Efficient colorimetric and fluorescent detection of fluoride in DMSO-water mixtures with arylaldoximes.
Rosen, Christian B.; Hansen, Dennis J.; Gothelf, Kurt V.; Organic & biomolecular chemistry 11 (2013) 7916–7922; doi:10.1039/c3ob41078a

data_7153136
_publ_section_title
;
 Efficient colorimetric and fluorescent detection of fluoride in
 DMSO-water mixtures with arylaldoximes.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7916
_journal_page_last               7922
_journal_paper_doi               10.1039/c3ob41078a
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'F, 2(C13 H13 N O3), C16 H36 N'
_chemical_formula_sum            'C42 H62 F N3 O6'
_chemical_formula_weight         723.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-12-05
_audit_creation_method
;
Olex2 1.2
(compiled Nov 5 2012 18:22:26, GUI svn.r4372)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.556(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4365(4)
_cell_length_b                   19.7096(17)
_cell_length_c                   11.9702(5)
_cell_measurement_reflns_used    15305
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      29.3225
_cell_measurement_theta_min      2.4095
_cell_volume                     1989.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 10.3590
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9905
_diffrn_measurement_details
;
1 omega -57.00 16.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 10.5301 -77.0000 150.0000 73

2 omega -93.00 -36.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- -11.9364 -19.0000 150.0000 57

3 omega -23.00 21.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- -11.9364 -19.0000 150.0000 44

4 omega -1.00 25.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- -11.9364 -99.0000 0.0000 26

5 omega -20.00 5.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 10.5301 -99.0000 -150.0000 25

6 omega -42.00 62.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- -11.9364 57.0000 -60.0000 104

7 omega -1.00 36.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 10.6864 -57.0000 -180.0000 37

8 omega 47.00 90.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 10.6864 -178.0000 120.0000 43

9 omega -65.00 -19.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- -11.9364 -38.0000 120.0000 46

10 omega -20.00 5.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- -11.9364 -99.0000 90.0000 25

11 omega -88.00 -63.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- -11.9364 -38.0000 -150.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0539242000
_diffrn_orient_matrix_UB_12      -0.0142650000
_diffrn_orient_matrix_UB_13      -0.0399245000
_diffrn_orient_matrix_UB_21      -0.0482009000
_diffrn_orient_matrix_UB_22      -0.0115773000
_diffrn_orient_matrix_UB_23      0.0437726000
_diffrn_orient_matrix_UB_31      -0.0428807000
_diffrn_orient_matrix_UB_32      0.0308952000
_diffrn_orient_matrix_UB_33      -0.0020380000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21857
_diffrn_reflns_theta_full        29.42
_diffrn_reflns_theta_max         29.42
_diffrn_reflns_theta_min         2.42
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2723
_exptl_crystal_size_mid          0.2115
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         9275
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.2795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                8558
_reflns_number_total             9275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41078a.txt
_cod_data_source_block           12jo0017s
_cod_database_code               7153136
_chemical_oxdiff_formula         'C42 H62 N3 O6 F'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H30 of C30, H18 of C18, H16 of C16, H11 of C11, H22 of C22, H27 of C27, H19
of C19, H26 of C26, H25 of C25, H38 of C38, H35 of C35, {H49A,H49B} of C49,
{H24A,H24B} of C24, {H33A,H33B} of C33, {H45A,H45B} of C45, {H51A,H51B} of
C51, H41 of C41, {H32A,H32B} of C32, {H28A,H28B} of C28, {H37A,H37B} of C37,
{H31A,H31B} of C31, {H52A,H52B} of C52, {H29A,H29B} of C29, {H50A,H50B} of C50
At 1.5 times of:
{H36A,H36B,H36C} of C36, {H42A,H42B,H42C} of C42, {H39A,H39B,H39C} of C39,
{H48A,H48B,H48C} of C48, {H47A,H47B,H47C} of C47, {H46A,H46B,H46C} of C46,
{H44A,H44B,H44C} of C44, {H43A,H43B,H43C} of C43
2.a Secondary CH2 refined with riding coordinates:
C24(H24A,H24B), C28(H28A,H28B), C29(H29A,H29B), C31(H31A,H31B), C32(H32A,
H32B), C33(H33A,H33B), C37(H37A,H37B), C45(H45A,H45B), C49(H49A,H49B),
C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B)
2.b Aromatic/amide H refined with riding coordinates:
C11(H11), C16(H16), C18(H18), C19(H19), C22(H22), C25(H25), C26(H26),
C27(H27), C30(H30), C35(H35), C38(H38), C41(H41)
2.c Idealised Me refined as rotating group:
C36(H36A,H36B,H36C), C39(H39A,H39B,H39C), C42(H42A,H42B,H42C), C44(H44A,H44B,
H44C), C43(H43A,H43B,H43C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,
H48B,H48C)
;