Long-lived Charge-Separated State of Spiro Compact Electron Donor-Acceptor Dyads Based on Rhodamine and Naphthalenediimide Chromophores
Xiao, Xiao; Kurganskii, Ivan; Maity, Partha; Zhao, Jianzhang; Jiang, Xiao; Mohammed, Omar F.; Fedin, Matvey V.; Chemical Science  (2022) –; doi:10.1039/D2SC04258D

data_1567864
_publ_section_title
;
 Long-lived Charge-Separated State of Spiro Compact Electron
 Donor-Acceptor Dyads Based on Rhodamine and Naphthalenediimide
 Chromophores
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04258D
_journal_year                    2022
_chemical_formula_moiety         'C45 H41 N5 O6'
_chemical_formula_sum            'C45 H41 N5 O6'
_chemical_formula_weight         747.857
_chemical_name_systematic        Rho-NDI
_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_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-15 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                74.238(2)
_cell_angle_beta                 88.581(2)
_cell_angle_gamma                86.213(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7228(6)
_cell_length_b                   12.0523(6)
_cell_length_c                   16.1605(10)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.46
_cell_volume                     1818.49(18)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.9967
_diffrn_reflns_Laue_measured_fraction_max 0.9947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35294
_diffrn_reflns_point_group_measured_fraction_full 0.9967
_diffrn_reflns_point_group_measured_fraction_max 0.9947
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.46
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1220 before and 0.0561 after correction.
The Ratio of minimum to maximum transmission is 0.9124.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             788.377
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Solvent diffusion'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.4308
_refine_diff_density_min         -0.3328
_refine_diff_density_rms         0.0625
_refine_ls_d_res_high            0.7703
_refine_ls_d_res_low             8.2755
_refine_ls_goodness_of_fit_ref   1.0636
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    66
_refine_ls_number_parameters     510
_refine_ls_number_reflns         8308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0636
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.5971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              -14
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                6508
_reflns_number_total             8308
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2sc04258d2.cif
_cod_data_source_block           1
_cod_database_code               1567864
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C18(H18a,H18b), C19(H19a,H19b), C43(H43a,H43b),
 C44(H44a,H44b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C5(H5), C13(H13), C15(H15), C16(H16), C25(H25), C26(H26),
 C27(H27), C28(H28), C38(H38), C33(H33), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C4(H4a,H4b,H4c), C17(H17a,H17b,H17c), C20(H20a,H20b,H20c),
 C45(H45a,H45b,H45c)
;
_olex2_submission_special_instructions 'No special instructions were received'