data_publication_text
_publ_requested_journal          'Beilstein J.Org.Chem.'
_publ_contact_author_name        "Suwiński, Jerzy"
_publ_contact_author_address     
;Silesian University of Technology
Faculty of Chemistry
ul. B. Krzywoustego 4
44-100 Gliwice
Poland
;
_publ_contact_author_email       jerzy.suwinski@polsl.pl
_publ_contact_author_phone       '+48 32 2371915'
_publ_contact_author_fax         '+48 32 2372094'
loop_
_publ_author_name
_publ_author_address

'Kurpet, Marta'
;Silesian University of Technology
Faculty of Chemistry
ul. B. Krzywoustego 4
44-100 Gliwice
Poland
;
'Suwiński, Jerzy'
;Silesian University of Technology
Faculty of Chemistry
ul. B. Krzywoustego 4
44-100 Gliwice
Poland
;
"Kuźnik, Nikodem"
;Silesian University of Technology
Faculty of Chemistry
ul. B. Krzywoustego 4
44-100 Gliwice
Poland
;
 
data_nkx3-15m 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
3-nitro-1-(4-(trifluoromethoxy)phenyl)-1H-pyrazole
; 
_chemical_name_common             ? 
_chemical_melting_point           56.5-58.0  
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C10 H6 F3 N3 O3' 
_chemical_formula_weight          273.18 
 
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' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P2~1~
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    4.2681(9) 
_cell_length_b                    10.435(2) 
_cell_length_c                    24.586(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.20(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1095.0(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     20
_cell_measurement_theta_min       3.3 
_cell_measurement_theta_max       11.6 
 
_exptl_crystal_description        needle 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.6 
_exptl_crystal_size_mid           0.3 
_exptl_crystal_size_min           0.3 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.657 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              552 
_exptl_absorpt_coefficient_mu     0.157 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'KM4 four-circle diffractometer' 
_diffrn_measurement_method        'ω/2θ' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          1 
_diffrn_standards_interval_count  100 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         1.43 
_diffrn_reflns_number             2336 
_diffrn_reflns_av_R_equivalents   0.0472 
_diffrn_reflns_av_sigmaI/netI     0.0337 
_diffrn_reflns_limit_h_min        -5 
_diffrn_reflns_limit_h_max        0 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        0 
_diffrn_reflns_limit_l_min        -29 
_diffrn_reflns_limit_l_max        29 
_diffrn_reflns_theta_min          2.12 
_diffrn_reflns_theta_max          25.06 
_reflns_number_total              2042 
_reflns_number_gt                 1454 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.1084P)²+0.1267P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1.2(18) 
_refine_ls_number_reflns          2042 
_refine_ls_number_parameters      391 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0806 
_refine_ls_R_factor_gt            0.0455 
_refine_ls_wR_factor_ref          0.1494 
_refine_ls_wR_factor_gt           0.1276 
_refine_ls_goodness_of_fit_ref    1.008 
_refine_ls_restrained_S_all       1.008 
_refine_ls_shift/su_max           0.101 
_refine_ls_shift/su_mean          0.008 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
N2B N 0.3205(10) 0.4457(4) 0.48251(17) 0.0583(11) Uani 1 1 d . . . 
N1B N 0.4193(10) 0.3725(4) 0.44114(18) 0.0567(11) Uani 1 1 d . . . 
N3B N 0.0362(12) 0.4090(6) 0.5646(2) 0.0721(14) Uani 1 1 d . . . 
O3B O 0.0866(14) 0.5185(5) 0.5795(2) 0.0901(14) Uani 1 1 d . . . 
O2B O -0.1302(14) 0.3327(6) 0.5896(2) 0.1033(17) Uani 1 1 d . . . 
C7B C 0.1731(12) 0.3638(5) 0.5145(2) 0.0577(13) Uani 1 1 d . . . 
F3B F 0.6528(11) 0.7173(5) 0.2275(2) 0.1023(14) Uani 1 1 d . . . 
C1B C 0.5749(12) 0.4295(5) 0.3952(2) 0.0561(12) Uani 1 1 d . . . 
C6B C 0.5485(15) 0.5590(6) 0.3867(2) 0.0643(14) Uani 1 1 d . . . 
C5B C 0.6905(16) 0.6128(7) 0.3418(3) 0.0710(15) Uani 1 1 d . . . 
O1B O 1.0182(9) 0.5929(6) 0.26242(18) 0.0916(17) Uani 1 1 d . . . 
F1B F 0.6805(13) 0.5300(5) 0.1993(2) 0.1143(16) Uani 1 1 d . . . 
C4B C 0.8538(13) 0.5370(8) 0.3064(2) 0.0699(16) Uani 1 1 d . . . 
C8B C 0.1739(17) 0.2412(6) 0.4951(3) 0.0711(17) Uani 1 1 d . . . 
C2B C 0.7410(15) 0.3545(8) 0.3596(3) 0.0727(16) Uani 1 1 d . . . 
C9B C 0.3337(16) 0.2483(6) 0.4480(3) 0.0719(16) Uani 1 1 d . . . 
C3B C 0.8812(15) 0.4082(8) 0.3146(3) 0.0760(19) Uani 1 1 d . . . 
F2B F 1.0428(9) 0.6629(7) 0.1805(2) 0.129(2) Uani 1 1 d . . . 
C10B C 0.8538(13) 0.6246(8) 0.2187(3) 0.0751(17) Uani 1 1 d . . . 
N2A N 0.8228(10) 0.1958(4) 0.01734(18) 0.0581(11) Uani 1 1 d . . . 
N1A N 0.9205(10) 0.2708(4) 0.05874(17) 0.0553(10) Uani 1 1 d . . . 
N3A N 0.5358(13) 0.2348(5) -0.0642(2) 0.0694(13) Uani 1 1 d . . . 
O3A O 0.3719(14) 0.3103(6) -0.0894(2) 0.1045(17) Uani 1 1 d . . . 
F3A F 1.1536(10) -0.0745(5) 0.2725(2) 0.1033(14) Uani 1 1 d . . . 
C7A C 0.6753(12) 0.2785(5) -0.0145(2) 0.0561(12) Uani 1 1 d . . . 
O2A O 0.5847(14) 0.1257(5) -0.0792(2) 0.0893(13) Uani 1 1 d . . . 
C6A C 1.0482(14) 0.0838(6) 0.1131(2) 0.0634(14) Uani 1 1 d . . . 
C1A C 1.0746(12) 0.2132(5) 0.1043(2) 0.0553(12) Uani 1 1 d . . . 
O1A O 1.5169(9) 0.0503(6) 0.23756(17) 0.0857(15) Uani 1 1 d . . . 
C4A C 1.3511(11) 0.1055(7) 0.1933(2) 0.0649(15) Uani 1 1 d . . . 
C5A C 1.1902(17) 0.0277(8) 0.1582(3) 0.0722(16) Uani 1 1 d . . . 
F2A F 1.1803(13) 0.1135(5) 0.3005(2) 0.1143(15) Uani 1 1 d . . . 
C8A C 0.6731(15) 0.4030(6) 0.0046(3) 0.0692(15) Uani 1 1 d . . . 
C10A C 1.3570(14) 0.0204(8) 0.2817(3) 0.0759(17) Uani 1 1 d . . . 
C2A C 1.2410(14) 0.2907(7) 0.1402(3) 0.0696(15) Uani 1 1 d . . . 
F1A F 1.5425(9) -0.0207(8) 0.31934(19) 0.137(3) Uani 1 1 d . . . 
C3A C 1.3811(14) 0.2343(8) 0.1853(3) 0.0755(18) Uani 1 1 d . . . 
C9A C 0.8332(14) 0.3946(6) 0.0524(3) 0.0680(14) Uani 1 1 d . . . 
H6A H 0.957(14) 0.027(7) 0.087(3) 0.074(18) Uiso 1 1 d . . . 
H6B H 0.459(17) 0.599(8) 0.415(4) 0.09(2) Uiso 1 1 d . . . 
H5B H 0.678(13) 0.700(7) 0.336(2) 0.061(16) Uiso 1 1 d . . . 
H3A H 1.50(2) 0.278(10) 0.211(5) 0.13(3) Uiso 1 1 d . . . 
H9B H 0.376(15) 0.190(7) 0.424(3) 0.073(18) Uiso 1 1 d . . . 
H3B H 0.98(2) 0.368(10) 0.296(4) 0.11(3) Uiso 1 1 d . . . 
H5A H 1.179(18) -0.057(10) 0.163(4) 0.10(3) Uiso 1 1 d . . . 
H9A H 0.882(16) 0.464(8) 0.077(3) 0.09(2) Uiso 1 1 d . . . 
H8A H 0.606(16) 0.477(8) -0.013(3) 0.09(2) Uiso 1 1 d . . . 
H2B H 0.755(13) 0.278(7) 0.365(3) 0.061(18) Uiso 1 1 d . . . 
H2A H 1.231(17) 0.387(9) 0.142(3) 0.10(2) Uiso 1 1 d . . . 
H8B H 0.110(12) 0.173(6) 0.504(2) 0.049(14) Uiso 1 1 d . . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
N2B C7B 1.322(7) . ? 
N2B N1B 1.341(6) . ? 
N1B C9B 1.357(8) . ? 
N1B C1B 1.440(7) . ? 
N3B O3B 1.218(8) . ? 
N3B O2B 1.231(8) . ? 
N3B C7B 1.445(8) . ? 
C7B C8B 1.365(9) . ? 
F3B C10B 1.311(8) . ? 
C1B C6B 1.372(8) . ? 
C1B C2B 1.373(9) . ? 
C6B C5B 1.381(10) . ? 
C5B C4B 1.368(10) . ? 
O1B C10B 1.323(8) . ? 
O1B C4B 1.418(8) . ? 
F1B C10B 1.321(8) . ? 
C4B C3B 1.363(11) . ? 
C8B C9B 1.347(10) . ? 
C2B C3B 1.378(10) . ? 
F2B C10B 1.303(8) . ? 
N2A C7A 1.323(7) . ? 
N2A N1A 1.349(6) . ? 
N1A C9A 1.354(8) . ? 
N1A C1A 1.429(7) . ? 
N3A O2A 1.215(7) . ? 
N3A O3A 1.221(7) . ? 
N3A C7A 1.432(8) . ? 
F3A C10A 1.336(9) . ? 
C7A C8A 1.381(9) . ? 
C6A C1A 1.373(8) . ? 
C6A C5A 1.392(10) . ? 
C1A C2A 1.389(9) . ? 
O1A C10A 1.321(8) . ? 
O1A C4A 1.418(7) . ? 
C4A C3A 1.365(10) . ? 
C4A C5A 1.368(10) . ? 
F2A C10A 1.315(8) . ? 
C8A C9A 1.361(9) . ? 
C10A F1A 1.289(8) . ? 
C2A C3A 1.389(10) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C7B N2B N1B 103.5(4) . . ? 
N2B N1B C9B 111.3(5) . . ? 
N2B N1B C1B 120.4(4) . . ? 
C9B N1B C1B 128.2(5) . . ? 
O3B N3B O2B 124.0(6) . . ? 
O3B N3B C7B 119.3(6) . . ? 
O2B N3B C7B 116.7(6) . . ? 
N2B C7B N3B 119.4(5) . . ? 
N2B C7B C8B 113.4(5) . . ? 
N3B C7B C8B 127.2(6) . . ? 
C6B C1B C2B 120.4(6) . . ? 
C6B C1B N1B 119.3(5) . . ? 
C2B C1B N1B 120.3(5) . . ? 
C1B C6B C5B 119.1(7) . . ? 
C4B C5B C6B 119.9(7) . . ? 
C10B O1B C4B 117.4(4) . . ? 
C3B C4B C5B 121.3(6) . . ? 
C3B C4B O1B 118.4(7) . . ? 
C5B C4B O1B 120.1(7) . . ? 
C9B C8B C7B 104.5(6) . . ? 
C3B C2B C1B 120.4(7) . . ? 
C8B C9B N1B 107.3(6) . . ? 
C4B C3B C2B 118.8(7) . . ? 
F1B C10B F3B 104.2(5) . . ? 
F1B C10B F2B 108.5(6) . . ? 
F3B C10B F2B 107.4(7) . . ? 
F1B C10B O1B 113.6(7) . . ? 
F3B C10B O1B 113.3(6) . . ? 
F2B C10B O1B 109.5(5) . . ? 
C7A N2A N1A 102.4(4) . . ? 
C9A N1A N2A 112.5(5) . . ? 
C9A N1A C1A 128.0(5) . . ? 
N2A N1A C1A 119.2(4) . . ? 
O2A N3A O3A 123.3(6) . . ? 
O2A N3A C7A 119.1(5) . . ? 
O3A N3A C7A 117.6(5) . . ? 
N2A C7A C8A 114.6(5) . . ? 
N2A C7A N3A 119.5(5) . . ? 
C8A C7A N3A 125.9(5) . . ? 
C1A C6A C5A 120.2(7) . . ? 
C6A C1A C2A 121.0(6) . . ? 
C6A C1A N1A 119.9(5) . . ? 
C2A C1A N1A 119.1(5) . . ? 
C10A O1A C4A 117.9(4) . . ? 
C3A C4A C5A 122.7(6) . . ? 
C3A C4A O1A 117.7(6) . . ? 
C5A C4A O1A 119.4(6) . . ? 
C4A C5A C6A 118.1(7) . . ? 
C9A C8A C7A 103.3(6) . . ? 
F1A C10A O1A 110.5(5) . . ? 
F1A C10A F2A 110.2(7) . . ? 
O1A C10A F2A 114.4(6) . . ? 
F1A C10A F3A 105.7(7) . . ? 
O1A C10A F3A 111.9(6) . . ? 
F2A C10A F3A 103.5(5) . . ? 
C1A C2A C3A 118.6(6) . . ? 
C4A C3A C2A 119.5(6) . . ? 
N1A C9A C8A 107.3(5) . . ? 
 
_diffrn_measured_fraction_theta_max    0.993 
_diffrn_reflns_theta_full              25.06 
_diffrn_measured_fraction_theta_full   0.993 
_refine_diff_density_max    0.185 
_refine_diff_density_min   -0.250 
_refine_diff_density_rms    0.054 
