#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/51/2225179.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_2225179
loop_
_publ_author_name
'Dardouri, R.'
'Kandri Rodi, Y.'
'Saffon, Natalie'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione
_journal_coeditor_code           BT5192
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o632
_journal_paper_doi               10.1107/S1600536810005313
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H21 N5 O2'
_chemical_formula_moiety         'C21 H21 N5 O2'
_chemical_formula_sum            'C21 H21 N5 O2'
_chemical_formula_weight         375.43
_chemical_name_systematic
;
3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-
1,5-benzodiazepine-2,4-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.385(2)
_cell_angle_beta                 107.840(2)
_cell_angle_gamma                101.768(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3380(3)
_cell_length_b                   9.1033(3)
_cell_length_c                   13.4796(4)
_cell_measurement_reflns_used    1894
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8
_cell_measurement_theta_min      2.3
_cell_volume                     939.97(6)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII diffractometer'
_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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7973
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0417
_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)+(0.0760P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                2132
_reflns_number_total             3279
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5192.cif
_cod_data_source_block           I
_cod_original_cell_volume        939.97(5)
_cod_database_code               2225179
_cod_database_fobs_code          2225179
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.50707(19) 0.14271(17) 0.38773(13) 0.0383(4) Uani d . 1 . .
O O2 0.8254(2) 0.2153(2) 0.23619(15) 0.0501(5) Uani d . 1 . .
N N1 0.8448(2) 0.2106(2) 0.71289(16) 0.0366(5) Uani d . 1 . .
N N2 0.9062(2) 0.3607(2) 0.71872(16) 0.0376(5) Uani d . 1 . .
N N3 0.9231(2) 0.3802(2) 0.62613(16) 0.0359(5) Uani d . 1 . .
N N4 0.4763(2) 0.37357(19) 0.34845(14) 0.0283(4) Uani d . 1 . .
N N5 0.6925(2) 0.4101(2) 0.21476(15) 0.0310(5) Uani d . 1 . .
C C1 0.9776(3) 0.1642(3) 0.89419(19) 0.0359(6) Uani d . 1 . .
C C2 1.0765(3) 0.0598(3) 0.8911(2) 0.0409(6) Uani d . 1 . .
H H2 1.0396 -0.0190 0.8339 0.049 Uiso calc R 1 . .
C C3 1.2289(4) 0.0720(4) 0.9720(3) 0.0650(9) Uani d . 1 . .
H H3 1.2943 0.0013 0.9694 0.078 Uiso calc R 1 . .
C C4 1.2843(5) 0.1865(6) 1.0557(3) 0.0935(15) Uani d . 1 . .
H H4 1.3868 0.1928 1.1106 0.112 Uiso calc R 1 . .
C C5 1.1909(6) 0.2932(5) 1.0604(3) 0.0947(16) Uani d . 1 . .
H H5 1.2312 0.3731 1.1171 0.114 Uiso calc R 1 . .
C C6 1.0353(5) 0.2807(3) 0.9796(2) 0.0610(9) Uani d . 1 . .
H H6 0.9699 0.3512 0.9831 0.073 Uiso calc R 1 . .
C C7 0.8123(3) 0.1525(3) 0.8049(2) 0.0442(7) Uani d . 1 . .
H H7A 0.7476 0.0468 0.7836 0.053 Uiso calc R 1 . .
H H7B 0.7415 0.2096 0.8294 0.053 Uiso calc R 1 . .
C C8 0.8216(3) 0.1340(3) 0.6177(2) 0.0364(6) Uani d . 1 . .
H H8 0.7799 0.0296 0.5944 0.044 Uiso calc R 1 . .
C C9 0.8726(3) 0.2424(3) 0.56202(19) 0.0321(6) Uani d . 1 . .
C C10 0.8729(3) 0.2271(3) 0.45103(19) 0.0346(6) Uani d . 1 . .
H H10A 0.8279 0.1209 0.4181 0.042 Uiso calc R 1 . .
H H10B 0.9915 0.2590 0.4515 0.042 Uiso calc R 1 . .
C C11 0.5716(3) 0.2698(2) 0.37552(18) 0.0282(5) Uani d . 1 . .
C C12 0.7630(3) 0.3225(2) 0.38576(18) 0.0284(5) Uani d . 1 . .
H H12 0.8070 0.4292 0.4202 0.034 Uiso calc R 1 . .
C C13 0.7673(3) 0.3110(3) 0.27368(19) 0.0324(6) Uani d . 1 . .
C C14 0.6468(3) 0.5362(2) 0.26045(17) 0.0286(5) Uani d . 1 . .
C C15 0.6992(3) 0.6803(3) 0.2368(2) 0.0357(6) Uani d . 1 . .
H H15 0.7607 0.6919 0.1898 0.043 Uiso calc R 1 . .
C C16 0.6620(3) 0.8055(3) 0.2814(2) 0.0403(6) Uani d . 1 . .
H H16 0.6977 0.9004 0.2641 0.048 Uiso calc R 1 . .
C C17 0.5715(3) 0.7908(3) 0.3521(2) 0.0385(6) Uani d . 1 . .
H H17 0.5500 0.8760 0.3844 0.046 Uiso calc R 1 . .
C C18 0.5137(3) 0.6485(2) 0.37394(19) 0.0324(5) Uani d . 1 . .
H H18 0.4513 0.6384 0.4205 0.039 Uiso calc R 1 . .
C C19 0.5468(3) 0.5196(2) 0.32765(17) 0.0268(5) Uani d . 1 . .
C C20 0.2922(3) 0.3329(3) 0.3420(2) 0.0364(6) Uani d . 1 . .
H H20A 0.2357 0.2351 0.2985 0.055 Uiso calc R 1 . .
H H20B 0.2356 0.4080 0.3118 0.055 Uiso calc R 1 . .
H H20C 0.2857 0.3293 0.4117 0.055 Uiso calc R 1 . .
C C21 0.7053(3) 0.4078(3) 0.1087(2) 0.0440(7) Uani d . 1 . .
H H21A 0.8197 0.4626 0.1138 0.066 Uiso calc R 1 . .
H H21B 0.6207 0.4549 0.0672 0.066 Uiso calc R 1 . .
H H21C 0.6841 0.3044 0.0756 0.066 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 N2 . . 111.21(19) ?
C8 N1 C7 . . 129.2(2) ?
N2 N1 C7 . . 119.6(2) ?
N3 N2 N1 . . 106.65(19) ?
N2 N3 C9 . . 109.22(18) ?
C11 N4 C19 . . 123.05(17) ?
C11 N4 C20 . . 117.89(17) ?
C19 N4 C20 . . 119.06(17) ?
C13 N5 C14 . . 122.66(19) ?
C13 N5 C21 . . 116.48(19) ?
C14 N5 C21 . . 118.77(18) ?
C6 C1 C2 . . 118.8(3) ?
C6 C1 C7 . . 120.7(3) ?
C2 C1 C7 . . 120.4(2) ?
C3 C2 C1 . . 120.4(3) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C4 C3 C2 . . 120.4(3) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C4 C5 C6 . . 119.4(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C1 C6 C5 . . 120.3(3) ?
C1 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
N1 C7 C1 . . 112.38(19) ?
N1 C7 H7A . . 109.1 ?
C1 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C1 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.9 ?
N1 C8 C9 . . 105.3(2) ?
N1 C8 H8 . . 127.4 ?
C9 C8 H8 . . 127.4 ?
N3 C9 C8 . . 107.7(2) ?
N3 C9 C10 . . 122.0(2) ?
C8 C9 C10 . . 130.3(2) ?
C9 C10 C12 . . 112.07(18) ?
C9 C10 H10A . . 109.2 ?
C12 C10 H10A . . 109.2 ?
C9 C10 H10B . . 109.2 ?
C12 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
O1 C11 N4 . . 122.12(19) ?
O1 C11 C12 . . 122.85(19) ?
N4 C11 C12 . . 115.00(18) ?
C13 C12 C11 . . 105.92(18) ?
C13 C12 C10 . . 112.28(18) ?
C11 C12 C10 . . 111.64(17) ?
C13 C12 H12 . . 109.0 ?
C11 C12 H12 . . 109.0 ?
C10 C12 H12 . . 109.0 ?
O2 C13 N5 . . 121.9(2) ?
O2 C13 C12 . . 122.3(2) ?
N5 C13 C12 . . 115.6(2) ?
C15 C14 C19 . . 118.5(2) ?
C15 C14 N5 . . 119.6(2) ?
C19 C14 N5 . . 121.94(19) ?
C16 C15 C14 . . 121.4(2) ?
C16 C15 H15 . . 119.3 ?
C14 C15 H15 . . 119.3 ?
C15 C16 C17 . . 120.2(2) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C18 C17 C16 . . 119.3(2) ?
C18 C17 H17 . . 120.4 ?
C16 C17 H17 . . 120.4 ?
C17 C18 C19 . . 121.4(2) ?
C17 C18 H18 . . 119.3 ?
C19 C18 H18 . . 119.3 ?
C18 C19 C14 . . 119.15(19) ?
C18 C19 N4 . . 119.24(19) ?
C14 C19 N4 . . 121.60(19) ?
N4 C20 H20A . . 109.5 ?
N4 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
N4 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N5 C21 H21A . . 109.5 ?
N5 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
N5 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . 1.221(2) ?
O2 C13 . 1.221(3) ?
N1 C8 . 1.340(3) ?
N1 N2 . 1.344(3) ?
N1 C7 . 1.470(3) ?
N2 N3 . 1.322(3) ?
N3 C9 . 1.362(3) ?
N4 C11 . 1.361(3) ?
N4 C19 . 1.429(3) ?
N4 C20 . 1.477(3) ?
N5 C13 . 1.376(3) ?
N5 C14 . 1.425(3) ?
N5 C21 . 1.464(3) ?
C1 C6 . 1.380(4) ?
C1 C2 . 1.385(3) ?
C1 C7 . 1.503(4) ?
C2 C3 . 1.374(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.355(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.371(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.390(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.372(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.490(3) ?
C10 C12 . 1.531(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.528(3) ?
C12 C13 . 1.517(3) ?
C12 H12 . 0.9800 ?
C14 C15 . 1.394(3) ?
C14 C19 . 1.406(3) ?
C15 C16 . 1.374(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.385(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.379(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.394(3) ?
C18 H18 . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 N2 N3 . . . . -0.3(2) ?
C7 N1 N2 N3 . . . . 179.89(18) ?
N1 N2 N3 C9 . . . . 0.0(2) ?
C6 C1 C2 C3 . . . . 0.4(3) ?
C7 C1 C2 C3 . . . . 179.0(2) ?
C1 C2 C3 C4 . . . . -0.2(4) ?
C2 C3 C4 C5 . . . . -0.9(5) ?
C3 C4 C5 C6 . . . . 1.8(5) ?
C2 C1 C6 C5 . . . . 0.5(4) ?
C7 C1 C6 C5 . . . . -178.1(2) ?
C4 C5 C6 C1 . . . . -1.6(5) ?
C8 N1 C7 C1 . . . . 110.1(3) ?
N2 N1 C7 C1 . . . . -70.1(3) ?
C6 C1 C7 N1 . . . . 100.6(3) ?
C2 C1 C7 N1 . . . . -78.0(3) ?
N2 N1 C8 C9 . . . . 0.5(2) ?
C7 N1 C8 C9 . . . . -179.7(2) ?
N2 N3 C9 C8 . . . . 0.3(2) ?
N2 N3 C9 C10 . . . . 178.56(19) ?
N1 C8 C9 N3 . . . . -0.5(2) ?
N1 C8 C9 C10 . . . . -178.5(2) ?
N3 C9 C10 C12 . . . . -56.4(3) ?
C8 C9 C10 C12 . . . . 121.4(2) ?
C19 N4 C11 O1 . . . . -176.2(2) ?
C20 N4 C11 O1 . . . . 4.7(3) ?
C19 N4 C11 C12 . . . . 1.9(3) ?
C20 N4 C11 C12 . . . . -177.20(19) ?
O1 C11 C12 C13 . . . . 101.1(2) ?
N4 C11 C12 C13 . . . . -76.9(2) ?
O1 C11 C12 C10 . . . . -21.4(3) ?
N4 C11 C12 C10 . . . . 160.55(19) ?
C9 C10 C12 C13 . . . . 178.25(18) ?
C9 C10 C12 C11 . . . . -63.0(2) ?
C14 N5 C13 O2 . . . . -170.7(2) ?
C21 N5 C13 O2 . . . . -7.4(3) ?
C14 N5 C13 C12 . . . . 12.8(3) ?
C21 N5 C13 C12 . . . . 176.14(18) ?
C11 C12 C13 O2 . . . . -109.6(2) ?
C10 C12 C13 O2 . . . . 12.5(3) ?
C11 C12 C13 N5 . . . . 66.9(2) ?
C10 C12 C13 N5 . . . . -171.04(18) ?
C13 N5 C14 C15 . . . . 130.3(2) ?
C21 N5 C14 C15 . . . . -32.6(3) ?
C13 N5 C14 C19 . . . . -50.9(3) ?
C21 N5 C14 C19 . . . . 146.1(2) ?
C19 C14 C15 C16 . . . . 3.0(3) ?
N5 C14 C15 C16 . . . . -178.2(2) ?
C14 C15 C16 C17 . . . . 0.4(4) ?
C15 C16 C17 C18 . . . . -2.4(4) ?
C16 C17 C18 C19 . . . . 1.0(3) ?
C17 C18 C19 C14 . . . . 2.4(3) ?
C17 C18 C19 N4 . . . . -176.7(2) ?
C15 C14 C19 C18 . . . . -4.3(3) ?
N5 C14 C19 C18 . . . . 176.90(19) ?
C15 C14 C19 N4 . . . . 174.74(18) ?
N5 C14 C19 N4 . . . . -4.0(3) ?
C11 N4 C19 C18 . . . . -132.9(2) ?
C20 N4 C19 C18 . . . . 46.1(3) ?
C11 N4 C19 C14 . . . . 48.0(3) ?
C20 N4 C19 C14 . . . . -132.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744499
