#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/88/2018809.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_2018809
loop_
_publ_author_name
'Portilla, Jaime'
'Ontiveros, Ina'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 5-Methyl-N-[2-nitro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-amine:
 a chain of hydrogen-bonded R₂²(6) and R₂²(16) rings
;
_journal_coeditor_code           YF3024
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              172
_journal_page_last               174
_journal_paper_doi               10.1107/S0108270113000607
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C11 H9 F3 N4 O2'
_chemical_formula_moiety         'C11 H9 F3 N4 O2'
_chemical_formula_sum            'C11 H9 F3 N4 O2'
_chemical_formula_weight         286.22
_chemical_name_systematic
;
5-Methyl-N-[2-nitro-4-(trifluoromethyl)phenyl]-1H-pyrazole-
3-amine
;
_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                93.22(3)
_cell_angle_beta                 97.02(3)
_cell_angle_gamma                91.05(3)
_cell_formula_units_Z            2
_cell_length_a                   4.957(2)
_cell_length_b                   8.737(3)
_cell_length_c                   13.562(5)
_cell_measurement_reflns_used    2670
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.86
_cell_volume                     581.8(4)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14609
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0582P)²+0.3103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                2109
_reflns_number_total             2670
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yf3024.cif
_cod_data_source_block           I
_cod_database_code               2018809
_cod_database_fobs_code          2018809
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_symmetry_multiplicity
N N1 0.8748(3) 0.09599(17) 0.58201(10) 0.0236(3) Uani d . 1 1
H H1 1.0137 0.0349 0.5916 0.028 Uiso calc R 1 1
N N2 0.7585(3) 0.13140(17) 0.48990(10) 0.0229(3) Uani d . 1 1
C C3 0.5602(3) 0.22565(18) 0.50934(12) 0.0189(3) Uani d . 1 1
C C4 0.5484(3) 0.24949(19) 0.61249(12) 0.0212(3) Uani d . 1 1
H H4 0.4247 0.3110 0.6444 0.025 Uiso calc R 1 1
C C5 0.7558(3) 0.16395(19) 0.65692(12) 0.0215(4) Uani d . 1 1
N N31 0.3848(3) 0.29445(16) 0.43711(10) 0.0201(3) Uani d . 1 1
H H31 0.2591 0.3513 0.4601 0.024 Uiso calc R 1 1
C C31 0.3799(3) 0.28642(18) 0.33628(12) 0.0182(3) Uani d . 1 1
C C32 0.1950(3) 0.36955(18) 0.27219(12) 0.0187(3) Uani d . 1 1
C C33 0.1965(3) 0.36258(19) 0.16914(12) 0.0215(4) Uani d . 1 1
H H33 0.0720 0.4212 0.1289 0.026 Uiso calc R 1 1
C C34 0.3776(3) 0.27112(19) 0.12573(12) 0.0218(4) Uani d . 1 1
C C35 0.5597(3) 0.18541(19) 0.18631(13) 0.0230(4) Uani d . 1 1
H H35 0.6838 0.1211 0.1567 0.028 Uiso calc R 1 1
C C36 0.5619(3) 0.19277(19) 0.28757(13) 0.0216(4) Uani d . 1 1
H H36 0.6886 0.1336 0.3265 0.026 Uiso calc R 1 1
N N32 -0.0104(3) 0.46636(16) 0.30907(10) 0.0202(3) Uani d . 1 1
O O1 -0.0295(2) 0.47603(14) 0.39979(9) 0.0245(3) Uani d . 1 1
O O2 -0.1633(3) 0.53477(14) 0.24871(9) 0.0263(3) Uani d . 1 1
C C37 0.3781(4) 0.2590(2) 0.01521(14) 0.0292(4) Uani d . 1 1
F F1 0.2346(3) 0.36757(15) -0.03101(8) 0.0431(3) Uani d . 1 1
F F2 0.2700(3) 0.12478(15) -0.02535(9) 0.0512(4) Uani d . 1 1
F F3 0.6293(3) 0.2679(2) -0.01064(9) 0.0552(4) Uani d . 1 1
C C51 0.8584(4) 0.1428(2) 0.76335(13) 0.0284(4) Uani d . 1 1
H H51A 0.8490 0.0337 0.7761 0.043 Uiso calc R 1 1
H H51B 0.7462 0.2004 0.8064 0.043 Uiso calc R 1 1
H H51C 1.0474 0.1805 0.7773 0.043 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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C5 N1 N2 113.33(14) ?
C5 N1 H1 123.3 ?
N2 N1 H1 123.3 ?
C3 N2 N1 103.60(13) ?
N2 C3 N31 124.68(15) ?
N2 C3 C4 111.95(14) ?
N31 C3 C4 123.36(14) ?
C5 C4 C3 104.96(14) ?
C5 C4 H4 127.5 ?
C3 C4 H4 127.5 ?
N1 C5 C4 106.16(15) ?
N1 C5 C51 121.45(15) ?
C4 C5 C51 132.36(16) ?
C31 N31 C3 129.53(14) y
C31 N31 H31 115.2 ?
C3 N31 H31 115.2 ?
N31 C31 C32 123.01(14) ?
N31 C31 C36 121.78(15) ?
C32 C31 C36 115.21(15) ?
C33 C32 C31 122.29(15) ?
C33 C32 N32 115.25(14) ?
C31 C32 N32 122.46(15) ?
C34 C33 C32 120.26(15) ?
C34 C33 H33 119.9 ?
C32 C33 H33 119.9 ?
C33 C34 C35 119.10(15) ?
C33 C34 C37 121.13(15) ?
C35 C34 C37 119.75(15) ?
C36 C35 C34 121.08(15) ?
C36 C35 H35 119.5 ?
C34 C35 H35 119.5 ?
C35 C36 C31 122.05(15) ?
C35 C36 H36 119.0 ?
C31 C36 H36 119.0 ?
O2 N32 O1 122.11(14) ?
O2 N32 C32 118.58(14) ?
O1 N32 C32 119.30(13) ?
F1 C37 F3 107.16(16) ?
F1 C37 F2 106.00(16) ?
F3 C37 F2 106.14(16) ?
F1 C37 C34 113.04(15) ?
F3 C37 C34 112.20(15) ?
F2 C37 C34 111.82(16) ?
C5 C51 H51A 109.5 ?
C5 C51 H51B 109.5 ?
H51A C51 H51B 109.5 ?
C5 C51 H51C 109.5 ?
H51A C51 H51C 109.5 ?
H51B C51 H51C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 1.365(2) y
N1 H1 0.8800 ?
N2 C3 1.335(2) y
C3 N31 1.398(2) ?
C3 C4 1.411(2) y
C4 C5 1.381(2) y
C4 H4 0.9500 ?
C5 N1 1.351(2) y
C5 C51 1.493(2) ?
C32 N32 1.453(2) y
N32 O1 1.2439(18) y
N32 O2 1.2338(18) y
C31 C32 1.422(2) y
C32 C33 1.396(2) y
C33 C34 1.376(2) y
C33 H33 0.9500 ?
C34 C35 1.401(2) y
C34 C37 1.497(2) ?
C35 C36 1.370(2) y
C35 H35 0.9500 ?
C36 C31 1.425(2) y
C36 H36 0.9500 ?
N31 C31 1.363(2) y
N31 H31 0.8800 ?
C37 F1 1.335(2) ?
C37 F3 1.336(2) ?
C37 F2 1.341(2) ?
C51 H51A 0.9800 ?
C51 H51B 0.9800 ?
C51 H51C 0.9800 ?
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
_geom_hbond_publ_flag
N1 H1 N2 2_756 0.88 2.19 2.924(2) 141 y
N31 H31 O1 . 0.88 1.94 2.636(2) 135 y
C4 H4 O2 2_566 0.95 2.43 3.369(2) 170 y
C36 H36 N2 . 0.95 2.20 2.881(2) 128 y
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
C5 N1 N2 C3 0.24(19) ?
N1 N2 C3 N31 179.11(15) ?
N1 N2 C3 C4 -0.40(18) ?
N2 C3 C4 C5 0.4(2) ?
N31 C3 C4 C5 -179.10(15) ?
N2 N1 C5 C4 0.0(2) ?
N2 N1 C5 C51 -178.36(15) ?
C3 C4 C5 N1 -0.25(19) ?
C3 C4 C5 C51 177.88(18) ?
N2 C3 N31 C31 -2.2(3) y
C4 C3 N31 C31 177.23(16) y
C3 N31 C31 C32 -176.90(15) y
C3 N31 C31 C36 3.2(3) y
N31 C31 C32 C33 178.59(15) ?
C36 C31 C32 C33 -1.5(2) ?
N31 C31 C32 N32 -2.1(2) ?
C36 C31 C32 N32 177.86(14) ?
C31 C32 C33 C34 1.1(3) ?
N32 C32 C33 C34 -178.23(15) ?
C32 C33 C34 C35 0.0(3) ?
C32 C33 C34 C37 178.50(16) ?
C33 C34 C35 C36 -0.7(3) ?
C37 C34 C35 C36 -179.25(16) ?
C34 C35 C36 C31 0.3(3) ?
N31 C31 C36 C35 -179.33(16) ?
C32 C31 C36 C35 0.7(2) ?
C31 C32 N32 O1 -1.0(2) y
C31 C32 N32 O2 -179.97(14) y
C33 C32 N32 O1 178.35(14) y
C33 C32 N32 O2 -0.6(2) y
C33 C34 C37 F1 13.9(3) ?
C35 C34 C37 F1 -167.61(16) ?
C33 C34 C37 F3 135.22(18) ?
C35 C34 C37 F3 -46.3(2) ?
C33 C34 C37 F2 -105.6(2) ?
C35 C34 C37 F2 72.9(2) ?
