(15)N NMR Spectroscopy, X-ray and Neutron Diffraction, Quantum-Chemical Calculations, and UV/vis-Spectrophotometric Titrations as Complementary Techniques for the Analysis of Pyridine-Supported Bicyclic Guanidine Superbases.
Schwamm, Ryan J.; Vianello, Robert; Maršavelski, Aleksandra; García, M Ángeles; Claramunt, Rosa M.; Alkorta, Ibon; Saame, Jaan; Leito, Ivo; Fitchett, Christopher M.; Edwards, Alison J.; Coles, Martyn P.; The Journal of organic chemistry 81 (2016) 7612–7625; doi:10.1021/acs.joc.6b01330

data_4037034
_publ_section_title
;
 (15)N NMR Spectroscopy, X-ray and Neutron Diffraction, Quantum-Chemical
 Calculations, and UV/vis-Spectrophotometric Titrations as Complementary
 Techniques for the Analysis of Pyridine-Supported Bicyclic Guanidine
 Superbases.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7612
_journal_page_last               7625
_journal_paper_doi               10.1021/acs.joc.6b01330
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C12 H17 N4, C24 H20 B'
_chemical_formula_sum            'C36 H37 B N4'
_chemical_formula_weight         536.50
_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             2014-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                69.939(4)
_cell_angle_beta                 76.544(3)
_cell_angle_gamma                69.975(3)
_cell_formula_units_Z            2
_cell_length_a                   10.6291(3)
_cell_length_b                   11.8059(5)
_cell_length_c                   13.0252(5)
_cell_measurement_reflns_used    6699
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.1590
_cell_measurement_theta_min      3.6370
_cell_volume                     1430.14(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0196477000
_diffrn_orient_matrix_UB_12      -0.0335429000
_diffrn_orient_matrix_UB_13      -0.0984204000
_diffrn_orient_matrix_UB_21      -0.0251521000
_diffrn_orient_matrix_UB_22      0.1390604000
_diffrn_orient_matrix_UB_23      -0.0689858000
_diffrn_orient_matrix_UB_31      0.1522876000
_diffrn_orient_matrix_UB_32      -0.0239611000
_diffrn_orient_matrix_UB_33      -0.0410346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12127
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.254
_diffrn_reflns_theta_min         3.644
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0724P)^2^+0.3590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5234
_reflns_number_total             5843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01330_si_002.cif
_cod_data_source_block           1a
_cod_original_cell_volume        1430.15(10)
_cod_database_code               4037034
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         c34h28n8O8Cl2co1
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.038) H2A(0.035) H2B(0.035) H3A(0.038) H3B(0.038) H4A(0.035)
 H4B(0.035) H5A(0.03) H5B(0.03) H6A(0.031) H6B(0.031) H7A(0.033) H7B(0.033)
 H9(0.031) H10(0.033) H11(0.032) H12(0.031) H14(0.027) H15(0.029) H16(0.03)
 H17(0.028) H18(0.026) H20(0.029) H21(0.034) H22(0.036) H23(0.035) H24(0.031)
 H26(0.03) H27(0.034) H28(0.033) H29(0.031) H30(0.027) H32(0.026) H33(0.029)
 H34(0.03) H35(0.031) H36(0.03)
 Fixed X: H2A(0.4158) H2B(0.4652) H3A(0.1916) H3B(0.2871) H4A(0.2978)
 H4B(0.1451) H5A(0.1033) H5B(0.2414) H6A(0.331) H6B(0.1852) H7A(0.2217)
 H7B(0.1025) H9(0.3271) H10(0.373) H11(0.4486) H12(0.4734) H14(0.572)
 H15(0.3471) H16(0.2059) H17(0.2957) H18(0.5221) H20(0.5879) H21(0.6468)
 H22(0.8724) H23(1.0376) H24(0.9776) H26(0.9245) H27(0.981) H28(0.8813)
 H29(0.7293) H30(0.6767) H32(0.8741) H33(0.9643) H34(0.9623) H35(0.8683)
 H36(0.7798)
 Fixed Y: H2A(0.2994) H2B(0.1708) H3A(0.3199) H3B(0.3133) H4A(0.1106)
 H4B(0.1711) H5A(-0.0247) H5B(-0.0862) H6A(-0.1997) H6B(-0.2158) H7A(-0.1591)
 H7B(-0.0538) H9(0.3862) H10(0.4405) H11(0.282) H12(0.0769) H14(0.0784)
 H15(0.118) H16(0.3231) H17(0.4884) H18(0.4482) H20(0.383) H21(0.4608)
 H22(0.4181) H23(0.2915) H24(0.2121) H26(0.3817) H27(0.4852) H28(0.4798)
 H29(0.3617) H30(0.2555) H32(0.0577) H33(-0.1583) H34(-0.2718) H35(-0.1653)
 H36(0.0503)
 Fixed Z: H2A(0.0151) H2B(0.1049) H3A(0.1058) H3B(0.185) H4A(0.2795)
 H4B(0.2621) H5A(0.2592) H5B(0.3074) H6A(0.1831) H6B(0.2259) H7A(0.0308)
 H7B(0.0706) H9(-0.1374) H10(-0.329) H11(-0.4168) H12(-0.3104) H14(0.3882)
 H15(0.4609) H16(0.4271) H17(0.3215) H18(0.2555) H20(0.0934) H21(-0.0933) H22(-
 0.1699) H23(-0.0559) H24(0.1302) H26(0.2158) H27(0.312) H28(0.4916)
 H29(0.5759) H30(0.4809) H32(0.4525) H33(0.5009) H34(0.3871) H35(0.2232)
 H36(0.1753)
;
_shelx_res_checksum              71980
_shelx_hkl_checksum              52012