#------------------------------------------------------------------------------
#$Date: 2022-12-05 12:24:36 +0200 (Mon, 05 Dec 2022) $
#$Revision: 279699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106323.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_8106323
loop_
_publ_author_name
'Li, Jing-Yao'
_publ_section_title
;
 Crystal structure of ethyl
 2-amino-4-(2,6-dichlorophenyl)-7-methyl-5-oxo-4H,5H-pyrano
 [4,3-b]pyran-3-carboxylate, C18H15Cl2NO5
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              857
_journal_page_last               858
_journal_paper_doi               10.1515/ncrs-2018-0054
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C18 H15 Cl2 N O5'
_chemical_formula_sum            'C18 H15 Cl2 N O5'
_chemical_formula_weight         396.21
_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                 117.62(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.423(5)
_cell_length_b                   27.798(3)
_cell_length_c                   9.550(2)
_cell_measurement_reflns_used    3004
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.52
_cell_volume                     1746.0(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8569
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.465
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.9348
_exptl_absorpt_correction_T_min  0.9027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0395
_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)+(0.0515P)²+0.1621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2430
_reflns_number_total             3061
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0054_suppl.cif
_cod_data_source_block           a
_cod_database_code               8106323
_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   0.935
_shelx_estimated_absorpt_t_min   0.903
_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 Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C16(H16), C17(H17)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C12(H12A,H12B,H12C)
;
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 1.0505(3) 0.14627(8) 1.3328(2) 0.0522(6) Uani 1 1 d . . . . .
H1A H 1.083603 0.117615 1.369882 0.063 Uiso 1 1 calc R . . . .
H1B H 1.105107 0.170698 1.392967 0.063 Uiso 1 1 calc R . . . .
Cl1 Cl 1.07403(9) 0.17300(2) 0.91678(7) 0.0472(2) Uani 1 1 d . . . . .
Cl2 Cl 0.39517(9) 0.05908(2) 0.64022(7) 0.04288(19) Uani 1 1 d . . . . .
O1 O 0.7478(2) 0.03749(5) 1.00297(17) 0.0406(4) Uani 1 1 d . . . . .
O2 O 0.9639(3) 0.05421(6) 1.25598(19) 0.0537(5) Uani 1 1 d . . . . .
O3 O 0.8871(2) 0.20136(6) 1.15152(17) 0.0451(4) Uani 1 1 d . . . . .
O4 O 0.3580(3) 0.18095(6) 0.62966(19) 0.0495(5) Uani 1 1 d . . . . .
O5 O 0.4524(2) 0.25377(5) 0.73158(19) 0.0430(4) Uani 1 1 d . . . . .
C1 C 0.6721(5) -0.04200(9) 0.8967(3) 0.0604(8) Uani 1 1 d . . . . .
H1C H 0.693298 -0.075652 0.921594 0.091 Uiso 1 1 calc GR . . . .
H1D H 0.723143 -0.033874 0.824014 0.091 Uiso 1 1 calc GR . . . .
H1E H 0.529281 -0.034972 0.849605 0.091 Uiso 1 1 calc GR . . . .
C2 C 0.7813(4) -0.01329(8) 1.0442(3) 0.0484(6) Uani 1 1 d . . . . .
H2A H 0.730500 -0.021235 1.118389 0.058 Uiso 1 1 calc R . . . .
H2B H 0.925612 -0.020471 1.093398 0.058 Uiso 1 1 calc R . . . .
C3 C 0.8517(4) 0.06857(8) 1.1220(3) 0.0371(5) Uani 1 1 d . . . . .
C4 C 0.8149(3) 0.11830(8) 1.0724(2) 0.0331(5) Uani 1 1 d . . . . .
C5 C 0.9151(4) 0.15279(8) 1.1829(3) 0.0375(5) Uani 1 1 d . . . . .
C6 C 0.7385(3) 0.21599(8) 1.0068(3) 0.0371(5) Uani 1 1 d . . . . .
C7 C 0.6305(3) 0.18470(8) 0.8888(2) 0.0321(5) Uani 1 1 d . . . . .
C8 C 0.6693(3) 0.13147(7) 0.9019(2) 0.0302(5) Uani 1 1 d . . . . .
H8 H 0.539530 0.115536 0.874872 0.036 Uiso 1 1 calc R . . . .
C9 C 0.4744(3) 0.20423(8) 0.7441(3) 0.0356(5) Uani 1 1 d . . . . .
C10 C 0.5704(4) 0.28397(8) 0.8527(3) 0.0431(6) Uani 1 1 d . . . . .
C11 C 0.7114(4) 0.26645(8) 0.9901(3) 0.0457(6) Uani 1 1 d . . . . .
H11 H 0.790175 0.286953 1.073010 0.055 Uiso 1 1 calc R . . . .
C12 C 0.5210(4) 0.33544(9) 0.8093(4) 0.0580(7) Uani 1 1 d . . . . .
H12A H 0.543144 0.342896 0.720278 0.087 Uiso 1 1 calc GR . . . .
H12B H 0.606777 0.355373 0.897180 0.087 Uiso 1 1 calc GR . . . .
H12C H 0.381215 0.341270 0.782291 0.087 Uiso 1 1 calc GR . . . .
C13 C 0.7420(3) 0.11351(7) 0.7844(2) 0.0285(5) Uani 1 1 d . . . . .
C14 C 0.9223(3) 0.12855(7) 0.7852(3) 0.0340(5) Uani 1 1 d . . . . .
C15 C 0.9915(4) 0.11016(8) 0.6847(3) 0.0414(6) Uani 1 1 d . . . . .
H15 H 1.111373 0.121656 0.688529 0.050 Uiso 1 1 calc R . . . .
C16 C 0.8820(4) 0.07467(9) 0.5786(3) 0.0465(6) Uani 1 1 d . . . . .
H16 H 0.930650 0.061119 0.513643 0.056 Uiso 1 1 calc R . . . .
C17 C 0.7007(4) 0.05934(8) 0.5690(3) 0.0400(6) Uani 1 1 d . . . . .
H17 H 0.624721 0.035791 0.496348 0.048 Uiso 1 1 calc R . . . .
C18 C 0.6323(3) 0.07917(7) 0.6680(2) 0.0322(5) Uani 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'
Cl Cl 0.1484 0.1585 '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 115.71(18) . .
C6 O3 C5 118.67(17) . .
C10 O5 C9 122.24(18) . .
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 108.3(2) . .
O1 C2 H2A 110.0 . .
O1 C2 H2B 110.0 . .
C1 C2 H2A 110.0 . .
C1 C2 H2B 110.0 . .
H2A C2 H2B 108.4 . .
O1 C3 C4 112.90(19) . .
O2 C3 O1 121.2(2) . .
O2 C3 C4 125.9(2) . .
C3 C4 C8 120.82(19) . .
C5 C4 C3 117.8(2) . .
C5 C4 C8 121.3(2) . .
N1 C5 O3 109.32(19) . .
N1 C5 C4 127.4(2) . .
C4 C5 O3 123.2(2) . .
O3 C6 C11 114.5(2) . .
C7 C6 O3 122.5(2) . .
C7 C6 C11 123.0(2) . .
C6 C7 C8 123.2(2) . .
C6 C7 C9 117.4(2) . .
C9 C7 C8 119.37(18) . .
C4 C8 H8 107.2 . .
C4 C8 C13 112.81(17) . .
C7 C8 C4 109.82(17) . .
C7 C8 H8 107.2 . .
C7 C8 C13 112.24(17) . .
C13 C8 H8 107.2 . .
O4 C9 O5 116.4(2) . .
O4 C9 C7 125.6(2) . .
O5 C9 C7 117.96(19) . .
O5 C10 C12 112.1(2) . .
C11 C10 O5 120.7(2) . .
C11 C10 C12 127.2(2) . .
C6 C11 H11 120.7 . .
C10 C11 C6 118.6(2) . .
C10 C11 H11 120.7 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C8 123.90(18) . .
C14 C13 C18 114.21(19) . .
C18 C13 C8 121.88(19) . .
C13 C14 Cl1 120.71(17) . .
C15 C14 Cl1 115.98(18) . .
C15 C14 C13 123.3(2) . .
C14 C15 H15 120.2 . .
C16 C15 C14 119.6(2) . .
C16 C15 H15 120.2 . .
C15 C16 H16 120.1 . .
C17 C16 C15 119.8(2) . .
C17 C16 H16 120.1 . .
C16 C17 H17 120.3 . .
C16 C17 C18 119.4(2) . .
C18 C17 H17 120.3 . .
C13 C18 Cl2 120.78(16) . .
C17 C18 Cl2 115.71(17) . .
C17 C18 C13 123.5(2) . .
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 1.326(3) .
Cl1 C14 1.750(2) .
Cl2 C18 1.746(3) .
O1 C2 1.456(3) .
O1 C3 1.349(3) .
O2 C3 1.226(3) .
O3 C5 1.378(3) .
O3 C6 1.370(3) .
O4 C9 1.218(3) .
O5 C9 1.385(3) .
O5 C10 1.368(3) .
C1 H1C 0.9600 .
C1 H1D 0.9600 .
C1 H1E 0.9600 .
C1 C2 1.490(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.445(3) .
C4 C5 1.363(3) .
C4 C8 1.524(3) .
C6 C7 1.353(3) .
C6 C11 1.415(3) .
C7 C8 1.502(3) .
C7 C9 1.436(3) .
C8 H8 0.9800 .
C8 C13 1.536(3) .
C10 C11 1.334(3) .
C10 C12 1.488(3) .
C11 H11 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 C14 1.399(3) .
C13 C18 1.404(3) .
C14 C15 1.380(3) .
C15 H15 0.9300 .
C15 C16 1.377(3) .
C16 H16 0.9300 .
C16 C17 1.374(4) .
C17 H17 0.9300 .
C17 C18 1.379(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Cl1 C14 C15 C16 179.32(18) . . . .
O1 C3 C4 C5 -178.89(19) . . . .
O1 C3 C4 C8 0.8(3) . . . .
O2 C3 C4 C5 0.9(4) . . . .
O2 C3 C4 C8 -179.3(2) . . . .
O3 C6 C7 C8 -3.1(3) . . . .
O3 C6 C7 C9 178.1(2) . . . .
O3 C6 C11 C10 179.7(2) . . . .
O5 C10 C11 C6 1.0(4) . . . .
C2 O1 C3 O2 -1.1(3) . . . .
C2 O1 C3 C4 178.76(19) . . . .
C3 O1 C2 C1 -174.4(2) . . . .
C3 C4 C5 N1 2.4(4) . . . .
C3 C4 C5 O3 -177.53(19) . . . .
C3 C4 C8 C7 170.00(19) . . . .
C3 C4 C8 C13 -64.0(3) . . . .
C4 C8 C13 C14 -62.5(3) . . . .
C4 C8 C13 C18 115.9(2) . . . .
C5 O3 C6 C7 -6.0(3) . . . .
C5 O3 C6 C11 175.58(19) . . . .
C5 C4 C8 C7 -10.3(3) . . . .
C5 C4 C8 C13 115.7(2) . . . .
C6 O3 C5 N1 -173.8(2) . . . .
C6 O3 C5 C4 6.1(3) . . . .
C6 C7 C8 C4 10.6(3) . . . .
C6 C7 C8 C13 -115.8(2) . . . .
C6 C7 C9 O4 -176.5(2) . . . .
C6 C7 C9 O5 3.6(3) . . . .
C7 C6 C11 C10 1.3(4) . . . .
C7 C8 C13 C14 62.2(3) . . . .
C7 C8 C13 C18 -119.4(2) . . . .
C8 C4 C5 N1 -177.4(2) . . . .
C8 C4 C5 O3 2.7(3) . . . .
C8 C7 C9 O4 4.6(3) . . . .
C8 C7 C9 O5 -175.28(18) . . . .
C8 C13 C14 Cl1 -4.1(3) . . . .
C8 C13 C14 C15 176.3(2) . . . .
C8 C13 C18 Cl2 5.7(3) . . . .
C8 C13 C18 C17 -174.56(19) . . . .
C9 O5 C10 C11 -0.9(3) . . . .
C9 O5 C10 C12 178.7(2) . . . .
C9 C7 C8 C4 -170.64(19) . . . .
C9 C7 C8 C13 63.0(3) . . . .
C10 O5 C9 O4 178.6(2) . . . .
C10 O5 C9 C7 -1.5(3) . . . .
C11 C6 C7 C8 175.3(2) . . . .
C11 C6 C7 C9 -3.6(3) . . . .
C12 C10 C11 C6 -178.5(2) . . . .
C13 C14 C15 C16 -1.0(3) . . . .
C14 C13 C18 Cl2 -175.73(15) . . . .
C14 C13 C18 C17 4.0(3) . . . .
C14 C15 C16 C17 2.8(3) . . . .
C15 C16 C17 C18 -1.1(3) . . . .
C16 C17 C18 Cl2 177.31(18) . . . .
C16 C17 C18 C13 -2.4(3) . . . .
C18 C13 C14 Cl1 177.40(15) . . . .
C18 C13 C14 C15 -2.3(3) . . . .
