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#$Date: 2023-04-03 10:35:20 +0300 (Mon, 03 Apr 2023) $
#$Revision: 282201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106994.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_8106994
loop_
_publ_author_name
'Song, Jing'
_publ_section_title
;
 Crystal structure of
 2-amino-7-methyl-5-oxo-4-phenyl-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile,
 C16H12N2O3
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              747
_journal_page_last               748
_journal_paper_doi               10.1515/ncrs-2015-0255
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C16 H12 N2 O3'
_chemical_formula_weight         280.28
_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                 103.65(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.707(5)
_cell_length_b                   8.749(5)
_cell_length_c                   15.002(6)
_cell_measurement_reflns_used    930
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.68
_cell_measurement_theta_min      2.72
_cell_volume                     1365.6(12)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6301
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0118(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0557
_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)+(0.0080P)²+0.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                1148
_reflns_number_total             2365
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0255_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1365.7(12)
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               8106994
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 0.4040(3) 0.4749(3) 0.3009(2) 0.0714(10) Uani 1 1 d . . .
H1A H 0.4194 0.4446 0.3570 0.086 Uiso 1 1 calc R . .
H1B H 0.3817 0.4100 0.2570 0.086 Uiso 1 1 calc R . .
N2 N 0.5035(4) 0.6770(4) 0.5121(2) 0.0909(12) Uani 1 1 d . . .
C1 C 0.6119(4) 0.9392(4) 0.3376(2) 0.0559(9) Uani 1 1 d . . .
C2 C 0.6956(4) 0.8683(4) 0.2946(2) 0.0682(11) Uani 1 1 d . . .
H2 H 0.6639 0.7978 0.2484 0.082 Uiso 1 1 calc R . .
C3 C 0.8248(5) 0.8985(6) 0.3180(3) 0.0942(15) Uani 1 1 d . . .
H3 H 0.8794 0.8504 0.2870 0.113 Uiso 1 1 calc R . .
C4 C 0.8733(6) 0.9998(7) 0.3872(4) 0.1077(19) Uani 1 1 d . . .
H4 H 0.9612 1.0188 0.4050 0.129 Uiso 1 1 calc R . .
C5 C 0.7912(6) 1.0716(5) 0.4292(4) 0.1043(17) Uani 1 1 d . . .
H5 H 0.8231 1.1424 0.4752 0.125 Uiso 1 1 calc R . .
C6 C 0.6599(5) 1.0418(4) 0.4050(3) 0.0778(12) Uani 1 1 d . . .
H6 H 0.6050 1.0920 0.4349 0.093 Uiso 1 1 calc R . .
C7 C 0.4699(3) 0.9003(3) 0.3135(2) 0.0527(9) Uani 1 1 d . . .
H7 H 0.4250 0.9704 0.3463 0.063 Uiso 1 1 calc R . .
C8 C 0.4129(3) 0.9147(4) 0.2131(2) 0.0492(9) Uani 1 1 d . . .
C9 C 0.3944(3) 1.0644(4) 0.1730(2) 0.0569(9) Uani 1 1 d . . .
C10 C 0.3246(4) 0.9484(4) 0.0262(2) 0.0608(10) Uani 1 1 d . . .
C11 C 0.3327(3) 0.8103(4) 0.0620(2) 0.0603(10) Uani 1 1 d . . .
H11 H 0.3095 0.7249 0.0248 0.072 Uiso 1 1 calc R . .
C12 C 0.3769(3) 0.7947(4) 0.1568(2) 0.0529(9) Uani 1 1 d . . .
C13 C 0.2821(5) 0.9908(4) -0.0721(2) 0.0889(14) Uani 1 1 d . . .
H13A H 0.2555 0.9007 -0.1080 0.133 Uiso 1 1 calc R . .
H13B H 0.3519 1.0384 -0.0916 0.133 Uiso 1 1 calc R . .
H13C H 0.2112 1.0608 -0.0801 0.133 Uiso 1 1 calc R . .
C14 C 0.4146(3) 0.6232(4) 0.2820(2) 0.0538(9) Uani 1 1 d . . .
C15 C 0.4478(3) 0.7384(4) 0.3410(2) 0.0516(9) Uani 1 1 d . . .
C16 C 0.4781(4) 0.7032(4) 0.4353(3) 0.0622(10) Uani 1 1 d . . .
O1 O 0.4140(3) 1.1832(3) 0.21557(17) 0.0751(8) Uani 1 1 d . . .
O2 O 0.3541(2) 1.0743(2) 0.08003(16) 0.0651(7) Uani 1 1 d . . .
O3 O 0.3823(2) 0.6466(2) 0.18891(16) 0.0620(7) 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
C14 N1 H1A 120.0 . .
C14 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C6 C1 C2 118.4(4) . .
C6 C1 C7 120.5(3) . .
C2 C1 C7 121.1(3) . .
C3 C2 C1 121.6(4) . .
C3 C2 H2 119.2 . .
C1 C2 H2 119.2 . .
C2 C3 C4 119.9(5) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C5 C4 C3 118.8(6) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
C4 C5 C6 121.3(5) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C1 C6 C5 119.9(4) . .
C1 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C8 C7 C15 107.6(3) . .
C8 C7 C1 111.7(3) . .
C15 C7 C1 111.0(3) . .
C8 C7 H7 108.8 . .
C15 C7 H7 108.8 . .
C1 C7 H7 108.8 . .
C12 C8 C9 117.2(3) . .
C12 C8 C7 123.8(3) . .
C9 C8 C7 119.0(3) . .
O1 C9 O2 117.3(3) . .
O1 C9 C8 124.9(3) . .
O2 C9 C8 117.8(3) . .
C11 C10 O2 121.2(3) . .
C11 C10 C13 127.6(3) . .
O2 C10 C13 111.2(3) . .
C10 C11 C12 118.6(3) . .
C10 C11 H11 120.7 . .
C12 C11 H11 120.7 . .
C8 C12 O3 122.1(3) . .
C8 C12 C11 122.8(3) . .
O3 C12 C11 115.1(3) . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 N1 127.9(3) . .
C15 C14 O3 121.8(3) . .
N1 C14 O3 110.3(3) . .
C14 C15 C16 117.6(3) . .
C14 C15 C7 124.2(3) . .
C16 C15 C7 117.8(3) . .
N2 C16 C15 178.9(4) . .
C10 O2 C9 122.0(3) . .
C14 O3 C12 118.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C14 1.339(4) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N2 C16 1.144(4) .
C1 C6 1.359(5) .
C1 C2 1.369(4) .
C1 C7 1.517(5) .
C2 C3 1.370(6) .
C2 H2 0.9300 .
C3 C4 1.371(7) .
C3 H3 0.9300 .
C4 C5 1.350(7) .
C4 H4 0.9300 .
C5 C6 1.392(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.490(5) .
C7 C15 1.510(4) .
C7 H7 0.9800 .
C8 C12 1.346(4) .
C8 C9 1.436(4) .
C9 O1 1.212(4) .
C9 O2 1.362(4) .
C10 C11 1.316(4) .
C10 O2 1.359(4) .
C10 C13 1.484(5) .
C11 C12 1.396(5) .
C11 H11 0.9300 .
C12 O3 1.379(4) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C15 1.333(4) .
C14 O3 1.373(4) .
C15 C16 1.408(5) .
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
C6 C1 C2 C3 0.0(5) . . . .
C7 C1 C2 C3 -177.7(3) . . . .
C1 C2 C3 C4 1.3(6) . . . .
C2 C3 C4 C5 -2.0(7) . . . .
C3 C4 C5 C6 1.6(7) . . . .
C2 C1 C6 C5 -0.5(6) . . . .
C7 C1 C6 C5 177.2(3) . . . .
C4 C5 C6 C1 -0.3(7) . . . .
C6 C1 C7 C8 128.7(3) . . . .
C2 C1 C7 C8 -53.7(4) . . . .
C6 C1 C7 C15 -111.1(4) . . . .
C2 C1 C7 C15 66.5(4) . . . .
C15 C7 C8 C12 -13.9(4) . . . .
C1 C7 C8 C12 108.2(4) . . . .
C15 C7 C8 C9 166.0(3) . . . .
C1 C7 C8 C9 -71.9(4) . . . .
C12 C8 C9 O1 174.9(3) . . . .
C7 C8 C9 O1 -5.0(5) . . . .
C12 C8 C9 O2 -6.4(4) . . . .
C7 C8 C9 O2 173.7(3) . . . .
O2 C10 C11 C12 -2.2(5) . . . .
C13 C10 C11 C12 179.2(4) . . . .
C9 C8 C12 O3 -175.6(3) . . . .
C7 C8 C12 O3 4.4(5) . . . .
C9 C8 C12 C11 5.0(5) . . . .
C7 C8 C12 C11 -175.0(3) . . . .
C10 C11 C12 C8 -0.7(5) . . . .
C10 C11 C12 O3 179.8(3) . . . .
N1 C14 C15 C16 1.3(5) . . . .
O3 C14 C15 C16 179.4(3) . . . .
N1 C14 C15 C7 173.8(3) . . . .
O3 C14 C15 C7 -8.1(5) . . . .
C8 C7 C15 C14 15.9(4) . . . .
C1 C7 C15 C14 -106.7(4) . . . .
C8 C7 C15 C16 -171.6(3) . . . .
C1 C7 C15 C16 65.8(4) . . . .
C14 C15 C16 N2 169(100) . . . .
C7 C15 C16 N2 -4(22) . . . .
C11 C10 O2 C9 0.6(5) . . . .
C13 C10 O2 C9 179.4(3) . . . .
O1 C9 O2 C10 -177.4(3) . . . .
C8 C9 O2 C10 3.8(5) . . . .
C15 C14 O3 C12 -3.9(5) . . . .
N1 C14 O3 C12 174.5(3) . . . .
C8 C12 O3 C14 5.8(4) . . . .
C11 C12 O3 C14 -174.7(3) . . . .
