#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:29:53 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/02/1560276.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_1560276
loop_
_publ_author_name
'Panetti, Grace B.'
'Carroll, Patrick J.'
'Gau, Michael R.'
'Manor, Brian C.'
'Schelter, Eric J.'
'Walsh, Patrick J.'
_publ_section_title
;
 Synthesis of an elusive, stable 2-azaallyl radical guided by
 electrochemical and reactivity studies of 2-azaallyl anions
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4405
_journal_page_last               4410
_journal_paper_doi               10.1039/D0SC04822D
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C12 H30 Na O6, C20 H16 N'
_chemical_formula_sum            'C32 H46 N Na O6'
_chemical_formula_weight         563.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-03-25 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                104.751(2)
_cell_angle_beta                 95.937(2)
_cell_angle_gamma                99.774(2)
_cell_formula_units_Z            2
_cell_length_a                   11.6153(5)
_cell_length_b                   11.6198(5)
_cell_length_c                   12.6450(6)
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.569
_cell_measurement_theta_min      2.712
_cell_volume                     1607.08(13)
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            40235
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.611
_diffrn_reflns_theta_min         1.685
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         7277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0471
_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)+(0.0583P)²+0.8412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                6191
_reflns_number_total             7277
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04822d3.cif
_cod_data_source_block           6233
_cod_depositor_comments
'Adding full bibliography for 1560274--1560278.cif.'
_cod_database_code               1560276
_shelx_shelxl_version_number     2017/1
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.23172(5) 0.19116(5) 0.81196(4) 0.02196(13) Uani 1 1 d . . . . .
O1 O 0.09849(9) 0.00023(9) 0.76168(9) 0.0299(2) Uani 1 1 d . . . . .
O2 O 0.31691(10) 0.04913(9) 0.68730(8) 0.0283(2) Uani 1 1 d . . . . .
O3 O 0.33923(10) 0.35204(10) 0.75995(10) 0.0344(3) Uani 1 1 d . . . . .
O4 O 0.09976(11) 0.25284(10) 0.68709(10) 0.0381(3) Uani 1 1 d . . . . .
O5 O 0.17756(9) 0.32317(9) 0.96649(8) 0.0240(2) Uani 1 1 d . . . . .
O6 O 0.32023(9) 0.15764(9) 0.97649(8) 0.0240(2) Uani 1 1 d . . . . .
N1 N 0.31629(11) 0.69755(10) 0.71904(10) 0.0227(2) Uani 1 1 d . . . . .
C1 C 0.37006(13) 0.73090(12) 0.82296(11) 0.0231(3) Uani 1 1 d . . . . .
H1 H 0.453961 0.751231 0.838144 0.028 Uiso 1 1 calc R . . . .
C2 C 0.30333(13) 0.73674(12) 0.91291(12) 0.0240(3) Uani 1 1 d . . . . .
C3 C 0.36202(15) 0.76736(13) 1.02338(12) 0.0285(3) Uani 1 1 d . . . . .
H3 H 0.445832 0.780280 1.037093 0.034 Uiso 1 1 calc R . . . .
C4 C 0.29930(17) 0.77881(14) 1.11179(13) 0.0352(4) Uani 1 1 d . . . . .
H4 H 0.340678 0.799644 1.185076 0.042 Uiso 1 1 calc R . . . .
C5 C 0.17680(17) 0.76017(15) 1.09443(14) 0.0384(4) Uani 1 1 d . . . . .
H5 H 0.134246 0.768975 1.155276 0.046 Uiso 1 1 calc R . . . .
C6 C 0.11727(15) 0.72839(14) 0.98662(14) 0.0336(4) Uani 1 1 d . . . . .
H6 H 0.033404 0.715163 0.974047 0.040 Uiso 1 1 calc R . . . .
C7 C 0.17853(13) 0.71575(13) 0.89726(13) 0.0270(3) Uani 1 1 d . . . . .
H7 H 0.135889 0.692588 0.824312 0.032 Uiso 1 1 calc R . . . .
C8 C 0.37205(12) 0.69208(12) 0.63113(11) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.30144(12) 0.64658(12) 0.52250(11) 0.0220(3) Uani 1 1 d . . . . .
C10 C 0.17906(13) 0.59575(13) 0.50908(12) 0.0263(3) Uani 1 1 d . . . . .
H10 H 0.143950 0.590768 0.572795 0.032 Uiso 1 1 calc R . . . .
C11 C 0.10934(14) 0.55330(14) 0.40641(13) 0.0303(3) Uani 1 1 d . . . . .
H11 H 0.027775 0.519483 0.400800 0.036 Uiso 1 1 calc R . . . .
C12 C 0.15724(14) 0.55946(15) 0.31072(13) 0.0314(3) Uani 1 1 d . . . . .
H12 H 0.109263 0.530512 0.240050 0.038 Uiso 1 1 calc R . . . .
C13 C 0.27690(14) 0.60902(14) 0.32145(12) 0.0291(3) Uani 1 1 d . . . . .
H13 H 0.310700 0.614083 0.257097 0.035 Uiso 1 1 calc R . . . .
C14 C 0.34800(13) 0.65123(13) 0.42397(12) 0.0250(3) Uani 1 1 d . . . . .
H14 H 0.429616 0.683953 0.428340 0.030 Uiso 1 1 calc R . . . .
C15 C 0.50266(12) 0.73496(12) 0.64244(11) 0.0221(3) Uani 1 1 d . . . . .
C16 C 0.55449(13) 0.85856(13) 0.68261(11) 0.0251(3) Uani 1 1 d . . . . .
H16 H 0.506210 0.915478 0.706553 0.030 Uiso 1 1 calc R . . . .
C17 C 0.67510(14) 0.90000(14) 0.68829(12) 0.0302(3) Uani 1 1 d . . . . .
H17 H 0.708408 0.984490 0.714764 0.036 Uiso 1 1 calc R . . . .
C18 C 0.74674(14) 0.81725(16) 0.65506(12) 0.0315(3) Uani 1 1 d . . . . .
H18 H 0.828802 0.845266 0.656581 0.038 Uiso 1 1 calc R . . . .
C19 C 0.69825(14) 0.69367(15) 0.61965(12) 0.0305(3) Uani 1 1 d . . . . .
H19 H 0.747573 0.636761 0.599752 0.037 Uiso 1 1 calc R . . . .
C20 C 0.57732(13) 0.65331(13) 0.61336(12) 0.0263(3) Uani 1 1 d . . . . .
H20 H 0.544778 0.568571 0.588817 0.032 Uiso 1 1 calc R . . . .
C21 C 0.15539(15) -0.09441(13) 0.71011(14) 0.0323(3) Uani 1 1 d . . . . .
H21a H 0.095480 -0.168698 0.671244 0.039 Uiso 1 1 calc R . . . .
H21b H 0.208196 -0.113915 0.766776 0.039 Uiso 1 1 calc R . . . .
C22 C 0.22584(15) -0.05228(14) 0.62907(12) 0.0322(3) Uani 1 1 d . . . . .
H22a H 0.260986 -0.118990 0.588384 0.039 Uiso 1 1 calc R . . . .
H22b H 0.173595 -0.028830 0.574719 0.039 Uiso 1 1 calc R . . . .
C23 C 0.03509(14) -0.02991(16) 0.84496(15) 0.0364(4) Uani 1 1 d . . . . .
H23a H -0.022626 -0.106256 0.812603 0.055 Uiso 1 1 calc GR . . . .
H23b H -0.006205 0.035165 0.874953 0.055 Uiso 1 1 calc GR . . . .
H23c H 0.090552 -0.039341 0.904556 0.055 Uiso 1 1 calc GR . . . .
C24 C 0.39303(17) 0.08803(17) 0.61558(15) 0.0395(4) Uani 1 1 d . . . . .
H24a H 0.428416 0.020608 0.579050 0.059 Uiso 1 1 calc GR . . . .
H24b H 0.455708 0.156303 0.659011 0.059 Uiso 1 1 calc GR . . . .
H24c H 0.347083 0.113807 0.559566 0.059 Uiso 1 1 calc GR . . . .
C25 C 0.26962(18) 0.40241(15) 0.68989(15) 0.0415(4) Uani 1 1 d . . . . .
H25a H 0.319623 0.435621 0.641411 0.050 Uiso 1 1 calc R . . . .
H25b H 0.239477 0.469904 0.735984 0.050 Uiso 1 1 calc R . . . .
C26 C 0.16936(17) 0.30863(18) 0.62132(15) 0.0410(4) Uani 1 1 d . . . . .
H26a H 0.119500 0.346257 0.577276 0.049 Uiso 1 1 calc R . . . .
H26b H 0.199787 0.246007 0.569193 0.049 Uiso 1 1 calc R . . . .
C27 C 0.44239(15) 0.43543(16) 0.82168(16) 0.0404(4) Uani 1 1 d . . . . .
H27a H 0.492104 0.462191 0.770873 0.061 Uiso 1 1 calc GR . . . .
H27b H 0.486521 0.395781 0.867192 0.061 Uiso 1 1 calc GR . . . .
H27c H 0.419827 0.505940 0.869627 0.061 Uiso 1 1 calc GR . . . .
C28 C -0.00377(16) 0.17340(16) 0.62399(15) 0.0414(4) Uani 1 1 d . . . . .
H28a H -0.054537 0.219943 0.593149 0.062 Uiso 1 1 calc GR . . . .
H28b H -0.046170 0.131961 0.671348 0.062 Uiso 1 1 calc GR . . . .
H28c H 0.017379 0.113039 0.563573 0.062 Uiso 1 1 calc GR . . . .
C29 C 0.25861(13) 0.33825(13) 1.06384(12) 0.0271(3) Uani 1 1 d . . . . .
H29a H 0.227619 0.380399 1.129855 0.032 Uiso 1 1 calc R . . . .
H29b H 0.335469 0.388189 1.060464 0.032 Uiso 1 1 calc R . . . .
C30 C 0.27483(13) 0.21561(14) 1.07197(11) 0.0260(3) Uani 1 1 d . . . . .
H30a H 0.330570 0.224161 1.139572 0.031 Uiso 1 1 calc R . . . .
H30b H 0.198187 0.166043 1.076409 0.031 Uiso 1 1 calc R . . . .
C31 C 0.15196(15) 0.43663(13) 0.95771(13) 0.0312(3) Uani 1 1 d . . . . .
H31a H 0.115026 0.472423 1.021045 0.047 Uiso 1 1 calc GR . . . .
H31b H 0.097798 0.423356 0.888982 0.047 Uiso 1 1 calc GR . . . .
H31c H 0.225472 0.491978 0.957072 0.047 Uiso 1 1 calc GR . . . .
C32 C 0.34986(14) 0.04567(13) 0.98572(13) 0.0290(3) Uani 1 1 d . . . . .
H32a H 0.412903 0.062137 1.048657 0.043 Uiso 1 1 calc GR . . . .
H32b H 0.377022 0.005521 0.917617 0.043 Uiso 1 1 calc GR . . . .
H32c H 0.279961 -0.007375 0.997226 0.043 Uiso 1 1 calc GR . . . .
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'
Na Na 0.0362 0.0249 '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'
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Na1 O2 72.32(4) . . ?
O1 Na1 O4 87.32(4) . . ?
O1 Na1 O6 92.56(4) . . ?
O2 Na1 O4 102.25(4) . . ?
O3 Na1 O1 149.51(5) . . ?
O3 Na1 O2 90.33(4) . . ?
O3 Na1 O4 71.73(4) . . ?
O3 Na1 O5 93.07(4) . . ?
O3 Na1 O6 114.53(4) . . ?
O5 Na1 O1 109.54(4) . . ?
O5 Na1 O2 166.94(4) . . ?
O5 Na1 O4 90.79(4) . . ?
O5 Na1 O6 71.14(4) . . ?
O6 Na1 O2 95.98(4) . . ?
O6 Na1 O4 160.79(5) . . ?
C21 O1 Na1 110.44(9) . . ?
C23 O1 Na1 116.98(10) . . ?
C23 O1 C21 112.24(12) . . ?
C22 O2 Na1 108.49(8) . . ?
C22 O2 C24 111.96(13) . . ?
C24 O2 Na1 121.04(9) . . ?
C25 O3 Na1 114.22(10) . . ?
C27 O3 Na1 126.58(10) . . ?
C27 O3 C25 113.22(13) . . ?
C26 O4 Na1 107.44(10) . . ?
C28 O4 Na1 122.02(10) . . ?
C28 O4 C26 112.06(14) . . ?
C29 O5 Na1 110.41(8) . . ?
C29 O5 C31 111.56(11) . . ?
C31 O5 Na1 119.18(8) . . ?
C30 O6 Na1 112.66(8) . . ?
C30 O6 C32 110.98(11) . . ?
C32 O6 Na1 125.39(8) . . ?
C1 N1 C8 124.46(13) . . ?
N1 C1 C2 120.94(13) . . ?
C3 C2 C1 120.35(13) . . ?
C7 C2 C1 122.69(13) . . ?
C7 C2 C3 116.94(13) . . ?
C4 C3 C2 121.20(15) . . ?
C3 C4 C5 120.77(15) . . ?
C4 C5 C6 119.01(14) . . ?
C7 C6 C5 120.97(16) . . ?
C6 C7 C2 121.08(15) . . ?
N1 C8 C9 117.92(12) . . ?
N1 C8 C15 122.11(12) . . ?
C9 C8 C15 119.93(12) . . ?
C10 C9 C8 120.99(12) . . ?
C14 C9 C8 123.04(13) . . ?
C14 C9 C10 115.96(13) . . ?
C11 C10 C9 122.12(13) . . ?
C10 C11 C12 120.79(14) . . ?
C13 C12 C11 118.31(14) . . ?
C14 C13 C12 121.45(14) . . ?
C13 C14 C9 121.37(14) . . ?
C16 C15 C8 120.98(12) . . ?
C20 C15 C8 121.36(13) . . ?
C20 C15 C16 117.65(13) . . ?
C17 C16 C15 121.45(14) . . ?
C18 C17 C16 119.70(15) . . ?
C19 C18 C17 119.92(14) . . ?
C18 C19 C20 119.86(14) . . ?
C19 C20 C15 121.32(14) . . ?
O1 C21 C22 108.72(12) . . ?
O2 C22 C21 109.19(12) . . ?
O3 C25 C26 110.54(13) . . ?
O4 C26 C25 111.49(14) . . ?
O5 C29 C30 108.74(12) . . ?
O6 C30 C29 108.66(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O1 2.3735(12) . ?
Na1 O2 2.3958(11) . ?
Na1 O3 2.3430(12) . ?
Na1 O4 2.4093(12) . ?
Na1 O5 2.3712(11) . ?
Na1 O6 2.3755(11) . ?
O1 C21 1.4290(19) . ?
O1 C23 1.4264(19) . ?
O2 C22 1.4225(19) . ?
O2 C24 1.4308(18) . ?
O3 C25 1.434(2) . ?
O3 C27 1.418(2) . ?
O4 C26 1.415(2) . ?
O4 C28 1.409(2) . ?
O5 C29 1.4237(17) . ?
O5 C31 1.4283(16) . ?
O6 C30 1.4240(16) . ?
O6 C32 1.4305(16) . ?
N1 C1 1.3250(18) . ?
N1 C8 1.3365(17) . ?
C1 C2 1.4353(18) . ?
C2 C3 1.418(2) . ?
C2 C7 1.413(2) . ?
C3 C4 1.387(2) . ?
C4 C5 1.388(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.386(2) . ?
C8 C9 1.445(2) . ?
C8 C15 1.4941(19) . ?
C9 C10 1.419(2) . ?
C9 C14 1.4183(19) . ?
C10 C11 1.380(2) . ?
C11 C12 1.396(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.386(2) . ?
C15 C16 1.398(2) . ?
C15 C20 1.3982(19) . ?
C16 C17 1.390(2) . ?
C17 C18 1.390(2) . ?
C18 C19 1.388(2) . ?
C19 C20 1.391(2) . ?
C21 C22 1.501(2) . ?
C25 C26 1.475(3) . ?
C29 C30 1.496(2) . ?
