#------------------------------------------------------------------------------
#$Date: 2022-06-30 11:59:33 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276441 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105586.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_8105586
loop_
_publ_author_name
'Liu, Xue-Kun'
'Geng, Xiao-Yu'
'Zhang, Meng'
'Ye, Bai-Jun'
'Shi, Zhan'
'Wang, Yan-Qiu'
_publ_section_title
;
 Crystal structure of ethyl
 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]
 chromene-3-carboxylate, C23H21NO6
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              193
_journal_page_last               194
_journal_paper_doi               10.1515/ncrs-2018-0151
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C23 H21 N O6'
_chemical_formula_sum            'C23 H21 N O6'
_chemical_formula_weight         407.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                94.13(3)
_cell_angle_beta                 102.27(3)
_cell_angle_gamma                106.72(3)
_cell_formula_units_Z            2
_cell_length_a                   7.624(4)
_cell_length_b                   9.197(5)
_cell_length_c                   15.058(5)
_cell_measurement_reflns_used    404
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      2.34
_cell_volume                     978.0(8)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0615
_diffrn_reflns_av_unetI/netI     0.1550
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4942
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.336
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.047(6)
_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   0.805
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.1579
_refine_ls_R_factor_gt           0.0662
_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)+(0.0720P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1362
_reflns_number_total             3393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0151_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        977.9(8)
_cod_database_code               8105586
_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.
;
_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), C15(H15A,H15B)
2.c Me refined with riding coordinates:
 C1(H1C,H1D,H1E), C16(H16A,H16B,H16C)
2.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C20(H20), C21(H21), C22(H22), C23(H23)
2.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.9912(4) 0.5063(4) 0.15831(19) 0.0543(10) Uani 1 1 d . . . . .
H1A H 1.001315 0.443769 0.197499 0.065 Uiso 1 1 calc R . . . .
H1B H 1.076472 0.534827 0.128300 0.065 Uiso 1 1 calc R . . . .
O1 O 0.5419(4) 0.4156(3) 0.28924(16) 0.0515(8) Uani 1 1 d . . . . .
O2 O 0.8004(4) 0.3542(3) 0.27445(16) 0.0587(8) Uani 1 1 d . . . . .
O3 O 0.7496(4) 1.0942(3) 0.46879(17) 0.0579(8) Uani 1 1 d . . . . .
O4 O 0.2531(4) 0.6949(3) 0.05293(17) 0.0606(9) Uani 1 1 d . . . . .
O5 O 0.4254(4) 0.8086(3) -0.03804(16) 0.0485(8) Uani 1 1 d . . . . .
O6 O 0.8640(4) 0.6587(3) 0.08029(16) 0.0493(8) Uani 1 1 d . . . . .
C1 C 0.3551(7) 0.3283(7) 0.3920(3) 0.0941(18) Uani 1 1 d . . . . .
H1C H 0.341139 0.269001 0.441409 0.141 Uiso 1 1 calc R . . . .
H1D H 0.364693 0.432383 0.412166 0.141 Uiso 1 1 calc R . . . .
H1E H 0.247208 0.285718 0.341032 0.141 Uiso 1 1 calc R . . . .
C2 C 0.5281(7) 0.3251(5) 0.3633(3) 0.0684(14) Uani 1 1 d . . . . .
H2A H 0.638277 0.367844 0.414194 0.082 Uiso 1 1 calc R . . . .
H2B H 0.520245 0.220496 0.342730 0.082 Uiso 1 1 calc R . . . .
C3 C 0.6888(6) 0.4256(5) 0.2510(2) 0.0431(10) Uani 1 1 d . . . . .
C4 C 0.6960(5) 0.5281(4) 0.1839(2) 0.0387(10) Uani 1 1 d . . . . .
C5 C 0.8439(6) 0.5586(4) 0.1441(2) 0.0404(10) Uani 1 1 d . . . . .
C6 C 0.7134(5) 0.7055(4) 0.0447(2) 0.0397(10) Uani 1 1 d . . . . .
C7 C 0.5612(5) 0.6823(4) 0.0802(2) 0.0368(9) Uani 1 1 d . . . . .
C8 C 0.5577(5) 0.6184(4) 0.1687(2) 0.0394(10) Uani 1 1 d . . . . .
H8 H 0.430513 0.549250 0.164288 0.047 Uiso 1 1 calc R . . . .
C9 C 0.6055(5) 0.7481(4) 0.2471(2) 0.0389(10) Uani 1 1 d . . . . .
C10 C 0.7770(6) 0.8588(5) 0.2675(2) 0.0495(11) Uani 1 1 d . . . . .
H10 H 0.861448 0.854249 0.231813 0.059 Uiso 1 1 calc R . . . .
C11 C 0.8305(6) 0.9780(5) 0.3393(2) 0.0491(11) Uani 1 1 d . . . . .
H11 H 0.947604 1.052765 0.350280 0.059 Uiso 1 1 calc R . . . .
C12 C 0.7097(6) 0.9852(5) 0.3941(2) 0.0460(10) Uani 1 1 d . . . . .
C13 C 0.5349(6) 0.8766(5) 0.3751(3) 0.0549(12) Uani 1 1 d . . . . .
H13 H 0.451202 0.881617 0.411164 0.066 Uiso 1 1 calc R . . . .
C14 C 0.4826(6) 0.7585(5) 0.3015(2) 0.0525(11) Uani 1 1 d . . . . .
H14 H 0.363595 0.685875 0.288809 0.063 Uiso 1 1 calc R . . . .
C15 C 0.9264(6) 1.2121(5) 0.4889(3) 0.0577(12) Uani 1 1 d . . . . .
H15A H 0.937257 1.267960 0.437054 0.069 Uiso 1 1 calc R . . . .
H15B H 1.028978 1.168203 0.501367 0.069 Uiso 1 1 calc R . . . .
C16 C 0.9358(7) 1.3180(5) 0.5715(3) 0.0788(16) Uani 1 1 d . . . . .
H16A H 1.054097 1.398917 0.586656 0.118 Uiso 1 1 calc R . . . .
H16B H 0.833954 1.361038 0.558411 0.118 Uiso 1 1 calc R . . . .
H16C H 0.925301 1.261688 0.622462 0.118 Uiso 1 1 calc R . . . .
C17 C 0.4040(6) 0.7255(5) 0.0337(3) 0.0453(10) Uani 1 1 d . . . . .
C18 C 0.5867(6) 0.8391(4) -0.0707(2) 0.0449(10) Uani 1 1 d . . . . .
C19 C 0.7325(5) 0.7845(4) -0.0331(2) 0.0400(10) Uani 1 1 d . . . . .
C20 C 0.8918(6) 0.8182(5) -0.0690(2) 0.0512(11) Uani 1 1 d . . . . .
H20 H 0.992177 0.783363 -0.044062 0.061 Uiso 1 1 calc R . . . .
C21 C 0.9022(7) 0.9014(5) -0.1402(3) 0.0599(12) Uani 1 1 d . . . . .
H21 H 1.006382 0.919831 -0.165533 0.072 Uiso 1 1 calc R . . . .
C22 C 0.7566(7) 0.9575(5) -0.1740(3) 0.0636(13) Uani 1 1 d . . . . .
H22 H 0.765838 1.018230 -0.220580 0.076 Uiso 1 1 calc R . . . .
C23 C 0.5981(7) 0.9261(5) -0.1406(2) 0.0556(12) Uani 1 1 d . . . . .
H23 H 0.499584 0.963361 -0.165067 0.067 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
H1A N1 H1B 120.0 . .
C5 N1 H1A 120.0 . .
C5 N1 H1B 120.0 . .
C3 O1 C2 117.1(3) . .
C12 O3 C15 117.6(3) . .
C17 O5 C18 122.0(3) . .
C6 O6 C5 117.6(3) . .
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 107.1(4) . .
O1 C2 H2A 110.3 . .
O1 C2 H2B 110.3 . .
C1 C2 H2A 110.3 . .
C1 C2 H2B 110.3 . .
H2A C2 H2B 108.6 . .
O1 C3 C4 111.9(3) . .
O2 C3 O1 121.7(4) . .
O2 C3 C4 126.4(4) . .
C3 C4 C8 120.0(4) . .
C5 C4 C3 118.8(3) . .
C5 C4 C8 120.6(3) . .
N1 C5 O6 108.4(3) . .
N1 C5 C4 129.1(3) . .
C4 C5 O6 122.5(3) . .
O6 C6 C19 114.0(3) . .
C7 C6 O6 123.1(3) . .
C7 C6 C19 122.9(3) . .
C6 C7 C8 121.2(3) . .
C6 C7 C17 118.8(3) . .
C17 C7 C8 119.9(3) . .
C4 C8 H8 108.9 . .
C4 C8 C9 111.5(3) . .
C7 C8 C4 108.8(3) . .
C7 C8 H8 108.9 . .
C7 C8 C9 109.8(3) . .
C9 C8 H8 108.9 . .
C10 C9 C8 119.9(4) . .
C10 C9 C14 117.2(4) . .
C14 C9 C8 122.8(4) . .
C9 C10 H10 118.7 . .
C9 C10 C11 122.7(4) . .
C11 C10 H10 118.7 . .
C10 C11 H11 120.2 . .
C12 C11 C10 119.7(4) . .
C12 C11 H11 120.2 . .
O3 C12 C11 124.9(4) . .
O3 C12 C13 115.8(4) . .
C11 C12 C13 119.4(4) . .
C12 C13 H13 120.0 . .
C12 C13 C14 120.0(4) . .
C14 C13 H13 120.0 . .
C9 C14 C13 121.0(4) . .
C9 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
O3 C15 H15A 110.2 . .
O3 C15 H15B 110.2 . .
O3 C15 C16 107.7(4) . .
H15A C15 H15B 108.5 . .
C16 C15 H15A 110.2 . .
C16 C15 H15B 110.2 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
O4 C17 O5 117.3(4) . .
O4 C17 C7 124.6(4) . .
O5 C17 C7 118.1(4) . .
C19 C18 O5 120.8(3) . .
C23 C18 O5 118.1(4) . .
C23 C18 C19 121.1(4) . .
C18 C19 C6 116.7(4) . .
C18 C19 C20 118.4(4) . .
C20 C19 C6 124.8(3) . .
C19 C20 H20 119.6 . .
C21 C20 C19 120.9(4) . .
C21 C20 H20 119.6 . .
C20 C21 H21 120.5 . .
C20 C21 C22 119.0(4) . .
C22 C21 H21 120.5 . .
C21 C22 H22 119.2 . .
C23 C22 C21 121.6(4) . .
C23 C22 H22 119.2 . .
C18 C23 H23 120.5 . .
C22 C23 C18 119.0(4) . .
C22 C23 H23 120.5 . .
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 1.328(4) .
O1 C2 1.442(4) .
O1 C3 1.348(4) .
O2 C3 1.228(4) .
O3 C12 1.371(4) .
O3 C15 1.422(5) .
O4 C17 1.205(5) .
O5 C17 1.379(4) .
O5 C18 1.382(5) .
O6 C5 1.379(4) .
O6 C6 1.359(4) .
C1 H1C 0.9600 .
C1 H1D 0.9600 .
C1 H1E 0.9600 .
C1 C2 1.480(6) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.430(5) .
C4 C5 1.355(5) .
C4 C8 1.511(5) .
C6 C7 1.347(5) .
C6 C19 1.434(5) .
C7 C8 1.497(5) .
C7 C17 1.429(5) .
C8 H8 0.9800 .
C8 C9 1.521(5) .
C9 C10 1.363(5) .
C9 C14 1.388(5) .
C10 H10 0.9300 .
C10 C11 1.386(5) .
C11 H11 0.9300 .
C11 C12 1.372(5) .
C12 C13 1.373(6) .
C13 H13 0.9300 .
C13 C14 1.399(5) .
C14 H14 0.9300 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.499(5) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C18 C19 1.379(5) .
C18 C23 1.371(5) .
C19 C20 1.396(5) .
C20 H20 0.9300 .
C20 C21 1.364(5) .
C21 H21 0.9300 .
C21 C22 1.373(5) .
C22 H22 0.9300 .
C22 C23 1.369(6) .
C23 H23 0.9300 .
