#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/63/2206385.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_2206385
loop_
_publ_author_name
'Feng-Qi He'
'Bao-Lei Wang'
'Zheng-Ming Li'
'Hai-Bin Song'
_publ_section_title
;
 1-[4-(4-Methylpyrimidin-2-yl)piperazin-1-ylmethyl]-1H-benzotriazole
;
_journal_coeditor_code           CI6611
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2602
_journal_page_last               o2604
_journal_paper_doi               10.1107/S1600536805022208
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H19 N7'
_chemical_formula_moiety         'C16 H19 N7'
_chemical_formula_sum            'C16 H19 N7'
_chemical_formula_weight         309.38
_chemical_name_systematic
;
1-[4-(4-Methylpyrimidin-2-yl)piperazin-1-ylmethyl]-1H-benzotriazole
;
_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
_cell_angle_alpha                102.108(8)
_cell_angle_beta                 94.112(7)
_cell_angle_gamma                101.504(8)
_cell_formula_units_Z            2
_cell_length_a                   6.5207(17)
_cell_length_b                   9.2488(16)
_cell_length_c                   13.429(4)
_cell_measurement_reflns_used    1635
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.17
_cell_measurement_theta_min      2.31
_cell_volume                     770.5(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.969
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4365
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.53
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0481
_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)+(0.0614P)²+0.1903P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                2102
_reflns_number_total             3104
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6611.cif
_cod_data_source_block           I
_cod_database_code               2206385
_cod_database_fobs_code          2206385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
N1 0.0256(2) 0.16368(18) 0.08980(12) 0.0448(4) Uani d . 1 N
N2 -0.1810(3) 0.1463(2) 0.10249(14) 0.0596(5) Uani d . 1 N
N3 -0.2741(3) 0.2019(2) 0.03535(14) 0.0624(5) Uani d . 1 N
N4 0.2611(2) 0.23005(17) 0.25140(11) 0.0396(4) Uani d . 1 N
N5 0.3795(3) 0.51160(17) 0.39374(11) 0.0416(4) Uani d . 1 N
N6 0.4797(3) 0.74315(18) 0.35356(12) 0.0488(4) Uani d . 1 N
N7 0.1601(3) 0.6799(2) 0.42649(14) 0.0583(5) Uani d . 1 N
C1 0.0669(3) 0.2329(2) 0.01128(13) 0.0409(4) Uani d . 1 C
C2 -0.1273(3) 0.2571(2) -0.02272(14) 0.0465(5) Uani d . 1 C
C3 -0.1475(4) 0.3256(3) -0.10485(16) 0.0598(6) Uani d . 1 C
H3 -0.2763 0.3430 -0.1280 0.072 Uiso calc R 1 H
C4 0.0276(4) 0.3657(3) -0.14938(18) 0.0676(7) Uani d . 1 C
H4 0.0191 0.4120 -0.2042 0.081 Uiso calc R 1 H
C5 0.2217(4) 0.3394(3) -0.11507(18) 0.0683(7) Uani d . 1 C
H5 0.3382 0.3682 -0.1483 0.082 Uiso calc R 1 H
C6 0.2461(3) 0.2730(3) -0.03465(16) 0.0544(6) Uani d . 1 C
H6 0.3754 0.2559 -0.0121 0.065 Uiso calc R 1 H
C7 0.1670(3) 0.1167(2) 0.16130(14) 0.0475(5) Uani d . 1 C
H7A 0.0879 0.0298 0.1823 0.057 Uiso calc R 1 H
H7B 0.2787 0.0838 0.1247 0.057 Uiso calc R 1 H
C8 0.1087(3) 0.2894(2) 0.31321(14) 0.0426(5) Uani d . 1 C
H8A 0.0066 0.2060 0.3266 0.051 Uiso calc R 1 H
H8B 0.0338 0.3461 0.2759 0.051 Uiso calc R 1 H
C9 0.2186(3) 0.3908(2) 0.41291(14) 0.0444(5) Uani d . 1 C
H9A 0.1170 0.4339 0.4520 0.053 Uiso calc R 1 H
H9B 0.2829 0.3321 0.4529 0.053 Uiso calc R 1 H
C10 0.5331(3) 0.4520(2) 0.33370(14) 0.0440(5) Uani d . 1 C
H10A 0.6055 0.3946 0.3714 0.053 Uiso calc R 1 H
H10B 0.6370 0.5350 0.3211 0.053 Uiso calc R 1 H
C11 0.4240(3) 0.3514(2) 0.23333(14) 0.0428(5) Uani d . 1 C
H11A 0.3610 0.4109 0.1934 0.051 Uiso calc R 1 H
H11B 0.5260 0.3084 0.1946 0.051 Uiso calc R 1 H
C12 0.3364(3) 0.6498(2) 0.39045(13) 0.0424(5) Uani d . 1 C
C13 0.4403(4) 0.8812(2) 0.35349(16) 0.0536(5) Uani d . 1 C
C14 0.2630(4) 0.9204(3) 0.38875(19) 0.0661(7) Uani d . 1 C
H14 0.2360 1.0154 0.3885 0.079 Uiso calc R 1 H
C15 0.1277(4) 0.8168(3) 0.42415(19) 0.0696(7) Uani d . 1 C
H15 0.0064 0.8426 0.4480 0.084 Uiso calc R 1 H
C16 0.5980(4) 0.9835(3) 0.3114(2) 0.0813(8) Uani d . 1 C
H16A 0.7356 0.9659 0.3271 0.122 Uiso calc R 1 H
H16B 0.5962 1.0870 0.3415 0.122 Uiso calc R 1 H
H16C 0.5645 0.9641 0.2384 0.122 Uiso calc R 1 H
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'
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
N2 N1 C1 109.99(16) ?
N2 N1 C7 119.05(16) ?
C1 N1 C7 130.86(16) ?
N3 N2 N1 109.01(17) ?
N2 N3 C2 108.31(17) ?
C7 N4 C8 113.74(15) ?
C7 N4 C11 114.47(15) ?
C8 N4 C11 111.63(14) ?
C12 N5 C9 120.77(16) ?
C12 N5 C10 121.44(15) ?
C9 N5 C10 111.52(15) ?
C12 N6 C13 116.02(18) ?
C15 N7 C12 115.34(19) ?
N1 C1 C6 133.72(18) ?
N1 C1 C2 103.99(17) ?
C6 C1 C2 122.27(18) ?
N3 C2 C1 108.69(18) ?
N3 C2 C3 130.69(19) ?
C1 C2 C3 120.61(19) ?
C4 C3 C2 117.2(2) ?
C4 C3 H3 121.4 ?
C2 C3 H3 121.4 ?
C3 C4 C5 121.6(2) ?
C3 C4 H4 119.2 ?
C5 C4 H4 119.2 ?
C6 C5 C4 122.4(2) ?
C6 C5 H5 118.8 ?
C4 C5 H5 118.8 ?
C5 C6 C1 115.9(2) ?
C5 C6 H6 122.1 ?
C1 C6 H6 122.1 ?
N4 C7 N1 115.55(15) y
N4 C7 H7A 108.4 ?
N1 C7 H7A 108.4 ?
N4 C7 H7B 108.4 ?
N1 C7 H7B 108.4 ?
H7A C7 H7B 107.5 ?
N4 C8 C9 110.24(16) ?
N4 C8 H8A 109.6 ?
C9 C8 H8A 109.6 ?
N4 C8 H8B 109.6 ?
C9 C8 H8B 109.6 ?
H8A C8 H8B 108.1 ?
N5 C9 C8 110.09(14) ?
N5 C9 H9A 109.6 ?
C8 C9 H9A 109.6 ?
N5 C9 H9B 109.6 ?
C8 C9 H9B 109.6 ?
H9A C9 H9B 108.2 ?
N5 C10 C11 109.74(15) ?
N5 C10 H10A 109.7 ?
C11 C10 H10A 109.7 ?
N5 C10 H10B 109.7 ?
C11 C10 H10B 109.7 ?
H10A C10 H10B 108.2 ?
N4 C11 C10 110.20(14) ?
N4 C11 H11A 109.6 ?
C10 C11 H11A 109.6 ?
N4 C11 H11B 109.6 ?
C10 C11 H11B 109.6 ?
H11A C11 H11B 108.1 ?
N7 C12 N6 126.34(19) y
N7 C12 N5 117.49(17) y
N6 C12 N5 116.15(18) ?
N6 C13 C14 121.1(2) ?
N6 C13 C16 115.8(2) y
C14 C13 C16 123.0(2) y
C15 C14 C13 118.0(2) ?
C15 C14 H14 121.0 ?
C13 C14 H14 121.0 ?
N7 C15 C14 123.2(2) ?
N7 C15 H15 118.4 ?
C14 C15 H15 118.4 ?
C13 C16 H16A 109.5 ?
C13 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C13 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 1.352(2) y
N1 C1 1.360(2) y
N1 C7 1.473(2) y
N2 N3 1.298(3) y
N3 C2 1.365(3) y
N4 C7 1.430(2) y
N4 C8 1.457(2) y
N4 C11 1.457(2) y
N5 C12 1.370(2) y
N5 C9 1.451(2) y
N5 C10 1.452(2) y
N6 C12 1.337(2) y
N6 C13 1.352(3) y
N7 C15 1.330(3) y
N7 C12 1.336(3) y
C1 C6 1.382(3) ?
C1 C2 1.391(3) ?
C2 C3 1.393(3) ?
C3 C4 1.349(3) ?
C3 H3 0.93 ?
C4 C5 1.400(3) ?
C4 H4 0.93 ?
C5 C6 1.364(3) ?
C5 H5 0.93 ?
C6 H6 0.93 ?
C7 H7A 0.97 ?
C7 H7B 0.97 ?
C8 C9 1.501(3) ?
C8 H8A 0.97 ?
C8 H8B 0.97 ?
C9 H9A 0.97 ?
C9 H9B 0.97 ?
C10 C11 1.504(3) ?
C10 H10A 0.97 ?
C10 H10B 0.97 ?
C11 H11A 0.97 ?
C11 H11B 0.97 ?
C13 C14 1.366(3) ?
C13 C16 1.481(3) ?
C14 C15 1.356(3) ?
C14 H14 0.93 ?
C15 H15 0.93 ?
C16 H16A 0.96 ?
C16 H16B 0.96 ?
C16 H16C 0.96 ?
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
C6 H6 N3 1_655 0.93 2.50 3.430(3) 176 yes
C9 H9A N7 . 0.97 2.34 2.746(3) 105 yes
C10 H10B N6 . 0.97 2.33 2.744(3) 105 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
C1 N1 N2 N3 -0.1(2)
C7 N1 N2 N3 176.62(17)
N1 N2 N3 C2 -0.1(2)
N2 N1 C1 C6 -177.9(2)
C7 N1 C1 C6 5.8(4)
N2 N1 C1 C2 0.3(2)
C7 N1 C1 C2 -175.98(18)
N2 N3 C2 C1 0.2(2)
N2 N3 C2 C3 179.1(2)
N1 C1 C2 N3 -0.3(2)
C6 C1 C2 N3 178.17(18)
N1 C1 C2 C3 -179.27(18)
C6 C1 C2 C3 -0.8(3)
N3 C2 C3 C4 -178.3(2)
C1 C2 C3 C4 0.4(3)
C2 C3 C4 C5 0.2(4)
C3 C4 C5 C6 -0.5(4)
C4 C5 C6 C1 0.1(4)
N1 C1 C6 C5 178.5(2)
C2 C1 C6 C5 0.6(3)
C8 N4 C7 N1 58.0(2)
C11 N4 C7 N1 -72.0(2)
N2 N1 C7 N4 -88.9(2)
C1 N1 C7 N4 87.1(2)
C7 N4 C8 C9 172.07(15)
C11 N4 C8 C9 -56.53(19)
C12 N5 C9 C8 94.3(2)
C10 N5 C9 C8 -58.2(2)
N4 C8 C9 N5 56.3(2)
C12 N5 C10 C11 -94.0(2)
C9 N5 C10 C11 58.37(19)
C7 N4 C11 C10 -172.10(15)
C8 N4 C11 C10 56.88(19)
N5 C10 C11 N4 -56.9(2)
C15 N7 C12 N6 0.3(3)
C15 N7 C12 N5 178.34(19)
C13 N6 C12 N7 0.2(3)
C13 N6 C12 N5 -177.93(16)
C9 N5 C12 N7 13.9(3)
C10 N5 C12 N7 163.73(17)
C9 N5 C12 N6 -167.80(15)
C10 N5 C12 N6 -18.0(3)
C12 N6 C13 C14 -0.4(3)
C12 N6 C13 C16 -179.30(19)
N6 C13 C14 C15 0.2(4)
C16 C13 C14 C15 179.0(2)
C12 N7 C15 C14 -0.5(4)
C13 C14 C15 N7 0.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17263303
