Red fluorescent zwitterionic naphthalenediimides with di/mono-benzimidazolium and a negatively-charged oxygen substituent.
Wang, Chunqin; Han, Songyan; Wang, Tianbao; Zheng, Xuesong; Zhou, Linsen; Liu, Yanhong; Zhang, Cheng; Gao, Ge; Chemical communications (Cambridge, England) 57 (2021) 9422–9425; doi:10.1039/d1cc03586j

data_7128818
_publ_section_title
;
 Red fluorescent zwitterionic naphthalenediimides with
 di/mono-benzimidazolium and a negatively-charged oxygen substituent.
;
_journal_issue                   74
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9422
_journal_page_last               9425
_journal_paper_doi               10.1039/d1cc03586j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C33 H34 N4 O5'
_chemical_formula_sum            'C33 H34 N4 O5'
_chemical_formula_weight         566.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-21 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.1040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0103(4)
_cell_length_b                   12.9385(3)
_cell_length_c                   15.5389(5)
_cell_measurement_reflns_used    7030
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.440
_cell_measurement_theta_min      2.810
_cell_volume                     2815.41(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43768
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.110
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.8934.
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    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6472
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.9533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4280
_reflns_number_total             6472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03586j2.cif
_cod_data_source_block           mo_wcq_2_150k_0m
_cod_depositor_comments          'Adding full bibliography for 7128818.cif.'
_cod_database_code               7128818
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C1, C2
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C015, C016
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
within 2A
C015 \\sim C016: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
Uanis(C015) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C015) = Uanis(C2)
4. Others
 Sof(H00L)=Sof(H00M)=Sof(C0)=Sof(H0A)=Sof(H0B)=1-FVAR(1)
 Sof(H00I)=Sof(H00J)=Sof(C014)=Sof(H01L)=Sof(H01M)=FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=1-FVAR(2)
 Sof(C016)=Sof(H01Q)=Sof(H01R)=FVAR(2)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=1-FVAR(3)
 Sof(C015)=Sof(H01N)=Sof(H01O)=Sof(H01P)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B), C00U(H00C,H00D), C00W(H00E,H00F), C00Y(H00G,H00H), C00Z(H00I,
 H00J), C00Z(H00L,H00M), C011(H01D,H01E), C014(H01L,H01M), C016(H01Q,H01R),
 C0(H0A,H0B), C1(H1A,H1B)
5.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00O(H00O), C00Q(H00Q), C00S(H00S), C00T(H00T), C00X(H00X)
5.c Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C), C012(H01F,H01G,H01H), C013(H01I,H01J,H01K), C015(H01N,
 H01O,H01P), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              41335
_olex2_submission_special_instructions 'No special instructions were received'