#------------------------------------------------------------------------------
#$Date: 2019-11-02 08:03:25 +0200 (Sat, 02 Nov 2019) $
#$Revision: 221036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/78/4127873.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_4127873
loop_
_publ_author_name
'Eymann, Léonard Y M'
'Varava, Paul'
'Shved, Andrei M.'
'Curchod, Basile F. E.'
'Liu, Yizhu'
'Planes, Ophélie M'
'Sienkiewicz, Andrzej'
'Scopelliti, Rosario'
'Fadaei Tirani, Farzaneh'
'Severin, Kay'
_publ_section_title
;
 Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide
 with N-Heterocyclic Olefins.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17112
_journal_page_last               17116
_journal_paper_doi               10.1021/jacs.9b10660
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C40 H42 N6'
_chemical_formula_sum            'C40 H42 N6'
_chemical_formula_weight         606.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.984(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.56119(15)
_cell_length_b                   11.3903(2)
_cell_length_c                   20.3054(5)
_cell_measurement_reflns_used    5051
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.9980
_cell_measurement_theta_min      4.3250
_cell_volume                     1747.74(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Mercury 4.1.2 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -67.00  22.00   1.00    8.89    --  -43.01  37.00 -60.00   89
  2  ω   -117.00 -21.00   1.00    8.89    --  -43.01 -37.00 120.00   96
  3  ω   -110.00 -82.00   1.00    8.89    --  -43.01 -99.00 -90.00   28
  4  ω   -123.00 -96.00   1.00    8.89    --  -43.01 -99.00-150.00   27
  5  ω     55.00  82.00   1.00    8.89    --   43.01-125.00-180.00   27
  6  ω     10.00  83.00   1.00    8.89    --   43.01 -99.00  30.00   73
  7  ω     39.00 134.00   1.00   35.57    --  105.68 -30.00  30.00   95
  8  ω     48.00  75.00   1.00   35.57    --  105.68-125.00  30.00   27
  9  ω     81.00 177.00   1.00   35.57    --  105.68  45.00-150.00   96
 10  ω     37.00 131.00   1.00   35.57    --  105.68 -77.00  60.00   94
 11  ω     29.00 144.00   1.00   35.57    --  105.68 -15.00-150.00  115
 12  ω     78.00 118.00   1.00   35.57    --  105.68-125.00  30.00   40
 13  ω    107.00 174.00   1.00   35.57    --  105.68 125.00 150.00   67
 14  ω    122.00 176.00   1.00   35.57    --  105.68 125.00 -30.00   54
 15  ω    103.00 132.00   1.00   35.57    --  105.68 -61.00 120.00   29
 16  ω     74.00 101.00   1.00   35.57    --  105.68 -94.00-120.00   27
 17  ω     93.00 118.00   1.00   35.57    --  105.68-125.00-180.00   25
 18  ω     34.00 111.00   1.00   35.57    --  105.68 -45.00-150.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11884
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.523
_diffrn_reflns_theta_min         4.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0355
_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)+(0.0525P)²+0.3281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3005
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b10660_si_003.cif
_cod_data_source_block           pv052
_cod_original_cell_volume        1747.73(7)
_cod_database_code               4127873
_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   0.821
_shelx_estimated_absorpt_t_max   0.952
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N1 N 0.24071(12) 0.52690(8) 0.34909(4) 0.0314(2) Uani 1 1 d . . .
C1 C 0.35747(13) 0.60659(9) 0.37854(5) 0.0269(2) Uani 1 1 d . . .
N2 N 0.36328(12) 0.69977(8) 0.33454(4) 0.0337(2) Uani 1 1 d . . .
C2 C 0.25672(17) 0.67439(13) 0.27897(6) 0.0460(3) Uani 1 1 d . . .
H2 H 0.249(2) 0.7302(16) 0.2432(9) 0.062(5) Uiso 1 1 d . . .
N3 N 0.44653(10) 0.49932(7) 0.47454(4) 0.02413(19) Uani 1 1 d . . .
C3 C 0.18056(17) 0.57084(13) 0.28792(6) 0.0439(3) Uani 1 1 d . . .
H3 H 0.097(2) 0.5242(14) 0.2594(8) 0.053(4) Uiso 1 1 d . . .
C4 C 0.45273(13) 0.59913(9) 0.43693(5) 0.0258(2) Uani 1 1 d . . .
H4 H 0.5307(17) 0.6647(11) 0.4495(6) 0.031(3) Uiso 1 1 d . . .
C5 C 0.16884(13) 0.42454(10) 0.37913(5) 0.0289(2) Uani 1 1 d . . .
C6 C 0.00230(14) 0.43293(11) 0.40655(5) 0.0363(3) Uani 1 1 d . . .
C7 C -0.06627(17) 0.33248(13) 0.43528(6) 0.0449(3) Uani 1 1 d . . .
H7 H -0.181(2) 0.3379(14) 0.4565(8) 0.058(4) Uiso 1 1 d . . .
C8 C 0.02682(19) 0.22864(13) 0.43615(7) 0.0483(3) Uani 1 1 d . . .
H8 H -0.020(2) 0.1571(15) 0.4567(9) 0.065(5) Uiso 1 1 d . . .
C9 C 0.19170(18) 0.22252(11) 0.40851(6) 0.0434(3) Uani 1 1 d . . .
H9 H 0.260(2) 0.1477(15) 0.4090(8) 0.059(4) Uiso 1 1 d . . .
C10 C 0.26644(15) 0.32093(10) 0.38002(5) 0.0329(2) Uani 1 1 d . . .
C11 C -0.09796(18) 0.54651(14) 0.40740(7) 0.0529(4) Uani 1 1 d . . .
H11A H -0.161237 0.557673 0.364923 0.063 Uiso 0.811(17) 1 calc R U P
H11B H -0.015020 0.611580 0.415141 0.063 Uiso 0.811(17) 1 calc R U P
H11C H -0.183111 0.544504 0.442684 0.063 Uiso 0.811(17) 1 calc R U P
H11D H -0.078342 0.584832 0.450242 0.063 Uiso 0.189(17) 1 calc R U P
H11E H -0.224559 0.530924 0.400024 0.063 Uiso 0.189(17) 1 calc R U P
H11F H -0.056467 0.598000 0.372481 0.063 Uiso 0.189(17) 1 calc R U P
C12 C 0.45046(17) 0.31709(12) 0.35455(7) 0.0427(3) Uani 1 1 d . . .
H12A H 0.456(2) 0.3622(15) 0.3118(9) 0.059(4) Uiso 1 1 d . . .
H12B H 0.490(2) 0.2332(15) 0.3461(8) 0.055(4) Uiso 1 1 d . . .
H12C H 0.532(2) 0.3530(15) 0.3882(9) 0.061(5) Uiso 1 1 d . . .
C13 C 0.47758(15) 0.79878(10) 0.34267(5) 0.0339(3) Uani 1 1 d . . .
C14 C 0.62752(16) 0.80592(11) 0.30461(6) 0.0386(3) Uani 1 1 d . . .
C15 C 0.73870(19) 0.90233(13) 0.31427(7) 0.0491(3) Uani 1 1 d . . .
H15 H 0.848(2) 0.9071(14) 0.2886(8) 0.057(4) Uiso 1 1 d . . .
C16 C 0.7031(2) 0.98675(13) 0.36061(8) 0.0533(4) Uani 1 1 d . . .
H16 H 0.784(2) 1.0526(16) 0.3684(9) 0.066(5) Uiso 1 1 d . . .
C17 C 0.5538(2) 0.97789(12) 0.39759(7) 0.0502(3) Uani 1 1 d . . .
H17 H 0.527(2) 1.0382(16) 0.4305(9) 0.061(5) Uiso 1 1 d . . .
C18 C 0.43701(17) 0.88462(10) 0.38885(6) 0.0415(3) Uani 1 1 d . . .
C19 C 0.6688(2) 0.71314(13) 0.25490(7) 0.0487(3) Uani 1 1 d . . .
H19A H 0.636(2) 0.6331(16) 0.2706(8) 0.060(5) Uiso 1 1 d . . .
H19B H 0.609(2) 0.7282(17) 0.2115(10) 0.075(5) Uiso 1 1 d . . .
H19C H 0.798(3) 0.7092(16) 0.2470(9) 0.070(5) Uiso 1 1 d . . .
C20 C 0.2711(2) 0.87626(13) 0.42765(8) 0.0559(4) Uani 1 1 d . . .
H20A H 0.278185 0.807266 0.456452 0.067 Uiso 0.855(18) 1 calc R U P
H20B H 0.168182 0.868919 0.397245 0.067 Uiso 0.855(18) 1 calc R U P
H20C H 0.259067 0.947158 0.454465 0.067 Uiso 0.855(18) 1 calc R U P
H20D H 0.192104 0.941629 0.415656 0.067 Uiso 0.145(18) 1 calc R U P
H20E H 0.302108 0.879976 0.474863 0.067 Uiso 0.145(18) 1 calc R U P
H20F H 0.211222 0.801737 0.417644 0.067 Uiso 0.145(18) 1 calc R U P
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 7 -4 0.0633
0 -7 4 0.0430
1 0 13 0.0239
-5 2 -1 0.1968
-1 0 13 0.0476
5 -2 0 0.1677
1 0 -13 0.0476
-2 -7 2 0.0838
0 1 -13 0.0624
2 6 5 0.1017
0 -6 -7 0.0482
-2 4 10 0.0913
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
C1 N1 C3 109.32(9) .
C1 N1 C5 126.48(8) .
C3 N1 C5 123.54(9) .
C4 C1 N1 129.86(9) .
C4 C1 N2 125.26(9) .
N1 C1 N2 104.86(8) .
C1 N2 C2 109.39(9) .
C1 N2 C13 124.19(9) .
C2 N2 C13 126.04(9) .
C3 C2 N2 108.34(10) .
N3 N3 C4 113.81(10) 3_666
C2 C3 N1 108.05(11) .
C1 C4 N3 120.46(9) .
C10 C5 C6 122.51(10) .
C10 C5 N1 119.16(9) .
C6 C5 N1 118.33(10) .
C7 C6 C5 117.67(12) .
C7 C6 C11 120.55(11) .
C5 C6 C11 121.75(11) .
C8 C7 C6 120.92(11) .
C7 C8 C9 120.32(12) .
C8 C9 C10 120.79(12) .
C9 C10 C5 117.78(11) .
C9 C10 C12 120.97(12) .
C5 C10 C12 121.16(10) .
C18 C13 C14 122.17(11) .
C18 C13 N2 119.01(10) .
C14 C13 N2 118.82(11) .
C15 C14 C13 117.75(12) .
C15 C14 C19 120.73(12) .
C13 C14 C19 121.51(11) .
C16 C15 C14 121.00(12) .
C15 C16 C17 120.18(13) .
C16 C17 C18 120.96(13) .
C17 C18 C13 117.91(12) .
C17 C18 C20 121.23(12) .
C13 C18 C20 120.86(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3872(14) .
N1 C3 1.4003(14) .
N1 C5 1.4316(14) .
C1 C4 1.3685(14) .
C1 N2 1.3890(13) .
N2 C2 1.3939(15) .
N2 C13 1.4270(15) .
C2 C3 1.3278(19) .
N3 N3 1.2902(16) 3_666
N3 C4 1.3713(13) .
C5 C10 1.3917(16) .
C5 C6 1.3977(15) .
C6 C7 1.3925(18) .
C6 C11 1.4999(18) .
C7 C8 1.376(2) .
C8 C9 1.387(2) .
C9 C10 1.3903(17) .
C10 C12 1.5017(16) .
C13 C18 1.3962(17) .
C13 C14 1.3964(16) .
C14 C15 1.3927(18) .
C14 C19 1.5017(19) .
C15 C16 1.378(2) .
C16 C17 1.381(2) .
C17 C18 1.3888(19) .
C18 C20 1.5072(18) .
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
C3 N1 C1 C4 -177.49(11) .
C5 N1 C1 C4 11.64(18) .
C3 N1 C1 N2 1.14(12) .
C5 N1 C1 N2 -169.73(10) .
C4 C1 N2 C2 176.76(11) .
N1 C1 N2 C2 -1.95(12) .
C4 C1 N2 C13 3.46(17) .
N1 C1 N2 C13 -175.25(10) .
C1 N2 C2 C3 2.09(15) .
C13 N2 C2 C3 175.25(11) .
N2 C2 C3 N1 -1.33(16) .
C1 N1 C3 C2 0.11(15) .
C5 N1 C3 C2 171.30(11) .
N1 C1 C4 N3 3.02(16) .
N2 C1 C4 N3 -175.35(9) .
N3 N3 C4 C1 174.67(10) 3_666
C1 N1 C5 C10 -84.30(13) .
C3 N1 C5 C10 106.05(13) .
C1 N1 C5 C6 95.69(13) .
C3 N1 C5 C6 -73.97(14) .
C10 C5 C6 C7 -0.35(16) .
N1 C5 C6 C7 179.67(10) .
C10 C5 C6 C11 177.64(11) .
N1 C5 C6 C11 -2.34(16) .
C5 C6 C7 C8 -0.38(18) .
C11 C6 C7 C8 -178.39(12) .
C6 C7 C8 C9 0.3(2) .
C7 C8 C9 C10 0.5(2) .
C8 C9 C10 C5 -1.22(17) .
C8 C9 C10 C12 175.41(12) .
C6 C5 C10 C9 1.13(16) .
N1 C5 C10 C9 -178.88(10) .
C6 C5 C10 C12 -175.49(10) .
N1 C5 C10 C12 4.49(15) .
C1 N2 C13 C18 -75.43(14) .
C2 N2 C13 C18 112.39(14) .
C1 N2 C13 C14 103.89(13) .
C2 N2 C13 C14 -68.29(16) .
C18 C13 C14 C15 0.41(18) .
N2 C13 C14 C15 -178.88(11) .
C18 C13 C14 C19 -179.70(12) .
N2 C13 C14 C19 1.01(17) .
C13 C14 C15 C16 1.0(2) .
C19 C14 C15 C16 -178.88(14) .
C14 C15 C16 C17 -1.2(2) .
C15 C16 C17 C18 -0.1(2) .
C16 C17 C18 C13 1.5(2) .
C16 C17 C18 C20 -178.21(14) .
C14 C13 C18 C17 -1.64(18) .
N2 C13 C18 C17 177.65(11) .
C14 C13 C18 C20 178.06(12) .
N2 C13 C18 C20 -2.64(18) .
