#------------------------------------------------------------------------------
#$Date: 2022-11-16 11:32:54 +0200 (Wed, 16 Nov 2022) $
#$Revision: 279318 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106114.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_8106114
loop_
_publ_author_name
'Song, Jing'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(4-nitro-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C18H17N3O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              251
_journal_page_last               252
_journal_paper_doi               10.1515/ncrs-2017-0252
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C18 H17 N3 O4'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         339.35
_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_Hall  '-P 2yn'
_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                 111.060(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5820(6)
_cell_length_b                   16.5417(11)
_cell_length_c                   10.6951(7)
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2270
_cell_measurement_theta_min      3.1870
_cell_volume                     1582.0(2)
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6244
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0437
_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)+(0.0730P)²+0.2075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                2163
_reflns_number_total             2787
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0252_suppl.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        1581.97(18)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8106114
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
C1 C -0.3273(2) 0.07147(14) 0.1299(2) 0.0499(6) Uani 1 1 d . . .
H1A H -0.3711 0.0698 0.1977 0.075 Uiso 1 1 calc R . .
H1B H -0.3342 0.0190 0.0897 0.075 Uiso 1 1 calc R . .
H1C H -0.3797 0.1102 0.0625 0.075 Uiso 1 1 calc R . .
C2 C -0.0814(2) 0.03662(14) 0.3041(2) 0.0508(6) Uani 1 1 d . . .
H2A H -0.1268 0.0368 0.3709 0.076 Uiso 1 1 calc R . .
H2B H 0.0216 0.0523 0.3443 0.076 Uiso 1 1 calc R . .
H2C H -0.0875 -0.0167 0.2670 0.076 Uiso 1 1 calc R . .
C3 C -0.1632(2) 0.09601(12) 0.19325(18) 0.0348(5) Uani 1 1 d . . .
C4 C -0.1515(2) 0.18125(12) 0.2511(2) 0.0397(5) Uani 1 1 d . . .
H4A H -0.2178 0.2165 0.1831 0.048 Uiso 1 1 calc R . .
H4B H -0.1864 0.1801 0.3257 0.048 Uiso 1 1 calc R . .
C5 C 0.0028(2) 0.21668(11) 0.29855(18) 0.0322(4) Uani 1 1 d . . .
C6 C 0.10666(19) 0.18889(11) 0.23535(17) 0.0289(4) Uani 1 1 d . . .
C7 C 0.05238(19) 0.14015(11) 0.12927(17) 0.0285(4) Uani 1 1 d . . .
C8 C -0.0943(2) 0.09839(12) 0.08433(18) 0.0365(5) Uani 1 1 d . . .
H8A H -0.0816 0.0435 0.0583 0.044 Uiso 1 1 calc R . .
H8B H -0.1624 0.1259 0.0061 0.044 Uiso 1 1 calc R . .
C9 C 0.25074(19) 0.17119(11) 0.05648(17) 0.0294(4) Uani 1 1 d . . .
C10 C 0.31476(19) 0.22024(11) 0.16249(17) 0.0303(4) Uani 1 1 d . . .
C11 C 0.26542(19) 0.21979(11) 0.28212(17) 0.0301(4) Uani 1 1 d . . .
H11A H 0.2649 0.2759 0.3116 0.036 Uiso 1 1 calc R . .
C12 C 0.4290(2) 0.27405(12) 0.16063(18) 0.0343(5) Uani 1 1 d . . .
C13 C 0.37009(19) 0.17106(11) 0.40153(17) 0.0297(4) Uani 1 1 d . . .
C14 C 0.5130(2) 0.15067(13) 0.41102(19) 0.0381(5) Uani 1 1 d . . .
H14A H 0.5459 0.1658 0.3425 0.046 Uiso 1 1 calc R . .
C15 C 0.6091(2) 0.10840(13) 0.51943(19) 0.0404(5) Uani 1 1 d . . .
H15A H 0.7055 0.0957 0.5245 0.049 Uiso 1 1 calc R . .
C16 C 0.55888(19) 0.08571(11) 0.61917(17) 0.0332(5) Uani 1 1 d . . .
C17 C 0.4173(2) 0.10426(13) 0.61380(18) 0.0403(5) Uani 1 1 d . . .
H17A H 0.3849 0.0881 0.6821 0.048 Uiso 1 1 calc R . .
C18 C 0.3238(2) 0.14713(13) 0.50571(18) 0.0402(5) Uani 1 1 d . . .
H18A H 0.2280 0.1604 0.5020 0.048 Uiso 1 1 calc R . .
O1 O 0.13056(13) 0.12379(8) 0.04652(11) 0.0331(3) Uani 1 1 d . . .
O2 O 0.03981(15) 0.27017(9) 0.38411(14) 0.0439(4) Uani 1 1 d . . .
O3 O 0.78893(19) 0.03345(14) 0.74607(17) 0.0874(7) Uani 1 1 d . . .
O4 O 0.60883(18) 0.01126(12) 0.81242(16) 0.0709(6) Uani 1 1 d . . .
N1 N 0.2906(2) 0.16040(11) -0.05033(16) 0.0394(4) Uani 1 1 d . . .
H1D H 0.373(2) 0.1866(13) -0.052(2) 0.047 Uiso 1 1 d . . .
H1E H 0.225(2) 0.1448(14) -0.120(2) 0.047 Uiso 1 1 d . . .
N2 N 0.5227(2) 0.31769(12) 0.16173(19) 0.0520(5) Uani 1 1 d . . .
N3 N 0.65883(19) 0.03974(11) 0.73353(16) 0.0441(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 C1 H1A 109.5 . .
C3 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C3 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 H2A 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C3 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C2 C3 C1 109.51(17) . .
C2 C3 C4 109.75(16) . .
C1 C3 C4 109.83(16) . .
C2 C3 C8 111.52(16) . .
C1 C3 C8 109.03(15) . .
C4 C3 C8 107.17(16) . .
C5 C4 C3 114.70(15) . .
C5 C4 H4A 108.6 . .
C3 C4 H4A 108.6 . .
C5 C4 H4B 108.6 . .
C3 C4 H4B 108.6 . .
H4A C4 H4B 107.6 . .
O2 C5 C6 120.50(17) . .
O2 C5 C4 121.24(16) . .
C6 C5 C4 118.19(16) . .
C7 C6 C5 117.39(16) . .
C7 C6 C11 121.63(15) . .
C5 C6 C11 120.80(16) . .
C6 C7 O1 121.95(16) . .
C6 C7 C8 126.25(16) . .
O1 C7 C8 111.80(14) . .
C7 C8 C3 112.51(15) . .
C7 C8 H8A 109.1 . .
C3 C8 H8A 109.1 . .
C7 C8 H8B 109.1 . .
C3 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
N1 C9 C10 127.87(17) . .
N1 C9 O1 110.33(16) . .
C10 C9 O1 121.80(15) . .
C9 C10 C12 119.10(16) . .
C9 C10 C11 121.41(16) . .
C12 C10 C11 119.48(16) . .
C6 C11 C10 107.75(14) . .
C6 C11 C13 112.11(15) . .
C10 C11 C13 113.30(15) . .
C6 C11 H11A 107.8 . .
C10 C11 H11A 107.8 . .
C13 C11 H11A 107.8 . .
N2 C12 C10 178.7(2) . .
C14 C13 C18 117.66(17) . .
C14 C13 C11 121.56(16) . .
C18 C13 C11 120.77(16) . .
C13 C14 C15 121.99(17) . .
C13 C14 H14A 119.0 . .
C15 C14 H14A 119.0 . .
C16 C15 C14 118.47(18) . .
C16 C15 H15A 120.8 . .
C14 C15 H15A 120.8 . .
C15 C16 C17 121.63(17) . .
C15 C16 N3 118.98(17) . .
C17 C16 N3 119.39(17) . .
C16 C17 C18 119.04(18) . .
C16 C17 H17A 120.5 . .
C18 C17 H17A 120.5 . .
C17 C18 C13 121.20(18) . .
C17 C18 H18A 119.4 . .
C13 C18 H18A 119.4 . .
C9 O1 C7 118.40(14) . .
C9 N1 H1D 118.3(13) . .
C9 N1 H1E 116.7(15) . .
H1D N1 H1E 121(2) . .
O4 N3 O3 122.80(18) . .
O4 N3 C16 118.79(17) . .
O3 N3 C16 118.39(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.526(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.522(3) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 C4 1.528(3) .
C3 C8 1.532(2) .
C4 C5 1.499(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 O2 1.230(2) .
C5 C6 1.464(2) .
C6 C7 1.335(3) .
C6 C11 1.510(2) .
C7 O1 1.376(2) .
C7 C8 1.482(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 N1 1.340(2) .
C9 C10 1.349(3) .
C9 O1 1.365(2) .
C10 C12 1.417(3) .
C10 C11 1.515(2) .
C11 C13 1.538(3) .
C11 H11A 0.9800 .
C12 N2 1.149(2) .
C13 C14 1.378(3) .
C13 C18 1.397(2) .
C14 C15 1.383(3) .
C14 H14A 0.9300 .
C15 C16 1.371(3) .
C15 H15A 0.9300 .
C16 C17 1.372(3) .
C16 N3 1.466(2) .
C17 C18 1.378(3) .
C17 H17A 0.9300 .
C18 H18A 0.9300 .
O3 N3 1.209(2) .
O4 N3 1.206(2) .
N1 H1D 0.91(2) .
N1 H1E 0.82(2) .
