Copper(I)-catalyzed [4 + 2] cycloaddition of aza-<i>ortho</i>-quinone methides with bicyclic alkenes.
Lei, Lu; Liang, Yu-Feng; Liang, Cui; Qin, Jiang-Ke; Pan, Cheng-Xue; Su, Gui-Fa; Mo, Dong-Liang; Organic & biomolecular chemistry 19 (2021) 3379–3383; doi:10.1039/d1ob00319d

data_7157981
_publ_section_title
;
 Copper(I)-catalyzed [4 + 2] cycloaddition of aza-<i>ortho</i>-quinone
 methides with bicyclic alkenes.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3379
_journal_page_last               3383
_journal_paper_doi               10.1039/d1ob00319d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C25 H20 N O3 S'
_chemical_formula_sum            'C25 H20 N O3 S'
_chemical_formula_weight         414.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-29 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.934(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.956(3)
_cell_length_b                   8.6435(12)
_cell_length_c                   24.548(3)
_cell_measurement_reflns_used    5342
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.55
_cell_volume                     4224.3(10)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            27754
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.705
_diffrn_reflns_theta_min         1.663
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.180
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_exptl_crystal_colour            white
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_exptl_crystal_description       block
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0527
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.2374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3420
_reflns_number_total             4950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00319d2.cif
_cod_data_source_block           aaaa_CCDC1
_cod_depositor_comments
;
Adding full bibliography for 7157980--7157981.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C3.85 H3.23 N0.15 O0.46 S0.15'
_cod_original_formula_weight         63.92
_cod_original_formula_moiety         '0.15(C25 H20 N O3 S)'
_cod_original_formula_units_Z            52
_cod_database_code               7157981
_shelx_shelxl_version_number     2014/7
_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
2.a Ternary CH refined with riding coordinates:
 C0AA(H0AA), C1AA(H1AA), C7AA(H7AA), C1CA(H1CA), C2CA(H2CA)
2.b Aromatic/amide H refined with riding coordinates:
 C8AA(H8AA), C5AA(H5AA), C3CA(H3CA), C9AA(H9AA), C0BA(H0BA), C1BA(H1BA),
 C2BA(H2BA), C3BA(H3BA), C4BA(H4BA), C6BA(H6BA), C7BA(H7BA), C8BA(H8BA)
2.c Idealised Me refined as rotating group:
 C0CA(H0CA,H0CB,H0CC)
;
_shelx_res_checksum              58856
_olex2_submission_special_instructions 'No special instructions were received'