#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151280.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_7151280
loop_
_publ_author_name
'Berkessel, Albrecht'
'Mukherjee, Santanu'
'Müller, Thomas N'
'Cleemann, Felix'
'Roland, Katrin'
'Brandenburg, Marc'
'Neudörfl, Jörg-M'
'Lex, Johann'
_publ_section_title
;
 Structural optimization of thiourea-based bifunctional organocatalysts
 for the highly enantioselective dynamic kinetic resolution of
 azlactones.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4319
_journal_page_last               4330
_journal_paper_doi               10.1039/b607574f
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_sum            'C17 H27 N3 O'
_chemical_formula_weight         289.42
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1661(4)
_cell_length_b                   11.3191(6)
_cell_length_c                   15.5757(8)
_cell_measurement_reflns_used    7841
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.22
_cell_volume                     1616.01(14)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7841
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0339
_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)+(0.0415P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                1677
_reflns_number_total             2021
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b607574f.txt
_cod_data_source_block           26b
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7151280
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20537(12) 0.27340(11) 0.02288(9) 0.0222(3) Uani 1 1 d . . .
N1 N 0.47777(16) -0.06805(14) 0.05998(10) 0.0193(4) Uani 1 1 d . . .
N2 N 0.41723(17) 0.17663(14) 0.05144(10) 0.0194(4) Uani 1 1 d . . .
H2 H 0.508(2) 0.1724(17) 0.0408(13) 0.016(5) Uiso 1 1 d . . .
N3 N 0.41206(17) 0.32491(14) -0.04976(10) 0.0193(4) Uani 1 1 d . . .
H3 H 0.502(2) 0.3177(17) -0.0487(13) 0.022(6) Uiso 1 1 d . . .
C1 C 0.43950(19) -0.00419(17) 0.13915(11) 0.0178(4) Uani 1 1 d . . .
H1A H 0.5380(18) 0.0200(16) 0.1645(10) 0.008(4) Uiso 1 1 d . . .
C2 C 0.35338(19) 0.10875(15) 0.12111(11) 0.0172(4) Uani 1 1 d . . .
H2A H 0.2544(18) 0.0863(14) 0.1036(10) 0.005(4) Uiso 1 1 d . . .
C3 C 0.3427(2) 0.18141(17) 0.20390(12) 0.0240(4) Uani 1 1 d . . .
H3A H 0.446(2) 0.2012(18) 0.2231(12) 0.022(5) Uiso 1 1 d . . .
H3B H 0.296(2) 0.2589(18) 0.1896(14) 0.029(5) Uiso 1 1 d . . .
C4 C 0.2640(2) 0.1128(2) 0.27398(14) 0.0272(5) Uani 1 1 d . . .
H4A H 0.1596(19) 0.1005(15) 0.2582(10) 0.013(4) Uiso 1 1 d . . .
H4B H 0.256(2) 0.1608(18) 0.3264(13) 0.028(5) Uiso 1 1 d . . .
C5 C 0.3390(2) -0.0052(2) 0.29090(13) 0.0285(5) Uani 1 1 d . . .
H5A H 0.288(2) -0.0503(18) 0.3307(13) 0.030(6) Uiso 1 1 d . . .
H5B H 0.439(2) 0.0062(19) 0.3174(12) 0.026(5) Uiso 1 1 d . . .
C6 C 0.3559(2) -0.07562(17) 0.20760(12) 0.0223(4) Uani 1 1 d . . .
H6A H 0.257(2) -0.0999(16) 0.1881(12) 0.020(5) Uiso 1 1 d . . .
H6B H 0.4013(19) -0.1544(19) 0.2194(13) 0.023(5) Uiso 1 1 d . . .
C7 C 0.5680(2) -0.17108(18) 0.07714(15) 0.0255(5) Uani 1 1 d . . .
H7A H 0.5097(19) -0.2414(17) 0.1034(11) 0.018(5) Uiso 1 1 d . . .
H7B H 0.609(2) -0.1952(19) 0.0224(14) 0.028(6) Uiso 1 1 d . . .
H7C H 0.650(2) -0.1491(16) 0.1183(12) 0.024(5) Uiso 1 1 d . . .
C8 C 0.3537(2) -0.10029(19) 0.00671(13) 0.0250(4) Uani 1 1 d . . .
H8A H 0.284(2) -0.161(2) 0.0374(14) 0.034(6) Uiso 1 1 d . . .
H8B H 0.302(2) -0.0244(18) -0.0107(12) 0.021(5) Uiso 1 1 d . . .
H8C H 0.391(2) -0.138(2) -0.0451(14) 0.030(6) Uiso 1 1 d . . .
C9 C 0.33821(19) 0.25958(15) 0.00949(11) 0.0176(4) Uani 1 1 d . . .
C10 C 0.3579(2) 0.44186(16) -0.07457(11) 0.0184(4) Uani 1 1 d . . .
H10 H 0.252(2) 0.4403(16) -0.0635(11) 0.019(5) Uiso 1 1 d . . .
C11 C 0.4282(2) 0.53697(19) -0.01956(14) 0.0250(4) Uani 1 1 d . . .
H11A H 0.537(2) 0.5378(18) -0.0309(13) 0.025(5) Uiso 1 1 d . . .
H11B H 0.4120(19) 0.5190(18) 0.0417(13) 0.019(5) Uiso 1 1 d . . .
H11C H 0.386(2) 0.615(2) -0.0332(13) 0.027(5) Uiso 1 1 d . . .
C12 C 0.37264(19) 0.45969(16) -0.17109(12) 0.0189(4) Uani 1 1 d . . .
C13 C 0.3264(2) 0.37071(18) -0.22670(13) 0.0240(4) Uani 1 1 d . . .
H13 H 0.297(2) 0.2984(18) -0.2018(13) 0.025(5) Uiso 1 1 d . . .
C14 C 0.3321(2) 0.38527(19) -0.31480(13) 0.0300(5) Uani 1 1 d . . .
H14 H 0.299(2) 0.3192(18) -0.3515(13) 0.027(5) Uiso 1 1 d . . .
C15 C 0.3851(2) 0.4892(2) -0.35014(14) 0.0291(5) Uani 1 1 d . . .
H15 H 0.390(2) 0.4940(19) -0.4099(13) 0.027(6) Uiso 1 1 d . . .
C16 C 0.4324(2) 0.57787(19) -0.29626(13) 0.0266(5) Uani 1 1 d . . .
H16 H 0.472(2) 0.649(2) -0.3203(14) 0.039(6) Uiso 1 1 d . . .
C17 C 0.4262(2) 0.56372(18) -0.20728(13) 0.0225(4) Uani 1 1 d . . .
H17 H 0.457(2) 0.6277(19) -0.1716(12) 0.024(5) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C7 110.38(16) . . ?
C8 N1 C1 114.52(14) . . ?
C7 N1 C1 112.05(15) . . ?
C9 N2 C2 120.78(15) . . ?
C9 N2 H2 117.9(13) . . ?
C2 N2 H2 120.7(13) . . ?
C9 N3 C10 120.02(15) . . ?
C9 N3 H3 115.2(14) . . ?
C10 N3 H3 115.6(14) . . ?
N1 C1 C2 112.32(14) . . ?
N1 C1 C6 116.11(15) . . ?
C2 C1 C6 108.00(15) . . ?
N1 C1 H1A 104.2(9) . . ?
C2 C1 H1A 107.6(10) . . ?
C6 C1 H1A 108.2(9) . . ?
N2 C2 C1 111.81(14) . . ?
N2 C2 C3 111.74(14) . . ?
C1 C2 C3 109.09(15) . . ?
N2 C2 H2A 107.6(9) . . ?
C1 C2 H2A 108.2(9) . . ?
C3 C2 H2A 108.3(9) . . ?
C4 C3 C2 111.09(16) . . ?
C4 C3 H3A 110.1(11) . . ?
C2 C3 H3A 107.7(11) . . ?
C4 C3 H3B 113.9(12) . . ?
C2 C3 H3B 108.1(12) . . ?
H3A C3 H3B 105.6(16) . . ?
C3 C4 C5 110.92(17) . . ?
C3 C4 H4A 110.4(10) . . ?
C5 C4 H4A 110.7(10) . . ?
C3 C4 H4B 110.5(11) . . ?
C5 C4 H4B 112.0(12) . . ?
H4A C4 H4B 102.0(15) . . ?
C4 C5 C6 110.81(17) . . ?
C4 C5 H5A 111.7(12) . . ?
C6 C5 H5A 109.3(13) . . ?
C4 C5 H5B 111.5(12) . . ?
C6 C5 H5B 108.7(11) . . ?
H5A C5 H5B 104.7(16) . . ?
C5 C6 C1 111.30(16) . . ?
C5 C6 H6A 108.1(11) . . ?
C1 C6 H6A 112.7(11) . . ?
C5 C6 H6B 110.5(11) . . ?
C1 C6 H6B 112.8(11) . . ?
H6A C6 H6B 100.9(15) . . ?
N1 C7 H7A 113.1(10) . . ?
N1 C7 H7B 106.4(13) . . ?
H7A C7 H7B 109.2(16) . . ?
N1 C7 H7C 109.9(11) . . ?
H7A C7 H7C 108.6(14) . . ?
H7B C7 H7C 109.6(15) . . ?
N1 C8 H8A 112.4(11) . . ?
N1 C8 H8B 107.8(10) . . ?
H8A C8 H8B 112.7(16) . . ?
N1 C8 H8C 108.0(12) . . ?
H8A C8 H8C 107.4(17) . . ?
H8B C8 H8C 108.3(16) . . ?
O1 C9 N2 121.96(16) . . ?
O1 C9 N3 122.08(16) . . ?
N2 C9 N3 115.94(15) . . ?
N3 C10 C11 110.33(15) . . ?
N3 C10 C12 110.47(15) . . ?
C11 C10 C12 115.16(16) . . ?
N3 C10 H10 105.8(11) . . ?
C11 C10 H10 109.4(10) . . ?
C12 C10 H10 105.2(10) . . ?
C10 C11 H11A 109.0(12) . . ?
C10 C11 H11B 109.6(11) . . ?
H11A C11 H11B 108.6(15) . . ?
C10 C11 H11C 110.1(12) . . ?
H11A C11 H11C 110.1(17) . . ?
H11B C11 H11C 109.4(17) . . ?
C13 C12 C17 117.75(18) . . ?
C13 C12 C10 119.37(17) . . ?
C17 C12 C10 122.83(17) . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 121.4(12) . . ?
C12 C13 H13 117.3(12) . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 118.1(11) . . ?
C15 C14 H14 121.3(11) . . ?
C16 C15 C14 119.09(19) . . ?
C16 C15 H15 123.4(13) . . ?
C14 C15 H15 117.5(13) . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.7(13) . . ?
C17 C16 H16 119.8(13) . . ?
C12 C17 C16 120.8(2) . . ?
C12 C17 H17 120.5(12) . . ?
C16 C17 H17 118.6(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.245(2) . ?
N1 C8 1.454(2) . ?
N1 C7 1.454(2) . ?
N1 C1 1.472(2) . ?
N2 C9 1.354(2) . ?
N2 C2 1.453(2) . ?
N2 H2 0.847(19) . ?
N3 C9 1.363(2) . ?
N3 C10 1.466(2) . ?
N3 H3 0.826(19) . ?
C1 C2 1.529(2) . ?
C1 C6 1.542(3) . ?
C1 H1A 1.023(17) . ?
C2 C3 1.533(2) . ?
C2 H2A 0.981(16) . ?
C3 C4 1.522(3) . ?
C3 H3A 1.020(18) . ?
C3 H3B 1.00(2) . ?
C4 C5 1.525(3) . ?
C4 H4A 0.998(17) . ?
C4 H4B 0.98(2) . ?
C5 C6 1.531(3) . ?
C5 H5A 0.93(2) . ?
C5 H5B 1.012(19) . ?
C6 H6A 0.994(18) . ?
C6 H6B 1.00(2) . ?
C7 H7A 1.042(19) . ?
C7 H7B 0.97(2) . ?
C7 H7C 1.022(19) . ?
C8 H8A 1.06(2) . ?
C8 H8B 1.02(2) . ?
C8 H8C 0.98(2) . ?
C10 C11 1.519(3) . ?
C10 C12 1.523(3) . ?
C10 H10 0.989(19) . ?
C11 H11A 1.01(2) . ?
C11 H11B 0.988(19) . ?
C11 H11C 0.99(2) . ?
C12 C13 1.394(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.95(2) . ?
C14 C15 1.386(3) . ?
C14 H14 0.99(2) . ?
C15 C16 1.378(3) . ?
C15 H15 0.934(19) . ?
C16 C17 1.396(3) . ?
C16 H16 0.96(2) . ?
C17 H17 0.95(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10163606
