An efficient pathway to high persistence length helicenes from scalable [4]-helicene synthons
Reinhard, Garrett L.; Dowling, Reed; Hewitt, Patrick; Varshney, Vikas; Simone, Davide L.; RSC Advances 15 (2025) 20935–20943; doi:10.1039/D5RA02685G

data_7250572
_publ_section_title
;
 An efficient pathway to high persistence length helicenes from scalable
 [4]-helicene synthons
;
_journal_issue                   26
_journal_name_full               'RSC Advances'
_journal_page_first              20935
_journal_page_last               20943
_journal_paper_doi               10.1039/D5RA02685G
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C31 H32 O3'
_chemical_formula_sum            'C31 H32 O3'
_chemical_formula_weight         452.56
_chemical_name_systematic
;
2-isopropyl-5-methyl cyclohexyl (11-vinylbenzo[c]phenanthren-3-yl)
;
_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   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2025-06-03 deposited with the CCDC.	2025-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4947(2)
_cell_length_b                   13.8436(4)
_cell_length_c                   27.5171(7)
_cell_measurement_reflns_used    3573
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      75.8570
_cell_measurement_theta_min      3.1960
_cell_volume                     2474.06(12)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8993
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.758
_diffrn_reflns_theta_min         3.212
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.70726
_exptl_absorpt_correction_T_min  0.68829
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       sphere
_exptl_crystal_F_000             968
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes'
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.004
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1182 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(17)
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0304P)^2^+0.3020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.534
_reflns_Friedel_fraction_full    0.779
_reflns_Friedel_fraction_max     0.675
_reflns_number_gt                3605
_reflns_number_total             4289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra02685g2.cif
_cod_data_source_block           4vinylhelicene_adsorp
_cod_database_code               7250572
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              19283