#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220685.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_2220685
loop_
_publ_author_name
'Wang, Wei'
'Mei, Zhen-Hua'
_publ_section_title
;
 2-(1H-Benzotriazol-1-yl)-1-(3-methoxybenzoyl)ethyl
 isonicotinate
;
_journal_coeditor_code           AT2705
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o357
_journal_paper_doi               10.1107/S1600536809001196
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H18 N4 O4'
_chemical_formula_moiety         'C22 H18 N4 O4'
_chemical_formula_sum            'C22 H18 N4 O4'
_chemical_formula_weight         402.40
_chemical_name_systematic
;
2-(1H-Benzotriazol-1-yl)-1-(3-methoxybenzoyl)ethyl isonicotinate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.342(3)
_cell_angle_beta                 102.664(3)
_cell_angle_gamma                97.985(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4839(18)
_cell_length_b                   10.3611(19)
_cell_length_c                   11.276(2)
_cell_measurement_reflns_used    1711
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.56
_cell_volume                     992.8(3)
_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 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5605
_diffrn_reflns_theta_full        26.07
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0462
_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)+(0.0502P)²+0.1574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                2822
_reflns_number_total             3819
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2705.cif
_cod_data_source_block           I
_cod_database_code               2220685
_cod_database_fobs_code          2220685
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O2 0.21549(13) 0.94145(12) 0.45684(11) 0.0511(3) Uani d . 1 . .
O O3 0.40290(15) 1.11047(14) 0.47141(13) 0.0639(4) Uani d . 1 . .
N N1 0.22089(16) 0.73861(15) 0.58935(14) 0.0498(4) Uani d . 1 . .
C C7 0.23974(18) 1.12532(18) 0.66726(18) 0.0474(4) Uani d . 1 . .
C C6 0.31816(18) 1.19911(18) 0.80934(17) 0.0457(4) Uani d . 1 . .
C C17 0.23003(19) 0.97219(18) 0.26265(17) 0.0481(4) Uani d . 1 . .
C C1 0.2728(2) 1.31472(19) 0.88006(18) 0.0526(5) Uani d . 1 . .
H H1A 0.1952 1.3441 0.8379 0.063 Uiso calc R 1 . .
C C16 0.29418(19) 1.01773(19) 0.40669(18) 0.0487(4) Uani d . 1 . .
O O1 0.15281(15) 1.17332(14) 0.60783(13) 0.0691(4) Uani d . 1 . .
C C8 0.26559(19) 0.98062(18) 0.59616(17) 0.0474(4) Uani d . 1 . .
H H8A 0.3712 0.9811 0.6233 0.057 Uiso calc R 1 . .
N N2 0.34386(18) 0.72584(18) 0.66902(16) 0.0642(5) Uani d . 1 . .
C C10 0.16172(19) 0.61663(18) 0.48299(17) 0.0457(4) Uani d . 1 . .
C C21 0.2851(2) 1.0500(2) 0.19695(19) 0.0556(5) Uani d . 1 . .
H H21A 0.3604 1.1310 0.2422 0.067 Uiso calc R 1 . .
C C9 0.1742(2) 0.86971(18) 0.62674(18) 0.0498(4) Uani d . 1 . .
H H9A 0.1837 0.9040 0.7199 0.060 Uiso calc R 1 . .
H H9B 0.0704 0.8535 0.5805 0.060 Uiso calc R 1 . .
C C15 0.0363(2) 0.57215(19) 0.37579(18) 0.0524(5) Uani d . 1 . .
H H15A -0.0264 0.6310 0.3634 0.063 Uiso calc R 1 . .
N N3 0.36612(19) 0.60040(18) 0.61744(17) 0.0687(5) Uani d . 1 . .
O O4 0.28449(18) 1.49647(15) 1.07256(15) 0.0812(5) Uani d . 1 . .
C C11 0.2550(2) 0.52895(19) 0.50226(18) 0.0522(5) Uani d . 1 . .
C C5 0.4361(2) 1.1570(2) 0.87303(19) 0.0565(5) Uani d . 1 . .
H H5A 0.4675 1.0791 0.8273 0.068 Uiso calc R 1 . .
C C2 0.3411(2) 1.38696(19) 1.01200(19) 0.0551(5) Uani d . 1 . .
N N4 0.1207(2) 0.8890(2) -0.00867(17) 0.0771(5) Uani d . 1 . .
C C3 0.4587(2) 1.3456(2) 1.0743(2) 0.0626(5) Uani d . 1 . .
H H3B 0.5059 1.3944 1.1632 0.075 Uiso calc R 1 . .
C C12 0.2266(2) 0.3910(2) 0.4131(2) 0.0615(5) Uani d . 1 . .
H H12A 0.2887 0.3316 0.4253 0.074 Uiso calc R 1 . .
C C14 0.0107(2) 0.4364(2) 0.28959(19) 0.0604(5) Uani d . 1 . .
H H14A -0.0717 0.4024 0.2164 0.072 Uiso calc R 1 . .
C C4 0.5054(2) 1.2319(2) 1.0041(2) 0.0670(6) Uani d . 1 . .
H H4B 0.5854 1.2052 1.0460 0.080 Uiso calc R 1 . .
C C13 0.1044(2) 0.3469(2) 0.3078(2) 0.0627(5) Uani d . 1 . .
H H13A 0.0826 0.2555 0.2466 0.075 Uiso calc R 1 . .
C C20 0.2260(2) 1.0049(2) 0.0634(2) 0.0680(6) Uani d . 1 . .
H H20A 0.2622 1.0593 0.0207 0.082 Uiso calc R 1 . .
C C19 0.0693(3) 0.8157(3) 0.0559(2) 0.0825(7) Uani d . 1 . .
H H19A -0.0042 0.7339 0.0076 0.099 Uiso calc R 1 . .
C C22 0.3532(3) 1.5758(2) 1.2089(2) 0.0840(7) Uani d . 1 . .
H H22A 0.3031 1.6493 1.2391 0.126 Uiso calc R 1 . .
H H22B 0.4555 1.6163 1.2223 0.126 Uiso calc R 1 . .
H H22C 0.3471 1.5151 1.2570 0.126 Uiso calc R 1 . .
C C18 0.1180(2) 0.8531(2) 0.1897(2) 0.0695(6) Uani d . 1 . .
H H18A 0.0762 0.7991 0.2302 0.083 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'
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
C16 O2 C8 . . 115.78(13) ?
N2 N1 C10 . . 109.89(14) ?
N2 N1 C9 . . 118.99(14) ?
C10 N1 C9 . . 131.12(15) ?
O1 C7 C6 . . 122.39(16) ?
O1 C7 C8 . . 119.34(16) ?
C6 C7 C8 . . 118.21(15) ?
C1 C6 C5 . . 119.12(17) ?
C1 C6 C7 . . 118.39(15) ?
C5 C6 C7 . . 122.49(16) ?
C18 C17 C21 . . 117.82(18) ?
C18 C17 C16 . . 122.72(18) ?
C21 C17 C16 . . 119.45(17) ?
C2 C1 C6 . . 120.96(17) ?
C2 C1 H1A . . 119.5 ?
C6 C1 H1A . . 119.5 ?
O3 C16 O2 . . 123.70(17) ?
O3 C16 C17 . . 124.81(18) ?
O2 C16 C17 . . 111.49(15) ?
O2 C8 C9 . . 106.06(13) ?
O2 C8 C7 . . 110.80(14) ?
C9 C8 C7 . . 109.81(14) ?
O2 C8 H8A . . 110.0 ?
C9 C8 H8A . . 110.0 ?
C7 C8 H8A . . 110.0 ?
N3 N2 N1 . . 109.04(15) ?
N1 C10 C11 . . 104.25(15) ?
N1 C10 C15 . . 133.49(16) ?
C11 C10 C15 . . 122.22(16) ?
C20 C21 C17 . . 118.61(19) ?
C20 C21 H21A . . 120.7 ?
C17 C21 H21A . . 120.7 ?
N1 C9 C8 . . 111.93(14) ?
N1 C9 H9A . . 109.2 ?
C8 C9 H9A . . 109.2 ?
N1 C9 H9B . . 109.2 ?
C8 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
C14 C15 C10 . . 115.92(17) ?
C14 C15 H15A . . 122.0 ?
C10 C15 H15A . . 122.0 ?
N2 N3 C11 . . 107.87(15) ?
C2 O4 C22 . . 117.93(18) ?
N3 C11 C10 . . 108.94(16) ?
N3 C11 C12 . . 130.21(18) ?
C10 C11 C12 . . 120.83(17) ?
C4 C5 C6 . . 119.33(18) ?
C4 C5 H5A . . 120.3 ?
C6 C5 H5A . . 120.3 ?
O4 C2 C1 . . 115.94(18) ?
O4 C2 C3 . . 124.37(18) ?
C1 C2 C3 . . 119.69(18) ?
C19 N4 C20 . . 116.16(19) ?
C4 C3 C2 . . 119.54(19) ?
C4 C3 H3B . . 120.2 ?
C2 C3 H3B . . 120.2 ?
C13 C12 C11 . . 117.29(18) ?
C13 C12 H12A . . 121.4 ?
C11 C12 H12A . . 121.4 ?
C15 C14 C13 . . 122.40(19) ?
C15 C14 H14A . . 118.8 ?
C13 C14 H14A . . 118.8 ?
C5 C4 C3 . . 121.34(19) ?
C5 C4 H4B . . 119.3 ?
C3 C4 H4B . . 119.3 ?
C12 C13 C14 . . 121.34(18) ?
C12 C13 H13A . . 119.3 ?
C14 C13 H13A . . 119.3 ?
N4 C20 C21 . . 124.4(2) ?
N4 C20 H20A . . 117.8 ?
C21 C20 H20A . . 117.8 ?
N4 C19 C18 . . 124.2(2) ?
N4 C19 H19A . . 117.9 ?
C18 C19 H19A . . 117.9 ?
O4 C22 H22A . . 109.5 ?
O4 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O4 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C19 C18 C17 . . 118.8(2) ?
C19 C18 H18A . . 120.6 ?
C17 C18 H18A . . 120.6 ?
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
O2 C16 . 1.349(2) ?
O2 C8 . 1.434(2) ?
O3 C16 . 1.204(2) ?
N1 N2 . 1.359(2) ?
N1 C10 . 1.362(2) ?
N1 C9 . 1.445(2) ?
C7 O1 . 1.212(2) ?
C7 C6 . 1.488(2) ?
C7 C8 . 1.531(2) ?
C6 C1 . 1.384(2) ?
C6 C5 . 1.395(2) ?
C17 C18 . 1.382(3) ?
C17 C21 . 1.385(3) ?
C17 C16 . 1.487(2) ?
C1 C2 . 1.378(3) ?
C1 H1A . 0.9300 ?
C8 C9 . 1.519(2) ?
C8 H8A . 0.9800 ?
N2 N3 . 1.304(2) ?
C10 C11 . 1.387(2) ?
C10 C15 . 1.392(2) ?
C21 C20 . 1.375(3) ?
C21 H21A . 0.9300 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C15 C14 . 1.371(3) ?
C15 H15A . 0.9300 ?
N3 C11 . 1.375(2) ?
O4 C2 . 1.363(2) ?
O4 C22 . 1.428(2) ?
C11 C12 . 1.396(3) ?
C5 C4 . 1.375(3) ?
C5 H5A . 0.9300 ?
C2 C3 . 1.382(3) ?
N4 C19 . 1.327(3) ?
N4 C20 . 1.329(3) ?
C3 C4 . 1.376(3) ?
C3 H3B . 0.9300 ?
C12 C13 . 1.361(3) ?
C12 H12A . 0.9300 ?
C14 C13 . 1.403(3) ?
C14 H14A . 0.9300 ?
C4 H4B . 0.9300 ?
C13 H13A . 0.9300 ?
C20 H20A . 0.9300 ?
C19 C18 . 1.378(3) ?
C19 H19A . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C18 H18A . 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
C3 H3B N3 . . 2_677 0.93 2.484 3.328(3) 150.92 yes
C9 H9B O1 . . 2_576 0.97 2.558 3.471(2) 157.06 yes
C15 H15A O1 . . 2_576 0.93 2.462 3.368(3) 164.41 yes
C20 H20A Cg3 . . 1_554 0.93 2.852 3.767 167.99 yes
C22 H22C Cg4 . . 1_566 0.96 2.871 3.530 126.65 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
O1 C7 C6 C1 . . . . 10.4(3) ?
C8 C7 C6 C1 . . . . -166.80(16) ?
O1 C7 C6 C5 . . . . -168.84(18) ?
C8 C7 C6 C5 . . . . 13.9(3) ?
C5 C6 C1 C2 . . . . -0.9(3) ?
C7 C6 C1 C2 . . . . 179.82(17) ?
C8 O2 C16 O3 . . . . 2.3(2) ?
C8 O2 C16 C17 . . . . -177.93(13) ?
C18 C17 C16 O3 . . . . 170.73(19) ?
C21 C17 C16 O3 . . . . -8.3(3) ?
C18 C17 C16 O2 . . . . -9.0(2) ?
C21 C17 C16 O2 . . . . 172.00(15) ?
C16 O2 C8 C9 . . . . -172.79(13) ?
C16 O2 C8 C7 . . . . 68.10(18) ?
O1 C7 C8 O2 . . . . 18.0(2) ?
C6 C7 C8 O2 . . . . -164.64(14) ?
O1 C7 C8 C9 . . . . -98.8(2) ?
C6 C7 C8 C9 . . . . 78.53(19) ?
C10 N1 N2 N3 . . . . 0.3(2) ?
C9 N1 N2 N3 . . . . -179.98(16) ?
N2 N1 C10 C11 . . . . 0.1(2) ?
C9 N1 C10 C11 . . . . -179.61(17) ?
N2 N1 C10 C15 . . . . 177.64(19) ?
C9 N1 C10 C15 . . . . -2.1(3) ?
C18 C17 C21 C20 . . . . -0.1(3) ?
C16 C17 C21 C20 . . . . 178.95(17) ?
N2 N1 C9 C8 . . . . 79.2(2) ?
C10 N1 C9 C8 . . . . -101.1(2) ?
O2 C8 C9 N1 . . . . 74.36(17) ?
C7 C8 C9 N1 . . . . -165.87(14) ?
N1 C10 C15 C14 . . . . -177.61(19) ?
C11 C10 C15 C14 . . . . -0.4(3) ?
N1 N2 N3 C11 . . . . -0.5(2) ?
N2 N3 C11 C10 . . . . 0.6(2) ?
N2 N3 C11 C12 . . . . -177.9(2) ?
N1 C10 C11 N3 . . . . -0.4(2) ?
C15 C10 C11 N3 . . . . -178.31(17) ?
N1 C10 C11 C12 . . . . 178.28(18) ?
C15 C10 C11 C12 . . . . 0.4(3) ?
C1 C6 C5 C4 . . . . -0.6(3) ?
C7 C6 C5 C4 . . . . 178.69(18) ?
C22 O4 C2 C1 . . . . -179.05(18) ?
C22 O4 C2 C3 . . . . 1.4(3) ?
C6 C1 C2 O4 . . . . -178.11(17) ?
C6 C1 C2 C3 . . . . 1.5(3) ?
O4 C2 C3 C4 . . . . 178.9(2) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
N3 C11 C12 C13 . . . . 178.3(2) ?
C10 C11 C12 C13 . . . . -0.1(3) ?
C10 C15 C14 C13 . . . . 0.2(3) ?
C6 C5 C4 C3 . . . . 1.5(3) ?
C2 C3 C4 C5 . . . . -0.9(3) ?
C11 C12 C13 C14 . . . . -0.1(3) ?
C15 C14 C13 C12 . . . . 0.0(3) ?
C19 N4 C20 C21 . . . . 1.4(3) ?
C17 C21 C20 N4 . . . . -1.5(3) ?
C20 N4 C19 C18 . . . . 0.2(4) ?
N4 C19 C18 C17 . . . . -1.7(4) ?
C21 C17 C18 C19 . . . . 1.6(3) ?
C16 C17 C18 C19 . . . . -177.42(19) ?
