#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:11:10 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298774 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/42/7134241.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_7134241
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 Cl2 F2'
_chemical_formula_sum            'C36 H20 Cl2 F2'
_chemical_formula_weight         561.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2lls33
_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                 117.617(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.2651(19)
_cell_length_b                   5.2855(2)
_cell_length_c                   20.7563(10)
_cell_measurement_reflns_used    4133
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      29.0660
_cell_measurement_theta_min      1.6860
_cell_volume                     2650.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -47.00   0.50    8.00    --    5.00  45.00   0.00   52
  2  ω    -80.00  61.00   0.50    8.00    --  -10.70  45.00  60.00  282
  3  ω     28.00  57.00   0.50    8.00    --  -10.70  45.00 162.35   58
  4  ω    -90.00  13.00   0.50    8.00    --  -10.70  45.00 162.35  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0049791000
_diffrn_orient_matrix_UB_12      0.0459606000
_diffrn_orient_matrix_UB_13      -0.0271694000
_diffrn_orient_matrix_UB_21      0.0348075000
_diffrn_orient_matrix_UB_22      0.0345421000
_diffrn_orient_matrix_UB_23      0.0076477000
_diffrn_orient_matrix_UB_31      0.0080496000
_diffrn_orient_matrix_UB_32      -0.1210985000
_diffrn_orient_matrix_UB_33      -0.0080960000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10675
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.790
_diffrn_reflns_theta_min         1.686
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0472
_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)+(0.0578P)²+1.6128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2813
_reflns_number_total             3485
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc00053j2.cif
_cod_data_source_block           2b-PVT
_cod_depositor_comments
'Adding full bibliography for 7134240--7134246.cif.'
_cod_database_code               7134241
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H F Cl'
_chemical_oxdiff_usercomment     2F2ClQSH
_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. Others
 Sof(Cl1A)=Sof(F1A)=1-FVAR(1)
 Sof(Cl1)=Sof(F1)=FVAR(1)
2.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 2.126
_oxdiff_exptl_absorpt_empirical_full_min 0.568
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.59843(6) 0.7433(3) 0.74150(8) 0.0306(3) Uani 1 1 d . . . . .
C2 C 0.65193(6) 0.6921(3) 0.80589(8) 0.0339(3) Uani 1 1 d . . . . .
C3 C 0.65592(8) 0.4952(3) 0.85254(9) 0.0443(4) Uani 1 1 d . . . . .
H3 H 0.624604 0.391371 0.841666 0.053 Uiso 1 1 calc R U . . .
C4 C 0.70475(9) 0.4494(4) 0.91427(10) 0.0565(5) Uani 1 1 d . . . . .
H4 H 0.707390 0.312531 0.945367 0.068 Uiso 1 1 calc R U . . .
C5 C 0.74975(8) 0.6029(5) 0.93073(10) 0.0590(6) Uani 1 1 d . . . . .
H5 H 0.783030 0.576119 0.974400 0.071 Uiso 1 1 calc R U . . .
C6 C 0.74690(7) 0.7942(4) 0.88454(10) 0.0534(5) Uani 1 1 d . . . . .
H6 H 0.778332 0.898927 0.896919 0.064 Uiso 1 1 calc R U . . .
C7 C 0.69861(6) 0.8387(3) 0.81943(9) 0.0394(4) Uani 1 1 d . . . . .
C8 C 0.69886(7) 1.0302(4) 0.76936(11) 0.0487(4) Uani 1 1 d . . . . .
H8 H 0.721471 1.174432 0.790415 0.058 Uiso 1 1 calc R U . . .
C9 C 0.67069(8) 1.0249(4) 0.69691(11) 0.0498(5) Uani 1 1 d . . . . .
H9 H 0.675613 1.165756 0.672063 0.060 Uiso 1 1 calc R U . . .
C10 C 0.63317(6) 0.8274(3) 0.65147(9) 0.0404(4) Uani 1 1 d . . . . .
C11 C 0.63028(8) 0.7741(4) 0.58388(10) 0.0554(5) Uani 1 1 d . . . . .
H11 H 0.650857 0.875205 0.567105 0.066 Uiso 1 1 calc R U . . .
C12 C 0.59851(9) 0.5797(5) 0.54109(10) 0.0602(6) Uani 1 1 d . . . . .
H12 H 0.597747 0.545987 0.495681 0.072 Uiso 1 1 calc R U . . .
C13 C 0.56765(8) 0.4330(4) 0.56398(10) 0.0539(5) Uani 1 1 d . . . . .
H13 H 0.546405 0.295346 0.535072 0.065 Uiso 1 1 calc R U . . .
C14 C 0.56786(7) 0.4876(3) 0.62912(9) 0.0433(4) Uani 1 1 d . . . . .
H14 H 0.546208 0.388095 0.644538 0.052 Uiso 1 1 calc R U . . .
C15 C 0.59925(6) 0.6856(3) 0.67236(8) 0.0335(3) Uani 1 1 d . . . . .
C16 C 0.55208(5) 0.8157(3) 0.74585(8) 0.0294(3) Uani 1 1 d . . . . .
C17 C 0.49852(6) 0.8636(3) 0.68293(7) 0.0292(3) Uani 1 1 d . . . . .
C18 C 0.45068(5) 0.8644(3) 0.68642(8) 0.0296(3) Uani 1 1 d . . . . .
Cl1 Cl 0.39518(4) 0.94461(19) 0.60323(7) 0.0355(3) Uani 0.586(3) 1 d . . P A 1
F1 F 0.50320(12) 0.9189(5) 0.62387(18) 0.0380(5) Uani 0.586(3) 1 d . . P A 1
Cl1A Cl 0.48645(7) 0.9547(3) 0.59535(9) 0.0335(4) Uani 0.414(3) 1 d . . P A 2
F1A F 0.40147(14) 0.9327(7) 0.6345(3) 0.0393(7) Uani 0.414(3) 1 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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
C2 C1 C15 112.82(12) . . ?
C16 C1 C2 123.29(13) . . ?
C16 C1 C15 123.67(13) . . ?
C3 C2 C1 119.54(14) . . ?
C3 C2 C7 120.20(15) . . ?
C7 C2 C1 120.25(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.64(18) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.65(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.44(17) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.43(18) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C8 123.11(15) . . ?
C6 C7 C2 117.37(16) . . ?
C6 C7 C8 119.52(16) . . ?
C7 C8 H8 116.6 . . ?
C9 C8 C7 126.89(17) . . ?
C9 C8 H8 116.6 . . ?
C8 C9 H9 116.3 . . ?
C8 C9 C10 127.44(16) . . ?
C10 C9 H9 116.3 . . ?
C11 C10 C9 119.30(16) . . ?
C11 C10 C15 117.60(17) . . ?
C15 C10 C9 123.10(15) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.73(18) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.05(17) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.56(19) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.87(17) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C1 119.85(14) . . ?
C14 C15 C1 120.13(14) . . ?
C14 C15 C10 120.00(15) . . ?
C1 C16 C17 124.25(13) . . ?
C1 C16 C18 125.07(13) . 2_656 ?
C17 C16 C18 110.65(11) . 2_656 ?
C16 C17 Cl1A 127.04(11) . . ?
C18 C17 C16 123.17(12) . . ?
C18 C17 Cl1A 109.57(12) . . ?
F1 C17 C16 112.39(16) . . ?
F1 C17 C18 124.35(17) . . ?
C16 C18 Cl1 125.96(11) 2_656 . ?
C17 C18 C16 122.40(13) . 2_656 ?
C17 C18 Cl1 111.57(11) . . ?
F1A C18 C17 127.0(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
C1 C2 1.477(2) . ?
C1 C15 1.477(2) . ?
C1 C16 1.3629(18) . ?
C2 C3 1.391(2) . ?
C2 C7 1.403(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.371(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.402(2) . ?
C7 C8 1.453(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.335(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.460(3) . ?
C10 C11 1.397(2) . ?
C10 C15 1.406(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.372(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C16 C17 1.4608(19) . ?
C16 C18 1.4651(19) 2_656 ?
C17 C18 1.3395(19) . ?
C17 F1 1.323(3) . ?
C17 Cl1A 1.758(2) . ?
C18 Cl1 1.7403(18) . ?
C18 F1A 1.324(4) . ?
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
C1 C2 C3 C4 -177.65(15) . . . . ?
C1 C2 C7 C6 174.84(14) . . . . ?
C1 C2 C7 C8 -5.5(2) . . . . ?
C1 C16 C17 C18 160.61(15) . . . . ?
C1 C16 C17 F1 -22.8(2) . . . . ?
C1 C16 C17 Cl1A -25.5(2) . . . . ?
C2 C1 C15 C10 -65.53(18) . . . . ?
C2 C1 C15 C14 112.67(15) . . . . ?
C2 C1 C16 C17 -179.01(13) . . . . ?
C2 C1 C16 C18 3.1(2) . . . 2_656 ?
C2 C3 C4 C5 1.3(3) . . . . ?
C2 C7 C8 C9 -33.3(3) . . . . ?
C3 C2 C7 C6 -6.0(2) . . . . ?
C3 C2 C7 C8 173.69(15) . . . . ?
C3 C4 C5 C6 -2.7(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C2 4.6(2) . . . . ?
C5 C6 C7 C8 -175.06(16) . . . . ?
C6 C7 C8 C9 146.39(18) . . . . ?
C7 C2 C3 C4 3.2(2) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 -145.91(18) . . . . ?
C8 C9 C10 C15 34.1(3) . . . . ?
C9 C10 C11 C12 175.66(18) . . . . ?
C9 C10 C15 C1 3.3(2) . . . . ?
C9 C10 C15 C14 -174.91(16) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C10 C15 C1 -176.73(14) . . . . ?
C11 C10 C15 C14 5.1(2) . . . . ?
C11 C12 C13 C14 1.7(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C1 179.23(15) . . . . ?
C13 C14 C15 C10 -2.6(2) . . . . ?
C15 C1 C2 C3 -111.90(16) . . . . ?
C15 C1 C2 C7 67.27(18) . . . . ?
C15 C1 C16 C17 -4.8(2) . . . . ?
C15 C1 C16 C18 177.40(13) . . . 2_656 ?
C15 C10 C11 C12 -4.3(3) . . . . ?
C16 C1 C2 C3 62.9(2) . . . . ?
C16 C1 C2 C7 -117.91(16) . . . . ?
C16 C1 C15 C10 119.68(16) . . . . ?
C16 C1 C15 C14 -62.1(2) . . . . ?
C16 C17 C18 C16 -0.3(2) . . . 2_656 ?
C16 C17 C18 Cl1 176.73(12) . . . . ?
C16 C17 C18 F1A 172.0(2) . . . . ?
C18 C16 C17 C18 -21.28(17) 2_656 . . . ?
C18 C16 C17 F1 155.32(15) 2_656 . . . ?
C18 C16 C17 Cl1A 152.66(12) 2_656 . . . ?
F1 C17 C18 C16 -176.50(17) . . . 2_656 ?
F1 C17 C18 Cl1 0.5(2) . . . . ?
Cl1A C17 C18 C16 -175.17(12) . . . 2_656 ?
Cl1A C17 C18 F1A -2.8(3) . . . . ?
