#------------------------------------------------------------------------------
#$Date: 2019-10-09 11:48:58 +0300 (Wed, 09 Oct 2019) $
#$Revision: 219201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/45/7234504.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_7234504
loop_
_publ_author_name
'Lisa M. Kozycz'
'Chang Guo'
'Joseph G. Manion'
'Andrew J. Tilley'
'Alan J. Lough'
'Yuning Li'
'Dwight S. Seferos'
_publ_section_title
;
 Enhanced electron mobility in crystalline thionated naphthalene diimides
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              11505
_journal_page_last               11515
_journal_paper_doi               10.1039/C5TC02753E
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C38 H54 N2 O4'
_chemical_formula_sum            'C38 H54 N2 O4'
_chemical_formula_weight         602.83
_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
_cell_angle_alpha                92.995(2)
_cell_angle_beta                 94.603(2)
_cell_angle_gamma                104.495(2)
_cell_formula_units_Z            1
_cell_length_a                   4.6352(2)
_cell_length_b                   6.6073(2)
_cell_length_c                   27.9285(9)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.80
_cell_measurement_theta_min      3.18
_cell_volume                     823.12(5)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            29125
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.391
_diffrn_reflns_theta_max         67.391
_diffrn_reflns_theta_min         1.591
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0451P)²+0.4910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2448
_reflns_number_total             2915
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2015-3-11505.cif
_cod_data_source_block           d1548_a
_cod_database_code               7234504
_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   0.893
_shelx_estimated_absorpt_t_max   0.976
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
O1 O 0.9639(3) 0.12340(18) 0.57406(4) 0.0304(3) Uani 1 1 d . . . . .
O2 O 0.5711(3) 0.60182(18) 0.65035(4) 0.0306(3) Uani 1 1 d . . . . .
N1 N 0.7705(3) 0.3647(2) 0.61243(5) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.4989(4) 0.4243(2) 0.43482(6) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.6522(4) 0.2705(2) 0.43718(6) 0.0227(4) Uani 1 1 d . . . . .
H2A H 0.6870 0.2013 0.4083 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7571(4) 0.2156(2) 0.48194(6) 0.0220(4) Uani 1 1 d . . . . .
H3A H 0.8624 0.1095 0.4832 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7091(4) 0.3140(2) 0.52405(6) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.5524(3) 0.4719(2) 0.52249(5) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.8246(4) 0.2571(2) 0.57121(6) 0.0218(4) Uani 1 1 d . . . . .
C7 C 0.6122(4) 0.5191(2) 0.61256(6) 0.0221(4) Uani 1 1 d . . . . .
C8 C 0.8859(4) 0.3098(3) 0.65966(6) 0.0251(4) Uani 1 1 d . . . . .
H8A H 0.9656 0.4398 0.6810 0.030 Uiso 1 1 calc R U . . .
H8B H 1.0535 0.2451 0.6550 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6482(4) 0.1593(3) 0.68429(6) 0.0249(4) Uani 1 1 d . . . . .
H9A H 0.5162 0.0567 0.6598 0.030 Uiso 1 1 calc R U . . .
H9B H 0.5235 0.2389 0.7003 0.030 Uiso 1 1 calc R U . . .
C10 C 0.7891(4) 0.0428(3) 0.72147(6) 0.0242(4) Uani 1 1 d . . . . .
H10A H 0.9138 -0.0361 0.7052 0.029 Uiso 1 1 calc R U . . .
H10B H 0.9224 0.1463 0.7457 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5586(4) -0.1090(3) 0.74713(6) 0.0238(4) Uani 1 1 d . . . . .
H11A H 0.4607 -0.0278 0.7685 0.029 Uiso 1 1 calc R U . . .
H11B H 0.4024 -0.1947 0.7229 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6951(4) -0.2537(3) 0.77693(6) 0.0254(4) Uani 1 1 d . . . . .
H12A H 0.8480 -0.1676 0.8016 0.031 Uiso 1 1 calc R U . . .
H12B H 0.7980 -0.3314 0.7557 0.031 Uiso 1 1 calc R U . . .
C13 C 0.4681(4) -0.4108(3) 0.80195(6) 0.0266(4) Uani 1 1 d . . . . .
H13A H 0.3128 -0.4953 0.7774 0.032 Uiso 1 1 calc R U . . .
H13B H 0.3684 -0.3333 0.8238 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6075(4) -0.5579(3) 0.83086(6) 0.0264(4) Uani 1 1 d . . . . .
H14A H 0.7012 -0.6386 0.8087 0.032 Uiso 1 1 calc R U . . .
H14B H 0.7681 -0.4728 0.8545 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3857(4) -0.7109(3) 0.85752(6) 0.0273(4) Uani 1 1 d . . . . .
H15A H 0.2242 -0.7953 0.8339 0.033 Uiso 1 1 calc R U . . .
H15B H 0.2934 -0.6304 0.8799 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5262(4) -0.8585(3) 0.88592(6) 0.0273(4) Uani 1 1 d . . . . .
H16A H 0.6163 -0.9402 0.8634 0.033 Uiso 1 1 calc R U . . .
H16B H 0.6895 -0.7740 0.9093 0.033 Uiso 1 1 calc R U . . .
C17 C 0.3052(4) -1.0100(3) 0.91313(6) 0.0285(4) Uani 1 1 d . . . . .
H17A H 0.1356 -1.0884 0.8901 0.034 Uiso 1 1 calc R U . . .
H17B H 0.2245 -0.9284 0.9370 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4421(4) -1.1659(3) 0.93906(7) 0.0324(4) Uani 1 1 d . . . . .
H18A H 0.6086 -1.0880 0.9627 0.039 Uiso 1 1 calc R U . . .
H18B H 0.5265 -1.2458 0.9153 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2165(5) -1.3194(3) 0.96523(7) 0.0399(5) Uani 1 1 d . . . . .
H19A H 0.3152 -1.4171 0.9808 0.060 Uiso 1 1 calc R U . . .
H19B H 0.0515 -1.3979 0.9420 0.060 Uiso 1 1 calc R U . . .
H19C H 0.1377 -1.2417 0.9897 0.060 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 N1 C7 124.88(13) . .
C6 N1 C8 117.67(14) . .
C7 N1 C8 117.44(14) . .
C2 C1 C5 120.09(15) . 2_666
C2 C1 C7 120.08(15) . 2_666
C5 C1 C7 119.84(15) 2_666 2_666
C1 C2 C3 120.34(15) . .
C1 C2 H2A 119.8 . .
C3 C2 H2A 119.8 . .
C4 C3 C2 120.68(15) . .
C4 C3 H3A 119.7 . .
C2 C3 H3A 119.7 . .
C3 C4 C5 119.94(15) . .
C3 C4 C6 120.30(15) . .
C5 C4 C6 119.76(14) . .
C1 C5 C5 119.40(19) 2_666 2_666
C1 C5 C4 121.04(15) 2_666 .
C5 C5 C4 119.55(18) 2_666 .
O1 C6 N1 121.03(15) . .
O1 C6 C4 121.74(15) . .
N1 C6 C4 117.23(14) . .
O2 C7 N1 120.30(15) . .
O2 C7 C1 122.46(16) . 2_666
N1 C7 C1 117.23(14) . 2_666
N1 C8 C9 112.98(14) . .
N1 C8 H8A 109.0 . .
C9 C8 H8A 109.0 . .
N1 C8 H8B 109.0 . .
C9 C8 H8B 109.0 . .
H8A C8 H8B 107.8 . .
C8 C9 C10 111.40(14) . .
C8 C9 H9A 109.3 . .
C10 C9 H9A 109.3 . .
C8 C9 H9B 109.3 . .
C10 C9 H9B 109.3 . .
H9A C9 H9B 108.0 . .
C11 C10 C9 113.08(14) . .
C11 C10 H10A 109.0 . .
C9 C10 H10A 109.0 . .
C11 C10 H10B 109.0 . .
C9 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
C12 C11 C10 112.78(14) . .
C12 C11 H11A 109.0 . .
C10 C11 H11A 109.0 . .
C12 C11 H11B 109.0 . .
C10 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
C11 C12 C13 113.83(15) . .
C11 C12 H12A 108.8 . .
C13 C12 H12A 108.8 . .
C11 C12 H12B 108.8 . .
C13 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
C12 C13 C14 113.20(15) . .
C12 C13 H13A 108.9 . .
C14 C13 H13A 108.9 . .
C12 C13 H13B 108.9 . .
C14 C13 H13B 108.9 . .
H13A C13 H13B 107.8 . .
C15 C14 C13 113.92(15) . .
C15 C14 H14A 108.8 . .
C13 C14 H14A 108.8 . .
C15 C14 H14B 108.8 . .
C13 C14 H14B 108.8 . .
H14A C14 H14B 107.7 . .
C14 C15 C16 113.58(15) . .
C14 C15 H15A 108.9 . .
C16 C15 H15A 108.9 . .
C14 C15 H15B 108.9 . .
C16 C15 H15B 108.9 . .
H15A C15 H15B 107.7 . .
C17 C16 C15 113.64(15) . .
C17 C16 H16A 108.8 . .
C15 C16 H16A 108.8 . .
C17 C16 H16B 108.8 . .
C15 C16 H16B 108.8 . .
H16A C16 H16B 107.7 . .
C16 C17 C18 113.53(15) . .
C16 C17 H17A 108.9 . .
C18 C17 H17A 108.9 . .
C16 C17 H17B 108.9 . .
C18 C17 H17B 108.9 . .
H17A C17 H17B 107.7 . .
C17 C18 C19 112.88(17) . .
C17 C18 H18A 109.0 . .
C19 C18 H18A 109.0 . .
C17 C18 H18B 109.0 . .
C19 C18 H18B 109.0 . .
H18A C18 H18B 107.8 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.220(2) .
O2 C7 1.214(2) .
N1 C6 1.394(2) .
N1 C7 1.398(2) .
N1 C8 1.480(2) .
C1 C2 1.380(2) .
C1 C5 1.411(2) 2_666
C1 C7 1.482(2) 2_666
C2 C3 1.403(2) .
C2 H2A 0.9500 .
C3 C4 1.375(2) .
C3 H3A 0.9500 .
C4 C5 1.413(2) .
C4 C6 1.484(2) .
C5 C1 1.411(2) 2_666
C5 C5 1.411(3) 2_666
C7 C1 1.482(2) 2_666
C8 C9 1.523(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.524(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.524(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.520(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.523(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.526(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.521(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.523(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.523(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.523(2) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.525(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 C1 C2 C3 0.3(2) 2_666 . . .
C7 C1 C2 C3 -179.79(15) 2_666 . . .
C1 C2 C3 C4 0.0(2) . . . .
C2 C3 C4 C5 0.1(2) . . . .
C2 C3 C4 C6 -179.13(15) . . . .
C3 C4 C5 C1 -179.76(15) . . . 2_666
C6 C4 C5 C1 -0.6(2) . . . 2_666
C3 C4 C5 C5 -0.3(3) . . . 2_666
C6 C4 C5 C5 178.86(17) . . . 2_666
C7 N1 C6 O1 -179.67(15) . . . .
C8 N1 C6 O1 -0.5(2) . . . .
C7 N1 C6 C4 1.0(2) . . . .
C8 N1 C6 C4 -179.75(13) . . . .
C3 C4 C6 O1 0.0(2) . . . .
C5 C4 C6 O1 -179.14(15) . . . .
C3 C4 C6 N1 179.32(14) . . . .
C5 C4 C6 N1 0.1(2) . . . .
C6 N1 C7 O2 178.60(15) . . . .
C8 N1 C7 O2 -0.6(2) . . . .
C6 N1 C7 C1 -1.7(2) . . . 2_666
C8 N1 C7 C1 179.10(14) . . . 2_666
C6 N1 C8 C9 -98.63(18) . . . .
C7 N1 C8 C9 80.64(18) . . . .
N1 C8 C9 C10 158.37(14) . . . .
C8 C9 C10 C11 179.77(14) . . . .
C9 C10 C11 C12 169.09(14) . . . .
C10 C11 C12 C13 -178.54(14) . . . .
C11 C12 C13 C14 178.80(14) . . . .
C12 C13 C14 C15 177.98(14) . . . .
C13 C14 C15 C16 179.48(15) . . . .
C14 C15 C16 C17 179.30(14) . . . .
C15 C16 C17 C18 176.55(15) . . . .
C16 C17 C18 C19 -178.78(15) . . . .
