Palladium-Catalyzed Dearomative syn-1,4-Diamination.
Wertjes, William C.; Okumura, Mikiko; Sarlah, David; Journal of the American Chemical Society 141 (2019) 163–167; doi:10.1021/jacs.8b13030

data_4133660
_publ_section_title
;
 Palladium-Catalyzed Dearomative syn-1,4-Diamination.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              163
_journal_page_last               167
_journal_paper_doi               10.1021/jacs.8b13030
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C16 H20 N4 O2, 0.66(H2 O)'
_chemical_formula_sum            'C16 H21.31 N4 O2.66'
_chemical_formula_weight         312.20
_chemical_name_systematic        naphthalene_nPrNH2_MTAD
_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     dual
_audit_creation_date             2018-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                101.9240(10)
_cell_angle_beta                 100.7390(10)
_cell_angle_gamma                100.1540(10)
_cell_formula_units_Z            4
_cell_length_a                   9.8206(4)
_cell_length_b                   11.1581(5)
_cell_length_c                   15.3236(7)
_cell_measurement_reflns_used    48171
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.29
_cell_volume                     1573.33(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_type            'photon counter area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            117799
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_min         2.165
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.745687
_exptl_absorpt_correction_T_min  0.578653
_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 0.1287 before and 0.0526 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1908 before and 0.0820 after correction.
 The Ratio of minimum to maximum transmission is 0.78.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 117894 reflections, Rint = 0.0542
 (78965 with I > 3sig(I), Rint = 0.0473)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       plate
_exptl_crystal_F_000             666
_exptl_crystal_recrystallization_method
'Crystallization was conducted by slow diffusion in dichloromethane/diethyl ether.'
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.238
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.051(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   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         117799
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0489P)^2^+0.5493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_number_gt                88361
_reflns_number_total             117799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13030_si_005.cif
_cod_data_source_block           twin5
_cod_database_code               4133660
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7544
 0.2456
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, All N(H,H) groups, All O(H,H) groups
3. Restrained distances
 O5-H5A \\sim O5-H5B
 with sigma of 0.01
4. Others
 Sof(O7)=Sof(H7A)=Sof(H7B)=FVAR(1)
 Sof(O6)=Sof(H6A)=Sof(H6B)=FVAR(2)
 Sof(O5)=Sof(H5A)=Sof(H5B)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C17(H17), C20(H20)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C30(H30A,H30B), C31(H31A,H31B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C19(H19), C22(H22),
 C23(H23), C24(H24), C25(H25)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C29(H29A,H29B,H29C), C32(H32A,H32B,
 H32C)
;
_shelx_res_checksum              90568
_shelx_hkl_checksum              38816
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on the spindle axis of 3 -3 4.'
_olex2_submission_original_sample_id naphthalene_nPrNH2_MTAD
_olex2_submission_special_instructions 'No special instructions were received'