#------------------------------------------------------------------------------
#$Date: 2023-10-11 11:50:06 +0300 (Wed, 11 Oct 2023) $
#$Revision: 286910 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107608.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_8107608
loop_
_publ_author_name
'Chen, Hai-Lin'
'Yao, Dong-Mei'
'Luo, Ze-Ping'
'Wang, Yan-Ping'
'Tang, Yu-Mei'
_publ_section_title
;
 Synthesis and crystal structure of
 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate,
 C18H17N3O9
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              949
_journal_page_last               951
_journal_paper_doi               10.1515/ncrs-2023-0294
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C18 H17 N2 O6, N O3'
_chemical_formula_sum            'C18 H17 N3 O9'
_chemical_formula_weight         419.34
_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
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 102.700(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3768(3)
_cell_length_b                   7.4510(2)
_cell_length_c                   15.6673(5)
_cell_measurement_reflns_used    5634
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3170
_cell_measurement_theta_min      2.9410
_cell_volume                     1751.13(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)[1]'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)[1]'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)[1]'
_computing_molecular_graphics    'Diamond 3.2 [2]'
_computing_publication_material  'SHELXL 2018/3 (Sheldrick, 2015)[3]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)[3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)[4]'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8608
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.484
_diffrn_reflns_theta_min         2.946
_exptl_absorpt_coefficient_mu    1.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0405
_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)+(0.0629P)²+0.4560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2867
_reflns_number_total             3365
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0294_suppl_001.cif
_cod_data_source_block           a
_cod_database_code               8107608
_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   0.869
_shelx_estimated_absorpt_t_min   0.808
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C11(H11), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.12061(7) 0.69595(17) 0.37594(7) 0.0244(3) Uani 1 1 d . . . . .
H1 H 0.113052 0.634840 0.418784 0.037 Uiso 1 1 calc R U . . .
O2 O 0.53339(7) 0.58249(16) 0.39153(7) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.32749(6) 0.75673(15) 0.19759(7) 0.0198(2) Uani 1 1 d . . . . .
O4 O 0.82537(7) 0.70179(17) 0.16493(8) 0.0256(3) Uani 1 1 d . . . . .
H4 H 0.823354 0.693987 0.111048 0.038 Uiso 1 1 calc R U . . .
O5 O 0.73960(7) 0.64011(19) 0.00372(8) 0.0322(3) Uani 1 1 d . . . . .
O6 O 0.60442(8) 0.54183(19) -0.02255(8) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.09657(8) 0.68739(18) 0.15205(8) 0.0192(3) Uani 1 1 d . . . . .
H1A H 0.052415 0.763503 0.111274 0.023 Uiso 1 1 calc R U . . .
N2 N 0.66921(8) 0.6071(2) 0.02719(9) 0.0238(3) Uani 1 1 d . . . . .
C1 C 0.20526(9) 0.6755(2) 0.36637(10) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.27290(10) 0.6086(2) 0.43455(10) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.259206 0.572554 0.488261 0.026 Uiso 1 1 calc R U . . .
C3 C 0.35888(9) 0.5956(2) 0.42317(10) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.404482 0.551862 0.469589 0.024 Uiso 1 1 calc R U . . .
C4 C 0.38002(9) 0.6459(2) 0.34403(10) 0.0186(3) Uani 1 1 d . . . . .
C5 C 0.31153(9) 0.7085(2) 0.27698(10) 0.0175(3) Uani 1 1 d . . . . .
C6 C 0.22313(9) 0.7269(2) 0.28627(10) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.47196(9) 0.6341(2) 0.33206(10) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.48336(9) 0.6853(2) 0.24492(10) 0.0187(3) Uani 1 1 d . . . . .
C9 C 0.41175(9) 0.7431(2) 0.18478(10) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.421175 0.776801 0.129042 0.024 Uiso 1 1 calc R U . . .
C10 C 0.57229(9) 0.6802(2) 0.22197(10) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.58094(9) 0.6404(2) 0.13793(10) 0.0204(3) Uani 1 1 d . . . . .
H11 H 0.529840 0.607637 0.094657 0.024 Uiso 1 1 calc R U . . .
C12 C 0.66455(10) 0.6481(2) 0.11624(10) 0.0207(3) Uani 1 1 d . . . . .
C13 C 0.74188(9) 0.6910(2) 0.17902(11) 0.0209(3) Uani 1 1 d . . . . .
C14 C 0.73261(9) 0.7221(2) 0.26399(10) 0.0214(3) Uani 1 1 d . . . . .
H14 H 0.784233 0.745257 0.308495 0.026 Uiso 1 1 calc R U . . .
C15 C 0.65004(10) 0.7203(2) 0.28530(10) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.645691 0.746403 0.343561 0.025 Uiso 1 1 calc R U . . .
C16 C 0.15256(9) 0.8146(2) 0.21697(10) 0.0189(3) Uani 1 1 d . . . . .
H16A H 0.181891 0.901023 0.184356 0.023 Uiso 1 1 calc R U . . .
H16B H 0.112438 0.883870 0.246167 0.023 Uiso 1 1 calc R U . . .
C17 C 0.04345(10) 0.5584(2) 0.19292(11) 0.0239(3) Uani 1 1 d . . . . .
H17A H 0.083930 0.480001 0.233581 0.036 Uiso 1 1 calc R U . . .
H17B H 0.005840 0.485584 0.147187 0.036 Uiso 1 1 calc R U . . .
H17C H 0.005735 0.625112 0.224820 0.036 Uiso 1 1 calc R U . . .
C18 C 0.14978(10) 0.5927(2) 0.09690(10) 0.0217(3) Uani 1 1 d . . . . .
H18A H 0.180231 0.681185 0.067531 0.033 Uiso 1 1 calc R U . . .
H18B H 0.110018 0.519481 0.052959 0.033 Uiso 1 1 calc R U . . .
H18C H 0.194055 0.515220 0.133985 0.033 Uiso 1 1 calc R U . . .
O7 O 0.06716(7) 0.31052(18) 0.59633(8) 0.0300(3) Uani 1 1 d . . . . .
O8 O 0.10530(7) 0.53271(16) 0.52423(7) 0.0242(3) Uani 1 1 d . . . . .
O9 O 0.06919(7) 0.27676(18) 0.45887(8) 0.0297(3) Uani 1 1 d . . . . .
N3 N 0.08034(7) 0.37109(18) 0.52690(9) 0.0213(3) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 H1 109.5 . .
C9 O3 C5 118.85(11) . .
C13 O4 H4 109.5 . .
C16 N1 H1A 106.3 . .
C17 N1 H1A 106.3 . .
C17 N1 C16 113.50(12) . .
C18 N1 H1A 106.3 . .
C18 N1 C16 112.48(11) . .
C18 N1 C17 111.43(12) . .
O5 N2 C12 118.39(13) . .
O6 N2 O5 122.08(14) . .
O6 N2 C12 119.53(12) . .
O1 C1 C2 121.64(14) . .
O1 C1 C6 116.98(13) . .
C6 C1 C2 121.37(13) . .
C1 C2 H2 120.1 . .
C3 C2 C1 119.82(14) . .
C3 C2 H2 120.1 . .
C2 C3 H3 119.6 . .
C2 C3 C4 120.84(14) . .
C4 C3 H3 119.6 . .
C3 C4 C7 120.94(13) . .
C5 C4 C3 118.22(13) . .
C5 C4 C7 120.84(14) . .
O3 C5 C4 121.09(13) . .
O3 C5 C6 116.07(13) . .
C4 C5 C6 122.84(14) . .
C1 C6 C5 116.89(13) . .
C1 C6 C16 120.96(13) . .
C5 C6 C16 121.88(13) . .
O2 C7 C4 121.40(14) . .
O2 C7 C8 123.82(13) . .
C8 C7 C4 114.77(13) . .
C7 C8 C10 121.52(13) . .
C9 C8 C7 119.10(13) . .
C9 C8 C10 119.35(14) . .
O3 C9 H9 117.3 . .
C8 C9 O3 125.31(13) . .
C8 C9 H9 117.3 . .
C11 C10 C8 121.37(13) . .
C11 C10 C15 118.13(13) . .
C15 C10 C8 120.48(14) . .
C10 C11 H11 119.8 . .
C10 C11 C12 120.46(14) . .
C12 C11 H11 119.8 . .
C11 C12 N2 117.92(13) . .
C11 C12 C13 121.37(14) . .
C13 C12 N2 120.70(13) . .
O4 C13 C12 126.00(15) . .
O4 C13 C14 116.59(13) . .
C14 C13 C12 117.39(13) . .
C13 C14 H14 119.2 . .
C15 C14 C13 121.53(14) . .
C15 C14 H14 119.2 . .
C10 C15 H15 119.5 . .
C14 C15 C10 120.99(14) . .
C14 C15 H15 119.5 . .
N1 C16 H16A 108.5 . .
N1 C16 H16B 108.5 . .
C6 C16 N1 115.22(12) . .
C6 C16 H16A 108.5 . .
C6 C16 H16B 108.5 . .
H16A C16 H16B 107.5 . .
N1 C17 H17A 109.5 . .
N1 C17 H17B 109.5 . .
N1 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N1 C18 H18A 109.5 . .
N1 C18 H18B 109.5 . .
N1 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O7 N3 O8 119.07(14) . .
O7 N3 O9 121.64(14) . .
O9 N3 O8 119.29(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8400 .
O1 C1 1.3514(17) .
O2 C7 1.2334(18) .
O3 C5 1.3678(18) .
O3 C9 1.3578(17) .
O4 H4 0.8400 .
O4 C13 1.3521(17) .
O5 N2 1.2419(17) .
O6 N2 1.2228(18) .
N1 H1A 1.0000 .
N1 C16 1.5132(19) .
N1 C17 1.4935(19) .
N1 C18 1.4914(19) .
N2 C12 1.445(2) .
C1 C2 1.408(2) .
C1 C6 1.396(2) .
C2 H2 0.9500 .
C2 C3 1.376(2) .
C3 H3 0.9500 .
C3 C4 1.400(2) .
C4 C5 1.394(2) .
C4 C7 1.4692(18) .
C5 C6 1.4053(19) .
C6 C16 1.5052(19) .
C7 C8 1.465(2) .
C8 C9 1.352(2) .
C8 C10 1.4890(19) .
C9 H9 0.9500 .
C10 C11 1.384(2) .
C10 C15 1.408(2) .
C11 H11 0.9500 .
C11 C12 1.4014(19) .
C12 C13 1.403(2) .
C13 C14 1.389(2) .
C14 H14 0.9500 .
C14 C15 1.382(2) .
C15 H15 0.9500 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
O7 N3 1.2349(18) .
O8 N3 1.2674(18) .
O9 N3 1.2566(18) .
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
O1 C1 C2 C3 -177.78(15) . . . .
O1 C1 C6 C5 178.91(13) . . . .
O1 C1 C6 C16 4.7(2) . . . .
O2 C7 C8 C9 -178.87(15) . . . .
O2 C7 C8 C10 -0.7(2) . . . .
O3 C5 C6 C1 178.97(13) . . . .
O3 C5 C6 C16 -6.9(2) . . . .
O4 C13 C14 C15 177.92(14) . . . .
O5 N2 C12 C11 169.03(15) . . . .
O5 N2 C12 C13 -12.1(2) . . . .
O6 N2 C12 C11 -10.9(2) . . . .
O6 N2 C12 C13 168.00(15) . . . .
N2 C12 C13 O4 1.1(3) . . . .
N2 C12 C13 C14 -177.61(15) . . . .
C1 C2 C3 C4 -0.8(2) . . . .
C1 C6 C16 N1 -91.32(17) . . . .
C2 C1 C6 C5 0.1(2) . . . .
C2 C1 C6 C16 -174.07(15) . . . .
C2 C3 C4 C5 -0.4(2) . . . .
C2 C3 C4 C7 179.30(14) . . . .
C3 C4 C5 O3 -178.82(14) . . . .
C3 C4 C5 C6 1.5(2) . . . .
C3 C4 C7 O2 -1.2(2) . . . .
C3 C4 C7 C8 177.94(15) . . . .
C4 C5 C6 C1 -1.4(2) . . . .
C4 C5 C6 C16 172.72(14) . . . .
C4 C7 C8 C9 2.0(2) . . . .
C4 C7 C8 C10 -179.79(13) . . . .
C5 O3 C9 C8 -0.3(2) . . . .
C5 C4 C7 O2 178.48(15) . . . .
C5 C4 C7 C8 -2.4(2) . . . .
C5 C6 C16 N1 94.82(17) . . . .
C6 C1 C2 C3 1.0(2) . . . .
C7 C4 C5 O3 1.5(2) . . . .
C7 C4 C5 C6 -178.16(14) . . . .
C7 C8 C9 O3 -0.8(2) . . . .
C7 C8 C10 C11 147.65(16) . . . .
C7 C8 C10 C15 -33.9(2) . . . .
C8 C10 C11 C12 175.67(14) . . . .
C8 C10 C15 C14 -177.69(14) . . . .
C9 O3 C5 C4 -0.1(2) . . . .
C9 O3 C5 C6 179.58(13) . . . .
C9 C8 C10 C11 -34.1(2) . . . .
C9 C8 C10 C15 144.31(16) . . . .
C10 C8 C9 O3 -179.01(14) . . . .
C10 C11 C12 N2 -179.30(14) . . . .
C10 C11 C12 C13 1.8(2) . . . .
C11 C10 C15 C14 0.8(2) . . . .
C11 C12 C13 O4 179.91(15) . . . .
C11 C12 C13 C14 1.2(2) . . . .
C12 C13 C14 C15 -3.3(2) . . . .
C13 C14 C15 C10 2.3(2) . . . .
C15 C10 C11 C12 -2.8(2) . . . .
C17 N1 C16 C6 62.49(16) . . . .
C18 N1 C16 C6 -65.18(16) . . . .
