Synthesis and properties of chiral fluorescent helicene-BODIPY conjugates.
Moneva Lorente, Pau; Wallabregue, Antoine; Zinna, Francesco; Besnard, Céline; Di Bari, Lorenzo; Lacour, Jérôme; Organic & biomolecular chemistry 18 (2020) 7677–7684; doi:10.1039/d0ob01809k

data_7157716
_publ_section_title
;
 Synthesis and properties of chiral fluorescent helicene-BODIPY
 conjugates.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7677
_journal_page_last               7684
_journal_paper_doi               10.1039/d0ob01809k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C32 H26 B F5 N3 O2, B F4'
_chemical_formula_sum            'C32 H26 B2 F9 N3 O2'
_chemical_formula_weight         677.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-08-19 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                92.741(3)
_cell_angle_beta                 106.371(3)
_cell_angle_gamma                107.992(3)
_cell_formula_units_Z            2
_cell_length_a                   11.2245(5)
_cell_length_b                   13.0227(5)
_cell_length_c                   13.7251(5)
_cell_measurement_reflns_used    8420
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      72.6820
_cell_measurement_theta_min      3.5710
_cell_volume                     1810.67(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_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   -110.00 -79.00   1.00    4.50    --  -38.94 -99.00 120.00   31
  2  \w   -122.00 -86.00   1.00    4.50    --  -38.94 -99.00  90.00   36
  3  \w   -123.00 -85.00   1.00    4.50    --  -38.94 -99.00  30.00   38
  4  \w   -116.00 -79.00   1.00    4.50    --  -38.94 -99.00 -30.00   37
  5  \w   -123.00 -81.00   1.00    4.50    --  -38.94 -99.00-120.00   42
  6  \w   -120.00 -79.00   1.00    4.50    --  -38.94 -99.00-180.00   41
  7  \w   -124.00 -94.00   1.00    4.50    --  -38.94 -99.00 -60.00   30
  8  \w     32.00  89.00   1.00   20.00    --  110.40 -61.00 -90.00   57
  9  \w     74.00  99.00   1.00   20.00    --  110.40 -94.00 -90.00   25
 10  \w     54.00 114.00   1.00   20.00    --  110.40-111.00-120.00   60
 11  \w     57.00 127.00   1.00   20.00    --  110.40 -77.00   0.00   70
 12  \w     63.00 106.00   1.00   20.00    --  110.40 -94.00 120.00   43
 13  \w     37.00 137.00   1.00   20.00    --  110.40 -30.00 -30.00  100
 14  \w     32.00 140.00   1.00   20.00    --  110.40 -45.00  90.00  108
 15  \w     29.00 112.00   1.00   20.00    --  110.40-111.00  30.00   83
 16  \w     26.00  70.00   1.00   20.00    --  110.40 -94.00 -90.00   44
 17  \w     28.00 178.00   1.00   20.00    --  110.40 -15.00-180.00  150
 18  \w     75.00 101.00   1.00    4.50    --   38.94-178.00-150.00   26
 19  \w     65.00 132.00   1.00    4.50    --   38.94 178.00 120.00   67
 20  \w     57.00  93.00   1.00    4.50    --   38.94 178.00  30.00   36
 21  \w     64.00 125.00   1.00    4.50    --   38.94 178.00 -30.00   61
 22  \w     61.00 112.00   1.00    4.50    --   38.94 178.00-120.00   51
 23  \w     57.00  83.00   1.00   20.00    --  110.40 178.00 120.00   26
 24  \w    -34.00  -8.00   1.00    4.50    --  -38.94 -57.00 120.00   26
 25  \w    -63.00 -13.00   1.00    4.50    --  -38.94 -38.00   0.00   50
 26  \w    -99.00 -48.00   1.00    4.50    --  -38.94 -57.00 -60.00   51
 27  \w    -86.00 -43.00   1.00    4.50    --  -38.94 -57.00 120.00   43
 28  \w    -45.00  -9.00   1.00    4.50    --  -38.94 -57.00 -60.00   36
 29  \w     -3.00  24.00   1.00    4.50    --   40.00  94.00-152.34   27
 30  \w      3.00  31.00   1.00    4.50    --   44.00  90.00  28.03   28
 31  \w      9.00  34.00   1.00    4.50    --   48.00  86.00 108.10   25
 32  \w     19.00  44.00   1.00    4.50    --   56.00  80.00-128.67   25
 33  \w     19.00  44.00   1.00    4.50    --   56.00  81.00-172.68   25
 34  \w     19.00  44.00   1.00    4.50    --   56.00  82.00 -77.56   25
 35  \w     19.00  46.00   1.00    4.50    --   56.00  81.00 141.61   27
 36  \w     19.00  44.00   1.00    4.50    --   56.00  82.00  12.96   25
 37  \w     29.00  80.00   1.00    4.50    --   64.00  75.00-143.72   51
 38  \w     28.00  71.00   1.00    4.50    --   64.00  76.00 -88.78   43
 39  \w     29.00  71.00   1.00    4.50    --   64.00  77.00  13.45   42
 40  \w     29.00  54.00   1.00    4.50    --   64.00  75.00  72.77   25
 41  \w     33.00  71.00   1.00    4.50    --   68.00  75.00 163.99   38
 42  \w     37.00  62.00   1.00    4.50    --   72.00  77.00 -31.64   25
 43  \w     36.00  82.00   1.00    4.50    --   72.00  76.00 103.47   46
 44  \w     41.00  46.00   1.00   20.00    --   76.00  66.00  52.13    5
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0280183000
_diffrn_orient_matrix_UB_12      -0.1033077000
_diffrn_orient_matrix_UB_13      0.0346548000
_diffrn_orient_matrix_UB_21      0.1466846000
_diffrn_orient_matrix_UB_22      0.0547660000
_diffrn_orient_matrix_UB_23      0.0102895000
_diffrn_orient_matrix_UB_31      0.0277895000
_diffrn_orient_matrix_UB_32      0.0463063000
_diffrn_orient_matrix_UB_33      0.1126272000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17797
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.657
_diffrn_reflns_theta_min         3.393
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.242
_exptl_crystal_description       plate
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.014
_platon_squeeze_details
;
One hole representing about  22 percent of the volume of the unit-cell was located containing 129 electrons, which could correspond to about 3 dichloromethane molecules. The solvent molecules were not added to the formula.

;
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7062
_refine_ls_number_restraints     172
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0878P)^2^+0.5896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5834
_reflns_number_total             7062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01809k2.cif
_cod_data_source_block           pml294_2_sq
_cod_depositor_comments          'Adding full bibliography for 7157716.cif.'
_cod_original_cell_volume        1810.66(12)
_cod_database_code               7157716
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C32.6666 H26 B2 F9 N3 O2 Cl3 H3'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.777
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_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
 F7A-B2 \\sim F7B-B2 \\sim F6A-B2 \\sim F8B-B2 \\sim F9B-B2 \\sim F8A-B2 \\sim
F9A-B2 \\sim F6B-B2
 with sigma of 0.02
 F7A-F6A \\sim F7A-F9A \\sim F7A-F8A \\sim F6A-F8A \\sim F6A-F9A \\sim F8A-F9A
 with sigma of 0.02
 F7B-F6B \\sim F7B-F8B \\sim F7B-F9B \\sim F6B-F8B \\sim F6B-F9B \\sim F8B-F9B
 with sigma of 0.02
 F3B-C37 \\sim F4A-C37 \\sim F3A-C37 \\sim F5B-C37 \\sim F5A-C37 \\sim F4B-C37
 with sigma of 0.02
 F4A-F5A \\sim F5A-F3A \\sim F3A-F4A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F8A) = Uanis(F8B)
Uanis(F3B) = Uanis(F4A)
4. Rigid body (RIGU) restrains
 F6A, F7A, F8A, F9A, B2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F6B, F7B, F8B, F9B, B2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3A, F4A, F5A, C37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3B, F4B, F5B, C37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F6B)=Sof(F7B)=Sof(F8B)=Sof(F9B)=1-FVAR(1)
 Sof(F6A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(1)
 Sof(F3A)=Sof(F4A)=Sof(F5A)=1-FVAR(2)
 Sof(F3B)=Sof(F4B)=Sof(F5B)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C27(H27), C28(H28),
 C29(H29), C32(H32), C33(H33), C35(H35), C36(H36)
6.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              20395
_shelx_hkl_checksum              80985
_shelx_fab_checksum              71487
_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 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.787
_platon_squeeze_void_probe_radius 1.20