#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:29:53 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/02/1560277.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_1560277
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         'C26 H20 N'
_chemical_formula_sum            'C26 H20 N'
_chemical_formula_weight         346.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-25 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.841(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8522(9)
_cell_length_b                   7.7653(7)
_cell_length_c                   12.2084(11)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.80
_cell_volume                     929.16(15)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0340
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20557
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_min         1.677
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plank
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.033
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4266
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0310
_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)+(0.0403P)²+0.1485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4039
_reflns_number_total             4266
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04822d3.cif
_cod_data_source_block           6241
_cod_depositor_comments
'Adding full bibliography for 1560274--1560278.cif.'
_cod_database_code               1560277
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.61791(14) 0.36137(19) 0.31885(11) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.71268(16) 0.4008(2) 0.40117(13) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.66312(16) 0.4027(2) 0.51076(13) 0.0164(3) Uani 1 1 d . . . . .
C3 C 0.54885(17) 0.3033(3) 0.52990(14) 0.0217(4) Uani 1 1 d . . . . .
H3 H 0.507132 0.231924 0.472903 0.026 Uiso 1 1 calc R . . . .
C4 C 0.49610(19) 0.3081(3) 0.63089(15) 0.0264(4) Uani 1 1 d . . . . .
H4 H 0.419502 0.238805 0.642847 0.032 Uiso 1 1 calc R . . . .
C5 C 0.55458(19) 0.4135(3) 0.71466(14) 0.0250(4) Uani 1 1 d . . . . .
H5 H 0.517569 0.417493 0.783496 0.030 Uiso 1 1 calc R . . . .
C6 C 0.66751(17) 0.5129(2) 0.69719(14) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.707593 0.585563 0.754203 0.026 Uiso 1 1 calc R . . . .
C7 C 0.72222(17) 0.5068(2) 0.59669(13) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.800478 0.573842 0.586075 0.021 Uiso 1 1 calc R . . . .
C8 C 0.85538(16) 0.4521(2) 0.38788(13) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.96377(16) 0.3928(2) 0.46186(13) 0.0184(3) Uani 1 1 d . . . . .
H9 H 0.945445 0.324031 0.523009 0.022 Uiso 1 1 calc R . . . .
C10 C 1.09772(17) 0.4341(2) 0.44617(14) 0.0226(4) Uani 1 1 d . . . . .
H10 H 1.170182 0.392675 0.496587 0.027 Uiso 1 1 calc R . . . .
C11 C 1.12678(18) 0.5349(3) 0.35792(15) 0.0252(4) Uani 1 1 d . . . . .
H11 H 1.218596 0.561638 0.347223 0.030 Uiso 1 1 calc R . . . .
C12 C 1.02040(19) 0.5963(2) 0.28536(15) 0.0234(4) Uani 1 1 d . . . . .
H12 H 1.039501 0.666528 0.225078 0.028 Uiso 1 1 calc R . . . .
C13 C 0.88632(18) 0.5561(2) 0.30007(14) 0.0190(3) Uani 1 1 d . . . . .
H13 H 0.814479 0.599701 0.249898 0.023 Uiso 1 1 calc R . . . .
C14 C 0.63463(15) 0.3092(2) 0.21731(13) 0.0158(3) Uani 1 1 d . . . . .
C15 C 0.51172(15) 0.3140(2) 0.13783(12) 0.0152(3) Uani 1 1 d . . . . .
C16 C 0.39721(16) 0.4092(2) 0.16242(13) 0.0173(3) Uani 1 1 d . . . . .
H16 H 0.400208 0.471058 0.229761 0.021 Uiso 1 1 calc R . . . .
C17 C 0.28041(17) 0.4136(2) 0.08955(14) 0.0202(3) Uani 1 1 d . . . . .
H17 H 0.203200 0.476696 0.107738 0.024 Uiso 1 1 calc R . . . .
C18 C 0.27507(16) 0.3261(2) -0.01039(13) 0.0197(4) Uani 1 1 d . . . . .
H18 H 0.195626 0.332425 -0.061317 0.024 Uiso 1 1 calc R . . . .
C19 C 0.38646(17) 0.2299(2) -0.03505(14) 0.0192(3) Uani 1 1 d . . . . .
H19 H 0.382739 0.168750 -0.102700 0.023 Uiso 1 1 calc R . . . .
C20 C 0.50350(16) 0.2222(2) 0.03855(13) 0.0176(3) Uani 1 1 d . . . . .
H20 H 0.578618 0.154033 0.021448 0.021 Uiso 1 1 calc R . . . .
C21 C 0.76304(16) 0.2358(2) 0.18399(13) 0.0164(3) Uani 1 1 d . . . . .
C22 C 0.81420(17) 0.2881(2) 0.08646(13) 0.0185(3) Uani 1 1 d . . . . .
H22 H 0.764030 0.367676 0.039075 0.022 Uiso 1 1 calc R . . . .
C23 C 0.93782(17) 0.2245(3) 0.05854(14) 0.0217(4) Uani 1 1 d . . . . .
H23 H 0.971854 0.260917 -0.007752 0.026 Uiso 1 1 calc R . . . .
C24 C 1.01177(17) 0.1082(3) 0.12696(15) 0.0241(4) Uani 1 1 d . . . . .
H24 H 1.096471 0.065178 0.107783 0.029 Uiso 1 1 calc R . . . .
C25 C 0.96161(18) 0.0547(2) 0.22367(15) 0.0228(4) Uani 1 1 d . . . . .
H25 H 1.011990 -0.025311 0.270603 0.027 Uiso 1 1 calc R . . . .
C26 C 0.83771(18) 0.1180(2) 0.25194(14) 0.0194(3) Uani 1 1 d . . . . .
H26 H 0.803783 0.080580 0.318063 0.023 Uiso 1 1 calc R . . . .
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N1 C1 128.87(14) . . ?
N1 C1 C2 114.55(14) . . ?
N1 C1 C8 125.17(14) . . ?
C2 C1 C8 120.14(14) . . ?
C3 C2 C1 119.48(14) . . ?
C7 C2 C1 122.36(15) . . ?
C7 C2 C3 118.10(14) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.86(16) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.38(17) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.58(16) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.34(16) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.72(16) . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C1 120.52(15) . . ?
C13 C8 C1 121.35(15) . . ?
C13 C8 C9 118.10(15) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.41(16) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.78(16) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.26(16) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.53(17) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.89(16) . . ?
C12 C13 H13 119.6 . . ?
N1 C14 C15 115.75(14) . . ?
N1 C14 C21 124.27(14) . . ?
C15 C14 C21 119.78(13) . . ?
C16 C15 C14 119.76(14) . . ?
C20 C15 C14 121.85(14) . . ?
C20 C15 C16 118.36(14) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.61(15) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.46(16) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.55(14) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.41(16) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.56(15) . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C14 120.88(15) . . ?
C26 C21 C14 120.19(15) . . ?
C26 C21 C22 118.88(15) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.42(16) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.28(17) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.78(16) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.14(16) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.49(16) . . ?
C25 C26 H26 119.8 . . ?
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
N1 C1 1.336(2) . ?
N1 C14 1.330(2) . ?
C1 C2 1.470(2) . ?
C1 C8 1.486(2) . ?
C2 C3 1.404(2) . ?
C2 C7 1.403(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(2) . ?
C8 C13 1.400(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.473(2) . ?
C14 C21 1.482(2) . ?
C15 C16 1.406(2) . ?
C15 C20 1.402(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.400(2) . ?
C21 C26 1.394(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.392(2) . ?
C26 H26 0.9500 . ?
