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_7134244
_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 F4'
_chemical_formula_sum            'C36 H20 F4'
_chemical_formula_weight         528.52
_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
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2lls22
_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                 108.206(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.7620(5)
_cell_length_b                   4.87070(10)
_cell_length_c                   19.2419(3)
_cell_measurement_reflns_used    9193
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.7030
_cell_measurement_theta_min      3.3240
_cell_volume                     2471.64(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (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 0.986
_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   -131.00 -99.00   0.50    0.91    -- -104.50 153.00 -91.08   64
  2  \w    -92.00 -66.00   0.50    0.91    -- -104.50 153.00 -91.08   52
  3  \w    -92.00 -66.00   0.50    0.91    -- -104.50 142.00   0.25   52
  4  \w   -124.00 -98.00   0.50    0.91    -- -104.50 142.00   0.25   52
  5  \w   -110.00 -81.00   0.50    0.91    -- -104.50 125.00  60.00   58
  6  \w    -76.00 -44.00   0.50    0.91    -- -104.50 125.00  60.00   64
  7  \w   -111.00 -36.00   0.50    0.91    -- -104.50 125.00 120.00  150
  8  \w   -108.00 -40.00   0.50    0.91    -- -104.50 125.00  90.00  136
  9  \w    -90.00 -48.00   0.50    0.23    --  -47.20 125.00-150.00   84
 10  \w    -92.00 -66.00   0.50    0.91    -- -104.50  77.00 -90.00   52
 11  \w    -93.00 -67.00   0.50    0.91    -- -104.50  77.00-120.00   52
 12  \w    -57.00 -32.00   0.50    0.91    -- -104.50  77.00-120.00   50
 13  \w    -56.00  20.00   0.50    0.23    --  -47.20  57.00  30.00  152
 14  \w   -147.00-116.00   0.50    0.91    -- -104.50   3.00 173.00   62
 15  \w    -20.00  26.00   0.50    0.23    --  -47.20   3.00 173.00   92
 16  \w    -12.00 120.00   0.50    0.23    --   47.20   3.00 173.00  264
 17  \w     31.00 176.00   0.50    0.91    --  103.25   3.00 173.00  290
 18  \w     40.00  70.00   0.50    0.23    --   47.20-125.00   0.00   60
 19  \w     79.00 108.00   0.50    0.91    --  103.25-125.00 -90.00   58
 20  \w     37.00  62.00   0.50    0.91    --  103.25-125.00 -90.00   50
 21  \w     35.00  76.00   0.50    0.91    --  103.25-110.00 -78.14   82
 22  \w     82.00 108.00   0.50    0.91    --  103.25-110.00 -78.14   52
 23  \w     35.00 104.00   0.50    0.91    --  103.25 -94.00 -60.00  138
 24  \w     33.00  72.00   0.50    0.91    --  103.25 -94.00  60.00   78
 25  \w     31.00  89.00   0.50    0.91    --  103.25 -94.00   0.00  116
 26  \w     48.00 106.00   0.50    0.91    --  103.25 -94.00 150.00  116
 27  \w     34.00  60.00   0.50    0.91    --  103.25 -94.00  90.00   52
 28  \w     31.00 174.00   0.50    0.91    --  103.25   0.00 -30.00  286
 29  \w    -21.00  25.00   0.50    0.23    --   47.20  -3.00  -3.00   92
 30  \w     31.00  74.00   0.50    0.91    --  103.25 -61.00  60.00   86
 31  \w     39.00  74.00   0.50    0.91    --  103.25 -77.00 -60.00   70
 32  \w     32.00  75.00   0.50    0.91    --  103.25 -61.00-180.00   86
 33  \w     33.00  67.00   0.50    0.91    --  103.25 -61.00-120.00   68
 34  \w    -18.00  67.00   0.50    0.23    --   47.20 -77.00-180.00  170
 35  \w     47.00  74.00   0.50    0.91    --  103.25 -61.00 -30.00   54
 36  \w     31.00  62.00   0.50    0.91    --  103.25 -61.00 150.00   62
 37  \w    -96.00 -65.00   0.50    0.23    --  -47.20  -3.00  -3.00   62
 38  \w   -160.00 -65.00   0.50    0.91    -- -104.50  -3.00  -3.00  190
 39  \w   -174.00-110.00   0.50    0.91    -- -104.50 -94.00 -90.00  128
;
_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      -0.0224588000
_diffrn_orient_matrix_UB_12      -0.2893424000
_diffrn_orient_matrix_UB_13      -0.0001678000
_diffrn_orient_matrix_UB_21      0.0498330000
_diffrn_orient_matrix_UB_22      -0.1276182000
_diffrn_orient_matrix_UB_23      -0.0040329000
_diffrn_orient_matrix_UB_31      0.0206234000
_diffrn_orient_matrix_UB_32      -0.0068397000
_diffrn_orient_matrix_UB_33      0.0841767000
_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  0.0458
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15288
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.541
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'fluorescent light yellow'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0493
_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/[\s^2^(Fo^2^)+(0.0765P)^2^+1.7770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2339
_reflns_number_total             2520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00053j2.cif
_cod_data_source_block           2a-solution
_cod_depositor_comments
'Adding full bibliography for 7134240--7134246.cif.'
_cod_database_code               7134244
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H F Cl'
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C8(H8), C9(H9), C13(H13), C12(H12), C11(H11), C4(H4),
 C6(H6), C5(H5)
;
_shelx_res_checksum              74025
_shelx_hkl_checksum              64577
_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 2.181
_oxdiff_exptl_absorpt_empirical_full_min 0.585