#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/81/2238163.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_2238163
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Castillo, Juan C.'
'Abonia, Rodrigo'
'Ellena, Javier'
'Tenorio, Juan C.'
_publ_section_title
;
 (+-)-3-(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-benzofuran-1(3H)-one
;
_journal_coeditor_code           GG2119
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1181
_journal_page_last               o1182
_journal_paper_doi               10.1107/S1600536813017479
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C18 H15 N3 O2'
_chemical_formula_moiety         'C18 H15 N3 O2'
_chemical_formula_sum            'C18 H15 N3 O2'
_chemical_formula_weight         305.33
_chemical_melting_point          464.0(10)
_chemical_name_common
(+-)-3-(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-benzofuran-1(3H)-one
_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                 123.257(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0451(2)
_cell_length_b                   15.0631(5)
_cell_length_c                   12.2008(4)
_cell_measurement_reflns_used    14996
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.546
_cell_volume                     1543.75(9)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15125
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1038P)²+0.1468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1733
_reflns_number_gt                2264
_reflns_number_total             3449
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2119.cif
_cod_data_source_block           I
_cod_original_cell_volume        1543.75(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238163
_cod_database_fobs_code          2238163
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
O O2 -0.07121(16) 0.81568(8) 0.27256(14) 0.0549(4) Uani d . 1 1
N N2 0.36978(18) 0.72091(10) 0.28921(14) 0.0438(4) Uani d . 1 1
N N3 0.27961(18) 0.77174(10) 0.17675(13) 0.0455(4) Uani d . 1 1
C C13 0.4909(2) 0.66591(12) 0.29898(16) 0.0413(4) Uani d . 1 1
O O1 -0.28573(17) 0.90333(11) 0.17908(17) 0.0733(5) Uani d . 1 1
C C11 0.1725(2) 0.81116(11) 0.19068(17) 0.0433(4) Uani d . 1 1
N N1 0.38101(19) 0.68232(11) 0.48354(14) 0.0532(5) Uani d . 1 1
H H1A 0.4582 0.6461 0.5063 0.064 Uiso calc R 1 1
H H1B 0.3447 0.6890 0.5325 0.064 Uiso calc R 1 1
C C7 0.1242(2) 0.92069(12) 0.39955(16) 0.0426(4) Uani d . 1 1
C C10 0.3162(2) 0.72929(11) 0.36959(16) 0.0402(4) Uani d . 1 1
C C14 0.5007(2) 0.57697(13) 0.33054(18) 0.0500(5) Uani d . 1 1
H H14 0.4357 0.5534 0.3556 0.060 Uiso calc R 1 1
C C9 0.1904(2) 0.78783(11) 0.31016(16) 0.0411(4) Uani d . 1 1
C C2 -0.0212(2) 0.96295(12) 0.33066(17) 0.0465(5) Uani d . 1 1
C C6 0.2622(2) 0.96761(14) 0.48389(18) 0.0527(5) Uani d . 1 1
H H6 0.3608 0.9395 0.5306 0.063 Uiso calc R 1 1
C C8 0.1023(2) 0.82334(12) 0.36679(18) 0.0446(4) Uani d . 1 1
C C18 0.5921(2) 0.70181(13) 0.26633(18) 0.0500(5) Uani d . 1 1
H H18 0.5900 0.7624 0.2506 0.060 Uiso calc R 1 1
C C12 0.0453(2) 0.86596(14) 0.08062(18) 0.0559(5) Uani d . 1 1
H H12A 0.0652 0.8701 0.0123 0.084 Uiso calc R 1 1
H H12B 0.0454 0.9244 0.1122 0.084 Uiso calc R 1 1
H H12C -0.0564 0.8386 0.0467 0.084 Uiso calc R 1 1
C C17 0.6953(2) 0.64713(15) 0.2575(2) 0.0588(5) Uani d . 1 1
H H17 0.7606 0.6705 0.2326 0.071 Uiso calc R 1 1
C C1 -0.1431(2) 0.89583(13) 0.2522(2) 0.0528(5) Uani d . 1 1
C C16 0.7027(3) 0.55779(16) 0.2851(2) 0.0637(6) Uani d . 1 1
H H16 0.7713 0.5210 0.2772 0.076 Uiso calc R 1 1
C C15 0.6087(3) 0.52322(14) 0.3245(2) 0.0603(5) Uani d . 1 1
H H15 0.6175 0.4636 0.3471 0.072 Uiso calc R 1 1
C C3 -0.0347(3) 1.05330(14) 0.3422(2) 0.0609(6) Uani d . 1 1
H H3 -0.1330 1.0816 0.2950 0.073 Uiso calc R 1 1
C C5 0.2482(3) 1.05762(15) 0.4961(2) 0.0646(6) Uani d . 1 1
H H5 0.3388 1.0907 0.5529 0.077 Uiso calc R 1 1
C C4 0.1022(3) 1.09962(15) 0.4257(2) 0.0676(6) Uani d . 1 1
H H4 0.0966 1.1605 0.4351 0.081 Uiso calc R 1 1
H H8 0.130(2) 0.7852(12) 0.4451(19) 0.049(5) Uiso d . 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
C1 O2 C8 110.83(14)
C10 N2 N3 111.11(13)
C10 N2 C13 130.77(14)
N3 N2 C13 117.96(13)
C11 N3 N2 104.90(13)
C14 C13 C18 120.37(17)
C14 C13 N2 121.01(16)
C18 C13 N2 118.44(16)
N3 C11 C9 111.71(16)
N3 C11 C12 119.26(15)
C9 C11 C12 128.82(17)
C10 N1 H1A 120.0
C10 N1 H1B 120.0
H1A N1 H1B 120.0
C2 C7 C6 120.81(18)
C2 C7 C8 109.70(16)
C6 C7 C8 129.49(17)
N2 C10 N1 122.01(15)
N2 C10 C9 106.96(14)
N1 C10 C9 130.99(15)
C13 C14 C15 119.29(18)
C13 C14 H14 120.4
C15 C14 H14 120.4
C10 C9 C11 105.30(15)
C10 C9 C8 126.36(15)
C11 C9 C8 128.18(16)
C7 C2 C3 121.57(18)
C7 C2 C1 107.81(16)
C3 C2 C1 130.63(18)
C5 C6 C7 117.50(19)
C5 C6 H6 121.2
C7 C6 H6 121.2
O2 C8 C9 111.06(14)
O2 C8 C7 102.78(14)
C9 C8 C7 115.86(15)
O2 C8 H8 106.9(11)
C9 C8 H8 107.7(10)
C7 C8 H8 112.2(11)
C17 C18 C13 119.47(18)
C17 C18 H18 120.3
C13 C18 H18 120.3
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C18 C17 C16 120.47(18)
C18 C17 H17 119.8
C16 C17 H17 119.8
O1 C1 O2 120.95(19)
O1 C1 C2 130.16(19)
O2 C1 C2 108.88(16)
C15 C16 C17 119.97(19)
C15 C16 H16 120.0
C17 C16 H16 120.0
C16 C15 C14 120.29(19)
C16 C15 H15 119.9
C14 C15 H15 119.9
C4 C3 C2 117.51(19)
C4 C3 H3 121.2
C2 C3 H3 121.2
C6 C5 C4 121.3(2)
C6 C5 H5 119.3
C4 C5 H5 119.3
C3 C4 C5 121.3(2)
C3 C4 H4 119.4
C5 C4 H4 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C1 1.358(2)
O2 C8 1.475(2)
N2 C10 1.359(2)
N2 N3 1.388(2)
N2 C13 1.422(2)
N3 C11 1.319(2)
C13 C14 1.382(3)
C13 C18 1.389(2)
O1 C1 1.208(2)
C11 C9 1.412(2)
C11 C12 1.495(3)
N1 C10 1.365(2)
N1 H1A 0.8600
N1 H1B 0.8600
C7 C2 1.377(3)
C7 C6 1.384(3)
C7 C8 1.504(3)
C10 C9 1.376(2)
C14 C15 1.388(3)
C14 H14 0.9300
C9 C8 1.489(2)
C2 C3 1.383(3)
C2 C1 1.467(3)
C6 C5 1.380(3)
C6 H6 0.9300
C8 H8 1.013(19)
C18 C17 1.375(3)
C18 H18 0.9300
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C17 C16 1.379(3)
C17 H17 0.9300
C16 C15 1.375(3)
C16 H16 0.9300
C15 H15 0.9300
C3 C4 1.371(3)
C3 H3 0.9300
C5 C4 1.381(3)
C5 H5 0.9300
C4 H4 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
N1 H1A O1 4_676 0.86 2.38 3.131(2) 146.0
N1 H1B N3 4_576 0.86 2.27 3.116(2) 169.4
C8 H8 N3 4_576 1.013(19) 2.51(2) 3.484(2) 159.9(15)
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
C10 N2 N3 C11 0.49(19)
C13 N2 N3 C11 176.40(15)
C10 N2 C13 C14 45.9(3)
N3 N2 C13 C14 -129.02(17)
C10 N2 C13 C18 -138.91(19)
N3 N2 C13 C18 46.1(2)
N2 N3 C11 C9 0.29(19)
N2 N3 C11 C12 -174.89(15)
N3 N2 C10 N1 176.82(16)
C13 N2 C10 N1 1.6(3)
N3 N2 C10 C9 -1.07(19)
C13 N2 C10 C9 -176.30(17)
C18 C13 C14 C15 -2.4(3)
N2 C13 C14 C15 172.66(17)
N2 C10 C9 C11 1.17(19)
N1 C10 C9 C11 -176.46(18)
N2 C10 C9 C8 -174.57(16)
N1 C10 C9 C8 7.8(3)
N3 C11 C9 C10 -0.9(2)
C12 C11 C9 C10 173.66(17)
N3 C11 C9 C8 174.71(17)
C12 C11 C9 C8 -10.7(3)
C6 C7 C2 C3 0.5(3)
C8 C7 C2 C3 -179.57(16)
C6 C7 C2 C1 -179.22(16)
C8 C7 C2 C1 0.73(19)
C2 C7 C6 C5 0.1(3)
C8 C7 C6 C5 -179.82(17)
C1 O2 C8 C9 -124.84(16)
C1 O2 C8 C7 -0.32(18)
C10 C9 C8 O2 -131.54(18)
C11 C9 C8 O2 53.7(2)
C10 C9 C8 C7 111.7(2)
C11 C9 C8 C7 -63.1(2)
C2 C7 C8 O2 -0.28(17)
C6 C7 C8 O2 179.67(16)
C2 C7 C8 C9 121.01(17)
C6 C7 C8 C9 -59.0(2)
C14 C13 C18 C17 4.1(3)
N2 C13 C18 C17 -171.06(16)
C13 C18 C17 C16 -2.3(3)
C8 O2 C1 O1 -179.17(17)
C8 O2 C1 C2 0.8(2)
C7 C2 C1 O1 179.0(2)
C3 C2 C1 O1 -0.7(4)
C7 C2 C1 O2 -0.9(2)
C3 C2 C1 O2 179.40(18)
C18 C17 C16 C15 -1.3(3)
C17 C16 C15 C14 3.1(3)
C13 C14 C15 C16 -1.2(3)
C7 C2 C3 C4 -0.4(3)
C1 C2 C3 C4 179.19(19)
C7 C6 C5 C4 -0.8(3)
C2 C3 C4 C5 -0.2(3)
C6 C5 C4 C3 0.8(3)
