#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/92/2219211.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_2219211
loop_
_publ_author_name
'Wang, Su-Qing'
'Jian, Fang-Fang'
'Liu, Huan-Qiang'
_publ_section_title
;
 N-[(3,5-Dimethylpyrazol-1-yl)methyl]phthalimide
;
_journal_coeditor_code           AT2593
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1733
_journal_paper_doi               10.1107/S160053680802518X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H13 N3 O2'
_chemical_formula_moiety         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27
_chemical_name_common
;
N-[(3,5-Dimethylpyrazol-1-yl)methyl]phthalimide
;
_chemical_name_systematic
;
2-[(3,5-Dimethylpyrazol-1-yl)methyl]isoindole-1,3-dione
;
_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                 127.566(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.285(2)
_cell_length_b                   8.4576(15)
_cell_length_c                   15.6162(19)
_cell_measurement_reflns_used    1464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.09
_cell_volume                     1286.1(4)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8080
_diffrn_reflns_theta_full        28.21
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.208
_refine_ls_extinction_coef       0.051(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0557
_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)+(0.0831P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                1464
_reflns_number_total             3090
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2593.cif
_cod_data_source_block           I
_cod_original_cell_volume        1286.1(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219211
_cod_database_fobs_code          2219211
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
O O1 0.66997(19) -0.2663(2) -0.13413(14) 0.0613(6) Uani d . 1
O O2 0.38437(19) -0.1191(2) -0.05358(15) 0.0610(6) Uani d . 1
N N1 0.50763(19) -0.1704(2) -0.11721(15) 0.0443(5) Uani d . 1
N N2 0.3078(2) -0.1271(2) -0.30016(15) 0.0481(6) Uani d . 1
N N3 0.3112(2) -0.2458(2) -0.35815(16) 0.0508(6) Uani d . 1
C C1 0.1467(3) 0.0376(4) -0.2904(2) 0.0729(9) Uani d . 1
H H1A 0.2309 0.0833 -0.2297 0.109 Uiso calc R 1
H H1B 0.0965 -0.0058 -0.2672 0.109 Uiso calc R 1
H H1C 0.0925 0.1178 -0.3439 0.109 Uiso calc R 1
C C2 0.1782(3) -0.0900(3) -0.3378(2) 0.0520(7) Uani d . 1
C C3 0.0937(3) -0.1884(3) -0.4239(2) 0.0575(7) Uani d . 1
H H3B -0.0016 -0.1922 -0.4669 0.069 Uiso calc R 1
C C4 0.1783(3) -0.2813(3) -0.4344(2) 0.0524(7) Uani d . 1
C C5 0.1404(3) -0.4075(4) -0.5153(2) 0.0737(9) Uani d . 1
H H5A 0.2223 -0.4502 -0.5013 0.111 Uiso calc R 1
H H5B 0.0833 -0.3632 -0.5867 0.111 Uiso calc R 1
H H5C 0.0914 -0.4901 -0.5099 0.111 Uiso calc R 1
C C6 0.4354(2) -0.0637(3) -0.20848(18) 0.0486(6) Uani d . 1
H H6A 0.4176 0.0345 -0.1870 0.058 Uiso calc R 1
H H6B 0.4937 -0.0397 -0.2292 0.058 Uiso calc R 1
C C7 0.6197(2) -0.2631(3) -0.0875(2) 0.0442(6) Uani d . 1
C C8 0.6612(2) -0.3498(3) 0.01092(18) 0.0460(6) Uani d . 1
C C9 0.7624(3) -0.4605(3) 0.0711(2) 0.0611(8) Uani d . 1
H H9A 0.8183 -0.4937 0.0531 0.073 Uiso calc R 1
C C10 0.7773(3) -0.5210(4) 0.1611(2) 0.0708(9) Uani d . 1
H H10A 0.8446 -0.5966 0.2038 0.085 Uiso calc R 1
C C11 0.6954(3) -0.4717(4) 0.1882(2) 0.0685(9) Uani d . 1
H H11A 0.7098 -0.5121 0.2498 0.082 Uiso calc R 1
C C12 0.5915(3) -0.3625(3) 0.12510(19) 0.0561(7) Uani d . 1
H H12A 0.5342 -0.3306 0.1420 0.067 Uiso calc R 1
C C13 0.5765(2) -0.3033(3) 0.03664(18) 0.0439(6) Uani d . 1
C C14 0.4762(3) -0.1880(3) -0.04554(19) 0.0454(6) 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'
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
O1 O1 C7 1 0(10)
C7 N1 C14 . 111.9(2)
C7 N1 C6 . 124.48(19)
C14 N1 C6 . 123.6(2)
C2 N2 N3 . 112.6(2)
C2 N2 C6 . 128.8(2)
N3 N2 C6 . 118.6(2)
C4 N3 N2 . 103.8(2)
C2 C1 H1A . 109.5
C2 C1 H1B . 109.5
H1A C1 H1B . 109.5
C2 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
N2 C2 C3 . 105.8(2)
N2 C2 C1 . 123.1(2)
C3 C2 C1 . 131.1(2)
C2 C3 C4 . 106.6(2)
C2 C3 H3B . 126.7
C4 C3 H3B . 126.7
N3 C4 C3 . 111.2(2)
N3 C4 C5 . 119.5(2)
C3 C4 C5 . 129.3(2)
C4 C5 H5A . 109.5
C4 C5 H5B . 109.5
H5A C5 H5B . 109.5
C4 C5 H5C . 109.5
H5A C5 H5C . 109.5
H5B C5 H5C . 109.5
N2 C6 N1 . 112.99(19)
N2 C6 H6A . 109.0
N1 C6 H6A . 109.0
N2 C6 H6B . 109.0
N1 C6 H6B . 109.0
H6A C6 H6B . 107.8
O1 C7 O1 1 0.00(8)
O1 C7 N1 1 125.1(2)
O1 C7 N1 . 125.1(2)
O1 C7 C8 1 129.3(2)
O1 C7 C8 . 129.3(2)
N1 C7 C8 . 105.5(2)
C9 C8 C13 . 121.6(2)
C9 C8 C7 . 129.9(2)
C13 C8 C7 . 108.5(2)
C8 C9 C10 . 116.5(3)
C8 C9 H9A . 121.7
C10 C9 H9A . 121.7
C11 C10 C9 . 121.8(3)
C11 C10 H10A . 119.1
C9 C10 H10A . 119.1
C10 C11 C12 . 120.9(3)
C10 C11 H11A . 119.5
C12 C11 H11A . 119.5
C13 C12 C11 . 117.4(3)
C13 C12 H12A . 121.3
C11 C12 H12A . 121.3
C12 C13 C8 . 121.7(3)
C12 C13 C14 . 130.1(2)
C8 C13 C14 . 108.2(2)
O2 C14 N1 . 124.3(2)
O2 C14 C13 . 129.8(2)
N1 C14 C13 . 105.9(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
O1 O1 1 0.000(5) ?
O1 C7 . 1.208(3) no
O2 C14 . 1.206(3) no
N1 C7 . 1.396(3) no
N1 C14 . 1.397(3) no
N1 C6 . 1.446(3) ?
N2 C2 . 1.355(3) ?
N2 N3 . 1.369(3) ?
N2 C6 . 1.435(3) ?
N3 C4 . 1.343(3) ?
C1 C2 . 1.487(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.370(4) ?
C3 C4 . 1.390(4) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.495(4) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 O1 1 1.208(3) ?
C7 C8 . 1.485(3) ?
C8 C9 . 1.372(3) ?
C8 C13 . 1.382(3) ?
C9 C10 . 1.399(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.373(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.385(4) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.372(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.479(4) ?
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
C6 H6B O1 1 0.97 2.58 2.917(3) 100.6
C11 H11A Cg2 3_645 0.93 2.96 3.723(3) 140
