#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/07/4030781.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_4030781
loop_
_publ_author_name
'Mal, Kanchan'
'Das, Supriya'
'Maiti, Nakul C.'
'Natarajan, Ramalingam'
'Das, Indrajit'
_publ_section_title
;
 ZnI2-Catalyzed Diastereoselective [4 + 2] Cycloadditions of
 β,γ-Unsaturated α-Ketothioesters with Olefins.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2972
_journal_page_last               2988
_journal_paper_doi               10.1021/jo5024766
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C26 H25 N O2'
_chemical_formula_sum            'C26 H25 N O2'
_chemical_formula_weight         383.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.098(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6199(11)
_cell_length_b                   18.4852(15)
_cell_length_c                   10.2680(10)
_cell_measurement_reflns_used    3605
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.34
_cell_measurement_theta_min      2.20
_cell_volume                     2156.5(3)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.787
_diffrn_measured_fraction_theta_max 0.765
_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  0.0431
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.787
_diffrn_reflns_Laue_measured_fraction_max 0.765
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13103
_diffrn_reflns_point_group_measured_fraction_full 0.787
_diffrn_reflns_point_group_measured_fraction_max 0.765
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.363
_diffrn_reflns_theta_min         1.792
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.708842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0817 before and 0.0398 after correction.
The Ratio of minimum to maximum transmission is 0.7088.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0499
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2068
_reflns_number_total             3742
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5024766_si_009.cif
_cod_data_source_block           km_395
_cod_depositor_comments
'Adding full bibliography for 4030777--4030784.cif.'
_cod_database_code               4030781
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014/6
_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, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.61608(13) 0.64049(6) 0.30850(16) 0.0494(5) Uani 1 1 d .
O2 O 0.51606(14) 0.70829(7) 0.58573(19) 0.0620(5) Uani 1 1 d .
N1 N 0.50231(14) 0.74972(8) 0.3746(2) 0.0502(6) Uani 1 1 d .
H1 H 0.5139 0.7396 0.2966 0.060 Uiso 1 1 calc R
C1 C 0.59668(19) 0.63560(9) 0.4355(2) 0.0418(6) Uani 1 1 d .
C2 C 0.62561(19) 0.57959(10) 0.5159(2) 0.0473(6) Uani 1 1 d .
H2 H 0.6108 0.5819 0.6013 0.057 Uiso 1 1 calc R
C3 C 0.6818(2) 0.51197(10) 0.4745(2) 0.0468(6) Uani 1 1 d .
H3 H 0.6196 0.4758 0.4488 0.056 Uiso 1 1 calc R
C4 C 0.7303(2) 0.52988(10) 0.3509(2) 0.0473(7) Uani 1 1 d .
H4A H 0.8022 0.5576 0.3774 0.057 Uiso 1 1 calc R
H4B H 0.7496 0.4852 0.3107 0.057 Uiso 1 1 calc R
C5 C 0.6432(2) 0.57285(9) 0.2476(2) 0.0451(6) Uani 1 1 d .
C006 C 0.53459(19) 0.70144(10) 0.4730(3) 0.0447(6) Uani 1 1 d .
C6 C 0.5261(2) 0.53323(12) 0.1985(3) 0.0617(8) Uani 1 1 d .
H6A H 0.4880 0.5259 0.2719 0.093 Uiso 1 1 calc GR
H6B H 0.5407 0.4873 0.1616 0.093 Uiso 1 1 calc GR
H6C H 0.4763 0.5618 0.1314 0.093 Uiso 1 1 calc GR
C7 C 0.7753(2) 0.47951(10) 0.5849(2) 0.0432(6) Uani 1 1 d .
C8 C 0.7587(2) 0.41079(11) 0.6341(3) 0.0619(8) Uani 1 1 d .
H8 H 0.6892 0.3857 0.6014 0.074 Uiso 1 1 calc R
C9 C 0.8459(3) 0.37961(14) 0.7319(3) 0.0779(10) Uani 1 1 d .
H9 H 0.8348 0.3338 0.7648 0.093 Uiso 1 1 calc R
C10 C 0.9478(3) 0.41668(16) 0.7793(3) 0.0818(10) Uani 1 1 d .
H10 H 1.0066 0.3958 0.8438 0.098 Uiso 1 1 calc R
C11 C 0.9637(3) 0.48451(15) 0.7321(3) 0.0756(9) Uani 1 1 d .
H11 H 1.0326 0.5099 0.7657 0.091 Uiso 1 1 calc R
C12 C 0.8783(2) 0.51487(12) 0.6358(3) 0.0597(8) Uani 1 1 d .
H12 H 0.8905 0.5607 0.6040 0.072 Uiso 1 1 calc R
C13 C 0.69922(19) 0.59460(11) 0.1320(2) 0.0483(6) Uani 1 1 d .
C14 C 0.7197(2) 0.54189(13) 0.0434(3) 0.0662(8) Uani 1 1 d .
H14 H 0.7018 0.4940 0.0583 0.079 Uiso 1 1 calc R
C15 C 0.7652(3) 0.55831(18) -0.0645(3) 0.0843(9) Uani 1 1 d .
H15 H 0.7779 0.5219 -0.1224 0.101 Uiso 1 1 calc R
C16 C 0.7925(3) 0.6284(2) -0.0879(3) 0.0869(10) Uani 1 1 d .
H16 H 0.8213 0.6398 -0.1633 0.104 Uiso 1 1 calc R
C17 C 0.7776(2) 0.68232(16) -0.0007(3) 0.0784(9) Uani 1 1 d .
H17 H 0.7984 0.7297 -0.0154 0.094 Uiso 1 1 calc R
C18 C 0.7308(2) 0.66510(12) 0.1101(3) 0.0614(8) Uani 1 1 d .
H18 H 0.7207 0.7013 0.1697 0.074 Uiso 1 1 calc R
C19 C 0.4479(2) 0.81900(10) 0.3956(3) 0.0627(8) Uani 1 1 d .
H19A H 0.4834 0.8568 0.3514 0.075 Uiso 1 1 calc R
H19B H 0.4649 0.8297 0.4902 0.075 Uiso 1 1 calc R
C20 C 0.3170(2) 0.82046(9) 0.3447(3) 0.0522(7) Uani 1 1 d .
C21 C 0.2689(3) 0.82411(12) 0.2096(3) 0.0642(8) Uani 1 1 d .
H21 H 0.3188 0.8258 0.1497 0.077 Uiso 1 1 calc R
C22 C 0.1498(3) 0.82529(13) 0.1624(3) 0.0754(9) Uani 1 1 d .
H22 H 0.1196 0.8277 0.0712 0.090 Uiso 1 1 calc R
C23 C 0.0748(3) 0.82295(14) 0.2493(5) 0.0858(10) Uani 1 1 d .
H23 H -0.0063 0.8234 0.2176 0.103 Uiso 1 1 calc R
C24 C 0.1210(4) 0.81996(17) 0.3839(5) 0.0965(11) Uani 1 1 d .
H24 H 0.0711 0.8187 0.4438 0.116 Uiso 1 1 calc R
C25 C 0.2417(3) 0.81886(13) 0.4306(3) 0.0778(9) Uani 1 1 d .
H25 H 0.2720 0.8170 0.5218 0.093 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C5 116.32(14)
C006 N1 H1 118.9
C006 N1 C19 122.2(2)
C19 N1 H1 118.9
O1 C1 C006 111.92(18)
C2 C1 O1 125.01(18)
C2 C1 C006 123.1(2)
C1 C2 H2 118.7
C1 C2 C3 122.7(2)
C3 C2 H2 118.7
C2 C3 H3 107.6
C2 C3 C4 108.06(16)
C2 C3 C7 113.60(19)
C4 C3 H3 107.6
C7 C3 H3 107.6
C7 C3 C4 112.04(18)
C3 C4 H4A 109.1
C3 C4 H4B 109.1
H4A C4 H4B 107.8
C5 C4 C3 112.59(18)
C5 C4 H4A 109.1
C5 C4 H4B 109.1
O1 C5 C4 108.61(17)
O1 C5 C6 107.01(17)
O1 C5 C13 105.87(15)
C4 C5 C6 113.13(18)
C13 C5 C4 110.49(18)
C13 C5 C6 111.4(2)
O2 C006 N1 124.41(19)
O2 C006 C1 120.9(2)
N1 C006 C1 114.7(2)
C5 C6 H6A 109.5
C5 C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6B 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C3 119.9(2)
C12 C7 C3 121.8(2)
C12 C7 C8 118.2(2)
C7 C8 H8 119.9
C9 C8 C7 120.2(3)
C9 C8 H8 119.9
C8 C9 H9 120.2
C10 C9 C8 119.6(3)
C10 C9 H9 120.2
C9 C10 H10 119.9
C9 C10 C11 120.3(3)
C11 C10 H10 119.9
C10 C11 H11 120.0
C12 C11 C10 120.0(3)
C12 C11 H11 120.0
C7 C12 H12 119.2
C11 C12 C7 121.7(2)
C11 C12 H12 119.2
C14 C13 C5 119.09(19)
C18 C13 C5 123.1(2)
C18 C13 C14 117.8(2)
C13 C14 H14 119.1
C15 C14 C13 121.9(3)
C15 C14 H14 119.1
C14 C15 H15 120.0
C14 C15 C16 119.9(3)
C16 C15 H15 120.0
C15 C16 H16 119.8
C15 C16 C17 120.5(3)
C17 C16 H16 119.8
C16 C17 H17 120.4
C16 C17 C18 119.3(3)
C18 C17 H17 120.4
C13 C18 C17 120.5(2)
C13 C18 H18 119.7
C17 C18 H18 119.7
N1 C19 H19A 108.8
N1 C19 H19B 108.8
N1 C19 C20 113.68(17)
H19A C19 H19B 107.7
C20 C19 H19A 108.8
C20 C19 H19B 108.8
C21 C20 C19 121.1(3)
C25 C20 C19 120.9(3)
C25 C20 C21 118.0(3)
C20 C21 H21 119.3
C22 C21 C20 121.5(3)
C22 C21 H21 119.3
C21 C22 H22 119.9
C21 C22 C23 120.2(3)
C23 C22 H22 119.9
C22 C23 H23 120.4
C22 C23 C24 119.1(3)
C24 C23 H23 120.4
C23 C24 H24 119.9
C23 C24 C25 120.2(3)
C25 C24 H24 119.9
C20 C25 C24 121.0(3)
C20 C25 H25 119.5
C24 C25 H25 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.372(2)
O1 C5 1.462(2)
O2 C006 1.227(3)
N1 H1 0.8600
N1 C006 1.342(3)
N1 C19 1.464(2)
C1 C2 1.323(3)
C1 C006 1.506(3)
C2 H2 0.9300
C2 C3 1.512(3)
C3 H3 0.9800
C3 C4 1.529(3)
C3 C7 1.519(3)
C4 H4A 0.9700
C4 H4B 0.9700
C4 C5 1.526(3)
C5 C6 1.535(3)
C5 C13 1.522(3)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C8 1.395(3)
C7 C12 1.368(3)
C8 H8 0.9300
C8 C9 1.394(4)
C9 H9 0.9300
C9 C10 1.366(4)
C10 H10 0.9300
C10 C11 1.371(4)
C11 H11 0.9300
C11 C12 1.367(4)
C12 H12 0.9300
C13 C14 1.387(3)
C13 C18 1.385(3)
C14 H14 0.9300
C14 C15 1.358(4)
C15 H15 0.9300
C15 C16 1.368(4)
C16 H16 0.9300
C16 C17 1.374(4)
C17 H17 0.9300
C17 C18 1.397(4)
C18 H18 0.9300
C19 H19A 0.9700
C19 H19B 0.9700
C19 C20 1.502(3)
C20 C21 1.384(4)
C20 C25 1.367(4)
C21 H21 0.9300
C21 C22 1.368(4)
C22 H22 0.9300
C22 C23 1.373(4)
C23 H23 0.9300
C23 C24 1.375(4)
C24 H24 0.9300
C24 C25 1.383(4)
C25 H25 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 -1.8(4)
O1 C1 C006 O2 -175.78(19)
O1 C1 C006 N1 4.5(3)
O1 C5 C13 C14 -171.1(2)
O1 C5 C13 C18 8.7(3)
N1 C19 C20 C21 -74.0(3)
N1 C19 C20 C25 106.6(2)
C1 O1 C5 C4 -43.2(2)
C1 O1 C5 C6 79.2(2)
C1 O1 C5 C13 -161.87(18)
C1 C2 C3 C4 16.9(3)
C1 C2 C3 C7 141.9(2)
C2 C1 C006 O2 5.8(3)
C2 C1 C006 N1 -173.9(2)
C2 C3 C4 C5 -45.4(2)
C2 C3 C7 C8 116.2(2)
C2 C3 C7 C12 -65.8(3)
C3 C4 C5 O1 59.6(2)
C3 C4 C5 C6 -59.0(2)
C3 C4 C5 C13 175.34(17)
C3 C7 C8 C9 177.7(2)
C3 C7 C12 C11 -177.9(2)
C4 C3 C7 C8 -121.0(2)
C4 C3 C7 C12 57.0(3)
C4 C5 C13 C14 71.5(3)
C4 C5 C13 C18 -108.7(2)
C5 O1 C1 C2 15.8(3)
C5 O1 C1 C006 -162.59(17)
C5 C13 C14 C15 177.5(2)
C5 C13 C18 C17 -177.4(2)
C006 N1 C19 C20 -102.2(3)
C006 C1 C2 C3 176.49(19)
C6 C5 C13 C14 -55.1(3)
C6 C5 C13 C18 124.6(2)
C7 C3 C4 C5 -171.26(17)
C7 C8 C9 C10 -0.1(4)
C8 C7 C12 C11 0.1(4)
C8 C9 C10 C11 0.8(4)
C9 C10 C11 C12 -1.1(4)
C10 C11 C12 C7 0.6(4)
C12 C7 C8 C9 -0.4(3)
C13 C14 C15 C16 0.2(5)
C14 C13 C18 C17 2.3(4)
C14 C15 C16 C17 2.0(5)
C15 C16 C17 C18 -2.0(4)
C16 C17 C18 C13 -0.2(4)
C18 C13 C14 C15 -2.3(4)
C19 N1 C006 O2 4.4(3)
C19 N1 C006 C1 -175.93(18)
C19 C20 C21 C22 179.84(18)
C19 C20 C25 C24 -179.8(2)
C20 C21 C22 C23 0.1(4)
C21 C20 C25 C24 0.8(3)
C21 C22 C23 C24 0.5(4)
C22 C23 C24 C25 -0.4(4)
C23 C24 C25 C20 -0.2(4)
C25 C20 C21 C22 -0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094162
