##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_journal_date_recd_electronic     2012-01-15
_journal_date_accepted     2012-03-26
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o179
_journal_page_last     o182
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270112013169
_journal_coeditor_code     KU3064
_publ_contact_author_name     'Bond, Marcus R.'
_publ_contact_author_address
;
Department of Chemistry
Southeast Missouri State University
Cape Girardeau
MO 63701
USA
;
_publ_contact_author_email     bond@mbond2.st.semo.edu
_publ_contact_author_fax     '573-986-6433'
_publ_contact_author_phone     '573-651-2580'
_publ_section_title
;
4,4'-(4,5-Dimethyl-1,2-phenylene)bis(2-methylbut-3-yn-2-ol): structural
variation in vicinal dialkynols
;
loop_
    _publ_author_name
    _publ_author_address
    'Marcus R. Bond'
;
Department of Chemistry
Southeast Missouri State University
Cape Girardeau
MO 63701
USA
;
    'Hathaway, Bruce A.'
;
Department of Chemistry and Physics
LeTourneau University
Longview
TX 75607-7001
USA
;
    'Uriah J. Kilgore'
;
Department of Chemistry
Southeast Missouri State University
Cape Girardeau
MO 63701
USA
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_chemical_name_systematic
;
4,4'-(4,5-Dimethyl-1,2-phenylene)bis(2-methylbut-3-yn-2-ol)
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C18 H22 O2'
_chemical_formula_sum     'C18 H22 O2'
_chemical_formula_iupac     'C18 H22 O2'
_chemical_formula_weight     270.37
_chemical_melting_point     414
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.47200(10)
_cell_length_b     22.7966(3)
_cell_length_c     16.8592(2)
_cell_angle_alpha     90
_cell_angle_beta     93.8860(10)
_cell_angle_gamma     90
_cell_volume     3248.58(7)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9685
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     30.034
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.106
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1168
_exptl_absorpt_coefficient_mu     0.07
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_device     '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method     'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     18231
_diffrn_reflns_av_R_equivalents     0.027
_diffrn_reflns_theta_min     3.3
_diffrn_reflns_theta_max     30.04
_diffrn_reflns_theta_full     30.04
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -31
_diffrn_reflns_limit_k_max     32
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_reflns_reduction_process
                                'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger.
;
_reflns_number_total     9466
_reflns_number_gt     7185
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0677
_refine_ls_R_factor_gt     0.0456
_refine_ls_wR_factor_gt     0.1102
_refine_ls_wR_factor_ref     0.1223
_refine_ls_goodness_of_fit_ref     1.012
_refine_ls_restrained_S_all     1.012
_refine_ls_number_reflns     9466
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0539P)²+1.0667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.332
_refine_diff_density_min     -0.241
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and ORTEPIII (Burnett & Johnson,
1996)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C01 0.12189(12) 0.54679(5) 0.13956(6) 0.0178(2) Uani d . 1 1 . .
    C C011 0.26338(13) 0.57407(5) 0.17362(7) 0.0207(2) Uani d . 1 1 . .
    C C012 0.38019(13) 0.59732(5) 0.20290(7) 0.0205(2) Uani d . 1 1 . .
    C C013 0.51886(13) 0.62516(5) 0.24553(6) 0.0191(2) Uani d . 1 1 . .
    C C014 0.64755(14) 0.57975(5) 0.26529(8) 0.0268(2) Uani d . 1 1 . .
    H H01A 0.7373 0.5985 0.2923 0.040 Uiso calc R 1 1 . .
    H H01B 0.6788 0.5621 0.2171 0.040 Uiso calc R 1 1 . .
    H H01C 0.6076 0.5500 0.2989 0.040 Uiso calc R 1 1 . .
    C C015 0.46812(15) 0.65488(6) 0.32068(7) 0.0296(3) Uani d . 1 1 . .
    H H01D 0.3904 0.6844 0.3066 0.044 Uiso calc R 1 1 . .
    H H01E 0.5584 0.6728 0.3484 0.044 Uiso calc R 1 1 . .
    H H01F 0.4236 0.6262 0.3544 0.044 Uiso calc R 1 1 . .
    O O01 0.58867(9) 0.66772(3) 0.19515(5) 0.02060(16) Uani d . 1 1 . .
    H H01 0.517(2) 0.6938(8) 0.1783(10) 0.045(5) Uiso d . 1 1 . .
    C C02 0.10278(12) 0.48552(4) 0.14195(6) 0.0173(2) Uani d . 1 1 . .
    C C021 0.22615(13) 0.44843(5) 0.17650(6) 0.0190(2) Uani d . 1 1 . .
    C C022 0.32716(13) 0.41642(5) 0.20475(7) 0.0197(2) Uani d . 1 1 . .
    C C023 0.45135(13) 0.37692(5) 0.23996(7) 0.0222(2) Uani d . 1 1 . .
    C C024 0.57684(18) 0.41224(6) 0.28769(11) 0.0476(4) Uani d . 1 1 . .
    H H02A 0.5283 0.4340 0.3283 0.071 Uiso calc R 1 1 . .
    H H02B 0.6265 0.4389 0.2530 0.071 Uiso calc R 1 1 . .
    H H02C 0.6550 0.3861 0.3118 0.071 Uiso calc R 1 1 . .
    C C025 0.52031(18) 0.34042(6) 0.17486(10) 0.0421(4) Uani d . 1 1 . .
    H H02D 0.5976 0.3137 0.1983 0.063 Uiso calc R 1 1 . .
    H H02E 0.5696 0.3659 0.1385 0.063 Uiso calc R 1 1 . .
    H H02F 0.4372 0.3187 0.1467 0.063 Uiso calc R 1 1 . .
    O O02 0.38340(9) 0.33821(3) 0.29603(5) 0.02102(17) Uani d . 1 1 . .
    H H02 0.323(2) 0.3122(9) 0.2692(11) 0.055(5) Uiso d . 1 1 . .
    C C03 -0.03836(13) 0.46092(5) 0.10931(6) 0.0192(2) Uani d . 1 1 . .
    H H03 -0.0513 0.4204 0.1110 0.023 Uiso calc R 1 1 . .
    C C04 -0.15985(12) 0.49517(5) 0.07439(6) 0.0188(2) Uani d . 1 1 . .
    C C041 -0.31044(13) 0.46667(5) 0.04079(7) 0.0262(2) Uani d . 1 1 . .
    H H04A -0.2979 0.4248 0.0415 0.039 Uiso calc R 1 1 . .
    H H04B -0.3333 0.4797 -0.0129 0.039 Uiso calc R 1 1 . .
    H H04C -0.3960 0.4774 0.0724 0.039 Uiso calc R 1 1 . .
    C C05 -0.14007(13) 0.55618(5) 0.07100(6) 0.0199(2) Uani d . 1 1 . .
    C C051 -0.26733(15) 0.59501(5) 0.03275(8) 0.0282(3) Uani d . 1 1 . .
    H H05A -0.2321 0.6350 0.0345 0.042 Uiso calc R 1 1 . .
    H H05B -0.3616 0.5914 0.0609 0.042 Uiso calc R 1 1 . .
    H H05C -0.2895 0.5833 -0.0216 0.042 Uiso calc R 1 1 . .
    C C06 -0.00020(13) 0.58079(5) 0.10354(7) 0.0209(2) Uani d . 1 1 . .
    H H06 0.0126 0.6213 0.1013 0.025 Uiso calc R 1 1 . .
    C C11 0.90438(12) 0.41337(5) 0.61033(7) 0.0189(2) Uani d . 1 1 . .
    C C111 0.95798(13) 0.35895(5) 0.64619(7) 0.0210(2) Uani d . 1 1 . .
    C C112 1.00338(13) 0.31420(5) 0.67745(7) 0.0225(2) Uani d . 1 1 . .
    C C113 1.05248(13) 0.25868(5) 0.71779(7) 0.0219(2) Uani d . 1 1 . .
    C C114 0.99869(18) 0.25759(6) 0.80203(9) 0.0363(3) Uani d . 1 1 . .
    H H11A 1.0478 0.2892 0.8321 0.054 Uiso calc R 1 1 . .
    H H11B 1.0285 0.2209 0.8268 0.054 Uiso calc R 1 1 . .
    H H11C 0.8858 0.2619 0.8004 0.054 Uiso calc R 1 1 . .
    C C115 0.98839(15) 0.20637(5) 0.66987(9) 0.0327(3) Uani d . 1 1 . .
    H H11D 1.0224 0.1707 0.6962 0.049 Uiso calc R 1 1 . .
    H H11E 1.0274 0.2075 0.6178 0.049 Uiso calc R 1 1 . .
    H H11F 0.8749 0.2079 0.6654 0.049 Uiso calc R 1 1 . .
    O O11 1.22185(9) 0.25272(3) 0.72007(5) 0.02400(18) Uani d . 1 1 . .
    H H11 1.268(2) 0.2828(8) 0.7459(11) 0.056(5) Uiso d . 1 1 . .
    C C12 0.79785(13) 0.41398(4) 0.54237(6) 0.0186(2) Uani d . 1 1 . .
    C C121 0.73837(13) 0.36031(5) 0.50684(7) 0.0208(2) Uani d . 1 1 . .
    C C122 0.68304(14) 0.31625(5) 0.47806(7) 0.0220(2) Uani d . 1 1 . .
    C C123 0.60726(14) 0.26113(5) 0.44850(7) 0.0220(2) Uani d . 1 1 . .
    C C124 0.70774(18) 0.20861(5) 0.47550(8) 0.0330(3) Uani d . 1 1 . .
    H H12A 0.8112 0.2124 0.4561 0.049 Uiso calc R 1 1 . .
    H H12B 0.6589 0.1733 0.4549 0.049 Uiso calc R 1 1 . .
    H H12C 0.7166 0.2070 0.5325 0.049 Uiso calc R 1 1 . .
    C C125 0.44035(17) 0.25707(6) 0.47704(8) 0.0316(3) Uani d . 1 1 . .
    H H12D 0.4456 0.2579 0.5341 0.047 Uiso calc R 1 1 . .
    H H12E 0.3919 0.2211 0.4584 0.047 Uiso calc R 1 1 . .
    H H12F 0.3786 0.2897 0.4566 0.047 Uiso calc R 1 1 . .
    O O12 0.59936(10) 0.25983(3) 0.36278(5) 0.02156(17) Uani d . 1 1 . .
    H H12 0.532(2) 0.2884(8) 0.3450(10) 0.048(5) Uiso d . 1 1 . .
    C C13 0.74574(14) 0.46813(5) 0.51116(7) 0.0216(2) Uani d . 1 1 . .
    H H13 0.6743 0.4686 0.4668 0.026 Uiso calc R 1 1 . .
    C C14 0.79717(14) 0.52118(5) 0.54430(7) 0.0208(2) Uani d . 1 1 . .
    C C141 0.73533(16) 0.57831(5) 0.50961(8) 0.0301(3) Uani d . 1 1 . .
    H H14A 0.6619 0.5705 0.4650 0.045 Uiso calc R 1 1 . .
    H H14B 0.8219 0.6012 0.4925 0.045 Uiso calc R 1 1 . .
    H H14C 0.6828 0.5997 0.5492 0.045 Uiso calc R 1 1 . .
    C C15 0.90619(13) 0.52068(5) 0.61104(7) 0.0198(2) Uani d . 1 1 . .
    C C151 0.96862(15) 0.57705(5) 0.64736(8) 0.0257(2) Uani d . 1 1 . .
    H H15A 1.0350 0.5685 0.6944 0.038 Uiso calc R 1 1 . .
    H H15B 0.8817 0.6012 0.6610 0.038 Uiso calc R 1 1 . .
    H H15C 1.0291 0.5974 0.6098 0.038 Uiso calc R 1 1 . .
    C C16 0.95592(13) 0.46705(5) 0.64329(7) 0.0201(2) Uani d . 1 1 . .
    H H16 1.0258 0.4668 0.6883 0.024 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C01 C06 . 1.3979(14) ?
    C01 C02 . 1.4070(14) ?
    C01 C011 . 1.4353(15) ?
    C011 C012 . 1.1990(15) ?
    C012 C013 . 1.4783(15) ?
    C013 O01 . 1.4424(13) ?
    O01 H01 . 0.886(18) ?
    C013 C014 . 1.5239(16) ?
    C014 H01A . 0.9600 ?
    C014 H01B . 0.9600 ?
    C014 H01C . 0.9600 ?
    C013 C015 . 1.5240(16) ?
    C015 H01D . 0.9600 ?
    C015 H01E . 0.9600 ?
    C015 H01F . 0.9600 ?
    C02 C021 . 1.4368(14) ?
    C021 C022 . 1.1985(15) ?
    C022 C023 . 1.4783(15) ?
    C023 O02 . 1.4414(14) ?
    O02 H02 . 0.886(19) ?
    C023 C024 . 1.5199(17) ?
    C024 H02A . 0.9600 ?
    C024 H02B . 0.9600 ?
    C024 H02C . 0.9600 ?
    C023 C025 . 1.5249(19) ?
    C025 H02D . 0.9600 ?
    C025 H02E . 0.9600 ?
    C025 H02F . 0.9600 ?
    C02 C03 . 1.3992(14) ?
    C03 C04 . 1.3906(14) ?
    C03 H03 . 0.9300 ?
    C04 C041 . 1.5074(15) ?
    C041 H04A . 0.9600 ?
    C041 H04B . 0.9600 ?
    C041 H04C . 0.9600 ?
    C04 C05 . 1.4025(15) ?
    C05 C051 . 1.5058(15) ?
    C051 H05A . 0.9600 ?
    C051 H05B . 0.9600 ?
    C051 H05C . 0.9600 ?
    C05 C06 . 1.3899(15) ?
    C06 H06 . 0.9300 ?
    C11 C16 . 1.4015(15) ?
    C11 C12 . 1.4096(15) ?
    C11 C111 . 1.4400(15) ?
    C111 C112 . 1.1996(15) ?
    C112 C113 . 1.4828(15) ?
    C113 O11 . 1.4392(13) ?
    O11 H11 . 0.886(19) ?
    C113 C114 . 1.5210(19) ?
    C114 H11A . 0.9600 ?
    C114 H11B . 0.9600 ?
    C114 H11C . 0.9600 ?
    C113 C115 . 1.5198(16) ?
    C115 H11D . 0.9600 ?
    C115 H11E . 0.9600 ?
    C115 H11F . 0.9600 ?
    C12 C121 . 1.4383(15) ?
    C121 C122 . 1.1971(15) ?
    C122 C123 . 1.4818(15) ?
    C123 O12 . 1.4425(13) ?
    O12 H12 . 0.904(18) ?
    C123 C124 . 1.5210(16) ?
    C124 H12A . 0.9600 ?
    C124 H12B . 0.9600 ?
    C124 H12C . 0.9600 ?
    C123 C125 . 1.5270(18) ?
    C125 H12D . 0.9600 ?
    C125 H12E . 0.9600 ?
    C125 H12F . 0.9600 ?
    C12 C13 . 1.4014(15) ?
    C13 C14 . 1.3899(15) ?
    C13 H13 . 0.9300 ?
    C14 C141 . 1.5070(15) ?
    C141 H14A . 0.9600 ?
    C141 H14B . 0.9600 ?
    C141 H14C . 0.9600 ?
    C14 C15 . 1.4066(16) ?
    C15 C151 . 1.5042(15) ?
    C151 H15A . 0.9600 ?
    C151 H15B . 0.9600 ?
    C151 H15C . 0.9600 ?
    C15 C16 . 1.3916(15) ?
    C16 H16 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C06 C01 C02 . . 118.66(9) ?
    C06 C01 C011 . . 120.46(10) ?
    C02 C01 C011 . . 120.88(9) ?
    C011 C011 C012 . . 178.97(13) ?
    C011 C012 C013 . . 175.22(12) ?
    C012 C013 O01 . . 110.28(9) ?
    C014 C013 O01 . . 105.66(9) ?
    C015 C013 O01 . . 109.91(9) ?
    C013 O01 H01 . . 109.8(11) ?
    C012 C013 C014 . . 110.35(9) ?
    C012 C013 C015 . . 109.59(9) ?
    C014 C013 C015 . . 110.99(10) ?
    C013 C014 H01A . . 109.5 ?
    C013 C014 H01B . . 109.5 ?
    H01A C014 H01B . . 109.5 ?
    C013 C014 H01C . . 109.5 ?
    H01A C014 H01C . . 109.5 ?
    H01B C014 H01C . . 109.5 ?
    C013 C015 H01D . . 109.5 ?
    C013 C015 H01E . . 109.5 ?
    H01D C015 H01E . . 109.5 ?
    C013 C015 H01F . . 109.5 ?
    H01D C015 H01F . . 109.5 ?
    H01E C015 H01F . . 109.5 ?
    C01 C02 C03 . . 118.92(9) ?
    C01 C02 C021 . . 120.92(9) ?
    C03 C02 C021 . . 120.15(9) ?
    C02 C021 C022 . . 178.54(11) ?
    C021 C022 C023 . . 179.71(13) ?
    C022 C023 O02 . . 109.35(9) ?
    C024 C023 O02 . . 105.86(10) ?
    C025 C023 O02 . . 109.12(9) ?
    C023 O02 H02 . . 108.5(12) ?
    C022 C023 C024 . . 110.07(10) ?
    C022 C023 C025 . . 109.89(10) ?
    C024 C023 C025 . . 112.44(12) ?
    C023 C024 H02A . . 109.5 ?
    C023 C024 H02B . . 109.5 ?
    H02A C024 H02B . . 109.5 ?
    C023 C024 H02C . . 109.5 ?
    H02A C024 H02C . . 109.5 ?
    H02B C024 H02C . . 109.5 ?
    C023 C025 H02D . . 109.5 ?
    C023 C025 H02E . . 109.5 ?
    H02D C025 H02E . . 109.5 ?
    C023 C025 H02F . . 109.5 ?
    H02D C025 H02F . . 109.5 ?
    H02E C025 H02F . . 109.5 ?
    C02 C03 C04 . . 121.98(10) ?
    C02 C03 H03 . . 119.0 ?
    C04 C03 H03 . . 119.0 ?
    C03 C04 C041 . . 120.02(10) ?
    C03 C04 C05 . . 119.15(10) ?
    C05 C04 C041 . . 120.83(10) ?
    C04 C041 H04A . . 109.5 ?
    C04 C041 H04B . . 109.5 ?
    H04A C041 H04B . . 109.5 ?
    C04 C041 H04C . . 109.5 ?
    H04A C041 H04C . . 109.5 ?
    H04B C041 H04C . . 109.5 ?
    C04 C05 C051 . . 121.08(10) ?
    C04 C05 C06 . . 119.03(10) ?
    C06 C05 C051 . . 119.89(10) ?
    C05 C051 H05A . . 109.5 ?
    C05 C051 H05B . . 109.5 ?
    H05A C051 H05B . . 109.5 ?
    C05 C051 H05C . . 109.5 ?
    H05A C051 H05C . . 109.5 ?
    H05B C051 H05C . . 109.5 ?
    C05 C06 C01 . . 122.25(10) ?
    C05 C06 H06 . . 118.9 ?
    C01 C06 H06 . . 118.9 ?
    C16 C11 C12 . . 118.62(10) ?
    C16 C11 C111 . . 120.32(10) ?
    C12 C11 C111 . . 121.06(10) ?
    C11 C111 C112 . . 178.70(12) ?
    C111 C112 C113 . . 177.37(12) ?
    C112 C113 O11 . . 109.94(9) ?
    C114 C113 O11 . . 109.56(10) ?
    C115 C113 O11 . . 105.05(9) ?
    C113 O11 H11 . . 110.0(12) ?
    C112 C113 C114 . . 110.48(10) ?
    C112 C113 C115 . . 110.29(10) ?
    C114 C113 C115 . . 111.38(11) ?
    C113 C114 H11A . . 109.5 ?
    C113 C114 H11B . . 109.5 ?
    H11A C114 H11B . . 109.5 ?
    C113 C114 H11C . . 109.5 ?
    H11A C114 H11C . . 109.5 ?
    H11B C114 H11C . . 109.5 ?
    C113 C115 H11D . . 109.5 ?
    C113 C115 H11E . . 109.5 ?
    H11D C115 H11E . . 109.5 ?
    C113 C115 H11F . . 109.5 ?
    H11D C115 H11F . . 109.5 ?
    H11E C115 H11F . . 109.5 ?
    C11 C12 C13 . . 118.80(10) ?
    C11 C12 C121 . . 121.14(10) ?
    C13 C12 C121 . . 120.02(10) ?
    C12 C121 C122 . . 177.42(12) ?
    C121 C122 C123 . . 175.21(12) ?
    C122 C123 O12 . . 110.12(9) ?
    C124 C123 O12 . . 105.70(9) ?
    C125 C123 O12 . . 109.47(10) ?
    C123 O12 H12 . . 107.6(11) ?
    C122 C123 C124 . . 110.24(10) ?
    C122 C123 C125 . . 109.56(10) ?
    C124 C123 C125 . . 111.68(11) ?
    C123 C124 H12A . . 109.5 ?
    C123 C124 H12B . . 109.5 ?
    H12A C124 H12B . . 109.5 ?
    C123 C124 H12C . . 109.5 ?
    H12A C124 H12C . . 109.5 ?
    H12B C124 H12C . . 109.5 ?
    C123 C125 H12D . . 109.5 ?
    C123 C125 H12E . . 109.5 ?
    H12D C125 H12E . . 109.5 ?
    C123 C125 H12F . . 109.5 ?
    H12D C125 H12F . . 109.5 ?
    H12E C125 H12F . . 109.5 ?
    C12 C13 C14 . . 122.24(10) ?
    C12 C13 H13 . . 118.9 ?
    C14 C13 H13 . . 118.9 ?
    C13 C14 C141 . . 120.32(11) ?
    C13 C14 C15 . . 119.04(10) ?
    C15 C14 C141 . . 120.64(10) ?
    C14 C141 H14A . . 109.5 ?
    C14 C141 H14B . . 109.5 ?
    H14A C141 H14B . . 109.5 ?
    C14 C141 H14C . . 109.5 ?
    H14A C141 H14C . . 109.5 ?
    H14B C141 H14C . . 109.5 ?
    C14 C15 C151 . . 120.82(10) ?
    C14 C15 C16 . . 118.99(10) ?
    C16 C15 C151 . . 120.18(10) ?
    C15 C151 H15A . . 109.5 ?
    C15 C151 H15B . . 109.5 ?
    H15A C151 H15B . . 109.5 ?
    C15 C151 H15C . . 109.5 ?
    H15A C151 H15C . . 109.5 ?
    H15B C151 H15C . . 109.5 ?
    C15 C16 C11 . . 122.29(10) ?
    C15 C16 H16 . . 118.9 ?
    C11 C16 H16 . . 118.9 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O01 H01 O12 2_655 0.886(18) 1.901(17) 2.7730(10)
                                                   167.5(16) yes
    O02 H02 O11 4_465 0.886(19) 1.876(19) 2.7520(10)
                                                   169.8(18) yes
    O11 H11 O01 3_766 0.886(19) 1.892(19) 2.7560(10)
                                                   164.3(18) yes
    O12 H12 O02 1_555 0.904(18) 1.847(17) 2.7440(10)
                                                   170.7(17) yes
