#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:11:10 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298774 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/42/7134243.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_7134243
loop_
_publ_author_name
'Shu, Yilin'
'Huang, Jianmin'
'Yang, Junfang'
'Shangguan, Zhichun'
'Ma, Junlong'
'Li, Cheng'
'Zhang, Guanxin'
'Peng, Qian'
'Zhang, Xi-Sha'
'Fan, Qitang'
'Wang, Bing'
'Zhang, Deqing'
_publ_section_title
;
 Heptene end-capped Thiele hydrocarbons with tunable configuration and
 emission and on-surface transformation via annulation.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3994
_journal_page_last               3997
_journal_paper_doi               10.1039/d5cc00053j
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C36 H20 Br2 F2'
_chemical_formula_sum            'C36 H20 Br2 F2'
_chemical_formula_weight         650.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lls66
_audit_creation_date             2024-04-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.492(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.3528(6)
_cell_length_b                   5.37990(10)
_cell_length_c                   25.3593(8)
_cell_measurement_reflns_used    3084
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      74.9580
_cell_measurement_theta_min      3.3010
_cell_volume                     2746.21(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  69.00   0.50    0.05    --  107.36 -57.00 -30.00   58
  2  ω     35.00  69.00   0.50    0.05    --  107.36 -57.00   0.00   68
  3  ω     38.00  69.00   0.50    0.05    --  107.36 -57.00  60.00   62
  4  ω     46.00  82.00   0.50    0.05    --  107.36 -77.00  60.00   72
  5  ω    113.00 170.00   0.50    0.05    --  107.36  19.00 -90.00  114
  6  ω    120.00 178.00   0.50    0.05    --  107.36  84.00 -44.00  116
  7  ω    -24.00  72.00   0.50    0.05    --   47.70 -84.00-164.00  192
  8  ω     56.00 132.00   0.50    0.05    --  107.36 -84.00-164.00  152
  9  ω    -17.00  28.00   0.50    0.05    --  -47.70  19.00  60.00   90
 10  ω    -20.00   7.00   0.50    0.05    --  -47.70  19.00  30.00   54
 11  ω    -82.00 -56.00   0.50    0.05    -- -104.50  77.00 -30.00   52
 12  ω    -59.00 -32.00   0.50    0.05    -- -104.50  57.00 -90.00   54
 13  ω    -62.00 -34.00   0.50    0.05    -- -104.50  57.00 -60.00   56
 14  ω    -62.00 -33.00   0.50    0.05    -- -104.50  57.00 -30.00   58
 15  ω    -59.00 -33.00   0.50    0.05    -- -104.50  57.00  60.00   52
 16  ω    -58.00 -32.00   0.50    0.05    -- -104.50  57.00 150.00   52
 17  ω   -116.00 -74.00   0.50    0.05    --  -47.70-125.00 -90.00   84
 18  ω   -105.00 -80.00   0.50    0.05    -- -104.50  84.00 -44.00   50
 19  ω   -170.00 -89.00   0.50    0.05    -- -104.50 -57.00-120.00  162
 20  ω   -174.00 -99.00   0.50    0.05    -- -104.50 -84.00-164.00  150
 21  ω    -61.00  22.00   0.50    0.05    --  -47.70  84.00 -44.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0177982000
_diffrn_orient_matrix_UB_12      -0.0610857000
_diffrn_orient_matrix_UB_13      0.0526622000
_diffrn_orient_matrix_UB_21      -0.0327125000
_diffrn_orient_matrix_UB_22      -0.2447825000
_diffrn_orient_matrix_UB_23      -0.0272022000
_diffrn_orient_matrix_UB_31      0.0668004000
_diffrn_orient_matrix_UB_32      -0.1357450000
_diffrn_orient_matrix_UB_33      0.0253179000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8586
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.796
_diffrn_reflns_theta_min         3.698
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0441
_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)+(0.0541P)²+3.4831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2171
_reflns_number_total             2756
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc00053j2.cif
_cod_data_source_block           2c-solution
_cod_depositor_comments
'Adding full bibliography for 7134240--7134246.cif.'
_cod_database_code               7134243
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C, H, Br, F'
_chemical_oxdiff_usercomment     'C, H, N'
_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. Restrained distances
 F1-C18 = F1A-C17
 1.36 with sigma of 0.01
 Br1-C17 = Br1A-C18
 1.9 with sigma of 0.01
2. Others
 Sof(Br1A)=Sof(F1A)=1-FVAR(1)
 Sof(Br1)=Sof(F1)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.595
_oxdiff_exptl_absorpt_empirical_full_min 0.627
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.39257(3) 0.03598(11) -0.01748(3) 0.0408(2) Uani 0.5528(15) 1 d D . P A
1
F1 F 0.2631(2) 0.0637(6) -0.10022(12) 0.0398(7) Uani 0.5528(15) 1 d D . P A 1
C1 C 0.35617(14) 0.2519(5) 0.09914(11) 0.0398(6) Uani 1 1 d . . . . .
C2 C 0.34591(15) 0.3040(6) 0.15292(12) 0.0437(7) Uani 1 1 d . . . . .
C3 C 0.30436(18) 0.4971(6) 0.15656(16) 0.0552(8) Uani 1 1 d . . . . .
H3 H 0.284173 0.599694 0.124948 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2923(2) 0.5405(9) 0.2061(2) 0.0800(14) Uani 1 1 d . . . . .
H4 H 0.264562 0.674795 0.208671 0.096 Uiso 1 1 calc R U . . .
C5 C 0.3202(3) 0.3901(13) 0.25154(18) 0.0925(18) Uani 1 1 d . . . . .
H5 H 0.310246 0.415415 0.284945 0.111 Uiso 1 1 calc R U . . .
C6 C 0.3622(2) 0.2050(10) 0.24879(15) 0.0802(14) Uani 1 1 d . . . . .
H6 H 0.381020 0.102255 0.280641 0.096 Uiso 1 1 calc R U . . .
C7 C 0.37882(16) 0.1597(7) 0.20034(13) 0.0554(9) Uani 1 1 d . . . . .
C8 C 0.4272(2) -0.0284(7) 0.20107(16) 0.0697(12) Uani 1 1 d . . . . .
H8 H 0.428563 -0.169778 0.223864 0.084 Uiso 1 1 calc R U . . .
C9 C 0.47019(19) -0.0257(7) 0.17338(18) 0.0680(11) Uani 1 1 d . . . . .
H9 H 0.499040 -0.164868 0.178823 0.082 Uiso 1 1 calc R U . . .
C10 C 0.47807(15) 0.1666(6) 0.13560(14) 0.0535(8) Uani 1 1 d . . . . .
C11 C 0.54109(17) 0.2148(9) 0.13271(17) 0.0697(11) Uani 1 1 d . . . . .
H11 H 0.577421 0.113395 0.153359 0.084 Uiso 1 1 calc R U . . .
C12 C 0.55182(19) 0.4063(9) 0.10055(18) 0.0721(12) Uani 1 1 d . . . . .
H12 H 0.595348 0.437732 0.099933 0.087 Uiso 1 1 calc R U . . .
C13 C 0.4994(2) 0.5522(8) 0.06926(16) 0.0649(10) Uani 1 1 d . . . . .
H13 H 0.506958 0.686998 0.047937 0.078 Uiso 1 1 calc R U . . .
C14 C 0.43599(17) 0.5016(6) 0.06910(14) 0.0508(8) Uani 1 1 d . . . . .
H14 H 0.399827 0.600422 0.047114 0.061 Uiso 1 1 calc R U . . .
C15 C 0.42456(14) 0.3062(5) 0.10100(12) 0.0418(7) Uani 1 1 d . . . . .
C16 C 0.30608(13) 0.1795(5) 0.05231(11) 0.0372(6) Uani 1 1 d . . . . .
C17 C 0.31312(12) 0.1300(5) -0.00222(12) 0.0361(6) Uani 1 1 d D . . . .
C18 C 0.26263(14) 0.1299(5) -0.04948(10) 0.0368(6) Uani 1 1 d D . . . .
Br1A Br 0.29531(4) 0.03571(15) -0.10897(3) 0.0425(3) Uani 0.4472(15) 1 d D . P A
2
F1A F 0.37608(18) 0.0645(7) 0.00626(19) 0.0400(9) Uani 0.4472(15) 1 d D . P A 2
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
_geom_angle_publ_flag
C15 C1 C2 112.5(2) . . ?
C16 C1 C2 122.9(3) . . ?
C16 C1 C15 124.4(3) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 C7 120.3(3) . . ?
C7 C2 C1 119.9(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.3(4) . . ?
C7 C6 H6 118.9 . . ?
C2 C7 C6 116.8(4) . . ?
C2 C7 C8 123.3(3) . . ?
C6 C7 C8 119.9(4) . . ?
C7 C8 H8 116.4 . . ?
C9 C8 C7 127.2(3) . . ?
C9 C8 H8 116.4 . . ?
C8 C9 H9 116.3 . . ?
C8 C9 C10 127.4(3) . . ?
C10 C9 H9 116.3 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 C15 117.7(4) . . ?
C15 C10 C9 122.8(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.5(4) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C1 120.3(3) . . ?
C14 C15 C1 119.6(3) . . ?
C14 C15 C10 120.1(3) . . ?
C1 C16 C17 125.2(3) . . ?
C1 C16 C18 125.1(3) . 2 ?
C17 C16 C18 109.7(2) . 2 ?
C16 C17 Br1 127.7(2) . . ?
C18 C17 Br1 109.0(2) . . ?
C18 C17 C16 123.2(2) . . ?
C18 C17 F1A 128.3(3) . . ?
F1A C17 C16 108.1(3) . . ?
F1 C18 C16 109.2(3) . 2 ?
C16 C18 Br1A 128.7(2) 2 . ?
C17 C18 F1 127.5(3) . . ?
C17 C18 C16 123.0(2) . 2 ?
C17 C18 Br1A 108.2(2) . . ?
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
Br1 C17 1.929(3) . ?
F1 C18 1.338(4) . ?
C1 C2 1.479(4) . ?
C1 C15 1.474(4) . ?
C1 C16 1.363(4) . ?
C2 C3 1.389(5) . ?
C2 C7 1.407(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.357(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.409(6) . ?
C7 C8 1.443(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.328(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.457(6) . ?
C10 C11 1.396(5) . ?
C10 C15 1.404(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(5) . ?
C16 C17 1.465(4) . ?
C16 C18 1.469(4) 2 ?
C17 C18 1.318(4) . ?
C17 F1A 1.336(4) . ?
C18 Br1A 1.929(3) . ?
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
Br1 C17 C18 F1 3.5(4) . . . . ?
Br1 C17 C18 C16 176.4(2) . . . 2 ?
C1 C2 C3 C4 177.3(3) . . . . ?
C1 C2 C7 C6 -174.5(3) . . . . ?
C1 C2 C7 C8 5.1(5) . . . . ?
C1 C16 C17 Br1 24.2(4) . . . . ?
C1 C16 C17 C18 -160.1(3) . . . . ?
C1 C16 C17 F1A 25.8(4) . . . . ?
C2 C1 C15 C10 65.7(3) . . . . ?
C2 C1 C15 C14 -112.8(3) . . . . ?
C2 C1 C16 C17 178.8(3) . . . . ?
C2 C1 C16 C18 -3.7(4) . . . 2 ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C2 C7 C8 C9 33.7(6) . . . . ?
C3 C2 C7 C6 6.2(4) . . . . ?
C3 C2 C7 C8 -174.2(3) . . . . ?
C3 C4 C5 C6 2.9(6) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C5 C6 C7 C2 -4.7(5) . . . . ?
C5 C6 C7 C8 175.7(4) . . . . ?
C6 C7 C8 C9 -146.7(4) . . . . ?
C7 C2 C3 C4 -3.4(5) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C8 C9 C10 C11 146.8(4) . . . . ?
C8 C9 C10 C15 -33.9(6) . . . . ?
C9 C10 C11 C12 -175.4(3) . . . . ?
C9 C10 C15 C1 -3.7(5) . . . . ?
C9 C10 C15 C14 174.7(3) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
C11 C10 C15 C1 175.6(3) . . . . ?
C11 C10 C15 C14 -5.9(4) . . . . ?
C11 C12 C13 C14 -1.8(6) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C1 -178.6(3) . . . . ?
C13 C14 C15 C10 3.0(5) . . . . ?
C15 C1 C2 C3 112.5(3) . . . . ?
C15 C1 C2 C7 -66.8(3) . . . . ?
C15 C1 C16 C17 3.9(4) . . . . ?
C15 C1 C16 C18 -178.6(3) . . . 2 ?
C15 C10 C11 C12 5.2(5) . . . . ?
C16 C1 C2 C3 -62.9(4) . . . . ?
C16 C1 C2 C7 117.8(3) . . . . ?
C16 C1 C15 C10 -119.0(3) . . . . ?
C16 C1 C15 C14 62.6(4) . . . . ?
C16 C17 C18 F1 -172.9(3) . . . . ?
C16 C17 C18 C16 0.0(4) . . . 2 ?
C16 C17 C18 Br1A -176.5(2) . . . . ?
C18 C16 C17 Br1 -153.6(2) 2 . . . ?
C18 C16 C17 C18 22.1(3) 2 . . . ?
C18 C16 C17 F1A -152.0(3) 2 . . . ?
F1A C17 C18 C16 172.8(3) . . . 2 ?
F1A C17 C18 Br1A -3.7(4) . . . . ?
