Synthesis of azuleno[2,1-b]thiophenes by cycloaddition of azulenylalkynes with elemental sulfur and their structural, optical and electrochemical properties
Shoji, Taku; Miura, Kota; Ohta, Akira; Sekiguchi, Ryuta; Ito, Shunji; Endo, Yuya; Nagahata, Tatsuki; Mori, Shigeki; Okujima, Tetsuo; Organic Chemistry Frontiers 6 (2019) 2801–; doi:10.1039/C9QO00593E

data_1554951
_publ_section_title
;
 Synthesis of azuleno[2,1-b]thiophenes by cycloaddition of azulenylalkynes
 with elemental sulfur and their structural, optical and electrochemical
 properties
;
_journal_issue                   15
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2801
_journal_paper_doi               10.1039/C9QO00593E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C24 H24 O2 S2'
_chemical_formula_sum            'C24 H24 O2 S2'
_chemical_formula_weight         408.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-07-12 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.617(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8323(16)
_cell_length_b                   5.5909(4)
_cell_length_c                   15.6580(11)
_cell_measurement_reflns_used    5867
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.91
_cell_measurement_theta_min      1.97
_cell_volume                     2027.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_publication_material  'CrystalStructure 4.2.4'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16795
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.758
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1203 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     281
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0709
_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^)+(0.0653P)^2^+3.0831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3749
_reflns_number_total             4907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00593e2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1554951
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.896
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              60523
_shelx_hkl_checksum              41816