#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/14/2211474.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_2211474
loop_
_publ_author_name
'Wu-Lan Zeng'
'Sai Bi'
'Fan Zhang'
'Jun Wan'
_publ_section_title
;
 3-(1H-Benzotriazol-1-yl)-1-(2-fluorophenyl)propan-1-one
;
_journal_coeditor_code           IS2101
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5453
_journal_page_last               o5454
_journal_paper_doi               10.1107/S1600536806046320
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H12 F N3 O'
_chemical_formula_moiety         'C15 H12 F N3 O'
_chemical_formula_sum            'C15 H12 F N3 O'
_chemical_formula_weight         269.28
_chemical_name_systematic
;
3-(1H-Benzotriazol-1-yl)-1-(2-fluorophenyl)propan-1-one
;
_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                 104.339(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.551(6)
_cell_length_b                   5.971(2)
_cell_length_c                   14.221(6)
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9
_cell_measurement_theta_min      9.3
_cell_volume                     1279.4(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6710
_diffrn_reflns_theta_full        26.10
_diffrn_reflns_theta_max         26.10
_diffrn_reflns_theta_min         2.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0426
_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)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                1923
_reflns_number_total             2520
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2101.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211474
_cod_database_fobs_code          2211474
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
F F1 0.73132(8) 0.0299(2) 0.82666(8) 0.0783(4) Uani d . 1
C C14 1.07969(11) 0.3440(3) 1.17473(11) 0.0476(4) Uani d . 1
H H14A 1.1198 0.2328 1.2026 0.057 Uiso calc R 1
N N1 0.84451(9) 0.5051(2) 1.09814(10) 0.0465(4) Uani d . 1
C C8 0.74309(10) 0.2240(3) 1.00551(10) 0.0415(4) Uani d . 1
H H8A 0.7236 0.3328 0.9540 0.050 Uiso calc R 1
H H8B 0.7925 0.1414 0.9922 0.050 Uiso calc R 1
N N2 0.82312(10) 0.7122(3) 1.06016(11) 0.0594(4) Uani d . 1
C C10 0.93446(10) 0.4781(2) 1.12024(9) 0.0391(4) Uani d . 1
N N3 0.89552(10) 0.8195(2) 1.05724(11) 0.0553(4) Uani d . 1
C C15 0.99127(11) 0.3037(3) 1.16131(10) 0.0431(4) Uani d . 1
H H15A 0.9700 0.1681 1.1785 0.052 Uiso calc R 1
C C12 1.05736(11) 0.7183(3) 1.10718(11) 0.0473(4) Uani d . 1
H H12A 1.0790 0.8525 1.0891 0.057 Uiso calc R 1
O O1 0.63199(9) 0.0660(3) 1.07216(10) 0.0762(5) Uani d . 1
C C11 0.96620(11) 0.6808(2) 1.09384(10) 0.0422(4) Uani d . 1
C C7 0.66832(10) 0.0648(3) 1.00583(12) 0.0473(4) Uani d . 1
C C6 0.63805(10) -0.1001(3) 0.92444(11) 0.0459(4) Uani d . 1
C C5 0.67040(11) -0.1186(3) 0.84222(12) 0.0516(4) Uani d . 1
C C9 0.77424(11) 0.3463(3) 1.10168(12) 0.0532(5) Uani d . 1
H H9A 0.7246 0.4255 1.1163 0.064 Uiso calc R 1
H H9B 0.7960 0.2385 1.1531 0.064 Uiso calc R 1
C C13 1.11281(11) 0.5484(3) 1.14793(11) 0.0484(4) Uani d . 1
H H13A 1.1738 0.5676 1.1583 0.058 Uiso calc R 1
C C1 0.57469(11) -0.2587(3) 0.93320(14) 0.0610(5) Uani d . 1
H H1A 0.5505 -0.2532 0.9868 0.073 Uiso calc R 1
C C4 0.64411(13) -0.2827(3) 0.77343(14) 0.0631(5) Uani d . 1
H H4A 0.6681 -0.2893 0.7198 0.076 Uiso calc R 1
C C3 0.58224(13) -0.4361(4) 0.78476(15) 0.0708(6) Uani d . 1
H H3B 0.5640 -0.5486 0.7389 0.085 Uiso calc R 1
C C2 0.54705(13) -0.4230(4) 0.86449(16) 0.0748(6) Uani d . 1
H H2B 0.5043 -0.5260 0.8719 0.090 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'
F F 0.0171 0.0103 '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
C15 C14 C13 122.51(15)
C15 C14 H14A 118.7
C13 C14 H14A 118.7
N2 N1 C10 109.59(14)
N2 N1 C9 119.65(14)
C10 N1 C9 130.50(14)
C7 C8 C9 112.06(13)
C7 C8 H8A 109.2
C9 C8 H8A 109.2
C7 C8 H8B 109.2
C9 C8 H8B 109.2
H8A C8 H8B 107.9
N3 N2 N1 109.36(14)
N1 C10 C11 104.27(14)
N1 C10 C15 133.66(15)
C11 C10 C15 122.06(15)
N2 N3 C11 107.96(14)
C14 C15 C10 116.04(14)
C14 C15 H15A 122.0
C10 C15 H15A 122.0
C13 C12 C11 116.79(15)
C13 C12 H12A 121.6
C11 C12 H12A 121.6
N3 C11 C10 108.82(15)
N3 C11 C12 130.09(15)
C10 C11 C12 121.09(14)
O1 C7 C8 120.52(15)
O1 C7 C6 119.02(15)
C8 C7 C6 120.46(13)
C5 C6 C1 115.68(16)
C5 C6 C7 126.25(15)
C1 C6 C7 117.98(15)
F1 C5 C4 116.57(16)
F1 C5 C6 119.99(15)
C4 C5 C6 123.44(17)
N1 C9 C8 110.86(13)
N1 C9 H9A 109.5
C8 C9 H9A 109.5
N1 C9 H9B 109.5
C8 C9 H9B 109.5
H9A C9 H9B 108.1
C12 C13 C14 121.50(16)
C12 C13 H13A 119.3
C14 C13 H13A 119.3
C2 C1 C6 121.61(18)
C2 C1 H1A 119.2
C6 C1 H1A 119.2
C3 C4 C5 119.24(19)
C3 C4 H4A 120.4
C5 C4 H4A 120.4
C4 C3 C2 119.59(19)
C4 C3 H3B 120.2
C2 C3 H3B 120.2
C1 C2 C3 120.44(19)
C1 C2 H2B 119.8
C3 C2 H2B 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C5 1.355(2)
C14 C15 1.362(2)
C14 C13 1.413(2)
C14 H14A 0.9300
N1 N2 1.357(2)
N1 C10 1.365(2)
N1 C9 1.457(2)
C8 C7 1.503(2)
C8 C9 1.520(2)
C8 H8A 0.9700
C8 H8B 0.9700
N2 N3 1.305(2)
C10 C11 1.393(2)
C10 C15 1.397(2)
N3 C11 1.372(2)
C15 H15A 0.9300
C12 C13 1.364(2)
C12 C11 1.401(2)
C12 H12A 0.9300
O1 C7 1.214(2)
C7 C6 1.503(2)
C6 C5 1.387(2)
C6 C1 1.394(2)
C5 C4 1.373(3)
C9 H9A 0.9700
C9 H9B 0.9700
C13 H13A 0.9300
C1 C2 1.377(3)
C1 H1A 0.9300
C4 C3 1.367(3)
C4 H4A 0.9300
C3 C2 1.378(3)
C3 H3B 0.9300
C2 H2B 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
_geom_hbond_publ_flag
C8 H8B F1 1_555 0.97 2.40 2.760(2) 101 yes
C8 H8B N3 1_545 0.97 2.53 3.336(3) 140 yes
C15 H15A Cg3 2_747 0.93 2.80 3.446(2) 127 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
C10 N1 N2 N3 -0.20(18)
C9 N1 N2 N3 -175.08(13)
N2 N1 C10 C11 0.23(16)
C9 N1 C10 C11 174.38(15)
N2 N1 C10 C15 178.92(15)
C9 N1 C10 C15 -6.9(3)
N1 N2 N3 C11 0.08(18)
C13 C14 C15 C10 -0.7(2)
N1 C10 C15 C14 -178.02(15)
C11 C10 C15 C14 0.5(2)
N2 N3 C11 C10 0.07(17)
N2 N3 C11 C12 -179.16(15)
N1 C10 C11 N3 -0.18(16)
C15 C10 C11 N3 -179.06(13)
N1 C10 C11 C12 179.13(13)
C15 C10 C11 C12 0.2(2)
C13 C12 C11 N3 178.45(15)
C13 C12 C11 C10 -0.7(2)
C9 C8 C7 O1 9.6(2)
C9 C8 C7 C6 -169.74(14)
O1 C7 C6 C5 177.82(17)
C8 C7 C6 C5 -2.8(3)
O1 C7 C6 C1 -5.7(2)
C8 C7 C6 C1 173.64(15)
C1 C6 C5 F1 179.10(15)
C7 C6 C5 F1 -4.4(3)
C1 C6 C5 C4 -1.0(3)
C7 C6 C5 C4 175.50(16)
N2 N1 C9 C8 83.72(18)
C10 N1 C9 C8 -89.93(19)
C7 C8 C9 N1 -177.98(13)
C11 C12 C13 C14 0.4(2)
C15 C14 C13 C12 0.3(2)
C5 C6 C1 C2 0.4(3)
C7 C6 C1 C2 -176.39(17)
F1 C5 C4 C3 -179.45(17)
C6 C5 C4 C3 0.7(3)
C5 C4 C3 C2 0.3(3)
C6 C1 C2 C3 0.5(3)
C4 C3 C2 C1 -0.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125894
