Synthesis, optical, and chemical properties of a π-extended rhodol derivative and its derivatives with selectivity and sensitivity for sensing Hg2+in aqueous media
Liang, Lijuan; Zhao, Liancheng; Zeng, Xianshun; RSC Adv. 6 (2016) 85165–; doi:10.1039/C6RA17024B

data_7226490
_publ_section_title
;
 Synthesis, optical, and chemical properties of a \p-extended rhodol
 derivative and its derivatives with selectivity and sensitivity for
 sensing Hg2+in aqueous media
;
_journal_issue                   88
_journal_name_full               'RSC Adv.'
_journal_page_first              85165
_journal_paper_doi               10.1039/C6RA17024B
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         '4(C38 H26.68 N O7), 11(C3 H7 N O)'
_chemical_formula_sum            'C185 H183.72 N15 O39'
_chemical_formula_weight         3241.18
_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             2015-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-10-27 deposited with the CCDC.
2016-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.302(3)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   24.9088(7)
_cell_length_b                   7.79540(17)
_cell_length_c                   22.8886(6)
_cell_measurement_reflns_used    7269
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.2110
_cell_measurement_theta_min      3.9730
_cell_volume                     4325.1(2)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega  -41.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   60.0000 74

  2 omega   38.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1514 -125.0000 -180.0000 26

  3 omega   90.00  122.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351 -125.0000 -120.0000 32

  4 omega   37.00   96.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351  -45.0000 -120.0000 59

  5 omega   99.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351   30.0000    0.0000 79

  6 omega  121.00  171.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351  125.0000    0.0000 50

  7 omega   52.00   89.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351  -30.0000   90.0000 37

  8 omega   75.00  107.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351  -95.0000   63.0000 32

  9 omega   41.00   86.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351  -30.0000   60.0000 45

 10 omega   41.00   73.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351  -95.0000   63.0000 32

 11 omega   33.00   86.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      106.0351  -30.0000 -180.0000 53

 12 omega -115.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000   60.0000 110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0279737000
_diffrn_orient_matrix_UB_12      0.0502810000
_diffrn_orient_matrix_UB_13      -0.0649929000
_diffrn_orient_matrix_UB_21      0.0523578000
_diffrn_orient_matrix_UB_22      -0.0529557000
_diffrn_orient_matrix_UB_23      -0.0205065000
_diffrn_orient_matrix_UB_31      -0.0226789000
_diffrn_orient_matrix_UB_32      -0.1836477000
_diffrn_orient_matrix_UB_33      -0.0118445000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16738
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.481
_diffrn_reflns_theta_min         3.647
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85940
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             1711
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         8556
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0874
_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^)+(0.1723P)^2^+3.5275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2535
_refine_ls_wR_factor_ref         0.2728
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6892
_reflns_number_total             8556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra17024b2.cif
_cod_data_source_block           a150527a
_cod_original_cell_volume        4325.13(19)
_cod_database_code               7226490
_reflns_odcompleteness_completeness 99.87
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N01E-C3 = N1-C3
 1.38 with sigma of 0.01
 N01E-C1C = N1-C37 = N1-C35 = N01E-C1A
 1.45 with sigma of 0.01
 C38-C37 = C1C-C1B = C1D-C1A = C36-C35
 1.5 with sigma of 0.01
 N01E-C1B
 2.44 with sigma of 0.01
 N01E-C1D
 2.44 with sigma of 0.01
 C36-N1
 2.44 with sigma of 0.01
 C38-N1
 2.44 with sigma of 0.01
 C37-C35 = C1C-C1A
 2.45 with sigma of 0.01
 N4'-C43' = N4'-C44'
 1.45 with sigma of 0.01
 N4'-C42'
 1.36 with sigma of 0.01
 O9'-C42'
 1.23 with sigma of 0.01
 H4-H1CB
 2.12 with sigma of 0.01
 C4-N01E \\sim N01E-C2
 with sigma of 0.001
 C4-N1 \\sim N1-C2
 with sigma of 0.001
 C44'-C42' \\sim C42'-C43'
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C43' \\sim N4' \\sim C44' \\sim C42' \\sim O9': within 2A with sigma of 0.001
and sigma for terminal atoms of 0.002
C44 \\sim C43 \\sim N4 \\sim C42 \\sim O9: within 2A with sigma of 0.001 and
sigma for terminal atoms of 0.002
Uanis(N1) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37)
\\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(C42) \\sim Ueq,
Uanis(N4) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C43) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(O9') \\sim Ueq, Uanis(N4') \\sim Ueq, Uanis(C44') \\sim Ueq, Uanis(C42')
\\sim Ueq, Uanis(C43') \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C37) = Uanis(C1C)
Uanis(N01E) = Uanis(N1)
Uanis(C1B) = Uanis(C38)
Uanis(C37) = Uanis(C1C)
Uanis(N1) = Uanis(N01E)
Uanis(C35) = Uanis(C1A)
Uanis(C36) = Uanis(C1D)
4. Others
 Sof(N01E)=Sof(C1A)=Sof(H1A)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C1C)=
 Sof(H1CA)=Sof(H1CB)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=1-FVAR(1)
 Sof(N1)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C35)=Sof(H35A)=Sof(H35B)=
 Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
 Fixed Sof: O9(0.75) N4(0.75) C43(0.75) H43A(0.75) H43B(0.75) H43C(0.75)
 C42(0.75) H42(0.75) C44(0.75) H44A(0.75) H44B(0.75) H44C(0.75) O10(0.75)
 N3(0.75) C47(0.75) H47A(0.75) H47B(0.75) H47C(0.75) C45(0.75) H45(0.75)
 C46(0.75) H46A(0.75) H46B(0.75) H46C(0.75) O9'(0.25) N4'(0.25) C44'(0.25)
 H44D(0.25) H44E(0.25) H44F(0.25) C42'(0.25) H42'(0.25) C43'(0.25) H43D(0.25)
 H43E(0.25) H43F(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C37(H37A,H37B), C1C(H1CA,H1CB)
5.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C16(H16), C11(H11), C17(H17), C26(H26), C23(H23), C33(H33),
 C25(H25), C12(H12), C24(H24), C5(H5A), C30(H30), C32(H32), C31(H31), C2(H2),
 C4(H4), C1A(H1A), C42(H42), C39(H39), C45(H45), C42'(H42')
5.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C36(H36A,H36B,H36C), C1B(H1BA,H1BB,H1BC), C1D(H1DA,H1DB,
 H1DC), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C41(H41A,H41B,H41C), C40(H40A,
 H40B,H40C), C47(H47A,H47B,H47C), C46(H46A,H46B,H46C), C44'(H44D,H44E,H44F),
 C43'(H43D,H43E,H43F)
5.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'