New chiral ECD-Raman spectroscopy of atropisomeric naphthalenediimides
Machalska, Ewa; Zając, Grzegorz; Baranska, Malgorzata; Bouř, Petr; Kaczorek, Dorota; Kawęcki, Robert; Rode, Joanna E.; Lyczko, Krzysztof; Dobrowolski, Jan Cz.; Chemical Communications  (2022) –; doi:10.1039/D1CC06974H

data_7129872
_publ_section_title
;
 New chiral ECD-Raman spectroscopy of atropisomeric naphthalenediimides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06974H
_journal_year                    2022
_chemical_formula_moiety         'C38 H25 N3 O6'
_chemical_formula_sum            'C38 H25 N3 O6'
_chemical_formula_weight         619.61
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-10-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2021-10-18 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                69.204(2)
_cell_angle_beta                 78.6911(18)
_cell_angle_gamma                75.309(2)
_cell_formula_units_Z            2
_cell_length_a                   8.83471(17)
_cell_length_b                   11.9486(3)
_cell_length_c                   15.9837(4)
_cell_measurement_reflns_used    35271
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      69.5960
_cell_measurement_theta_min      4.0280
_cell_volume                     1515.25(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0131
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -21.00  32.00   1.00    1.00    --    0.00 -77.00 -30.00   53
  2  \w    -74.00  49.00   1.00    1.00    --    0.00 -19.00  30.00  123
  3  \w    -32.00  42.00   1.00    1.00    --    0.00  77.00 150.00   74
  4  \w    -21.00  15.00   1.00    1.00    --   24.00 101.00  11.95   36
  5  \w      1.00  29.00   1.00    1.15    --   40.00  90.00  38.01   28
  6  \w     10.00  42.00   1.00    1.15    --   44.00  81.00-124.13   32
  7  \w     10.00  42.00   1.00    1.15    --   44.00  82.00 175.90   32
  8  \w     14.00  42.00   1.00    1.15    --   48.00  81.00  27.47   28
  9  \w     14.00  42.00   1.00    1.15    --   48.00  82.00 105.41   28
 10  \w     14.00  42.00   1.00    1.15    --   48.00  81.00 -83.23   28
 11  \w     15.00  42.00   1.00    1.15    --   48.00  80.00 -38.15   27
 12  \w     15.00  42.00   1.00    1.15    --   48.00  80.00-159.03   27
 13  \w    -15.00  76.00   1.00    1.15    --   54.00 -57.00   0.00   91
 14  \w     28.00 123.00   1.00    1.15    --   54.00  67.00 -14.06   95
 15  \w      6.00  98.00   1.00    1.15    --   54.00 -99.00 150.00   92
 16  \w     32.00 123.00   1.00    1.15    --   54.00  57.00  90.00   91
 17  \w    -17.00  86.00   1.00    1.15    --   54.00 -77.00 -90.00  103
 18  \w     32.00 123.00   1.00    1.15    --   54.00  57.00-180.00   91
 19  \w     24.00 124.00   1.00    1.15    --   54.00  74.00 114.18  100
 20  \w     28.00 123.00   1.00    1.15    --   54.00  67.00  52.31   95
 21  \w     27.00 126.00   1.00    1.15    --   56.00  72.00-139.61   99
 22  \w     34.00 134.00   1.00    1.15    --   64.00  74.00 124.61  100
 23  \w     40.00 132.00   1.00    1.15    --   64.00  62.00 -86.29   92
 24  \w     37.00 134.00   1.00    1.15    --   64.00  69.00-121.11   97
 25  \w     45.00 136.00   1.00    1.15    --   68.00  61.00 -52.14   91
 26  \w     40.00 138.00   1.00    1.15    --   68.00  70.00-176.34   98
 27  \w     42.00 145.00   1.00    1.15    --   72.00  34.00 131.29  103
 28  \w     49.00 142.00   1.00    1.15    --   72.00  52.00 -70.75   93
 29  \w     45.00 142.00   1.00    1.15    --   72.00  69.00 120.58   97
 30  \w     42.00 142.00   1.00    1.15    --   72.00  74.00 -25.55  100
 31  \w     49.00 146.00   1.00    1.15    --   76.00  68.00 177.07   97
 32  \w     54.00 146.00   1.00    1.15    --   76.00  53.00  45.37   92
 33  \w     55.00 145.00   1.00    1.15    --   76.00  58.00-116.13   90
 34  \w     59.00 149.00   1.00    1.15    --   80.00  58.00-154.77   90
 35  \w     57.00 148.00   1.00    1.15    --   80.00  61.00  46.14   91
 36  \w     58.00 153.00   1.00    2.75    --   84.00  67.00 -63.43   95
 37  \w     65.00 162.00   1.00    2.75    --   92.00  69.00  74.83   97
 38  \w     68.00 163.00   1.00    2.75    --   92.00  48.00   6.78   95
 39  \w     64.00 162.00   1.00    2.75    --   92.00  71.00 165.07   98
 40  \w     70.00 161.00   1.00    2.75    --   92.00  56.00-143.36   91
 41  \w     66.00 161.00   1.00    2.75    --   92.00  67.00  27.01   95
 42  \w     67.00 166.00   1.00    2.75    --   96.00  73.00-119.03   99
 43  \w     75.00 168.00   1.00    2.75    --  100.00  64.00 -60.98   93
 44  \w     78.00 173.00   1.00    2.75    --  104.00  66.00 -44.84   95
 45  \w     84.00 175.00   1.00    2.75    --  108.00  63.00 -60.00   91
 46  \w     37.00 140.00   1.00    2.75    --  108.00 -77.00-180.00  103
 47  \w     85.00 178.00   1.00    2.75    --  108.00  50.00  30.00   93
 48  \w     84.00 175.00   1.00    2.75    --  108.00  63.00-180.00   91
 49  \w     35.00 109.00   1.00    2.75    --  108.00-111.00 120.00   74
 50  \w     81.00 178.00   1.00    2.75    --  108.00  37.00  30.00   97
 51  \w     84.00 175.00   1.00    2.75    --  108.00  63.00 -90.00   91
 52  \w     84.00 175.00   1.00    2.75    --  108.00  63.00 120.00   91
 53  \w     85.00 178.00   1.00    2.75    --  108.00  50.00  60.00   93
 54  \w    103.00 178.00   1.00    2.75    --  108.00  77.00   0.00   75
 55  \w     84.00 175.00   1.00    2.75    --  108.00  63.00  60.00   91
 56  \w     84.00 175.00   1.00    2.75    --  108.00  63.00  90.00   91
 57  \w     35.00 109.00   1.00    2.75    --  108.00-111.00 -60.00   74
 58  \w     35.00 106.00   1.00    2.75    --  108.00 -91.00  60.00   71
 59  \w     35.00 106.00   1.00    2.75    --  108.00 -91.00 -30.00   71
 60  \w     35.00 109.00   1.00    2.75    --  108.00-111.00-180.00   74
 61  \w     84.00 175.00   1.00    2.75    --  108.00  63.00-150.00   91
 62  \w     80.00 178.00   1.00    2.75    --  108.00  71.00 -38.86   98
 63  \w     83.00 176.00   1.00    2.75    --  108.00  64.00 146.32   93
 64  \w     85.00 178.00   1.00    2.75    --  108.00  50.00-180.00   93
 65  \w     35.00 109.00   1.00    2.75    --  108.00-111.00  30.00   74
 66  \w     35.00 106.00   1.00    2.75    --  108.00 -91.00 120.00   71
 67  \w     85.00 178.00   1.00    2.75    --  108.00  50.00-120.00   93
 68  \w     85.00 178.00   1.00    2.75    --  108.00  50.00 120.00   93
 69  \w    -74.00  74.00   1.00    1.00    --    0.00   0.00-180.00  148
 70  \w    -31.00  10.00   1.00    1.00    --   16.00 106.00 -83.71   41
 71  \w    -25.00  14.00   1.00    1.00    --   20.00 102.00 102.14   39
 72  \w    -26.00   7.00   1.00    1.00    --   24.00 110.00  80.32   33
 73  \w     16.00  42.00   1.00    1.15    --   48.00  77.00 -23.00   26
 74  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00   0.00  148
 75  \w     32.00 123.00   1.00    1.15    --   54.00  57.00 120.00   91
 76  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00  90.00  148
 77  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00 -30.00  148
 78  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00 150.00  148
 79  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00-120.00  148
 80  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00 120.00  148
 81  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00  30.00  148
 82  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00-180.00  148
 83  \w     27.00 112.00   1.00    1.15    --   54.00-125.00-180.00   85
 84  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00 -60.00  148
 85  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00-150.00  148
 86  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00 -90.00  148
 87  \w    -20.00 128.00   1.00    1.15    --   54.00   0.00  60.00  148
 88  \w     35.00 125.00   1.00    1.15    --   56.00  58.00 -40.99   90
 89  \w     32.00 127.00   1.00    1.15    --   56.00  48.00  48.04   95
 90  \w     35.00 128.00   1.00    1.15    --   60.00  64.00 -27.37   93
 91  \w     34.00 129.00   1.00    1.15    --   60.00  66.00-168.46   95
 92  \w     38.00 128.00   1.00    1.15    --   60.00  60.00-125.74   90
 93  \w     42.00 133.00   1.00    1.15    --   64.00  57.00 -50.52   91
 94  \w     46.00 138.00   1.00    1.15    --   68.00  55.00 -68.42   92
 95  \w     51.00 141.00   1.00    1.15    --   72.00  58.00 134.42   90
 96  \w     53.00 147.00   1.00    1.15    --   76.00  51.00 -77.21   94
 97  \w     74.00 165.00   1.00    2.75    --   96.00  56.00-131.12   91
 98  \w     85.00 178.00   1.00    2.75    --  108.00  50.00   0.00   93
 99  \w     85.00 178.00   1.00    2.75    --  108.00  50.00 -90.00   93
100  \w     34.00 172.00   1.00    2.75    --  108.00   0.00-180.00  138
101  \w     81.00 178.00   1.00    2.75    --  108.00  37.00 120.00   97
102  \w     85.00 178.00   1.00    2.75    --  108.00  50.00 -60.00   93
103  \w     84.00 175.00   1.00    2.75    --  108.00  63.00-120.00   91
104  \w     35.00 106.00   1.00    2.75    --  108.00 -91.00-180.00   71
105  \w     85.00 178.00   1.00    2.75    --  108.00  50.00  90.00   93
106  \w     84.00 175.00   1.00    2.75    --  108.00  63.00  30.00   91
107  \w     84.00 175.00   1.00    2.75    --  108.00  63.00   0.00   91
108  \w     85.00 178.00   1.00    2.75    --  108.00  50.00-150.00   93
109  \w     35.00 106.00   1.00    2.75    --  108.00 -91.00  30.00   71
110  \w     85.00 178.00   1.00    2.75    --  108.00  50.00 150.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1767419000
_diffrn_orient_matrix_UB_12      -0.0589418000
_diffrn_orient_matrix_UB_13      -0.0029464000
_diffrn_orient_matrix_UB_21      0.0314213000
_diffrn_orient_matrix_UB_22      0.0947202000
_diffrn_orient_matrix_UB_23      -0.0930856000
_diffrn_orient_matrix_UB_31      0.0269299000
_diffrn_orient_matrix_UB_32      0.0858696000
_diffrn_orient_matrix_UB_33      0.0458728000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            64114
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        64.991
_diffrn_reflns_theta_max         64.991
_diffrn_reflns_theta_min         2.978
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 4188 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(6)
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     890
_refine_ls_number_reflns         9583
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.3009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                9360
_reflns_number_total             9583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06974h1.cif
_cod_data_source_block           ndib-no2
_cod_database_code               7129872
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C38 H25 N3 O6'
_chemical_oxdiff_usercomment     'yellow block, 100K, Cu, 0.20x015x0.10'
_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. Others
 Sof(H73C)=Sof(H73D)=Sof(C74B)=Sof(H74C)=Sof(H74D)=Sof(C75B)=Sof(H75D)=
 Sof(H75E)=Sof(H75F)=1-FVAR(1)
 Sof(H73A)=Sof(H73B)=Sof(C74A)=Sof(H74A)=Sof(H74B)=Sof(C75A)=Sof(H75A)=
 Sof(H75B)=Sof(H75C)=FVAR(1)
 Sof(H35C)=Sof(H35D)=Sof(C36B)=Sof(H36C)=Sof(H36D)=Sof(C37B)=Sof(H37D)=
 Sof(H37E)=Sof(H37F)=1-FVAR(2)
 Sof(H35A)=Sof(H35B)=Sof(C36A)=Sof(H36A)=Sof(H36B)=Sof(C37A)=Sof(H37A)=
 Sof(H37B)=Sof(H37C)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C35(H35A,H35B), C35(H35C,H35D), C72(H72A,H72B), C73(H73A,
 H73B), C73(H73C,H73D), C74A(H74A,H74B), C74B(H74C,H74D), C36A(H36A,H36B),
 C36B(H36C,H36D)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C3(H3), C32(H32), C33(H33), C27(H27), C4(H4), C28(H28),
 C31(H31), C30(H30), C23(H23), C19(H19), C18(H18), C24(H24), C20(H20), C21(H21),
  C41(H41), C40(H40), C47(H47), C46(H46), C70(H70), C69(H69), C58(H58),
 C68(H68), C61(H61), C56(H56), C60(H60), C64(H64), C65(H65), C57(H57), C55(H55),
  C67(H67)
3.c Idealised Me refined as rotating group:
 C75A(H75A,H75B,H75C), C75B(H75D,H75E,H75F), C37A(H37A,H37B,H37C), C37B(H37D,
 H37E,H37F)
;
_shelx_res_checksum              48934
_shelx_hkl_checksum              22210
_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 1.672
_oxdiff_exptl_absorpt_empirical_full_min 0.537