#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/12/7101250.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_7101250
loop_
_publ_author_name
'Yoshinao Tamaru'
'Masanari Kimura'
'Keisuke Kojima'
'Masahiko Mori'
'Nahoko Mukai'
_publ_section_title
;
Nickel catalyzed stereoselective conjugate addition of
dimethylzinc upon aldimines across 1,?-dienynes
;
_journal_issue                   26
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b605728d
_journal_year                    2006
_chemical_formula_moiety         'C25 H31 N O2 '
_chemical_formula_sum            'C25 H31 N O2'
_chemical_formula_weight         377.53
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                85.224(5)
_cell_angle_beta                 85.589(3)
_cell_angle_gamma                76.189(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8531(8)
_cell_length_b                   10.122(2)
_cell_length_c                   12.351(2)
_cell_measurement_temperature    297.2
_cell_volume                     1069.2(3)
_computing_cell_refinement       D*TREK
_computing_data_collection       D*TREK
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9244
_diffrn_measured_fraction_theta_max 0.9244
_diffrn_measurement_device_type  'Quantum CCD/Rigaku AFC7'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9132
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.638
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4498
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.0007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.02000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                2394
_reflns_number_total             4501
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b605728d.txt
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C25 H31 N O2 '
_cod_database_code               7101250
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_calc_flag
O(1) O 0.2581(2) 0.2530(2) 0.9429(1) 0.0590(5) Uani 1.00 d
O(2) O -0.4070(4) 1.2984(3) 0.5898(4) 0.174(2) Uani 1.00 d
N(1) N -0.3014(2) 0.7791(2) 0.8032(2) 0.0528(6) Uani 1.00 d
C(1) C 0.2834(3) 0.1214(3) 0.8998(2) 0.0600(8) Uani 1.00 d
C(2) C 0.1582(3) 0.1177(3) 0.8250(2) 0.0543(8) Uani 1.00 d
C(3) C 0.1465(2) 0.2289(2) 0.7347(2) 0.0434(6) Uani 1.00 d
C(4) C 0.1414(2) 0.3662(2) 0.7773(2) 0.0442(7) Uani 1.00 d
C(5) C 0.2677(3) 0.3533(3) 0.8564(2) 0.0557(8) Uani 1.00 d
C(6) C 0.1383(2) 0.2083(3) 0.6301(2) 0.0526(7) Uani 1.00 d
C(7) C 0.1326(4) 0.3175(3) 0.5391(2) 0.085(1) Uani 1.00 d
C(8) C 0.1332(3) 0.0717(3) 0.5913(2) 0.0740(10) Uani 1.00 d
C(9) C -0.0185(3) 0.4258(2) 0.8294(2) 0.0504(7) Uani 1.00 d
C(10) C -0.1399(3) 0.4894(3) 0.7797(2) 0.0569(8) Uani 1.00 d
C(11) C -0.3016(3) 0.5397(3) 0.8295(2) 0.0548(8) Uani 1.00 d
C(12) C -0.3862(2) 0.6793(2) 0.7800(2) 0.0483(7) Uani 1.00 d
C(13) C -0.5574(2) 0.7107(2) 0.8197(2) 0.0453(7) Uani 1.00 d
C(14) C -0.6710(3) 0.7015(3) 0.7521(3) 0.0605(9) Uani 1.00 d
C(15) C -0.8275(3) 0.7234(3) 0.7911(3) 0.0688(10) Uani 1.00 d
C(16) C -0.8689(3) 0.7534(3) 0.8963(3) 0.0670(9) Uani 1.00 d
C(17) C -0.7574(3) 0.7641(3) 0.9635(3) 0.0658(9) Uani 1.00 d
C(18) C -0.6024(3) 0.7428(2) 0.9257(2) 0.0523(7) Uani 1.00 d
C(19) C -0.3310(2) 0.9099(2) 0.7527(2) 0.0494(7) Uani 1.00 d
C(20) C -0.4365(3) 0.9533(3) 0.6720(2) 0.0554(8) Uani 1.00 d
C(21) C -0.4566(4) 1.0819(3) 0.6207(3) 0.0707(10) Uani 1.00 d
C(22) C -0.3738(4) 1.1705(3) 0.6481(3) 0.088(1) Uani 1.00 d
C(23) C -0.2709(4) 1.1309(4) 0.7272(4) 0.089(1) Uani 1.00 d
C(24) C -0.2486(3) 1.0022(3) 0.7800(3) 0.0692(10) Uani 1.00 d
C(25) C -0.3141(9) 1.3597(7) 0.5651(6) 0.193(3) Uani 1.00 d
H(1) H 0.286(3) 0.058(3) 0.965(2) 0.080(8) Uiso 1.00 calc
H(2) H 0.391(3) 0.103(3) 0.861(2) 0.073(8) Uiso 1.00 calc
H(3) H 0.189(3) 0.029(3) 0.794(2) 0.072(8) Uiso 1.00 calc
H(4) H 0.055(3) 0.128(3) 0.869(2) 0.075(8) Uiso 1.00 calc
H(5) H 0.160(2) 0.429(2) 0.718(2) 0.046(6) Uiso 1.00 calc
H(6) H 0.255(3) 0.435(3) 0.892(2) 0.073(8) Uiso 1.00 calc
H(7) H 0.376(3) 0.329(2) 0.816(2) 0.059(7) Uiso 1.00 calc
H(8) H 0.0432 0.3906 0.5511 0.1059 Uiso 1.00 calc
H(9) H 0.2238 0.3535 0.5373 0.1059 Uiso 1.00 calc
H(10) H 0.1276 0.2822 0.4714 0.1059 Uiso 1.00 calc
H(11) H 0.1285 0.0784 0.5130 0.0887 Uiso 1.00 calc
H(12) H 0.2250 0.0046 0.6093 0.0887 Uiso 1.00 calc
H(13) H 0.0445 0.0431 0.6227 0.0887 Uiso 1.00 calc
H(14) H -0.032(3) 0.421(3) 0.901(2) 0.087(10) Uiso 1.00 calc
H(15) H -0.129(4) 0.500(4) 0.702(3) 0.12(1) Uiso 1.00 calc
H(16) H -0.295(2) 0.546(2) 0.911(2) 0.059(7) Uiso 1.00 calc
H(17) H -0.363(3) 0.478(3) 0.820(2) 0.085(9) Uiso 1.00 calc
H(18) H -0.384(2) 0.672(2) 0.698(2) 0.044(6) Uiso 1.00 calc
H(19) H -0.645(3) 0.679(3) 0.673(2) 0.066(7) Uiso 1.00 calc
H(20) H -0.899(3) 0.718(3) 0.742(2) 0.084(9) Uiso 1.00 calc
H(21) H -0.983(3) 0.767(3) 0.917(2) 0.073(8) Uiso 1.00 calc
H(22) H -0.787(3) 0.789(3) 1.039(3) 0.094(10) Uiso 1.00 calc
H(23) H -0.526(3) 0.752(3) 0.975(2) 0.068(8) Uiso 1.00 calc
H(24) H -0.278(3) 0.768(3) 0.866(2) 0.08(1) Uiso 1.00 calc
H(25) H -0.496(3) 0.894(2) 0.652(2) 0.054(7) Uiso 1.00 calc
H(26) H -0.526(3) 1.110(3) 0.567(2) 0.087(10) Uiso 1.00 calc
H(27) H -0.210(4) 1.182(3) 0.747(3) 0.10(1) Uiso 1.00 calc
H(28) H -0.175(3) 0.969(3) 0.831(2) 0.080(9) Uiso 1.00 calc
H(29) H -0.2315 1.3118 0.5128 0.2268 Uiso 1.00 calc
H(30) H -0.2584 1.3795 0.6230 0.2268 Uiso 1.00 calc
H(31) H -0.3557 1.4475 0.5254 0.2268 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) O(1) C(5) 109.6(2) yes
C(22) O(2) C(25) 123.1(5) yes
C(12) N(1) C(19) 122.1(2) yes
O(1) C(1) C(2) 111.0(2) yes
C(1) C(2) C(3) 111.4(2) yes
C(2) C(3) C(4) 111.9(2) yes
C(2) C(3) C(6) 123.6(2) yes
C(4) C(3) C(6) 124.4(2) yes
C(3) C(4) C(5) 110.5(2) yes
C(3) C(4) C(9) 110.5(2) yes
C(5) C(4) C(9) 111.4(2) yes
O(1) C(5) C(4) 111.9(2) yes
C(3) C(6) C(7) 123.9(2) yes
C(3) C(6) C(8) 123.0(2) yes
C(7) C(6) C(8) 113.1(2) yes
C(4) C(9) C(10) 126.5(3) yes
C(9) C(10) C(11) 127.0(3) yes
C(10) C(11) C(12) 113.6(2) yes
N(1) C(12) C(11) 108.1(2) yes
N(1) C(12) C(13) 115.2(2) yes
C(11) C(12) C(13) 110.1(2) yes
C(12) C(13) C(14) 120.8(2) yes
C(12) C(13) C(18) 120.9(2) yes
C(14) C(13) C(18) 118.2(2) yes
C(13) C(14) C(15) 120.5(3) yes
C(14) C(15) C(16) 120.3(3) yes
C(15) C(16) C(17) 119.7(3) yes
C(16) C(17) C(18) 120.5(3) yes
C(13) C(18) C(17) 121.0(3) yes
N(1) C(19) C(20) 123.1(2) yes
N(1) C(19) C(24) 119.6(2) yes
C(20) C(19) C(24) 117.2(3) yes
C(19) C(20) C(21) 121.0(3) yes
C(20) C(21) C(22) 120.8(3) yes
O(2) C(22) C(21) 114.7(4) yes
O(2) C(22) C(23) 126.0(4) yes
C(21) C(22) C(23) 119.2(3) yes
C(22) C(23) C(24) 121.1(3) yes
C(19) C(24) C(23) 120.6(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.437(3) yes
O(1) C(5) 1.424(3) yes
O(2) C(22) 1.406(4) yes
O(2) C(25) 1.152(6) yes
N(1) C(12) 1.452(3) yes
N(1) C(19) 1.390(3) yes
C(1) C(2) 1.505(4) yes
C(2) C(3) 1.508(3) yes
C(3) C(4) 1.516(3) yes
C(3) C(6) 1.336(3) yes
C(4) C(5) 1.516(3) yes
C(4) C(9) 1.517(3) yes
C(6) C(7) 1.504(4) yes
C(6) C(8) 1.512(4) yes
C(9) C(10) 1.285(3) yes
C(10) C(11) 1.501(3) yes
C(11) C(12) 1.534(3) yes
C(12) C(13) 1.523(3) yes
C(13) C(14) 1.380(3) yes
C(13) C(18) 1.381(3) yes
C(14) C(15) 1.403(4) yes
C(15) C(16) 1.362(4) yes
C(16) C(17) 1.366(4) yes
C(17) C(18) 1.388(3) yes
C(19) C(20) 1.391(3) yes
C(19) C(24) 1.391(4) yes
C(20) C(21) 1.378(4) yes
C(21) C(22) 1.363(4) yes
C(22) C(23) 1.358(5) yes
C(23) C(24) 1.384(4) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) N(1) 3.169(3) 2_567
O(1) C(18) 3.573(3) 2_567
C(6) C(21) 3.505(4) 1_645
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O(1) C(1) C(2) C(3) 55.8(3) yes
O(1) C(5) C(4) C(3) -55.2(3) yes
O(1) C(5) C(4) C(9) 68.0(3) yes
O(2) C(22) C(21) C(20) -179.5(3) yes
O(2) C(22) C(23) C(24) 179.4(3) yes
N(1) C(12) C(11) C(10) -63.7(3) yes
N(1) C(12) C(13) C(14) 132.6(2) yes
N(1) C(12) C(13) C(18) -50.5(3) yes
N(1) C(19) C(20) C(21) -176.9(2) yes
N(1) C(19) C(24) C(23) 177.0(3) yes
C(1) O(1) C(5) C(4) 63.1(3) yes
C(1) C(2) C(3) C(4) -48.1(3) yes
C(1) C(2) C(3) C(6) 133.2(2) yes
C(2) C(1) O(1) C(5) -63.1(3) yes
C(2) C(3) C(4) C(5) 47.3(3) yes
C(2) C(3) C(4) C(9) -76.4(2) yes
C(2) C(3) C(6) C(7) -177.6(2) yes
C(2) C(3) C(6) C(8) 2.6(3) yes
C(3) C(4) C(9) C(10) -80.8(3) yes
C(4) C(3) C(6) C(7) 3.9(3) yes
C(4) C(3) C(6) C(8) -175.9(2) yes
C(4) C(9) C(10) C(11) 175.1(3) yes
C(5) C(4) C(3) C(6) -134.1(2) yes
C(5) C(4) C(9) C(10) 156.0(3) yes
C(6) C(3) C(4) C(9) 102.2(3) yes
C(9) C(10) C(11) C(12) 140.8(3) yes
C(10) C(11) C(12) C(13) 169.7(2) yes
C(11) C(12) N(1) C(19) 167.9(2) yes
C(11) C(12) C(13) C(14) -104.9(3) yes
C(11) C(12) C(13) C(18) 72.0(3) yes
C(12) N(1) C(19) C(20) -3.9(3) yes
C(12) N(1) C(19) C(24) 178.6(2) yes
C(12) C(13) C(14) C(15) 176.5(2) yes
C(12) C(13) C(18) C(17) -176.5(2) yes
C(13) C(12) N(1) C(19) -68.6(3) yes
C(13) C(14) C(15) C(16) -0.3(4) yes
C(13) C(18) C(17) C(16) 0.2(4) yes
C(14) C(13) C(18) C(17) 0.5(4) yes
C(14) C(15) C(16) C(17) 1.0(4) yes
C(15) C(14) C(13) C(18) -0.4(4) yes
C(15) C(16) C(17) C(18) -0.9(4) yes
C(19) C(20) C(21) C(22) -0.2(4) yes
C(19) C(24) C(23) C(22) 0.2(5) yes
C(20) C(19) C(24) C(23) -0.6(4) yes
C(20) C(21) C(22) C(23) -0.2(5) yes
C(21) C(20) C(19) C(24) 0.7(4) yes
C(21) C(22) O(2) C(25) -145.1(6) yes
C(21) C(22) C(23) C(24) 0.2(5) yes
C(23) C(22) O(2) C(25) 35.7(8) yes
C(23) C(22) O(2) C(25) 35.7(8) yes
