#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/41/4024152.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_4024152
loop_
_publ_author_name
'Jesús López-Cantarero'
'M. Belén Cid'
'Thomas B. Poulsen'
'Marco Bella'
'José Luis García Ruano'
'Karl Anker Jørgensen'
_publ_contact_author             'Farrugia, Louis J.'
_publ_contact_author_email       louis@chem.gla.ac.uk
_publ_section_title
;
 Intriguing Behavior of Cinchona Alkaloids in the Enantioselective
 Organocatalytic Hydroxyamination of α-Substituted-α-cyanoacetates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7062
_journal_page_last               7065
_journal_paper_doi               10.1021/jo071186o
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H20 N2 O2'
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2007-05-14T10:49:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.906(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0966(2)
_cell_length_b                   15.7561(7)
_cell_length_c                   8.7435(3)
_cell_measurement_reflns_used    1806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.06
_cell_measurement_theta_min      5.21
_cell_measurement_wavelength     0.71073
_cell_volume                     815.27(5)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 0.0833
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       'φ-scans and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7566
_diffrn_reflns_theta_full        64
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_min         5.21
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1158 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0406(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.0600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                2481
_reflns_number_total             2568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo071186o-File002.cif
_cod_data_source_block           07jo0016cu_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024152
_refine_friedel_coverage         0.821
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8231(2) 1.02461(11) 0.73450(18) 0.0160(4) Uani 1 1 d . . .
C2 C 1.0512(3) 1.03207(11) 0.84495(19) 0.0168(4) Uani 1 1 d . . .
C3 C 0.7386(3) 0.93145(11) 0.74319(18) 0.0160(4) Uani 1 1 d . . .
C4 C 0.8560(3) 0.78886(11) 0.67650(19) 0.0178(4) Uani 1 1 d . . .
C5 C 0.7896(3) 0.73833(11) 0.8049(2) 0.0237(4) Uani 1 1 d . . .
H5A H 0.8993 0.7484 0.9052 0.036 Uiso 1 1 calc R . .
H5B H 0.7872 0.6778 0.7789 0.036 Uiso 1 1 calc R . .
H5C H 0.6391 0.756 0.8138 0.036 Uiso 1 1 calc R . .
C6 C 1.0834(3) 0.76213(12) 0.6530(2) 0.0230(4) Uani 1 1 d . . .
H6A H 1.1968 0.7663 0.7534 0.035 Uiso 1 1 calc R . .
H6B H 1.1261 0.7994 0.5752 0.035 Uiso 1 1 calc R . .
H6C H 1.0749 0.7034 0.6153 0.035 Uiso 1 1 calc R . .
C7 C 0.6769(3) 0.78861(13) 0.5220(2) 0.0263(4) Uani 1 1 d . . .
H7A H 0.6637 0.7314 0.4767 0.039 Uiso 1 1 calc R . .
H7B H 0.7202 0.8285 0.4484 0.039 Uiso 1 1 calc R . .
H7C H 0.5314 0.8058 0.5412 0.039 Uiso 1 1 calc R . .
C11 C 0.7003(3) 1.16698(11) 0.80765(18) 0.0168(4) Uani 1 1 d . . .
C12 C 0.5603(3) 1.21152(11) 0.8855(2) 0.0201(4) Uani 1 1 d . . .
H12 H 0.4459 1.1821 0.9211 0.024 Uiso 1 1 calc R . .
C13 C 0.5873(3) 1.29810(11) 0.9108(2) 0.0224(4) Uani 1 1 d . . .
H13 H 0.4912 1.3276 0.9636 0.027 Uiso 1 1 calc R . .
C14 C 0.7533(3) 1.34205(12) 0.8598(2) 0.0237(4) Uani 1 1 d . . .
H14 H 0.771 1.4015 0.8768 0.028 Uiso 1 1 calc R . .
C15 C 0.8932(3) 1.29821(12) 0.7837(2) 0.0220(4) Uani 1 1 d . . .
H15 H 1.0083 1.3278 0.7493 0.026 Uiso 1 1 calc R . .
C16 C 0.8671(3) 1.21154(11) 0.75721(19) 0.0188(4) Uani 1 1 d . . .
H16 H 0.9638 1.1824 0.7043 0.023 Uiso 1 1 calc R . .
C21 C 0.8374(3) 1.03470(10) 0.56245(19) 0.0160(4) Uani 1 1 d . . .
C22 C 0.6425(3) 1.05551(10) 0.44969(19) 0.0182(4) Uani 1 1 d . . .
H22 H 0.5095 1.0711 0.4814 0.022 Uiso 1 1 calc R . .
C23 C 0.6415(3) 1.05356(11) 0.2909(2) 0.0227(4) Uani 1 1 d . . .
H23 H 0.5069 1.0668 0.2142 0.027 Uiso 1 1 calc R . .
C24 C 0.8351(3) 1.03245(11) 0.2435(2) 0.0227(4) Uani 1 1 d . . .
H24 H 0.834 1.0311 0.1347 0.027 Uiso 1 1 calc R . .
C25 C 1.0310(3) 1.01332(11) 0.3564(2) 0.0213(4) Uani 1 1 d . . .
H25 H 1.1652 0.9998 0.3244 0.026 Uiso 1 1 calc R . .
C26 C 1.0329(3) 1.01374(11) 0.5152(2) 0.0178(4) Uani 1 1 d . . .
H26 H 1.1673 0.9998 0.5916 0.021 Uiso 1 1 calc R . .
N1 N 1.2231(2) 1.03984(10) 0.93270(17) 0.0229(3) Uani 1 1 d . . .
N2 N 0.6629(2) 1.08006(9) 0.78074(16) 0.0180(3) Uani 1 1 d . . .
H2 H 0.5352 1.0582 0.7927 0.022 Uiso 1 1 calc R . .
O1 O 0.90109(17) 0.87921(7) 0.72799(13) 0.0177(3) Uani 1 1 d . . .
O2 O 0.55122(19) 0.91526(8) 0.75576(15) 0.0242(3) Uani 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N2 C1 C2 111.08(13) . . ?
N2 C1 C21 114.51(13) . . ?
C2 C1 C21 111.18(12) . . ?
N2 C1 C3 107.62(13) . . ?
C2 C1 C3 107.97(12) . . ?
C21 C1 C3 103.98(12) . . ?
N1 C2 C1 177.59(18) . . ?
O2 C3 O1 129.10(16) . . ?
O2 C3 C1 122.37(14) . . ?
O1 C3 C1 108.48(13) . . ?
O1 C4 C5 109.91(13) . . ?
O1 C4 C6 101.40(13) . . ?
C5 C4 C6 111.92(14) . . ?
O1 C4 C7 108.08(13) . . ?
C5 C4 C7 113.35(14) . . ?
C6 C4 C7 111.44(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C11 N2 122.87(15) . . ?
C16 C11 C12 118.56(15) . . ?
N2 C11 C12 118.55(15) . . ?
C13 C12 C11 120.51(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.58(16) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.14(17) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.78(17) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.44(16) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C22 C21 C26 119.54(15) . . ?
C22 C21 C1 118.63(13) . . ?
C26 C21 C1 121.39(14) . . ?
C23 C22 C21 120.14(15) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.45(15) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.37(15) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.66(15) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 119.81(15) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
C11 N2 C1 123.18(13) . . ?
C11 N2 H2 118.4 . . ?
C1 N2 H2 118.4 . . ?
C3 O1 C4 122.35(13) . . ?
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
C1 N2 1.439(2) . ?
C1 C2 1.495(2) . ?
C1 C21 1.536(2) . ?
C1 C3 1.563(2) . ?
C2 N1 1.147(2) . ?
C3 O2 1.2011(19) . ?
C3 O1 1.319(2) . ?
C4 O1 1.498(2) . ?
C4 C5 1.508(2) . ?
C4 C6 1.509(2) . ?
C4 C7 1.519(2) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C11 C16 1.392(2) . ?
C11 N2 1.399(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.95 . ?
C13 C14 1.386(3) . ?
C13 H13 0.95 . ?
C14 C15 1.386(3) . ?
C14 H14 0.95 . ?
C15 C16 1.388(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C21 C22 1.389(2) . ?
C21 C26 1.392(2) . ?
C22 C23 1.388(2) . ?
C22 H22 0.95 . ?
C23 C24 1.382(3) . ?
C23 H23 0.95 . ?
C24 C25 1.387(2) . ?
C24 H24 0.95 . ?
C25 C26 1.386(2) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
N2 H2 0.88 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.88 2.51 3.327(2) 153.8 1_455
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C3 O2 13.2(2) . . . . ?
C2 C1 C3 O2 133.21(16) . . . . ?
C21 C1 C3 O2 -108.61(17) . . . . ?
N2 C1 C3 O1 -169.29(12) . . . . ?
C2 C1 C3 O1 -49.31(16) . . . . ?
C21 C1 C3 O1 68.87(15) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
N2 C11 C12 C13 -178.24(15) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 -0.4(2) . . . . ?
N2 C11 C16 C15 178.40(15) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
N2 C1 C21 C22 -33.6(2) . . . . ?
C2 C1 C21 C22 -160.47(14) . . . . ?
C3 C1 C21 C22 83.59(17) . . . . ?
N2 C1 C21 C26 154.14(15) . . . . ?
C2 C1 C21 C26 27.2(2) . . . . ?
C3 C1 C21 C26 -88.70(17) . . . . ?
C26 C21 C22 C23 1.4(2) . . . . ?
C1 C21 C22 C23 -171.01(15) . . . . ?
C21 C22 C23 C24 -1.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 1.2(3) . . . . ?
C24 C25 C26 C21 -0.9(3) . . . . ?
C22 C21 C26 C25 -0.4(2) . . . . ?
C1 C21 C26 C25 171.83(16) . . . . ?
C16 C11 N2 C1 15.7(2) . . . . ?
C12 C11 N2 C1 -165.85(14) . . . . ?
C2 C1 N2 C11 52.88(19) . . . . ?
C21 C1 N2 C11 -74.07(18) . . . . ?
C3 C1 N2 C11 170.87(13) . . . . ?
O2 C3 O1 C4 18.5(3) . . . . ?
C1 C3 O1 C4 -158.71(12) . . . . ?
C5 C4 O1 C3 -70.11(18) . . . . ?
C6 C4 O1 C3 171.33(14) . . . . ?
C7 C4 O1 C3 54.07(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194017
