##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-07-11
_journal_date_accepted     2008-08-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      9
_journal_page_first     o1782
_journal_page_last     o1782
_journal_paper_category     QO
_journal_coeditor_code     BH2185
_publ_contact_author_name     'Fang-Fang Jian'
_publ_contact_author_address
;
Microscale Science Institute
Weifang University
Weifang 261061
People's Republic of China
;
_publ_contact_author_email     ffjian2008@163.com
_publ_contact_author_fax         .536E-305
_publ_contact_author_phone         .536E-305
_publ_section_title
;
N-(1H-1,2,3-Benzotriazol-1-ylmethyl)phthalimide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    "Wang, Su-Qing" .
;
Microscale Science Institute
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
    "Jian, Fang-Fang" .
;
Microscale Science Institute
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
    "Liu, Huan-Qiang" .
;
Department of Chemistry and Chemical Engineering,
Weifang University
Weifang 261061
People's Republic of China
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-(1H-1,2,3-Benzotriazol-1-ylmethyl)phthalimide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H10 N4 O2'
_chemical_formula_sum     'C15 H10 N4 O2'
_chemical_formula_iupac     'C15 H10 N4 O2'
_chemical_formula_weight     278.27
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.9481(11)
_cell_length_b     8.0041(13)
_cell_length_c     12.030(2)
_cell_angle_alpha     85.715(3)
_cell_angle_beta     81.283(3)
_cell_angle_gamma     73.398(3)
_cell_volume     633.38(18)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1689
_cell_measurement_theta_min     1.71
_cell_measurement_theta_max     28.16
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.459
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     288
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3364
_diffrn_reflns_av_R_equivalents     0.0228
_diffrn_reflns_av_sigmaI/netI     0.0398
_diffrn_reflns_theta_min     1.71
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
;
_reflns_number_total     2229
_reflns_number_gt     1689
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0559
_refine_ls_R_factor_gt     0.0408
_refine_ls_wR_factor_gt     0.1003
_refine_ls_wR_factor_ref     0.1104
_refine_ls_goodness_of_fit_ref     1.085
_refine_ls_restrained_S_all     1.085
_refine_ls_number_reflns     2229
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0531P)²+0.0288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.158
_refine_diff_density_min     -0.175
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.069(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 O1 0.2735(2) 0.98906(15) 0.49784(11) 0.0591(4) Uani d . 1 . .
    O O2 0.2515(2) 1.39679(17) 0.74744(10) 0.0621(4) Uani d . 1 . .
    N N1 0.0501(2) 1.05193(18) 0.79484(11) 0.0462(4) Uani d . 1 . .
    N N2 -0.0680(3) 0.9651(2) 0.75689(14) 0.0626(5) Uani d . 1 . .
    N N3 -0.2433(3) 1.0032(2) 0.81950(15) 0.0680(5) Uani d . 1 . .
    N N4 0.2525(2) 1.16565(17) 0.64463(11) 0.0445(4) Uani d . 1 . .
    C C1 -0.2400(3) 1.1155(3) 0.89974(16) 0.0547(5) Uani d . 1 . .
    C C2 -0.3877(3) 1.1919(3) 0.9873(2) 0.0747(7) Uani d . 1 . .
    H H2B -0.5150 1.1724 0.9984 0.090 Uiso calc R 1 . .
    C C3 -0.3374(4) 1.2959(3) 1.0557(2) 0.0806(8) Uani d . 1 . .
    H H3B -0.4333 1.3491 1.1145 0.097 Uiso calc R 1 . .
    C C4 -0.1461(4) 1.3255(3) 1.04057(17) 0.0696(6) Uani d . 1 . .
    H H4A -0.1176 1.3961 1.0902 0.083 Uiso calc R 1 . .
    C C5 -0.0002(3) 1.2536(2) 0.95475(15) 0.0528(5) Uani d . 1 . .
    H H5A 0.1265 1.2742 0.9437 0.063 Uiso calc R 1 . .
    C C6 -0.0523(3) 1.1476(2) 0.88493(14) 0.0429(4) Uani d . 1 . .
    C C7 0.2508(3) 1.0372(2) 0.73567(15) 0.0502(5) Uani d . 1 . .
    H H7A 0.3062 0.9215 0.7056 0.060 Uiso calc R 1 . .
    H H7B 0.3375 1.0507 0.7884 0.060 Uiso calc R 1 . .
    C C8 0.2638(2) 1.1293(2) 0.53142(14) 0.0431(4) Uani d . 1 . .
    C C9 0.2639(2) 1.2957(2) 0.46837(14) 0.0402(4) Uani d . 1 . .
    C C10 0.2701(3) 1.3351(2) 0.35476(14) 0.0486(5) Uani d . 1 . .
    H H10A 0.2770 1.2515 0.3035 0.058 Uiso calc R 1 . .
    C C11 0.2658(3) 1.5050(2) 0.32021(15) 0.0526(5) Uani d . 1 . .
    H H11A 0.2706 1.5361 0.2440 0.063 Uiso calc R 1 . .
    C C12 0.2547(3) 1.6289(2) 0.39629(16) 0.0518(5) Uani d . 1 . .
    H H12A 0.2528 1.7416 0.3703 0.062 Uiso calc R 1 . .
    C C13 0.2461(3) 1.5891(2) 0.51025(16) 0.0496(5) Uani d . 1 . .
    H H13A 0.2360 1.6732 0.5618 0.060 Uiso calc R 1 . .
    C C14 0.2534(2) 1.4194(2) 0.54433(13) 0.0407(4) Uani d . 1 . .
    C C15 0.2517(2) 1.3373(2) 0.65864(15) 0.0436(4) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0823(9) 0.0380(8) 0.0593(8) -0.0198(7) -0.0060(7) -0.0107(6)
    O2 0.0844(10) 0.0616(9) 0.0486(8) -0.0343(7) -0.0012(7) -0.0140(7)
    N1 0.0559(9) 0.0451(9) 0.0434(8) -0.0227(7) -0.0100(7) 0.0027(7)
    N2 0.0816(12) 0.0697(11) 0.0536(10) -0.0451(10) -0.0189(9) 0.0052(8)
    N3 0.0719(12) 0.0840(13) 0.0634(11) -0.0445(10) -0.0191(9) 0.0122(10)
    N4 0.0525(9) 0.0381(8) 0.0426(8) -0.0151(7) -0.0009(6) -0.0019(6)
    C1 0.0514(11) 0.0585(12) 0.0545(11) -0.0193(9) -0.0101(9) 0.0187(10)
    C2 0.0557(13) 0.0744(16) 0.0823(16) -0.0124(12) 0.0023(11) 0.0249(13)
    C3 0.0859(17) 0.0606(15) 0.0698(15) -0.0006(12) 0.0246(13) 0.0083(12)
    C4 0.1028(18) 0.0470(12) 0.0529(12) -0.0193(11) 0.0055(12) -0.0028(9)
    C5 0.0687(12) 0.0429(11) 0.0485(10) -0.0211(9) -0.0042(9) 0.0018(8)
    C6 0.0503(10) 0.0377(9) 0.0407(9) -0.0136(8) -0.0085(8) 0.0088(8)
    C7 0.0539(11) 0.0445(10) 0.0498(10) -0.0118(9) -0.0045(8) 0.0009(8)
    C8 0.0411(10) 0.0404(10) 0.0469(10) -0.0112(8) -0.0003(7) -0.0075(8)
    C9 0.0354(9) 0.0382(9) 0.0455(10) -0.0104(7) 0.0005(7) -0.0040(7)
    C10 0.0478(10) 0.0486(11) 0.0462(10) -0.0108(8) 0.0009(8) -0.0072(8)
    C11 0.0465(10) 0.0565(12) 0.0495(11) -0.0114(9) 0.0007(8) 0.0062(9)
    C12 0.0449(10) 0.0413(11) 0.0655(13) -0.0123(8) 0.0005(9) 0.0055(9)
    C13 0.0461(10) 0.0405(10) 0.0631(12) -0.0165(8) 0.0015(8) -0.0075(8)
    C14 0.0357(9) 0.0377(9) 0.0483(10) -0.0123(7) 0.0011(7) -0.0053(8)
    C15 0.0420(10) 0.0430(10) 0.0477(10) -0.0164(8) 0.0008(8) -0.0088(8)
_geom_special_details
;
;
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
    O1 C8 . 1.2013(19) ?
    O2 C15 . 1.201(2) ?
    N1 C6 . 1.359(2) ?
    N1 N2 . 1.361(2) ?
    N1 C7 . 1.443(2) ?
    N2 N3 . 1.299(2) ?
    N3 C1 . 1.375(3) ?
    N4 C15 . 1.395(2) ?
    N4 C8 . 1.400(2) ?
    N4 C7 . 1.446(2) ?
    C1 C6 . 1.383(2) ?
    C1 C2 . 1.395(3) ?
    C2 C3 . 1.360(3) ?
    C2 H2B . 0.9300 ?
    C3 C4 . 1.398(3) ?
    C3 H3B . 0.9300 ?
    C4 C5 . 1.365(3) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.390(2) ?
    C5 H5A . 0.9300 ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.483(2) ?
    C9 C10 . 1.377(2) ?
    C9 C14 . 1.377(2) ?
    C10 C11 . 1.385(2) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.377(3) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.380(3) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.378(2) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.479(2) ?
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
    C6 N1 N2 . . 110.53(15) ?
    C6 N1 C7 . . 130.37(15) ?
    N2 N1 C7 . . 119.04(15) ?
    N3 N2 N1 . . 108.31(16) ?
    N2 N3 C1 . . 108.26(16) ?
    C15 N4 C8 . . 112.24(14) ?
    C15 N4 C7 . . 124.16(15) ?
    C8 N4 C7 . . 123.55(14) ?
    N3 C1 C6 . . 109.09(17) ?
    N3 C1 C2 . . 130.8(2) ?
    C6 C1 C2 . . 120.1(2) ?
    C3 C2 C1 . . 117.1(2) ?
    C3 C2 H2B . . 121.4 ?
    C1 C2 H2B . . 121.4 ?
    C2 C3 C4 . . 122.1(2) ?
    C2 C3 H3B . . 118.9 ?
    C4 C3 H3B . . 118.9 ?
    C5 C4 C3 . . 121.7(2) ?
    C5 C4 H4A . . 119.2 ?
    C3 C4 H4A . . 119.2 ?
    C4 C5 C6 . . 116.0(2) ?
    C4 C5 H5A . . 122.0 ?
    C6 C5 H5A . . 122.0 ?
    N1 C6 C1 . . 103.80(16) ?
    N1 C6 C5 . . 133.27(17) ?
    C1 C6 C5 . . 122.91(17) ?
    N1 C7 N4 . . 112.73(14) ?
    N1 C7 H7A . . 109.0 ?
    N4 C7 H7A . . 109.0 ?
    N1 C7 H7B . . 109.0 ?
    N4 C7 H7B . . 109.0 ?
    H7A C7 H7B . . 107.8 ?
    O1 C8 N4 . . 124.63(16) ?
    O1 C8 C9 . . 130.09(16) ?
    N4 C8 C9 . . 105.28(14) ?
    C10 C9 C14 . . 121.57(16) ?
    C10 C9 C8 . . 130.10(16) ?
    C14 C9 C8 . . 108.33(14) ?
    C9 C10 C11 . . 116.98(17) ?
    C9 C10 H10A . . 121.5 ?
    C11 C10 H10A . . 121.5 ?
    C12 C11 C10 . . 121.42(17) ?
    C12 C11 H11A . . 119.3 ?
    C10 C11 H11A . . 119.3 ?
    C11 C12 C13 . . 121.36(17) ?
    C11 C12 H12A . . 119.3 ?
    C13 C12 H12A . . 119.3 ?
    C14 C13 C12 . . 117.14(17) ?
    C14 C13 H13A . . 121.4 ?
    C12 C13 H13A . . 121.4 ?
    C9 C14 C13 . . 121.52(16) ?
    C9 C14 C15 . . 108.84(15) ?
    C13 C14 C15 . . 129.64(16) ?
    O2 C15 N4 . . 124.42(16) ?
    O2 C15 C14 . . 130.33(16) ?
    N4 C15 C14 . . 105.24(14) ?
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
    C7 H7A O1 1 0.97 2.55 2.890(2) 100.7 yes
