The copper-catalyzed synthesis of (<i>Z</i>)-2<i>H</i>-naphtho[1,8-<i>bc</i>]thiophenes with solid emission.
Zhang, Yuan; Lai, Weiping; Zhang, Lianpeng; Gao, Xiaoxing; Qiu, Guanyinsheng; Zhou, Hongwei; Organic & biomolecular chemistry 19 (2021) 1827–1834; doi:10.1039/d0ob02233k

data_7157859
_publ_section_title
;
 The copper-catalyzed synthesis of
 (<i>Z</i>)-2<i>H</i>-naphtho[1,8-<i>bc</i>]thiophenes with solid
 emission.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1827
_journal_page_last               1834
_journal_paper_doi               10.1039/d0ob02233k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H11 F S'
_chemical_formula_sum            'C18 H11 F S'
_chemical_formula_weight         278.34
_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
_audit_creation_date             2018-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-04-09 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                63.737(6)
_cell_angle_beta                 72.360(6)
_cell_angle_gamma                82.226(5)
_cell_formula_units_Z            6
_cell_length_a                   11.1078(7)
_cell_length_b                   14.2349(9)
_cell_length_c                   14.7424(10)
_cell_measurement_reflns_used    3650
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5680
_cell_measurement_theta_min      3.4120
_cell_volume                     1992.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.835
_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    -25.00  20.00   1.00    2.33    --  -15.89 -99.00  60.00   45
  2  \w    -73.00 -42.00   1.00    2.33    --  -15.89 149.00 -78.00   31
  3  \w    -25.00  23.00   1.00    2.33    --  -15.89 -99.00-120.00   48
  4  \w    -56.00 -28.00   1.00    2.33    --  -15.89 124.00 117.00   28
  5  \w    -41.00  24.00   1.00    2.33    --   16.05 -19.00-150.00   65
  6  \w    -22.00   5.00   1.00    2.33    --   16.05 -57.00  60.00   27
  7  \w    -53.00  74.00   1.00    2.33    --   16.05   0.00 -90.00  127
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0350292000
_diffrn_orient_matrix_UB_12      0.0123305000
_diffrn_orient_matrix_UB_13      0.0263253000
_diffrn_orient_matrix_UB_21      -0.0134434000
_diffrn_orient_matrix_UB_22      0.0539299000
_diffrn_orient_matrix_UB_23      -0.0264713000
_diffrn_orient_matrix_UB_31      -0.0555171000
_diffrn_orient_matrix_UB_32      -0.0051863000
_diffrn_orient_matrix_UB_33      0.0414461000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16509
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.438
_diffrn_reflns_theta_min         2.887
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_F_000             1120
_refine_diff_density_max         1.550
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         9215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0676
_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^)+(0.0852P)^2^+1.4389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.2023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5889
_reflns_number_total             9215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02233k2.cif
_cod_data_source_block           20180705-1
_cod_depositor_comments
;
         Adding full bibliography for 7157859.cif.

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C14 H14 F14 O14 S14'
_cod_original_formula_weight         1121.09
_cod_original_formula_moiety         '3(C18 H11 F S)'
_cod_original_formula_units_Z            2
_cod_database_code               7157859
_chemical_oxdiff_formula         'C H O S F'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00P(H00P), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016),
 C018(H018), C019(H019), C01A(H01A), C01C(H01C), C01D(H01D), C01E(H01E),
 C01F(H01F), C01G(H01G), C01H(H01H), C01J(H01J), C01K(H01K), C01L(H01L),
 C01M(H01M), C01N(H01N), C01O(H01O)
;
_shelx_res_checksum              93474
_shelx_shelxl_version_number     2014/7
_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 1.157
_oxdiff_exptl_absorpt_empirical_full_min 0.860