#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150633.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_7150633
loop_
_publ_author_name
'Coldham, Iain'
'Jana, Samaresh'
'Watson, Luke'
'Martin, Nathaniel G.'
_publ_section_title
;
 Cascade condensation, cyclization, intermolecular dipolar
 cycloaddition by multi-component coupling and application to a
 synthesis of (+-)-crispine A
;
_journal_issue                   8
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1674
_journal_page_last               1679
_journal_paper_doi               10.1039/b822743h
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C27 H28 Cl3 N O6 S2'
_chemical_formula_weight         632.97
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.777(2)
_cell_angle_beta                 73.519(2)
_cell_angle_gamma                80.784(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0677(3)
_cell_length_b                   12.2382(4)
_cell_length_c                   13.3377(4)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.21
_cell_measurement_theta_min      2.21
_cell_volume                     1400.53(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17709
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  0.9402
_exptl_absorpt_correction_T_min  0.8513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.7191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                5686
_reflns_number_total             6433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b822743h.txt
_cod_data_source_block           sj223_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150633
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.03154(4) 0.71645(3) 0.88235(2) 0.01390(8) Uani 1 1 d . . .
S2 S 0.26039(4) 0.96276(3) 0.73521(3) 0.01467(8) Uani 1 1 d . . .
N1 N -0.02524(14) 0.80478(10) 0.65214(8) 0.0135(2) Uani 1 1 d . . .
O1 O 0.04671(13) 0.78500(9) 0.96462(7) 0.0192(2) Uani 1 1 d . . .
O2 O -0.12180(12) 0.70334(9) 0.87874(8) 0.0198(2) Uani 1 1 d . . .
O3 O 0.37773(12) 0.90766(9) 0.64642(8) 0.0207(2) Uani 1 1 d . . .
O4 O 0.21048(13) 1.08083(9) 0.73306(8) 0.0214(2) Uani 1 1 d . . .
O5 O -0.27559(12) 1.28962(8) 0.76839(8) 0.0181(2) Uani 1 1 d . . .
O6 O -0.46056(12) 1.26792(8) 0.65653(8) 0.0186(2) Uani 1 1 d . . .
C1 C 0.13740(16) 0.76952(11) 0.76043(10) 0.0135(3) Uani 1 1 d . . .
H1 H 0.2517 0.7517 0.7526 0.016 Uiso 1 1 calc R . .
C2 C 0.10287(17) 0.72291(12) 0.66484(10) 0.0155(3) Uani 1 1 d . . .
H2A H 0.1943 0.7177 0.6023 0.019 Uiso 1 1 calc R . .
H2B H 0.0714 0.6489 0.6785 0.019 Uiso 1 1 calc R . .
C3 C -0.06443(17) 0.79607(12) 0.55352(10) 0.0160(3) Uani 1 1 d . . .
H3A H -0.0815 0.7198 0.5429 0.019 Uiso 1 1 calc R . .
H3B H 0.0224 0.8130 0.4942 0.019 Uiso 1 1 calc R . .
C4 C -0.21234(17) 0.87816(12) 0.55805(11) 0.0163(3) Uani 1 1 d . . .
H4A H -0.2191 0.8918 0.4859 0.020 Uiso 1 1 calc R . .
H4B H -0.3040 0.8446 0.5963 0.020 Uiso 1 1 calc R . .
C5 C -0.21870(16) 0.98804(11) 0.61088(10) 0.0137(3) Uani 1 1 d . . .
C6 C -0.33811(16) 1.07564(12) 0.60782(10) 0.0148(3) Uani 1 1 d . . .
H6 H -0.4103 1.0656 0.5707 0.018 Uiso 1 1 calc R . .
C7 C -0.35252(16) 1.17645(12) 0.65799(10) 0.0141(3) Uani 1 1 d . . .
C8 C -0.24792(17) 1.18951(11) 0.71597(10) 0.0142(3) Uani 1 1 d . . .
C9 C -0.12835(16) 1.10504(11) 0.71739(10) 0.0136(3) Uani 1 1 d . . .
H9 H -0.0562 1.1154 0.7545 0.016 Uiso 1 1 calc R . .
C10 C -0.11178(16) 1.00395(11) 0.66475(10) 0.0132(3) Uani 1 1 d . . .
C11 C 0.02299(16) 0.91218(11) 0.66048(10) 0.0130(3) Uani 1 1 d . . .
H11 H 0.1099 0.9212 0.5967 0.016 Uiso 1 1 calc R . .
C12 C 0.08993(16) 0.89680(11) 0.75589(10) 0.0123(3) Uani 1 1 d . . .
H12 H 0.0089 0.9262 0.8216 0.015 Uiso 1 1 calc R . .
C13 C 0.32273(16) 0.93393(12) 0.84837(10) 0.0145(3) Uani 1 1 d . . .
C14 C 0.24500(17) 0.99639(12) 0.93948(11) 0.0176(3) Uani 1 1 d . . .
H14 H 0.1612 1.0545 0.9407 0.021 Uiso 1 1 calc R . .
C15 C 0.29319(18) 0.97156(13) 1.02845(11) 0.0210(3) Uani 1 1 d . . .
H15 H 0.2423 1.0133 1.0914 0.025 Uiso 1 1 calc R . .
C16 C 0.41537(18) 0.88599(13) 1.02605(11) 0.0208(3) Uani 1 1 d . . .
H16 H 0.4457 0.8687 1.0879 0.025 Uiso 1 1 calc R . .
C17 C 0.49342(18) 0.82572(13) 0.93423(12) 0.0202(3) Uani 1 1 d . . .
H17 H 0.5780 0.7683 0.9328 0.024 Uiso 1 1 calc R . .
C18 C 0.44705(17) 0.84977(13) 0.84399(11) 0.0182(3) Uani 1 1 d . . .
H18 H 0.4997 0.8092 0.7806 0.022 Uiso 1 1 calc R . .
C19 C 0.14238(17) 0.58404(11) 0.88401(10) 0.0143(3) Uani 1 1 d . . .
C20 C 0.28091(18) 0.57544(13) 0.91166(11) 0.0187(3) Uani 1 1 d . . .
H20 H 0.3136 0.6394 0.9320 0.022 Uiso 1 1 calc R . .
C21 C 0.37030(18) 0.47132(13) 0.90886(11) 0.0215(3) Uani 1 1 d . . .
H21 H 0.4651 0.4639 0.9273 0.026 Uiso 1 1 calc R . .
C22 C 0.32181(19) 0.37843(13) 0.87932(11) 0.0218(3) Uani 1 1 d . . .
H22 H 0.3839 0.3077 0.8774 0.026 Uiso 1 1 calc R . .
C23 C 0.1835(2) 0.38773(13) 0.85248(12) 0.0240(3) Uani 1 1 d . . .
H23 H 0.1508 0.3236 0.8327 0.029 Uiso 1 1 calc R . .
C24 C 0.09246(18) 0.49141(12) 0.85453(12) 0.0202(3) Uani 1 1 d . . .
H24 H -0.0023 0.4986 0.8360 0.024 Uiso 1 1 calc R . .
C25 C -0.56563(18) 1.25891(13) 0.59573(12) 0.0195(3) Uani 1 1 d . . .
H25A H -0.5059 1.2371 0.5235 0.029 Uiso 1 1 calc R . .
H25B H -0.6322 1.3305 0.5965 0.029 Uiso 1 1 calc R . .
H25C H -0.6306 1.2029 0.6256 0.029 Uiso 1 1 calc R . .
C26 C -0.1624(2) 1.30802(13) 0.81926(12) 0.0230(3) Uani 1 1 d . . .
H26A H -0.1546 1.2502 0.8703 0.035 Uiso 1 1 calc R . .
H26B H -0.1940 1.3806 0.8552 0.035 Uiso 1 1 calc R . .
H26C H -0.0609 1.3058 0.7672 0.035 Uiso 1 1 calc R . .
C1S C 0.64844(18) 0.50783(13) 0.66029(12) 0.0206(3) Uani 1 1 d . . .
H1S H 0.6282 0.4374 0.6971 0.025 Uiso 1 1 calc R . .
Cl1 Cl 0.79730(5) 0.47604(4) 0.54215(4) 0.04017(12) Uani 1 1 d . . .
Cl2 Cl 0.71000(5) 0.59294(3) 0.74091(3) 0.02615(9) Uani 1 1 d . . .
Cl3 Cl 0.47577(5) 0.57321(3) 0.63430(3) 0.02698(10) Uani 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'
Cl Cl 0.1484 0.1585 '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
O2 S1 O1 119.00(7) . . ?
O2 S1 C19 108.90(7) . . ?
O1 S1 C19 108.75(6) . . ?
O2 S1 C1 110.20(6) . . ?
O1 S1 C1 106.55(6) . . ?
C19 S1 C1 102.11(6) . . ?
O3 S2 O4 119.29(7) . . ?
O3 S2 C13 108.69(7) . . ?
O4 S2 C13 108.36(7) . . ?
O3 S2 C12 107.39(6) . . ?
O4 S2 C12 107.55(6) . . ?
C13 S2 C12 104.59(6) . . ?
C2 N1 C11 105.11(11) . . ?
C2 N1 C3 115.39(11) . . ?
C11 N1 C3 110.01(10) . . ?
C8 O5 C26 116.02(11) . . ?
C7 O6 C25 116.78(11) . . ?
C2 C1 C12 104.46(10) . . ?
C2 C1 S1 112.94(10) . . ?
C12 C1 S1 111.32(9) . . ?
C2 C1 H1 109.3 . . ?
C12 C1 H1 109.3 . . ?
S1 C1 H1 109.3 . . ?
N1 C2 C1 102.24(11) . . ?
N1 C2 H2A 111.3 . . ?
C1 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C1 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
N1 C3 C4 108.78(11) . . ?
N1 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C5 C4 C3 113.39(11) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C10 C5 C6 119.02(13) . . ?
C10 C5 C4 122.02(12) . . ?
C6 C5 C4 118.94(12) . . ?
C7 C6 C5 121.26(12) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O6 C7 C6 125.81(12) . . ?
O6 C7 C8 115.19(12) . . ?
C6 C7 C8 119.01(13) . . ?
O5 C8 C9 124.49(12) . . ?
O5 C8 C7 115.44(12) . . ?
C9 C8 C7 120.08(13) . . ?
C8 C9 C10 120.82(12) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 119.71(13) . . ?
C5 C10 C11 118.40(12) . . ?
C9 C10 C11 121.84(12) . . ?
N1 C11 C10 109.58(11) . . ?
N1 C11 C12 102.33(10) . . ?
C10 C11 C12 118.93(11) . . ?
N1 C11 H11 108.5 . . ?
C10 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C1 C12 C11 104.16(10) . . ?
C1 C12 S2 109.48(9) . . ?
C11 C12 S2 110.88(9) . . ?
C1 C12 H12 110.7 . . ?
C11 C12 H12 110.7 . . ?
S2 C12 H12 110.7 . . ?
C18 C13 C14 122.05(12) . . ?
C18 C13 S2 119.19(11) . . ?
C14 C13 S2 118.76(11) . . ?
C15 C14 C13 118.22(14) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 120.49(14) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.61(13) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.69(14) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 118.91(14) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C24 C19 C20 121.45(13) . . ?
C24 C19 S1 119.42(11) . . ?
C20 C19 S1 119.09(11) . . ?
C21 C20 C19 118.64(14) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C20 120.39(14) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.55(14) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 119.94(15) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 119.03(14) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
Cl3 C1S Cl1 110.05(8) . . ?
Cl3 C1S Cl2 111.15(8) . . ?
Cl1 C1S Cl2 109.44(9) . . ?
Cl3 C1S H1S 108.7 . . ?
Cl1 C1S H1S 108.7 . . ?
Cl2 C1S H1S 108.7 . . ?
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 O2 1.4391(11) . ?
S1 O1 1.4452(10) . ?
S1 C19 1.7681(14) . ?
S1 C1 1.8046(13) . ?
S2 O3 1.4417(11) . ?
S2 O4 1.4455(11) . ?
S2 C13 1.7663(13) . ?
S2 C12 1.8070(14) . ?
N1 C2 1.4539(17) . ?
N1 C11 1.4660(18) . ?
N1 C3 1.4667(16) . ?
O5 C8 1.3752(17) . ?
O5 C26 1.4282(17) . ?
O6 C7 1.3682(17) . ?
O6 C25 1.4330(16) . ?
C1 C2 1.5375(18) . ?
C1 C12 1.5528(18) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.529(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5169(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.3986(18) . ?
C5 C6 1.4052(19) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.4118(18) . ?
C8 C9 1.3771(19) . ?
C9 C10 1.4013(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.5105(19) . ?
C11 C12 1.5540(17) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C18 1.389(2) . ?
C13 C14 1.392(2) . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3944(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.389(2) . ?
C19 C20 1.394(2) . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C1S Cl3 1.7626(15) . ?
C1S Cl1 1.7628(16) . ?
C1S Cl2 1.7685(16) . ?
C1S H1S 1.0000 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190151
