Glycosylated naphthalimides and naphthalimide Tröger's bases as fluorescent aggregation probes for Con A.
Calatrava-Pérez, Elena; Delente, Jason M.; Shanmugaraju, Sankarasekaran; Hawes, Chris S.; Williams, Clive D.; Gunnlaugsson, Thorfinnur; Scanlan, Eoin M.; Organic & biomolecular chemistry 17 (2019) 2116–2125; doi:10.1039/c8ob02980f

data_7156648
_publ_section_title
;
 Glycosylated naphthalimides and naphthalimide Tr\"oger's bases as
 fluorescent aggregation probes for Con A.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2116
_journal_page_last               2125
_journal_paper_doi               10.1039/c8ob02980f
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C18 H17 N5 O3), 0.5(H2 O)'
_chemical_formula_sum            'C36 H35 N10 O6.5'
_chemical_formula_weight         711.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-09-07 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0714(12)
_cell_length_b                   27.849(2)
_cell_length_c                   6.8249(3)
_cell_measurement_reflns_used    3070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.10
_cell_measurement_theta_min      3.174
_cell_volume                     3244.7(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21933
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.524
_diffrn_reflns_theta_min         3.036
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1261 before and 0.0758 after correction. The Ratio of minimum to maximum transmission is 0.7951. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       rod
_exptl_crystal_F_000             1492
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         5941
_refine_ls_number_restraints     452
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0754
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1250P)^2^+0.3800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.2039
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4626
_reflns_number_total             5941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02980f2.cif
_cod_data_source_block           7
_cod_depositor_comments          'Adding full bibliography for 7156648.cif.'
_cod_original_formula_sum        'C36 H35 N10 O6.50'
_cod_database_code               7156648
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.753
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5(6)
 0.5(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Restrained distances
 H7B-O6A_$1
 2 with sigma of 0.02
 H7A-O6A
 1.994 with sigma of 0.01
 H1A-O7
 2.2 with sigma of 0.02
 C26-C27 \\sim C28-C27 \\sim C28-C29 \\sim C30-C29 \\sim C31-C30 \\sim C26-C31
\\sim C31-C35 \\sim C34-C35
 \\sim C34-C33 \\sim C33-C32 \\sim C30-C32
 with sigma of 0.02
 C17A-C16A \\sim C17A-C13A \\sim C12A-C13A \\sim C12A-C14A \\sim C15A-C14A
\\sim C15A-C16A
 with sigma of 0.02
 C13-C17 \\sim C12-C13 \\sim C14-C12 \\sim C14-C15 \\sim C16-C17 \\sim C16-C15
 with sigma of 0.02
 C8-C13 \\sim C9-C8 \\sim C9-C10 \\sim C10-C11 \\sim C11-C12 \\sim C12-C13
 with sigma of 0.02
 C12A-C13A \\sim C8-C13A \\sim C8-C9A \\sim C10A-C9A \\sim C11A-C12A \\sim
C10A-C11A
 with sigma of 0.02
 C26A-C31A \\sim C26A-C27A \\sim C28A-C27A \\sim C29A-C28A \\sim C30A-C32A
\\sim C30A-C29A \\sim C31A-
 C30A \\sim C35A-C31A \\sim C34A-C35A \\sim C34A-C33A \\sim C32A-C33A
 with sigma of 0.02
 C35A-C36A \\sim C26A-C25A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C32) = Uanis(C33A)
Uanis(C28) = Uanis(C29A)
Uanis(C25) = Uanis(C25A)
Uanis(C36) = Uanis(C36A)
Uanis(O3) = Uanis(O3A)
5. Rigid body (RIGU) restrains
 C9A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C9, C10, C11, C12, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O3, C17, C18
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O3A, C17A, C18A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O1A, C1A, C2A, C3A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O1, C1, C2, C3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C30A, C31A, C32A, C33A, C34A, C35A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N1, N2, N3, C4, C5
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Fixed Sof: O1(0.6667) H1(0.6667) O1A(0.33333) H1A(0.33333) O3(0.5) O3A(0.5)
 N5(0.33333) H5A(0.33333) H5B(0.33333) N5A(0.6667) H5AA(0.6667) H5AB(0.6667)
 C1(0.6667) H1B(0.6667) H1C(0.6667) C1A(0.33333) H1AA(0.33333) H1AB(0.33333)
 C2(0.6667) H2A(0.6667) H2B(0.6667) C2A(0.33333) H2AA(0.33333) H2AB(0.33333)
 C3(0.6667) H3A(0.6667) H3B(0.6667) C3A(0.33333) H3AA(0.33333) H3AB(0.33333)
 C9(0.5) H9(0.5) C9A(0.5) H9A(0.5) C10(0.5) H10(0.5) C10A(0.5) H10A(0.5)
 C11(0.5) C11A(0.5) H11A(0.5) C12(0.5) C12A(0.5) C13(0.5) C13A(0.5) C14(0.5)
 H14(0.5) C14A(0.5) C15(0.5) H15(0.5) C15A(0.5) H15A(0.5) C16(0.5) H16(0.5)
 C16A(0.5) H16A(0.5) C17(0.5) C17A(0.5) C18(0.5) C18A(0.5) O5(0.6667)
 O5A(0.33333) O6(0.6667) O6A(0.33333) N10(0.6667) H10B(0.6667) H10C(0.6667)
 N10A(0.33333) H10D(0.33333) H10E(0.33333) C25(0.6667) C25A(0.33333)
 C26(0.6667) C26A(0.33333) C27(0.6667) H27(0.6667) C27A(0.33333) H27A(0.33333)
 C28(0.6667) H28(0.6667) C28A(0.33333) H28A(0.33333) C29(0.6667) C29A(0.33333)
 H29A(0.33333) C30(0.6667) C30A(0.33333) C31(0.6667) C31A(0.33333) C32(0.6667)
 H32(0.6667) C32A(0.33333) C33(0.6667) H33(0.6667) C33A(0.33333) H33A(0.33333)
 C34(0.6667) H34(0.6667) C34A(0.33333) H34A(0.33333) C35(0.6667) C35A(0.33333)
 C36(0.6667) C36A(0.33333) H7A(0.5) H7B(0.5)
7.a Free rotating group:
 O7(H7A,H7B)
7.b Secondary CH2 refined with riding coordinates:
 C1(H1B,H1C), C1A(H1AA,H1AB), C2(H2A,H2B), C2A(H2AA,H2AB), C3(H3A,H3B),
 C3A(H3AA,H3AB), C6(H6A,H6B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C24(H24A,H24B)
7.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C9A(H9A), C10(H10), C10A(H10A), C11A(H11A), C14(H14),
 C15(H15), C15A(H15A), C16(H16), C16A(H16A), C22(H22), C27(H27), C27A(H27A),
 C28(H28), C28A(H28A), C29A(H29A), C32(H32), C33(H33), C33A(H33A), C34(H34),
 C34A(H34A)
7.d X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N5A(H5AA,H5AB), N10(H10B,H10C), N10A(H10D,H10E)
7.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A), O4(H4A)
;
_shelx_res_checksum              18980
_olex2_submission_special_instructions 'No special instructions were received'