#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:27:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180394 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/63/7206399.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_7206399
loop_
_publ_author_name
'Tominaga, Masahide'
'Masu, Hyuma'
'Azumaya, Isao'
_publ_section_title
;
 Pseudopolymorphism of an adamantane-based bisphenol containing water
 molecules: a role of clathrate hydrates in hydrogen-bonded networks
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              5299
_journal_paper_doi               10.1039/c1ce05253e
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C22 H22 Cl2 O2, 3(H2 O)'
_chemical_formula_sum            'C22 H28 Cl2 O5'
_chemical_formula_weight         443.34
_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                 114.943(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.283(3)
_cell_length_b                   20.730(4)
_cell_length_c                   7.3864(13)
_cell_measurement_reflns_used    1882
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.76
_cell_volume                     2260.7(7)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5331
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9110
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            coloueless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0590
_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)+(0.1253P)²+0.3428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2060
_reflns_number_gt                1588
_reflns_number_total             2263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05253e.txt
_cod_data_source_block           a1007162mas
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C2/c '
_cod_database_code               7206399
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
C1 C 0.18959(17) 0.41836(16) 0.2455(4) 0.0374(7) Uani 1 1 d . . .
C2 C 0.23114(18) 0.37942(17) 0.1584(4) 0.0454(9) Uani 1 1 d . . .
C3 C 0.30537(18) 0.34114(19) 0.2715(4) 0.0461(8) Uani 1 1 d . . .
H3 H 0.3321 0.3143 0.2068 0.055 Uiso 1 1 calc R . .
C4 C 0.34054(17) 0.34204(16) 0.4783(4) 0.0392(7) Uani 1 1 d . . .
C5 C 0.29940(17) 0.38251(15) 0.5654(4) 0.0375(7) Uani 1 1 d . . .
H5 H 0.3232 0.3847 0.7068 0.045 Uiso 1 1 calc R . .
C6 C 0.22462(17) 0.41983(15) 0.4519(4) 0.0373(7) Uani 1 1 d . . .
H6 H 0.1974 0.4465 0.5159 0.045 Uiso 1 1 calc R . .
C7 C 0.41956(17) 0.29884(17) 0.6097(4) 0.0424(8) Uani 1 1 d . . .
C8 C 0.45403(19) 0.25581(18) 0.4865(5) 0.0477(9) Uani 1 1 d . . .
H8A H 0.4038 0.2286 0.3946 0.057 Uiso 1 1 calc R . .
H8B H 0.4752 0.2833 0.4051 0.057 Uiso 1 1 calc R . .
C9 C 0.53201(19) 0.21255(18) 0.6238(5) 0.0504(9) Uani 1 1 d . . .
H9 H 0.5527 0.1847 0.5405 0.061 Uiso 1 1 calc R . .
C10 C 0.5000 0.1698(3) 0.7500 0.0558(13) Uani 1 2 d S . .
H10A H 0.5503 0.1418 0.8380 0.067 Uiso 0.50 1 calc PR . .
H10B H 0.4497 0.1418 0.6620 0.067 Uiso 0.50 1 calc PR . .
C11 C 0.5000 0.3416(2) 0.7500 0.0408(10) Uani 1 2 d S . .
H11A H 0.5205 0.3696 0.6686 0.049 Uiso 0.50 1 calc PR . .
H11B H 0.4795 0.3696 0.8314 0.049 Uiso 0.50 1 calc PR . .
C12 C 0.38921(18) 0.25463(18) 0.7392(5) 0.0465(8) Uani 1 1 d . . .
H12A H 0.3673 0.2814 0.8208 0.056 Uiso 1 1 calc R . .
H12B H 0.3386 0.2268 0.6516 0.056 Uiso 1 1 calc R . .
Cl1 Cl 0.18857(5) 0.37694(5) -0.10192(10) 0.0632(4) Uani 1 1 d . . .
O1 O 0.11532(12) 0.45385(11) 0.1277(3) 0.0423(6) Uani 1 1 d . . .
H1 H 0.0970 0.4751 0.2002 0.063 Uiso 1 1 calc R . .
O2 O 0.0000 0.48431(16) 0.7500 0.0434(8) Uani 1 2 d S . .
O3 O 0.5694(9) 0.4782(6) 0.160(3) 0.208(11) Uani 0.456(18) 1 d PU A -1
O4 O 0.4412(11) 0.4735(4) 0.086(3) 0.243(11) Uani 0.544(18) 1 d PU A -2
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'
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
O1 C1 C2 119.7(2) . .
O1 C1 C6 122.1(3) . .
C2 C1 C6 118.2(3) . .
C1 C2 C3 121.9(3) . .
C1 C2 Cl1 119.1(2) . .
C3 C2 Cl1 119.0(2) . .
C4 C3 C2 120.3(3) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C3 C4 C5 117.5(3) . .
C3 C4 C7 122.4(3) . .
C5 C4 C7 120.0(2) . .
C6 C5 C4 122.0(3) . .
C6 C5 H5 119.0 . .
C4 C5 H5 119.0 . .
C1 C6 C5 120.2(3) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C4 C7 C8 112.5(2) . .
C4 C7 C12 109.6(2) . .
C8 C7 C12 108.3(3) . .
C4 C7 C11 109.6(3) . .
C8 C7 C11 108.0(2) . .
C12 C7 C11 108.8(2) . .
C9 C8 C7 110.7(3) . .
C9 C8 H8A 109.5 . .
C7 C8 H8A 109.5 . .
C9 C8 H8B 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
C10 C9 C12 109.5(2) . 2_656
C10 C9 C8 110.0(2) . .
C12 C9 C8 109.5(3) 2_656 .
C10 C9 H9 109.3 . .
C12 C9 H9 109.3 2_656 .
C8 C9 H9 109.3 . .
C9 C10 C9 109.1(4) . 2_656
C9 C10 H10A 109.9 . .
C9 C10 H10A 109.9 2_656 .
C9 C10 H10B 109.9 . .
C9 C10 H10B 109.9 2_656 .
H10A C10 H10B 108.3 . .
C7 C11 C7 110.8(4) 2_656 .
C7 C11 H11A 109.5 2_656 .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 2_656 .
C7 C11 H11B 109.5 . .
H11A C11 H11B 108.1 . .
C9 C12 C7 110.4(2) 2_656 .
C9 C12 H12A 109.6 2_656 .
C7 C12 H12A 109.6 . .
C9 C12 H12B 109.6 2_656 .
C7 C12 H12B 109.6 . .
H12A C12 H12B 108.1 . .
C1 O1 H1 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.369(3) .
C1 C2 1.375(4) .
C1 C6 1.385(4) .
C2 C3 1.392(4) .
C2 Cl1 1.748(3) .
C3 C4 1.387(4) .
C3 H3 0.9500 .
C4 C5 1.389(4) .
C4 C7 1.532(4) .
C5 C6 1.387(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.539(4) .
C7 C12 1.549(4) .
C7 C11 1.558(4) .
C8 C9 1.536(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.528(5) .
C9 C12 1.528(4) 2_656
C9 H9 1.0000 .
C10 C9 1.528(5) 2_656
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C7 1.558(4) 2_656
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C9 1.528(4) 2_656
C12 H12A 0.9900 .
C12 H12B 0.9900 .
O1 H1 0.8400 .
