#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029237.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4029237
loop_
_publ_author_name
'Iaroshenko, Viktor O'
'Gevorgyan, Ashot'
'Davydova, Olena'
'Villinger, Alexander'
'Langer, Peter'
_publ_section_title
;
 Regioselective and guided C-h activation of 4-nitropyrazoles.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2906
_journal_page_last               2915
_journal_paper_doi               10.1021/jo4025418
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C17 H11 F3 N4 O4'
_chemical_formula_sum            'C17 H11 F3 N4 O4'
_chemical_formula_weight         392.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.7090(10)
_cell_angle_beta                 95.9810(10)
_cell_angle_gamma                106.2500(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7337(2)
_cell_length_b                   9.7692(2)
_cell_length_c                   11.6204(3)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      63.888
_cell_measurement_theta_min      4.439
_cell_volume                     820.10(3)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27547
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_correction_T_min  0.9293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.2994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                4327
_reflns_number_total             5917
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo4025418_si_002.cif
_cod_data_source_block           is_ag506ff
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029237.cif.
;
_cod_database_code               4029237
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.15188(15) 0.79293(12) 0.64624(9) 0.0277(2) Uani 1 1 d .
N2 N 0.14431(15) 0.70254(12) 0.72368(9) 0.0262(2) Uani 1 1 d .
N3 N 0.27413(13) 0.49020(11) 0.48839(9) 0.0229(2) Uani 1 1 d .
N4 N 0.55541(17) 0.34257(13) 0.90683(10) 0.0319(2) Uani 1 1 d .
O1 O 0.26153(13) 0.50018(10) 0.38380(8) 0.0303(2) Uani 1 1 d .
O2 O 0.31289(15) 0.38934(11) 0.52433(9) 0.0354(2) Uani 1 1 d .
O3 O 0.69295(14) 0.42515(14) 0.88525(10) 0.0445(3) Uani 1 1 d .
O4 O 0.55676(19) 0.24576(15) 0.96105(12) 0.0550(3) Uani 1 1 d .
F1 F 0.35919(19) 1.21596(10) 0.23968(10) 0.0654(3) Uani 1 1 d .
F2 F 0.20623(15) 1.03102(11) 0.10744(9) 0.0552(3) Uani 1 1 d .
F3 F 0.49492(15) 1.07641(13) 0.15203(10) 0.0597(3) Uani 1 1 d .
C1 C 0.20910(16) 0.73161(13) 0.55222(10) 0.0235(2) Uani 1 1 d .
C2 C 0.23749(15) 0.59989(13) 0.57168(10) 0.0215(2) Uani 1 1 d .
C3 C 0.19694(15) 0.58539(13) 0.68414(10) 0.0224(2) Uani 1 1 d .
C4 C 0.20699(15) 0.47781(13) 0.75763(10) 0.0223(2) Uani 1 1 d .
C5 C 0.37432(15) 0.45672(13) 0.79165(10) 0.0220(2) Uani 1 1 d .
H5 H 0.4814 0.5060 0.7643 0.026 Uiso 1 1 calc R
C6 C 0.37884(17) 0.36136(14) 0.86684(10) 0.0246(2) Uani 1 1 d .
C7 C 0.22565(19) 0.28575(15) 0.90818(11) 0.0308(3) Uani 1 1 d .
H7 H 0.2335 0.2198 0.9586 0.037 Uiso 1 1 calc R
C8 C 0.06149(19) 0.30915(16) 0.87393(12) 0.0335(3) Uani 1 1 d .
H8 H -0.0451 0.2600 0.9019 0.040 Uiso 1 1 calc R
C9 C 0.05179(17) 0.40404(15) 0.79896(11) 0.0289(3) Uani 1 1 d .
H9 H -0.0618 0.4190 0.7755 0.035 Uiso 1 1 calc R
C10 C 0.0856(2) 0.74323(18) 0.83629(12) 0.0367(3) Uani 1 1 d .
H10A H -0.0464 0.6986 0.8291 0.055 Uiso 1 1 calc R
H10B H 0.1151 0.8495 0.8577 0.055 Uiso 1 1 calc R
H10C H 0.1487 0.7089 0.8978 0.055 Uiso 1 1 calc R
C11 C 0.24339(17) 0.81299(13) 0.45662(10) 0.0246(2) Uani 1 1 d .
C12 C 0.39898(18) 0.82468(14) 0.40374(11) 0.0264(2) Uani 1 1 d .
H12 H 0.4812 0.7733 0.4246 0.032 Uiso 1 1 calc R
C13 C 0.43402(19) 0.91164(14) 0.32038(11) 0.0281(2) Uani 1 1 d .
H13 H 0.5401 0.9199 0.2842 0.034 Uiso 1 1 calc R
C14 C 0.31294(19) 0.98637(14) 0.29038(11) 0.0294(3) Uani 1 1 d .
C15 C 0.1589(2) 0.97701(15) 0.34389(12) 0.0338(3) Uani 1 1 d .
H15 H 0.0781 1.0299 0.3240 0.041 Uiso 1 1 calc R
C16 C 0.1239(2) 0.88989(15) 0.42657(12) 0.0309(3) Uani 1 1 d .
H16 H 0.0182 0.8825 0.4630 0.037 Uiso 1 1 calc R
C17 C 0.3449(2) 1.07686(16) 0.19820(13) 0.0366(3) Uani 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 N2 106.06(10)
C3 N2 N1 113.20(9)
C3 N2 C10 128.68(11)
N1 N2 C10 118.11(10)
O2 N3 O1 123.43(10)
O2 N3 C2 118.43(10)
O1 N3 C2 118.12(9)
O3 N4 O4 123.60(12)
O3 N4 C6 118.27(11)
O4 N4 C6 118.13(12)
N1 C1 C2 109.11(10)
N1 C1 C11 117.77(10)
C2 C1 C11 132.93(10)
C3 C2 C1 106.82(10)
C3 C2 N3 124.91(10)
C1 C2 N3 127.70(10)
N2 C3 C2 104.79(10)
N2 C3 C4 121.54(10)
C2 C3 C4 133.64(11)
C9 C4 C5 120.07(11)
C9 C4 C3 120.03(10)
C5 C4 C3 119.78(10)
C6 C5 C4 117.61(10)
C6 C5 H5 121.2
C4 C5 H5 121.2
C5 C6 C7 123.27(11)
C5 C6 N4 118.09(11)
C7 C6 N4 118.63(11)
C8 C7 C6 118.09(12)
C8 C7 H7 121.0
C6 C7 H7 121.0
C7 C8 C9 120.26(12)
C7 C8 H8 119.9
C9 C8 H8 119.9
C8 C9 C4 120.69(11)
C8 C9 H9 119.7
C4 C9 H9 119.7
N2 C10 H10A 109.5
N2 C10 H10B 109.5
H10A C10 H10B 109.5
N2 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C16 119.77(11)
C12 C11 C1 121.58(10)
C16 C11 C1 118.41(11)
C13 C12 C11 120.00(11)
C13 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C12 119.62(12)
C14 C13 H13 120.2
C12 C13 H13 120.2
C15 C14 C13 120.76(11)
C15 C14 C17 118.72(12)
C13 C14 C17 120.51(13)
C16 C15 C14 119.51(12)
C16 C15 H15 120.2
C14 C15 H15 120.2
C15 C16 C11 120.32(12)
C15 C16 H16 119.8
C11 C16 H16 119.8
F3 C17 F1 106.62(13)
F3 C17 F2 106.50(13)
F1 C17 F2 105.23(13)
F3 C17 C14 113.51(12)
F1 C17 C14 112.52(12)
F2 C17 C14 111.89(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3330(15)
N1 N2 1.3575(14)
N2 C3 1.3450(15)
N2 C10 1.4580(16)
N3 O2 1.2302(13)
N3 O1 1.2315(13)
N3 C2 1.4293(15)
N4 O3 1.2201(17)
N4 O4 1.2235(16)
N4 C6 1.4667(16)
F1 C17 1.3324(18)
F2 C17 1.3413(18)
F3 C17 1.3287(19)
C1 C2 1.4145(16)
C1 C11 1.4757(16)
C2 C3 1.3961(15)
C3 C4 1.4747(16)
C4 C9 1.3941(16)
C4 C5 1.3941(16)
C5 C6 1.3852(16)
C5 H5 0.9500
C6 C7 1.3887(18)
C7 C8 1.382(2)
C7 H7 0.9500
C8 C9 1.3862(18)
C8 H8 0.9500
C9 H9 0.9500
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.3926(17)
C11 C16 1.3962(17)
C12 C13 1.3917(17)
C12 H12 0.9500
C13 C14 1.3899(18)
C13 H13 0.9500
C14 C15 1.388(2)
C14 C17 1.4974(18)
C15 C16 1.3862(18)
C15 H15 0.9500
C16 H16 0.9500
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
C1 N1 N2 C3 0.84(14)
C1 N1 N2 C10 179.82(12)
N2 N1 C1 C2 0.08(14)
N2 N1 C1 C11 -175.48(11)
N1 C1 C2 C3 -0.92(14)
C11 C1 C2 C3 173.73(13)
N1 C1 C2 N3 170.63(11)
C11 C1 C2 N3 -14.7(2)
O2 N3 C2 C3 -16.94(17)
O1 N3 C2 C3 161.60(11)
O2 N3 C2 C1 172.94(12)
O1 N3 C2 C1 -8.51(18)
N1 N2 C3 C2 -1.39(14)
C10 N2 C3 C2 179.76(13)
N1 N2 C3 C4 176.98(10)
C10 N2 C3 C4 -1.9(2)
C1 C2 C3 N2 1.35(13)
N3 C2 C3 N2 -170.49(11)
C1 C2 C3 C4 -176.73(13)
N3 C2 C3 C4 11.4(2)
N2 C3 C4 C9 58.71(17)
C2 C3 C4 C9 -123.47(15)
N2 C3 C4 C5 -117.35(13)
C2 C3 C4 C5 60.48(19)
C9 C4 C5 C6 -0.09(18)
C3 C4 C5 C6 175.97(11)
C4 C5 C6 C7 0.71(19)
C4 C5 C6 N4 -177.71(11)
O3 N4 C6 C5 9.55(18)
O4 N4 C6 C5 -171.15(12)
O3 N4 C6 C7 -168.94(12)
O4 N4 C6 C7 10.35(18)
C5 C6 C7 C8 -1.1(2)
N4 C6 C7 C8 177.26(12)
C6 C7 C8 C9 1.0(2)
C7 C8 C9 C4 -0.4(2)
C5 C4 C9 C8 -0.1(2)
C3 C4 C9 C8 -176.10(12)
N1 C1 C11 C12 135.29(13)
C2 C1 C11 C12 -39.0(2)
N1 C1 C11 C16 -39.12(18)
C2 C1 C11 C16 146.60(14)
C16 C11 C12 C13 -0.64(19)
C1 C11 C12 C13 -174.98(12)
C11 C12 C13 C14 -0.03(19)
C12 C13 C14 C15 1.0(2)
C12 C13 C14 C17 -178.10(12)
C13 C14 C15 C16 -1.2(2)
C17 C14 C15 C16 177.87(13)
C14 C15 C16 C11 0.5(2)
C12 C11 C16 C15 0.4(2)
C1 C11 C16 C15 174.91(13)
C15 C14 C17 F3 -179.19(13)
C13 C14 C17 F3 -0.10(19)
C15 C14 C17 F1 59.61(19)
C13 C14 C17 F1 -121.30(15)
C15 C14 C17 F2 -58.62(18)
C13 C14 C17 F2 120.47(15)
