Synthesis of near-infrared fluorescent rhodamines via an S<sub>N</sub>Ar<sup>H</sup> reaction and their biological applications.
Wang, Qing; Huang, Kun; Cai, Songtao; Liu, Chang; Jiao, Xiaojie; He, Song; Zhao, Liancheng; Zeng, Xianshun; Organic & biomolecular chemistry 16 (2018) 7163–7169; doi:10.1039/c8ob01701h

data_7156438
_publ_section_title
;
 Synthesis of near-infrared fluorescent rhodamines via an
 S<sub>N</sub>Ar<sup>H</sup> reaction and their biological applications.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7163
_journal_page_last               7169
_journal_paper_doi               10.1039/c8ob01701h
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C31 H26 N2 O4'
_chemical_formula_sum            'C31 H26 N2 O4'
_chemical_formula_weight         490.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-10-30 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.873(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.190(2)
_cell_length_b                   19.621(3)
_cell_length_c                   8.6624(15)
_cell_measurement_reflns_used    1490
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.2460
_cell_measurement_theta_min      2.4640
_cell_volume                     2737.3(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -75.00 120.00   1.00   10.00    --   30.00  54.00 240.00  195
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319269000
_diffrn_orient_matrix_UB_12      -0.0248987000
_diffrn_orient_matrix_UB_13      0.0110736000
_diffrn_orient_matrix_UB_21      0.0303387000
_diffrn_orient_matrix_UB_22      0.0261398000
_diffrn_orient_matrix_UB_23      0.0060318000
_diffrn_orient_matrix_UB_31      -0.0019735000
_diffrn_orient_matrix_UB_32      0.0014240000
_diffrn_orient_matrix_UB_33      0.0813204000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8430
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.431
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0714P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2520
_reflns_number_total             4819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01701h3.cif
_cod_data_source_block           14
_cod_depositor_comments          'Adding full bibliography for 7156438.cif.'
_cod_database_code               7156438
_reflns_odcompleteness_completeness 84.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.86
_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.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C18(H18), C10(H10), C2(H2), C15(H15), C16(H16), C3(H3), C26(H26),
 C5(H5), C27(H27), C4(H4), C29(H29), C28(H28)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C), C31(H31A,H31B,H31C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.629