Activation of C-H, N-H, and O-H Bonds via Proton-Coupled Electron Transfer to a Mn(III) Complex of Redox-Noninnocent Octaazacyclotetradecadiene, a Catenated-Nitrogen Macrocyclic Ligand.
Vaddypally, Shivaiah; Tomlinson, Warren; O'Sullivan, Owen T; Ding, Ran; Van Vliet, Megan M.; Wayland, Bradford B.; Hooper, Joseph P.; Zdilla, Michael J.; Journal of the American Chemical Society 141 (2019) 5699–5709; doi:10.1021/jacs.8b10250

data_4128404
_publ_section_title
;
 Activation of C-H, N-H, and O-H Bonds via Proton-Coupled Electron
 Transfer to a Mn(III) Complex of Redox-Noninnocent
 Octaazacyclotetradecadiene, a Catenated-Nitrogen Macrocyclic Ligand.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5699
_journal_page_last               5709
_journal_paper_doi               10.1021/jacs.8b10250
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H20 Mn N9'
_chemical_formula_sum            'C10 H20 Mn N9'
_chemical_formula_weight         321.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5991(15)
_cell_length_b                   9.5866(19)
_cell_length_c                   20.193(4)
_cell_measurement_reflns_used    3388
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.35
_cell_volume                     1471.1(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BrukerAXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6006
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.869
_diffrn_reflns_theta_min         2.017
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0544 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.8915.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0549P)^2^+0.8784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2943
_reflns_number_total             3170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10250_si_002.cif
_cod_data_source_block           ct1_a
_cod_database_code               4128404
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.812
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.96(4)
 0.04(4)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C5(H5A,H5B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1A)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              53731
_shelx_hkl_checksum              13059
_olex2_exptl_crystal_mounting_method
'mounted using a Mit-e-Gen cryoloop with Paratone-N oil'
_olex2_submission_special_instructions 'No special instructions were received'