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_7248909
_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      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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-28
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-01-12 deposited with the CCDC.	2024-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.40620(10)
_cell_length_b                   13.48000(10)
_cell_length_c                   20.5669(2)
_cell_measurement_reflns_used    17016
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8490
_cell_measurement_theta_min      3.9150
_cell_volume                     3716.76(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_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     35.00 121.00   0.50    0.06    --   47.93  64.00 142.00  172
  2  \w     90.00 173.00   0.50    0.25    --  107.38  63.00  -4.00  166
  3  \w    152.00 178.00   0.50    0.25    --  107.38  38.00 -60.00   52
  4  \w     95.00 124.00   0.50    0.25    --  107.38  38.00 -60.00   58
  5  \w     -7.00  26.00   0.50    0.06    --   47.93 -19.00-120.00   66
  6  \w     35.00  67.00   0.50    0.25    --  107.38 -63.00-141.00   64
  7  \w     37.00  62.00   0.50    0.25    --  107.38 -57.00 -90.00   50
  8  \w     35.00  61.00   0.50    0.25    --  107.38 -57.00 -60.00   52
  9  \w    -12.00  20.00   0.50    0.06    --   47.93 -19.00-150.00   64
 10  \w     38.00  72.00   0.50    0.25    --  107.38 -64.00   6.00   68
 11  \w     39.00  66.00   0.50    0.25    --  107.38 -57.00 150.00   54
 12  \w     40.00 104.00   0.50    0.25    --  107.38-102.00 129.00  128
 13  \w     44.00 103.00   0.50    0.25    --  107.38 -99.00 150.00  118
 14  \w    -15.00  16.00   0.50    0.06    --  -47.93  19.00 150.00   62
 15  \w    -54.00 -28.00   0.50    0.25    --  -91.75  57.00 -60.00   52
 16  \w    -38.00  14.00   0.50    0.06    --  -47.93  38.00-120.00  104
 17  \w   -161.00 -77.00   0.50    0.25    --  -91.75 -57.00  60.00  168
 18  \w   -150.00-124.00   0.50    0.25    --  -91.75-102.00 129.00   52
 19  \w   -138.00 -90.00   0.50    0.25    --  -91.75 -99.00 -30.00   96
 20  \w   -159.00 -77.00   0.50    0.25    --  -91.75-125.00 -60.00  164
;
_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      0.0223578000
_diffrn_orient_matrix_UB_12      -0.0244431000
_diffrn_orient_matrix_UB_13      0.0717152000
_diffrn_orient_matrix_UB_21      0.0817044000
_diffrn_orient_matrix_UB_22      0.0803725000
_diffrn_orient_matrix_UB_23      0.0009571000
_diffrn_orient_matrix_UB_31      -0.0776296000
_diffrn_orient_matrix_UB_32      0.0774735000
_diffrn_orient_matrix_UB_33      0.0216563000
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.304
_diffrn_reflns_theta_min         3.921
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2920 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.18(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         7386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0381P)^2^+0.3465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0746
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                7014
_reflns_number_total             7386
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {470b1412-454a-4832-b902-d6ec02b6d2a5}
_cod_data_source_file            d4ce00495g2.cif
_cod_data_source_block           231227_2_morisue_anti_5_autored
_cod_depositor_comments
'Adding full bibliography for 7248908--7248909.cif.'
_cod_database_code               7248909
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C50 H42 O2'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.907
_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:
 C39(H39A,H39B), C38(H38A,H38B), C49(H49A,H49B), C50(H50A,H50B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C27(H27), C33(H33), C16(H16), C12(H12), C17(H17), C45(H45), C24(H24),
 C20(H20), C11(H11), C25(H25), C8(H8), C7(H7), C34(H34), C10(H10), C48(H48),
 C21(H21), C37(H37), C44(H44), C22(H22), C36(H36), C47(H47)
2.c Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C40(H40A,H40B,H40C), C29(H29A,H29B,H29C), C51(H51A,H51B,
 H51C)
;
_shelx_res_checksum              72642
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.817
_publcif_funding_html
;
;