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#$Date: 2022-11-28 12:27:16 +0200 (Mon, 28 Nov 2022) $
#$Revision: 279607 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106286.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_8106286
loop_
_publ_author_name
'He, Jing'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(3,4,5-trimethoxy-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile,
 C19H18N2O6
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              757
_journal_page_last               758
_journal_paper_doi               10.1515/ncrs-2017-0316
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C19 H18 N2 O6'
_chemical_formula_sum            'C19 H18 N2 O6'
_chemical_formula_weight         370.35
_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'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 114.446(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.052(8)
_cell_length_b                   10.091(6)
_cell_length_c                   14.454(9)
_cell_measurement_reflns_used    1671
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.46
_cell_measurement_theta_min      2.54
_cell_volume                     1733.0(18)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8487
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.714
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0779P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2083
_reflns_number_total             3041
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0316_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1733.0(19)
_cod_database_code               8106286
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C19(H19)
2.b Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C18(H18A,H18B,H18C)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C16(H16)
2.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07794(13) 0.62356(15) 0.66102(12) 0.0482(5) Uani 1 1 d . . . . .
O2 O 0.07846(13) 0.74641(16) 0.50112(11) 0.0511(5) Uani 1 1 d . . . . .
O3 O 0.20953(14) 0.95803(17) 0.51976(12) 0.0549(5) Uani 1 1 d . . . . .
O4 O 0.29142(12) 0.91682(15) 1.07149(11) 0.0426(4) Uani 1 1 d . . . . .
O5 O 0.54182(13) 0.70363(17) 1.04858(13) 0.0536(5) Uani 1 1 d . . . . .
O6 O 0.51258(15) 0.7891(2) 0.89905(14) 0.0647(6) Uani 1 1 d . . . . .
N1 N 0.1548(2) 1.2354(2) 0.80994(18) 0.0689(7) Uani 1 1 d . . . . .
N2 N 0.15421(17) 1.0640(2) 1.02712(15) 0.0528(6) Uani 1 1 d . . . . .
H2A H 0.111785 1.126552 0.990864 0.063 Uiso 1 1 calc R . . . .
H2B H 0.147108 1.036796 1.080554 0.063 Uiso 1 1 calc R . . . .
C1 C 0.0811(2) 0.5490(3) 0.74526(19) 0.0581(7) Uani 1 1 d . . . . .
H1A H 0.032470 0.473498 0.721429 0.087 Uiso 1 1 calc R . . . .
H1B H 0.156752 0.519646 0.784835 0.087 Uiso 1 1 calc R . . . .
H1C H 0.056375 0.603344 0.786571 0.087 Uiso 1 1 calc R . . . .
C2 C 0.14261(18) 0.7354(2) 0.68065(17) 0.0371(6) Uani 1 1 d . . . . .
C3 C 0.14185(18) 0.7982(2) 0.59557(16) 0.0389(6) Uani 1 1 d . . . . .
C4 C -0.0175(2) 0.8244(3) 0.4445(2) 0.0626(8) Uani 1 1 d . . . . .
H4A H -0.058673 0.784011 0.379407 0.094 Uiso 1 1 calc R . . . .
H4B H -0.064701 0.830260 0.480578 0.094 Uiso 1 1 calc R . . . .
H4C H 0.006005 0.911625 0.435180 0.094 Uiso 1 1 calc R . . . .
C5 C 0.20973(18) 0.9080(2) 0.60686(16) 0.0403(6) Uani 1 1 d . . . . .
C6 C 0.2868(2) 1.0616(3) 0.5288(2) 0.0636(8) Uani 1 1 d . . . . .
H6A H 0.278490 1.088305 0.462299 0.095 Uiso 1 1 calc R . . . .
H6B H 0.271873 1.135721 0.562968 0.095 Uiso 1 1 calc R . . . .
H6C H 0.362180 1.030683 0.567140 0.095 Uiso 1 1 calc R . . . .
C7 C 0.27312(17) 0.9567(2) 0.70329(16) 0.0395(6) Uani 1 1 d . . . . .
H7 H 0.318132 1.031006 0.711375 0.047 Uiso 1 1 calc R . . . .
C8 C 0.27008(17) 0.8959(2) 0.78732(16) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.20601(18) 0.7840(2) 0.77693(17) 0.0389(6) Uani 1 1 d . . . . .
H9 H 0.205381 0.741761 0.833860 0.047 Uiso 1 1 calc R . . . .
C10 C 0.48324(19) 0.7879(2) 0.96785(19) 0.0454(6) Uani 1 1 d . . . . .
C11 C 0.39532(17) 0.8643(2) 0.97471(16) 0.0370(6) Uani 1 1 d . . . . .
C12 C 0.25409(18) 1.0380(2) 0.92081(17) 0.0374(6) Uani 1 1 d . . . . .
C13 C 0.1978(2) 1.1457(2) 0.85876(18) 0.0460(6) Uani 1 1 d . . . . .
C14 C 0.23108(18) 1.0091(2) 1.00046(17) 0.0393(6) Uani 1 1 d . . . . .
C15 C 0.37471(17) 0.8509(2) 1.05793(16) 0.0367(6) Uani 1 1 d . . . . .
C16 C 0.43902(18) 0.7670(2) 1.13985(18) 0.0432(6) Uani 1 1 d . . . . .
H16 H 0.424258 0.762000 1.197426 0.052 Uiso 1 1 calc R . . . .
C17 C 0.5198(2) 0.6965(2) 1.13289(19) 0.0481(6) Uani 1 1 d . . . . .
C18 C 0.5964(2) 0.6030(3) 1.2090(2) 0.0699(9) Uani 1 1 d . . . . .
H18A H 0.647405 0.565111 1.183892 0.105 Uiso 1 1 calc R . . . .
H18B H 0.638312 0.649445 1.271275 0.105 Uiso 1 1 calc R . . . .
H18C H 0.553089 0.533740 1.221261 0.105 Uiso 1 1 calc R . . . .
C19 C 0.33355(17) 0.9592(2) 0.89078(16) 0.0370(6) Uani 1 1 d . . . . .
H19 H 0.388731 1.020886 0.885187 0.044 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
C2 O1 C1 117.64(18) . .
C3 O2 C4 112.81(18) . .
C5 O3 C6 117.42(19) . .
C15 O4 C14 118.17(19) . .
C17 O5 C10 122.43(19) . .
O1 C2 C3 114.70(19) . .
O1 C2 C9 124.3(2) . .
C3 C2 C9 121.0(2) . .
O2 C3 C2 119.4(2) . .
O2 C3 C5 120.9(2) . .
C2 C3 C5 119.58(19) . .
O3 C5 C3 115.66(19) . .
O3 C5 C7 125.0(2) . .
C7 C5 C3 119.3(2) . .
C8 C7 C5 120.5(2) . .
C7 C8 C19 118.6(2) . .
C9 C8 C7 120.5(2) . .
C9 C8 C19 120.8(2) . .
C8 C9 C2 119.0(2) . .
O5 C10 C11 117.0(2) . .
O6 C10 O5 116.6(2) . .
O6 C10 C11 126.5(2) . .
C10 C11 C19 118.2(2) . .
C15 C11 C10 118.4(2) . .
C15 C11 C19 123.4(2) . .
C13 C12 C19 117.7(2) . .
C14 C12 C13 118.3(2) . .
C14 C12 C19 124.0(2) . .
N1 C13 C12 178.0(3) . .
N2 C14 O4 109.5(2) . .
N2 C14 C12 128.4(2) . .
C12 C14 O4 122.0(2) . .
O4 C15 C16 114.0(2) . .
C11 C15 O4 123.4(2) . .
C11 C15 C16 122.7(2) . .
C17 C16 C15 118.6(2) . .
O5 C17 C18 111.8(2) . .
C16 C17 O5 120.9(2) . .
C16 C17 C18 127.3(3) . .
C11 C19 C8 114.90(19) . .
C11 C19 C12 108.01(19) . .
C12 C19 C8 110.24(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.417(3) .
O1 C2 1.367(3) .
O2 C3 1.373(3) .
O2 C4 1.417(3) .
O3 C5 1.355(3) .
O3 C6 1.420(3) .
O4 C14 1.368(3) .
O4 C15 1.356(3) .
O5 C10 1.389(3) .
O5 C17 1.365(3) .
O6 C10 1.205(3) .
N1 C13 1.142(3) .
N2 C14 1.335(3) .
C2 C3 1.380(3) .
C2 C9 1.381(3) .
C3 C5 1.386(3) .
C5 C7 1.383(3) .
C7 C8 1.376(3) .
C8 C9 1.375(3) .
C8 C19 1.519(3) .
C10 C11 1.420(3) .
C11 C15 1.344(3) .
C11 C19 1.493(3) .
C12 C13 1.407(3) .
C12 C14 1.337(3) .
C12 C19 1.506(3) .
C15 C16 1.415(3) .
C16 C17 1.310(3) .
C17 C18 1.480(3) .
