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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/95/4109544.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4109544
loop_
_publ_author_name
'Haifeng Du'
'Weicheng Yuan'
'Baoguo Zhao'
'Yian Shi'
_publ_section_title
;
 A Pd(0)-Catalyzed Diamination of Terminal Olefins at Allylic and
 Homoallylic Carbons via Formal C-H Activation under Solvent-Free
 Conditions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7496
_journal_page_last               7497
_journal_paper_doi               10.1021/ja072080d
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C28 H50 N4 O2'
_chemical_formula_weight         474.72
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Bruker SHELXTL'
_cell_angle_alpha                90.00
_cell_angle_beta                 112.968(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4248(4)
_cell_length_b                   12.8075(4)
_cell_length_c                   11.7988(4)
_cell_measurement_reflns_used    3941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.14
_cell_measurement_theta_min      2.46
_cell_volume                     1450.44(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  "'Bruker SHELXTL"
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Apex2  area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13979
_diffrn_reflns_theta_full        30.37
_diffrn_reflns_theta_max         30.37
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.9862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       cube
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         4336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.0098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                2855
_reflns_number_total             4336
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja072080dsi20070510_124113.cif
_cod_data_source_block           ys157_0m
_cod_database_code               4109544
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.71320(10) 0.17318(7) 0.39603(9) 0.0196(2) Uani 1 1 d .
N1 N 0.88703(11) 0.28021(8) 0.38456(11) 0.0153(2) Uani 1 1 d .
N2 N 0.68095(11) 0.35078(8) 0.35337(10) 0.0149(2) Uani 1 1 d .
C1 C 0.90632(13) 0.39261(9) 0.37784(12) 0.0142(3) Uani 1 1 d .
H1A H 0.9622 0.4073 0.3273 0.017 Uiso 1 1 calc R
C2 C 0.75412(13) 0.42744(10) 0.30773(12) 0.0151(3) Uani 1 1 d .
H2A H 0.7398 0.4996 0.3328 0.018 Uiso 1 1 calc R
C3 C 0.75569(13) 0.25885(10) 0.37951(12) 0.0149(3) Uani 1 1 d .
C4 C 0.99624(13) 0.19935(10) 0.40969(13) 0.0176(3) Uani 1 1 d .
C5 C 0.94329(15) 0.11565(11) 0.30963(14) 0.0267(3) Uani 1 1 d .
H5A H 0.9204 0.1479 0.2288 0.040 Uiso 1 1 calc R
H5B H 0.8598 0.0827 0.3125 0.040 Uiso 1 1 calc R
H5C H 1.0158 0.0627 0.3235 0.040 Uiso 1 1 calc R
C6 C 1.12715(14) 0.24870(11) 0.40353(15) 0.0232(3) Uani 1 1 d .
H6A H 1.1046 0.2787 0.3216 0.035 Uiso 1 1 calc R
H6B H 1.1992 0.1951 0.4194 0.035 Uiso 1 1 calc R
H6C H 1.1614 0.3038 0.4657 0.035 Uiso 1 1 calc R
C7 C 1.03212(15) 0.15171(11) 0.53724(14) 0.0245(3) Uani 1 1 d .
H7A H 0.9484 0.1203 0.5415 0.037 Uiso 1 1 calc R
H7B H 1.0672 0.2064 0.5999 0.037 Uiso 1 1 calc R
H7C H 1.1037 0.0979 0.5521 0.037 Uiso 1 1 calc R
C8 C 0.52966(13) 0.35433(10) 0.32808(13) 0.0189(3) Uani 1 1 d .
C9 C 0.44595(14) 0.29102(12) 0.21265(14) 0.0251(3) Uani 1 1 d .
H9A H 0.4607 0.3200 0.1418 0.038 Uiso 1 1 calc R
H9B H 0.3467 0.2945 0.1975 0.038 Uiso 1 1 calc R
H9C H 0.4769 0.2181 0.2248 0.038 Uiso 1 1 calc R
C10 C 0.50806(15) 0.31088(12) 0.44010(15) 0.0258(3) Uani 1 1 d .
H10A H 0.5621 0.3523 0.5130 0.039 Uiso 1 1 calc R
H10B H 0.5392 0.2381 0.4534 0.039 Uiso 1 1 calc R
H10C H 0.4090 0.3144 0.4257 0.039 Uiso 1 1 calc R
C11 C 0.48190(15) 0.46791(11) 0.30973(15) 0.0249(3) Uani 1 1 d .
H11A H 0.4946 0.4966 0.2378 0.037 Uiso 1 1 calc R
H11B H 0.5372 0.5085 0.3830 0.037 Uiso 1 1 calc R
H11C H 0.3832 0.4716 0.2966 0.037 Uiso 1 1 calc R
C12 C 0.97391(14) 0.44505(10) 0.50394(12) 0.0157(3) Uani 1 1 d .
H12A H 0.9051 0.4485 0.5426 0.019 Uiso 1 1 calc R
H12B H 1.0531 0.4018 0.5574 0.019 Uiso 1 1 calc R
C13 C 0.71486(13) 0.42213(11) 0.17068(13) 0.0178(3) Uani 1 1 d .
H13A H 0.7249 0.3569 0.1366 0.021 Uiso 1 1 calc R
C14 C 0.66771(14) 0.50149(12) 0.09480(14) 0.0254(3) Uani 1 1 d .
H14A H 0.6564 0.5679 0.1256 0.030 Uiso 1 1 calc R
H14B H 0.6450 0.4924 0.0092 0.030 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C3 N1 C1 110.48(10) .
C3 N1 C4 122.99(10) .
C1 N1 C4 126.08(10) .
C3 N2 C2 108.90(10) .
C3 N2 C8 122.25(10) .
C2 N2 C8 124.61(10) .
N1 C1 C12 113.62(11) .
N1 C1 C2 100.35(9) .
C12 C1 C2 112.43(10) .
N2 C2 C13 113.64(10) .
N2 C2 C1 100.54(10) .
C13 C2 C1 110.76(11) .
O1 C3 N1 125.90(12) .
O1 C3 N2 126.27(12) .
N1 C3 N2 107.83(10) .
N1 C4 C7 110.48(11) .
N1 C4 C5 108.53(11) .
C7 C4 C5 110.86(12) .
N1 C4 C6 109.37(11) .
C7 C4 C6 109.34(11) .
C5 C4 C6 108.21(12) .
N2 C8 C11 108.63(11) .
N2 C8 C10 108.52(11) .
C11 C8 C10 108.64(12) .
N2 C8 C9 110.73(11) .
C11 C8 C9 109.72(12) .
C10 C8 C9 110.54(12) .
C12 C12 C1 112.67(13) 3_766
C14 C13 C2 124.61(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.2269(15) .
N1 C3 1.3745(16) .
N1 C1 1.4600(16) .
N1 C4 1.4809(17) .
N2 C3 1.3788(16) .
N2 C2 1.4685(16) .
N2 C8 1.4870(16) .
C1 C12 1.5307(18) .
C1 C2 1.5416(17) .
C2 C13 1.5068(19) .
C4 C7 1.529(2) .
C4 C5 1.5295(19) .
C4 C6 1.5312(19) .
C8 C11 1.5253(19) .
C8 C10 1.530(2) .
C8 C9 1.532(2) .
C12 C12 1.525(2) 3_766
C13 C14 1.3163(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102087646
