#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/81/2218131.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_2218131
loop_
_publ_author_name
'Zeng, Wu-Lan'
_publ_section_title
;
 2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl
 2,4-dichlorobenzoate
;
_journal_coeditor_code           HB2721
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o941
_journal_paper_doi               10.1107/S1600536808011963
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C23 H17 Cl2 N3 O3'
_chemical_formula_moiety         'C23 H17 Cl2 N3 O3'
_chemical_formula_sum            'C23 H17 Cl2 N3 O3'
_chemical_formula_weight         454.30
_chemical_name_systematic
;
2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl
2,4-dichlorobenzoate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3395(19)
_cell_length_b                   9.3065(19)
_cell_length_c                   23.538(5)
_cell_measurement_reflns_used    5663
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.920
_cell_measurement_theta_min      1.731
_cell_volume                     2044.5(7)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_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      113(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11260
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0327
_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)+(0.0569P)²+0.0675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                3138
_reflns_number_total             3585
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2721.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      'P 21/c'
_cod_database_code               2218131
_cod_database_fobs_code          2218131
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
Cl Cl1 0.16956(4) 0.45085(4) 0.044626(17) 0.02736(13) Uani d . 1
Cl Cl2 0.48958(4) 0.53198(5) -0.135572(17) 0.03077(14) Uani d . 1
O O1 0.28238(12) 1.07298(12) 0.10792(5) 0.0272(3) Uani d . 1
O O2 0.37879(10) 0.80863(11) 0.11568(4) 0.0208(3) Uani d . 1
O O3 0.14534(11) 0.76130(12) 0.09646(5) 0.0309(3) Uani d . 1
N N1 0.58217(13) 0.98801(13) 0.18828(6) 0.0199(3) Uani d . 1
N N2 0.61195(13) 1.10055(14) 0.22405(6) 0.0255(3) Uani d . 1
N N3 0.71818(13) 1.17383(14) 0.20467(6) 0.0279(3) Uani d . 1
C C1 0.22159(14) 1.10721(16) 0.20360(7) 0.0189(3) Uani d . 1
C C2 0.18316(15) 1.04219(16) 0.25408(7) 0.0194(3) Uani d . 1
H H2 0.1983 0.9441 0.2590 0.023 Uiso calc R 1
C C3 0.12259(14) 1.12125(16) 0.29721(7) 0.0209(3) Uani d . 1
C C4 0.10223(15) 1.26887(16) 0.28894(7) 0.0228(4) Uani d . 1
H H4 0.0603 1.3232 0.3170 0.027 Uiso calc R 1
C C5 0.14371(15) 1.33491(17) 0.23954(7) 0.0244(4) Uani d . 1
H H5 0.1320 1.4336 0.2352 0.029 Uiso calc R 1
C C6 0.20216(15) 1.25563(16) 0.19677(7) 0.0231(4) Uani d . 1
H H6 0.2287 1.3004 0.1634 0.028 Uiso calc R 1
C C7 0.08028(17) 1.05045(18) 0.35132(7) 0.0272(4) Uani d . 1
H H7A -0.0178 1.0198 0.3476 0.041 Uiso calc R 1
H H7B 0.0908 1.1176 0.3822 0.041 Uiso calc R 1
H H7C 0.1407 0.9687 0.3588 0.041 Uiso calc R 1
C C8 0.27983(15) 1.02509(16) 0.15583(7) 0.0197(3) Uani d . 1
C C9 0.34219(15) 0.87504(16) 0.16804(6) 0.0198(3) Uani d . 1
H H9 0.2707 0.8162 0.1867 0.024 Uiso calc R 1
C C10 0.26778(15) 0.75666(16) 0.08292(7) 0.0213(3) Uani d . 1
C C11 0.32137(15) 0.69822(16) 0.02907(7) 0.0194(3) Uani d . 1
C C12 0.28115(15) 0.56368(16) 0.00791(7) 0.0193(3) Uani d . 1
C C13 0.33423(15) 0.51230(17) -0.04221(6) 0.0212(4) Uani d . 1
H H13 0.3086 0.4214 -0.0555 0.025 Uiso calc R 1
C C14 0.42553(15) 0.59738(17) -0.07222(7) 0.0221(3) Uani d . 1
C C15 0.46799(15) 0.73162(17) -0.05280(7) 0.0239(4) Uani d . 1
H H15 0.5301 0.7878 -0.0734 0.029 Uiso calc R 1
C C16 0.41582(15) 0.77997(17) -0.00211(7) 0.0220(3) Uani d . 1
H H16 0.4445 0.8696 0.0116 0.026 Uiso calc R 1
C C17 0.47953(15) 0.87985(16) 0.20522(7) 0.0210(3) Uani d . 1
H H17A 0.4545 0.8983 0.2442 0.025 Uiso calc R 1
H H17B 0.5251 0.7863 0.2043 0.025 Uiso calc R 1
C C18 0.67506(14) 0.98839(16) 0.14484(7) 0.0188(3) Uani d . 1
C C19 0.69518(16) 0.89704(17) 0.09888(7) 0.0227(4) Uani d . 1
H H19 0.6366 0.8177 0.0919 0.027 Uiso calc R 1
C C20 0.80604(16) 0.93045(19) 0.06451(8) 0.0300(4) Uani d . 1
H H20 0.8227 0.8727 0.0332 0.036 Uiso calc R 1
C C21 0.89552(17) 1.05053(19) 0.07554(8) 0.0342(4) Uani d . 1
H H21 0.9701 1.0692 0.0515 0.041 Uiso calc R 1
C C22 0.87541(16) 1.13949(18) 0.12039(8) 0.0301(4) Uani d . 1
H H22 0.9346 1.2184 0.1273 0.036 Uiso calc R 1
C C23 0.76221(15) 1.10800(16) 0.15590(7) 0.0239(4) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 O2 C9 116.18(11)
C18 N1 N2 109.82(12)
C18 N1 C17 130.54(13)
N2 N1 C17 118.85(13)
N3 N2 N1 109.06(13)
N2 N3 C23 108.31(13)
C2 C1 C6 119.34(14)
C2 C1 C8 122.52(14)
C6 C1 C8 118.13(14)
C3 C2 C1 121.17(14)
C3 C2 H2 119.4
C1 C2 H2 119.4
C2 C3 C4 118.33(15)
C2 C3 C7 120.96(14)
C4 C3 C7 120.72(14)
C5 C4 C3 120.83(15)
C5 C4 H4 119.6
C3 C4 H4 119.6
C6 C5 C4 120.49(15)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 119.82(15)
C5 C6 H6 120.1
C1 C6 H6 120.1
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O1 C8 C1 122.46(14)
O1 C8 C9 119.18(14)
C1 C8 C9 118.34(13)
O2 C9 C17 106.50(11)
O2 C9 C8 109.41(12)
C17 C9 C8 112.67(12)
O2 C9 H9 109.4
C17 C9 H9 109.4
C8 C9 H9 109.4
O3 C10 O2 123.50(15)
O3 C10 C11 126.53(14)
O2 C10 C11 109.96(12)
C16 C11 C12 118.02(15)
C16 C11 C10 119.32(14)
C12 C11 C10 122.67(14)
C13 C12 C11 121.03(14)
C13 C12 Cl1 117.22(12)
C11 C12 Cl1 121.69(12)
C14 C13 C12 119.16(15)
C14 C13 H13 120.4
C12 C13 H13 120.4
C13 C14 C15 121.67(15)
C13 C14 Cl2 118.56(13)
C15 C14 Cl2 119.77(12)
C16 C15 C14 118.29(14)
C16 C15 H15 120.9
C14 C15 H15 120.9
C15 C16 C11 121.81(15)
C15 C16 H16 119.1
C11 C16 H16 119.1
N1 C17 C9 114.27(12)
N1 C17 H17A 108.7
C9 C17 H17A 108.7
N1 C17 H17B 108.7
C9 C17 H17B 108.7
H17A C17 H17B 107.6
N1 C18 C19 133.41(14)
N1 C18 C23 104.14(14)
C19 C18 C23 122.41(15)
C20 C19 C18 116.44(15)
C20 C19 H19 121.8
C18 C19 H19 121.8
C19 C20 C21 121.62(17)
C19 C20 H20 119.2
C21 C20 H20 119.2
C22 C21 C20 121.75(16)
C22 C21 H21 119.1
C20 C21 H21 119.1
C21 C22 C23 117.64(15)
C21 C22 H22 121.2
C23 C22 H22 121.2
N3 C23 C18 108.66(14)
N3 C23 C22 131.17(14)
C18 C23 C22 120.13(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C12 1.7326(15)
Cl2 C14 1.7370(16)
O1 C8 1.2136(19)
O2 C10 1.3582(18)
O2 C9 1.4313(18)
O3 C10 1.1990(18)
N1 C18 1.365(2)
N1 N2 1.3660(18)
N1 C17 1.4557(19)
N2 N3 1.3004(19)
N3 C23 1.377(2)
C1 C2 1.392(2)
C1 C6 1.402(2)
C1 C8 1.480(2)
C2 C3 1.391(2)
C2 H2 0.9300
C3 C4 1.400(2)
C3 C7 1.500(2)
C4 C5 1.383(2)
C4 H4 0.9300
C5 C6 1.377(2)
C5 H5 0.9300
C6 H6 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.536(2)
C9 C17 1.527(2)
C9 H9 0.9800
C10 C11 1.483(2)
C11 C16 1.394(2)
C11 C12 1.394(2)
C12 C13 1.382(2)
C13 C14 1.377(2)
C13 H13 0.9300
C14 C15 1.383(2)
C15 C16 1.381(2)
C15 H15 0.9300
C16 H16 0.9300
C17 H17A 0.9700
C17 H17B 0.9700
C18 C19 1.394(2)
C18 C23 1.398(2)
C19 C20 1.373(2)
C19 H19 0.9300
C20 C21 1.414(2)
C20 H20 0.9300
C21 C22 1.360(3)
C21 H21 0.9300
C22 C23 1.403(2)
C22 H22 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
C15 H15 O1 3_675 0.93 2.35 3.263(2) 168
C4 H4 Cg1 2_655 0.93 2.86 3.4645(19) 124
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
C18 N1 N2 N3 1.08(16)
C17 N1 N2 N3 171.98(12)
N1 N2 N3 C23 -1.23(16)
C6 C1 C2 C3 1.6(2)
C8 C1 C2 C3 -177.02(13)
C1 C2 C3 C4 -0.6(2)
C1 C2 C3 C7 179.50(13)
C2 C3 C4 C5 -1.2(2)
C7 C3 C4 C5 178.73(13)
C3 C4 C5 C6 1.9(2)
C4 C5 C6 C1 -0.9(2)
C2 C1 C6 C5 -0.9(2)
C8 C1 C6 C5 177.82(13)
C2 C1 C8 O1 162.53(14)
C6 C1 C8 O1 -16.1(2)
C2 C1 C8 C9 -18.9(2)
C6 C1 C8 C9 162.47(13)
C10 O2 C9 C17 162.00(12)
C10 O2 C9 C8 -75.96(15)
O1 C8 C9 O2 -7.23(18)
C1 C8 C9 O2 174.12(11)
O1 C8 C9 C17 111.04(15)
C1 C8 C9 C17 -67.61(17)
C9 O2 C10 O3 -1.8(2)
C9 O2 C10 C11 177.09(12)
O3 C10 C11 C16 130.70(17)
O2 C10 C11 C16 -48.10(18)
O3 C10 C11 C12 -49.3(2)
O2 C10 C11 C12 131.91(14)
C16 C11 C12 C13 0.5(2)
C10 C11 C12 C13 -179.47(13)
C16 C11 C12 Cl1 177.60(11)
C10 C11 C12 Cl1 -2.4(2)
C11 C12 C13 C14 -1.6(2)
Cl1 C12 C13 C14 -178.78(11)
C12 C13 C14 C15 1.5(2)
C12 C13 C14 Cl2 -179.24(11)
C13 C14 C15 C16 -0.3(2)
Cl2 C14 C15 C16 -179.58(11)
C14 C15 C16 C11 -0.8(2)
C12 C11 C16 C15 0.7(2)
C10 C11 C16 C15 -179.33(13)
C18 N1 C17 C9 -77.26(19)
N2 N1 C17 C9 114.04(14)
O2 C9 C17 N1 74.44(15)
C8 C9 C17 N1 -45.52(17)
N2 N1 C18 C19 177.33(15)
C17 N1 C18 C19 7.8(3)
N2 N1 C18 C23 -0.46(16)
C17 N1 C18 C23 -169.96(14)
N1 C18 C19 C20 -177.49(16)
C23 C18 C19 C20 0.0(2)
C18 C19 C20 C21 0.5(2)
C19 C20 C21 C22 -0.6(3)
C20 C21 C22 C23 0.2(3)
N2 N3 C23 C18 0.94(17)
N2 N3 C23 C22 -176.75(16)
N1 C18 C23 N3 -0.27(17)
C19 C18 C23 N3 -178.38(13)
N1 C18 C23 C22 177.72(14)
C19 C18 C23 C22 -0.4(2)
C21 C22 C23 N3 177.76(16)
C21 C22 C23 C18 0.3(2)
