#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220948.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_2220948
loop_
_publ_author_name
'Hu, Kong-Cheng'
'Li, Guang-Jiu'
_publ_section_title
;
 2-(1H-Benzotriazol-1-yl)-1-(4-bromobenzoyl)ethyl
 2-chlorobenzoate
;
_journal_coeditor_code           WN2306
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o443
_journal_paper_doi               10.1107/S1600536809002712
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H15 Br Cl N3 O3'
_chemical_formula_moiety         'C22 H15 Br Cl N3 O3'
_chemical_formula_sum            'C22 H15 Br Cl N3 O3'
_chemical_formula_weight         484.72
_chemical_name_systematic
;
2-(1H-Benzotriazol-1-yl)-1-(4-bromobenzoyl)ethyl 2-chlorobenzoate
;
_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                 90.878(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2613(7)
_cell_length_b                   36.688(4)
_cell_length_c                   8.7919(9)
_cell_measurement_reflns_used    3180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.93
_cell_measurement_theta_min      2.22
_cell_volume                     2019.4(4)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11039
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.198
_exptl_absorpt_correction_T_max  0.8267
_exptl_absorpt_correction_T_min  0.5050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.435
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0413
_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)+(0.0492P)²+0.6802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                2968
_reflns_number_total             3978
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2306.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220948
_cod_database_fobs_code          2220948
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
Br Br1 0.29655(6) 0.490655(9) 0.67871(4) 0.06861(15) Uani d . 1 . .
Cl Cl1 0.06423(18) 0.75440(3) 1.24666(14) 0.0966(4) Uani d . 1 . .
O O2 0.0115(3) 0.64041(5) 1.3681(2) 0.0511(5) Uani d . 1 . .
N N1 0.3152(3) 0.59119(6) 1.5238(2) 0.0427(5) Uani d . 1 . .
C C3 0.1975(5) 0.52390(8) 0.8274(3) 0.0463(7) Uani d . 1 . .
C C18 0.5177(4) 0.61307(7) 1.7051(3) 0.0413(6) Uani d . 1 . .
N N2 0.5149(4) 0.57773(6) 1.5071(3) 0.0518(6) Uani d . 1 . .
O O1 -0.2188(3) 0.60500(7) 1.1628(2) 0.0696(7) Uani d . 1 . .
C C17 0.3102(4) 0.61371(7) 1.6470(3) 0.0380(6) Uani d . 1 . .
C C5 -0.0818(5) 0.55733(8) 0.9389(3) 0.0501(7) Uani d . 1 . .
H H5A -0.2247 0.5642 0.9399 0.060 Uiso calc R 1 . .
C C6 0.0564(4) 0.57085(7) 1.0497(3) 0.0406(6) Uani d . 1 . .
C C21 0.2051(5) 0.65309(8) 1.8413(3) 0.0524(7) Uani d . 1 . .
H H21A 0.1020 0.6669 1.8898 0.063 Uiso calc R 1 . .
C C10 -0.0114(5) 0.67132(8) 1.2854(3) 0.0567(8) Uani d . 1 . .
C C9 0.1469(5) 0.58149(7) 1.4157(3) 0.0458(7) Uani d . 1 . .
H H9A 0.0144 0.5782 1.4698 0.055 Uiso calc R 1 . .
H H9B 0.1823 0.5585 1.3681 0.055 Uiso calc R 1 . .
O O3 0.0745(5) 0.67563(7) 1.1669(3) 0.0951(9) Uani d . 1 . .
N N3 0.6384(4) 0.59032(7) 1.6152(3) 0.0523(6) Uani d . 1 . .
C C20 0.4137(5) 0.65259(8) 1.9019(3) 0.0524(7) Uani d . 1 . .
H H20A 0.4446 0.6659 1.9895 0.063 Uiso calc R 1 . .
C C19 0.5718(5) 0.63304(8) 1.8356(3) 0.0510(7) Uani d . 1 . .
H H19A 0.7102 0.6330 1.8755 0.061 Uiso calc R 1 . .
C C22 0.1482(5) 0.63403(8) 1.7136(3) 0.0486(7) Uani d . 1 . .
H H22A 0.0099 0.6346 1.6736 0.058 Uiso calc R 1 . .
C C2 0.3391(5) 0.53722(8) 0.9333(4) 0.0550(8) Uani d . 1 . .
H H2B 0.4818 0.5303 0.9306 0.066 Uiso calc R 1 . .
C C8 0.1142(5) 0.61048(7) 1.2923(3) 0.0472(7) Uani d . 1 . .
H H8A 0.2516 0.6181 1.2510 0.057 Uiso calc R 1 . .
C C1 0.2703(4) 0.56101(8) 1.0444(3) 0.0491(7) Uani d . 1 . .
H H1A 0.3671 0.5704 1.1154 0.059 Uiso calc R 1 . .
C C4 -0.0131(5) 0.53398(8) 0.8277(3) 0.0527(8) Uani d . 1 . .
H H4A -0.1079 0.5252 0.7540 0.063 Uiso calc R 1 . .
C C7 -0.0336(5) 0.59603(8) 1.1656(3) 0.0472(7) Uani d . 1 . .
C C16 -0.3280(6) 0.68352(9) 1.4437(4) 0.0716(10) Uani d . 1 . .
H H16A -0.3416 0.6585 1.4564 0.086 Uiso calc R 1 . .
C C11 -0.1591(5) 0.69699(8) 1.3596(3) 0.0524(7) Uani d . 1 . .
C C13 -0.2875(6) 0.75732(9) 1.4121(5) 0.0779(11) Uani d . 1 . .
H H13A -0.2728 0.7824 1.4022 0.093 Uiso calc R 1 . .
C C14 -0.4524(6) 0.74321(10) 1.4933(5) 0.0866(12) Uani d . 1 . .
H H14A -0.5498 0.7588 1.5385 0.104 Uiso calc R 1 . .
C C15 -0.4754(7) 0.70624(11) 1.5085(5) 0.0896(13) Uani d . 1 . .
H H15A -0.5894 0.6967 1.5621 0.108 Uiso calc R 1 . .
C C12 -0.1430(5) 0.73429(8) 1.3451(4) 0.0599(8) 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C10 O2 C8 . . 115.7(2) ?
N2 N1 C17 . . 109.9(2) ?
N2 N1 C9 . . 120.1(2) ?
C17 N1 C9 . . 130.0(2) ?
C2 C3 C4 . . 121.1(3) ?
C2 C3 Br1 . . 118.9(2) ?
C4 C3 Br1 . . 120.0(2) ?
N3 C18 C17 . . 108.5(2) ?
N3 C18 C19 . . 131.1(3) ?
C17 C18 C19 . . 120.4(3) ?
N3 N2 N1 . . 109.3(2) ?
N1 C17 C18 . . 104.4(2) ?
N1 C17 C22 . . 133.1(2) ?
C18 C17 C22 . . 122.5(2) ?
C4 C5 C6 . . 121.7(3) ?
C4 C5 H5A . . 119.2 ?
C6 C5 H5A . . 119.2 ?
C5 C6 C1 . . 118.4(2) ?
C5 C6 C7 . . 117.6(2) ?
C1 C6 C7 . . 124.0(2) ?
C22 C21 C20 . . 122.4(3) ?
C22 C21 H21A . . 118.8 ?
C20 C21 H21A . . 118.8 ?
O3 C10 O2 . . 122.4(3) ?
O3 C10 C11 . . 126.5(3) ?
O2 C10 C11 . . 111.0(2) ?
N1 C9 C8 . . 112.4(2) ?
N1 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
N1 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.9 ?
N2 N3 C18 . . 108.0(2) ?
C19 C20 C21 . . 121.5(3) ?
C19 C20 H20A . . 119.2 ?
C21 C20 H20A . . 119.2 ?
C20 C19 C18 . . 117.3(3) ?
C20 C19 H19A . . 121.3 ?
C18 C19 H19A . . 121.3 ?
C21 C22 C17 . . 115.9(3) ?
C21 C22 H22A . . 122.1 ?
C17 C22 H22A . . 122.1 ?
C3 C2 C1 . . 120.1(3) ?
C3 C2 H2B . . 120.0 ?
C1 C2 H2B . . 120.0 ?
O2 C8 C9 . . 104.9(2) ?
O2 C8 C7 . . 109.3(2) ?
C9 C8 C7 . . 110.4(2) ?
O2 C8 H8A . . 110.7 ?
C9 C8 H8A . . 110.7 ?
C7 C8 H8A . . 110.7 ?
C2 C1 C6 . . 119.9(3) ?
C2 C1 H1A . . 120.0 ?
C6 C1 H1A . . 120.0 ?
C3 C4 C5 . . 118.8(3) ?
C3 C4 H4A . . 120.6 ?
C5 C4 H4A . . 120.6 ?
O1 C7 C6 . . 121.9(3) ?
O1 C7 C8 . . 119.4(3) ?
C6 C7 C8 . . 118.7(2) ?
C15 C16 C11 . . 121.8(3) ?
C15 C16 H16A . . 119.1 ?
C11 C16 H16A . . 119.1 ?
C12 C11 C16 . . 117.3(3) ?
C12 C11 C10 . . 123.0(3) ?
C16 C11 C10 . . 119.6(3) ?
C14 C13 C12 . . 119.9(3) ?
C14 C13 H13A . . 120.1 ?
C12 C13 H13A . . 120.1 ?
C13 C14 C15 . . 120.5(3) ?
C13 C14 H14A . . 119.8 ?
C15 C14 H14A . . 119.8 ?
C14 C15 C16 . . 119.2(4) ?
C14 C15 H15A . . 120.4 ?
C16 C15 H15A . . 120.4 ?
C13 C12 C11 . . 121.4(3) ?
C13 C12 Cl1 . . 117.0(3) ?
C11 C12 Cl1 . . 121.6(2) ?
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
Br1 C3 . 1.899(3) ?
Cl1 C12 . 1.736(3) ?
O2 C10 . 1.353(3) ?
O2 C8 . 1.441(3) ?
N1 N2 . 1.355(3) ?
N1 C17 . 1.363(3) ?
N1 C9 . 1.452(3) ?
C3 C2 . 1.366(4) ?
C3 C4 . 1.369(4) ?
C18 N3 . 1.382(3) ?
C18 C17 . 1.388(4) ?
C18 C19 . 1.399(4) ?
N2 N3 . 1.301(3) ?
O1 C7 . 1.205(3) ?
C17 C22 . 1.395(4) ?
C5 C4 . 1.374(4) ?
C5 C6 . 1.385(4) ?
C5 H5A . 0.9300 ?
C6 C1 . 1.388(4) ?
C6 C7 . 1.492(4) ?
C21 C22 . 1.365(4) ?
C21 C20 . 1.403(4) ?
C21 H21A . 0.9300 ?
C10 O3 . 1.191(3) ?
C10 C11 . 1.479(4) ?
C9 C8 . 1.531(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C20 C19 . 1.361(4) ?
C20 H20A . 0.9300 ?
C19 H19A . 0.9300 ?
C22 H22A . 0.9300 ?
C2 C1 . 1.384(4) ?
C2 H2B . 0.9300 ?
C8 C7 . 1.532(4) ?
C8 H8A . 0.9800 ?
C1 H1A . 0.9300 ?
C4 H4A . 0.9300 ?
C16 C15 . 1.374(5) ?
C16 C11 . 1.390(4) ?
C16 H16A . 0.9300 ?
C11 C12 . 1.378(4) ?
C13 C14 . 1.366(5) ?
C13 C12 . 1.377(5) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.371(5) ?
C14 H14A . 0.9300 ?
C15 H15A . 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_D
_geom_hbond_site_symmetry_H
_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
C16 H16A Cg1 . . 1_455 0.93 2.872 3.707 150.22 yes
C21 H21A O3 . . 1_556 0.93 2.466 3.101(4) 125.71 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C17 N1 N2 N3 . . . . 0.7(3) ?
C9 N1 N2 N3 . . . . 179.3(2) ?
N2 N1 C17 C18 . . . . -0.3(3) ?
C9 N1 C17 C18 . . . . -178.8(2) ?
N2 N1 C17 C22 . . . . -179.7(3) ?
C9 N1 C17 C22 . . . . 1.8(5) ?
N3 C18 C17 N1 . . . . -0.1(3) ?
C19 C18 C17 N1 . . . . -179.0(2) ?
N3 C18 C17 C22 . . . . 179.4(3) ?
C19 C18 C17 C22 . . . . 0.4(4) ?
C4 C5 C6 C1 . . . . 1.6(4) ?
C4 C5 C6 C7 . . . . -180.0(3) ?
C8 O2 C10 O3 . . . . -10.7(5) ?
C8 O2 C10 C11 . . . . 167.3(2) ?
N2 N1 C9 C8 . . . . -97.1(3) ?
C17 N1 C9 C8 . . . . 81.3(3) ?
N1 N2 N3 C18 . . . . -0.7(3) ?
C17 C18 N3 N2 . . . . 0.5(3) ?
C19 C18 N3 N2 . . . . 179.3(3) ?
C22 C21 C20 C19 . . . . 0.3(5) ?
C21 C20 C19 C18 . . . . -0.7(4) ?
N3 C18 C19 C20 . . . . -178.4(3) ?
C17 C18 C19 C20 . . . . 0.3(4) ?
C20 C21 C22 C17 . . . . 0.4(4) ?
N1 C17 C22 C21 . . . . 178.5(3) ?
C18 C17 C22 C21 . . . . -0.7(4) ?
C4 C3 C2 C1 . . . . 0.7(5) ?
Br1 C3 C2 C1 . . . . -178.9(2) ?
C10 O2 C8 C9 . . . . 172.5(2) ?
C10 O2 C8 C7 . . . . -69.2(3) ?
N1 C9 C8 O2 . . . . -72.9(3) ?
N1 C9 C8 C7 . . . . 169.5(2) ?
C3 C2 C1 C6 . . . . 1.1(5) ?
C5 C6 C1 C2 . . . . -2.2(4) ?
C7 C6 C1 C2 . . . . 179.5(3) ?
C2 C3 C4 C5 . . . . -1.3(5) ?
Br1 C3 C4 C5 . . . . 178.3(2) ?
C6 C5 C4 C3 . . . . 0.1(4) ?
C5 C6 C7 O1 . . . . -1.2(4) ?
C1 C6 C7 O1 . . . . 177.1(3) ?
C5 C6 C7 C8 . . . . 178.2(3) ?
C1 C6 C7 C8 . . . . -3.5(4) ?
O2 C8 C7 O1 . . . . -14.2(4) ?
C9 C8 C7 O1 . . . . 100.7(3) ?
O2 C8 C7 C6 . . . . 166.4(2) ?
C9 C8 C7 C6 . . . . -78.7(3) ?
C15 C16 C11 C12 . . . . 0.8(5) ?
C15 C16 C11 C10 . . . . -176.8(4) ?
O3 C10 C11 C12 . . . . -32.0(6) ?
O2 C10 C11 C12 . . . . 150.1(3) ?
O3 C10 C11 C16 . . . . 145.5(4) ?
O2 C10 C11 C16 . . . . -32.4(4) ?
C12 C13 C14 C15 . . . . 0.0(7) ?
C13 C14 C15 C16 . . . . 1.3(7) ?
C11 C16 C15 C14 . . . . -1.7(6) ?
C14 C13 C12 C11 . . . . -0.9(6) ?
C14 C13 C12 Cl1 . . . . -179.0(3) ?
C16 C11 C12 C13 . . . . 0.5(5) ?
C10 C11 C12 C13 . . . . 178.0(3) ?
C16 C11 C12 Cl1 . . . . 178.5(3) ?
C10 C11 C12 Cl1 . . . . -3.9(5) ?
