#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/4/50/26/4502652.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_4502652
loop_
_publ_author_name
'Naik, Anil D.'
'D\^irtu, Marinela M.'
'L\'eonard, Alexandre'
'Tinant, Bernard'
'Marchand-Brynaert, Jacqueline'
'Su, Bao-Lian'
'Garcia, Yann'
_publ_section_title
;
 Engineering Three-Dimensional Chains of Porous Nanoballs from a
 1,2,4-Triazole-carboxylate Supramolecular Synthon
;
_journal_issue                   4
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              1798
_journal_paper_doi               10.1021/cg901473d
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C4 H5 N3 O2'
_chemical_formula_weight         127.11
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   22.360(8)
_cell_length_b                   19.782(8)
_cell_length_c                   4.691(2)
_cell_measurement_reflns_used    ' all '
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.6
_cell_volume                     2074.9(14)
_computing_cell_refinement       ' mar '
_computing_data_collection       ' mar '
_computing_data_reduction        ' marhkl '
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3210
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ' parallelipided '
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1012
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.266
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0341
_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/[\s^2^(Fo^2^)+(0.0204P)^2^+4.1194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                1008
_reflns_number_total             1012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg901473d_si_002.cif
_cod_data_source_block           glybt
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      ' F dd2 '
_cod_database_code               4502652
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'
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
N1 N -0.01906(8) 0.09348(8) 1.2640(4) 0.0193(4) Uani 1 1 d .
N2 N -0.04962(8) 0.14428(9) 1.1209(4) 0.0205(4) Uani 1 1 d .
N4 N 0.04296(7) 0.13822(8) 0.9629(4) 0.0157(4) Uani 1 1 d .
C3 C -0.01064(8) 0.17035(10) 0.9430(5) 0.0196(4) Uani 1 1 d .
C5 C 0.03584(8) 0.09088(9) 1.1668(5) 0.0178(4) Uani 1 1 d .
C6 C 0.09909(9) 0.15705(10) 0.8268(5) 0.0171(4) Uani 1 1 d .
C7 C 0.13007(8) 0.21328(9) 0.9940(4) 0.0160(4) Uani 1 1 d .
O8 O 0.18272(6) 0.23113(7) 0.8990(3) 0.0200(4) Uani 1 1 d D
O9 O 0.10652(6) 0.24032(7) 1.1977(3) 0.0204(3) Uani 1 1 d .
H3 H -0.0185(12) 0.2076(13) 0.801(6) 0.025(3) Uiso 1 1 d .
H5 H 0.0677(12) 0.0559(13) 1.233(6) 0.025(3) Uiso 1 1 d .
H6A H 0.0906(11) 0.1755(14) 0.644(7) 0.025(3) Uiso 1 1 d .
H6B H 0.1262(12) 0.1170(14) 0.817(7) 0.025(3) Uiso 1 1 d .
H8 H 0.1984(12) 0.1986(12) 0.747(5) 0.025(3) Uiso 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0190(8) 0.0212(8) 0.0176(10) 0.0020(7) 0.0029(6) -0.0004(6)
N2 0.0154(8) 0.0213(8) 0.0247(10) 0.0013(7) 0.0032(7) 0.0019(6)
N4 0.0148(8) 0.0164(7) 0.0159(8) 0.0006(6) 0.0023(7) -0.0004(5)
C3 0.0148(9) 0.0215(9) 0.0224(11) 0.0041(8) -0.0010(8) 0.0007(6)
C5 0.0185(9) 0.0165(8) 0.0184(10) 0.0025(8) 0.0023(8) 0.0001(7)
C6 0.0170(9) 0.0196(9) 0.0147(10) 0.0003(7) 0.0032(8) -0.0010(8)
C7 0.0148(9) 0.0172(8) 0.0160(10) 0.0024(8) 0.0017(7) 0.0022(7)
O8 0.0145(7) 0.0211(7) 0.0243(9) -0.0029(6) 0.0047(6) -0.0027(5)
O9 0.0186(7) 0.0220(6) 0.0204(8) -0.0040(6) 0.0052(6) 0.0003(5)
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
C5 N1 N2 108.74(17)
C3 N2 N1 105.37(17)
C5 N4 C3 105.63(17)
C5 N4 C6 126.18(17)
C3 N4 C6 127.58(17)
N2 C3 N4 110.98(18)
N2 C3 H3 126.3(16)
N4 C3 H3 122.7(16)
N1 C5 N4 109.27(17)
N1 C5 H5 124.2(15)
N4 C5 H5 126.4(15)
N4 C6 C7 110.61(17)
N4 C6 H6A 108.8(16)
C7 C6 H6A 105.9(17)
N4 C6 H6B 109.8(16)
C7 C6 H6B 109.0(15)
H6A C6 H6B 113(2)
O9 C7 O8 122.63(18)
O9 C7 C6 121.88(17)
O8 C7 C6 115.47(17)
C7 O8 H8 112.1(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.311(3)
N1 N2 1.388(2)
N2 C3 1.312(3)
N4 C5 1.348(3)
N4 C3 1.360(2)
N4 C6 1.457(3)
C3 H3 1.01(3)
C5 H5 1.04(3)
C6 C7 1.527(3)
C6 H6A 0.95(3)
C6 H6B 1.00(3)
C7 O9 1.215(3)
C7 O8 1.307(2)
O8 H8 1.02(2)
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
C5 N1 N2 C3 -0.4(2)
N1 N2 C3 N4 0.8(2)
C5 N4 C3 N2 -0.9(2)
C6 N4 C3 N2 -172.23(19)
N2 N1 C5 N4 -0.1(2)
C3 N4 C5 N1 0.6(2)
C6 N4 C5 N1 172.1(2)
C5 N4 C6 C7 -89.0(2)
C3 N4 C6 C7 80.7(3)
N4 C6 C7 O9 -5.4(3)
N4 C6 C7 O8 176.06(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13958629
2 PubChem 12888432
