#------------------------------------------------------------------------------
#$Date: 2022-11-30 10:50:50 +0200 (Wed, 30 Nov 2022) $
#$Revision: 279645 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106305.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_8106305
loop_
_publ_author_name
'Wang, Ning'
'Liu, Yu-Hang'
'Liu, Da-Wei'
'Zhao, Ye'
'Wen, Ping'
_publ_section_title
;
 Crystal structure of ethyl
 2-amino-4-(3-hydroxy-4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate,
 C22H19NO7
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              813
_journal_page_last               814
_journal_paper_doi               10.1515/ncrs-2018-0021
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C22 H19 N O7'
_chemical_formula_sum            'C22 H19 N O7'
_chemical_formula_weight         409.38
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 106.04(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.292(5)
_cell_length_b                   13.230(3)
_cell_length_c                   17.115(4)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.75
_cell_volume                     2022.1(14)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0534
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9575
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.975
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.079(4)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0441
_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)+(0.0564P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2422
_reflns_number_total             3545
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0021_suppl.cif
_cod_data_source_block           a
_cod_database_code               8106305
_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   0.983
_shelx_estimated_absorpt_t_min   0.974
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Me refined with riding coordinates:
 C1(H1C,H1D,H1E), C22(H22A,H22B,H22C)
2.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C21(H21)
2.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_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
N1 N 0.37739(19) 0.22910(14) -0.09055(9) 0.0680(5) Uani 1 1 d . . . . .
H1A H 0.454562 0.197290 -0.096259 0.082 Uiso 1 1 calc R . . . .
H1B H 0.318954 0.260025 -0.131310 0.082 Uiso 1 1 calc R . . . .
O1 O 0.62435(13) 0.08891(10) 0.12659(7) 0.0581(4) Uani 1 1 d . . . . .
O2 O 0.60726(16) 0.11426(12) -0.00619(8) 0.0728(5) Uani 1 1 d . . . . .
O3 O 0.21916(13) 0.28623(10) -0.02442(7) 0.0541(4) Uani 1 1 d . . . . .
O4 O 0.19830(13) 0.20025(10) 0.24259(7) 0.0540(4) Uani 1 1 d . . . . .
O5 O 0.00619(13) 0.27437(11) 0.15738(8) 0.0602(4) Uani 1 1 d . . . . .
O6 O 0.78606(13) 0.48778(10) 0.32840(7) 0.0588(4) Uani 1 1 d . . . . .
O7 O 0.60742(18) 0.54015(11) 0.18141(9) 0.0645(4) Uani 1 1 d . . . . .
C1 C 0.8186(3) 0.0013(3) 0.21988(17) 0.1226(12) Uani 1 1 d . . . . .
H1C H 0.909765 -0.036119 0.226885 0.184 Uiso 1 1 calc R . . . .
H1D H 0.837722 0.060055 0.254155 0.184 Uiso 1 1 calc R . . . .
H1E H 0.745486 -0.040469 0.234352 0.184 Uiso 1 1 calc R . . . .
C2 C 0.7611(2) 0.03309(18) 0.13369(13) 0.0733(7) Uani 1 1 d . . . . .
H2A H 0.834017 0.075368 0.118271 0.088 Uiso 1 1 calc R . . . .
H2B H 0.741357 -0.025617 0.098376 0.088 Uiso 1 1 calc R . . . .
C3 C 0.5577(2) 0.12786(15) 0.05236(11) 0.0515(5) Uani 1 1 d . . . . .
C4 C 0.42644(18) 0.18663(13) 0.05266(10) 0.0436(4) Uani 1 1 d . . . . .
C5 C 0.3484(2) 0.23048(14) -0.01861(11) 0.0481(5) Uani 1 1 d . . . . .
C6 C 0.15629(18) 0.28150(13) 0.03908(10) 0.0434(4) Uani 1 1 d . . . . .
C7 C 0.22544(17) 0.24035(13) 0.11173(10) 0.0408(4) Uani 1 1 d . . . . .
C8 C 0.38501(17) 0.20304(13) 0.13204(10) 0.0400(4) Uani 1 1 d . . . . .
H8 H 0.391033 0.138050 0.160236 0.048 Uiso 1 1 calc R . . . .
C9 C 0.14842(19) 0.23563(14) 0.17463(11) 0.0457(4) Uani 1 1 d . . . . .
C10 C -0.0612(2) 0.31983(15) 0.08299(12) 0.0549(5) Uani 1 1 d . . . . .
C11 C 0.00879(19) 0.32583(13) 0.02177(11) 0.0465(5) Uani 1 1 d . . . . .
C12 C -0.0658(2) 0.37428(15) -0.05158(12) 0.0591(5) Uani 1 1 d . . . . .
H12 H -0.020063 0.379295 -0.093380 0.071 Uiso 1 1 calc R . . . .
C13 C -0.2060(2) 0.41400(17) -0.06122(15) 0.0724(7) Uani 1 1 d . . . . .
H13 H -0.255085 0.446773 -0.109264 0.087 Uiso 1 1 calc R . . . .
C14 C -0.2743(2) 0.40502(19) 0.00127(17) 0.0853(8) Uani 1 1 d . . . . .
H14 H -0.370039 0.431131 -0.005972 0.102 Uiso 1 1 calc R . . . .
C15 C -0.2036(2) 0.35845(19) 0.07343(15) 0.0795(7) Uani 1 1 d . . . . .
H15 H -0.250180 0.352987 0.114844 0.095 Uiso 1 1 calc R . . . .
C16 C 0.48983(17) 0.27794(13) 0.18823(9) 0.0390(4) Uani 1 1 d . . . . .
C17 C 0.57893(18) 0.24937(14) 0.26417(10) 0.0478(5) Uani 1 1 d . . . . .
H17 H 0.572204 0.183833 0.282492 0.057 Uiso 1 1 calc R . . . .
C18 C 0.67800(19) 0.31702(15) 0.31329(10) 0.0508(5) Uani 1 1 d . . . . .
H18 H 0.736644 0.296821 0.364184 0.061 Uiso 1 1 calc R . . . .
C19 C 0.68936(17) 0.41454(14) 0.28639(10) 0.0450(5) Uani 1 1 d . . . . .
C20 C 0.59896(18) 0.44494(13) 0.21065(10) 0.0429(4) Uani 1 1 d . . . . .
C21 C 0.50009(17) 0.37731(13) 0.16279(10) 0.0431(4) Uani 1 1 d . . . . .
H21 H 0.439137 0.398231 0.112659 0.052 Uiso 1 1 calc R . . . .
C22 C 0.8763(2) 0.46398(18) 0.40787(12) 0.0715(7) Uani 1 1 d . . . . .
H22A H 0.937872 0.521066 0.430042 0.107 Uiso 1 1 calc R . . . .
H22B H 0.813132 0.447741 0.442003 0.107 Uiso 1 1 calc R . . . .
H22C H 0.938879 0.407061 0.405224 0.107 Uiso 1 1 calc R . . . .
H7 H 0.677(2) 0.5736(18) 0.2113(15) 0.084(8) Uiso 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
H1A N1 H1B 120.0 . .
C5 N1 H1A 120.0 . .
C5 N1 H1B 120.0 . .
C3 O1 C2 115.92(15) . .
C6 O3 C5 117.94(14) . .
C9 O5 C10 121.47(14) . .
C19 O6 C22 118.01(15) . .
C20 O7 H7 112.3(16) . .
H1C C1 H1D 109.5 . .
H1C C1 H1E 109.5 . .
H1D C1 H1E 109.5 . .
C2 C1 H1C 109.5 . .
C2 C1 H1D 109.5 . .
C2 C1 H1E 109.5 . .
O1 C2 C1 107.16(18) . .
O1 C2 H2A 110.3 . .
O1 C2 H2B 110.3 . .
C1 C2 H2A 110.3 . .
C1 C2 H2B 110.3 . .
H2A C2 H2B 108.5 . .
O1 C3 C4 111.63(16) . .
O2 C3 O1 122.31(17) . .
O2 C3 C4 126.05(18) . .
C3 C4 C8 119.96(16) . .
C5 C4 C3 117.74(16) . .
C5 C4 C8 122.19(15) . .
N1 C5 O3 109.44(16) . .
N1 C5 C4 128.87(17) . .
C4 C5 O3 121.68(16) . .
O3 C6 C11 114.02(15) . .
C7 C6 O3 123.47(15) . .
C7 C6 C11 122.50(17) . .
C6 C7 C8 122.18(16) . .
C6 C7 C9 119.71(16) . .
C9 C7 C8 118.04(15) . .
C4 C8 H8 108.6 . .
C4 C8 C16 112.24(14) . .
C7 C8 C4 108.35(14) . .
C7 C8 H8 108.6 . .
C7 C8 C16 110.33(14) . .
C16 C8 H8 108.6 . .
O4 C9 O5 115.99(16) . .
O4 C9 C7 126.09(16) . .
O5 C9 C7 117.92(16) . .
C11 C10 O5 122.18(16) . .
C15 C10 O5 116.20(19) . .
C15 C10 C11 121.61(19) . .
C10 C11 C6 116.13(16) . .
C10 C11 C12 118.92(17) . .
C12 C11 C6 124.94(18) . .
C11 C12 H12 120.1 . .
C13 C12 C11 119.9(2) . .
C13 C12 H12 120.1 . .
C12 C13 H13 120.2 . .
C12 C13 C14 119.6(2) . .
C14 C13 H13 120.2 . .
C13 C14 H14 119.3 . .
C15 C14 C13 121.5(2) . .
C15 C14 H14 119.3 . .
C10 C15 H15 120.8 . .
C14 C15 C10 118.4(2) . .
C14 C15 H15 120.8 . .
C17 C16 C8 121.63(16) . .
C17 C16 C21 118.32(15) . .
C21 C16 C8 120.04(14) . .
C16 C17 H17 119.5 . .
C16 C17 C18 121.07(17) . .
C18 C17 H17 119.5 . .
C17 C18 H18 120.1 . .
C19 C18 C17 119.90(15) . .
C19 C18 H18 120.1 . .
O6 C19 C18 125.43(15) . .
O6 C19 C20 114.82(16) . .
C18 C19 C20 119.75(16) . .
O7 C20 C19 121.71(16) . .
O7 C20 C21 118.51(15) . .
C21 C20 C19 119.77(17) . .
C16 C21 H21 119.4 . .
C20 C21 C16 121.17(15) . .
C20 C21 H21 119.4 . .
O6 C22 H22A 109.5 . .
O6 C22 H22B 109.5 . .
O6 C22 H22C 109.5 . .
H22A C22 H22B 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 H1A 0.8600 .
N1 H1B 0.8600 .
N1 C5 1.331(2) .
O1 C2 1.445(2) .
O1 C3 1.352(2) .
O2 C3 1.226(2) .
O3 C5 1.389(2) .
O3 C6 1.370(2) .
O4 C9 1.220(2) .
O5 C9 1.371(2) .
O5 C10 1.391(2) .
O6 C19 1.381(2) .
O6 C22 1.422(2) .
O7 C20 1.366(2) .
O7 H7 0.83(2) .
C1 H1C 0.9600 .
C1 H1D 0.9600 .
C1 H1E 0.9600 .
C1 C2 1.484(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.448(2) .
C4 C5 1.364(2) .
C4 C8 1.527(2) .
C6 C7 1.347(2) .
C6 C11 1.444(2) .
C7 C8 1.509(2) .
C7 C9 1.449(2) .
C8 H8 0.9800 .
C8 C16 1.529(2) .
C10 C11 1.380(3) .
C10 C15 1.385(3) .
C11 C12 1.409(3) .
C12 H12 0.9300 .
C12 C13 1.372(3) .
C13 H13 0.9300 .
C13 C14 1.392(3) .
C14 H14 0.9300 .
C14 C15 1.374(3) .
C15 H15 0.9300 .
C16 C17 1.387(2) .
C16 C21 1.396(2) .
C17 H17 0.9300 .
C17 C18 1.388(3) .
C18 H18 0.9300 .
C18 C19 1.384(3) .
C19 C20 1.395(2) .
C20 C21 1.378(2) .
C21 H21 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
