#------------------------------------------------------------------------------
#$Date: 2020-04-05 12:59:57 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250157 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/59/7125960.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_7125960
loop_
_publ_author_name
'Wang, Wenqing'
'Tan, Gengwen'
'Feng, Rui'
'Fang, Yong'
'Chen, Chao'
'Ruan, Huapeng'
'Zhao, Yue'
'Wang, Xinping'
_publ_section_title
;
 Stable, yet "naked", azo radical anion ArNNAr⁻ and
 dianion ArNNAr²⁻ (Ar =
 4-CN-2,6-ⁱPr₂-C₆H₂) with
 selective CO₂ activation.
;
_journal_issue                   22
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3285
_journal_page_last               3288
_journal_paper_doi               10.1039/c9cc07382e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C26 H32 N4'
_chemical_formula_weight         400.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-11-08 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.844(8)
_cell_length_b                   9.534(5)
_cell_length_c                   16.867(8)
_cell_measurement_reflns_used    1880
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      24.60
_cell_measurement_theta_min      2.41
_cell_volume                     2387(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'd8 advance'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1197
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11676
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.415
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0712
_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)+(0.0644P)²+2.1417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1261
_reflns_number_total             2109
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc07382e2.cif
_cod_data_source_block           2_a
_cod_depositor_comments
'Adding full bibliography for 7125960--7125964.cif.'
_cod_database_code               7125960
_shelx_shelxl_version_number     2018/3
_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   0.980
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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 0.4308(2) 0.4735(3) 0.33719(19) 0.0262(8) Uani 1 1 d . .
C2 C 0.4325(2) 0.3862(3) 0.4052(2) 0.0263(8) Uani 1 1 d . .
C3 C 0.3651(2) 0.4039(3) 0.46184(19) 0.0271(8) Uani 1 1 d . .
H3 H 0.363614 0.345290 0.507374 0.032 Uiso 1 1 calc R U
C4 C 0.2999(2) 0.5076(3) 0.45166(19) 0.0257(8) Uani 1 1 d . .
C5 C 0.2999(2) 0.5938(3) 0.38492(18) 0.0275(8) Uani 1 1 d . .
H5 H 0.254798 0.663830 0.379436 0.033 Uiso 1 1 calc R U
C6 C 0.3653(2) 0.5788(3) 0.32601(19) 0.0269(8) Uani 1 1 d . .
C7 C 0.2329(2) 0.5315(3) 0.5129(2) 0.0273(8) Uani 1 1 d . .
C8 C 0.3632(2) 0.6829(3) 0.2569(2) 0.0321(9) Uani 1 1 d . .
H8 H 0.418083 0.665917 0.223952 0.039 Uiso 1 1 calc R U
C9 C 0.3667(3) 0.8342(3) 0.2853(2) 0.0522(12) Uani 1 1 d . .
H9A H 0.419884 0.847617 0.318834 0.078 Uiso 1 1 calc R U
H9B H 0.370161 0.897022 0.239418 0.078 Uiso 1 1 calc R U
H9C H 0.312241 0.855378 0.315899 0.078 Uiso 1 1 calc R U
C10 C 0.2819(4) 0.6576(5) 0.2048(3) 0.0849(19) Uani 1 1 d . .
H10A H 0.281338 0.559521 0.187454 0.127 Uiso 1 1 calc R U
H10B H 0.226882 0.677584 0.234903 0.127 Uiso 1 1 calc R U
H10C H 0.284802 0.719228 0.158422 0.127 Uiso 1 1 calc R U
C11 C 0.5049(2) 0.2738(3) 0.41432(19) 0.0298(8) Uani 1 1 d . .
H11 H 0.561750 0.310447 0.390272 0.036 Uiso 1 1 calc R U
C12 C 0.4768(2) 0.1411(3) 0.3678(2) 0.0373(9) Uani 1 1 d . .
H12A H 0.523310 0.068963 0.373698 0.056 Uiso 1 1 calc R U
H12B H 0.419513 0.105768 0.388689 0.056 Uiso 1 1 calc R U
H12C H 0.469729 0.164588 0.311597 0.056 Uiso 1 1 calc R U
C13 C 0.5245(2) 0.2360(3) 0.5008(2) 0.0333(9) Uani 1 1 d . .
H13A H 0.571276 0.163596 0.502773 0.050 Uiso 1 1 calc R U
H13B H 0.545285 0.319684 0.529121 0.050 Uiso 1 1 calc R U
H13C H 0.469428 0.200557 0.525828 0.050 Uiso 1 1 calc R U
N1 N 0.50905(19) 0.4610(2) 0.28619(14) 0.0299(7) Uani 1 1 d . .
N2 N 0.1800(2) 0.5540(3) 0.56125(17) 0.0367(8) 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'
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
C6 C1 C2 122.5(3) .
C6 C1 N1 122.1(3) .
C2 C1 N1 114.7(3) .
C3 C2 C1 118.1(3) .
C3 C2 C11 121.4(3) .
C1 C2 C11 120.4(3) .
C2 C3 C4 120.0(3) .
C2 C3 H3 120.0 .
C4 C3 H3 120.0 .
C5 C4 C3 121.1(3) .
C5 C4 C7 118.8(3) .
C3 C4 C7 120.0(3) .
C4 C5 C6 121.0(3) .
C4 C5 H5 119.5 .
C6 C5 H5 119.5 .
C5 C6 C1 117.2(3) .
C5 C6 C8 117.4(3) .
C1 C6 C8 125.3(3) .
N2 C7 C4 178.3(3) .
C10 C8 C9 111.2(3) .
C10 C8 C6 110.8(3) .
C9 C8 C6 112.0(3) .
C10 C8 H8 107.5 .
C9 C8 H8 107.5 .
C6 C8 H8 107.5 .
C8 C9 H9A 109.5 .
C8 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C8 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C8 C10 H10A 109.5 .
C8 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C8 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C2 C11 C13 113.3(3) .
C2 C11 C12 109.5(3) .
C13 C11 C12 110.0(3) .
C2 C11 H11 107.9 .
C13 C11 H11 107.9 .
C12 C11 H11 107.9 .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C11 C13 H13A 109.5 .
C11 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C11 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
N1 N1 C1 114.0(4) 3_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.411(4) .
C1 C2 1.418(4) .
C1 N1 1.450(4) .
C2 C3 1.393(4) .
C2 C11 1.525(4) .
C3 C4 1.395(4) .
C3 H3 0.9500 .
C4 C5 1.394(4) .
C4 C7 1.453(5) .
C5 C6 1.396(4) .
C5 H5 0.9500 .
C6 C8 1.531(4) .
C7 N2 1.151(4) .
C8 C10 1.512(5) .
C8 C9 1.520(4) .
C8 H8 1.0000 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C13 1.530(4) .
C11 C12 1.545(4) .
C11 H11 1.0000 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
N1 N1 1.250(5) 3_655
