#------------------------------------------------------------------------------
#$Date: 2022-11-15 11:11:06 +0200 (Tue, 15 Nov 2022) $
#$Revision: 279288 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106094.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_8106094
loop_
_publ_author_name
'Su, Yi-Yan'
_publ_section_title
;
 Crystal structural of
 2-amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C17H16N2O3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              187
_journal_page_last               188
_journal_paper_doi               10.1515/ncrs-2017-0162
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_cell_angle_alpha                90
_cell_angle_beta                 104.304(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6539(4)
_cell_length_b                   16.7491(9)
_cell_length_c                   10.5511(5)
_cell_measurement_reflns_used    1650
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7030
_cell_measurement_theta_min      3.1330
_cell_volume                     1481.92(13)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6045
_diffrn_reflns_theta_full        24.9999
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.984
_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    1.3281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624.3192
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.1731
_refine_diff_density_min         -0.2409
_refine_diff_density_rms         0.0506
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.4983
_refine_ls_goodness_of_fit_ref   1.0276
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0276
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0554P)²+0.1719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1957
_reflns_number_total             2608
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            suppl_ncrs-2017-0162_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_database_code               8106094
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C7(H7a,H7b), C8(H8a,H8b)
2.c Me refined with riding coordinates:
 C17(H17a,H17b,H17c)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
2.e X=CH2 refined with riding coordinates:
 N1(H1a,H1b)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-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_refinement_flags_posn
C1 C 0.2760(2) 0.03846(12) 0.08044(17) 0.0428(5) Uani 1.000000 .
C2 C 0.2377(2) 0.00329(11) -0.03849(16) 0.0393(4) Uani 1.000000 .
C3 C 0.1270(2) 0.04119(11) -0.15751(15) 0.0364(4) Uani 1.000000 .
H3 H 0.0410(2) 0.00321(11) -0.19284(15) 0.0437(5) Uiso 1.000000 R
C4 C 0.05350(19) 0.11484(11) -0.11491(16) 0.0373(4) Uani 1.000000 .
C5 C 0.1009(2) 0.14567(11) 0.00536(17) 0.0407(4) Uani 1.000000 .
C6 C 0.0402(2) 0.22047(12) 0.05100(18) 0.0531(5) Uani 1.000000 .
H6a H -0.0378(2) 0.20766(12) 0.09999(18) 0.0638(6) Uiso 1.000000 R
H6b H 0.1275(2) 0.24891(12) 0.10869(18) 0.0638(6) Uiso 1.000000 R
C7 C -0.0361(3) 0.27324(12) -0.0646(2) 0.0586(6) Uani 1.000000 .
H7a H -0.0901(3) 0.31763(12) -0.0350(2) 0.0703(7) Uiso 1.000000 R
H7b H 0.0458(3) 0.29472(12) -0.1033(2) 0.0703(7) Uiso 1.000000 R
C8 C -0.1544(2) 0.22566(12) -0.16587(18) 0.0518(5) Uani 1.000000 .
H8a H -0.2429(2) 0.21023(12) -0.12995(18) 0.0622(6) Uiso 1.000000 R
H8b H -0.1962(2) 0.25915(12) -0.24158(18) 0.0622(6) Uiso 1.000000 R
C9 C -0.0819(2) 0.15199(11) -0.20849(18) 0.0425(5) Uani 1.000000 .
C10 C 0.21119(19) 0.06002(10) -0.26529(15) 0.0336(4) Uani 1.000000 .
C11 C 0.1853(2) 0.01365(11) -0.37656(16) 0.0423(5) Uani 1.000000 .
H11 H 0.1165(2) -0.02976(11) -0.38516(16) 0.0508(6) Uiso 1.000000 R
C12 C 0.2591(2) 0.03023(11) -0.47534(17) 0.0467(5) Uani 1.000000 .
H12 H 0.2401(2) -0.00195(11) -0.54942(17) 0.0560(6) Uiso 1.000000 R
C13 C 0.3609(2) 0.09450(11) -0.46424(16) 0.0381(4) Uani 1.000000 .
C14 C 0.3918(2) 0.14108(11) -0.35320(16) 0.0417(5) Uani 1.000000 .
H14 H 0.4617(2) 0.18403(11) -0.34441(16) 0.0500(5) Uiso 1.000000 R
C15 C 0.3166(2) 0.12290(11) -0.25431(16) 0.0402(4) Uani 1.000000 .
H15 H 0.3381(2) 0.15396(11) -0.17892(16) 0.0483(5) Uiso 1.000000 R
C16 C 0.3062(2) -0.07179(12) -0.05294(17) 0.0473(5) Uani 1.000000 .
C17 C 0.5260(3) 0.17426(14) -0.5668(2) 0.0691(7) Uani 1.000000 .
H17a H 0.5609(3) 0.17588(14) -0.6463(2) 0.1036(10) Uiso 1.000000 R
H17b H 0.4692(3) 0.22245(14) -0.5587(2) 0.1036(10) Uiso 1.000000 R
H17c H 0.6169(3) 0.16956(14) -0.4936(2) 0.1036(10) Uiso 1.000000 R
N1 N 0.3733(2) 0.01043(11) 0.19053(14) 0.0612(5) Uani 1.000000 .
H1a H 0.4194(2) -0.03502(11) 0.19025(14) 0.0734(6) Uiso 1.000000 R
H1b H 0.3896(2) 0.03789(11) 0.26147(14) 0.0734(6) Uiso 1.000000 R
N2 N 0.3601(3) -0.13303(11) -0.06592(19) 0.0732(6) Uani 1.000000 .
O1 O 0.21487(15) 0.11061(8) 0.10376(11) 0.0514(4) Uani 1.000000 .
O2 O -0.13484(16) 0.12240(9) -0.31601(13) 0.0593(4) Uani 1.000000 .
O3 O 0.42439(16) 0.10782(9) -0.56944(12) 0.0560(4) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
N1 C1 C2 127.58(19) . .
O1 C1 C2 122.40(16) . .
O1 C1 N1 110.01(16) . .
C3 C2 C1 123.10(16) . .
C16 C2 C1 118.32(17) . .
C16 C2 C3 118.58(15) . .
H3 C3 C2 107.94(9) . .
C4 C3 C2 108.80(13) . .
C4 C3 H3 107.94(9) . .
C10 C3 C2 112.51(13) . .
C10 C3 H3 107.94(9) . .
C10 C3 C4 111.54(14) . .
C5 C4 C3 123.11(16) . .
C9 C4 C3 118.11(14) . .
C9 C4 C5 118.72(16) . .
C6 C5 C4 125.71(17) . .
O1 C5 C4 123.13(16) . .
O1 C5 C6 111.16(15) . .
H6a C6 C5 109.57(10) . .
H6b C6 C5 109.57(10) . .
H6b C6 H6a 108.1 . .
C7 C6 C5 110.43(15) . .
C7 C6 H6a 109.57(10) . .
C7 C6 H6b 109.57(11) . .
H7a C7 C6 109.62(10) . .
H7b C7 C6 109.62(11) . .
H7b C7 H7a 108.1 . .
C8 C7 C6 110.18(17) . .
C8 C7 H7a 109.62(10) . .
C8 C7 H7b 109.62(10) . .
H8a C8 C7 109.07(10) . .
H8b C8 C7 109.07(11) . .
H8b C8 H8a 107.8 . .
C9 C8 C7 112.62(15) . .
C9 C8 H8a 109.07(10) . .
C9 C8 H8b 109.07(10) . .
C8 C9 C4 117.96(16) . .
O2 C9 C4 120.46(17) . .
O2 C9 C8 121.56(17) . .
C11 C10 C3 120.68(15) . .
C15 C10 C3 121.50(15) . .
C15 C10 C11 117.81(15) . .
H11 C11 C10 119.27(10) . .
C12 C11 C10 121.47(17) . .
C12 C11 H11 119.27(11) . .
H12 C12 C11 120.03(11) . .
C13 C12 C11 119.95(16) . .
C13 C12 H12 120.03(10) . .
C14 C13 C12 120.01(15) . .
O3 C13 C12 115.69(15) . .
O3 C13 C14 124.30(16) . .
H14 C14 C13 120.49(10) . .
C15 C14 C13 119.03(16) . .
C15 C14 H14 120.49(10) . .
C14 C15 C10 121.71(16) . .
H15 C15 C10 119.15(10) . .
H15 C15 C14 119.15(10) . .
N2 C16 C2 179.1(2) . .
H17b C17 H17a 109.5 . .
H17c C17 H17a 109.5 . .
H17c C17 H17b 109.5 . .
O3 C17 H17a 109.5 . .
O3 C17 H17b 109.5 . .
O3 C17 H17c 109.5 . .
H1a N1 C1 120.0 . .
H1b N1 C1 120.0 . .
H1b N1 H1a 120.0 . .
C5 O1 C1 118.66(14) . .
C17 O3 C13 118.87(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.351(2) .
C1 N1 1.340(2) .
C1 O1 1.366(2) .
C2 C3 1.518(2) .
C2 C16 1.415(3) .
C3 H3 0.9800 .
C3 C4 1.506(2) .
C3 C10 1.527(2) .
C4 C5 1.337(2) .
C4 C9 1.471(2) .
C5 C6 1.484(2) .
C5 O1 1.375(2) .
C6 H6a 0.9700 .
C6 H6b 0.9700 .
C6 C7 1.519(3) .
C7 H7a 0.9700 .
C7 H7b 0.9700 .
C7 C8 1.511(3) .
C8 H8a 0.9700 .
C8 H8b 0.9700 .
C8 C9 1.503(3) .
C9 O2 1.219(2) .
C10 C11 1.379(2) .
C10 C15 1.379(2) .
C11 H11 0.9300 .
C11 C12 1.378(2) .
C12 H12 0.9300 .
C12 C13 1.378(2) .
C13 C14 1.378(2) .
C13 O3 1.3729(19) .
C14 H14 0.9300 .
C14 C15 1.393(2) .
C15 H15 0.9300 .
C16 N2 1.149(2) .
C17 H17a 0.9600 .
C17 H17b 0.9600 .
C17 H17c 0.9600 .
C17 O3 1.414(2) .
N1 H1a 0.8600 .
N1 H1b 0.8600 .
