Development of a Fluorophore with Enhanced Unorthodox Chalcogen Bonding for Highly Sensitive Detection of Trimethyl Arsine Vapor
Cui, Linfeng; Gong, Yanjun; Yu, Xinting; Lv, Chunxiao; Du, Xiaoming; Zhao, Jincai; Che, Yanke; ACS Sensors  (2021) –; doi:10.1021/acssensors.1c01185

data_4518916
_publ_section_title
;
 Development of a Fluorophore with Enhanced Unorthodox Chalcogen Bonding
 for Highly Sensitive Detection of Trimethyl Arsine Vapor
;
_journal_name_full               'ACS Sensors'
_journal_paper_doi               10.1021/acssensors.1c01185
_journal_year                    2021
_chemical_formula_moiety         '3(C H Cl3), 2(C88 H96 N6 O2 S3)'
_chemical_formula_sum            'C179 H195 Cl9 N12 O4 S6'
_chemical_formula_weight         3089.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90.1890(10)
_cell_angle_beta                 102.678(2)
_cell_angle_gamma                97.3800(10)
_cell_formula_units_Z            2
_cell_length_a                   19.1376(4)
_cell_length_b                   19.3087(3)
_cell_length_c                   22.5989(3)
_cell_measurement_reflns_used    33571
_cell_measurement_temperature    170.00(13)
_cell_measurement_theta_max      73.7830
_cell_measurement_theta_min      2.2830
_cell_volume                     8075.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_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    -19.00  26.00   0.50    1.00    --  -47.45  19.00 -30.00   90
  2  \w    -23.00  27.00   0.50    1.00    --  -47.45  19.00-120.00  100
  3  \w     34.00 110.00   0.50    1.00    --   47.45  57.00 -90.00  152
  4  \w     80.00 150.00   0.50    4.00    --  103.25 127.00 -25.00  140
  5  \w     91.00 168.00   0.50    4.00    --  103.25  45.00  90.00  154
  6  \w    111.00 169.00   0.50    4.00    --  103.25  54.00 135.84  116
  7  \w     94.00 119.00   0.50    4.00    --  103.25 143.00 144.00   50
  8  \w     81.00 162.00   0.50    4.00    --  103.25 125.00 120.00  162
  9  \w     76.00 119.00   0.50    1.00    --   47.45 143.00 144.00   86
 10  \w     40.00 117.00   0.50    1.00    --   47.45  77.00 150.00  154
 11  \w     33.00  71.00   0.50    4.00    --  103.25 -61.00 150.00   76
 12  \w     68.00 105.00   0.50    4.00    --  103.25 -94.00 120.00   74
 13  \w     78.00 105.00   0.50    4.00    --  103.25 -94.00  60.00   54
 14  \w     80.00 105.00   0.50    4.00    --  103.25 -94.00  30.00   50
 15  \w     43.00  69.00   0.50    1.00    --   47.45-143.00  89.00   52
 16  \w     34.00 125.00   0.50    4.00    --  103.25-143.00  89.00  182
 17  \w     47.00  74.00   0.50    4.00    --  103.25-125.00 150.00   54
 18  \w     35.00  60.00   0.50    4.00    --  103.25 -94.00 120.00   50
 19  \w     43.00  75.00   0.50    4.00    --  103.25 -61.00  60.00   64
 20  \w     31.00  70.00   0.50    4.00    --  103.25 -94.00  60.00   78
 21  \w     40.00  69.00   0.50    4.00    --  103.25 -61.00  90.00   58
 22  \w     47.00  74.00   0.50    4.00    --  103.25 -61.00 -60.00   54
 23  \w     60.00 104.00   0.50    4.00    --  103.25 -77.00-120.00   88
 24  \w     48.00  73.00   0.50    4.00    --  103.25-127.00-100.00   50
 25  \w     31.00 102.00   0.50    4.00    --  103.25 -94.00-120.00  142
 26  \w     48.00  75.00   0.50    4.00    --  103.25 -61.00 -90.00   54
 27  \w     34.00  59.00   0.50    1.00    --   47.45-127.00-100.00   50
 28  \w    -67.00 -26.00   0.50    4.00    --  -99.00  61.00-120.00   82
 29  \w    -69.00 -44.00   0.50    4.00    --  -99.00  77.00-180.00   50
 30  \w   -106.00 -68.00   0.50    4.00    --  -99.00 125.00 -60.00   76
 31  \w   -104.00 -61.00   0.50    4.00    --  -99.00 127.00 -25.00   86
 32  \w    -95.00 -35.00   0.50    1.00    --  -47.45 127.00 -25.00  120
 33  \w    -67.00 -41.00   0.50    4.00    --  -99.00  61.00 -30.00   52
 34  \w   -112.00 -86.00   0.50    4.00    --  -99.00 125.00   0.00   52
 35  \w   -127.00 -31.00   0.50    4.00    --  -99.00 146.00  82.31  192
 36  \w   -102.00 -63.00   0.50    1.00    --  -47.45 143.00 144.00   78
 37  \w   -125.00 -92.00   0.50    4.00    --  -99.00 143.00 144.00   66
 38  \w   -165.00 -87.00   0.50    4.00    --  -99.00 -50.00 -77.60  156
 39  \w   -112.00 -86.00   0.50    1.00    --  -47.45-127.00-100.00   52
 40  \w   -120.00 -65.00   0.50    1.00    --  -47.45-143.00  89.00  110
 41  \w   -120.00 -76.00   0.50    1.00    --  -47.45-125.00  30.00   88
 42  \w   -132.00 -85.00   0.50    4.00    --  -99.00 -48.00 -35.54   94
 43  \w   -125.00 -80.00   0.50    4.00    --  -99.00-127.00-100.00   90
 44  \w   -146.00 -82.00   0.50    4.00    --  -99.00 -61.00-180.00  128
 45  \w   -161.00-136.00   0.50    4.00    --  -99.00 -48.00 -35.54   50
 46  \w   -167.00 -87.00   0.50    4.00    --  -99.00 -54.00 -91.87  160
 47  \w   -139.00-114.00   0.50    4.00    --  -99.00-143.00  89.00   50
 48  \w   -112.00 -71.00   0.50    4.00    --  -99.00 125.00-180.00   82
 49  \w   -112.00 -48.00   0.50    4.00    --  -99.00 125.00-150.00  128
 50  \w   -131.00-104.00   0.50    4.00    --  -99.00 153.00-153.82   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0624116000
_diffrn_orient_matrix_UB_12      -0.0242377000
_diffrn_orient_matrix_UB_13      0.0312529000
_diffrn_orient_matrix_UB_21      -0.0528304000
_diffrn_orient_matrix_UB_22      -0.0106049000
_diffrn_orient_matrix_UB_23      -0.0624281000
_diffrn_orient_matrix_UB_31      0.0155979000
_diffrn_orient_matrix_UB_32      -0.0760232000
_diffrn_orient_matrix_UB_33      -0.0036644000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            123172
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.518
_diffrn_reflns_theta_min         2.309
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       plate
_exptl_crystal_F_000             3268
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.291
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2022
_refine_ls_number_reflns         32021
_refine_ls_number_restraints     497
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0965
_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^)+(0.1764P)^2^+7.9680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2712
_refine_ls_wR_factor_ref         0.2924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                23843
_reflns_number_total             32021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            se1c01185_si_002.cif
_cod_data_source_block           tx5285
_cod_database_code               4518916
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOS
_reflns_odcompleteness_completeness 99.82
_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
2. Restrained distances
 Cl1A-C88A = Cl2A-C88A = Cl3A-C88A
 1.76 with sigma of 0.01
 C93-C3 = C4-C3 = C93-C91 = C92-C3 = C3-C2 = C2-C1A
 1.54 with sigma of 0.01
 C3A-C2A = C3B-C2B = C2A-C1B = C2B-C1C = C4B-C3B
 1.54 with sigma of 0.01
 O1B-C3B = O1A-C3A
 1.47 with sigma of 0.01
 C87-C84 = C85-C84 = C86-C85
 1.54 with sigma of 0.01
 C85A-C84A = C86A-C85A = C87A-C84A
 1.54 with sigma of 0.01
 C1C-C3B
 2.5 with sigma of 0.02
 C1B-C3A
 2.5 with sigma of 0.02
3. Rigid bond restraints
 O2, C84, C87
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C63A, C64A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C27A, C36A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
O1A \\sim C1B \\sim C2A \\sim C3A \\sim C4A \\sim O1B \\sim C3B \\sim C4B \\sim
C2B \\sim C1C: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
O1 \\sim C1A \\sim C2 \\sim C3 \\sim C4 \\sim C91 \\sim C92 \\sim C93: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C88A \\sim Cl3A \\sim Cl2A \\sim Cl1A \\sim C88 \\sim Cl1 \\sim Cl2 \\sim Cl3:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
O2 \\sim C84 \\sim C85 \\sim C86 \\sim C87: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 1.7A
O2A \\sim C84A \\sim C87A \\sim C85A \\sim C86A: within 1.7A with sigma of 0.02
and sigma for terminal atoms of 0.04 within 1.7A
Uanis(C88) \\sim Ueq, Uanis(C88A) \\sim Ueq, Uanis(Cl3A) \\sim Ueq, Uanis(Cl2A)
\\sim Ueq, Uanis(Cl1A) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl1) \\sim Ueq,
Uanis(Cl2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1A) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A)
\\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(O1B) \\sim Ueq, Uanis(C3B) \\sim Ueq,
Uanis(C4B) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C1C) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C92) \\sim Ueq,
Uanis(C93) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2) \\sim Ueq, Uanis(C84) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C86)
\\sim Ueq, Uanis(C87) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C87A) \\sim Ueq, Uanis(C84A) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(C85A)
\\sim Ueq, Uanis(C86A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Others
 Sof(C88A)=Sof(H88A)=Sof(Cl3A)=Sof(Cl2A)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C88)=Sof(H88)=FVAR(1)
 Sof(O1B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(H4BC)=Sof(C2B)=
 Sof(H2BA)=Sof(H2BB)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=1-FVAR(2)
 Sof(O1A)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=FVAR(2)
 Sof(H3BB)=Sof(C91)=Sof(H91A)=Sof(H91B)=Sof(H91C)=Sof(C92)=Sof(H92A)=Sof(H92B)=
 Sof(H92C)=Sof(C93)=Sof(H93A)=Sof(H93B)=1-FVAR(3)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H3AA)=
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C88(H88), C89(H89), C90(H90), C3(H3AA), C3(H3BB), C84(H84), C3A(H3A),
 C84A(H84A), C88A(H88A), C3B(H3B)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C30(H30C,H30D), C31(H31C,H31D), C32(H32C,H32D), C33(H33C,H33D),
 C34(H34C,H34D), C36(H36C,H36D), C37(H37C,H37D), C38(H38C,H38D), C39(H39C,H39D),
  C40(H40C,H40D), C61(H61C,H61D), C62(H62C,H62D), C63(H63C,H63D), C64(H64C,
 H64D), C65(H65C,H65D), C67(H67C,H67D), C68(H68C,H68D), C69(H69C,H69D),
 C70(H70C,H70D), C85(H85C,H85D), C110(H11A,H11B), C1(H1A,H1B), C2A(H2AA,H2AB),
 C30A(H30A,H30B), C31A(H31A,H31B), C32A(H32A,H32B), C33A(H33A,H33B), C34A(H34A,
 H34B), C36A(H36A,H36B), C37A(H37A,H37B), C38A(H38A,H38B), C39A(H39A,H39B),
 C40A(H40A,H40B), C61A(H61A,H61B), C62A(H62A,H62B), C63A(H63A,H63B), C64A(H64A,
 H64B), C65A(H65A,H65B), C67A(H67A,H67B), C68A(H68A,H68B), C69A(H69A,H69B),
 C70A(H70A,H70B), C85A(H85A,H85B), C2B(H2BA,H2BB), C93(H93A,H93B)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C18(H18), C19(H19),
 C22(H22), C23(H23), C25(H25), C29(H29), C43(H43), C44(H44), C49(H49), C50(H50),
  C53(H53), C54(H54), C56(H56), C60(H60), C73(H73), C74(H74), C79(H79),
 C80(H80), C82(H82), C83(H83), C6A(H6A), C7A(H7A), C9A(H9A), C10A(H10A),
 C12A(H12A), C13A(H13A), C18A(H18A), C19A(H19A), C22A(H22A), C23A(H23A),
 C25A(H25A), C29A(H29A), C43A(H43A), C44A(H44A), C49A(H49A), C50A(H50A),
 C53A(H53A), C54A(H54A), C56A(H56A), C60A(H60A), C73A(H73A), C74A(H74A),
 C79A(H79A), C80A(H80A), C82A(H82A), C83A(H83A)
6.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C4(H4A,H4B,H4C), C35(H35D,H35E,H35F), C41(H41D,H41E,
 H41F), C66(H66D,H66E,H66F), C71(H71D,H71E,H71F), C86(H86D,H86E,H86F), C87(H87D,
 H87E,H87F), C1B(H1BA,H1BB,H1BC), C4A(H4AA,H4AB,H4AC), C35A(H35A,H35B,H35C),
 C41A(H41A,H41B,H41C), C66A(H66A,H66B,H66C), C71A(H71A,H71B,H71C), C86A(H86A,
 H86B,H86C), C87A(H87A,H87B,H87C), C4B(H4BA,H4BB,H4BC), C1C(H1CA,H1CB,H1CC),
 C91(H91A,H91B,H91C), C92(H92A,H92B,H92C)
;
_shelx_res_checksum              15917
_shelx_hkl_checksum              75911
_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 1.899
_oxdiff_exptl_absorpt_empirical_full_min 0.499