#------------------------------------------------------------------------------
#$Date: 2018-09-14 12:35:05 +0300 (Fri, 14 Sep 2018) $
#$Revision: 210947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/25/7052513.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_7052513
loop_
_publ_author_name
'Kiviniemi, Sari'
'Nissinen, Maija'
'Lämsä, Markku T.'
'Jalonen, Jorma'
'Rissanen, Kari'
'Pursiainen, Jouni'
_publ_section_title
;
 Complexation of planar, organic, five-membered cations with crown ethers
;
_journal_coden_ASTM              NJCHE5
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              47
_journal_page_last               52
_journal_paper_doi               10.1039/a907608e
_journal_volume                  24
_journal_year                    2000
_chemical_formula_moiety         'C20 H24 O6, (C3 H5 N2)+ (Cl O4)-'
_chemical_formula_sum            'C23 H29 Cl N2 O10'
_chemical_formula_weight         528.93
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 129.34(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.802(4)
_cell_length_b                   14.255(4)
_cell_length_c                   12.199(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173.0(1)
_cell_measurement_theta_max      12.25
_cell_measurement_theta_min      8.01
_cell_volume                     2394.2(11)
_computing_cell_refinement       'CAD4 (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD4 (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4/WinGX-97 (Farrugia, 1997)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX-98 (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173.0(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2184
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_correction_T_min  0.9167
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         2184
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0420
_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)+(0.0405P)²+7.6190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                1887
_reflns_number_total             2184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a907608e.txt
_cod_data_source_block           COMP7
_cod_original_cell_volume        2394(1)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7052513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
C2 C -0.0882(5) -0.2744(5) -0.2264(7) 0.0289(14) Uani 1 1 d . . .
H2A H -0.063(5) -0.265(5) -0.285(7) 0.033(19) Uiso 1 1 d . . .
H2B H -0.105(6) -0.209(5) -0.213(8) 0.04(2) Uiso 1 1 d . . .
C3 C -0.0048(5) -0.3202(5) -0.0904(7) 0.0317(15) Uani 1 1 d . . .
H3A H -0.022(5) -0.328(5) -0.025(7) 0.029(17) Uiso 1 1 d . . .
H3B H 0.045(5) -0.283(5) -0.047(8) 0.04(2) Uiso 1 1 d . . .
C5 C 0.1124(5) -0.4417(5) 0.0017(7) 0.0305(15) Uani 1 1 d . . .
H5A H 0.168(6) -0.390(6) 0.051(9) 0.06(3) Uiso 1 1 d . . .
H5B H 0.080(4) -0.458(4) 0.049(6) 0.019(15) Uiso 1 1 d . . .
C6 C 0.1473(5) -0.5135(5) -0.0444(6) 0.0274(14) Uani 1 1 d . . .
H6A H 0.212(6) -0.546(6) 0.041(9) 0.06(2) Uiso 1 1 d . . .
H6B H 0.155(5) -0.484(4) -0.112(7) 0.022(16) Uiso 1 1 d . . .
C8 C 0.0918(4) -0.6592(4) -0.1711(6) 0.0257(13) Uani 1 1 d . . .
C9 C 0.1702(5) -0.6666(5) -0.1680(7) 0.0313(15) Uani 1 1 d . . .
H9 H 0.217(5) -0.608(5) -0.121(7) 0.04(2) Uiso 1 1 d . . .
C10 C 0.1790(5) -0.7438(5) -0.2266(7) 0.0342(16) Uani 1 1 d . . .
H10 H 0.227(5) -0.756(5) -0.228(7) 0.028(18) Uiso 1 1 d . . .
C11 C 0.1091(5) -0.8128(5) -0.2914(7) 0.0346(16) Uani 1 1 d . . .
H11 H 0.108(5) -0.866(6) -0.339(8) 0.04(2) Uiso 1 1 d . . .
C12 C 0.0292(5) -0.8057(5) -0.2975(7) 0.0314(15) Uani 1 1 d . . .
H12 H -0.021(5) -0.857(5) -0.347(7) 0.028(17) Uiso 1 1 d . . .
C13 C 0.0210(5) -0.7286(4) -0.2364(6) 0.0270(14) Uani 1 1 d . . .
C15 C -0.1356(5) -0.7788(5) -0.3162(7) 0.0309(15) Uani 1 1 d . . .
H15A H -0.155(4) -0.788(4) -0.410(6) 0.008(13) Uiso 1 1 d . . .
H15B H -0.126(7) -0.844(6) -0.276(9) 0.06(3) Uiso 1 1 d . . .
C16 C -0.2142(5) -0.7422(5) -0.3169(7) 0.0302(14) Uani 1 1 d . . .
H16A H -0.188(4) -0.738(4) -0.220(6) 0.014(14) Uiso 1 1 d . . .
H16B H -0.264(5) -0.789(5) -0.364(7) 0.032(18) Uiso 1 1 d . . .
C18 C -0.3330(5) -0.6232(5) -0.4159(7) 0.0315(15) Uani 1 1 d . . .
H18A H -0.383(4) -0.679(4) -0.465(6) 0.014(14) Uiso 1 1 d . . .
H18B H -0.320(4) -0.604(4) -0.330(7) 0.020(15) Uiso 1 1 d . . .
C19 C -0.3701(5) -0.5392(5) -0.5100(7) 0.0307(15) Uani 1 1 d . . .
H19A H -0.440(5) -0.519(5) -0.550(7) 0.029(18) Uiso 1 1 d . . .
H19B H -0.375(4) -0.548(4) -0.579(7) 0.006(14) Uiso 1 1 d . . .
C21 C -0.3164(4) -0.3864(4) -0.5128(6) 0.0252(13) Uani 1 1 d . . .
C22 C -0.3947(5) -0.3748(5) -0.6560(7) 0.0298(14) Uani 1 1 d . . .
H22 H -0.447(6) -0.431(5) -0.717(8) 0.05(2) Uiso 1 1 d . . .
C23 C -0.3997(5) -0.2947(5) -0.7267(7) 0.0332(15) Uani 1 1 d . . .
H23 H -0.468(5) -0.294(5) -0.848(7) 0.032(18) Uiso 1 1 d . . .
C24 C -0.3288(5) -0.2270(5) -0.6555(7) 0.0333(15) Uani 1 1 d . . .
H24 H -0.325(5) -0.164(5) -0.703(7) 0.035(18) Uiso 1 1 d . . .
C25 C -0.2495(5) -0.2384(5) -0.5109(7) 0.0320(15) Uani 1 1 d . . .
H25 H -0.198(6) -0.195(5) -0.457(8) 0.04(2) Uiso 1 1 d . . .
C26 C -0.2435(4) -0.3171(4) -0.4405(6) 0.0254(13) Uani 1 1 d . . .
C28 C -0.1506(6) -0.5365(5) -0.4965(8) 0.0406(18) Uani 1 1 d . . .
H28 H -0.191(5) -0.581(4) -0.493(6) 0.018(15) Uiso 1 1 d . . .
C31 C -0.0517(6) -0.4246(6) -0.4494(9) 0.050(2) Uani 1 1 d . . .
H31 H -0.003(6) -0.377(6) -0.394(8) 0.05(2) Uiso 1 1 d . . .
C30 C -0.0991(6) -0.4467(5) -0.5828(8) 0.0374(17) Uani 1 1 d . . .
H30 H -0.090(5) -0.432(5) -0.641(8) 0.033(18) Uiso 1 1 d . . .
O1 O -0.1698(3) -0.3366(3) -0.2993(4) 0.0276(10) Uani 1 1 d . . .
O4 O 0.0242(3) -0.4015(3) -0.1222(4) 0.0277(10) Uani 1 1 d . . .
O7 O 0.0755(3) -0.5865(3) -0.1141(4) 0.0293(10) Uani 1 1 d . . .
O14 O -0.0563(3) -0.7138(3) -0.2367(4) 0.0296(10) Uani 1 1 d . . .
O17 O -0.2481(3) -0.6551(3) -0.3910(4) 0.0297(10) Uani 1 1 d . . .
O20 O -0.3023(3) -0.4629(3) -0.4334(4) 0.0287(10) Uani 1 1 d . . .
O100 O -0.1285(4) -0.0064(5) -0.4505(6) 0.0580(16) Uani 1 1 d . . .
O101 O -0.0670(4) -0.1034(5) -0.5324(6) 0.0631(17) Uani 1 1 d . . .
O102 O -0.2252(4) -0.0449(4) -0.6899(6) 0.0548(14) Uani 1 1 d . . .
O103 O -0.0903(6) 0.0557(5) -0.5875(8) 0.080(2) Uani 1 1 d . . .
N29 N -0.1610(4) -0.5175(4) -0.6117(6) 0.0377(14) Uani 1 1 d . . .
H29 H -0.203(6) -0.552(5) -0.702(8) 0.04(2) Uiso 1 1 d . . .
N27 N -0.0830(4) -0.4777(5) -0.3974(6) 0.0466(18) Uani 1 1 d . . .
H27 H -0.069(6) -0.459(6) -0.313(9) 0.05(2) Uiso 1 1 d . . .
Cl1 Cl -0.12799(11) -0.02396(11) -0.56607(15) 0.0330(4) Uani 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'
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'
Cl Cl 0.1484 0.1585 '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 C2 C3 108.7(5) . . ?
O4 C3 C2 109.2(5) . . ?
O4 C5 C6 108.6(5) . . ?
O7 C6 C5 107.2(5) . . ?
C9 C8 O7 125.3(6) . . ?
C9 C8 C13 119.8(6) . . ?
O7 C8 C13 114.9(5) . . ?
C10 C9 C8 119.7(7) . . ?
C9 C10 C11 120.7(7) . . ?
C10 C11 C12 120.3(7) . . ?
C11 C12 C13 119.0(7) . . ?
C12 C13 C8 120.4(6) . . ?
C12 C13 O14 124.1(6) . . ?
C8 C13 O14 115.5(5) . . ?
O14 C15 C16 107.3(6) . . ?
O17 C16 C15 109.1(5) . . ?
O17 C18 C19 108.4(5) . . ?
O20 C19 C18 109.1(5) . . ?
O20 C21 C22 124.8(6) . . ?
O20 C21 C26 115.5(5) . . ?
C22 C21 C26 119.6(6) . . ?
C21 C22 C23 119.5(6) . . ?
C24 C23 C22 120.6(6) . . ?
C23 C24 C25 120.1(6) . . ?
C26 C25 C24 119.8(7) . . ?
C25 C26 O1 125.5(6) . . ?
C25 C26 C21 120.3(6) . . ?
O1 C26 C21 114.2(5) . . ?
N29 C28 N27 105.9(7) . . ?
C30 C31 N27 108.8(7) . . ?
C31 C30 N29 106.2(7) . . ?
C26 O1 C2 116.0(5) . . ?
C3 O4 C5 112.5(5) . . ?
C8 O7 C6 116.8(5) . . ?
C13 O14 C15 116.9(5) . . ?
C18 O17 C16 112.4(5) . . ?
C21 O20 C19 116.0(5) . . ?
C28 N29 C30 109.2(6) . . ?
C31 N27 C28 109.8(6) . . ?
O103 Cl1 O102 111.6(4) . . ?
O103 Cl1 O100 109.7(4) . . ?
O102 Cl1 O100 108.4(3) . . ?
O103 Cl1 O101 108.8(5) . . ?
O102 Cl1 O101 109.0(4) . . ?
O100 Cl1 O101 109.3(4) . . ?
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
C2 O1 1.431(7) . ?
C2 C3 1.503(10) . ?
C3 O4 1.419(8) . ?
C5 O4 1.439(8) . ?
C5 C6 1.481(9) . ?
C6 O7 1.436(8) . ?
C8 C9 1.376(9) . ?
C8 O7 1.377(8) . ?
C8 C13 1.388(9) . ?
C9 C10 1.375(10) . ?
C10 C11 1.376(10) . ?
C11 C12 1.380(10) . ?
C12 C13 1.386(9) . ?
C13 O14 1.389(8) . ?
C15 O14 1.435(8) . ?
C15 C16 1.488(10) . ?
C16 O17 1.425(8) . ?
C18 O17 1.415(8) . ?
C18 C19 1.493(10) . ?
C19 O20 1.443(8) . ?
C21 O20 1.371(8) . ?
C21 C22 1.391(9) . ?
C21 C26 1.410(9) . ?
C22 C23 1.400(10) . ?
C23 C24 1.375(10) . ?
C24 C25 1.405(10) . ?
C25 C26 1.375(9) . ?
C26 O1 1.379(7) . ?
C28 N29 1.324(10) . ?
C28 N27 1.329(10) . ?
C31 C30 1.311(11) . ?
C31 N27 1.319(11) . ?
C30 N29 1.365(10) . ?
O100 Cl1 1.437(5) . ?
O101 Cl1 1.437(6) . ?
O102 Cl1 1.432(5) . ?
O103 Cl1 1.425(6) . ?
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
N29 H29 O20 0.99(8) 2.19(8) 3.048(7) 144(6) 2_544
N29 H29 O1 0.99(8) 2.28(8) 3.022(7) 132(6) 2_544
N27 H27 O4 0.94(9) 1.99(9) 2.823(7) 148(7) .
N27 H27 O1 0.94(9) 2.58(8) 3.195(7) 124(6) .
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 C2 C3 O4 65.0(7) . . . . ?
O4 C5 C6 O7 -64.0(6) . . . . ?
O7 C8 C9 C10 178.8(6) . . . . ?
C13 C8 C9 C10 -1.6(9) . . . . ?
C8 C9 C10 C11 1.5(9) . . . . ?
C9 C10 C11 C12 -0.4(10) . . . . ?
C10 C11 C12 C13 -0.6(9) . . . . ?
C11 C12 C13 C8 0.5(9) . . . . ?
C11 C12 C13 O14 179.6(6) . . . . ?
C9 C8 C13 C12 0.5(9) . . . . ?
O7 C8 C13 C12 -179.8(5) . . . . ?
C9 C8 C13 O14 -178.6(5) . . . . ?
O7 C8 C13 O14 1.0(7) . . . . ?
O14 C15 C16 O17 64.2(7) . . . . ?
O17 C18 C19 O20 -67.6(7) . . . . ?
O20 C21 C22 C23 -178.1(6) . . . . ?
C26 C21 C22 C23 0.5(9) . . . . ?
C21 C22 C23 C24 -1.0(9) . . . . ?
C22 C23 C24 C25 1.0(10) . . . . ?
C23 C24 C25 C26 -0.5(9) . . . . ?
C24 C25 C26 O1 179.9(6) . . . . ?
C24 C25 C26 C21 0.1(9) . . . . ?
O20 C21 C26 C25 178.7(5) . . . . ?
C22 C21 C26 C25 -0.1(9) . . . . ?
O20 C21 C26 O1 -1.2(7) . . . . ?
C22 C21 C26 O1 -180.0(5) . . . . ?
N27 C31 C30 N29 -0.9(9) . . . . ?
C25 C26 O1 C2 -7.7(8) . . . . ?
C21 C26 O1 C2 172.2(5) . . . . ?
C3 C2 O1 C26 -163.9(5) . . . . ?
C2 C3 O4 C5 171.6(5) . . . . ?
C6 C5 O4 C3 -168.9(5) . . . . ?
C9 C8 O7 C6 -0.9(8) . . . . ?
C13 C8 O7 C6 179.5(5) . . . . ?
C5 C6 O7 C8 177.3(5) . . . . ?
C12 C13 O14 C15 -5.5(8) . . . . ?
C8 C13 O14 C15 173.6(5) . . . . ?
C16 C15 O14 C13 -172.7(5) . . . . ?
C19 C18 O17 C16 -172.6(5) . . . . ?
C15 C16 O17 C18 170.6(5) . . . . ?
C22 C21 O20 C19 5.8(8) . . . . ?
C26 C21 O20 C19 -172.9(5) . . . . ?
C18 C19 O20 C21 168.2(5) . . . . ?
N27 C28 N29 C30 0.1(8) . . . . ?
C31 C30 N29 C28 0.5(8) . . . . ?
C30 C31 N27 C28 1.0(9) . . . . ?
N29 C28 N27 C31 -0.7(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21142489
