#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/62/1506264.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_1506264
loop_
_publ_author_name
'Arnott, Gareth'
'Clayden, Jonathan'
'Hamilton, Stuart D.'
_publ_contact_author
;
    Madeleine Helliwell 
;
_publ_section_title
;
 Azabicyclic amino acids by stereoselective dearomatizing cyclization of
 the enolates of N-nicotinoyl glycine derivatives.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5325
_journal_page_last               5328
_journal_paper_doi               10.1021/ol062126s
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H26 Cl3 F3 N2 O6 S'
_chemical_formula_weight         621.87
_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                   6.4308(3)
_cell_length_b                   14.8616(7)
_cell_length_c                   29.0316(14)
_cell_measurement_reflns_used    9672
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.51
_cell_volume                     2774.6(2)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15978
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  0.8003
_exptl_absorpt_correction_T_min  0.7672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_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     348
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0284
_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)+(0.0447P)²+0.4864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                5365
_reflns_number_total             5587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062126ssi20060829_090842.cif
_cod_data_source_block           z:\s2359\work\s2359abs
_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_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1506264
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
S1 S -0.05747(7) 0.65751(3) 0.196178(15) 0.02344(10) Uani 1 1 d .
F1 F 0.0329(2) 0.80717(8) 0.23834(4) 0.0378(3) Uani 1 1 d .
F2 F 0.28832(18) 0.71369(9) 0.23314(4) 0.0377(3) Uani 1 1 d .
F3 F 0.0397(2) 0.68934(8) 0.28156(4) 0.0373(3) Uani 1 1 d .
O1 O -0.2694(2) 0.68055(10) 0.20305(5) 0.0339(3) Uani 1 1 d .
O2 O 0.0183(2) 0.56808(9) 0.19897(5) 0.0310(3) Uani 1 1 d .
O3 O 0.1069(2) 0.77691(8) -0.00876(4) 0.0262(3) Uani 1 1 d .
O4 O 0.50413(18) 0.94315(8) 0.13715(4) 0.0195(2) Uani 1 1 d .
O5 O 0.2545(2) 1.01508(8) 0.09614(4) 0.0244(3) Uani 1 1 d .
O6 O 0.7800(2) 1.24238(9) 0.06853(5) 0.0293(3) Uani 1 1 d .
N1 N 0.0229(2) 0.70204(10) 0.14825(5) 0.0212(3) Uani 1 1 d .
N2 N 0.3318(2) 0.88765(9) 0.02170(4) 0.0170(3) Uani 1 1 d .
C1 C 0.0859(3) 0.72099(13) 0.24006(7) 0.0279(4) Uani 1 1 d .
C2 C -0.0619(3) 0.78497(11) 0.13296(6) 0.0203(3) Uani 1 1 d .
H2 H -0.1843 0.8076 0.1471 0.024 Uiso 1 1 calc R
C3 C 0.0264(3) 0.83131(11) 0.09937(6) 0.0195(3) Uani 1 1 d .
H3 H -0.0360 0.8866 0.0905 0.023 Uiso 1 1 calc R
C4 C 0.2187(3) 0.80202(11) 0.07447(6) 0.0177(3) Uani 1 1 d .
C5 C 0.2905(3) 0.71213(10) 0.09117(6) 0.0189(3) Uani 1 1 d .
H5 H 0.4051 0.6848 0.0760 0.023 Uiso 1 1 calc R
C6 C 0.2039(3) 0.66860(11) 0.12583(6) 0.0206(3) Uani 1 1 d .
H6 H 0.2637 0.6137 0.1361 0.025 Uiso 1 1 calc R
C7 C 0.2014(3) 0.81534(10) 0.02137(6) 0.0189(3) Uani 1 1 d .
C8 C 0.3985(3) 0.87490(11) 0.06954(6) 0.0173(3) Uani 1 1 d .
H8 H 0.5398 0.8472 0.0716 0.021 Uiso 1 1 calc R
C9 C 0.3759(3) 0.95470(11) 0.10144(6) 0.0176(3) Uani 1 1 d .
C10 C 0.5009(3) 1.00676(11) 0.17664(6) 0.0226(4) Uani 1 1 d .
C11 C 0.5645(4) 1.09924(13) 0.16007(7) 0.0405(5) Uani 1 1 d .
H11A H 0.7017 1.0958 0.1455 0.061 Uiso 1 1 calc R
H11B H 0.5703 1.1406 0.1863 0.061 Uiso 1 1 calc R
H11C H 0.4625 1.1212 0.1376 0.061 Uiso 1 1 calc R
C12 C 0.2888(3) 1.00605(15) 0.19881(7) 0.0357(5) Uani 1 1 d .
H12A H 0.1874 1.0333 0.1778 0.054 Uiso 1 1 calc R
H12B H 0.2933 1.0405 0.2276 0.054 Uiso 1 1 calc R
H12C H 0.2478 0.9439 0.2054 0.054 Uiso 1 1 calc R
C13 C 0.6624(4) 0.96697(14) 0.20895(7) 0.0352(5) Uani 1 1 d .
H13A H 0.6218 0.9055 0.2173 0.053 Uiso 1 1 calc R
H13B H 0.6715 1.0039 0.2368 0.053 Uiso 1 1 calc R
H13C H 0.7979 0.9658 0.1935 0.053 Uiso 1 1 calc R
C14 C 0.4569(3) 0.92842(11) -0.01554(6) 0.0202(3) Uani 1 1 d .
H14 H 0.5731 0.8863 -0.0231 0.024 Uiso 1 1 calc R
C15 C 0.3233(3) 0.93979(12) -0.05834(6) 0.0259(4) Uani 1 1 d .
H15A H 0.2822 0.8805 -0.0699 0.039 Uiso 1 1 calc R
H15B H 0.4029 0.9716 -0.0821 0.039 Uiso 1 1 calc R
H15C H 0.1988 0.9746 -0.0506 0.039 Uiso 1 1 calc R
C16 C 0.5504(3) 1.01490(11) 0.00252(6) 0.0191(3) Uani 1 1 d .
C17 C 0.7514(3) 1.01355(11) 0.02046(6) 0.0205(4) Uani 1 1 d .
H17 H 0.8320 0.9602 0.0178 0.025 Uiso 1 1 calc R
C18 C 0.8367(3) 1.08845(12) 0.04211(6) 0.0241(4) Uani 1 1 d .
H18 H 0.9737 1.0864 0.0543 0.029 Uiso 1 1 calc R
C19 C 0.7188(3) 1.16602(11) 0.04560(6) 0.0222(3) Uani 1 1 d .
C20 C 0.5222(3) 1.17018(11) 0.02563(6) 0.0237(4) Uani 1 1 d .
H20 H 0.4452 1.2247 0.0266 0.028 Uiso 1 1 calc R
C21 C 0.4389(3) 1.09533(11) 0.00442(6) 0.0219(4) Uani 1 1 d .
H21 H 0.3044 1.0986 -0.0090 0.026 Uiso 1 1 calc R
C22 C 0.9816(3) 1.24136(15) 0.08930(8) 0.0364(5) Uani 1 1 d .
H22A H 0.9875 1.1936 0.1126 0.055 Uiso 1 1 calc R
H22B H 1.0084 1.2996 0.1040 0.055 Uiso 1 1 calc R
H22C H 1.0870 1.2301 0.0656 0.055 Uiso 1 1 calc R
Cl1 Cl 0.86985(9) 0.08200(4) 0.90694(2) 0.04148(14) Uani 1 1 d .
Cl2 Cl 1.19341(9) 0.07425(4) 0.836970(19) 0.04707(15) Uani 1 1 d .
Cl3 Cl 0.81540(9) 0.17269(4) 0.819772(19) 0.04619(15) Uani 1 1 d .
C23 C 0.9965(3) 0.14000(14) 0.86185(7) 0.0310(4) Uani 1 1 d .
H23 H 1.0616 0.1955 0.8749 0.037 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'
F F 0.0171 0.0103 '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
O2 S1 O1 123.23(9)
O2 S1 N1 108.75(8)
O1 S1 N1 109.11(8)
O2 S1 C1 105.65(9)
O1 S1 C1 105.14(9)
N1 S1 C1 103.02(8)
C9 O4 C10 120.56(13)
C19 O6 C22 117.10(16)
C2 N1 C6 118.32(14)
C2 N1 S1 119.97(12)
C6 N1 S1 120.62(12)
C7 N2 C8 94.86(12)
C7 N2 C14 130.77(14)
C8 N2 C14 125.94(13)
F2 C1 F1 109.07(17)
F2 C1 F3 109.24(16)
F1 C1 F3 108.60(16)
F2 C1 S1 110.33(14)
F1 C1 S1 109.96(13)
F3 C1 S1 109.61(14)
C3 C2 N1 121.23(16)
C3 C2 H2 119.4
N1 C2 H2 119.4
C2 C3 C4 124.01(15)
C2 C3 H3 118.0
C4 C3 H3 118.0
C5 C4 C3 111.03(14)
C5 C4 C7 117.16(14)
C3 C4 C7 112.46(14)
C5 C4 C8 114.39(14)
C3 C4 C8 116.48(13)
C7 C4 C8 82.88(12)
C6 C5 C4 123.71(16)
C6 C5 H5 118.1
C4 C5 H5 118.1
C5 C6 N1 121.52(15)
C5 C6 H6 119.2
N1 C6 H6 119.2
O3 C7 N2 133.41(16)
O3 C7 C4 133.76(15)
N2 C7 C4 92.83(12)
N2 C8 C9 116.81(14)
N2 C8 C4 87.75(12)
C9 C8 C4 114.15(13)
N2 C8 H8 112.0
C9 C8 H8 112.0
C4 C8 H8 112.0
O5 C9 O4 126.70(15)
O5 C9 C8 124.80(15)
O4 C9 C8 108.39(13)
O4 C10 C12 109.71(14)
O4 C10 C11 109.20(14)
C12 C10 C11 112.73(18)
O4 C10 C13 102.67(14)
C12 C10 C13 110.60(16)
C11 C10 C13 111.43(17)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N2 C14 C16 108.14(13)
N2 C14 C15 109.63(14)
C16 C14 C15 114.42(14)
N2 C14 H14 108.2
C16 C14 H14 108.2
C15 C14 H14 108.2
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C21 C16 C17 118.31(16)
C21 C16 C14 122.51(16)
C17 C16 C14 119.08(15)
C18 C17 C16 121.54(16)
C18 C17 H17 119.2
C16 C17 H17 119.2
C19 C18 C17 118.92(16)
C19 C18 H18 120.5
C17 C18 H18 120.5
O6 C19 C18 124.54(16)
O6 C19 C20 115.18(16)
C18 C19 C20 120.28(16)
C21 C20 C19 120.17(16)
C21 C20 H20 119.9
C19 C20 H20 119.9
C20 C21 C16 120.60(16)
C20 C21 H21 119.7
C16 C21 H21 119.7
O6 C22 H22A 109.5
O6 C22 H22B 109.5
H22A C22 H22B 109.5
O6 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
Cl2 C23 Cl3 110.25(11)
Cl2 C23 Cl1 111.47(11)
Cl3 C23 Cl1 110.16(11)
Cl2 C23 H23 108.3
Cl3 C23 H23 108.3
Cl1 C23 H23 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4179(14)
S1 O1 1.4195(14)
S1 N1 1.6251(14)
S1 C1 1.834(2)
F1 C1 1.326(2)
F2 C1 1.321(2)
F3 C1 1.327(2)
O3 C7 1.209(2)
O4 C9 1.336(2)
O4 C10 1.4861(19)
O5 C9 1.199(2)
O6 C19 1.373(2)
O6 C22 1.430(3)
N1 C2 1.419(2)
N1 C6 1.423(2)
N2 C7 1.363(2)
N2 C8 1.466(2)
N2 C14 1.478(2)
C2 C3 1.322(2)
C2 H2 0.9500
C3 C4 1.497(2)
C3 H3 0.9500
C4 C5 1.494(2)
C4 C7 1.558(2)
C4 C8 1.591(2)
C5 C6 1.320(2)
C5 H5 0.9500
C6 H6 0.9500
C8 C9 1.512(2)
C8 H8 1.0000
C10 C12 1.509(3)
C10 C11 1.512(3)
C10 C13 1.519(3)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C16 1.513(2)
C14 C15 1.520(2)
C14 H14 1.0000
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 C21 1.395(2)
C16 C17 1.394(2)
C17 C18 1.391(3)
C17 H17 0.9500
C18 C19 1.384(2)
C18 H18 0.9500
C19 C20 1.392(3)
C20 C21 1.380(3)
C20 H20 0.9500
C21 H21 0.9500
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
Cl1 C23 1.766(2)
Cl2 C23 1.755(2)
Cl3 C23 1.756(2)
C23 H23 1.0000
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
O2 S1 N1 C2 168.39(13)
O1 S1 N1 C2 31.50(16)
C1 S1 N1 C2 -79.84(14)
O2 S1 N1 C6 -23.74(16)
O1 S1 N1 C6 -160.63(13)
C1 S1 N1 C6 88.04(15)
O2 S1 C1 F2 56.34(15)
O1 S1 C1 F2 -171.95(13)
N1 S1 C1 F2 -57.70(15)
O2 S1 C1 F1 176.70(13)
O1 S1 C1 F1 -51.60(15)
N1 S1 C1 F1 62.65(15)
O2 S1 C1 F3 -63.99(15)
O1 S1 C1 F3 67.71(14)
N1 S1 C1 F3 -178.04(13)
C6 N1 C2 C3 -1.3(2)
S1 N1 C2 C3 166.85(14)
N1 C2 C3 C4 0.3(3)
C2 C3 C4 C5 2.6(2)
C2 C3 C4 C7 136.08(17)
C2 C3 C4 C8 -130.70(18)
C3 C4 C5 C6 -5.0(2)
C7 C4 C5 C6 -136.10(18)
C8 C4 C5 C6 129.33(17)
C4 C5 C6 N1 4.5(3)
C2 N1 C6 C5 -1.1(2)
S1 N1 C6 C5 -169.14(14)
C8 N2 C7 O3 -170.3(2)
C14 N2 C7 O3 -21.9(3)
C8 N2 C7 C4 10.42(13)
C14 N2 C7 C4 158.75(16)
C5 C4 C7 O3 57.2(3)
C3 C4 C7 O3 -73.2(2)
C8 C4 C7 O3 171.1(2)
C5 C4 C7 N2 -123.44(15)
C3 C4 C7 N2 106.13(15)
C8 C4 C7 N2 -9.63(12)
C7 N2 C8 C9 -126.23(15)
C14 N2 C8 C9 83.18(19)
C7 N2 C8 C4 -10.20(13)
C14 N2 C8 C4 -160.79(15)
C5 C4 C8 N2 125.59(14)
C3 C4 C8 N2 -102.64(15)
C7 C4 C8 N2 8.95(11)
C5 C4 C8 C9 -115.92(16)
C3 C4 C8 C9 15.8(2)
C7 C4 C8 C9 127.44(14)
C10 O4 C9 O5 2.4(2)
C10 O4 C9 C8 -173.98(13)
N2 C8 C9 O5 24.6(2)
C4 C8 C9 O5 -75.6(2)
N2 C8 C9 O4 -158.92(13)
C4 C8 C9 O4 100.81(15)
C9 O4 C10 C12 60.6(2)
C9 O4 C10 C11 -63.4(2)
C9 O4 C10 C13 178.23(15)
C7 N2 C14 C16 172.52(16)
C8 N2 C14 C16 -47.7(2)
C7 N2 C14 C15 47.1(2)
C8 N2 C14 C15 -173.10(15)
N2 C14 C16 C21 -81.03(19)
C15 C14 C16 C21 41.5(2)
N2 C14 C16 C17 95.13(18)
C15 C14 C16 C17 -142.38(16)
C21 C16 C17 C18 3.5(2)
C14 C16 C17 C18 -172.81(16)
C16 C17 C18 C19 -0.3(3)
C22 O6 C19 C18 1.3(3)
C22 O6 C19 C20 -179.56(17)
C17 C18 C19 O6 175.84(16)
C17 C18 C19 C20 -3.3(3)
O6 C19 C20 C21 -175.60(16)
C18 C19 C20 C21 3.6(3)
C19 C20 C21 C16 -0.3(3)
C17 C16 C21 C20 -3.2(3)
C14 C16 C21 C20 173.00(16)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199665 ChemSpider
2 139039521 PubChem
