#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/71/2217183.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2217183
loop_
_publ_author_name
'Li, Jian'
_publ_section_title
;
 1-(4-Nitrophenoxymethyl)-1H-1,2,4-triazole
;
_journal_coeditor_code           LN2005
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o17
_journal_page_last               o17
_journal_paper_doi               10.1107/S1600536807060758
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H8 N4 O3'
_chemical_formula_moiety         'C9 H8 N4 O3'
_chemical_formula_sum            'C9 H8 N4 O3'
_chemical_formula_weight         220.19
_chemical_name_systematic
;
1-(4-Nitrophenoxymethyl)-1H-1,2,4-triazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.7300(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.2344(4)
_cell_length_b                   7.7197(3)
_cell_length_c                   22.7890(10)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.38
_cell_measurement_theta_min      3.12
_cell_volume                     1969.67(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18061
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.063P)²+0.0478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                2540
_reflns_number_total             3863
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ln2005.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        1969.65(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2217183
_cod_database_fobs_code          2217183
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.81377(17) 0.3196(3) 1.03182(8) 0.0408(5) Uani d . 1
C C2 0.93247(17) 0.3426(3) 1.04813(8) 0.0458(5) Uani d . 1
H H2 0.9670 0.4517 1.0461 0.055 Uiso calc R 1
C C3 1.00048(18) 0.2022(3) 1.06769(9) 0.0462(5) Uani d . 1
H H3 1.0817 0.2155 1.0783 0.055 Uiso calc R 1
C C4 0.94708(17) 0.0410(3) 1.07144(8) 0.0413(5) Uani d . 1
C C5 0.82669(17) 0.0197(3) 1.05410(9) 0.0465(5) Uani d . 1
H H5 0.7916 -0.0890 1.0559 0.056 Uiso calc R 1
C C6 0.75967(18) 0.1595(3) 1.03423(9) 0.0452(5) Uani d . 1
H H6 0.6789 0.1466 1.0225 0.054 Uiso calc R 1
C C7 1.12463(17) -0.0840(3) 1.11700(10) 0.0521(6) Uani d . 1
H H7A 1.1301 0.0134 1.1440 0.063 Uiso calc R 1
H H7B 1.1768 -0.0623 1.0860 0.063 Uiso calc R 1
C C8 1.15858(19) -0.2774(3) 1.20432(10) 0.0543(6) Uani d . 1
H H8 1.1336 -0.2011 1.2324 0.065 Uiso calc R 1
C C9 1.22169(18) -0.4899(3) 1.16231(11) 0.0572(6) Uani d . 1
H H9 1.2515 -0.6003 1.1563 0.069 Uiso calc R 1
C C10 0.1692(2) 0.7068(3) 0.80842(8) 0.0473(5) Uani d . 1
C C11 0.2882(2) 0.7309(3) 0.82472(9) 0.0533(6) Uani d . 1
H H11 0.3213 0.8413 0.8243 0.064 Uiso calc R 1
C C12 0.35811(18) 0.5906(3) 0.84169(9) 0.0494(6) Uani d . 1
H H12 0.4390 0.6050 0.8529 0.059 Uiso calc R 1
C C13 0.30677(17) 0.4276(3) 0.84194(9) 0.0440(5) Uani d . 1
C C14 0.18569(18) 0.4057(3) 0.82638(10) 0.0529(6) Uani d . 1
H H14 0.1515 0.2962 0.8278 0.064 Uiso calc R 1
C C15 0.11677(19) 0.5457(3) 0.80901(10) 0.0536(6) Uani d . 1
H H15 0.0358 0.5323 0.7978 0.064 Uiso calc R 1
C C16 0.49184(17) 0.2917(3) 0.87293(10) 0.0522(6) Uani d . 1
H H16A 0.5060 0.3587 0.9088 0.063 Uiso calc R 1
H H16B 0.5322 0.3479 0.8421 0.063 Uiso calc R 1
C C17 0.58384(17) 0.0123(3) 0.84480(10) 0.0543(6) Uani d . 1
H H17 0.5990 0.0408 0.8065 0.065 Uiso calc R 1
C C18 0.5699(2) -0.1152(3) 0.92397(12) 0.0624(6) Uani d . 1
H H18 0.5755 -0.2018 0.9524 0.075 Uiso calc R 1
N N1 0.74171(17) 0.4702(2) 1.01202(8) 0.0516(5) Uani d . 1
N N2 1.15923(14) -0.2405(2) 1.14761(7) 0.0444(4) Uani d . 1
N N3 1.20085(17) -0.3790(3) 1.11895(8) 0.0605(5) Uani d . 1
N N4 1.19720(17) -0.4338(3) 1.21593(9) 0.0617(5) Uani d . 1
N N5 0.0937(2) 0.8560(3) 0.79082(8) 0.0630(6) Uani d . 1
N N6 0.53437(14) 0.1182(2) 0.88181(7) 0.0460(4) Uani d . 1
N N7 0.52429(16) 0.0362(3) 0.93374(8) 0.0588(5) Uani d . 1
N N8 0.60847(16) -0.1386(3) 0.86990(9) 0.0631(6) Uani d . 1
O O1 0.79196(15) 0.6084(2) 1.00659(8) 0.0747(5) Uani d . 1
O O2 0.63420(14) 0.4506(2) 1.00168(8) 0.0744(5) Uani d . 1
O O3 0.13855(18) 0.9998(2) 0.79477(7) 0.0843(6) Uani d . 1
O O4 -0.01089(19) 0.8306(3) 0.77307(8) 0.0874(6) Uani d . 1
O O5 0.36738(12) 0.27844(18) 0.85648(7) 0.0563(4) Uani d . 1
O O6 1.00523(12) -0.10510(18) 1.09272(6) 0.0532(4) Uani d . 1
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
C2 C1 C6 121.91(19)
C2 C1 N1 118.85(19)
C6 C1 N1 119.23(18)
C1 C2 C3 119.2(2)
C1 C2 H2 120.4
C3 C2 H2 120.4
C2 C3 C4 119.62(19)
C2 C3 H3 120.2
C4 C3 H3 120.2
O6 C4 C3 124.31(17)
O6 C4 C5 115.34(18)
C3 C4 C5 120.34(19)
C6 C5 C4 119.80(19)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C6 C1 119.09(19)
C5 C6 H6 120.5
C1 C6 H6 120.5
O6 C7 N2 107.66(16)
O6 C7 H7A 110.2
N2 C7 H7A 110.2
O6 C7 H7B 110.2
N2 C7 H7B 110.2
H7A C7 H7B 108.5
N4 C8 N2 111.6(2)
N4 C8 H8 124.2
N2 C8 H8 124.2
N3 C9 N4 115.9(2)
N3 C9 H9 122.1
N4 C9 H9 122.1
C11 C10 C15 121.9(2)
C11 C10 N5 119.8(2)
C15 C10 N5 118.3(2)
C10 C11 C12 119.4(2)
C10 C11 H11 120.3
C12 C11 H11 120.3
C11 C12 C13 119.25(19)
C11 C12 H12 120.4
C13 C12 H12 120.4
O5 C13 C12 124.62(18)
O5 C13 C14 114.73(18)
C12 C13 C14 120.7(2)
C15 C14 C13 119.8(2)
C15 C14 H14 120.1
C13 C14 H14 120.1
C14 C15 C10 118.9(2)
C14 C15 H15 120.5
C10 C15 H15 120.5
O5 C16 N6 106.23(16)
O5 C16 H16A 110.5
N6 C16 H16A 110.5
O5 C16 H16B 110.5
N6 C16 H16B 110.5
H16A C16 H16B 108.7
N8 C17 N6 110.6(2)
N8 C17 H17 124.7
N6 C17 H17 124.7
N7 C18 N8 115.9(2)
N7 C18 H18 122.1
N8 C18 H18 122.1
O1 N1 O2 123.24(19)
O1 N1 C1 118.48(18)
O2 N1 C1 118.28(19)
C8 N2 N3 109.30(18)
C8 N2 C7 129.31(19)
N3 N2 C7 121.39(17)
C9 N3 N2 101.46(18)
C8 N4 C9 101.73(19)
O3 N5 O4 123.3(2)
O3 N5 C10 117.9(2)
O4 N5 C10 118.8(2)
C17 N6 N7 109.65(18)
C17 N6 C16 129.68(19)
N7 N6 C16 120.66(18)
C18 N7 N6 101.97(19)
C17 N8 C18 101.9(2)
N1 O2 H16A 132.4
C13 O5 C16 117.61(16)
C4 O6 C7 116.82(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.366(3)
C1 C6 1.381(3)
C1 N1 1.466(3)
C2 C3 1.379(3)
C2 H2 0.9300
C3 C4 1.387(3)
C3 H3 0.9300
C4 O6 1.372(2)
C4 C5 1.387(3)
C5 C6 1.371(3)
C5 H5 0.9300
C6 H6 0.9300
C7 O6 1.418(2)
C7 N2 1.433(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 N4 1.303(3)
C8 N2 1.324(2)
C8 H8 0.9300
C9 N3 1.314(3)
C9 N4 1.346(3)
C9 H9 0.9300
C10 C11 1.370(3)
C10 C15 1.376(3)
C10 N5 1.467(3)
C11 C12 1.375(3)
C11 H11 0.9300
C12 C13 1.384(3)
C12 H12 0.9300
C13 O5 1.365(2)
C13 C14 1.387(3)
C14 C15 1.369(3)
C14 H14 0.9300
C15 H15 0.9300
C16 O5 1.421(2)
C16 N6 1.431(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 N8 1.317(3)
C17 N6 1.329(3)
C17 H17 0.9300
C18 N7 1.302(3)
C18 N8 1.352(3)
C18 H18 0.9300
N1 O1 1.218(2)
N1 O2 1.221(2)
N2 N3 1.356(2)
N5 O3 1.219(3)
N5 O4 1.226(3)
N6 N7 1.355(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 O1 1_545 0.93 2.59 3.367(3) 141
C14 H14 O3 1_545 0.93 2.41 3.249(3) 150
C17 H17 N4 4 0.93 2.56 3.351(3) 144
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
C6 C1 C2 C3 -0.1(3)
N1 C1 C2 C3 178.99(17)
C1 C2 C3 C4 -1.1(3)
C2 C3 C4 O6 -176.99(18)
C2 C3 C4 C5 1.8(3)
O6 C4 C5 C6 177.62(18)
C3 C4 C5 C6 -1.3(3)
C4 C5 C6 C1 0.1(3)
C2 C1 C6 C5 0.6(3)
N1 C1 C6 C5 -178.46(17)
C15 C10 C11 C12 0.6(3)
N5 C10 C11 C12 179.39(18)
C10 C11 C12 C13 0.0(3)
C11 C12 C13 O5 178.33(19)
C11 C12 C13 C14 -1.2(3)
O5 C13 C14 C15 -177.77(19)
C12 C13 C14 C15 1.8(3)
C13 C14 C15 C10 -1.2(3)
C11 C10 C15 C14 0.0(3)
N5 C10 C15 C14 -178.81(19)
C2 C1 N1 O1 5.4(3)
C6 C1 N1 O1 -175.47(19)
C2 C1 N1 O2 -174.71(18)
C6 C1 N1 O2 4.4(3)
N4 C8 N2 N3 -0.2(2)
N4 C8 N2 C7 -179.68(19)
O6 C7 N2 C8 -96.5(2)
O6 C7 N2 N3 84.1(2)
N4 C9 N3 N2 -0.1(2)
C8 N2 N3 C9 0.2(2)
C7 N2 N3 C9 179.73(17)
N2 C8 N4 C9 0.1(2)
N3 C9 N4 C8 0.0(3)
C11 C10 N5 O3 -4.4(3)
C15 C10 N5 O3 174.4(2)
C11 C10 N5 O4 175.75(19)
C15 C10 N5 O4 -5.5(3)
N8 C17 N6 N7 -0.4(2)
N8 C17 N6 C16 -178.74(19)
O5 C16 N6 C17 94.9(2)
O5 C16 N6 N7 -83.2(2)
N8 C18 N7 N6 -0.2(2)
C17 N6 N7 C18 0.3(2)
C16 N6 N7 C18 178.84(18)
N6 C17 N8 C18 0.3(2)
N7 C18 N8 C17 -0.1(3)
C12 C13 O5 C16 0.5(3)
C14 C13 O5 C16 -179.93(18)
N6 C16 O5 C13 -176.10(17)
C3 C4 O6 C7 5.8(3)
C5 C4 O6 C7 -173.07(17)
N2 C7 O6 C4 167.68(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3523519
