Modulation of Chiroptical Properties in a Series of Helicene-like Compounds.
Guy, Laure; Mosser, Maëlle; Pitrat, Delphine; Mulatier, Jean-Christophe; Kukułka, Mercedes; Srebro-Hooper, Monika; Jeanneau, Erwann; Bensalah-Ledoux, Amina; Baguenard, Bruno; Guy, Stéphan; The Journal of organic chemistry 84 (2019) 10870–10876; doi:10.1021/acs.joc.9b01465

data_4033798
_publ_section_title
;
 Modulation of Chiroptical Properties in a Series of Helicene-like
 Compounds.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10870
_journal_page_last               10876
_journal_paper_doi               10.1021/acs.joc.9b01465
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C44 H32 N2 O2, 2(C2 H3 N)'
_chemical_formula_sum            'C48 H38 N4 O2'
_chemical_formula_weight         702.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 117.408(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.080(2)
_cell_length_b                   8.0155(5)
_cell_length_c                   20.6822(18)
_cell_measurement_reflns_used    13629
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.9000
_cell_measurement_theta_min      4.0850
_cell_volume                     3543.8(6)
_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_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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   -114.00 -13.00   1.00    5.00    --  -41.64 -61.00  42.00  101
  2  \w     13.00 114.00   1.00    5.00    --   41.64  61.00-179.00  101
  3  \w     63.00 165.00   1.00   20.00    --   92.50  61.00-179.00  102
  4  \w     20.00 122.00   1.00   20.00    --   92.50 -61.00  42.00  102
  5  \w     -3.00  24.00   1.00    5.00    --   32.00  84.00-109.21   27
  6  \w    -71.00  31.00   1.00    5.00    --  -41.64  61.00-179.00  102
  7  \w     -3.00  96.00   1.00    5.00    --   41.64-125.00  60.00   99
  8  \w     17.00 116.00   1.00    5.00    --   41.64  37.00 120.00   99
  9  \w      1.00 122.00   1.00    5.00    --   41.64  19.00  60.00  121
 10  \w    -29.00  70.00   1.00    5.00    --   41.64 -61.00  42.00   99
 11  \w     15.00  47.00   1.00    5.00    --   48.00  79.00 124.78   32
 12  \w     15.00  45.00   1.00    5.00    --   48.00  79.00  12.90   30
 13  \w     20.00  51.00   1.00    5.00    --   52.00  78.00 179.00   31
 14  \w     19.00  51.00   1.00    5.00    --   52.00  79.00-100.43   32
 15  \w     23.00  61.00   1.00    5.00    --   56.00  77.00-152.16   38
 16  \w     25.00  58.00   1.00    5.00    --   56.00  77.00 -61.20   33
 17  \w     27.00  53.00   1.00    5.00    --   60.00  78.00  56.33   26
 18  \w     27.00  54.00   1.00    5.00    --   60.00  77.00  24.89   27
 19  \w     27.00  54.00   1.00    5.00    --   60.00  79.00 -43.61   27
 20  \w    112.00 137.00   1.00    5.00    --   60.00  78.00  56.33   25
 21  \w     32.00  59.00   1.00    5.00    --   64.00  79.00 103.53   27
 22  \w     31.00  63.00   1.00    5.00    --   64.00  78.00-115.87   32
 23  \w     35.00  69.00   1.00   20.00    --   68.00  79.00-154.10   34
 24  \w     36.00  77.00   1.00   20.00    --   68.00  76.00 -46.95   41
 25  \w     36.00  61.00   1.00   20.00    --   68.00  78.00  57.42   25
 26  \w     39.00  65.00   1.00   20.00    --   72.00  77.00 128.00   26
 27  \w    111.00 147.00   1.00   20.00    --   72.00  78.00  33.13   36
 28  \w     39.00  66.00   1.00   20.00    --   72.00  78.00 -11.25   27
 29  \w     39.00  65.00   1.00   20.00    --   72.00  78.00  33.13   26
 30  \w     40.00  67.00   1.00   20.00    --   72.00  79.00  74.61   27
 31  \w     40.00  67.00   1.00   20.00    --   72.00  78.00 148.71   27
 32  \w     40.00  67.00   1.00   20.00    --   72.00  77.00-179.65   27
 33  \w     39.00  68.00   1.00   20.00    --   72.00  79.00-109.41   29
 34  \w     47.00  84.00   1.00   20.00    --   80.00  79.00 -45.22   37
 35  \w    123.00 164.00   1.00   20.00    --   92.50  77.00 150.00   41
 36  \w     60.00  86.00   1.00   20.00    --   92.50  77.00 150.00   26
 37  \w     10.00  46.00   1.00   20.00    --   92.50 -92.00  47.05   36
 38  \w    129.00 156.00   1.00   20.00    --   92.50  77.00  60.00   27
 39  \w     60.00  86.00   1.00   20.00    --   92.50  77.00  60.00   26
 40  \w    116.00 155.00   1.00   20.00    --   92.50  77.00 -60.00   39
 41  \w     60.00 126.00   1.00   20.00    --   92.50  77.00 120.00   66
 42  \w     12.00  37.00   1.00   20.00    --   92.50 -94.00 -60.00   25
 43  \w     60.00 150.00   1.00   20.00    --   92.50  77.00-150.00   90
 44  \w     60.00 101.00   1.00   20.00    --   92.50  77.00 -60.00   41
 45  \w     74.00 130.00   1.00   20.00    --   92.50 -93.00 166.60   56
 46  \w     21.00  46.00   1.00   20.00    --   92.50 -93.00 166.60   25
 47  \w     99.00 126.00   1.00   20.00    --   92.50 -93.00 -74.03   27
 48  \w    132.00 158.00   1.00   20.00    --   92.50  45.00  90.00   26
 49  \w     20.00  55.00   1.00   20.00    --   92.50 -45.00-150.00   35
 50  \w     21.00  74.00   1.00   20.00    --   92.50 -45.00  60.00   53
 51  \w    118.00 163.00   1.00   20.00    --   92.50  77.00-120.00   45
 52  \w     60.00 151.00   1.00   20.00    --   92.50  77.00   0.00   91
 53  \w     60.00  87.00   1.00   20.00    --   92.50  77.00-120.00   27
 54  \w     10.00  61.00   1.00   20.00    --   92.50 -93.00 -74.03   51
 55  \w     10.00  58.00   1.00   20.00    --   92.50 -93.00  -4.94   48
 56  \w     71.00 109.00   1.00   20.00    --   92.50 -93.00  -4.94   38
 57  \w     20.00  70.00   1.00   20.00    --   92.50 -61.00 -90.00   50
 58  \w     53.00  80.00   1.00   20.00    --   92.50 -94.00 -60.00   27
 59  \w     29.00  68.00   1.00   20.00    --   92.50 -45.00  30.00   39
 60  \w     71.00 115.00   1.00   20.00    --   92.50  61.00-150.00   44
 61  \w    128.00 154.00   1.00   20.00    --   92.50  77.00 -90.00   26
 62  \w     60.00  92.00   1.00   20.00    --   92.50-125.00  90.00   32
 63  \w     20.00  76.00   1.00   20.00    --   92.50 -45.00 120.00   56
 64  \w     20.00  45.00   1.00   20.00    --   92.50-125.00  90.00   25
 65  \w     33.00 119.00   1.00   20.00    --   92.50 -61.00 120.00   86
 66  \w     56.00  93.00   1.00   20.00    --   92.50  15.00 150.00   37
 67  \w     62.00  88.00   1.00   20.00    --   92.50 -54.00-169.96   26
 68  \w     60.00 116.00   1.00   20.00    --   92.50  77.00 -90.00   56
 69  \w     67.00 113.00   1.00   20.00    --   92.50  45.00  90.00   46
 70  \w     44.00  91.00   1.00   20.00    --   92.50  15.00 -90.00   47
 71  \w     98.00 151.00   1.00   20.00    --   92.50  61.00 150.00   53
 72  \w    123.00 167.00   1.00   20.00    --   92.50  77.00 -30.00   44
 73  \w     75.00 162.00   1.00   20.00    --   92.50  45.00 -30.00   87
 74  \w     60.00  92.00   1.00   20.00    --   92.50  77.00 -30.00   32
 75  \w    130.00 169.00   1.00   20.00    --   92.50  77.00  90.00   39
 76  \w     78.00 131.00   1.00   20.00    --   92.50 125.00  60.00   53
 77  \w     19.00  48.00   1.00   20.00    --   92.50 -92.00-126.15   29
 78  \w     66.00 130.00   1.00   20.00    --   92.50 -92.00-126.15   64
 79  \w    140.00 168.00   1.00   20.00    --   92.50  77.00-180.00   28
 80  \w     40.00  99.00   1.00   20.00    --   92.50 -77.00  60.00   59
 81  \w     60.00  97.00   1.00   20.00    --   92.50  77.00-180.00   37
 82  \w    121.00 158.00   1.00   20.00    --   92.50  15.00 -90.00   37
 83  \w     60.00 101.00   1.00   20.00    --   92.50  77.00  90.00   41
 84  \w    135.00 161.00   1.00   20.00    --   92.50  61.00 -13.76   26
 85  \w     63.00 130.00   1.00   20.00    --   92.50  61.00 -13.76   67
 86  \w    108.00 142.00   1.00   20.00    --   92.50  77.00  30.00   34
 87  \w    147.00 172.00   1.00   20.00    --   92.50  15.00 150.00   25
 88  \w    119.00 145.00   1.00   20.00    --   92.50  61.00-150.00   26
 89  \w     98.00 124.00   1.00   20.00    --   92.50  15.00 150.00   26
 90  \w     74.00 120.00   1.00   20.00    --   92.50 -61.00 -90.00   46
 91  \w     60.00  93.00   1.00   20.00    --   92.50  77.00  30.00   33
 92  \w     79.00 131.00   1.00   20.00    --   92.50 -92.00  47.05   52
 93  \w    141.00 167.00   1.00   20.00    --   92.50  77.00 120.00   26
 94  \w     66.00 168.00   1.00   20.00    --   92.50  30.00 -60.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0542060000
_diffrn_orient_matrix_UB_12      0.0367086000
_diffrn_orient_matrix_UB_13      0.0760587000
_diffrn_orient_matrix_UB_21      0.0222794000
_diffrn_orient_matrix_UB_22      0.1429358000
_diffrn_orient_matrix_UB_23      -0.0321948000
_diffrn_orient_matrix_UB_31      -0.0418725000
_diffrn_orient_matrix_UB_32      0.1232010000
_diffrn_orient_matrix_UB_33      0.0148722000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47158
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.270
_diffrn_reflns_theta_max         67.270
_diffrn_reflns_theta_min         4.136
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             1480
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by'
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+3.1270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             3157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01465_si_003.cif
_cod_data_source_block           bisfnaphome
_cod_original_cell_volume        3543.9(6)
_cod_database_code               4033798
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C94 H75 N6 O8'
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              51281
_shelx_hkl_checksum              89541
_olex2_date_sample_data_collection 2015-03-25
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id BisFNaphOME
_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 1.707
_oxdiff_exptl_absorpt_empirical_full_min 0.596