#------------------------------------------------------------------------------
#$Date: 2019-04-03 05:52:35 +0300 (Wed, 03 Apr 2019) $
#$Revision: 214473 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/08/1550833.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_1550833
loop_
_publ_author_name
'Hebishy, Ali M.'
'Elgemeie, Galal H.'
'Salama, Hagar T.'
'Jones, Peter G.'
_publ_section_title
;
 3-Ethoxy-5-phenyl-1H-1,2,4-triazole
;
_journal_coeditor_code           SU4171
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x190378
_journal_paper_doi               10.1107/S241431461900378X
_journal_volume                  4
_journal_year                    2019
_chemical_formula_iupac          'C10 H11 N3 O'
_chemical_formula_moiety         'C10 H11 N3 O'
_chemical_formula_sum            'C10 H11 N3 O'
_chemical_formula_weight         189.22
_chemical_name_systematic
;
3-Ethoxy-5-phenyl-1H-1,2,4-triazole
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                79.554(4)
_cell_angle_beta                 81.137(4)
_cell_angle_gamma                70.517(5)
_cell_formula_units_Z            4
_cell_length_a                   8.0664(4)
_cell_length_b                   10.0476(5)
_cell_length_c                   12.5229(5)
_cell_measurement_reflns_used    16098
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0810
_cell_measurement_theta_min      3.5780
_cell_volume                     936.17(8)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Atlas Nova'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30281
_diffrn_reflns_theta_full        75.000
_diffrn_reflns_theta_max         76.287
_diffrn_reflns_theta_min         3.607
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0463P)²+0.2414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                3397
_reflns_number_total             3894
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4171sup1.cif
_cod_data_source_block           I
_cod_database_code               1550833
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.964
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
N N1 0.30398(12) 0.33959(10) 0.29129(7) 0.0186(2) Uani d 1
H H01 0.309(2) 0.2538(18) 0.2700(13) 0.033(4) Uiso d 1
N N2 0.31227(12) 0.34480(10) 0.39915(7) 0.0189(2) Uani d 1
C C3 0.30430(14) 0.47855(12) 0.39607(9) 0.0173(2) Uani d 1
N N4 0.29269(12) 0.55939(10) 0.29610(7) 0.0184(2) Uani d 1
C C5 0.29156(14) 0.46660(12) 0.23169(9) 0.0176(2) Uani d 1
C C6 0.31423(15) 0.44416(12) 0.58656(9) 0.0205(2) Uani d 1
H H6A 0.367766 0.477794 0.638132 0.025 Uiso calc 1
H H6B 0.390314 0.346689 0.574971 0.025 Uiso calc 1
C C7 0.13224(15) 0.44054(13) 0.63501(9) 0.0245(2) Uani d 1
H H7A 0.055441 0.537604 0.643488 0.037 Uiso calc 1
H H7B 0.140288 0.381170 0.706524 0.037 Uiso calc 1
H H7C 0.082810 0.400500 0.586489 0.037 Uiso calc 1
C C11 0.27486(14) 0.49708(12) 0.11405(9) 0.0191(2) Uani d 1
C C12 0.29281(16) 0.62379(13) 0.05453(9) 0.0236(2) Uani d 1
H H12 0.314085 0.691340 0.090316 0.028 Uiso calc 1
C C13 0.27955(17) 0.65127(13) -0.05738(10) 0.0259(3) Uani d 1
H H13 0.292318 0.737445 -0.097986 0.031 Uiso calc 1
C C14 0.24777(16) 0.55318(13) -0.10967(9) 0.0251(3) Uani d 1
H H14 0.238324 0.572415 -0.185999 0.030 Uiso calc 1
C C15 0.22973(18) 0.42703(14) -0.05082(10) 0.0286(3) Uani d 1
H H15 0.208292 0.359830 -0.086908 0.034 Uiso calc 1
C C16 0.24296(17) 0.39880(13) 0.06086(10) 0.0256(3) Uani d 1
H H16 0.230276 0.312403 0.101083 0.031 Uiso calc 1
O O1 0.30570(10) 0.53820(8) 0.48320(6) 0.01994(18) Uani d 1
N N1' 0.34778(13) -0.16318(10) 0.26565(8) 0.0196(2) Uani d 1
H H01' 0.325(2) -0.2465(18) 0.2761(12) 0.030(4) Uiso d 1
N N2' 0.51220(13) -0.15849(10) 0.21821(8) 0.0208(2) Uani d 1
C C3' 0.49143(15) -0.02159(12) 0.21179(9) 0.0196(2) Uani d 1
N N4' 0.33042(13) 0.06147(10) 0.25005(7) 0.0197(2) Uani d 1
C C5' 0.24252(15) -0.03317(12) 0.28387(8) 0.0185(2) Uani d 1
C C6' 0.78367(15) -0.05107(13) 0.12871(10) 0.0240(2) Uani d 1
H H6'1 0.808590 -0.147414 0.171531 0.029 Uiso calc 1
H H6'2 0.879139 -0.012801 0.135839 0.029 Uiso calc 1
C C7' 0.78071(18) -0.06106(14) 0.01023(10) 0.0293(3) Uani d 1
H H7'1 0.686086 -0.098850 0.003246 0.044 Uiso calc 1
H H7'2 0.894582 -0.124760 -0.017045 0.044 Uiso calc 1
H H7'3 0.759557 0.033952 -0.032440 0.044 Uiso calc 1
C C11' 0.05810(15) -0.00021(12) 0.33152(8) 0.0192(2) Uani d 1
C C12' -0.05513(16) 0.13969(12) 0.31547(10) 0.0238(2) Uani d 1
H H12' -0.012250 0.212809 0.274291 0.029 Uiso calc 1
C C13' -0.23009(16) 0.17204(13) 0.35957(10) 0.0263(3) Uani d 1
H H13' -0.306704 0.267400 0.348484 0.032 Uiso calc 1
C C14' -0.29414(16) 0.06579(13) 0.41993(10) 0.0248(3) Uani d 1
H H14' -0.414184 0.088374 0.449939 0.030 Uiso calc 1
C C15' -0.18179(16) -0.07356(13) 0.43617(10) 0.0248(2) Uani d 1
H H15' -0.225243 -0.146391 0.477316 0.030 Uiso calc 1
C C16' -0.00612(16) -0.10682(12) 0.39246(9) 0.0227(2) Uani d 1
H H16' 0.070371 -0.202176 0.404035 0.027 Uiso calc 1
O O1' 0.61578(11) 0.04083(9) 0.17153(7) 0.02334(19) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 110.54(9)
C5 N1 H01 130.1(10)
N2 N1 H01 119.4(10)
C3 N2 N1 101.40(9)
N2 C3 O1 124.72(10)
N2 C3 N4 116.09(10)
O1 C3 N4 119.19(10)
C5 N4 C3 102.22(9)
N1 C5 N4 109.75(9)
N1 C5 C11 123.83(10)
N4 C5 C11 126.40(10)
O1 C6 C7 110.87(9)
O1 C6 H6A 109.5
C7 C6 H6A 109.5
O1 C6 H6B 109.5
C7 C6 H6B 109.5
H6A C6 H6B 108.1
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C12 C11 C16 119.61(10)
C12 C11 C5 120.15(10)
C16 C11 C5 120.24(10)
C13 C12 C11 119.94(11)
C13 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C12 120.13(11)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 120.14(11)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 C16 120.06(12)
C14 C15 H15 120.0
C16 C15 H15 120.0
C15 C16 C11 120.12(11)
C15 C16 H16 119.9
C11 C16 H16 119.9
C3 O1 C6 115.05(9)
C5' N1' N2' 110.63(9)
C5' N1' H01' 130.4(10)
N2' N1' H01' 118.8(10)
C3' N2' N1' 100.98(9)
N2' C3' O1' 125.44(10)
N2' C3' N4' 116.40(10)
O1' C3' N4' 118.16(10)
C5' N4' C3' 102.35(9)
N1' C5' N4' 109.64(10)
N1' C5' C11' 124.66(10)
N4' C5' C11' 125.69(10)
O1' C6' C7' 110.59(10)
O1' C6' H6'1 109.5
C7' C6' H6'1 109.5
O1' C6' H6'2 109.5
C7' C6' H6'2 109.5
H6'1 C6' H6'2 108.1
C6' C7' H7'1 109.5
C6' C7' H7'2 109.5
H7'1 C7' H7'2 109.5
C6' C7' H7'3 109.5
H7'1 C7' H7'3 109.5
H7'2 C7' H7'3 109.5
C12' C11' C16' 119.52(11)
C12' C11' C5' 119.52(10)
C16' C11' C5' 120.96(10)
C13' C12' C11' 120.06(11)
C13' C12' H12' 120.0
C11' C12' H12' 120.0
C12' C13' C14' 120.41(11)
C12' C13' H13' 119.8
C14' C13' H13' 119.8
C15' C14' C13' 119.69(11)
C15' C14' H14' 120.2
C13' C14' H14' 120.2
C14' C15' C16' 120.25(11)
C14' C15' H15' 119.9
C16' C15' H15' 119.9
C15' C16' C11' 120.06(11)
C15' C16' H16' 120.0
C11' C16' H16' 120.0
C3' O1' C6' 116.23(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.3372(14)
N1 N2 1.3739(13)
N1 H01 0.935(17)
N2 C3 1.3176(15)
C3 O1 1.3399(13)
C3 N4 1.3610(14)
N4 C5 1.3418(14)
C5 C11 1.4670(15)
C6 O1 1.4537(13)
C6 C7 1.5092(15)
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C11 C12 1.3940(16)
C11 C16 1.3949(17)
C12 C13 1.3921(16)
C12 H12 0.9500
C13 C14 1.3857(18)
C13 H13 0.9500
C14 C15 1.3864(17)
C14 H14 0.9500
C15 C16 1.3892(16)
C15 H15 0.9500
C16 H16 0.9500
N1' C5' 1.3372(14)
N1' N2' 1.3795(13)
N1' H01' 0.898(17)
N2' C3' 1.3179(15)
C3' O1' 1.3428(14)
C3' N4' 1.3576(15)
N4' C5' 1.3407(15)
C5' C11' 1.4656(15)
C6' O1' 1.4477(14)
C6' C7' 1.5095(17)
C6' H6'1 0.9900
C6' H6'2 0.9900
C7' H7'1 0.9800
C7' H7'2 0.9800
C7' H7'3 0.9800
C11' C12' 1.3958(16)
C11' C16' 1.3964(16)
C12' C13' 1.3861(17)
C12' H12' 0.9500
C13' C14' 1.3903(17)
C13' H13' 0.9500
C14' C15' 1.3893(17)
C14' H14' 0.9500
C15' C16' 1.3896(17)
C15' H15' 0.9500
C16' H16' 0.9500
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
N1 H01 N4' . 0.94(2) 1.94(2) 2.8660(10) 170.0(10) yes
N1' H01' N4 1_545 0.90(2) 2.02(2) 2.9160(10) 176.0(10) yes
C13 H13 O1' 2_665 0.95 2.55 3.478(2) 165 yes
C15' H15' N2 2_556 0.95 2.52 3.463(2) 172 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
C5 N1 N2 C3 -0.12(11)
N1 N2 C3 O1 179.17(10)
N1 N2 C3 N4 -0.36(12)
N2 C3 N4 C5 0.68(12)
O1 C3 N4 C5 -178.88(9)
N2 N1 C5 N4 0.55(12)
N2 N1 C5 C11 -178.03(9)
C3 N4 C5 N1 -0.70(12)
C3 N4 C5 C11 177.83(10)
N1 C5 C11 C12 -169.05(11)
N4 C5 C11 C12 12.60(17)
N1 C5 C11 C16 10.20(17)
N4 C5 C11 C16 -168.14(11)
C16 C11 C12 C13 -0.25(18)
C5 C11 C12 C13 179.02(10)
C11 C12 C13 C14 0.28(18)
C12 C13 C14 C15 -0.25(19)
C13 C14 C15 C16 0.2(2)
C14 C15 C16 C11 -0.2(2)
C12 C11 C16 C15 0.18(18)
C5 C11 C16 C15 -179.08(11)
N2 C3 O1 C6 -0.91(15)
N4 C3 O1 C6 178.61(9)
C7 C6 O1 C3 -84.57(11)
C5' N1' N2' C3' 0.07(12)
N1' N2' C3' O1' 179.42(10)
N1' N2' C3' N4' -0.15(12)
N2' C3' N4' C5' 0.17(13)
O1' C3' N4' C5' -179.43(10)
N2' N1' C5' N4' 0.03(12)
N2' N1' C5' C11' 178.84(10)
C3' N4' C5' N1' -0.11(12)
C3' N4' C5' C11' -178.90(10)
N1' C5' C11' C12' -159.54(11)
N4' C5' C11' C12' 19.07(17)
N1' C5' C11' C16' 20.26(17)
N4' C5' C11' C16' -161.13(11)
C16' C11' C12' C13' -0.19(17)
C5' C11' C12' C13' 179.61(11)
C11' C12' C13' C14' -0.02(19)
C12' C13' C14' C15' 0.09(19)
C13' C14' C15' C16' 0.07(18)
C14' C15' C16' C11' -0.28(18)
C12' C11' C16' C15' 0.34(17)
C5' C11' C16' C15' -179.46(10)
N2' C3' O1' C6' 2.20(16)
N4' C3' O1' C6' -178.24(9)
C7' C6' O1' C3' 87.32(12)

_cod_database_fobs_code 1550833
