#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/33/7103306.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_7103306
loop_
_publ_author_name
'Arnold, Kenny'
'Batsanov, Andrei S'
'Davies, Bryan'
'Grosjean, Christophe'
'Schütz, Thorben'
'Whiting, Andrew'
'Zawatzky, Kerstin'
_publ_section_title
;
 The first example of enamine-Lewis acid cooperative bifunctional
 catalysis: application to the asymmetric aldol reaction.
;
_journal_issue                   33
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3879
_journal_page_last               3881
_journal_paper_doi               10.1039/b806779a
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H20 B N O4'
_chemical_formula_sum            'C10 H20 B N O4'
_chemical_formula_weight         229.08
_chemical_melting_point          373
_chemical_name_common
;(S)-N-(1,1-Dimethylethoxycarbonyl)-(pyrrolidin-2-
yl)methylboronic acid
;
_chemical_name_systematic
; (S)-N-(1,1-Dimethylethoxycarbonyl)-(pyrrolidin-2-
yl)methylboronic acid
;
_chemical_optical_rotation       '[\a]~D~^22^=-60 (c 1.00 in CH~2~Cl~2~)'
_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   difmap
_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                   9.3385(9)
_cell_length_b                   11.5001(11)
_cell_length_c                   12.0643(11)
_cell_measurement_reflns_used    7045
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.95
_cell_measurement_theta_min      2.45
_cell_volume                     1295.6(2)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method       'ω 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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13209
_diffrn_reflns_theta_full        28.96
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
'undeterminable, all \Df" set to 0, Friedel equivalents merged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         1968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0306
_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)+(0.0469P)²+0.0994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.74
_reflns_number_gt                1798
_reflns_number_total             1968
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b806779a.txt
_cod_data_source_block           (S)-6
_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_database_code               7103306
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
_atom_site_disorder_assembly
_atom_site_disorder_group
B B 0.08781(17) 0.25166(14) 0.50012(14) 0.0200(3) Uani 1 1 d . . .
O1 O 0.19867(12) 0.17739(9) 0.50937(10) 0.0298(3) Uani 1 1 d . . .
H01 H 0.283(3) 0.213(2) 0.503(2) 0.053(7) Uiso 1 1 d . . .
O2 O -0.04763(11) 0.20865(9) 0.50966(9) 0.0230(2) Uani 1 1 d . . .
H02 H -0.052(2) 0.141(2) 0.5283(18) 0.049(7) Uiso 1 1 d . . .
O3 O 0.35581(11) 0.68124(8) 0.34303(8) 0.0234(2) Uani 1 1 d . . .
O4 O 0.41529(11) 0.51781(8) 0.44002(8) 0.0238(2) Uani 1 1 d . . .
N1 N 0.20960(12) 0.52995(10) 0.34006(9) 0.0184(2) Uani 1 1 d . . .
C1 C 0.33376(15) 0.57160(11) 0.37901(11) 0.0191(3) Uani 1 1 d . . .
C2 C 0.16457(15) 0.40863(11) 0.35915(11) 0.0180(3) Uani 1 1 d . . .
H2 H 0.2489(19) 0.3578(15) 0.3452(13) 0.020(4) Uiso 1 1 d . . .
C3 C 0.05019(19) 0.39207(13) 0.26907(13) 0.0287(3) Uani 1 1 d . . .
H31 H 0.103(2) 0.3702(18) 0.1959(17) 0.037(5) Uiso 1 1 d . . .
H32 H -0.023(2) 0.3347(19) 0.2904(16) 0.038(5) Uiso 1 1 d . . .
C4 C -0.01351(18) 0.51336(14) 0.25333(14) 0.0300(3) Uani 1 1 d . . .
H41 H -0.082(2) 0.5296(18) 0.3166(16) 0.037(5) Uiso 1 1 d . . .
H42 H -0.061(2) 0.5224(18) 0.1819(17) 0.042(5) Uiso 1 1 d . . .
C5 C 0.11606(17) 0.59301(13) 0.26250(12) 0.0240(3) Uani 1 1 d . . .
H51 H 0.094(2) 0.6709(18) 0.2933(15) 0.032(5) Uiso 1 1 d . . .
H52 H 0.164(2) 0.6014(18) 0.1896(17) 0.039(5) Uiso 1 1 d . . .
C6 C 0.49237(17) 0.74089(13) 0.36452(12) 0.0246(3) Uani 1 1 d . . .
C7 C 0.4679(2) 0.85843(14) 0.31018(14) 0.0330(4) Uani 1 1 d . . .
H71 H 0.559(2) 0.9055(19) 0.3206(17) 0.040(5) Uiso 1 1 d . . .
H72 H 0.448(2) 0.850(2) 0.2312(19) 0.049(6) Uiso 1 1 d . . .
H73 H 0.387(2) 0.904(2) 0.3498(18) 0.045(6) Uiso 1 1 d . . .
C8 C 0.5167(2) 0.75590(16) 0.48835(14) 0.0373(4) Uani 1 1 d . . .
H81 H 0.431(2) 0.7909(18) 0.5227(18) 0.043(6) Uiso 1 1 d . . .
H82 H 0.542(2) 0.684(2) 0.5266(17) 0.046(6) Uiso 1 1 d . . .
H83 H 0.597(2) 0.8112(19) 0.4974(18) 0.043(5) Uiso 1 1 d . . .
C9 C 0.6128(2) 0.67456(16) 0.30876(15) 0.0343(4) Uani 1 1 d . . .
H91 H 0.601(2) 0.6668(19) 0.2314(18) 0.045(6) Uiso 1 1 d . . .
H92 H 0.627(2) 0.6021(19) 0.3463(17) 0.044(6) Uiso 1 1 d . . .
H93 H 0.703(3) 0.718(2) 0.3216(17) 0.049(6) Uiso 1 1 d . . .
C10 C 0.10697(15) 0.38742(11) 0.47650(11) 0.0189(3) Uani 1 1 d . . .
H101 H 0.016(2) 0.4308(15) 0.4873(15) 0.029(5) Uiso 1 1 d . . .
H102 H 0.175(2) 0.4201(15) 0.5304(14) 0.025(4) 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 0.0000 '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'
B B 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
O1 B O2 118.44(13) . . ?
O1 B C10 123.27(13) . . ?
O2 B C10 118.28(12) . . ?
B O1 H01 112.2(15) . . ?
B O2 H02 114.7(17) . . ?
C1 O3 C6 120.75(11) . . ?
C1 N1 C5 124.11(12) . . ?
C1 N1 C2 122.01(11) . . ?
C5 N1 C2 113.34(11) . . ?
O4 C1 N1 124.58(12) . . ?
O4 C1 O3 124.73(13) . . ?
N1 C1 O3 110.69(12) . . ?
N1 C2 C10 113.23(10) . . ?
N1 C2 C3 101.84(11) . . ?
C10 C2 C3 112.92(12) . . ?
N1 C2 H2 107.7(10) . . ?
C10 C2 H2 109.9(9) . . ?
C3 C2 H2 110.9(9) . . ?
C4 C3 C2 104.21(12) . . ?
C4 C3 H31 107.4(11) . . ?
C2 C3 H31 107.5(11) . . ?
C4 C3 H32 112.1(12) . . ?
C2 C3 H32 112.3(12) . . ?
H31 C3 H32 112.8(16) . . ?
C5 C4 C3 103.35(13) . . ?
C5 C4 H41 109.6(11) . . ?
C3 C4 H41 108.7(12) . . ?
C5 C4 H42 111.1(12) . . ?
C3 C4 H42 112.5(12) . . ?
H41 C4 H42 111.3(16) . . ?
N1 C5 C4 102.81(11) . . ?
N1 C5 H51 109.2(11) . . ?
C4 C5 H51 114.1(11) . . ?
N1 C5 H52 110.1(12) . . ?
C4 C5 H52 110.7(12) . . ?
H51 C5 H52 109.7(16) . . ?
O3 C6 C9 109.30(12) . . ?
O3 C6 C7 102.02(12) . . ?
C9 C6 C7 111.57(13) . . ?
O3 C6 C8 110.82(12) . . ?
C9 C6 C8 112.47(15) . . ?
C7 C6 C8 110.19(14) . . ?
C6 C7 H71 107.2(12) . . ?
C6 C7 H72 111.3(13) . . ?
H71 C7 H72 109.4(18) . . ?
C6 C7 H73 111.0(12) . . ?
H71 C7 H73 106.6(15) . . ?
H72 C7 H73 111.1(18) . . ?
C6 C8 H81 109.8(12) . . ?
C6 C8 H82 113.8(12) . . ?
H81 C8 H82 110.3(19) . . ?
C6 C8 H83 107.1(12) . . ?
H81 C8 H83 108.0(16) . . ?
H82 C8 H83 107.7(17) . . ?
C6 C9 H91 113.5(13) . . ?
C6 C9 H92 109.1(13) . . ?
H91 C9 H92 113.6(19) . . ?
C6 C9 H93 107.8(13) . . ?
H91 C9 H93 107.6(19) . . ?
H92 C9 H93 104.6(19) . . ?
C2 C10 B 111.07(11) . . ?
C2 C10 H101 109.9(11) . . ?
B C10 H101 111.9(10) . . ?
C2 C10 H102 108.8(10) . . ?
B C10 H102 109.1(10) . . ?
H101 C10 H102 106.0(14) . . ?
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
B O1 1.3467(19) . ?
B O2 1.3629(18) . ?
B C10 1.597(2) . ?
O1 H01 0.89(3) . ?
O2 H02 0.81(2) . ?
O3 C1 1.3493(16) . ?
O3 C6 1.4711(17) . ?
O4 C1 1.2264(16) . ?
N1 C1 1.3396(18) . ?
N1 C5 1.4712(17) . ?
N1 C2 1.4753(17) . ?
C2 C10 1.5340(18) . ?
C2 C3 1.536(2) . ?
C2 H2 0.995(17) . ?
C3 C4 1.528(2) . ?
C3 H31 1.04(2) . ?
C3 H32 0.98(2) . ?
C4 C5 1.522(2) . ?
C4 H41 1.01(2) . ?
C4 H42 0.97(2) . ?
C5 H51 0.99(2) . ?
C5 H52 0.99(2) . ?
C6 C9 1.517(2) . ?
C6 C7 1.520(2) . ?
C6 C8 1.521(2) . ?
C7 H71 1.01(2) . ?
C7 H72 0.97(2) . ?
C7 H73 1.04(2) . ?
C8 H81 0.99(2) . ?
C8 H82 0.98(2) . ?
C8 H83 0.99(2) . ?
C9 H91 0.94(2) . ?
C9 H92 0.96(2) . ?
C9 H93 0.99(2) . ?
C10 H101 0.99(2) . ?
C10 H102 0.986(18) . ?
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
O1 H01 O2 0.89(3) 1.83(3) 2.7172(15) 178(2) 4_556
O2 H02 O4 0.81(2) 1.89(2) 2.6964(14) 172(2) 4_456
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
C5 N1 C1 O4 -176.83(13) . . . . ?
C2 N1 C1 O4 -5.8(2) . . . . ?
C5 N1 C1 O3 3.94(18) . . . . ?
C2 N1 C1 O3 174.94(11) . . . . ?
C6 O3 C1 O4 7.6(2) . . . . ?
C6 O3 C1 N1 -173.13(11) . . . . ?
C1 N1 C2 C10 77.22(16) . . . . ?
C5 N1 C2 C10 -110.90(13) . . . . ?
C1 N1 C2 C3 -161.25(12) . . . . ?
C5 N1 C2 C3 10.64(15) . . . . ?
N1 C2 C3 C4 -29.97(15) . . . . ?
C10 C2 C3 C4 91.78(14) . . . . ?
C2 C3 C4 C5 38.72(16) . . . . ?
C1 N1 C5 C4 -175.32(12) . . . . ?
C2 N1 C5 C4 12.99(15) . . . . ?
C3 C4 C5 N1 -31.25(15) . . . . ?
C1 O3 C6 C9 61.82(16) . . . . ?
C1 O3 C6 C7 -179.96(12) . . . . ?
C1 O3 C6 C8 -62.67(18) . . . . ?
N1 C2 C10 B -169.26(12) . . . . ?
C3 C2 C10 B 75.66(15) . . . . ?
O1 B C10 C2 68.22(19) . . . . ?
O2 B C10 C2 -110.72(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653050
