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_7250574
_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         'C23 H28 O3'
_chemical_formula_sum            'C23 H28 O3'
_chemical_formula_weight         352.45
_chemical_name_systematic
;
2-isopropyl-5-methyl-cyclohexyl (6-vinylnaphthalen-2-yl) carbonate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-06-02
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-06-02 deposited with the CCDC.	2025-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.808(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6154(2)
_cell_length_b                   6.24730(10)
_cell_length_c                   13.6735(3)
_cell_measurement_reflns_used    6651
_cell_measurement_temperature    200.15
_cell_measurement_theta_max      75.2700
_cell_measurement_theta_min      3.8580
_cell_volume                     977.71(3)
_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-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Hypix'
_diffrn_measurement_method       'XtaLAB Synergy, Dualflex, Hypix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11946
_diffrn_reflns_point_group_measured_fraction_full 0.772
_diffrn_reflns_point_group_measured_fraction_max 0.727
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.257
_diffrn_reflns_theta_min         3.862
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.83418
_exptl_absorpt_correction_T_min  0.83013
_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    1.197
_exptl_crystal_description       sphere
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.041
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.019
_exptl_crystal_size_rad          0.402
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.35(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0378P)^2^+0.0613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.378
_reflns_Friedel_fraction_full    0.493
_reflns_Friedel_fraction_max     0.441
_reflns_number_gt                2721
_reflns_number_total             2981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra02685g2.cif
_cod_data_source_block           ov_vinylmenthyl_200kelvin_absorpt
_cod_database_code               7250574
_shelx_shelxl_version_number     2016/6
_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 Ternary CH refined with riding coordinates:
 C008(H008), C009(H009), C00H(H00H), C00J(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00D), C00G(H00E,H00G), C00I(H00I,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00C(H00C), C00F(H00F), C00K(H00L), C00L(H00M),
 C00M(H00N)
2.d Idealised Me refined as rotating group:
 C00N(H00O,H00P,H00Q), C00O(H00R,H00S,H00T), C00P(H00U,H00V,H00W)
;
_shelx_res_checksum              38483
_olex2_submission_special_instructions 'No special instructions were received'