Organocatalytic [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates.
Cheng, Yu-Chun; Wang, Cong-Shuai; Li, Tian-Zhen; Gao, Feng; Jiao, Yinchun; Shi, Feng; Organic & biomolecular chemistry 17 (2019) 6662–6670; doi:10.1039/c9ob00918c

data_7156922
_publ_section_title
;
 Organocatalytic [4 + 2] cyclizations of para-quinone methide derivatives
 with isocyanates.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6662
_journal_page_last               6670
_journal_paper_doi               10.1039/c9ob00918c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C29 H33 N O5 S'
_chemical_formula_sum            'C29 H33 N O5 S'
_chemical_formula_weight         507.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-04-14 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.2440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9129(11)
_cell_length_b                   13.7709(13)
_cell_length_c                   18.7714(18)
_cell_measurement_reflns_used    4596
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.54
_cell_measurement_theta_min      2.404
_cell_volume                     2756.8(5)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16031
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.404
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0464 before and 0.0369 after correction.
The Ratio of minimum to maximum transmission is 0.9158.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1035P)^2^+0.5857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4095
_reflns_number_total             6186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00918c2.cif
_cod_data_source_block           sf20180426_1_0m
_cod_depositor_comments          'Adding full bibliography for 7156922.cif.'
_cod_database_code               7156922
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H3-H17A
 2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C14(H14), C24(H24), C25(H25),
 C27(H27), C28(H28)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C29(H29A,H29B,H29C)
3.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              81111
_olex2_submission_special_instructions 'No special instructions were received'