#------------------------------------------------------------------------------
#$Date: 2024-01-06 11:31:03 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159651.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_7159651
loop_
_publ_author_name
'Dahiya, Pooja'
'Yadav, Anoop'
'Peddinti, Rama Krishna'
_publ_section_title
;
 Spirocyclization and Michael addition of 3-benzylidene succinimides:
 route to spirocyclopentapyrrolidine-tetraones and benzylidene
 N-arylpyrrolidine-diones.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9192
_journal_page_last               9199
_journal_paper_doi               10.1039/d3ob01629c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C33 H23 N O5 S'
_chemical_formula_sum            'C33 H22 N O5 S'
_chemical_formula_weight         544.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2022-12-17 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                114.144(6)
_cell_angle_beta                 108.931(7)
_cell_angle_gamma                92.315(7)
_cell_formula_units_Z            2
_cell_length_a                   10.988(2)
_cell_length_b                   11.648(2)
_cell_length_c                   12.588(3)
_cell_measurement_reflns_used    9083
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.19
_cell_volume                     1362.4(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      250.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46666
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.000
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0903 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9443.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       cubic
_exptl_crystal_F_000             566
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0915P)²+0.9165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1770
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4133
_reflns_number_total             4779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01629c2.cif
_cod_data_source_block           mo_jrk_pd_51a_0m
_cod_depositor_comments
'Adding full bibliography for 7159651--7159652.cif.'
_cod_database_code               7159651
_shelx_shelxl_version_number     2018/3
_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:
 C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C1(H1)
2.c Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.65678(11) 0.23482(11) 0.61297(11) 0.0913(4) Uani 1 1 d . . . . .
O1 O 0.6586(2) 0.56955(18) 0.26412(19) 0.0693(6) Uani 1 1 d . . . . .
O2 O 0.7185(2) 0.17853(17) 0.24555(18) 0.0646(6) Uani 1 1 d . . . . .
O3 O 0.9242(2) 0.77130(19) 0.5888(2) 0.0781(7) Uani 1 1 d . . . . .
O4 O 1.00823(17) 0.5639(2) 0.69494(18) 0.0629(6) Uani 1 1 d . . . . .
O5 O 0.56407(17) 0.5435(2) 0.65299(18) 0.0605(5) Uani 1 1 d . . . . .
N1 N 0.67116(19) 0.35999(17) 0.22323(17) 0.0362(4) Uani 1 1 d . . . . .
C1 C 0.7011(3) 0.4926(2) 0.2987(2) 0.0423(5) Uani 1 1 d . . . . .
C2 C 0.7946(2) 0.5197(2) 0.4272(2) 0.0374(5) Uani 1 1 d . . . . .
H00H H 0.882657 0.561426 0.441713 0.045 Uiso 1 1 calc R . . . .
C3 C 0.7514(2) 0.6023(2) 0.5340(2) 0.0375(5) Uani 1 1 d . . . . .
H00A H 0.657036 0.603162 0.498074 0.045 Uiso 1 1 calc R . . . .
C4 C 0.7689(2) 0.5294(2) 0.6163(2) 0.0387(5) Uani 1 1 d . . . . .
C5 C 0.7314(2) 0.3855(2) 0.5136(2) 0.0381(5) Uani 1 1 d . . . . .
H00G H 0.635677 0.366351 0.465545 0.046 Uiso 1 1 calc R . . . .
C6 C 0.8006(2) 0.3888(2) 0.4258(2) 0.0370(5) Uani 1 1 d . . . . .
H00D H 0.892612 0.378550 0.456396 0.044 Uiso 1 1 calc R . . . .
C7 C 0.7280(2) 0.2930(2) 0.2906(2) 0.0404(5) Uani 1 1 d . . . . .
C8 C 0.8290(2) 0.7404(2) 0.6059(2) 0.0446(6) Uani 1 1 d . . . . .
C9 C 0.7871(3) 0.8356(2) 0.7019(2) 0.0446(6) Uani 1 1 d . . . . .
C10 C 0.8825(3) 0.9327(3) 0.8078(3) 0.0611(8) Uani 1 1 d . . . . .
H00U H 0.971687 0.936909 0.818950 0.073 Uiso 1 1 calc R . . . .
C11 C 0.8445(5) 1.0244(3) 0.8979(3) 0.0819(12) Uani 1 1 d . . . . .
H00Y H 0.908440 1.089001 0.971612 0.098 Uiso 1 1 calc R . . . .
C12 C 0.7132(5) 1.0200(4) 0.8784(4) 0.0830(12) Uani 1 1 d . . . . .
H013 H 0.688323 1.081907 0.939435 0.100 Uiso 1 1 calc R . . . .
C13 C 0.6194(4) 0.9279(3) 0.7729(4) 0.0735(10) Uani 1 1 d . . . . .
H00Z H 0.530141 0.928186 0.759338 0.088 Uiso 1 1 calc R . . . .
C14 C 0.6554(3) 0.8336(3) 0.6854(3) 0.0563(7) Uani 1 1 d . . . . .
H00T H 0.590437 0.767472 0.614023 0.068 Uiso 1 1 calc R . . . .
C15 C 0.9077(2) 0.5636(2) 0.7146(2) 0.0421(5) Uani 1 1 d . . . . .
C16 C 0.8974(2) 0.5970(2) 0.8376(2) 0.0420(5) Uani 1 1 d . . . . .
C17 C 0.9977(3) 0.6332(3) 0.9533(3) 0.0559(7) Uani 1 1 d . . . . .
H00Q H 1.086336 0.640721 0.962139 0.067 Uiso 1 1 calc R . . . .
C18 C 0.9616(4) 0.6578(3) 1.0548(3) 0.0685(9) Uani 1 1 d . . . . .
H00X H 1.027060 0.682811 1.134438 0.082 Uiso 1 1 calc R . . . .
C19 C 0.8316(4) 0.6463(3) 1.0416(3) 0.0687(9) Uani 1 1 d . . . . .
H011 H 0.810632 0.663508 1.112657 0.082 Uiso 1 1 calc R . . . .
C20 C 0.7313(3) 0.6103(3) 0.9272(3) 0.0546(7) Uani 1 1 d . . . . .
H00R H 0.642776 0.601645 0.918842 0.066 Uiso 1 1 calc R . . . .
C21 C 0.7664(2) 0.5872(2) 0.8249(2) 0.0418(5) Uani 1 1 d . . . . .
C22 C 0.6818(2) 0.5527(2) 0.6943(2) 0.0417(5) Uani 1 1 d . . . . .
C23 C 0.7593(3) 0.2858(2) 0.5596(2) 0.0476(6) Uani 1 1 d . . . . .
C24 C 0.8708(3) 0.2186(2) 0.5650(2) 0.0441(6) Uani 1 1 d . . . . .
H1 H 0.941702 0.232193 0.542437 0.053 Uiso 1 1 calc R . . . .
C25 C 0.8498(5) 0.1286(3) 0.6115(3) 0.0808(11) Uani 1 1 d . . . . .
H012 H 0.907200 0.072662 0.620880 0.097 Uiso 1 1 calc R . . . .
C26 C 0.7445(5) 0.1299(3) 0.6400(3) 0.0838(12) Uani 1 1 d . . . . .
H010 H 0.721133 0.076593 0.672607 0.101 Uiso 1 1 calc R . . . .
C27 C 0.5908(2) 0.2999(2) 0.0924(2) 0.0388(5) Uani 1 1 d . . . . .
C28 C 0.4945(3) 0.1918(2) 0.0436(2) 0.0505(6) Uani 1 1 d . . . . .
H00N H 0.482886 0.157064 0.096008 0.061 Uiso 1 1 calc R . . . .
C29 C 0.4155(3) 0.1355(3) -0.0823(3) 0.0616(8) Uani 1 1 d . . . . .
H00S H 0.350442 0.062023 -0.115195 0.074 Uiso 1 1 calc R . . . .
C30 C 0.4309(3) 0.1858(3) -0.1612(3) 0.0646(8) Uani 1 1 d . . . . .
C31 C 0.5264(3) 0.2935(3) -0.1107(3) 0.0633(8) Uani 1 1 d . . . . .
H00W H 0.537002 0.329452 -0.162568 0.076 Uiso 1 1 calc R . . . .
C32 C 0.6073(3) 0.3503(3) 0.0152(2) 0.0492(6) Uani 1 1 d . . . . .
H00O H 0.673273 0.422935 0.047712 0.059 Uiso 1 1 calc R . . . .
C33 C 0.3432(5) 0.1230(4) -0.2994(3) 0.1044(16) Uani 1 1 d . . . . .
H01A H 0.395451 0.087168 -0.349542 0.157 Uiso 1 1 calc GR . . . .
H01B H 0.302422 0.186678 -0.321331 0.157 Uiso 1 1 calc GR . . . .
H01C H 0.275623 0.055010 -0.315740 0.157 Uiso 1 1 calc GR . . . .
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
C26 S1 C23 93.47(19) . . ?
C1 N1 C7 112.22(19) . . ?
C1 N1 C27 123.81(19) . . ?
C7 N1 C27 123.97(18) . . ?
O1 C1 N1 124.7(2) . . ?
O1 C1 C2 126.9(2) . . ?
N1 C1 C2 108.37(19) . . ?
C1 C2 C3 114.34(19) . . ?
C1 C2 C6 105.29(18) . . ?
C6 C2 C3 108.46(18) . . ?
C2 C3 C4 104.42(18) . . ?
C8 C3 C2 112.17(19) . . ?
C8 C3 C4 113.72(19) . . ?
C3 C4 C5 101.38(17) . . ?
C15 C4 C3 113.65(19) . . ?
C15 C4 C5 112.49(19) . . ?
C15 C4 C22 103.22(19) . . ?
C22 C4 C3 116.0(2) . . ?
C22 C4 C5 110.39(18) . . ?
C6 C5 C4 102.77(17) . . ?
C23 C5 C4 116.82(19) . . ?
C23 C5 C6 115.2(2) . . ?
C2 C6 C5 104.92(18) . . ?
C7 C6 C2 105.03(18) . . ?
C7 C6 C5 113.44(19) . . ?
O2 C7 N1 124.5(2) . . ?
O2 C7 C6 127.3(2) . . ?
N1 C7 C6 108.22(18) . . ?
O3 C8 C3 121.4(2) . . ?
O3 C8 C9 120.4(2) . . ?
C9 C8 C3 118.2(2) . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 C14 119.5(3) . . ?
C14 C9 C8 122.0(2) . . ?
C9 C10 C11 119.2(3) . . ?
C12 C11 C10 119.9(3) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 C14 119.7(4) . . ?
C13 C14 C9 120.5(3) . . ?
O4 C15 C4 125.8(2) . . ?
O4 C15 C16 126.0(2) . . ?
C16 C15 C4 108.2(2) . . ?
C17 C16 C15 128.6(2) . . ?
C17 C16 C21 121.3(2) . . ?
C21 C16 C15 110.1(2) . . ?
C18 C17 C16 117.2(3) . . ?
C19 C18 C17 121.3(3) . . ?
C18 C19 C20 121.9(3) . . ?
C19 C20 C21 117.2(3) . . ?
C16 C21 C22 110.0(2) . . ?
C20 C21 C16 120.9(2) . . ?
C20 C21 C22 129.1(2) . . ?
O5 C22 C4 124.8(2) . . ?
O5 C22 C21 126.9(2) . . ?
C21 C22 C4 108.3(2) . . ?
C5 C23 S1 120.8(2) . . ?
C24 C23 S1 110.87(19) . . ?
C24 C23 C5 128.3(2) . . ?
C25 C24 C23 106.7(3) . . ?
C26 C25 C24 115.3(3) . . ?
C25 C26 S1 113.6(3) . . ?
C28 C27 N1 119.9(2) . . ?
C32 C27 N1 120.2(2) . . ?
C32 C27 C28 119.9(2) . . ?
C29 C28 C27 119.7(3) . . ?
C28 C29 C30 121.0(3) . . ?
C29 C30 C33 120.4(3) . . ?
C31 C30 C29 118.4(3) . . ?
C31 C30 C33 121.2(3) . . ?
C30 C31 C32 121.3(3) . . ?
C27 C32 C31 119.8(3) . . ?
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
S1 C23 1.684(3) . ?
S1 C26 1.661(4) . ?
O1 C1 1.197(3) . ?
O2 C7 1.201(3) . ?
O3 C8 1.204(3) . ?
O4 C15 1.208(3) . ?
O5 C22 1.210(3) . ?
N1 C1 1.397(3) . ?
N1 C7 1.398(3) . ?
N1 C27 1.430(3) . ?
C1 C2 1.500(3) . ?
C3 C2 1.534(3) . ?
C3 C4 1.560(3) . ?
C3 C8 1.526(3) . ?
C4 C5 1.574(3) . ?
C4 C15 1.529(3) . ?
C4 C22 1.537(3) . ?
C5 C23 1.497(3) . ?
C6 C2 1.522(3) . ?
C6 C5 1.542(3) . ?
C7 C6 1.508(3) . ?
C8 C9 1.486(3) . ?
C9 C10 1.385(4) . ?
C9 C14 1.391(4) . ?
C10 C11 1.397(5) . ?
C11 C12 1.378(6) . ?
C13 C12 1.354(6) . ?
C14 C13 1.380(4) . ?
C16 C15 1.479(3) . ?
C16 C17 1.390(4) . ?
C16 C21 1.391(3) . ?
C17 C18 1.382(5) . ?
C18 C19 1.378(5) . ?
C20 C19 1.380(4) . ?
C21 C20 1.388(4) . ?
C22 C21 1.472(3) . ?
C23 C24 1.478(4) . ?
C25 C24 1.437(4) . ?
C26 C25 1.317(6) . ?
C27 C28 1.385(4) . ?
C27 C32 1.377(4) . ?
C28 C29 1.381(4) . ?
C29 C30 1.391(5) . ?
C30 C31 1.374(5) . ?
C30 C33 1.518(4) . ?
C32 C31 1.386(4) . ?
