Controlling helicene's pitch by molecular tethering
Agrawal, Abhijeet R.; Shiouki, Israa; Deree, Yinon; Bogoslavsky, Benny; Gidron, Ori; Organic & Biomolecular Chemistry 22 (2024) 1365–1368; doi:10.1039/D3OB02075D

data_7159774
_publ_section_title
;
 Controlling helicene's pitch by molecular tethering
;
_journal_issue                   7
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1365
_journal_page_last               1368
_journal_paper_doi               10.1039/D3OB02075D
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C48 H44 O2, C0.5 O0.25'
_chemical_formula_sum            'C48.5 H44 O2.25'
_chemical_formula_weight         662.83
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.799(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9449(7)
_cell_length_b                   9.9148(4)
_cell_length_c                   22.8990(9)
_cell_measurement_reflns_used    5720
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.2950
_cell_measurement_theta_min      2.2480
_cell_volume                     3956.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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    -32.00   4.00   0.50  520.00    --   -3.94 -13.00-154.00   72
  2  \w    -72.00 -41.00   0.50  520.00    --   -3.94 -13.00-154.00   62
  3  \w    -13.00  33.00   0.50  520.00    --    2.69 -99.00-150.00   92
  4  \w    -22.00  24.00   0.50  520.00    --   -3.94 -99.00   0.00   92
  5  \w     -6.00  65.00   0.50  520.00    --   -3.94  13.00  17.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0308161000
_diffrn_orient_matrix_UB_12      -0.0042105000
_diffrn_orient_matrix_UB_13      -0.0259010000
_diffrn_orient_matrix_UB_21      -0.0264720000
_diffrn_orient_matrix_UB_22      0.0109775000
_diffrn_orient_matrix_UB_23      0.0181093000
_diffrn_orient_matrix_UB_31      0.0022652000
_diffrn_orient_matrix_UB_32      0.0705547000
_diffrn_orient_matrix_UB_33      -0.0043814000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28702
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.249
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_description       needle
_exptl_crystal_F_000             1412
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.042
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         7751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0791
_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^)+(0.1712P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2177
_refine_ls_wR_factor_ref         0.2474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4905
_reflns_number_total             7751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02075d2.cif
_cod_data_source_block           origi95
_cod_depositor_comments
'Adding full bibliography for 7159772--7159774.cif.'
_cod_original_formula_sum        'C48.50 H44 O2.25'
_cod_database_code               7159774
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C50 H44 O2'
_chemical_oxdiff_usercomment     ARA_2_32C6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.983
_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. Others
 Fixed Sof: O1E(0.25) C1EA(0.125) C1EB(0.125) C2EA(0.125) C2EB(0.125)
3.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,
 H47B), C48(H48A,H48B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C11(H11), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28)
3.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              70848
_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 2.037
_oxdiff_exptl_absorpt_empirical_full_min 0.589