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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/58/7225839.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_7225839
loop_
_publ_author_name
'Zhu, Bingqing'
'Wang, Jian-Rong'
'Zhang, Qi'
'Mei, Xuefeng'
_publ_section_title
;
 Greener solid-state synthesis: stereo-selective [2 + 2] photodimerization
 of vitamin K3controlled by halogen bonding
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              6327
_journal_paper_doi               10.1039/C6CE01236A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         '2(Br C3 F2), C11 H8 O2'
_chemical_formula_sum            'C17 H8 Br2 F4 O2'
_chemical_formula_weight         480.05
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-03-29 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                93.626(3)
_cell_angle_beta                 96.888(3)
_cell_angle_gamma                93.357(4)
_cell_formula_units_Z            2
_cell_length_a                   3.8981(3)
_cell_length_b                   13.3018(10)
_cell_length_c                   15.2307(11)
_cell_measurement_reflns_used    8377
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.70
_cell_volume                     780.72(10)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12713
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.558
_diffrn_reflns_theta_min         1.537
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1183 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.5268.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'yellowish yellow'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.042
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0257P)²+0.4292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3170
_reflns_number_total             3519
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01236a2.cif
_cod_data_source_block           2015565
_cod_depositor_comments
'Adding full bibliography for 7225839--7225840.cif.'
_cod_database_code               7225839
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C7(H7), C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Br1 Br 0.11532(5) 0.44333(2) 0.79418(2) 0.01838(6) Uani 1 1 d .
Br2 Br 0.81159(5) 0.08647(2) 0.19305(2) 0.01971(6) Uani 1 1 d .
F2 F 0.2356(3) 0.68439(8) 1.07766(7) 0.0238(2) Uani 1 1 d .
F3 F 1.1493(3) 0.19752(8) 0.05328(7) 0.0248(2) Uani 1 1 d .
F1 F 0.3234(3) 0.63762(8) 0.90838(7) 0.0240(2) Uani 1 1 d .
F4 F 0.7036(3) -0.12787(9) 0.10549(7) 0.0254(3) Uani 1 1 d .
O2 O 0.2287(4) 0.41389(10) 0.60855(9) 0.0243(3) Uani 1 1 d .
O1 O 0.6756(4) 0.16149(11) 0.36658(9) 0.0268(3) Uani 1 1 d .
C15 C 0.9206(5) 0.03674(14) 0.08290(11) 0.0167(4) Uani 1 1 d .
C14 C 0.1167(5) 0.59341(13) 1.03996(12) 0.0168(4) Uani 1 1 d .
C9 C 0.6010(5) 0.19314(14) 0.51704(12) 0.0177(4) Uani 1 1 d .
C16 C 1.0722(5) 0.10030(14) 0.02764(12) 0.0174(4) Uani 1 1 d .
C12 C 0.0462(5) 0.47576(14) 0.91176(11) 0.0157(3) Uani 1 1 d .
C6 C 0.6634(5) 0.14552(16) 0.69270(13) 0.0252(4) Uani 1 1 d .
H6 H 0.6864 0.1298 0.7517 0.030 Uiso 1 1 calc R
C17 C 0.8514(5) -0.06376(14) 0.05412(12) 0.0178(4) Uani 1 1 d .
C8 C 0.7372(5) 0.10350(15) 0.54025(13) 0.0218(4) Uani 1 1 d .
H8 H 0.8093 0.0596 0.4972 0.026 Uiso 1 1 calc R
C13 C 0.1614(5) 0.56934(13) 0.95279(12) 0.0168(4) Uani 1 1 d .
C7 C 0.7659(5) 0.07914(15) 0.62853(13) 0.0249(4) Uani 1 1 d .
H7 H 0.8538 0.0184 0.6443 0.030 Uiso 1 1 calc R
C10 C 0.4914(5) 0.26031(14) 0.58169(12) 0.0186(4) Uani 1 1 d .
C2 C 0.4237(5) 0.31451(14) 0.39805(12) 0.0196(4) Uani 1 1 d .
C11 C 0.4056(5) 0.33623(16) 0.30277(13) 0.0257(4) Uani 1 1 d .
H11A H 0.3138 0.4009 0.2948 0.038 Uiso 1 1 calc GR
H11B H 0.2577 0.2850 0.2673 0.038 Uiso 1 1 calc GR
H11C H 0.6336 0.3368 0.2849 0.038 Uiso 1 1 calc GR
C1 C 0.5732(5) 0.21832(14) 0.42263(13) 0.0189(4) Uani 1 1 d .
C4 C 0.3380(5) 0.35429(14) 0.55546(13) 0.0192(4) Uani 1 1 d .
C5 C 0.5257(5) 0.23596(15) 0.66913(13) 0.0222(4) Uani 1 1 d .
H5 H 0.4566 0.2801 0.7125 0.027 Uiso 1 1 calc R
C3 C 0.3133(5) 0.37629(14) 0.45997(13) 0.0201(4) Uani 1 1 d .
H3 H 0.2170 0.4354 0.4428 0.024 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 C15 Br2 120.65(14) . .
C17 C15 Br2 121.16(14) . .
C17 C15 C16 118.19(16) . .
F2 C14 C12 120.30(16) . 2_567
F2 C14 C13 119.09(16) . .
C13 C14 C12 120.61(16) . 2_567
C8 C9 C10 120.62(17) . .
C8 C9 C1 119.14(16) . .
C10 C9 C1 120.24(17) . .
F3 C16 C15 120.32(16) . .
F3 C16 C17 119.09(16) . 2_755
C17 C16 C15 120.59(17) 2_755 .
C14 C12 Br1 121.06(13) 2_567 .
C13 C12 Br1 120.43(14) . .
C13 C12 C14 118.51(16) . 2_567
C7 C6 H6 119.9 . .
C7 C6 C5 120.21(18) . .
C5 C6 H6 119.9 . .
F4 C17 C15 120.11(16) . .
F4 C17 C16 118.67(16) . 2_755
C16 C17 C15 121.21(17) 2_755 .
C9 C8 H8 120.1 . .
C9 C8 C7 119.75(18) . .
C7 C8 H8 120.1 . .
F1 C13 C14 119.03(16) . .
F1 C13 C12 120.08(16) . .
C14 C13 C12 120.88(17) . .
C6 C7 C8 119.96(19) . .
C6 C7 H7 120.0 . .
C8 C7 H7 120.0 . .
C9 C10 C4 119.93(17) . .
C5 C10 C9 119.08(18) . .
C5 C10 C4 120.98(17) . .
C1 C2 C11 116.47(16) . .
C3 C2 C11 123.39(19) . .
C3 C2 C1 120.13(18) . .
C2 C11 H11A 109.5 . .
C2 C11 H11B 109.5 . .
C2 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O1 C1 C9 120.54(17) . .
O1 C1 C2 120.62(17) . .
C2 C1 C9 118.83(16) . .
O2 C4 C10 122.63(18) . .
O2 C4 C3 119.34(18) . .
C10 C4 C3 118.03(16) . .
C6 C5 H5 119.8 . .
C10 C5 C6 120.37(17) . .
C10 C5 H5 119.8 . .
C2 C3 C4 122.80(18) . .
C2 C3 H3 118.6 . .
C4 C3 H3 118.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C12 1.8702(17) .
Br2 C15 1.8699(17) .
F2 C14 1.339(2) .
F3 C16 1.333(2) .
F1 C13 1.340(2) .
F4 C17 1.344(2) .
O2 C4 1.227(2) .
O1 C1 1.223(2) .
C15 C16 1.387(2) .
C15 C17 1.381(3) .
C14 C12 1.386(3) 2_567
C14 C13 1.380(2) .
C9 C8 1.382(3) .
C9 C10 1.409(2) .
C9 C1 1.490(3) .
C16 C17 1.380(2) 2_755
C12 C14 1.385(3) 2_567
C12 C13 1.382(3) .
C6 H6 0.9300 .
C6 C7 1.386(3) .
C6 C5 1.396(3) .
C17 C16 1.380(2) 2_755
C8 H8 0.9300 .
C8 C7 1.396(3) .
C7 H7 0.9300 .
C10 C4 1.474(3) .
C10 C5 1.383(3) .
C2 C11 1.492(3) .
C2 C1 1.487(3) .
C2 C3 1.338(3) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C4 C3 1.495(3) .
C5 H5 0.9300 .
C3 H3 0.9300 .
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_4
Br1 C12 C13 F1 0.1(2) . .
Br1 C12 C13 C14 -178.92(14) . .
Br2 C15 C16 F3 1.5(2) . .
Br2 C15 C16 C17 -179.18(14) . 2_755
Br2 C15 C17 F4 -0.1(2) . .
Br2 C15 C17 C16 179.18(14) . 2_755
F2 C14 C13 F1 0.2(3) . .
F2 C14 C13 C12 179.21(16) . .
O2 C4 C3 C2 -179.37(19) . .
C14 C12 C13 F1 179.25(16) 2_567 .
C14 C12 C13 C14 0.3(3) 2_567 .
C9 C8 C7 C6 -1.1(3) . .
C9 C10 C4 O2 177.72(18) . .
C9 C10 C4 C3 -1.7(3) . .
C9 C10 C5 C6 -0.7(3) . .
C16 C15 C17 F4 -179.80(16) . .
C16 C15 C17 C16 -0.6(3) . 2_755
C12 C14 C13 F1 -179.26(16) 2_567 .
C12 C14 C13 C12 -0.3(3) 2_567 .
C17 C15 C16 F3 -178.81(16) . .
C17 C15 C16 C17 0.5(3) . 2_755
C8 C9 C10 C4 -178.33(17) . .
C8 C9 C10 C5 0.8(3) . .
C8 C9 C1 O1 -1.4(3) . .
C8 C9 C1 C2 179.51(17) . .
C7 C6 C5 C10 -0.2(3) . .
C10 C9 C8 C7 0.1(3) . .
C10 C9 C1 O1 178.21(18) . .
C10 C9 C1 C2 -0.9(3) . .
C10 C4 C3 C2 0.1(3) . .
C11 C2 C1 O1 0.3(3) . .
C11 C2 C1 C9 179.41(17) . .
C11 C2 C3 C4 -179.05(18) . .
C1 C9 C8 C7 179.76(17) . .
C1 C9 C10 C4 2.0(3) . .
C1 C9 C10 C5 -178.87(17) . .
C1 C2 C3 C4 1.1(3) . .
C4 C10 C5 C6 178.37(17) . .
C5 C6 C7 C8 1.1(3) . .
C5 C10 C4 O2 -1.3(3) . .
C5 C10 C4 C3 179.26(17) . .
C3 C2 C1 O1 -179.83(19) . .
C3 C2 C1 C9 -0.8(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202374
