Deep-Red and Near-Infrared Xanthene Dyes for Rapid Live Cell Imaging.
Niu, Guangle; Liu, Weimin; Zhou, Bingjiang; Xiao, Hongyan; Zhang, Hongyan; Wu, Jiasheng; Ge, Jiechao; Wang, Pengfei; The Journal of organic chemistry 81 (2016) 7393–7399; doi:10.1021/acs.joc.6b00981

data_4036928
_publ_section_title
;
 Deep-Red and Near-Infrared Xanthene Dyes for Rapid Live Cell Imaging.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7393
_journal_page_last               7399
_journal_paper_doi               10.1021/acs.joc.6b00981
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C24 H26 F3 N2 O, Cl O4'
_chemical_formula_sum            'C24 H26 Cl F3 N2 O5'
_chemical_formula_weight         514.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.89(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.165(4)
_cell_length_b                   7.1874(14)
_cell_length_c                   34.207(7)
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4805
_cell_measurement_theta_min      1.2320
_cell_volume                     4791.3(18)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'

;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1064
	          2theta: -19.9311
scan:
	Number of images: 270
	           Slice: -76.2500 - 58.7500
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1064
	          2theta: -19.9311
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0501
_diffrn_orient_matrix_UB_12      0.0072
_diffrn_orient_matrix_UB_13      0.0083
_diffrn_orient_matrix_UB_21      0.0297
_diffrn_orient_matrix_UB_22      -0.0914
_diffrn_orient_matrix_UB_23      -0.1006
_diffrn_orient_matrix_UB_31      0.0077
_diffrn_orient_matrix_UB_32      0.0227
_diffrn_orient_matrix_UB_33      -0.0184
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            15566
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.686
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       rod
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5441
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0751
_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^)+(0.1035P)^2^+7.3976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2019
_refine_ls_wR_factor_ref         0.2096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4837
_reflns_number_total             5441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00981_si_002.cif
_cod_data_source_block           sa4192
_cod_original_cell_volume        4791.2(18)
_cod_database_code               4036928
_diffrn_number_total             5882
_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
 Cl2-O7 = Cl2-O4 = Cl2-O5 = Cl2-O6
 1.43 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: Cl2(0.5) O4(0.5) O5(0.5) O6(0.5) O7(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,H17B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C18(H18), C19(H19), C21(H21)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              8174
_shelx_hkl_checksum              82312
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'