#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150028.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_7150028
loop_
_publ_author_name
'Cobb, Alexander J. A.'
'Shaw, David M.'
'Longbottom, Deborah A.'
'Gold, Johan B.'
'Ley, Steven V.'
_publ_section_title
;
 Organocatalysis with proline derivatives: improved catalysts for the
 asymmetric Mannich, nitro-Michael and aldol reactions.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              84
_journal_page_last               96
_journal_paper_doi               10.1039/b414742a
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C14 H17 N O3'
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.29
_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                   5.5369(4)
_cell_length_b                   8.5297(8)
_cell_length_c                   27.769(3)
_cell_measurement_temperature    180(2)
_cell_volume                     1311.5(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            4884
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.75
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.018
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0649
_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)+(0.0590P)²+0.9507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1726
_reflns_number_gt                1289
_reflns_number_total             1661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b414742a.txt
_cod_data_source_block           sl0408
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7150028
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 0.5565(6) 0.8827(4) 0.73177(10) 0.0466(8) Uani 1 1 d . . .
O2 O 0.1869(6) 1.2278(4) 0.64485(13) 0.0486(8) Uani 1 1 d . . .
O3 O 0.4627(8) 1.3940(4) 0.62594(16) 0.0713(12) Uani 1 1 d . . .
N1 N 0.3993(7) 1.2681(4) 0.64258(14) 0.0409(9) Uani 1 1 d . . .
C1 C 0.7352(8) 0.8476(5) 0.70853(14) 0.0332(9) Uani 1 1 d . . .
C2 C 0.7640(8) 0.8898(5) 0.65587(13) 0.0320(9) Uani 1 1 d . . .
H2A H 0.9225 0.9445 0.6519 0.038 Uiso 1 1 calc R . .
C3 C 0.7767(10) 0.7323(5) 0.62798(15) 0.0417(11) Uani 1 1 d . . .
H3A H 0.6197 0.6775 0.6309 0.050 Uiso 1 1 calc R . .
H3B H 0.8050 0.7541 0.5934 0.050 Uiso 1 1 calc R . .
C4 C 0.9754(10) 0.6261(5) 0.64657(16) 0.0484(12) Uani 1 1 d . . .
H4A H 0.9714 0.5259 0.6286 0.058 Uiso 1 1 calc R . .
H4B H 1.1338 0.6762 0.6405 0.058 Uiso 1 1 calc R . .
C5 C 0.9508(11) 0.5924(5) 0.69977(16) 0.0492(12) Uani 1 1 d . . .
H5A H 1.0925 0.5316 0.7109 0.059 Uiso 1 1 calc R . .
H5B H 0.8043 0.5284 0.7055 0.059 Uiso 1 1 calc R . .
C6 C 0.9330(10) 0.7464(6) 0.72858(15) 0.0459(11) Uani 1 1 d . . .
H6A H 0.8992 0.7227 0.7628 0.055 Uiso 1 1 calc R . .
H6B H 1.0887 0.8032 0.7269 0.055 Uiso 1 1 calc R . .
C7 C 0.5645(8) 0.9989(4) 0.63646(14) 0.0320(9) Uani 1 1 d . . .
H7A H 0.4048 0.9533 0.6458 0.038 Uiso 1 1 calc R . .
C8 C 0.5886(8) 1.1596(5) 0.66094(15) 0.0355(10) Uani 1 1 d . . .
H8A H 0.5714 1.1474 0.6962 0.043 Uiso 1 1 calc R . .
H8B H 0.7505 1.2038 0.6543 0.043 Uiso 1 1 calc R . .
C9 C 0.5710(9) 1.0122(5) 0.58181(14) 0.0345(9) Uani 1 1 d . . .
C10 C 0.3921(10) 0.9425(6) 0.55450(16) 0.0468(12) Uani 1 1 d . . .
H10A H 0.2605 0.8925 0.5702 0.056 Uiso 1 1 calc R . .
C11 C 0.4012(12) 0.9442(7) 0.50441(18) 0.0621(16) Uani 1 1 d . . .
H11A H 0.2783 0.8947 0.4860 0.074 Uiso 1 1 calc R . .
C12 C 0.5936(13) 1.0198(8) 0.48157(18) 0.0657(16) Uani 1 1 d . . .
H12A H 0.6028 1.0212 0.4474 0.079 Uiso 1 1 calc R . .
C13 C 0.7680(11) 1.0916(7) 0.50828(17) 0.0557(14) Uani 1 1 d . . .
H13A H 0.8966 1.1447 0.4926 0.067 Uiso 1 1 calc R . .
C14 C 0.7590(9) 1.0878(5) 0.55818(16) 0.0440(11) Uani 1 1 d . . .
H14A H 0.8827 1.1373 0.5764 0.053 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N1 O2 122.8(4) . . ?
O3 N1 C8 118.3(4) . . ?
O2 N1 C8 118.9(4) . . ?
O1 C1 C6 122.5(4) . . ?
O1 C1 C2 122.6(4) . . ?
C6 C1 C2 114.7(4) . . ?
C1 C2 C7 113.9(3) . . ?
C1 C2 C3 106.3(3) . . ?
C7 C2 C3 112.4(3) . . ?
C1 C2 H2A 108.0 . . ?
C7 C2 H2A 108.0 . . ?
C3 C2 H2A 108.0 . . ?
C4 C3 C2 112.4(4) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 112.4(4) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 110.6(4) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C1 C6 C5 110.1(4) . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C9 C7 C8 111.9(3) . . ?
C9 C7 C2 112.1(3) . . ?
C8 C7 C2 108.8(3) . . ?
C9 C7 H7A 108.0 . . ?
C8 C7 H7A 108.0 . . ?
C2 C7 H7A 108.0 . . ?
N1 C8 C7 110.0(3) . . ?
N1 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C14 118.5(4) . . ?
C10 C9 C7 119.9(4) . . ?
C14 C9 C7 121.5(4) . . ?
C9 C10 C11 121.2(5) . . ?
C9 C10 H10A 119.4 . . ?
C11 C10 H10A 119.4 . . ?
C10 C11 C12 119.1(5) . . ?
C10 C11 H11A 120.5 . . ?
C12 C11 H11A 120.5 . . ?
C13 C12 C11 120.0(5) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.5(5) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C13 C14 C9 120.6(5) . . ?
C13 C14 H14A 119.7 . . ?
C9 C14 H14A 119.7 . . ?
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 C1 1.219(5) . ?
O2 N1 1.227(5) . ?
O3 N1 1.220(5) . ?
N1 C8 1.488(6) . ?
C1 C6 1.501(6) . ?
C1 C2 1.515(5) . ?
C2 C7 1.541(6) . ?
C2 C3 1.553(5) . ?
C2 H2A 1.0000 . ?
C3 C4 1.516(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.511(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.542(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.522(6) . ?
C7 C8 1.536(5) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.382(6) . ?
C9 C14 1.390(6) . ?
C10 C11 1.392(7) . ?
C10 H10A 0.9500 . ?
C11 C12 1.398(9) . ?
C11 H11A 0.9500 . ?
C12 C13 1.363(8) . ?
C12 H12A 0.9500 . ?
C13 C14 1.387(6) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
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
O1 C1 C2 C7 7.7(6) . . . . ?
C6 C1 C2 C7 -177.8(3) . . . . ?
O1 C1 C2 C3 -116.6(5) . . . . ?
C6 C1 C2 C3 57.9(5) . . . . ?
C1 C2 C3 C4 -55.6(5) . . . . ?
C7 C2 C3 C4 179.1(4) . . . . ?
C2 C3 C4 C5 56.5(5) . . . . ?
C3 C4 C5 C6 -53.7(6) . . . . ?
O1 C1 C6 C5 116.3(5) . . . . ?
C2 C1 C6 C5 -58.2(5) . . . . ?
C4 C5 C6 C1 53.2(6) . . . . ?
C1 C2 C7 C9 -168.6(4) . . . . ?
C3 C2 C7 C9 -47.6(5) . . . . ?
C1 C2 C7 C8 67.1(5) . . . . ?
C3 C2 C7 C8 -171.9(4) . . . . ?
O3 N1 C8 C7 -125.5(4) . . . . ?
O2 N1 C8 C7 54.6(5) . . . . ?
C9 C7 C8 N1 55.1(5) . . . . ?
C2 C7 C8 N1 179.5(3) . . . . ?
C8 C7 C9 C10 -128.7(4) . . . . ?
C2 C7 C9 C10 108.8(5) . . . . ?
C8 C7 C9 C14 54.0(6) . . . . ?
C2 C7 C9 C14 -68.5(5) . . . . ?
C14 C9 C10 C11 1.4(7) . . . . ?
C7 C9 C10 C11 -175.9(5) . . . . ?
C9 C10 C11 C12 -0.9(8) . . . . ?
C10 C11 C12 C13 -0.5(9) . . . . ?
C11 C12 C13 C14 1.3(9) . . . . ?
C12 C13 C14 C9 -0.7(8) . . . . ?
C10 C9 C14 C13 -0.7(7) . . . . ?
C7 C9 C14 C13 176.7(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 718411
