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_7129869
_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         'C39 H29 N3 O4, 1.5(C7 H8)'
_chemical_formula_sum            'C49.5 H41 N3 O4'
_chemical_formula_weight         741.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.04517(12)
_cell_length_b                   24.0736(3)
_cell_length_c                   36.4747(5)
_cell_measurement_reflns_used    12451
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      68.6810
_cell_measurement_theta_min      3.0310
_cell_volume                     7942.36(18)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -68.00  42.00   1.00    7.65    --  -22.92  77.00  30.00  110
  2  \w    -23.00  42.00   1.00    7.65    --   22.92  77.00 120.00   65
  3  \w     61.00 120.00   1.00    7.65    --   22.92 178.00   0.00   59
  4  \w     61.00 120.00   1.00    7.65    --   22.92 178.00-120.00   59
  5  \w    -83.00   6.00   1.00   30.50    --  -69.12 111.00 -90.00   89
  6  \w   -158.00 -82.00   1.00   30.50    --  -69.12 -77.00  30.00   76
  7  \w   -156.00 -83.00   1.00   30.50    --  -69.12-111.00 -30.00   73
  8  \w   -156.00 -83.00   1.00   30.50    --  -69.12-111.00 -90.00   73
  9  \w    104.00 156.00   1.00   30.50    --   69.12 111.00 -30.00   52
 10  \w    103.00 158.00   1.00   30.50    --   69.12  77.00  60.00   55
 11  \w    104.00 156.00   1.00   30.50    --   69.12 111.00-180.00   52
 12  \w     61.00 147.00   1.00   30.50    --   69.12 178.00   0.00   86
 13  \w    104.00 178.00   1.00   32.00    --  115.32  99.00 -60.00   74
 14  \w    104.00 178.00   1.00   32.00    --  115.32  77.00 120.00   74
 15  \w     66.00 144.00   1.00   32.00    --  115.32 178.00-150.00   78
 16  \w    100.00 176.00   1.00   32.00    --  115.32 125.00 -90.00   76
 17  \w    107.00 174.00   1.00   32.00    --  115.32  99.00-150.00   67
 18  \w    130.00 178.00   1.00   32.00    --  115.32  99.00-180.00   48
 19  \w    126.00 152.00   1.00   32.00    --  115.32  77.00  60.00   26
 20  \w    105.00 170.00   1.00   32.00    --  115.32  99.00  60.00   65
 21  \w    107.00 156.00   1.00   32.00    --  115.32  77.00 -90.00   49
 22  \w    104.00 177.00   1.00   32.00    --  115.32  77.00  90.00   73
 23  \w    125.00 175.00   1.00   32.00    --  115.32  65.00  30.00   50
;
_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  0.0197
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            27455
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        65.997
_diffrn_reflns_theta_max         65.997
_diffrn_reflns_theta_min         2.423
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86619
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       needle
_exptl_crystal_F_000             3128
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 5322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     963
_refine_ls_number_reflns         13818
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1059P)^2^+6.0781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                12824
_reflns_number_total             13818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06974h1.cif
_cod_data_source_block           ndib-nhme-tol
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C99 H82 N6 O8'
_cod_original_formula_weight         1483.70
_cod_original_formula_moiety         '2(C39 H29 N3 O4), 3(C7 H8)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        7942.37(17)
_cod_database_code               7129869
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C92-C86
 1.51 with sigma of 0.02
 C86-C87 = C86-C91 = C88-C89
 1.39 with sigma of 0.02
 C87-C88 = C89-C90 = C90-C91
 1.38 with sigma of 0.02
 C99-C93
 1.51 with sigma of 0.02
 C93-C94 = C93-C98 = C95-C96
 1.39 with sigma of 0.02
 C94-C95 = C96-C97 = C97-C98
 1.38 with sigma of 0.02
 C86-C88
 2.42 with sigma of 0.04
 C87-C89
 2.39 with sigma of 0.04
 C86-C90
 2.41 with sigma of 0.04
 C88-C90 = C89-C91
 2.4 with sigma of 0.04
 C92-C87 = C92-C91
 2.52 with sigma of 0.04
 C95-C97 = C96-C98
 2.4 with sigma of 0.04
 C93-C97
 2.41 with sigma of 0.04
 C99-C94 = C99-C98
 2.52 with sigma of 0.04
 C93-C95
 2.42 with sigma of 0.04
 C94-C96
 2.39 with sigma of 0.04
 C86-C87 \\sim C87-C88 \\sim C88-C89 \\sim C89-C90 \\sim C90-C91 \\sim C91-C86
 with sigma of 0.02
 C86-C90 \\sim C86-C88 \\sim C91-C89 \\sim C87-C91 \\sim C88-C90 \\sim C87-C89
 with sigma of 0.04
 C92-C91 \\sim C92-C87
 with sigma of 0.04
 C93-C97 \\sim C93-C95 \\sim C98-C96 \\sim C94-C98 \\sim C95-C97 \\sim C94-C96
 with sigma of 0.04
 C99-C98 \\sim C99-C94
 with sigma of 0.04
 C93-C94 \\sim C94-C95 \\sim C95-C96 \\sim C96-C97 \\sim C97-C98 \\sim C98-C93
 with sigma of 0.02
3. Restrained planarity
 C92, C86, C87, C88, C89, C90, C91
 with sigma of 0.1
 C99, C93, C94, C95, C96, C97, C98
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C92 \\sim C86 \\sim C87 \\sim C88 \\sim C89 \\sim C90 \\sim C91: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C99 \\sim C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97 \\sim C98: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C92, C86, C87, C88, C89, C90, C91
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C99, C93, C94, C95, C96, C97, C98
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C75(H75A,H75B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C76(H76A,
 H76B), C77(H77A,H77B)
6.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C3(H3), C10(H10), C49(H49), C42(H42), C4(H4), C48(H48), C43(H43),
 C24(H24), C62(H62), C23(H23), C32(H32), C63(H63), C60(H60), C33(H33), C58(H58),
  C27(H27), C18(H18), C21(H21), C59(H59), C57(H57), C72(H72), C28(H28),
 C31(H31), C20(H20), C30(H30), C19(H19), C70(H70), C71(H71), C66(H66), C69(H69),
  C67(H67), C84(H84), C80(H80), C83(H83), C82(H82), C81(H81), C87(H87),
 C88(H88), C89(H89), C90(H90), C91(H91), C94(H94), C95(H95), C96(H96), C97(H97),
  C98(H98)
6.c Idealised Me refined as rotating group:
 C74(H74A,H74B,H74C), C78(H78A,H78B,H78C), C39(H39A,H39B,H39C), C35(H35A,H35B,
 H35C), C85(H85A,H85B,H85C), C92(H92A,H92B,H92C), C99(H99A,H99B,H99C)
;
_shelx_res_checksum              11256
_shelx_hkl_checksum              48452
_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
;