#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:47:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180096 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/42/7054253.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_7054253
loop_
_publ_author_name
'Muñoz, Bianca K.'
'Ojo, Wilfried-Solo'
'Jacob, Kane'
'Romero, Nuria'
'Vendier, Laure'
'Despagnet-Ayoub, Emmanuelle'
'Etienne, Michel'
_publ_section_title
;
 Perfluorinated 1H-indazoles and hydrotris(indazol-1-yl)borates.
 Supramolecular organization and a new synthetic procedure to form
 scorpionate ligands
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2451
_journal_paper_doi               10.1039/c4nj00136b
_journal_volume                  38
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H F11 N2'
_chemical_formula_sum            'C10 H F11 N2'
_chemical_formula_weight         358.13
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1335(3)
_cell_length_b                   9.1624(5)
_cell_length_c                   24.8250(15)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.36
_cell_measurement_theta_min      2.76
_cell_measurement_wavelength     0.71073
_cell_volume                     1167.65(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            26389
_diffrn_reflns_theta_full        33.04
_diffrn_reflns_theta_max         33.04
_diffrn_reflns_theta_min         3.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0553P)²+0.2036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                2121
_reflns_number_total             2432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj00136b1.cif
_cod_data_source_block           3
_cod_database_code               7054253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
C3 C 0.1879(3) 0.61736(19) 0.09062(6) 0.0190(3) Uani 1 1 d
C3A C 0.0397(3) 0.48733(18) 0.09405(6) 0.0178(3) Uani 1 1 d
C4 C 0.0207(4) 0.36625(19) 0.12846(6) 0.0226(3) Uani 1 1 d
C5 C -0.1633(4) 0.2626(2) 0.11816(7) 0.0273(4) Uani 1 1 d
C6 C -0.3345(4) 0.2755(2) 0.07424(8) 0.0271(4) Uani 1 1 d
C7 C -0.3189(4) 0.3912(2) 0.03969(7) 0.0240(3) Uani 1 1 d
C7A C -0.1282(3) 0.49606(19) 0.04940(6) 0.0193(3) Uani 1 1 d
C8 C 0.3791(4) 0.6804(2) 0.12956(6) 0.0211(3) Uani 1 1 d
C9 C 0.2408(4) 0.7638(2) 0.17568(7) 0.0224(3) Uani 1 1 d
C10 C 0.4131(4) 0.8200(2) 0.22198(7) 0.0287(4) Uani 1 1 d
N1 N -0.0701(3) 0.62094(17) 0.02298(6) 0.0225(3) Uani 1 1 d
H1 H -0.153(5) 0.660(3) -0.0025(9) 0.027 Uiso 1 1 d
N2 N 0.1194(3) 0.69622(17) 0.04806(5) 0.0217(3) Uani 1 1 d
F4 F 0.1801(3) 0.35088(14) 0.17024(5) 0.0340(3) Uani 1 1 d
F5 F -0.1865(3) 0.14584(13) 0.14966(6) 0.0432(4) Uani 1 1 d
F6 F -0.5129(3) 0.17152(15) 0.06662(6) 0.0431(4) Uani 1 1 d
F7 F -0.4821(3) 0.40479(15) -0.00199(5) 0.0359(3) Uani 1 1 d
F8 F 0.5410(2) 0.77454(14) 0.10416(4) 0.0329(3) Uani 1 1 d
F9 F 0.5261(2) 0.57401(13) 0.15185(4) 0.0285(2) Uani 1 1 d
F10 F 0.1192(3) 0.87931(16) 0.15384(6) 0.0414(3) Uani 1 1 d
F11 F 0.0633(2) 0.67451(15) 0.19719(5) 0.0342(3) Uani 1 1 d
F12 F 0.2675(3) 0.89501(17) 0.25614(5) 0.0457(4) Uani 1 1 d
F13 F 0.5998(3) 0.90559(16) 0.20384(6) 0.0441(4) Uani 1 1 d
F14 F 0.5208(4) 0.71035(16) 0.24818(5) 0.0443(4) 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0 '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
N2 C3 C3A 111.31(15)
N2 C3 C8 118.59(15)
C3A C3 C8 129.76(14)
C4 C3A C7A 118.82(16)
C4 C3A C3 137.63(16)
C7A C3A C3 103.54(14)
F4 C4 C5 119.95(15)
F4 C4 C3A 121.07(17)
C5 C4 C3A 118.98(16)
F5 C5 C4 120.79(18)
F5 C5 C6 117.90(18)
C4 C5 C6 121.31(16)
F6 C6 C7 120.33(18)
F6 C6 C5 118.59(17)
C7 C6 C5 121.08(17)
F7 C7 C6 121.46(18)
F7 C7 C7A 120.65(16)
C6 C7 C7A 117.89(16)
N1 C7A C7 130.91(16)
N1 C7A C3A 107.18(15)
C7 C7A C3A 121.86(15)
F9 C8 F8 107.89(15)
F9 C8 C3 110.66(14)
F8 C8 C3 110.40(13)
F9 C8 C9 108.01(13)
F8 C8 C9 108.15(15)
C3 C8 C9 111.61(15)
F11 C9 F10 109.09(17)
F11 C9 C10 107.34(14)
F10 C9 C10 107.77(15)
F11 C9 C8 107.81(15)
F10 C9 C8 107.66(14)
C10 C9 C8 117.00(16)
F13 C10 F14 108.5(2)
F13 C10 F12 108.69(17)
F14 C10 F12 108.46(17)
F13 C10 C9 111.22(15)
F14 C10 C9 110.78(16)
F12 C10 C9 109.15(18)
N2 N1 C7A 111.64(14)
N2 N1 H1 119.5(17)
C7A N1 H1 127.9(18)
C3 N2 N1 106.31(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 N2 1.327(2)
C3 C3A 1.416(2)
C3 C8 1.494(2)
C3A C4 1.404(2)
C3A C7A 1.406(2)
C4 F4 1.329(2)
C4 C5 1.364(3)
C5 F5 1.330(2)
C5 C6 1.406(3)
C6 F6 1.335(2)
C6 C7 1.365(3)
C7 F7 1.337(2)
C7 C7A 1.393(2)
C7A N1 1.352(2)
C8 F9 1.351(2)
C8 F8 1.354(2)
C8 C9 1.549(2)
C9 F11 1.336(2)
C9 F10 1.343(2)
C9 C10 1.539(3)
C10 F13 1.318(2)
C10 F14 1.318(3)
C10 F12 1.323(2)
N1 N2 1.345(2)
N1 H1 0.84(2)
