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#$Date: 2025-10-24 11:00:34 +0300 (Fri, 24 Oct 2025) $
#$Revision: 302982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/60/1576052.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_1576052
loop_
_publ_author_name
'Mohanty, Aisworika'
'Singh, Vijay Pal'
'Hussain, Ch Mudasar'
'DEY, MANDIRA'
'Ghosh, Debashree'
'Mukhopadhyay, Pritam'
'Dasgupta, Jyotishman'
_publ_section_title
;
 An Order of Magnitude Modulation of Singlet Fission Rates in NDI
 Cyclophanes by Tuning Inter-chromophoric Electronic Coupling
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC05995J
_journal_year                    2025
_chemical_compound_source        synthesised
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03
_chemical_melting_point          'above 573 K'
_chemical_name_common            'ortho-meta dimer'
_chemical_name_systematic        'meta-meta macrocycle'
_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
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-02-18 deposited with the CCDC.	2025-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                97.382(5)
_cell_angle_beta                 95.436(5)
_cell_angle_gamma                103.911(4)
_cell_formula_units_Z            25
_cell_length_a                   8.7657(12)
_cell_length_b                   12.0705(14)
_cell_length_c                   12.3241(14)
_cell_measurement_temperature    100(2)
_cell_volume                     1244.5(3)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_min         2.235
_exptl_absorpt_coefficient_mu    0.129
_exptl_crystal_colour            'deep blue'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       rectaangular
_exptl_crystal_F_000             550
_refine_diff_density_max         3.207
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       0.005(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   2.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.128
_refine_ls_R_factor_all          0.2580
_refine_ls_R_factor_gt           0.1955
_refine_ls_shift/su_max          0.945
_refine_ls_shift/su_mean         0.102
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5305
_refine_ls_wR_factor_ref         0.5732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3530
_reflns_number_total             6191
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc05995j2.cif
_cod_data_source_block           PMVP72_LT_1_0m_a
_cod_database_code               1576052
_shelx_shelxl_version_number     2019/1
_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.
;
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
O001 O 0.8751(5) 0.7383(4) 0.7883(4) 0.0594(13) Uani 1 1 d . . . . .
O002 O 0.4597(5) 0.1437(4) 0.3198(4) 0.0632(14) Uani 1 1 d . . . . .
O003 O 0.5500(5) 0.4186(4) 0.8764(4) 0.0667(14) Uani 1 1 d . . . . .
C2 C 0.8793(5) 0.8500(4) 0.4052(4) 0.0303(11) Uani 1 1 d . . . . .
H2 H 0.807590 0.795820 0.437871 0.036 Uiso 1 1 calc R U . . .
N005 N 0.7059(6) 0.5792(4) 0.8320(5) 0.0520(14) Uani 1 1 d . . . . .
O006 O 0.7976(7) 0.4560(4) 0.2371(4) 0.0801(17) Uani 1 1 d . . . . .
N007 N 0.6139(6) 0.3077(4) 0.2780(5) 0.0539(14) Uani 1 1 d . . . . .
C1 C 1.0824(7) 1.0055(5) 0.3064(5) 0.0495(16) Uani 1 1 d . . . . .
H1 H 1.152919 1.059607 0.272841 0.059 Uiso 1 1 calc R U . . .
C009 C 0.5083(6) 0.2940(5) 0.6615(6) 0.0491(16) Uani 1 1 d . . . . .
H009 H 0.459807 0.253087 0.715403 0.059 Uiso 1 1 calc R U . . .
C00A C 0.6592(6) 0.4126(5) 0.5028(6) 0.0478(16) Uani 1 1 d . . . . .
C00B C 0.6770(6) 0.4670(5) 0.6106(6) 0.0438(15) Uani 1 1 d . . . . .
C00C C 0.5965(6) 0.4091(5) 0.6911(6) 0.0494(16) Uani 1 1 d . . . . .
C00D C 0.7914(7) 0.6387(5) 0.7562(6) 0.0498(16) Uani 1 1 d . . . . .
C00E C 0.8675(7) 0.6329(5) 0.5669(6) 0.0543(18) Uani 1 1 d . . . . .
C00F C 0.4914(6) 0.2382(5) 0.5496(6) 0.0520(17) Uani 1 1 d . . . . .
C00G C 0.5617(6) 0.2990(5) 0.4705(6) 0.0494(16) Uani 1 1 d . . . . .
C00H C 0.7787(6) 0.5810(5) 0.6436(6) 0.0470(15) Uani 1 1 d . . . . .
C00I C 0.6135(7) 0.4662(6) 0.8061(6) 0.0519(16) Uani 1 1 d . . . . .
C00J C 0.7477(7) 0.4694(5) 0.4234(6) 0.0491(16) Uani 1 1 d . . . . .
C00K C 0.5404(7) 0.2417(5) 0.3541(7) 0.0561(18) Uani 1 1 d . . . . .
C00L C 0.8556(8) 0.5773(5) 0.4573(6) 0.0555(18) Uani 1 1 d . . . . .
H00L H 0.920192 0.612668 0.407158 0.067 Uiso 1 1 calc R U . . .
C00M C 0.6927(7) 0.1784(6) 0.1320(5) 0.0560(17) Uani 1 1 d . . . . .
H00A H 0.671587 0.112638 0.173726 0.067 Uiso 1 1 calc R U . . .
H00B H 0.804021 0.223074 0.155667 0.067 Uiso 1 1 calc R U . . .
C00N C 0.7257(8) 0.4146(5) 0.3082(6) 0.0588(18) Uani 1 1 d . . . . .
C00O C 1.0320(7) 0.8514(5) 0.4148(7) 0.065(2) Uani 1 1 d . . . . .
C00P C 0.7314(8) 0.6355(6) 0.9470(6) 0.0584(17) Uani 1 1 d . . . . .
H00C H 0.637802 0.604570 0.983458 0.070 Uiso 1 1 calc R U . . .
H00D H 0.744003 0.719548 0.949583 0.070 Uiso 1 1 calc R U . . .
C00Q C 0.8803(9) 0.6146(5) 1.0092(6) 0.0626(19) Uani 1 1 d . . . . .
H00E H 0.969081 0.632731 0.965017 0.075 Uiso 1 1 calc R U . . .
H00F H 0.859860 0.531795 1.016508 0.075 Uiso 1 1 calc R U . . .
C00R C 0.5852(9) 0.2544(6) 0.1613(6) 0.066(2) Uani 1 1 d . . . . .
H00G H 0.599506 0.316306 0.114846 0.079 Uiso 1 1 calc R U . . .
H00H H 0.473886 0.207867 0.143914 0.079 Uiso 1 1 calc R U . . .
C00S C 0.9283(9) 0.6848(5) 1.1206(6) 0.068(2) Uani 1 1 d . . . . .
H00I H 0.945006 0.767844 1.115231 0.081 Uiso 1 1 calc R U . . .
H00J H 0.844074 0.663361 1.167914 0.081 Uiso 1 1 calc R U . . .
C00T C 0.8257(7) 0.9249(7) 0.3495(8) 0.081(3) Uani 1 1 d . . . . .
C00U C 0.9265(8) 1.0021(7) 0.2994(7) 0.081(3) Uani 1 1 d . . . . .
H00U H 0.886317 1.053491 0.259404 0.097 Uiso 1 1 calc R U . . .
C00V C 1.1358(8) 0.9295(5) 0.3626(9) 0.090(3) Uani 1 1 d . . . . .
H00V H 1.244473 0.929131 0.366806 0.108 Uiso 1 1 calc R U . . .
C00W C 0.6739(11) 0.1322(9) 0.0119(6) 0.089(3) Uani 1 1 d . . . . .
H00K H 0.561356 0.090859 -0.012356 0.106 Uiso 1 1 calc R U . . .
H00M H 0.699791 0.198040 -0.029332 0.106 Uiso 1 1 calc R U . . .
C00X C 1.0813(9) 0.6621(6) 1.1707(9) 0.089(3) Uani 1 1 d . . . . .
H00N H 1.058606 0.584615 1.191400 0.134 Uiso 1 1 calc R U . . .
H00O H 1.127095 0.719705 1.236452 0.134 Uiso 1 1 calc R U . . .
H00P H 1.156677 0.667351 1.116565 0.134 Uiso 1 1 calc R U . . .
C00Y C 0.7714(15) 0.0548(11) -0.0167(7) 0.122(5) Uani 1 1 d . . . . .
H00Q H 0.882737 0.093385 0.010313 0.183 Uiso 1 1 calc R U . . .
H00R H 0.758778 0.033277 -0.097102 0.183 Uiso 1 1 calc R U . . .
H00S H 0.738879 -0.014854 0.017218 0.183 Uiso 1 1 calc R U . . .
N2 N 0.9730(11) 0.7357(7) 0.5868(7) 0.108(3) Uani 1 1 d . . . . .
H2A H 0.982327 0.783848 0.648540 0.130 Uiso 1 1 calc R U . . .
N1 N 0.4135(12) 0.1185(9) 0.5290(10) 0.138(4) Uani 1 1 d . . . . .
H1A H 0.398837 0.074421 0.464268 0.165 Uiso 1 1 calc R U . . .
C013 C 1.0929(9) 0.7696(9) 0.4818(16) 0.186(8) Uani 1 1 d . . . . .
H01A H 1.091719 0.697767 0.432539 0.223 Uiso 1 1 calc R U . . .
H01B H 1.203610 0.806291 0.515415 0.223 Uiso 1 1 calc R U . . .
C014 C 0.3501(11) 0.0700(13) 0.650(2) 0.293(15) Uani 1 1 d . . . . .
H01C H 0.416836 0.119899 0.715856 0.352 Uiso 1 1 calc R U . . .
H01D H 0.358680 -0.010223 0.650936 0.352 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'
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
C00O C2 C00T 120.3(5) . . ?
C00I N005 C00D 123.6(6) . . ?
C00I N005 C00P 118.3(5) . . ?
C00D N005 C00P 117.7(5) . . ?
C00N N007 C00K 124.0(6) . . ?
C00N N007 C00R 118.1(6) . . ?
C00K N007 C00R 117.5(6) . . ?
C00U C1 C00V 118.3(5) . . ?
C00C C009 C00F 119.7(6) . . ?
C00B C00A C00J 119.9(6) . . ?
C00B C00A C00G 120.6(6) . . ?
C00J C00A C00G 119.4(7) . . ?
C00A C00B C00C 120.3(6) . . ?
C00A C00B C00H 120.4(5) . . ?
C00C C00B C00H 119.2(6) . . ?
C009 C00C C00B 119.4(7) . . ?
C009 C00C C00I 119.6(6) . . ?
C00B C00C C00I 120.9(6) . . ?
O001 C00D N005 118.8(6) . . ?
O001 C00D C00H 122.3(5) . . ?
N005 C00D C00H 118.9(5) . . ?
N2 C00E C00H 125.8(8) . . ?
N2 C00E C00L 112.6(7) . . ?
C00H C00E C00L 121.6(6) . . ?
C00G C00F N1 123.9(8) . . ?
C00G C00F C009 119.9(6) . . ?
N1 C00F C009 116.0(7) . . ?
C00F C00G C00A 119.8(7) . . ?
C00F C00G C00K 119.6(6) . . ?
C00A C00G C00K 120.5(6) . . ?
C00E C00H C00B 118.9(6) . . ?
C00E C00H C00D 121.4(6) . . ?
C00B C00H C00D 119.7(5) . . ?
O003 C00I N005 120.2(7) . . ?
O003 C00I C00C 122.4(6) . . ?
N005 C00I C00C 117.4(5) . . ?
C00L C00J C00A 119.7(7) . . ?
C00L C00J C00N 119.8(6) . . ?
C00A C00J C00N 120.5(6) . . ?
O002 C00K N007 118.3(7) . . ?
O002 C00K C00G 124.6(6) . . ?
N007 C00K C00G 117.0(6) . . ?
C00J C00L C00E 119.2(6) . . ?
C00R C00M C00W 113.8(6) . . ?
O006 C00N N007 118.2(7) . . ?
O006 C00N C00J 124.3(6) . . ?
N007 C00N C00J 117.6(6) . . ?
C2 C00O C00V 119.1(6) . . ?
C2 C00O C013 120.0(5) . . ?
C00V C00O C013 120.9(6) . . ?
N005 C00P C00Q 110.7(5) . . ?
C00P C00Q C00S 113.5(6) . . ?
N007 C00R C00M 113.6(5) . . ?
C00X C00S C00Q 108.5(6) . . ?
C2 C00T C00U 120.9(6) . . ?
C2 C00T C014 119.1(6) . 2_666 ?
C00U C00T C014 119.8(6) . 2_666 ?
C1 C00U C00T 120.6(6) . . ?
C1 C00V C00O 120.8(6) . . ?
C00Y C00W C00M 114.4(8) . . ?
C00E N2 C013 116.1(9) . . ?
C00F N1 C014 111.1(10) . . ?
N2 C013 C00O 110.4(7) . . ?
N1 C014 C00T 107.6(9) . 2_666 ?
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
O001 C00D 1.241(7) . ?
O002 C00K 1.221(8) . ?
O003 C00I 1.207(7) . ?
C2 C00O 1.328(8) . ?
C2 C00T 1.347(7) . ?
N005 C00I 1.388(8) . ?
N005 C00D 1.413(7) . ?
N005 C00P 1.463(9) . ?
O006 C00N 1.216(8) . ?
N007 C00N 1.402(9) . ?
N007 C00K 1.411(8) . ?
N007 C00R 1.470(9) . ?
C1 C00U 1.352(10) . ?
C1 C00V 1.360(10) . ?
C009 C00C 1.400(9) . ?
C009 C00F 1.433(10) . ?
C00A C00B 1.381(10) . ?
C00A C00J 1.445(8) . ?
C00A C00G 1.415(9) . ?
C00B C00C 1.430(8) . ?
C00B C00H 1.432(8) . ?
C00C C00I 1.471(10) . ?
C00D C00H 1.452(10) . ?
C00E N2 1.335(10) . ?
C00E C00H 1.395(8) . ?
C00E C00L 1.412(10) . ?
C00F C00G 1.397(8) . ?
C00F N1 1.420(12) . ?
C00G C00K 1.484(10) . ?
C00J C00L 1.400(9) . ?
C00J C00N 1.462(10) . ?
C00M C00R 1.502(10) . ?
C00M C00W 1.493(10) . ?
C00O C00V 1.409(8) . ?
C00O C013 1.524(11) . ?
C00P C00Q 1.540(10) . ?
C00Q C00S 1.483(10) . ?
C00S C00X 1.522(11) . ?
C00T C00U 1.373(8) . ?
C00T C014 1.558(12) 2_666 ?
C00W C00Y 1.444(16) . ?
N2 C013 1.771(17) . ?
N1 C014 1.76(2) . ?
