A formal [4 + 2] cycloaddition of sulfur-containing alkylidene heterocycles with allenic compounds
Dočekal, Vojtěch; Formánek, Bedřich; Císařová, Ivana; Veselý, Jan; Organic Chemistry Frontiers 6 (2019) 3259–; doi:10.1039/C9QO00886A

data_1555111
_publ_section_title
;
 A formal [4 + 2] cycloaddition of sulfur-containing alkylidene
 heterocycles with allenic compounds
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3259
_journal_paper_doi               10.1039/C9QO00886A
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C27 H21 N O3 S'
_chemical_formula_sum            'C27 H21 N O3 S'
_chemical_formula_weight         439.51
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-05-19 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_c                   22.0104(8)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      66.5949
_cell_measurement_theta_min      3.2955
_cell_volume                     2139.34(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
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_diffrn_measured_fraction_theta_max 1.000
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_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
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_diffrn_reflns_limit_k_min       -20
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_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         3.295
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.589
_exptl_absorpt_correction_T_max  0.93
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
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_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1498 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0349P)^2^+0.3493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0633
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3662
_reflns_number_total             3770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00886a2.cif
_cod_data_source_block           vd1225_vesely
_cod_database_code               1555111
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.566
_shelx_estimated_absorpt_t_max   0.925
_shelx_res_checksum              38277
_shelx_hkl_checksum              5909