O8'
_chemical_formula_weight         605.87
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-18 deposited with the CCDC.    2019-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.134(2)
_cell_length_b                   9.964(3)
_cell_length_c                   23.849(6)
_cell_measurement_reflns_used    9675
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      3.031
_cell_volume                     1932.9(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.032
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.362
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1808 before and 0.0987 after correction. The Ratio of minimum to maximum transmission is 0.4953. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.082
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.501
_refine_diff_density_min         -1.135
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.0034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1968
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0494P)²+6.4579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1544
_reflns_number_total             1968
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01140d2.cif
_cod_data_source_block           4eg_rt
_cod_depositor_comments
;Adding full bibliography for 7234791--7234798.cif.

 Adding full bibliography for 7234791--7234798.cif.
;
_cod_original_cell_volume        1933.0(9)
_cod_database_code               7234796
_shelx_shelxl_version_number     2018/3
_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_max   0.286
_shelx_estimated_absorpt_t_min   0.261
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 O1-H1 = O3-H3 = O4-H4
 0.82 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(Br2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(Br1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C1, C2, C4, Br2, C3, Br1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C1, C2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
;
_shelx_res_file
;
TITL KCKS9_0m_a.res in Pbca
    4eg_rt.res
    created by SHELXL-2018/3 at 18:55:58 on 18-Jul-2019
REM Old TITL KCKS9_0m in Pbca
REM SHELXT solution in Pbca
REM R1 0.254, Rweak 0.005, Alpha 0.053, Orientation as input
REM Formula found by SHELXT: C8 Br2 O2
CELL 0.71073 8.1339 9.9645 23.849 90 90 90
ZERR 4 0.0023 0.0027 0.0061 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br O
UNIT 48 56 16 32
EQIV $1 0.5-X,0.5+Y,+Z
EQIV $2 -0.5+X,1.5-Y,1-Z
EQIV $3 1-X,-0.5+Y,0.5-Z
EQIV $4 -0.5+X,+Y,0.5-Z
DFIX 0.82 0.01 O1 H1 O3 H3 O4 H4
RIGU 0.0001 0.0001 C1 C2 C4 Br2 C3 Br1
RIGU 0.0001 0.0001 C1 C2
ISOR 0.01 0.02 C2 C4 Br2 C3 Br1
ISOR 0.01 0.02 C2

L.S. 12
PLAN  8
SIZE 0.22 0.22 0.2
TEMP 22.85
HTAB O1 O3
HTAB O3 O4_$3
HTAB O4 O2_$4
BIND Br2 O2_$2
BIND Br1 O1_$1
BOND $H
list 4
more -3
fmap 2
acta
OMIT 0 2 2
REM <olex2.extras>
REM <HklSrc "%.\\4EG_RT.hkl">
REM </olex2.extras>

WGHT    0.049400    6.457900
EXTI    0.003359
FVAR       0.28153
BR1   3    0.272807    0.709055    0.427331    11.00000    0.04591    0.04792 =
         0.02912    0.00841   -0.00073    0.02359
BR2   3    0.728456    0.283369    0.431990    11.00000    0.05237    0.04408 =
         0.03017   -0.00256    0.00887    0.02534
O1    4    0.416288    0.416060    0.353737    11.00000    0.05222    0.04497 =
         0.01876   -0.00417   -0.00156   -0.01831
H1    2    0.434821    0.403565    0.320204    11.00000    0.05343
O2    4    0.611459    0.573726    0.354683    11.00000    0.04562    0.03773 =
         0.02756    0.00134    0.00706   -0.01170
O3    4    0.518917    0.350797    0.256476    11.00000    0.12993    0.04664 =
         0.03002   -0.00545   -0.00947    0.03815
H3    2    0.562766    0.277007    0.258228    11.00000    0.04624
O4    4    0.373841    0.600019    0.223811    11.00000    0.05768    0.03905 =
         0.05988   -0.00745   -0.01859   -0.00170
H4    2    0.289580    0.588480    0.205553    11.00000    0.10471
C1    1    0.515766    0.500054    0.378133    11.00000    0.02680    0.02304 =
         0.02040   -0.00060    0.00200    0.00303
C2    1    0.502488    0.498238    0.441152    11.00000    0.02242    0.02216 =
         0.02038   -0.00071    0.00171    0.00092
C3    1    0.403397    0.589145    0.469822    11.00000    0.02451    0.02428 =
         0.02009   -0.00071    0.00132    0.00322
C4    1    0.599066    0.408461    0.472145    11.00000    0.02462    0.02524 =
         0.02060    0.00024    0.00287    0.00379
C5    1    0.477752    0.380494    0.200432    11.00000    0.07028    0.05389 =
         0.02883   -0.01060   -0.00095    0.00609
AFIX  23
H5A   2    0.366744    0.350144    0.192683    11.00000   -1.20000
H5B   2    0.551977    0.333635    0.175330    11.00000   -1.20000
AFIX   0
C6    1    0.489414    0.527259    0.190537    11.00000    0.05617    0.06533 =
         0.04347    0.01163    0.00342   -0.01013
AFIX  23
H6A   2    0.599748    0.557470    0.199418    11.00000   -1.20000
H6B   2    0.469327    0.545753    0.151197    11.00000   -1.20000
AFIX   0
HKLF 4




REM  KCKS9_0m_a.res in Pbca
REM wR2 = 0.1122, GooF = S = 1.037, Restrained GooF = 1.032 for all data
REM R1 = 0.0417 for 1544 Fo > 4sig(Fo) and 0.0549 for all 1968 data
REM 122 parameters refined using 59 restraints

END

WGHT      0.0494      6.4578

REM Highest difference peak  1.501,  deepest hole -1.135,  1-sigma level  0.117
Q1    1   0.7984  0.3443  0.4388  11.00000  0.05    1.50
Q2    1   0.2184  0.6394  0.4322  11.00000  0.05    0.87
Q3    1   0.6066  0.4009  0.5000  11.00000  0.05    0.49
Q4    1   0.4477  0.5249  0.4492  11.00000  0.05    0.45
Q5    1   0.5267  0.4260  0.4431  11.00000  0.05    0.44
Q6    1   0.9286  0.3798  0.4241  11.00000  0.05    0.38
Q7    1   0.4117  0.3200  0.2512  11.00000  0.05    0.34
Q8    1   0.6993  0.2596  0.4589  11.00000  0.05    0.33
;
_shelx_res_checksum              59978
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.27281(6) 0.70906(5) 0.42733(2) 0.0410(2) Uani 1 1 d . U
Br2 Br 0.72846(7) 0.28337(5) 0.43199(2) 0.0422(2) Uani 1 1 d . U
O1 O 0.4163(4) 0.4161(3) 0.35374(12) 0.0387(8) Uani 1 1 d D .
H1 H 0.435(7) 0.404(5) 0.3202(7) 0.053(16) Uiso 1 1 d D .
O2 O 0.6115(4) 0.5737(3) 0.35468(12) 0.0370(7) Uani 1 1 d . .
O3 O 0.5189(7) 0.3508(4) 0.25648(14) 0.0689(14) Uani 1 1 d D .
H3 H 0.563(7) 0.277(3) 0.258(2) 0.046(16) Uiso 1 1 d D .
O4 O 0.3738(5) 0.6000(4) 0.22381(17) 0.0522(10) Uani 1 1 d D .
H4 H 0.290(5) 0.588(9) 0.206(3) 0.10(3) Uiso 1 1 d D .
C1 C 0.5158(5) 0.5001(3) 0.37813(16) 0.0234(7) Uani 1 1 d . U
C2 C 0.5025(4) 0.4982(3) 0.44115(16) 0.0217(6) Uani 1 1 d . U
C3 C 0.4034(5) 0.5891(4) 0.46982(15) 0.0230(7) Uani 1 1 d . U
C4 C 0.5991(5) 0.4085(4) 0.47215(16) 0.0235(7) Uani 1 1 d . U
C5 C 0.4778(8) 0.3805(5) 0.20043(19) 0.0510(14) Uani 1 1 d . .
H5A H 0.366744 0.350144 0.192683 0.061 Uiso 1 1 calc R .
H5B H 0.551977 0.333635 0.175330 0.061 Uiso 1 1 calc R .
C6 C 0.4894(7) 0.5273(5) 0.1905(2) 0.0550(14) Uani 1 1 d . .
H6A H 0.599748 0.557470 0.199418 0.066 Uiso 1 1 calc R .
H6B H 0.469327 0.545753 0.151197 0.066 Uiso 1 1 calc R .
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 0.0459(3) 0.0479(3) 0.0291(3) 0.00841(18) -0.00073(18) 0.0236(2)
Br2 0.0524(4) 0.0441(3) 0.0302(3) -0.00256(18) 0.00887(19) 0.0253(2)
O1 0.052(2) 0.0450(18) 0.0188(15) -0.0042(14) -0.0016(14) -0.0183(16)
O2 0.0456(19) 0.0377(16) 0.0276(16) 0.0013(13) 0.0071(14) -0.0117(14)
O3 0.130(4) 0.047(2) 0.0300(19) -0.0055(16) -0.009(2) 0.038(2)
O4 0.058(2) 0.0391(19) 0.060(2) -0.0075(16) -0.019(2) -0.0017(18)
C1 0.0268(17) 0.0230(16) 0.0204(8) -0.0006(8) 0.0020(8) 0.0030(12)
C2 0.0224(11) 0.0222(10) 0.0204(9) -0.0007(7) 0.0017(7) 0.0009(10)
C3 0.0245(12) 0.0243(11) 0.0201(9) -0.0007(8) 0.0013(8) 0.0032(11)
C4 0.0246(13) 0.0252(11) 0.0206(9) 0.0002(8) 0.0029(8) 0.0038(11)
C5 0.070(4) 0.054(3) 0.029(3) -0.011(2) -0.001(2) 0.006(3)
C6 0.056(3) 0.065(4) 0.043(3) 0.012(3) 0.003(2) -0.010(3)
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'
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
C3 Br1 O1 175.45(14) . 8_665
C4 Br2 O2 2.40(12) . 4_466
C1 O1 H1 115(4) . .
C5 O3 H3 110(4) . .
C6 O4 H4 101(6) . .
O1 C1 C2 113.2(3) . .
O2 C1 O1 125.8(4) . .
O2 C1 C2 121.0(3) . .
C3 C2 C1 121.6(3) . .
C3 C2 C4 118.7(4) . .
C4 C2 C1 119.6(3) . .
C2 C3 Br1 118.2(3) . .
C4 C3 Br1 121.1(3) 5_666 .
C4 C3 C2 120.7(3) 5_666 .
C2 C4 Br2 117.7(3) . .
C3 C4 Br2 121.7(3) 5_666 .
C3 C4 C2 120.5(3) 5_666 .
O3 C5 H5A 109.7 . .
O3 C5 H5B 109.7 . .
O3 C5 C6 110.0(4) . .
H5A C5 H5B 108.2 . .
C6 C5 H5A 109.7 . .
C6 C5 H5B 109.7 . .
O4 C6 C5 111.7(4) . .
O4 C6 H6A 109.3 . .
O4 C6 H6B 109.3 . .
C5 C6 H6A 109.3 . .
C5 C6 H6B 109.3 . .
H6A C6 H6B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 O1 3.115(3) 8_665
Br1 C3 1.893(4) .
Br2 O2 9.597(3) 4_466
Br2 C4 1.892(4) .
O1 H1 0.823(10) .
O1 C1 1.301(5) .
O2 C1 1.207(5) .
O3 H3 0.818(10) .
O3 C5 1.409(6) .
O4 H4 0.820(10) .
O4 C6 1.428(7) .
C1 C2 1.507(5) .
C2 C3 1.392(5) .
C2 C4 1.401(5) .
C3 C4 1.384(5) 5_666
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C5 C6 1.484(7) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
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
_geom_hbond_publ_flag
O1 H1 O3 0.823(10) 1.748(18) 2.550(5) 164(6) . yes
O3 H3 O4 0.818(10) 1.887(17) 2.688(5) 166(5) 3_645 yes
O4 H4 O2 0.820(10) 2.05(2) 2.851(5) 167(8) 6_556 yes
