#------------------------------------------------------------------------------
#$Date: 2022-06-29 10:32:15 +0300 (Wed, 29 Jun 2022) $
#$Revision: 276379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105553.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_8105553
loop_
_publ_author_name
'Gou, Wei'
'Chen, Wei-Yong'
'Chen, Gang'
'Li, Wen-Jun'
_publ_section_title
;
 Crystal structure of ethyl
 2-amino-4-(3-bromophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate,
 C21H16BrNO5
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              95
_journal_page_last               96
_journal_paper_doi               10.1515/ncrs-2018-0201
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C21 H16 Br N O5'
_chemical_formula_sum            'C21 H16 Br N O5'
_chemical_formula_weight         442.26
_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                 90.720(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.146(5)
_cell_length_b                   8.188(4)
_cell_length_c                   22.204(4)
_cell_measurement_reflns_used    1142
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.40
_cell_measurement_theta_min      2.74
_cell_volume                     1844.5(13)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART (Bruker Apex-II, 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 0.998
_diffrn_measured_fraction_theta_max 0.991
_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  0.0706
_diffrn_reflns_av_unetI/netI     0.0990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10769
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.834
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.263
_exptl_absorpt_correction_T_max  0.6480
_exptl_absorpt_correction_T_min  0.5599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0565P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2046
_reflns_number_total             4194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0201_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1844.4(12)
_cod_database_code               8105553
_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   0.648
_shelx_estimated_absorpt_t_min   0.560
_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(H1A,H1B,H1C)
2.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C19(H19), C20(H20), C21(H21)
2.e X=CH2 refined with riding coordinates:
 N1(H1D,H1E)
;
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
Br1 Br 1.01226(5) -0.12388(7) 0.24669(2) 0.0624(2) Uani 1 1 d . . . . .
O1 O 0.7422(3) 0.4555(3) 0.11012(12) 0.0414(7) Uani 1 1 d . . . . .
O2 O 0.6199(3) 0.5111(3) 0.19100(13) 0.0477(8) Uani 1 1 d . . . . .
O3 O 0.4599(2) 0.0407(3) 0.17621(11) 0.0363(7) Uani 1 1 d . . . . .
O4 O 0.5304(3) -0.2497(4) 0.02994(12) 0.0442(7) Uani 1 1 d . . . . .
O5 O 0.6772(3) -0.0783(4) -0.00514(12) 0.0491(8) Uani 1 1 d . . . . .
C1 C 0.9029(5) 0.6287(6) 0.0674(2) 0.0734(16) Uani 1 1 d . . . . .
H1A H 0.948331 0.731139 0.071240 0.110 Uiso 1 1 calc R . . . .
H1B H 0.965638 0.540977 0.069044 0.110 Uiso 1 1 calc R . . . .
H1C H 0.855980 0.625487 0.029644 0.110 Uiso 1 1 calc R . . . .
C2 C 0.8088(4) 0.6111(5) 0.1172(2) 0.0490(12) Uani 1 1 d . . . . .
H2A H 0.855307 0.614691 0.155665 0.059 Uiso 1 1 calc R . . . .
H2B H 0.745224 0.699529 0.116112 0.059 Uiso 1 1 calc R . . . .
C3 C 0.6536(4) 0.4161(5) 0.15114(18) 0.0354(10) Uani 1 1 d . . . . .
C4 C 0.6034(3) 0.2515(5) 0.14284(16) 0.0302(9) Uani 1 1 d . . . . .
C5 C 0.5094(4) 0.1977(5) 0.17949(17) 0.0326(9) Uani 1 1 d . . . . .
C6 C 0.4916(3) -0.0519(5) 0.12734(17) 0.0309(9) Uani 1 1 d . . . . .
C7 C 0.5823(3) -0.0078(5) 0.08732(16) 0.0285(9) Uani 1 1 d . . . . .
C8 C 0.6639(4) 0.1452(4) 0.09459(17) 0.0301(9) Uani 1 1 d . . . . .
H8 H 0.660580 0.205441 0.056449 0.036 Uiso 1 1 calc R . . . .
C9 C 0.6029(4) -0.1084(5) 0.03497(18) 0.0366(10) Uani 1 1 d . . . . .
C10 C 0.4410(4) -0.2956(5) 0.07250(19) 0.0391(10) Uani 1 1 d . . . . .
C11 C 0.4169(4) -0.2006(5) 0.12251(18) 0.0328(9) Uani 1 1 d . . . . .
C12 C 0.3251(4) -0.2552(5) 0.16407(18) 0.0392(10) Uani 1 1 d . . . . .
H12 H 0.307500 -0.192940 0.198080 0.047 Uiso 1 1 calc R . . . .
C13 C 0.2606(4) -0.4003(6) 0.1550(2) 0.0524(12) Uani 1 1 d . . . . .
H13 H 0.199674 -0.436797 0.182837 0.063 Uiso 1 1 calc R . . . .
C14 C 0.2862(5) -0.4918(6) 0.1046(2) 0.0621(14) Uani 1 1 d . . . . .
H14 H 0.241980 -0.590205 0.098941 0.075 Uiso 1 1 calc R . . . .
C15 C 0.3749(4) -0.4419(6) 0.0627(2) 0.0563(13) Uani 1 1 d . . . . .
H15 H 0.390575 -0.504154 0.028517 0.068 Uiso 1 1 calc R . . . .
C16 C 0.8068(4) 0.1037(5) 0.10859(17) 0.0325(9) Uani 1 1 d . . . . .
C17 C 0.8398(4) 0.0270(5) 0.16149(18) 0.0368(10) Uani 1 1 d . . . . .
H17 H 0.774407 -0.000324 0.188690 0.044 Uiso 1 1 calc R . . . .
C18 C 0.9698(4) -0.0098(5) 0.17456(18) 0.0396(10) Uani 1 1 d . . . . .
C19 C 1.0680(4) 0.0286(6) 0.1352(2) 0.0571(14) Uani 1 1 d . . . . .
H19 H 1.155557 0.004736 0.144382 0.068 Uiso 1 1 calc R . . . .
C20 C 1.0337(4) 0.1038(6) 0.0813(2) 0.0575(14) Uani 1 1 d . . . . .
H20 H 1.098992 0.130157 0.053904 0.069 Uiso 1 1 calc R . . . .
C21 C 0.9046(4) 0.1398(5) 0.0678(2) 0.0433(11) Uani 1 1 d . . . . .
H21 H 0.882756 0.188522 0.031138 0.052 Uiso 1 1 calc R . . . .
N1 N 0.4490(3) 0.2753(4) 0.22416(14) 0.0426(9) Uani 1 1 d . . . . .
H1D H 0.469606 0.374688 0.232595 0.051 Uiso 1 1 calc R . . . .
H1E H 0.389401 0.226059 0.244531 0.051 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'
Br Br -0.2901 2.4595 '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
C3 O1 C2 117.2(3) . .
C6 O3 C5 118.0(3) . .
C10 O4 C9 122.2(3) . .
O1 C2 C1 108.0(4) . .
O1 C3 C4 112.2(3) . .
O2 C3 O1 122.5(4) . .
O2 C3 C4 125.3(4) . .
C3 C4 C8 118.6(3) . .
C5 C4 C3 118.7(3) . .
C5 C4 C8 122.6(4) . .
C4 C5 O3 122.4(3) . .
N1 C5 O3 108.2(3) . .
N1 C5 C4 129.3(4) . .
O3 C6 C11 113.6(3) . .
C7 C6 O3 123.3(4) . .
C7 C6 C11 123.1(4) . .
C6 C7 C8 122.3(3) . .
C6 C7 C9 119.3(4) . .
C9 C7 C8 118.4(3) . .
C4 C8 C16 112.2(3) . .
C7 C8 C4 109.0(3) . .
C7 C8 C16 110.9(3) . .
O4 C9 C7 117.6(3) . .
O5 C9 O4 117.0(4) . .
O5 C9 C7 125.4(4) . .
O4 C10 C11 121.7(4) . .
O4 C10 C15 116.8(4) . .
C11 C10 C15 121.4(4) . .
C10 C11 C6 116.0(3) . .
C10 C11 C12 118.6(4) . .
C12 C11 C6 125.3(4) . .
C13 C12 C11 120.1(4) . .
C12 C13 C14 119.9(4) . .
C15 C14 C13 121.6(4) . .
C14 C15 C10 118.2(4) . .
C17 C16 C8 120.1(3) . .
C17 C16 C21 119.3(4) . .
C21 C16 C8 120.6(4) . .
C16 C17 C18 120.2(4) . .
C17 C18 Br1 119.4(3) . .
C19 C18 Br1 119.5(3) . .
C19 C18 C17 121.1(4) . .
C18 C19 C20 118.4(4) . .
C21 C20 C19 120.8(4) . .
C20 C21 C16 120.1(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C18 1.899(4) .
O1 C2 1.450(5) .
O1 C3 1.327(4) .
O2 C3 1.230(4) .
O3 C5 1.382(5) .
O3 C6 1.365(4) .
O4 C9 1.374(5) .
O4 C10 1.371(4) .
O5 C9 1.200(4) .
C1 C2 1.477(6) .
C3 C4 1.451(5) .
C4 C5 1.337(5) .
C4 C8 1.516(5) .
C5 N1 1.334(4) .
C6 C7 1.337(5) .
C6 C11 1.437(5) .
C7 C8 1.510(5) .
C7 C9 1.442(5) .
C8 C16 1.517(5) .
C10 C11 1.380(5) .
C10 C15 1.389(6) .
C11 C12 1.393(5) .
C12 C13 1.370(6) .
C13 C14 1.373(6) .
C14 C15 1.365(6) .
C16 C17 1.370(5) .
C16 C21 1.385(5) .
C17 C18 1.381(5) .
C18 C19 1.370(6) .
C19 C20 1.387(6) .
C20 C21 1.372(6) .
