#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/54/1505419.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_1505419
loop_
_publ_author_name
'Hoang, Cam Thuy'
'Alezra, Valérie'
'Guillot, Régis'
'Kouklovsky, Cyrille'
_publ_section_title
;
 A stereoselective entry into functionalized 1,2-diamines by zinc-mediated
 homologation of alpha-aminoacids.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2521
_journal_page_last               2524
_journal_paper_doi               10.1021/ol0708020
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C12 H22 N2 O3, O0.50'
_chemical_formula_sum            'C12 H22 N2 O3.5'
_chemical_formula_weight         250.32
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.286(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.4890(17)
_cell_length_b                   14.7552(14)
_cell_length_c                   14.3559(13)
_cell_measurement_reflns_used    2504
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.51
_cell_volume                     3425.2(6)
_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(1)
_diffrn_measured_fraction_theta_full 0.789
_diffrn_measured_fraction_theta_max 0.789
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7034
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'X8 Apex Bruker'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            none
_exptl_crystal_density_diffrn    0.971
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.000(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0695
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                1949
_reflns_number_total             3097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0708020si20070405_055114.cif
_cod_data_source_block           181hoang100k
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C12 H22 N2 O3.50'
_cod_database_code               1505419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
OW1 O 0.5000 -0.2305(16) -0.2500 0.88(7) Uani 1 2 d S
O1 O 0.48033(17) 0.00615(19) 0.36998(17) 0.0410(9) Uani 1 1 d .
N2 N 0.6049(2) -0.0148(2) 0.3236(2) 0.0363(9) Uani 1 1 d .
H2 H 0.5927 0.0087 0.2678 0.044 Uiso 1 1 calc R
N1 N 0.59860(19) -0.0424(2) 0.4727(2) 0.0326(9) Uani 1 1 d .
H1N H 0.5776 -0.0568 0.5210 0.039 Uiso 1 1 calc R
O3 O 0.62500(18) -0.2497(2) 0.2044(2) 0.0526(10) Uani 1 1 d .
C2 C 0.5548(2) -0.0151(3) 0.3869(3) 0.0337(10) Uani 1 1 d .
C6 C 0.6836(3) -0.0603(3) 0.3632(3) 0.0372(10) Uani 1 1 d .
H6 H 0.7303 -0.0312 0.3419 0.045 Uiso 1 1 calc R
C3 C 0.7374(2) -0.1087(3) 0.5407(3) 0.0398(11) Uani 1 1 d .
H3 H 0.7181 -0.1705 0.5238 0.048 Uiso 1 1 calc R
C1 C 0.6865(2) -0.0436(3) 0.4702(3) 0.0348(10) Uani 1 1 d .
H1 H 0.7081 0.0176 0.4853 0.042 Uiso 1 1 calc R
C5 C 0.7260(3) -0.0897(3) 0.6417(3) 0.0524(13) Uani 1 1 d .
H5A H 0.7583 -0.1320 0.6845 0.079 Uiso 1 1 calc R
H5B H 0.6687 -0.0961 0.6449 0.079 Uiso 1 1 calc R
H5C H 0.7439 -0.0291 0.6593 0.079 Uiso 1 1 calc R
C7 C 0.6776(3) -0.1614(3) 0.3371(3) 0.0419(11) Uani 1 1 d .
H7A H 0.7262 -0.1927 0.3713 0.050 Uiso 1 1 calc R
H7B H 0.6295 -0.1873 0.3566 0.050 Uiso 1 1 calc R
C4 C 0.8282(3) -0.1026(4) 0.5336(3) 0.0586(14) Uani 1 1 d .
H4A H 0.8340 -0.1155 0.4697 0.088 Uiso 1 1 calc R
H4B H 0.8596 -0.1459 0.5760 0.088 Uiso 1 1 calc R
H4C H 0.8484 -0.0427 0.5508 0.088 Uiso 1 1 calc R
O2 O 0.7011(5) -0.1298(3) 0.1808(3) 0.141(3) Uani 1 1 d .
C8 C 0.6711(4) -0.1758(3) 0.2326(3) 0.0614(15) Uani 1 1 d .
C9 C 0.6113(4) -0.2826(4) 0.1057(3) 0.0687(17) Uani 1 1 d .
C11 C 0.6929(4) -0.3111(4) 0.0825(4) 0.085(2) Uani 1 1 d .
H11A H 0.7178 -0.3566 0.1268 0.127 Uiso 1 1 calc R
H11B H 0.7289 -0.2595 0.0866 0.127 Uiso 1 1 calc R
H11C H 0.6838 -0.3353 0.0192 0.127 Uiso 1 1 calc R
C12 C 0.5642(5) -0.3677(7) 0.1111(6) 0.155(5) Uani 1 1 d .
H12A H 0.5973 -0.4090 0.1543 0.233 Uiso 1 1 calc R
H12B H 0.5506 -0.3948 0.0492 0.233 Uiso 1 1 calc R
H12C H 0.5142 -0.3542 0.1333 0.233 Uiso 1 1 calc R
C10 C 0.5715(10) -0.2102(8) 0.0407(6) 0.274(10) Uani 1 1 d .
H10A H 0.5200 -0.1933 0.0573 0.411 Uiso 1 1 calc R
H10B H 0.5616 -0.2320 -0.0235 0.411 Uiso 1 1 calc R
H10C H 0.6073 -0.1583 0.0462 0.411 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
C2 N2 C6 110.5(3)
C2 N1 C1 109.6(3)
C8 O3 C9 121.9(4)
O1 C2 N2 125.6(3)
O1 C2 N1 125.4(4)
N2 C2 N1 109.0(3)
N2 C6 C7 109.8(3)
N2 C6 C1 99.4(3)
C7 C6 C1 112.5(3)
C4 C3 C1 109.9(4)
C4 C3 C5 111.0(3)
C1 C3 C5 111.3(3)
N1 C1 C3 114.4(3)
N1 C1 C6 100.9(3)
C3 C1 C6 117.8(3)
C8 C7 C6 111.7(3)
O2 C8 O3 123.8(5)
O2 C8 C7 126.2(5)
O3 C8 C7 109.9(4)
C12 C9 O3 102.3(5)
C12 C9 C11 105.9(6)
O3 C9 C11 109.2(4)
C12 C9 C10 118.0(8)
O3 C9 C10 109.4(4)
C11 C9 C10 111.4(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.244(5)
N2 C2 1.342(5)
N2 C6 1.473(5)
N1 C2 1.361(5)
N1 C1 1.457(5)
O3 C8 1.345(6)
O3 C9 1.473(5)
C6 C7 1.537(5)
C6 C1 1.547(5)
C3 C4 1.524(6)
C3 C1 1.522(5)
C3 C5 1.524(6)
C7 C8 1.498(6)
O2 C8 1.183(6)
C9 C12 1.486(11)
C9 C11 1.508(8)
C9 C10 1.485(10)
