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_7159772
_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         'C42 H34'
_chemical_formula_sum            'C42 H34'
_chemical_formula_weight         538.69
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-23
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.138(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7697(4)
_cell_length_b                   15.4363(5)
_cell_length_c                   14.6704(5)
_cell_measurement_reflns_used    8510
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      32.7220
_cell_measurement_theta_min      2.0030
_cell_volume                     3100.36(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_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 0.834
_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    -64.00   0.00   0.50   60.00    --    6.81 -19.00  60.00  128
  2  \w     22.00  69.00   0.50   60.00    --    6.81  37.00  30.00   94
  3  \w    -14.00  21.00   0.50   60.00    --   -7.90 -99.00  60.00   70
  4  \w    -27.00  57.00   0.50   60.00    --   -7.90  77.00-120.00  168
;
_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      -0.0189444000
_diffrn_orient_matrix_UB_12      -0.0320255000
_diffrn_orient_matrix_UB_13      0.0279222000
_diffrn_orient_matrix_UB_21      -0.0005337000
_diffrn_orient_matrix_UB_22      0.0305688000
_diffrn_orient_matrix_UB_23      0.0360488000
_diffrn_orient_matrix_UB_31      -0.0482122000
_diffrn_orient_matrix_UB_32      0.0122462000
_diffrn_orient_matrix_UB_33      -0.0169541000
_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  0.0290
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27445
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.302
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
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    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         9200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0630
_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^)+(0.1009P)^2^+0.3143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6176
_reflns_number_total             9200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02075d2.cif
_cod_data_source_block           origi116
_cod_depositor_comments
'Adding full bibliography for 7159772--7159774.cif.'
_cod_database_code               7159772
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C42H34
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C40A(0.5) H40A(0.5) H40B(0.5) H40C(0.5) C40B(0.5) H40D(0.5)
 H40E(0.5) H40F(0.5) C41A(0.5) H41A(0.5) H41B(0.5) H41C(0.5) C41B(0.5)
 H41D(0.5) H41E(0.5) H41F(0.5) C42A(0.5) H42A(0.5) H42B(0.5) H42C(0.5)
 C42B(0.5) H42D(0.5) H42E(0.5) H42F(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27)
3.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C40A(H40A,H40B,
 H40C), C40B(H40D,H40E,H40F), C41A(H41A,H41B,H41C), C41B(H41D,H41E,H41F),
 C42A(H42A,H42B,H42C), C42B(H42D,H42E,H42F)
;
_shelx_res_checksum              23108
_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 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.790