#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:49:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178825 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/79/4107991.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_4107991
loop_
_publ_author_name
'Haifeng Du'
'Baoguo Zhao'
'Yian Shi'
_publ_section_title
;
 Catalytic Asymmetric Allylic and Homoallylic Diamination of Terminal
 Olefins via Formal C-H Activation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8590
_journal_page_last               8591
_journal_paper_doi               10.1021/ja8027394
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_sum            'C15 H28 N2 O2'
_chemical_formula_weight         268.39
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4727(3)
_cell_length_b                   12.8011(5)
_cell_length_c                   17.0678(6)
_cell_measurement_reflns_used    5621
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.37
_cell_measurement_theta_min      2.98
_cell_volume                     1632.68(11)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker kappa Apex 2 CCD 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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13061
_diffrn_reflns_theta_full        32.42
_diffrn_reflns_theta_max         32.42
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_description       plates
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         5780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0730P)²+0.0906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                4462
_reflns_number_total             5780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8027394-file004.cif
_cod_data_source_block           ys181_0m
_cod_database_code               4107991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.88336(17) 0.90957(8) 0.73186(6) 0.0294(2) Uani 1 1 d .
O2 O 0.9840(2) 0.60683(9) 0.79295(9) 0.0442(4) Uani 1 1 d .
HA H 1.015(3) 0.5455(17) 0.7856(12) 0.040(6) Uiso 1 1 d .
N1 N 0.71276(16) 0.76110(8) 0.71494(6) 0.0196(2) Uani 1 1 d .
N2 N 0.80415(17) 0.80341(8) 0.83581(6) 0.0188(2) Uani 1 1 d .
C1 C 0.80746(18) 0.83174(9) 0.75823(7) 0.0187(2) Uani 1 1 d .
C2 C 0.6367(2) 0.67996(11) 0.76538(8) 0.0245(3) Uani 1 1 d .
H2A H 0.6701 0.6096 0.7445 0.029 Uiso 1 1 calc R
C3 C 0.73120(18) 0.69791(9) 0.84482(7) 0.0191(2) Uani 1 1 d .
H3A H 0.6408 0.6972 0.8880 0.023 Uiso 1 1 calc R
C4 C 0.4374(2) 0.68656(19) 0.77367(10) 0.0439(5) Uani 1 1 d .
H4A H 0.3776 0.6273 0.7946 0.053 Uiso 1 1 calc R
C5 C 0.3406(3) 0.7655(3) 0.75480(14) 0.0677(8) Uani 1 1 d .
H5A H 0.3950 0.8263 0.7336 0.081 Uiso 1 1 calc R
H5B H 0.2147 0.7631 0.7620 0.081 Uiso 1 1 calc R
C6 C 0.8766(2) 0.61600(11) 0.86123(9) 0.0287(3) Uani 1 1 d .
H6A H 0.9535 0.6418 0.9051 0.034 Uiso 1 1 calc R
C7 C 0.7945(3) 0.51250(13) 0.88526(11) 0.0469(5) Uani 1 1 d .
H7A H 0.7058 0.5243 0.9266 0.070 Uiso 1 1 calc R
H7B H 0.8885 0.4660 0.9049 0.070 Uiso 1 1 calc R
H7C H 0.7362 0.4803 0.8398 0.070 Uiso 1 1 calc R
C8 C 0.8430(2) 0.87836(11) 0.89975(8) 0.0266(3) Uani 1 1 d .
C9 C 1.0402(3) 0.90709(16) 0.89870(11) 0.0450(5) Uani 1 1 d .
H9A H 1.0705 0.9383 0.8480 0.068 Uiso 1 1 calc R
H9B H 1.1124 0.8441 0.9068 0.068 Uiso 1 1 calc R
H9C H 1.0649 0.9574 0.9406 0.068 Uiso 1 1 calc R
C10 C 0.7270(4) 0.97581(14) 0.88842(11) 0.0496(6) Uani 1 1 d .
H10A H 0.7552 1.0081 0.8378 0.074 Uiso 1 1 calc R
H10B H 0.7513 1.0257 0.9306 0.074 Uiso 1 1 calc R
H10C H 0.6004 0.9560 0.8895 0.074 Uiso 1 1 calc R
C11 C 0.7965(3) 0.82976(13) 0.97897(8) 0.0326(3) Uani 1 1 d .
H11A H 0.8695 0.7671 0.9872 0.049 Uiso 1 1 calc R
H11B H 0.6695 0.8106 0.9797 0.049 Uiso 1 1 calc R
H11C H 0.8206 0.8803 1.0208 0.049 Uiso 1 1 calc R
C12 C 0.7388(2) 0.75038(11) 0.62897(8) 0.0262(3) Uani 1 1 d .
C13 C 0.9349(3) 0.72717(14) 0.61171(10) 0.0371(4) Uani 1 1 d .
H13A H 1.0092 0.7850 0.6307 0.056 Uiso 1 1 calc R
H13B H 0.9517 0.7192 0.5551 0.056 Uiso 1 1 calc R
H13C H 0.9701 0.6624 0.6382 0.056 Uiso 1 1 calc R
C14 C 0.6790(3) 0.85068(14) 0.58802(10) 0.0391(4) Uani 1 1 d .
H14B H 0.7509 0.9095 0.6070 0.059 Uiso 1 1 calc R
H14C H 0.5524 0.8637 0.5995 0.059 Uiso 1 1 calc R
H14D H 0.6953 0.8432 0.5313 0.059 Uiso 1 1 calc R
C15 C 0.6249(3) 0.65939(14) 0.59875(9) 0.0370(4) Uani 1 1 d .
H15A H 0.4983 0.6735 0.6094 0.056 Uiso 1 1 calc R
H15B H 0.6606 0.5949 0.6254 0.056 Uiso 1 1 calc R
H15C H 0.6428 0.6516 0.5422 0.056 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
C1 N1 C2 110.66(11)
C1 N1 C12 121.84(11)
C2 N1 C12 124.46(11)
C1 N2 C3 110.59(10)
C1 N2 C8 122.39(11)
C3 N2 C8 126.34(11)
O1 C1 N1 125.22(12)
O1 C1 N2 125.05(12)
N1 C1 N2 109.73(11)
N1 C2 C4 113.66(15)
N1 C2 C3 103.48(10)
C4 C2 C3 111.27(12)
N2 C3 C6 112.66(12)
N2 C3 C2 102.41(10)
C6 C3 C2 112.44(11)
C5 C4 C2 125.49(19)
O2 C6 C7 112.24(13)
O2 C6 C3 107.86(12)
C7 C6 C3 111.06(15)
N2 C8 C9 109.76(14)
N2 C8 C11 110.09(11)
C9 C8 C11 109.24(13)
N2 C8 C10 108.88(12)
C9 C8 C10 110.51(16)
C11 C8 C10 108.34(15)
N1 C12 C13 109.54(13)
N1 C12 C14 109.61(13)
C13 C12 C14 110.88(14)
N1 C12 C15 109.26(12)
C13 C12 C15 108.72(13)
C14 C12 C15 108.80(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2316(16)
O2 C6 1.4197(19)
N1 C1 1.3654(17)
N1 C2 1.4639(17)
N1 C12 1.4865(17)
N2 C1 1.3731(17)
N2 C3 1.4645(16)
N2 C8 1.4819(17)
C2 C4 1.499(2)
C2 C3 1.5459(19)
C3 C6 1.536(2)
C4 C5 1.283(3)
C6 C7 1.517(2)
C8 C9 1.519(3)
C8 C11 1.528(2)
C8 C10 1.531(2)
C12 C13 1.525(2)
C12 C14 1.529(2)
C12 C15 1.532(2)
