#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:20:00 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567665.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_1567665
loop_
_publ_author_name
'Bansal, Deepak'
'Kundu, Arup'
'Singh, Vijay Pal'
'Pal, Arun K.'
'Datta, Ayan'
'Dasgupta, Jyotishman'
'Mukhopadhyay, Pritam'
_publ_section_title
;
 A highly contorted push-pull naphthalenediimide dimer and evidence of
 intramolecular singlet exciton fission.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              11506
_journal_page_last               11512
_journal_paper_doi               10.1039/d2sc04187a
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C34 H44 Br0 N4 O4'
_chemical_formula_sum            'C34 H44 Br0 N4 O4'
_chemical_formula_weight         572.73
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-07 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                78.569(8)
_cell_angle_beta                 86.876(8)
_cell_angle_gamma                82.105(8)
_cell_formula_units_Z            1
_cell_length_a                   4.7183(13)
_cell_length_b                   12.508(3)
_cell_length_c                   13.014(4)
_cell_measurement_reflns_used    2634
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.998
_cell_measurement_theta_min      2.528
_cell_volume                     745.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1508
_diffrn_reflns_av_unetI/netI     0.1243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19100
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.528
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       blocks
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.089(19)
_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   0.892
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.892
_refine_ls_R_factor_all          0.1903
_refine_ls_R_factor_gt           0.0879
_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)+(0.1593P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2131
_refine_ls_wR_factor_ref         0.2603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1195
_reflns_number_total             2634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04187a2.cif
_cod_data_source_block           PP-NDI
_cod_depositor_comments
'Adding full bibliography for 1567665--1567666.cif.'
_cod_original_cell_volume        745.4(3)
_cod_database_code               1567665
_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   0.983
_shelx_estimated_absorpt_t_max   0.986
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
C1 C 0.5486(9) 0.6056(3) 0.6487(3) 0.0408(11) Uani 1 1 d . . . . .
C2 C 0.7939(8) 0.5298(3) 0.6185(3) 0.0379(10) Uani 1 1 d . . . . .
C3 C 0.8805(8) 0.5366(3) 0.5111(3) 0.0367(10) Uani 1 1 d . . . . .
C4 C 0.7274(8) 0.6119(3) 0.4321(3) 0.0377(10) Uani 1 1 d . . . . .
C5 C 0.4838(9) 0.6866(3) 0.4603(3) 0.0425(11) Uani 1 1 d . . . . .
C6 C 0.8191(9) 0.6184(3) 0.3255(3) 0.0418(11) Uani 1 1 d . . . . .
C7 C 0.9395(9) 0.4566(3) 0.6958(3) 0.0420(11) Uani 1 1 d . . . . .
H7 H 0.878786 0.455503 0.765145 0.050 Uiso 1 1 calc R U . . .
C8 C 0.7697(10) 0.7066(3) 0.1351(3) 0.0458(12) Uani 1 1 d . . . . .
C9 C 0.6482(11) 0.8212(4) 0.0808(3) 0.0652(15) Uani 1 1 d . . . . .
H9A H 0.440916 0.829049 0.087413 0.078 Uiso 1 1 calc R U . . .
H9B H 0.714602 0.875016 0.114951 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7377(13) 0.8433(4) -0.0346(3) 0.0738(16) Uani 1 1 d . . . . .
H10A H 0.942556 0.845852 -0.041114 0.089 Uiso 1 1 calc R U . . .
H10B H 0.642842 0.914464 -0.068252 0.089 Uiso 1 1 calc R U . . .
C11 C 0.6625(12) 0.7553(4) -0.0900(3) 0.0723(15) Uani 1 1 d . . . . .
H11A H 0.455968 0.760129 -0.092704 0.087 Uiso 1 1 calc R U . . .
H11B H 0.738665 0.768172 -0.161487 0.087 Uiso 1 1 calc R U . . .
C12 C 0.7813(11) 0.6413(4) -0.0348(3) 0.0647(14) Uani 1 1 d . . . . .
H12A H 0.988784 0.633227 -0.039790 0.078 Uiso 1 1 calc R U . . .
H12B H 0.717052 0.587104 -0.068974 0.078 Uiso 1 1 calc R U . . .
C13 C 0.6852(10) 0.6206(3) 0.0799(3) 0.0530(13) Uani 1 1 d . . . . .
H13A H 0.478908 0.621862 0.084948 0.064 Uiso 1 1 calc R U . . .
H13B H 0.771271 0.548317 0.114219 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1771(8) 0.7598(3) 0.5969(3) 0.0434(11) Uani 1 1 d . . . . .
H14A H 0.075832 0.725462 0.658865 0.052 Uiso 1 1 calc R U . . .
H14B H 0.042127 0.782490 0.540600 0.052 Uiso 1 1 calc R U . . .
C15 C 0.2920(10) 0.8596(3) 0.6189(3) 0.0522(12) Uani 1 1 d . . . . .
H15A H 0.383113 0.895810 0.555322 0.063 Uiso 1 1 calc R U . . .
H15B H 0.437569 0.835584 0.671378 0.063 Uiso 1 1 calc R U . . .
C16 C 0.0661(10) 0.9420(4) 0.6571(4) 0.0619(14) Uani 1 1 d . . . . .
H16A H -0.067789 0.972318 0.601529 0.074 Uiso 1 1 calc R U . . .
H16B H -0.039423 0.904131 0.716082 0.074 Uiso 1 1 calc R U . . .
C17 C 0.1851(13) 1.0339(4) 0.6897(5) 0.099(2) Uani 1 1 d . . . . .
H17A H 0.031671 1.083103 0.713007 0.148 Uiso 1 1 calc R U . . .
H17B H 0.314314 1.004855 0.745948 0.148 Uiso 1 1 calc R U . . .
H17C H 0.285927 1.073090 0.631314 0.148 Uiso 1 1 calc R U . . .
N1 N 0.4097(7) 0.6793(2) 0.5669(2) 0.0418(9) Uani 1 1 d . . . . .
N2 N 0.6828(9) 0.6899(3) 0.2465(2) 0.0506(11) Uani 1 1 d . . . . .
O1 O 0.4729(6) 0.6060(2) 0.7394(2) 0.0556(9) Uani 1 1 d . . . . .
O2 O 0.3433(6) 0.7566(2) 0.3963(2) 0.0557(9) Uani 1 1 d . . . . .
H2 H 0.530(11) 0.735(4) 0.264(4) 0.078(17) Uiso 1 1 d . . . . .
H8 H 0.989(7) 0.710(2) 0.130(2) 0.026(9) Uiso 1 1 d . . . . .
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'
Br Br -0.2901 2.4595 '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
O1 C1 N1 121.0(4) . . ?
O1 C1 C2 122.8(3) . . ?
N1 C1 C2 116.1(3) . . ?
C7 C2 C3 121.2(4) . . ?
C7 C2 C1 118.5(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C3 C4 122.5(4) 2_766 . ?
C3 C3 C2 116.8(4) 2_766 . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C6 119.8(4) . . ?
C3 C4 C5 119.9(3) . . ?
C6 C4 C5 120.2(3) . . ?
O2 C5 N1 118.3(4) . . ?
O2 C5 C4 123.9(4) . . ?
N1 C5 C4 117.7(3) . . ?
N2 C6 C4 122.5(4) . . ?
N2 C6 C7 120.5(4) . 2_766 ?
C4 C6 C7 117.0(3) . 2_766 ?
C2 C7 C6 122.6(4) . 2_766 ?
C2 C7 H7 118.7 . . ?
C6 C7 H7 118.7 2_766 . ?
N2 C8 C9 109.4(4) . . ?
N2 C8 C13 113.2(3) . . ?
C9 C8 C13 110.8(3) . . ?
N2 C8 H8 107.6(17) . . ?
C9 C8 H8 102.9(17) . . ?
C13 C8 H8 112.3(18) . . ?
C10 C9 C8 111.4(4) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 111.6(4) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 111.7(4) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 111.1(4) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C8 C13 C12 111.1(3) . . ?
C8 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C8 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N1 C14 C15 111.3(3) . . ?
N1 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N1 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 113.9(4) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 113.5(4) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 C5 125.3(3) . . ?
C1 N1 C14 116.4(3) . . ?
C5 N1 C14 118.2(3) . . ?
C6 N2 C8 126.4(4) . . ?
C6 N2 H2 117(3) . . ?
C8 N2 H2 116(3) . . ?
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
C1 O1 1.216(4) . ?
C1 N1 1.390(5) . ?
C1 C2 1.480(5) . ?
C2 C7 1.365(5) . ?
C2 C3 1.424(5) . ?
C3 C3 1.407(7) 2_766 ?
C3 C4 1.405(5) . ?
C4 C6 1.420(5) . ?
C4 C5 1.458(6) . ?
C5 O2 1.229(4) . ?
C5 N1 1.401(5) . ?
C6 N2 1.349(5) . ?
C6 C7 1.424(5) 2_766 ?
C7 H7 0.9300 . ?
C8 N2 1.468(5) . ?
C8 C9 1.516(6) . ?
C8 C13 1.512(6) . ?
C8 H8 1.04(3) . ?
C9 C10 1.520(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.519(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.510(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.518(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.475(4) . ?
C14 C15 1.510(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.513(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.488(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N2 H2 0.90(5) . ?
