#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230547.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_2230547
loop_
_publ_author_name
'Wu, Ming-Shu'
'Kong, Du-Lin'
'Zhang, Xiang-Zhu'
_publ_section_title
;
 6-Amino-3-methyl-4-(3-nitrophenyl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile
;
_journal_coeditor_code           ZK2006
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1454
_journal_page_last               o1455
_journal_paper_doi               10.1107/S1600536811017387
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H15 N5 O3'
_chemical_formula_moiety         'C20 H15 N5 O3'
_chemical_formula_sum            'C20 H15 N5 O3'
_chemical_formula_weight         373.37
_chemical_name_systematic
;
6-Amino-3-methyl-4-(3-nitrophenyl)-1-phenyl-1H,4H-
pyrano[2,3-c]pyrazole-5-carbonitrile
;
_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                 96.2630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5089(8)
_cell_length_b                   13.9137(11)
_cell_length_c                   13.3747(12)
_cell_measurement_reflns_used    2416
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.498
_cell_measurement_theta_min      2.605
_cell_volume                     1759.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8659
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9550
_exptl_absorpt_correction_T_min  0.9522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.47
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.173
_refine_ls_extinction_coef       0.0100(13)
_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   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0420
_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)+(0.0397P)²+0.6842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                1961
_reflns_number_total             3087
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zk2006.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230547
_cod_database_fobs_code          2230547
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.71933(19) 0.52908(13) 0.63123(13) 0.0440(5) Uani d . 1 1 . .
N N2 0.8060(2) 0.46605(13) 0.58687(15) 0.0507(5) Uani d . 1 1 . .
N N3 0.3851(2) 0.75499(15) 0.52319(15) 0.0565(6) Uani d . 1 1 . .
H H3A 0.3339 0.7879 0.4785 0.068 Uiso calc R 1 1 . .
H H3B 0.3776 0.7641 0.5860 0.068 Uiso calc R 1 1 . .
N N4 0.3550(2) 0.74422(18) 0.24916(17) 0.0741(7) Uani d . 1 1 . .
N N5 1.0378(2) 0.80263(17) 0.3702(2) 0.0674(7) Uani d . 1 1 . .
O O1 0.54812(16) 0.64832(11) 0.57873(10) 0.0471(4) Uani d . 1 1 . .
O O2 1.0555(2) 0.79273(15) 0.46155(19) 0.0900(7) Uani d . 1 1 . .
O O3 1.1104(2) 0.85581(18) 0.3254(2) 0.1121(9) Uani d . 1 1 . .
C C1 0.6433(2) 0.57976(15) 0.55812(16) 0.0404(5) Uani d . 1 1 . .
C C2 0.6769(2) 0.55266(16) 0.46700(16) 0.0418(5) Uani d . 1 1 . .
C C3 0.7801(2) 0.48064(16) 0.48860(18) 0.0466(6) Uani d . 1 1 . .
C C4 0.8571(3) 0.42635(18) 0.4160(2) 0.0625(7) Uani d . 1 1 . .
H H4A 0.9190 0.4691 0.3853 0.094 Uiso calc R 1 1 . .
H H4B 0.7903 0.3987 0.3651 0.094 Uiso calc R 1 1 . .
H H4C 0.9118 0.3761 0.4508 0.094 Uiso calc R 1 1 . .
C C5 0.4761(2) 0.68993(16) 0.49508(17) 0.0429(6) Uani d . 1 1 . .
C C6 0.5006(2) 0.66700(16) 0.40010(16) 0.0429(6) Uani d . 1 1 . .
C C7 0.6133(2) 0.59767(16) 0.37153(16) 0.0434(6) Uani d . 1 1 . .
H H7 0.5673 0.5474 0.3283 0.052 Uiso calc R 1 1 . .
C C8 0.7221(2) 0.64836(16) 0.31459(16) 0.0412(5) Uani d . 1 1 . .
C C9 0.8293(2) 0.70132(16) 0.36589(17) 0.0445(6) Uani d . 1 1 . .
H H9 0.8368 0.7053 0.4357 0.053 Uiso calc R 1 1 . .
C C10 0.9247(2) 0.74805(16) 0.31350(19) 0.0482(6) Uani d . 1 1 . .
C C11 0.9187(3) 0.74412(19) 0.2108(2) 0.0650(7) Uani d . 1 1 . .
H H11 0.9848 0.7762 0.1767 0.078 Uiso calc R 1 1 . .
C C12 0.8126(3) 0.6916(2) 0.1602(2) 0.0722(8) Uani d . 1 1 . .
H H12 0.8063 0.6875 0.0904 0.087 Uiso calc R 1 1 . .
C C13 0.7148(3) 0.64464(19) 0.21116(17) 0.0567(7) Uani d . 1 1 . .
H H13 0.6426 0.6098 0.1752 0.068 Uiso calc R 1 1 . .
C C14 0.4173(3) 0.71120(18) 0.31880(18) 0.0510(6) Uani d . 1 1 . .
C C15 0.7217(3) 0.52889(16) 0.73764(17) 0.0466(6) Uani d . 1 1 . .
C C16 0.6181(3) 0.57274(18) 0.78491(18) 0.0575(7) Uani d . 1 1 . .
H H16 0.5454 0.6060 0.7476 0.069 Uiso calc R 1 1 . .
C C17 0.6223(4) 0.5672(2) 0.8885(2) 0.0740(9) Uani d . 1 1 . .
H H17 0.5521 0.5967 0.9208 0.089 Uiso calc R 1 1 . .
C C18 0.7290(4) 0.5184(2) 0.9436(2) 0.0851(10) Uani d . 1 1 . .
H H18 0.7303 0.5137 1.0131 0.102 Uiso calc R 1 1 . .
C C19 0.8331(4) 0.4768(2) 0.8965(2) 0.0856(10) Uani d . 1 1 . .
H H19 0.9066 0.4449 0.9343 0.103 Uiso calc R 1 1 . .
C C20 0.8312(3) 0.4813(2) 0.7935(2) 0.0684(8) Uani d . 1 1 . .
H H20 0.9028 0.4527 0.7619 0.082 Uiso calc R 1 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
C1 N1 N2 . . 108.55(17) ?
C1 N1 C15 . . 132.5(2) ?
N2 N1 C15 . . 118.94(18) ?
C3 N2 N1 . . 105.87(18) ?
C5 N3 H3A . . 120.0 ?
C5 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
O3 N5 O2 . . 122.6(3) ?
O3 N5 C10 . . 119.1(3) ?
O2 N5 C10 . . 118.3(2) ?
C1 O1 C5 . . 114.40(17) ?
C2 C1 N1 . . 110.4(2) ?
C2 C1 O1 . . 127.4(2) ?
N1 C1 O1 . . 122.27(19) ?
C1 C2 C3 . . 104.0(2) ?
C1 C2 C7 . . 123.0(2) ?
C3 C2 C7 . . 133.0(2) ?
N2 C3 C2 . . 111.2(2) ?
N2 C3 C4 . . 121.2(2) ?
C2 C3 C4 . . 127.5(2) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N3 C5 C6 . . 127.4(2) ?
N3 C5 O1 . . 109.72(19) ?
C6 C5 O1 . . 122.9(2) ?
C5 C6 C14 . . 118.6(2) ?
C5 C6 C7 . . 125.7(2) ?
C14 C6 C7 . . 115.70(19) ?
C2 C7 C6 . . 106.39(18) ?
C2 C7 C8 . . 112.92(18) ?
C6 C7 C8 . . 111.56(18) ?
C2 C7 H7 . . 108.6 ?
C6 C7 H7 . . 108.6 ?
C8 C7 H7 . . 108.6 ?
C9 C8 C13 . . 118.2(2) ?
C9 C8 C7 . . 120.29(19) ?
C13 C8 C7 . . 121.5(2) ?
C10 C9 C8 . . 119.6(2) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 122.5(2) ?
C9 C10 N5 . . 118.2(2) ?
C11 C10 N5 . . 119.3(2) ?
C12 C11 C10 . . 117.8(2) ?
C12 C11 H11 . . 121.1 ?
C10 C11 H11 . . 121.1 ?
C11 C12 C13 . . 120.8(2) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C8 . . 121.1(2) ?
C12 C13 H13 . . 119.5 ?
C8 C13 H13 . . 119.5 ?
N4 C14 C6 . . 175.8(3) ?
C16 C15 C20 . . 120.0(2) ?
C16 C15 N1 . . 121.8(2) ?
C20 C15 N1 . . 118.1(2) ?
C15 C16 C17 . . 119.5(3) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C18 C17 C16 . . 120.4(3) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C19 C18 C17 . . 119.7(3) ?
C19 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
C18 C19 C20 . . 120.9(3) ?
C18 C19 H19 . . 119.5 ?
C20 C19 H19 . . 119.5 ?
C19 C20 C15 . . 119.3(3) ?
C19 C20 H20 . . 120.3 ?
C15 C20 H20 . . 120.3 ?
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
N1 C1 . 1.350(3) ?
N1 N2 . 1.381(2) ?
N1 C15 . 1.421(3) ?
N2 C3 . 1.326(3) ?
N3 C5 . 1.334(3) ?
N3 H3A . 0.8600 ?
N3 H3B . 0.8600 ?
N4 C14 . 1.144(3) ?
N5 O3 . 1.214(3) ?
N5 O2 . 1.222(3) ?
N5 C10 . 1.460(3) ?
O1 C1 . 1.364(3) ?
O1 C5 . 1.374(2) ?
C1 C2 . 1.347(3) ?
C2 C3 . 1.411(3) ?
C2 C7 . 1.490(3) ?
C3 C4 . 1.484(3) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.354(3) ?
C6 C14 . 1.414(3) ?
C6 C7 . 1.522(3) ?
C7 C8 . 1.523(3) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.378(3) ?
C8 C13 . 1.379(3) ?
C9 C10 . 1.369(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(3) ?
C11 C12 . 1.364(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.377(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C15 C16 . 1.371(3) ?
C15 C20 . 1.382(3) ?
C16 C17 . 1.384(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.367(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.360(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.377(4) ?
C19 H19 . 0.9300 ?
C20 H20 . 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_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A O2 1_455 0.86 2.63 3.196(3) 124
N3 H3B N4 4_576 0.86 2.22 3.067(3) 169
C19 H19 O2 2_746 0.93 2.54 3.294(4) 139
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
C1 N1 N2 C3 . . . . 0.1(2) ?
C15 N1 N2 C3 . . . . 178.88(19) ?
N2 N1 C1 C2 . . . . -0.1(2) ?
C15 N1 C1 C2 . . . . -178.6(2) ?
N2 N1 C1 O1 . . . . -179.75(18) ?
C15 N1 C1 O1 . . . . 1.7(3) ?
C5 O1 C1 C2 . . . . 3.0(3) ?
C5 O1 C1 N1 . . . . -177.44(18) ?
N1 C1 C2 C3 . . . . 0.1(2) ?
O1 C1 C2 C3 . . . . 179.7(2) ?
N1 C1 C2 C7 . . . . -178.24(19) ?
O1 C1 C2 C7 . . . . 1.4(3) ?
N1 N2 C3 C2 . . . . -0.1(2) ?
N1 N2 C3 C4 . . . . 178.7(2) ?
C1 C2 C3 N2 . . . . 0.0(3) ?
C7 C2 C3 N2 . . . . 178.1(2) ?
C1 C2 C3 C4 . . . . -178.7(2) ?
C7 C2 C3 C4 . . . . -0.7(4) ?
C1 O1 C5 N3 . . . . 179.41(18) ?
C1 O1 C5 C6 . . . . -2.0(3) ?
N3 C5 C6 C14 . . . . -4.0(4) ?
O1 C5 C6 C14 . . . . 177.69(19) ?
N3 C5 C6 C7 . . . . 175.1(2) ?
O1 C5 C6 C7 . . . . -3.3(3) ?
C1 C2 C7 C6 . . . . -5.6(3) ?
C3 C2 C7 C6 . . . . 176.6(2) ?
C1 C2 C7 C8 . . . . 117.1(2) ?
C3 C2 C7 C8 . . . . -60.7(3) ?
C5 C6 C7 C2 . . . . 6.7(3) ?
C14 C6 C7 C2 . . . . -174.27(19) ?
C5 C6 C7 C8 . . . . -116.9(2) ?
C14 C6 C7 C8 . . . . 62.2(2) ?
C2 C7 C8 C9 . . . . -40.3(3) ?
C6 C7 C8 C9 . . . . 79.5(2) ?
C2 C7 C8 C13 . . . . 141.2(2) ?
C6 C7 C8 C13 . . . . -99.0(2) ?
C13 C8 C9 C10 . . . . -0.2(3) ?
C7 C8 C9 C10 . . . . -178.7(2) ?
C8 C9 C10 C11 . . . . -0.3(4) ?
C8 C9 C10 N5 . . . . -179.3(2) ?
O3 N5 C10 C9 . . . . -169.2(2) ?
O2 N5 C10 C9 . . . . 10.8(3) ?
O3 N5 C10 C11 . . . . 11.8(4) ?
O2 N5 C10 C11 . . . . -168.2(3) ?
C9 C10 C11 C12 . . . . 0.3(4) ?
N5 C10 C11 C12 . . . . 179.3(2) ?
C10 C11 C12 C13 . . . . 0.3(4) ?
C11 C12 C13 C8 . . . . -0.7(4) ?
C9 C8 C13 C12 . . . . 0.7(4) ?
C7 C8 C13 C12 . . . . 179.2(2) ?
C5 C6 C14 N4 . . . . 175(4) ?
C7 C6 C14 N4 . . . . -5(4) ?
C1 N1 C15 C16 . . . . 13.3(4) ?
N2 N1 C15 C16 . . . . -165.1(2) ?
C1 N1 C15 C20 . . . . -167.8(2) ?
N2 N1 C15 C20 . . . . 13.8(3) ?
C20 C15 C16 C17 . . . . -1.4(4) ?
N1 C15 C16 C17 . . . . 177.4(2) ?
C15 C16 C17 C18 . . . . 0.1(4) ?
C16 C17 C18 C19 . . . . 1.3(5) ?
C17 C18 C19 C20 . . . . -1.4(5) ?
C18 C19 C20 C15 . . . . 0.0(5) ?
C16 C15 C20 C19 . . . . 1.4(4) ?
N1 C15 C20 C19 . . . . -177.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2112463
