#------------------------------------------------------------------------------
#$Date: 2016-05-06 04:33:53 +0300 (Fri, 06 May 2016) $
#$Revision: 182712 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/86/7038683.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_7038683
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 H4 Cl2 F6 N4'
_chemical_formula_sum            'C12 H4 Cl2 F6 N4'
_chemical_formula_weight         389.09
_chemical_name_systematic
(E)-1,2-bis(5-chloro-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_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
_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                75.795(8)
_cell_angle_beta                 86.893(8)
_cell_angle_gamma                88.052(8)
_cell_formula_units_Z            1
_cell_length_a                   4.7813(5)
_cell_length_b                   6.6169(7)
_cell_length_c                   11.6910(12)
_cell_measurement_reflns_used    5535
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      1.80
_cell_volume                     357.95(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1694
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4600
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.799
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_description       needle
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0348
_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)+0.0052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1106
_reflns_number_total             1265
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt00858e2.cif
_cod_data_source_block           AR01
_cod_depositor_comments
'Adding full bibliography for 7038683--7038687.cif.'
_cod_database_code               7038683
_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   0.719
_shelx_estimated_absorpt_t_max   0.974
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
Cl1 Cl 0.05487(8) 0.19284(6) 0.84001(4) 0.04375(18) Uani 1 1 d . .
F3 F 0.5150(2) -0.40794(15) 0.85211(11) 0.0526(3) Uani 1 1 d . .
F2 F 0.4291(3) -0.19452(18) 0.96173(10) 0.0548(3) Uani 1 1 d . .
F1 F 0.1017(2) -0.28154(17) 0.86635(12) 0.0554(3) Uani 1 1 d . .
N2 N 0.9288(3) 0.0826(2) 0.49042(13) 0.0367(3) Uani 1 1 d . .
N1 N 0.5914(3) 0.2745(2) 0.56600(14) 0.0405(4) Uani 1 1 d . .
C5 C 0.7200(3) 0.0886(2) 0.58117(15) 0.0334(4) Uani 1 1 d . .
C3 C 0.4454(3) -0.0555(2) 0.75663(15) 0.0322(4) Uani 1 1 d . .
C4 C 0.6498(3) -0.0816(2) 0.67414(15) 0.0331(4) Uani 1 1 d . .
H4 H 0.7419 -0.2131 0.6802 0.040 Uiso 1 1 calc R U
C2 C 0.3127(3) 0.1403(2) 0.74278(16) 0.0350(4) Uani 1 1 d . .
C1 C 0.3942(3) 0.2986(2) 0.64532(17) 0.0392(4) Uani 1 1 d . .
H1 H 0.3028 0.4311 0.6354 0.047 Uiso 1 1 calc R U
C6 C 0.3714(3) -0.2355(3) 0.85993(16) 0.0389(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 0.0016 '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'
Cl Cl 0.1484 0.1585 '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
N2 N2 C5 113.33(16) 2_756
C1 N1 C5 117.80(13) .
N1 C5 C4 123.19(15) .
N1 C5 N2 112.47(13) .
C4 C5 N2 124.31(14) .
C4 C3 C2 118.49(14) .
C4 C3 C6 119.78(14) .
C2 C3 C6 121.73(15) .
C3 C4 C5 118.75(13) .
C1 C2 C3 118.17(16) .
C1 C2 Cl1 118.90(12) .
C3 C2 Cl1 122.93(12) .
N1 C1 C2 123.56(14) .
F2 C6 F1 107.45(15) .
F2 C6 F3 107.43(14) .
F1 C6 F3 106.65(14) .
F2 C6 C3 111.33(15) .
F1 C6 C3 112.50(13) .
F3 C6 C3 111.20(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7163(18) .
F3 C6 1.331(2) .
F2 C6 1.329(2) .
F1 C6 1.329(2) .
N2 N2 1.246(3) 2_756
N2 C5 1.424(2) .
N1 C1 1.320(2) .
N1 C5 1.332(2) .
C5 C4 1.396(2) .
C3 C4 1.372(2) .
C3 C2 1.400(2) .
C3 C6 1.510(2) .
C2 C1 1.393(2) .
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_1
C1 N1 C5 C4 2.1(3) .
C1 N1 C5 N2 -179.68(16) .
N2 N2 C5 N1 172.90(18) 2_756
N2 N2 C5 C4 -8.9(3) 2_756
C2 C3 C4 C5 1.0(3) .
C6 C3 C4 C5 -178.29(16) .
N1 C5 C4 C3 -2.4(3) .
N2 C5 C4 C3 179.62(15) .
C4 C3 C2 C1 0.4(3) .
C6 C3 C2 C1 179.68(17) .
C4 C3 C2 Cl1 -179.84(13) .
C6 C3 C2 Cl1 -0.5(2) .
C5 N1 C1 C2 -0.5(3) .
C3 C2 C1 N1 -0.7(3) .
Cl1 C2 C1 N1 179.54(15) .
C4 C3 C6 F2 116.36(18) .
C2 C3 C6 F2 -62.9(2) .
C4 C3 C6 F1 -122.96(18) .
C2 C3 C6 F1 57.7(2) .
C4 C3 C6 F3 -3.4(2) .
C2 C3 C6 F3 177.29(15) .
