# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b17062r
_database_code_depnum_ccdc_archive 'CCDC 1558622'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
;
p-Hydroxyphenyl-2,2,4,7-tetramethylchroman
;
_chemical_name_common            
;
7-Methyl Dianin's compound
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 O2'
_chemical_formula_sum            'C19 H22 O2'
_chemical_formula_weight         282.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.77030(15)
_cell_length_b                   12.02971(18)
_cell_length_c                   12.7860(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.6565(14)
_cell_angle_gamma                90
_cell_volume                     1502.69(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4374
_cell_measurement_theta_min      3.5040
_cell_measurement_theta_max      76.4160

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.207
_exptl_absorpt_coefficient_mu    0.620
_shelx_estimated_absorpt_T_min   0.816
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43a (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dualflex, AtlasS2'
_diffrn_detector_area_resol_mean 5.2921
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6135
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.048
_diffrn_reflns_theta_max         74.481
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3058
_reflns_number_gt                2866
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXD-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.5500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0050(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.91655(7) 0.47553(6) 0.76770(6) 0.01758(18) Uani 1 1 d . . . . .
O2 O 0.15204(8) 0.59236(7) 0.83216(6) 0.02145(19) Uani 1 1 d . . . . .
H2 H 0.0839(17) 0.5474(14) 0.8223(13) 0.039(4) Uiso 1 1 d . . . . .
C1 C 1.00098(12) 0.72030(10) 0.47302(9) 0.0244(3) Uani 1 1 d . . . . .
H1A H 0.9545 0.7925 0.4721 0.037 Uiso 1 1 calc R U . . .
H1B H 1.0184 0.6965 0.4011 0.037 Uiso 1 1 calc R U . . .
H1C H 1.0881 0.7269 0.5113 0.037 Uiso 1 1 calc R U . . .
C2 C 0.82110(10) 0.41879(9) 0.83738(8) 0.0160(2) Uani 1 1 d . . . . .
C3 C 0.73189(10) 0.34056(8) 0.77214(8) 0.0166(2) Uani 1 1 d . . . . .
H3A H 0.6675 0.3023 0.8194 0.020 Uiso 1 1 calc R U . . .
H3B H 0.7914 0.2830 0.7411 0.020 Uiso 1 1 calc R U . . .
C4 C 0.64824(10) 0.39640(8) 0.68315(8) 0.0159(2) Uani 1 1 d . . . . .
C5 C 0.70647(11) 0.52500(9) 0.53137(8) 0.0195(2) Uani 1 1 d . . . . .
H5 H 0.6238 0.5017 0.4983 0.023 Uiso 1 1 calc R U . . .
C6 C 0.78805(11) 0.60165(9) 0.48087(8) 0.0203(2) Uani 1 1 d . . . . .
H6 H 0.7598 0.6312 0.4152 0.024 Uiso 1 1 calc R U . . .
C7 C 0.91179(11) 0.63577(9) 0.52615(8) 0.0181(2) Uani 1 1 d . . . . .
C8 C 0.94968(10) 0.59052(8) 0.62206(8) 0.0167(2) Uani 1 1 d . . . . .
H8 H 1.0346 0.6112 0.6533 0.020 Uiso 1 1 calc R U . . .
C9 C 0.86512(10) 0.51506(8) 0.67345(8) 0.0151(2) Uani 1 1 d . . . . .
C10 C 0.74094(10) 0.48031(8) 0.62938(8) 0.0157(2) Uani 1 1 d . . . . .
C11 C 0.51617(10) 0.45053(9) 0.72411(8) 0.0160(2) Uani 1 1 d . . . . .
C12 C 0.41693(11) 0.38488(9) 0.77213(8) 0.0187(2) Uani 1 1 d . . . . .
H12 H 0.4330 0.3074 0.7800 0.022 Uiso 1 1 calc R U . . .
C13 C 0.29538(11) 0.42987(9) 0.80867(8) 0.0195(2) Uani 1 1 d . . . . .
H13 H 0.2300 0.3835 0.8416 0.023 Uiso 1 1 calc R U . . .
C14 C 0.26965(10) 0.54304(9) 0.79688(8) 0.0177(2) Uani 1 1 d . . . . .
C15 C 0.36676(11) 0.60983(9) 0.74979(8) 0.0186(2) Uani 1 1 d . . . . .
H15 H 0.3503 0.6872 0.7419 0.022 Uiso 1 1 calc R U . . .
C16 C 0.48831(11) 0.56385(9) 0.71409(8) 0.0177(2) Uani 1 1 d . . . . .
H16 H 0.5539 0.6107 0.6821 0.021 Uiso 1 1 calc R U . . .
C17 C 0.60603(11) 0.30396(9) 0.60495(9) 0.0208(2) Uani 1 1 d . . . . .
H17A H 0.5462 0.3355 0.5505 0.031 Uiso 1 1 calc R U . . .
H17B H 0.5571 0.2451 0.6421 0.031 Uiso 1 1 calc R U . . .
H17C H 0.6881 0.2728 0.5727 0.031 Uiso 1 1 calc R U . . .
C18 C 0.91346(11) 0.35241(9) 0.91083(8) 0.0200(2) Uani 1 1 d . . . . .
H18A H 0.9673 0.2993 0.8702 0.030 Uiso 1 1 calc R U . . .
H18B H 0.8573 0.3121 0.9612 0.030 Uiso 1 1 calc R U . . .
H18C H 0.9753 0.4031 0.9483 0.030 Uiso 1 1 calc R U . . .
C19 C 0.74233(11) 0.50651(9) 0.89814(9) 0.0204(2) Uani 1 1 d . . . . .
H19A H 0.8061 0.5489 0.9424 0.031 Uiso 1 1 calc R U . . .
H19B H 0.6741 0.4701 0.9421 0.031 Uiso 1 1 calc R U . . .
H19C H 0.6962 0.5570 0.8490 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3845(12) . ?
O1 C2 1.4657(12) . ?
O2 C14 1.3740(12) . ?
O2 H2 0.866(18) . ?
C1 C7 1.5061(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C18 1.5213(14) . ?
C2 C19 1.5242(14) . ?
C2 C3 1.5247(14) . ?
C3 C4 1.5468(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C10 1.5252(14) . ?
C4 C11 1.5424(14) . ?
C4 C17 1.5483(14) . ?
C5 C6 1.3836(16) . ?
C5 C10 1.4011(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3961(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3881(15) . ?
C8 C9 1.3967(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.3959(14) . ?
C11 C16 1.3957(15) . ?
C11 C12 1.3979(14) . ?
C12 C13 1.3908(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3923(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3862(15) . ?
C15 C16 1.3917(15) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
_geom_angle_publ_flag
C9 O1 C2 117.51(8) . . ?
C14 O2 H2 109.1(11) . . ?
C7 C1 H1A 109.5 . . ?
C7 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C7 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C18 104.04(8) . . ?
O1 C2 C19 108.42(8) . . ?
C18 C2 C19 110.38(9) . . ?
O1 C2 C3 108.58(8) . . ?
C18 C2 C3 110.18(9) . . ?
C19 C2 C3 114.67(8) . . ?
C2 C3 C4 115.36(8) . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C10 C4 C11 112.15(8) . . ?
C10 C4 C3 107.91(8) . . ?
C11 C4 C3 111.75(8) . . ?
C10 C4 C17 109.85(8) . . ?
C11 C4 C17 107.75(8) . . ?
C3 C4 C17 107.32(8) . . ?
C6 C5 C10 122.63(10) . . ?
C6 C5 H5 118.7 . . ?
C10 C5 H5 118.7 . . ?
C5 C6 C7 120.21(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 118.16(10) . . ?
C8 C7 C1 120.89(10) . . ?
C6 C7 C1 120.94(10) . . ?
C7 C8 C9 121.15(10) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
O1 C9 C10 123.61(9) . . ?
O1 C9 C8 114.96(9) . . ?
C10 C9 C8 121.38(10) . . ?
C9 C10 C5 116.43(10) . . ?
C9 C10 C4 122.28(9) . . ?
C5 C10 C4 121.27(9) . . ?
C16 C11 C12 117.17(9) . . ?
C16 C11 C4 122.97(9) . . ?
C12 C11 C4 119.86(9) . . ?
C13 C12 C11 121.80(10) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.86(10) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
O2 C14 C15 118.14(10) . . ?
O2 C14 C13 122.50(10) . . ?
C15 C14 C13 119.35(10) . . ?
C14 C15 C16 120.20(10) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 121.62(10) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C2 C18 160.74(8) . . . . ?
C9 O1 C2 C19 -81.77(10) . . . . ?
C9 O1 C2 C3 43.40(11) . . . . ?
O1 C2 C3 C4 -58.20(11) . . . . ?
C18 C2 C3 C4 -171.55(8) . . . . ?
C19 C2 C3 C4 63.21(12) . . . . ?
C2 C3 C4 C10 42.65(11) . . . . ?
C2 C3 C4 C11 -81.10(11) . . . . ?
C2 C3 C4 C17 160.98(9) . . . . ?
C10 C5 C6 C7 1.46(17) . . . . ?
C5 C6 C7 C8 0.17(16) . . . . ?
C5 C6 C7 C1 -179.15(10) . . . . ?
C6 C7 C8 C9 -1.61(15) . . . . ?
C1 C7 C8 C9 177.72(9) . . . . ?
C2 O1 C9 C10 -17.12(14) . . . . ?
C2 O1 C9 C8 165.25(8) . . . . ?
C7 C8 C9 O1 179.17(9) . . . . ?
C7 C8 C9 C10 1.49(15) . . . . ?
O1 C9 C10 C5 -177.37(9) . . . . ?
C8 C9 C10 C5 0.11(15) . . . . ?
O1 C9 C10 C4 1.37(15) . . . . ?
C8 C9 C10 C4 178.86(9) . . . . ?
C6 C5 C10 C9 -1.57(16) . . . . ?
C6 C5 C10 C4 179.67(10) . . . . ?
C11 C4 C10 C9 109.53(11) . . . . ?
C3 C4 C10 C9 -13.98(13) . . . . ?
C17 C4 C10 C9 -130.68(10) . . . . ?
C11 C4 C10 C5 -71.78(12) . . . . ?
C3 C4 C10 C5 164.71(9) . . . . ?
C17 C4 C10 C5 48.01(13) . . . . ?
C10 C4 C11 C16 -1.22(14) . . . . ?
C3 C4 C11 C16 120.11(11) . . . . ?
C17 C4 C11 C16 -122.23(11) . . . . ?
C10 C4 C11 C12 177.60(9) . . . . ?
C3 C4 C11 C12 -61.07(12) . . . . ?
C17 C4 C11 C12 56.59(12) . . . . ?
C16 C11 C12 C13 -0.05(15) . . . . ?
C4 C11 C12 C13 -178.93(9) . . . . ?
C11 C12 C13 C14 0.59(16) . . . . ?
C12 C13 C14 O2 -179.43(9) . . . . ?
C12 C13 C14 C15 -0.77(16) . . . . ?
O2 C14 C15 C16 179.14(9) . . . . ?
C13 C14 C15 C16 0.42(15) . . . . ?
C14 C15 C16 C11 0.13(16) . . . . ?
C12 C11 C16 C15 -0.31(15) . . . . ?
C4 C11 C16 C15 178.54(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.866(18) 1.970(18) 2.8115(11) 163.5(16) 1_455

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p11028_1
_database_code_depnum_ccdc_archive 'CCDC 1541849'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'4S-4-p-hydroxyphenyl-2,2,4-trimethylchroman, 2S,4R-4-p-hydroxyphenyl-2,4-dimethylchroman, 0.33 Tetrachloromethane solvate'
_chemical_name_common            
'JACQ03 Quasiracemate, 4S-Dianins, 2S,4R nor analogue0.33 Tetrachloromethane solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C18 H20 O2),3(C17 H18 O2),C Cl4'
_chemical_formula_sum            'C106 H114 Cl4 O12'
_chemical_formula_weight         1721.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   26.5576(5)
_cell_length_b                   26.5576(5)
_cell_length_c                   11.1274(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6796.8(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9035
_cell_measurement_theta_min      3.3255
_cell_measurement_theta_max      76.1340

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             2742
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.687
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.786
_exptl_absorpt_correction_T_min  0.84604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5598
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            16141
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.532
_diffrn_reflns_theta_max         74.483
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             5821
_reflns_number_gt                5617
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    0.902

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2001), Mercury CSD 3.5.1 (Macrae et al., 2008)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, 2001), Mercury CSD 3.5.1 (Macrae et al., 2008)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+4.7500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5821
_refine_ls_number_parameters     378
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.26301(8) 0.17725(8) 1.27414(16) 0.0183(4) Uani 1 1 d . . . . .
O2A O 0.11719(9) 0.05350(10) 0.68027(19) 0.0274(4) Uani 1 1 d . . . . .
H2AB H 0.1025(19) 0.0236(19) 0.681(4) 0.033 Uiso 1 1 d . U . . .
C2A C 0.22600(11) 0.11591(10) 1.2445(2) 0.0177(5) Uani 1 1 d . . . . .
C3A C 0.26120(10) 0.09549(10) 1.1723(2) 0.0165(5) Uani 1 1 d . . . . .
H3AA H 0.2357 0.0539 1.1521 0.020 Uiso 1 1 calc R U . . .
H3AB H 0.2930 0.0984 1.2238 0.020 Uiso 1 1 calc R U . . .
C4A C 0.28801(10) 0.12932(10) 1.0549(2) 0.0152(5) Uani 1 1 d . . . . .
C5A C 0.31421(10) 0.19384(10) 1.0823(2) 0.0146(5) Uani 1 1 d . . . . .
C6A C 0.35460(11) 0.23653(11) 1.0041(2) 0.0170(5) Uani 1 1 d . . . . .
H6AA H 0.3655 0.2246 0.9330 0.020 Uiso 1 1 calc R U . . .
C7A C 0.37902(11) 0.29549(11) 1.0274(2) 0.0188(5) Uani 1 1 d . . . . .
H7AA H 0.4056 0.3233 0.9720 0.023 Uiso 1 1 calc R U . . .
C8A C 0.36441(11) 0.31358(11) 1.1323(2) 0.0188(5) Uani 1 1 d . . . . .
H8AA H 0.3810 0.3539 1.1489 0.023 Uiso 1 1 calc R U . . .
C9A C 0.32544(10) 0.27246(11) 1.2129(2) 0.0181(5) Uani 1 1 d . . . . .
H9AA H 0.3163 0.2848 1.2857 0.022 Uiso 1 1 calc R U . . .
C10A C 0.29978(10) 0.21320(10) 1.1873(2) 0.0159(5) Uani 1 1 d . . . . .
C11A C 0.24365(10) 0.10982(10) 0.9523(2) 0.0156(5) Uani 1 1 d . . . . .
C12A C 0.21265(11) 0.05122(11) 0.9179(2) 0.0186(5) Uani 1 1 d . . . . .
H12A H 0.2202 0.0240 0.9577 0.022 Uiso 1 1 calc R U . . .
C13A C 0.17111(11) 0.03176(11) 0.8271(2) 0.0193(5) Uani 1 1 d . . . . .
H13A H 0.1509 -0.0082 0.8051 0.023 Uiso 1 1 calc R U . . .
C14A C 0.15925(11) 0.07096(11) 0.7687(2) 0.0180(5) Uani 1 1 d . . . . .
C15A C 0.19004(11) 0.12918(11) 0.7990(2) 0.0185(5) Uani 1 1 d . . . . .
H15A H 0.1828 0.1563 0.7578 0.022 Uiso 1 1 calc R U . . .
C16A C 0.23145(11) 0.14806(10) 0.8894(2) 0.0174(5) Uani 1 1 d . . . . .
H16A H 0.2522 0.1882 0.9092 0.021 Uiso 1 1 calc R U . . .
C17A C 0.33665(11) 0.11660(11) 1.0186(2) 0.0199(5) Uani 1 1 d . . . . .
H17A H 0.3535 0.1356 0.9417 0.030 Uiso 1 1 calc R U . . .
H17B H 0.3204 0.0745 1.0104 0.030 Uiso 1 1 calc R U . . .
H17C H 0.3669 0.1316 1.0805 0.030 Uiso 1 1 calc R U . . .
C18A C 0.20941(12) 0.08528(12) 1.3653(2) 0.0227(5) Uani 1 1 d . . . . .
H18A H 0.2445 0.0913 1.4069 0.034 Uiso 1 1 calc R U . . .
H18B H 0.1831 0.0436 1.3529 0.034 Uiso 1 1 calc R U . . .
H18C H 0.1899 0.1012 1.4140 0.034 Uiso 1 1 calc R U . . .
C19A C 0.17227(11) 0.10894(11) 1.1794(2) 0.0217(5) Uani 1 1 d . . . . .
H19A H 0.1495 0.1186 1.2343 0.033 Uiso 1 1 calc R U . . .
H19B H 0.1484 0.0686 1.1521 0.033 Uiso 1 1 calc R U . . .
H19C H 0.1844 0.1351 1.1099 0.033 Uiso 1 1 calc R U . . .
O1B O 0.08489(8) 0.26364(8) 0.02737(16) 0.0186(4) Uani 1 1 d . . . . .
O2B O 0.06500(9) 0.11949(9) 0.64765(18) 0.0245(4) Uani 1 1 d . . . . .
H2BB H 0.0797(18) 0.1056(18) 0.652(4) 0.029 Uiso 1 1 d . U . . .
C2B C 0.13521(11) 0.25601(11) 0.0270(2) 0.0185(5) Uani 1 1 d . . . . .
H2BA H 0.1709 0.2942 0.0105 0.022 Uiso 1 1 calc R U . . .
C3B C 0.14055(11) 0.23387(11) 0.1483(2) 0.0193(5) Uani 1 1 d . . . . .
H3BA H 0.1733 0.2261 0.1464 0.023 Uiso 1 1 calc R U . . .
H3BB H 0.1046 0.1967 0.1652 0.023 Uiso 1 1 calc R U . . .
C4B C 0.15086(10) 0.27765(10) 0.2513(2) 0.0161(5) Uani 1 1 d . . . . .
C5B C 0.11652(10) 0.30820(10) 0.2248(2) 0.0151(5) Uani 1 1 d . . . . .
C6B C 0.11638(11) 0.34832(10) 0.3067(2) 0.0169(5) Uani 1 1 d . . . . .
H6BA H 0.1385 0.3565 0.3786 0.020 Uiso 1 1 calc R U . . .
C7B C 0.08500(11) 0.37631(11) 0.2858(2) 0.0194(5) Uani 1 1 d . . . . .
H7BA H 0.0856 0.4032 0.3427 0.023 Uiso 1 1 calc R U . . .
C8B C 0.05257(11) 0.36454(11) 0.1802(2) 0.0193(5) Uani 1 1 d . . . . .
H8BA H 0.0299 0.3826 0.1662 0.023 Uiso 1 1 calc R U . . .
C9B C 0.05334(11) 0.32688(11) 0.0966(2) 0.0184(5) Uani 1 1 d . . . . .
H9BA H 0.0320 0.3197 0.0240 0.022 Uiso 1 1 calc R U . . .
C10B C 0.08552(10) 0.29908(10) 0.1180(2) 0.0159(5) Uani 1 1 d . . . . .
C11B C 0.13066(10) 0.24081(10) 0.3668(2) 0.0147(5) Uani 1 1 d . . . . .
C12B C 0.16256(11) 0.21569(11) 0.4115(2) 0.0175(5) Uani 1 1 d . . . . .
H12B H 0.1992 0.2261 0.3767 0.021 Uiso 1 1 calc R U . . .
C13B C 0.14166(11) 0.17592(11) 0.5054(2) 0.0179(5) Uani 1 1 d . . . . .
H13B H 0.1639 0.1595 0.5342 0.022 Uiso 1 1 calc R U . . .
C14B C 0.08825(11) 0.16023(11) 0.5572(2) 0.0174(5) Uani 1 1 d . . . . .
C15B C 0.05621(11) 0.18512(11) 0.5165(2) 0.0184(5) Uani 1 1 d . . . . .
H15B H 0.0201 0.1754 0.5531 0.022 Uiso 1 1 calc R U . . .
C16B C 0.07753(11) 0.22467(11) 0.4211(2) 0.0163(5) Uani 1 1 d . . . . .
H16B H 0.0551 0.2410 0.3926 0.020 Uiso 1 1 calc R U . . .
C17B C 0.21592(11) 0.32424(12) 0.2576(3) 0.0216(5) Uani 1 1 d . . . . .
H17D H 0.2224 0.3506 0.3249 0.032 Uiso 1 1 calc R U . . .
H17E H 0.2276 0.3464 0.1824 0.032 Uiso 1 1 calc R U . . .
H17F H 0.2391 0.3053 0.2695 0.032 Uiso 1 1 calc R U . . .
C18B C 0.12628(13) 0.21397(12) -0.0733(3) 0.0251(6) Uani 1 1 d . . . . .
H18D H 0.1186 0.2281 -0.1485 0.038 Uiso 1 1 calc R U . . .
H18E H 0.0931 0.1757 -0.0541 0.038 Uiso 1 1 calc R U . . .
H18F H 0.1613 0.2108 -0.0823 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.04628(3) -0.02459(3) 1.32859(9) 0.0426(2) Uani 1 1 d . . . . .
Cl2 Cl 0.0000 0.0000 1.11885(14) 0.0534(4) Uani 1 3 d S T P . .
C1 C 0.0000 0.0000 1.2752(5) 0.0296(10) Uani 1 3 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C10A 1.366(3) . ?
O1A C2A 1.459(3) . ?
O2A C14A 1.383(3) . ?
O2A H2AB 0.69(4) . ?
C2A C18A 1.518(4) . ?
C2A C3A 1.523(3) . ?
C2A C19A 1.527(3) . ?
C3A C4A 1.543(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C5A 1.523(3) . ?
C4A C11A 1.533(3) . ?
C4A C17A 1.544(3) . ?
C5A C6A 1.406(3) . ?
C5A C10A 1.405(4) . ?
C6A C7A 1.387(3) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.389(4) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.392(4) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.396(3) . ?
C9A H9AA 0.9500 . ?
C11A C16A 1.399(3) . ?
C11A C12A 1.402(3) . ?
C12A C13A 1.390(4) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.391(4) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.381(4) . ?
C15A C16A 1.386(4) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
O1B C10B 1.374(3) . ?
O1B C2B 1.448(3) . ?
O2B C14B 1.377(3) . ?
O2B H2BB 0.66(4) . ?
C2B C3B 1.507(4) . ?
C2B C18B 1.511(4) . ?
C2B H2BA 1.0000 . ?
C3B C4B 1.556(3) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B C5B 1.522(3) . ?
C4B C11B 1.540(3) . ?
C4B C17B 1.544(3) . ?
C5B C10B 1.396(4) . ?
C5B C6B 1.403(3) . ?
C6B C7B 1.386(3) . ?
C6B H6BA 0.9500 . ?
C7B C8B 1.397(4) . ?
C7B H7BA 0.9500 . ?
C8B C9B 1.374(4) . ?
C8B H8BA 0.9500 . ?
C9B C10B 1.401(3) . ?
C9B H9BA 0.9500 . ?
C11B C16B 1.391(3) . ?
C11B C12B 1.406(3) . ?
C12B C13B 1.389(4) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.388(4) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.389(3) . ?
C15B C16B 1.398(4) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
Cl1 C1 1.759(2) . ?
Cl2 C1 1.740(6) . ?
C1 Cl1 1.759(2) 3 ?
C1 Cl1 1.759(2) 2 ?

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
_geom_angle_publ_flag
C10A O1A C2A 117.89(19) . . ?
C14A O2A H2AB 106(4) . . ?
O1A C2A C18A 104.6(2) . . ?
O1A C2A C3A 109.04(19) . . ?
C18A C2A C3A 110.0(2) . . ?
O1A C2A C19A 108.03(19) . . ?
C18A C2A C19A 110.6(2) . . ?
C3A C2A C19A 114.1(2) . . ?
C2A C3A C4A 115.21(19) . . ?
C2A C3A H3AA 108.5 . . ?
C4A C3A H3AA 108.5 . . ?
C2A C3A H3AB 108.5 . . ?
C4A C3A H3AB 108.5 . . ?
H3AA C3A H3AB 107.5 . . ?
C5A C4A C11A 111.73(19) . . ?
C5A C4A C3A 107.7(2) . . ?
C11A C4A C3A 112.39(19) . . ?
C5A C4A C17A 109.69(19) . . ?
C11A C4A C17A 108.5(2) . . ?
C3A C4A C17A 106.71(19) . . ?
C6A C5A C10A 117.2(2) . . ?
C6A C5A C4A 121.3(2) . . ?
C10A C5A C4A 121.5(2) . . ?
C7A C6A C5A 122.2(2) . . ?
C7A C6A H6AA 118.9 . . ?
C5A C6A H6AA 118.9 . . ?
C6A C7A C8A 119.6(2) . . ?
C6A C7A H7AA 120.2 . . ?
C8A C7A H7AA 120.2 . . ?
C7A C8A C9A 119.8(2) . . ?
C7A C8A H8AA 120.1 . . ?
C9A C8A H8AA 120.1 . . ?
C8A C9A C10A 120.3(2) . . ?
C8A C9A H9AA 119.8 . . ?
C10A C9A H9AA 119.8 . . ?
O1A C10A C9A 114.8(2) . . ?
O1A C10A C5A 124.3(2) . . ?
C9A C10A C5A 120.9(2) . . ?
C16A C11A C12A 116.6(2) . . ?
C16A C11A C4A 123.1(2) . . ?
C12A C11A C4A 120.3(2) . . ?
C13A C12A C11A 121.8(2) . . ?
C13A C12A H12A 119.1 . . ?
C11A C12A H12A 119.1 . . ?
C14A C13A C12A 119.7(2) . . ?
C14A C13A H13A 120.1 . . ?
C12A C13A H13A 120.1 . . ?
O2A C14A C15A 118.4(2) . . ?
O2A C14A C13A 121.9(2) . . ?
C15A C14A C13A 119.7(2) . . ?
C14A C15A C16A 120.0(2) . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A C11A 122.0(2) . . ?
C15A C16A H16A 119.0 . . ?
C11A C16A H16A 119.0 . . ?
C4A C17A H17A 109.5 . . ?
C4A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C4A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C2A C18A H18A 109.5 . . ?
C2A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C2A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C2A C19A H19A 109.5 . . ?
C2A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C2A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C10B O1B C2B 113.71(19) . . ?
C14B O2B H2BB 110(4) . . ?
O1B C2B C3B 109.0(2) . . ?
O1B C2B C18B 106.9(2) . . ?
C3B C2B C18B 112.6(2) . . ?
O1B C2B H2BA 109.4 . . ?
C3B C2B H2BA 109.4 . . ?
C18B C2B H2BA 109.4 . . ?
C2B C3B C4B 112.6(2) . . ?
C2B C3B H3BA 109.1 . . ?
C4B C3B H3BA 109.1 . . ?
C2B C3B H3BB 109.1 . . ?
C4B C3B H3BB 109.1 . . ?
H3BA C3B H3BB 107.8 . . ?
C5B C4B C11B 112.9(2) . . ?
C5B C4B C17B 108.08(19) . . ?
C11B C4B C17B 111.5(2) . . ?
C5B C4B C3B 109.1(2) . . ?
C11B C4B C3B 105.34(19) . . ?
C17B C4B C3B 109.9(2) . . ?
C10B C5B C6B 117.3(2) . . ?
C10B C5B C4B 122.1(2) . . ?
C6B C5B C4B 120.6(2) . . ?
C7B C6B C5B 121.9(2) . . ?
C7B C6B H6BA 119.0 . . ?
C5B C6B H6BA 119.0 . . ?
C6B C7B C8B 119.4(2) . . ?
C6B C7B H7BA 120.3 . . ?
C8B C7B H7BA 120.3 . . ?
C9B C8B C7B 120.0(2) . . ?
C9B C8B H8BA 120.0 . . ?
C7B C8B H8BA 120.0 . . ?
C8B C9B C10B 120.2(2) . . ?
C8B C9B H9BA 119.9 . . ?
C10B C9B H9BA 119.9 . . ?
O1B C10B C5B 123.2(2) . . ?
O1B C10B C9B 115.8(2) . . ?
C5B C10B C9B 121.0(2) . . ?
C16B C11B C12B 117.3(2) . . ?
C16B C11B C4B 122.4(2) . . ?
C12B C11B C4B 119.7(2) . . ?
C13B C12B C11B 121.4(2) . . ?
C13B C12B H12B 119.3 . . ?
C11B C12B H12B 119.3 . . ?
C14B C13B C12B 120.0(2) . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
O2B C14B C15B 118.1(2) . . ?
O2B C14B C13B 121.9(2) . . ?
C15B C14B C13B 119.9(2) . . ?
C14B C15B C16B 119.4(2) . . ?
C14B C15B H15B 120.3 . . ?
C16B C15B H15B 120.3 . . ?
C11B C16B C15B 121.9(2) . . ?
C11B C16B H16B 119.0 . . ?
C15B C16B H16B 119.0 . . ?
C4B C17B H17D 109.5 . . ?
C4B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C4B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C2B C18B H18D 109.5 . . ?
C2B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C2B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
Cl2 C1 Cl1 109.75(18) . . ?
Cl2 C1 Cl1 109.75(18) . 3 ?
Cl1 C1 Cl1 109.20(18) . 3 ?
Cl2 C1 Cl1 109.75(18) . 2 ?
Cl1 C1 Cl1 109.19(18) . 2 ?
Cl1 C1 Cl1 109.19(18) 3 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10A O1A C2A C18A 158.8(2) . . . . ?
C10A O1A C2A C3A 41.2(3) . . . . ?
C10A O1A C2A C19A -83.3(2) . . . . ?
O1A C2A C3A C4A -57.8(3) . . . . ?
C18A C2A C3A C4A -172.0(2) . . . . ?
C19A C2A C3A C4A 63.0(3) . . . . ?
C2A C3A C4A C5A 44.1(3) . . . . ?
C2A C3A C4A C11A -79.4(3) . . . . ?
C2A C3A C4A C17A 161.8(2) . . . . ?
C11A C4A C5A C6A -72.9(3) . . . . ?
C3A C4A C5A C6A 163.1(2) . . . . ?
C17A C4A C5A C6A 47.4(3) . . . . ?
C11A C4A C5A C10A 108.1(2) . . . . ?
C3A C4A C5A C10A -15.8(3) . . . . ?
C17A C4A C5A C10A -131.6(2) . . . . ?
C10A C5A C6A C7A -0.9(4) . . . . ?
C4A C5A C6A C7A -179.9(2) . . . . ?
C5A C6A C7A C8A 1.4(4) . . . . ?
C6A C7A C8A C9A 0.0(4) . . . . ?
C7A C8A C9A C10A -1.8(4) . . . . ?
C2A O1A C10A C9A 168.2(2) . . . . ?
C2A O1A C10A C5A -15.1(3) . . . . ?
C8A C9A C10A O1A 179.1(2) . . . . ?
C8A C9A C10A C5A 2.3(4) . . . . ?
C6A C5A C10A O1A -177.5(2) . . . . ?
C4A C5A C10A O1A 1.5(4) . . . . ?
C6A C5A C10A C9A -0.9(3) . . . . ?
C4A C5A C10A C9A 178.1(2) . . . . ?
C5A C4A C11A C16A 2.6(3) . . . . ?
C3A C4A C11A C16A 123.9(3) . . . . ?
C17A C4A C11A C16A -118.4(3) . . . . ?
C5A C4A C11A C12A -176.8(2) . . . . ?
C3A C4A C11A C12A -55.6(3) . . . . ?
C17A C4A C11A C12A 62.1(3) . . . . ?
C16A C11A C12A C13A -1.0(4) . . . . ?
C4A C11A C12A C13A 178.5(2) . . . . ?
C11A C12A C13A C14A -0.5(4) . . . . ?
C12A C13A C14A O2A -178.1(2) . . . . ?
C12A C13A C14A C15A 1.9(4) . . . . ?
O2A C14A C15A C16A 178.3(2) . . . . ?
C13A C14A C15A C16A -1.7(4) . . . . ?
C14A C15A C16A C11A 0.2(4) . . . . ?
C12A C11A C16A C15A 1.2(4) . . . . ?
C4A C11A C16A C15A -178.3(2) . . . . ?
C10B O1B C2B C3B 55.3(3) . . . . ?
C10B O1B C2B C18B 177.3(2) . . . . ?
O1B C2B C3B C4B -62.6(3) . . . . ?
C18B C2B C3B C4B 179.0(2) . . . . ?
C2B C3B C4B C5B 36.1(3) . . . . ?
C2B C3B C4B C11B 157.5(2) . . . . ?
C2B C3B C4B C17B -82.3(3) . . . . ?
C11B C4B C5B C10B -121.3(2) . . . . ?
C17B C4B C5B C10B 114.9(3) . . . . ?
C3B C4B C5B C10B -4.6(3) . . . . ?
C11B C4B C5B C6B 60.6(3) . . . . ?
C17B C4B C5B C6B -63.2(3) . . . . ?
C3B C4B C5B C6B 177.3(2) . . . . ?
C10B C5B C6B C7B 2.6(4) . . . . ?
C4B C5B C6B C7B -179.2(2) . . . . ?
C5B C6B C7B C8B -0.1(4) . . . . ?
C6B C7B C8B C9B -2.0(4) . . . . ?
C7B C8B C9B C10B 1.5(4) . . . . ?
C2B O1B C10B C5B -24.2(3) . . . . ?
C2B O1B C10B C9B 154.9(2) . . . . ?
C6B C5B C10B O1B 176.1(2) . . . . ?
C4B C5B C10B O1B -2.1(4) . . . . ?
C6B C5B C10B C9B -3.0(3) . . . . ?
C4B C5B C10B C9B 178.8(2) . . . . ?
C8B C9B C10B O1B -178.1(2) . . . . ?
C8B C9B C10B C5B 1.0(4) . . . . ?
C5B C4B C11B C16B 16.5(3) . . . . ?
C17B C4B C11B C16B 138.4(2) . . . . ?
C3B C4B C11B C16B -102.5(2) . . . . ?
C5B C4B C11B C12B -172.2(2) . . . . ?
C17B C4B C11B C12B -50.3(3) . . . . ?
C3B C4B C11B C12B 68.8(3) . . . . ?
C16B C11B C12B C13B 0.6(4) . . . . ?
C4B C11B C12B C13B -171.1(2) . . . . ?
C11B C12B C13B C14B 0.0(4) . . . . ?
C12B C13B C14B O2B 177.7(2) . . . . ?
C12B C13B C14B C15B -1.2(4) . . . . ?
O2B C14B C15B C16B -177.2(2) . . . . ?
C13B C14B C15B C16B 1.8(4) . . . . ?
C12B C11B C16B C15B 0.0(4) . . . . ?
C4B C11B C16B C15B 171.5(2) . . . . ?
C14B C15B C16B C11B -1.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2A H2AB O2B 0.69(4) 2.07(4) 2.751(3) 168(5) 3
O2B H2BB O2A 0.66(4) 2.09(4) 2.748(3) 172(5) .

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.043

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CCl4'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p11028
_database_code_depnum_ccdc_archive 'CCDC 1541892'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'2R,4R-4-p-hydroxyphenyl-2,4-dimethylchroman,2R,4S-4-p-hydroxyphenyl-2,4-dimethylchroman.0.33 Tetrachloromethane solvate'
_chemical_name_common            
'JACQ02 Quasiracemate, 2R,4R AND 2R,4S nor methyl analogues0.33 Tetrachloromethane solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '6(C17 H18 O2),C Cl4'
_chemical_formula_sum            'C103 H108 Cl4 O12'
_chemical_formula_weight         1679.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   26.3307(3)
_cell_length_b                   26.3307(3)
_cell_length_c                   11.1874(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6717.1(2)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    10075
_cell_measurement_theta_min      3.3542
_cell_measurement_theta_max      76.0617

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             2670
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.450
_exptl_absorpt_coefficient_mu    1.694
_shelx_estimated_absorpt_T_min   0.485
_shelx_estimated_absorpt_T_max   0.516
_exptl_absorpt_correction_T_min  0.72099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5598
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            15436
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.357
_diffrn_reflns_theta_max         74.495
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             5891
_reflns_number_gt                5838
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.937

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2001), Mercury CSD 3.5.1 (Macrae et al., 2008)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, 2001), Mercury CSD 3.5.1 (Macrae et al., 2008)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+9.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5891
_refine_ls_number_parameters     364
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.08579(10) 0.26510(10) -0.3337(2) 0.0214(4) Uani 1 1 d . . . . .
O2A O 0.06513(12) 0.11793(10) 0.2858(2) 0.0292(5) Uani 1 1 d . . . . .
H2A H 0.0825 0.0984 0.2868 0.035 Uiso 1 1 calc R U . . .
C2A C 0.13507(13) 0.25521(14) -0.3330(3) 0.0224(6) Uani 1 1 d . . . . .
H2B H 0.1720 0.2931 -0.3482 0.027 Uiso 1 1 calc R U . . .
C3A C 0.13855(13) 0.23171(13) -0.2121(3) 0.0213(6) Uani 1 1 d . . . . .
H3AA H 0.1703 0.2220 -0.2132 0.026 Uiso 1 1 calc R U . . .
H3AB H 0.1012 0.1951 -0.1961 0.026 Uiso 1 1 calc R U . . .
C4A C 0.15036(13) 0.27611(13) -0.1096(3) 0.0184(6) Uani 1 1 d . . . . .
C5A C 0.11635(12) 0.30823(13) -0.1350(3) 0.0174(6) Uani 1 1 d . . . . .
C6A C 0.11634(13) 0.34779(14) -0.0528(3) 0.0206(6) Uani 1 1 d . . . . .
H6AA H 0.1376 0.3548 0.0197 0.025 Uiso 1 1 calc R U . . .
C7A C 0.08595(14) 0.37737(14) -0.0739(3) 0.0227(6) Uani 1 1 d . . . . .
H7AA H 0.0866 0.4043 -0.0166 0.027 Uiso 1 1 calc R U . . .
C8A C 0.05449(14) 0.36725(14) -0.1797(3) 0.0217(6) Uani 1 1 d . . . . .
H8AA H 0.0323 0.3862 -0.1935 0.026 Uiso 1 1 calc R U . . .
C9A C 0.05551(13) 0.32968(13) -0.2645(3) 0.0200(6) Uani 1 1 d . . . . .
H9AA H 0.0351 0.3237 -0.3378 0.024 Uiso 1 1 calc R U . . .
C10A C 0.08659(12) 0.30057(12) -0.2425(3) 0.0172(6) Uani 1 1 d . . . . .
C11A C 0.12983(13) 0.23926(13) 0.0044(3) 0.0180(6) Uani 1 1 d . . . . .
C12A C 0.07539(14) 0.22143(14) 0.0563(3) 0.0209(6) Uani 1 1 d . . . . .
H12A H 0.0520 0.2366 0.0260 0.025 Uiso 1 1 calc R U . . .
C13A C 0.05424(14) 0.18205(14) 0.1512(3) 0.0224(6) Uani 1 1 d . . . . .
H13A H 0.0174 0.1715 0.1862 0.027 Uiso 1 1 calc R U . . .
C14A C 0.08711(14) 0.15828(13) 0.1942(3) 0.0200(6) Uani 1 1 d . . . . .
C15A C 0.14191(14) 0.17503(14) 0.1448(3) 0.0210(6) Uani 1 1 d . . . . .
H15A H 0.1649 0.1594 0.1751 0.025 Uiso 1 1 calc R U . . .
C16A C 0.16242(14) 0.21475(14) 0.0510(3) 0.0211(6) Uani 1 1 d . . . . .
H16A H 0.1996 0.2257 0.0171 0.025 Uiso 1 1 calc R U . . .
C17A C 0.21571(13) 0.32247(14) -0.1041(3) 0.0242(7) Uani 1 1 d . . . . .
H17A H 0.2234 0.3464 -0.0320 0.036 Uiso 1 1 calc R U . . .
H17B H 0.2263 0.3477 -0.1749 0.036 Uiso 1 1 calc R U . . .
H17C H 0.2391 0.3030 -0.1020 0.036 Uiso 1 1 calc R U . . .
C18A C 0.12531(16) 0.21293(16) -0.4327(3) 0.0290(7) Uani 1 1 d . . . . .
H18A H 0.1211 0.2291 -0.5084 0.044 Uiso 1 1 calc R U . . .
H18B H 0.0896 0.1755 -0.4169 0.044 Uiso 1 1 calc R U . . .
H18C H 0.1589 0.2066 -0.4377 0.044 Uiso 1 1 calc R U . . .
O1B O -0.17681(10) 0.08304(10) 0.9085(2) 0.0233(5) Uani 1 1 d . . . . .
O2B O -0.05149(12) 0.06491(12) 0.3236(2) 0.0303(5) Uani 1 1 d . . . . .
H2C H -0.0149 0.0852 0.3167 0.036 Uiso 1 1 calc R U . . .
C2B C -0.11646(13) 0.10621(13) 0.8710(3) 0.0230(6) Uani 1 1 d . . . . .
H2D H -0.1142 0.0786 0.8129 0.028 Uiso 1 1 calc R U . . .
C3B C -0.09481(13) 0.16521(13) 0.8120(3) 0.0210(6) Uani 1 1 d . . . . .
H3C H -0.0526 0.1827 0.7932 0.025 Uiso 1 1 calc R U . . .
H3D H -0.0993 0.1917 0.8684 0.025 Uiso 1 1 calc R U . . .
C4B C -0.12866(13) 0.15998(13) 0.6968(3) 0.0182(6) Uani 1 1 d . . . . .
C5B C -0.19406(13) 0.12087(12) 0.7238(3) 0.0180(6) Uani 1 1 d . . . . .
C6B C -0.23664(14) 0.11955(13) 0.6467(3) 0.0206(6) Uani 1 1 d . . . . .
H6B H -0.2243 0.1431 0.5766 0.025 Uiso 1 1 calc R U . . .
C7B C -0.29626(14) 0.08492(14) 0.6693(3) 0.0241(6) Uani 1 1 d . . . . .
H7B H -0.3243 0.0838 0.6142 0.029 Uiso 1 1 calc R U . . .
C8B C -0.31435(13) 0.05199(14) 0.7738(3) 0.0232(6) Uani 1 1 d . . . . .
H8B H -0.3550 0.0288 0.7912 0.028 Uiso 1 1 calc R U . . .
C9B C -0.27349(14) 0.05279(13) 0.8525(3) 0.0224(6) Uani 1 1 d . . . . .
H9B H -0.2861 0.0308 0.9245 0.027 Uiso 1 1 calc R U . . .
C10B C -0.21356(14) 0.08604(13) 0.8263(3) 0.0200(6) Uani 1 1 d . . . . .
C11B C -0.10908(13) 0.13397(13) 0.5954(3) 0.0174(6) Uani 1 1 d . . . . .
C12B C -0.05063(13) 0.16397(14) 0.5562(3) 0.0216(6) Uani 1 1 d . . . . .
H12B H -0.0237 0.2004 0.5921 0.026 Uiso 1 1 calc R U . . .
C13B C -0.03148(14) 0.14136(14) 0.4660(3) 0.0234(6) Uani 1 1 d . . . . .
H13B H 0.0083 0.1623 0.4410 0.028 Uiso 1 1 calc R U . . .
C14B C -0.07014(14) 0.08847(14) 0.4123(3) 0.0205(6) Uani 1 1 d . . . . .
C15B C -0.12809(14) 0.05837(14) 0.4479(3) 0.0229(6) Uani 1 1 d . . . . .
H15B H -0.1549 0.0225 0.4103 0.027 Uiso 1 1 calc R U . . .
C16B C -0.14700(14) 0.08087(13) 0.5393(3) 0.0206(6) Uani 1 1 d . . . . .
H16B H -0.1868 0.0595 0.5641 0.025 Uiso 1 1 calc R U . . .
C17B C -0.11585(14) 0.22179(13) 0.6615(3) 0.0234(6) Uani 1 1 d . . . . .
H17D H -0.1287 0.2381 0.7257 0.035 Uiso 1 1 calc R U . . .
H17E H -0.1370 0.2195 0.5878 0.035 Uiso 1 1 calc R U . . .
H17F H -0.0736 0.2472 0.6484 0.035 Uiso 1 1 calc R U . . .
C18B C -0.08201(16) 0.11014(18) 0.9829(4) 0.0358(8) Uani 1 1 d . . . . .
H18D H -0.0969 0.0708 1.0163 0.054 Uiso 1 1 calc R U . . .
H18E H -0.0865 0.1351 1.0419 0.054 Uiso 1 1 calc R U . . .
H18F H -0.0404 0.1270 0.9626 0.054 Uiso 1 1 calc R U . . .
Cl1A Cl -0.02659(13) 0.04580(14) 0.6797(4) 0.1041(8) Uani 0.707(4) 1 d D . P A
1
Cl2A Cl 0.0000 0.0000 0.8713(13) 0.350(8) Uani 0.707(4) 3 d DS T P A 1
C1A C 0.0000 0.0000 0.7300(17) 0.350(8) Uani 0.707(4) 3 d DS T P A 1
Cl1B Cl 0.0234(3) -0.0467(3) 0.9082(9) 0.1041(8) Uani 0.293(4) 1 d D . P A 2
Cl2B Cl 0.0000 0.0000 0.7300(17) 0.350(8) Uani 0.293(4) 3 d DS T P A 2
C1B C 0.0000 0.0000 0.8713(13) 0.350(8) Uani 0.293(4) 3 d DS T P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C10A 1.376(4) . ?
O1A C2A 1.446(4) . ?
O2A C14A 1.378(4) . ?
O2A H2A 0.8400 . ?
C2A C18A 1.504(4) . ?
C2A C3A 1.510(4) . ?
C2A H2B 1.0000 . ?
C3A C4A 1.554(4) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C11A 1.528(4) . ?
C4A C17A 1.534(4) . ?
C4A C5A 1.535(4) . ?
C5A C6A 1.390(4) . ?
C5A C10A 1.394(4) . ?
C6A C7A 1.388(4) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.391(5) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.381(5) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.395(4) . ?
C9A H9AA 0.9500 . ?
C11A C12A 1.392(4) . ?
C11A C16A 1.406(4) . ?
C12A C13A 1.390(5) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.384(4) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.395(4) . ?
C15A C16A 1.386(5) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
O1B C10B 1.366(4) . ?
O1B C2B 1.450(4) . ?
O2B C14B 1.384(4) . ?
O2B H2C 0.8400 . ?
C2B C3B 1.513(4) . ?
C2B C18B 1.519(4) . ?
C2B H2D 1.0000 . ?
C3B C4B 1.533(4) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C4B C5B 1.531(4) . ?
C4B C17B 1.539(4) . ?
C4B C11B 1.541(4) . ?
C5B C10B 1.395(4) . ?
C5B C6B 1.401(4) . ?
C6B C7B 1.389(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.390(5) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.382(5) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.401(4) . ?
C9B H9B 0.9500 . ?
C11B C16B 1.397(4) . ?
C11B C12B 1.403(4) . ?
C12B C13B 1.389(5) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.385(5) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.381(4) . ?
C15B C16B 1.392(4) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
Cl1A C1A 1.762(6) . ?
Cl2A C1A 1.581(15) . ?
C1A Cl1A 1.762(6) 3 ?
C1A Cl1A 1.762(6) 2 ?
Cl1B C1B 1.680(7) . ?
Cl2B C1B 1.581(15) . ?
C1B Cl1B 1.680(7) 2 ?
C1B Cl1B 1.680(7) 3 ?

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
_geom_angle_publ_flag
C10A O1A C2A 114.1(2) . . ?
C14A O2A H2A 109.5 . . ?
O1A C2A C18A 107.0(3) . . ?
O1A C2A C3A 108.8(2) . . ?
C18A C2A C3A 112.6(3) . . ?
O1A C2A H2B 109.5 . . ?
C18A C2A H2B 109.5 . . ?
C3A C2A H2B 109.5 . . ?
C2A C3A C4A 112.5(2) . . ?
C2A C3A H3AA 109.1 . . ?
C4A C3A H3AA 109.1 . . ?
C2A C3A H3AB 109.1 . . ?
C4A C3A H3AB 109.1 . . ?
H3AA C3A H3AB 107.8 . . ?
C11A C4A C17A 111.9(2) . . ?
C11A C4A C5A 112.7(2) . . ?
C17A C4A C5A 107.5(2) . . ?
C11A C4A C3A 105.3(2) . . ?
C17A C4A C3A 110.5(2) . . ?
C5A C4A C3A 109.0(2) . . ?
C6A C5A C10A 118.0(3) . . ?
C6A C5A C4A 120.6(3) . . ?
C10A C5A C4A 121.4(3) . . ?
C7A C6A C5A 121.6(3) . . ?
C7A C6A H6AA 119.2 . . ?
C5A C6A H6AA 119.2 . . ?
C6A C7A C8A 119.5(3) . . ?
C6A C7A H7AA 120.2 . . ?
C8A C7A H7AA 120.2 . . ?
C9A C8A C7A 119.9(3) . . ?
C9A C8A H8AA 120.0 . . ?
C7A C8A H8AA 120.0 . . ?
C8A C9A C10A 119.9(3) . . ?
C8A C9A H9AA 120.0 . . ?
C10A C9A H9AA 120.0 . . ?
O1A C10A C5A 123.7(3) . . ?
O1A C10A C9A 115.3(3) . . ?
C5A C10A C9A 121.0(3) . . ?
C12A C11A C16A 116.9(3) . . ?
C12A C11A C4A 122.7(3) . . ?
C16A C11A C4A 119.8(3) . . ?
C13A C12A C11A 122.0(3) . . ?
C13A C12A H12A 119.0 . . ?
C11A C12A H12A 119.0 . . ?
C14A C13A C12A 119.7(3) . . ?
C14A C13A H13A 120.2 . . ?
C12A C13A H13A 120.2 . . ?
O2A C14A C13A 119.4(3) . . ?
O2A C14A C15A 120.5(3) . . ?
C13A C14A C15A 120.1(3) . . ?
C16A C15A C14A 119.3(3) . . ?
C16A C15A H15A 120.3 . . ?
C14A C15A H15A 120.3 . . ?
C15A C16A C11A 122.0(3) . . ?
C15A C16A H16A 119.0 . . ?
C11A C16A H16A 119.0 . . ?
C4A C17A H17A 109.5 . . ?
C4A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C4A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C2A C18A H18A 109.5 . . ?
C2A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C2A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C10B O1B C2B 116.1(2) . . ?
C14B O2B H2C 109.5 . . ?
O1B C2B C3B 109.2(2) . . ?
O1B C2B C18B 106.4(3) . . ?
C3B C2B C18B 112.6(3) . . ?
O1B C2B H2D 109.5 . . ?
C3B C2B H2D 109.5 . . ?
C18B C2B H2D 109.5 . . ?
C2B C3B C4B 111.8(2) . . ?
C2B C3B H3C 109.3 . . ?
C4B C3B H3C 109.3 . . ?
C2B C3B H3D 109.3 . . ?
C4B C3B H3D 109.3 . . ?
H3C C3B H3D 107.9 . . ?
C5B C4B C3B 107.6(2) . . ?
C5B C4B C17B 109.9(2) . . ?
C3B C4B C17B 108.1(2) . . ?
C5B C4B C11B 111.1(2) . . ?
C3B C4B C11B 110.5(2) . . ?
C17B C4B C11B 109.6(2) . . ?
C10B C5B C6B 117.6(3) . . ?
C10B C5B C4B 121.6(3) . . ?
C6B C5B C4B 120.8(3) . . ?
C7B C6B C5B 122.1(3) . . ?
C7B C6B H6B 118.9 . . ?
C5B C6B H6B 118.9 . . ?
C6B C7B C8B 119.0(3) . . ?
C6B C7B H7B 120.5 . . ?
C8B C7B H7B 120.5 . . ?
C9B C8B C7B 120.3(3) . . ?
C9B C8B H8B 119.8 . . ?
C7B C8B H8B 119.8 . . ?
C8B C9B C10B 120.1(3) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
O1B C10B C5B 123.6(3) . . ?
O1B C10B C9B 115.6(3) . . ?
C5B C10B C9B 120.8(3) . . ?
C16B C11B C12B 117.2(3) . . ?
C16B C11B C4B 123.1(3) . . ?
C12B C11B C4B 119.7(3) . . ?
C13B C12B C11B 121.1(3) . . ?
C13B C12B H12B 119.4 . . ?
C11B C12B H12B 119.4 . . ?
C14B C13B C12B 120.3(3) . . ?
C14B C13B H13B 119.8 . . ?
C12B C13B H13B 119.8 . . ?
C15B C14B C13B 119.8(3) . . ?
C15B C14B O2B 119.2(3) . . ?
C13B C14B O2B 121.0(3) . . ?
C14B C15B C16B 119.7(3) . . ?
C14B C15B H15B 120.1 . . ?
C16B C15B H15B 120.1 . . ?
C15B C16B C11B 121.8(3) . . ?
C15B C16B H16B 119.1 . . ?
C11B C16B H16B 119.1 . . ?
C4B C17B H17D 109.5 . . ?
C4B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C4B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C2B C18B H18D 109.5 . . ?
C2B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C2B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
Cl2A C1A Cl1A 108.6(6) . 3 ?
Cl2A C1A Cl1A 108.6(6) . 2 ?
Cl1A C1A Cl1A 110.3(6) 3 2 ?
Cl2A C1A Cl1A 108.6(6) . . ?
Cl1A C1A Cl1A 110.3(6) 3 . ?
Cl1A C1A Cl1A 110.3(6) 2 . ?
Cl1B C1B Cl1B 114.2(5) 2 3 ?
Cl1B C1B Cl1B 114.2(5) 2 . ?
Cl1B C1B Cl1B 114.2(5) 3 . ?
Cl1B C1B Cl2B 104.2(6) 2 . ?
Cl1B C1B Cl2B 104.2(6) 3 . ?
Cl1B C1B Cl2B 104.2(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10A O1A C2A C18A 176.4(3) . . . . ?
C10A O1A C2A C3A 54.5(3) . . . . ?
O1A C2A C3A C4A -63.1(3) . . . . ?
C18A C2A C3A C4A 178.4(3) . . . . ?
C2A C3A C4A C11A 159.1(2) . . . . ?
C2A C3A C4A C17A -79.9(3) . . . . ?
C2A C3A C4A C5A 38.0(3) . . . . ?
C11A C4A C5A C6A 59.3(4) . . . . ?
C17A C4A C5A C6A -64.4(4) . . . . ?
C3A C4A C5A C6A 175.8(3) . . . . ?
C11A C4A C5A C10A -123.3(3) . . . . ?
C17A C4A C5A C10A 113.0(3) . . . . ?
C3A C4A C5A C10A -6.8(4) . . . . ?
C10A C5A C6A C7A 2.4(4) . . . . ?
C4A C5A C6A C7A 179.9(3) . . . . ?
C5A C6A C7A C8A 0.2(5) . . . . ?
C6A C7A C8A C9A -2.4(5) . . . . ?
C7A C8A C9A C10A 2.0(5) . . . . ?
C2A O1A C10A C5A -23.8(4) . . . . ?
C2A O1A C10A C9A 155.6(3) . . . . ?
C6A C5A C10A O1A 176.5(3) . . . . ?
C4A C5A C10A O1A -1.0(4) . . . . ?
C6A C5A C10A C9A -2.9(4) . . . . ?
C4A C5A C10A C9A 179.6(3) . . . . ?
C8A C9A C10A O1A -178.7(3) . . . . ?
C8A C9A C10A C5A 0.7(4) . . . . ?
C17A C4A C11A C12A 140.9(3) . . . . ?
C5A C4A C11A C12A 19.7(4) . . . . ?
C3A C4A C11A C12A -99.0(3) . . . . ?
C17A C4A C11A C16A -48.5(4) . . . . ?
C5A C4A C11A C16A -169.7(3) . . . . ?
C3A C4A C11A C16A 71.6(3) . . . . ?
C16A C11A C12A C13A 1.1(5) . . . . ?
C4A C11A C12A C13A 171.9(3) . . . . ?
C11A C12A C13A C14A -1.7(5) . . . . ?
C12A C13A C14A O2A -178.0(3) . . . . ?
C12A C13A C14A C15A 1.7(5) . . . . ?
O2A C14A C15A C16A 178.6(3) . . . . ?
C13A C14A C15A C16A -1.2(5) . . . . ?
C14A C15A C16A C11A 0.6(5) . . . . ?
C12A C11A C16A C15A -0.5(5) . . . . ?
C4A C11A C16A C15A -171.6(3) . . . . ?
C10B O1B C2B C3B 46.5(3) . . . . ?
C10B O1B C2B C18B 168.2(3) . . . . ?
O1B C2B C3B C4B -64.2(3) . . . . ?
C18B C2B C3B C4B 177.9(3) . . . . ?
C2B C3B C4B C5B 46.6(3) . . . . ?
C2B C3B C4B C17B 165.2(3) . . . . ?
C2B C3B C4B C11B -74.9(3) . . . . ?
C3B C4B C5B C10B -15.1(4) . . . . ?
C17B C4B C5B C10B -132.6(3) . . . . ?
C11B C4B C5B C10B 106.0(3) . . . . ?
C3B C4B C5B C6B 163.9(3) . . . . ?
C17B C4B C5B C6B 46.5(4) . . . . ?
C11B C4B C5B C6B -75.0(3) . . . . ?
C10B C5B C6B C7B -0.3(4) . . . . ?
C4B C5B C6B C7B -179.4(3) . . . . ?
C5B C6B C7B C8B 2.2(5) . . . . ?
C6B C7B C8B C9B -1.4(5) . . . . ?
C7B C8B C9B C10B -1.1(5) . . . . ?
C2B O1B C10B C5B -15.1(4) . . . . ?
C2B O1B C10B C9B 166.8(3) . . . . ?
C6B C5B C10B O1B 179.7(3) . . . . ?
C4B C5B C10B O1B -1.2(4) . . . . ?
C6B C5B C10B C9B -2.3(4) . . . . ?
C4B C5B C10B C9B 176.8(3) . . . . ?
C8B C9B C10B O1B -178.8(3) . . . . ?
C8B C9B C10B C5B 3.1(5) . . . . ?
C5B C4B C11B C16B -1.3(4) . . . . ?
C3B C4B C11B C16B 118.1(3) . . . . ?
C17B C4B C11B C16B -122.9(3) . . . . ?
C5B C4B C11B C12B 179.0(3) . . . . ?
C3B C4B C11B C12B -61.6(3) . . . . ?
C17B C4B C11B C12B 57.4(4) . . . . ?
C16B C11B C12B C13B -0.4(5) . . . . ?
C4B C11B C12B C13B 179.3(3) . . . . ?
C11B C12B C13B C14B 0.3(5) . . . . ?
C12B C13B C14B C15B 0.6(5) . . . . ?
C12B C13B C14B O2B -178.9(3) . . . . ?
C13B C14B C15B C16B -1.2(5) . . . . ?
O2B C14B C15B C16B 178.3(3) . . . . ?
C14B C15B C16B C11B 1.0(5) . . . . ?
C12B C11B C16B C15B -0.2(5) . . . . ?
C4B C11B C16B C15B -179.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2A H2A O2B 0.84 1.90 2.724(4) 167.7 3
O2B H2C O2A 0.84 1.87 2.696(4) 169.2 .

_refine_diff_density_max         0.900
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.056

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b17061r
_database_code_depnum_ccdc_archive 'CCDC 1558621'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
;
p-Hydroxyphenyl-2,2,4,6-tetramethylchroman
;
_chemical_name_common            
;
6-Methyl Dianin's compound
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 O2'
_chemical_formula_sum            'C19 H22 O2'
_chemical_formula_weight         282.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.14913(16)
_cell_length_b                   6.42088(6)
_cell_length_c                   18.3566(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.9730(13)
_cell_angle_gamma                90
_cell_volume                     1546.55(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    8173
_cell_measurement_theta_min      4.9570
_cell_measurement_theta_max      76.3570

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    0.603
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43a (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dualflex, AtlasS2'
_diffrn_detector_area_resol_mean 5.2921
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            13535
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.397
_diffrn_reflns_theta_max         74.480
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3154
_reflns_number_gt                2924
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXD-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, 2001), Mercury CSD 2.0 (Macrae et al., 2008)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3154
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53718(5) 0.42589(12) 0.82312(4) 0.01700(17) Uani 1 1 d . . . . .
O2 O 0.06122(6) 0.36999(14) 0.44038(5) 0.0261(2) Uani 1 1 d . . . . .
H2 H 0.0652(12) 0.264(3) 0.4093(10) 0.046(5) Uiso 1 1 d . . . . .
C1 C 0.70371(9) 0.20511(19) 0.59573(6) 0.0239(2) Uani 1 1 d . . . . .
H1A H 0.6723 0.0755 0.5696 0.036 Uiso 1 1 calc R U . . .
H1B H 0.7772 0.1843 0.6228 0.036 Uiso 1 1 calc R U . . .
H1C H 0.6915 0.3158 0.5565 0.036 Uiso 1 1 calc R U . . .
C2 C 0.43750(7) 0.52719(17) 0.79928(6) 0.0168(2) Uani 1 1 d . . . . .
C3 C 0.43563(8) 0.70148(16) 0.74240(6) 0.0169(2) Uani 1 1 d . . . . .
H3A H 0.4913 0.8005 0.7697 0.020 Uiso 1 1 calc R U . . .
H3B H 0.3704 0.7778 0.7283 0.020 Uiso 1 1 calc R U . . .
C4 C 0.44734(7) 0.62922(15) 0.66608(6) 0.0144(2) Uani 1 1 d . . . . .
C5 C 0.57726(7) 0.40606(16) 0.63566(6) 0.0159(2) Uani 1 1 d . . . . .
H5 H 0.5518 0.4645 0.5844 0.019 Uiso 1 1 calc R U . . .
C6 C 0.65768(7) 0.26611(16) 0.65463(6) 0.0164(2) Uani 1 1 d . . . . .
C7 C 0.69484(7) 0.18199(16) 0.73034(6) 0.0169(2) Uani 1 1 d . . . . .
H7 H 0.7504 0.0872 0.7451 0.020 Uiso 1 1 calc R U . . .
C8 C 0.65161(7) 0.23523(16) 0.78393(6) 0.0164(2) Uani 1 1 d . . . . .
H8 H 0.6771 0.1756 0.8350 0.020 Uiso 1 1 calc R U . . .
C9 C 0.57070(7) 0.37620(16) 0.76342(6) 0.0147(2) Uani 1 1 d . . . . .
C10 C 0.53171(7) 0.46538(16) 0.68849(6) 0.0144(2) Uani 1 1 d . . . . .
C11 C 0.34524(7) 0.54930(16) 0.60547(5) 0.0144(2) Uani 1 1 d . . . . .
C12 C 0.25796(8) 0.67360(17) 0.58707(6) 0.0171(2) Uani 1 1 d . . . . .
H12 H 0.2631 0.8043 0.6125 0.021 Uiso 1 1 calc R U . . .
C13 C 0.16434(8) 0.61111(18) 0.53276(6) 0.0196(2) Uani 1 1 d . . . . .
H13 H 0.1062 0.6975 0.5222 0.024 Uiso 1 1 calc R U . . .
C14 C 0.15539(8) 0.42227(18) 0.49373(6) 0.0186(2) Uani 1 1 d . . . . .
C15 C 0.24068(8) 0.29642(17) 0.51048(6) 0.0177(2) Uani 1 1 d . . . . .
H15 H 0.2353 0.1666 0.4844 0.021 Uiso 1 1 calc R U . . .
C16 C 0.33442(8) 0.36077(16) 0.56576(6) 0.0163(2) Uani 1 1 d . . . . .
H16 H 0.3923 0.2735 0.5765 0.020 Uiso 1 1 calc R U . . .
C17 C 0.48005(8) 0.82103(17) 0.63038(6) 0.0199(2) Uani 1 1 d . . . . .
H17A H 0.4305 0.9335 0.6230 0.030 Uiso 1 1 calc R U . . .
H17B H 0.4830 0.7834 0.5795 0.030 Uiso 1 1 calc R U . . .
H17C H 0.5474 0.8679 0.6660 0.030 Uiso 1 1 calc R U . . .
C18 C 0.43324(9) 0.6188(2) 0.87445(6) 0.0244(2) Uani 1 1 d . . . . .
H18A H 0.4484 0.5097 0.9146 0.037 Uiso 1 1 calc R U . . .
H18B H 0.3649 0.6747 0.8639 0.037 Uiso 1 1 calc R U . . .
H18C H 0.4836 0.7308 0.8933 0.037 Uiso 1 1 calc R U . . .
C19 C 0.35626(8) 0.35961(18) 0.76617(6) 0.0209(2) Uani 1 1 d . . . . .
H19A H 0.3675 0.2865 0.7232 0.031 Uiso 1 1 calc R U . . .
H19B H 0.2887 0.4245 0.7463 0.031 Uiso 1 1 calc R U . . .
H19C H 0.3604 0.2601 0.8077 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3844(12) . ?
O1 C2 1.4635(11) . ?
O2 C14 1.3677(12) . ?
O2 H2 0.902(19) . ?
C1 C6 1.5078(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C18 1.5218(14) . ?
C2 C3 1.5240(14) . ?
C2 C19 1.5250(14) . ?
C3 C4 1.5425(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C10 1.5276(13) . ?
C4 C11 1.5445(13) . ?
C4 C17 1.5450(14) . ?
C5 C6 1.3882(14) . ?
C5 C10 1.4031(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3975(14) . ?
C7 C8 1.3816(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.3962(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.3986(14) . ?
C11 C16 1.3916(14) . ?
C11 C12 1.4014(14) . ?
C12 C13 1.3861(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.3898(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3879(15) . ?
C15 C16 1.3973(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
_geom_angle_publ_flag
C9 O1 C2 116.29(7) . . ?
C14 O2 H2 111.3(11) . . ?
C6 C1 H1A 109.5 . . ?
C6 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C6 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C18 105.15(8) . . ?
O1 C2 C3 107.39(8) . . ?
C18 C2 C3 109.94(9) . . ?
O1 C2 C19 107.69(8) . . ?
C18 C2 C19 110.75(9) . . ?
C3 C2 C19 115.33(8) . . ?
C2 C3 C4 114.91(8) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C10 C4 C3 107.53(8) . . ?
C10 C4 C11 113.03(8) . . ?
C3 C4 C11 111.39(8) . . ?
C10 C4 C17 109.59(8) . . ?
C3 C4 C17 107.24(8) . . ?
C11 C4 C17 107.89(8) . . ?
C6 C5 C10 123.21(9) . . ?
C6 C5 H5 118.4 . . ?
C10 C5 H5 118.4 . . ?
C5 C6 C7 117.89(9) . . ?
C5 C6 C1 121.45(9) . . ?
C7 C6 C1 120.66(9) . . ?
C8 C7 C6 120.69(9) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.35(9) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O1 C9 C8 115.16(9) . . ?
O1 C9 C10 123.93(9) . . ?
C8 C9 C10 120.83(9) . . ?
C9 C10 C5 117.03(9) . . ?
C9 C10 C4 121.85(9) . . ?
C5 C10 C4 121.04(9) . . ?
C16 C11 C12 117.05(9) . . ?
C16 C11 C4 123.80(9) . . ?
C12 C11 C4 119.13(9) . . ?
C13 C12 C11 121.82(10) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 120.10(10) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O2 C14 C15 123.30(10) . . ?
O2 C14 C13 117.37(10) . . ?
C15 C14 C13 119.32(9) . . ?
C14 C15 C16 119.94(10) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 121.75(9) . . ?
C11 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C2 C18 -164.18(9) . . . . ?
C9 O1 C2 C3 -47.11(11) . . . . ?
C9 O1 C2 C19 77.68(10) . . . . ?
O1 C2 C3 C4 61.95(10) . . . . ?
C18 C2 C3 C4 175.84(8) . . . . ?
C19 C2 C3 C4 -58.10(12) . . . . ?
C2 C3 C4 C10 -43.38(11) . . . . ?
C2 C3 C4 C11 80.98(10) . . . . ?
C2 C3 C4 C17 -161.17(8) . . . . ?
C10 C5 C6 C7 -0.34(15) . . . . ?
C10 C5 C6 C1 179.40(10) . . . . ?
C5 C6 C7 C8 0.80(15) . . . . ?
C1 C6 C7 C8 -178.94(10) . . . . ?
C6 C7 C8 C9 -0.76(15) . . . . ?
C2 O1 C9 C8 -164.43(9) . . . . ?
C2 O1 C9 C10 18.68(14) . . . . ?
C7 C8 C9 O1 -176.76(9) . . . . ?
C7 C8 C9 C10 0.23(15) . . . . ?
O1 C9 C10 C5 176.94(9) . . . . ?
C8 C9 C10 C5 0.22(14) . . . . ?
O1 C9 C10 C4 0.26(15) . . . . ?
C8 C9 C10 C4 -176.46(9) . . . . ?
C6 C5 C10 C9 -0.16(15) . . . . ?
C6 C5 C10 C4 176.55(9) . . . . ?
C3 C4 C10 C9 12.04(13) . . . . ?
C11 C4 C10 C9 -111.33(10) . . . . ?
C17 C4 C10 C9 128.30(10) . . . . ?
C3 C4 C10 C5 -164.51(9) . . . . ?
C11 C4 C10 C5 72.12(12) . . . . ?
C17 C4 C10 C5 -48.25(12) . . . . ?
C10 C4 C11 C16 -9.67(13) . . . . ?
C3 C4 C11 C16 -130.88(10) . . . . ?
C17 C4 C11 C16 111.67(11) . . . . ?
C10 C4 C11 C12 171.98(9) . . . . ?
C3 C4 C11 C12 50.77(12) . . . . ?
C17 C4 C11 C12 -66.68(11) . . . . ?
C16 C11 C12 C13 1.06(15) . . . . ?
C4 C11 C12 C13 179.53(9) . . . . ?
C11 C12 C13 C14 -1.19(16) . . . . ?
C12 C13 C14 O2 -179.48(10) . . . . ?
C12 C13 C14 C15 0.83(16) . . . . ?
O2 C14 C15 C16 179.94(10) . . . . ?
C13 C14 C15 C16 -0.39(16) . . . . ?
C12 C11 C16 C15 -0.61(15) . . . . ?
C4 C11 C16 C15 -179.00(9) . . . . ?
C14 C15 C16 C11 0.30(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.902(19) 1.919(19) 2.7947(11) 163.4(16) 4_565

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6

