Chiral and non-conjugated fluorescent salen ligands: AIE, anion probes, chiral recognition of unprotected amino acids, and cell imaging applications
Shen, Guangyu; Gou, Fei; Cheng, Jinghui; Zhang, Xiaohong; Zhou, Xiangge; Xiang, Haifeng; RSC Adv. 7 (2017) 40640–; doi:10.1039/C7RA08267C

data_7228959
_publ_section_title
;
 Chiral and non-conjugated fluorescent salen ligands: AIE, anion probes,
 chiral recognition of unprotected amino acids, and cell imaging
 applications
;
_journal_issue                   64
_journal_name_full               'RSC Adv.'
_journal_page_first              40640
_journal_paper_doi               10.1039/C7RA08267C
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C20 H20 F2 N2 O2'
_chemical_formula_sum            'C20 H20 F2 N2 O2'
_chemical_formula_weight         358.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-05-19 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                95.216(3)
_cell_angle_beta                 96.508(3)
_cell_angle_gamma                110.291(4)
_cell_formula_units_Z            4
_cell_length_a                   10.4661(4)
_cell_length_b                   11.0082(5)
_cell_length_c                   17.6201(5)
_cell_measurement_reflns_used    7859
_cell_measurement_temperature    293.28(10)
_cell_measurement_theta_max      72.3470
_cell_measurement_theta_min      4.5290
_cell_volume                     1873.25(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      air
_diffrn_ambient_temperature      293.28(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

  2 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88

  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  150.0000 84

  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   90.0000 84

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -180.0000 84

  6 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -90.0000 67

  7 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

  8 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

  9 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 94

 10 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -30.0000 74

 11 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

 12 omega   39.00  109.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

 13 omega   40.00   98.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 14 omega   39.00  109.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 15 omega   41.00  126.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 85

 16 omega   39.00  177.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -150.0000 138

 17 omega   40.00   98.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 18 omega   39.00  109.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 19 omega   39.00  109.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 20 omega   38.00   91.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 21 omega   38.00   91.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 22 omega   91.00  176.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

 23 omega   37.00   99.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -22.0000 -152.0000 62

 24 omega   40.00   98.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 25 omega   41.00  126.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 85

 26 omega   38.00  116.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 27 omega  -35.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -22.0000 -152.0000 99

 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

 29 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000    0.0000 84

 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   30.0000 94

 31 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1519572000
_diffrn_orient_matrix_UB_12      0.0825816000
_diffrn_orient_matrix_UB_13      -0.0020485000
_diffrn_orient_matrix_UB_21      -0.0253796000
_diffrn_orient_matrix_UB_22      0.1245456000
_diffrn_orient_matrix_UB_23      0.0294041000
_diffrn_orient_matrix_UB_31      0.0387295000
_diffrn_orient_matrix_UB_32      -0.0193431000
_diffrn_orient_matrix_UB_33      0.0838407000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19736
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         4.559
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0979P)^2^+0.1978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1621
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5515
_reflns_number_total             6681
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08267c2.cif
_cod_data_source_block           zxg-ljy-f
_cod_depositor_comments
;

2017-11-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1873.27(13)
_cod_original_formula_moiety     '2(C20 H20 F2 N2 O2)'
_cod_original_formula_sum        'C40 H40 F4 N4 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     716.76
_cod_database_code               7228959
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00O(H00O), C00S(H00S), C00Y(H00Y)
2.b Secondary CH2 refined with riding coordinates:
 C00X(H00C,H00D), C00Z(H00A,H00B), C010(H01A,H01B), C015(H01C,H01D), C017(H01E,
 H01F), C018(H01J,H01K), C01B(H01M,H01N), C01E(H01P,H01Q)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00N(H00N), C00P(H00P), C00Q(H00Q), C00T(H00T),
 C00U(H00U), C00V(H00V), C011(H011), C013(H013), C014(H014), C01A(H01L),
 C01C(H01O), C01D(H01G), C01F(H01H), C01G(H01I)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003), O005(H005), O006(H006)
;
_shelx_res_checksum              24163
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-24
_olex2_submission_special_instructions 'No special instructions were received'