#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2204099.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_2204099
loop_
_publ_author_name
'Li-Rong Wen'
'Shu-Wen Wang'
'Hai-Zhen Xu'
'Xiu-Li Zhang'
'Ming Li'
'Jin-Hong Liu'
_publ_section_title
;
7-(4-Methylphenyl)pyrazolo[2,3-a]pyrimidine-3-carbonitrile
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1294
_journal_page_last               o1295
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C14 H10 N4'
_chemical_formula_moiety         'C14 H10 N4'
_chemical_formula_sum            'C14 H10 N4'
_chemical_formula_weight         234.26
_chemical_name_systematic
;
7-(4-Methylphenyl)pyrazolo[2,3-a]pyrimidine-3-carbonitrile
;
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.404(3)
_cell_length_b                   10.276(4)
_cell_length_c                   14.963(5)
_cell_measurement_reflns_used    696
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.08
_cell_measurement_theta_min      3.37
_cell_volume                     1138.4(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6603
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            ' yellow '
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.124
_refine_ls_extinction_coef       0.035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0361
_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/[\s^2^(Fo^2^)+(0.0427P)^2^+0.1275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                1097
_reflns_number_total             1364
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    wn6260.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_database_code               2204099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_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_type_symbol
N1 0.0356(3) 0.48741(19) 0.57263(12) 0.0447(5) Uani d . 1 N
N2 0.1152(3) 0.52414(18) 0.49387(12) 0.0368(5) Uani d . 1 N
N3 0.1765(3) 0.44069(19) 0.34719(13) 0.0459(5) Uani d . 1 N
N4 -0.0517(4) 0.1074(2) 0.39411(16) 0.0628(7) Uani d . 1 N
C1 -0.0176(4) 0.3665(2) 0.55726(17) 0.0471(6) Uani d . 1 C
H1 -0.0774 0.3158 0.5994 0.057 Uiso calc R 1 H
C2 0.0251(4) 0.3226(2) 0.47122(16) 0.0429(6) Uani d . 1 C
C3 -0.0183(4) 0.2020(2) 0.42924(17) 0.0464(6) Uani d . 1 C
C4 0.1112(3) 0.4263(2) 0.43020(15) 0.0388(5) Uani d . 1 C
C5 0.2399(4) 0.5571(2) 0.32872(15) 0.0476(6) Uani d . 1 C
H5 0.2827 0.5719 0.2712 0.057 Uiso calc R 1 H
C6 0.2475(3) 0.6600(2) 0.38950(15) 0.0430(6) Uani d . 1 C
H6 0.2944 0.7398 0.3716 0.052 Uiso calc R 1 H
C7 0.1863(3) 0.6445(2) 0.47547(14) 0.0360(5) Uani d . 1 C
C8 0.1957(3) 0.7464(2) 0.54441(14) 0.0366(5) Uani d . 1 C
C9 0.2463(4) 0.7203(2) 0.63219(15) 0.0442(6) Uani d . 1 C
H9 0.2704 0.6352 0.6498 0.053 Uiso calc R 1 H
C10 0.2606(4) 0.8202(2) 0.69288(15) 0.0474(6) Uani d . 1 C
H10 0.2957 0.8014 0.7511 0.057 Uiso calc R 1 H
C11 0.2241(4) 0.9484(2) 0.66965(15) 0.0440(6) Uani d . 1 C
C12 0.1738(4) 0.9728(2) 0.58231(15) 0.0450(6) Uani d . 1 C
H12 0.1484 1.0578 0.5650 0.054 Uiso calc R 1 H
C13 0.1602(3) 0.8744(2) 0.52041(15) 0.0414(6) Uani d . 1 C
H13 0.1269 0.8937 0.4620 0.050 Uiso calc R 1 H
C14 0.2359(4) 1.0580(2) 0.73653(17) 0.0595(8) Uani d . 1 C
H14A 0.1204 1.0699 0.7646 0.089 Uiso calc R 1 H
H14B 0.2702 1.1367 0.7065 0.089 Uiso calc R 1 H
H14C 0.3245 1.0371 0.7811 0.089 Uiso calc R 1 H
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
N1 0.0496(12) 0.0465(11) 0.0381(11) -0.0023(10) 0.0068(10) 0.0017(9)
N2 0.0374(10) 0.0382(10) 0.0348(10) 0.0004(9) 0.0025(9) 0.0002(8)
N3 0.0473(12) 0.0515(13) 0.0390(11) -0.0006(11) 0.0025(10) -0.0056(10)
N4 0.0706(16) 0.0488(13) 0.0690(15) -0.0117(12) 0.0016(13) -0.0038(12)
C1 0.0483(16) 0.0445(14) 0.0486(15) -0.0041(13) 0.0037(13) 0.0043(12)
C2 0.0452(14) 0.0395(13) 0.0438(14) 0.0001(12) -0.0026(12) 0.0008(10)
C3 0.0468(15) 0.0415(14) 0.0511(14) -0.0017(12) -0.0018(13) 0.0027(12)
C4 0.0373(13) 0.0389(12) 0.0402(12) 0.0059(11) -0.0052(11) -0.0039(11)
C5 0.0508(16) 0.0567(17) 0.0354(12) -0.0045(14) 0.0045(12) -0.0006(12)
C6 0.0443(14) 0.0469(14) 0.0378(12) -0.0035(12) -0.0008(12) 0.0036(11)
C7 0.0322(11) 0.0390(12) 0.0367(12) 0.0007(10) -0.0025(11) 0.0030(10)
C8 0.0352(12) 0.0387(12) 0.0358(12) -0.0006(11) 0.0003(10) -0.0005(10)
C9 0.0527(15) 0.0390(13) 0.0408(13) 0.0029(12) -0.0010(12) 0.0029(10)
C10 0.0585(17) 0.0506(15) 0.0331(12) -0.0016(14) -0.0009(12) 0.0005(11)
C11 0.0466(15) 0.0463(15) 0.0392(13) -0.0067(12) 0.0075(12) -0.0061(11)
C12 0.0492(14) 0.0360(12) 0.0499(15) -0.0031(11) 0.0029(12) 0.0027(11)
C13 0.0455(14) 0.0412(13) 0.0376(12) -0.0064(11) -0.0022(11) 0.0048(11)
C14 0.074(2) 0.0559(16) 0.0485(14) -0.0081(16) 0.0106(15) -0.0135(13)
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 0.0000 '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 0.0000 '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
_geom_angle_publ_flag
C1 N1 N2 103.7(2) yes
N1 N2 C7 125.9(2) no
N1 N2 C4 112.5(2) yes
C7 N2 C4 121.6(2) no
C5 N3 C4 115.1(2) yes
N1 C1 C2 113.3(2) yes
N1 C1 H1 123.4 no
C2 C1 H1 123.4 no
C4 C2 C1 105.3(2) yes
C4 C2 C3 125.2(2) no
C1 C2 C3 129.4(2) no
N4 C3 C2 178.5(3) no
N3 C4 N2 123.3(2) no
N3 C4 C2 131.4(2) no
N2 C4 C2 105.3(2) yes
N3 C5 C6 124.5(2) no
N3 C5 H5 117.7 no
C6 C5 H5 117.7 no
C7 C6 C5 120.6(2) no
C7 C6 H6 119.7 no
C5 C6 H6 119.7 no
N2 C7 C6 114.8(2) no
N2 C7 C8 121.2(2) no
C6 C7 C8 124.0(2) no
C13 C8 C9 118.5(2) no
C13 C8 C7 118.9(2) no
C9 C8 C7 122.5(2) no
C10 C9 C8 120.0(2) no
C10 C9 H9 120.0 no
C8 C9 H9 120.0 no
C9 C10 C11 121.9(2) no
C9 C10 H10 119.1 no
C11 C10 H10 119.1 no
C12 C11 C10 117.5(2) no
C12 C11 C14 120.5(2) no
C10 C11 C14 122.0(2) no
C13 C12 C11 121.5(2) no
C13 C12 H12 119.2 no
C11 C12 H12 119.2 no
C12 C13 C8 120.6(2) no
C12 C13 H13 119.7 no
C8 C13 H13 119.7 no
C11 C14 H14A 109.5 no
C11 C14 H14B 109.5 no
H14A C14 H14B 109.5 no
C11 C14 H14C 109.5 no
H14A C14 H14C 109.5 no
H14B C14 H14C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.323(3) yes
N1 N2 1.371(2) yes
N2 C7 1.372(3) yes
N2 C4 1.385(3) yes
N3 C5 1.314(3) yes
N3 C4 1.341(3) yes
N4 C3 1.133(3) yes
C1 C2 1.400(3) yes
C1 H1 0.9300 no
C2 C4 1.385(3) yes
C2 C3 1.426(3) yes
C5 C6 1.396(3) yes
C5 H5 0.9300 yes
C6 C7 1.373(3) no
C6 H6 0.9300 no
C7 C8 1.472(3) no
C8 C13 1.388(3) no
C8 C9 1.392(3) no
C9 C10 1.375(3) no
C9 H9 0.9300 no
C10 C11 1.389(3) no
C10 H10 0.9300 no
C11 C12 1.382(3) no
C11 C14 1.509(3) no
C12 C13 1.375(3) no
C12 H12 0.9300 no
C13 H13 0.9300 no
C14 H14A 0.9600 no
C14 H14B 0.9600 no
C14 H14C 0.9600 no
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
_geom_torsion_publ_flag
C1 N1 N2 C7 177.5(2) yes
C1 N1 N2 C4 0.0(3) yes
N2 N1 C1 C2 0.2(3) yes
N1 C1 C2 C4 -0.4(3) yes
N1 C1 C2 C3 -176.3(3) yes
C4 C2 C3 N4 -0.90(10) yes
C1 C2 C3 N4 166(11) yes
C5 N3 C4 N2 -2.4(3) yes
C5 N3 C4 C2 175.6(3) yes
N1 N2 C4 N3 178.1(2) yes
C7 N2 C4 N3 0.5(3) yes
N1 N2 C4 C2 -0.2(3) no
C7 N2 C4 C2 -177.8(2) no
C1 C2 C4 N3 -177.8(3) no
C3 C2 C4 N3 -1.7(4) no
C1 C2 C4 N2 0.4(3) no
C3 C2 C4 N2 176.5(2) no
C4 N3 C5 C6 2.1(4) no
N3 C5 C6 C7 -0.1(4) no
N1 N2 C7 C6 -175.7(2) no
C4 N2 C7 C6 1.6(3) no
N1 N2 C7 C8 4.8(3) no
C4 N2 C7 C8 -177.9(2) no
C5 C6 C7 N2 -1.8(3) no
C5 C6 C7 C8 177.7(2) no
N2 C7 C8 C13 -141.1(2) no
C6 C7 C8 C13 39.5(3) no
N2 C7 C8 C9 41.7(3) no
C6 C7 C8 C9 -137.7(3) no
C13 C8 C9 C10 -0.2(4) no
C7 C8 C9 C10 177.0(2) no
C8 C9 C10 C11 0.6(4) no
C9 C10 C11 C12 -0.5(4) no
C9 C10 C11 C14 178.7(3) no
C10 C11 C12 C13 -0.1(4) no
C14 C11 C12 C13 -179.3(2) no
C11 C12 C13 C8 0.5(4) no
C9 C8 C13 C12 -0.4(4) no
C7 C8 C13 C12 -177.7(2) no