#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/44/1504493.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_1504493
loop_
_publ_author_name
'Boratyński, Przemysław J'
'Turowska-Tyrk, Ilona'
'Skarzewski, Jacek'
_publ_section_title
;
 Stereoselective C9 arylation and vinylation of Cinchona alkaloids.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              385
_journal_page_last               388
_journal_paper_doi               10.1021/ol7026625
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H29 N3 O S'
_chemical_formula_weight         443.59
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4513(7)
_cell_length_b                   10.0331(8)
_cell_length_c                   24.638(2)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      3
_cell_volume                     2336.3(3)
_computing_cell_refinement       'CRYSALIS (Oxford Diffraction, 2003)'
_computing_data_collection       'CRYSALIS (Oxford Diffraction, 2003)'
_computing_data_reduction        'CRYSALIS (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Kuma KM4CCD'
_diffrn_measurement_method       'ω 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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12653
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1027P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1529
_reflns_number_gt                3299
_reflns_number_total             4125
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7026625-file001.cif
_cod_data_source_block           JS6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1504493
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.2249(3) 0.0184(3) 0.57813(11) 0.0449(6) Uani 1 1 d .
C2 C 0.1080(4) -0.0327(3) 0.55139(13) 0.0590(8) Uani 1 1 d .
H2 H 0.0176 -0.0123 0.5637 0.071 Uiso 1 1 calc R
C3 C 0.1251(6) -0.1143(4) 0.50623(15) 0.0833(13) Uani 1 1 d .
H3 H 0.0460 -0.1480 0.4884 0.100 Uiso 1 1 calc R
C4 C 0.2570(7) -0.1449(4) 0.48799(16) 0.0932(15) Uani 1 1 d .
H4 H 0.2675 -0.2002 0.4580 0.112 Uiso 1 1 calc R
C5 C 0.3749(5) -0.0947(4) 0.51352(17) 0.0821(12) Uani 1 1 d .
H5 H 0.4648 -0.1152 0.5006 0.099 Uiso 1 1 calc R
C6 C 0.3589(3) -0.0128(3) 0.55888(14) 0.0590(8) Uani 1 1 d .
H6 H 0.4385 0.0210 0.5763 0.071 Uiso 1 1 calc R
C7 C 0.2078(3) 0.1059(2) 0.62754(10) 0.0374(6) Uani 1 1 d .
H7 H 0.1065 0.1099 0.6359 0.045 Uiso 1 1 calc R
C8 C 0.2822(3) 0.0461(3) 0.67675(10) 0.0410(6) Uani 1 1 d .
C9 C 0.4135(3) 0.0889(4) 0.69281(12) 0.0592(8) Uani 1 1 d .
H9 H 0.4574 0.1586 0.6745 0.071 Uiso 1 1 calc R
C10 C 0.4815(4) 0.0274(4) 0.73685(16) 0.0744(11) Uani 1 1 d .
H10 H 0.5699 0.0598 0.7469 0.089 Uiso 1 1 calc R
N1 N 0.4298(3) -0.0718(3) 0.76466(11) 0.0648(7) Uani 1 1 d .
C11 C 0.2999(3) -0.1162(3) 0.74956(11) 0.0464(7) Uani 1 1 d .
C12 C 0.2440(3) -0.2254(3) 0.77875(12) 0.0539(7) Uani 1 1 d .
H12 H 0.2942 -0.2600 0.8080 0.065 Uiso 1 1 calc R
C13 C 0.1190(3) -0.2801(3) 0.76476(12) 0.0528(7) Uani 1 1 d .
H13 H 0.0851 -0.3540 0.7835 0.063 Uiso 1 1 calc R
C14 C 0.0395(3) -0.2256(3) 0.72178(11) 0.0468(7) Uani 1 1 d .
C15 C 0.0876(3) -0.1182(3) 0.69322(10) 0.0405(6) Uani 1 1 d .
H15 H 0.0328 -0.0822 0.6655 0.049 Uiso 1 1 calc R
C16 C 0.2205(3) -0.0617(3) 0.70568(10) 0.0376(6) Uani 1 1 d .
O1 O -0.0842(2) -0.2911(2) 0.71263(9) 0.0656(6) Uani 1 1 d .
C17 C -0.1756(4) -0.2385(5) 0.6739(2) 0.1052(16) Uani 1 1 d .
H17A H -0.2075 -0.1522 0.6855 0.126 Uiso 1 1 calc R
H17B H -0.2555 -0.2967 0.6697 0.126 Uiso 1 1 calc R
H17C H -0.1269 -0.2305 0.6399 0.126 Uiso 1 1 calc R
C18 C 0.2585(3) 0.2505(3) 0.61703(10) 0.0398(6) Uani 1 1 d .
H18 H 0.3610 0.2492 0.6113 0.048 Uiso 1 1 calc R
C19 C 0.0339(3) 0.3330(3) 0.57365(13) 0.0563(8) Uani 1 1 d .
H19A H -0.0145 0.2508 0.5829 0.068 Uiso 1 1 calc R
H19B H -0.0054 0.3663 0.5399 0.068 Uiso 1 1 calc R
C20 C 0.0127(4) 0.4346(4) 0.61826(15) 0.0712(10) Uani 1 1 d .
H20A H -0.0480 0.3978 0.6463 0.085 Uiso 1 1 calc R
H20B H -0.0329 0.5134 0.6036 0.085 Uiso 1 1 calc R
C21 C 0.1570(4) 0.4726(3) 0.64283(12) 0.0549(7) Uani 1 1 d .
H21 H 0.1436 0.5361 0.6726 0.066 Uiso 1 1 calc R
C22 C 0.2258(3) 0.3454(3) 0.66409(11) 0.0502(7) Uani 1 1 d .
H22A H 0.1626 0.3020 0.6896 0.060 Uiso 1 1 calc R
H22B H 0.3126 0.3674 0.6830 0.060 Uiso 1 1 calc R
C23 C 0.2493(3) 0.5349(3) 0.59875(12) 0.0533(7) Uani 1 1 d .
H23 H 0.2002 0.6138 0.5848 0.064 Uiso 1 1 calc R
C24 C 0.2636(3) 0.4349(3) 0.55217(11) 0.0485(7) Uani 1 1 d .
H24A H 0.2224 0.4720 0.5194 0.058 Uiso 1 1 calc R
H24B H 0.3628 0.4171 0.5453 0.058 Uiso 1 1 calc R
N2 N 0.1888(2) 0.3069(2) 0.56687(8) 0.0425(5) Uani 1 1 d .
H2A H 0.2005 0.2479 0.5392 0.051 Uiso 1 1 calc R
C25 C 0.3948(4) 0.5790(4) 0.61972(14) 0.0686(9) Uani 1 1 d .
H25 H 0.4644 0.5142 0.6237 0.082 Uiso 1 1 calc R
C26 C 0.4265(6) 0.6974(5) 0.63188(18) 0.0950(13) Uani 1 1 d .
H26A H 0.3594 0.7647 0.6284 0.114 Uiso 1 1 calc R
H26B H 0.5168 0.7174 0.6444 0.114 Uiso 1 1 calc R
S1 S 0.15609(10) 0.21438(12) 0.43977(4) 0.0773(3) Uani 1 1 d .
C27 C 0.2190(4) 0.3499(4) 0.41648(15) 0.0708(10) Uani 1 1 d .
N3 N 0.2579(3) 0.4507(3) 0.39670(10) 0.0639(8) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.8(3)
C2 C1 C7 120.9(3)
C6 C1 C7 120.3(3)
C1 C2 C3 120.4(4)
C1 C2 H2 119.8
C3 C2 H2 119.8
C4 C3 C2 120.2(4)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 120.6(4)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 119.6(4)
C4 C5 H5 120.2
C6 C5 H5 120.2
C1 C6 C5 120.4(4)
C1 C6 H6 119.8
C5 C6 H6 119.8
C1 C7 C8 111.3(2)
C1 C7 C18 112.1(2)
C8 C7 C18 111.0(2)
C1 C7 H7 107.4
C8 C7 H7 107.4
C18 C7 H7 107.4
C9 C8 C16 117.7(2)
C9 C8 C7 121.5(2)
C16 C8 C7 120.6(2)
C8 C9 C10 120.0(3)
C8 C9 H9 120.0
C10 C9 H9 120.0
N1 C10 C9 124.8(3)
N1 C10 H10 117.6
C9 C10 H10 117.6
C10 N1 C11 116.4(3)
N1 C11 C12 116.9(3)
N1 C11 C16 123.9(3)
C12 C11 C16 119.2(3)
C13 C12 C11 120.9(3)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 120.1(3)
C12 C13 H13 120.0
C14 C13 H13 120.0
O1 C14 C15 125.6(3)
O1 C14 C13 113.3(3)
C15 C14 C13 121.1(3)
C14 C15 C16 120.1(2)
C14 C15 H15 120.0
C16 C15 H15 120.0
C15 C16 C8 124.2(2)
C15 C16 C11 118.6(2)
C8 C16 C11 117.2(2)
C14 O1 C17 117.7(3)
O1 C17 H17A 109.5
O1 C17 H17B 109.5
H17A C17 H17B 109.5
O1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N2 C18 C22 107.4(2)
N2 C18 C7 110.7(2)
C22 C18 C7 113.2(2)
N2 C18 H18 108.5
C22 C18 H18 108.5
C7 C18 H18 108.5
N2 C19 C20 109.2(3)
N2 C19 H19A 109.8
C20 C19 H19A 109.8
N2 C19 H19B 109.8
C20 C19 H19B 109.8
H19A C19 H19B 108.3
C19 C20 C21 109.6(3)
C19 C20 H20A 109.8
C21 C20 H20A 109.8
C19 C20 H20B 109.8
C21 C20 H20B 109.8
H20A C20 H20B 108.2
C22 C21 C23 110.0(3)
C22 C21 C20 107.8(3)
C23 C21 C20 109.1(3)
C22 C21 H21 109.9
C23 C21 H21 109.9
C20 C21 H21 109.9
C21 C22 C18 110.3(2)
C21 C22 H22A 109.6
C18 C22 H22A 109.6
C21 C22 H22B 109.6
C18 C22 H22B 109.6
H22A C22 H22B 108.1
C21 C23 C24 108.4(2)
C21 C23 C25 113.0(3)
C24 C23 C25 111.3(3)
C21 C23 H23 108.0
C24 C23 H23 108.0
C25 C23 H23 108.0
N2 C24 C23 109.7(2)
N2 C24 H24A 109.7
C23 C24 H24A 109.7
N2 C24 H24B 109.7
C23 C24 H24B 109.7
H24A C24 H24B 108.2
C19 N2 C18 113.6(2)
C19 N2 C24 109.6(2)
C18 N2 C24 108.1(2)
C19 N2 H2A 108.5
C18 N2 H2A 108.5
C24 N2 H2A 108.5
C26 C25 C23 124.4(4)
C26 C25 H25 117.8
C23 C25 H25 117.8
C25 C26 H26A 120.0
C25 C26 H26B 120.0
H26A C26 H26B 120.0
N3 C27 S1 175.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.384(4)
C1 C6 1.389(4)
C1 C7 1.510(4)
C2 C3 1.390(5)
C2 H2 0.9300
C3 C4 1.360(7)
C3 H3 0.9300
C4 C5 1.375(7)
C4 H4 0.9300
C5 C6 1.395(5)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.525(3)
C7 C18 1.549(4)
C7 H7 0.9800
C8 C9 1.371(4)
C8 C16 1.420(4)
C9 C10 1.404(4)
C9 H9 0.9300
C10 N1 1.303(5)
C10 H10 0.9300
N1 C11 1.359(4)
C11 C12 1.413(4)
C11 C16 1.425(4)
C12 C13 1.348(5)
C12 H12 0.9300
C13 C14 1.409(4)
C13 H13 0.9300
C14 O1 1.360(4)
C14 C15 1.365(4)
C15 C16 1.412(4)
C15 H15 0.9300
O1 C17 1.390(5)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 N2 1.510(3)
C18 C22 1.532(4)
C18 H18 0.9800
C19 N2 1.496(4)
C19 C20 1.513(5)
C19 H19A 0.9700
C19 H19B 0.9700
C20 C21 1.540(5)
C20 H20A 0.9700
C20 H20B 0.9700
C21 C22 1.525(4)
C21 C23 1.527(4)
C21 H21 0.9800
C22 H22A 0.9700
C22 H22B 0.9700
C23 C24 1.530(4)
C23 C25 1.535(5)
C23 H23 0.9800
C24 N2 1.511(4)
C24 H24A 0.9700
C24 H24B 0.9700
N2 H2A 0.9100
C25 C26 1.261(6)
C25 H25 0.9300
C26 H26A 0.9300
C26 H26B 0.9300
S1 C27 1.591(5)
C27 N3 1.182(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038602
