Asymmetric Construction of Spiro[thiopyranoindole-benzoisothiazole] Scaffold via a Formal [3 + 3] Spiroannulation.
Chen, Xiang; Zhang, Jun-Qi; Yin, Shao-Jie; Li, Hai-Yan; Zhou, Wei-Qun; Wang, Xing-Wang; Organic letters 17 (2015) 4188–4191; doi:10.1021/acs.orglett.5b01951

data_1555183
_publ_section_title
;
 Asymmetric Construction of Spiro[thiopyranoindole-benzoisothiazole]
 Scaffold via a Formal [3 + 3] Spiroannulation.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4188
_journal_page_last               4191
_journal_paper_doi               10.1021/acs.orglett.5b01951
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C48 H38 Cl2 N4 O4 S4'
_chemical_formula_sum            'C48 H38 Cl2 N4 O4 S4'
_chemical_formula_weight         933.96
_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
_audit_creation_date             2015-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.652(2)
_cell_length_b                   19.153(4)
_cell_length_c                   22.403(4)
_cell_measurement_reflns_used    2883
_cell_measurement_temperature    130
_cell_measurement_theta_max      19.512
_cell_measurement_theta_min      2.31
_cell_volume                     5428.8(17)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.1227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            35619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.331
_diffrn_reflns_theta_min         1.818
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1058 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.6808.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       plate
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2137 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         12195
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0654P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6515
_reflns_number_total             12195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01951_si_003.cif
_cod_data_source_block           mo_dm15331_0m
_cod_original_cell_volume        5429.1(18)
_cod_database_code               1555183
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C9(H9), C34(H34)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C41(H41A,H41B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14),
  C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C28(H28), C29(H29),
 C30(H30), C31(H31), C36(H36), C38(H38), C39(H39), C40(H40), C44(H44), C45(H45),
  C46(H46), C47(H47)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              2063
_shelx_hkl_checksum              44019
_olex2_submission_special_instructions 'No special instructions were received'