#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/12/2211222.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_2211222
loop_
_publ_author_name
'Wang, Hong-Mei'
'Zeng, Xiao-Hua'
'Hu, Zong-Qiu'
'Li, Gui-Hua'
'Tian, Jia-Hua'
_publ_section_title
;Ethyl
 1-benzyl-5-[2-(2,4-dichlorophenyl)-3-isopropylisoureido]-1H-1,2,3-triazole-4-carboxylate
;
_journal_coeditor_code           WK2029
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5174
_journal_page_last               o5175
_journal_paper_doi               10.1107/S1600536806043558
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H23 Cl2 N5 O3'
_chemical_formula_moiety         'C22 H23 Cl2 N5 O3'
_chemical_formula_sum            'C22 H23 Cl2 N5 O3'
_chemical_formula_weight         476.35
_chemical_name_systematic
;
 1-Benzyl-5-[2-(2,3-dichloro-phenyl)-3-isopropyl-isoureido]
-1H-1,2,3-triazole-4-carboxylic acid ethyl ester
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.639(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1692(8)
_cell_length_b                   10.1164(9)
_cell_length_c                   25.360(2)
_cell_measurement_reflns_used    2743
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      20.22
_cell_measurement_theta_min      2.58
_cell_volume                     2351.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART ccd area detector'
_diffrn_measurement_method       'φ and ω '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14845
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.9609
_exptl_absorpt_correction_T_min  0.9129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.620
_refine_ls_extinction_coef       0.00050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0651
_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)+(0.1039P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1954
_reflns_number_gt                2418
_reflns_number_total             4092
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            wk2029.cif
_cod_data_source_block           I
_cod_original_cell_volume        2351.4(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211222
_cod_database_fobs_code          2211222
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
C C1 0.5226(4) 0.4110(4) 0.19477(12) 0.0753(10) Uani d . 1
C C2 0.4942(4) 0.4461(5) 0.24625(14) 0.0899(12) Uani d . 1
H H2 0.4182 0.5036 0.2536 0.108 Uiso calc R 1
C C3 0.5792(5) 0.3949(5) 0.28567(15) 0.0953(13) Uani d . 1
C C4 0.6905(5) 0.3102(5) 0.27669(15) 0.1034(14) Uani d . 1
H H4 0.7466 0.2761 0.3046 0.124 Uiso calc R 1
C C5 0.7194(5) 0.2749(4) 0.22447(15) 0.0898(11) Uani d . 1
H H5 0.7952 0.2170 0.2174 0.108 Uiso calc R 1
C C6 0.6356(4) 0.3263(3) 0.18415(12) 0.0679(9) Uani d . 1
C C7 0.7364(3) 0.3688(3) 0.10123(12) 0.0595(8) Uani d . 1
C C8 0.6091(4) 0.2450(4) 0.02921(14) 0.0828(11) Uani d . 1
H H8 0.5275 0.2383 0.0532 0.099 Uiso calc R 1
C C9 0.6808(7) 0.1117(5) 0.0261(3) 0.149(2) Uani d . 1
H H9A 0.7581 0.1152 0.0014 0.223 Uiso calc R 1
H H9B 0.6100 0.0471 0.0146 0.223 Uiso calc R 1
H H9C 0.7201 0.0876 0.0602 0.223 Uiso calc R 1
C C10 0.5504(5) 0.2915(5) -0.02346(16) 0.1033(13) Uani d . 1
H H10A 0.5093 0.3782 -0.0199 0.155 Uiso calc R 1
H H10B 0.4762 0.2315 -0.0362 0.155 Uiso calc R 1
H H10C 0.6280 0.2945 -0.0480 0.155 Uiso calc R 1
C C11 0.9048(3) 0.5380(3) 0.09657(9) 0.0502(7) Uani d . 1
C C12 1.0310(3) 0.5239(3) 0.06778(11) 0.0567(8) Uani d . 1
C C13 1.1161(4) 0.4103(3) 0.05203(11) 0.0645(9) Uani d . 1
C C14 1.1448(6) 0.1802(4) 0.05943(19) 0.1201(17) Uani d . 1
H H14A 1.1398 0.1660 0.0216 0.144 Uiso calc R 1
H H14B 1.2466 0.1903 0.0702 0.144 Uiso calc R 1
C C15 1.0866(8) 0.0730(4) 0.0846(2) 0.145(2) Uani d . 1
H H15A 1.0715 0.0948 0.1209 0.218 Uiso calc R 1
H H15B 1.1527 -0.0004 0.0828 0.218 Uiso calc R 1
H H15C 0.9950 0.0497 0.0678 0.218 Uiso calc R 1
C C16 0.7712(4) 0.7427(3) 0.12449(12) 0.0672(9) Uani d . 1
H H16A 0.6827 0.6902 0.1238 0.081 Uiso calc R 1
H H16B 0.7511 0.8237 0.1052 0.081 Uiso calc R 1
C C17 0.8120(3) 0.7766(3) 0.18105(12) 0.0603(8) Uani d . 1
C C18 0.8885(5) 0.8877(4) 0.19436(16) 0.0948(12) Uani d . 1
H H18 0.9159 0.9456 0.1679 0.114 Uiso calc R 1
C C19 0.9264(5) 0.9164(5) 0.2466(2) 0.1112(15) Uani d . 1
H H19 0.9808 0.9916 0.2548 0.133 Uiso calc R 1
C C20 0.8832(5) 0.8332(6) 0.28574(16) 0.1009(14) Uani d . 1
H H20 0.9063 0.8521 0.3209 0.121 Uiso calc R 1
C C21 0.8080(6) 0.7253(5) 0.27298(16) 0.1082(15) Uani d . 1
H H21 0.7784 0.6684 0.2994 0.130 Uiso calc R 1
C C22 0.7730(5) 0.6963(4) 0.22111(14) 0.0884(11) Uani d . 1
H H22 0.7210 0.6194 0.2133 0.106 Uiso calc R 1
Cl Cl1 0.41980(12) 0.47759(15) 0.14379(4) 0.1179(5) Uani d . 1
Cl Cl2 0.54512(17) 0.44246(19) 0.35027(4) 0.1568(7) Uani d . 1
N N1 0.7129(3) 0.3429(3) 0.05081(9) 0.0697(8) Uani d . 1
H H1A 0.7733 0.3834 0.0243 0.084 Uiso d R 1
N N2 0.8169(3) 0.4551(2) 0.12456(9) 0.0557(6) Uani d . 1
N N3 0.8853(3) 0.6698(2) 0.09831(8) 0.0580(7) Uani d . 1
N N4 0.9900(4) 0.7343(3) 0.07156(11) 0.0780(9) Uani d . 1
N N5 1.0775(3) 0.6460(3) 0.05353(11) 0.0738(8) Uani d . 1
O O1 0.6565(3) 0.2862(2) 0.13251(8) 0.0763(7) Uani d . 1
O O2 1.0656(3) 0.2991(2) 0.07224(9) 0.0792(7) Uani d . 1
O O3 1.2201(3) 0.4157(3) 0.02441(9) 0.0855(8) 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'
cl cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C6 C1 C2 120.4(3) ?
C6 C1 Cl1 119.8(3) ?
C2 C1 Cl1 119.7(3) ?
C3 C2 C1 118.6(4) ?
C3 C2 H2 120.7 ?
C1 C2 H2 120.7 ?
C2 C3 C4 122.5(4) ?
C2 C3 Cl2 118.2(4) ?
C4 C3 Cl2 119.2(4) ?
C3 C4 C5 118.8(4) ?
C3 C4 H4 120.6 ?
C5 C4 H4 120.6 ?
C6 C5 C4 119.5(4) ?
C6 C5 H5 120.2 ?
C4 C5 H5 120.2 ?
C5 C6 C1 120.1(3) ?
C5 C6 O1 120.3(3) ?
C1 C6 O1 119.4(3) ?
N2 C7 N1 131.5(3) ?
N2 C7 O1 117.2(3) ?
N1 C7 O1 111.3(3) ?
N1 C8 C10 109.5(3) ?
N1 C8 C9 110.2(3) ?
C10 C8 C9 112.3(4) ?
N1 C8 H8 108.3 ?
C10 C8 H8 108.3 ?
C9 C8 H8 108.3 ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C8 C10 H10A 109.5 ?
C8 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C8 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
N3 C11 N2 120.5(2) y
N3 C11 C12 103.4(2) y
N2 C11 C12 135.7(3) y
N5 C12 C11 108.5(3) y
N5 C12 C13 118.1(3) ?
C11 C12 C13 133.4(3) ?
O3 C13 O2 123.8(3) ?
O3 C13 C12 124.6(3) ?
O2 C13 C12 111.7(3) ?
C15 C14 O2 110.3(4) ?
C15 C14 H14A 109.6 ?
O2 C14 H14A 109.6 ?
C15 C14 H14B 109.6 ?
O2 C14 H14B 109.6 ?
H14A C14 H14B 108.1 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N3 C16 C17 112.7(3) ?
N3 C16 H16A 109.0 ?
C17 C16 H16A 109.0 ?
N3 C16 H16B 109.0 ?
C17 C16 H16B 109.0 ?
H16A C16 H16B 107.8 ?
C22 C17 C18 117.0(3) ?
C22 C17 C16 120.7(3) ?
C18 C17 C16 122.3(3) ?
C17 C18 C19 121.4(4) ?
C17 C18 H18 119.3 ?
C19 C18 H18 119.3 ?
C20 C19 C18 119.5(4) ?
C20 C19 H19 120.2 ?
C18 C19 H19 120.2 ?
C21 C20 C19 119.2(4) ?
C21 C20 H20 120.4 ?
C19 C20 H20 120.4 ?
C20 C21 C22 120.9(4) ?
C20 C21 H21 119.5 ?
C22 C21 H21 119.5 ?
C17 C22 C21 121.9(4) ?
C17 C22 H22 119.1 ?
C21 C22 H22 119.1 ?
C7 N1 C8 125.7(3) ?
C7 N1 H1A 120.3 ?
C8 N1 H1A 113.8 ?
C7 N2 C11 121.1(2) y
C11 N3 N4 111.3(3) ?
C11 N3 C16 127.9(2) ?
N4 N3 C16 120.8(3) ?
N5 N4 N3 107.4(3) ?
N4 N5 C12 109.4(3) ?
C7 O1 C6 117.1(2) ?
C13 O2 C14 115.8(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.377(5) ?
C1 C2 1.385(5) ?
C1 Cl1 1.716(4) ?
C2 C3 1.353(6) ?
C2 H2 0.9300 ?
C3 C4 1.357(6) ?
C3 Cl2 1.744(4) ?
C4 C5 1.404(6) ?
C4 H4 0.9300 ?
C5 C6 1.364(5) ?
C5 H5 0.9300 ?
C6 O1 1.389(4) ?
C7 N2 1.278(4) y
C7 N1 1.317(4) y
C7 O1 1.377(3) y
C8 N1 1.468(4) ?
C8 C10 1.501(5) ?
C8 C9 1.504(6) ?
C8 H8 0.9800 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 N3 1.346(4) y
C11 N2 1.374(3) y
C11 C12 1.394(4) y
C12 N5 1.359(4) y
C12 C13 1.450(4) ?
C13 O3 1.201(4) ?
C13 O2 1.325(4) ?
C14 C15 1.375(6) ?
C14 O2 1.447(4) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 N3 1.456(4) ?
C16 C17 1.512(4) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 C22 1.357(4) ?
C17 C18 1.362(5) ?
C18 C19 1.390(6) ?
C18 H18 0.9300 ?
C19 C20 1.370(6) ?
C19 H19 0.9300 ?
C20 C21 1.326(6) ?
C20 H20 0.9300 ?
C21 C22 1.377(5) ?
C21 H21 0.9300 ?
C22 H22 0.9300 ?
N1 H1A 0.9733 ?
N3 N4 1.358(3) y
N4 N5 1.293(4) y
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
N1 H1A N5 3_765 0.97 2.45 3.317(3) 147.8
N1 H1A O3 3_765 0.97 2.38 3.170(4) 137.9
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(6) ?
Cl1 C1 C2 C3 -178.3(3) ?
C1 C2 C3 C4 -0.3(6) ?
C1 C2 C3 Cl2 178.6(3) ?
C2 C3 C4 C5 0.5(6) ?
Cl2 C3 C4 C5 -178.4(3) ?
C3 C4 C5 C6 0.0(6) ?
C4 C5 C6 C1 -0.7(5) ?
C4 C5 C6 O1 -175.9(3) ?
C2 C1 C6 C5 0.8(5) ?
Cl1 C1 C6 C5 178.8(3) ?
C2 C1 C6 O1 176.1(3) ?
Cl1 C1 C6 O1 -5.9(4) ?
N3 C11 C12 N5 -1.0(3) y
N2 C11 C12 N5 -173.3(3) ?
N3 C11 C12 C13 178.3(3) ?
N2 C11 C12 C13 5.9(6) ?
N5 C12 C13 O3 -4.8(5) ?
C11 C12 C13 O3 176.0(3) ?
N5 C12 C13 O2 174.7(3) ?
C11 C12 C13 O2 -4.5(5) ?
N3 C16 C17 C22 -93.5(4) ?
N3 C16 C17 C18 86.6(4) ?
C22 C17 C18 C19 0.9(6) ?
C16 C17 C18 C19 -179.2(4) ?
C17 C18 C19 C20 -1.6(7) ?
C18 C19 C20 C21 1.2(7) ?
C19 C20 C21 C22 -0.1(7) ?
C18 C17 C22 C21 0.3(6) ?
C16 C17 C22 C21 -179.6(4) ?
C20 C21 C22 C17 -0.7(7) ?
N2 C7 N1 C8 -175.8(3) ?
O1 C7 N1 C8 3.5(5) ?
C10 C8 N1 C7 148.3(3) ?
C9 C8 N1 C7 -87.7(5) ?
N1 C7 N2 C11 -3.3(5) ?
O1 C7 N2 C11 177.4(3) ?
N3 C11 N2 C7 118.7(3) y
C12 C11 N2 C7 -69.9(5) y
N2 C11 N3 N4 175.1(2) y
C12 C11 N3 N4 1.2(3) ?
N2 C11 N3 C16 -4.7(4) ?
C12 C11 N3 C16 -178.5(3) ?
C17 C16 N3 C11 89.1(4) ?
C17 C16 N3 N4 -90.6(3) ?
C11 N3 N4 N5 -1.1(3) y
C16 N3 N4 N5 178.7(3) ?
N3 N4 N5 C12 0.4(3) ?
C11 C12 N5 N4 0.3(3) y
C13 C12 N5 N4 -179.0(3) ?
N2 C7 O1 C6 18.4(4) ?
N1 C7 O1 C6 -161.1(3) ?
C5 C6 O1 C7 -100.1(4) ?
C1 C6 O1 C7 84.6(4) ?
O3 C13 O2 C14 0.5(5) ?
C12 C13 O2 C14 -179.1(3) ?
C15 C14 O2 C13 177.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126063
