#------------------------------------------------------------------------------
#$Date: 2020-03-05 01:42:07 +0200 (Thu, 05 Mar 2020) $
#$Revision: 248854 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/43/4134332.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_4134332
loop_
_publ_author_name
'Peterson, Joshua P.'
'Ellern, Arkady'
'Winter, Arthur H.'
_publ_section_title
;
 Spin Delocalization, Polarization, and London Dispersion Forces Govern
 the Formation of Diradical Pimers.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c00190
_journal_year                    2020
_chemical_formula_sum            'C22 H14 N4 O2'
_chemical_formula_weight         366.37
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                73.7000(10)
_cell_angle_beta                 88.894(2)
_cell_angle_gamma                65.047(2)
_cell_formula_units_Z            1
_cell_length_a                   7.2535(2)
_cell_length_b                   7.5984(2)
_cell_length_c                   9.1524(2)
_cell_measurement_reflns_used    2690
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      66.2049
_cell_measurement_theta_min      5.0678
_cell_volume                     436.11(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 Suite (Bruker AXS Inc. , 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_measurement_method
'ω and φ scans, narrow frame width, shutterless'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5843
_diffrn_reflns_theta_full        66.47
_diffrn_reflns_theta_max         66.47
_diffrn_reflns_theta_min         5.07
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

SADABS (Spek A. L., 2015) was used for an absorption correction and scalling
of observed data
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             190
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0380
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1427
_reflns_number_gt                1334
_reflns_number_total             1477
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c00190_si_003.cif
_cod_data_source_block           Win034Cu
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4134332
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.44532(16) 0.27169(16) 0.92195(12) 0.0361(4) Uani d . . . 1 . .
N N1 0.22025(19) 1.07972(19) 0.23606(14) 0.0338(4) Uani d . . . 1 . .
N N2 0.87579(18) 0.78455(19) 0.37018(14) 0.0330(4) Uani d . . . 1 . .
C C1 0.4462(2) 0.4286(2) 0.80660(16) 0.0261(4) Uani d . . . 1 . .
C C2 0.2775(2) 0.5724(2) 0.70471(17) 0.0297(4) Uani d . . . 1 . .
H H2 0.149078 0.566911 0.71107 0.036 Uiso calc U . R 1 . .
C C3 0.3015(2) 0.7250(2) 0.59282(16) 0.0261(4) Uani d . . . 1 . .
H H3 0.187318 0.826826 0.522065 0.031 Uiso calc U . R 1 . .
C C4 0.4911(2) 0.73126(19) 0.58264(14) 0.0215(4) Uani d . . . 1 . .
C C5 0.51179(19) 0.90811(19) 0.46477(14) 0.0219(4) Uani d . . . 1 . .
C C6 0.3519(2) 1.0017(2) 0.33272(14) 0.0243(4) Uani d . . . 1 . .
C C7 0.7155(2) 0.83974(18) 0.40846(14) 0.0235(4) Uani d . . . 1 . .
C C8 0.66141(19) 0.57997(19) 0.68492(14) 0.0226(4) Uani d . . . 1 . .
H H8 0.791864 0.580593 0.676138 0.027 Uiso calc U . R 1 . .
C C9 0.6373(2) 0.4308(2) 0.79807(15) 0.0235(4) Uani d . . . 1 . .
C C10 0.7870(2) 0.2518(2) 0.92260(16) 0.0304(4) Uani d . . . 1 . .
H H10A 0.857283 0.294919 0.987413 0.037 Uiso calc U . R 1 . .
H H10B 0.890423 0.150382 0.879853 0.037 Uiso calc U . R 1 . .
C C11 0.6452(2) 0.1678(2) 1.01267(15) 0.0314(4) Uani d . . . 1 . .
H H11A 0.701335 0.019224 1.0299 0.038 Uiso calc U . R 1 . .
H H11B 0.633123 0.19334 1.113505 0.038 Uiso calc U . R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C11 . . 107.64(10) ?
O1 C1 C2 . . 124.39(13) ?
O1 C1 C9 . . 113.36(13) ?
C2 C1 C9 . . 122.25(13) ?
C1 C2 C3 . . 117.89(12) ?
C1 C2 H2 . . 121.1 ?
C3 C2 H2 . . 121.1 ?
C2 C3 C4 . . 120.92(12) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C3 C4 C8 . . 120.04(13) ?
C3 C4 C5 . . 120.20(11) ?
C8 C4 C5 . . 119.70(11) ?
C6 C5 C7 . . 108.98(10) ?
C6 C5 C4 . . 111.32(10) ?
C7 C5 C4 . . 111.09(10) ?
C6 C5 C5 . 2_676 106.21(12) ?
C7 C5 C5 . 2_676 106.21(12) ?
C4 C5 C5 . 2_676 112.77(12) ?
N1 C6 C5 . . 175.89(13) ?
N2 C7 C5 . . 177.60(13) ?
C9 C8 C4 . . 119.18(12) ?
C9 C8 H8 . . 120.4 ?
C4 C8 H8 . . 120.4 ?
C8 C9 C1 . . 119.68(13) ?
C8 C9 C10 . . 131.62(12) ?
C1 C9 C10 . . 108.68(13) ?
C9 C10 C11 . . 101.56(11) ?
C9 C10 H10A . . 111.5 ?
C11 C10 H10A . . 111.5 ?
C9 C10 H10B . . 111.5 ?
C11 C10 H10B . . 111.5 ?
H10A C10 H10B . . 109.3 ?
O1 C11 C10 . . 107.52(10) ?
O1 C11 H11A . . 110.2 ?
C10 C11 H11A . . 110.2 ?
O1 C11 H11B . . 110.2 ?
C10 C11 H11B . . 110.2 ?
H11A C11 H11B . . 108.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.3551(17) ?
O1 C11 . 1.4588(17) ?
N1 C6 . 1.1433(17) ?
N2 C7 . 1.1426(18) ?
C1 C2 . 1.380(2) ?
C1 C9 . 1.393(2) ?
C2 C3 . 1.3857(19) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3964(19) ?
C3 H3 . 0.95 ?
C4 C8 . 1.4023(17) ?
C4 C5 . 1.5305(18) ?
C5 C6 . 1.4787(17) ?
C5 C7 . 1.4806(18) ?
C5 C5 2_676 1.642(2) ?
C8 C9 . 1.3747(19) ?
C8 H8 . 0.95 ?
C9 C10 . 1.5030(18) ?
C10 C11 . 1.540(2) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
