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_7134246
_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         '2(C18 H12)'
_chemical_formula_sum            'C36 H24'
_chemical_formula_weight         456.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2lls77
_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                72.986(2)
_cell_angle_beta                 78.424(3)
_cell_angle_gamma                66.751(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2666(3)
_cell_length_b                   10.9440(3)
_cell_length_c                   13.7572(4)
_cell_measurement_reflns_used    9058
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      76.7640
_cell_measurement_theta_min      3.3520
_cell_volume                     1220.00(7)
_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 0.953
_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     -6.00  21.00   0.50    0.05    --   46.67 -57.00 150.00   54
  2  \w     27.00  63.00   0.50    0.05    --   46.67 -57.00 150.00   72
  3  \w    -22.00  29.00   0.50    0.05    --  -46.67  19.00 150.00  102
  4  \w     17.00  43.00   0.50    0.05    --   46.67 -40.00-144.00   52
  5  \w    -20.00   8.00   0.50    0.05    --   46.67 -40.00-144.00   56
  6  \w    -41.00  20.00   0.50    0.05    --  -46.67  40.00   8.00  122
  7  \w    -18.00   8.00   0.50    0.05    --  -46.67  19.00-120.00   52
  8  \w     95.00 122.00   0.50    0.12    --  108.85  45.00 -60.00   54
  9  \w    127.00 173.00   0.50    0.12    --  108.85  45.00 -60.00   92
 10  \w    144.00 176.00   0.50    0.12    --  108.85  40.00   8.00   64
 11  \w    113.00 141.00   0.50    0.12    --  108.85  40.00   8.00   56
 12  \w     97.00 167.00   0.50    0.12    --  108.85  30.00  60.00  140
 13  \w    110.00 162.00   0.50    0.12    --  108.85  30.00  90.00  104
 14  \w     91.00 177.00   0.50    0.12    --  108.85  15.00 150.00  172
 15  \w     34.00 119.00   0.50    0.05    --   46.67  40.00   8.00  170
 16  \w     36.00  61.00   0.50    0.12    --  108.85 -61.00 -90.00   50
 17  \w     38.00 106.00   0.50    0.12    --  108.85 -77.00-120.00  136
 18  \w     37.00 106.00   0.50    0.12    --  108.85 -77.00 -30.00  138
 19  \w     41.00  73.00   0.50    0.12    --  108.85 -61.00  90.00   64
 20  \w     26.00  85.00   0.50    0.05    --   46.67-125.00  60.00  118
 21  \w     49.00  98.00   0.50    0.12    --  108.85-125.00 120.00   98
 22  \w     45.00  81.00   0.50    0.12    --  108.85-125.00  30.00   72
 23  \w     41.00  79.00   0.50    0.12    --  108.85-125.00   0.00   76
 24  \w     85.00 111.00   0.50    0.12    --  108.85-125.00   0.00   52
 25  \w     85.00 111.00   0.50    0.12    --  108.85-125.00  60.00   52
 26  \w     86.00 112.00   0.50    0.12    --  108.85-125.00  30.00   52
 27  \w     44.00  70.00   0.50    0.12    --  108.85-125.00  60.00   52
 28  \w     43.00  69.00   0.50    0.12    --  108.85-125.00 -90.00   52
 29  \w     86.00 111.00   0.50    0.12    --  108.85-125.00 -90.00   50
 30  \w     41.00  91.00   0.50    0.12    --  108.85 -94.00-150.00  100
 31  \w     48.00  97.00   0.50    0.12    --  108.85 -94.00 -90.00   98
 32  \w    -76.00 -50.00   0.50    0.12    -- -104.50 146.00  80.44   52
 33  \w   -109.00 -49.00   0.50    0.12    -- -104.50 117.00  22.19  120
 34  \w   -127.00 -98.00   0.50    0.12    -- -104.50 146.00  80.44   58
 35  \w   -111.00 -71.00   0.50    0.12    -- -104.50 125.00 150.00   80
 36  \w    -66.00 -39.00   0.50    0.12    -- -104.50 125.00 150.00   54
 37  \w    -68.00 -36.00   0.50    0.12    -- -104.50  61.00 120.00   64
 38  \w   -102.00 -77.00   0.50    0.12    -- -104.50  77.00 -90.00   50
 39  \w   -102.00 -39.00   0.50    0.12    -- -104.50  77.00-180.00  126
 40  \w   -122.00 -91.00   0.50    0.12    -- -104.50 -15.00 -90.00   62
 41  \w   -168.00 -99.00   0.50    0.12    -- -104.50 -40.00-144.00  138
 42  \w   -174.00-129.00   0.50    0.12    -- -104.50 -15.00 -90.00   90
 43  \w   -103.00 -34.00   0.50    0.05    --  -46.67 -40.00-144.00  138
;
_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      -0.1752180000
_diffrn_orient_matrix_UB_12      0.0153558000
_diffrn_orient_matrix_UB_13      0.0220406000
_diffrn_orient_matrix_UB_21      -0.0477090000
_diffrn_orient_matrix_UB_22      0.1525425000
_diffrn_orient_matrix_UB_23      -0.0556007000
_diffrn_orient_matrix_UB_31      0.0085309000
_diffrn_orient_matrix_UB_32      -0.0369505000
_diffrn_orient_matrix_UB_33      -0.1013259000
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14799
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.814
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88250
_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            'fluorescent light yellow'
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       cube
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0059(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0497P)^2^+0.2171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1085
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4238
_reflns_number_total             4955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00053j2.cif
_cod_data_source_block           2d-PVT
_cod_depositor_comments
'Adding full bibliography for 7134240--7134246.cif.'
_cod_database_code               7134246
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'C H Cl'
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C36(H36), C35(H35), C3(H3), C17(H17), C14(H14), C32(H32), C13(H13),
 C21(H21), C4(H4), C26(H26), C27(H27), C24(H24), C11(H11), C29(H29), C9(H9),
 C8(H8), C6(H6), C12(H12), C5(H5), C22(H22), C31(H31), C23(H23), C30(H30)
;
_shelx_res_checksum              14345
_shelx_hkl_checksum              7136
_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.652