Asymmetric sequential annulation/aldol process of 4-isothiocyanato pyrazolones and allenones: access to novel spiro[pyrrole-pyrazolones] and spiro[thiopyranopyrrole-pyrazolones].
Wang, Wenyao; Bao, Xiaoze; Wei, Shiqiang; Nawaz, Shah; Qu, Jingping; Wang, Baomin; Chemical communications (Cambridge, England) 57 (2021) 363–366; doi:10.1039/d0cc07113g

data_7127556
_publ_section_title
;
 Asymmetric sequential annulation/aldol process of 4-isothiocyanato
 pyrazolones and allenones: access to novel spiro[pyrrole-pyrazolones] and
 spiro[thiopyranopyrrole-pyrazolones].
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              363
_journal_page_last               366
_journal_paper_doi               10.1039/d0cc07113g
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration s
_chemical_formula_moiety         'C36 H25 Br2 N3 O3 S'
_chemical_formula_sum            'C36 H25 Br2 N3 O3 S'
_chemical_formula_weight         739.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2020-10-24 deposited with the CCDC.	2020-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.503(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.5755(11)
_cell_length_b                   10.6535(9)
_cell_length_c                   13.6818(12)
_cell_measurement_reflns_used    6753
_cell_measurement_temperature    297.0
_cell_measurement_theta_max      22.414
_cell_measurement_theta_min      2.525
_cell_volume                     1654.4(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28869
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         2.525
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.553
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6380
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1217 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.8557.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1340
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0185P)^2^+0.3811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4193
_reflns_number_total             7582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07113g2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7127555--7127556.cif.'
_cod_database_code               7127556
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.749
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C00O(H00O), C22(H22), C25(H25), C2(H2A), C12(H12), C8(H8), C1(H1),
 C11(H11), C5(H5), C24(H24), C9(H9), C30(H30), C34(H34), C3(H3), C31(H31),
 C21(H21), C10(H10), C33(H33)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              5534
_olex2_submission_special_instructions 'No special instructions were received'