#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/38/7203859.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_7203859
loop_
_publ_author_name
'Kozsda-Kovács, Éva'
'Keserü, György Miklós'
'Böcskei, Zsolt'
'Szilágyi, Ildikó'
'Simon, Kálmán'
'Bertók, Béla'
'Fogassy, Elemér'
_publ_contact_author             'Zsolt Bocskei'
_publ_section_title
;
 Role of the solvent in optical resolution of trans-chrysanthemic acid
 via diastereomeric salt formation with
 (1R,2R)-1-(4-nitrophenyl)-2-dimethylaminopropane-1,3-diol
;
_journal_issue                   1
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              149
_journal_paper_doi               10.1039/a904682h
_journal_year                    2000
_chemical_compound_source        preparation
_chemical_formula_sum            'C21 H32 N2 O6'
_chemical_formula_weight         408.49
_chemical_melting_point          387.95
_chemical_name_common            ' d-trans chrysanthemic acid DMAD salt'
_chemical_name_systematic
; 
(1R,3R)-2,2-dimethyl-3-(methylpropenyl)-cyclopropanecarboxylic 
acid (1R,2R)-1-(4-nitrophenyl)-
-2-dimethylamino-1,3-propanediol salt
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 107.02(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.923(10)
_cell_length_b                   7.658(10)
_cell_length_c                   15.573(10)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1132(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan: PROCESS (MSC)'
_computing_publication_material  'teXsan: FINISH (MSC)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Rigaku Raxis-II'
_diffrn_measurement_method       'omega scans with profile analysis'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0905
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1269
_diffrn_reflns_theta_max         20.89
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       ' colourless plates'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.64(613)
_refine_ls_extinction_coef       0.1589(369)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.017
_refine_ls_goodness_of_fit_obs   1.105
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         1269
_refine_ls_number_restraints     179
_refine_ls_restrained_S_all      0.941
_refine_ls_restrained_S_obs      0.973
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_obs          0.0989
_refine_ls_shift/esd_max         0.026
_refine_ls_shift/esd_mean        0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2301P)²+0.0282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3124
_refine_ls_wR_factor_obs         0.2649
_reflns_number_observed          849
_reflns_number_total             1269
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            a904682h.txt
_cod_data_source_block           a1146
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '114.8 C' was changed to '387.95' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.2301P)^2^+0.0282P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.2301P)^2^+0.0282P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1131.6(20)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7203859
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1A O 0.8390(7) 0.8719(26) 0.3988(4) 0.100(3) Uani 1 d U .
H1AO H 0.8688(23) 0.7986(149) 0.4382(75) 0.149 Uiso 1 calc R .
O2A O 0.4631(11) 1.0634 0.4237(8) 0.182(6) Uani 1 d U .
H2AO H 0.3773(33) 1.0687(413) 0.4136(97) 0.273 Uiso 1 calc R .
O3A O 0.4656(21) 0.5231(41) -0.0042(14) 0.240(10) Uani 1 d U .
O4A O 0.3101(22) 0.4248(34) 0.0552(12) 0.230(8) Uani 1 d U .
N1A N 0.7604(10) 1.1927(27) 0.4352(6) 0.098(3) Uani 1 d U .
H1AN H 0.8473(10) 1.1584(27) 0.4333(6) 0.084(12) Uiso 1 calc R .
N2A N 0.4142(18) 0.5110(31) 0.0571(10) 0.147(5) Uani 1 d DU .
C1A C 0.6895(11) 0.8874(28) 0.3802(8) 0.094(4) Uani 1 d DU .
H1A H 0.6606(11) 0.8447(28) 0.4315(8) 0.084(12) Uiso 1 calc R .
C2A C 0.6570(11) 1.0810(29) 0.3664(8) 0.096(3) Uani 1 d U .
H2A H 0.6719(11) 1.1100(29) 0.3086(8) 0.084(12) Uiso 1 calc R .
C3A C 0.4981(13) 1.1284(34) 0.3560(9) 0.130(5) Uani 1 d U .
H3A H 0.4864(13) 1.2543(34) 0.3546(9) 0.071(17) Uiso 1 calc R .
H3B H 0.4378(13) 1.0808(34) 0.3003(9) 0.071(17) Uiso 1 calc R .
C4A C 0.6166(12) 0.7851(28) 0.2979(8) 0.097(3) Uani 1 d DU .
C7A C 0.4823(19) 0.5963(34) 0.1401(9) 0.128(6) Uani 1 d DU .
C10A C 0.7623(13) 1.1732(33) 0.5279(7) 0.119(4) Uani 1 d U .
H10A H 0.7692(13) 1.0516(33) 0.5436(7) 0.244(26) Uiso 1 calc R .
H10B H 0.6770(13) 1.2204(33) 0.5357(7) 0.244(26) Uiso 1 calc R .
H10C H 0.8418(13) 1.2346(33) 0.5660(7) 0.244(26) Uiso 1 calc R .
C11A C 0.7500(15) 1.3830(29) 0.4104(10) 0.123(4) Uani 1 d U .
H11A H 0.7495(15) 1.3957(29) 0.3490(10) 0.244(26) Uiso 1 calc R .
H11B H 0.8294(15) 1.4444(29) 0.4487(10) 0.244(26) Uiso 1 calc R .
H11C H 0.6646(15) 1.4305(29) 0.4178(10) 0.244(26) Uiso 1 calc R .
O1 O 1.2229(9) 1.2408(25) 0.4085(6) 0.116(3) Uani 1 d U .
O2 O 1.0363(8) 1.1955(27) 0.4534(5) 0.112(3) Uani 1 d U .
C1 C 1.0116(13) 1.1520(30) 0.3012(7) 0.103(4) Uani 1 d U .
H1 H 0.9390(13) 1.0644(30) 0.2999(7) 0.084(12) Uiso 1 calc R .
C2 C 0.9664(14) 1.2842(31) 0.2296(8) 0.109(4) Uani 1 d U .
C3 C 1.0704(12) 1.1388(30) 0.2226(8) 0.106(4) Uani 1 d U .
H3 H 1.1687(12) 1.1758(30) 0.2346(8) 0.084(12) Uiso 1 calc R .
C4 C 1.0986(12) 1.2007(29) 0.3955(8) 0.096(3) Uani 1 d U .
C5 C 1.0250(18) 1.4718(34) 0.2485(10) 0.143(6) Uani 1 d U .
H5B H 0.9872(18) 1.5428(34) 0.1962(10) 0.244(26) Uiso 1 calc R .
H5C H 1.1259(18) 1.4691(34) 0.2631(10) 0.244(26) Uiso 1 calc R .
H5D H 0.9983(18) 1.5200(34) 0.2981(10) 0.244(26) Uiso 1 calc R .
C6 C 0.8156(16) 1.2726(34) 0.1684(9) 0.144(6) Uani 1 d U .
H6B H 0.7991(16) 1.3644(34) 0.1246(9) 0.244(26) Uiso 1 calc R .
H6C H 0.7512(16) 1.2844(34) 0.2036(9) 0.244(26) Uiso 1 calc R .
H6D H 0.8013(16) 1.1616(34) 0.1384(9) 0.244(26) Uiso 1 calc R .
C7 C 1.0281(14) 0.9912(29) 0.1605(8) 0.110(4) Uani 1 d U .
H26 H 0.9452(14) 0.9322(29) 0.1582(8) 0.122(19) Uiso 1 calc R .
C8 C 1.1054(18) 0.9368(29) 0.1061(9) 0.121(5) Uani 1 d U .
C5A C 0.6687(14) 0.7831(30) 0.2244(8) 0.112(4) Uani 1 d DU .
H5A H 0.7501(14) 0.8455(30) 0.2268(8) 0.122(19) Uiso 1 calc R .
C6A C 0.6023(18) 0.6904(31) 0.1479(8) 0.121(4) Uani 1 d DU .
H6A H 0.6405(18) 0.6919(31) 0.1000(8) 0.122(19) Uiso 1 calc R .
C9 C 1.0499(22) 0.7932(34) 0.0429(10) 0.154(6) Uani 1 d U .
H9B H 1.1147(22) 0.7683(34) 0.0093(10) 0.244(26) Uiso 1 calc R .
H9C H 0.9605(22) 0.8265(34) 0.0025(10) 0.244(26) Uiso 1 calc R .
H9D H 1.0381(22) 0.6910(34) 0.0757(10) 0.244(26) Uiso 1 calc R .
C8A C 0.4334(17) 0.5980(30) 0.2083(12) 0.143(6) Uani 1 d DU .
H8A H 0.3530(17) 0.5325(30) 0.2045(12) 0.122(19) Uiso 1 calc R .
C9A C 0.4932(15) 0.6921(32) 0.2882(9) 0.123(5) Uani 1 d DU .
H9A H 0.4504(15) 0.6917(32) 0.3339(9) 0.122(19) Uiso 1 calc R .
C10 C 1.2419(14) 1.0082(34) 0.1056(10) 0.135(5) Uani 1 d U .
H10D H 1.2748(14) 0.9477(34) 0.0616(10) 0.244(26) Uiso 1 calc R .
H10E H 1.3085(14) 0.9935(34) 0.1638(10) 0.244(26) Uiso 1 calc R .
H10F H 1.2318(14) 1.1302(34) 0.0909(10) 0.244(26) Uiso 1 calc R .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
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
C10A N1A C11A 109.6(11) . . ?
C10A N1A C2A 117.1(10) . . ?
C11A N1A C2A 112.7(10) . . ?
O3A N2A O4A 124.9(18) . . ?
O3A N2A C7A 118.7(18) . . ?
O4A N2A C7A 116.3(18) . . ?
O1A C1A C4A 110.0(9) . . ?
O1A C1A C2A 105.9(9) . . ?
C4A C1A C2A 111.1(10) . . ?
C1A C2A N1A 112.3(10) . . ?
C1A C2A C3A 113.8(11) . . ?
N1A C2A C3A 113.1(10) . . ?
O2A C3A C2A 108.9(12) . . ?
C9A C4A C5A 115.8(12) . . ?
C9A C4A C1A 123.5(10) . . ?
C5A C4A C1A 120.7(11) . . ?
C8A C7A C6A 116.6(16) . . ?
C8A C7A N2A 123.8(19) . . ?
C6A C7A N2A 119.4(14) . . ?
C2 C1 C3 62.4(8) . . ?
C2 C1 C4 121.6(13) . . ?
C3 C1 C4 124.0(11) . . ?
C1 C2 C6 117.3(13) . . ?
C1 C2 C5 118.7(13) . . ?
C6 C2 C5 114.8(14) . . ?
C1 C2 C3 59.8(9) . . ?
C6 C2 C3 117.9(13) . . ?
C5 C2 C3 117.5(12) . . ?
C7 C3 C1 118.9(12) . . ?
C7 C3 C2 122.3(11) . . ?
C1 C3 C2 57.9(8) . . ?
O1 C4 O2 125.5(11) . . ?
O1 C4 C1 118.6(10) . . ?
O2 C4 C1 115.8(10) . . ?
C8 C7 C3 122.7(13) . . ?
C7 C8 C10 125.4(14) . . ?
C7 C8 C9 118.3(16) . . ?
C10 C8 C9 116.2(14) . . ?
C6A C5A C4A 121.3(13) . . ?
C5A C6A C7A 122.2(13) . . ?
C7A C8A C9A 124.7(17) . . ?
C4A C9A C8A 119.3(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
O1A C1A 1.431(12) . ?
O2A C3A 1.30(2) . ?
O3A N2A 1.21(2) . ?
O4A N2A 1.22(2) . ?
N1A C10A 1.447(14) . ?
N1A C11A 1.50(2) . ?
N1A C2A 1.51(2) . ?
N2A C7A 1.43(2) . ?
C1A C4A 1.50(2) . ?
C1A C2A 1.52(2) . ?
C2A C3A 1.58(2) . ?
C4A C9A 1.39(2) . ?
C4A C5A 1.39(2) . ?
C7A C8A 1.29(2) . ?
C7A C6A 1.37(2) . ?
O1 C4 1.230(12) . ?
O2 C4 1.234(12) . ?
C1 C2 1.48(2) . ?
C1 C3 1.505(14) . ?
C1 C4 1.52(2) . ?
C2 C6 1.52(2) . ?
C2 C5 1.55(2) . ?
C2 C3 1.54(2) . ?
C3 C7 1.47(2) . ?
C7 C8 1.36(2) . ?
C8 C10 1.46(2) . ?
C8 C9 1.47(2) . ?
C5A C6A 1.38(2) . ?
C8A C9A 1.41(2) . ?
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
O1A C1A C2A N1A -43.2(12) . . . . ?
C4A C1A C2A N1A -162.6(8) . . . . ?
O1A C1A C2A C3A -173.3(8) . . . . ?
C4A C1A C2A C3A 67.3(12) . . . . ?
C10A N1A C2A C1A -64.4(12) . . . . ?
C11A N1A C2A C1A 167.1(10) . . . . ?
C10A N1A C2A C3A 66.1(15) . . . . ?
C11A N1A C2A C3A -62.5(14) . . . . ?
C1A C2A C3A O2A 52.8(17) . . . . ?
N1A C2A C3A O2A -76.9(17) . . . . ?
O1A C1A C4A C9A 142.4(12) . . . . ?
C2A C1A C4A C9A -100.6(13) . . . . ?
O1A C1A C4A C5A -39.5(14) . . . . ?
C2A C1A C4A C5A 77.4(12) . . . . ?
O3A N2A C7A C8A 177.0(20) . . . . ?
O4A N2A C7A C8A -5.9(25) . . . . ?
O3A N2A C7A C6A 0.7(27) . . . . ?
O4A N2A C7A C6A 177.8(17) . . . . ?
C3 C1 C2 C6 108.0(14) . . . . ?
C4 C1 C2 C6 -137.3(13) . . . . ?
C3 C1 C2 C5 -106.9(13) . . . . ?
C4 C1 C2 C5 7.8(17) . . . . ?
C3 C1 C2 C3 0.000(15) . . . . ?
C4 C1 C2 C3 114.7(13) . . . . ?
C2 C1 C3 C7 -112.0(13) . . . . ?
C4 C1 C3 C7 136.9(14) . . . . ?
C2 C1 C3 C2 0.00(2) . . . . ?
C4 C1 C3 C2 -111.1(16) . . . . ?
C1 C2 C3 C7 106.1(14) . . . . ?
C6 C2 C3 C7 -0.8(17) . . . . ?
C5 C2 C3 C7 -145.1(12) . . . . ?
C1 C2 C3 C1 0.00(2) . . . . ?
C6 C2 C3 C1 -107.0(14) . . . . ?
C5 C2 C3 C1 108.8(14) . . . . ?
C2 C1 C4 O1 -72.1(15) . . . . ?
C3 C1 C4 O1 3.9(20) . . . . ?
C2 C1 C4 O2 108.2(14) . . . . ?
C3 C1 C4 O2 -175.8(12) . . . . ?
C1 C3 C7 C8 -158.7(13) . . . . ?
C2 C3 C7 C8 133.0(14) . . . . ?
C3 C7 C8 C10 3.9(21) . . . . ?
C3 C7 C8 C9 -176.8(14) . . . . ?
C9A C4A C5A C6A -1.4(18) . . . . ?
C1A C4A C5A C6A -179.6(12) . . . . ?
C4A C5A C6A C7A 0.1(21) . . . . ?
C8A C7A C6A C5A -0.1(22) . . . . ?
N2A C7A C6A C5A 176.5(13) . . . . ?
C6A C7A C8A C9A 1.4(22) . . . . ?
N2A C7A C8A C9A -175.0(14) . . . . ?
C5A C4A C9A C8A 2.6(18) . . . . ?
C1A C4A C9A C8A -179.3(11) . . . . ?
C7A C8A C9A C4A -2.8(22) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189848
