Boron functionalization of BODIPY by various alcohols and phenols.
Brizet, Bertrand; Bernhard, Claire; Volkova, Yulia; Rousselin, Yoann; Harvey, Pierre D.; Goze, Christine; Denat, Franck; Organic & biomolecular chemistry 11 (2013) 7729–7737; doi:10.1039/c3ob41370e

data_7153153
_publ_section_title
;
 Boron functionalization of BODIPY by various alcohols and phenols.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7729
_journal_page_last               7737
_journal_paper_doi               10.1039/c3ob41370e
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C39 H39 B N2 O6'
_chemical_formula_sum            'C39 H39 B N2 O6'
_chemical_formula_weight         642.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2013.03.22 svn.r2654, GUI svn.r4446)
;
_audit_update_record
;
2013-03-29 # Formatted by publCIF
;
_cell_angle_alpha                86.5400(10)
_cell_angle_beta                 68.923(2)
_cell_angle_gamma                65.630(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8262(3)
_cell_length_b                   12.7507(4)
_cell_length_c                   14.1556(4)
_cell_measurement_reflns_used    6976
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1651.94(9)
_computing_cell_refinement       'DENZO, (Otwinowski & Minor, 1997)'
_computing_data_collection
'Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.'
_computing_data_reduction        'DENZO, (Otwinowski & Minor, 1997)'
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14266
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         1.550
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     440
_refine_ls_number_reflns         7527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0274P)^2^+1.4389P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6118
_reflns_number_total             7527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3ob41370e.txt
_cod_data_source_block           09cb659
_cod_database_code               7153153
_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.a Secondary CH2 refined with riding coordinates:
C11(H11A,H11B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
C19(H19), C20(H20), C22(H22), C23(H23), C27(H27), C28(H28), C30(H30),
C31(H31), C32(H32), C34(H34), C35(H35), C37(H37), C38(H38), C39(H39)
2.c Idealised Me refined as rotating group:
C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C)
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.979
_shelx_hkl_checksum              66936
_shelx_res_checksum              1670
_shelxl_version_number           2013-2