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#$Date: 2023-01-06 12:05:14 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280221 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106427.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_8106427
loop_
_publ_author_name
'Li, Jingwei'
'Lin, Jiali'
'Zhang, Mingna'
'Wang, Ke'
'He, Jieli'
_publ_section_title
;
 Crystal structure of
 2-amino-5-oxo-4-(3,4,5-trimethoxy-phenyl)-4,5,6,7-tetrahydro-cyclopenta[b]pyran-3-carbonitrile,
 C18H18N2O5
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              47
_journal_page_last               48
_journal_paper_doi               10.1515/ncrs-2016-0133
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C18 H18 N2 O5'
_chemical_formula_weight         342.34
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.853(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.605(5)
_cell_length_b                   8.496(4)
_cell_length_c                   23.771(5)
_cell_measurement_reflns_used    1990
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.42
_cell_measurement_theta_min      2.45
_cell_volume                     1728.8(13)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8366
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0461
_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)+(0.0686P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                1955
_reflns_number_total             3037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0133_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1728.7(12)
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               8106427
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8123(2) 1.0451(2) 0.01158(9) 0.0690(6) Uani 1 1 d . . .
N2 N 1.00818(19) 0.6845(2) 0.04280(8) 0.0650(5) Uani 1 1 d . . .
H2A H 1.0359 0.7715 0.0282 0.078 Uiso 1 1 calc R . .
H2B H 1.0739 0.6084 0.0482 0.078 Uiso 1 1 calc R . .
C1 C 0.7802(2) 0.9242(3) 0.02946(9) 0.0493(5) Uani 1 1 d . . .
C2 C 0.7445(2) 0.7751(2) 0.05173(8) 0.0448(5) Uani 1 1 d . . .
C3 C 0.8629(2) 0.6678(2) 0.05715(8) 0.0475(5) Uani 1 1 d . . .
C4 C 0.6944(2) 0.4769(2) 0.08666(8) 0.0484(5) Uani 1 1 d . . .
C5 C 0.5695(2) 0.5721(2) 0.07979(8) 0.0442(5) Uani 1 1 d . . .
C6 C 0.5810(2) 0.7465(2) 0.06923(8) 0.0440(5) Uani 1 1 d . . .
H6A H 0.5045 0.7745 0.0374 0.053 Uiso 1 1 calc R . .
C7 C 0.4306(3) 0.4763(2) 0.08262(9) 0.0543(6) Uani 1 1 d . . .
C8 C 0.4827(3) 0.3097(2) 0.09900(10) 0.0649(6) Uani 1 1 d . . .
H8A H 0.4386 0.2347 0.0710 0.078 Uiso 1 1 calc R . .
H8B H 0.4495 0.2816 0.1355 0.078 Uiso 1 1 calc R . .
C9 C 0.6624(3) 0.3103(2) 0.10160(10) 0.0646(6) Uani 1 1 d . . .
H9A H 0.7102 0.2841 0.1392 0.078 Uiso 1 1 calc R . .
H9B H 0.6992 0.2375 0.0744 0.078 Uiso 1 1 calc R . .
C10 C 0.5444(2) 0.8420(2) 0.12145(8) 0.0438(5) Uani 1 1 d . . .
C11 C 0.6590(2) 0.8680(2) 0.16691(8) 0.0537(6) Uani 1 1 d . . .
H11A H 0.7597 0.8297 0.1654 0.064 Uiso 1 1 calc R . .
C12 C 0.6219(3) 0.9515(3) 0.21457(9) 0.0563(6) Uani 1 1 d . . .
C13 C 0.4717(2) 1.0114(2) 0.21694(9) 0.0533(6) Uani 1 1 d . . .
C14 C 0.3591(2) 0.9870(2) 0.17102(10) 0.0521(5) Uani 1 1 d . . .
C15 C 0.3939(2) 0.9013(2) 0.12385(9) 0.0477(5) Uani 1 1 d . . .
H15A H 0.3171 0.8836 0.0941 0.057 Uiso 1 1 calc R . .
C16 C 0.8881(3) 0.9768(4) 0.25528(11) 0.0914(9) Uani 1 1 d . . .
H16A H 0.9469 1.0012 0.2907 0.137 Uiso 1 1 calc R . .
H16B H 0.9123 1.0517 0.2272 0.137 Uiso 1 1 calc R . .
H16C H 0.9147 0.8729 0.2436 0.137 Uiso 1 1 calc R . .
C17 C 0.3517(4) 1.0338(4) 0.30189(12) 0.1085(11) Uani 1 1 d . . .
H17A H 0.3360 1.1076 0.3314 0.163 Uiso 1 1 calc R . .
H17B H 0.4059 0.9430 0.3179 0.163 Uiso 1 1 calc R . .
H17C H 0.2523 1.0023 0.2833 0.163 Uiso 1 1 calc R . .
C18 C 0.1045(3) 1.0585(3) 0.12766(12) 0.0881(9) Uani 1 1 d . . .
H18A H 0.0119 1.1117 0.1367 0.132 Uiso 1 1 calc R . .
H18B H 0.0792 0.9521 0.1167 0.132 Uiso 1 1 calc R . .
H18C H 0.1466 1.1120 0.0970 0.132 Uiso 1 1 calc R . .
O1 O 0.84418(15) 0.51881(15) 0.07943(6) 0.0566(4) Uani 1 1 d . . .
O2 O 0.29468(19) 0.51813(19) 0.07199(8) 0.0786(5) Uani 1 1 d . . .
O3 O 0.7275(2) 0.9834(2) 0.26161(7) 0.0848(6) Uani 1 1 d . . .
O4 O 0.44150(19) 1.1052(2) 0.26220(7) 0.0787(5) Uani 1 1 d . . .
O5 O 0.21707(18) 1.0581(2) 0.17584(7) 0.0767(5) 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'
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
C3 N2 H2A 120.0 . .
C3 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
N1 C1 C2 178.7(2) . .
C3 C2 C1 116.34(17) . .
C3 C2 C6 124.62(17) . .
C1 C2 C6 119.02(16) . .
N2 C3 C2 127.88(18) . .
N2 C3 O1 110.05(16) . .
C2 C3 O1 122.07(17) . .
C5 C4 O1 125.62(18) . .
C5 C4 C9 115.83(19) . .
O1 C4 C9 118.52(17) . .
C4 C5 C7 108.03(18) . .
C4 C5 C6 123.16(18) . .
C7 C5 C6 128.78(17) . .
C5 C6 C2 106.27(14) . .
C5 C6 C10 111.15(15) . .
C2 C6 C10 113.90(15) . .
C5 C6 H6A 108.5 . .
C2 C6 H6A 108.5 . .
C10 C6 H6A 108.5 . .
O2 C7 C5 127.0(2) . .
O2 C7 C8 124.9(2) . .
C5 C7 C8 108.06(18) . .
C7 C8 C9 105.97(17) . .
C7 C8 H8A 110.5 . .
C9 C8 H8A 110.5 . .
C7 C8 H8B 110.5 . .
C9 C8 H8B 110.5 . .
H8A C8 H8B 108.7 . .
C4 C9 C8 101.68(16) . .
C4 C9 H9A 111.4 . .
C8 C9 H9A 111.4 . .
C4 C9 H9B 111.4 . .
C8 C9 H9B 111.4 . .
H9A C9 H9B 109.3 . .
C15 C10 C11 119.57(18) . .
C15 C10 C6 119.27(17) . .
C11 C10 C6 121.15(16) . .
C12 C11 C10 120.16(19) . .
C12 C11 H11A 119.9 . .
C10 C11 H11A 119.9 . .
O3 C12 C13 115.32(19) . .
O3 C12 C11 124.3(2) . .
C13 C12 C11 120.35(19) . .
O4 C13 C12 119.30(19) . .
O4 C13 C14 121.40(19) . .
C12 C13 C14 119.04(19) . .
O5 C14 C15 124.12(19) . .
O5 C14 C13 114.80(18) . .
C15 C14 C13 121.04(18) . .
C14 C15 C10 119.82(19) . .
C14 C15 H15A 120.1 . .
C10 C15 H15A 120.1 . .
O3 C16 H16A 109.5 . .
O3 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
O3 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
O4 C17 H17A 109.5 . .
O4 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
O4 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O5 C18 H18A 109.5 . .
O5 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O5 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C4 O1 C3 115.74(14) . .
C12 O3 C16 118.28(18) . .
C13 O4 C17 115.4(2) . .
C14 O5 C18 118.06(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.156(3) .
N2 C3 1.336(2) .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
C1 C2 1.419(3) .
C2 C3 1.364(3) .
C2 C6 1.526(3) .
C3 O1 1.388(2) .
C4 C5 1.342(3) .
C4 O1 1.365(2) .
C4 C9 1.492(3) .
C5 C7 1.453(3) .
C5 C6 1.508(3) .
C6 C10 1.542(3) .
C6 H6A 0.9800 .
C7 O2 1.224(2) .
C7 C8 1.524(3) .
C8 C9 1.541(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C15 1.396(3) .
C10 C11 1.404(3) .
C11 C12 1.401(3) .
C11 H11A 0.9300 .
C12 O3 1.393(3) .
C12 C13 1.395(3) .
C13 O4 1.385(2) .
C13 C14 1.400(3) .
C14 O5 1.379(2) .
C14 C15 1.395(3) .
C15 H15A 0.9300 .
C16 O3 1.406(3) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 O4 1.416(3) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 O5 1.422(3) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 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
N1 C1 C2 C3 -20(10) . . . .
N1 C1 C2 C6 159(100) . . . .
C1 C2 C3 N2 -1.7(3) . . . .
C6 C2 C3 N2 179.97(19) . . . .
C1 C2 C3 O1 178.67(17) . . . .
C6 C2 C3 O1 0.3(3) . . . .
O1 C4 C5 C7 171.03(19) . . . .
C9 C4 C5 C7 -6.8(2) . . . .
O1 C4 C5 C6 -7.2(3) . . . .
C9 C4 C5 C6 174.98(18) . . . .
C4 C5 C6 C2 15.9(2) . . . .
C7 C5 C6 C2 -161.95(19) . . . .
C4 C5 C6 C10 -108.6(2) . . . .
C7 C5 C6 C10 73.6(2) . . . .
C3 C2 C6 C5 -12.7(2) . . . .
C1 C2 C6 C5 169.03(17) . . . .
C3 C2 C6 C10 110.0(2) . . . .
C1 C2 C6 C10 -68.3(2) . . . .
C4 C5 C7 O2 -171.2(2) . . . .
C6 C5 C7 O2 6.9(3) . . . .
C4 C5 C7 C8 6.5(2) . . . .
C6 C5 C7 C8 -175.48(19) . . . .
O2 C7 C8 C9 173.8(2) . . . .
C5 C7 C8 C9 -3.9(2) . . . .
C5 C4 C9 C8 4.1(2) . . . .
O1 C4 C9 C8 -173.89(18) . . . .
C7 C8 C9 C4 0.2(2) . . . .
C5 C6 C10 C15 -96.6(2) . . . .
C2 C6 C10 C15 143.38(17) . . . .
C5 C6 C10 C11 82.3(2) . . . .
C2 C6 C10 C11 -37.7(2) . . . .
C15 C10 C11 C12 0.6(3) . . . .
C6 C10 C11 C12 -178.27(18) . . . .
C10 C11 C12 O3 -179.87(19) . . . .
C10 C11 C12 C13 -0.9(3) . . . .
O3 C12 C13 O4 4.7(3) . . . .
C11 C12 C13 O4 -174.35(19) . . . .
O3 C12 C13 C14 178.95(19) . . . .
C11 C12 C13 C14 -0.1(3) . . . .
O4 C13 C14 O5 -2.3(3) . . . .
C12 C13 C14 O5 -176.42(18) . . . .
O4 C13 C14 C15 175.54(18) . . . .
C12 C13 C14 C15 1.4(3) . . . .
O5 C14 C15 C10 175.92(18) . . . .
C13 C14 C15 C10 -1.7(3) . . . .
C11 C10 C15 C14 0.7(3) . . . .
C6 C10 C15 C14 179.59(17) . . . .
C5 C4 O1 C3 -7.4(3) . . . .
C9 C4 O1 C3 170.37(18) . . . .
N2 C3 O1 C4 -169.08(17) . . . .
C2 C3 O1 C4 10.6(3) . . . .
C13 C12 O3 C16 -158.5(2) . . . .
C11 C12 O3 C16 20.6(3) . . . .
C12 C13 O4 C17 -107.1(3) . . . .
C14 C13 O4 C17 78.8(3) . . . .
C15 C14 O5 C18 -6.9(3) . . . .
C13 C14 O5 C18 170.9(2) . . . .
