Unusual spectroscopic and photophysical properties of meso-tert-butylBODIPY in comparison to related alkylated BODIPY dyes
Jiao, Lijuan; Yu, Changjiang; Wang, Jun; Briggs, Edward A.; Besley, Nicholas A.; Robinson, David; Ruedas-Rama, María J.; Orte, Angel; Crovetto, Luis; Talavera, Eva M.; Alvarez-Pez, Jose M.; Van der Auweraer, Mark; Boens, Noël; RSC Advances 5 (2015) 89375–; doi:10.1039/C5RA17419H

data_7235976
_publ_section_title
;
 Unusual spectroscopic and photophysical properties of
 meso-tert-butylBODIPY in comparison to related alkylated BODIPY dyes
;
_journal_issue                   109
_journal_name_full               'RSC Advances'
_journal_page_first              89375
_journal_paper_doi               10.1039/C5RA17419H
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C12 H13 B F2 N2)'
_chemical_formula_sum            'C24 H26 B2 F4 N4'
_chemical_formula_weight         468.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2014-04-02 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 120.2280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.054(2)
_cell_length_b                   12.6204(19)
_cell_length_c                   13.685(3)
_cell_measurement_reflns_used    4092
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.69
_cell_measurement_theta_min      2.28
_cell_volume                     2395.7(7)
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9286
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_coef       0.0077(6)
_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   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.3109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                3418
_reflns_number_total             4704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra17419h2.cif
_cod_data_source_block           131106b
_cod_original_cell_volume        2395.7(8)
_cod_database_code               7235976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1DA-C1CA
 1.54 with sigma of 0.02
 C1CA-C1EA
 1.54 with sigma of 0.02
 C18A-C17A
 1.54 with sigma of 0.02
 C18A-C14A
 1.54 with sigma of 0.02
 C1CB-C1EB
 1.54 with sigma of 0.02
 C1CB-C1DB
 1.54 with sigma of 0.02
 C18B-C14B
 1.54 with sigma of 0.02
 C17B-C18B
 1.54 with sigma of 0.02
3. Others
 Sof(C14B)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C17B)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=Sof(C18B)=Sof(H18B)=1-FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C14A)=
 Sof(H14D)=Sof(H14E)=Sof(H14F)=FVAR(1)
 Sof(C1CB)=Sof(H1CB)=Sof(C1DB)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=Sof(C1EB)=
 Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=1-FVAR(2)
 Sof(C1CA)=Sof(H1CA)=Sof(C1DA)=Sof(H1DD)=Sof(H1DE)=Sof(H1DF)=Sof(C1EA)=
 Sof(H1ED)=Sof(H1EE)=Sof(H1EF)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C1CB(H1CB), C18B(H18B), C18A(H18A), C1CA(H1CA)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C7(H7), C8(H8), C15(H15), C11(H11), C13(H13), C16(H16),
 C19(H19), C10(H10), C1A(H1A), C1B(H1B)
4.c Idealised Me refined as rotating group:
 C1DB(H1DA,H1DB,H1DC), C1EB(H1EA,H1EB,H1EC), C14B(H14A,H14B,H14C), C17B(H17A,
 H17B,H17C), C17A(H17D,H17E,H17F), C14A(H14D,H14E,H14F), C1DA(H1DD,H1DE,H1DF),
 C1EA(H1ED,H1EE,H1EF)
;