# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_bq130
_database_code_depnum_ccdc_archive 'CCDC 2409400'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        9,9'-bifluorenyl-9,9'-diol
_chemical_name_common            ?
_chemical_temperature_decomposition 344.35
_chemical_formula_moiety         'C26 H18 O2, C5 H5 N'
_chemical_formula_sum            'C31 H23 N O2'
_chemical_formula_weight         441.50

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'
N N 0.0061 0.0033 '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           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   20.3320(8)
_cell_length_b                   9.1554(4)
_cell_length_c                   26.9029(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.8120(10)
_cell_angle_gamma                90
_cell_volume                     4740.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9277
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.28

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.411
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_absorpt_special_details   
'Additional spherical absorption correction applied with mu*r =  0.20'
_diffrn_ambient_temperature      200(2)
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_power             70
_diffrn_source_voltage           50
_diffrn_source_current           1.4
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Bruker PHOTON II 7 CCD detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            198861
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.116
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_full        25.242
_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             11766
_reflns_number_gt                10130
_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       'Bruker Instrument Service V6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2019/3 (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2019/3 (Sheldrick, 2015b) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows V2023.1 (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were
placed in calculated positions and were included in the refinement in the riding
model approximation, with Uiso(H) set to 1.2 Ueq(C).

The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program  (Sheldrick, 2015b)) and Uiso(H) allowed to 
refine freely.

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²+1.5055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0076(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11766
_refine_ls_number_parameters     622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
O11 O 0.83208(4) 0.69285(8) 0.28918(3) 0.02592(16) Uani 1 1 d . . . . .
H11 H 0.870170 0.712368 0.284734 0.055(5) Uiso 1 1 calc R . . . .
O12 O 0.72400(4) 0.53705(8) 0.30374(3) 0.02620(16) Uani 1 1 d . . . . .
H12 H 0.712523 0.591491 0.277193 0.044(4) Uiso 1 1 calc R . . . .
O21 O 0.31851(4) 0.25598(9) 0.30750(3) 0.02895(17) Uani 1 1 d . . . . .
H21 H 0.361098 0.275192 0.315853 0.063(5) Uiso 1 1 calc R . . . .
O22 O 0.19316(4) 0.11088(9) 0.28756(3) 0.02843(17) Uani 1 1 d . . . . .
H22 H 0.197206 0.162060 0.262793 0.049(4) Uiso 1 1 calc R . . . .
N3 N 0.94457(6) 0.78278(13) 0.26484(5) 0.0410(3) Uani 1 1 d . . . . .
N4 N 0.45534(6) 0.32328(16) 0.32896(5) 0.0502(3) Uani 1 1 d . . . . .
C11 C 0.84455(5) 0.61753(11) 0.33764(4) 0.0224(2) Uani 1 1 d . . . . .
C12 C 0.77228(5) 0.61157(11) 0.34653(4) 0.0229(2) Uani 1 1 d . . . . .
C21 C 0.30493(5) 0.18303(12) 0.34991(4) 0.0260(2) Uani 1 1 d . . . . .
C22 C 0.22377(5) 0.18510(11) 0.33592(4) 0.0240(2) Uani 1 1 d . . . . .
C31 C 0.99284(8) 0.86795(17) 0.29676(7) 0.0490(3) Uani 1 1 d . . . . .
H31 H 0.995764 0.872329 0.332689 0.059 Uiso 1 1 calc R U . . .
C32 C 1.03854(9) 0.94963(19) 0.28067(9) 0.0640(5) Uani 1 1 d . . . . .
H32 H 1.072109 1.009336 0.304895 0.077 Uiso 1 1 calc R U . . .
C33 C 1.03510(10) 0.9439(2) 0.22986(10) 0.0736(6) Uani 1 1 d . . . . .
H33 H 1.066243 0.999927 0.217756 0.088 Uiso 1 1 calc R U . . .
C34 C 0.98581(11) 0.8558(3) 0.19546(8) 0.0777(6) Uani 1 1 d . . . . .
H34 H 0.982492 0.849765 0.159479 0.093 Uiso 1 1 calc R U . . .
C35 C 0.94138(8) 0.7765(2) 0.21492(7) 0.0571(4) Uani 1 1 d . . . . .
H35 H 0.907427 0.715488 0.191623 0.069 Uiso 1 1 calc R U . . .
C41 C 0.50412(9) 0.3374(2) 0.37539(7) 0.0632(5) Uani 1 1 d . . . . .
H41 H 0.491384 0.325053 0.406145 0.076 Uiso 1 1 calc R U . . .
C42 C 0.57237(9) 0.3692(2) 0.38102(9) 0.0732(6) Uani 1 1 d . . . . .
H42 H 0.605907 0.378438 0.414912 0.088 Uiso 1 1 calc R U . . .
C43 C 0.59085(9) 0.3871(2) 0.33688(10) 0.0739(6) Uani 1 1 d . . . . .
H43 H 0.637629 0.408064 0.339574 0.089 Uiso 1 1 calc R U . . .
C44 C 0.54112(10) 0.3744(2) 0.28885(9) 0.0730(6) Uani 1 1 d . . . . .
H44 H 0.552467 0.388231 0.257576 0.088 Uiso 1 1 calc R U . . .
C45 C 0.47420(8) 0.3411(2) 0.28661(7) 0.0589(4) Uani 1 1 d . . . . .
H45 H 0.439932 0.330433 0.253106 0.071 Uiso 1 1 calc R U . . .
C111 C 0.89995(6) 0.68939(12) 0.38381(4) 0.0256(2) Uani 1 1 d . . . . .
C112 C 0.95059(6) 0.58723(13) 0.40958(4) 0.0287(2) Uani 1 1 d . . . . .
C113 C 1.00646(6) 0.62726(15) 0.45309(5) 0.0366(3) Uani 1 1 d . . . . .
H113 H 1.040388 0.557383 0.470965 0.044 Uiso 1 1 calc R U . . .
C114 C 1.01151(7) 0.77102(16) 0.46974(5) 0.0423(3) Uani 1 1 d . . . . .
H114 H 1.049163 0.799972 0.499508 0.051 Uiso 1 1 calc R U . . .
C115 C 0.96222(7) 0.87347(15) 0.44347(5) 0.0410(3) Uani 1 1 d . . . . .
H115 H 0.967087 0.972097 0.455059 0.049 Uiso 1 1 calc R U . . .
C116 C 0.90559(7) 0.83343(13) 0.40023(5) 0.0332(2) Uani 1 1 d . . . . .
H116 H 0.871688 0.903515 0.382480 0.040 Uiso 1 1 calc R U . . .
C121 C 0.87491(5) 0.46464(11) 0.33781(4) 0.0248(2) Uani 1 1 d . . . . .
C122 C 0.93457(6) 0.44779(12) 0.38151(4) 0.0284(2) Uani 1 1 d . . . . .
C123 C 0.96930(7) 0.31509(15) 0.39167(5) 0.0402(3) Uani 1 1 d . . . . .
H123 H 1.009222 0.303167 0.421766 0.048 Uiso 1 1 calc R U . . .
C124 C 0.94471(8) 0.20055(15) 0.35720(6) 0.0454(3) Uani 1 1 d . . . . .
H124 H 0.967990 0.109087 0.363727 0.054 Uiso 1 1 calc R U . . .
C125 C 0.88642(8) 0.21754(14) 0.31315(5) 0.0406(3) Uani 1 1 d . . . . .
H125 H 0.870516 0.137947 0.289678 0.049 Uiso 1 1 calc R U . . .
C126 C 0.85102(6) 0.35030(12) 0.30303(5) 0.0309(2) Uani 1 1 d . . . . .
H126 H 0.811237 0.362043 0.272821 0.037 Uiso 1 1 calc R U . . .
C131 C 0.74628(6) 0.76309(12) 0.35557(4) 0.0268(2) Uani 1 1 d . . . . .
C132 C 0.73601(6) 0.76843(13) 0.40452(4) 0.0300(2) Uani 1 1 d . . . . .
C133 C 0.71083(7) 0.89419(15) 0.42109(5) 0.0416(3) Uani 1 1 d . . . . .
H133 H 0.703973 0.897729 0.454364 0.050 Uiso 1 1 calc R U . . .
C134 C 0.69595(8) 1.01432(16) 0.38792(6) 0.0485(3) Uani 1 1 d . . . . .
H134 H 0.678571 1.101024 0.398577 0.058 Uiso 1 1 calc R U . . .
C135 C 0.70612(8) 1.00947(15) 0.33939(6) 0.0452(3) Uani 1 1 d . . . . .
H135 H 0.695912 1.093099 0.317309 0.054 Uiso 1 1 calc R U . . .
C136 C 0.73111(7) 0.88346(13) 0.32262(5) 0.0352(3) Uani 1 1 d . . . . .
H136 H 0.737635 0.880136 0.289226 0.042 Uiso 1 1 calc R U . . .
C141 C 0.77412(5) 0.53193(12) 0.39682(4) 0.0249(2) Uani 1 1 d . . . . .
C142 C 0.75320(6) 0.62538(13) 0.42994(4) 0.0286(2) Uani 1 1 d . . . . .
C143 C 0.74756(7) 0.57537(16) 0.47716(5) 0.0382(3) Uani 1 1 d . . . . .
H143 H 0.733975 0.639428 0.499874 0.046 Uiso 1 1 calc R U . . .
C144 C 0.76220(7) 0.42981(17) 0.49036(5) 0.0426(3) Uani 1 1 d . . . . .
H144 H 0.758727 0.393854 0.522549 0.051 Uiso 1 1 calc R U . . .
C145 C 0.78183(7) 0.33614(15) 0.45722(5) 0.0390(3) Uani 1 1 d . . . . .
H145 H 0.791297 0.236596 0.466844 0.047 Uiso 1 1 calc R U . . .
C146 C 0.78789(6) 0.38623(13) 0.40982(4) 0.0305(2) Uani 1 1 d . . . . .
H146 H 0.801157 0.321806 0.387042 0.037 Uiso 1 1 calc R U . . .
C211 C 0.34154(6) 0.25200(14) 0.40343(4) 0.0303(2) Uani 1 1 d . . . . .
C212 C 0.37840(6) 0.14547(16) 0.43887(5) 0.0373(3) Uani 1 1 d . . . . .
C213 C 0.41587(8) 0.1829(2) 0.49045(6) 0.0518(4) Uani 1 1 d . . . . .
H213 H 0.439232 0.110194 0.514988 0.062 Uiso 1 1 calc R U . . .
C214 C 0.41839(8) 0.3277(2) 0.50520(6) 0.0557(4) Uani 1 1 d . . . . .
H214 H 0.444148 0.354829 0.540151 0.067 Uiso 1 1 calc R U . . .
C215 C 0.38382(8) 0.43399(19) 0.46970(5) 0.0480(3) Uani 1 1 d . . . . .
H215 H 0.387047 0.533343 0.480412 0.058 Uiso 1 1 calc R U . . .
C216 C 0.34430(7) 0.39698(15) 0.41837(5) 0.0363(3) Uani 1 1 d . . . . .
H216 H 0.319886 0.469737 0.394290 0.044 Uiso 1 1 calc R U . . .
C221 C 0.33330(6) 0.02696(13) 0.35844(5) 0.0318(2) Uani 1 1 d . . . . .
C222 C 0.37294(6) 0.00614(15) 0.41101(5) 0.0382(3) Uani 1 1 d . . . . .
C223 C 0.40281(8) -0.12943(18) 0.42819(7) 0.0522(4) Uani 1 1 d . . . . .
H223 H 0.429294 -0.144444 0.464006 0.063 Uiso 1 1 calc R U . . .
C224 C 0.39317(8) -0.24197(17) 0.39208(8) 0.0567(4) Uani 1 1 d . . . . .
H224 H 0.413415 -0.334812 0.403267 0.068 Uiso 1 1 calc R U . . .
C225 C 0.35454(8) -0.22073(16) 0.34010(7) 0.0505(4) Uani 1 1 d . . . . .
H225 H 0.348579 -0.299089 0.315899 0.061 Uiso 1 1 calc R U . . .
C226 C 0.32408(7) -0.08553(14) 0.32259(6) 0.0396(3) Uani 1 1 d . . . . .
H226 H 0.297544 -0.071164 0.286751 0.048 Uiso 1 1 calc R U . . .
C231 C 0.19581(5) 0.34008(12) 0.33571(4) 0.0260(2) Uani 1 1 d . . . . .
C232 C 0.16498(6) 0.35527(13) 0.37500(4) 0.0281(2) Uani 1 1 d . . . . .
C233 C 0.13388(7) 0.48580(15) 0.38125(5) 0.0392(3) Uani 1 1 d . . . . .
H233 H 0.112680 0.495760 0.407792 0.047 Uiso 1 1 calc R U . . .
C234 C 0.13426(8) 0.60131(15) 0.34812(6) 0.0445(3) Uani 1 1 d . . . . .
H234 H 0.113371 0.691442 0.352111 0.053 Uiso 1 1 calc R U . . .
C235 C 0.16483(8) 0.58674(14) 0.30918(6) 0.0422(3) Uani 1 1 d . . . . .
H235 H 0.164601 0.666974 0.286738 0.051 Uiso 1 1 calc R U . . .
C236 C 0.19588(7) 0.45573(13) 0.30260(5) 0.0339(3) Uani 1 1 d . . . . .
H236 H 0.216736 0.445950 0.275855 0.041 Uiso 1 1 calc R U . . .
C241 C 0.20016(5) 0.11227(12) 0.37826(4) 0.0263(2) Uani 1 1 d . . . . .
C242 C 0.16896(6) 0.21456(13) 0.40206(4) 0.0282(2) Uani 1 1 d . . . . .
C243 C 0.14515(6) 0.17434(15) 0.44312(5) 0.0365(3) Uani 1 1 d . . . . .
H243 H 0.126098 0.244931 0.460485 0.044 Uiso 1 1 calc R U . . .
C244 C 0.14987(7) 0.02889(17) 0.45809(5) 0.0424(3) Uani 1 1 d . . . . .
H244 H 0.134020 -0.000593 0.486132 0.051 Uiso 1 1 calc R U . . .
C245 C 0.17738(7) -0.07376(15) 0.43270(5) 0.0420(3) Uani 1 1 d . . . . .
H245 H 0.178389 -0.173593 0.442547 0.050 Uiso 1 1 calc R U . . .
C246 C 0.20371(6) -0.03305(14) 0.39282(5) 0.0341(3) Uani 1 1 d . . . . .
H246 H 0.223631 -0.103610 0.376060 0.041 Uiso 1 1 calc R U . . .


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 1.00 3.00 0.1580
-4.00 -1.00 3.00 0.1620
-3.00 0.00 4.00 0.1350
-3.00 3.00 -2.00 0.1810
-3.00 4.00 1.00 0.1610
-3.00 -1.00 -2.00 0.2500
-2.00 0.00 1.00 0.2160
-1.00 1.00 -4.00 0.2410
-1.00 -1.00 4.00 0.1600
-1.00 0.00 1.00 0.1570
-1.00 -3.00 0.00 0.2090
-1.00 0.00 4.00 0.1410
-1.00 0.00 2.00 0.1180
-1.00 4.00 -4.00 0.2050
0.00 -1.00 -4.00 0.2050
0.00 1.00 -4.00 0.2240
1.00 0.00 -4.00 0.2480
1.00 -1.00 -3.00 0.2330
1.00 4.00 3.00 0.2020
1.00 -4.00 3.00 0.1960
1.00 0.00 4.00 0.1660
2.00 -3.00 -4.00 0.2250
3.00 0.00 -4.00 0.2130
3.00 -1.00 0.00 0.2350
3.00 1.00 4.00 0.1790
3.00 2.00 -1.00 0.2370
3.00 -3.00 -2.00 0.2260
3.00 2.00 4.00 0.1830
4.00 1.00 0.00 0.1960
4.00 0.00 -1.00 0.1770
4.00 1.00 -3.00 0.2300
4.00 -1.00 3.00 0.2010

_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
O11 C11 1.4236(12) . ?
O11 H11 0.8400 . ?
O12 C12 1.4232(12) . ?
O12 H12 0.8400 . ?
O21 C21 1.4240(12) . ?
O21 H21 0.8400 . ?
O22 C22 1.4212(13) . ?
O22 H22 0.8400 . ?
N3 C35 1.325(2) . ?
N3 C31 1.3287(19) . ?
N4 C45 1.324(2) . ?
N4 C41 1.327(2) . ?
C11 C121 1.5293(14) . ?
C11 C111 1.5304(14) . ?
C11 C12 1.5638(14) . ?
C12 C141 1.5268(14) . ?
C12 C131 1.5317(14) . ?
C21 C211 1.5279(15) . ?
C21 C221 1.5303(16) . ?
C21 C22 1.5697(14) . ?
C22 C241 1.5248(14) . ?
C22 C231 1.5279(15) . ?
C31 C32 1.367(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.347(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.383(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C41 C42 1.378(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.366(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.365(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.376(2) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C111 C116 1.3837(16) . ?
C111 C112 1.3984(16) . ?
C112 C113 1.3919(16) . ?
C112 C122 1.4655(16) . ?
C113 C114 1.383(2) . ?
C113 H113 0.9500 . ?
C114 C115 1.388(2) . ?
C114 H114 0.9500 . ?
C115 C116 1.3963(17) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C121 C126 1.3835(15) . ?
C121 C122 1.3991(15) . ?
C122 C123 1.3873(17) . ?
C123 C124 1.382(2) . ?
C123 H123 0.9500 . ?
C124 C125 1.388(2) . ?
C124 H124 0.9500 . ?
C125 C126 1.3940(17) . ?
C125 H125 0.9500 . ?
C126 H126 0.9500 . ?
C131 C136 1.3852(16) . ?
C131 C132 1.3991(15) . ?
C132 C133 1.3905(17) . ?
C132 C142 1.4667(16) . ?
C133 C134 1.387(2) . ?
C133 H133 0.9500 . ?
C134 C135 1.387(2) . ?
C134 H134 0.9500 . ?
C135 C136 1.3930(18) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C141 C146 1.3846(16) . ?
C141 C142 1.3969(15) . ?
C142 C143 1.3893(16) . ?
C143 C144 1.387(2) . ?
C143 H143 0.9500 . ?
C144 C145 1.385(2) . ?
C144 H144 0.9500 . ?
C145 C146 1.3977(16) . ?
C145 H145 0.9500 . ?
C146 H146 0.9500 . ?
C211 C216 1.3827(18) . ?
C211 C212 1.4005(17) . ?
C212 C213 1.3936(19) . ?
C212 C222 1.465(2) . ?
C213 C214 1.380(3) . ?
C213 H213 0.9500 . ?
C214 C215 1.386(2) . ?
C214 H214 0.9500 . ?
C215 C216 1.3971(18) . ?
C215 H215 0.9500 . ?
C216 H216 0.9500 . ?
C221 C226 1.3818(18) . ?
C221 C222 1.3968(18) . ?
C222 C223 1.3936(19) . ?
C223 C224 1.386(3) . ?
C223 H223 0.9500 . ?
C224 C225 1.379(2) . ?
C224 H224 0.9500 . ?
C225 C226 1.3963(19) . ?
C225 H225 0.9500 . ?
C226 H226 0.9500 . ?
C231 C236 1.3839(15) . ?
C231 C232 1.3989(15) . ?
C232 C233 1.3874(17) . ?
C232 C242 1.4691(16) . ?
C233 C234 1.3847(19) . ?
C233 H233 0.9500 . ?
C234 C235 1.386(2) . ?
C234 H234 0.9500 . ?
C235 C236 1.3930(18) . ?
C235 H235 0.9500 . ?
C236 H236 0.9500 . ?
C241 C246 1.3823(16) . ?
C241 C242 1.3968(16) . ?
C242 C243 1.3913(15) . ?
C243 C244 1.386(2) . ?
C243 H243 0.9500 . ?
C244 C245 1.382(2) . ?
C244 H244 0.9500 . ?
C245 C246 1.3953(17) . ?
C245 H245 0.9500 . ?
C246 H246 0.9500 . ?

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
C11 O11 H11 109.5 . . ?
C12 O12 H12 109.5 . . ?
C21 O21 H21 109.5 . . ?
C22 O22 H22 109.5 . . ?
C35 N3 C31 117.72(13) . . ?
C45 N4 C41 117.52(13) . . ?
O11 C11 C121 113.49(8) . . ?
O11 C11 C111 113.71(8) . . ?
C121 C11 C111 101.56(8) . . ?
O11 C11 C12 104.98(8) . . ?
C121 C11 C12 111.46(8) . . ?
C111 C11 C12 111.89(8) . . ?
O12 C12 C141 107.53(8) . . ?
O12 C12 C131 112.28(8) . . ?
C141 C12 C131 101.70(8) . . ?
O12 C12 C11 109.28(8) . . ?
C141 C12 C11 113.36(8) . . ?
C131 C12 C11 112.47(8) . . ?
O21 C21 C211 113.56(9) . . ?
O21 C21 C221 113.39(9) . . ?
C211 C21 C221 101.48(9) . . ?
O21 C21 C22 105.23(8) . . ?
C211 C21 C22 112.09(9) . . ?
C221 C21 C22 111.32(9) . . ?
O22 C22 C241 108.92(8) . . ?
O22 C22 C231 112.83(9) . . ?
C241 C22 C231 101.68(8) . . ?
O22 C22 C21 109.27(8) . . ?
C241 C22 C21 112.05(8) . . ?
C231 C22 C21 111.91(8) . . ?
N3 C31 C32 123.52(17) . . ?
N3 C31 H31 118.2 . . ?
C32 C31 H31 118.2 . . ?
C33 C32 C31 118.81(17) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C34 119.38(16) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C33 C34 C35 118.20(18) . . ?
C33 C34 H34 120.9 . . ?
C35 C34 H34 120.9 . . ?
N3 C35 C34 122.37(17) . . ?
N3 C35 H35 118.8 . . ?
C34 C35 H35 118.8 . . ?
N4 C41 C42 122.99(17) . . ?
N4 C41 H41 118.5 . . ?
C42 C41 H41 118.5 . . ?
C43 C42 C41 118.65(18) . . ?
C43 C42 H42 120.7 . . ?
C41 C42 H42 120.7 . . ?
C44 C43 C42 119.04(15) . . ?
C44 C43 H43 120.5 . . ?
C42 C43 H43 120.5 . . ?
C43 C44 C45 118.70(18) . . ?
C43 C44 H44 120.6 . . ?
C45 C44 H44 120.6 . . ?
N4 C45 C44 123.09(17) . . ?
N4 C45 H45 118.5 . . ?
C44 C45 H45 118.5 . . ?
C116 C111 C112 120.48(10) . . ?
C116 C111 C11 129.23(10) . . ?
C112 C111 C11 110.27(9) . . ?
C113 C112 C111 120.77(11) . . ?
C113 C112 C122 130.41(11) . . ?
C111 C112 C122 108.75(9) . . ?
C114 C113 C112 118.55(12) . . ?
C114 C113 H113 120.7 . . ?
C112 C113 H113 120.7 . . ?
C113 C114 C115 120.80(11) . . ?
C113 C114 H114 119.6 . . ?
C115 C114 H114 119.6 . . ?
C114 C115 C116 120.85(12) . . ?
C114 C115 H115 119.6 . . ?
C116 C115 H115 119.6 . . ?
C111 C116 C115 118.51(12) . . ?
C111 C116 H116 120.7 . . ?
C115 C116 H116 120.7 . . ?
C126 C121 C122 120.33(10) . . ?
C126 C121 C11 129.59(10) . . ?
C122 C121 C11 110.08(9) . . ?
C123 C122 C121 120.70(11) . . ?
C123 C122 C112 130.30(11) . . ?
C121 C122 C112 108.98(10) . . ?
C124 C123 C122 118.76(12) . . ?
C124 C123 H123 120.6 . . ?
C122 C123 H123 120.6 . . ?
C123 C124 C125 120.81(12) . . ?
C123 C124 H124 119.6 . . ?
C125 C124 H124 119.6 . . ?
C124 C125 C126 120.61(12) . . ?
C124 C125 H125 119.7 . . ?
C126 C125 H125 119.7 . . ?
C121 C126 C125 118.76(11) . . ?
C121 C126 H126 120.6 . . ?
C125 C126 H126 120.6 . . ?
C136 C131 C132 120.30(10) . . ?
C136 C131 C12 129.49(10) . . ?
C132 C131 C12 110.18(9) . . ?
C133 C132 C131 120.85(11) . . ?
C133 C132 C142 130.30(11) . . ?
C131 C132 C142 108.80(10) . . ?
C134 C133 C132 118.48(12) . . ?
C134 C133 H133 120.8 . . ?
C132 C133 H133 120.8 . . ?
C133 C134 C135 120.83(12) . . ?
C133 C134 H134 119.6 . . ?
C135 C134 H134 119.6 . . ?
C134 C135 C136 120.80(13) . . ?
C134 C135 H135 119.6 . . ?
C136 C135 H135 119.6 . . ?
C131 C136 C135 118.74(12) . . ?
C131 C136 H136 120.6 . . ?
C135 C136 H136 120.6 . . ?
C146 C141 C142 120.50(10) . . ?
C146 C141 C12 128.97(10) . . ?
C142 C141 C12 110.33(9) . . ?
C143 C142 C141 120.88(11) . . ?
C143 C142 C132 130.03(11) . . ?
C141 C142 C132 108.98(9) . . ?
C144 C143 C142 118.48(12) . . ?
C144 C143 H143 120.8 . . ?
C142 C143 H143 120.8 . . ?
C145 C144 C143 120.84(11) . . ?
C145 C144 H144 119.6 . . ?
C143 C144 H144 119.6 . . ?
C144 C145 C146 120.84(12) . . ?
C144 C145 H145 119.6 . . ?
C146 C145 H145 119.6 . . ?
C141 C146 C145 118.44(11) . . ?
C141 C146 H146 120.8 . . ?
C145 C146 H146 120.8 . . ?
C216 C211 C212 120.53(11) . . ?
C216 C211 C21 129.23(11) . . ?
C212 C211 C21 110.17(11) . . ?
C213 C212 C211 120.48(14) . . ?
C213 C212 C222 130.57(13) . . ?
C211 C212 C222 108.81(11) . . ?
C214 C213 C212 118.72(14) . . ?
C214 C213 H213 120.6 . . ?
C212 C213 H213 120.6 . . ?
C213 C214 C215 120.86(13) . . ?
C213 C214 H214 119.6 . . ?
C215 C214 H214 119.6 . . ?
C214 C215 C216 120.87(15) . . ?
C214 C215 H215 119.6 . . ?
C216 C215 H215 119.6 . . ?
C211 C216 C215 118.47(13) . . ?
C211 C216 H216 120.8 . . ?
C215 C216 H216 120.8 . . ?
C226 C221 C222 120.61(12) . . ?
C226 C221 C21 129.16(11) . . ?
C222 C221 C21 110.23(11) . . ?
C223 C222 C221 120.32(14) . . ?
C223 C222 C212 130.74(13) . . ?
C221 C222 C212 108.83(11) . . ?
C224 C223 C222 118.79(14) . . ?
C224 C223 H223 120.6 . . ?
C222 C223 H223 120.6 . . ?
C225 C224 C223 120.76(14) . . ?
C225 C224 H224 119.6 . . ?
C223 C224 H224 119.6 . . ?
C224 C225 C226 120.85(15) . . ?
C224 C225 H225 119.6 . . ?
C226 C225 H225 119.6 . . ?
C221 C226 C225 118.66(14) . . ?
C221 C226 H226 120.7 . . ?
C225 C226 H226 120.7 . . ?
C236 C231 C232 120.26(10) . . ?
C236 C231 C22 129.44(10) . . ?
C232 C231 C22 110.27(9) . . ?
C233 C232 C231 120.66(11) . . ?
C233 C232 C242 130.53(10) . . ?
C231 C232 C242 108.70(10) . . ?
C234 C233 C232 118.84(12) . . ?
C234 C233 H233 120.6 . . ?
C232 C233 H233 120.6 . . ?
C233 C234 C235 120.66(12) . . ?
C233 C234 H234 119.7 . . ?
C235 C234 H234 119.7 . . ?
C234 C235 C236 120.73(12) . . ?
C234 C235 H235 119.6 . . ?
C236 C235 H235 119.6 . . ?
C231 C236 C235 118.84(11) . . ?
C231 C236 H236 120.6 . . ?
C235 C236 H236 120.6 . . ?
C246 C241 C242 120.35(10) . . ?
C246 C241 C22 129.23(10) . . ?
C242 C241 C22 110.37(9) . . ?
C243 C242 C241 120.82(11) . . ?
C243 C242 C232 130.38(11) . . ?
C241 C242 C232 108.75(9) . . ?
C244 C243 C242 118.42(12) . . ?
C244 C243 H243 120.8 . . ?
C242 C243 H243 120.8 . . ?
C245 C244 C243 120.74(11) . . ?
C245 C244 H244 119.6 . . ?
C243 C244 H244 119.6 . . ?
C244 C245 C246 121.02(12) . . ?
C244 C245 H245 119.5 . . ?
C246 C245 H245 119.5 . . ?
C241 C246 C245 118.50(12) . . ?
C241 C246 H246 120.8 . . ?
C245 C246 H246 120.8 . . ?

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
O11 C11 C12 O12 59.23(10) . . . . ?
C121 C11 C12 O12 -64.03(10) . . . . ?
C111 C11 C12 O12 -176.98(8) . . . . ?
O11 C11 C12 C141 179.14(8) . . . . ?
C121 C11 C12 C141 55.87(11) . . . . ?
C111 C11 C12 C141 -57.07(11) . . . . ?
O11 C11 C12 C131 -66.17(10) . . . . ?
C121 C11 C12 C131 170.57(8) . . . . ?
C111 C11 C12 C131 57.62(11) . . . . ?
O21 C21 C22 O22 60.02(10) . . . . ?
C211 C21 C22 O22 -176.09(9) . . . . ?
C221 C21 C22 O22 -63.20(11) . . . . ?
O21 C21 C22 C241 -179.17(8) . . . . ?
C211 C21 C22 C241 -55.28(12) . . . . ?
C221 C21 C22 C241 57.62(12) . . . . ?
O21 C21 C22 C231 -65.70(11) . . . . ?
C211 C21 C22 C231 58.19(11) . . . . ?
C221 C21 C22 C231 171.09(9) . . . . ?
C35 N3 C31 C32 0.6(2) . . . . ?
N3 C31 C32 C33 -0.3(3) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C31 N3 C35 C34 -0.5(3) . . . . ?
C33 C34 C35 N3 0.2(3) . . . . ?
C45 N4 C41 C42 -0.1(3) . . . . ?
N4 C41 C42 C43 0.0(3) . . . . ?
C41 C42 C43 C44 0.6(3) . . . . ?
C42 C43 C44 C45 -1.2(3) . . . . ?
C41 N4 C45 C44 -0.6(3) . . . . ?
C43 C44 C45 N4 1.2(3) . . . . ?
O11 C11 C111 C116 50.45(15) . . . . ?
C121 C11 C111 C116 172.73(11) . . . . ?
C12 C11 C111 C116 -68.28(14) . . . . ?
O11 C11 C111 C112 -127.58(10) . . . . ?
C121 C11 C111 C112 -5.29(11) . . . . ?
C12 C11 C111 C112 113.69(10) . . . . ?
C116 C111 C112 C113 1.91(17) . . . . ?
C11 C111 C112 C113 -179.86(10) . . . . ?
C116 C111 C112 C122 -175.43(10) . . . . ?
C11 C111 C112 C122 2.80(12) . . . . ?
C111 C112 C113 C114 -1.17(18) . . . . ?
C122 C112 C113 C114 175.51(12) . . . . ?
C112 C113 C114 C115 -0.4(2) . . . . ?
C113 C114 C115 C116 1.3(2) . . . . ?
C112 C111 C116 C115 -1.03(17) . . . . ?
C11 C111 C116 C115 -178.88(11) . . . . ?
C114 C115 C116 C111 -0.5(2) . . . . ?
O11 C11 C121 C126 -52.85(15) . . . . ?
C111 C11 C121 C126 -175.29(11) . . . . ?
C12 C11 C121 C126 65.42(14) . . . . ?
O11 C11 C121 C122 128.49(9) . . . . ?
C111 C11 C121 C122 6.05(11) . . . . ?
C12 C11 C121 C122 -113.24(10) . . . . ?
C126 C121 C122 C123 -2.24(17) . . . . ?
C11 C121 C122 C123 176.56(10) . . . . ?
C126 C121 C122 C112 176.42(10) . . . . ?
C11 C121 C122 C112 -4.77(12) . . . . ?
C113 C112 C122 C123 2.7(2) . . . . ?
C111 C112 C122 C123 179.73(12) . . . . ?
C113 C112 C122 C121 -175.76(12) . . . . ?
C111 C112 C122 C121 1.24(12) . . . . ?
C121 C122 C123 C124 1.36(19) . . . . ?
C112 C122 C123 C124 -176.99(12) . . . . ?
C122 C123 C124 C125 0.1(2) . . . . ?
C123 C124 C125 C126 -0.6(2) . . . . ?
C122 C121 C126 C125 1.65(17) . . . . ?
C11 C121 C126 C125 -176.89(11) . . . . ?
C124 C125 C126 C121 -0.23(19) . . . . ?
O12 C12 C131 C136 -62.44(15) . . . . ?
C141 C12 C131 C136 -177.10(12) . . . . ?
C11 C12 C131 C136 61.31(15) . . . . ?
O12 C12 C131 C132 115.49(10) . . . . ?
C141 C12 C131 C132 0.83(11) . . . . ?
C11 C12 C131 C132 -120.76(10) . . . . ?
C136 C131 C132 C133 -0.31(18) . . . . ?
C12 C131 C132 C133 -178.46(11) . . . . ?
C136 C131 C132 C142 177.56(11) . . . . ?
C12 C131 C132 C142 -0.60(13) . . . . ?
C131 C132 C133 C134 0.1(2) . . . . ?
C142 C132 C133 C134 -177.21(13) . . . . ?
C132 C133 C134 C135 -0.2(2) . . . . ?
C133 C134 C135 C136 0.4(2) . . . . ?
C132 C131 C136 C135 0.51(19) . . . . ?
C12 C131 C136 C135 178.27(12) . . . . ?
C134 C135 C136 C131 -0.6(2) . . . . ?
O12 C12 C141 C146 55.82(14) . . . . ?
C131 C12 C141 C146 173.95(11) . . . . ?
C11 C12 C141 C146 -65.08(14) . . . . ?
O12 C12 C141 C142 -118.92(9) . . . . ?
C131 C12 C141 C142 -0.79(11) . . . . ?
C11 C12 C141 C142 120.18(10) . . . . ?
C146 C141 C142 C143 1.73(17) . . . . ?
C12 C141 C142 C143 176.98(10) . . . . ?
C146 C141 C142 C132 -174.77(10) . . . . ?
C12 C141 C142 C132 0.48(12) . . . . ?
C133 C132 C142 C143 1.6(2) . . . . ?
C131 C132 C142 C143 -176.00(12) . . . . ?
C133 C132 C142 C141 177.66(13) . . . . ?
C131 C132 C142 C141 0.07(13) . . . . ?
C141 C142 C143 C144 -0.93(19) . . . . ?
C132 C142 C143 C144 174.75(12) . . . . ?
C142 C143 C144 C145 -0.2(2) . . . . ?
C143 C144 C145 C146 0.5(2) . . . . ?
C142 C141 C146 C145 -1.38(17) . . . . ?
C12 C141 C146 C145 -175.65(11) . . . . ?
C144 C145 C146 C141 0.29(19) . . . . ?
O21 C21 C211 C216 48.52(16) . . . . ?
C221 C21 C211 C216 170.56(11) . . . . ?
C22 C21 C211 C216 -70.58(15) . . . . ?
O21 C21 C211 C212 -128.43(10) . . . . ?
C221 C21 C211 C212 -6.39(11) . . . . ?
C22 C21 C211 C212 112.48(10) . . . . ?
C216 C211 C212 C213 2.95(18) . . . . ?
C21 C211 C212 C213 -179.79(11) . . . . ?
C216 C211 C212 C222 -173.27(11) . . . . ?
C21 C211 C212 C222 3.99(13) . . . . ?
C211 C212 C213 C214 -2.8(2) . . . . ?
C222 C212 C213 C214 172.49(14) . . . . ?
C212 C213 C214 C215 0.7(2) . . . . ?
C213 C214 C215 C216 1.4(2) . . . . ?
C212 C211 C216 C215 -0.89(18) . . . . ?
C21 C211 C216 C215 -177.57(11) . . . . ?
C214 C215 C216 C211 -1.3(2) . . . . ?
O21 C21 C221 C226 -51.54(16) . . . . ?
C211 C21 C221 C226 -173.70(12) . . . . ?
C22 C21 C221 C226 66.88(15) . . . . ?
O21 C21 C221 C222 128.87(10) . . . . ?
C211 C21 C221 C222 6.71(12) . . . . ?
C22 C21 C221 C222 -112.71(10) . . . . ?
C226 C221 C222 C223 -1.07(19) . . . . ?
C21 C221 C222 C223 178.56(11) . . . . ?
C226 C221 C222 C212 175.60(11) . . . . ?
C21 C221 C222 C212 -4.76(13) . . . . ?
C213 C212 C222 C223 1.0(2) . . . . ?
C211 C212 C222 C223 176.70(13) . . . . ?
C213 C212 C222 C221 -175.23(13) . . . . ?
C211 C212 C222 C221 0.49(14) . . . . ?
C221 C222 C223 C224 0.8(2) . . . . ?
C212 C222 C223 C224 -175.01(13) . . . . ?
C222 C223 C224 C225 -0.2(2) . . . . ?
C223 C224 C225 C226 -0.1(2) . . . . ?
C222 C221 C226 C225 0.69(19) . . . . ?
C21 C221 C226 C225 -178.87(12) . . . . ?
C224 C225 C226 C221 -0.1(2) . . . . ?
O22 C22 C231 C236 -57.84(15) . . . . ?
C241 C22 C231 C236 -174.35(12) . . . . ?
C21 C22 C231 C236 65.90(15) . . . . ?
O22 C22 C231 C232 120.15(10) . . . . ?
C241 C22 C231 C232 3.64(11) . . . . ?
C21 C22 C231 C232 -116.12(10) . . . . ?
C236 C231 C232 C233 0.25(17) . . . . ?
C22 C231 C232 C233 -177.95(11) . . . . ?
C236 C231 C232 C242 176.89(10) . . . . ?
C22 C231 C232 C242 -1.31(12) . . . . ?
C231 C232 C233 C234 -0.43(19) . . . . ?
C242 C232 C233 C234 -176.24(12) . . . . ?
C232 C233 C234 C235 0.4(2) . . . . ?
C233 C234 C235 C236 -0.1(2) . . . . ?
C232 C231 C236 C235 0.01(18) . . . . ?
C22 C231 C236 C235 177.83(12) . . . . ?
C234 C235 C236 C231 -0.1(2) . . . . ?
O22 C22 C241 C246 53.26(15) . . . . ?
C231 C22 C241 C246 172.58(12) . . . . ?
C21 C22 C241 C246 -67.76(15) . . . . ?
O22 C22 C241 C242 -124.14(10) . . . . ?
C231 C22 C241 C242 -4.82(11) . . . . ?
C21 C22 C241 C242 114.84(10) . . . . ?
C246 C241 C242 C243 4.33(17) . . . . ?
C22 C241 C242 C243 -178.00(10) . . . . ?
C246 C241 C242 C232 -173.34(10) . . . . ?
C22 C241 C242 C232 4.32(12) . . . . ?
C233 C232 C242 C243 -3.1(2) . . . . ?
C231 C232 C242 C243 -179.26(12) . . . . ?
C233 C232 C242 C241 174.31(12) . . . . ?
C231 C232 C242 C241 -1.88(13) . . . . ?
C241 C242 C243 C244 -3.24(18) . . . . ?
C232 C242 C243 C244 173.87(12) . . . . ?
C242 C243 C244 C245 -0.2(2) . . . . ?
C243 C244 C245 C246 2.6(2) . . . . ?
C242 C241 C246 C245 -1.87(18) . . . . ?
C22 C241 C246 C245 -179.05(11) . . . . ?
C244 C245 C246 C241 -1.6(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
O11 H11 N3 0.84 1.87 2.7024(13) 169 . yes
O12 H12 O11 0.84 1.96 2.7831(10) 168 2_655 yes
O21 H21 N4 0.84 1.89 2.7234(14) 175 . yes
O22 H22 O21 0.84 2.01 2.8230(11) 164 2 yes
C43 H43 O12 0.95 2.55 3.4009(19) 149 . yes
C126 H126 O12 0.95 2.52 3.2674(14) 135 2_655 yes
C136 H136 O11 0.95 2.57 3.0431(15) 111 . yes

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_bq124
_database_code_depnum_ccdc_archive 'CCDC 2409402'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        9,9'-bifluorenyl-9,9'-diol
_chemical_name_common            ?
_chemical_temperature_decomposition 353.65
_chemical_formula_moiety         'C26 H18 O2, C6 H7 N'
_chemical_formula_sum            'C32 H25 N O2'
_chemical_formula_weight         455.53

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'
N N 0.0061 0.0033 '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'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4369(5)
_cell_length_b                   10.7155(4)
_cell_length_c                   21.6126(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2417.08(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9451
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.257
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_absorpt_special_details   
'Additional spherical absorption correction applied with mu*r =  0.20'
_diffrn_ambient_temperature      200(2)
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_power             70
_diffrn_source_voltage           50
_diffrn_source_current           1.4
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Bruker PHOTON II 7 CCD detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            74747
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5532
_reflns_number_gt                5265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       'Bruker Instrument Service V6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2019/3 (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2019/3 (Sheldrick, 2015b) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows V2023.1 (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were
placed in calculated positions and were included in the refinement in the riding
model approximation, with Uiso(H) set to 1.2 Ueq(C).

The H atoms of the methyl group were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015b)), with Uiso(H) set to
1.5Ueq(C).

The H atoms of the hydroxyl group were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program  (Sheldrick, 2015b)) and Uiso(H) allowed to 
refine freely.

A number of reflections with large differences between their observed and
calculated intensities were omitted.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.2608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0055(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2203 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(16)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5532
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.32073(13) 0.40393(11) 0.14877(6) 0.0401(3) Uani 1 1 d . . . . .
H1 H 0.310777 0.384400 0.186104 0.070(8) Uiso 1 1 calc R . . . .
O2 O 0.23702(12) 0.54263(11) 0.24395(5) 0.0348(3) Uani 1 1 d . . . . .
H2 H 0.261024 0.580641 0.275902 0.072(8) Uiso 1 1 calc R . . . .
N5 N 0.31214(15) 0.65001(14) 0.35176(7) 0.0408(3) Uani 1 1 d . . . . .
C1 C 0.25246(15) 0.51596(14) 0.13609(7) 0.0314(3) Uani 1 1 d . . . . .
C2 C 0.27680(14) 0.60977(14) 0.19074(7) 0.0288(3) Uani 1 1 d . . . . .
C11 C 0.29139(16) 0.56952(14) 0.07366(7) 0.0329(3) Uani 1 1 d . . . . .
C12 C 0.18252(17) 0.59024(15) 0.03709(8) 0.0359(3) Uani 1 1 d . . . . .
C13 C 0.1938(2) 0.64315(17) -0.02141(8) 0.0438(4) Uani 1 1 d . . . . .
H13 H 0.119986 0.659466 -0.045861 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3153(2) 0.67151(18) -0.04318(8) 0.0485(5) Uani 1 1 d . . . . .
H14 H 0.324654 0.708973 -0.082764 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4229(2) 0.64623(18) -0.00831(8) 0.0454(4) Uani 1 1 d . . . . .
H15 H 0.505296 0.663445 -0.024925 0.055 Uiso 1 1 calc R U . . .
C16 C 0.41261(18) 0.59572(16) 0.05107(7) 0.0381(4) Uani 1 1 d . . . . .
H16 H 0.486767 0.579770 0.075295 0.046 Uiso 1 1 calc R U . . .
C21 C 0.10962(16) 0.49344(15) 0.12662(8) 0.0352(3) Uani 1 1 d . . . . .
C22 C 0.07000(17) 0.54133(15) 0.06984(8) 0.0372(4) Uani 1 1 d . . . . .
C23 C -0.05748(19) 0.53227(19) 0.05177(10) 0.0506(5) Uani 1 1 d . . . . .
H23 H -0.085006 0.563939 0.012920 0.061 Uiso 1 1 calc R U . . .
C24 C -0.1435(2) 0.4758(2) 0.09189(12) 0.0583(6) Uani 1 1 d . . . . .
H24 H -0.231447 0.471521 0.080854 0.070 Uiso 1 1 calc R U . . .
C25 C -0.10369(19) 0.4257(2) 0.14771(11) 0.0547(5) Uani 1 1 d . . . . .
H25 H -0.164014 0.385312 0.173849 0.066 Uiso 1 1 calc R U . . .
C26 C 0.02366(19) 0.43386(17) 0.16577(9) 0.0451(4) Uani 1 1 d . . . . .
H26 H 0.051367 0.399506 0.204015 0.054 Uiso 1 1 calc R U . . .
C31 C 0.41736(15) 0.65026(15) 0.19370(6) 0.0306(3) Uani 1 1 d . . . . .
C32 C 0.42804(15) 0.77743(15) 0.18091(7) 0.0319(3) Uani 1 1 d . . . . .
C33 C 0.54728(17) 0.83546(18) 0.18082(8) 0.0411(4) Uani 1 1 d . . . . .
H33 H 0.554730 0.921774 0.171440 0.049 Uiso 1 1 calc R U . . .
C34 C 0.65474(17) 0.7653(2) 0.19461(9) 0.0467(4) Uani 1 1 d . . . . .
H34 H 0.736635 0.804038 0.194980 0.056 Uiso 1 1 calc R U . . .
C35 C 0.64426(17) 0.6389(2) 0.20793(8) 0.0447(4) Uani 1 1 d . . . . .
H35 H 0.718958 0.592094 0.217572 0.054 Uiso 1 1 calc R U . . .
C36 C 0.52508(16) 0.57999(18) 0.20727(8) 0.0388(4) Uani 1 1 d . . . . .
H36 H 0.517964 0.493359 0.215959 0.047 Uiso 1 1 calc R U . . .
C41 C 0.20913(14) 0.73460(14) 0.18137(7) 0.0299(3) Uani 1 1 d . . . . .
C42 C 0.29889(16) 0.82981(14) 0.17287(7) 0.0320(3) Uani 1 1 d . . . . .
C43 C 0.26038(18) 0.95201(16) 0.16279(8) 0.0410(4) Uani 1 1 d . . . . .
H43 H 0.321719 1.015934 0.155713 0.049 Uiso 1 1 calc R U . . .
C44 C 0.1301(2) 0.97893(18) 0.16326(8) 0.0452(4) Uani 1 1 d . . . . .
H44 H 0.101942 1.062134 0.156515 0.054 Uiso 1 1 calc R U . . .
C45 C 0.04108(17) 0.88537(18) 0.17349(8) 0.0411(4) Uani 1 1 d . . . . .
H45 H -0.047516 0.905603 0.174501 0.049 Uiso 1 1 calc R U . . .
C46 C 0.07930(16) 0.76195(16) 0.18234(7) 0.0353(3) Uani 1 1 d . . . . .
H46 H 0.017720 0.698005 0.188887 0.042 Uiso 1 1 calc R U . . .
C51 C 0.36066(17) 0.74541(16) 0.47033(8) 0.0363(3) Uani 1 1 d . . . . .
C52 C 0.25259(17) 0.67524(16) 0.45786(8) 0.0385(4) Uani 1 1 d . . . . .
H52 H 0.192678 0.657940 0.489824 0.046 Uiso 1 1 calc R U . . .
C53 C 0.23198(18) 0.63037(16) 0.39882(8) 0.0407(4) Uani 1 1 d . . . . .
H53 H 0.156657 0.582958 0.391312 0.049 Uiso 1 1 calc R U . . .
C54 C 0.41646(18) 0.71776(19) 0.36388(8) 0.0438(4) Uani 1 1 d . . . . .
H54 H 0.474997 0.733051 0.331085 0.053 Uiso 1 1 calc R U . . .
C55 C 0.44401(18) 0.76681(18) 0.42132(9) 0.0428(4) Uani 1 1 d . . . . .
H55 H 0.519447 0.814903 0.427367 0.051 Uiso 1 1 calc R U . . .
C56 C 0.3853(2) 0.7981(2) 0.53353(9) 0.0547(5) Uani 1 1 d . . . . .
H56A H 0.306792 0.793006 0.558297 0.082 Uiso 1 1 calc R U . . .
H56B H 0.411787 0.885468 0.529827 0.082 Uiso 1 1 calc R U . . .
H56C H 0.453353 0.750068 0.553772 0.082 Uiso 1 1 calc R U . . .


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 3.00 1.00 0.0880
-4.00 -1.00 0.00 0.1710
-3.00 -1.00 3.00 0.1590
-3.00 2.00 -4.00 0.0990
-1.00 -1.00 -4.00 0.2140
-1.00 -2.00 2.00 0.1540
-1.00 3.00 -1.00 0.0990
-1.00 1.00 -1.00 0.0710
-1.00 1.00 -4.00 0.1040
-1.00 -4.00 1.00 0.1770
-1.00 0.00 3.00 0.1500
-1.00 3.00 4.00 0.1000
0.00 -1.00 2.00 0.1140
0.00 -1.00 -4.00 0.2180
0.00 2.00 1.00 0.1150
0.00 -2.00 1.00 0.1490
0.00 -1.00 4.00 0.1230
1.00 1.00 0.00 0.1470
1.00 0.00 -3.00 0.1550
1.00 -3.00 2.00 0.1220
1.00 3.00 4.00 0.1260
2.00 1.00 -2.00 0.1410
3.00 -1.00 -3.00 0.1210
4.00 -1.00 -3.00 0.1270
4.00 -4.00 -1.00 0.1420
4.00 0.00 3.00 0.1940

_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 1.423(2) . ?
O1 H1 0.8400 . ?
O2 C2 1.4187(18) . ?
O2 H2 0.8400 . ?
N5 C53 1.334(2) . ?
N5 C54 1.335(3) . ?
C1 C11 1.522(2) . ?
C1 C21 1.524(2) . ?
C1 C2 1.5715(19) . ?
C2 C41 1.526(2) . ?
C2 C31 1.531(2) . ?
C11 C16 1.385(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.391(2) . ?
C12 C22 1.468(2) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.389(2) . ?
C21 C22 1.393(3) . ?
C22 C23 1.390(3) . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.385(2) . ?
C31 C32 1.395(2) . ?
C32 C33 1.391(2) . ?
C32 C42 1.470(2) . ?
C33 C34 1.382(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.395(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.387(2) . ?
C41 C42 1.397(2) . ?
C42 C43 1.387(2) . ?
C43 C44 1.390(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.385(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.395(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.382(3) . ?
C51 C55 1.390(2) . ?
C51 C56 1.500(2) . ?
C52 C53 1.380(2) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 C55 1.378(3) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 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 109.5 . . ?
C2 O2 H2 109.5 . . ?
C53 N5 C54 116.61(15) . . ?
O1 C1 C11 110.82(12) . . ?
O1 C1 C21 112.47(13) . . ?
C11 C1 C21 101.64(13) . . ?
O1 C1 C2 108.30(12) . . ?
C11 C1 C2 112.45(12) . . ?
C21 C1 C2 111.12(12) . . ?
O2 C2 C41 114.62(12) . . ?
O2 C2 C31 112.96(12) . . ?
C41 C2 C31 101.57(12) . . ?
O2 C2 C1 103.74(11) . . ?
C41 C2 C1 112.71(12) . . ?
C31 C2 C1 111.57(12) . . ?
C16 C11 C12 120.63(15) . . ?
C16 C11 C1 129.28(16) . . ?
C12 C11 C1 110.08(14) . . ?
C13 C12 C11 120.59(17) . . ?
C13 C12 C22 130.65(17) . . ?
C11 C12 C22 108.66(15) . . ?
C14 C13 C12 118.35(18) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C15 C14 C13 121.09(16) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.03(17) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 118.21(17) . . ?
C11 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C26 C21 C22 120.96(17) . . ?
C26 C21 C1 128.53(17) . . ?
C22 C21 C1 110.51(14) . . ?
C23 C22 C21 120.39(17) . . ?
C23 C22 C12 130.93(18) . . ?
C21 C22 C12 108.60(15) . . ?
C24 C23 C22 118.3(2) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C25 C24 C23 121.4(2) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 120.50(19) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 118.5(2) . . ?
C25 C26 H26 120.8 . . ?
C21 C26 H26 120.8 . . ?
C36 C31 C32 120.56(15) . . ?
C36 C31 C2 129.25(15) . . ?
C32 C31 C2 110.19(14) . . ?
C33 C32 C31 120.56(16) . . ?
C33 C32 C42 130.49(15) . . ?
C31 C32 C42 108.85(13) . . ?
C34 C33 C32 118.85(17) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C33 C34 C35 120.71(17) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C34 C35 C36 120.61(18) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 118.70(17) . . ?
C31 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
C46 C41 C42 120.19(15) . . ?
C46 C41 C2 129.46(14) . . ?
C42 C41 C2 110.31(13) . . ?
C43 C42 C41 121.05(16) . . ?
C43 C42 C32 130.13(15) . . ?
C41 C42 C32 108.68(14) . . ?
C42 C43 C44 118.57(16) . . ?
C42 C43 H43 120.7 . . ?
C44 C43 H43 120.7 . . ?
C45 C44 C43 120.48(16) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C44 C45 C46 121.11(17) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 H45 119.4 . . ?
C41 C46 C45 118.54(16) . . ?
C41 C46 H46 120.7 . . ?
C45 C46 H46 120.7 . . ?
C52 C51 C55 116.87(16) . . ?
C52 C51 C56 121.46(16) . . ?
C55 C51 C56 121.65(17) . . ?
C53 C52 C51 119.80(16) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
N5 C53 C52 123.52(17) . . ?
N5 C53 H53 118.2 . . ?
C52 C53 H53 118.2 . . ?
N5 C54 C55 123.66(16) . . ?
N5 C54 H54 118.2 . . ?
C55 C54 H54 118.2 . . ?
C54 C55 C51 119.53(17) . . ?
C54 C55 H55 120.2 . . ?
C51 C55 H55 120.2 . . ?
C51 C56 H56A 109.5 . . ?
C51 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C51 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 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 -56.27(14) . . . . ?
C11 C1 C2 O2 -179.07(13) . . . . ?
C21 C1 C2 O2 67.74(16) . . . . ?
O1 C1 C2 C41 179.17(12) . . . . ?
C11 C1 C2 C41 56.37(17) . . . . ?
C21 C1 C2 C41 -56.82(16) . . . . ?
O1 C1 C2 C31 65.63(15) . . . . ?
C11 C1 C2 C31 -57.17(17) . . . . ?
C21 C1 C2 C31 -170.35(13) . . . . ?
O1 C1 C11 C16 -52.2(2) . . . . ?
C21 C1 C11 C16 -171.91(16) . . . . ?
C2 C1 C11 C16 69.2(2) . . . . ?
O1 C1 C11 C12 126.82(14) . . . . ?
C21 C1 C11 C12 7.10(16) . . . . ?
C2 C1 C11 C12 -111.80(15) . . . . ?
C16 C11 C12 C13 -3.2(2) . . . . ?
C1 C11 C12 C13 177.74(14) . . . . ?
C16 C11 C12 C22 173.65(14) . . . . ?
C1 C11 C12 C22 -5.46(17) . . . . ?
C11 C12 C13 C14 1.8(2) . . . . ?
C22 C12 C13 C14 -174.24(17) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 -2.5(3) . . . . ?
C12 C11 C16 C15 1.7(2) . . . . ?
C1 C11 C16 C15 -179.41(15) . . . . ?
C14 C15 C16 C11 1.1(3) . . . . ?
O1 C1 C21 C26 54.5(2) . . . . ?
C11 C1 C21 C26 173.04(16) . . . . ?
C2 C1 C21 C26 -67.1(2) . . . . ?
O1 C1 C21 C22 -124.91(14) . . . . ?
C11 C1 C21 C22 -6.36(16) . . . . ?
C2 C1 C21 C22 113.48(14) . . . . ?
C26 C21 C22 C23 1.2(2) . . . . ?
C1 C21 C22 C23 -179.36(15) . . . . ?
C26 C21 C22 C12 -175.96(14) . . . . ?
C1 C21 C22 C12 3.50(17) . . . . ?
C13 C12 C22 C23 0.9(3) . . . . ?
C11 C12 C22 C23 -175.51(17) . . . . ?
C13 C12 C22 C21 177.60(16) . . . . ?
C11 C12 C22 C21 1.23(18) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C12 C22 C23 C24 177.09(17) . . . . ?
C22 C23 C24 C25 -2.2(3) . . . . ?
C23 C24 C25 C26 1.8(3) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C22 C21 C26 C25 -1.5(2) . . . . ?
C1 C21 C26 C25 179.12(16) . . . . ?
O2 C2 C31 C36 50.2(2) . . . . ?
C41 C2 C31 C36 173.44(15) . . . . ?
C1 C2 C31 C36 -66.2(2) . . . . ?
O2 C2 C31 C32 -129.08(13) . . . . ?
C41 C2 C31 C32 -5.81(15) . . . . ?
C1 C2 C31 C32 114.51(14) . . . . ?
C36 C31 C32 C33 0.8(2) . . . . ?
C2 C31 C32 C33 -179.87(13) . . . . ?
C36 C31 C32 C42 -175.79(13) . . . . ?
C2 C31 C32 C42 3.53(16) . . . . ?
C31 C32 C33 C34 -1.0(2) . . . . ?
C42 C32 C33 C34 174.72(16) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C32 C31 C36 C35 0.0(2) . . . . ?
C2 C31 C36 C35 -179.13(15) . . . . ?
C34 C35 C36 C31 -0.6(3) . . . . ?
O2 C2 C41 C46 -49.5(2) . . . . ?
C31 C2 C41 C46 -171.63(15) . . . . ?
C1 C2 C41 C46 68.86(19) . . . . ?
O2 C2 C41 C42 128.31(13) . . . . ?
C31 C2 C41 C42 6.18(15) . . . . ?
C1 C2 C41 C42 -113.33(13) . . . . ?
C46 C41 C42 C43 -2.6(2) . . . . ?
C2 C41 C42 C43 179.34(14) . . . . ?
C46 C41 C42 C32 173.58(13) . . . . ?
C2 C41 C42 C32 -4.47(16) . . . . ?
C33 C32 C42 C43 0.2(3) . . . . ?
C31 C32 C42 C43 176.31(16) . . . . ?
C33 C32 C42 C41 -175.57(16) . . . . ?
C31 C32 C42 C41 0.58(17) . . . . ?
C41 C42 C43 C44 2.0(2) . . . . ?
C32 C42 C43 C44 -173.25(16) . . . . ?
C42 C43 C44 C45 -0.1(3) . . . . ?
C43 C44 C45 C46 -1.3(3) . . . . ?
C42 C41 C46 C45 1.2(2) . . . . ?
C2 C41 C46 C45 178.84(15) . . . . ?
C44 C45 C46 C41 0.7(3) . . . . ?
C55 C51 C52 C53 -0.1(3) . . . . ?
C56 C51 C52 C53 178.76(18) . . . . ?
C54 N5 C53 C52 -0.5(3) . . . . ?
C51 C52 C53 N5 0.5(3) . . . . ?
C53 N5 C54 C55 0.0(3) . . . . ?
N5 C54 C55 C51 0.4(3) . . . . ?
C52 C51 C55 C54 -0.4(3) . . . . ?
C56 C51 C55 C54 -179.18(19) . . . . ?

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 0.84 2.24 2.6839(16) 113 . yes
O2 H2 N5 0.84 1.88 2.7145(18) 174 . yes
C55 H55 O1 0.95 2.53 3.238(2) 131 3_655 yes

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_bq165
_database_code_depnum_ccdc_archive 'CCDC 2409401'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        9,9'-bifluorenyl-9,9'-diol
_chemical_name_common            ?
_chemical_temperature_decomposition 352.45
_chemical_formula_moiety         'C26 H18 O2, C6 H7 N'
_chemical_formula_sum            'C32 H25 N O2'
_chemical_formula_weight         455.53

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'
N N 0.0061 0.0033 '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           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   20.6545(7)
_cell_length_b                   9.0895(3)
_cell_length_c                   27.2828(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.2720(10)
_cell_angle_gamma                90
_cell_volume                     4835.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9069
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             1920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.249
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_absorpt_special_details   
'Additional spherical absorption correction applied with mu*r =  0.20'
_diffrn_ambient_temperature      200(2)
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_power             70
_diffrn_source_voltage           50
_diffrn_source_current           1.4
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Bruker PHOTON II 7 CCD detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            164342
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.089
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12019
_reflns_number_gt                10384
_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       'Bruker Instrument Service V6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2019/3 (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2019/3 (Sheldrick, 2015b) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows V2023.1 (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were
placed in calculated positions and were included in the refinement in the riding
model approximation, with Uiso(H) set to 1.2 Ueq(C).

The H atoms of the methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program  (Sheldrick, 2015b)) and Uiso(H) allowed to 
refine freely.

A number of reflections with large differences between their observed and
calculated intensities were omitted.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+2.0737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12019
_refine_ls_number_parameters     642
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
O11 O 0.30434(4) 0.40291(10) 0.71541(3) 0.02483(18) Uani 1 1 d . . . . .
H11 H 0.345086 0.429680 0.721061 0.045(5) Uiso 1 1 calc R . . . .
O12 O 0.17901(4) 0.25987(10) 0.68904(3) 0.02654(19) Uani 1 1 d . . . . .
H12 H 0.190456 0.309388 0.716580 0.046(5) Uiso 1 1 calc R . . . .
O21 O 0.33585(5) 0.19774(10) 0.29228(3) 0.02741(19) Uani 1 1 d . . . . .
H21 H 0.314753 0.146645 0.266253 0.046(5) Uiso 1 1 calc R . . . .
O22 O 0.22423(4) 0.04519(10) 0.30188(3) 0.02498(18) Uani 1 1 d . . . . .
H22 H 0.189267 0.015716 0.308226 0.047(5) Uiso 1 1 calc R . . . .
N3 N 0.43318(6) 0.50819(15) 0.73547(5) 0.0377(3) Uani 1 1 d . . . . .
N4 N 0.10732(6) 0.93935(16) 0.31614(5) 0.0411(3) Uani 1 1 d . . . . .
C11 C 0.27937(6) 0.33159(13) 0.66613(4) 0.0218(2) Uani 1 1 d . . . . .
C12 C 0.19920(6) 0.33560(14) 0.65074(4) 0.0236(2) Uani 1 1 d . . . . .
C21 C 0.34130(6) 0.11805(14) 0.33837(4) 0.0234(2) Uani 1 1 d . . . . .
C22 C 0.27005(6) 0.11475(13) 0.34703(4) 0.0227(2) Uani 1 1 d . . . . .
C31 C 0.51882(7) 0.64765(19) 0.80013(6) 0.0405(3) Uani 1 1 d . . . . .
C32 C 0.46068(7) 0.55921(19) 0.78372(6) 0.0385(3) Uani 1 1 d . . . . .
H32 H 0.439228 0.533557 0.808436 0.046 Uiso 1 1 calc R U . . .
C33 C 0.46453(7) 0.54218(18) 0.70137(6) 0.0393(3) Uani 1 1 d . . . . .
H33 H 0.445747 0.506493 0.666833 0.047 Uiso 1 1 calc R U . . .
C34 C 0.52313(8) 0.62708(19) 0.71422(6) 0.0415(3) Uani 1 1 d . . . . .
H34 H 0.544519 0.648349 0.689086 0.050 Uiso 1 1 calc R U . . .
C35 C 0.55004(7) 0.68036(18) 0.76398(7) 0.0423(4) Uani 1 1 d . . . . .
H35 H 0.590136 0.739704 0.773440 0.051 Uiso 1 1 calc R U . . .
C36 C 0.54474(10) 0.7060(3) 0.85467(8) 0.0687(6) Uani 1 1 d . . . . .
H36A H 0.593864 0.727319 0.864252 0.103 Uiso 1 1 calc R U . . .
H36B H 0.537313 0.632285 0.878494 0.103 Uiso 1 1 calc R U . . .
H36C H 0.519955 0.796333 0.856844 0.103 Uiso 1 1 calc R U . . .
C41 C 0.04118(9) 0.8355(2) 0.36536(7) 0.0462(4) Uani 1 1 d . . . . .
C42 C 0.10091(7) 0.89304(18) 0.36082(6) 0.0399(3) Uani 1 1 d . . . . .
H42 H 0.139826 0.900087 0.391361 0.048 Uiso 1 1 calc R U . . .
C43 C 0.05267(8) 0.9283(2) 0.27323(7) 0.0470(4) Uani 1 1 d . . . . .
H43 H 0.056453 0.960393 0.241146 0.056 Uiso 1 1 calc R U . . .
C44 C -0.00906(8) 0.8721(2) 0.27383(8) 0.0560(5) Uani 1 1 d . . . . .
H44 H -0.047024 0.865158 0.242643 0.067 Uiso 1 1 calc R U . . .
C45 C -0.01487(8) 0.8263(2) 0.32007(8) 0.0561(5) Uani 1 1 d . . . . .
H45 H -0.057223 0.788347 0.321149 0.067 Uiso 1 1 calc R U . . .
C46 C 0.03848(14) 0.7836(3) 0.41700(9) 0.0777(7) Uani 1 1 d . . . . .
H46A H 0.010317 0.851411 0.429315 0.117 Uiso 1 1 calc R U . . .
H46B H 0.085028 0.780631 0.442149 0.117 Uiso 1 1 calc R U . . .
H46C H 0.018339 0.684867 0.413176 0.117 Uiso 1 1 calc R U . . .
C111 C 0.30750(6) 0.17548(14) 0.66777(5) 0.0243(2) Uani 1 1 d . . . . .
C112 C 0.33919(6) 0.15822(15) 0.63000(5) 0.0274(3) Uani 1 1 d . . . . .
C113 C 0.37002(8) 0.02587(17) 0.62506(6) 0.0373(3) Uani 1 1 d . . . . .
H113 H 0.391658 0.014480 0.599503 0.045 Uiso 1 1 calc R U . . .
C114 C 0.36873(8) -0.08906(17) 0.65790(6) 0.0418(3) Uani 1 1 d . . . . .
H114 H 0.389493 -0.180286 0.654806 0.050 Uiso 1 1 calc R U . . .
C115 C 0.33729(8) -0.07212(17) 0.69540(6) 0.0392(3) Uani 1 1 d . . . . .
H115 H 0.336659 -0.152173 0.717620 0.047 Uiso 1 1 calc R U . . .
C116 C 0.30672(7) 0.06054(15) 0.70083(5) 0.0311(3) Uani 1 1 d . . . . .
H116 H 0.285695 0.071978 0.726756 0.037 Uiso 1 1 calc R U . . .
C121 C 0.30393(6) 0.40313(14) 0.62465(5) 0.0246(2) Uani 1 1 d . . . . .
C122 C 0.33584(6) 0.29868(15) 0.60283(5) 0.0271(3) Uani 1 1 d . . . . .
C123 C 0.36065(7) 0.33761(18) 0.56288(5) 0.0352(3) Uani 1 1 d . . . . .
H123 H 0.380475 0.265731 0.546900 0.042 Uiso 1 1 calc R U . . .
C124 C 0.35586(8) 0.48283(19) 0.54697(6) 0.0407(3) Uani 1 1 d . . . . .
H124 H 0.372435 0.510893 0.519732 0.049 Uiso 1 1 calc R U . . .
C125 C 0.32714(8) 0.58774(18) 0.57033(6) 0.0392(3) Uani 1 1 d . . . . .
H125 H 0.325893 0.687646 0.559829 0.047 Uiso 1 1 calc R U . . .
C126 C 0.30000(7) 0.54884(16) 0.60908(5) 0.0309(3) Uani 1 1 d . . . . .
H126 H 0.279297 0.620674 0.624429 0.037 Uiso 1 1 calc R U . . .
C131 C 0.17159(6) 0.49295(15) 0.64133(5) 0.0279(3) Uani 1 1 d . . . . .
C132 C 0.13044(7) 0.51095(17) 0.58940(5) 0.0330(3) Uani 1 1 d . . . . .
C133 C 0.09983(8) 0.64629(19) 0.57187(7) 0.0447(4) Uani 1 1 d . . . . .
H133 H 0.072000 0.658856 0.536644 0.054 Uiso 1 1 calc R U . . .
C134 C 0.11058(9) 0.76185(19) 0.60650(8) 0.0490(4) Uani 1 1 d . . . . .
H134 H 0.089773 0.854417 0.594952 0.059 Uiso 1 1 calc R U . . .
C135 C 0.15124(8) 0.74453(18) 0.65779(7) 0.0445(4) Uani 1 1 d . . . . .
H135 H 0.158253 0.825369 0.681038 0.053 Uiso 1 1 calc R U . . .
C136 C 0.18209(7) 0.60935(16) 0.67572(6) 0.0353(3) Uani 1 1 d . . . . .
H136 H 0.209864 0.597510 0.711001 0.042 Uiso 1 1 calc R U . . .
C141 C 0.16386(6) 0.26461(15) 0.59795(5) 0.0271(3) Uani 1 1 d . . . . .
C142 C 0.12605(7) 0.37021(17) 0.56251(5) 0.0331(3) Uani 1 1 d . . . . .
C143 C 0.08954(8) 0.3306(2) 0.51161(6) 0.0449(4) Uani 1 1 d . . . . .
H143 H 0.064967 0.402416 0.487246 0.054 Uiso 1 1 calc R U . . .
C144 C 0.08968(9) 0.1849(2) 0.49712(6) 0.0493(4) Uani 1 1 d . . . . .
H144 H 0.064896 0.156413 0.462492 0.059 Uiso 1 1 calc R U . . .
C145 C 0.12551(8) 0.0802(2) 0.53251(6) 0.0432(4) Uani 1 1 d . . . . .
H145 H 0.124417 -0.019637 0.521971 0.052 Uiso 1 1 calc R U . . .
C146 C 0.16327(7) 0.11901(17) 0.58347(5) 0.0332(3) Uani 1 1 d . . . . .
H146 H 0.187973 0.046861 0.607614 0.040 Uiso 1 1 calc R U . . .
C211 C 0.39661(6) 0.18861(14) 0.38406(5) 0.0255(2) Uani 1 1 d . . . . .
C212 C 0.44674(7) 0.08498(16) 0.40887(5) 0.0305(3) Uani 1 1 d . . . . .
C213 C 0.50300(7) 0.12372(19) 0.45154(6) 0.0396(3) Uani 1 1 d . . . . .
H213 H 0.536986 0.053099 0.468341 0.048 Uiso 1 1 calc R U . . .
C214 C 0.50817(8) 0.2676(2) 0.46888(6) 0.0449(4) Uani 1 1 d . . . . .
H214 H 0.545850 0.295778 0.498279 0.054 Uiso 1 1 calc R U . . .
C215 C 0.45911(8) 0.37151(19) 0.44394(6) 0.0430(4) Uani 1 1 d . . . . .
H215 H 0.464054 0.470158 0.456118 0.052 Uiso 1 1 calc R U . . .
C216 C 0.40248(7) 0.33271(16) 0.40109(5) 0.0336(3) Uani 1 1 d . . . . .
H216 H 0.368840 0.403788 0.384097 0.040 Uiso 1 1 calc R U . . .
C221 C 0.36987(6) -0.03742(14) 0.33865(5) 0.0259(2) Uani 1 1 d . . . . .
C222 C 0.42980(6) -0.05528(16) 0.38116(5) 0.0294(3) Uani 1 1 d . . . . .
C223 C 0.46329(8) -0.18979(18) 0.39088(6) 0.0404(3) Uani 1 1 d . . . . .
H223 H 0.503520 -0.202162 0.420132 0.049 Uiso 1 1 calc R U . . .
C224 C 0.43717(9) -0.30573(18) 0.35728(7) 0.0434(4) Uani 1 1 d . . . . .
H224 H 0.459413 -0.398687 0.363746 0.052 Uiso 1 1 calc R U . . .
C225 C 0.37884(9) -0.28749(17) 0.31425(6) 0.0394(3) Uani 1 1 d . . . . .
H225 H 0.362111 -0.367453 0.291102 0.047 Uiso 1 1 calc R U . . .
C226 C 0.34448(7) -0.15295(15) 0.30462(5) 0.0316(3) Uani 1 1 d . . . . .
H226 H 0.304376 -0.140769 0.275247 0.038 Uiso 1 1 calc R U . . .
C231 C 0.27350(6) 0.03766(14) 0.39748(4) 0.0239(2) Uani 1 1 d . . . . .
C232 C 0.25747(6) 0.13659(15) 0.43112(5) 0.0283(3) Uani 1 1 d . . . . .
C233 C 0.25558(8) 0.09042(18) 0.47921(5) 0.0378(3) Uani 1 1 d . . . . .
H233 H 0.244735 0.157673 0.501999 0.045 Uiso 1 1 calc R U . . .
C234 C 0.26976(9) -0.05499(19) 0.49320(5) 0.0421(4) Uani 1 1 d . . . . .
H234 H 0.268648 -0.087903 0.525960 0.051 Uiso 1 1 calc R U . . .
C235 C 0.28563(8) -0.15392(18) 0.46004(5) 0.0377(3) Uani 1 1 d . . . . .
H235 H 0.295372 -0.253522 0.470403 0.045 Uiso 1 1 calc R U . . .
C236 C 0.28740(7) -0.10818(15) 0.41155(5) 0.0295(3) Uani 1 1 d . . . . .
H236 H 0.297934 -0.175872 0.388738 0.035 Uiso 1 1 calc R U . . .
C241 C 0.24577(6) 0.26843(14) 0.35568(5) 0.0270(3) Uani 1 1 d . . . . .
C242 C 0.24107(7) 0.27979(15) 0.40557(5) 0.0296(3) Uani 1 1 d . . . . .
C243 C 0.22093(8) 0.41064(18) 0.42264(6) 0.0413(3) Uani 1 1 d . . . . .
H243 H 0.218601 0.418801 0.456732 0.050 Uiso 1 1 calc R U . . .
C244 C 0.20429(9) 0.52914(18) 0.38863(7) 0.0489(4) Uani 1 1 d . . . . .
H244 H 0.190347 0.619423 0.399591 0.059 Uiso 1 1 calc R U . . .
C245 C 0.20778(9) 0.51735(17) 0.33875(7) 0.0453(4) Uani 1 1 d . . . . .
H245 H 0.195683 0.599392 0.315967 0.054 Uiso 1 1 calc R U . . .
C246 C 0.22872(8) 0.38716(16) 0.32171(6) 0.0355(3) Uani 1 1 d . . . . .
H246 H 0.231312 0.379604 0.287677 0.043 Uiso 1 1 calc R U . . .


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 -1.00 0.00 0.1650
-3.00 -1.00 -4.00 0.1690
-3.00 0.00 1.00 0.0970
-2.00 0.00 -3.00 0.1440
-2.00 -3.00 1.00 0.2020
-1.00 0.00 1.00 0.0950
0.00 1.00 -4.00 0.1510
0.00 0.00 -1.00 0.1220
0.00 0.00 1.00 0.1900
1.00 0.00 -1.00 0.1220
1.00 -1.00 1.00 0.1910
1.00 -3.00 -2.00 0.1830
1.00 0.00 1.00 0.1990
1.00 0.00 -2.00 0.1200
1.00 -1.00 -1.00 0.1620
1.00 -1.00 -4.00 0.1600
1.00 1.00 4.00 0.1640
2.00 -1.00 -1.00 0.1720
2.00 2.00 3.00 0.1510
2.00 1.00 -4.00 0.1310
2.00 -1.00 -4.00 0.1540
3.00 4.00 -1.00 0.1040
3.00 1.00 -3.00 0.1330
3.00 0.00 -2.00 0.1390
3.00 -1.00 -4.00 0.1490
3.00 -2.00 -2.00 0.1680
3.00 1.00 4.00 0.1660
4.00 0.00 -1.00 0.1580
4.00 -1.00 -2.00 0.1570
4.00 -1.00 -4.00 0.1480

_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
O11 C11 1.4269(14) . ?
O11 H11 0.8400 . ?
O12 C12 1.4239(14) . ?
O12 H12 0.8400 . ?
O21 C21 1.4229(14) . ?
O21 H21 0.8400 . ?
O22 C22 1.4294(14) . ?
O22 H22 0.8400 . ?
N3 C32 1.3332(19) . ?
N3 C33 1.3332(19) . ?
N4 C43 1.335(2) . ?
N4 C42 1.337(2) . ?
C11 C111 1.5283(17) . ?
C11 C121 1.5297(16) . ?
C11 C12 1.5685(16) . ?
C12 C141 1.5263(17) . ?
C12 C131 1.5297(18) . ?
C21 C211 1.5266(16) . ?
C21 C221 1.5305(18) . ?
C21 C22 1.5658(16) . ?
C22 C231 1.5252(16) . ?
C22 C241 1.5287(17) . ?
C31 C35 1.377(2) . ?
C31 C32 1.391(2) . ?
C31 C36 1.502(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.380(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.374(2) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C41 C42 1.383(2) . ?
C41 C45 1.389(3) . ?
C41 C46 1.504(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.379(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.371(3) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C111 C116 1.3837(18) . ?
C111 C112 1.4002(17) . ?
C112 C113 1.388(2) . ?
C112 C122 1.4665(19) . ?
C113 C114 1.382(2) . ?
C113 H113 0.9500 . ?
C114 C115 1.389(2) . ?
C114 H114 0.9500 . ?
C115 C116 1.392(2) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C121 C126 1.3851(19) . ?
C121 C122 1.3961(18) . ?
C122 C123 1.3944(18) . ?
C123 C124 1.383(2) . ?
C123 H123 0.9500 . ?
C124 C125 1.384(2) . ?
C124 H124 0.9500 . ?
C125 C126 1.3960(19) . ?
C125 H125 0.9500 . ?
C126 H126 0.9500 . ?
C131 C136 1.383(2) . ?
C131 C132 1.4006(19) . ?
C132 C133 1.394(2) . ?
C132 C142 1.463(2) . ?
C133 C134 1.381(3) . ?
C133 H133 0.9500 . ?
C134 C135 1.383(3) . ?
C134 H134 0.9500 . ?
C135 C136 1.396(2) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C141 C146 1.380(2) . ?
C141 C142 1.4027(19) . ?
C142 C143 1.391(2) . ?
C143 C144 1.382(3) . ?
C143 H143 0.9500 . ?
C144 C145 1.384(3) . ?
C144 H144 0.9500 . ?
C145 C146 1.3965(19) . ?
C145 H145 0.9500 . ?
C146 H146 0.9500 . ?
C211 C216 1.3817(19) . ?
C211 C212 1.3982(19) . ?
C212 C213 1.3915(19) . ?
C212 C222 1.465(2) . ?
C213 C214 1.383(2) . ?
C213 H213 0.9500 . ?
C214 C215 1.388(3) . ?
C214 H214 0.9500 . ?
C215 C216 1.399(2) . ?
C215 H215 0.9500 . ?
C216 H216 0.9500 . ?
C221 C226 1.3850(19) . ?
C221 C222 1.3985(18) . ?
C222 C223 1.387(2) . ?
C223 C224 1.384(2) . ?
C223 H223 0.9500 . ?
C224 C225 1.387(2) . ?
C224 H224 0.9500 . ?
C225 C226 1.395(2) . ?
C225 H225 0.9500 . ?
C226 H226 0.9500 . ?
C231 C236 1.3836(18) . ?
C231 C232 1.4004(18) . ?
C232 C233 1.3901(19) . ?
C232 C242 1.463(2) . ?
C233 C234 1.380(2) . ?
C233 H233 0.9500 . ?
C234 C235 1.389(2) . ?
C234 H234 0.9500 . ?
C235 C236 1.3988(18) . ?
C235 H235 0.9500 . ?
C236 H236 0.9500 . ?
C241 C246 1.3901(19) . ?
C241 C242 1.3998(18) . ?
C242 C243 1.390(2) . ?
C243 C244 1.389(2) . ?
C243 H243 0.9500 . ?
C244 C245 1.390(3) . ?
C244 H244 0.9500 . ?
C245 C246 1.392(2) . ?
C245 H245 0.9500 . ?
C246 H246 0.9500 . ?

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
C11 O11 H11 109.5 . . ?
C12 O12 H12 109.5 . . ?
C21 O21 H21 109.5 . . ?
C22 O22 H22 109.5 . . ?
C32 N3 C33 117.49(13) . . ?
C43 N4 C42 117.80(13) . . ?
O11 C11 C111 112.24(9) . . ?
O11 C11 C121 113.51(10) . . ?
C111 C11 C121 101.58(10) . . ?
O11 C11 C12 105.25(9) . . ?
C111 C11 C12 112.76(10) . . ?
C121 C11 C12 111.76(9) . . ?
O12 C12 C141 108.88(10) . . ?
O12 C12 C131 113.07(10) . . ?
C141 C12 C131 101.61(10) . . ?
O12 C12 C11 109.34(9) . . ?
C141 C12 C11 112.13(10) . . ?
C131 C12 C11 111.64(10) . . ?
O21 C21 C211 109.11(10) . . ?
O21 C21 C221 113.10(10) . . ?
C211 C21 C221 101.56(10) . . ?
O21 C21 C22 109.81(9) . . ?
C211 C21 C22 111.85(9) . . ?
C221 C21 C22 111.20(10) . . ?
O22 C22 C231 113.26(10) . . ?
O22 C22 C241 112.31(10) . . ?
C231 C22 C241 101.56(10) . . ?
O22 C22 C21 105.46(9) . . ?
C231 C22 C21 112.26(10) . . ?
C241 C22 C21 112.23(10) . . ?
C35 C31 C32 116.93(14) . . ?
C35 C31 C36 122.36(15) . . ?
C32 C31 C36 120.70(15) . . ?
N3 C32 C31 124.07(14) . . ?
N3 C32 H32 118.0 . . ?
C31 C32 H32 118.0 . . ?
N3 C33 C34 122.68(14) . . ?
N3 C33 H33 118.7 . . ?
C34 C33 H33 118.7 . . ?
C35 C34 C33 118.86(14) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 C31 119.95(14) . . ?
C34 C35 H35 120.0 . . ?
C31 C35 H35 120.0 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C42 C41 C45 116.70(16) . . ?
C42 C41 C46 120.83(17) . . ?
C45 C41 C46 122.46(17) . . ?
N4 C42 C41 124.10(15) . . ?
N4 C42 H42 118.0 . . ?
C41 C42 H42 118.0 . . ?
N4 C43 C44 122.34(17) . . ?
N4 C43 H43 118.8 . . ?
C44 C43 H43 118.8 . . ?
C45 C44 C43 119.05(16) . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C44 C45 C41 120.00(15) . . ?
C44 C45 H45 120.0 . . ?
C41 C45 H45 120.0 . . ?
C41 C46 H46A 109.5 . . ?
C41 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C41 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C116 C111 C112 120.26(12) . . ?
C116 C111 C11 129.35(11) . . ?
C112 C111 C11 110.37(11) . . ?
C113 C112 C111 120.62(13) . . ?
C113 C112 C122 130.69(12) . . ?
C111 C112 C122 108.60(11) . . ?
C114 C113 C112 118.98(13) . . ?
C114 C113 H113 120.5 . . ?
C112 C113 H113 120.5 . . ?
C113 C114 C115 120.47(14) . . ?
C113 C114 H114 119.8 . . ?
C115 C114 H114 119.8 . . ?
C114 C115 C116 120.88(14) . . ?
C114 C115 H115 119.6 . . ?
C116 C115 H115 119.6 . . ?
C111 C116 C115 118.79(13) . . ?
C111 C116 H116 120.6 . . ?
C115 C116 H116 120.6 . . ?
C126 C121 C122 120.51(12) . . ?
C126 C121 C11 129.28(12) . . ?
C122 C121 C11 110.18(11) . . ?
C123 C122 C121 120.52(13) . . ?
C123 C122 C112 130.38(13) . . ?
C121 C122 C112 109.06(11) . . ?
C124 C123 C122 118.74(14) . . ?
C124 C123 H123 120.6 . . ?
C122 C123 H123 120.6 . . ?
C123 C124 C125 120.67(13) . . ?
C123 C124 H124 119.7 . . ?
C125 C124 H124 119.7 . . ?
C124 C125 C126 120.96(14) . . ?
C124 C125 H125 119.5 . . ?
C126 C125 H125 119.5 . . ?
C121 C126 C125 118.48(14) . . ?
C121 C126 H126 120.8 . . ?
C125 C126 H126 120.8 . . ?
C136 C131 C132 120.26(13) . . ?
C136 C131 C12 129.43(12) . . ?
C132 C131 C12 110.31(12) . . ?
C133 C132 C131 120.35(15) . . ?
C133 C132 C142 130.85(14) . . ?
C131 C132 C142 108.77(12) . . ?
C134 C133 C132 118.98(15) . . ?
C134 C133 H133 120.5 . . ?
C132 C133 H133 120.5 . . ?
C133 C134 C135 120.83(15) . . ?
C133 C134 H134 119.6 . . ?
C135 C134 H134 119.6 . . ?
C134 C135 C136 120.62(16) . . ?
C134 C135 H135 119.7 . . ?
C136 C135 H135 119.7 . . ?
C131 C136 C135 118.96(14) . . ?
C131 C136 H136 120.5 . . ?
C135 C136 H136 120.5 . . ?
C146 C141 C142 120.57(12) . . ?
C146 C141 C12 129.18(12) . . ?
C142 C141 C12 110.20(12) . . ?
C143 C142 C141 120.41(15) . . ?
C143 C142 C132 130.57(14) . . ?
C141 C142 C132 108.94(12) . . ?
C144 C143 C142 118.79(15) . . ?
C144 C143 H143 120.6 . . ?
C142 C143 H143 120.6 . . ?
C143 C144 C145 120.71(14) . . ?
C143 C144 H144 119.6 . . ?
C145 C144 H144 119.6 . . ?
C144 C145 C146 121.02(16) . . ?
C144 C145 H145 119.5 . . ?
C146 C145 H145 119.5 . . ?
C141 C146 C145 118.46(14) . . ?
C141 C146 H146 120.8 . . ?
C145 C146 H146 120.8 . . ?
C216 C211 C212 120.47(12) . . ?
C216 C211 C21 129.19(12) . . ?
C212 C211 C21 110.33(11) . . ?
C213 C212 C211 121.00(14) . . ?
C213 C212 C222 130.05(14) . . ?
C211 C212 C222 108.90(11) . . ?
C214 C213 C212 118.31(15) . . ?
C214 C213 H213 120.8 . . ?
C212 C213 H213 120.8 . . ?
C213 C214 C215 120.95(14) . . ?
C213 C214 H214 119.5 . . ?
C215 C214 H214 119.5 . . ?
C214 C215 C216 120.80(15) . . ?
C214 C215 H215 119.6 . . ?
C216 C215 H215 119.6 . . ?
C211 C216 C215 118.45(14) . . ?
C211 C216 H216 120.8 . . ?
C215 C216 H216 120.8 . . ?
C226 C221 C222 120.24(12) . . ?
C226 C221 C21 129.54(12) . . ?
C222 C221 C21 110.21(11) . . ?
C223 C222 C221 120.66(13) . . ?
C223 C222 C212 130.52(13) . . ?
C221 C222 C212 108.81(12) . . ?
C224 C223 C222 118.95(14) . . ?
C224 C223 H223 120.5 . . ?
C222 C223 H223 120.5 . . ?
C223 C224 C225 120.62(14) . . ?
C223 C224 H224 119.7 . . ?
C225 C224 H224 119.7 . . ?
C224 C225 C226 120.68(14) . . ?
C224 C225 H225 119.7 . . ?
C226 C225 H225 119.7 . . ?
C221 C226 C225 118.82(13) . . ?
C221 C226 H226 120.6 . . ?
C225 C226 H226 120.6 . . ?
C236 C231 C232 120.38(12) . . ?
C236 C231 C22 129.35(11) . . ?
C232 C231 C22 110.23(11) . . ?
C233 C232 C231 120.73(13) . . ?
C233 C232 C242 130.11(13) . . ?
C231 C232 C242 109.07(11) . . ?
C234 C233 C232 118.73(14) . . ?
C234 C233 H233 120.6 . . ?
C232 C233 H233 120.6 . . ?
C233 C234 C235 120.93(13) . . ?
C233 C234 H234 119.5 . . ?
C235 C234 H234 119.5 . . ?
C234 C235 C236 120.60(14) . . ?
C234 C235 H235 119.7 . . ?
C236 C235 H235 119.7 . . ?
C231 C236 C235 118.64(13) . . ?
C231 C236 H236 120.7 . . ?
C235 C236 H236 120.7 . . ?
C246 C241 C242 120.49(13) . . ?
C246 C241 C22 129.07(12) . . ?
C242 C241 C22 110.44(11) . . ?
C243 C242 C241 120.89(14) . . ?
C243 C242 C232 130.51(13) . . ?
C241 C242 C232 108.56(11) . . ?
C244 C243 C242 118.37(14) . . ?
C244 C243 H243 120.8 . . ?
C242 C243 H243 120.8 . . ?
C243 C244 C245 120.84(15) . . ?
C243 C244 H244 119.6 . . ?
C245 C244 H244 119.6 . . ?
C244 C245 C246 120.99(15) . . ?
C244 C245 H245 119.5 . . ?
C246 C245 H245 119.5 . . ?
C241 C246 C245 118.40(14) . . ?
C241 C246 H246 120.8 . . ?
C245 C246 H246 120.8 . . ?

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
O11 C11 C12 O12 -59.88(12) . . . . ?
C111 C11 C12 O12 62.79(13) . . . . ?
C121 C11 C12 O12 176.48(10) . . . . ?
O11 C11 C12 C141 179.26(10) . . . . ?
C111 C11 C12 C141 -58.07(13) . . . . ?
C121 C11 C12 C141 55.62(14) . . . . ?
O11 C11 C12 C131 66.00(12) . . . . ?
C111 C11 C12 C131 -171.33(10) . . . . ?
C121 C11 C12 C131 -57.65(13) . . . . ?
O21 C21 C22 O22 59.27(12) . . . . ?
C211 C21 C22 O22 -179.44(10) . . . . ?
C221 C21 C22 O22 -66.67(12) . . . . ?
O21 C21 C22 C231 -176.96(10) . . . . ?
C211 C21 C22 C231 -55.68(14) . . . . ?
C221 C21 C22 C231 57.10(13) . . . . ?
O21 C21 C22 C241 -63.31(12) . . . . ?
C211 C21 C22 C241 57.97(13) . . . . ?
C221 C21 C22 C241 170.75(10) . . . . ?
C33 N3 C32 C31 1.4(2) . . . . ?
C35 C31 C32 N3 -1.6(3) . . . . ?
C36 C31 C32 N3 177.31(18) . . . . ?
C32 N3 C33 C34 -0.2(2) . . . . ?
N3 C33 C34 C35 -0.7(3) . . . . ?
C33 C34 C35 C31 0.5(3) . . . . ?
C32 C31 C35 C34 0.5(3) . . . . ?
C36 C31 C35 C34 -178.33(19) . . . . ?
C43 N4 C42 C41 -0.5(3) . . . . ?
C45 C41 C42 N4 0.1(3) . . . . ?
C46 C41 C42 N4 179.03(19) . . . . ?
C42 N4 C43 C44 0.3(3) . . . . ?
N4 C43 C44 C45 0.3(3) . . . . ?
C43 C44 C45 C41 -0.7(3) . . . . ?
C42 C41 C45 C44 0.5(3) . . . . ?
C46 C41 C45 C44 -178.4(2) . . . . ?
O11 C11 C111 C116 52.81(16) . . . . ?
C121 C11 C111 C116 174.39(13) . . . . ?
C12 C11 C111 C116 -65.86(16) . . . . ?
O11 C11 C111 C112 -125.28(11) . . . . ?
C121 C11 C111 C112 -3.71(12) . . . . ?
C12 C11 C111 C112 116.04(11) . . . . ?
C116 C111 C112 C113 0.19(19) . . . . ?
C11 C111 C112 C113 178.49(12) . . . . ?
C116 C111 C112 C122 -176.76(11) . . . . ?
C11 C111 C112 C122 1.53(13) . . . . ?
C111 C112 C113 C114 0.3(2) . . . . ?
C122 C112 C113 C114 176.45(14) . . . . ?
C112 C113 C114 C115 -0.2(2) . . . . ?
C113 C114 C115 C116 -0.2(2) . . . . ?
C112 C111 C116 C115 -0.64(19) . . . . ?
C11 C111 C116 C115 -178.58(12) . . . . ?
C114 C115 C116 C111 0.7(2) . . . . ?
O11 C11 C121 C126 -52.54(17) . . . . ?
C111 C11 C121 C126 -173.23(12) . . . . ?
C12 C11 C121 C126 66.31(16) . . . . ?
O11 C11 C121 C122 125.39(11) . . . . ?
C111 C11 C121 C122 4.70(12) . . . . ?
C12 C11 C121 C122 -115.76(11) . . . . ?
C126 C121 C122 C123 -3.79(19) . . . . ?
C11 C121 C122 C123 178.07(11) . . . . ?
C126 C121 C122 C112 174.06(11) . . . . ?
C11 C121 C122 C112 -4.09(14) . . . . ?
C113 C112 C122 C123 2.6(2) . . . . ?
C111 C112 C122 C123 179.16(13) . . . . ?
C113 C112 C122 C121 -174.95(14) . . . . ?
C111 C112 C122 C121 1.60(14) . . . . ?
C121 C122 C123 C124 2.9(2) . . . . ?
C112 C122 C123 C124 -174.42(13) . . . . ?
C122 C123 C124 C125 0.2(2) . . . . ?
C123 C124 C125 C126 -2.4(2) . . . . ?
C122 C121 C126 C125 1.51(19) . . . . ?
C11 C121 C126 C125 179.25(12) . . . . ?
C124 C125 C126 C121 1.6(2) . . . . ?
O12 C12 C131 C136 59.67(17) . . . . ?
C141 C12 C131 C136 176.19(13) . . . . ?
C11 C12 C131 C136 -64.13(17) . . . . ?
O12 C12 C131 C132 -120.35(11) . . . . ?
C141 C12 C131 C132 -3.83(13) . . . . ?
C11 C12 C131 C132 115.85(11) . . . . ?
C136 C131 C132 C133 0.1(2) . . . . ?
C12 C131 C132 C133 -179.84(12) . . . . ?
C136 C131 C132 C142 -177.86(12) . . . . ?
C12 C131 C132 C142 2.16(14) . . . . ?
C131 C132 C133 C134 -0.2(2) . . . . ?
C142 C132 C133 C134 177.33(14) . . . . ?
C132 C133 C134 C135 0.3(2) . . . . ?
C133 C134 C135 C136 -0.3(3) . . . . ?
C132 C131 C136 C135 -0.2(2) . . . . ?
C12 C131 C136 C135 179.79(13) . . . . ?
C134 C135 C136 C131 0.3(2) . . . . ?
O12 C12 C141 C146 -53.63(17) . . . . ?
C131 C12 C141 C146 -173.17(13) . . . . ?
C11 C12 C141 C146 67.50(17) . . . . ?
O12 C12 C141 C142 123.78(11) . . . . ?
C131 C12 C141 C142 4.24(13) . . . . ?
C11 C12 C141 C142 -115.10(12) . . . . ?
C146 C141 C142 C143 -2.5(2) . . . . ?
C12 C141 C142 C143 179.79(12) . . . . ?
C146 C141 C142 C132 174.44(12) . . . . ?
C12 C141 C142 C132 -3.23(14) . . . . ?
C133 C132 C142 C143 -0.5(3) . . . . ?
C131 C132 C142 C143 177.24(14) . . . . ?
C133 C132 C142 C141 -177.06(14) . . . . ?
C131 C132 C142 C141 0.67(15) . . . . ?
C141 C142 C143 C144 1.8(2) . . . . ?
C132 C142 C143 C144 -174.41(15) . . . . ?
C142 C143 C144 C145 -0.1(2) . . . . ?
C143 C144 C145 C146 -1.0(3) . . . . ?
C142 C141 C146 C145 1.5(2) . . . . ?
C12 C141 C146 C145 178.63(13) . . . . ?
C144 C145 C146 C141 0.3(2) . . . . ?
O21 C21 C211 C216 55.04(17) . . . . ?
C221 C21 C211 C216 174.69(13) . . . . ?
C22 C21 C211 C216 -66.65(17) . . . . ?
O21 C21 C211 C212 -123.34(11) . . . . ?
C221 C21 C211 C212 -3.70(13) . . . . ?
C22 C21 C211 C212 114.97(12) . . . . ?
C216 C211 C212 C213 0.9(2) . . . . ?
C21 C211 C212 C213 179.43(12) . . . . ?
C216 C211 C212 C222 -176.72(12) . . . . ?
C21 C211 C212 C222 1.82(14) . . . . ?
C211 C212 C213 C214 0.0(2) . . . . ?
C222 C212 C213 C214 177.03(14) . . . . ?
C212 C213 C214 C215 -1.0(2) . . . . ?
C213 C214 C215 C216 1.1(3) . . . . ?
C212 C211 C216 C215 -0.8(2) . . . . ?
C21 C211 C216 C215 -179.01(13) . . . . ?
C214 C215 C216 C211 -0.2(2) . . . . ?
O21 C21 C221 C226 -59.68(17) . . . . ?
C211 C21 C221 C226 -176.46(13) . . . . ?
C22 C21 C221 C226 64.41(16) . . . . ?
O21 C21 C221 C222 121.16(11) . . . . ?
C211 C21 C221 C222 4.38(13) . . . . ?
C22 C21 C221 C222 -114.75(11) . . . . ?
C226 C221 C222 C223 -2.2(2) . . . . ?
C21 C221 C222 C223 177.04(12) . . . . ?
C226 C221 C222 C212 177.18(12) . . . . ?
C21 C221 C222 C212 -3.57(14) . . . . ?
C213 C212 C222 C223 3.1(3) . . . . ?
C211 C212 C222 C223 -179.59(14) . . . . ?
C213 C212 C222 C221 -176.22(14) . . . . ?
C211 C212 C222 C221 1.10(15) . . . . ?
C221 C222 C223 C224 1.1(2) . . . . ?
C212 C222 C223 C224 -178.09(14) . . . . ?
C222 C223 C224 C225 0.7(2) . . . . ?
C223 C224 C225 C226 -1.4(2) . . . . ?
C222 C221 C226 C225 1.4(2) . . . . ?
C21 C221 C226 C225 -177.67(13) . . . . ?
C224 C225 C226 C221 0.4(2) . . . . ?
O22 C22 C231 C236 54.02(17) . . . . ?
C241 C22 C231 C236 174.66(12) . . . . ?
C21 C22 C231 C236 -65.28(16) . . . . ?
O22 C22 C231 C232 -123.81(11) . . . . ?
C241 C22 C231 C232 -3.17(13) . . . . ?
C21 C22 C231 C232 116.90(11) . . . . ?
C236 C231 C232 C233 0.33(19) . . . . ?
C22 C231 C232 C233 178.38(12) . . . . ?
C236 C231 C232 C242 -176.56(11) . . . . ?
C22 C231 C232 C242 1.49(14) . . . . ?
C231 C232 C233 C234 -0.1(2) . . . . ?
C242 C232 C233 C234 176.10(14) . . . . ?
C232 C233 C234 C235 0.0(2) . . . . ?
C233 C234 C235 C236 -0.2(2) . . . . ?
C232 C231 C236 C235 -0.52(19) . . . . ?
C22 C231 C236 C235 -178.15(12) . . . . ?
C234 C235 C236 C231 0.4(2) . . . . ?
O22 C22 C241 C246 -54.18(17) . . . . ?
C231 C22 C241 C246 -175.49(13) . . . . ?
C21 C22 C241 C246 64.43(17) . . . . ?
O22 C22 C241 C242 125.15(11) . . . . ?
C231 C22 C241 C242 3.85(13) . . . . ?
C21 C22 C241 C242 -116.23(11) . . . . ?
C246 C241 C242 C243 -1.6(2) . . . . ?
C22 C241 C242 C243 179.03(12) . . . . ?
C246 C241 C242 C232 176.20(12) . . . . ?
C22 C241 C242 C232 -3.19(14) . . . . ?
C233 C232 C242 C243 2.1(2) . . . . ?
C231 C232 C242 C243 178.56(14) . . . . ?
C233 C232 C242 C241 -175.44(14) . . . . ?
C231 C232 C242 C241 1.07(14) . . . . ?
C241 C242 C243 C244 1.2(2) . . . . ?
C232 C242 C243 C244 -176.01(14) . . . . ?
C242 C243 C244 C245 -0.1(3) . . . . ?
C243 C244 C245 C246 -0.7(3) . . . . ?
C242 C241 C246 C245 0.8(2) . . . . ?
C22 C241 C246 C245 -179.97(13) . . . . ?
C244 C245 C246 C241 0.4(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
O11 H11 N3 0.84 1.87 2.7084(14) 174 . yes
O12 H12 O11 0.84 2.01 2.8306(12) 165 2_556 yes
O21 H21 O22 0.84 1.99 2.8210(12) 169 2 yes
O22 H22 N4 0.84 1.91 2.7436(15) 174 1_545 yes
C45 H45 O12 0.95 2.48 3.4079(18) 167 3_566 yes

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.044

