Non-symmetric benzo[b]-fused BODIPYs as a versatile fluorophore platform reaching the NIR: a systematic study of the underlying structure-property relationship.
Bessette, André; Auvray, Thomas; Désilets, Denis; Hanan, Garry S.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 7589–7604; doi:10.1039/c5dt04444h

data_7038818
_publ_section_title
;
 Non-symmetric benzo[b]-fused BODIPYs as a versatile fluorophore platform
 reaching the NIR: a systematic study of the underlying structure-property
 relationship.
;
_journal_issue                   18
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7589
_journal_page_last               7604
_journal_paper_doi               10.1039/c5dt04444h
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C26 H19 B F2 N2 O'
_chemical_formula_sum            'C26 H19 B F2 N2 O'
_chemical_formula_weight         424.24
_chemical_name_common            BbF5
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-13 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.415(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5702(9)
_cell_length_b                   12.2670(5)
_cell_length_c                   7.9969(4)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    105
_cell_measurement_theta_max      60.694
_cell_measurement_theta_min      3.664
_cell_volume                     1990.71(16)
_computing_cell_refinement
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
 Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
'APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_reduction
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
 Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      105
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            30340
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.833
_diffrn_reflns_theta_min         3.663
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1289 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.8005.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       rod
_exptl_crystal_F_000             880
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Slow diffusion of heptane in a concentrated solution in dichloromethane'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4579
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0550P)^2^+1.1739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3472
_reflns_number_total             4579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt04444h2.cif
_cod_data_source_block           BbF5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7038816--7038819.cif.
;
_cod_database_code               7038818
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.843
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 0.9A with sigma of 0.04 and sigma
for terminal atoms of 0.08
3. Others
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C18B)=Sof(H18B)=Sof(C19B)=
 Sof(H19B)=1-FVAR(1)
 Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C15A(H15A),
 C15B(H15B), C16A(H16A), C16B(H16B), C18A(H18A), C18B(H18B), C19A(H19A),
 C19B(H19B), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
4.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              56995
_olex2_submission_special_instructions 'No special instructions were received'