#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/15/2231522.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_2231522
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
Nithinchandra
'Kalluraya, Balakrishna'
_publ_section_title
;
 Ethyl
 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate
;
_journal_coeditor_code           HB6375
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2416
_journal_paper_doi               10.1107/S1600536811033940
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H12 N4 O4'
_chemical_formula_moiety         'C12 H12 N4 O4'
_chemical_formula_sum            'C12 H12 N4 O4'
_chemical_formula_weight         276.26
_chemical_name_systematic
;
Ethyl 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 99.5740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5309(3)
_cell_length_b                   7.3014(2)
_cell_length_c                   12.6058(3)
_cell_measurement_reflns_used    8459
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.56
_cell_measurement_theta_min      3.05
_cell_volume                     1228.04(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL  (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16800
_diffrn_reflns_theta_full        32.64
_diffrn_reflns_theta_max         32.64
_diffrn_reflns_theta_min         3.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0579P)²+0.3698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                3699
_reflns_number_total             4469
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6375.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231522
_cod_database_fobs_code          2231522
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_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
_atom_site_symmetry_multiplicity
O O1 0.17538(5) 0.16665(10) -0.05384(5) 0.01804(15) Uani d . 1 1
O O2 0.81492(6) 0.19872(12) 0.56912(6) 0.02603(18) Uani d . 1 1
O O3 0.88912(6) 0.04601(13) 0.45702(7) 0.02874(19) Uani d . 1 1
O O4 0.14766(5) 0.02184(11) 0.09686(6) 0.02182(16) Uani d . 1 1
N N1 0.45814(6) 0.12739(11) 0.18124(6) 0.01308(15) Uani d . 1 1
N N2 0.46803(6) 0.17529(12) 0.07841(6) 0.01609(16) Uani d . 1 1
N N3 0.37872(6) 0.17308(12) 0.02083(6) 0.01568(16) Uani d . 1 1
N N4 0.81564(6) 0.12105(13) 0.48264(7) 0.01954(17) Uani d . 1 1
C C1 0.63468(7) 0.05446(13) 0.22772(7) 0.01570(17) Uani d . 1 1
H H1A 0.6336 0.0113 0.1564 0.019 Uiso calc R 1 1
C C2 0.72344(7) 0.05470(13) 0.30098(7) 0.01654(17) Uani d . 1 1
H H2A 0.7841 0.0126 0.2807 0.020 Uiso calc R 1 1
C C3 0.72162(7) 0.11789(13) 0.40463(7) 0.01516(17) Uani d . 1 1
C C4 0.63467(7) 0.17883(13) 0.43757(7) 0.01519(17) Uani d . 1 1
H H4A 0.6358 0.2197 0.5093 0.018 Uiso calc R 1 1
C C5 0.54574(7) 0.17947(13) 0.36424(7) 0.01414(16) Uani d . 1 1
H H5A 0.4852 0.2209 0.3850 0.017 Uiso calc R 1 1
C C6 0.54695(6) 0.11829(13) 0.25977(7) 0.01296(16) Uani d . 1 1
C C7 0.36061(6) 0.09299(12) 0.18864(7) 0.01266(16) Uani d . 1 1
C C8 0.31097(7) 0.12254(13) 0.08482(7) 0.01365(16) Uani d . 1 1
C C9 0.20306(7) 0.09756(13) 0.04465(7) 0.01549(17) Uani d . 1 1
C C10 0.32346(7) 0.03491(14) 0.28808(7) 0.01660(18) Uani d . 1 1
H H10A 0.3749 -0.0389 0.3327 0.025 Uiso calc R 1 1
H H10B 0.2624 -0.0381 0.2686 0.025 Uiso calc R 1 1
H H10C 0.3087 0.1434 0.3284 0.025 Uiso calc R 1 1
C C11 0.06813(7) 0.14784(16) -0.09678(8) 0.0212(2) Uani d . 1 1
H H11A 0.0276 0.1941 -0.0440 0.025 Uiso calc R 1 1
H H11B 0.0510 0.0175 -0.1116 0.025 Uiso calc R 1 1
C C12 0.04675(8) 0.25753(17) -0.19890(8) 0.0252(2) Uani d . 1 1
H H12A -0.0243 0.2459 -0.2301 0.038 Uiso calc R 1 1
H H12B 0.0879 0.2116 -0.2502 0.038 Uiso calc R 1 1
H H12C 0.0627 0.3866 -0.1830 0.038 Uiso calc R 1 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
C9 O1 C11 114.50(8)
C7 N1 N2 111.11(7)
C7 N1 C6 131.17(7)
N2 N1 C6 117.71(7)
N3 N2 N1 107.24(7)
N2 N3 C8 108.98(7)
O3 N4 O2 124.49(9)
O3 N4 C3 117.77(9)
O2 N4 C3 117.74(8)
C2 C1 C6 119.36(8)
C2 C1 H1A 120.3
C6 C1 H1A 120.3
C1 C2 C3 118.52(8)
C1 C2 H2A 120.7
C3 C2 H2A 120.7
C4 C3 C2 122.51(8)
C4 C3 N4 118.52(8)
C2 C3 N4 118.97(8)
C3 C4 C5 119.11(8)
C3 C4 H4A 120.4
C5 C4 H4A 120.4
C4 C5 C6 118.85(8)
C4 C5 H5A 120.6
C6 C5 H5A 120.6
C5 C6 C1 121.66(8)
C5 C6 N1 120.02(8)
C1 C6 N1 118.27(8)
N1 C7 C8 103.28(7)
N1 C7 C10 125.27(8)
C8 C7 C10 131.44(8)
N3 C8 C7 109.38(8)
N3 C8 C9 123.56(8)
C7 C8 C9 127.01(8)
O4 C9 O1 125.10(9)
O4 C9 C8 122.48(8)
O1 C9 C8 112.41(8)
C7 C10 H10A 109.5
C7 C10 H10B 109.5
H10A C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O1 C11 C12 107.67(8)
O1 C11 H11A 110.2
C12 C11 H11A 110.2
O1 C11 H11B 110.2
C12 C11 H11B 110.2
H11A C11 H11B 108.5
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.3348(11)
O1 C11 1.4685(11)
O2 N4 1.2303(12)
O3 N4 1.2246(12)
O4 C9 1.2103(12)
N1 C7 1.3616(11)
N1 N2 1.3705(10)
N1 C6 1.4258(11)
N2 N3 1.3022(11)
N3 C8 1.3686(11)
N4 C3 1.4730(12)
C1 C2 1.3879(13)
C1 C6 1.3962(13)
C1 H1A 0.9500
C2 C3 1.3897(13)
C2 H2A 0.9500
C3 C4 1.3846(13)
C4 C5 1.3901(12)
C4 H4A 0.9500
C5 C6 1.3933(12)
C5 H5A 0.9500
C7 C8 1.3849(12)
C7 C10 1.4878(12)
C8 C9 1.4751(13)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.5029(14)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
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
_geom_hbond_publ_flag
C1 H1A N3 3_655 0.95 2.59 3.5243(12) 168 yes
C5 H5A N2 4_566 0.95 2.60 3.2347(12) 125 yes
C5 H5A N3 4_566 0.95 2.54 3.4127(12) 154 yes
C10 H10B O4 . 0.98 2.48 3.0936(12) 120 yes
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
C7 N1 N2 N3 0.42(10)
C6 N1 N2 N3 179.36(8)
N1 N2 N3 C8 -0.58(10)
C6 C1 C2 C3 0.41(14)
C1 C2 C3 C4 0.58(14)
C1 C2 C3 N4 -179.20(8)
O3 N4 C3 C4 171.06(9)
O2 N4 C3 C4 -8.86(13)
O3 N4 C3 C2 -9.16(13)
O2 N4 C3 C2 170.93(9)
C2 C3 C4 C5 -0.85(14)
N4 C3 C4 C5 178.93(8)
C3 C4 C5 C6 0.12(14)
C4 C5 C6 C1 0.87(14)
C4 C5 C6 N1 -176.36(8)
C2 C1 C6 C5 -1.14(14)
C2 C1 C6 N1 176.14(8)
C7 N1 C6 C5 -40.05(14)
N2 N1 C6 C5 141.26(9)
C7 N1 C6 C1 142.62(10)
N2 N1 C6 C1 -36.07(12)
N2 N1 C7 C8 -0.07(10)
C6 N1 C7 C8 -178.83(9)
N2 N1 C7 C10 179.02(9)
C6 N1 C7 C10 0.27(15)
N2 N3 C8 C7 0.56(11)
N2 N3 C8 C9 -177.07(9)
N1 C7 C8 N3 -0.28(10)
C10 C7 C8 N3 -179.30(9)
N1 C7 C8 C9 177.24(9)
C10 C7 C8 C9 -1.78(17)
C11 O1 C9 O4 1.16(14)
C11 O1 C9 C8 -179.05(8)
N3 C8 C9 O4 166.28(9)
C7 C8 C9 O4 -10.92(16)
N3 C8 C9 O1 -13.51(13)
C7 C8 C9 O1 169.29(9)
C9 O1 C11 C12 171.11(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 613751
