1,1′-Bi(2-naphthol-4,5-dicarboximide)s: blue emissive axially chiral scaffolds with aggregation-enhanced emission properties
Chen, Meng-Ting; Zhang, Yang; Vysotsky, Myroslav O.; Lindner, Joachim O.; Li, Meng-Hua; Lin, Mei-Jin; Würthner, Frank; Organic Chemistry Frontiers 6 (2019) 3731–; doi:10.1039/C9QO01090D

data_1555179
_publ_section_title
;
 1,1&#x2032;-Bi(2-naphthol-4,5-dicarboximide)s: blue emissive axially
 chiral scaffolds with aggregation-enhanced emission properties
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3731
_journal_paper_doi               10.1039/C9QO01090D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety
'C50 H48 N2 O6, 0.62(C H4 O), 0.38(O)'
_chemical_formula_sum            'C51 H52 N2 O7'
_chemical_formula_weight         804.94
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-06 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                86.660(13)
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2870(13)
_cell_length_b                   13.2979(16)
_cell_length_c                   27.850(4)
_cell_measurement_reflns_used    25172
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.260
_cell_measurement_theta_min      3.530
_cell_volume                     4542.7(10)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_unetI/netI     0.2130
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25172
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        23.256
_diffrn_reflns_theta_max         23.256
_diffrn_reflns_theta_min         3.528
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       colorless
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1104
_refine_ls_number_reflns         12376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.2354
_refine_ls_R_factor_gt           0.1070
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1332P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2667
_refine_ls_wR_factor_ref         0.3490
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4690
_reflns_number_total             12376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01090d2.cif
_cod_data_source_block           8b
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C102 H104 N4 O14'
_cod_original_formula_weight         1609.89
_cod_original_formula_moiety
'2(C50 H48 N2 O6), C H O, C H4 O0.62, 0.38(O)'
_cod_original_formula_units_Z            2
_cod_database_code               1555179
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(O03C)=Sof(O0)=1-FVAR(1)
 Sof(O039)=Sof(O03B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C01G(H01G), C01Y(H01Y), C023(H023), C02A(H02Z), C02C(H02), C02L(H02L),
 C02O(H5AA), C02Q(H02Q)
3.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00N(H00N), C019(H019), C01B(H01B), C01H(H01H), C01M(H01M),
 C01N(H01N), C01O(H01O), C01W(H01W), C01Z(H01Z), C020(H020), C021(H021),
 C022(H022), C024(H024), C027(H027), C029(H029), C02B(H02D), C02D(H0AA),
 C02E(H1AA), C02F(H02F), C02G(H02G), C02H(H02H), C02I(H2AA), C02J(H3AA),
 C02M(H4AA), C02N(H02N), C02R(H02R), C02S(H7AA)
3.c Idealised Me refined as rotating group:
 C01Q(H01A,H01C,H01D), C026(H02A,H02B,H02C), C02K(H02E,H02I,H02J), C02P(H6AA,H,
 HA), C02T(H02K,H02M,H02O), C02U(H8AA,HB,HC), C02V(H02P,H02S,H02T), C02W(H9AA,
 HD,HE), C02X(H0BA,HF,HG), C02Y(H02U,H02V,H02W), C02Z(H02X,H02Y,HH), C030(H03M,
 H03N,H03O), C031(H03A,H03B,H03C), C032(H03P,H03Q,H03R), C033(H03D,H03E,H03F),
 C034(H03G,H03H,H03I), C035(H03S,H03T,H03U), C036(H03V,H03W,H03X), C037(H03J,
 H03K,H03L), C038(H03Y,HI,HJ), C03C(H1BA,HM,HN)
3.d Idealised tetrahedral OH refined as rotating group:
 O039(H039), O03B(H03)
;
_shelx_res_checksum              34921
_shelx_hkl_checksum              4257
_olex2_submission_special_instructions 'No special instructions were received'