#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:12:36 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262665 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/21/7242163.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_7242163
loop_
_publ_author_name
'Morita, Shunya'
'Yoshimura, Tomoyuki'
'Matsuo, Jun-ichi'
_publ_section_title
;
 Catalytic intermolecular aldol reactions of transient amide enolates in
 domino Michael/aldol reactions of nitroalkanes, acrylamides, and
 aldehydes
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1160
_journal_page_last               1164
_journal_paper_doi               10.1039/D0GC04111D
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C15 H22 N2 O4'
_chemical_formula_sum            'C15 H22 N2 O4'
_chemical_formula_weight         294.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   9.448(7)
_cell_length_b                   11.423(9)
_cell_length_c                   30.49(2)
_cell_measurement_reflns_used    4603
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.00
_cell_volume                     3291(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            27508
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         2.536
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             1264.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2338
_refine_ls_R_factor_gt           0.1122
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1135P)²+1.0897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2330
_refine_ls_wR_factor_ref         0.2951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1703
_reflns_number_total             3737
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d0gc04111d2.cif
_cod_data_source_block           amide_H_sita3n2
_cod_depositor_comments          'Adding full bibliography for 7242163.cif.'
_cod_database_code               7242163
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8178(3) 0.2538(3) 0.18467(8) 0.0652(10) Uani 1 1 d . . . . .
H1 H 0.765453 0.197210 0.181415 0.078 Uiso 1 1 calc R U . . .
O2 O 0.8433(3) 0.5530(3) 0.19362(10) 0.0696(10) Uani 1 1 d . . . . .
O3 O 1.2165(5) 0.3835(4) 0.07641(15) 0.1164(17) Uani 1 1 d . . . . .
O4 O 1.3103(4) 0.4536(4) 0.13361(17) 0.1188(16) Uani 1 1 d . . . . .
N1 N 1.2221(5) 0.4550(4) 0.10471(16) 0.0702(12) Uani 1 1 d . . . . .
N2 N 1.0087(4) 0.4450(3) 0.22793(11) 0.0574(10) Uani 1 1 d . . . . .
C1 C 0.9299(4) 0.4734(4) 0.19242(13) 0.0455(10) Uani 1 1 d . . . . .
C2 C 0.8306(4) 0.2436(4) 0.10496(13) 0.0458(10) Uani 1 1 d . . . . .
C3 C 0.7493(5) 0.2672(4) 0.06799(14) 0.0643(13) Uani 1 1 d . . . . .
H3 H 0.686800 0.330027 0.068129 0.077 Uiso 1 1 calc R U . . .
C4 C 0.7609(7) 0.1976(6) 0.03094(16) 0.0809(17) Uani 1 1 d . . . . .
H4 H 0.705952 0.214000 0.006385 0.097 Uiso 1 1 calc R U . . .
C5 C 0.8519(6) 0.1056(6) 0.03029(18) 0.0856(18) Uani 1 1 d . . . . .
H5 H 0.859852 0.059504 0.005278 0.103 Uiso 1 1 calc R U . . .
C6 C 0.9324(6) 0.0809(5) 0.06686(18) 0.0783(16) Uani 1 1 d . . . . .
H6 H 0.994433 0.017697 0.066596 0.094 Uiso 1 1 calc R U . . .
C7 C 0.9211(4) 0.1495(4) 0.10363(15) 0.0591(12) Uani 1 1 d . . . . .
H7 H 0.975728 0.131926 0.128131 0.071 Uiso 1 1 calc R U . . .
C8 C 0.8205(4) 0.3210(4) 0.14525(13) 0.0486(11) Uani 1 1 d . . . . .
H8 H 0.734157 0.368264 0.143469 0.058 Uiso 1 1 calc R U . . .
C9 C 0.9494(4) 0.4030(3) 0.15019(12) 0.0428(10) Uani 1 1 d . . . . .
H9 H 1.035467 0.355598 0.152643 0.051 Uiso 1 1 calc R U . . .
C10 C 1.1087(6) 0.3468(5) 0.23090(16) 0.0839(16) Uani 1 1 d . . . . .
H10A H 1.151040 0.345700 0.259527 0.101 Uiso 1 1 calc R U . . .
H10B H 1.059263 0.274534 0.226002 0.101 Uiso 1 1 calc R U . . .
H10C H 1.181271 0.355884 0.209114 0.101 Uiso 1 1 calc R U . . .
C11 C 0.9866(6) 0.5129(5) 0.26814(16) 0.0966(19) Uani 1 1 d . . . . .
H11A H 1.048434 0.484304 0.290716 0.116 Uiso 1 1 calc R U . . .
H11B H 1.006832 0.593851 0.262558 0.116 Uiso 1 1 calc R U . . .
H11C H 0.890052 0.504864 0.277473 0.116 Uiso 1 1 calc R U . . .
C12 C 0.9643(4) 0.4867(4) 0.11086(13) 0.0508(11) Uani 1 1 d . . . . .
H12A H 0.948281 0.442054 0.084269 0.061 Uiso 1 1 calc R U . . .
H12B H 0.889546 0.544714 0.112810 0.061 Uiso 1 1 calc R U . . .
C13 C 1.1061(5) 0.5518(4) 0.10603(14) 0.0543(11) Uani 1 1 d . . . . .
C14 C 1.1417(6) 0.6350(5) 0.14278(19) 0.0895(18) Uani 1 1 d . . . . .
H14A H 1.134469 0.594821 0.170343 0.107 Uiso 1 1 calc R U . . .
H14B H 1.236463 0.663582 0.139022 0.107 Uiso 1 1 calc R U . . .
H14C H 1.076750 0.699657 0.142397 0.107 Uiso 1 1 calc R U . . .
C15 C 1.1162(5) 0.6119(5) 0.06153(17) 0.0805(16) Uani 1 1 d . . . . .
H15A H 1.093032 0.556967 0.038820 0.097 Uiso 1 1 calc R U . . .
H15B H 1.051062 0.676393 0.060556 0.097 Uiso 1 1 calc R U . . .
H15C H 1.210776 0.640318 0.057182 0.097 Uiso 1 1 calc R U . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H1 109.5 . . ?
O3 N1 O4 123.3(6) . . ?
O3 N1 C13 118.4(5) . . ?
O4 N1 C13 118.3(5) . . ?
C1 N2 C11 117.6(4) . . ?
C1 N2 C10 125.9(4) . . ?
C11 N2 C10 116.4(4) . . ?
O2 C1 N2 121.5(4) . . ?
O2 C1 C9 119.8(4) . . ?
N2 C1 C9 118.7(4) . . ?
C7 C2 C3 118.1(4) . . ?
C7 C2 C8 121.3(4) . . ?
C3 C2 C8 120.6(4) . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.0(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 121.3(5) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
O1 C8 C2 111.7(3) . . ?
O1 C8 C9 105.0(3) . . ?
C2 C8 C9 112.6(3) . . ?
O1 C8 H8 109.2 . . ?
C2 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C1 C9 C12 109.9(3) . . ?
C1 C9 C8 107.8(3) . . ?
C12 C9 C8 111.9(3) . . ?
C1 C9 H9 109.1 . . ?
C12 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 117.0(3) . . ?
C13 C12 H12A 108.0 . . ?
C9 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C9 C12 H12B 108.0 . . ?
H12A C12 H12B 107.3 . . ?
C14 C13 C15 111.3(4) . . ?
C14 C13 C12 115.3(4) . . ?
C15 C13 C12 110.9(4) . . ?
C14 C13 N1 108.1(4) . . ?
C15 C13 N1 104.7(4) . . ?
C12 C13 N1 105.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.427(5) . ?
O1 H1 0.8200 . ?
O2 C1 1.224(5) . ?
O3 N1 1.189(5) . ?
O4 N1 1.213(5) . ?
N1 C13 1.557(6) . ?
N2 C1 1.354(5) . ?
N2 C11 1.466(5) . ?
N2 C10 1.470(6) . ?
C1 C9 1.529(5) . ?
C2 C7 1.375(6) . ?
C2 C3 1.390(6) . ?
C2 C8 1.516(6) . ?
C3 C4 1.385(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.543(5) . ?
C8 H8 0.9800 . ?
C9 C12 1.540(5) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.540(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.507(6) . ?
C13 C15 1.523(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 C1 O2 0.2(6) . . . . ?
C10 N2 C1 O2 175.9(4) . . . . ?
C11 N2 C1 C9 -179.2(4) . . . . ?
C10 N2 C1 C9 -3.5(6) . . . . ?
C7 C2 C3 C4 -0.4(6) . . . . ?
C8 C2 C3 C4 178.7(4) . . . . ?
C2 C3 C4 C5 -0.1(8) . . . . ?
C3 C4 C5 C6 0.5(8) . . . . ?
C4 C5 C6 C7 -0.4(8) . . . . ?
C5 C6 C7 C2 -0.1(7) . . . . ?
C3 C2 C7 C6 0.6(6) . . . . ?
C8 C2 C7 C6 -178.6(4) . . . . ?
C7 C2 C8 O1 -43.4(5) . . . . ?
C3 C2 C8 O1 137.5(4) . . . . ?
C7 C2 C8 C9 74.4(5) . . . . ?
C3 C2 C8 C9 -104.7(4) . . . . ?
O2 C1 C9 C12 48.0(5) . . . . ?
N2 C1 C9 C12 -132.6(4) . . . . ?
O2 C1 C9 C8 -74.2(4) . . . . ?
N2 C1 C9 C8 105.3(4) . . . . ?
O1 C8 C9 C1 -56.5(4) . . . . ?
C2 C8 C9 C1 -178.2(3) . . . . ?
O1 C8 C9 C12 -177.4(3) . . . . ?
C2 C8 C9 C12 60.8(4) . . . . ?
C1 C9 C12 C13 74.6(4) . . . . ?
C8 C9 C12 C13 -165.7(3) . . . . ?
C9 C12 C13 C14 -63.4(5) . . . . ?
C9 C12 C13 C15 168.9(4) . . . . ?
C9 C12 C13 N1 56.0(5) . . . . ?
O3 N1 C13 C14 -176.5(4) . . . . ?
O4 N1 C13 C14 6.4(5) . . . . ?
O3 N1 C13 C15 -57.8(5) . . . . ?
O4 N1 C13 C15 125.1(5) . . . . ?
O3 N1 C13 C12 59.5(5) . . . . ?
O4 N1 C13 C12 -117.6(4) . . . . ?
