#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/68/1506827.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_1506827
loop_
_publ_author_name
'Jian, Fang F.'
'Zhao, Pu S.'
'Yu, Qing'
'Wang, Qing X.'
'Jiao, Kui'
_publ_section_title
;
 Density Functional Calculations, Synthesis, and Characterization on Two
 Novel Quadruple Hydrogen-Bonded Supramolecular Complexes
;
_journal_issue                   24
_journal_name_full               'The Journal of Physical Chemistry A'
_journal_page_first              5258
_journal_paper_doi               10.1021/jp037926o
_journal_volume                  108
_journal_year                    2004
_chemical_formula_sum            'C9 H10 N O3'
_chemical_formula_weight         180.18
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8436(18)
_cell_length_b                   5.3476(11)
_cell_length_c                   18.839(4)
_cell_measurement_temperature    293(2)
_cell_volume                     878.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.825
_diffrn_measured_fraction_theta_max 0.825
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2696
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.103
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0906P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1584
_reflns_number_gt                1209
_reflns_number_total             1665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp037926osi20040307_093946.cif
_cod_data_source_block           compound_1
_cod_database_code               1506827
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.63762(19) 1.0692(3) -0.10701(10) 0.0528(5) Uani 1 1 d .
O2 O 0.8526(2) 1.1635(3) -0.03140(10) 0.0549(5) Uani 1 1 d .
O3 O 0.7810(2) 0.7723(3) 0.05013(9) 0.0576(5) Uani 1 1 d .
H3B H 0.8235 0.8923 0.0348 0.086 Uiso 1 1 d R
N1 N 0.6459(2) 0.7173(3) 0.00275(10) 0.0417(5) Uani 1 1 d .
C1 C 0.7016(3) 1.4079(4) -0.20892(13) 0.0496(6) Uani 1 1 d .
H1A H 0.6227 1.2937 -0.2223 0.060 Uiso 1 1 d R
C2 C 0.7321(3) 1.5910(5) -0.25763(14) 0.0560(7) Uani 1 1 d .
H2A H 0.6736 1.5991 -0.3034 0.067 Uiso 1 1 d R
C3 C 0.8489(3) 1.7604(4) -0.23709(15) 0.0539(7) Uani 1 1 d .
H3A H 0.8690 1.8828 -0.2693 0.065 Uiso 1 1 d R
C4 C 0.9358(3) 1.7485(5) -0.16898(14) 0.0503(7) Uani 1 1 d .
H4A H 1.0142 1.8638 -0.1557 0.060 Uiso 1 1 d R
C5 C 0.9077(3) 1.5677(4) -0.12068(14) 0.0445(6) Uani 1 1 d .
H5A H 0.9668 1.5606 -0.0750 0.053 Uiso 1 1 d R
C6 C 0.7900(3) 1.3957(4) -0.14063(12) 0.0399(6) Uani 1 1 d .
C7 C 0.7650(3) 1.2016(4) -0.08764(13) 0.0416(6) Uani 1 1 d .
C9 C 0.6245(3) 0.3875(5) 0.09235(14) 0.0512(7) Uani 1 1 d .
H9A H 0.7198 0.4552 0.1166 0.077 Uiso 1 1 d R
H9B H 0.6385 0.2149 0.0810 0.077 Uiso 1 1 d R
H9C H 0.5485 0.4005 0.1231 0.077 Uiso 1 1 d R
C8 C 0.5721(2) 0.5311(4) 0.02418(12) 0.0366(5) Uani 1 1 d .
H1B H 0.635(4) 0.933(6) -0.071(2) 0.094(11) 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
C8 N1 O3 112.66(18) . .
C6 C1 C2 120.0(2) . .
C3 C2 C1 119.5(2) . .
C2 C3 C4 120.3(2) . .
C5 C4 C3 120.8(2) . .
C4 C5 C6 119.6(2) . .
C1 C6 C5 119.9(2) . .
C1 C6 C7 122.1(2) . .
C5 C6 C7 118.0(2) . .
O2 C7 O1 122.4(2) . .
O2 C7 C6 123.8(2) . .
O1 C7 C6 113.8(2) . .
N1 C8 C8 114.2(2) . 3_665
N1 C8 C9 124.2(2) . .
C8 C8 C9 121.6(2) 3_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.329(3) .
O2 C7 1.221(3) .
O3 N1 1.398(2) .
N1 C8 1.291(3) .
C1 C6 1.391(3) .
C1 C2 1.399(4) .
C2 C3 1.380(4) .
C3 C4 1.382(4) .
C4 C5 1.379(3) .
C5 C6 1.393(3) .
C6 C7 1.482(3) .
C9 C8 1.502(3) .
C8 C8 1.476(4) 3_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139039782
