# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_fayz002
_database_code_depnum_ccdc_archive 'CCDC 2306559'
loop_
_audit_author_name
_audit_author_address
'Robert R. Fayzullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, RAS
Russia
;
_audit_update_record             
;
2023-11-08 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      102(2)
_chemical_formula_weight         210.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   16.589(2)
_cell_length_b                   8.8658(11)
_cell_length_c                   8.1243(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.606(4)
_cell_angle_gamma                90
_cell_volume                     1161.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    102(2)
_cell_measurement_reflns_used    5214
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.46
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8594
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Stalke et al., 2015)

 Equivalent reflections defined by point group 2/m for scaling and error model
 Mean and maximum errors in direction cosine check function =   0.001   0.015
 Restraint esd for equal adjacent scale factors =  0.0060
 Maximum odd and even orders for spherical harmonics =   1   4
 wR2(int) =  0.1376 (selected reflections only, before parameter refinement)
 wR2(int) =  0.0546 (selected reflections only, after parameter refinement)

   12304 total and   2785 unique reflections assuming Friedel's law
 plus   1288 total and   800 unique reflections in fast scans
 Reflections rejected for which |I-|/su >   3.00
 where:  su^2 = sigma(I)^2 + (  0.04000 )^2  (sigma(I) from SAINT)

   12112 total and   2783 unique reflections left after |I-|/su test
 plus   1135 total and   745 unique reflections in fast scans
 su^2 = [K*sigma(I)]^2 + [g]^2  where sigma(I) is from SAINT

 Error model 5: refine all K and overall g
 Run 2theta R(int) Incid. factors Diffr. factors    K      g   I/s(lim) Total I>2sig(I)
   1  15.9  0.0426  0.208 - 0.440  0.903 - 1.044  0.922  0.0405  24.7    4174    2820
   2  15.9  0.0386  0.145 - 0.233  0.937 - 1.044  0.884  0.0405  24.7    2491    1882
   3  15.9  0.0443  0.175 - 0.387  0.903 - 1.038  0.918  0.0405  24.7    4279    2994
   4  15.9  0.0415  0.108 - 0.208  0.924 - 1.023  1.011  0.0405  24.7    1168     830
   5f  0.0  0.1101  0.117 - 0.323  0.903 - 1.038  1.721  0.0405  24.7    1135     630

       3 Overloads replaced by fast scan measurements
   12115 Corrected reflections written to file hkl
 Estimated minimum and maximum transmission:  0.8594  1.0000
 Additional spherical absorption correction applied with mu*r =  0.0000
 3lambda correction factor = 0.00150
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus Mo X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11487
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.526
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2609
_reflns_number_gt                2097
_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       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_cell_refinement       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_data_reduction        'APEX4 v2021.10-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_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 > 2sigma(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+0.6249P] 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         2609
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1408
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.50618(8) 0.30866(15) 0.07296(15) 0.0266(3) Uani 1 1 d D . . . .
H1 H 0.5184(13) 0.347(3) -0.019(2) 0.036(6) Uiso 1 1 d D . . . .
O2 O 0.44768(8) 0.59054(14) 0.19919(15) 0.0256(3) Uani 1 1 d D . . . .
H2 H 0.4560(14) 0.647(3) 0.291(3) 0.050(7) Uiso 1 1 d D . . . .
O3 O 0.35073(7) 0.52190(15) 0.43456(14) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.42411(11) 0.3440(2) 0.0826(2) 0.0240(4) Uani 1 1 d . . . . .
H1A H 0.393208 0.249766 0.090171 0.029 Uiso 1 1 calc R U . . .
H1B H 0.395472 0.398177 -0.021352 0.029 Uiso 1 1 calc R U . . .
C2 C 0.42497(10) 0.44187(19) 0.2366(2) 0.0213(4) Uani 1 1 d . . . . .
H2A H 0.467534 0.401985 0.335268 0.026 Uiso 1 1 calc R U . . .
C3 C 0.34140(11) 0.4407(2) 0.2796(2) 0.0240(4) Uani 1 1 d . . . . .
H3A H 0.299358 0.489732 0.188522 0.029 Uiso 1 1 calc R U . . .
H3B H 0.323525 0.335795 0.293175 0.029 Uiso 1 1 calc R U . . .
C4 C 0.28537(10) 0.52147(19) 0.5114(2) 0.0216(4) Uani 1 1 d . . . . .
C9 C 0.21122(11) 0.4449(2) 0.4518(2) 0.0247(4) Uani 1 1 d . . . . .
H9 H 0.202230 0.388413 0.349729 0.030 Uiso 1 1 calc R U . . .
C8 C 0.15021(11) 0.4521(2) 0.5435(2) 0.0244(4) Uani 1 1 d . . . . .
H8 H 0.099885 0.398369 0.502995 0.029 Uiso 1 1 calc R U . . .
C7 C 0.16028(11) 0.53479(19) 0.6920(2) 0.0226(4) Uani 1 1 d . . . . .
C6 C 0.23563(11) 0.6113(2) 0.7485(2) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.244534 0.668921 0.849780 0.033 Uiso 1 1 calc R U . . .
C5 C 0.29728(11) 0.6049(2) 0.6602(2) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.347917 0.657477 0.701178 0.033 Uiso 1 1 calc R U . . .
C10 C 0.09185(10) 0.5434(2) 0.7864(2) 0.0231(4) Uani 1 1 d . . . . .
H10 H 0.047392 0.470926 0.731681 0.028 Uiso 1 1 calc R U . . .
C11 C 0.05337(11) 0.7012(2) 0.7738(2) 0.0266(4) Uani 1 1 d . . . . .
H11A H 0.034430 0.729748 0.654404 0.040 Uiso 1 1 calc R U . . .
H11B H 0.094935 0.773891 0.832001 0.040 Uiso 1 1 calc R U . . .
H11C H 0.006113 0.701099 0.826990 0.040 Uiso 1 1 calc R U . . .
C12 C 0.12214(12) 0.4975(2) 0.9725(2) 0.0297(4) Uani 1 1 d . . . . .
H12A H 0.163294 0.570612 1.031119 0.044 Uiso 1 1 calc R U . . .
H12B H 0.147435 0.397099 0.979256 0.044 Uiso 1 1 calc R U . . .
H12C H 0.075061 0.495387 1.026135 0.044 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 C1 1.417(2) . ?
O1 H1 0.884(18) . ?
O2 C2 1.423(2) . ?
O2 H2 0.884(19) . ?
O3 C4 1.3724(19) . ?
O3 C3 1.4271(19) . ?
C1 C2 1.520(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.507(2) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.388(2) . ?
C4 C5 1.391(2) . ?
C9 C8 1.392(2) . ?
C9 H9 0.9500 . ?
C8 C7 1.388(2) . ?
C8 H8 0.9500 . ?
C7 C6 1.401(2) . ?
C7 C10 1.514(2) . ?
C6 C5 1.382(2) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C10 C12 1.531(2) . ?
C10 C11 1.532(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 O1 H1 112.0(14) . . ?
C2 O2 H2 110.0(17) . . ?
C4 O3 C3 117.81(13) . . ?
O1 C1 C2 110.40(14) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
O2 C2 C3 111.11(14) . . ?
O2 C2 C1 107.72(13) . . ?
C3 C2 C1 110.84(14) . . ?
O2 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
O3 C3 C2 106.63(13) . . ?
O3 C3 H3A 110.4 . . ?
C2 C3 H3A 110.4 . . ?
O3 C3 H3B 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O3 C4 C9 124.94(15) . . ?
O3 C4 C5 115.33(15) . . ?
C9 C4 C5 119.73(15) . . ?
C4 C9 C8 119.15(15) . . ?
C4 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C7 C8 C9 122.36(16) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C7 C6 117.14(15) . . ?
C8 C7 C10 121.04(15) . . ?
C6 C7 C10 121.81(15) . . ?
C5 C6 C7 121.47(16) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C5 C4 120.14(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C10 C12 112.07(14) . . ?
C7 C10 C11 111.24(14) . . ?
C12 C10 C11 110.09(14) . . ?
C7 C10 H10 107.7 . . ?
C12 C10 H10 107.7 . . ?
C11 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O1 C1 C2 O2 75.81(17) . . . . ?
O1 C1 C2 C3 -162.45(13) . . . . ?
C4 O3 C3 C2 -172.37(13) . . . . ?
O2 C2 C3 O3 -66.17(17) . . . . ?
C1 C2 C3 O3 174.10(13) . . . . ?
C3 O3 C4 C9 1.6(2) . . . . ?
C3 O3 C4 C5 -178.79(15) . . . . ?
O3 C4 C9 C8 179.04(15) . . . . ?
C5 C4 C9 C8 -0.6(3) . . . . ?
C4 C9 C8 C7 0.8(3) . . . . ?
C9 C8 C7 C6 -0.6(3) . . . . ?
C9 C8 C7 C10 178.46(16) . . . . ?
C8 C7 C6 C5 0.0(3) . . . . ?
C10 C7 C6 C5 -178.97(16) . . . . ?
C7 C6 C5 C4 0.2(3) . . . . ?
O3 C4 C5 C6 -179.57(16) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C8 C7 C10 C12 126.14(18) . . . . ?
C6 C7 C10 C12 -54.9(2) . . . . ?
C8 C7 C10 C11 -110.13(18) . . . . ?
C6 C7 C10 C11 68.8(2) . . . . ?

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
_geom_hbond_publ_flag
O1 H1 O2 0.884(18) 1.779(18) 2.6589(16) 174(2) 3_665 yes
O2 H2 O1 0.884(19) 1.83(2) 2.6619(17) 157(2) 2_655 yes

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_fayz003
_database_code_depnum_ccdc_archive 'CCDC 2306560'
loop_
_audit_author_name
_audit_author_address
'Robert R. Fayzullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, RAS
Russia
;
_audit_update_record             
;
2023-11-08 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      102(2)
_chemical_formula_weight         210.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_chemical_absolute_configuration rmad

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

_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.
;

_cell_length_a                   4.83470(10)
_cell_length_b                   20.8619(5)
_cell_length_c                   22.8684(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2306.53(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    102(2)
_cell_measurement_reflns_used    40004
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      32.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9416
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Stalke et al., 2015)

 Equivalent reflections defined by point group 222 for scaling and error model
 Mean and maximum errors in direction cosine check function =   0.000   0.000
 Restraint esd for equal adjacent scale factors =  0.0110
 Maximum odd and even orders for spherical harmonics =   1   4
 wR2(int) =  0.1670 (selected reflections only, before parameter refinement)
 wR2(int) =  0.0594 (selected reflections only, after parameter refinement)

  120704 total and   8448 unique reflections.
 Reflections rejected for which |I-|/su >   3.00
 where:  su^2 = sigma(I)^2 + (  0.04000 )^2  (sigma(I) from SAINT)

  119301 total and   8446 unique reflections left after |I-|/su test
 su^2 = [K*sigma(I)]^2 + [g]^2  where sigma(I) is from SAINT

 Error model 5: refine all K and overall g
 Run 2theta R(int) Incid. factors Diffr. factors    K      g   I/s(lim) Total I>2sig(I)
   1  22.0  0.0568  0.123 - 0.412  0.992 - 1.023  0.946  0.0249  40.1   14826   10212
   2  22.0  0.0504  0.330 - 0.414  0.998 - 1.036  0.895  0.0249  40.1   11728    8500
   3  21.9  0.0538  0.105 - 0.336  0.992 - 1.036  0.967  0.0249  40.1   14619   10104
   4  21.9  0.0504  0.063 - 0.313  0.992 - 1.036  0.978  0.0249  40.1   14428   10368
   5  21.9  0.0566  0.192 - 0.281  0.992 - 1.036  0.967  0.0249  40.1   14577   10543
   6  21.9  0.0538  0.074 - 0.342  0.992 - 1.036  0.971  0.0249  40.1   14404   10125
   7  21.9  0.0502  0.102 - 0.311  0.992 - 1.024  1.049  0.0249  40.1   11207    8564
   8   0.0  0.0464  0.180 - 0.318  0.992 - 1.033  1.010  0.0249  40.1   10816    8935
   9   0.0  0.0492  0.241 - 0.399  0.996 - 1.036  0.988  0.0249  40.1    8595    7011
  10   0.0  0.0764  0.266 - 0.307  0.993 - 1.017  1.017  0.0249  40.1    4101    3056

  119301 Corrected reflections written to file hkl
 Estimated minimum and maximum transmission:  0.9416  1.0000
 The ratio of these values is more reliable than their absolute values!
 3lambda correction factor = 0.00150
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus Mo X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            117718
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         32.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8031
_reflns_number_gt                7012
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_cell_refinement       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_data_reduction        'APEX4 v2021.10-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_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 > 2sigma(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0711P)²+0.3186P] 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 2761 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_number_reflns         8031
_refine_ls_number_parameters     291
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.8685(2) 0.24258(6) 0.40864(6) 0.0220(2) Uani 1 1 d D . . . .
H1A H 0.929(6) 0.2810(9) 0.4127(11) 0.034(7) Uiso 1 1 d D . . . .
O2A O 0.2386(2) 0.15462(6) 0.44017(5) 0.0205(2) Uani 1 1 d D . . . .
H2A H 0.130(5) 0.1839(11) 0.4261(11) 0.038(7) Uiso 1 1 d D . . . .
O3A O 0.3355(3) 0.19910(6) 0.32504(5) 0.0213(2) Uani 1 1 d . . . . .
C1A C 0.5973(3) 0.23363(8) 0.43140(7) 0.0181(3) Uani 1 1 d . . . . .
H1AA H 0.468179 0.264956 0.413720 0.022 Uiso 1 1 calc R U . . .
H1AB H 0.597289 0.239953 0.474305 0.022 Uiso 1 1 calc R U . . .
C2A C 0.5075(3) 0.16565(7) 0.41660(7) 0.0168(3) Uani 1 1 d . . . . .
H2AA H 0.639009 0.135295 0.435895 0.020 Uiso 1 1 calc R U . . .
C3A C 0.5091(3) 0.15193(8) 0.35136(7) 0.0190(3) Uani 1 1 d . . . . .
H3AA H 0.699401 0.154963 0.335626 0.023 Uiso 1 1 calc R U . . .
H3AB H 0.436987 0.108362 0.343491 0.023 Uiso 1 1 calc R U . . .
C4A C 0.2298(3) 0.18749(8) 0.27053(7) 0.0181(3) Uani 1 1 d . . . . .
C5A C 0.3061(4) 0.13664(9) 0.23494(8) 0.0255(3) Uani 1 1 d . . . . .
H5A H 0.442289 0.106949 0.247694 0.031 Uiso 1 1 calc R U . . .
C6A C 0.1818(4) 0.12935(9) 0.18034(8) 0.0270(4) Uani 1 1 d . . . . .
H6A H 0.233372 0.094030 0.156499 0.032 Uiso 1 1 calc R U . . .
C7A C -0.0154(4) 0.17223(8) 0.15979(7) 0.0217(3) Uani 1 1 d . . . . .
C8A C -0.0904(4) 0.22269(8) 0.19688(8) 0.0262(4) Uani 1 1 d . . . . .
H8A H -0.227293 0.252311 0.184328 0.031 Uiso 1 1 calc R U . . .
C9A C 0.0297(4) 0.23061(8) 0.25139(8) 0.0255(4) Uani 1 1 d . . . . .
H9A H -0.024445 0.265380 0.275653 0.031 Uiso 1 1 calc R U . . .
C10A C -0.1444(4) 0.16702(9) 0.09942(8) 0.0272(4) Uani 1 1 d . . . . .
H10A H -0.328338 0.188884 0.101026 0.033 Uiso 1 1 calc R U . . .
C11A C -0.1945(5) 0.09809(11) 0.07943(9) 0.0363(5) Uani 1 1 d . . . . .
H11A H -0.016546 0.076555 0.073551 0.054 Uiso 1 1 calc R U . . .
H11B H -0.298157 0.098333 0.042602 0.054 Uiso 1 1 calc R U . . .
H11C H -0.300992 0.075194 0.109319 0.054 Uiso 1 1 calc R U . . .
C12A C 0.0317(6) 0.20245(11) 0.05414(9) 0.0388(5) Uani 1 1 d . . . . .
H12A H 0.059414 0.246883 0.066765 0.058 Uiso 1 1 calc R U . . .
H12B H -0.063022 0.202007 0.016255 0.058 Uiso 1 1 calc R U . . .
H12C H 0.211520 0.181153 0.050408 0.058 Uiso 1 1 calc R U . . .
O1B O 0.5603(3) 0.39558(6) 0.45898(5) 0.0218(2) Uani 1 1 d D . . . .
H1B H 0.620(6) 0.3770(12) 0.4904(10) 0.047(8) Uiso 1 1 d D . . . .
O2B O 1.0855(2) 0.36221(6) 0.40523(6) 0.0218(2) Uani 1 1 d D . . . .
H2B H 1.235(4) 0.3733(13) 0.4234(11) 0.039(7) Uiso 1 1 d D . . . .
O3B O 0.5742(3) 0.44859(5) 0.32342(5) 0.0185(2) Uani 1 1 d . . . . .
C1B C 0.7578(3) 0.44171(8) 0.44008(7) 0.0184(3) Uani 1 1 d . . . . .
H1BA H 0.881998 0.452490 0.473060 0.022 Uiso 1 1 calc R U . . .
H1BB H 0.660353 0.481373 0.428218 0.022 Uiso 1 1 calc R U . . .
C2B C 0.9293(3) 0.41742(7) 0.38916(7) 0.0170(3) Uani 1 1 d . . . . .
H2BA H 1.059321 0.452015 0.376475 0.020 Uiso 1 1 calc R U . . .
C3B C 0.7554(3) 0.39674(8) 0.33708(7) 0.0174(3) Uani 1 1 d . . . . .
H3BA H 0.875771 0.386919 0.303222 0.021 Uiso 1 1 calc R U . . .
H3BB H 0.647424 0.357886 0.346898 0.021 Uiso 1 1 calc R U . . .
C4B C 0.4175(3) 0.44257(7) 0.27402(6) 0.0163(3) Uani 1 1 d . . . . .
C5B C 0.4125(4) 0.38923(8) 0.23778(7) 0.0202(3) Uani 1 1 d . . . . .
H5B H 0.522352 0.352748 0.246660 0.024 Uiso 1 1 calc R U . . .
C6B C 0.2444(4) 0.38972(8) 0.18809(7) 0.0222(3) Uani 1 1 d . . . . .
H6B H 0.242016 0.353082 0.163432 0.027 Uiso 1 1 calc R U . . .
C7B C 0.0808(4) 0.44195(8) 0.17362(7) 0.0210(3) Uani 1 1 d . . . . .
C8B C 0.0829(4) 0.49442(8) 0.21197(7) 0.0214(3) Uani 1 1 d . . . . .
H8B H -0.030898 0.530421 0.203707 0.026 Uiso 1 1 calc R U . . .
C9B C 0.2465(4) 0.49494(7) 0.26143(7) 0.0186(3) Uani 1 1 d . . . . .
H9B H 0.243074 0.530857 0.286955 0.022 Uiso 1 1 calc R U . . .
C10B C -0.0867(5) 0.44701(9) 0.11790(8) 0.0290(4) Uani 1 1 d . . . . .
H10B H -0.269130 0.466669 0.128074 0.035 Uiso 1 1 calc R U . . .
C11B C -0.1432(5) 0.38325(10) 0.08817(10) 0.0359(5) Uani 1 1 d . . . . .
H11D H 0.031234 0.364914 0.074175 0.054 Uiso 1 1 calc R U . . .
H11E H -0.268251 0.389919 0.054990 0.054 Uiso 1 1 calc R U . . .
H11F H -0.229175 0.353783 0.116164 0.054 Uiso 1 1 calc R U . . .
C12B C 0.0601(7) 0.49218(11) 0.07522(10) 0.0458(6) Uani 1 1 d . . . . .
H12D H 0.081018 0.534499 0.093297 0.069 Uiso 1 1 calc R U . . .
H12E H -0.049683 0.496109 0.039379 0.069 Uiso 1 1 calc R U . . .
H12F H 0.243036 0.474851 0.065673 0.069 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
O1A C1A 1.4233(19) . ?
O1A H1A 0.857(18) . ?
O2A C2A 1.4261(19) . ?
O2A H2A 0.868(17) . ?
O3A C4A 1.3689(19) . ?
O3A C3A 1.426(2) . ?
C1A C2A 1.521(2) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C2A C3A 1.519(2) . ?
C2A H2AA 1.0000 . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C5A 1.387(2) . ?
C4A C9A 1.392(2) . ?
C5A C6A 1.394(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.389(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.400(2) . ?
C7A C10A 1.519(2) . ?
C8A C9A 1.385(3) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.528(3) . ?
C10A C12A 1.531(3) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
O1B C1B 1.4231(19) . ?
O1B H1B 0.865(18) . ?
O2B C2B 1.4252(19) . ?
O2B H2B 0.867(18) . ?
O3B C4B 1.3661(18) . ?
O3B C3B 1.4267(19) . ?
C1B C2B 1.517(2) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B C3B 1.520(2) . ?
C2B H2BA 1.0000 . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B C5B 1.388(2) . ?
C4B C9B 1.400(2) . ?
C5B C6B 1.397(2) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.386(2) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.403(2) . ?
C7B C10B 1.514(2) . ?
C8B C9B 1.380(2) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.518(3) . ?
C10B C12B 1.531(3) . ?
C10B H10B 1.0000 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 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
C1A O1A H1A 113.3(19) . . ?
C2A O2A H2A 107.4(19) . . ?
C4A O3A C3A 118.81(12) . . ?
O1A C1A C2A 107.69(13) . . ?
O1A C1A H1AA 110.2 . . ?
C2A C1A H1AA 110.2 . . ?
O1A C1A H1AB 110.2 . . ?
C2A C1A H1AB 110.2 . . ?
H1AA C1A H1AB 108.5 . . ?
O2A C2A C3A 110.21(13) . . ?
O2A C2A C1A 109.06(13) . . ?
C3A C2A C1A 113.11(13) . . ?
O2A C2A H2AA 108.1 . . ?
C3A C2A H2AA 108.1 . . ?
C1A C2A H2AA 108.1 . . ?
O3A C3A C2A 106.35(12) . . ?
O3A C3A H3AA 110.5 . . ?
C2A C3A H3AA 110.5 . . ?
O3A C3A H3AB 110.5 . . ?
C2A C3A H3AB 110.5 . . ?
H3AA C3A H3AB 108.7 . . ?
O3A C4A C5A 124.78(15) . . ?
O3A C4A C9A 115.57(14) . . ?
C5A C4A C9A 119.65(16) . . ?
C4A C5A C6A 119.63(16) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C7A C6A C5A 121.91(16) . . ?
C7A C6A H6A 119.0 . . ?
C5A C6A H6A 119.0 . . ?
C6A C7A C8A 117.20(16) . . ?
C6A C7A C10A 122.91(16) . . ?
C8A C7A C10A 119.88(16) . . ?
C9A C8A C7A 121.78(17) . . ?
C9A C8A H8A 119.1 . . ?
C7A C8A H8A 119.1 . . ?
C8A C9A C4A 119.82(16) . . ?
C8A C9A H9A 120.1 . . ?
C4A C9A H9A 120.1 . . ?
C7A C10A C11A 113.84(16) . . ?
C7A C10A C12A 110.60(17) . . ?
C11A C10A C12A 109.89(17) . . ?
C7A C10A H10A 107.4 . . ?
C11A C10A H10A 107.4 . . ?
C12A C10A H10A 107.4 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C1B O1B H1B 109(2) . . ?
C2B O2B H2B 110.5(18) . . ?
C4B O3B C3B 116.88(12) . . ?
O1B C1B C2B 111.97(13) . . ?
O1B C1B H1BA 109.2 . . ?
C2B C1B H1BA 109.2 . . ?
O1B C1B H1BB 109.2 . . ?
C2B C1B H1BB 109.2 . . ?
H1BA C1B H1BB 107.9 . . ?
O2B C2B C1B 111.20(13) . . ?
O2B C2B C3B 105.40(12) . . ?
C1B C2B C3B 113.19(13) . . ?
O2B C2B H2BA 109.0 . . ?
C1B C2B H2BA 109.0 . . ?
C3B C2B H2BA 109.0 . . ?
O3B C3B C2B 107.22(12) . . ?
O3B C3B H3BA 110.3 . . ?
C2B C3B H3BA 110.3 . . ?
O3B C3B H3BB 110.3 . . ?
C2B C3B H3BB 110.3 . . ?
H3BA C3B H3BB 108.5 . . ?
O3B C4B C5B 125.26(14) . . ?
O3B C4B C9B 115.20(13) . . ?
C5B C4B C9B 119.53(14) . . ?
C4B C5B C6B 119.33(15) . . ?
C4B C5B H5B 120.3 . . ?
C6B C5B H5B 120.3 . . ?
C7B C6B C5B 122.13(15) . . ?
C7B C6B H6B 118.9 . . ?
C5B C6B H6B 118.9 . . ?
C6B C7B C8B 117.39(15) . . ?
C6B C7B C10B 124.13(15) . . ?
C8B C7B C10B 118.40(15) . . ?
C9B C8B C7B 121.50(15) . . ?
C9B C8B H8B 119.2 . . ?
C7B C8B H8B 119.2 . . ?
C8B C9B C4B 120.05(14) . . ?
C8B C9B H9B 120.0 . . ?
C4B C9B H9B 120.0 . . ?
C7B C10B C11B 114.33(16) . . ?
C7B C10B C12B 109.35(18) . . ?
C11B C10B C12B 109.70(18) . . ?
C7B C10B H10B 107.7 . . ?
C11B C10B H10B 107.7 . . ?
C12B C10B H10B 107.7 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 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
O1A C1A C2A O2A 178.54(12) . . . . ?
O1A C1A C2A C3A -58.45(17) . . . . ?
C4A O3A C3A C2A -160.01(14) . . . . ?
O2A C2A C3A O3A 66.24(16) . . . . ?
C1A C2A C3A O3A -56.13(17) . . . . ?
C3A O3A C4A C5A -8.8(2) . . . . ?
C3A O3A C4A C9A 170.51(15) . . . . ?
O3A C4A C5A C6A 179.35(17) . . . . ?
C9A C4A C5A C6A 0.1(3) . . . . ?
C4A C5A C6A C7A 0.9(3) . . . . ?
C5A C6A C7A C8A -1.5(3) . . . . ?
C5A C6A C7A C10A 177.19(18) . . . . ?
C6A C7A C8A C9A 1.2(3) . . . . ?
C10A C7A C8A C9A -177.56(18) . . . . ?
C7A C8A C9A C4A -0.3(3) . . . . ?
O3A C4A C9A C8A -179.73(17) . . . . ?
C5A C4A C9A C8A -0.4(3) . . . . ?
C6A C7A C10A C11A 36.7(3) . . . . ?
C8A C7A C10A C11A -144.6(2) . . . . ?
C6A C7A C10A C12A -87.6(2) . . . . ?
C8A C7A C10A C12A 91.1(2) . . . . ?
O1B C1B C2B O2B -62.08(17) . . . . ?
O1B C1B C2B C3B 56.35(17) . . . . ?
C4B O3B C3B C2B 173.68(13) . . . . ?
O2B C2B C3B O3B 173.99(12) . . . . ?
C1B C2B C3B O3B 52.25(16) . . . . ?
C3B O3B C4B C5B 2.8(2) . . . . ?
C3B O3B C4B C9B -178.76(14) . . . . ?
O3B C4B C5B C6B -179.29(15) . . . . ?
C9B C4B C5B C6B 2.4(2) . . . . ?
C4B C5B C6B C7B -0.1(3) . . . . ?
C5B C6B C7B C8B -1.9(3) . . . . ?
C5B C6B C7B C10B 174.85(18) . . . . ?
C6B C7B C8B C9B 1.7(3) . . . . ?
C10B C7B C8B C9B -175.31(17) . . . . ?
C7B C8B C9B C4B 0.6(3) . . . . ?
O3B C4B C9B C8B 178.85(15) . . . . ?
C5B C4B C9B C8B -2.6(2) . . . . ?
C6B C7B C10B C11B 19.7(3) . . . . ?
C8B C7B C10B C11B -163.57(19) . . . . ?
C6B C7B C10B C12B -103.7(2) . . . . ?
C8B C7B C10B C12B 73.0(2) . . . . ?

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
_geom_hbond_publ_flag
O1A H1A O2B 0.857(18) 1.865(18) 2.7084(17) 168(3) . yes
O2A H2A O1A 0.868(17) 1.804(18) 2.6624(17) 170(3) 1_455 yes
O1B H1B O2A 0.865(18) 1.813(18) 2.6754(17) 174(3) 4_556 yes
O2B H2B O1B 0.867(18) 1.829(18) 2.6954(17) 178(3) 1_655 yes

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052

