#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/37/1553746.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_1553746
loop_
_publ_author_name
'Wang, Bin'
'Xu, Tong'
'Zhu, Lei'
'Lan, Yu'
'Wang, Jingdong'
'Lu, Ning'
'Wei, Zhonglin'
'Lin, Yingjie'
'Duan, Haifeng'
_publ_section_title
;
 Highly enantioselective nitro-Mannich reaction of ketimines under
 phase-transfer catalysis
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1266
_journal_paper_doi               10.1039/C7QO00124J
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_sum            'C15 H17 N3 O4 S'
_chemical_formula_weight         335.38
_chemical_name_systematic
(R)-6-methyl-N-(1-nitro-2-phenylpropan-2-yl)pyridine-2-sulfonamide
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2016-06-27 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.429(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6132(15)
_cell_length_b                   7.4744(14)
_cell_length_c                   12.867(3)
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.51
_cell_volume                     781.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5194
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0352
_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)+(0.0499P)²+0.0523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                2581
_reflns_number_total             2777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00124j2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

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

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/RSC/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      P2(1)
_cod_database_code               1553746
_solvent_exptl_crystal_recrystallization_method 'dichloromethane, isopropanol'
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 1.0316(3) 0.2617(6) 0.5061(3) 0.0672(11) Uani 1 1 d .
H1A H 1.0049 0.3220 0.5638 0.101 Uiso 1 1 calc R
H1B H 1.0984 0.3383 0.4785 0.101 Uiso 1 1 calc R
H1C H 1.0912 0.1539 0.5347 0.101 Uiso 1 1 calc R
C2 C 0.8766(3) 0.2160(4) 0.4148(2) 0.0392(6) Uani 1 1 d .
C3 C 0.8802(3) 0.1439(4) 0.3166(2) 0.0395(6) Uani 1 1 d .
H3 H 0.9802 0.1300 0.3045 0.047 Uiso 1 1 calc R
C4 C 0.7369(3) 0.0930(4) 0.2372(2) 0.0417(7) Uani 1 1 d .
H4 H 0.7386 0.0439 0.1712 0.050 Uiso 1 1 calc R
C5 C 0.5901(3) 0.1155(4) 0.2565(2) 0.0357(6) Uani 1 1 d .
H5 H 0.4905 0.0797 0.2054 0.043 Uiso 1 1 calc R
C6 C 0.5975(3) 0.1930(3) 0.35452(19) 0.0283(5) Uani 1 1 d .
C7 C 0.5237(3) 0.4434(4) 0.0394(2) 0.0384(6) Uani 1 1 d .
H7 H 0.5074 0.3892 -0.0285 0.046 Uiso 1 1 calc R
C8 C 0.6717(3) 0.5218(4) 0.0942(2) 0.0394(6) Uani 1 1 d .
H8 H 0.7556 0.5217 0.0636 0.047 Uiso 1 1 calc R
C9 C 0.6957(3) 0.6010(4) 0.1950(2) 0.0395(6) Uani 1 1 d .
H9 H 0.7959 0.6551 0.2326 0.047 Uiso 1 1 calc R
C10 C 0.5716(3) 0.6001(3) 0.24040(19) 0.0318(5) Uani 1 1 d .
H10 H 0.5893 0.6528 0.3089 0.038 Uiso 1 1 calc R
C11 C 0.4205(2) 0.5217(3) 0.18516(18) 0.0241(5) Uani 1 1 d .
C12 C 0.3978(3) 0.4438(4) 0.08385(19) 0.0327(6) Uani 1 1 d .
H12 H 0.2972 0.3913 0.0452 0.039 Uiso 1 1 calc R
C13 C 0.2873(3) 0.5188(3) 0.24059(18) 0.0254(5) Uani 1 1 d .
C14 C 0.1302(3) 0.4219(4) 0.1724(2) 0.0362(6) Uani 1 1 d .
H14A H 0.1571 0.3030 0.1559 0.054 Uiso 1 1 calc R
H14B H 0.0792 0.4861 0.1050 0.054 Uiso 1 1 calc R
H14C H 0.0556 0.4158 0.2136 0.054 Uiso 1 1 calc R
C15 C 0.2435(3) 0.7098(3) 0.26739(19) 0.0314(6) Uani 1 1 d .
H15A H 0.1786 0.7024 0.3160 0.038 Uiso 1 1 calc R
H15B H 0.3441 0.7739 0.3060 0.038 Uiso 1 1 calc R
N1 N 0.7345(2) 0.2431(4) 0.43392(15) 0.0347(4) Uani 1 1 d .
N2 N 0.3535(2) 0.4393(3) 0.35362(15) 0.0268(4) Uani 1 1 d .
H2 H 0.3616 0.5098 0.4080 0.032 Uiso 1 1 calc R
N3 N 0.1496(3) 0.8114(3) 0.16674(19) 0.0386(5) Uani 1 1 d .
O1 O 0.44980(18) 0.2246(3) 0.50096(13) 0.0399(4) Uani 1 1 d .
O2 O 0.2900(2) 0.1182(2) 0.31421(15) 0.0396(4) Uani 1 1 d .
O3 O 0.0055(2) 0.8400(4) 0.1511(2) 0.0695(7) Uani 1 1 d .
O4 O 0.2229(3) 0.8613(3) 0.10723(17) 0.0612(6) Uani 1 1 d .
S1 S 0.41150(6) 0.23440(7) 0.38395(4) 0.02731(15) 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
N1 C2 C3 121.7(2)
N1 C2 C1 116.9(2)
C3 C2 C1 121.4(2)
C4 C3 C2 120.1(2)
C3 C4 C5 119.1(3)
C6 C5 C4 116.9(2)
N1 C6 C5 125.7(2)
N1 C6 S1 114.56(17)
C5 C6 S1 119.75(17)
C8 C7 C12 120.7(2)
C7 C8 C9 119.4(2)
C10 C9 C8 120.2(2)
C9 C10 C11 120.8(2)
C12 C11 C10 118.4(2)
C12 C11 C13 122.56(19)
C10 C11 C13 119.00(19)
C11 C12 C7 120.4(2)
N2 C13 C14 110.36(18)
N2 C13 C11 110.71(17)
C14 C13 C11 113.26(18)
N2 C13 C15 101.09(18)
C14 C13 C15 109.31(19)
C11 C13 C15 111.43(18)
N3 C15 C13 112.33(19)
C6 N1 C2 116.5(2)
C13 N2 S1 126.68(16)
O4 N3 O3 124.5(2)
O4 N3 C15 117.7(2)
O3 N3 C15 117.8(2)
O2 S1 O1 119.67(11)
O2 S1 N2 108.80(10)
O1 S1 N2 104.28(11)
O2 S1 C6 106.42(11)
O1 S1 C6 107.69(10)
N2 S1 C6 109.78(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.496(4)
C2 N1 1.341(3)
C2 C3 1.384(4)
C3 C4 1.369(4)
C4 C5 1.378(4)
C5 C6 1.370(3)
C6 N1 1.332(3)
C6 S1 1.792(2)
C7 C8 1.366(4)
C7 C12 1.384(3)
C8 C9 1.378(4)
C9 C10 1.378(3)
C10 C11 1.388(3)
C11 C12 1.381(3)
C11 C13 1.540(3)
C13 N2 1.497(3)
C13 C14 1.528(3)
C13 C15 1.545(3)
C15 N3 1.487(3)
N2 S1 1.618(2)
N3 O4 1.202(3)
N3 O3 1.209(3)
O1 S1 1.4320(17)
O2 S1 1.4250(17)
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
N1 C2 C3 C4 -2.1(4)
C1 C2 C3 C4 175.9(3)
C2 C3 C4 C5 0.3(4)
C3 C4 C5 C6 1.7(4)
C4 C5 C6 N1 -2.3(4)
C4 C5 C6 S1 177.8(2)
C12 C7 C8 C9 0.4(4)
C7 C8 C9 C10 0.4(4)
C8 C9 C10 C11 -0.7(4)
C9 C10 C11 C12 0.3(4)
C9 C10 C11 C13 178.1(2)
C10 C11 C12 C7 0.5(4)
C13 C11 C12 C7 -177.3(2)
C8 C7 C12 C11 -0.8(4)
C12 C11 C13 N2 124.6(2)
C10 C11 C13 N2 -53.1(3)
C12 C11 C13 C14 0.0(3)
C10 C11 C13 C14 -177.7(2)
C12 C11 C13 C15 -123.7(2)
C10 C11 C13 C15 58.5(3)
N2 C13 C15 N3 -171.07(18)
C14 C13 C15 N3 -54.7(2)
C11 C13 C15 N3 71.3(2)
C5 C6 N1 C2 0.6(4)
S1 C6 N1 C2 -179.4(2)
C3 C2 N1 C6 1.6(4)
C1 C2 N1 C6 -176.4(3)
C14 C13 N2 S1 60.1(2)
C11 C13 N2 S1 -66.1(2)
C15 C13 N2 S1 175.72(15)
C13 C15 N3 O4 -72.2(3)
C13 C15 N3 O3 108.7(3)
C13 N2 S1 O2 -46.3(2)
C13 N2 S1 O1 -175.03(17)
C13 N2 S1 C6 69.83(19)
N1 C6 S1 O2 -159.02(19)
C5 C6 S1 O2 21.0(2)
N1 C6 S1 O1 -29.5(2)
C5 C6 S1 O1 150.4(2)
N1 C6 S1 N2 83.4(2)
C5 C6 S1 N2 -96.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304006
