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#$Date: 2022-11-30 10:34:57 +0200 (Wed, 30 Nov 2022) $
#$Revision: 279643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106303.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_8106303
loop_
_publ_author_name
'Wang, Ning'
'Liu, Yu-Hang'
'Gao, Ming-Lei'
'Zhao, Ye'
'Wen, Ping'
_publ_section_title
;
 Crystal structure of ethyl
 2-amino-4-(2-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate,
 C22H19NO6
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              807
_journal_page_last               808
_journal_paper_doi               10.1515/ncrs-2018-0019
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C22 H19 N O6'
_chemical_formula_weight         393.38
_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                 91.361(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.055(3)
_cell_length_b                   17.601(6)
_cell_length_c                   11.817(4)
_cell_measurement_reflns_used    3788
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.53
_cell_volume                     1882.8(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXL (Sheldrick, 2015)'
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9235
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0207(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.3170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                2602
_reflns_number_total             3309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2018-0019_suppl.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               8106303
_publcif_funding_html
;
;
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 0.00892(15) 0.37449(7) 1.08055(11) 0.0439(4) Uani 1 1 d . . .
H1D H -0.0043 0.4202 1.0568 0.053 Uiso 1 1 calc R . .
H1E H -0.0293 0.3601 1.1429 0.053 Uiso 1 1 calc R . .
O1 O 0.25622(13) 0.41895(6) 0.78774(10) 0.0492(3) Uani 1 1 d . . .
O2 O 0.12129(14) 0.47091(6) 0.92437(10) 0.0545(3) Uani 1 1 d . . .
O3 O 0.09717(11) 0.25761(5) 1.07831(8) 0.0376(3) Uani 1 1 d . . .
O4 O 0.41121(12) 0.09878(6) 0.99804(9) 0.0450(3) Uani 1 1 d . . .
O5 O 0.45281(13) 0.15414(7) 0.83486(9) 0.0481(3) Uani 1 1 d . . .
O6 O -0.04601(12) 0.19744(7) 0.87216(9) 0.0494(3) Uani 1 1 d . . .
C1 C 0.3545(3) 0.48979(13) 0.63596(18) 0.0784(7) Uani 1 1 d . . .
H1A H 0.3770 0.5398 0.6089 0.118 Uiso 1 1 calc R . .
H1B H 0.2856 0.4657 0.5844 0.118 Uiso 1 1 calc R . .
H1C H 0.4435 0.4602 0.6411 0.118 Uiso 1 1 calc R . .
C2 C 0.2890(2) 0.49531(10) 0.74861(16) 0.0624(5) Uani 1 1 d . . .
H2A H 0.3576 0.5200 0.8011 0.075 Uiso 1 1 calc R . .
H2B H 0.1991 0.5253 0.7442 0.075 Uiso 1 1 calc R . .
C3 C 0.17231(17) 0.41424(8) 0.88048(13) 0.0372(4) Uani 1 1 d . . .
C4 C 0.15777(16) 0.33722(8) 0.92105(12) 0.0330(3) Uani 1 1 d . . .
C5 C 0.08833(16) 0.32616(8) 1.02088(12) 0.0331(3) Uani 1 1 d . . .
C6 C 0.20157(15) 0.20666(8) 1.04618(12) 0.0322(3) Uani 1 1 d . . .
C7 C 0.26878(16) 0.21041(8) 0.94647(12) 0.0310(3) Uani 1 1 d . . .
C8 C 0.23180(16) 0.27143(8) 0.86100(12) 0.0329(3) Uani 1 1 d . . .
H8A H 0.3260 0.2907 0.8335 0.039 Uiso 1 1 calc R . .
C9 C 0.38176(17) 0.15551(8) 0.92011(12) 0.0355(3) Uani 1 1 d . . .
C10 C 0.33928(17) 0.09472(8) 1.09934(13) 0.0389(4) Uani 1 1 d . . .
C11 C 0.23447(17) 0.14834(8) 1.12883(12) 0.0355(3) Uani 1 1 d . . .
C12 C 0.1692(2) 0.14256(9) 1.23457(13) 0.0475(4) Uani 1 1 d . . .
H12A H 0.0998 0.1783 1.2566 0.057 Uiso 1 1 calc R . .
C13 C 0.2081(2) 0.08371(10) 1.30576(15) 0.0563(5) Uani 1 1 d . . .
H13A H 0.1654 0.0801 1.3764 0.068 Uiso 1 1 calc R . .
C14 C 0.3097(2) 0.03004(10) 1.27358(15) 0.0571(5) Uani 1 1 d . . .
H14A H 0.3335 -0.0099 1.3222 0.069 Uiso 1 1 calc R . .
C15 C 0.3763(2) 0.03475(10) 1.17061(15) 0.0532(5) Uani 1 1 d . . .
H15A H 0.4448 -0.0015 1.1491 0.064 Uiso 1 1 calc R . .
C16 C 0.14789(17) 0.23866(8) 0.75833(12) 0.0349(4) Uani 1 1 d . . .
C17 C 0.2116(2) 0.24207(9) 0.65301(13) 0.0467(4) Uani 1 1 d . . .
H17A H 0.3001 0.2682 0.6454 0.056 Uiso 1 1 calc R . .
C18 C 0.1467(2) 0.20756(11) 0.55865(14) 0.0566(5) Uani 1 1 d . . .
H18A H 0.1916 0.2104 0.4888 0.068 Uiso 1 1 calc R . .
C19 C 0.0164(2) 0.16934(11) 0.56927(14) 0.0561(5) Uani 1 1 d . . .
H19A H -0.0266 0.1456 0.5064 0.067 Uiso 1 1 calc R . .
C20 C -0.0522(2) 0.16564(10) 0.67227(15) 0.0506(4) Uani 1 1 d . . .
H20A H -0.1418 0.1403 0.6784 0.061 Uiso 1 1 calc R . .
C21 C 0.01327(17) 0.20005(9) 0.76692(13) 0.0387(4) Uani 1 1 d . . .
C22 C -0.1749(2) 0.15283(13) 0.88628(18) 0.0708(6) Uani 1 1 d . . .
H22A H -0.2048 0.1557 0.9636 0.106 Uiso 1 1 calc R . .
H22B H -0.1542 0.1009 0.8673 0.106 Uiso 1 1 calc R . .
H22C H -0.2529 0.1717 0.8375 0.106 Uiso 1 1 calc R . .
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
C5 N1 H1D 120.0 . .
C5 N1 H1E 120.0 . .
H1D N1 H1E 120.0 . .
C3 O1 C2 115.96(12) . .
C6 O3 C5 117.95(11) . .
C10 O4 C9 121.96(11) . .
C21 O6 C22 117.85(13) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 C1 108.42(15) . .
O1 C2 H2A 110.0 . .
C1 C2 H2A 110.0 . .
O1 C2 H2B 110.0 . .
C1 C2 H2B 110.0 . .
H2A C2 H2B 108.4 . .
O2 C3 O1 121.38(13) . .
O2 C3 C4 125.98(14) . .
O1 C3 C4 112.59(12) . .
C5 C4 C3 117.93(12) . .
C5 C4 C8 120.79(12) . .
C3 C4 C8 120.96(12) . .
N1 C5 C4 129.40(13) . .
N1 C5 O3 108.87(12) . .
C4 C5 O3 121.70(12) . .
C7 C6 O3 122.99(13) . .
C7 C6 C11 122.63(13) . .
O3 C6 C11 114.38(12) . .
C6 C7 C9 119.64(13) . .
C6 C7 C8 121.74(12) . .
C9 C7 C8 118.61(12) . .
C7 C8 C4 108.85(11) . .
C7 C8 C16 111.18(12) . .
C4 C8 C16 116.16(12) . .
C7 C8 H8A 106.7 . .
C4 C8 H8A 106.7 . .
C16 C8 H8A 106.7 . .
O5 C9 O4 116.33(13) . .
O5 C9 C7 125.89(14) . .
O4 C9 C7 117.78(13) . .
O4 C10 C15 117.05(14) . .
O4 C10 C11 121.50(13) . .
C15 C10 C11 121.45(15) . .
C10 C11 C12 118.72(14) . .
C10 C11 C6 116.42(13) . .
C12 C11 C6 124.86(14) . .
C13 C12 C11 119.58(16) . .
C13 C12 H12A 120.2 . .
C11 C12 H12A 120.2 . .
C12 C13 C14 120.71(16) . .
C12 C13 H13A 119.6 . .
C14 C13 H13A 119.6 . .
C15 C14 C13 120.85(16) . .
C15 C14 H14A 119.6 . .
C13 C14 H14A 119.6 . .
C14 C15 C10 118.66(16) . .
C14 C15 H15A 120.7 . .
C10 C15 H15A 120.7 . .
C17 C16 C21 117.87(14) . .
C17 C16 C8 119.13(14) . .
C21 C16 C8 122.83(13) . .
C16 C17 C18 121.72(17) . .
C16 C17 H17A 119.1 . .
C18 C17 H17A 119.1 . .
C19 C18 C17 119.43(17) . .
C19 C18 H18A 120.3 . .
C17 C18 H18A 120.3 . .
C18 C19 C20 120.77(16) . .
C18 C19 H19A 119.6 . .
C20 C19 H19A 119.6 . .
C19 C20 C21 119.71(17) . .
C19 C20 H20A 120.1 . .
C21 C20 H20A 120.1 . .
O6 C21 C20 123.19(15) . .
O6 C21 C16 116.31(13) . .
C20 C21 C16 120.49(15) . .
O6 C22 H22A 109.5 . .
O6 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
O6 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.3274(18) .
N1 H1D 0.8600 .
N1 H1E 0.8600 .
O1 C3 1.3508(18) .
O1 C2 1.4541(19) .
O2 C3 1.2200(18) .
O3 C6 1.3635(17) .
O3 C5 1.3857(17) .
O4 C10 1.3782(18) .
O4 C9 1.3801(18) .
O5 C9 1.2084(18) .
O6 C21 1.3669(18) .
O6 C22 1.420(2) .
C1 C2 1.473(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.445(2) .
C4 C5 1.364(2) .
C4 C8 1.5219(19) .
C6 C7 1.341(2) .
C6 C11 1.443(2) .
C7 C9 1.446(2) .
C7 C8 1.507(2) .
C8 C16 1.529(2) .
C8 H8A 0.9800 .
C10 C15 1.386(2) .
C10 C11 1.389(2) .
C11 C12 1.399(2) .
C12 C13 1.375(2) .
C12 H12A 0.9300 .
C13 C14 1.379(3) .
C13 H13A 0.9300 .
C14 C15 1.373(2) .
C14 H14A 0.9300 .
C15 H15A 0.9300 .
C16 C17 1.385(2) .
C16 C21 1.401(2) .
C17 C18 1.388(2) .
C17 H17A 0.9300 .
C18 C19 1.367(3) .
C18 H18A 0.9300 .
C19 C20 1.381(2) .
C19 H19A 0.9300 .
C20 C21 1.392(2) .
C20 H20A 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
