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_4034546
_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         'C24 H36 N6'
_chemical_formula_sum            'C24 H36 N6'
_chemical_formula_weight         408.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                89.257(2)
_cell_angle_beta                 74.918(2)
_cell_angle_gamma                67.207(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3851(19)
_cell_length_b                   10.325(2)
_cell_length_c                   13.344(3)
_cell_measurement_reflns_used    6230
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.431
_cell_measurement_theta_min      2.450
_cell_volume                     1145.4(4)
_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      110.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13527
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         1.588
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1236 before and 0.0351 after correction.
The Ratio of minimum to maximum transmission is 0.9052.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.452
_exptl_crystal_size_min          0.316
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0543P)^2^+0.5178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4538
_reflns_number_total             5195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01908_si_002.cif
_cod_data_source_block           out16
_cod_original_cell_volume        1145.3(4)
_cod_database_code               4034546
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H3 of N3, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H4 of N4
2.a Riding coordinates:
 N4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4A), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              75051
_shelx_hkl_checksum              88423
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'