#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/79/2207942.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_2207942
loop_
_publ_author_name
'Jing Wang'
'Song-Lei Zhu'
_publ_section_title
4-(4-Fluorophenyl)-3-methyl-6-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
_journal_coeditor_code           XU6071
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o47
_journal_page_last               o48
_journal_paper_doi               10.1107/S1600536805039462
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H15 F N4 O'
_chemical_formula_moiety         'C20 H15 F N4 O'
_chemical_formula_sum            'C20 H15 F N4 O'
_chemical_formula_weight         346.36
_chemical_melting_point          .497E-305
_chemical_name_systematic
;
4-(4-Fluorophenyl)-3-methyl-6-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-
pyrazolo[3,4-b]pyridine-5-carbonitrile
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.856(5)
_cell_length_b                   8.245(4)
_cell_length_c                   38.898(17)
_cell_measurement_reflns_used    2536
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.1
_cell_measurement_theta_min      2.1
_cell_volume                     3482(3)
_computing_cell_refinement       SAINT
_computing_data_collection       'SMART (Bruker, 1999)'
_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      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_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  0.061
_diffrn_reflns_av_sigmaI/netI    0.052
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            17020
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.114
_refine_ls_R_factor_gt           0.057
_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)+(0.054P)²+3.1712P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.134
_refine_ls_wR_factor_ref         0.165
_reflns_number_gt                1712
_reflns_number_total             3069
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu6071.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2207942
_cod_database_fobs_code          2207942
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'
'-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
F1 0.5985(3) 0.3427(4) 0.49399(7) 0.1356(12) Uani d . 1 F
N1 0.4743(2) 0.1085(3) 0.66799(7) 0.0479(7) Uani d . 1 N
H1 0.4430 0.1726 0.6831 0.058 Uiso calc R 1 H
N2 0.2834(2) -0.0461(3) 0.66026(7) 0.0468(7) Uani d . 1 N
N3 0.2384(2) -0.1592(3) 0.63736(7) 0.0511(7) Uani d . 1 N
N4 0.8660(3) 0.0407(4) 0.61601(9) 0.0696(9) Uani d . 1 N
O1 0.6632(2) 0.2236(3) 0.67158(6) 0.0589(7) Uani d . 1 O
C1 0.5971(3) 0.1169(4) 0.66039(8) 0.0462(8) Uani d . 1 C
C2 0.6450(2) -0.0233(4) 0.63825(9) 0.0463(8) Uani d . 1 C
H2 0.6520 -0.1179 0.6534 0.056 Uiso calc R 1 H
C3 0.5599(3) -0.0737(4) 0.60773(8) 0.0450(8) Uani d . 1 C
H3 0.5860 -0.1817 0.6001 0.054 Uiso calc R 1 H
C4 0.4338(3) -0.0907(4) 0.62334(8) 0.0447(8) Uani d . 1 C
C5 0.4001(3) -0.0040(4) 0.65128(8) 0.0443(8) Uani d . 1 C
C6 0.3311(3) -0.1871(4) 0.61542(9) 0.0477(8) Uani d . 1 C
C7 0.7699(3) 0.0152(4) 0.62641(9) 0.0525(9) Uani d . 1 C
C8 0.5677(3) 0.0389(4) 0.57698(9) 0.0472(8) Uani d . 1 C
C9 0.6277(4) -0.0099(5) 0.54775(10) 0.0795(13) Uani d . 1 C
H9 0.6622 -0.1131 0.5468 0.095 Uiso calc R 1 H
C10 0.6378(5) 0.0929(7) 0.51946(11) 0.1000(16) Uani d . 1 C
H10 0.6781 0.0592 0.4996 0.120 Uiso calc R 1 H
C11 0.5878(4) 0.2421(6) 0.52155(10) 0.0813(13) Uani d . 1 C
C12 0.5286(4) 0.2951(5) 0.54961(10) 0.0719(11) Uani d . 1 C
H12 0.4950 0.3989 0.5502 0.086 Uiso calc R 1 H
C13 0.5183(3) 0.1936(4) 0.57759(9) 0.0581(9) Uani d . 1 C
H13 0.4774 0.2296 0.5972 0.070 Uiso calc R 1 H
C14 0.2059(3) 0.0187(4) 0.68625(9) 0.0489(8) Uani d . 1 C
C15 0.0829(3) 0.0493(5) 0.67888(10) 0.0618(10) Uani d . 1 C
H15 0.0513 0.0240 0.6573 0.074 Uiso calc R 1 H
C16 0.0082(4) 0.1170(6) 0.70340(12) 0.0799(13) Uani d . 1 C
H16 -0.0749 0.1343 0.6988 0.096 Uiso calc R 1 H
C17 0.0563(4) 0.1593(6) 0.73481(13) 0.0911(15) Uani d . 1 C
H17 0.0064 0.2096 0.7511 0.109 Uiso calc R 1 H
C18 0.1774(4) 0.1280(6) 0.74243(11) 0.0914(15) Uani d . 1 C
H18 0.2088 0.1552 0.7639 0.110 Uiso calc R 1 H
C19 0.2525(4) 0.0561(5) 0.71824(9) 0.0683(11) Uani d . 1 C
H19 0.3342 0.0331 0.7235 0.082 Uiso calc R 1 H
C20 0.3188(3) -0.3058(5) 0.58706(9) 0.0667(11) Uani d . 1 C
H20A 0.2540 -0.3810 0.5923 0.100 Uiso calc R 1 H
H20B 0.3949 -0.3637 0.5843 0.100 Uiso calc R 1 H
H20C 0.2996 -0.2497 0.5661 0.100 Uiso calc R 1 H
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'
F F 0.0171 0.0103 '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 C5 119.8(3) yes
C1 N1 H1 120.1 ?
C5 N1 H1 120.1 ?
C5 N2 N3 109.7(3) ?
C5 N2 C14 129.7(3) ?
N3 N2 C14 120.3(2) ?
C6 N3 N2 105.2(2) ?
O1 C1 N1 122.3(3) ?
O1 C1 C2 123.2(3) ?
N1 C1 C2 114.5(3) yes
C7 C2 C1 109.1(3) yes
C7 C2 C3 111.5(3) yes
C1 C2 C3 115.3(2) yes
C7 C2 H2 106.8 ?
C1 C2 H2 106.8 ?
C3 C2 H2 106.8 ?
C4 C3 C8 115.3(3) yes
C4 C3 C2 104.9(3) yes
C8 C3 C2 113.8(3) yes
C4 C3 H3 107.5 ?
C8 C3 H3 107.5 ?
C2 C3 H3 107.5 ?
C5 C4 C6 105.1(3) ?
C5 C4 C3 121.5(3) yes
C6 C4 C3 133.4(3) ?
C4 C5 N2 108.9(3) ?
C4 C5 N1 124.9(3) yes
N2 C5 N1 126.2(3) ?
N3 C6 C4 111.1(3) ?
N3 C6 C20 121.3(3) ?
C4 C6 C20 127.5(3) ?
N4 C7 C2 177.0(4) ?
C9 C8 C13 117.9(3) ?
C9 C8 C3 120.1(3) ?
C13 C8 C3 121.9(3) ?
C8 C9 C10 121.0(4) ?
C8 C9 H9 119.5 ?
C10 C9 H9 119.5 ?
C11 C10 C9 118.4(4) ?
C11 C10 H10 120.8 ?
C9 C10 H10 120.8 ?
C12 C11 C10 122.7(4) ?
C12 C11 F1 118.9(5) ?
C10 C11 F1 118.4(4) ?
C11 C12 C13 119.0(4) ?
C11 C12 H12 120.5 ?
C13 C12 H12 120.5 ?
C12 C13 C8 121.0(3) ?
C12 C13 H13 119.5 ?
C8 C13 H13 119.5 ?
C19 C14 C15 119.9(3) ?
C19 C14 N2 120.6(3) ?
C15 C14 N2 119.4(3) ?
C16 C15 C14 120.0(4) ?
C16 C15 H15 120.0 ?
C14 C15 H15 120.0 ?
C15 C16 C17 119.8(4) ?
C15 C16 H16 120.1 ?
C17 C16 H16 120.1 ?
C18 C17 C16 120.6(4) ?
C18 C17 H17 119.7 ?
C16 C17 H17 119.7 ?
C17 C18 C19 120.0(4) ?
C17 C18 H18 120.0 ?
C19 C18 H18 120.0 ?
C14 C19 C18 119.7(4) ?
C14 C19 H19 120.2 ?
C18 C19 H19 120.2 ?
C6 C20 H20A 109.5 ?
C6 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C6 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C11 1.360(5) ?
N1 C1 1.368(4) yes
N1 C5 1.389(4) yes
N1 H1 0.8600 ?
N2 C5 1.359(4) ?
N2 N3 1.379(4) ?
N2 C14 1.420(4) ?
N3 C6 1.339(4) ?
N4 C7 1.139(4) ?
O1 C1 1.216(4) ?
C1 C2 1.532(5) yes
C2 C7 1.466(4) ?
C2 C3 1.561(4) yes
C2 H2 0.9800 ?
C3 C4 1.503(4) yes
C3 C8 1.516(5) ?
C3 H3 0.9800 ?
C4 C5 1.351(4) yes
C4 C6 1.403(4) ?
C6 C20 1.481(5) ?
C8 C9 1.370(5) ?
C8 C13 1.385(5) ?
C9 C10 1.393(6) ?
C9 H9 0.9300 ?
C10 C11 1.347(6) ?
C10 H10 0.9300 ?
C11 C12 1.340(6) ?
C12 C13 1.377(5) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 C19 1.378(5) ?
C14 C15 1.388(5) ?
C15 C16 1.371(5) ?
C15 H15 0.9300 ?
C16 C17 1.374(6) ?
C16 H16 0.9300 ?
C17 C18 1.372(6) ?
C17 H17 0.9300 ?
C18 C19 1.379(5) ?
C18 H18 0.9300 ?
C19 H19 0.9300 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
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
C5 N2 N3 C6 1.9(3)
C14 N2 N3 C6 176.4(3)
C5 N1 C1 O1 172.2(3)
C5 N1 C1 C2 -10.7(4)
O1 C1 C2 C7 -13.8(4)
N1 C1 C2 C7 169.2(3)
O1 C1 C2 C3 -140.1(3)
N1 C1 C2 C3 42.8(4)
C7 C2 C3 C4 -173.9(3)
C1 C2 C3 C4 -48.8(3)
C7 C2 C3 C8 -47.1(4)
C1 C2 C3 C8 78.0(3)
C8 C3 C4 C5 -97.6(4)
C2 C3 C4 C5 28.3(4)
C8 C3 C4 C6 83.4(4)
C2 C3 C4 C6 -150.6(3)
C6 C4 C5 N2 0.6(4)
C3 C4 C5 N2 -178.5(3)
C6 C4 C5 N1 -179.9(3)
C3 C4 C5 N1 0.9(5)
N3 N2 C5 C4 -1.6(4)
C14 N2 C5 C4 -175.4(3)
N3 N2 C5 N1 179.0(3)
C14 N2 C5 N1 5.1(5)
C1 N1 C5 C4 -11.9(5)
C1 N1 C5 N2 167.5(3)
N2 N3 C6 C4 -1.5(4)
N2 N3 C6 C20 178.8(3)
C5 C4 C6 N3 0.6(4)
C3 C4 C6 N3 179.6(3)
C5 C4 C6 C20 -179.8(3)
C3 C4 C6 C20 -0.7(6)
C4 C3 C8 C9 -132.2(4)
C2 C3 C8 C9 106.5(4)
C4 C3 C8 C13 49.4(4)
C2 C3 C8 C13 -71.8(4)
C13 C8 C9 C10 -0.4(6)
C3 C8 C9 C10 -178.9(4)
C8 C9 C10 C11 0.4(8)
C9 C10 C11 C12 -0.3(8)
C9 C10 C11 F1 179.6(4)
C10 C11 C12 C13 0.1(7)
F1 C11 C12 C13 -179.7(4)
C11 C12 C13 C8 -0.1(6)
C9 C8 C13 C12 0.3(5)
C3 C8 C13 C12 178.7(3)
C5 N2 C14 C19 -41.8(5)
N3 N2 C14 C19 144.9(3)
C5 N2 C14 C15 136.0(4)
N3 N2 C14 C15 -37.2(5)
C19 C14 C15 C16 0.1(6)
N2 C14 C15 C16 -177.8(4)
C14 C15 C16 C17 2.2(7)
C15 C16 C17 C18 -2.8(7)
C16 C17 C18 C19 1.2(8)
C15 C14 C19 C18 -1.8(6)
N2 C14 C19 C18 176.1(4)
C17 C18 C19 C14 1.1(7)
