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_4034547
_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         '2(C15 H18 N3)'
_chemical_formula_sum            'C30 H36 N6'
_chemical_formula_weight         480.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-23
_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                 123.115(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.9278(11)
_cell_length_b                   10.4781(4)
_cell_length_c                   23.3336(10)
_cell_measurement_reflns_used    5870
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      50.467
_cell_measurement_theta_min      4.072
_cell_volume                     5309.5(4)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0604
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5131
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        49.996
_diffrn_reflns_theta_max         49.996
_diffrn_reflns_theta_min         4.071
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1249 before and 0.0795 after correction.
 The Ratio of minimum to maximum transmission is 0.70.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 34942 reflections, Rint = 0.1324
 (15545 with I > 3sig(I), Rint = 0.0963)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       needle
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     123
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0579P)^2^+3.8036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1939
_reflns_number_total             2686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01908_si_004.cif
_cod_data_source_block           out21
_cod_database_code               4034547
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.875
_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. Restrained distances
 C30-C27 \\sim C28A-C27 \\sim C28-C27 \\sim C29A-C27 \\sim C29-C27 \\sim
C30A-C27
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C27 \\sim C28 \\sim C29 \\sim C30 \\sim C28A \\sim C29A \\sim C30A: within 2A
with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C27, C28, C29, C30, C28A, C29A, C30A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C29A)=Sof(H29D)=Sof(H29E)=
 Sof(H29F)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C26(H26A,H26B)
6.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C6(H6A), C7(H7), C8(H8), C9(H9), N6(H6), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
6.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C28A(H28D,H28E,H28F),
 C29A(H29D,H29E,H29F), C30A(H30D,H30E,H30F)
;
_shelx_res_checksum              54786
_shelx_hkl_checksum              21865
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'