Rhodamine-naphthalimide demonstrated a distinct aggregation-induced emission mechanism: elimination of dark-states via dimer interactions (EDDI)
Qi, Qingkai; Huang, Lu; Yang, Runqing; Li, Jin; Qiao, Qinglong; Xu, Bin; Tian, Wenjing; Liu, Xiaogang; Xu, Zhaochao; Chemical Communications  (2019) –; doi:10.1039/C8CC09212E

data_7122838
_publ_section_title
;
 Rhodamine-naphthalimide demonstrated a distinct aggregation-induced
 emission mechanism: elimination of dark-states via dimer interactions
 (EDDI)
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09212E
_journal_year                    2019
_chemical_formula_moiety         'C44 H42 N4 O4'
_chemical_formula_sum            'C44 H42 N4 O4'
_chemical_formula_weight         690.81
_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_date             2018-07-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-07-31 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                78.776(7)
_cell_angle_beta                 75.149(7)
_cell_angle_gamma                83.468(7)
_cell_formula_units_Z            2
_cell_length_a                   9.9350(8)
_cell_length_b                   12.2145(10)
_cell_length_c                   15.7216(13)
_cell_measurement_reflns_used    1531
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.8180
_cell_measurement_theta_min      3.3920
_cell_volume                     1804.7(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_unetI/netI     0.1914
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16857
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.786
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9894
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7385
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.2419
_refine_ls_R_factor_gt           0.0821
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0952P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2042
_refine_ls_wR_factor_ref         0.2870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2332
_reflns_number_total             7385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09212e4.cif
_cod_data_source_block           rha-nxya
_cod_database_code               7122838
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.989
_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. Restrained distances
 N1-C35 = N1-C35A
 1.5 with sigma of 0.005
 C36-C35 = C36A-C35A
 1.54 with sigma of 0.005
 N2-C37A = N2-C37
 1.5 with sigma of 0.005
 C38-C37 = C38A-C37A
 1.54 with sigma of 0.005
 C42-C41
 1.54 with sigma of 0.005
 H2-H35C
 2.1 with sigma of 0.005
 H10-H37A
 2.1 with sigma of 0.005
 N1-C36 \\sim N1-C36A
 with sigma of 0.02
 N2-C38 \\sim N2-C38A
 with sigma of 0.02
3. Rigid bond restraints
 C42, C43, C29, C30, N1, C35, C35A, C36A, C43, C44
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C36) = Uanis(C36A)
Uanis(C35A) = Uanis(C35)
Uanis(C37A) = Uanis(C37)
Uanis(C38) = Uanis(C38A)
5. Others
 Sof(C38A)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C36A)=Sof(H36D)=Sof(H36E)=
 Sof(H36F)=Sof(C35A)=Sof(H35C)=Sof(H35D)=Sof(C37A)=Sof(H37C)=Sof(H37D)=1-FVAR(1)
 Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=
 Sof(H36B)=Sof(H36C)=Sof(C38)=Sof(H38D)=Sof(H38E)=Sof(H38F)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C37(H37A,H37B), C39(H39A,H39B), C41(H41A,H41B), C35(H35A,
 H35B), C35A(H35C,H35D), C37A(H37C,H37D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C23(H23), C24(H24), C25(H25), C29(H29), C30(H30), C42(H42),
  C43(H43)
6.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C38A(H38A,H38B,H38C), C40(H40A,H40B,H40C), C44(H44A,H44B,
 H44C), C36(H36A,H36B,H36C), C36A(H36D,H36E,H36F), C38(H38D,H38E,H38F)
;
_shelx_res_checksum              2171
_olex2_submission_special_instructions 'No special instructions were received'