#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/14/4511431.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_4511431
loop_
_publ_author_name
'Sakurai, Rumiko'
'Yuzawa, Atsushi'
'Sakai, Kenichi'
'Hirayama, Noriaki'
_publ_section_title
;
 Dielectrically Controlled Enantiomeric Resolution (DCR) of (R)- and
 (S)-2-Methylpyrrolidine by (R,R)-Tartaric Acid
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1606
_journal_paper_doi               10.1021/cg060041s
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C9 H17 N O6 '
_chemical_formula_sum            'C9 H17 N O6'
_chemical_formula_weight         235.24
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.833(15)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   4.9095(9)
_cell_length_b                   17.009(3)
_cell_length_c                   6.6979(11)
_cell_measurement_reflns_used    3998
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      68.4
_cell_measurement_theta_min      5.2
_cell_volume                     547.43(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4147
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             252.00
_exptl_crystal_preparation       methanol
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       10(4)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   0.781
_refine_ls_number_parameters     166
_refine_ls_number_reflns         705
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0010Fo² + 3.0000σ(Fo²) + 0.5000]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                702
_reflns_number_total             1777
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cg060041ssi20060122_090537.cif
_cod_data_source_block           '_(R)-2-methylpyrrolidine:(R,R)-tartaric_acid'
_cod_original_cell_volume        547.41(16)
_cod_original_formula_sum        'C9 H17 N O6 '
_cod_database_code               4511431
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-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
O2 O 0.4029(9) 0.6282(3) 0.9432(7) 0.0448(14) Uani 1.00 1 d .
O1 O 0.5726(10) 0.7457(2) 0.8798(7) 0.0471(14) Uani 1.00 1 d .
O3 O -0.0278(11) 0.6428(3) 0.6298(8) 0.0455(15) Uani 1.00 1 d .
O4 O 0.4229(10) 0.6761(3) 0.4224(8) 0.0456(15) Uani 1.00 1 d .
O5 O -0.0170(10) 0.7173(3) 0.1522(7) 0.0486(14) Uani 1.00 1 d .
O6 O -0.1424(11) 0.8135(3) 0.3427(8) 0.0566(17) Uani 1.00 1 d .
N1 N 0.9084(17) 0.5411(3) 0.9747(10) 0.0458(19) Uani 1.00 1 d .
C1 C 0.8321(18) 0.4673(4) 0.8543(12) 0.053(2) Uani 1.00 1 d .
C2 C 0.767(2) 0.4110(5) 1.0124(16) 0.097(4) Uani 1.00 1 d .
C3 C 0.951(2) 0.4328(5) 1.2032(17) 0.096(3) Uani 1.00 1 d .
C4 C 1.022(2) 0.5174(5) 1.1944(12) 0.069(2) Uani 1.00 1 d .
C5 C 0.601(2) 0.4780(6) 0.6752(15) 0.076(3) Uani 1.00 1 d .
C6 C 0.3896(14) 0.6913(4) 0.8463(9) 0.0360(19) Uani 1.00 1 d .
C7 C 0.1488(13) 0.7088(4) 0.6725(9) 0.0342(18) Uani 1.00 1 d .
C8 C 0.2561(13) 0.7368(4) 0.4821(9) 0.0368(17) Uani 1.00 1 d .
C9 C 0.0101(13) 0.7594(4) 0.3147(10) 0.040(2) Uani 1.00 1 d .
H(1) H 0.9909 0.4493 0.8071 0.141 Uiso 1.00 1 c R
H(2) H 0.5790 0.4145 1.0203 0.388 Uiso 1.00 1 c R
H(3) H 0.8062 0.3576 0.9755 0.101 Uiso 1.00 1 c R
H(4) H 1.1170 0.4027 1.2250 0.256 Uiso 1.00 1 c R
H(5) H 0.8588 0.4235 1.3149 0.186 Uiso 1.00 1 c R
H(6) H 1.2162 0.5254 1.2315 0.189 Uiso 1.00 1 c R
H(7) H 0.9318 0.5470 1.2838 0.111 Uiso 1.00 1 c R
H(8) H 0.4776 0.5179 0.7059 0.060 Uiso 1.00 1 c R
H(9) H 0.6675 0.4934 0.5578 0.169 Uiso 1.00 1 c R
H(10) H 0.4985 0.4302 0.6472 0.126 Uiso 1.00 1 c R
H(11) H 0.0415 0.7507 0.7140 0.013 Uiso 1.00 1 c R
H(12) H 0.3711 0.7824 0.5177 0.024 Uiso 1.00 1 c R
H(13) H 0.768(18) 0.568(4) 0.963(11) 0.04(2) Uiso 1.00 1 c .
H(14) H 1.039(16) 0.571(4) 0.934(11) 0.04(2) Uiso 1.00 1 c .
H(15) H -0.163(15) 0.655(4) 0.571(11) 0.03(2) Uiso 1.00 1 c .
H(16) H 0.37(2) 0.669(6) 0.303(16) 0.09(3) Uiso 1.00 1 c .
H(17) H 0.75(2) 0.739(6) 1.042(15) 0.10(3) Uiso 1.00 1 c .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, 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
C(1) N(1) C(4) 107.6(6)
N(1) C(1) C(2) 102.7(6)
N(1) C(1) C(5) 113.4(6)
C(2) C(1) C(5) 114.0(8)
C(1) C(2) C(3) 105.8(9)
C(2) C(3) C(4) 108.7(8)
N(1) C(4) C(3) 104.7(7)
O(2) C(6) O(1) 124.8(5)
O(2) C(6) C(7) 121.3(6)
O(1) C(6) C(7) 113.8(5)
O(3) C(7) C(6) 110.5(5)
O(3) C(7) C(8) 112.0(5)
C(6) C(7) C(8) 110.5(5)
O(4) C(8) C(7) 108.7(5)
O(4) C(8) C(9) 113.1(5)
C(7) C(8) C(9) 109.4(5)
O(5) C(9) O(6) 125.9(5)
O(5) C(9) C(8) 114.4(6)
O(6) C(9) C(8) 119.7(6)
C(6) O(1) H(17) 115(5)
C(7) O(3) H(15) 110(5)
C(8) O(4) H(16) 108(7)
C(1) N(1) H(13) 108(5)
C(1) N(1) H(14) 115(4)
C(4) N(1) H(13) 112(5)
C(4) N(1) H(14) 107(4)
H(13) N(1) H(14) 107(7)
N(1) C(1) H(1) 108.6
C(2) C(1) H(1) 109.5
C(5) C(1) H(1) 108.4
C(1) C(2) H(2) 110.7
C(1) C(2) H(3) 109.5
C(3) C(2) H(2) 112.1
C(3) C(2) H(3) 110.0
H(2) C(2) H(3) 108.8
C(2) C(3) H(4) 110.9
C(2) C(3) H(5) 109.5
C(4) C(3) H(4) 109.3
C(4) C(3) H(5) 110.0
H(4) C(3) H(5) 108.5
N(1) C(4) H(6) 111.5
N(1) C(4) H(7) 110.1
C(3) C(4) H(6) 111.1
C(3) C(4) H(7) 110.1
H(6) C(4) H(7) 109.3
C(1) C(5) H(8) 109.0
C(1) C(5) H(9) 111.4
C(1) C(5) H(10) 109.8
H(8) C(5) H(9) 108.9
H(8) C(5) H(10) 108.5
H(9) C(5) H(10) 109.2
O(3) C(7) H(11) 107.4
C(6) C(7) H(11) 108.2
C(8) C(7) H(11) 108.0
O(4) C(8) H(12) 108.2
C(7) C(8) H(12) 109.0
C(9) C(8) H(12) 108.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(2) C(6) 1.249(9)
O(1) C(6) 1.277(8)
O(3) C(7) 1.412(8)
O(4) C(8) 1.424(9)
O(5) C(9) 1.286(8)
O(6) C(9) 1.225(9)
N(1) C(1) 1.497(10)
N(1) C(4) 1.517(10)
C(1) C(2) 1.510(14)
C(1) C(5) 1.485(12)
C(2) C(3) 1.454(15)
C(3) C(4) 1.485(13)
C(6) C(7) 1.509(8)
C(7) C(8) 1.551(9)
C(8) C(9) 1.519(8)
O(1) H(17) 1.24(9)
O(3) H(15) 0.73(6)
O(4) H(16) 0.79(10)
N(1) H(13) 0.82(8)
N(1) H(14) 0.90(8)
C(1) H(1) 0.950
C(2) H(2) 0.937
C(2) H(3) 0.971
C(3) H(4) 0.948
C(3) H(5) 0.964
C(4) H(6) 0.946
C(4) H(7) 0.956
C(5) H(8) 0.957
C(5) H(9) 0.949
C(5) H(10) 0.954
C(7) H(11) 0.961
C(8) H(12) 0.961
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
C(1) N(1) C(4) C(3) -11.9(10)
C(4) N(1) C(1) C(2) 27.3(10)
C(4) N(1) C(1) C(5) 150.8(8)
N(1) C(1) C(2) C(3) -32.9(11)
C(5) C(1) C(2) C(3) -156.0(9)
C(1) C(2) C(3) C(4) 26.6(13)
C(2) C(3) C(4) N(1) -9.2(13)
O(2) C(6) C(7) O(3) -5.7(9)
O(2) C(6) C(7) C(8) -130.3(7)
O(1) C(6) C(7) O(3) 173.4(6)
O(1) C(6) C(7) C(8) 48.8(8)
O(3) C(7) C(8) O(4) -63.7(6)
O(3) C(7) C(8) C(9) 60.2(7)
C(6) C(7) C(8) O(4) 60.0(6)
C(6) C(7) C(8) C(9) -176.1(5)
O(4) C(8) C(9) O(5) 4.0(9)
O(4) C(8) C(9) O(6) -176.4(6)
C(7) C(8) C(9) O(5) -117.3(6)
C(7) C(8) C(9) O(6) 62.3(8)
