Tuning the tautomeric behavior of tris(salicylaldimines)
Mehr, S. Hessam M.; Oshima, Hiroya; Carta, Veronica; Patrick, Brian O.; White, Nicholas G.; MacLachlan, Mark J.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02058A

data_7155893
_publ_section_title
;
 Tuning the tautomeric behavior of tris(salicylaldimines)
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02058A
_journal_year                    2017
_chemical_formula_moiety         '1(C27 H6 F15 N3 O3)'
_chemical_formula_sum            'C27 H6 F15 N3 O3'
_chemical_formula_weight         705.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-08-16 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.23(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.834(4)
_cell_length_b                   4.9270(10)
_cell_length_c                   22.042(4)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.72
_cell_volume                     2352.3(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       'Bruker-Nonius Kappa diffractometer'
_diffrn_measurement_device_type  'MAR300 CCD'
_diffrn_measurement_method       '\k and \w scans'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'bending magnet'
_diffrn_radiation_wavelength     0.68879
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            35158
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.411
_diffrn_reflns_theta_max         27.311
_diffrn_reflns_theta_min         0.911
_diffrn_source                   synchrotron
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0596 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.6934.
The \l/2 correction factor is 0.0000.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1102
_refine_ls_number_reflns         11208
_refine_ls_number_restraints     1136
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0568P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                9991
_reflns_number_total             11208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02058a15.cif
_cod_data_source_block           Compound8
_cod_original_cell_volume        2352.4(8)
_cod_database_code               7155893
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(4) 0.0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C6A) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C3A)
\\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C28A) \\sim Ueq,
Uanis(C29A) \\sim Ueq, Uanis(C30A) \\sim Ueq, Uanis(C31A) \\sim Ueq,
Uanis(C32A) \\sim Ueq, Uanis(C33A) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.02
Uanis(N2) = Uanis(N2A)
Uanis(N3) = Uanis(N3A)
Uanis(N3A) = Uanis(N3)
Uanis(N1A) = Uanis(N1)
Uanis(N6A) = Uanis(N6)
Uanis(N4A) = Uanis(N4)
Uanis(N5A) = Uanis(N5)
Uanis(O4) = Uanis(O4A)
Uanis(O5A) = Uanis(O5)
Uanis(O6) = Uanis(O6A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C7A)=Sof(H7A)=Sof(C14A)=Sof(H14A)=Sof(N3A)=Sof(C21A)=Sof(H21A)=Sof(O2A)=
 Sof(H2A)=Sof(N1A)=Sof(C2A)=Sof(C6A)=Sof(C1A)=Sof(C5A)=Sof(O1A)=Sof(H1A)=
 Sof(O3A)=Sof(H3A)=Sof(N2A)=Sof(C4A)=Sof(C3A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(N1)=Sof(H1)=Sof(N2)=Sof(H2)=Sof(N3)=Sof(H3)=
 Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C14)=
 Sof(H14)=Sof(C21)=Sof(H21)=FVAR(1)
 Sof(N4A)=Sof(O6A)=Sof(H6A)=Sof(C41A)=Sof(H41A)=Sof(O4A)=Sof(H4A)=Sof(C48A)=
 Sof(H48A)=Sof(O5A)=Sof(H5A)=Sof(N5A)=Sof(N6A)=Sof(C32A)=Sof(C31A)=Sof(C28A)=
 Sof(C30A)=Sof(C29A)=Sof(C33A)=Sof(C34A)=Sof(H34A)=1-FVAR(2)
 Sof(O4)=Sof(O5)=Sof(O6)=Sof(N4)=Sof(H4)=Sof(N5)=Sof(H5)=Sof(N6)=Sof(H6)=
 Sof(C28)=Sof(C29)=Sof(C30)=Sof(C31)=Sof(C32)=Sof(C33)=Sof(C34)=Sof(H34)=
 Sof(C41)=Sof(H41)=Sof(C48)=Sof(H48)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C14(H14), C21(H21), N4(H4), C34(H34), C41(H41), C48(H48),
 C7A(H7A), C14A(H14A), C21A(H21A), C41A(H41A), C48A(H48A), C34A(H34A)
6.b Idealised tetrahedral OH refined as rotating group:
 O6A(H6A), O4A(H4A), O2A(H2A), O5A(H5A), O1A(H1A), O3A(H3A)
;
_shelx_res_checksum              55998