Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles.
Kurpet, Marta K.; Dąbrowska, Aleksandra; Jarosz, Małgorzata M; Kajewska-Kania, Katarzyna; Kuźnik, Nikodem; Suwiński, Jerzy W; Beilstein journal of organic chemistry 9 (2013) 1517–1525; doi:10.3762/bjoc.9.173

data_4029695
_publ_section_title
;
 Coupling of C-nitro-NH-azoles with arylboronic acids. A route to
 N-aryl-C-nitroazoles.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1517
_journal_page_last               1525
_journal_paper_doi               10.3762/bjoc.9.173
_journal_volume                  9
_journal_year                    2013
_chemical_formula_sum            'C10 H6 F3 N3 O3'
_chemical_formula_weight         273.18
_chemical_melting_point          57.2(8)
_chemical_name_systematic
; 
3-nitro-1-(4-(trifluoromethoxy)phenyl)-1H-pyrazole
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.2681(9)
_cell_length_b                   10.435(2)
_cell_length_c                   24.586(5)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.6
_cell_measurement_theta_min      3.3
_cell_volume                     1095.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'KM4 four-circle diffractometer'
_diffrn_measurement_method       \w/2\q
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2336
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        1.43
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.2(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.101
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1084P)^2^+0.1267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                1454
_reflns_number_total             2042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-9-173-S2.cif
_cod_data_source_block           nkx3-15m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '56.5-58.0' was changed to '57.2(8)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2~1~
_cod_database_code               4029695