Indolizine-Cyanine Dyes: Near Infrared Emissive Cyanine Dyes with Increased Stokes Shifts.
Gayton, Jacqueline; Autry, Shane A.; Meador, William; Parkin, Sean R.; Hill, Jr, Glake Alton; Hammer, Nathan I.; Delcamp, Jared H.; The Journal of organic chemistry 84 (2019) 687–697; doi:10.1021/acs.joc.8b02521

data_4035976
_publ_section_title
;
 Indolizine-Cyanine Dyes: Near Infrared Emissive Cyanine Dyes with
 Increased Stokes Shifts.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              687
_journal_page_last               697
_journal_paper_doi               10.1021/acs.joc.8b02521
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C33 H27 N2), 2(Cl O4), C H4 O'
_chemical_formula_sum            'C33.5 H29 Cl N2 O4.5'
_chemical_formula_weight         567.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 108.702(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2142(6)
_cell_length_b                   25.3615(11)
_cell_length_c                   11.4422(7)
_cell_measurement_reflns_used    9632
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.36
_cell_volume                     3082.4(3)
_computing_cell_refinement       '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_data_reduction        '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_molecular_graphics    '<i>XP in SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material
'<i>SHELX</i> (Sheldrick, 2008) and <i>CIFFIX</i> (Parkin, 2013)'
_computing_structure_refinement  '<i>SHELXL-2018/3</i> (Sheldrick, 2015b)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            84864
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.501
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Krause et al., 2015)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       'irregular wedge'
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
Flack 'x' determined using 5226 quotients [(I+)-(I-)]/[(I+)+(I-)] 
[Parsons, Flack and Wagner (2013)]. 
;
_refine_ls_abs_structure_Flack   0.092(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     784
_refine_ls_number_reflns         14089
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+2.1794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1436
_reflns_Friedel_coverage         0.954
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                12294
_reflns_number_total             14089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02521_si_002.cif
_cod_data_source_block           m18106s
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C33.50 H29 Cl N2 O4.50'
_cod_database_code               4035976
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.976
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
_shelx_res_checksum              4008
_shelx_hkl_checksum              7768
_shelx_fab_checksum              17173