Comprehensive analysis of C–H⋯π(alkyne) interactions in the crystal packing of diastereomers of 1,2-di(7′-methoxynaphth-1′-yl)-3,6-di(4′′-n-propylphenylethynyl)benzene
Nakamura, Minami; Kashiwagi, Yukiyasu; Morisue, Mitsuhiko; CrystEngComm 26 (2024) 3964–3972; doi:10.1039/D4CE00495G

data_7248908
_publ_section_title
;
 Comprehensive analysis of C--H&#x22EF;\p(alkyne) interactions in the
 crystal packing of diastereomers of
 1,2-di(7&#x2032;-methoxynaphth-1&#x2032;-yl)-3,6-di(4&#x2032;&#x2032;-n-propylphenylethynyl)benzene
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              3964
_journal_page_last               3972
_journal_paper_doi               10.1039/D4CE00495G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C50 H42 O2'
_chemical_formula_sum            'C50 H42 O2'
_chemical_formula_weight         674.83
_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             2023-03-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-11 deposited with the CCDC.	2024-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                97.3650(10)
_cell_angle_beta                 102.2750(10)
_cell_angle_gamma                93.9240(10)
_cell_formula_units_Z            2
_cell_length_a                   9.53810(10)
_cell_length_b                   11.07600(10)
_cell_length_c                   18.5558(2)
_cell_measurement_reflns_used    36629
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.7450
_cell_measurement_theta_min      4.0280
_cell_volume                     1890.41(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.939
_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     44.00 108.00   0.50    0.15    --  107.51-125.00 150.00  128
  2  \w     82.00 107.00   0.50    0.15    --  107.51-102.00  74.29   50
  3  \w     37.00  90.00   0.50    0.15    --  107.51 -99.00  60.00  106
  4  \w     37.00  65.00   0.50    0.15    --  107.51 -99.00   0.00   56
  5  \w     74.00  99.00   0.50    0.15    --  107.51 -99.00   0.00   50
  6  \w     44.00 110.00   0.50    0.15    --  107.51-125.00-150.00  132
  7  \w     49.00  96.00   0.50    0.15    --  107.51 -99.00-150.00   94
  8  \w     37.00  99.00   0.50    0.15    --  107.51 -99.00-120.00  124
  9  \w     54.00 104.00   0.50    0.15    --  107.51 -99.00 -90.00  100
 10  \w     44.00 104.00   0.50    0.15    --  107.51 -93.00 -49.00  120
 11  \w     37.00  96.00   0.50    0.15    --  107.51 -99.00 150.00  118
 12  \w     13.00  77.00   0.50    0.05    --   47.80 -93.00 -49.00  128
 13  \w     -5.00  40.00   0.50    0.05    --   47.80 -38.00   0.00   90
 14  \w     37.00  66.00   0.50    0.15    --  107.51 -57.00   0.00   58
 15  \w     40.00  65.00   0.50    0.15    --  107.51 -57.00 -30.00   50
 16  \w     35.00  61.00   0.50    0.15    --  107.51 -57.00 -60.00   52
 17  \w     37.00  65.00   0.50    0.15    --  107.51 -57.00-120.00   56
 18  \w     37.00  65.00   0.50    0.15    --  107.51 -57.00 -90.00   56
 19  \w     35.00  66.00   0.50    0.15    --  107.51 -57.00 150.00   62
 20  \w    132.00 157.00   0.50    0.15    --  107.51  93.00  62.00   50
 21  \w     28.00  54.00   0.50    0.05    --   50.00  77.00 -88.84   52
 22  \w     43.00  77.00   0.50    0.05    --   66.00  77.00 -68.05   68
 23  \w     57.00  82.00   0.50    0.05    --   50.00  77.00 -88.84   50
 24  \w    102.00 139.00   0.50    0.05    --   66.00  77.00 -68.05   74
 25  \w     97.00 124.00   0.50    0.05    --   58.00  77.00 -30.38   54
 26  \w     47.00  73.00   0.50    0.05    --   70.00  77.00  10.54   52
 27  \w      3.00  28.00   0.50    0.05    --   26.00  78.00  29.17   50
 28  \w     37.00  78.00   0.50    0.05    --   58.00  76.00  74.15   82
 29  \w     84.00 110.00   0.50    0.05    --   70.00  77.00  10.54   52
 30  \w     48.00  74.00   0.50    0.05    --   70.00  76.00  44.69   52
 31  \w     43.00  70.00   0.50    0.05    --   66.00  77.00  -7.76   54
 32  \w     35.00  74.00   0.50    0.05    --   58.00  77.00 -30.38   78
 33  \w     48.00  74.00   0.50    0.05    --   70.00  75.00-106.72   52
 34  \w     49.00  75.00   0.50    0.05    --   70.00  75.00-133.28   52
 35  \w     32.00  58.00   0.50    0.05    --   54.00  75.00-149.45   52
 36  \w     47.00  73.00   0.50    0.05    --   70.00  77.00-165.50   52
 37  \w    103.00 129.00   0.50    0.05    --   70.00  75.00-106.72   52
 38  \w    139.00 168.00   0.50    0.15    --   98.00  75.00 -77.27   58
 39  \w     78.00 126.00   0.50    0.15    --   98.00  75.00 -77.27   96
 40  \w     37.00  63.00   0.50    0.05    --   58.00  74.00 -76.04   52
 41  \w     37.00  64.00   0.50    0.05    --   58.00  72.00  70.13   54
 42  \w     43.00  70.00   0.50    0.05    --   62.00  72.00 100.57   54
 43  \w     12.00  40.00   0.50    0.05    --   38.00  86.00 154.57   56
 44  \w     17.00  42.00   0.50    0.05    --   46.00  90.00  63.84   50
 45  \w    -13.00  18.00   0.50    0.05    --   18.00  96.00 149.51   62
 46  \w     14.00  39.00   0.50    0.05    --   42.00  88.00 -32.64   50
 47  \w      7.00  32.00   0.50    0.05    --   34.00  86.00-111.14   50
 48  \w    -19.00  15.00   0.50    0.05    --   14.00 101.00 -67.75   68
 49  \w    -61.00 -22.00   0.50    0.05    --  -47.80  93.00  62.00   78
 50  \w    -78.00 -33.00   0.50    0.15    --  -91.75  93.00  62.00   90
 51  \w    -15.00  20.00   0.50    0.05    --  -47.80  93.00  62.00   70
 52  \w    -65.00 -23.00   0.50    0.15    --  -91.75  57.00 120.00   84
 53  \w   -158.00 -79.00   0.50    0.15    --  -91.75 -60.00 -11.15  158
 54  \w    -95.00 -69.00   0.50    0.15    --  -91.75 -77.00 -60.00   52
 55  \w   -154.00 -72.00   0.50    0.15    --  -91.75 -77.00 -90.00  164
 56  \w   -142.00 -69.00   0.50    0.15    --  -91.75 -77.00-120.00  146
 57  \w   -162.00-100.00   0.50    0.15    --  -91.75 -77.00 -60.00  124
 58  \w   -163.00-135.00   0.50    0.15    --  -91.75 -76.00 113.77   56
 59  \w   -129.00 -69.00   0.50    0.15    --  -91.75 -76.00 113.77  120
 60  \w    -81.00 -56.00   0.50    0.15    --  -78.00 -75.00 137.63   50
 61  \w    -97.00 -71.00   0.50    0.15    --  -91.75 -77.00 150.00   52
 62  \w    -77.00 -51.00   0.50    0.15    --  -74.00 -76.00  89.19   52
 63  \w    -86.00 -60.00   0.50    0.15    --  -82.00 -75.00  82.61   52
 64  \w   -104.00 -69.00   0.50    0.15    --  -91.75 -76.00 -42.98   70
 65  \w   -140.00 -70.00   0.50    0.15    --  -91.75 -75.00 -52.88  140
 66  \w   -130.00-104.00   0.50    0.15    --  -86.00 -75.00 -94.46   52
 67  \w    -89.00 -64.00   0.50    0.15    --  -86.00 -75.00-159.49   50
 68  \w   -163.00 -71.00   0.50    0.15    --  -91.75 -75.00-160.23  184
 69  \w    -81.00 -56.00   0.50    0.15    --  -78.00 -75.00-119.56   50
 70  \w    -89.00 -64.00   0.50    0.15    --  -86.00 -75.00 -94.46   50
 71  \w   -117.00 -70.00   0.50    0.15    --  -91.75 -75.00 -12.22   94
 72  \w   -161.00-135.00   0.50    0.15    --  -91.75 -75.00 -12.22   52
 73  \w   -142.00-116.00   0.50    0.15    --  -78.00 -75.00 137.63   52
 74  \w   -159.00-108.00   0.50    0.15    --  -86.00 -74.00 119.96  102
 75  \w   -104.00 -64.00   0.50    0.15    --  -86.00 -74.00 119.96   80
 76  \w    -66.00 -41.00   0.50    0.05    --  -62.00 -74.00 145.38   50
 77  \w   -163.00 -70.00   0.50    0.15    --  -91.75 -74.00  92.55  186
 78  \w   -147.00-121.00   0.50    0.15    --  -86.00 -74.00  17.42   52
 79  \w   -110.00 -64.00   0.50    0.15    --  -86.00 -74.00  58.89   92
 80  \w    -72.00 -41.00   0.50    0.05    --  -62.00 -73.00 104.99   62
 81  \w    -95.00 -64.00   0.50    0.15    --  -86.00 -74.00  17.42   62
 82  \w    -83.00 -53.00   0.50    0.15    --  -74.00 -73.00  56.00   60
 83  \w    -84.00 -57.00   0.50    0.15    --  -78.00 -73.00 -83.50   54
 84  \w    -79.00 -53.00   0.50    0.15    --  -74.00 -73.00-114.32   52
 85  \w   -106.00 -73.00   0.50    0.15    --  -91.75 -73.00-131.92   66
 86  \w   -150.00-115.00   0.50    0.15    --  -91.75 -73.00-131.92   70
 87  \w   -142.00-116.00   0.50    0.15    --  -82.00 -72.00-158.73   52
 88  \w    -87.00 -61.00   0.50    0.15    --  -82.00 -72.00-158.73   52
 89  \w    -83.00 -57.00   0.50    0.15    --  -78.00 -72.00 -61.24   52
 90  \w   -152.00 -71.00   0.50    0.15    --  -91.75 -71.00  36.65  162
 91  \w   -142.00 -73.00   0.50    0.15    --  -91.75 -71.00 162.75  138
 92  \w    -88.00 -57.00   0.50    0.15    --  -78.00 -72.00 149.38   62
 93  \w   -163.00 -72.00   0.50    0.15    --  -91.75 -69.00 145.21  182
 94  \w   -162.00 -73.00   0.50    0.15    --  -90.00 -67.00  46.99  178
 95  \w    -73.00 -47.00   0.50    0.05    --  -66.00 -70.00  89.56   52
 96  \w   -144.00-118.00   0.50    0.15    --  -82.00 -67.00 -13.75   52
 97  \w   -143.00-110.00   0.50    0.15    --  -82.00 -67.00-104.26   66
 98  \w   -104.00 -63.00   0.50    0.15    --  -82.00 -67.00-104.26   82
 99  \w    -94.00 -60.00   0.50    0.15    --  -78.00 -66.00 -48.68   68
100  \w    -89.00 -63.00   0.50    0.15    --  -82.00 -67.00 -13.75   52
101  \w    -99.00 -74.00   0.50    0.15    --  -91.75 -65.00  57.16   50
102  \w   -156.00-115.00   0.50    0.15    --  -91.75 -65.00  57.16   82
103  \w   -162.00-117.00   0.50    0.15    --  -91.75 -64.00 176.44   90
104  \w   -100.00 -75.00   0.50    0.15    --  -91.75 -64.00 176.44   50
105  \w   -120.00 -40.00   0.50    0.05    --  -47.80 -19.00  60.00  160
106  \w    -68.00 -25.00   0.50    0.05    --  -47.80 -77.00 120.00   86
107  \w    -74.00 -25.00   0.50    0.05    --  -47.80 -77.00 -30.00   98
108  \w    -66.00 -26.00   0.50    0.05    --  -47.80 -77.00 -90.00   80
109  \w    -64.00 -25.00   0.50    0.05    --  -47.80 -77.00-180.00   78
110  \w   -118.00 -74.00   0.50    0.05    --  -47.80 -77.00 -90.00   88
111  \w   -147.00-122.00   0.50    0.15    --  -91.75 -93.00 -49.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0291787000
_diffrn_orient_matrix_UB_12      -0.0019756000
_diffrn_orient_matrix_UB_13      -0.0786527000
_diffrn_orient_matrix_UB_21      -0.0774863000
_diffrn_orient_matrix_UB_22      0.1165733000
_diffrn_orient_matrix_UB_23      -0.0087958000
_diffrn_orient_matrix_UB_31      0.1440004000
_diffrn_orient_matrix_UB_32      0.0791806000
_diffrn_orient_matrix_UB_33      0.0333733000
_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  0.0466
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            58698
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.186
_diffrn_reflns_theta_min         2.463
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         7493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0514P)^2^+0.4560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6749
_reflns_number_total             7493
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {68db14d6-b355-456a-9492-69366699ba75}
_cod_data_source_file            d4ce00495g2.cif
_cod_data_source_block           230317_helicenepre_syn_01_autored
_cod_depositor_comments
'Adding full bibliography for 7248908--7248909.cif.'
_cod_database_code               7248908
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.803
_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:
 C50(H50A,H50B), C27(H27A,H27B), C26(H26A,H26B), C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C40(H40), C21(H21), C5(H5), C41(H41), C24(H24), C19(H19), C23(H23),
 C8(H8), C20(H20), C49(H49), C45(H45), C48(H48), C10(H10), C12(H12), C46(H46),
 C13(H13), C33(H33), C32(H32), C9(H9), C30(H30), C29(H29)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C3(H3A,H3B,H3C), C25(H25A,H25B,H25C), C52(H52A,H52B,H52C)
;
_shelx_res_checksum              79903
_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 1.638
_oxdiff_exptl_absorpt_empirical_full_min 0.463
_publcif_funding_html
;
;