#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157981.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7157981
loop_
_publ_author_name
'Lei, Lu'
'Liang, Yu-Feng'
'Liang, Cui'
'Qin, Jiang-Ke'
'Pan, Cheng-Xue'
'Su, Gui-Fa'
'Mo, Dong-Liang'
_publ_section_title
;
 Copper(I)-catalyzed [4 + 2] cycloaddition of aza-ortho-quinone
 methides with bicyclic alkenes.
;
_journal_issue                   15
_journal_name_full               'Organic & 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       'φ and ω 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
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.906
_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/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S0A S 0.41732(3) 0.07188(7) 0.35400(2) 0.0449(2) Uani 1 1 d . . . . .
C8AA C 0.41471(15) 0.5304(3) 0.46817(11) 0.0548(7) Uani 1 1 d . . . . .
H8AA H 0.4383 0.6219 0.4750 0.066 Uiso 1 1 calc R . . . .
N N 0.38562(10) 0.2460(2) 0.35670(8) 0.0418(5) Uani 1 1 d . . . . .
C2AA C 0.50236(13) 0.0860(3) 0.37735(10) 0.0417(5) Uani 1 1 d . . . . .
C3AA C 0.41966(12) 0.4546(3) 0.41824(10) 0.0419(5) Uani 1 1 d . . . . .
C0AA C 0.38296(12) 0.3469(3) 0.30791(10) 0.0406(5) Uani 1 1 d . . . . .
H0AA H 0.3991 0.2914 0.2766 0.049 Uiso 1 1 calc R . . . .
C4AA C 0.34386(12) 0.6228(3) 0.24935(10) 0.0438(6) Uani 1 1 d . . . . .
C5AA C 0.55190(15) 0.0927(3) 0.34027(11) 0.0526(7) Uani 1 1 d . . . . .
H5AA H 0.5405 0.0896 0.3029 0.063 Uiso 1 1 calc R . . . .
C6AA C 0.30905(13) 0.4849(3) 0.23953(10) 0.0470(6) Uani 1 1 d . . . . .
C C 0.38237(12) 0.3193(3) 0.40898(9) 0.0403(5) Uani 1 1 d . . . . .
C3CA C 0.34014(15) 0.3383(4) 0.49769(11) 0.0597(7) Uani 1 1 d . . . . .
H3CA H 0.3144 0.2984 0.5246 0.072 Uiso 1 1 calc R . . . .
C9AA C 0.34235(13) 0.2621(3) 0.44826(10) 0.0494(6) Uani 1 1 d . . . . .
H9AA H 0.3171 0.1730 0.4415 0.059 Uiso 1 1 calc R . . . .
C0BA C 0.28335(15) 0.4435(4) 0.18799(12) 0.0573(7) Uani 1 1 d . . . . .
H0BA H 0.2602 0.3511 0.1818 0.069 Uiso 1 1 calc R . . . .
C1BA C 0.61823(16) 0.1041(3) 0.35986(12) 0.0589(7) Uani 1 1 d . . . . .
H1BA H 0.6513 0.1093 0.3350 0.071 Uiso 1 1 calc R . . . .
C2BA C 0.29371(16) 0.5472(4) 0.14515(11) 0.0601(8) Uani 1 1 d . . . . .
H2BA H 0.2766 0.5242 0.1099 0.072 Uiso 1 1 calc R . . . .
C1AA C 0.42263(12) 0.5017(3) 0.31796(10) 0.0406(5) Uani 1 1 d . . . . .
H1AA H 0.4536 0.5155 0.2890 0.049 Uiso 1 1 calc R . . . .
C3BA C 0.35568(14) 0.7230(3) 0.20725(11) 0.0551(7) Uani 1 1 d . . . . .
H3BA H 0.3803 0.8134 0.2134 0.066 Uiso 1 1 calc R . . . .
C7AA C 0.46274(12) 0.5069(3) 0.37394(11) 0.0459(6) Uani 1 1 d . . . . .
H7AA H 0.4991 0.4312 0.3725 0.055 Uiso 1 1 calc R . . . .
C4BA C 0.51992(15) 0.0898(3) 0.43309(11) 0.0520(6) Uani 1 1 d . . . . .
H4BA H 0.4868 0.0847 0.4579 0.062 Uiso 1 1 calc R . . . .
C5BA C 0.63748(15) 0.1083(3) 0.41510(12) 0.0538(7) Uani 1 1 d . . . . .
C6BA C 0.32898(16) 0.6824(4) 0.15496(11) 0.0616(8) Uani 1 1 d . . . . .
H6BA H 0.3353 0.7489 0.1260 0.074 Uiso 1 1 calc R . . . .
C7BA C 0.37586(16) 0.4725(4) 0.50717(11) 0.0613(8) Uani 1 1 d . . . . .
H7BA H 0.3736 0.5243 0.5402 0.074 Uiso 1 1 calc R . . . .
C8BA C 0.58641(15) 0.1012(3) 0.45163(11) 0.0563(7) Uani 1 1 d . . . . .
H8BA H 0.5977 0.1042 0.4890 0.068 Uiso 1 1 calc R . . . .
C0CA C 0.49562(16) 0.6632(3) 0.38401(15) 0.0683(9) Uani 1 1 d . . . . .
H0CA H 0.4619 0.7385 0.3910 0.102 Uiso 1 1 calc GR . . . .
H0CB H 0.5182 0.6934 0.3524 0.102 Uiso 1 1 calc GR . . . .
H0CC H 0.5275 0.6566 0.4150 0.102 Uiso 1 1 calc GR . . . .
C1CA C 0.31112(13) 0.4065(3) 0.29483(11) 0.0481(6) Uani 1 1 d . . . . .
H1CA H 0.2757 0.3296 0.2989 0.058 Uiso 1 1 calc R . . . .
C2CA C 0.36483(13) 0.6202(3) 0.30972(10) 0.0453(6) Uani 1 1 d . . . . .
H2CA H 0.3741 0.7219 0.3262 0.054 Uiso 1 1 calc R . . . .
O O 0.30908(9) 0.5377(2) 0.33084(7) 0.0511(5) Uani 1 1 d . . . . .
O1 O 0.41368(11) 0.0280(2) 0.29779(8) 0.0594(5) Uani 1 1 d . . . . .
O2 O 0.38518(11) -0.0210(2) 0.39287(8) 0.0584(5) Uani 1 1 d . . . . .
C1 C 0.7101(2) 0.1206(5) 0.43639(16) 0.0805(10) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N S0A C2AA 106.89(11) . . ?
O1 S0A N 106.82(11) . . ?
O1 S0A C2AA 108.51(13) . . ?
O2 S0A N 107.25(11) . . ?
O2 S0A C2AA 106.75(12) . . ?
O2 S0A O1 119.97(13) . . ?
C7BA C8AA C3AA 121.3(3) . . ?
C0AA N S0A 120.13(15) . . ?
C N S0A 118.90(15) . . ?
C N C0AA 117.51(18) . . ?
C5AA C2AA S0A 120.2(2) . . ?
C5AA C2AA C4BA 120.1(2) . . ?
C4BA C2AA S0A 119.7(2) . . ?
C8AA C3AA C7AA 124.9(2) . . ?
C C3AA C8AA 117.8(2) . . ?
C C3AA C7AA 117.4(2) . . ?
N C0AA C1AA 112.74(19) . . ?
N C0AA C1CA 110.35(19) . . ?
C1CA C0AA C1AA 101.59(19) . . ?
C6AA C4AA C3BA 121.1(2) . . ?
C6AA C4AA C2CA 105.0(2) . . ?
C3BA C4AA C2CA 133.9(3) . . ?
C1BA C5AA C2AA 118.9(2) . . ?
C4AA C6AA C0BA 122.0(2) . . ?
C4AA C6AA C1CA 104.2(2) . . ?
C0BA C6AA C1CA 133.8(3) . . ?
C3AA C N 117.3(2) . . ?
C3AA C C9AA 120.8(2) . . ?
C9AA C N 121.9(2) . . ?
C7BA C3CA C9AA 120.2(3) . . ?
C3CA C9AA C 119.7(3) . . ?
C6AA C0BA C2BA 117.1(3) . . ?
C5AA C1BA C5BA 122.6(3) . . ?
C6BA C2BA C0BA 120.6(3) . . ?
C7AA C1AA C0AA 113.02(19) . . ?
C2CA C1AA C0AA 100.44(19) . . ?
C2CA C1AA C7AA 115.7(2) . . ?
C4AA C3BA C6BA 117.1(3) . . ?
C3AA C7AA C1AA 110.4(2) . . ?
C3AA C7AA C0CA 114.4(2) . . ?
C0CA C7AA C1AA 111.3(2) . . ?
C8BA C4BA C2AA 120.0(3) . . ?
C1BA C5BA C1 122.4(3) . . ?
C8BA C5BA C1BA 117.4(3) . . ?
C8BA C5BA C1 120.2(3) . . ?
C2BA C6BA C3BA 122.0(3) . . ?
C8AA C7BA C3CA 120.2(3) . . ?
C4BA C8BA C5BA 121.2(3) . . ?
C6AA C1CA C0AA 107.7(2) . . ?
O C1CA C0AA 101.59(19) . . ?
O C1CA C6AA 101.4(2) . . ?
C4AA C2CA C1AA 107.0(2) . . ?
O C2CA C4AA 101.0(2) . . ?
O C2CA C1AA 102.21(19) . . ?
C2CA O C1CA 96.53(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S0A N 1.636(2) . ?
S0A C2AA 1.758(3) . ?
S0A O1 1.4281(19) . ?
S0A O2 1.432(2) . ?
C8AA C3AA 1.399(3) . ?
C8AA C7BA 1.367(4) . ?
N C0AA 1.479(3) . ?
N C 1.437(3) . ?
C2AA C5AA 1.390(4) . ?
C2AA C4BA 1.389(3) . ?
C3AA C 1.397(3) . ?
C3AA C7AA 1.501(4) . ?
C0AA C1AA 1.566(3) . ?
C0AA C1CA 1.536(3) . ?
C4AA C6AA 1.393(4) . ?
C4AA C3BA 1.381(3) . ?
C4AA C2CA 1.512(3) . ?
C5AA C1BA 1.380(4) . ?
C6AA C0BA 1.379(4) . ?
C6AA C1CA 1.515(3) . ?
C C9AA 1.385(3) . ?
C3CA C9AA 1.384(4) . ?
C3CA C7BA 1.374(5) . ?
C0BA C2BA 1.408(4) . ?
C1BA C5BA 1.384(4) . ?
C2BA C6BA 1.377(5) . ?
C1AA C7AA 1.543(3) . ?
C1AA C2CA 1.546(3) . ?
C3BA C6BA 1.400(4) . ?
C7AA C0CA 1.514(4) . ?
C4BA C8BA 1.376(4) . ?
C5BA C8BA 1.404(4) . ?
C5BA C1 1.510(5) . ?
C1CA O 1.440(3) . ?
C2CA O 1.447(3) . ?
