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_7155078
_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 ad
_chemical_formula_moiety         'C38 H34 B2 N4 O6'
_chemical_formula_sum            'C38 H34 B2 N4 O6'
_chemical_formula_weight         664.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3239(5)
_cell_length_b                   12.8880(7)
_cell_length_c                   25.7528(11)
_cell_measurement_reflns_used    3857
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      72.9160
_cell_measurement_theta_min      4.8620
_cell_volume                     3758.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2299
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -54.00  32.00   1.00   10.00    --  -38.50  38.00 -60.00   86
  2  \w     20.00  75.00   1.00   10.00    --   43.14 -99.00 -90.00   55
  3  \w     56.00 143.00   1.00   40.00    --  104.54 -15.00 -60.00   87
  4  \w     74.00 148.00   1.00   40.00    --  104.54  77.00 120.00   74
  5  \w     25.00 100.00   1.00   40.00    --  104.54 -94.00  90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0839652000
_diffrn_orient_matrix_UB_12      -0.0267067000
_diffrn_orient_matrix_UB_13      0.0448278000
_diffrn_orient_matrix_UB_21      0.1002964000
_diffrn_orient_matrix_UB_22      0.0204194000
_diffrn_orient_matrix_UB_23      0.0394867000
_diffrn_orient_matrix_UB_31      -0.0371845000
_diffrn_orient_matrix_UB_32      0.1147554000
_diffrn_orient_matrix_UB_33      0.0036071000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9143
_diffrn_reflns_point_group_measured_fraction_full 0.813
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         3.835
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1490 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         5540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0828P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.494
_reflns_Friedel_fraction_full    0.613
_reflns_Friedel_fraction_max     0.630
_reflns_number_gt                4867
_reflns_number_total             5540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00726k2.cif
_cod_data_source_block           1to2_alpha_glucoseptanoseBODIPY
_cod_depositor_comments
'Adding full bibliography for 7155078--7155079.cif.'
_cod_database_code               7155078
_chemical_oxdiff_formula         'C152 H136 B8 N16 O24'
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelxl_version_number           2013-2
_shelx_res_checksum              60088
_shelx_hkl_checksum              97233