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_7134245
_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      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.cc2lls55
_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                81.594(4)
_cell_angle_beta                 80.336(3)
_cell_angle_gamma                81.165(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7937(3)
_cell_length_b                   11.0552(5)
_cell_length_c                   14.1737(6)
_cell_measurement_reflns_used    9634
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.0810
_cell_measurement_theta_min      1.8710
_cell_volume                     1331.95(10)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_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 0.847
_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   -100.00 -27.00   0.50    1.83    --  -10.70  45.00  90.00  146
  2  \w    -22.00  78.00   0.50    1.83    --  -10.70  45.00  90.00  200
  3  \w    -21.00  78.00   0.50    1.83    --  -10.70  45.00 175.50  198
  4  \w    -68.00 -42.00   0.50    1.83    --  -10.70  45.00  20.80   52
  5  \w    -12.00  40.00   0.50    1.83    --  -10.70  45.00  20.80  104
  6  \w   -100.00  -1.00   0.50    1.83    --  -10.70  45.00 150.00  198
  7  \w     -6.00  68.00   0.50    1.83    --  -10.70  45.00 -15.82  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0227032000
_diffrn_orient_matrix_UB_12      0.0101329000
_diffrn_orient_matrix_UB_13      -0.0465308000
_diffrn_orient_matrix_UB_21      -0.0787555000
_diffrn_orient_matrix_UB_22      0.0140085000
_diffrn_orient_matrix_UB_23      0.0209263000
_diffrn_orient_matrix_UB_31      0.0098024000
_diffrn_orient_matrix_UB_32      0.0631067000
_diffrn_orient_matrix_UB_33      -0.0037298000
_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  0.0262
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.918
_diffrn_reflns_theta_min         1.879
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91800
_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    1.622
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         7129
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0228P)^2^+0.6974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5904
_reflns_number_total             7129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00053j2.cif
_cod_data_source_block           2c-PVT
_cod_depositor_comments
'Adding full bibliography for 7134240--7134246.cif.'
_cod_database_code               7134245
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C F Cl H'
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.607
_olex2_refinement_description
;
1. Restrained distances
 F2A-C20 = F1A-C17
 1.34 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
Br1A \\sim Br2A \\sim F1 \\sim F2 \\sim Br1 \\sim Br2 \\sim F1A \\sim F2A:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
Uanis(F2A) \\sim Ueq, Uanis(F1A) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
3. Others
 Sof(Br1)=Sof(Br2)=Sof(F1A)=Sof(F2A)=1-FVAR(1)
 Sof(Br1A)=Sof(Br2A)=Sof(F1)=Sof(F2)=FVAR(1)
4.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), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C32(H32),
  C33(H33), C34(H34), C35(H35)
;
_shelx_res_checksum              52101
_shelx_hkl_checksum              14529
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.848