#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:07:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179614 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/78/4507876.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_4507876
loop_
_publ_author_name
'Li, Shigeng'
'Luo, Junhua'
'Sun, Zhihua'
'Zhang, Shuquan'
'Li, Lina'
'Shi, Xiaojun'
'Hong, Maochun'
_publ_section_title
;
 Phase Transition Triggered by Ordering of Unique Pendulum-Like Motions in
 a Supramolecular Complex: Potassium Hydrogen
 Bis(dichloroacetate)-18-Crown-6
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2675
_journal_paper_doi               10.1021/cg4004565
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C16 H27 Cl4 K O10'
_chemical_formula_weight         560.63
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 99.704(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.447(4)
_cell_length_b                   9.0676(15)
_cell_length_c                   14.438(3)
_cell_measurement_reflns_used    2965
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5281
_cell_measurement_theta_min      2.4610
_cell_volume                     2638.6(9)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  ω
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9953
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         3619
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2000)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0760P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                1815
_reflns_number_total             3020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4004565_si_002.cif
_cod_data_source_block           e:RT
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4507876
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'
'-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
K1 K 0.2500 0.2500 0.0000 0.0689(3) Uani 1 2 d S . .
Cl1A Cl 0.44176(10) 0.6348(5) 0.14639(15) 0.103(2) Uani 0.86(2) 1 d PD A 1
Cl2A Cl 0.44403(8) 0.6575(3) -0.05392(16) 0.078(2) Uani 0.753(15) 1 d PD A 1
O5 O 0.2969(2) 0.5137(5) 0.0481(4) 0.100(2) Uani 0.491(7) 1 d PU A 1
O5' O 0.2964(2) 0.5128(5) -0.0330(4) 0.0900(18) Uani 0.509(7) 1 d PU A 2
O4 O 0.31203(9) 0.7400(2) 0.0132(2) 0.0936(7) Uani 1 1 d . . .
O1 O 0.19281(11) 0.3179(2) 0.15795(15) 0.0884(6) Uani 1 1 d . A .
O2 O 0.31830(12) 0.1765(2) 0.18108(15) 0.0915(7) Uani 1 1 d . A .
O3 O 0.38722(9) 0.1751(2) 0.02543(14) 0.0729(5) Uani 1 1 d . A .
C1 C 0.12238(17) 0.3144(4) 0.1401(3) 0.0914(10) Uani 1 1 d . . .
H1A H 0.1049 0.3563 0.1944 0.110 Uiso 1 1 calc R A .
H1B H 0.1068 0.2111 0.1314 0.110 Uiso 1 1 calc R . .
C2 C 0.2212(2) 0.2415(5) 0.2418(2) 0.1095(13) Uani 1 1 d . . .
H2A H 0.2075 0.1367 0.2370 0.131 Uiso 1 1 calc R A .
H2B H 0.2049 0.2853 0.2964 0.131 Uiso 1 1 calc R . .
C3 C 0.2944(2) 0.2514(5) 0.2560(2) 0.1088(13) Uani 1 1 d . A .
H3A H 0.3081 0.3562 0.2574 0.131 Uiso 1 1 calc R . .
H3B H 0.3136 0.2059 0.3169 0.131 Uiso 1 1 calc R . .
C4 C 0.38776(18) 0.1788(4) 0.1902(2) 0.0947(10) Uani 1 1 d . . .
H4A H 0.4078 0.1332 0.2506 0.114 Uiso 1 1 calc R A .
H4B H 0.4036 0.2819 0.1897 0.114 Uiso 1 1 calc R . .
C5 C 0.40796(18) 0.0956(4) 0.1108(3) 0.0936(10) Uani 1 1 d . A .
H5A H 0.4567 0.0829 0.1217 0.112 Uiso 1 1 calc R . .
H5B H 0.3873 -0.0035 0.1063 0.112 Uiso 1 1 calc R . .
C6 C 0.40238(18) 0.0987(4) -0.0543(3) 0.0933(10) Uani 1 1 d . . .
H6A H 0.3811 0.0002 -0.0588 0.112 Uiso 1 1 calc R A .
H6B H 0.4510 0.0848 -0.0480 0.112 Uiso 1 1 calc R . .
C7 C 0.40492(11) 0.5792(3) 0.03421(16) 0.0589(6) Uani 1 1 d D . .
H15A H 0.4105 0.4699 0.0309 0.071 Uiso 1 1 calc R A 1
C8 C 0.33025(11) 0.6111(3) 0.01552(19) 0.0677(7) Uani 1 1 d . A .
Cl1B Cl 0.44778(11) 0.6975(3) 0.13391(19) 0.089(6) Uani 0.087(11) 1 d PRD A 2
Cl1C Cl 0.43128(11) 0.5779(3) 0.16100(19) 0.111(13) Uani 0.058(11) 1 d PRD A 3
Cl2C Cl 0.45408(11) 0.7049(3) -0.02689(19) 0.080(4) Uani 0.144(9) 1 d PRD A 3
Cl2B Cl 0.43248(11) 0.6042(3) -0.07729(19) 0.063(3) Uani 0.103(8) 1 d PRD A 2
H4C H 0.2500 0.7500 0.0000 0.075 Uiso 1 2 d SR . .
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'
K K 0.2009 0.2494 '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
O5 K1 O5 180.0(3) 7 .
O5 K1 O5' 25.68(13) 7 7
O5 K1 O5' 154.32(13) . 7
O5 K1 O5' 154.32(13) 7 .
O5 K1 O5' 25.68(13) . .
O5' K1 O5' 180.0(3) 7 .
O5 K1 O1 103.39(13) 7 .
O5 K1 O1 76.61(13) . .
O5' K1 O1 80.75(12) 7 .
O5' K1 O1 99.25(12) . .
O5 K1 O1 76.61(13) 7 7
O5 K1 O1 103.39(13) . 7
O5' K1 O1 99.25(12) 7 7
O5' K1 O1 80.75(12) . 7
O1 K1 O1 180.0 . 7
O5 K1 O2 97.54(14) 7 .
O5 K1 O2 82.46(14) . .
O5' K1 O2 75.91(12) 7 .
O5' K1 O2 104.09(12) . .
O1 K1 O2 60.53(7) . .
O1 K1 O2 119.47(7) 7 .
O5 K1 O2 82.46(14) 7 7
O5 K1 O2 97.54(14) . 7
O5' K1 O2 104.09(12) 7 7
O5' K1 O2 75.91(12) . 7
O1 K1 O2 119.47(7) . 7
O1 K1 O2 60.53(7) 7 7
O2 K1 O2 180.0 . 7
O5 K1 O3 97.15(11) 7 .
O5 K1 O3 82.85(11) . .
O5' K1 O3 97.90(10) 7 .
O5' K1 O3 82.10(10) . .
O1 K1 O3 118.99(6) . .
O1 K1 O3 61.01(6) 7 .
O2 K1 O3 60.18(6) . .
O2 K1 O3 119.82(6) 7 .
O5 K1 O3 82.85(11) 7 7
O5 K1 O3 97.15(11) . 7
O5' K1 O3 82.10(10) 7 7
O5' K1 O3 97.90(10) . 7
O1 K1 O3 61.01(6) . 7
O1 K1 O3 118.99(6) 7 7
O2 K1 O3 119.82(6) . 7
O2 K1 O3 60.18(6) 7 7
O3 K1 O3 180.00(2) . 7
C8 O5 K1 137.7(4) . .
C8 O5' K1 135.7(3) . .
C8 O4 H4C 111.6 . .
C1 O1 C2 113.4(3) . .
C1 O1 K1 113.42(18) . .
C2 O1 K1 114.6(2) . .
C4 O2 C3 113.0(3) . .
C4 O2 K1 114.67(18) . .
C3 O2 K1 114.1(2) . .
C6 O3 C5 112.3(2) . .
C6 O3 K1 110.87(18) . .
C5 O3 K1 111.95(18) . .
O1 C1 C6 109.4(3) . 7
O1 C1 H1A 109.8 . .
C6 C1 H1A 109.8 7 .
O1 C1 H1B 109.8 . .
C6 C1 H1B 109.8 7 .
H1A C1 H1B 108.2 . .
O1 C2 C3 110.2(3) . .
O1 C2 H2A 109.6 . .
C3 C2 H2A 109.6 . .
O1 C2 H2B 109.6 . .
C3 C2 H2B 109.6 . .
H2A C2 H2B 108.1 . .
O2 C3 C2 109.5(3) . .
O2 C3 H3A 109.8 . .
C2 C3 H3A 109.8 . .
O2 C3 H3B 109.8 . .
C2 C3 H3B 109.8 . .
H3A C3 H3B 108.2 . .
O2 C4 C5 109.1(3) . .
O2 C4 H4A 109.9 . .
C5 C4 H4A 109.9 . .
O2 C4 H4B 109.9 . .
C5 C4 H4B 109.9 . .
H4A C4 H4B 108.3 . .
O3 C5 C4 109.2(2) . .
O3 C5 H5A 109.8 . .
C4 C5 H5A 109.8 . .
O3 C5 H5B 109.8 . .
C4 C5 H5B 109.8 . .
H5A C5 H5B 108.3 . .
O3 C6 C1 109.1(2) . 7
O3 C6 H6A 109.9 . .
C1 C6 H6A 109.9 7 .
O3 C6 H6B 109.9 . .
C1 C6 H6B 109.9 7 .
H6A C6 H6B 108.3 . .
C8 C7 Cl1A 111.77(17) . .
C8 C7 Cl2A 110.91(16) . .
Cl1A C7 Cl2A 112.2(2) . .
C8 C7 Cl2B 105.70(19) . .
Cl1A C7 Cl2B 129.9(2) . .
Cl2A C7 Cl2B 19.73(9) . .
C8 C7 Cl1C 107.20(18) . .
Cl1A C7 Cl1C 19.57(17) . .
Cl2A C7 Cl1C 129.47(18) . .
Cl2B C7 Cl1C 144.41(19) . .
C8 C7 Cl2C 114.0(2) . .
Cl1A C7 Cl2C 94.6(2) . .
Cl2A C7 Cl2C 18.81(10) . .
Cl2B C7 Cl2C 38.54(7) . .
Cl1C C7 Cl2C 113.16(18) . .
C8 C7 Cl1B 110.34(19) . .
Cl1A C7 Cl1B 18.96(17) . .
Cl2A C7 Cl1B 96.48(16) . .
Cl2B C7 Cl1B 115.69(17) . .
Cl1C C7 Cl1B 38.36(7) . .
Cl2C C7 Cl1B 78.04(13) . .
C8 C7 H15A 107.2 . .
Cl1A C7 H15A 107.2 . .
Cl2A C7 H15A 107.2 . .
Cl2B C7 H15A 91.6 . .
Cl1C C7 H15A 91.4 . .
Cl2C C7 H15A 121.1 . .
Cl1B C7 H15A 123.9 . .
O4 C8 O5 120.0(3) . .
O4 C8 O5' 121.4(3) . .
O5 C8 O5' 55.3(3) . .
O4 C8 C7 118.3(2) . .
O5 C8 C7 113.0(3) . .
O5' C8 C7 113.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
K1 O5 2.625(5) 7
K1 O5 2.625(5) .
K1 O5' 2.638(4) 7
K1 O5' 2.638(4) .
K1 O1 2.801(2) .
K1 O1 2.801(2) 7
K1 O2 2.828(2) .
K1 O2 2.828(2) 7
K1 O3 2.8498(19) .
K1 O3 2.8498(19) 7
Cl1A C7 1.742(3) .
Cl2A C7 1.762(3) .
O5 C8 1.255(5) .
O5' C8 1.266(5) .
O4 C8 1.226(3) .
O4 H4C 1.2537 .
O1 C1 1.420(4) .
O1 C2 1.431(4) .
O2 C4 1.404(4) .
O2 C3 1.431(4) .
O3 C6 1.422(4) .
O3 C5 1.429(4) .
C1 C6 1.484(5) 7
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.478(6) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.488(5) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C1 1.484(5) 7
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.532(3) .
C7 Cl2B 1.807(3) .
C7 Cl1C 1.819(3) .
C7 Cl2C 1.840(3) .
C7 Cl1B 1.888(3) .
C7 H15A 1.0000 .
