Coumarin- and Rhodamine-Fused Deep Red Fluorescent Dyes: Synthesis, Photophysical Properties, and Bioimaging in Vitro
Jianhong Chen; Weimin Liu; Bingjiang Zhou; Guangle Niu; Hongyan Zhang; Jiasheng Wu; Ying Wang; Weigang Ju; Pengfei Wang; Journal of Organic Chemistry 78 (2013) 6121–6130; doi:10.1021/jo400783x

data_4028360
_publ_section_title
;
 Coumarin- and Rhodamine-Fused Deep Red Fluorescent Dyes: Synthesis,
 Photophysical Properties, and Bioimaging in Vitro
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6121
_journal_page_last               6130
_journal_paper_doi               10.1021/jo400783x
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C35 H35 N2 O5, Cl O4'
_chemical_formula_sum            'C35 H35 Cl N2 O9'
_chemical_formula_weight         663.10
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.346(3)
_cell_length_b                   16.964(3)
_cell_length_c                   15.303(3)
_cell_measurement_reflns_used    3672
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.98
_cell_volume                     3077.0(12)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19899
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.98
_exptl_absorpt_coefficient_mu    1.624
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T. Higashi, March, 2001'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0923
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1317P)^2^+3.3296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2432
_refine_ls_wR_factor_ref         0.2611
_reflns_number_gt                3672
_reflns_number_total             5594
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400783x_si_004.cif
_cod_data_source_block           a
_cod_original_cell_volume        3077.0(11)
_cod_database_code               4028360