#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/14/7011432.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_7011432
loop_
_publ_author_name
'Bernauer, Klaus'
'Cabort, Amel'
'Guicher, Nathalie'
'Stoeckli-Evans, Helen'
'Süss-Fink, Georg'
_publ_section_title
;
 Carbonate binding to copper(ii) in solution: mixed-ligand complex
 formation and its application to the isolation and separation of the
 three isomers of [Cu(bpp)(H2O)][ClO4]2 [bpp =
 2,6-bis(pyrrolidin-2-yl)pyridine]
;
_journal_issue                   9
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              2069
_journal_paper_doi               10.1039/b111501b
_journal_year                    2002
_chemical_formula_sum            'C13 H25 Cl2 N3 O10'
_chemical_formula_weight         454.26
_chemical_name_systematic
; 
bis(pyrrolidin-2-yl)-2,6-pyridine
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_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                 91.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.313(6)
_cell_length_b                   11.416(4)
_cell_length_c                   12.481(5)
_cell_measurement_reflns_used    12
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      11.50
_cell_measurement_theta_min      10.00
_cell_volume                     2038.9(14)
_computing_cell_refinement       'STADI4 (Stoe & Cie GmbH, Darmstadt, 1997)'
_computing_data_collection       'STADI4 (Stoe & Cie GmbH, Darmstadt, 1997)'
_computing_data_reduction        'X-RED (Stoe & Cie GmbH, Darmstadt, 1997)'
_computing_molecular_graphics    'PLATON/PLUTON (Spek, 1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE AED2 4-circle diffractometer'
_diffrn_measurement_method       2θ/ω
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4231
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        7
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0019(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0767P)²+4.7077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1660
_reflns_number_gt                1577
_reflns_number_total             2001
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b111501b.txt
_cod_data_source_block           CCDC175425
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7011432
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'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
N1 N 0.0164(2) 0.0000 0.2750(3) 0.0350(8) Uani 1 2 d S . .
C2 C -0.0190(2) 0.1006(3) 0.3110(2) 0.0376(7) Uani 1 1 d . . .
C3 C -0.0891(2) 0.1040(3) 0.3858(3) 0.0482(8) Uani 1 1 d . . .
H3 H -0.1127 0.1759 0.4100 0.058 Uiso 1 1 calc R . .
C4 C -0.1232(4) 0.0000 0.4237(4) 0.0553(13) Uani 1 2 d S . .
H4 H -0.1699 0.0000 0.4757 0.066 Uiso 1 2 calc SR . .
C5 C 0.0215(2) 0.2121(3) 0.2692(3) 0.0458(8) Uani 1 1 d . . .
H5 H -0.0299 0.2675 0.2520 0.055 Uiso 1 1 calc R . .
C6 C 0.0920(4) 0.2717(4) 0.3461(3) 0.0891(17) Uani 1 1 d . . .
H6A H 0.0606 0.3270 0.3934 0.107 Uiso 1 1 calc R . .
H6B H 0.1257 0.2137 0.3899 0.107 Uiso 1 1 calc R . .
C7 C 0.1562(4) 0.3336(5) 0.2735(4) 0.0921(16) Uani 1 1 d . . .
H7A H 0.1284 0.4074 0.2484 0.110 Uiso 1 1 calc R . .
H7B H 0.2158 0.3507 0.3103 0.110 Uiso 1 1 calc R . .
C8 C 0.1699(3) 0.2528(4) 0.1833(4) 0.0668(11) Uani 1 1 d . . .
H8A H 0.2200 0.1966 0.1997 0.080 Uiso 1 1 calc R . .
H8B H 0.1853 0.2957 0.1180 0.080 Uiso 1 1 calc R . .
N9 N 0.0775(2) 0.1920(3) 0.1710(2) 0.0434(7) Uani 1 1 d . . .
H9NA H 0.085(2) 0.124(4) 0.163(3) 0.047(11) Uiso 1 1 d . . .
H9NB H 0.046(3) 0.223(4) 0.120(4) 0.072(14) Uiso 1 1 d . . .
Cl1 Cl 0.33883(11) 0.0000 0.36916(11) 0.0616(4) Uani 1 2 d S . .
O11 O 0.4184(5) 0.0000 0.3043(5) 0.134(3) Uani 1 2 d S . .
O12 O 0.3361(4) 0.0983(5) 0.4285(5) 0.167(2) Uani 1 1 d . . .
O13 O 0.2563(5) 0.0000 0.3026(5) 0.128(2) Uani 1 2 d S . .
Cl2 Cl 0.34865(8) 0.5000 0.04931(8) 0.0411(4) Uani 1 2 d S . .
O21 O 0.3222(2) 0.5000 -0.0634(3) 0.0539(9) Uani 1 2 d S . .
O22 O 0.2659(3) 0.5000 0.1084(4) 0.0786(13) Uani 1 2 d S . .
O23 O 0.4002(2) 0.3969(3) 0.0724(2) 0.0868(11) Uani 1 1 d . . .
O1W O 0.3815(3) 0.0000 0.0831(4) 0.0585(11) Uani 1 2 d S . .
H1WA H 0.388(6) 0.0000 0.152(8) 0.11(3) Uiso 1 2 d S . .
H1WB H 0.337(5) 0.0000 0.069(6) 0.09(3) Uiso 1 2 d S . .
O2W O 0.0000 0.3317(3) 0.0000 0.0491(9) Uani 1 2 d S . .
H2WA H 0.039(3) 0.369(4) -0.021(3) 0.058(13) 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 0.0016 '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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C2 118.4(4) 6 . ?
N1 C2 C3 122.4(3) . . ?
N1 C2 C5 117.5(3) . . ?
C3 C2 C5 120.1(3) . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C3 119.9(4) . 6 ?
C3 C4 H4 120.1 . . ?
C3 C4 H4 120.1 6 . ?
C2 C5 N9 111.9(3) . . ?
C2 C5 C6 114.4(3) . . ?
N9 C5 C6 102.9(3) . . ?
C2 C5 H5 109.1 . . ?
N9 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
C7 C6 C5 103.8(3) . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C6 105.2(4) . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C7 C8 N9 103.7(4) . . ?
C7 C8 H8A 111.0 . . ?
N9 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
N9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C5 N9 C8 109.4(3) . . ?
C5 N9 H9NA 109(3) . . ?
C8 N9 H9NA 110(3) . . ?
C5 N9 H9NB 106(3) . . ?
C8 N9 H9NB 109(3) . . ?
H9NA N9 H9NB 113(4) . . ?
O12 Cl1 O12 113.1(6) . 6 ?
O12 Cl1 O11 110.4(3) . . ?
O12 Cl1 O11 110.4(3) 6 . ?
O12 Cl1 O13 106.7(3) . . ?
O12 Cl1 O13 106.7(3) 6 . ?
O11 Cl1 O13 109.5(4) . . ?
O22 Cl2 O23 109.49(19) . 6_565 ?
O22 Cl2 O23 109.49(19) . . ?
O23 Cl2 O23 112.5(3) 6_565 . ?
O22 Cl2 O21 107.6(3) . . ?
O23 Cl2 O21 108.83(15) 6_565 . ?
O23 Cl2 O21 108.83(15) . . ?
H1WA O1W H1WB 110(9) . . ?
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
N1 C2 1.337(4) 6 ?
N1 C2 1.337(4) . ?
C2 C3 1.384(4) . ?
C2 C5 1.496(5) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9400 . ?
C4 C3 1.372(4) 6 ?
C4 H4 0.9400 . ?
C5 N9 1.496(4) . ?
C5 C6 1.537(5) . ?
C5 H5 0.9900 . ?
C6 C7 1.482(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.473(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 N9 1.499(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
N9 H9NA 0.79(4) . ?
N9 H9NB 0.85(5) . ?
Cl1 O12 1.346(4) . ?
Cl1 O12 1.346(4) 6 ?
Cl1 O11 1.410(6) . ?
Cl1 O13 1.431(6) . ?
Cl2 O22 1.407(4) . ?
Cl2 O23 1.416(3) 6_565 ?
Cl2 O23 1.416(3) . ?
Cl2 O21 1.449(3) . ?
O1W H1WA 0.86(9) . ?
O1W H1WB 0.66(8) . ?
O2W H2WA 0.74(4) . ?
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
N9 H9NA N1 0.79(4) 2.23(4) 2.701(4) 119(3) .
N9 H9NA O21 0.79(4) 2.32(4) 2.957(4) 139(3) 7
N9 H9NB O2W 0.85(5) 2.04(5) 2.870(4) 164(4) .
O1W H1WA O11 0.86(9) 1.94(9) 2.801(8) 173(8) .
O1W H1WB O21 0.66(8) 2.28(8) 2.922(6) 167(9) 7
O1W H1WB O22 0.66(8) 2.64(8) 3.157(7) 138(8) 7
O2W H2WA O1W 0.74(4) 2.05(4) 2.777(4) 166(4) 7
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
C2 N1 C2 C3 1.6(6) 6 . . . ?
C2 N1 C2 C5 -179.8(2) 6 . . . ?
N1 C2 C3 C4 -0.1(5) . . . . ?
C5 C2 C3 C4 -178.8(4) . . . . ?
C2 C3 C4 C3 -1.3(7) . . . 6 ?
N1 C2 C5 N9 15.7(4) . . . . ?
C3 C2 C5 N9 -165.6(3) . . . . ?
N1 C2 C5 C6 -100.8(4) . . . . ?
C3 C2 C5 C6 77.9(4) . . . . ?
C2 C5 C6 C7 150.4(4) . . . . ?
N9 C5 C6 C7 28.8(5) . . . . ?
C5 C6 C7 C8 -39.7(5) . . . . ?
C6 C7 C8 N9 34.0(5) . . . . ?
C2 C5 N9 C8 -131.6(3) . . . . ?
C6 C5 N9 C8 -8.3(4) . . . . ?
C7 C8 N9 C5 -15.4(4) . . . . ?
