#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/43/4504399.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_4504399
loop_
_publ_author_name
'Wang, Yong-Tao'
'Tang, Gui-Mei'
'Liu, Zhi-Min'
'Yi, Xiang-Hui'
_publ_section_title
;
 Can One-Dimensional Water Be Controlled by Transformation of Substitution
 Groups Based on Organic Hosts?
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2272
_journal_paper_doi               10.1021/cg070487o
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2515(18)
_cell_length_b                   9.199(3)
_cell_length_c                   19.577(6)
_cell_measurement_temperature    298(2)
_cell_volume                     1125.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0847
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4967
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0471
_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)+(0.0527P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                1904
_reflns_number_total             2176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg070487o-file003.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1125.9(6)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4504399
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
O1 O -0.3080(3) -0.29938(18) -0.16647(9) 0.0600(5) Uani 1 1 d
O2 O -0.4252(3) -0.52802(17) -0.16181(9) 0.0600(5) Uani 1 1 d
N1 N -1.4617(3) -0.6069(2) -0.56826(10) 0.0502(5) Uani 1 1 d
N2 N -1.5131(3) -0.4574(2) -0.48183(8) 0.0423(5) Uani 1 1 d
C1 C -1.6534(4) -0.6370(3) -0.53742(15) 0.0641(8) Uani 1 1 d
C2 C -1.6851(4) -0.5471(3) -0.48460(13) 0.0593(7) Uani 1 1 d
H2 H -1.786(5) -0.546(3) -0.4529(15) 0.075(9) Uiso 1 1 d
C3 C -1.3843(4) -0.4996(3) -0.53312(12) 0.0457(6) Uani 1 1 d
H3 H -1.269(4) -0.451(2) -0.5415(13) 0.051(7) Uiso 1 1 d
C4 C -1.4721(4) -0.3401(3) -0.43291(12) 0.0488(6) Uani 1 1 d
H4B H -1.460(4) -0.245(3) -0.4570(11) 0.050(6) Uiso 1 1 d
H4A H -1.600(4) -0.335(3) -0.4031(12) 0.064(8) Uiso 1 1 d
C5 C -1.2796(3) -0.3708(2) -0.38832(11) 0.0381(5) Uani 1 1 d
C6 C -1.1405(4) -0.2582(2) -0.37258(11) 0.0406(5) Uani 1 1 d
H6 H -1.167(4) -0.160(3) -0.3894(12) 0.047(6) Uiso 1 1 d
C7 C -0.9647(4) -0.2826(2) -0.33022(11) 0.0416(5) Uani 1 1 d
H7 H -0.877(4) -0.198(2) -0.3199(12) 0.051(6) Uiso 1 1 d
C8 C -0.9289(3) -0.4193(2) -0.30268(10) 0.0377(5) Uani 1 1 d
C9 C -1.0676(4) -0.5319(3) -0.31919(10) 0.0435(5) Uani 1 1 d
H9 H -1.046(4) -0.631(2) -0.3023(11) 0.044(6) Uiso 1 1 d
C10 C -1.2433(4) -0.5074(2) -0.36134(12) 0.0433(5) Uani 1 1 d
H10 H -1.335(3) -0.590(2) -0.3701(11) 0.044(6) Uiso 1 1 d
C11 C -0.7504(4) -0.4498(3) -0.25554(11) 0.0424(5) Uani 1 1 d
H11 H -0.740(3) -0.547(2) -0.2393(11) 0.034(5) Uiso 1 1 d
C12 C -0.6009(4) -0.3591(3) -0.23450(11) 0.0442(5) Uani 1 1 d
H12 H -0.595(3) -0.257(2) -0.2477(9) 0.031(5) Uiso 1 1 d
C13 C -0.4377(4) -0.4066(2) -0.18464(11) 0.0431(5) Uani 1 1 d
H1 H -1.726(4) -0.721(3) -0.5504(13) 0.069(8) Uiso 1 1 d
H1A H -0.205(5) -0.340(3) -0.1344(16) 0.093(10) 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
C13 O1 H1A 106.8(18)
C3 N1 C1 104.2(2)
C3 N2 C2 105.6(2)
C3 N2 C4 126.6(2)
C2 N2 C4 127.79(19)
C2 C1 N1 110.2(2)
C2 C1 H1 130.6(17)
N1 C1 H1 118.3(16)
C1 C2 N2 106.8(2)
C1 C2 H2 130.9(19)
N2 C2 H2 122.0(19)
N1 C3 N2 113.1(2)
N1 C3 H3 127.2(16)
N2 C3 H3 119.4(16)
N2 C4 C5 112.25(18)
N2 C4 H4B 110.6(13)
C5 C4 H4B 112.0(14)
N2 C4 H4A 106.2(15)
C5 C4 H4A 108.1(14)
H4B C4 H4A 107.2(19)
C10 C5 C6 119.44(19)
C10 C5 C4 121.4(2)
C6 C5 C4 119.15(19)
C5 C6 C7 120.4(2)
C5 C6 H6 120.5(14)
C7 C6 H6 119.1(14)
C8 C7 C6 120.3(2)
C8 C7 H7 123.6(13)
C6 C7 H7 116.1(13)
C7 C8 C9 119.01(19)
C7 C8 C11 122.6(2)
C9 C8 C11 118.41(19)
C8 C9 C10 120.7(2)
C8 C9 H9 121.8(13)
C10 C9 H9 117.5(13)
C5 C10 C9 120.2(2)
C5 C10 H10 123.3(13)
C9 C10 H10 116.5(13)
C12 C11 C8 127.6(2)
C12 C11 H11 116.3(13)
C8 C11 H11 116.1(12)
C11 C12 C13 120.5(2)
C11 C12 H12 123.5(12)
C13 C12 H12 115.9(12)
O2 C13 O1 123.4(2)
O2 C13 C12 124.3(2)
O1 C13 C12 112.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.325(3)
O1 H1A 0.98(3)
O2 C13 1.206(3)
N1 C3 1.297(3)
N1 C1 1.370(3)
N2 C3 1.344(3)
N2 C2 1.356(3)
N2 C4 1.466(3)
C1 C2 1.339(4)
C1 H1 0.93(3)
C2 H2 0.88(3)
C3 H3 0.87(3)
C4 C5 1.513(3)
C4 H4B 1.00(2)
C4 H4A 0.99(2)
C5 C10 1.381(3)
C5 C6 1.387(3)
C6 C7 1.395(3)
C6 H6 0.98(2)
C7 C8 1.387(3)
C7 H7 0.97(2)
C8 C9 1.389(3)
C8 C11 1.475(3)
C9 C10 1.392(3)
C9 H9 0.98(2)
C10 H10 0.96(2)
C11 C12 1.319(3)
C11 H11 0.95(2)
C12 C13 1.478(3)
C12 H12 0.97(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4445594
2 PubChem 5282440
