#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/83/2228315.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228315
loop_
_publ_author_name
'Zhu, Xue-wen'
'Zhang, Ying-Jun'
'Zhang, Chun-Xia'
'Li, Gang-Sen'
'Qian, Heng-Yu'
_publ_section_title
;
 1-Chloromethyl-1H-1,2,3-benzotriazole
;
_journal_coeditor_code           FL2325
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3173
_journal_paper_doi               10.1107/S1600536810046052
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H6 Cl N3'
_chemical_formula_moiety         'C7 H6 Cl N3'
_chemical_formula_sum            'C7 H6 Cl N3'
_chemical_formula_weight         167.60
_chemical_melting_point          409.5
_chemical_name_common            1-(Chloromethyl)benzotriazole
_chemical_name_systematic
;
1-Chloromethyl-1H-1,2,3-benzotriazole
;
_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                 108.49(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5081(17)
_cell_length_b                   9.6045(14)
_cell_length_c                   10.984(2)
_cell_measurement_reflns_used    1327
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.6
_cell_volume                     751.2(3)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2865
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         2865
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_T_max  0.9215
_exptl_absorpt_correction_T_min  0.9138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0381P)²+0.0967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                1218
_reflns_number_total             1530
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fl2325.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228315
_cod_database_fobs_code          2228315
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.28373(7) 0.06214(5) 0.48763(5) 0.0569(2) Uani d . 1 . .
N N1 0.12629(19) 0.31134(15) 0.42214(12) 0.0387(3) Uani d . 1 . .
C C6 0.2688(2) 0.44038(19) 0.63087(16) 0.0411(4) Uani d . 1 . .
H H6A 0.2580 0.3716 0.6877 0.049 Uiso calc R 1 . .
N N2 0.0960(2) 0.34462(18) 0.29614(13) 0.0509(4) Uani d . 1 . .
C C7 0.0840(2) 0.17530(18) 0.45677(18) 0.0436(4) Uani d . 1 . .
H H7A -0.0195 0.1369 0.3878 0.052 Uiso calc R 1 . .
H H7B 0.0453 0.1810 0.5329 0.052 Uiso calc R 1 . .
N N3 0.1527(2) 0.47155(18) 0.29024(14) 0.0534(4) Uani d . 1 . .
C C2 0.2235(2) 0.52323(19) 0.41342(16) 0.0403(4) Uani d . 1 . .
C C1 0.2084(2) 0.42052(17) 0.49813(15) 0.0332(4) Uani d . 1 . .
C C4 0.3611(3) 0.6730(2) 0.5873(2) 0.0557(5) Uani d . 1 . .
H H4A 0.4140 0.7581 0.6204 0.067 Uiso calc R 1 . .
C C3 0.3011(3) 0.6533(2) 0.4584(2) 0.0514(5) Uani d . 1 . .
H H3B 0.3111 0.7231 0.4023 0.062 Uiso calc R 1 . .
C C5 0.3451(3) 0.5681(2) 0.67153(19) 0.0504(5) Uani d . 1 . .
H H5A 0.3884 0.5860 0.7592 0.061 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0606(3) 0.0432(3) 0.0670(4) 0.0114(2) 0.0204(3) 0.0072(2)
N1 0.0447(8) 0.0379(8) 0.0319(7) 0.0053(6) 0.0098(6) 0.0008(6)
C6 0.0460(10) 0.0417(10) 0.0365(9) 0.0045(8) 0.0142(8) 0.0023(8)
N2 0.0602(10) 0.0574(11) 0.0318(8) 0.0121(8) 0.0099(7) 0.0023(7)
C7 0.0432(10) 0.0380(10) 0.0489(10) 0.0000(8) 0.0135(8) -0.0045(8)
N3 0.0648(11) 0.0583(11) 0.0393(8) 0.0149(9) 0.0198(8) 0.0126(8)
C2 0.0421(10) 0.0433(10) 0.0390(9) 0.0114(8) 0.0178(8) 0.0094(8)
C1 0.0325(8) 0.0337(9) 0.0348(9) 0.0063(7) 0.0125(7) 0.0021(7)
C4 0.0531(12) 0.0403(11) 0.0729(13) -0.0051(9) 0.0188(10) -0.0092(11)
C3 0.0534(12) 0.0393(11) 0.0682(13) 0.0027(9) 0.0286(10) 0.0137(10)
C5 0.0539(11) 0.0513(12) 0.0432(10) 0.0019(9) 0.0114(9) -0.0100(9)
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 N2 . . 109.78(14) ?
C1 N1 C7 . . 129.74(13) ?
N2 N1 C7 . . 120.34(14) ?
C5 C6 C1 . . 115.31(17) ?
C5 C6 H6A . . 122.3 ?
C1 C6 H6A . . 122.3 ?
N3 N2 N1 . . 108.53(14) ?
N1 C7 Cl1 . . 111.25(12) ?
N1 C7 H7A . . 109.4 ?
Cl1 C7 H7A . . 109.4 ?
N1 C7 H7B . . 109.4 ?
Cl1 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
N2 N3 C2 . . 108.61(14) ?
N3 C2 C1 . . 108.32(16) ?
N3 C2 C3 . . 130.89(17) ?
C1 C2 C3 . . 120.79(16) ?
N1 C1 C2 . . 104.75(14) ?
N1 C1 C6 . . 132.87(15) ?
C2 C1 C6 . . 122.38(16) ?
C3 C4 C5 . . 121.34(18) ?
C3 C4 H4A . . 119.3 ?
C5 C4 H4A . . 119.3 ?
C4 C3 C2 . . 117.14(17) ?
C4 C3 H3B . . 121.4 ?
C2 C3 H3B . . 121.4 ?
C6 C5 C4 . . 123.04(18) ?
C6 C5 H5A . . 118.5 ?
C4 C5 H5A . . 118.5 ?
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
Cl1 C7 . 1.7950(18) ?
N1 C1 . 1.360(2) ?
N1 N2 . 1.3674(19) ?
N1 C7 . 1.424(2) ?
C6 C5 . 1.367(3) ?
C6 C1 . 1.396(2) ?
C6 H6A . 0.9300 ?
N2 N3 . 1.299(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
N3 C2 . 1.380(2) ?
C2 C1 . 1.385(2) ?
C2 C3 . 1.401(3) ?
C4 C3 . 1.356(3) ?
C4 C5 . 1.399(3) ?
C4 H4A . 0.9300 ?
C3 H3B . 0.9300 ?
C5 H5A . 0.9300 ?
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
C7 H7A N3 2_545 0.97 2.47 3.360(2) 152.3
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
C1 N1 N2 N3 . . . . -1.26(19) ?
C7 N1 N2 N3 . . . . -177.32(15) ?
C1 N1 C7 Cl1 . . . . -84.43(19) ?
N2 N1 C7 Cl1 . . . . 90.74(16) ?
N1 N2 N3 C2 . . . . 0.7(2) ?
N2 N3 C2 C1 . . . . 0.1(2) ?
N2 N3 C2 C3 . . . . 179.91(18) ?
N2 N1 C1 C2 . . . . 1.27(18) ?
C7 N1 C1 C2 . . . . 176.84(16) ?
N2 N1 C1 C6 . . . . -179.43(17) ?
C7 N1 C1 C6 . . . . -3.9(3) ?
N3 C2 C1 N1 . . . . -0.84(18) ?
C3 C2 C1 N1 . . . . 179.33(15) ?
N3 C2 C1 C6 . . . . 179.77(15) ?
C3 C2 C1 C6 . . . . -0.1(3) ?
C5 C6 C1 N1 . . . . -179.59(17) ?
C5 C6 C1 C2 . . . . -0.4(2) ?
C5 C4 C3 C2 . . . . -0.3(3) ?
N3 C2 C3 C4 . . . . -179.37(18) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C1 C6 C5 C4 . . . . 0.5(3) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2575483
