Fluorescent functionalised naphthalimides and their Au(i)-NHC complexes for potential use in cellular bioimaging.
Groves, Lara M.; Williams, Catrin F.; Hayes, Anthony J.; Ward, Benjamin D.; Isaacs, Marc D.; Symonds, Nadine O.; Lloyd, David; Horton, Peter N.; Coles, Simon J.; Pope, Simon J. A.; Dalton transactions (Cambridge, England : 2003) 48 (2019) 1599–1612; doi:10.1039/c8dt04069a

data_7048392
_publ_section_title
;
 Fluorescent functionalised naphthalimides and their Au(i)-NHC complexes
 for potential use in cellular bioimaging.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1599
_journal_page_last               1612
_journal_paper_doi               10.1039/c8dt04069a
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C20 H21 Au Cl N3 O2'
_chemical_formula_sum            'C20 H21 Au Cl N3 O2'
_chemical_formula_weight         567.81
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-19
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.03.09 svn.r3491 for OlexSys, GUI svn.r5480)
;
_audit_update_record
;
2018-03-20 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                67.576(2)
_cell_angle_beta                 72.828(2)
_cell_angle_gamma                76.121(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0951(2)
_cell_length_b                   10.0127(2)
_cell_length_c                   12.2157(3)
_cell_measurement_reflns_used    31702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7040
_cell_measurement_theta_min      1.8590
_cell_volume                     972.23(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;

List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames

  1  \w    -45.00  81.00   0.50    2.00    --   -8.10  38.00  60.00  252

  2  \w    -45.00  81.00   0.50    2.00    --   -8.10  38.00 -90.00  252

  3  \w    -97.00  26.00   0.50    2.00    --   -8.10 -65.00 -60.00  246

  4  \w    -97.00  26.00   0.50    2.00    --   -8.10 -65.00  60.00  246

  5  \w    -97.00  25.00   0.50    2.00    --   -8.10 -57.00-150.00  244

  6  \w    -42.00  81.00   0.50    2.00    --   -8.10  65.00 -30.00  246

  7  \w    -45.00  81.00   0.50    2.00    --   -8.10  38.00 150.00  252

  8  \w    -84.00  94.00   0.50    2.00    --    5.00   0.00-180.00  356

  9  \w    -41.00  81.00   0.50    2.00    --   -8.10  57.00  90.00  244

 10  \w    -42.00  81.00   0.50    2.00    --   -8.10  65.00 -90.00  246

 11  \w    -97.00  29.00   0.50    2.00    --   -8.10 -38.00 120.00  252

 12  \w    -41.00  81.00   0.50    2.00    --   -8.10  57.00 -60.00  244

 13  \w    -41.00  81.00   0.50    2.00    --   -8.10  57.00-180.00  244

 14  \w    -84.00 -59.00   0.50    2.00    --    5.00   0.00-150.00   50

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 \k goniometer'
_diffrn_measurement_device_type
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0506954000
_diffrn_orient_matrix_UB_12      -0.0502732000
_diffrn_orient_matrix_UB_13      0.0418373000
_diffrn_orient_matrix_UB_21      0.0118171000
_diffrn_orient_matrix_UB_22      0.0149560000
_diffrn_orient_matrix_UB_23      0.0488064000
_diffrn_orient_matrix_UB_31      -0.0639866000
_diffrn_orient_matrix_UB_32      0.0569767000
_diffrn_orient_matrix_UB_33      -0.0052567000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            50364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.852
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    7.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method
'The material was recrystallised from ether'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0142
_refine_ls_R_factor_gt           0.0133
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0166P)^2^+0.7625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0322
_refine_ls_wR_factor_ref         0.0324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4313
_reflns_number_total             4450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt04069a2.cif
_cod_data_source_block           AuClL3
_cod_depositor_comments
'Adding full bibliography for 7048391--7048392.cif.'
_cod_database_code               7048392
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H21 N3 O2 Cl Au'
_chemical_oxdiff_usercomment
'LG220 - recollection previously split crystal'
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.577
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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. Restrained distances
 C19B-C20B \\sim C20-C19
 with sigma of 0.02
 C19B-N3 \\sim N3-C19
 with sigma of 0.02
 C18B-C20B \\sim C20-C18
 with sigma of 0.02
 C18B-N3 \\sim N3-C18
 with sigma of 0.02
 C19B-C18B \\sim C18-C19
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N3, C18, C19, C20, C19B, C20B, C18B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C19B)=Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=
 Sof(C18B)=Sof(H18C)=Sof(H18D)=1-FVAR(1)
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B),
 C19B(H19C,H19D), C18B(H18C,H18D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C11(H11), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_shelx_res_checksum              74411
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id LG220
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;

Empirical correction (ABSPACK) includes:

- Absorption correction using spherical harmonics

- Frame scaling

;
_oxdiff_exptl_absorpt_empirical_full_max 2.197
_oxdiff_exptl_absorpt_empirical_full_min 0.530