#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/64/4036425.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_4036425
loop_
_publ_author_name
'Maury, Julien'
'Clayden, Jonathan'
_publ_section_title
;
 α-Quaternary Proline Derivatives by Intramolecular Diastereoselective
 Arylation of N-Carboxamido Proline Ester Enolates.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10757
_journal_page_last               10768
_journal_paper_doi               10.1021/acs.joc.5b01912
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C17 H20 N2 O2'
_chemical_formula_weight         284.35
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 92.635(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2307(4)
_cell_length_b                   8.9399(2)
_cell_length_c                   10.0149(3)
_cell_measurement_reflns_used    2703
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.24
_cell_measurement_theta_min      5.46
_cell_volume                     1451.63(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4147
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         72.23
_diffrn_reflns_theta_min         4.42
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.9599
_exptl_absorpt_correction_T_min  0.793165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0276
_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)+(0.0348P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                2146
_reflns_number_total             2234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01912_si_004.cif
_cod_data_source_block           s4189ma
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4036425
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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 0.85853(9) 0.60260(16) 0.26114(15) 0.0155(3) Uani 1 1 d .
C2 C 0.83034(9) 0.70722(18) 0.37163(15) 0.0169(3) Uani 1 1 d .
C3 C 0.94462(9) 0.81242(18) 0.28080(15) 0.0170(3) Uani 1 1 d .
C4 C 1.00133(9) 0.57277(17) 0.19414(15) 0.0162(3) Uani 1 1 d .
H4 H 1.0237 0.5889 0.1039 0.019 Uiso 1 1 calc R
C5 C 1.07119(9) 0.58573(18) 0.30223(15) 0.0191(3) Uani 1 1 d .
H5A H 1.1041 0.6765 0.2857 0.023 Uiso 1 1 calc R
H5B H 1.0472 0.5965 0.3908 0.023 Uiso 1 1 calc R
C6 C 1.12757(10) 0.4489(2) 0.30353(17) 0.0224(3) Uani 1 1 d .
H6A H 1.1545 0.4417 0.2171 0.027 Uiso 1 1 calc R
H6B H 1.1712 0.4602 0.3751 0.027 Uiso 1 1 calc R
C7 C 1.07908(10) 0.30641(19) 0.32683(16) 0.0210(3) Uani 1 1 d .
H7A H 1.0535 0.3119 0.4146 0.025 Uiso 1 1 calc R
H7B H 1.1168 0.2194 0.3282 0.025 Uiso 1 1 calc R
C8 C 1.01208(10) 0.28594(18) 0.21634(16) 0.0214(3) Uani 1 1 d .
H8A H 0.9782 0.1978 0.2377 0.026 Uiso 1 1 calc R
H8B H 1.0386 0.2652 0.1312 0.026 Uiso 1 1 calc R
C9 C 0.95557(9) 0.42156(17) 0.19716(15) 0.0171(3) Uani 1 1 d .
H9 H 0.9247 0.4095 0.1091 0.020 Uiso 1 1 calc R
C10 C 0.89155(9) 0.44781(18) 0.30361(15) 0.0173(3) Uani 1 1 d .
H10A H 0.8475 0.3711 0.2988 0.021 Uiso 1 1 calc R
H10B H 0.9176 0.4497 0.3949 0.021 Uiso 1 1 calc R
C11 C 0.78907(9) 0.59192(17) 0.15283(15) 0.0169(3) Uani 1 1 d .
C12 C 0.79713(10) 0.65267(18) 0.02662(17) 0.0209(3) Uani 1 1 d .
H12 H 0.8466 0.7029 0.0061 0.025 Uiso 1 1 calc R
C13 C 0.73296(11) 0.6403(2) -0.07022(18) 0.0251(4) Uani 1 1 d .
H13 H 0.7390 0.6815 -0.1567 0.030 Uiso 1 1 calc R
C14 C 0.66062(11) 0.5681(2) -0.04088(18) 0.0252(4) Uani 1 1 d .
H14 H 0.6171 0.5592 -0.1072 0.030 Uiso 1 1 calc R
C15 C 0.65170(10) 0.5088(2) 0.08574(17) 0.0229(3) Uani 1 1 d .
H15 H 0.6017 0.4605 0.1065 0.027 Uiso 1 1 calc R
C16 C 0.71579(10) 0.51975(18) 0.18224(16) 0.0198(3) Uani 1 1 d .
H16 H 0.7097 0.4780 0.2685 0.024 Uiso 1 1 calc R
C17 C 0.87114(11) 0.96465(18) 0.44986(17) 0.0238(4) Uani 1 1 d .
H17A H 0.8136 0.9757 0.4738 0.036 Uiso 1 1 calc R
H17B H 0.8880 1.0534 0.4006 0.036 Uiso 1 1 calc R
H17C H 0.9064 0.9537 0.5313 0.036 Uiso 1 1 calc R
N1 N 0.87911(8) 0.83216(14) 0.36609(13) 0.0181(3) Uani 1 1 d .
N2 N 0.93252(7) 0.67968(15) 0.21495(12) 0.0157(3) Uani 1 1 d .
O1 O 0.77484(6) 0.68792(14) 0.44697(11) 0.0220(2) Uani 1 1 d .
O2 O 1.00076(7) 0.90043(12) 0.27111(12) 0.0224(3) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N2 C1 C11 112.95(12)
N2 C1 C2 102.42(12)
C11 C1 C2 108.34(11)
N2 C1 C10 103.21(11)
C11 C1 C10 112.09(12)
C2 C1 C10 117.45(12)
O1 C2 N1 125.95(14)
O1 C2 C1 128.02(14)
N1 C2 C1 105.99(12)
O2 C3 N2 128.09(14)
O2 C3 N1 124.07(14)
N2 C3 N1 107.83(12)
N2 C4 C5 112.74(12)
N2 C4 C9 101.21(11)
C5 C4 C9 113.12(12)
N2 C4 H4 109.8
C5 C4 H4 109.8
C9 C4 H4 109.8
C6 C5 C4 111.60(13)
C6 C5 H5A 109.3
C4 C5 H5A 109.3
C6 C5 H5B 109.3
C4 C5 H5B 109.3
H5A C5 H5B 108.0
C7 C6 C5 110.98(12)
C7 C6 H6A 109.4
C5 C6 H6A 109.4
C7 C6 H6B 109.4
C5 C6 H6B 109.4
H6A C6 H6B 108.0
C6 C7 C8 110.22(13)
C6 C7 H7A 109.6
C8 C7 H7A 109.6
C6 C7 H7B 109.6
C8 C7 H7B 109.6
H7A C7 H7B 108.1
C7 C8 C9 113.56(13)
C7 C8 H8A 108.9
C9 C8 H8A 108.9
C7 C8 H8B 108.9
C9 C8 H8B 108.9
H8A C8 H8B 107.7
C8 C9 C10 117.01(13)
C8 C9 C4 114.28(12)
C10 C9 C4 102.74(11)
C8 C9 H9 107.4
C10 C9 H9 107.4
C4 C9 H9 107.4
C1 C10 C9 100.57(11)
C1 C10 H10A 111.7
C9 C10 H10A 111.7
C1 C10 H10B 111.7
C9 C10 H10B 111.7
H10A C10 H10B 109.4
C12 C11 C16 119.34(14)
C12 C11 C1 121.59(13)
C16 C11 C1 119.07(13)
C11 C12 C13 120.25(15)
C11 C12 H12 119.9
C13 C12 H12 119.9
C14 C13 C12 120.24(16)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 119.83(16)
C13 C14 H14 120.1
C15 C14 H14 120.1
C14 C15 C16 120.12(15)
C14 C15 H15 119.9
C16 C15 H15 119.9
C15 C16 C11 120.22(15)
C15 C16 H16 119.9
C11 C16 H16 119.9
N1 C17 H17A 109.5
N1 C17 H17B 109.5
H17A C17 H17B 109.5
N1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C2 N1 C3 112.11(12)
C2 N1 C17 124.80(13)
C3 N1 C17 122.71(13)
C3 N2 C1 110.77(12)
C3 N2 C4 122.11(12)
C1 N2 C4 111.68(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.4772(18)
C1 C11 1.531(2)
C1 C2 1.535(2)
C1 C10 1.537(2)
C2 O1 1.2138(18)
C2 N1 1.372(2)
C3 O2 1.2112(19)
C3 N2 1.367(2)
C3 N1 1.4053(19)
C4 N2 1.4919(18)
C4 C5 1.536(2)
C4 C9 1.543(2)
C4 H4 1.0000
C5 C6 1.528(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.521(2)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.526(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.527(2)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.5406(19)
C9 H9 1.0000
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.387(2)
C11 C16 1.396(2)
C12 C13 1.395(2)
C12 H12 0.9500
C13 C14 1.383(3)
C13 H13 0.9500
C14 C15 1.388(3)
C14 H14 0.9500
C15 C16 1.390(2)
C15 H15 0.9500
C16 H16 0.9500
C17 N1 1.4606(19)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
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
N2 C1 C2 O1 -174.55(15)
C11 C1 C2 O1 65.87(19)
C10 C1 C2 O1 -62.3(2)
N2 C1 C2 N1 7.50(15)
C11 C1 C2 N1 -112.08(13)
C10 C1 C2 N1 119.72(14)
N2 C4 C5 C6 163.37(12)
C9 C4 C5 C6 49.28(16)
C4 C5 C6 C7 -58.20(17)
C5 C6 C7 C8 59.82(17)
C6 C7 C8 C9 -53.60(18)
C7 C8 C9 C10 -74.31(18)
C7 C8 C9 C4 45.79(18)
N2 C4 C9 C8 -164.18(12)
C5 C4 C9 C8 -43.31(17)
N2 C4 C9 C10 -36.38(13)
C5 C4 C9 C10 84.49(14)
N2 C1 C10 C9 -36.28(14)
C11 C1 C10 C9 85.56(13)
C2 C1 C10 C9 -148.05(13)
C8 C9 C10 C1 171.51(13)
C4 C9 C10 C1 45.46(13)
N2 C1 C11 C12 -1.2(2)
C2 C1 C11 C12 111.57(15)
C10 C1 C11 C12 -117.24(15)
N2 C1 C11 C16 179.09(13)
C2 C1 C11 C16 -68.18(17)
C10 C1 C11 C16 63.01(17)
C16 C11 C12 C13 -0.7(2)
C1 C11 C12 C13 179.57(15)
C11 C12 C13 C14 0.4(2)
C12 C13 C14 C15 0.4(3)
C13 C14 C15 C16 -1.0(2)
C14 C15 C16 C11 0.7(2)
C12 C11 C16 C15 0.1(2)
C1 C11 C16 C15 179.88(14)
O1 C2 N1 C3 172.16(16)
C1 C2 N1 C3 -9.83(15)
O1 C2 N1 C17 -0.9(2)
C1 C2 N1 C17 177.07(14)
O2 C3 N1 C2 -171.53(15)
N2 C3 N1 C2 8.21(16)
O2 C3 N1 C17 1.7(2)
N2 C3 N1 C17 -178.53(14)
O2 C3 N2 C1 176.99(15)
N1 C3 N2 C1 -2.74(16)
O2 C3 N2 C4 42.2(2)
N1 C3 N2 C4 -137.53(13)
C11 C1 N2 C3 113.42(14)
C2 C1 N2 C3 -2.88(15)
C10 C1 N2 C3 -125.33(13)
C11 C1 N2 C4 -106.89(13)
C2 C1 N2 C4 136.81(12)
C10 C1 N2 C4 14.36(15)
C5 C4 N2 C3 27.03(19)
C9 C4 N2 C3 148.17(13)
C5 C4 N2 C1 -107.40(14)
C9 C4 N2 C1 13.74(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168329953
