#------------------------------------------------------------------------------
#$Date: 2023-12-01 19:20:38 +0200 (Fri, 01 Dec 2023) $
#$Revision: 287940 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225269.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_7225269
loop_
_publ_author_name
'Payne, Abby-Jo'
'Hendsbee, Arthur D.'
'McAfee, Seth M.'
'Paul, Devproshad K.'
'Karan, Kunal'
'Welch, Gregory C.'
_publ_section_exptl_refinement
;
The H atoms were placed in geometrically idealized positions 
with C-H 
distances of 0.93Å (aromatic),0.97Å 
(idealized CH₂) and 0.96Å
(idealized CH₃) and were
 constrained to ride on the parent C atom 
with Uiso(H) 
= 1.2Ueq(C) for the aromatic, CH₂ and C-H protons and 
Uiso(H) 
= 1.5Ueq(C) for the idealized CH₃ protons. 
;
_publ_section_title
;
 Synthesis and structure-property relationships of phthalimide and
 naphthalimide based organic π-conjugated small molecules.
;
_journal_issue                   21
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              14709
_journal_page_last               14719
_journal_paper_doi               10.1039/c6cp01596d
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C48 H48 N2 O4 S2'
_chemical_formula_sum            'C48 H48 N2 O4 S2'
_chemical_formula_weight         781.02
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-11-06 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                94.98(2)
_cell_angle_beta                 93.06(2)
_cell_angle_gamma                116.609(15)
_cell_formula_units_Z            1
_cell_length_a                   8.870(13)
_cell_length_b                   9.773(14)
_cell_length_c                   13.13(3)
_cell_measurement_temperature    125(2)
_cell_volume                     1008(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v.  5.4.5'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2034
_diffrn_reflns_av_unetI/netI     0.3251
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11387
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.435
_diffrn_reflns_theta_min         2.349
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.2914
_refine_ls_R_factor_gt           0.1161
_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)+(0.0100P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2137
_refine_ls_wR_factor_ref         0.2638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1483
_reflns_number_total             4660
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cp01596d2.cif
_cod_data_source_block           06_02_2014_ADH2nap2_0ma
_cod_depositor_comments
'Adding full bibliography for 7225267--7225270.cif.'
_cod_database_code               7225269
_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   0.3515
_shelx_estimated_absorpt_t_max   0.7457
_shelxl_version_number           2013-4
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
S1 S -0.2796(2) -0.4095(2) 0.11603(15) 0.0386(6) Uani 1 1 d . .
O1 O 0.5819(6) -0.1905(6) 0.3531(4) 0.0529(15) Uani 1 1 d . .
O2 O 0.7937(6) 0.2427(5) 0.1928(4) 0.0447(14) Uani 1 1 d . .
N1 N 0.6854(6) 0.0258(6) 0.2742(4) 0.0376(16) Uani 1 1 d . .
C1 C -0.4055(8) -0.4663(7) 0.0001(5) 0.0322(18) Uani 1 1 d . .
C2 C -0.3123(8) -0.4332(7) -0.0802(5) 0.0349(18) Uani 1 1 d . .
H2 H -0.3599 -0.4553 -0.1498 0.042 Uiso 1 1 calc R U
C3 C -0.1335(8) -0.3612(8) -0.0495(6) 0.039(2) Uani 1 1 d . .
H3 H -0.0501 -0.3319 -0.0966 0.047 Uiso 1 1 calc R U
C4 C -0.0961(7) -0.3393(7) 0.0536(5) 0.0303(17) Uani 1 1 d . .
C5 C 0.0710(8) -0.2779(8) 0.1165(6) 0.0377(19) Uani 1 1 d . .
C6 C 0.0937(8) -0.3554(8) 0.1935(6) 0.044(2) Uani 1 1 d . .
H6 H 0.0005 -0.4463 0.2088 0.052 Uiso 1 1 calc R U
C7 C 0.2546(8) -0.3016(8) 0.2509(5) 0.0398(19) Uani 1 1 d . .
H7 H 0.2693 -0.3594 0.3016 0.048 Uiso 1 1 calc R U
C8 C 0.3889(8) -0.1664(8) 0.2333(5) 0.0355(18) Uani 1 1 d . .
C9 C 0.3694(8) -0.0782(8) 0.1587(5) 0.0330(18) Uani 1 1 d . .
C10 C 0.2062(8) -0.1326(8) 0.0993(5) 0.0341(18) Uani 1 1 d . .
C11 C 0.1926(8) -0.0386(8) 0.0273(5) 0.0362(18) Uani 1 1 d . .
H11 H 0.0870 -0.0717 -0.0126 0.043 Uiso 1 1 calc R U
C12 C 0.3248(8) 0.0977(8) 0.0128(5) 0.0357(18) Uani 1 1 d . .
H12 H 0.3105 0.1571 -0.0370 0.043 Uiso 1 1 calc R U
C13 C 0.4851(8) 0.1517(8) 0.0723(5) 0.0366(18) Uani 1 1 d . .
H13 H 0.5775 0.2469 0.0625 0.044 Uiso 1 1 calc R U
C14 C 0.5035(8) 0.0642(8) 0.1437(5) 0.0315(17) Uani 1 1 d . .
C15 C 0.6736(9) 0.1213(9) 0.2046(5) 0.0379(19) Uani 1 1 d . .
C16 C 0.5592(8) -0.1142(8) 0.2923(6) 0.0376(19) Uani 1 1 d . .
C17 C 0.8556(8) 0.0757(9) 0.3331(5) 0.043(2) Uani 1 1 d . .
H17A H 0.8398 0.0507 0.4045 0.052 Uiso 1 1 calc R U
H17B H 0.9238 0.1887 0.3359 0.052 Uiso 1 1 calc R U
C18 C 0.9509(8) -0.0056(8) 0.2820(5) 0.0410(19) Uani 1 1 d . .
H18A H 0.9674 0.0201 0.2108 0.049 Uiso 1 1 calc R U
H18B H 0.8820 -0.1187 0.2786 0.049 Uiso 1 1 calc R U
C19 C 1.1244(8) 0.0436(8) 0.3423(5) 0.0373(18) Uani 1 1 d . .
H19A H 1.1103 0.0439 0.4166 0.045 Uiso 1 1 calc R U
H19B H 1.1641 -0.0340 0.3226 0.045 Uiso 1 1 calc R U
C20 C 1.2604(8) 0.2024(8) 0.3243(6) 0.044(2) Uani 1 1 d . .
H20A H 1.2196 0.2798 0.3416 0.053 Uiso 1 1 calc R U
H20B H 1.2783 0.2012 0.2505 0.053 Uiso 1 1 calc R U
C21 C 1.4310(8) 0.2514(8) 0.3884(5) 0.0400(19) Uani 1 1 d . .
H21A H 1.4117 0.2495 0.4620 0.048 Uiso 1 1 calc R U
H21B H 1.4720 0.1745 0.3699 0.048 Uiso 1 1 calc R U
C22 C 1.5668(8) 0.4079(8) 0.3748(6) 0.049(2) Uani 1 1 d . .
H22A H 1.5249 0.4846 0.3919 0.059 Uiso 1 1 calc R U
H22B H 1.5879 0.4091 0.3016 0.059 Uiso 1 1 calc R U
C23 C 1.7355(8) 0.4579(9) 0.4405(6) 0.052(2) Uani 1 1 d . .
H23A H 1.7136 0.4503 0.5135 0.062 Uiso 1 1 calc R U
H23B H 1.7818 0.3855 0.4202 0.062 Uiso 1 1 calc R U
C24 C 1.8690(9) 0.6223(8) 0.4309(6) 0.057(2) Uani 1 1 d . .
H24A H 1.8933 0.6306 0.3591 0.085 Uiso 1 1 calc R U
H24B H 1.9732 0.6460 0.4743 0.085 Uiso 1 1 calc R U
H24C H 1.8261 0.6954 0.4532 0.085 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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C1 S1 C4 91.3(3) . .
C16 N1 C15 127.0(6) . .
C16 N1 C17 115.6(6) . .
C15 N1 C17 117.4(6) . .
C2 C1 C1 128.7(7) . 2_445
C2 C1 S1 111.8(5) . .
C1 C1 S1 119.4(6) 2_445 .
C1 C2 C3 112.8(6) . .
C1 C2 H2 123.6 . .
C3 C2 H2 123.6 . .
C4 C3 C2 112.9(6) . .
C4 C3 H3 123.5 . .
C2 C3 H3 123.5 . .
C3 C4 C5 130.2(6) . .
C3 C4 S1 111.2(5) . .
C5 C4 S1 118.5(5) . .
C6 C5 C10 120.0(6) . .
C6 C5 C4 120.6(6) . .
C10 C5 C4 119.4(7) . .
C5 C6 C7 120.9(7) . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C8 C7 C6 120.4(7) . .
C8 C7 H7 119.8 . .
C6 C7 H7 119.8 . .
C7 C8 C9 120.7(6) . .
C7 C8 C16 119.6(7) . .
C9 C8 C16 119.7(6) . .
C14 C9 C8 121.2(6) . .
C14 C9 C10 119.5(6) . .
C8 C9 C10 119.3(6) . .
C11 C10 C5 124.6(6) . .
C11 C10 C9 117.0(6) . .
C5 C10 C9 118.4(6) . .
C12 C11 C10 122.6(7) . .
C12 C11 H11 118.7 . .
C10 C11 H11 118.7 . .
C11 C12 C13 120.2(7) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C14 C13 C12 119.1(6) . .
C14 C13 H13 120.4 . .
C12 C13 H13 120.4 . .
C13 C14 C9 121.6(6) . .
C13 C14 C15 118.5(6) . .
C9 C14 C15 119.8(6) . .
O2 C15 N1 122.2(6) . .
O2 C15 C14 121.9(7) . .
N1 C15 C14 115.9(6) . .
O1 C16 N1 122.4(7) . .
O1 C16 C8 121.3(6) . .
N1 C16 C8 116.3(7) . .
N1 C17 C18 110.8(5) . .
N1 C17 H17A 109.5 . .
C18 C17 H17A 109.5 . .
N1 C17 H17B 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 108.1 . .
C17 C18 C19 111.2(6) . .
C17 C18 H18A 109.4 . .
C19 C18 H18A 109.4 . .
C17 C18 H18B 109.4 . .
C19 C18 H18B 109.4 . .
H18A C18 H18B 108.0 . .
C20 C19 C18 114.0(6) . .
C20 C19 H19A 108.7 . .
C18 C19 H19A 108.7 . .
C20 C19 H19B 108.7 . .
C18 C19 H19B 108.7 . .
H19A C19 H19B 107.6 . .
C19 C20 C21 113.0(6) . .
C19 C20 H20A 109.0 . .
C21 C20 H20A 109.0 . .
C19 C20 H20B 109.0 . .
C21 C20 H20B 109.0 . .
H20A C20 H20B 107.8 . .
C22 C21 C20 114.8(6) . .
C22 C21 H21A 108.6 . .
C20 C21 H21A 108.6 . .
C22 C21 H21B 108.6 . .
C20 C21 H21B 108.6 . .
H21A C21 H21B 107.6 . .
C21 C22 C23 114.7(6) . .
C21 C22 H22A 108.6 . .
C23 C22 H22A 108.6 . .
C21 C22 H22B 108.6 . .
C23 C22 H22B 108.6 . .
H22A C22 H22B 107.6 . .
C24 C23 C22 113.9(6) . .
C24 C23 H23A 108.8 . .
C22 C23 H23A 108.8 . .
C24 C23 H23B 108.8 . .
C22 C23 H23B 108.8 . .
H23A C23 H23B 107.7 . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.729(7) .
S1 C4 1.741(7) .
O1 C16 1.206(7) .
O2 C15 1.218(8) .
N1 C16 1.376(8) .
N1 C15 1.394(8) .
N1 C17 1.505(8) .
C1 C2 1.346(9) .
C1 C1 1.502(12) 2_445
C2 C3 1.434(9) .
C2 H2 0.9500 .
C3 C4 1.351(9) .
C3 H3 0.9500 .
C4 C5 1.492(9) .
C5 C6 1.373(9) .
C5 C10 1.436(9) .
C6 C7 1.423(9) .
C6 H6 0.9500 .
C7 C8 1.375(9) .
C7 H7 0.9500 .
C8 C9 1.412(9) .
C8 C16 1.503(9) .
C9 C14 1.407(9) .
C9 C10 1.451(9) .
C10 C11 1.411(9) .
C11 C12 1.362(9) .
C11 H11 0.9500 .
C12 C13 1.431(9) .
C12 H12 0.9500 .
C13 C14 1.373(9) .
C13 H13 0.9500 .
C14 C15 1.505(9) .
C17 C18 1.538(9) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.539(9) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.529(9) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.540(9) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.497(9) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.535(9) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.532(9) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 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_4
C4 S1 C1 C2 0.0(6) . .
C4 S1 C1 C1 -176.4(7) . 2_445
C1 C1 C2 C3 176.6(8) 2_445 .
S1 C1 C2 C3 0.6(8) . .
C1 C2 C3 C4 -1.0(9) . .
C2 C3 C4 C5 175.9(7) . .
C2 C3 C4 S1 1.0(8) . .
C1 S1 C4 C3 -0.6(6) . .
C1 S1 C4 C5 -176.1(6) . .
C3 C4 C5 C6 -130.7(8) . .
S1 C4 C5 C6 43.8(9) . .
C3 C4 C5 C10 52.4(10) . .
S1 C4 C5 C10 -133.0(6) . .
C10 C5 C6 C7 -6.0(10) . .
C4 C5 C6 C7 177.2(6) . .
C5 C6 C7 C8 3.1(11) . .
C6 C7 C8 C9 0.5(10) . .
C6 C7 C8 C16 -178.1(6) . .
C7 C8 C9 C14 176.7(6) . .
C16 C8 C9 C14 -4.7(10) . .
C7 C8 C9 C10 -0.9(10) . .
C16 C8 C9 C10 177.6(6) . .
C6 C5 C10 C11 -175.4(7) . .
C4 C5 C10 C11 1.5(10) . .
C6 C5 C10 C9 5.4(10) . .
C4 C5 C10 C9 -177.7(6) . .
C14 C9 C10 C11 1.1(9) . .
C8 C9 C10 C11 178.8(6) . .
C14 C9 C10 C5 -179.7(6) . .
C8 C9 C10 C5 -2.0(10) . .
C5 C10 C11 C12 -179.2(7) . .
C9 C10 C11 C12 0.0(10) . .
C10 C11 C12 C13 -0.6(10) . .
C11 C12 C13 C14 0.1(10) . .
C12 C13 C14 C9 0.9(10) . .
C12 C13 C14 C15 179.1(6) . .
C8 C9 C14 C13 -179.2(7) . .
C10 C9 C14 C13 -1.5(10) . .
C8 C9 C14 C15 2.6(10) . .
C10 C9 C14 C15 -179.7(6) . .
C16 N1 C15 O2 -178.8(7) . .
C17 N1 C15 O2 -1.8(10) . .
C16 N1 C15 C14 0.4(10) . .
C17 N1 C15 C14 177.4(6) . .
C13 C14 C15 O2 0.6(10) . .
C9 C14 C15 O2 178.8(7) . .
C13 C14 C15 N1 -178.6(6) . .
C9 C14 C15 N1 -0.3(9) . .
C15 N1 C16 O1 178.7(7) . .
C17 N1 C16 O1 1.7(10) . .
C15 N1 C16 C8 -2.4(10) . .
C17 N1 C16 C8 -179.4(6) . .
C7 C8 C16 O1 2.0(11) . .
C9 C8 C16 O1 -176.6(7) . .
C7 C8 C16 N1 -177.0(6) . .
C9 C8 C16 N1 4.5(9) . .
C16 N1 C17 C18 80.0(8) . .
C15 N1 C17 C18 -97.4(7) . .
N1 C17 C18 C19 -179.5(6) . .
C17 C18 C19 C20 -77.5(8) . .
C18 C19 C20 C21 177.9(6) . .
C19 C20 C21 C22 -178.8(6) . .
C20 C21 C22 C23 178.8(6) . .
C21 C22 C23 C24 -176.2(6) . .
