#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223236.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_2223236
loop_
_publ_author_name
'Chen, Jun-qiang'
'Li, He-ping'
'Huang, Chang-shan'
'Wu, Jin-ying'
_publ_section_title
;
 5-(2-Furyl)-3-methyl-1-(3-nitrophenyl)-4,5-dihydro-1H-pyrazole
;
_journal_coeditor_code           XU2580
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2147
_journal_paper_doi               10.1107/S1600536809031419
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H13 N3 O3'
_chemical_formula_moiety         'C14 H13 N3 O3'
_chemical_formula_sum            'C14 H13 N3 O3'
_chemical_formula_weight         271.27
_chemical_name_systematic
;
5-(2-Furyl)-3-methyl-1-(3-nitrophenyl)-4,5-dihydro-1H-pyrazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                105.764(2)
_cell_angle_beta                 97.054(2)
_cell_angle_gamma                96.944(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2089(2)
_cell_length_b                   7.8581(3)
_cell_length_c                   14.3800(4)
_cell_measurement_reflns_used    1598
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      3.45
_cell_volume                     661.31(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(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       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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9707
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0608P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                1778
_reflns_number_total             2590
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2580.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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               2223236
_cod_database_fobs_code          2223236
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
O O 0.36743(18) 0.34679(15) 0.90208(8) 0.0586(3) Uani d . 1 . .
N N1 0.1661(2) 0.62239(17) 0.78604(10) 0.0496(4) Uani d . 1 . .
N N2 0.2000(2) 0.45740(16) 0.72794(10) 0.0491(4) Uani d . 1 . .
C C9 0.3755(2) 0.4521(2) 0.67745(11) 0.0429(4) Uani d . 1 . .
C C14 0.5059(2) 0.6102(2) 0.67820(11) 0.0460(4) Uani d . 1 . .
H H14A 0.4772 0.7211 0.7132 0.055 Uiso calc R 1 . .
C C7 0.0168(3) 0.5942(2) 0.83623(13) 0.0534(4) Uani d . 1 . .
C C10 0.4224(3) 0.2892(2) 0.62195(12) 0.0546(4) Uani d . 1 . .
H H10A 0.3347 0.1826 0.6191 0.066 Uiso calc R 1 . .
C C4 0.2531(2) 0.2318(2) 0.81601(12) 0.0477(4) Uani d . 1 . .
C C13 0.6784(2) 0.5987(2) 0.62600(12) 0.0514(4) Uani d . 1 . .
N N3 0.8105(2) 0.7665(2) 0.62761(12) 0.0680(5) Uani d . 1 . .
O O1 0.9707(2) 0.7615(2) 0.58611(11) 0.0934(5) Uani d . 1 . .
C C5 0.0941(2) 0.3072(2) 0.75855(12) 0.0508(4) Uani d . 1 . .
H H5A 0.0138 0.2126 0.7010 0.061 Uiso calc R 1 . .
C C12 0.7298(3) 0.4395(3) 0.57272(12) 0.0611(5) Uani d . 1 . .
H H12A 0.8487 0.4365 0.5391 0.073 Uiso calc R 1 . .
C C6 -0.0684(3) 0.4007(3) 0.81836(14) 0.0615(5) Uani d . 1 . .
H H6A -0.2166 0.3686 0.7817 0.074 Uiso calc R 1 . .
H H6B -0.0677 0.3706 0.8795 0.074 Uiso calc R 1 . .
C C1 0.4967(3) 0.2476(3) 0.94299(14) 0.0607(5) Uani d . 1 . .
H H1B 0.5924 0.2920 1.0022 0.073 Uiso calc R 1 . .
O O2 0.7571(3) 0.9062(2) 0.67000(14) 0.1046(6) Uani d . 1 . .
C C11 0.5976(3) 0.2848(3) 0.57136(13) 0.0642(5) Uani d . 1 . .
H H11A 0.6270 0.1748 0.5355 0.077 Uiso calc R 1 . .
C C3 0.3090(3) 0.0707(2) 0.80439(14) 0.0660(5) Uani d . 1 . .
H H3A 0.2550 -0.0308 0.7518 0.079 Uiso calc R 1 . .
C C2 0.4665(3) 0.0818(3) 0.88708(14) 0.0673(5) Uani d . 1 . .
H H2A 0.5350 -0.0108 0.8992 0.081 Uiso calc R 1 . .
C C8 -0.0654(3) 0.7433(3) 0.90245(15) 0.0793(6) Uani d . 1 . .
H H8A 0.0141 0.8556 0.9019 0.119 Uiso calc R 1 . .
H H8B -0.0444 0.7329 0.9678 0.119 Uiso calc R 1 . .
H H8C -0.2191 0.7381 0.8806 0.119 Uiso calc R 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
C4 O C1 . . 105.97(13) ?
C7 N1 N2 . . 108.34(13) ?
C9 N2 N1 . . 118.80(12) ?
C9 N2 C5 . . 125.31(13) ?
N1 N2 C5 . . 111.64(12) ?
N2 C9 C14 . . 120.55(14) ?
N2 C9 C10 . . 120.96(14) ?
C14 C9 C10 . . 118.47(14) ?
C13 C14 C9 . . 118.59(15) ?
C13 C14 H14A . . 120.7 ?
C9 C14 H14A . . 120.7 ?
N1 C7 C8 . . 121.87(16) ?
N1 C7 C6 . . 113.46(15) ?
C8 C7 C6 . . 124.64(16) ?
C11 C10 C9 . . 120.67(16) ?
C11 C10 H10A . . 119.7 ?
C9 C10 H10A . . 119.7 ?
C3 C4 O . . 109.50(15) ?
C3 C4 C5 . . 134.10(17) ?
O C4 C5 . . 116.37(14) ?
C12 C13 C14 . . 123.72(16) ?
C12 C13 N3 . . 119.04(15) ?
C14 C13 N3 . . 117.24(15) ?
O2 N3 O1 . . 122.13(17) ?
O2 N3 C13 . . 118.76(15) ?
O1 N3 C13 . . 119.11(17) ?
N2 C5 C4 . . 112.93(12) ?
N2 C5 C6 . . 100.18(13) ?
C4 C5 C6 . . 113.50(14) ?
N2 C5 H5A . . 110.0 ?
C4 C5 H5A . . 110.0 ?
C6 C5 H5A . . 110.0 ?
C13 C12 C11 . . 117.03(16) ?
C13 C12 H12A . . 121.5 ?
C11 C12 H12A . . 121.5 ?
C7 C6 C5 . . 103.00(13) ?
C7 C6 H6A . . 111.2 ?
C5 C6 H6A . . 111.2 ?
C7 C6 H6B . . 111.2 ?
C5 C6 H6B . . 111.2 ?
H6A C6 H6B . . 109.1 ?
C2 C1 O . . 110.60(15) ?
C2 C1 H1B . . 124.7 ?
O C1 H1B . . 124.7 ?
C12 C11 C10 . . 121.50(17) ?
C12 C11 H11A . . 119.3 ?
C10 C11 H11A . . 119.3 ?
C4 C3 C2 . . 107.27(16) ?
C4 C3 H3A . . 126.4 ?
C2 C3 H3A . . 126.4 ?
C1 C2 C3 . . 106.65(16) ?
C1 C2 H2A . . 126.7 ?
C3 C2 H2A . . 126.7 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
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
O C4 . 1.3689(18) ?
O C1 . 1.372(2) ?
N1 C7 . 1.277(2) ?
N1 N2 . 1.3940(18) ?
N2 C9 . 1.3803(19) ?
N2 C5 . 1.4784(19) ?
C9 C14 . 1.396(2) ?
C9 C10 . 1.397(2) ?
C14 C13 . 1.379(2) ?
C14 H14A . 0.9300 ?
C7 C8 . 1.482(2) ?
C7 C6 . 1.489(3) ?
C10 C11 . 1.380(2) ?
C10 H10A . 0.9300 ?
C4 C3 . 1.325(2) ?
C4 C5 . 1.488(2) ?
C13 C12 . 1.375(2) ?
C13 N3 . 1.459(2) ?
N3 O2 . 1.208(2) ?
N3 O1 . 1.2209(19) ?
C5 C6 . 1.532(2) ?
C5 H5A . 0.9800 ?
C12 C11 . 1.376(3) ?
C12 H12A . 0.9300 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C1 C2 . 1.309(2) ?
C1 H1B . 0.9300 ?
C11 H11A . 0.9300 ?
C3 C2 . 1.420(2) ?
C3 H3A . 0.9300 ?
C2 H2A . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
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
C12 H12A O1 2_766 0.93 2.51 3.311(2) 144
