Assembly of unsymmetrical 1,3,5-triarylbenzenes via tandem reaction of β-arylethenesulfonyl fluorides and α-cyano-β-methylenones
Zhang, Fang; An, Yi; Liu, Jichang; Du, Guangfen; Cai, Zhihua; He, Lin; New Journal of Chemistry 46 (2022) 12367–12371; doi:10.1039/D2NJ01549H

data_7061560
_publ_section_title
;
 Assembly of unsymmetrical 1,3,5-triarylbenzenes via tandem reaction of
 \b-arylethenesulfonyl fluorides and \a-cyano-\b-methylenones
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12367
_journal_page_last               12371
_journal_paper_doi               10.1039/D2NJ01549H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C19 H14 N'
_chemical_formula_sum            'C19 H14 N'
_chemical_formula_weight         256.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-29 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.1719(5)
_cell_length_b                   8.9226(3)
_cell_length_c                   5.6638(2)
_cell_measurement_reflns_used    5296
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.04
_cell_measurement_theta_min      5.86
_cell_volume                     716.19(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8521
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.166
_diffrn_reflns_theta_min         4.956
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1108 before and 0.0593 after correction. The Ratio of minimum to maximum transmission is 0.8730. The \l/2 correction factor is Not present.'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       block
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.008(3)
_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   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1417
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0518P)^2^+0.0881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1360
_reflns_number_total             1417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj01549h2.cif
_cod_data_source_block           11
_cod_depositor_comments          'Adding full bibliography for 7061560.cif.'
_cod_database_code               7061560
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C10A \\sim C10 \\sim C9 \\sim C9A \\sim C9 \\sim C9A: within 3.8A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C10) \\sim Ueq, Uanis(C10A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 C7, C9, C10, C9, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C9A, C10A, C9A, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(C10A)=Sof(H10C)=Sof(H10D)=0.5*(1-FVAR(2))
 Sof(C10)=Sof(H10A)=Sof(H10B)=0.5*FVAR(2)
 Sof(C9)=Sof(H9)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10A(H10C,H10D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C9A(H9A)
;
_shelx_res_checksum              38886
_olex2_submission_special_instructions 'No special instructions were received'