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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/47/4104770.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.
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data_4104770
loop_
_publ_author_name
'Mathieu Branca'
'Sébastien Pena'
'Régis Guillot'
'Didier Gori'
'Valérie Alezra'
'Cyrille Kouklovsky'
_publ_contact_author_address
;Laboratoire de Chimie des Procédés et Substances Naturelles,
ICMMO, 
CNRS UMR 8182,
Bât 410, 
Univ. Paris-Sud,
F-91405 Orsay. 
;
_publ_contact_author_email       valezra@icmo.u-psud.fr
_publ_contact_author_fax         '(00) 33 1 69 15 46 7'
_publ_contact_author_name        'Valérie Alezra'
_publ_contact_author_phone       '(00) 33 1 69 15 76 5'
_publ_section_title
;
 Memory of Chirality of Tertiary Aromatic Amides: A Simple and Efficient
 Method for the Enantioselective Synthesis of Quaternary α-Amino Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10711
_journal_page_last               10718
_journal_paper_doi               10.1021/ja9039604
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C17 H17 N O3'
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 105.3900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8660(3)
_cell_length_b                   6.7057(2)
_cell_length_c                   14.2336(5)
_cell_measurement_reflns_used    9575
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      47.53
_cell_measurement_theta_min      2.69
_cell_volume                     723.86(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27440
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         47.77
_diffrn_reflns_theta_min         2.69
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         11346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0440
_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)+(0.0765P)²+0.0553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                10407
_reflns_number_total             11346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9039604_si_003.cif
_cod_data_source_block           761GuillotICMMO
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4104770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.13898(7) 0.01787(9) 0.35693(4) 0.01217(8) Uani 1 1 d .
C10 C 0.10254(7) 0.05598(8) 0.25487(4) 0.01047(7) Uani 1 1 d .
C9 C -0.06423(7) 0.02732(9) 0.19484(4) 0.01201(8) Uani 1 1 d .
H9 H -0.0861 0.0522 0.1284 0.014 Uiso 1 1 calc R
C11 C 0.25031(7) 0.10988(9) 0.21108(4) 0.01175(8) Uani 1 1 d .
C6 C -0.00222(8) -0.04815(10) 0.39474(4) 0.01378(8) Uani 1 1 d .
C8 C -0.20257(7) -0.03947(10) 0.23308(4) 0.01402(9) Uani 1 1 d .
H8 H -0.3145 -0.0592 0.1917 0.017 Uiso 1 1 calc R
C7 C -0.17239(8) -0.07525(10) 0.33088(5) 0.01543(9) Uani 1 1 d .
H7 H -0.2645 -0.1177 0.3556 0.019 Uiso 1 1 calc R
C5 C 0.03028(11) -0.08648(12) 0.49596(5) 0.02067(12) Uani 1 1 d .
H5 H -0.0614 -0.1295 0.5208 0.025 Uiso 1 1 calc R
C2 C 0.30810(9) 0.04534(12) 0.42259(5) 0.01812(10) Uani 1 1 d .
H2 H 0.4014 0.0896 0.3994 0.022 Uiso 1 1 calc R
C4 C 0.19477(13) -0.06087(15) 0.55734(5) 0.02570(15) Uani 1 1 d .
H4 H 0.2148 -0.0879 0.6235 0.031 Uiso 1 1 calc R
C3 C 0.33453(11) 0.00673(15) 0.52039(5) 0.02463(14) Uani 1 1 d .
H3 H 0.4458 0.0254 0.5627 0.030 Uiso 1 1 calc R
O1 O 0.37784(6) -0.00213(9) 0.22048(4) 0.01789(9) Uani 1 1 d .
C12 C 0.36578(7) 0.34722(10) 0.10945(4) 0.01239(8) Uani 1 1 d .
C14 C 0.38696(9) 0.19884(12) 0.03308(5) 0.01779(10) Uani 1 1 d .
H14A H 0.2750 0.1779 -0.0132 0.027 Uiso 1 1 calc R
H14B H 0.4297 0.0746 0.0639 0.027 Uiso 1 1 calc R
H14C H 0.4696 0.2500 0.0002 0.027 Uiso 1 1 calc R
C13 C 0.53862(8) 0.40942(12) 0.18029(5) 0.01824(11) Uani 1 1 d .
H13A H 0.6194 0.4533 0.1445 0.027 Uiso 1 1 calc R
H13B H 0.5884 0.2979 0.2206 0.027 Uiso 1 1 calc R
H13C H 0.5172 0.5163 0.2206 0.027 Uiso 1 1 calc R
N1 N 0.23450(6) 0.28319(8) 0.16039(3) 0.01115(7) Uani 1 1 d .
O2 O 0.28576(6) 0.52447(8) 0.05787(3) 0.01472(7) Uani 1 1 d .
O3 O 0.05630(7) 0.72519(9) 0.04852(4) 0.01640(8) Uani 1 1 d .
C16 C 0.10228(7) 0.43725(9) 0.15719(4) 0.01141(7) Uani 1 1 d .
H16 H -0.0160 0.3806 0.1325 0.014 Uiso 1 1 calc R
C15 C 0.13991(7) 0.58057(9) 0.08302(4) 0.01201(8) Uani 1 1 d .
C17 C 0.11727(11) 0.54037(11) 0.25482(5) 0.01928(11) Uani 1 1 d .
H17A H 0.1044 0.4434 0.3021 0.029 Uiso 1 1 calc R
H17B H 0.0263 0.6392 0.2471 0.029 Uiso 1 1 calc R
H17C H 0.2306 0.6033 0.2766 0.029 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
C2 C1 C6 118.61(5)
C2 C1 C10 123.13(5)
C6 C1 C10 118.25(5)
C9 C10 C1 120.53(5)
C9 C10 C11 119.43(5)
C1 C10 C11 119.81(4)
C10 C9 C8 120.66(5)
C10 C9 H9 119.7
C8 C9 H9 119.7
O1 C11 N1 122.50(5)
O1 C11 C10 120.40(5)
N1 C11 C10 117.09(5)
C7 C6 C5 120.91(6)
C7 C6 C1 119.70(5)
C5 C6 C1 119.39(6)
C7 C8 C9 120.24(5)
C7 C8 H8 119.9
C9 C8 H8 119.9
C8 C7 C6 120.61(5)
C8 C7 H7 119.7
C6 C7 H7 119.7
C4 C5 C6 120.77(7)
C4 C5 H5 119.6
C6 C5 H5 119.6
C3 C2 C1 120.32(7)
C3 C2 H2 119.8
C1 C2 H2 119.8
C5 C4 C3 120.04(6)
C5 C4 H4 120.0
C3 C4 H4 120.0
C2 C3 C4 120.87(7)
C2 C3 H3 119.6
C4 C3 H3 119.6
O2 C12 N1 102.77(4)
O2 C12 C14 106.90(5)
N1 C12 C14 112.72(5)
O2 C12 C13 107.61(5)
N1 C12 C13 111.93(5)
C14 C12 C13 114.00(5)
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 N1 C16 125.99(4)
C11 N1 C12 122.27(4)
C16 N1 C12 111.42(4)
C15 O2 C12 112.42(4)
N1 C16 C15 101.64(4)
N1 C16 C17 114.20(5)
C15 C16 C17 111.38(5)
N1 C16 H16 109.8
C15 C16 H16 109.8
C17 C16 H16 109.8
O3 C15 O2 122.07(5)
O3 C15 C16 127.63(5)
O2 C15 C16 110.30(5)
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.4203(8)
C1 C6 1.4271(8)
C1 C10 1.4271(7)
C10 C9 1.3759(7)
C10 C11 1.5016(7)
C9 C8 1.4126(7)
C9 H9 0.9300
C11 O1 1.2317(7)
C11 N1 1.3562(8)
C6 C7 1.4160(9)
C6 C5 1.4183(8)
C8 C7 1.3697(9)
C8 H8 0.9300
C7 H7 0.9300
C5 C4 1.3663(12)
C5 H5 0.9300
C2 C3 1.3764(10)
C2 H2 0.9300
C4 C3 1.4133(13)
C4 H4 0.9300
C3 H3 0.9300
C12 O2 1.4501(8)
C12 N1 1.4744(7)
C12 C14 1.5151(9)
C12 C13 1.5203(8)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
N1 C16 1.4580(7)
O2 C15 1.3431(7)
O3 C15 1.2011(8)
C16 C15 1.5138(8)
C16 C17 1.5285(8)
C16 H16 0.9800
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
C2 C1 C10 C9 -179.76(6)
C6 C1 C10 C9 -0.71(9)
C2 C1 C10 C11 5.80(9)
C6 C1 C10 C11 -175.16(5)
C1 C10 C9 C8 0.27(9)
C11 C10 C9 C8 174.73(5)
C9 C10 C11 O1 -117.63(7)
C1 C10 C11 O1 56.87(8)
C9 C10 C11 N1 61.32(7)
C1 C10 C11 N1 -124.18(6)
C2 C1 C6 C7 179.53(6)
C10 C1 C6 C7 0.45(9)
C2 C1 C6 C5 -0.71(9)
C10 C1 C6 C5 -179.80(6)
C10 C9 C8 C7 0.47(10)
C9 C8 C7 C6 -0.74(10)
C5 C6 C7 C8 -179.48(7)
C1 C6 C7 C8 0.27(10)
C7 C6 C5 C4 179.77(8)
C1 C6 C5 C4 0.01(11)
C6 C1 C2 C3 0.67(11)
C10 C1 C2 C3 179.71(7)
C6 C5 C4 C3 0.73(14)
C1 C2 C3 C4 0.06(14)
C5 C4 C3 C2 -0.78(15)
O1 C11 N1 C16 -170.66(6)
C10 C11 N1 C16 10.41(8)
O1 C11 N1 C12 2.35(9)
C10 C11 N1 C12 -176.58(5)
O2 C12 N1 C11 173.91(5)
C14 C12 N1 C11 59.20(7)
C13 C12 N1 C11 -70.89(7)
O2 C12 N1 C16 -12.16(6)
C14 C12 N1 C16 -126.87(5)
C13 C12 N1 C16 103.04(6)
N1 C12 O2 C15 7.84(6)
C14 C12 O2 C15 126.70(5)
C13 C12 O2 C15 -110.44(6)
C11 N1 C16 C15 -174.88(5)
C12 N1 C16 C15 11.47(6)
C11 N1 C16 C17 65.08(8)
C12 N1 C16 C17 -108.58(6)
C12 O2 C15 O3 179.38(6)
C12 O2 C15 C16 -0.96(7)
N1 C16 C15 O3 173.23(6)
C17 C16 C15 O3 -64.77(8)
N1 C16 C15 O2 -6.41(6)
C17 C16 C15 O2 115.59(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101481067
