#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/01/2210177.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_2210177
loop_
_publ_author_name
'Jun Wan'
'Wu-Lan Zeng'
'Yue-Qin Yu'
'Sai Bi'
'Shu-Sheng Zhang'
_publ_section_title
;
 3-(1H-Benzotriazol-1-yl)-1-(4-chlorophenyl)propan-1-one
;
_journal_coeditor_code           CI2150
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4203
_journal_page_last               o4204
_journal_paper_doi               10.1107/S1600536806034246
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H12 Cl N3 O'
_chemical_formula_moiety         'C15 H12 Cl N3 O'
_chemical_formula_sum            'C15 H12 Cl N3 O'
_chemical_formula_weight         285.73
_chemical_name_systematic
;
3-(1H-Benzotriazol-1-yl)-1-(4-chlorophenyl)propan-1-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 106.705(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.183(7)
_cell_length_b                   10.444(3)
_cell_length_c                   12.326(4)
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      2.2
_cell_volume                     2735.2(15)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Siemens SMART 1000 CCD area-detector
;
_diffrn_measurement_method       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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7533
_diffrn_reflns_theta_full        26.09
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_correction_T_min  0.9263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.305
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0451
_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)+(0.0531P)²+0.759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1874
_reflns_number_total             2694
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2150.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210177
_cod_database_fobs_code          2210177
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Cl Cl1 0.39704(3) 0.57924(7) 0.76194(5) 0.0899(3) Uani d . 1
O O1 0.23967(8) 0.29607(15) 0.28099(14) 0.0843(5) Uani d . 1
N N1 0.11542(8) 0.51589(16) 0.04037(13) 0.0574(4) Uani d . 1
N N2 0.12757(9) 0.5246(2) -0.06127(15) 0.0721(5) Uani d . 1
N N3 0.08987(9) 0.6092(2) -0.12391(15) 0.0739(6) Uani d . 1
C C1 0.30917(10) 0.3668(2) 0.49752(19) 0.0657(6) Uani d . 1
H H1 0.3050 0.2801 0.4797 0.079 Uiso calc R 1
C C2 0.34505(10) 0.4039(2) 0.60331(19) 0.0673(6) Uani d . 1
H H2 0.3647 0.3431 0.6570 0.081 Uiso calc R 1
C C3 0.35145(9) 0.5320(2) 0.62852(17) 0.0598(5) Uani d . 1
C C4 0.32295(10) 0.6224(2) 0.55013(18) 0.0640(6) Uani d . 1
H H4 0.3281 0.7090 0.5679 0.077 Uiso calc R 1
C C5 0.28659(9) 0.58393(19) 0.44449(18) 0.0582(5) Uani d . 1
H H5 0.2669 0.6451 0.3912 0.070 Uiso calc R 1
C C6 0.27910(9) 0.45572(18) 0.41702(16) 0.0520(5) Uani d . 1
C C7 0.23949(9) 0.4089(2) 0.30502(17) 0.0563(5) Uani d . 1
C C8 0.19881(9) 0.50084(18) 0.22248(16) 0.0547(5) Uani d . 1
H H8A 0.2251 0.5552 0.1912 0.066 Uiso calc R 1
H H8B 0.1764 0.5551 0.2617 0.066 Uiso calc R 1
C C9 0.15190(10) 0.4309(2) 0.12722(18) 0.0656(6) Uani d . 1
H H9A 0.1743 0.3706 0.0931 0.079 Uiso calc R 1
H H9B 0.1235 0.3823 0.1584 0.079 Uiso calc R 1
C C10 0.06817(9) 0.59735(18) 0.04265(14) 0.0493(5) Uani d . 1
C C11 0.03666(9) 0.6226(2) 0.12346(15) 0.0561(5) Uani d . 1
H H11 0.0465 0.5801 0.1926 0.067 Uiso calc R 1
C C12 -0.00922(10) 0.7131(2) 0.09512(17) 0.0623(6) Uani d . 1
H H12 -0.0316 0.7324 0.1463 0.075 Uiso calc R 1
C C13 -0.02406(10) 0.7786(2) -0.00867(18) 0.0679(6) Uani d . 1
H H13 -0.0549 0.8417 -0.0234 0.081 Uiso calc R 1
C C14 0.00579(10) 0.7514(2) -0.08815(17) 0.0712(6) Uani d . 1
H H14 -0.0047 0.7938 -0.1574 0.085 Uiso calc R 1
C C15 0.05253(9) 0.6580(2) -0.06210(15) 0.0570(5) 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'
Cl Cl 0.1484 0.1585 '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
C10 N1 N2 109.67(17)
C10 N1 C9 129.88(17)
N2 N1 C9 120.44(18)
N3 N2 N1 109.12(17)
N2 N3 C15 107.99(17)
C2 C1 C6 121.3(2)
C2 C1 H1 119.3
C6 C1 H1 119.3
C3 C2 C1 119.0(2)
C3 C2 H2 120.5
C1 C2 H2 120.5
C4 C3 C2 121.1(2)
C4 C3 Cl1 119.82(18)
C2 C3 Cl1 119.09(17)
C3 C4 C5 119.4(2)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 C4 120.72(19)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C1 118.47(19)
C5 C6 C7 122.91(18)
C1 C6 C7 118.61(19)
O1 C7 C6 120.11(19)
O1 C7 C8 119.97(19)
C6 C7 C8 119.92(18)
C7 C8 C9 111.28(16)
C7 C8 H8A 109.4
C9 C8 H8A 109.4
C7 C8 H8B 109.4
C9 C8 H8B 109.4
H8A C8 H8B 108.0
N1 C9 C8 113.03(17)
N1 C9 H9A 109.0
C8 C9 H9A 109.0
N1 C9 H9B 109.0
C8 C9 H9B 109.0
H9A C9 H9B 107.8
N1 C10 C15 104.75(17)
N1 C10 C11 132.96(18)
C15 C10 C11 122.3(2)
C12 C11 C10 116.08(19)
C12 C11 H11 122.0
C10 C11 H11 122.0
C11 C12 C13 122.3(2)
C11 C12 H12 118.8
C13 C12 H12 118.8
C14 C13 C12 121.3(2)
C14 C13 H13 119.3
C12 C13 H13 119.3
C13 C14 C15 117.7(2)
C13 C14 H14 121.2
C15 C14 H14 121.2
N3 C15 C10 108.45(19)
N3 C15 C14 131.27(19)
C10 C15 C14 120.27(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.736(2)
O1 C7 1.215(2)
N1 C10 1.356(2)
N1 N2 1.358(2)
N1 C9 1.446(3)
N2 N3 1.305(3)
N3 C15 1.375(3)
C1 C2 1.374(3)
C1 C6 1.383(3)
C1 H1 0.93
C2 C3 1.371(3)
C2 H2 0.93
C3 C4 1.369(3)
C4 C5 1.380(3)
C4 H4 0.93
C5 C6 1.380(3)
C5 H5 0.93
C6 C7 1.490(3)
C7 C8 1.498(3)
C8 C9 1.514(3)
C8 H8A 0.97
C8 H8B 0.97
C9 H9A 0.97
C9 H9B 0.97
C10 C15 1.390(3)
C10 C11 1.397(3)
C11 C12 1.359(3)
C11 H11 0.93
C12 C13 1.404(3)
C12 H12 0.93
C13 C14 1.361(3)
C13 H13 0.93
C14 C15 1.392(3)
C14 H14 0.93
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
C10 N1 N2 N3 0.2(2)
C9 N1 N2 N3 -178.43(18)
N1 N2 N3 C15 0.6(2)
C6 C1 C2 C3 -0.7(3)
C1 C2 C3 C4 -0.2(3)
C1 C2 C3 Cl1 -179.71(17)
C2 C3 C4 C5 0.8(3)
Cl1 C3 C4 C5 -179.72(16)
C3 C4 C5 C6 -0.5(3)
C4 C5 C6 C1 -0.4(3)
C4 C5 C6 C7 178.90(18)
C2 C1 C6 C5 1.0(3)
C2 C1 C6 C7 -178.34(19)
C5 C6 C7 O1 172.4(2)
C1 C6 C7 O1 -8.3(3)
C5 C6 C7 C8 -8.3(3)
C1 C6 C7 C8 170.95(18)
O1 C7 C8 C9 12.4(3)
C6 C7 C8 C9 -166.91(17)
C10 N1 C9 C8 -73.0(3)
N2 N1 C9 C8 105.4(2)
C7 C8 C9 N1 -174.88(17)
N2 N1 C10 C15 -0.9(2)
C9 N1 C10 C15 177.61(18)
N2 N1 C10 C11 177.58(19)
C9 N1 C10 C11 -3.9(3)
N1 C10 C11 C12 179.94(19)
C15 C10 C11 C12 -1.8(3)
C10 C11 C12 C13 -0.5(3)
C11 C12 C13 C14 2.1(3)
C12 C13 C14 C15 -1.2(3)
N2 N3 C15 C10 -1.1(2)
N2 N3 C15 C14 178.7(2)
N1 C10 C15 N3 1.2(2)
C11 C10 C15 N3 -177.47(17)
N1 C10 C15 C14 -178.66(18)
C11 C10 C15 C14 2.7(3)
C13 C14 C15 N3 179.1(2)
C13 C14 C15 C10 -1.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127557
