#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:11:10 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298774 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/42/7134240.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_7134240
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 F4'
_chemical_formula_sum            'C36 H20 F4'
_chemical_formula_weight         528.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2lls11
_audit_creation_date             2025-01-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-01-31 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.00760(10)
_cell_length_b                   9.6663(2)
_cell_length_c                   25.6388(4)
_cell_measurement_reflns_used    5237
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      76.4710
_cell_measurement_theta_min      3.4470
_cell_volume                     1239.57(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  27.00   0.50    0.05    --  -46.66  38.00   0.00  124
  2  ω    -18.00  29.00   0.50    0.05    --  -46.66  19.00 -30.00   94
  3  ω    -23.00  13.00   0.50    0.05    --  -46.66  19.00 -90.00   72
  4  ω    -22.00  13.00   0.50    0.05    --  -46.66  19.00-120.00   70
  5  ω     98.00 178.00   0.50    0.05    --  108.85  45.00 -90.00  160
  6  ω    140.00 171.00   0.50    0.05    --  108.85  61.00 -30.00   62
  7  ω    105.00 131.00   0.50    0.05    --  108.85 112.00-110.00   52
  8  ω    102.00 132.00   0.50    0.05    --  108.85  61.00 -30.00   60
  9  ω     41.00  73.00   0.50    0.05    --  108.85 -61.00-180.00   64
 10  ω     58.00 111.00   0.50    0.05    --  108.85-125.00 -90.00  106
 11  ω     45.00 109.00   0.50    0.05    --  108.85 -77.00   0.00  128
 12  ω     36.00  73.00   0.50    0.05    --  108.85 -61.00  30.00   74
 13  ω     43.00  77.00   0.50    0.05    --  108.85-112.00 156.00   68
 14  ω     36.00 104.00   0.50    0.05    --  108.85 -94.00 150.00  136
 15  ω     11.00  84.00   0.50    0.05    --   46.66-112.00 156.00  146
 16  ω   -174.00-122.00   0.50    0.05    -- -104.50 -30.00  60.00  104
 17  ω   -143.00-117.00   0.50    0.05    -- -104.50-112.00 156.00   52
 18  ω   -163.00 -87.00   0.50    0.05    -- -104.50 -94.00 120.00  152
 19  ω    -59.00  -6.00   0.50    0.05    --  -46.66 112.00-110.00  106
 20  ω    -82.00 -37.00   0.50    0.05    -- -104.50 112.00-110.00   90
;
_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      0.0665749000
_diffrn_orient_matrix_UB_12      0.1440299000
_diffrn_orient_matrix_UB_13      0.0228308000
_diffrn_orient_matrix_UB_21      -0.0073718000
_diffrn_orient_matrix_UB_22      0.0611145000
_diffrn_orient_matrix_UB_23      -0.0555432000
_diffrn_orient_matrix_UB_31      -0.3006793000
_diffrn_orient_matrix_UB_32      0.0303391000
_diffrn_orient_matrix_UB_33      0.0034326000
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7613
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.572
_diffrn_reflns_theta_min         3.452
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       cube
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0035(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   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0386
_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)+(0.0382P)²+0.7059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2329
_reflns_number_total             2535
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc00053j2.cif
_cod_data_source_block           2a-PVT
_cod_depositor_comments
'Adding full bibliography for 7134240--7134246.cif.'
_cod_database_code               7134240
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHF
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C14(H14), C8(H8), C4(H4), C13(H13), C5(H5), C6(H6), C11(H11),
 C12(H12)
;
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.604
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
F19 F 0.89309(17) 0.34253(8) 0.41385(3) 0.0265(2) Uani 1 1 d . . . . .
F20 F 1.11572(18) 0.22673(8) 0.49347(3) 0.0275(2) Uani 1 1 d . . . . .
C17 C 1.0650(3) 0.36280(14) 0.49770(5) 0.0195(3) Uani 1 1 d . . . . .
C18 C 0.9402(3) 0.42308(14) 0.45612(5) 0.0194(3) Uani 1 1 d . . . . .
C15 C 0.6585(3) 0.55706(14) 0.36111(5) 0.0207(3) Uani 1 1 d . . . . .
C7 C 0.7771(3) 0.86896(15) 0.37519(5) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.6533(3) 0.77772(14) 0.40911(5) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.7350(3) 0.62966(14) 0.41085(5) 0.0198(3) Uani 1 1 d . . . . .
C10 C 0.7839(3) 0.59376(15) 0.31526(5) 0.0235(3) Uani 1 1 d . . . . .
C16 C 0.8581(3) 0.56734(14) 0.45350(5) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.4494(3) 0.82546(15) 0.43965(6) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.362361 0.762571 0.461674 0.030 Uiso 1 1 calc R U . . .
C9 C 0.9841(3) 0.70387(16) 0.31365(5) 0.0264(3) Uani 1 1 d . . . . .
H9 H 1.129989 0.688870 0.291985 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4566(3) 0.45728(15) 0.35918(6) 0.0266(3) Uani 1 1 d . . . . .
H14 H 0.367899 0.435062 0.390005 0.032 Uiso 1 1 calc R U . . .
C8 C 0.9812(3) 0.82366(16) 0.33981(5) 0.0260(3) Uani 1 1 d . . . . .
H8 H 1.125566 0.885380 0.334973 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3720(3) 0.96261(16) 0.43840(6) 0.0297(3) Uani 1 1 d . . . . .
H4 H 0.231734 0.993570 0.459153 0.036 Uiso 1 1 calc R U . . .
C13 C 0.3842(3) 0.39029(17) 0.31289(7) 0.0332(4) Uani 1 1 d . . . . .
H13 H 0.245723 0.323047 0.311937 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5005(3) 1.05469(16) 0.40667(6) 0.0340(4) Uani 1 1 d . . . . .
H5 H 0.450775 1.149536 0.406167 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7011(3) 1.00884(16) 0.37572(6) 0.0310(3) Uani 1 1 d . . . . .
H6 H 0.789126 1.073139 0.354420 0.037 Uiso 1 1 calc R U . . .
C11 C 0.7113(3) 0.52159(18) 0.26927(6) 0.0325(4) Uani 1 1 d . . . . .
H11 H 0.799952 0.542120 0.238271 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5150(4) 0.42187(18) 0.26785(6) 0.0365(4) Uani 1 1 d . . . . .
H12 H 0.469049 0.374754 0.236151 0.044 Uiso 1 1 calc R U . . .
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'
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
F20 C17 C16 118.64(12) . 3_766 ?
C18 C17 F20 116.30(12) . . ?
C18 C17 C16 125.04(12) . 3_766 ?
F19 C18 C16 118.65(11) . . ?
C17 C18 F19 116.42(12) . . ?
C17 C18 C16 124.93(12) . . ?
C10 C15 C1 119.38(12) . . ?
C14 C15 C1 120.77(12) . . ?
C14 C15 C10 119.80(13) . . ?
C2 C7 C8 122.55(13) . . ?
C2 C7 C6 118.05(14) . . ?
C6 C7 C8 119.40(13) . . ?
C7 C2 C1 119.55(12) . . ?
C3 C2 C7 119.83(13) . . ?
C3 C2 C1 120.59(13) . . ?
C2 C1 C15 111.62(11) . . ?
C16 C1 C15 124.33(12) . . ?
C16 C1 C2 124.02(12) . . ?
C15 C10 C9 122.80(12) . . ?
C11 C10 C15 118.01(14) . . ?
C11 C10 C9 119.19(13) . . ?
C18 C16 C17 110.02(11) . 3_766 ?
C1 C16 C17 124.90(12) . 3_766 ?
C1 C16 C18 125.04(12) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.12(14) . . ?
C4 C3 H3 119.4 . . ?
C10 C9 H9 116.9 . . ?
C8 C9 C10 126.19(14) . . ?
C8 C9 H9 116.9 . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.82(14) . . ?
C13 C14 H14 119.6 . . ?
C7 C8 H8 116.8 . . ?
C9 C8 C7 126.40(14) . . ?
C9 C8 H8 116.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.50(15) . . ?
C5 C4 H4 120.3 . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.70(15) . . ?
C12 C13 H13 120.2 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.14(14) . . ?
C6 C5 H5 119.9 . . ?
C7 C6 H6 119.4 . . ?
C5 C6 C7 121.25(15) . . ?
C5 C6 H6 119.4 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.76(15) . . ?
C12 C11 H11 119.1 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.81(14) . . ?
C11 C12 H12 120.1 . . ?
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
F19 C18 1.3459(15) . ?
F20 C17 1.3449(15) . ?
C17 C18 1.3421(19) . ?
C17 C16 1.4570(18) 3_766 ?
C18 C16 1.4545(19) . ?
C15 C1 1.4893(18) . ?
C15 C10 1.405(2) . ?
C15 C14 1.396(2) . ?
C7 C2 1.404(2) . ?
C7 C8 1.466(2) . ?
C7 C6 1.405(2) . ?
C2 C1 1.4887(18) . ?
C2 C3 1.395(2) . ?
C1 C16 1.3686(18) . ?
C10 C9 1.464(2) . ?
C10 C11 1.403(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.339(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.385(2) . ?
C8 H8 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.376(2) . ?
C12 H12 0.9500 . ?
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
F19 C18 C16 C17 -178.03(11) . . . 3_766 ?
F19 C18 C16 C1 -0.1(2) . . . . ?
F20 C17 C18 F19 -3.55(18) . . . . ?
F20 C17 C18 C16 177.48(12) . . . . ?
C17 C18 C16 C17 0.9(2) . . . 3_766 ?
C17 C18 C16 C1 178.80(13) . . . . ?
C15 C1 C16 C17 179.72(12) . . . 3_766 ?
C15 C1 C16 C18 2.2(2) . . . . ?
C15 C10 C9 C8 -37.7(2) . . . . ?
C15 C10 C11 C12 2.9(2) . . . . ?
C15 C14 C13 C12 0.5(2) . . . . ?
C7 C2 C1 C15 -67.22(16) . . . . ?
C7 C2 C1 C16 114.60(15) . . . . ?
C7 C2 C3 C4 -2.1(2) . . . . ?
C2 C7 C8 C9 37.8(2) . . . . ?
C2 C7 C6 C5 -3.3(2) . . . . ?
C2 C1 C16 C17 -2.3(2) . . . 3_766 ?
C2 C1 C16 C18 -179.89(13) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C1 C15 C10 C9 -1.6(2) . . . . ?
C1 C15 C10 C11 178.76(13) . . . . ?
C1 C15 C14 C13 179.61(13) . . . . ?
C1 C2 C3 C4 179.94(13) . . . . ?
C10 C15 C1 C2 67.11(16) . . . . ?
C10 C15 C1 C16 -114.71(15) . . . . ?
C10 C15 C14 C13 2.2(2) . . . . ?
C10 C9 C8 C7 -0.2(2) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C16 C17 C18 F19 177.92(12) 3_766 . . . ?
C16 C17 C18 C16 -1.1(2) 3_766 . . . ?
C3 C2 C1 C15 110.80(14) . . . . ?
C3 C2 C1 C16 -67.39(18) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C9 C10 C11 C12 -176.75(15) . . . . ?
C14 C15 C1 C2 -110.30(14) . . . . ?
C14 C15 C1 C16 67.88(19) . . . . ?
C14 C15 C10 C9 175.81(13) . . . . ?
C14 C15 C10 C11 -3.8(2) . . . . ?
C14 C13 C12 C11 -1.4(2) . . . . ?
C8 C7 C2 C1 1.8(2) . . . . ?
C8 C7 C2 C3 -176.27(13) . . . . ?
C8 C7 C6 C5 176.90(14) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C6 C7 C2 C1 -178.06(13) . . . . ?
C6 C7 C2 C3 3.9(2) . . . . ?
C6 C7 C8 C9 -142.41(16) . . . . ?
C11 C10 C9 C8 141.93(16) . . . . ?
