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_1556886
_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         '2(F6 P), 3(C H2 Cl2), 2(C46 H36 N3 O)'
_chemical_formula_sum            'C95 H78 Cl6 F12 N6 O2 P2'
_chemical_formula_weight         1838.27
_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             2019-04-16
_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                 90.912(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6780(4)
_cell_length_b                   12.9347(5)
_cell_length_c                   27.785(9)
_cell_measurement_reflns_used    9818
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      70.1910
_cell_measurement_theta_min      3.7840
_cell_volume                     4196.4(14)
_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      N~2~
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4670
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.947
_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    -91.00 -12.00   1.00    6.00    --  -41.74 125.00  30.00   79
  2  \w   -110.00  -1.00   1.00    6.00    --  -41.74 -19.00 -60.00  109
  3  \w   -116.00 -31.00   1.00    6.00    --  -41.74 -38.00-120.00   85
  4  \w     23.00  50.00   1.00    6.00    --   41.74-125.00-150.00   27
  5  \w     33.00  96.00   1.00    6.00    --   41.74-125.00 -90.00   63
  6  \w    114.00 169.00   1.00   15.00    --  100.00 125.00 150.00   55
  7  \w     75.00 172.00   1.00   15.00    --  100.00  30.00 150.00   97
  8  \w     96.00 173.00   1.00   15.00    --  100.00  30.00-120.00   77
  9  \w     58.00 101.00   1.00   15.00    --  100.00 -94.00 -30.00   43
 10  \w    112.00 139.00   1.00   15.00    --  100.00 125.00 120.00   27
 11  \w     86.00 116.00   1.00   15.00    --  100.00-125.00-120.00   30
 12  \w     77.00 170.00   1.00   15.00    --  100.00  61.00-180.00   93
 13  \w     91.00 117.00   1.00   15.00    --  100.00  61.00  90.00   26
 14  \w    121.00 163.00   1.00   15.00    --  100.00  61.00  90.00   42
 15  \w     17.00  66.00   1.00   15.00    --  100.00 -94.00   0.00   49
 16  \w     80.00 122.00   1.00   15.00    --  100.00 -61.00 120.00   42
 17  \w     30.00  57.00   1.00   15.00    --  100.00 -61.00 120.00   27
 18  \w     82.00 107.00   1.00   15.00    --  100.00 -94.00   0.00   25
 19  \w     33.00 118.00   1.00   15.00    --  100.00-125.00 -60.00   85
 20  \w     24.00 132.00   1.00   15.00    --  100.00 -77.00  60.00  108
 21  \w     36.00  89.00   1.00   15.00    --  100.00 -45.00-120.00   53
;
_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      0.0075595000
_diffrn_orient_matrix_UB_12      0.0470548000
_diffrn_orient_matrix_UB_13      -0.0509108000
_diffrn_orient_matrix_UB_21      -0.0284470000
_diffrn_orient_matrix_UB_22      -0.1062394000
_diffrn_orient_matrix_UB_23      -0.0218701000
_diffrn_orient_matrix_UB_31      -0.1285654000
_diffrn_orient_matrix_UB_32      0.0262489000
_diffrn_orient_matrix_UB_33      0.0028377000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32242
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.791
_diffrn_reflns_theta_min         3.770
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.927
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.552
_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            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       plate
_exptl_crystal_F_000             1892
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         7916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0670
_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^)+(0.1026P)^2^+5.7864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1913
_refine_ls_wR_factor_ref         0.2057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6203
_reflns_number_total             7916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05407c2.cif
_cod_data_source_block           compound4
_cod_depositor_comments
;Adding full bibliography for 1556884--1556886.cif.

 Adding full bibliography for 1556884--1556886.cif.
;
_cod_database_code               1556886
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C47.5 H38 Cl3 F6 N3 O1 P1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
3. Uiso/Uaniso restraints and constraints
Uanis(C52_1) = Uanis(C52_2)
4. Rigid body (RIGU) restrains
 Cl2_1
 Cl2_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl3)=Sof(Cl2)=Sof(C52)=Sof(H52A)=Sof(H52B)=1-FVAR(1)
 Sof(Cl3)=Sof(Cl2)=Sof(C52)=Sof(H52A)=Sof(H52B)=FVAR(1)
 Fixed Sof: C51(0.5) H51A(0.5) H51B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C32(H32A,H32B), C33(H33A,H33B), C24(H24A,H24B), C51(H51A,
 H51B), C52(H52A,H52B), C52(H52A,H52B)
6.b Aromatic/amide H refined with riding coordinates:
 C49(H49), C17(H17), C36(H36), C42(H42), C37(H37), C19(H19), C27(H27),
 C29(H29), C28(H28), C20(H20), C41(H41), C39(H39), C7(H7), C40(H40), C3(H3),
 C12(H12), C9(H9), C4(H4), C6(H6), C5(H5), C11(H11), C10(H10)
6.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              99207
_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 1.993
_oxdiff_exptl_absorpt_empirical_full_min 0.712