Heptene end-capped Thiele hydrocarbons with tunable configuration and emission and on-surface transformation <i>via</i> annulation.
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; Chemical communications (Cambridge, England) 61 (2025) 3994–3997; doi:10.1039/d5cc00053j

data_7134243
_publ_section_title
;
 Heptene end-capped Thiele hydrocarbons with tunable configuration and
 emission and on-surface transformation <i>via</i> 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  t~exp~   \w     \q     \k     \f   Frames
  1  \w     40.00  69.00   0.50    0.05    --  107.36 -57.00 -30.00   58
  2  \w     35.00  69.00   0.50    0.05    --  107.36 -57.00   0.00   68
  3  \w     38.00  69.00   0.50    0.05    --  107.36 -57.00  60.00   62
  4  \w     46.00  82.00   0.50    0.05    --  107.36 -77.00  60.00   72
  5  \w    113.00 170.00   0.50    0.05    --  107.36  19.00 -90.00  114
  6  \w    120.00 178.00   0.50    0.05    --  107.36  84.00 -44.00  116
  7  \w    -24.00  72.00   0.50    0.05    --   47.70 -84.00-164.00  192
  8  \w     56.00 132.00   0.50    0.05    --  107.36 -84.00-164.00  152
  9  \w    -17.00  28.00   0.50    0.05    --  -47.70  19.00  60.00   90
 10  \w    -20.00   7.00   0.50    0.05    --  -47.70  19.00  30.00   54
 11  \w    -82.00 -56.00   0.50    0.05    -- -104.50  77.00 -30.00   52
 12  \w    -59.00 -32.00   0.50    0.05    -- -104.50  57.00 -90.00   54
 13  \w    -62.00 -34.00   0.50    0.05    -- -104.50  57.00 -60.00   56
 14  \w    -62.00 -33.00   0.50    0.05    -- -104.50  57.00 -30.00   58
 15  \w    -59.00 -33.00   0.50    0.05    -- -104.50  57.00  60.00   52
 16  \w    -58.00 -32.00   0.50    0.05    -- -104.50  57.00 150.00   52
 17  \w   -116.00 -74.00   0.50    0.05    --  -47.70-125.00 -90.00   84
 18  \w   -105.00 -80.00   0.50    0.05    -- -104.50  84.00 -44.00   50
 19  \w   -170.00 -89.00   0.50    0.05    -- -104.50 -57.00-120.00  162
 20  \w   -174.00 -99.00   0.50    0.05    -- -104.50 -84.00-164.00  150
 21  \w    -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       '\w 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/[\s^2^(Fo^2^)+(0.0541P)^2^+3.4831P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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'
_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)
;
_shelx_res_checksum              65718
_shelx_hkl_checksum              38444
_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