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_7129870
_publ_section_title
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 New chiral ECD-Raman spectroscopy of atropisomeric naphthalenediimides
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06974H
_journal_year                    2022
_chemical_formula_moiety         'C39 H28 N2 O5'
_chemical_formula_sum            'C39 H28 N2 O5'
_chemical_formula_weight         604.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                90
_cell_angle_beta                 98.765(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8341(3)
_cell_length_b                   8.3172(2)
_cell_length_c                   14.9538(5)
_cell_measurement_reflns_used    5151
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      69.8980
_cell_measurement_theta_min      3.7670
_cell_volume                     1454.66(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_temperature      100.15
_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  30.00   1.00    2.10    --    0.00 -77.00-150.00   51
  2  \w    -69.00  21.00   1.00    2.10    --    0.00 -57.00 -60.00   90
  3  \w    -30.00  42.00   1.00    2.10    --    0.00  77.00  30.00   72
  4  \w     31.00 121.00   1.00    7.50    --   54.00  64.00-134.96   90
  5  \w     33.00 123.00   1.00    7.50    --   54.00  57.00 -60.00   90
  6  \w     33.00 116.00   1.00    7.50    --   54.00-133.00-140.00   83
  7  \w    -15.00  75.00   1.00    7.50    --   54.00 -57.00-150.00   90
  8  \w     32.00 122.00   1.00    7.50    --   54.00  61.00 158.11   90
  9  \w     33.00 123.00   1.00    7.50    --   54.00  57.00 120.00   90
 10  \w     27.00 111.00   1.00    7.50    --   54.00-125.00   0.00   84
 11  \w    -15.00  75.00   1.00    7.50    --   54.00 -57.00   0.00   90
 12  \w     36.00 134.00   1.00   13.50    --  108.00 -37.00-180.00   98
 13  \w     36.00 109.00   1.00   13.50    --  108.00-111.00  90.00   73
 14  \w     72.00  97.00   1.00   13.50    --  108.00 -91.00-180.00   25
 15  \w     86.00 174.00   1.00   13.50    --  108.00  63.00 -30.00   88
 16  \w    105.00 134.00   1.00   13.50    --  108.00 111.00 -90.00   29
 17  \w    138.00 175.00   1.00   13.50    --  108.00  67.00   7.33   37
 18  \w     41.00 129.00   1.00   13.50    --  108.00 -63.00-120.00   88
 19  \w     86.00 113.00   1.00   13.50    --  108.00  67.00   7.33   27
 20  \w     44.00 129.00   1.00   13.50    --  108.00 -50.00   0.00   85
 21  \w     58.00 108.00   1.00   13.50    --  108.00-111.00 -90.00   50
 22  \w     36.00 108.00   1.00   13.50    --  108.00-111.00-180.00   72
 23  \w    136.00 163.00   1.00   13.50    --  108.00  77.00 -60.00   27
 24  \w     80.00 107.00   1.00   13.50    --  108.00 -91.00 -60.00   27
 25  \w     39.00  95.00   1.00   13.50    --  108.00 -91.00  30.00   56
 26  \w     54.00 109.00   1.00   13.50    --  108.00 -50.00 120.00   55
 27  \w     49.00 178.00   1.00   13.50    --  108.00 -12.00 -60.00  129
 28  \w     52.00  79.00   1.00   13.50    --  108.00-111.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0314
_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       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11660
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        65.961
_diffrn_reflns_theta_max         65.961
_diffrn_reflns_theta_min         2.990
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67049
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(14)
_refine_ls_extinction_coef       0.0013(5)
_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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         4920
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0772P)^2^+0.3848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                4450
_reflns_number_total             4920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06974h1.cif
_cod_data_source_block           ndib-ome
_cod_original_cell_volume        1454.67(7)
_cod_database_code               7129870
_shelx_shelxl_version_number     2017/1
_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(H37C)=Sof(H37D)=Sof(C39B)=Sof(H39D)=Sof(H39E)=Sof(H39F)=Sof(C38B)=
 Sof(H38C)=Sof(H38D)=1-FVAR(1)
 Sof(H37A)=Sof(H37B)=Sof(C38A)=Sof(H38A)=Sof(H38B)=Sof(C39A)=Sof(H39A)=
 Sof(H39B)=Sof(H39C)=FVAR(1)
 Sof(C35B)=Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(2)
 Sof(C35A)=Sof(H35A)=Sof(H35B)=Sof(H35C)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C37(H37A,H37B), C37(H37C,H37D), C38A(H38A,H38B), C38B(H38C,
 H38D)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4), C10(H10), C18(H18), C19(H19), C3(H3), C32(H32), C30(H30),
 C24(H24), C33(H33), C31(H31), C28(H28), C23(H23), C20(H20), C27(H27), C21(H21)
3.c Idealised Me refined as rotating group:
 C39A(H39A,H39B,H39C), C39B(H39D,H39E,H39F), C35A(H35A,H35B,H35C), C35B(H35D,
 H35E,H35F)
;
_shelx_res_checksum              32011
_shelx_hkl_checksum              84998
_olex2_date_sample_data_collection 2021-08-12
_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
;