#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:37:57 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178878 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/07/4110775.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_4110775
loop_
_publ_author_name
'Haile Zhang'
'Maria Mifsud'
'Fujie Tanaka'
'Carlos F. Barbas'
_publ_section_title
;
 3-Pyrrolidinecarboxylic Acid for Direct Catalytic
 Asymmetricanti-Mannich-Type Reactions of Unmodified Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9630
_journal_page_last               9631
_journal_paper_doi               10.1021/ja062950b
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C15 H21 N O4'
_chemical_formula_weight         279.33
_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                   5.3458(11)
_cell_length_b                   15.312(3)
_cell_length_c                   18.622(4)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.80
_cell_measurement_theta_min      2.56
_cell_volume                     1524.3(5)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  '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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11267
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.2722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      0
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             600
_exptl_crystal_size_max          20.00
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0643P)²+0.2450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                2170
_reflns_number_total             2690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja062950bsi20060505_030030.cif
_cod_data_source_block           zpnp
_cod_database_code               4110775
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
O1 O -0.0779(4) 0.05087(13) 0.73398(13) 0.0788(6) Uani 1 1 d .
O2 O 0.6087(5) 0.24506(17) 0.85059(15) 0.1067(9) Uani 1 1 d .
O3 O 0.2317(4) 0.30403(16) 0.85044(12) 0.0859(7) Uani 1 1 d .
O4 O 0.5611(5) 0.43125(14) 0.50891(11) 0.0839(7) Uani 1 1 d .
N1 N 0.4488(4) 0.16971(14) 0.71486(12) 0.0590(6) Uani 1 1 d .
H1A H 0.5236 0.1207 0.7080 0.071 Uiso 1 1 calc R
C1 C 0.2374(7) -0.05483(19) 0.74411(19) 0.0809(10) Uani 1 1 d .
H1C H 0.1291 -0.0880 0.7134 0.097 Uiso 1 1 calc R
H1D H 0.2636 -0.0861 0.7882 0.097 Uiso 1 1 calc R
H1E H 0.3951 -0.0459 0.7206 0.097 Uiso 1 1 calc R
C2 C 0.1211(5) 0.03070(17) 0.75982(14) 0.0543(7) Uani 1 1 d .
C3 C 0.2551(5) 0.09105(17) 0.81226(15) 0.0571(7) Uani 1 1 d .
H3 H 0.4204 0.0665 0.8228 0.069 Uiso 1 1 calc R
C4 C 0.1048(7) 0.0958(2) 0.88207(16) 0.0767(9) Uani 1 1 d .
H4A H 0.0838 0.0380 0.9012 0.092 Uiso 1 1 calc R
H4B H -0.0563 0.1209 0.8726 0.092 Uiso 1 1 calc R
H4C H 0.1926 0.1313 0.9163 0.092 Uiso 1 1 calc R
C5 C 0.2897(5) 0.18092(16) 0.77686(14) 0.0535(6) Uani 1 1 d .
H5 H 0.1261 0.2023 0.7609 0.064 Uiso 1 1 calc R
C6 C 0.3980(5) 0.24535(18) 0.83010(16) 0.0616(7) Uani 1 1 d .
C7 C 0.2998(8) 0.3681(3) 0.9047(2) 0.1093(14) Uani 1 1 d .
H7A H 0.4727 0.3596 0.9189 0.131 Uiso 1 1 calc R
H7B H 0.2835 0.4265 0.8851 0.131 Uiso 1 1 calc R
C8 C 0.1419(9) 0.3590(3) 0.9653(2) 0.1292(17) Uani 1 1 d .
H8A H 0.1897 0.3080 0.9919 0.155 Uiso 1 1 calc R
H8B H -0.0284 0.3531 0.9496 0.155 Uiso 1 1 calc R
H8C H 0.1572 0.4096 0.9953 0.155 Uiso 1 1 calc R
C9 C 0.4828(5) 0.23838(16) 0.66548(14) 0.0508(6) Uani 1 1 d .
C10 C 0.6815(5) 0.23519(19) 0.61745(17) 0.0660(8) Uani 1 1 d .
H10 H 0.7959 0.1896 0.6209 0.079 Uiso 1 1 calc R
C11 C 0.7145(5) 0.2976(2) 0.56470(16) 0.0667(8) Uani 1 1 d .
H11 H 0.8490 0.2936 0.5332 0.080 Uiso 1 1 calc R
C12 C 0.5493(5) 0.36528(18) 0.55891(15) 0.0600(7) Uani 1 1 d .
C13 C 0.3509(6) 0.36970(18) 0.60730(15) 0.0637(7) Uani 1 1 d .
H13 H 0.2378 0.4157 0.6041 0.076 Uiso 1 1 calc R
C14 C 0.3193(5) 0.30741(18) 0.65963(15) 0.0581(7) Uani 1 1 d .
H14 H 0.1859 0.3120 0.6915 0.070 Uiso 1 1 calc R
C15 C 0.7486(8) 0.4253(3) 0.45587(19) 0.0975(12) Uani 1 1 d .
H15A H 0.7324 0.3708 0.4308 0.117 Uiso 1 1 calc R
H15B H 0.9102 0.4283 0.4782 0.117 Uiso 1 1 calc R
H15C H 0.7308 0.4727 0.4225 0.117 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
C6 O3 C7 119.3(3)
C12 O4 C15 117.4(3)
C9 N1 C5 120.6(2)
O1 C2 C1 121.2(3)
O1 C2 C3 121.0(2)
C1 C2 C3 117.8(2)
C2 C3 C4 109.1(2)
C2 C3 C5 109.0(2)
C4 C3 C5 112.7(2)
N1 C5 C6 112.1(2)
N1 C5 C3 107.9(2)
C6 C5 C3 110.4(2)
O2 C6 O3 123.3(3)
O2 C6 C5 124.7(3)
O3 C6 C5 112.0(2)
C8 C7 O3 109.7(3)
C14 C9 C10 117.5(3)
C14 C9 N1 122.9(2)
C10 C9 N1 119.5(2)
C11 C10 C9 122.0(3)
C12 C11 C10 119.9(3)
C11 C12 O4 125.5(3)
C11 C12 C13 118.6(3)
O4 C12 C13 115.9(3)
C14 C13 C12 121.2(3)
C13 C14 C9 120.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.208(3)
O2 C6 1.189(3)
O3 C6 1.319(3)
O3 C7 1.455(4)
O4 C12 1.375(3)
O4 C15 1.410(4)
N1 C9 1.408(3)
N1 C5 1.444(3)
C1 C2 1.479(4)
C2 C3 1.523(4)
C3 C4 1.530(4)
C3 C5 1.537(4)
C5 C6 1.514(4)
C7 C8 1.416(5)
C9 C14 1.376(4)
C9 C10 1.390(4)
C10 C11 1.382(4)
C11 C12 1.366(4)
C12 C13 1.393(4)
C13 C14 1.374(4)
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
O1 C2 C3 C4 68.0(3)
C1 C2 C3 C4 -109.5(3)
O1 C2 C3 C5 -55.4(3)
C1 C2 C3 C5 127.2(3)
C9 N1 C5 C6 -68.0(3)
C9 N1 C5 C3 170.3(2)
C2 C3 C5 N1 -63.1(3)
C4 C3 C5 N1 175.8(2)
C2 C3 C5 C6 174.1(2)
C4 C3 C5 C6 53.0(3)
C7 O3 C6 O2 -4.9(5)
C7 O3 C6 C5 176.5(3)
N1 C5 C6 O2 -47.3(4)
C3 C5 C6 O2 73.0(4)
N1 C5 C6 O3 131.2(2)
C3 C5 C6 O3 -108.5(3)
C6 O3 C7 C8 -119.0(4)
C5 N1 C9 C14 -20.1(4)
C5 N1 C9 C10 163.5(2)
C14 C9 C10 C11 -1.0(4)
N1 C9 C10 C11 175.6(3)
C9 C10 C11 C12 0.3(4)
C10 C11 C12 O4 -179.9(3)
C10 C11 C12 C13 0.5(4)
C15 O4 C12 C11 4.9(4)
C15 O4 C12 C13 -175.4(3)
C11 C12 C13 C14 -0.4(4)
O4 C12 C13 C14 179.9(3)
C12 C13 C14 C9 -0.3(4)
C10 C9 C14 C13 1.1(4)
N1 C9 C14 C13 -175.4(3)
