Anion control of tautomeric equilibria: Fe‒H vs. N‒H influenced by NH⋯F hydrogen bonding
Chambers, Geoffrey M.; Johnson, Samantha I.; Raugei, Simone; Bullock, R. Morris; Chemical Science  (2019) –; doi:10.1039/C8SC04239J

data_1550284
_publ_section_title
;
 Anion control of tautomeric equilibria: Fe--H vs. N--H influenced by
 NH&#x22EF;F hydrogen bonding
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC04239J
_journal_year                    2019
_chemical_formula_moiety         'C14 H28 Fe N O3 P2, B1 F4'
_chemical_formula_sum            'C14 H28 B F4 Fe N O3 P2'
_chemical_formula_weight         462.97
_chemical_name_systematic
; 
 ? 
;
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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
_audit_creation_date             2017-12-11
_audit_creation_method
; 
Olex2 1.2 
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) 
;
_audit_update_record
;
2017-12-12 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.783(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7564(9)
_cell_length_b                   10.0345(7)
_cell_length_c                   15.8101(14)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.50
_cell_volume                     2071.2(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2013.10-0 (Bruker, 2013)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2013/3, SADABS V2012/1, TWINABS V2012/1 
(Bruker, 2012 & 2013) 
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELX-2013-4 (Sheldrick, 2013)'
_computing_structure_solution    'SHELX-2013-4 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  a18a_0m
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3827
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.549
_diffrn_reflns_theta_min         2.498
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.745211
_exptl_absorpt_correction_T_min  0.662752
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
; 
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction. 
 
For component 1: 
 wR2(int) was 0.0569 before and 0.0489 after correction. 
 The Ratio of minimum to maximum transmission not present. 
 The \l/2 correction factor is Not present 
 
For component 2: 
 wR2(int) was 0.0672 before and 0.0588 after correction. 
 The Ratio of minimum to maximum transmission is 0.89. 
 The \l/2 correction factor is Not present 
 
Final HKLF 4 output contains 71960 reflections, Rint = 0.0630 
 (26573 with I > 3sig(I), Rint = 0.0370) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_id                a18a_0m
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research). 
;
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     433
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+2.1578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3281
_reflns_number_total             3827
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc04239j3.cif
_cod_data_source_block           a18a_0mout
_cod_database_code               1550284
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.683
_olex2_refinement_description
; 
1. Twinned data refinement 
 Scales: 0.698(1) 
 0.302(1) 
2. Fixed Uiso 
 At 1.2 times of: 
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
3. Restrained distances 
 F2-B1 \\sim F2A-B1A \\sim F3-B1 \\sim F3A-B1A \\sim F1-B1 \\sim F4A-B1A \\sim 
F4-B1 \\sim F1A-B1A 
 with sigma of 0.02 
 F1-F2 \\sim F1-F3 \\sim F1-F4 \\sim F2-F3 \\sim F2-F4 \\sim F3-F4 \\sim 
F1A-F2A \\sim F1A-F3A \\sim F1A-F4A ~ 
 F2A-F3A \\sim F2A-F4A \\sim F3A-F4A 
 with sigma of 0.02 
 N1-C5 \\sim N1A-C4A \\sim N1-C4 
 with sigma of 0.01 
4. Uiso/Uaniso restraints and constraints 
F2 \\sim F1 \\sim F4 \\sim F3 \\sim B1 \\sim F1A \\sim F2A \\sim B1A \\sim F4A 
\\sim F3A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 
P1 \\sim N1 \\sim C5 \\sim C6 \\sim C10 \\sim C7 \\sim C9 \\sim C8 \\sim C4 
\\sim N1A \\sim C6A \\sim C10A \\sim C4A \\sim C9A \\sim C7A \\sim C8A: within 
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 
5. Rigid body (RIGU) restrains 
 P1, N1, C5, C6, C10, C7, C9, C8, C4, N1A, C6A, C10A, C4A, C9A, C7A, C8A 
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002 
6. Others 
 Sof(F1A)=Sof(F2A)=Sof(B1A)=Sof(F4A)=Sof(F3A)=1-FVAR(1) 
 Sof(F2)=Sof(F1)=Sof(F4)=Sof(F3)=Sof(B1)=FVAR(1) 
 Sof(H5bc)=Sof(H5bd)=Sof(N1A)=Sof(H1A)=Sof(C6A)=Sof(H6Aa)=Sof(H6Ab)=Sof(H6Ac)= 
 Sof(C10A)=Sof(H10d)=Sof(H10e)=Sof(H10f)=Sof(C4A)=Sof(H4Aa)=Sof(H4Ab)=Sof(C9A)= 
 Sof(H9Aa)=Sof(H9Ab)=Sof(C7A)=Sof(H7Aa)=Sof(H7Ab)=Sof(C8A)=Sof(H8Aa)=Sof(H8Ab)= 
 Sof(H8Ac)=1-FVAR(2) 
 Sof(N1)=Sof(H1)=Sof(H5aa)=Sof(H5ab)=Sof(C6)=Sof(H6a)=Sof(H6b)=Sof(H6c)= 
 Sof(C10)=Sof(H10a)=Sof(H10b)=Sof(H10c)=Sof(C7)=Sof(H7a)=Sof(H7b)=Sof(C9)= 
 Sof(H9a)=Sof(H9b)=Sof(C8)=Sof(H8a)=Sof(H8b)=Sof(H8c)=Sof(C4)=Sof(H4a)=Sof(H4b)= 
 FVAR(2) 
7.a Ternary CH refined with riding coordinates: 
 N1(H1), N1A(H1A) 
7.b Secondary CH2 refined with riding coordinates: 
 C11(H11a,H11b), C13(H13a,H13b), C5(H5aa,H5ab), C5(H5bc,H5bd), C7(H7a,H7b), 
 C9(H9a,H9b), C4(H4a,H4b), C4A(H4Aa,H4Ab), C9A(H9Aa,H9Ab), C7A(H7Aa,H7Ab) 
7.c Idealised Me refined as rotating group: 
 C12(H12a,H12b,H12c), C14(H14a,H14b,H14c), C6(H6a,H6b,H6c), C10(H10a,H10b, 
 H10c), C8(H8a,H8b,H8c), C6A(H6Aa,H6Ab,H6Ac), C10A(H10d,H10e,H10f), C8A(H8Aa, 
 H8Ab,H8Ac) 
;
_shelx_res_checksum              13993
_olex2_submission_special_instructions 'No special instructions were received'