Merging polyacenes and cationic helicenes: from weak to intense chiroptical properties in the far red region
Duwald, Romain; Bosson, Johann; Pascal, Simon; Grass, Stéphane; Zinna, Francesco; Besnard, Céline; Di Bari, Lorenzo; Jacquemin, Denis; Lacour, Jérôme; Chemical Science 11 (2020) 1165–1169; doi:10.1039/C9SC05407C

data_1556884
_publ_section_title
;
 Merging polyacenes and cationic helicenes: from weak to intense
 chiroptical properties in the far red region
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1165
_journal_page_last               1169
_journal_paper_doi               10.1039/C9SC05407C
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'F6 P, C40 H36 N3 O3'
_chemical_formula_sum            'C40 H36 F6 N3 O3 P'
_chemical_formula_weight         751.69
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-21 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.223(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.20579(16)
_cell_length_b                   29.4208(8)
_cell_length_c                   16.5731(3)
_cell_measurement_reflns_used    5376
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      73.1660
_cell_measurement_theta_min      3.9590
_cell_volume                     3994.76(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_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    -53.00  38.00   1.00   12.50    --  -37.69  57.00   0.00   91
  2  \w     84.00 121.00   1.00   23.00    --   37.69 178.00 -90.00   37
  3  \w     77.00 104.00   1.00   23.00    --  110.40  77.00 -60.00   27
  4  \w     79.00 175.00   1.00   23.00    --  110.40  45.00 -90.00   96
  5  \w    104.00 151.00   1.00   23.00    --  110.40 111.00 -30.00   47
  6  \w     98.00 130.00   1.00   23.00    --   37.69 178.00  90.00   32
  7  \w     75.00 161.00   1.00   23.00    --  110.40  77.00 150.00   86
  8  \w     29.00  98.00   1.00   23.00    --  110.40-111.00  60.00   69
  9  \w     26.00 146.00   1.00   23.00    --  110.40 -77.00 150.00  120
 10  \w    -74.00  40.00   1.00   23.00    --  -37.69  77.00  90.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0684700000
_diffrn_orient_matrix_UB_12      -0.0385931000
_diffrn_orient_matrix_UB_13      -0.0510721000
_diffrn_orient_matrix_UB_21      0.0061070000
_diffrn_orient_matrix_UB_22      -0.0315320000
_diffrn_orient_matrix_UB_23      0.0744016000
_diffrn_orient_matrix_UB_31      -0.1750963000
_diffrn_orient_matrix_UB_32      -0.0160526000
_diffrn_orient_matrix_UB_33      -0.0230127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14983
_diffrn_reflns_point_group_measured_fraction_full 0.718
_diffrn_reflns_point_group_measured_fraction_max 0.686
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.588
_diffrn_reflns_theta_min         3.004
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.193
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.401
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       plate
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.581
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1056
_refine_ls_number_reflns         11054
_refine_ls_number_restraints     445
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0679
_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^)+(0.1355P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.2124
_reflns_Friedel_coverage         0.391
_reflns_Friedel_fraction_full    0.426
_reflns_Friedel_fraction_max     0.394
_reflns_number_gt                7802
_reflns_number_total             11054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05407c2.cif
_cod_data_source_block           compound2
_cod_depositor_comments
;Adding full bibliography for 1556884--1556886.cif.

 Adding full bibliography for 1556884--1556886.cif.
;
_cod_database_code               1556884
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C40 H36 F6 N3 O3 P1'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.50(6)
 0.50(6)
2. 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
3. Restrained distances
 F4B-F1B \\sim F4B-F3B \\sim F4B-F6B \\sim F1B-F5B \\sim F1B-F2B \\sim F1B-F3B
\\sim F5B-F2B \\sim F5B-F6B
 \\sim F2B-F3B \\sim F2B-F6B \\sim F3B-F6B
 with sigma of 0.04
 P1-F4B \\sim P1-F1AA \\sim P1-F5 \\sim P1-F5B \\sim P1-F1 \\sim P1-F1B \\sim
P1-F2B \\sim P1-F3 \\sim P1-F3B
 \\sim P1-F6 \\sim P1-F6B \\sim P1-F4
 with sigma of 0.02
 P1-F4B \\sim P1-F1B \\sim P1-F5B \\sim P1-F2B \\sim P1-F3B \\sim P1-F6B
 with sigma of 0.02
 P1-F5 \\sim P1-F6 \\sim P1-F4 \\sim P1-F3 \\sim P1-F1AA \\sim P1-F1
 with sigma of 0.02
 F1-F6 \\sim F1-F3 \\sim F1-F5 \\sim F5-F1AA \\sim F4-F6 \\sim F4-F3 \\sim
F4-F5 \\sim F4-F1AA
 with sigma of 0.04
 F6-F3 \\sim F3-F5 \\sim F5-F1AA \\sim F1AA-F6
 with sigma of 0.04
 F1B-F2B \\sim F1B-F3B \\sim F1B-F4B \\sim F1B-F5B \\sim F6B-F2B \\sim F6B-F3B
\\sim F6B-F4B \\sim F6B-F5B
 with sigma of 0.04
 F2B-F3B \\sim F3B-F4B \\sim F4B-F5B \\sim F5B-F2B
 with sigma of 0.04
 F9-F12 \\sim F12-F11 \\sim F11-F10 \\sim F10-F9
 with sigma of 0.03
 F9B-F10B \\sim F10B-F11B \\sim F11B-F12B \\sim F12B-F9B
 with sigma of 0.02
 F8-F9 \\sim F8-F10 \\sim F8-F11 \\sim F8-F12 \\sim F7-F9 \\sim F7-F10 \\sim
F7-F11 \\sim F7-F12
 with sigma of 0.04
 F8-F9B \\sim F8-F10B \\sim F8-F11B \\sim F8-F12B \\sim F7-F9B \\sim F7-F10B
\\sim F7-F11B \\sim F7-F12B
 with sigma of 0.04
4. Rigid body (RIGU) restrains
 P1, F1B, F2B, F3B, F4B, F5B, F6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P1, F1, F1AA, F3, F4, F5, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P2, F7, F8, F9, F10, F11, F12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F1)=Sof(F1AA)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=1-FVAR(1)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=FVAR(1)
 Sof(F9B)=Sof(F10B)=Sof(F11B)=Sof(F12B)=1-FVAR(2)
 Sof(F9)=Sof(F10)=Sof(F11)=Sof(F12)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C35(H35A,H35B), C44(H44A,H44B), C45(H45A,H45B), C34B(H34C,
 H34D), C35B(H35C,H35D), C44B(H44C,H44D), C45B(H45C,H45D)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C21(H21), C29(H29), C30(H30), C31(H31), C39(H39), C40(H40), C41(H41),
  C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B), C11B(H11B), C12B(H12B), C13B(H13B),
 C14B(H14B), C15B(H15B), C21B(H21B), C29B(H29B), C30B(H30B), C31B(H31B),
 C39B(H39B), C40B(H40B), C41B(H41B)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C28(H28A,H28B,H28C), C36(H36A,H36B,H36C), C46(H46A,H46B,
 H46C), C23B(H23D,H23E,H23F), C28B(H28D,H28E,H28F), C36B(H36D,H36E,H36F),
 C46B(H46D,H46E,H46F)
;
_shelx_res_checksum              20767
_shelx_fab_checksum              85776
_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 1.312
_oxdiff_exptl_absorpt_empirical_full_min 0.796