#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/03/4500321.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_4500321
loop_
_publ_author_name
'Tominaga, Masahide'
'Masu, Hyuma'
'Azumaya, Isao'
_publ_section_title
;
 Hydrogen-Bonding Networks of Adamantane-Based Bisphenol Molecules: Toward
 the Preparation of Molecular Crystals with Channels
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              542
_journal_paper_doi               10.1021/cg101427k
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C22 H24 O2, 0.5(C H Cl3)'
_chemical_formula_sum            'C22.5 H24.5 Cl1.5 O2'
_chemical_formula_weight         380.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.671(2)
_cell_angle_beta                 90.941(2)
_cell_angle_gamma                99.691(2)
_cell_formula_units_Z            2
_cell_length_a                   6.354(1)
_cell_length_b                   12.695(2)
_cell_length_c                   13.196(3)
_cell_measurement_reflns_used    2157
_cell_measurement_temperature    120
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     923.8(3)
_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 0.968
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4621
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.23
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_correction_T_min  0.8916
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.824
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.824
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0461
_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)+(0.0415P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                3145
_reflns_number_total             3539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101427k_si_004.cif
_cod_data_source_block           a1010031tom
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      'P-1   '
_cod_original_formula_sum        'C22.50 H24.50 Cl1.50 O2'
_cod_database_code               4500321
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.6724(3) -0.29723(14) 0.07604(13) 0.0202(4) Uani 1 1 d .
C2 C 0.8422(3) -0.22401(15) 0.06183(15) 0.0284(4) Uani 1 1 d .
H2 H 0.9621 -0.2562 0.0268 0.034 Uiso 1 1 calc R
C3 C 0.8372(3) -0.10277(15) 0.09894(14) 0.0251(4) Uani 1 1 d .
H3 H 0.9552 -0.0531 0.0887 0.030 Uiso 1 1 calc R
C4 C 0.6656(3) -0.05177(14) 0.15051(13) 0.0172(3) Uani 1 1 d .
C5 C 0.4959(3) -0.12905(16) 0.16106(16) 0.0296(4) Uani 1 1 d .
H5 H 0.3742 -0.0977 0.1945 0.035 Uiso 1 1 calc R
C6 C 0.4974(3) -0.25033(16) 0.12458(16) 0.0286(4) Uani 1 1 d .
H6 H 0.3783 -0.3008 0.1330 0.034 Uiso 1 1 calc R
C7 C 0.9049(3) 0.42464(14) 0.76127(13) 0.0196(4) Uani 1 1 d .
C8 C 1.0366(3) 0.36203(14) 0.68169(13) 0.0208(4) Uani 1 1 d .
H8 H 1.1678 0.3505 0.7067 0.025 Uiso 1 1 calc R
C9 C 0.9762(3) 0.31614(14) 0.56531(13) 0.0200(4) Uani 1 1 d .
H9 H 1.0678 0.2732 0.5114 0.024 Uiso 1 1 calc R
C10 C 0.7841(3) 0.33104(13) 0.52460(13) 0.0175(3) Uani 1 1 d .
C11 C 0.6544(3) 0.39348(14) 0.60708(13) 0.0203(4) Uani 1 1 d .
H11 H 0.5218 0.4042 0.5826 0.024 Uiso 1 1 calc R
C12 C 0.7132(3) 0.44064(15) 0.72419(14) 0.0222(4) Uani 1 1 d .
H12 H 0.6223 0.4837 0.7786 0.027 Uiso 1 1 calc R
C13 C 0.6688(2) 0.08417(14) 0.20184(13) 0.0168(3) Uani 1 1 d .
C14 C 0.7188(3) 0.14172(13) 0.33362(13) 0.0170(3) Uani 1 1 d .
H14A H 0.6075 0.1024 0.3636 0.020 Uiso 1 1 calc R
H14B H 0.8588 0.1261 0.3513 0.020 Uiso 1 1 calc R
C15 C 0.7269(3) 0.27979(14) 0.39539(13) 0.0171(3) Uani 1 1 d .
C16 C 0.5084(3) 0.30115(14) 0.36565(13) 0.0185(4) Uani 1 1 d .
H16A H 0.3942 0.2625 0.3948 0.022 Uiso 1 1 calc R
H16B H 0.5098 0.3893 0.4037 0.022 Uiso 1 1 calc R
C17 C 0.4601(3) 0.24807(14) 0.23517(14) 0.0198(4) Uani 1 1 d .
H17 H 0.3177 0.2634 0.2181 0.024 Uiso 1 1 calc R
C18 C 0.4513(3) 0.11073(14) 0.17639(13) 0.0188(4) Uani 1 1 d .
H18A H 0.4174 0.0762 0.0922 0.023 Uiso 1 1 calc R
H18B H 0.3362 0.0718 0.2048 0.023 Uiso 1 1 calc R
C19 C 0.8429(3) 0.14793(14) 0.15805(13) 0.0183(3) Uani 1 1 d .
H19A H 0.9845 0.1328 0.1740 0.022 Uiso 1 1 calc R
H19B H 0.8126 0.1137 0.0737 0.022 Uiso 1 1 calc R
C20 C 0.9006(3) 0.33945(14) 0.34656(13) 0.0191(4) Uani 1 1 d .
H20A H 0.9056 0.4280 0.3836 0.023 Uiso 1 1 calc R
H20B H 1.0431 0.3264 0.3641 0.023 Uiso 1 1 calc R
C21 C 0.6335(3) 0.30858(15) 0.18939(14) 0.0218(4) Uani 1 1 d .
H21A H 0.6374 0.3970 0.2263 0.026 Uiso 1 1 calc R
H21B H 0.6013 0.2748 0.1052 0.026 Uiso 1 1 calc R
C22 C 0.8504(3) 0.28496(14) 0.21635(13) 0.0190(4) Uani 1 1 d .
H22 H 0.9649 0.3238 0.1863 0.023 Uiso 1 1 calc R
C23 C 0.1278(7) -0.0173(4) 0.4955(4) 0.0346(10) Uani 0.50 1 d P
Cl1 Cl 0.06347(19) -0.05916(10) 0.34888(10) 0.0414(3) Uani 0.50 1 d P
Cl2 Cl 0.33452(18) 0.11268(9) 0.55936(9) 0.0446(3) Uani 0.50 1 d P
Cl3 Cl -0.1044(2) 0.00760(12) 0.56681(14) 0.0505(3) Uani 0.50 1 d P
H23 H 0.187(7) -0.075(4) 0.505(3) 0.041(12) Uiso 0.50 1 d P
H1A H 0.562(7) -0.463(3) 0.022(3) 0.029(12) Uiso 0.50 1 d P
H2A H 0.847(7) 0.511(4) 0.917(3) 0.034(10) Uiso 0.50 1 d P
H1B H 0.781(8) -0.435(4) 0.036(4) 0.032(14) Uiso 0.50 1 d P
H2B H 1.067(8) 0.445(4) 0.891(4) 0.041(13) Uiso 0.50 1 d P
O1 O 0.6780(3) -0.41768(12) 0.04113(12) 0.0321(3) Uani 1 1 d .
O2 O 0.9645(2) 0.47189(12) 0.87703(10) 0.0261(3) 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'
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
C2 C1 C6 119.75(15) . .
C2 C1 O1 119.94(16) . .
C6 C1 O1 120.30(16) . .
C1 C2 C3 119.62(16) . .
C1 C2 H2 120.2 . .
C3 C2 H2 120.2 . .
C4 C3 C2 122.20(16) . .
C4 C3 H3 118.9 . .
C2 C3 H3 118.9 . .
C5 C4 C3 116.43(15) . .
C5 C4 C13 121.09(14) . .
C3 C4 C13 122.30(14) . .
C6 C5 C4 122.33(16) . .
C6 C5 H5 118.8 . .
C4 C5 H5 118.8 . .
C1 C6 C5 119.63(16) . .
C1 C6 H6 120.2 . .
C5 C6 H6 120.2 . .
O2 C7 C8 120.20(15) . .
O2 C7 C12 119.92(15) . .
C8 C7 C12 119.88(14) . .
C7 C8 C9 119.68(15) . .
C7 C8 H8 120.2 . .
C9 C8 H8 120.2 . .
C8 C9 C10 122.09(15) . .
C8 C9 H9 119.0 . .
C10 C9 H9 119.0 . .
C11 C10 C9 116.70(14) . .
C11 C10 C15 123.47(14) . .
C9 C10 C15 119.83(14) . .
C12 C11 C10 121.93(15) . .
C12 C11 H11 119.0 . .
C10 C11 H11 119.0 . .
C7 C12 C11 119.72(15) . .
C7 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C4 C13 C19 112.49(13) . .
C4 C13 C14 107.82(11) . .
C19 C13 C14 107.84(12) . .
C4 C13 C18 112.54(12) . .
C19 C13 C18 107.81(12) . .
C14 C13 C18 108.15(12) . .
C15 C14 C13 112.63(12) . .
C15 C14 H14A 109.1 . .
C13 C14 H14A 109.1 . .
C15 C14 H14B 109.1 . .
C13 C14 H14B 109.1 . .
H14A C14 H14B 107.8 . .
C10 C15 C16 112.99(13) . .
C10 C15 C14 109.73(12) . .
C16 C15 C14 107.86(12) . .
C10 C15 C20 109.86(12) . .
C16 C15 C20 107.98(12) . .
C14 C15 C20 108.29(13) . .
C17 C16 C15 110.61(13) . .
C17 C16 H16A 109.5 . .
C15 C16 H16A 109.5 . .
C17 C16 H16B 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 108.1 . .
C21 C17 C16 110.01(12) . .
C21 C17 C18 109.95(13) . .
C16 C17 C18 109.60(12) . .
C21 C17 H17 109.1 . .
C16 C17 H17 109.1 . .
C18 C17 H17 109.1 . .
C17 C18 C13 110.28(12) . .
C17 C18 H18A 109.6 . .
C13 C18 H18A 109.6 . .
C17 C18 H18B 109.6 . .
C13 C18 H18B 109.6 . .
H18A C18 H18B 108.1 . .
C22 C19 C13 111.14(13) . .
C22 C19 H19A 109.4 . .
C13 C19 H19A 109.4 . .
C22 C19 H19B 109.4 . .
C13 C19 H19B 109.4 . .
H19A C19 H19B 108.0 . .
C22 C20 C15 110.40(12) . .
C22 C20 H20A 109.6 . .
C15 C20 H20A 109.6 . .
C22 C20 H20B 109.6 . .
C15 C20 H20B 109.6 . .
H20A C20 H20B 108.1 . .
C17 C21 C22 108.64(12) . .
C17 C21 H21A 110.0 . .
C22 C21 H21A 110.0 . .
C17 C21 H21B 110.0 . .
C22 C21 H21B 110.0 . .
H21A C21 H21B 108.3 . .
C20 C22 C21 109.57(13) . .
C20 C22 C19 109.99(12) . .
C21 C22 C19 109.47(12) . .
C20 C22 H22 109.3 . .
C21 C22 H22 109.3 . .
C19 C22 H22 109.3 . .
Cl3 C23 C23 75.9(4) 2_556 2_556
Cl3 C23 Cl3 105.7(4) 2_556 .
C23 C23 Cl3 29.76(17) 2_556 .
Cl3 C23 Cl2 92.5(3) 2_556 .
C23 C23 Cl2 113.0(4) 2_556 .
Cl3 C23 Cl2 111.4(2) . .
Cl3 C23 Cl1 21.91(18) 2_556 .
C23 C23 Cl1 81.5(3) 2_556 .
Cl3 C23 Cl1 109.1(3) . .
Cl2 C23 Cl1 110.2(2) . .
Cl3 C23 H23 131(3) 2_556 .
C23 C23 H23 134(3) 2_556 .
Cl3 C23 H23 111(3) . .
Cl2 C23 H23 103(3) . .
Cl1 C23 H23 112(2) . .
Cl3 Cl1 C23 19.71(15) 2_556 .
C23 Cl2 Cl3 26.53(14) . 2_556
C23 Cl3 Cl1 138.4(3) 2_556 2_556
C23 Cl3 C23 74.3(4) 2_556 .
Cl1 Cl3 C23 109.8(2) 2_556 .
C23 Cl3 Cl2 60.9(3) 2_556 2_556
Cl1 Cl3 Cl2 146.78(12) 2_556 2_556
C23 Cl3 Cl2 101.44(18) . 2_556
C23 Cl3 Cl3 50.9(3) 2_556 2_556
Cl1 Cl3 Cl3 125.54(15) 2_556 2_556
C23 Cl3 Cl3 23.40(14) . 2_556
Cl2 Cl3 Cl3 87.68(11) 2_556 2_556
C1 O1 H1A 115(3) . .
C1 O1 H1B 118(4) . .
H1A O1 H1B 127(5) . .
C7 O2 H2A 106(2) . .
C7 O2 H2B 113(3) . .
H2A O2 H2B 138(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.376(2) .
C1 C6 1.376(2) .
C1 O1 1.384(2) .
C2 C3 1.388(2) .
C2 H2 0.9500 .
C3 C4 1.387(2) .
C3 H3 0.9500 .
C4 C5 1.386(2) .
C4 C13 1.530(2) .
C5 C6 1.385(2) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 O2 1.3747(19) .
C7 C8 1.383(2) .
C7 C12 1.386(2) .
C8 C9 1.385(2) .
C8 H8 0.9500 .
C9 C10 1.401(2) .
C9 H9 0.9500 .
C10 C11 1.393(2) .
C10 C15 1.527(2) .
C11 C12 1.390(2) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C19 1.538(2) .
C13 C14 1.544(2) .
C13 C18 1.544(2) .
C14 C15 1.543(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.537(2) .
C15 C20 1.550(2) .
C16 C17 1.532(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C21 1.529(2) .
C17 C18 1.534(2) .
C17 H17 1.0000 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C22 1.532(2) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C22 1.529(2) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.529(2) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22 1.0000 .
C23 Cl3 0.900(4) 2_556
C23 C23 1.745(9) 2_556
C23 Cl3 1.758(4) .
C23 Cl2 1.761(5) .
C23 Cl1 1.772(4) .
C23 H23 0.93(4) .
Cl1 Cl3 0.9953(16) 2_556
Cl2 Cl3 2.0122(19) 2_556
Cl3 C23 0.900(4) 2_556
Cl3 Cl1 0.9953(16) 2_556
Cl3 Cl2 2.0122(19) 2_556
Cl3 Cl3 2.180(3) 2_556
O1 H1A 0.81(4) .
O1 H1B 0.72(5) .
O2 H2A 0.99(4) .
O2 H2B 0.84(5) .
