#------------------------------------------------------------------------------
#$Date: 2016-05-06 04:33:53 +0300 (Fri, 06 May 2016) $
#$Revision: 182712 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/86/7038684.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_7038684
loop_
_publ_author_name
'Kottelat, E.'
'Ruggi, A.'
'Zobi, F.'
_publ_section_title
;
 Red-light activated photoCORMs of Mn(i) species bearing electron
 deficient 2,2'-azopyridines.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6920
_journal_page_last               6927
_journal_paper_doi               10.1039/c6dt00858e
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C12 H6 F6 N4'
_chemical_formula_sum            'C12 H6 F6 N4'
_chemical_formula_weight         320.21
_chemical_name_systematic
(E)-1,2-bis(4-(trifluoromethyl)pyridin-2-yl)diazene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-10-08 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                113.797(8)
_cell_angle_beta                 93.861(8)
_cell_angle_gamma                100.985(8)
_cell_formula_units_Z            2
_cell_length_a                   4.6634(4)
_cell_length_b                   11.6504(12)
_cell_length_c                   13.1188(14)
_cell_measurement_reflns_used    2161
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.90
_cell_measurement_theta_min      1.96
_cell_volume                     631.90(12)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2009)'
_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8137
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         1.719
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.779
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.779
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0408P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                868
_reflns_number_total             2095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt00858e2.cif
_cod_data_source_block           AR-02
_cod_depositor_comments
'Adding full bibliography for 7038683--7038687.cif.'
_cod_database_code               7038684
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.7338(9) 0.2765(4) 0.0653(4) 0.0560(11) Uani 1 1 d . .
H1 H 0.8524 0.3220 0.0311 0.067 Uiso 1 1 calc R U
C2 C 0.8204(9) 0.3077(4) 0.1764(4) 0.0529(11) Uani 1 1 d . .
H2 H 0.9942 0.3730 0.2177 0.063 Uiso 1 1 calc R U
C3 C 0.6521(8) 0.2431(3) 0.2277(3) 0.0431(9) Uani 1 1 d . .
C4 C 0.4032(8) 0.1471(3) 0.1644(3) 0.0441(9) Uani 1 1 d . .
H4 H 0.2847 0.0989 0.1966 0.053 Uiso 1 1 calc R U
C5 C 0.3336(8) 0.1241(3) 0.0528(3) 0.0429(9) Uani 1 1 d . .
C6 C 0.7373(10) 0.2778(4) 0.3498(3) 0.0580(11) Uani 1 1 d . .
C7 C -0.4644(10) 0.6231(4) 0.3323(3) 0.0650(13) Uani 1 1 d . .
H7 H -0.5413 0.5976 0.3872 0.078 Uiso 1 1 calc R U
C8 C -0.2471(9) 0.7376(4) 0.3700(3) 0.0580(12) Uani 1 1 d . .
H8 H -0.1764 0.7891 0.4482 0.070 Uiso 1 1 calc R U
C9 C -0.1387(9) 0.7732(3) 0.2891(3) 0.0455(10) Uani 1 1 d . .
C10 C -0.2414(8) 0.6962(3) 0.1769(3) 0.0447(10) Uani 1 1 d . .
H10 H -0.1681 0.7192 0.1202 0.054 Uiso 1 1 calc R U
C11 C -0.4555(9) 0.5839(3) 0.1492(3) 0.0460(10) Uani 1 1 d . .
C12 C 0.0868(10) 0.8973(4) 0.3231(3) 0.0591(12) Uani 1 1 d . .
N1 N 0.4917(7) 0.1854(3) 0.0009(3) 0.0509(9) Uani 1 1 d . .
N2 N 0.0780(7) 0.0281(3) -0.0234(2) 0.0489(8) Uani 1 1 d . .
N4 N -0.5802(7) 0.4950(3) 0.0346(2) 0.0472(8) Uani 1 1 d . .
N3 N -0.5714(8) 0.5468(3) 0.2237(3) 0.0576(10) Uani 1 1 d . .
F1 F 1.0216(6) 0.2862(3) 0.3773(2) 0.0934(10) Uani 1 1 d . .
F2 F 0.5886(6) 0.1963(2) 0.38587(18) 0.0749(8) Uani 1 1 d . .
F3 F 0.6890(6) 0.3930(2) 0.41486(19) 0.0853(9) Uani 1 1 d . .
F4 F 0.2701(6) 0.8922(2) 0.2496(2) 0.0821(8) Uani 1 1 d . .
F5 F 0.2543(6) 0.9340(3) 0.4214(2) 0.1031(10) Uani 1 1 d . .
F6 F -0.0354(6) 0.9946(2) 0.3340(2) 0.0917(10) 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'
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
_geom_angle_site_symmetry_1
N1 C1 C2 124.3(3) .
N1 C1 H1 117.9 .
C2 C1 H1 117.9 .
C1 C2 C3 118.9(4) .
C1 C2 H2 120.6 .
C3 C2 H2 120.6 .
C4 C3 C2 119.0(3) .
C4 C3 C6 121.1(3) .
C2 C3 C6 120.0(3) .
C3 C4 C5 117.4(3) .
C3 C4 H4 121.3 .
C5 C4 H4 121.3 .
N1 C5 C4 124.9(3) .
N1 C5 N2 111.3(3) .
C4 C5 N2 123.8(3) .
F1 C6 F2 106.3(4) .
F1 C6 F3 106.1(3) .
F2 C6 F3 105.0(3) .
F1 C6 C3 112.7(3) .
F2 C6 C3 114.6(3) .
F3 C6 C3 111.5(4) .
N3 C7 C8 124.0(4) .
N3 C7 H7 118.0 .
C8 C7 H7 118.0 .
C9 C8 C7 117.1(4) .
C9 C8 H8 121.4 .
C7 C8 H8 121.4 .
C10 C9 C8 120.2(3) .
C10 C9 C12 119.5(3) .
C8 C9 C12 120.3(3) .
C9 C10 C11 117.6(3) .
C9 C10 H10 121.2 .
C11 C10 H10 121.2 .
N3 C11 C10 124.5(3) .
N3 C11 N4 112.6(3) .
C10 C11 N4 122.9(3) .
F5 C12 F4 106.2(4) .
F5 C12 F6 105.6(4) .
F4 C12 F6 106.0(4) .
F5 C12 C9 112.9(4) .
F4 C12 C9 113.1(4) .
F6 C12 C9 112.4(4) .
C1 N1 C5 115.5(3) .
N2 N2 C5 112.8(4) 2
N4 N4 C11 113.2(4) 2_465
C11 N3 C7 116.5(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.344(5) .
C1 C2 1.362(5) .
C1 H1 0.9500 .
C2 C3 1.375(5) .
C2 H2 0.9500 .
C3 C4 1.383(5) .
C3 C6 1.489(5) .
C4 C5 1.381(5) .
C4 H4 0.9500 .
C5 N1 1.333(4) .
C5 N2 1.449(4) .
C6 F1 1.325(5) .
C6 F2 1.328(4) .
C6 F3 1.341(5) .
C7 N3 1.335(5) .
C7 C8 1.392(5) .
C7 H7 0.9500 .
C8 C9 1.379(5) .
C8 H8 0.9500 .
C9 C10 1.369(5) .
C9 C12 1.495(5) .
C10 C11 1.382(4) .
C10 H10 0.9500 .
C11 N3 1.325(4) .
C11 N4 1.438(4) .
C12 F5 1.322(5) .
C12 F4 1.322(5) .
C12 F6 1.325(5) .
N2 N2 1.239(5) 2
N4 N4 1.240(5) 2_465
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_site_symmetry_4
N1 C1 C2 C3 -0.1(6) .
C1 C2 C3 C4 1.1(6) .
C1 C2 C3 C6 -178.4(4) .
C2 C3 C4 C5 -1.7(5) .
C6 C3 C4 C5 177.7(4) .
C3 C4 C5 N1 1.5(6) .
C3 C4 C5 N2 -179.1(3) .
C4 C3 C6 F1 132.6(4) .
C2 C3 C6 F1 -48.0(5) .
C4 C3 C6 F2 10.9(6) .
C2 C3 C6 F2 -169.7(4) .
C4 C3 C6 F3 -108.1(4) .
C2 C3 C6 F3 71.3(5) .
N3 C7 C8 C9 0.2(7) .
C7 C8 C9 C10 -0.9(6) .
C7 C8 C9 C12 177.7(4) .
C8 C9 C10 C11 0.3(6) .
C12 C9 C10 C11 -178.3(4) .
C9 C10 C11 N3 1.2(6) .
C9 C10 C11 N4 -179.8(4) .
C10 C9 C12 F5 -153.2(4) .
C8 C9 C12 F5 28.1(6) .
C10 C9 C12 F4 -32.6(6) .
C8 C9 C12 F4 148.8(4) .
C10 C9 C12 F6 87.5(5) .
C8 C9 C12 F6 -91.2(5) .
C2 C1 N1 C5 -0.2(6) .
C4 C5 N1 C1 -0.6(5) .
N2 C5 N1 C1 -180.0(3) .
N1 C5 N2 N2 -178.1(4) 2
C4 C5 N2 N2 2.5(6) 2
N3 C11 N4 N4 -159.2(4) 2_465
C10 C11 N4 N4 21.7(6) 2_465
C10 C11 N3 C7 -1.9(6) .
N4 C11 N3 C7 179.0(4) .
C8 C7 N3 C11 1.2(6) .
