Porphyrin-based colorimetric sensing of perfluorooctanoic acid as proof of concept for perfluoroalkyl substance detection.
Taylor, Chloe M.; Ellingsen, Theo A.; Breadmore, Michael C.; Kilah, Nathan L.; Chemical communications (Cambridge, England)  (2021) –; doi:10.1039/d1cc04903h

data_7129201
_publ_section_title
;
 Porphyrin-based colorimetric sensing of perfluorooctanoic acid as proof
 of concept for perfluoroalkyl substance detection.
;
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d1cc04903h
_journal_year                    2021
_chemical_formula_moiety         'C76 H30 F60 N8 O4, 0.5(C6 H14)'
_chemical_formula_sum            'C79 H37 F60 N8 O4'
_chemical_formula_weight         2302.16
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-28
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-29 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                101.49(3)
_cell_angle_beta                 106.91(3)
_cell_angle_gamma                96.71(3)
_cell_formula_units_Z            2
_cell_length_a                   13.920(3)
_cell_length_b                   14.710(3)
_cell_length_c                   22.500(5)
_cell_measurement_reflns_used    71163
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.250
_cell_measurement_theta_min      0.976
_cell_volume                     4243.9(19)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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      100(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 21
_diffrn_detector_type            'ADSC Quantum 210r'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            71163
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.250
_diffrn_reflns_theta_min         0.976
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_description       block
_exptl_crystal_F_000             2278
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1767
_refine_ls_number_reflns         19307
_refine_ls_number_restraints     221
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0744P)^2^+1.2061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13675
_reflns_number_total             19307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04903h2.cif
_cod_data_source_block           19cmt4391
_cod_original_cell_volume        4243.9(17)
_cod_database_code               7129201
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.990
_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
 C32-C33 \\sim C32-C33A
 with sigma of 0.02
 F46-C33 \\sim F46A-C33A
 with sigma of 0.02
 F47-C33 \\sim F47A-C33A
 with sigma of 0.02
 C33-C34 \\sim C33A-C34A
 with sigma of 0.02
 C32-F46 \\sim C32-F46A
 with sigma of 0.04
 C32-F47 \\sim C32-F47A
 with sigma of 0.04
 F46-F47 \\sim F46A-F47A
 with sigma of 0.04
 F46-C34 \\sim F46A-C34
 with sigma of 0.04
 F47-C34 \\sim F47A-C34
 with sigma of 0.04
 F49-C34 \\sim F49A-C34A
 with sigma of 0.02
 F48-C34 \\sim F48A-C34A
 with sigma of 0.02
 C33-C34 \\sim C33-C34A
 with sigma of 0.02
 C35-C34 \\sim C35-C34A
 with sigma of 0.02
 C34-C33A \\sim C34A-C33A
 with sigma of 0.02
 F49-F48 \\sim F49A-F48A
 with sigma of 0.04
 F49-C33 \\sim F49A-C33
 with sigma of 0.04
 F49-C35 \\sim F49A-C35
 with sigma of 0.04
 F49-C33A \\sim F49A-C33A
 with sigma of 0.04
 F48-C33 \\sim F48A-C33
 with sigma of 0.04
 F48-C35 \\sim F48A-C35
 with sigma of 0.04
 F48-C33A \\sim F48A-C33A
 with sigma of 0.04
 F50-C35 \\sim F50A-C35A
 with sigma of 0.02
 F51-C35 \\sim F51A-C35A
 with sigma of 0.02
 F51-F48A \\sim F51A-F48A
 with sigma of 0.02
 C35-C34 \\sim C35A-C34
 with sigma of 0.02
 C35-C36 \\sim C35A-C36
 with sigma of 0.02
 C35-C34A \\sim C35A-C34A
 with sigma of 0.02
 F50-F51 \\sim F50A-F51A
 with sigma of 0.04
 F50-C34 \\sim F50A-C34
 with sigma of 0.04
 F50-C36 \\sim F50A-C36
 with sigma of 0.04
 F50-C34A \\sim F50A-C34A
 with sigma of 0.04
 F51-C34 \\sim F51A-C34
 with sigma of 0.04
 F51-C36 \\sim F51A-C36
 with sigma of 0.04
 F51-C34A \\sim F51A-C34A
 with sigma of 0.04
 C35-F48A \\sim C35A-F48A
 with sigma of 0.04
 F54-C36 \\sim F52A-C36A
 with sigma of 0.02
 F52-C36 \\sim F53A-C36A
 with sigma of 0.02
 F53-C36 \\sim F54A-C36A
 with sigma of 0.02
 F53-F50A \\sim F54A-F50A
 with sigma of 0.02
 C35-C36 \\sim C35-C36A
 with sigma of 0.02
 C36-C35A \\sim C36A-C35A
 with sigma of 0.02
 F54-F52 \\sim F52A-F53A
 with sigma of 0.04
 F54-F53 \\sim F52A-F54A
 with sigma of 0.04
 F54-C35 \\sim F52A-C35
 with sigma of 0.04
 F54-C35A \\sim F52A-C35A
 with sigma of 0.04
 F52-F53 \\sim F53A-F54A
 with sigma of 0.04
 F52-C35 \\sim F53A-C35
 with sigma of 0.04
 F52-C35A \\sim F53A-C35A
 with sigma of 0.04
 F53-C35 \\sim F54A-C35
 with sigma of 0.04
 F53-C35A \\sim F54A-C35A
 with sigma of 0.04
 C36-F50A \\sim C36A-F50A
 with sigma of 0.04
 F57-C41 \\sim F57A-C41A
 with sigma of 0.02
 F58-C41 \\sim F58A-C41A
 with sigma of 0.02
 C40-C41 \\sim C40-C41A
 with sigma of 0.02
 C41-C42 \\sim C41A-C42
 with sigma of 0.02
 F57-F58 \\sim F57A-F58A
 with sigma of 0.04
 F57-C40 \\sim F57A-C40
 with sigma of 0.04
 F57-C42 \\sim F57A-C42
 with sigma of 0.04
 F58-C40 \\sim F58A-C40
 with sigma of 0.04
 F58-C42 \\sim F58A-C42
 with sigma of 0.04
 F60-C42 \\sim F60A-C42A
 with sigma of 0.02
 F59-C42 \\sim F59A-C42A
 with sigma of 0.02
 F61-C43 \\sim F61A-C43A
 with sigma of 0.02
 F62-C43 \\sim F62A-C43A
 with sigma of 0.02
 F64-C44 \\sim F64A-C44A
 with sigma of 0.02
 F63-C44 \\sim F63A-C44A
 with sigma of 0.02
 F65-C45 \\sim F65A-C45A
 with sigma of 0.02
 F66-C45 \\sim F66A-C45A
 with sigma of 0.02
 F68-C46 \\sim F68A-C46A
 with sigma of 0.02
 F67-C46 \\sim F67A-C46A
 with sigma of 0.02
 F69-C46 \\sim F69A-C46A
 with sigma of 0.02
 C41-C42 \\sim C41-C42A
 with sigma of 0.02
 C42-C43 \\sim C42A-C43A
 with sigma of 0.02
 C42-C41A \\sim C42A-C41A
 with sigma of 0.02
 C43-C44 \\sim C43A-C44A
 with sigma of 0.02
 C44-C45 \\sim C44A-C45A
 with sigma of 0.02
 C45-C46 \\sim C45A-C46A
 with sigma of 0.02
 F60-F59 \\sim F60A-F59A
 with sigma of 0.04
 F60-C41 \\sim F60A-C41
 with sigma of 0.04
 F60-C43 \\sim F60A-C43A
 with sigma of 0.04
 F60-C41A \\sim F60A-C41A
 with sigma of 0.04
 F59-C41 \\sim F59A-C41
 with sigma of 0.04
 F59-C43 \\sim F59A-C43A
 with sigma of 0.04
 F59-C41A \\sim F59A-C41A
 with sigma of 0.04
 F61-F62 \\sim F61A-F62A
 with sigma of 0.04
 F61-C42 \\sim F61A-C42A
 with sigma of 0.04
 F61-C44 \\sim F61A-C44A
 with sigma of 0.04
 F62-C42 \\sim F62A-C42A
 with sigma of 0.04
 F62-C44 \\sim F62A-C44A
 with sigma of 0.04
 F64-F63 \\sim F64A-F63A
 with sigma of 0.04
 F64-C43 \\sim F64A-C43A
 with sigma of 0.04
 F64-C45 \\sim F64A-C45A
 with sigma of 0.04
 F63-C43 \\sim F63A-C43A
 with sigma of 0.04
 F63-C45 \\sim F63A-C45A
 with sigma of 0.04
 F65-F66 \\sim F65A-F66A
 with sigma of 0.04
 F65-C44 \\sim F65A-C44A
 with sigma of 0.04
 F65-C46 \\sim F65A-C46A
 with sigma of 0.04
 F66-C44 \\sim F66A-C44A
 with sigma of 0.04
 F66-C46 \\sim F66A-C46A
 with sigma of 0.04
 F68-F67 \\sim F68A-F67A
 with sigma of 0.04
 F68-F69 \\sim F68A-F69A
 with sigma of 0.04
 F68-C45 \\sim F68A-C45A
 with sigma of 0.04
 F67-F69 \\sim F67A-F69A
 with sigma of 0.04
 F67-C45 \\sim F67A-C45A
 with sigma of 0.04
 F69-C45 \\sim F69A-C45A
 with sigma of 0.04
 C41-C43 \\sim C41-C43A
 with sigma of 0.04
 C42-C44 \\sim C42A-C44A
 with sigma of 0.04
 C43-C45 \\sim C43A-C45A
 with sigma of 0.04
 C43-C41A \\sim C43A-C41A
 with sigma of 0.04
 C44-C46 \\sim C44A-C46A
 with sigma of 0.04
 C31-C30 \\sim C31-C30A
 with sigma of 0.02
 C314-C30 \\sim C314-C30A
 with sigma of 0.02
 F40-C30 \\sim F40A-C30A
 with sigma of 0.02
 F41-C30 \\sim F41A-C30A
 with sigma of 0.02
 C31-F40 \\sim C31-F40A
 with sigma of 0.04
 C31-F41 \\sim C31-F41A
 with sigma of 0.04
 C314-F40 \\sim C314-F40A
 with sigma of 0.04
 C314-F41 \\sim C314-F41A
 with sigma of 0.04
 F40-F41 \\sim F40A-F41A
 with sigma of 0.04
 C24-C25 \\sim C24-C25A
 with sigma of 0.02
 F36-C25 \\sim F36A-C25A
 with sigma of 0.02
 F35-C25 \\sim F35A-C25A
 with sigma of 0.02
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 F39-C26 \\sim F39A-C26A
 with sigma of 0.02
 F37-C26 \\sim F37A-C26A
 with sigma of 0.02
 F38-C26 \\sim F38A-C26A
 with sigma of 0.02
 C24-F36 \\sim C24-F36A
 with sigma of 0.04
 C24-F35 \\sim C24-F35A
 with sigma of 0.04
 C24-C26 \\sim C24-C26A
 with sigma of 0.04
 F36-F35 \\sim F36A-F35A
 with sigma of 0.04
 F36-C26 \\sim F36A-C26A
 with sigma of 0.04
 F35-C26 \\sim F35A-C26A
 with sigma of 0.04
 C25-F39 \\sim C25A-F39A
 with sigma of 0.04
 C25-F37 \\sim C25A-F37A
 with sigma of 0.04
 C25-F38 \\sim C25A-F38A
 with sigma of 0.04
 F39-F37 \\sim F39A-F37A
 with sigma of 0.04
 F39-F38 \\sim F39A-F38A
 with sigma of 0.04
 F37-F38 \\sim F37A-F38A
 with sigma of 0.04
3. Others
 Sof(F57A)=Sof(F58A)=Sof(F59A)=Sof(F60A)=Sof(F61A)=Sof(F62A)=Sof(F63A)=
 Sof(F64A)=Sof(F65A)=Sof(F66A)=Sof(F67A)=Sof(F68A)=Sof(F69A)=Sof(C41A)=
 Sof(C42A)=Sof(C43A)=Sof(C44A)=Sof(C45A)=Sof(C46A)=1-FVAR(1)
 Sof(F57)=Sof(F58)=Sof(F59)=Sof(F60)=Sof(F61)=Sof(F62)=Sof(F63)=Sof(F64)=
 Sof(F65)=Sof(F66)=Sof(F67)=Sof(F68)=Sof(F69)=Sof(C41)=Sof(C42)=Sof(C43)=
 Sof(C44)=Sof(C45)=Sof(C46)=FVAR(1)
 Sof(F40A)=Sof(F41A)=Sof(C30A)=1-FVAR(2)
 Sof(F40)=Sof(F41)=Sof(C30)=FVAR(2)
 Sof(F46A)=Sof(F47A)=Sof(F48A)=Sof(F49A)=Sof(F50A)=Sof(F51A)=Sof(F52A)=
 Sof(F53A)=Sof(F54A)=Sof(C33A)=Sof(C34A)=Sof(C35A)=Sof(C36A)=1-FVAR(3)
 Sof(F46)=Sof(F47)=Sof(F48)=Sof(F49)=Sof(F50)=Sof(F51)=Sof(F52)=Sof(F53)=
 Sof(F54)=Sof(C33)=Sof(C34)=Sof(C35)=Sof(C36)=FVAR(3)
 Sof(F35A)=Sof(F36A)=Sof(F37A)=Sof(F38A)=Sof(F39A)=Sof(C25A)=Sof(C26A)=1-FVAR(4)
 Sof(F35)=Sof(F36)=Sof(F37)=Sof(F38)=Sof(F39)=Sof(C25)=Sof(C26)=FVAR(4)
4.a Secondary CH2 refined with riding coordinates:
 C502(H50D,H50E), C503(H50F,H50G)
4.b Aromatic/amide H refined with riding coordinates:
 C103(H103), C104(H104), C108(H108), C109(H109), C110(H110), C111(H111),
 C203(H203), C204(H204), C208(H208), C209(H209), C210(H210), C211(H211),
 C303(H303), C304(H304), C308(H308), C309(H309), C310(H310), C311(H311),
 C403(H403), C404(H404), C408(H408), C409(H409), C410(H410), C411(H411)
4.c Idealised Me refined as rotating group:
 C501(H50A,H50B,H50C)
;
_shelx_res_checksum              54313
_shelx_hkl_checksum              31831
_olex2_submission_special_instructions 'No special instructions were received'