#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/10/10/1101055.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_1101055
loop_
_publ_author_name
'Yamamura, Kimiaki'
'Kawashima Taiga'
'Eda, Kazuo'
'Tajima, Fukue'
'Hashimoto, Masao'
_publ_section_title
;
 Solid solution of triptycenequinone and triptycenehydroquinone as
 a non-stoichiometric quinhydrone. Bathochromic changes in color
 caused by local intermolecular interaction between p-benzoquinone
 and hydroquinone moieties
;
_journal_issue                   1
_journal_name_full               'Journal of Molecular Structure'
_journal_page_first              1
_journal_page_last               6
_journal_paper_doi               10.1016/j.molstruc.2004.10.002
_journal_volume                  737
_journal_year                    2005
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.33
_chemical_melting_point          'ca.600 K with decomposition'
_chemical_name_common            'triptycenehydroquinone (TPHQ)'
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            24
_cell_length_a                   27.864(3)
_cell_length_b                   27.864(3)
_cell_length_c                   12.9830(17)
_cell_measurement_temperature    293(2)
_cell_volume                     8729.7(16)
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0982
_diffrn_reflns_av_sigmaI/netI    0.1077
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            49798
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         0.84
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      1.32
_exptl_crystal_density_method    floating
_exptl_crystal_description       prism
_exptl_crystal_F_000             3600
_exptl_crystal_preparation       acetonitrile
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     761
_refine_ls_number_reflns         12100
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.2565
_refine_ls_R_factor_gt           0.1194
_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)+(0.0797P)²+25.3957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2649
_refine_ls_wR_factor_ref         0.3423
_reflns_number_gt                4971
_reflns_number_total             12100
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P6(3)
_cod_database_code               1101055
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, 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
C101 C 0.4408(4) 0.8898(4) 0.6797(8) 0.049(2) Uani 1 1 d . . .
C102 C 0.4911(4) 0.9132(4) 0.6284(9) 0.052(2) Uani 1 1 d . . .
H102 H 0.5242 0.9293 0.6654 0.062 Uiso 1 1 calc R . .
C103 C 0.4920(4) 0.9123(4) 0.5244(8) 0.051(3) Uani 1 1 d . . .
H103 H 0.5257 0.9276 0.4899 0.061 Uiso 1 1 calc R . .
C104 C 0.4440(4) 0.8895(4) 0.4697(7) 0.042(2) Uiso 1 1 d . . .
C105 C 0.2827(5) 0.7281(5) 0.4573(14) 0.093(5) Uani 1 1 d . . .
H105 H 0.2860 0.7266 0.3863 0.112 Uiso 1 1 calc R . .
C106 C 0.2538(6) 0.6798(6) 0.523(2) 0.126(8) Uani 1 1 d . . .
H106 H 0.2294 0.6463 0.4911 0.151 Uiso 1 1 calc R . .
C107 C 0.2590(7) 0.6794(8) 0.6149(17) 0.129(10) Uani 1 1 d . . .
H107 H 0.2487 0.6457 0.6466 0.155 Uiso 1 1 calc R . .
C108 C 0.2808(4) 0.7300(4) 0.6811(16) 0.103(7) Uani 1 1 d . . .
H108 H 0.2773 0.7301 0.7524 0.123 Uiso 1 1 calc R . .
C109 C 0.3338(4) 0.8357(4) 0.6684(9) 0.051(3) Uani 1 1 d . . .
H109 H 0.3321 0.8351 0.7438 0.061 Uiso 1 1 calc R . .
C110 C 0.3356(4) 0.8348(4) 0.4684(9) 0.051(2) Uani 1 1 d . . .
H110 H 0.3367 0.8347 0.3930 0.062 Uiso 1 1 calc R . .
C111 C 0.3926(4) 0.8643(4) 0.6258(9) 0.040(2) Uani 1 1 d . . .
C112 C 0.3925(4) 0.8640(4) 0.5186(8) 0.043(2) Uani 1 1 d . . .
C113 C 0.2783(3) 0.8884(4) 0.6741(9) 0.056(3) Uani 1 1 d . . .
H113 H 0.2779 0.8907 0.7456 0.067 Uiso 1 1 calc R . .
C114 C 0.2518(6) 0.9100(6) 0.6046(14) 0.102(8) Uani 1 1 d . . .
H114 H 0.2305 0.9233 0.6354 0.122 Uiso 1 1 calc R . .
C115 C 0.2547(5) 0.9123(6) 0.5121(12) 0.071(3) Uani 1 1 d . . .
H115 H 0.2406 0.9313 0.4759 0.085 Uiso 1 1 calc R . .
C116 C 0.2795(4) 0.8864(5) 0.4582(10) 0.064(3) Uani 1 1 d . . .
H116 H 0.2782 0.8848 0.3867 0.077 Uiso 1 1 calc R . .
C117 C 0.3053(4) 0.7782(4) 0.5151(11) 0.063(3) Uani 1 1 d . . .
C118 C 0.3074(4) 0.7768(4) 0.6185(12) 0.070(4) Uani 1 1 d . . .
C119 C 0.3057(4) 0.8635(4) 0.5128(9) 0.051(3) Uani 1 1 d . . .
C120 C 0.3051(5) 0.8633(5) 0.6189(12) 0.069(4) Uani 1 1 d . . .
C201 C 0.4448(4) 0.0590(4) 0.6815(9) 0.049(3) Uani 1 1 d . . .
C202 C 0.4200(4) 0.0086(4) 0.6294(9) 0.051(3) Uani 1 1 d . . .
H202 H 0.4023 -0.0246 0.6659 0.061 Uiso 1 1 calc R . .
C203 C 0.4218(4) 0.0081(3) 0.5258(8) 0.048(3) Uani 1 1 d . . .
H203 H 0.4047 -0.0256 0.4911 0.058 Uiso 1 1 calc R . .
C204 C 0.4482(4) 0.0560(4) 0.4709(8) 0.042(2) Uani 1 1 d . . .
C205 C 0.4463(4) 0.2173(4) 0.4537(11) 0.071(3) Uani 1 1 d . . .
H205 H 0.4452 0.2154 0.3822 0.085 Uiso 1 1 calc R . .
C206 C 0.4228(5) 0.2445(5) 0.5125(14) 0.078(4) Uani 1 1 d . . .
H206 H 0.4087 0.2637 0.4768 0.094 Uiso 1 1 calc R . .
C207 C 0.4202(6) 0.2437(6) 0.6108(13) 0.087(6) Uani 1 1 d . . .
H207 H 0.4012 0.2590 0.6431 0.104 Uiso 1 1 calc R . .
C208 C 0.4454(4) 0.2202(4) 0.6729(11) 0.070(4) Uani 1 1 d . . .
H208 H 0.4456 0.2222 0.7444 0.084 Uiso 1 1 calc R . .
C209 C 0.4989(4) 0.1662(4) 0.6686(9) 0.051(3) Uani 1 1 d . . .
H209 H 0.4993 0.1679 0.7440 0.062 Uiso 1 1 calc R . .
C210 C 0.5004(4) 0.1641(4) 0.4710(9) 0.061(3) Uani 1 1 d . . .
H210 H 0.5005 0.1632 0.3955 0.073 Uiso 1 1 calc R . .
C211 C 0.4703(4) 0.1075(4) 0.6279(9) 0.039(2) Uani 1 1 d . . .
C212 C 0.4721(4) 0.1069(4) 0.5197(8) 0.048(3) Uani 1 1 d . . .
C213 C 0.6066(4) 0.2209(4) 0.6851(14) 0.091(6) Uani 1 1 d . . .
H213 H 0.6073 0.2209 0.7567 0.109 Uiso 1 1 calc R . .
C214 C 0.6566(9) 0.2490(8) 0.616(2) 0.164(14) Uani 1 1 d . . .
H214 H 0.6903 0.2731 0.6470 0.197 Uiso 1 1 calc R . .
C215 C 0.6563(10) 0.2430(9) 0.5281(18) 0.115(8) Uani 1 1 d . . .
H215 H 0.6899 0.2542 0.4951 0.138 Uiso 1 1 calc R . .
C216 C 0.6067(6) 0.2192(6) 0.4667(14) 0.095(5) Uani 1 1 d . . .
H216 H 0.6084 0.2209 0.3952 0.113 Uiso 1 1 calc R . .
C217 C 0.4712(4) 0.1939(4) 0.5153(10) 0.051(3) Uani 1 1 d . . .
C218 C 0.4700(5) 0.1940(4) 0.6204(12) 0.069(4) Uani 1 1 d . . .
C219 C 0.5573(5) 0.1941(5) 0.5169(13) 0.075(4) Uani 1 1 d . . .
C220 C 0.5569(5) 0.1938(4) 0.6220(13) 0.077(5) Uani 1 1 d . . .
C301 C 0.3905(4) 0.9461(5) 0.1837(8) 0.054(3) Uiso 1 1 d . . .
C302 C 0.4130(4) 0.9206(4) 0.1277(9) 0.051(2) Uani 1 1 d . . .
H302 H 0.4295 0.9031 0.1615 0.061 Uiso 1 1 calc R . .
C303 C 0.4116(4) 0.9207(4) 0.0240(8) 0.050(3) Uani 1 1 d . . .
H303 H 0.4265 0.9025 -0.0127 0.060 Uiso 1 1 calc R . .
C304 C 0.3879(4) 0.9476(4) -0.0298(8) 0.045(3) Uani 1 1 d . . .
C305 C 0.2252(5) 0.9471(5) -0.0199(14) 0.083(4) Uani 1 1 d . . .
H305 H 0.2243 0.9468 -0.0916 0.100 Uiso 1 1 calc R . .
C306 C 0.1770(5) 0.9230(5) 0.0340(11) 0.070(3) Uani 1 1 d . . .
H306 H 0.1433 0.9082 -0.0007 0.084 Uiso 1 1 calc R . .
C307 C 0.1777(5) 0.9207(5) 0.1384(14) 0.081(4) Uani 1 1 d . . .
H307 H 0.1447 0.9019 0.1750 0.098 Uiso 1 1 calc R . .
C308 C 0.2286(5) 0.9467(4) 0.1905(11) 0.065(3) Uani 1 1 d . . .
H308 H 0.2292 0.9478 0.2621 0.078 Uiso 1 1 calc R . .
C309 C 0.3363(4) 1.0001(4) 0.1801(9) 0.055(3) Uani 1 1 d . . .
H309 H 0.3379 0.9999 0.2555 0.066 Uiso 1 1 calc R . .
C310 C 0.3326(5) 1.0007(4) -0.0169(8) 0.058(3) Uani 1 1 d . . .
H310 H 0.3316 1.0014 -0.0923 0.070 Uiso 1 1 calc R . .
C311 C 0.3643(3) 0.9712(3) 0.1286(8) 0.0363(19) Uani 1 1 d . . .
C312 C 0.3638(4) 0.9717(4) 0.0243(8) 0.054(3) Uani 1 1 d . . .
C313 C 0.3892(4) 1.1074(4) 0.1951(12) 0.073(4) Uani 1 1 d . . .
H313 H 0.3917 1.1070 0.2665 0.088 Uiso 1 1 calc R . .
C314 C 0.4098(6) 1.1562(5) 0.139(2) 0.158(11) Uani 1 1 d . . .
H314 H 0.4228 1.1895 0.1743 0.190 Uiso 1 1 calc R . .
C315 C 0.4117(6) 1.1571(6) 0.0309(12) 0.079(4) Uani 1 1 d . . .
H315 H 0.4303 1.1908 -0.0038 0.095 Uiso 1 1 calc R . .
C316 C 0.3860(5) 1.1080(5) -0.0241(10) 0.070(3) Uiso 1 1 d . . .
H316 H 0.3843 1.1077 -0.0957 0.084 Uiso 1 1 calc R . .
C317 C 0.2754(4) 0.9719(4) 0.0305(8) 0.047(3) Uani 1 1 d . . .
C318 C 0.2769(4) 0.9704(4) 0.1369(11) 0.055(3) Uani 1 1 d . . .
C319 C 0.3633(4) 1.0599(4) 0.0312(10) 0.058(3) Uani 1 1 d . . .
C320 C 0.3636(4) 1.0575(4) 0.1342(12) 0.063(3) Uani 1 1 d . . .
C401 C 0.1116(3) 0.0535(3) 0.7382(5) 0.0085(14) Uiso 1 1 d . . .
C402 C 0.0872(3) 0.0790(3) 0.6871(5) 0.0195(17) Uani 1 1 d . . .
H402 H 0.0703 0.0953 0.7235 0.023 Uiso 1 1 calc R . .
C403 C 0.0883(4) 0.0801(4) 0.5791(6) 0.030(2) Uani 1 1 d . . .
H403 H 0.0737 0.0987 0.5433 0.036 Uiso 1 1 calc R . .
C404 C 0.1113(3) 0.0531(3) 0.5253(6) 0.0168(17) Uiso 1 1 d . . .
C405 C 0.2721(5) 0.0532(5) 0.5203(8) 0.047(3) Uani 1 1 d . . .
H405 H 0.2717 0.0533 0.4487 0.057 Uiso 1 1 calc R . .
C406 C 0.3215(5) 0.0771(6) 0.5714(13) 0.079(4) Uani 1 1 d . . .
H406 H 0.3548 0.0924 0.5354 0.095 Uiso 1 1 calc R . .
C407 C 0.3210(5) 0.0783(5) 0.6836(12) 0.073(4) Uani 1 1 d . . .
H407 H 0.3541 0.0963 0.7201 0.088 Uiso 1 1 calc R . .
C408 C 0.2730(4) 0.0535(4) 0.7333(8) 0.044(3) Uani 1 1 d . . .
H408 H 0.2731 0.0528 0.8049 0.052 Uiso 1 1 calc R . .
C409 C 0.1649(3) -0.0010(3) 0.7312(6) 0.0230(17) Uiso 1 1 d . . .
H409 H 0.1654 -0.0008 0.8067 0.028 Uiso 1 1 calc R . .
C410 C 0.1647(3) -0.0002(3) 0.5305(5) 0.0214(17) Uani 1 1 d . . .
H410 H 0.1641 0.0001 0.4551 0.026 Uiso 1 1 calc R . .
C411 C 0.1353(3) 0.0284(3) 0.6855(5) 0.0153(16) Uani 1 1 d . . .
C412 C 0.1360(3) 0.0288(3) 0.5784(6) 0.0219(18) Uani 1 1 d . . .
C413 C 0.1118(4) -0.1078(4) 0.7392(8) 0.037(2) Uani 1 1 d . . .
H413 H 0.1097 -0.1077 0.8107 0.044 Uiso 1 1 calc R . .
C414 C 0.0903(5) -0.1563(4) 0.6870(10) 0.062(3) Uani 1 1 d . . .
H414 H 0.0771 -0.1894 0.7228 0.074 Uiso 1 1 calc R . .
C415 C 0.0876(5) -0.1567(4) 0.5706(10) 0.053(3) Uani 1 1 d . . .
H415 H 0.0694 -0.1896 0.5335 0.064 Uiso 1 1 calc R . .
C416 C 0.1124(5) -0.1080(4) 0.5245(8) 0.047(3) Uani 1 1 d . . .
H416 H 0.1139 -0.1074 0.4530 0.057 Uiso 1 1 calc R . .
C417 C 0.2227(4) 0.0288(4) 0.5736(7) 0.031(2) Uani 1 1 d . . .
C418 C 0.2239(3) 0.0293(3) 0.6833(7) 0.030(2) Uani 1 1 d . . .
C419 C 0.1357(3) -0.0589(4) 0.5751(7) 0.027(2) Uani 1 1 d . . .
C420 C 0.1365(3) -0.0592(3) 0.6856(6) 0.0216(18) Uani 1 1 d . . .
O101 O 0.4385(3) 0.8921(4) 0.7856(7) 0.072(3) Uani 1 1 d . . .
H10A H 0.4699 0.9061 0.8094 0.108 Uiso 1 1 calc R . .
O102 O 0.4429(3) 0.8893(3) 0.3610(5) 0.0584(19) Uani 1 1 d . . .
H10B H 0.4739 0.8985 0.3388 0.088 Uiso 1 1 calc R . .
O201 O 0.4466(3) 0.0608(3) 0.7883(7) 0.067(2) Uani 1 1 d . . .
H20A H 0.4245 0.0301 0.8114 0.100 Uiso 1 1 calc R . .
O202 O 0.4530(3) 0.0570(3) 0.3629(5) 0.0552(19) Uani 1 1 d . . .
H20B H 0.4327 0.0258 0.3400 0.083 Uiso 1 1 calc R . .
O301 O 0.3933(3) 0.9481(3) 0.2875(7) 0.066(2) Uani 1 1 d . . .
H30A H 0.4065 0.9293 0.3081 0.099 Uiso 1 1 calc R . .
O302 O 0.3888(3) 0.9506(3) -0.1366(5) 0.062(2) Uani 1 1 d . . .
H30B H 0.3961 0.9277 -0.1603 0.092 Uiso 1 1 calc R . .
O401 O 0.1093(2) 0.0506(2) 0.8459(4) 0.0238(13) Uiso 1 1 d . . .
H40A H 0.0815 0.0507 0.8661 0.036 Uiso 1 1 calc R . .
O402 O 0.1090(2) 0.0504(2) 0.4176(5) 0.0299(14) Uiso 1 1 d . . .
H40B H 0.0877 0.0605 0.3966 0.045 Uiso 1 1 calc R . .
