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_1556885
_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, C59 H43 N4 O2, C2 H3 N'
_chemical_formula_sum            'C61 H46 F6 N5 O2 P'
_chemical_formula_weight         1026.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-08
_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                 106.545(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.6234(11)
_cell_length_b                   16.7146(5)
_cell_length_c                   21.7661(9)
_cell_measurement_reflns_used    4769
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      68.3490
_cell_measurement_theta_min      4.0220
_cell_volume                     9633.6(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4670
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_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    -62.00  30.00   1.00   25.00    --  -40.65  38.00   0.00   92
  2  \w   -107.00 -17.00   1.00   25.00    --  -40.65 -38.00-180.00   90
  3  \w   -113.00 -76.00   1.00   25.00    --  -40.65-138.00 -69.00   37
  4  \w     29.00  91.00   1.00   45.00    --  100.00 -30.00 150.00   62
  5  \w     73.00 168.00   1.00   45.00    --  100.00  45.00 -30.00   95
  6  \w    101.00 170.00   1.00   45.00    --  100.00 111.00-180.00   69
  7  \w    103.00 170.00   1.00   45.00    --  100.00 111.00 150.00   67
  8  \w    147.00 177.00   1.00   45.00    --  100.00 111.00   0.00   30
  9  \w     92.00 157.00   1.00   45.00    --  100.00  45.00  90.00   65
 10  \w    104.00 154.00   1.00   45.00    --  100.00 111.00  30.00   50
 11  \w    125.00 167.00   1.00   45.00    --  100.00 111.00 120.00   42
;
_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      -0.0454642000
_diffrn_orient_matrix_UB_12      -0.0347530000
_diffrn_orient_matrix_UB_13      -0.0517764000
_diffrn_orient_matrix_UB_21      0.0362826000
_diffrn_orient_matrix_UB_22      -0.0467847000
_diffrn_orient_matrix_UB_23      -0.0288289000
_diffrn_orient_matrix_UB_31      -0.0018106000
_diffrn_orient_matrix_UB_32      -0.0713761000
_diffrn_orient_matrix_UB_33      0.0440700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20397
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.175
_diffrn_reflns_theta_min         4.036
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.151
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       plate
_exptl_crystal_F_000             4256
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     745
_refine_ls_number_reflns         8977
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0840P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1556
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5789
_reflns_number_total             8977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05407c2.cif
_cod_data_source_block           compound6
_cod_depositor_comments
;Adding full bibliography for 1556884--1556886.cif.

 Adding full bibliography for 1556884--1556886.cif.
;
_cod_database_code               1556885
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C61 H46 F6 N5 O2 P'
_reflns_odcompleteness_completeness 99.72
_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
 C36B-C35 \\sim C35-C36
 with sigma of 0.02
 N34-C35B \\sim N34-C35
 with sigma of 0.02
 C36-C35 \\sim C35B-C36B
 with sigma of 0.02
 C37-C36 \\sim C36B-C37B
 with sigma of 0.02
 P1-F6 \\sim P1-F10 \\sim P1-F5 \\sim P1-F9 \\sim P1-F4 \\sim P1-F7 \\sim
P1-F11 \\sim P1-F8
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C36B, C37B, C35B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C35, C36, C37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C35)=Sof(H35C)=Sof(H35D)=Sof(C36)=Sof(H36C)=Sof(H36D)=Sof(C37)=Sof(H37D)=
 Sof(H37E)=Sof(H37F)=1-FVAR(1)
 Sof(C36B)=Sof(H36A)=Sof(H36B)=Sof(C37B)=Sof(H37A)=Sof(H37B)=Sof(H37C)=
 Sof(C35B)=Sof(H35A)=Sof(H35B)=FVAR(1)
 Sof(F8)=Sof(F9)=Sof(F10)=Sof(F11)=1-FVAR(2)
 Sof(F4)=Sof(F5)=Sof(F6)=Sof(F7)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C36B(H36A,H36B), C35B(H35A,H35B), C26(H26A,H26B), C27(H27A,H27B), C35(H35C,
 H35D), C36(H36C,H36D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C20(H20), C22(H22), C23(H23), C30(H30), C31(H31), C32(H32),
  C42(H42), C43(H43), C46(H46), C50(H50), C51(H51), C52(H52), C53(H53),
 C54(H54), C56(H56), C57(H57), C58(H58), C59(H59), C64(H64)
5.c Idealised Me refined as rotating group:
 C37B(H37A,H37B,H37C), C28(H28A,H28B,H28C), C37(H37D,H37E,H37F), C72(H72A,H72B,
 H72C)
;
_shelx_res_checksum              58845
_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 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.826