DANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible fluorophore.
Johnson, Lewis E.; Kingsbury, Jason S.; Elder, Delwin L.; Cattolico, Rose Ann; Latimer, Luke N.; Hardin, William; De Meulenaere, Evelien; Deodato, Chloe; Depotter, Griet; Madabushi, Sowmya; Bigelow, Nicholas W.; Smolarski, Brittany A.; Hougen, Trevor K.; Kaminsky, Werner; Clays, Koen; Robinson, Bruce H.; Organic & biomolecular chemistry 17 (2019) 3765–3780; doi:10.1039/c8ob02536c

data_7156735
_publ_section_title
;
 DANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible
 fluorophore.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3765
_journal_page_last               3780
_journal_paper_doi               10.1039/c8ob02536c
_journal_volume                  17
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H19 N2, I3'
_chemical_formula_sum            'C18 H19 I3 N2'
_chemical_formula_weight         644.05
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     direct
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2018-07-24T15:15:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-08-20 deposited with the CCDC.    2019-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.807(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   28.113(3)
_cell_length_b                   13.9070(15)
_cell_length_c                   20.473(2)
_cell_measurement_reflns_used    9813
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.57
_cell_measurement_wavelength     0.71073
_cell_volume                     7976.1(14)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.457
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.048124
_diffrn_orient_matrix_UB_12      -0.007112
_diffrn_orient_matrix_UB_13      0.009091
_diffrn_orient_matrix_UB_21      -0.006941
_diffrn_orient_matrix_UB_22      0.019231
_diffrn_orient_matrix_UB_23      0.033507
_diffrn_orient_matrix_UB_31      -0.006904
_diffrn_orient_matrix_UB_32      -0.068914
_diffrn_orient_matrix_UB_33      0.008412
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.457
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            39746
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.457
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.466
_diffrn_reflns_theta_min         1.454
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.704
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4800
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         5.073
_refine_diff_density_min         -2.755
_refine_diff_density_rms         0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     842
_refine_ls_number_reflns         19882
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+19.8087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0
_reflns_number_gt                12034
_reflns_number_total             19882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02536c6.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7156735.cif.'
_cod_original_cell_volume        7976.3(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7156735
_shelx_estimated_absorpt_t_min   0.165
_shelx_estimated_absorpt_t_max   0.912
_shelx_res_checksum              20932
_shelx_hkl_checksum              58893