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_1554952
_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         'C25 H25 N O2 S'
_chemical_formula_sum            'C25 H25 N O2 S'
_chemical_formula_weight         403.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.07714(18)
_cell_length_b                   13.1618(3)
_cell_length_c                   27.1117(8)
_cell_measurement_reflns_used    20425
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.21
_cell_measurement_theta_min      2.12
_cell_volume                     2168.56(10)
_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 0.998
_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  0.0662
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            37355
_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         27.999
_diffrn_reflns_theta_min         1.720
_diffrn_source                   'rotating anode X-ray generator'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.789
_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    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1837 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0366P)^2^+0.8909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4763
_reflns_number_total             5220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00593e2.cif
_cod_data_source_block           shelxl_CCDC1
_cod_database_code               1554952
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              15423
_shelx_hkl_checksum              32928