Lighting up sugars: fluorescent BODIPY-gluco-furanose and -septanose conjugates linked by direct B-O-C bonds.
Liu, Bowen; Novikova, Nina; Simpson, M. Cather; Timmer, Mattie S. M.; Stocker, Bridget L.; Söhnel, Tilo; Ware, David C.; Brothers, Penelope J.; Organic & biomolecular chemistry 14 (2016) 5205–5209; doi:10.1039/c6ob00726k

data_7155079
_publ_section_title
;
 Lighting up sugars: fluorescent BODIPY-gluco-furanose and -septanose
 conjugates linked by direct B-O-C bonds.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5205
_journal_page_last               5209
_journal_paper_doi               10.1039/c6ob00726k
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C22 H23 B N2 O6), 5(O)'
_chemical_formula_sum            'C44 H46 B2 N4 O17'
_chemical_formula_weight         924.47
_chemical_name_common            '1:1 ?-glucofuranose BODIPY ester'
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-01-21 deposited with the CCDC.
2016-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.381(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   37.5988(15)
_cell_length_b                   14.8713(6)
_cell_length_c                   8.2281(3)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.162
_cell_measurement_theta_min      3.515
_cell_volume                     4592.7(3)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2008)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2008)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.497
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.497
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            23480
_diffrn_reflns_point_group_measured_fraction_full 0.492
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         19.705
_diffrn_reflns_theta_min         1.085
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9212
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       'not regular'
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(4)
_refine_ls_extinction_coef       0.0058(16)
_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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         4060
_refine_ls_number_restraints     267
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0871
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1760P)^2^+12.8124P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2318
_refine_ls_wR_factor_ref         0.2389
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.486
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3733
_reflns_number_total             4060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00726k2.cif
_cod_data_source_block           1to1_alpha-GlucofuranoseBODIPY
_cod_depositor_comments
'Adding full bibliography for 7155078--7155079.cif.'
_cod_database_code               7155079
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-2
_shelx_res_checksum              16490
_shelx_hkl_checksum              35308