Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines.
Yang, Mengchen; Chen, Chen; Yi, Xing; Li, Yuan; Wu, Xiaoqin; Li, Qingshan; Ban, Shurong; Organic & biomolecular chemistry 17 (2019) 2883–2886; doi:10.1039/c9ob00330d

data_7156694
_publ_section_title
;
 Thiosquaramide-catalysed asymmetric double Michael addition of
 2-(3H)-furanones to nitroolefines.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2883
_journal_page_last               2886
_journal_paper_doi               10.1039/c9ob00330d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         '0.5(C21 H20 N2 O7)'
_chemical_formula_sum            'C10.5 H10 N O3.5'
_chemical_formula_weight         206.19
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-30 deposited with the CCDC.    2019-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.396(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5334(7)
_cell_length_b                   16.5353(19)
_cell_length_c                   9.6045(11)
_cell_measurement_reflns_used    6917
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      36.71
_cell_measurement_theta_min      3.70
_cell_volume                     1023.7(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.05
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7216
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         4.104
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0793 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.9024.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       Block
_exptl_crystal_F_000             432
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1456 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0663
_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^)+(0.1051P)^2^+0.5531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1842
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                3325
_reflns_number_total             3446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00330d2.cif
_cod_data_source_block           mo_180912a_0m
_cod_depositor_comments          'Adding full bibliography for 7156694.cif.'
_cod_original_formula_sum        'C10.50 H10 N O3.50'
_cod_database_code               7156694
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details   SADABS
_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
2. Uiso/Uaniso restraints and constraints
Uanis(O00T) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C008(H008), C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00B), C00I(H00G,H00I)
3.c Aromatic/amide H refined with riding coordinates:
 C004(H004), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S)
3.d Idealised Me refined as rotating group:
 C00F(H00C,H00E,H00F)
;
_shelx_res_checksum              36426
_olex2_submission_special_instructions 'No special instructions were received'