Ethylene-Bridged Hexadentate Bis(amidines) and Bis(amidinates) with Variable Binding Sites.
O'Dea, Connor; Ugarte Trejo, Omar; Arras, Janet; Ehnbom, Andreas; Bhuvanesh, Nattamai; Stollenz, Michael; The Journal of organic chemistry 84 (2019) 14217–14226; doi:10.1021/acs.joc.9b01908

data_4034548
_publ_section_title
;
 Ethylene-Bridged Hexadentate Bis(amidines) and Bis(amidinates) with
 Variable Binding Sites.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14217
_journal_page_last               14226
_journal_paper_doi               10.1021/acs.joc.9b01908
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C26 H40 N6, C6 H6'
_chemical_formula_sum            'C32 H46 N6'
_chemical_formula_weight         514.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.060(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0095(6)
_cell_length_b                   23.1808(13)
_cell_length_c                   13.2505(7)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.299
_cell_measurement_theta_min      3.814
_cell_volume                     3087.8(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19670
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        54.985
_diffrn_reflns_theta_max         54.985
_diffrn_reflns_theta_min         3.814
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1232 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8169.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     385
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0690
_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^)+(0.1315P)^2^+0.7023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.2012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2954
_reflns_number_total             3840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01908_si_003.cif
_cod_data_source_block           stufout17
_cod_database_code               4034548
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.902
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C20, C20A}
3. Restrained distances
 N5-C20 \\sim N5-C20A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim N6 \\sim C25 \\sim C26 \\sim
C20A \\sim C21A \\sim C22A \\sim C23A \\sim C24A \\sim N6A \\sim C25A \\sim
C26A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C20) = Uanis(C20A)
5. Rigid body (RIGU) restrains
 C20, C21, C22, C23, C24, N6, C25, C26, C20A, C21A, C22A, C23A, C24A, N6A,
 C25A, C26A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C20, C21, C22, C23, C24, N6, C25, C26} sigma for 1-2: 0.02, 1-3: 0.04
as
{C20A, C21A, C22A, C23A, C24A, N6A, C25A, C26A}
7. Others
 Sof(C1T)=Sof(H1T)=Sof(C2T)=Sof(H2T)=Sof(C3T)=Sof(H3T)=Sof(C4T)=Sof(H4T)=
 Sof(C5T)=Sof(H5T)=Sof(C6T)=Sof(H6T)=Sof(C20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=
 Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(N6A)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=
 Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(N6)=
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C1S)=Sof(H1S)=Sof(C2S)=Sof(H2S)=Sof(C3S)=Sof(H3S)=Sof(C4S)=Sof(H4S)=
 Sof(C5S)=Sof(H5S)=Sof(C6S)=Sof(H6S)=FVAR(1)
8.a Riding coordinates:
 C10(H10A,H10B,H10C)
8.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
8.c Me refined with riding coordinates:
 C6(H6A,H6B,H6C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C25A(H25D,H25E,
 H25F), C26A(H26D,H26E,H26F)
8.d Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C2(H2), C4(H4A), C21(H21), C23(H23), C1S(H1S), C2S(H2S),
 C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S), C1T(H1T), C2T(H2T), C3T(H3T), C4T(H4T),
  C5T(H5T), C6T(H6T), C21A(H21A), C23A(H23A)
8.e Fitted hexagon refined as free rotating group:
 C1S(C2S,C3S,C4S,C5S,C6S), C1T(C2T,C3T,C4T,C5T,C6T)
8.f Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              70816
_shelx_hkl_checksum              10840
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'