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_1554953
_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         'C32 H30 O4 S, 0.258(H2 O)'
_chemical_formula_sum            'C32 H30.52 O4.26 S'
_chemical_formula_weight         515.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-09-20 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.298(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9336(7)
_cell_length_b                   19.7182(9)
_cell_length_c                   20.3209(11)
_cell_measurement_reflns_used    14523
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      1.82
_cell_volume                     5433.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 Varimax with Saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            46281
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.823
_diffrn_source                   'rotating anode X-ray generator'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.431
_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_colour            violet
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2181
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6557
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0847
_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^)+(0.1164P)^2^+8.8350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4029
_reflns_number_total             6557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00593e2.cif
_cod_data_source_block           shelxl_CCDC2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1554953
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              77742
_shelx_hkl_checksum              27574