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_7048391
_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 H22 N3 O2, F6 P'
_chemical_formula_sum            'C20 H22 F6 N3 O2 P'
_chemical_formula_weight         481.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.03.09 svn.r3491 for OlexSys, GUI svn.r5479)
;
_audit_update_record
;
2018-03-20 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.075(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6492(11)
_cell_length_b                   8.2325(6)
_cell_length_c                   16.7492(11)
_cell_measurement_reflns_used    4820
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5810
_cell_measurement_theta_min      2.5890
_cell_volume                     2093.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -35.00  55.00   1.00   80.00    --  -17.00  72.00  30.00   90
  2  \w    -69.00  22.00   1.00   80.00    --  -17.00 -72.00  90.00   91
  3  \w    -18.00   2.00   1.00   80.00    --  -17.00  54.00-150.00   20
  4  \w    -35.00  73.00   1.00   80.00    --  -17.00  72.00 -60.00  108
  5  \w    -68.00  -7.00   1.00   80.00    --  -17.00 -72.00-180.00   61
;
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ 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      0.0418936000
_diffrn_orient_matrix_UB_12      0.0364210000
_diffrn_orient_matrix_UB_13      0.0040437000
_diffrn_orient_matrix_UB_21      0.0013111000
_diffrn_orient_matrix_UB_22      -0.0300433000
_diffrn_orient_matrix_UB_23      -0.0393651000
_diffrn_orient_matrix_UB_31      -0.0206218000
_diffrn_orient_matrix_UB_32      0.0721573000
_diffrn_orient_matrix_UB_33      -0.0184117000
_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  0.0679
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15009
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.023
_diffrn_reflns_theta_min         2.507
_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    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method
'The material was obtained by vapour diffusion of ether into acetone.'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     378
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.0969
_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^)+(0.1067P)^2^+7.5167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2411
_refine_ls_wR_factor_ref         0.2652
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2687
_reflns_number_total             4111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt04069a2.cif
_cod_data_source_block           HL3PF6
_cod_depositor_comments
'Adding full bibliography for 7048391--7048392.cif.'
_cod_database_code               7048391
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H22 N3 O2 P F6'
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.978
_reflns_odcompleteness_completeness 99.90
_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. Uiso/Uaniso restraints and constraints
P1 \\sim P1A \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F1A
\\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim F6A: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
P1 \\sim P1A: within 2A with sigma of 0.003 and sigma for terminal atoms of
0.006
3. Rigid body (RIGU) restrains
 P1, P1A, F1, F2, F3, F4, F5, F6, F1A, F2A, F3A, F4A, F5A, F6A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(P1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(P1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C16(H16)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              97969
_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 LG215
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_full_max 2.646
_oxdiff_exptl_absorpt_empirical_full_min 0.435