Axially chiral BODIPYs
Reinner I. Lerrick; Thomas P. L. Winstanley; Karen Haggerty; Corinne Wills; William Clegg; Ross W. Harrington; Patrick Bultinck; Wouter Herrebout; Andrew C. Benniston; Michael J. Hall; Chem.Commun. 50 (2014) 4714–; doi:10.1039/C4CC00851K

data_7112596
_publ_section_title
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 Axially chiral BODIPYs
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_journal_name_full               Chem.Commun.
_journal_page_first              4714
_journal_paper_doi               10.1039/C4CC00851K
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C27 H31 B F2 N2 O2'
_chemical_formula_sum            'C27 H31 B F2 N2 O2'
_chemical_formula_weight         464.35
_chemical_name_systematic
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 ?
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_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-01-24
_audit_creation_method
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Olex2 1.2-alpha
(compiled 2014.01.21 svn.r2874 for OlexSys, GUI svn.r4743)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.318(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.712(5)
_cell_length_b                   25.125(15)
_cell_length_c                   12.348(7)
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    150
_cell_measurement_theta_max      22.09
_cell_measurement_theta_min      3.01
_cell_volume                     2391(3)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.670
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_Laue_measured_fraction_full 0.670
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10761
_diffrn_reflns_point_group_measured_fraction_full 0.670
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         21.257
_diffrn_reflns_theta_min         1.782
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1490 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8783.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     320
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0877P)^2^+0.4420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1819
_reflns_number_total             2897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7112284
_cod_data_source_file            c4cc00851k2.cif
_cod_data_source_block           mjh120032
_cod_database_code               7112596
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.996
_olex2_refinement_description
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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
 O2A-C18 \\sim O2-C18
 with sigma of 0.02
 O2A-C19A \\sim O2-C19
 with sigma of 0.02
 C20-C19 \\sim C20A-C19A
 with sigma of 0.02
 C20A-O2A \\sim C20-O2
 with sigma of 0.02
 O1-C18 \\sim O1A-C18
 with sigma of 0.02
 O2A-O1 \\sim O1A-O2
 with sigma of 0.02
3. Restrained planarity
 C22, C23, C24, C25, C26, C21
 with sigma of 0.1
 O1, C18, O2, C17
 with sigma of 0.1
 O2A, C18, O1A, C17
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
Uanis(O1) = Uanis(O1A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: O1(0.8) O2(0.8) C19(0.8) H19A(0.8) H19B(0.8) C20(0.8) H20A(0.8)
 H20B(0.8) H20C(0.8) O2A(0.2) C19A(0.2) H19C(0.2) H19D(0.2) C20A(0.2) H20D(0.2)
 H20E(0.2) H20F(0.2) O1A(0.2)
7.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B), C19A(H19C,H19D)
7.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C25(H25)
7.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F),
 C27(H27A,H27B,H27C)
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_shelx_res_checksum              5737
_shelx_hkl_checksum              73596