Asymmetric Synthesis, Structures, and Chiroptical Properties of Helical Cycloparaphenylenes
Nogami, Juntaro; Nagashima, Yuki; Miyamoto, Kazunori; Muranaka, Atsuya; Uchiyama, Masanobu; Tanaka, Ken; Chemical Science  (2021) –; doi:10.1039/D1SC00861G

data_1562235
_publ_section_title
;
 Asymmetric Synthesis, Structures, and Chiroptical Properties of Helical
 Cycloparaphenylenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC00861G
_journal_year                    2021
_chemical_formula_moiety         'C96 H80 O8, C H2 Cl2'
_chemical_formula_sum            'C97 H80 Cl2 O8'
_chemical_formula_weight         1444.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-12-17 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                96.529(2)
_cell_angle_beta                 97.374(3)
_cell_angle_gamma                110.822(3)
_cell_formula_units_Z            2
_cell_length_a                   12.9562(5)
_cell_length_b                   14.7057(5)
_cell_length_c                   21.8040(3)
_cell_measurement_reflns_used    11735
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.1870
_cell_measurement_theta_min      3.2790
_cell_volume                     3793.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -66.00 -41.00   0.50   12.47    --  -39.95 119.00  14.00   50
  2  \w    -84.00 -59.00   0.50   56.00    --  -84.50 119.00  14.00   50
  3  \w    -42.00  -5.00   0.50   56.00    --  -84.50  45.00 120.00   74
  4  \w    -29.00  -2.00   0.50   56.00    --  -84.50  30.00 150.00   54
  5  \w    -84.00 -48.00   0.50   56.00    --  -84.50 157.00 169.00   72
  6  \w    -98.00 -73.00   0.50   12.47    --  -39.95 157.00 169.00   50
  7  \w     -1.00  29.00   0.50   12.47    --   39.95  96.00  92.09   60
  8  \w     53.00  90.00   0.50   12.47    --   39.95 157.00 169.00   74
  9  \w     91.00 128.00   0.50   56.00    --  113.69 119.00  14.00   74
 10  \w     86.00 177.00   0.50   56.00    --  113.69  61.00   0.00  182
 11  \w    140.00 176.00   0.50   56.00    --  113.69  61.00  90.00   72
 12  \w     91.00 120.00   0.50   56.00    --  113.69  61.00  90.00   58
 13  \w     79.00 175.00   0.50   56.00    --  113.69  77.00 150.00  192
 14  \w     82.00 107.00   0.50   56.00    --  113.69 157.00 169.00   50
 15  \w     30.00 178.00   0.50   56.00    --  113.69   0.00 -30.00  296
 16  \w     92.00 154.00   0.50   56.00    --  113.69  45.00 -60.00  124
 17  \w     77.00 178.00   0.50   56.00    --  113.69  30.00-120.00  202
 18  \w     70.00 105.00   0.50   56.00    --  113.69 -95.00 -90.00   70
 19  \w     69.00  95.00   0.50   56.00    --  113.69-119.00 -70.00   52
 20  \w     39.00  73.00   0.50   56.00    --  113.69 -61.00-120.00   68
 21  \w     69.00 105.00   0.50   56.00    --  113.69 -95.00-180.00   72
 22  \w     35.00  68.00   0.50   56.00    --  113.69-119.00 -70.00   66
 23  \w     40.00  76.00   0.50   56.00    --  113.69 -61.00-150.00   72
 24  \w     34.00 105.00   0.50   56.00    --  113.69 -95.00-150.00  142
 25  \w     40.00  74.00   0.50   56.00    --  113.69 -61.00 -60.00   68
 26  \w     47.00  73.00   0.50   56.00    --  113.69 -61.00   0.00   52
 27  \w     43.00  72.00   0.50   56.00    --  113.69 -61.00  30.00   58
 28  \w     45.00  74.00   0.50   56.00    --  113.69 -61.00  90.00   58
 29  \w     49.00  95.00   0.50   56.00    --  113.69 -95.00 150.00   92
 30  \w     62.00  87.00   0.50   56.00    --  113.69-157.00 134.00   50
 31  \w     97.00 129.00   0.50   56.00    --  113.69-148.00  44.48   64
 32  \w     60.00 105.00   0.50   56.00    --  113.69 -95.00  30.00   90
 33  \w     35.00 105.00   0.50   56.00    --  113.69 -95.00 120.00  140
 34  \w     35.00 102.00   0.50   56.00    --  113.69 -95.00  60.00  134
 35  \w     35.00  84.00   0.50   56.00    --  113.69 -95.00 -30.00   98
 36  \w     64.00 110.00   0.50   12.47    --   39.95-157.00 134.00   92
 37  \w     10.00  95.00   0.50   12.47    --   39.95-119.00 -70.00  170
 38  \w     37.00  73.00   0.50   56.00    --  113.69-125.00-180.00   72
 39  \w    -43.00  25.00   0.50   12.47    --   39.95 -19.00   0.00  136
 40  \w    -40.00  45.00   0.50   12.47    --   39.95 -38.00 120.00  170
 41  \w      2.00  27.00   0.50   12.47    --   39.95 -19.00 150.00   50
 42  \w    -43.00 -10.00   0.50   12.47    --   39.95 -19.00 150.00   66
 43  \w    -15.00  23.00   0.50   12.47    --  -39.95  19.00 -30.00   76
 44  \w    -29.00  -4.00   0.50   56.00    --  -84.50  30.00 -60.00   50
 45  \w    -28.00  -3.00   0.50   56.00    --  -84.50  30.00-120.00   50
 46  \w    -11.00  15.00   0.50   12.47    --  -39.95  19.00-180.00   52
 47  \w     54.00  93.00   0.50   12.47    --   39.95 178.00 -90.00   78
 48  \w     82.00 142.00   0.50   56.00    --  113.69 125.00 -60.00  120
 49  \w    -78.00 -52.00   0.50   12.47    --  -39.95-157.00 134.00   52
 50  \w   -109.00 -83.00   0.50   12.47    --  -39.95-157.00 134.00   52
 51  \w   -125.00-100.00   0.50   56.00    --  -84.50-157.00 134.00   50
 52  \w   -154.00-111.00   0.50   56.00    --  -84.50 -60.00 170.76   86
 53  \w   -145.00-120.00   0.50   56.00    --  -84.50-119.00 -70.00   50
 54  \w   -123.00 -39.00   0.50   56.00    --  -84.50 140.00 -48.15  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0404114000
_diffrn_orient_matrix_UB_12      0.0009964000
_diffrn_orient_matrix_UB_13      0.0634220000
_diffrn_orient_matrix_UB_21      -0.1163539000
_diffrn_orient_matrix_UB_22      -0.0093082000
_diffrn_orient_matrix_UB_23      -0.0335247000
_diffrn_orient_matrix_UB_31      -0.0395555000
_diffrn_orient_matrix_UB_32      -0.1133868000
_diffrn_orient_matrix_UB_33      -0.0091627000
_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  0.0561
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            44112
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         2.074
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane, CH2Cl2'
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.943
_refine_diff_density_min         -1.514
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     968
_refine_ls_number_reflns         13862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.1189
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1830P)^2^+8.0754P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3223
_refine_ls_wR_factor_ref         0.3345
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11268
_reflns_number_total             13862
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00861g2.cif
_cod_data_source_block           exp_775
_cod_database_code               1562235
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C95 H78 O8'
_reflns_odcompleteness_completeness 99.88
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C85(H85A,H85B), C35(H35A,H35B), C63(H63A,H63B), C21(H21A,
 H21B), C11(H11A,H11B), C77(H77A,H77B), C73(H73A,H73B), C89(H89A,H89B),
 C93(H93A,H93B), C86(H86A,H86B), C87(H87A,H87B), C74(H74A,H74B), C94(H94A,H94B),
  C75(H75A,H75B), C57(H57A,H57B), C95(H95A,H95B), C90(H90A,H90B), C51(H51A,
 H51B), C91(H91A,H91B), C106(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C60(H60), C16(H16), C83(H83), C39(H39), C15(H15), C24(H24), C40(H40),
 C100(H100), C3(H3), C69(H69), C104(H104), C103(H103), C59(H59), C50(H50),
 C99(H99), C82(H82), C58(H58), C97(H97), C98(H98), C80(H80), C54(H54),
 C101(H101), C47(H47), C81(H81), C68(H68), C102(H102), C66(H66), C67(H67)
2.c Idealised Me refined as rotating group:
 C76(H76A,H76B,H76C), C96(H96A,H96B,H96C), C88(H88A,H88B,H88C), C92(H92A,H92B,
 H92C)
;
_shelx_res_checksum              94620
_shelx_hkl_checksum              81569
_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 2.296
_oxdiff_exptl_absorpt_empirical_full_min 0.384