Coordination chemistry of N-picolyl-1,8-naphthalimides: colourful low molecular weight metallo-gelators and unique chelation behaviours
Lovitt, June I.; Hawes, Chris S.; Lynes, Amy D.; Haffner, Benjamin; Möbius, Matthias E.; Gunnlaugsson, Thorfinnur; Inorganic Chemistry Frontiers 4 (2017) 296–; doi:10.1039/C6QI00498A

data_4349619
_publ_section_title
;
 Coordination chemistry of N-picolyl-1,8-naphthalimides: colourful low
 molecular weight metallo-gelators and unique chelation behaviours
;
_journal_issue                   2
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              296
_journal_paper_doi               10.1039/C6QI00498A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C18 H11 N3 O4'
_chemical_formula_sum            'C18 H11 N3 O4'
_chemical_formula_weight         333.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4265(6)
_cell_length_b                   11.5416(5)
_cell_length_c                   17.5201(8)
_cell_measurement_reflns_used    6050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.542
_cell_volume                     2917.2(2)
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_reduction        'SAINT V8.35A (2016)'
_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      100.03
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.914
_diffrn_reflns_theta_min         2.325
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0690 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.8931.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0560P)^2^+2.7100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2356
_reflns_number_total             3485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qi00498a2.cif
_cod_data_source_block           L2
_cod_database_code               4349619
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C21-C16
 1.375 with sigma of 0.01
 C21-C20
 1.375 with sigma of 0.01
 C15-C14
 1.375 with sigma of 0.01
 C15-C16
 1.375 with sigma of 0.01
 C21-O1
 2.8 with sigma of 0.02
 C20-C19
 1.375 with sigma of 0.01
 C19-C12
 1.375 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C20)
Uanis(C15) = Uanis(C21)
Uanis(C13) = Uanis(C19)
4. Rigid body (RIGU) restrains
 C12, C13, C14, N4, O6, O5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O4(0.8) O3(0.8) H11(0.2) C15(0.8) H15(0.8) N3(0.8) C13(0.8)
 H13(0.8) C14(0.8) H14(0.8) O5(0.2) O6(0.2) N4(0.2) C19(0.2) C20(0.2) H20(0.2)
 C21(0.2) H21(0.2)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3), C1(H1), C9(H9), C11(H11), C10(H10), C15(H15),
 C13(H13), C14(H14), C20(H20), C21(H21)
;
_shelx_res_checksum              46343
_shelx_hkl_checksum              22725
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'