#------------------------------------------------------------------------------
#$Date: 2018-09-14 12:35:05 +0300 (Fri, 14 Sep 2018) $
#$Revision: 210947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/25/7052514.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_7052514
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
_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                 129.003(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.804(1)
_cell_length_b                   14.131(1)
_cell_length_c                   12.317(1)
_cell_measurement_reflns_used    1342
_cell_measurement_temperature    173.0(1)
_cell_volume                     2408.1(3)
_computing_cell_refinement       'Denzo-SMN v0.93.0 (Otwinowki, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'Denzo-SMN v0.93.0 (Otwinowki, 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 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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    0.0890
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2828
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_correction_T_min  0.9075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0076(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         2828
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0887
_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)+(0.1138P)²+10.7147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2289
_refine_ls_wR_factor_ref         0.2535
_reflns_number_gt                1953
_reflns_number_total             2828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a907608e.txt
_cod_data_source_block           COMP14
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7052514
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
Cl1 Cl -0.22851(16) -0.02106(17) -0.4899(2) 0.0387(6) Uani 1 1 d . . .
C2 C 0.0213(7) 0.0347(7) 0.0507(11) 0.034(2) Uani 1 1 d . . .
H2A H -0.0435 0.0167 0.0187 0.041 Uiso 1 1 calc R . .
H2B H 0.0161 0.0500 -0.0322 0.041 Uiso 1 1 calc R . .
C3 C 0.0584(7) 0.1177(7) 0.1457(11) 0.036(2) Uani 1 1 d . . .
H3A H 0.0090 0.1684 0.1017 0.043 Uiso 1 1 calc R . .
H3B H 0.0723 0.0993 0.2343 0.043 Uiso 1 1 calc R . .
C5 C 0.1790(7) 0.2387(8) 0.2520(10) 0.038(2) Uani 1 1 d . . .
H5A H 0.2022 0.2271 0.3480 0.045 Uiso 1 1 calc R . .
H5B H 0.1261 0.2857 0.2067 0.045 Uiso 1 1 calc R . .
C6 C 0.2595(7) 0.2749(7) 0.2566(11) 0.034(2) Uani 1 1 d . . .
H6A H 0.2384 0.2803 0.1609 0.040 Uiso 1 1 calc R . .
H6B H 0.2802 0.3381 0.3011 0.040 Uiso 1 1 calc R . .
C8 C 0.4141(7) 0.2213(7) 0.3374(10) 0.035(2) Uani 1 1 d . . .
C9 C 0.4229(7) 0.2971(7) 0.2755(10) 0.036(2) Uani 1 1 d . . .
H9 H 0.3742 0.3445 0.2286 0.043 Uiso 1 1 calc R . .
C10 C 0.5050(7) 0.3035(7) 0.2828(11) 0.041(2) Uani 1 1 d . . .
H10 H 0.5118 0.3555 0.2407 0.049 Uiso 1 1 calc R . .
C11 C 0.5741(8) 0.2357(8) 0.3498(10) 0.040(2) Uani 1 1 d . . .
H11 H 0.6290 0.2403 0.3535 0.048 Uiso 1 1 calc R . .
C12 C 0.5661(7) 0.1593(8) 0.4131(11) 0.040(2) Uani 1 1 d . . .
H12 H 0.6154 0.1126 0.4609 0.048 Uiso 1 1 calc R . .
C13 C 0.4851(7) 0.1521(7) 0.4056(9) 0.032(2) Uani 1 1 d . . .
C15 C 0.5398(7) 0.0067(8) 0.5331(11) 0.041(2) Uani 1 1 d . . .
H15A H 0.6031 0.0305 0.6164 0.049 Uiso 1 1 calc R . .
H15B H 0.5484 -0.0205 0.4674 0.049 Uiso 1 1 calc R . .
C16 C 0.5007(7) -0.0671(8) 0.5746(10) 0.037(2) Uani 1 1 d . . .
H16A H 0.5485 -0.1185 0.6284 0.045 Uiso 1 1 calc R . .
H16B H 0.4868 -0.0383 0.6336 0.045 Uiso 1 1 calc R . .
C18 C 0.3822(8) -0.1892(7) 0.4725(10) 0.037(2) Uani 1 1 d . . .
H18A H 0.3595 -0.1745 0.5262 0.044 Uiso 1 1 calc R . .
H18B H 0.4368 -0.2342 0.5277 0.044 Uiso 1 1 calc R . .
C19 C 0.3024(7) -0.2325(7) 0.3363(11) 0.037(2) Uani 1 1 d . . .
H19A H 0.3237 -0.2435 0.2799 0.045 Uiso 1 1 calc R . .
H19B H 0.2842 -0.2942 0.3518 0.045 Uiso 1 1 calc R . .
C21 C 0.1487(6) -0.1882(7) 0.1231(10) 0.031(2) Uani 1 1 d . . .
C22 C 0.1432(7) -0.2680(7) 0.0522(11) 0.037(2) Uani 1 1 d . . .
H22 H 0.1913 -0.3158 0.1013 0.044 Uiso 1 1 calc R . .
C23 C 0.0686(7) -0.2781(7) -0.0890(11) 0.038(2) Uani 1 1 d . . .
H23 H 0.0664 -0.3320 -0.1371 0.045 Uiso 1 1 calc R . .
C24 C -0.0021(7) -0.2113(7) -0.1599(11) 0.039(2) Uani 1 1 d . . .
H24 H -0.0541 -0.2192 -0.2568 0.047 Uiso 1 1 calc R . .
C25 C 0.0018(7) -0.1309(7) -0.0901(10) 0.035(2) Uani 1 1 d . . .
H25 H -0.0476 -0.0844 -0.1398 0.042 Uiso 1 1 calc R . .
C26 C 0.0758(7) -0.1191(6) 0.0483(10) 0.030(2) Uani 1 1 d . . .
O1 O 0.0882(5) -0.0416(5) 0.1277(7) 0.0345(15) Uani 1 1 d . . .
O4 O 0.1449(5) 0.1518(5) 0.1736(7) 0.0342(15) Uani 1 1 d . . .
O7 O 0.3375(5) 0.2084(5) 0.3368(7) 0.0342(15) Uani 1 1 d . . .
O14 O 0.4697(4) 0.0825(5) 0.4668(7) 0.0340(15) Uani 1 1 d . . .
O17 O 0.4134(4) -0.1042(5) 0.4482(6) 0.0349(15) Uani 1 1 d . . .
O20 O 0.2209(4) -0.1695(5) 0.2635(7) 0.0340(15) Uani 1 1 d . . .
O101 O -0.1703(7) -0.1039(7) -0.4602(10) 0.067(3) Uani 1 1 d . . .
O102 O -0.3242(6) -0.0400(8) -0.6176(9) 0.067(3) Uani 1 1 d . . .
O103 O -0.2331(6) -0.0065(6) -0.3812(8) 0.049(2) Uani 1 1 d . . .
O104 O -0.1869(9) 0.0573(7) -0.5056(12) 0.079(3) Uani 1 1 d . . .
C30 C 0.2752(9) -0.0313(8) -0.0094(12) 0.046(3) Uani 1 1 d . . .
H30 H 0.2736 -0.0515 -0.0844 0.056 Uiso 1 1 calc R . .
C29 C 0.2209(7) 0.0366(8) -0.0144(11) 0.038(2) Uani 1 1 d . . .
H29 H 0.1752 0.0750 -0.0929 0.046 Uiso 1 1 calc R . .
C31 C 0.3324(7) -0.0656(8) 0.1214(11) 0.039(2) Uani 1 1 d . . .
H31 H 0.3803 -0.1131 0.1560 0.047 Uiso 1 1 calc R . .
N27 N 0.3116(6) -0.0234(6) 0.1925(8) 0.0342(18) Uani 1 1 d . . .
H27 H 0.3385 -0.0346 0.2804 0.041 Uiso 1 1 calc R . .
N28 N 0.2418(5) 0.0408(6) 0.1094(8) 0.0326(18) Uani 1 1 d . . .
H28 H 0.2149 0.0787 0.1331 0.039 Uiso 1 1 calc R . .
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
O103 Cl1 O104 111.5(6) . . ?
O103 Cl1 O102 109.2(5) . . ?
O104 Cl1 O102 110.9(7) . . ?
O103 Cl1 O101 109.8(6) . . ?
O104 Cl1 O101 108.3(6) . . ?
O102 Cl1 O101 107.0(6) . . ?
O1 C2 C3 107.4(8) . . ?
O4 C3 C2 109.5(7) . . ?
O4 C5 C6 108.0(8) . . ?
O7 C6 C5 107.1(7) . . ?
O7 C8 C9 123.9(9) . . ?
O7 C8 C13 115.7(8) . . ?
C9 C8 C13 120.4(9) . . ?
C8 C9 C10 119.2(9) . . ?
C11 C10 C9 120.1(10) . . ?
C10 C11 C12 121.0(10) . . ?
C13 C12 C11 119.2(10) . . ?
O14 C13 C8 114.9(8) . . ?
O14 C13 C12 125.1(9) . . ?
C8 C13 C12 120.0(9) . . ?
O14 C15 C16 106.5(8) . . ?
O17 C16 C15 107.4(8) . . ?
O17 C18 C19 109.3(7) . . ?
O20 C19 C18 108.7(8) . . ?
O20 C21 C22 125.6(8) . . ?
O20 C21 C26 115.7(8) . . ?
C22 C21 C26 118.7(9) . . ?
C23 C22 C21 120.4(10) . . ?
C24 C23 C22 120.3(10) . . ?
C23 C24 C25 120.0(10) . . ?
C26 C25 C24 120.3(10) . . ?
C25 C26 O1 125.4(9) . . ?
C25 C26 C21 120.2(9) . . ?
O1 C26 C21 114.4(8) . . ?
C26 O1 C2 115.4(7) . . ?
C3 O4 C5 112.6(7) . . ?
C8 O7 C6 116.5(7) . . ?
C13 O14 C15 116.3(7) . . ?
C18 O17 C16 112.1(7) . . ?
C21 O20 C19 116.1(7) . . ?
C29 C30 C31 107.1(9) . . ?
N28 C29 C30 108.0(9) . . ?
N27 C31 C30 108.8(10) . . ?
C31 N27 N28 108.5(8) . . ?
C29 N28 N27 107.5(8) . . ?
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
Cl1 O103 1.407(7) . ?
Cl1 O104 1.411(9) . ?
Cl1 O102 1.441(8) . ?
Cl1 O101 1.450(9) . ?
C2 O1 1.434(11) . ?
C2 C3 1.486(14) . ?
C3 O4 1.432(12) . ?
C5 O4 1.438(13) . ?
C5 C6 1.488(14) . ?
C6 O7 1.436(11) . ?
C8 O7 1.371(11) . ?
C8 C9 1.379(14) . ?
C8 C13 1.386(14) . ?
C9 C10 1.409(15) . ?
C10 C11 1.356(15) . ?
C11 C12 1.391(16) . ?
C12 C13 1.390(13) . ?
C13 O14 1.367(12) . ?
C15 O14 1.445(11) . ?
C15 C16 1.512(16) . ?
C16 O17 1.438(12) . ?
C18 O17 1.433(12) . ?
C18 C19 1.486(15) . ?
C19 O20 1.437(11) . ?
C21 O20 1.384(12) . ?
C21 C22 1.391(14) . ?
C21 C26 1.408(13) . ?
C22 C23 1.379(15) . ?
C23 C24 1.362(15) . ?
C24 C25 1.399(15) . ?
C25 C26 1.358(13) . ?
C26 O1 1.391(11) . ?
C30 C29 1.336(15) . ?
C30 C31 1.343(16) . ?
C29 N28 1.324(12) . ?
C31 N27 1.292(13) . ?
N27 N28 1.347(11) . ?
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
N27 H27 O17 0.88 1.88 2.706(10) 154.9 .
N27 H27 O14 0.88 2.59 3.099(10) 117.6 .
N28 H28 O4 0.88 1.91 2.789(9) 173.8 .
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 68.8(10) . . . . ?
O4 C5 C6 O7 -66.0(10) . . . . ?
O7 C8 C9 C10 179.8(9) . . . . ?
C13 C8 C9 C10 -0.1(14) . . . . ?
C8 C9 C10 C11 0.1(14) . . . . ?
C9 C10 C11 C12 -0.5(15) . . . . ?
C10 C11 C12 C13 0.9(15) . . . . ?
O7 C8 C13 O14 -2.2(12) . . . . ?
C9 C8 C13 O14 177.8(8) . . . . ?
O7 C8 C13 C12 -179.4(8) . . . . ?
C9 C8 C13 C12 0.6(14) . . . . ?
C11 C12 C13 O14 -177.8(9) . . . . ?
C11 C12 C13 C8 -0.9(14) . . . . ?
O14 C15 C16 O17 65.0(10) . . . . ?
O17 C18 C19 O20 -64.5(9) . . . . ?
O20 C21 C22 C23 -178.7(8) . . . . ?
C26 C21 C22 C23 1.1(13) . . . . ?
C21 C22 C23 C24 -1.8(14) . . . . ?
C22 C23 C24 C25 1.2(14) . . . . ?
C23 C24 C25 C26 0.0(14) . . . . ?
C24 C25 C26 O1 178.6(9) . . . . ?
C24 C25 C26 C21 -0.7(13) . . . . ?
O20 C21 C26 C25 179.9(8) . . . . ?
C22 C21 C26 C25 0.2(13) . . . . ?
O20 C21 C26 O1 0.6(11) . . . . ?
C22 C21 C26 O1 -179.2(8) . . . . ?
C25 C26 O1 C2 -6.4(12) . . . . ?
C21 C26 O1 C2 173.0(7) . . . . ?
C3 C2 O1 C26 -167.7(7) . . . . ?
C2 C3 O4 C5 173.4(8) . . . . ?
C6 C5 O4 C3 -171.7(8) . . . . ?
C9 C8 O7 C6 5.2(13) . . . . ?
C13 C8 O7 C6 -174.9(8) . . . . ?
C5 C6 O7 C8 171.0(8) . . . . ?
C8 C13 O14 C15 177.1(8) . . . . ?
C12 C13 O14 C15 -5.9(13) . . . . ?
C16 C15 O14 C13 -172.4(8) . . . . ?
C19 C18 O17 C16 -170.3(8) . . . . ?
C15 C16 O17 C18 166.4(8) . . . . ?
C22 C21 O20 C19 8.1(12) . . . . ?
C26 C21 O20 C19 -171.6(8) . . . . ?
C18 C19 O20 C21 165.9(7) . . . . ?
C31 C30 C29 N28 -2.5(13) . . . . ?
C29 C30 C31 N27 2.4(13) . . . . ?
C30 C31 N27 N28 -1.4(12) . . . . ?
C30 C29 N28 N27 1.7(11) . . . . ?
C31 N27 N28 C29 -0.2(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21142483
