#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/18/7111809.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_7111809
loop_
_publ_author_name
'Alex Lauber'
'Benjamin Zelenay'
'Jan Cvengros'
_publ_section_title
;
 Asymmetric synthesis of N-stereogenic molecules: diastereoselective
 double aza-Michael reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              1195
_journal_paper_doi               10.1039/c3cc48486f
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C19 H20 N2 O2, 0.5 (C2 H4 Cl2)'
_chemical_formula_sum            'C20 H22 Cl N2 O2'
_chemical_formula_weight         357.85
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.755(2)
_cell_angle_beta                 99.390(2)
_cell_angle_gamma                92.439(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1957(9)
_cell_length_b                   8.7315(9)
_cell_length_c                   12.9688(14)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.52
_cell_volume                     907.46(17)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0847
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11358
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9394
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS-2004/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       'not measured'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                2918
_reflns_number_total             4654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48486f.txt
_cod_data_source_block           bz_057_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7111809
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 0.39810(7) 0.18385(6) 0.58961(5) 0.04042(17) Uani 1 1 d .
C20 C 0.5010(3) 0.0124(2) 0.55768(16) 0.0344(5) Uani 1 1 d .
H20A H 0.6168 0.0232 0.5955 0.041 Uiso 1 1 calc R
H20B H 0.4441 -0.0774 0.5798 0.041 Uiso 1 1 calc R
O1 O 0.32551(15) 0.50641(13) 1.04028(9) 0.0215(3) Uani 1 1 d .
H1 H 0.3720 0.4385 1.0733 0.032 Uiso 1 1 calc R
O2 O 0.32644(15) 0.32988(14) 0.89996(10) 0.0250(3) Uani 1 1 d .
N1 N 0.48358(16) 0.67003(15) 0.84076(11) 0.0144(3) Uani 1 1 d .
N2 N 0.24502(16) 0.82351(15) 0.81183(10) 0.0142(3) Uani 1 1 d .
C1 C 0.3137(2) 0.65097(19) 0.66156(13) 0.0167(4) Uani 1 1 d .
C2 C 0.22353(19) 0.76989(19) 0.70133(13) 0.0158(4) Uani 1 1 d .
C3 C 0.1054(2) 0.8350(2) 0.63217(14) 0.0214(4) Uani 1 1 d .
H3 H 0.0450 0.9172 0.6583 0.026 Uiso 1 1 calc R
C4 C 0.0757(2) 0.7803(2) 0.52557(15) 0.0261(4) Uani 1 1 d .
H4 H -0.0036 0.8269 0.4792 0.031 Uiso 1 1 calc R
C5 C 0.1602(2) 0.6584(2) 0.48547(14) 0.0250(4) Uani 1 1 d .
C6 C 0.2792(2) 0.5962(2) 0.55451(14) 0.0220(4) Uani 1 1 d .
H6 H 0.3390 0.5138 0.5280 0.026 Uiso 1 1 calc R
C7 C 0.1235(3) 0.5953(3) 0.36986(15) 0.0369(5) Uani 1 1 d .
H7A H 0.2138 0.6291 0.3351 0.055 Uiso 1 1 calc R
H7B H 0.0194 0.6337 0.3371 0.055 Uiso 1 1 calc R
H7C H 0.1136 0.4821 0.3624 0.055 Uiso 1 1 calc R
C8 C 0.4453(2) 0.58063(19) 0.73376(13) 0.0178(4) Uani 1 1 d .
H8A H 0.4073 0.4734 0.7399 0.021 Uiso 1 1 calc R
H8B H 0.5477 0.5762 0.7024 0.021 Uiso 1 1 calc R
C9 C 0.32553(19) 0.71307(18) 0.87603(13) 0.0152(3) Uani 1 1 d .
H9 H 0.3536 0.7650 0.9502 0.018 Uiso 1 1 calc R
C10 C 0.34094(19) 0.97351(18) 0.84101(13) 0.0158(3) Uani 1 1 d .
H10A H 0.3206 1.0207 0.9106 0.019 Uiso 1 1 calc R
H10B H 0.3030 1.0439 0.7887 0.019 Uiso 1 1 calc R
C11 C 0.52459(19) 0.95541(18) 0.84568(12) 0.0145(3) Uani 1 1 d .
C12 C 0.6344(2) 1.08453(19) 0.85367(13) 0.0169(4) Uani 1 1 d .
H12 H 0.5921 1.1842 0.8555 0.020 Uiso 1 1 calc R
C13 C 0.8044(2) 1.0715(2) 0.85905(13) 0.0182(4) Uani 1 1 d .
C14 C 0.8630(2) 0.9234(2) 0.85304(14) 0.0207(4) Uani 1 1 d .
H14 H 0.9781 0.9116 0.8549 0.025 Uiso 1 1 calc R
C15 C 0.7572(2) 0.7945(2) 0.84449(13) 0.0187(4) Uani 1 1 d .
H15 H 0.7995 0.6948 0.8402 0.022 Uiso 1 1 calc R
C16 C 0.58758(19) 0.80965(19) 0.84216(12) 0.0145(3) Uani 1 1 d .
C17 C 0.9244(2) 1.2104(2) 0.87282(15) 0.0258(4) Uani 1 1 d .
H17A H 0.8631 1.3042 0.8711 0.039 Uiso 1 1 calc R
H17B H 0.9897 1.2020 0.8157 0.039 Uiso 1 1 calc R
H17C H 0.9987 1.2155 0.9407 0.039 Uiso 1 1 calc R
C18 C 0.2078(2) 0.57195(19) 0.87550(14) 0.0181(4) Uani 1 1 d .
H18A H 0.1096 0.6053 0.9056 0.022 Uiso 1 1 calc R
H18B H 0.1692 0.5242 0.8020 0.022 Uiso 1 1 calc R
C19 C 0.2914(2) 0.45454(19) 0.93822(14) 0.0179(4) 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'
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
_geom_angle_site_symmetry_1
C20 C20 Cl1 109.10(19) 2_656
C16 N1 C8 111.84(13) .
C16 N1 C9 109.13(12) .
C8 N1 C9 109.11(12) .
C2 N2 C9 112.23(12) .
C2 N2 C10 113.17(13) .
C9 N2 C10 108.07(12) .
C6 C1 C2 119.25(16) .
C6 C1 C8 120.16(15) .
C2 C1 C8 120.58(14) .
C3 C2 C1 119.21(15) .
C3 C2 N2 118.94(14) .
C1 C2 N2 121.81(14) .
C4 C3 C2 120.35(16) .
C3 C4 C5 121.07(17) .
C6 C5 C4 118.12(16) .
C6 C5 C7 120.85(17) .
C4 C5 C7 121.03(17) .
C5 C6 C1 121.94(16) .
N1 C8 C1 112.30(13) .
N2 C9 N1 110.43(13) .
N2 C9 C18 110.81(13) .
N1 C9 C18 112.36(13) .
N2 C10 C11 111.51(13) .
C16 C11 C12 118.63(15) .
C16 C11 C10 120.69(14) .
C12 C11 C10 120.67(14) .
C13 C12 C11 121.95(15) .
C12 C13 C14 117.93(15) .
C12 C13 C17 122.26(16) .
C14 C13 C17 119.80(15) .
C15 C14 C13 121.18(16) .
C14 C15 C16 120.22(16) .
C11 C16 C15 120.04(15) .
C11 C16 N1 122.20(14) .
C15 C16 N1 117.70(14) .
C19 C18 C9 111.33(13) .
O2 C19 O1 124.36(16) .
O2 C19 C18 124.02(16) .
O1 C19 C18 111.60(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C20 1.7884(19) .
C20 C20 1.484(4) 2_656
O1 C19 1.328(2) .
O2 C19 1.208(2) .
N1 C16 1.454(2) .
N1 C8 1.489(2) .
N1 C9 1.491(2) .
N2 C2 1.434(2) .
N2 C9 1.457(2) .
N2 C10 1.475(2) .
C1 C6 1.393(2) .
C1 C2 1.398(2) .
C1 C8 1.510(2) .
C2 C3 1.396(2) .
C3 C4 1.387(2) .
C4 C5 1.390(3) .
C5 C6 1.387(3) .
C5 C7 1.512(3) .
C9 C18 1.531(2) .
C10 C11 1.512(2) .
C11 C16 1.392(2) .
C11 C12 1.396(2) .
C12 C13 1.393(2) .
C13 C14 1.397(2) .
C13 C17 1.503(2) .
C14 C15 1.373(2) .
C15 C16 1.398(2) .
C18 C19 1.502(2) .
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
C6 C1 C2 C3 -2.4(3)
C8 C1 C2 C3 178.51(15)
C6 C1 C2 N2 175.46(15)
C8 C1 C2 N2 -3.6(2)
C9 N2 C2 C3 159.85(15)
C10 N2 C2 C3 -77.50(18)
C9 N2 C2 C1 -18.0(2)
C10 N2 C2 C1 104.63(17)
C1 C2 C3 C4 1.2(3)
N2 C2 C3 C4 -176.73(16)
C2 C3 C4 C5 1.1(3)
C3 C4 C5 C6 -2.1(3)
C3 C4 C5 C7 177.88(18)
C4 C5 C6 C1 0.9(3)
C7 C5 C6 C1 -179.13(17)
C2 C1 C6 C5 1.4(3)
C8 C1 C6 C5 -179.52(17)
C16 N1 C8 C1 -77.06(17)
C9 N1 C8 C1 43.76(18)
C6 C1 C8 N1 170.69(15)
C2 C1 C8 N1 -10.2(2)
C2 N2 C9 N1 53.24(16)
C10 N2 C9 N1 -72.25(15)
C2 N2 C9 C18 -71.92(17)
C10 N2 C9 C18 162.59(13)
C16 N1 C9 N2 55.04(16)
C8 N1 C9 N2 -67.42(16)
C16 N1 C9 C18 179.32(13)
C8 N1 C9 C18 56.86(17)
C2 N2 C10 C11 -77.73(17)
C9 N2 C10 C11 47.20(17)
N2 C10 C11 C16 -11.3(2)
N2 C10 C11 C12 168.76(14)
C16 C11 C12 C13 -0.5(2)
C10 C11 C12 C13 179.42(15)
C11 C12 C13 C14 1.9(2)
C11 C12 C13 C17 -177.04(16)
C12 C13 C14 C15 -1.4(3)
C17 C13 C14 C15 177.50(17)
C13 C14 C15 C16 -0.3(3)
C12 C11 C16 C15 -1.3(2)
C10 C11 C16 C15 178.76(15)
C12 C11 C16 N1 175.93(15)
C10 C11 C16 N1 -4.0(2)
C14 C15 C16 C11 1.7(3)
C14 C15 C16 N1 -175.61(15)
C8 N1 C16 C11 103.75(17)
C9 N1 C16 C11 -17.1(2)
C8 N1 C16 C15 -78.99(17)
C9 N1 C16 C15 160.20(14)
N2 C9 C18 C19 177.92(13)
N1 C9 C18 C19 53.86(19)
C9 C18 C19 O2 -110.95(19)
C9 C18 C19 O1 67.45(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184211
