#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/54/1505455.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_1505455
loop_
_publ_author_name
'Yuan, Weicheng'
'Du, Haifeng'
'Zhao, Baoguo'
'Shi, Yian'
_publ_section_title
;
 A mild Cu(I)-catalyzed regioselective diamination of conjugated dienes.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2589
_journal_page_last               2591
_journal_paper_doi               10.1021/ol071105a
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C15 H26 N2 O3'
_chemical_formula_weight         282.38
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Bruker SHELXTL'
_cell_angle_alpha                109.931(2)
_cell_angle_beta                 91.021(3)
_cell_angle_gamma                104.591(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6652(3)
_cell_length_b                   10.3560(5)
_cell_length_c                   12.7813(6)
_cell_measurement_reflns_used    8683
_cell_measurement_temperature    100(2)
_cell_volume                     797.41(7)
_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 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker Kappa Apex2 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  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15010
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.094
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0822
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0733P)²+2.2085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2410
_refine_ls_wR_factor_ref         0.2495
_reflns_number_gt                3807
_reflns_number_total             4842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol071105asi20070514_020004.cif
_cod_data_source_block           ys159_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        797.41(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505455
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.4072(3) 0.4135(2) 0.14782(16) 0.0207(4) Uani 1 1 d .
O2 O -0.3680(4) 0.0748(3) 0.3751(2) 0.0342(5) Uani 1 1 d .
O3 O -0.6588(3) 0.1470(2) 0.36844(18) 0.0249(4) Uani 1 1 d .
N1 N 0.0940(3) 0.4409(2) 0.21315(18) 0.0178(4) Uani 1 1 d .
N2 N 0.0872(3) 0.2585(2) 0.05315(17) 0.0159(4) Uani 1 1 d .
C1 C 0.2157(4) 0.3755(3) 0.1389(2) 0.0161(5) Uani 1 1 d .
C2 C -0.1263(4) 0.2694(3) 0.0601(2) 0.0176(5) Uani 1 1 d .
H2A H -0.2273 0.1738 0.0382 0.021 Uiso 1 1 calc R
H2B H -0.1612 0.3193 0.0116 0.021 Uiso 1 1 calc R
C3 C -0.1255(4) 0.3571(3) 0.1848(2) 0.0178(5) Uani 1 1 d .
H3A H -0.2175 0.4219 0.1927 0.021 Uiso 1 1 calc R
C4 C 0.1821(4) 0.5605(3) 0.3206(2) 0.0212(5) Uani 1 1 d .
C5 C 0.3080(6) 0.5122(4) 0.3950(2) 0.0338(7) Uani 1 1 d .
H5A H 0.4228 0.4818 0.3561 0.051 Uiso 1 1 calc R
H5B H 0.2166 0.4323 0.4107 0.051 Uiso 1 1 calc R
H5C H 0.3648 0.5919 0.4655 0.051 Uiso 1 1 calc R
C6 C 0.3219(5) 0.6854(3) 0.2955(3) 0.0296(6) Uani 1 1 d .
H6A H 0.2399 0.7155 0.2484 0.044 Uiso 1 1 calc R
H6B H 0.4366 0.6555 0.2561 0.044 Uiso 1 1 calc R
H6C H 0.3788 0.7653 0.3659 0.044 Uiso 1 1 calc R
C7 C 0.0040(5) 0.6093(3) 0.3816(3) 0.0291(6) Uani 1 1 d .
H7A H -0.0755 0.6408 0.3345 0.044 Uiso 1 1 calc R
H7B H 0.0617 0.6887 0.4522 0.044 Uiso 1 1 calc R
H7C H -0.0883 0.5297 0.3973 0.044 Uiso 1 1 calc R
C8 C 0.1564(4) 0.2070(3) -0.0604(2) 0.0177(5) Uani 1 1 d .
C9 C 0.3498(4) 0.1561(3) -0.0541(2) 0.0248(6) Uani 1 1 d .
H9A H 0.4635 0.2360 -0.0056 0.037 Uiso 1 1 calc R
H9B H 0.3916 0.1200 -0.1293 0.037 Uiso 1 1 calc R
H9C H 0.3187 0.0796 -0.0231 0.037 Uiso 1 1 calc R
C10 C 0.2022(5) 0.3281(3) -0.1077(2) 0.0249(6) Uani 1 1 d .
H10A H 0.3144 0.4086 -0.0587 0.037 Uiso 1 1 calc R
H10B H 0.0761 0.3594 -0.1118 0.037 Uiso 1 1 calc R
H10C H 0.2452 0.2935 -0.1829 0.037 Uiso 1 1 calc R
C11 C -0.0183(4) 0.0813(3) -0.1364(2) 0.0229(5) Uani 1 1 d .
H11A H -0.0463 0.0041 -0.1061 0.034 Uiso 1 1 calc R
H11B H 0.0241 0.0468 -0.2117 0.034 Uiso 1 1 calc R
H11C H -0.1448 0.1121 -0.1401 0.034 Uiso 1 1 calc R
C12 C -0.1950(4) 0.2617(3) 0.2520(2) 0.0200(5) Uani 1 1 d .
H12A H -0.0986 0.2203 0.2751 0.024 Uiso 1 1 calc R
C13 C -0.3880(4) 0.2349(3) 0.2791(2) 0.0200(5) Uani 1 1 d .
H13A H -0.4825 0.2770 0.2552 0.024 Uiso 1 1 calc R
C14 C -0.4637(4) 0.1429(3) 0.3447(2) 0.0213(5) Uani 1 1 d .
C15 C -0.7555(5) 0.0645(4) 0.4343(3) 0.0315(7) Uani 1 1 d .
H15A H -0.8963 0.0754 0.4455 0.047 Uiso 1 1 calc R
H15B H -0.6720 0.0987 0.5072 0.047 Uiso 1 1 calc R
H15C H -0.7639 -0.0364 0.3949 0.047 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
C14 O3 C15 117.0(2)
C1 N1 C3 110.7(2)
C1 N1 C4 123.0(2)
C3 N1 C4 124.9(2)
C1 N2 C2 108.0(2)
C1 N2 C8 120.5(2)
C2 N2 C8 117.85(19)
O1 C1 N1 125.2(2)
O1 C1 N2 125.7(2)
N1 C1 N2 109.0(2)
N2 C2 C3 103.21(19)
N1 C3 C12 114.2(2)
N1 C3 C2 100.52(19)
C12 C3 C2 111.7(2)
N1 C4 C6 109.0(2)
N1 C4 C7 109.3(2)
C6 C4 C7 108.6(2)
N1 C4 C5 110.3(2)
C6 C4 C5 110.2(3)
C7 C4 C5 109.5(2)
N2 C8 C9 110.1(2)
N2 C8 C11 108.4(2)
C9 C8 C11 108.6(2)
N2 C8 C10 109.6(2)
C9 C8 C10 110.4(2)
C11 C8 C10 109.8(2)
C13 C12 C3 121.1(2)
C12 C13 C14 123.3(3)
O2 C14 O3 123.8(3)
O2 C14 C13 126.5(3)
O3 C14 C13 109.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.228(3)
O2 C14 1.208(4)
O3 C14 1.349(3)
O3 C15 1.444(3)
N1 C1 1.372(3)
N1 C3 1.467(3)
N1 C4 1.487(3)
N2 C1 1.394(3)
N2 C2 1.457(3)
N2 C8 1.491(3)
C2 C3 1.541(4)
C3 C12 1.514(4)
C4 C6 1.526(4)
C4 C7 1.529(4)
C4 C5 1.538(4)
C8 C9 1.521(4)
C8 C11 1.526(4)
C8 C10 1.537(4)
C12 C13 1.324(4)
C13 C14 1.478(4)
