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_1555180
_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         'C32 H28 N2 O6'
_chemical_formula_sum            'C32 H28 N2 O6'
_chemical_formula_weight         536.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-29 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   32.9549(8)
_cell_length_b                   12.7486(2)
_cell_length_c                   24.5123(6)
_cell_measurement_reflns_used    17914
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9060
_cell_measurement_theta_min      3.2120
_cell_volume                     10298.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -60.00  18.00   0.50    0.80    --  -46.75  19.00 -30.00  156
  2  \w    -40.00 -15.00   0.50    2.40    --  -88.50 125.00-180.00   50
  3  \w    -88.00 -63.00   0.50    2.40    --  -88.50 146.00-134.00   50
  4  \w   -104.00 -71.00   0.50    0.80    --  -46.75 146.00-134.00   66
  5  \w    -91.00 -26.00   0.50    0.80    --  -46.75 125.00  59.00  130
  6  \w     33.00  94.00   0.50    0.80    --   46.75-125.00 -19.00  122
  7  \w     72.00 117.00   0.50    2.40    --  110.00-125.00 -19.00   90
  8  \w     83.00 109.00   0.50    2.40    --  110.00 -94.00  30.00   52
  9  \w     40.00  83.00   0.50    2.40    --  110.00-125.00 -60.00   86
 10  \w     79.00 105.00   0.50    2.40    --  110.00 -94.00 -90.00   52
 11  \w     65.00 119.00   0.50    2.40    --  110.00 -30.00 -90.00  108
 12  \w     97.00 177.00   0.50    2.40    --  110.00  30.00-120.00  160
 13  \w    142.00 168.00   0.50    2.40    --  110.00  45.00-150.00   52
 14  \w    126.00 177.00   0.50    2.40    --  110.00 125.00-180.00  102
 15  \w    102.00 127.00   0.50    2.40    --  110.00 146.00-134.00   50
 16  \w     99.00 173.00   0.50    2.40    --  110.00 125.00 -60.00  148
 17  \w    124.00 150.00   0.50    2.40    --  110.00 125.00   0.00   52
 18  \w    102.00 146.00   0.50    2.40    --  110.00 125.00  59.00   88
 19  \w    153.00 178.00   0.50    2.40    --  110.00  45.00 150.00   50
 20  \w     97.00 146.00   0.50    2.40    --  110.00  45.00 150.00   98
 21  \w     94.00 123.00   0.50    2.40    --  110.00 125.00   0.00   58
 22  \w     36.00  61.00   0.50    2.40    --  110.00 -30.00 -90.00   50
 23  \w     38.00 120.00   0.50    2.40    --  110.00 -45.00 -60.00  164
 24  \w     39.00 112.00   0.50    2.40    --  110.00-125.00-120.00  146
 25  \w     35.00 113.00   0.50    2.40    --  110.00 -30.00  30.00  156
 26  \w     44.00  69.00   0.50    2.40    --  110.00 -45.00 120.00   50
 27  \w     44.00  78.00   0.50    0.80    --   46.75-146.00 174.00   68
 28  \w     44.00  78.00   0.50    2.40    --  110.00-146.00 174.00   68
 29  \w     82.00 131.00   0.50    2.40    --  110.00-146.00 174.00   98
 30  \w     38.00 102.00   0.50    2.40    --  110.00 -94.00 -30.00  128
 31  \w     41.00 116.00   0.50    2.40    --  110.00-125.00 -90.00  150
 32  \w    -78.00 -38.00   0.50    2.40    --  -88.50 125.00  59.00   80
 33  \w   -161.00-103.00   0.50    2.40    --  -88.50 -45.00 -30.00  116
 34  \w   -114.00 -24.00   0.50    0.80    --  -46.75 -77.00   0.00  180
 35  \w   -100.00 -63.00   0.50    0.80    --  -46.75-146.00 174.00   74
 36  \w   -117.00 -87.00   0.50    2.40    --  -88.50-146.00 174.00   60
 37  \w   -118.00 -70.00   0.50    0.80    --  -46.75-125.00  90.00   96
 38  \w   -119.00 -94.00   0.50    0.80    --  -46.75-125.00 -19.00   50
 39  \w   -119.00 -75.00   0.50    0.80    --  -46.75-125.00  30.00   88
 40  \w   -139.00-114.00   0.50    2.40    --  -88.50-125.00 -19.00   50
 41  \w   -150.00 -76.00   0.50    2.40    --  -88.50 -45.00  30.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438322000
_diffrn_orient_matrix_UB_12      0.0197164000
_diffrn_orient_matrix_UB_13      -0.0180585000
_diffrn_orient_matrix_UB_21      -0.0158370000
_diffrn_orient_matrix_UB_22      -0.0458226000
_diffrn_orient_matrix_UB_23      0.0718990000
_diffrn_orient_matrix_UB_31      0.0036386000
_diffrn_orient_matrix_UB_32      0.0382247000
_diffrn_orient_matrix_UB_33      0.0954399000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2070
_diffrn_reflns_av_unetI/netI     0.1042
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            130600
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.708
_diffrn_reflns_theta_min         2.682
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             4418
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.083
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details
;
 Flack x determined using 4758 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.39(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.351
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1428
_refine_ls_number_reflns         20878
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.351
_refine_ls_R_factor_all          0.1779
_refine_ls_R_factor_gt           0.1534
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3425
_refine_ls_wR_factor_ref         0.3669
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                15222
_reflns_number_total             20878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01090d2.cif
_cod_data_source_block           yzq-2018-1129-1
_cod_original_formula_sum        'C125.84 H101.50 N8 O24'
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         2109.78
_cod_original_formula_moiety
'2.05(C30.54 H24.45 N2 O6), C31.13 H23 N2 O6, C32 H28 N2 O6, 0.26(C)'
_cod_original_formula_units_Z            4
_cod_database_code               1555180
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         ' C S H'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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, All O(H) groups
2. Restrained distances
 C047-C04B \\sim C047-C04C
 with sigma of 0.02
 C046-C049 \\sim C046-C0
 with sigma of 0.02
 C049-C2AA \\sim C0-C2AB
 with sigma of 0.02
 C2AA-C10A \\sim C2AB-C10A
 with sigma of 0.02
 C046-C2AA \\sim C046-C2AB
 with sigma of 0.04
 C049-C10A \\sim C0-C10A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
: with sigma of 0.1 and sigma for terminal atoms of 0.2
: with sigma of 0.1 and sigma for terminal atoms of 0.2
: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Sof(H04C)=Sof(C04C)=Sof(H04G)=Sof(H04H)=Sof(H04I)=1-FVAR(1)
 Sof(H047)=Sof(C04B)=FVAR(1)
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(2)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C1AB)=Sof(H1AA)=
 Sof(H1AB)=Sof(H1AC)=FVAR(3)
 Sof(H04Q)=Sof(H04R)=Sof(C0)=Sof(H0A)=Sof(H0B)=Sof(C2AB)=1-FVAR(4)
 Sof(H04O)=Sof(H04P)=Sof(C049)=Sof(C2AA)=Sof(H2AC)=Sof(H2AD)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C021(H02C,H02D), C022(H02I,H02J), C02U(H02A,H02B), C02Y(H02G,H02H), C031(H03P,
 H03Q), C03B(H03B,H03C), C03D(H03L,H03M), C03F(H03D,H03E), C03L(H03R,H03S),
 C03O(H03H,H03I), C03P(H03F,H03G), C03T(H03X,H03Y), C03W(H4AA,H), C03Z(H03J,
 H03K), C041(H04J,H04K), C042(H04A,H04B), C043(H04S,H04T), C046(H04O,H04P),
 C046(H04Q,H04R), C0AA(H0AA,H0AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C2AA(H2AC,
 H2AD), C0(H0A,H0B)
5.b Aromatic/amide H refined with riding coordinates:
 C00Q(H00Q), C017(H017), C019(H019), C01I(H01I), C01K(H01K), C01L(H01L),
 C01M(H01M), C01T(H01T), C01U(H01U), C01W(H01W), C01Y(H01Y), C025(H025),
 C027(H027), C028(H028), C029(H029), C02D(H02F), C02E(H02E), C02P(H02P),
 C02Q(H02Q), C02T(H02T), C034(H034), C035(H035), C039(H039), C03A(H03A),
 C03G(H03N), C03H(H03O), C03M(H03T), C03N(H03U), C03Q(H03V), C03S(H03W),
 C03U(H03Z), C03V(H03), C047(H047), C047(H04C)
5.c Idealised Me refined as rotating group:
 C03Y(H5AA,HA,HB), C040(H04L,H04M,H04N), C044(H04U,H04V,H04W), C04A(H04D,H04E,
 H04F), C04C(H04G,H04H,H04I), C4(H4A,H4B,H4C), C1AB(H1AA,H1AB,H1AC)
5.d Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005), O007(H007), O00A(H00A), O00D(H00D), O00K(H00K),
 O00L(H00L), O00S(H00S)
;
_shelx_res_checksum              12560
_shelx_hkl_checksum              31229
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 17.961
_oxdiff_exptl_absorpt_empirical_full_min 0.422