# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_123Ka
_database_code_depnum_ccdc_archive 'CCDC 2012784'
loop_
_audit_author_name
_audit_author_address
'Kunlin Wang'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2-(Benzhydryloxy)-N,N-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate
;
_chemical_name_common            'Diphenhydramine citrate salt'
_chemical_melting_point          424
_chemical_formula_moiety         'C17 H22 N O, C6 H7 O7'
_chemical_formula_sum            'C23 H29 N O8'
_chemical_formula_weight         447.47

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   21.893(8)
_cell_length_b                   9.298(4)
_cell_length_c                   11.082(4)
_cell_angle_alpha                90.070(5)
_cell_angle_beta                 92.648(5)
_cell_angle_gamma                92.006(6)
_cell_volume                     2252.0(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2923
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   0.675
_exptl_transmission_factor_max   0.745
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.673073
_exptl_absorpt_correction_T_max  0.745552
_exptl_absorpt_process_details   TWINABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'normal focus'
_diffrn_measurement_device_type  'Bruker-axs APEX-II Platform CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10156
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.840
_diffrn_reflns_theta_max         27.664
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             10156
_reflns_number_gt                7158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'SMART, Bruker'
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;Refined as a 2-component twin. Form I is in space group P2(1)/c. Below 
 ~148K Form II is found as a twin by non-merohedry. The transformation
 from point group 2/m to -1 necessitates either a rotation or mirror 
 twin symmetry element. The twin law found by Cell_Now is found below: 

 Cell_Now indexing based on the conventional triclinic cell:
 ----------------------------------------------------------------------------

 Cell for domain  1:    9.287   11.079   21.867    92.59    92.00    90.14

 Figure of merit: 0.728   %(0.1):  78.3   %(0.2):  88.6   %(0.3):  91.6

 Orientation matrix:  0.00967874 -0.02147413  0.04387834
                     -0.08850674 -0.05150867 -0.00537914
                      0.06067884 -0.07105938 -0.01199770

 Percentages of reflections in this domain not consistent with lattice types:
 A: 52.2,  B: 48.8,  C: 51.9,  I: 50.5,  F: 76.4,  O: 63.0  and  R: 68.0%

 Percentages of reflections in this domain that do not have:
 h=2n: 48.8,  k=2n: 50.2,  l=2n: 49.2,  h=3n: 71.7,  k=3n: 72.7,  l=3n: 67.3%

 RLATT color-coding employed in file: vgy1a.p4p
 White: indexed for first domain
 Red: not yet indexed

   297 reflections within tolerance assigned to domain  1,
   297 of them exclusively;    35 reflections not yet assigned to a domain

 ----------------------------------------------------------------------------

 Cell for domain  2:    9.287   11.079   21.867    92.59    92.00    90.14

 Figure of merit: 0.678   %(0.1):  82.9   %(0.2):  85.7   %(0.3):  94.3

 Orientation matrix:  0.00227321  0.02144488 -0.04389058
                     -0.08741790  0.05135886  0.00546177
                      0.06294429  0.07117654  0.01191529

 Rotated from first domain by 180.0 degrees about
 reciprocal axis  1.000 -0.002 -0.085  and real axis  1.000  0.001 -0.001

 Twin law to convert hkl from first to      1.000   0.002  -0.001
 this domain (SHELXL TWIN matrix):         -0.003  -1.000   0.000
                                           -0.170   0.001  -1.000

 RLATT color-coding employed in file: vgy1b.p4p
 White: indexed for first domain
 Green: current domain (but not in a previous domain)
 Red: not yet indexed

   181 reflections within tolerance assigned to domain  2,
    31 of them exclusively;     4 reflections not yet assigned to a domain

 ----------------------------------------------------------------------------
 Final conventional triclinic cell from SAINT:


 Orientation ('UB') matrix (Component 1.1(1)):
   0.0095281  -0.0215247   0.0438132
  -0.0883497  -0.0514023  -0.0054473
   0.0607071  -0.0710527  -0.0120006

 Orientation ('UB') matrix (Component 1.2(2)):
   0.0023707   0.0215182  -0.0438161
  -0.0874190   0.0513369   0.0054625
   0.0627224   0.0711019   0.0119832

         A         B         C     Alpha      Beta     Gamma           Vol
    9.2976   11.0859   21.8928    92.627    91.977    90.044       2252.84
    0.0013    0.0015    0.0030     0.002     0.002     0.002          0.91
 Corrected for goodness of fit:
    0.0041    0.0048    0.0094     0.006     0.006     0.006          2.92
 ----------------------------------------------------------------------------
 Final merging statistics from TWINABS:


 Statistics for singles of twin component  1
 -------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K    Total I>2sig(I)
    1   28.0  0.0283   0.997 - 1.062   0.974 - 1.017   0.701     116      88
    2   28.0  0.0273   0.938 - 1.017   0.969 - 1.051   0.710     324     300
    3   28.0  0.0257   0.950 - 1.006   0.979 - 1.060   0.708     154     113
    4   28.0  0.0242   0.984 - 1.041   0.974 - 1.044   0.713      86      69

   All scans  0.0264   0.938 - 1.062   0.969 - 1.060   0.708     680     570


 Statistics for all composite reflections
 ----------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K    Total I>2sig(I)
    1   28.0  0.0480   0.987 - 1.073   0.969 - 1.020   0.701    4354    2964
    2   28.0  0.0449   0.937 - 1.027   0.967 - 1.066   0.710    4046    2913
    3   28.0  0.0431   0.939 - 1.010   0.976 - 1.064   0.708    4150    2854
    4   28.0  0.0453   0.981 - 1.051   0.966 - 1.071   0.713    4196    2995

   All scans  0.0454   0.937 - 1.073   0.966 - 1.071   0.708   16746   11726


 Statistics for all single and composite reflections
 ---------------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K    Total I>2sig(I)
    1   28.0  0.0477   0.987 - 1.073   0.969 - 1.020   0.701    4576    3116
    2   28.0  0.0438   0.937 - 1.027   0.967 - 1.066   0.710    4694    3471
    3   28.0  0.0422   0.939 - 1.010   0.976 - 1.064   0.708    4457    3072
    4   28.0  0.0450   0.981 - 1.051   0.966 - 1.071   0.713    4351    3115

   All scans  0.0447   0.937 - 1.073   0.966 - 1.071   0.708   18078   12774

 su = K * Sqrt[ sigma^2(I) + (g)^2 ]  where sigma(I) is estimated by SAINT

 The above statistics are based on all non-rejected data, ignoring
 reflections without equivalents when estimating R(int) and K.

 ============================================================================

 PART 3 - Output Postscript diagnostics and corrected data

 Diagnostic plots written to Postscript file 17011a.eps


 The R(int) and R(sigma) plots are based on all singles and composites,
 <|E^2-1|> is calculated for all individual contributions from domain 1
 assuming SAINT partitioning and the chi^2 and spatial plots show only
 those single and composite reflections actually fitted.


 HKLF 5 dataset constructed from all observations involving domain 1
   16206 Corrected reflections written to file 17011_hklf5.hkl
 Reflections merged according to point-group -1    
 Single reflections that also occur in composites omitted
 Minimum and maximum apparent transmission:  0.673073  0.745552
 Additional spherical absorption correction applied with mu*r =  0.2000

 The non-standard triclinic unit cell was adopted for calculations to mirror
 the axes used in the parent Form I crystal structure. End of notes on 
 twinning.

 ============================================================================,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10156
_refine_ls_number_parameters     592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.78039(7) 0.40030(17) 0.58397(13) 0.0240(4) Uani 1 1 d . . . . .
N1A N 0.68413(8) 0.4239(2) 0.35556(16) 0.0235(4) Uani 1 1 d . . . . .
H1A H 0.673952 0.527784 0.349917 0.028 Uiso 1 1 calc R U . . .
C1A C 0.90197(11) 0.2977(3) 0.6207(2) 0.0291(6) Uani 1 1 d . . . . .
H1AA H 0.885907 0.290528 0.539744 0.035 Uiso 1 1 calc R U . . .
C2A C 0.95315(11) 0.2218(3) 0.6559(2) 0.0313(6) Uani 1 1 d . . . . .
H2AA H 0.971919 0.162995 0.599116 0.038 Uiso 1 1 calc R U . . .
C3A C 0.97695(11) 0.2315(3) 0.7738(2) 0.0297(6) Uani 1 1 d . . . . .
H3AA H 1.012317 0.180435 0.797711 0.036 Uiso 1 1 calc R U . . .
C4A C 0.94895(11) 0.3161(3) 0.8566(2) 0.0276(5) Uani 1 1 d . . . . .
H4AA H 0.965035 0.323049 0.937545 0.033 Uiso 1 1 calc R U . . .
C5A C 0.89765(10) 0.3900(2) 0.8211(2) 0.0242(5) Uani 1 1 d . . . . .
H5AA H 0.878157 0.446055 0.878807 0.029 Uiso 1 1 calc R U . . .
C6A C 0.87389(10) 0.3843(2) 0.70253(19) 0.0217(5) Uani 1 1 d . . . . .
C7A C 0.82127(10) 0.4791(3) 0.66736(19) 0.0225(5) Uani 1 1 d . . . . .
H7AA H 0.798717 0.499616 0.741545 0.027 Uiso 1 1 calc R U . . .
C8A C 0.84280(10) 0.6219(3) 0.6140(2) 0.0231(5) Uani 1 1 d . . . . .
C9A C 0.86793(11) 0.6284(3) 0.5004(2) 0.0296(6) Uani 1 1 d . . . . .
H9AA H 0.873705 0.542175 0.456892 0.036 Uiso 1 1 calc R U . . .
C10A C 0.88443(11) 0.7601(3) 0.4512(2) 0.0348(6) Uani 1 1 d . . . . .
H10A H 0.900338 0.764255 0.372903 0.042 Uiso 1 1 calc R U . . .
C11A C 0.87784(11) 0.8851(3) 0.5153(2) 0.0338(6) Uani 1 1 d . . . . .
H11A H 0.889099 0.975363 0.481211 0.041 Uiso 1 1 calc R U . . .
C12A C 0.85488(11) 0.8792(3) 0.6291(2) 0.0334(6) Uani 1 1 d . . . . .
H12A H 0.851827 0.965209 0.674534 0.040 Uiso 1 1 calc R U . . .
C13A C 0.83631(10) 0.7488(3) 0.6773(2) 0.0273(5) Uani 1 1 d . . . . .
H13A H 0.818973 0.745981 0.754274 0.033 Uiso 1 1 calc R U . . .
C14A C 0.72353(10) 0.4696(3) 0.5692(2) 0.0242(5) Uani 1 1 d . . . . .
H14A H 0.730123 0.566812 0.534701 0.029 Uiso 1 1 calc R U . . .
H14B H 0.705071 0.479995 0.648451 0.029 Uiso 1 1 calc R U . . .
C15A C 0.68116(10) 0.3795(3) 0.48515(19) 0.0227(5) Uani 1 1 d . . . . .
H15A H 0.692025 0.277305 0.492569 0.027 Uiso 1 1 calc R U . . .
H15B H 0.638633 0.387421 0.510489 0.027 Uiso 1 1 calc R U . . .
C16A C 0.74615(11) 0.4081(3) 0.3084(2) 0.0307(6) Uani 1 1 d . . . . .
H16A H 0.745702 0.436752 0.223327 0.046 Uiso 1 1 calc R U . . .
H16B H 0.757747 0.307531 0.315694 0.046 Uiso 1 1 calc R U . . .
H16C H 0.775812 0.469647 0.355244 0.046 Uiso 1 1 calc R U . . .
C17A C 0.63744(11) 0.3395(3) 0.2800(2) 0.0319(6) Uani 1 1 d . . . . .
H17A H 0.638279 0.372357 0.196102 0.048 Uiso 1 1 calc R U . . .
H17B H 0.596755 0.353452 0.310522 0.048 Uiso 1 1 calc R U . . .
H17C H 0.646612 0.237113 0.283772 0.048 Uiso 1 1 calc R U . . .
O2A O 0.71712(7) 0.9259(2) 0.54608(14) 0.0333(4) Uani 1 1 d . . . . .
H2A H 0.694444 0.888655 0.597504 0.040 Uiso 1 1 calc R U . . .
O3A O 0.70667(7) 1.03106(18) 0.36949(14) 0.0295(4) Uani 1 1 d . . . . .
O4A O 0.59937(7) 0.86150(17) 0.18449(12) 0.0243(4) Uani 1 1 d . . . . .
O5A O 0.66395(7) 0.69136(17) 0.24025(12) 0.0220(4) Uani 1 1 d . . . . .
O6A O 0.52867(8) 0.5639(2) 0.24808(15) 0.0384(5) Uani 1 1 d . . . . .
O7A O 0.44854(8) 0.59179(19) 0.36113(16) 0.0365(4) Uani 1 1 d . . . . .
H7A H 0.437561 0.511459 0.331137 0.044 Uiso 1 1 calc R U . . .
O8A O 0.62531(7) 0.66807(16) 0.45438(12) 0.0225(4) Uani 1 1 d G . . . .
H8A H 0.614518 0.669858 0.526116 0.027 Uiso 1 1 calc R U . . .
C18A C 0.68336(10) 0.9655(2) 0.45096(19) 0.0214(5) Uani 1 1 d . . . . .
C19A C 0.61563(10) 0.9280(2) 0.44968(18) 0.0200(5) Uani 1 1 d . . . . .
H19A H 0.593222 1.004279 0.406094 0.024 Uiso 1 1 calc R U . . .
H19B H 0.602318 0.926253 0.533850 0.024 Uiso 1 1 calc R U . . .
C20A C 0.59824(10) 0.7811(2) 0.38928(18) 0.0183(5) Uani 1 1 d . . . . .
C21A C 0.62279(10) 0.7769(2) 0.26063(19) 0.0192(5) Uani 1 1 d . . . . .
C22A C 0.52841(10) 0.7651(2) 0.38549(19) 0.0218(5) Uani 1 1 d . . . . .
H22A H 0.514582 0.766749 0.469265 0.026 Uiso 1 1 calc R U . . .
H22B H 0.511186 0.848997 0.342718 0.026 Uiso 1 1 calc R U . . .
C23A C 0.50324(10) 0.6299(3) 0.3244(2) 0.0239(5) Uani 1 1 d . . . . .
O1B O 0.21064(7) 0.85313(16) -0.09455(13) 0.0241(4) Uani 1 1 d . . . . .
N1B N 0.30547(8) 0.9006(2) 0.13789(16) 0.0231(4) Uani 1 1 d . . . . .
H1B H 0.315603 1.006094 0.144335 0.028 Uiso 1 1 calc R U . . .
C1B C 0.12056(11) 0.6676(3) -0.1860(2) 0.0272(5) Uani 1 1 d . . . . .
H1BB H 0.154119 0.634829 -0.137382 0.033 Uiso 1 1 calc R U . . .
C2B C 0.07538(11) 0.5698(3) -0.2294(2) 0.0335(6) Uani 1 1 d . . . . .
H2BB H 0.078399 0.470598 -0.210516 0.040 Uiso 1 1 calc R U . . .
C3B C 0.02622(11) 0.6153(3) -0.2997(2) 0.0312(6) Uani 1 1 d . . . . .
H3BB H -0.004207 0.547733 -0.330208 0.037 Uiso 1 1 calc R U . . .
C4B C 0.02154(11) 0.7596(3) -0.3253(2) 0.0304(6) Uani 1 1 d . . . . .
H4BB H -0.012559 0.792100 -0.372507 0.037 Uiso 1 1 calc R U . . .
C5B C 0.06658(10) 0.8572(3) -0.28213(19) 0.0258(5) Uani 1 1 d . . . . .
H5BB H 0.062937 0.956517 -0.300077 0.031 Uiso 1 1 calc R U . . .
C6B C 0.11711(10) 0.8126(3) -0.21293(19) 0.0223(5) Uani 1 1 d . . . . .
C7B C 0.16503(10) 0.9241(2) -0.16754(19) 0.0217(5) Uani 1 1 d . . . . .
H7BB H 0.184850 0.968968 -0.238466 0.026 Uiso 1 1 calc R U . . .
C8B C 0.13690(10) 1.0423(2) -0.09399(19) 0.0227(5) Uani 1 1 d . . . . .
C9B C 0.09426(11) 1.0057(3) -0.0091(2) 0.0294(6) Uani 1 1 d . . . . .
H9BB H 0.081874 0.907577 0.000600 0.035 Uiso 1 1 calc R U . . .
C10B C 0.06960(11) 1.1095(3) 0.0613(2) 0.0315(6) Uani 1 1 d . . . . .
H10B H 0.040136 1.083063 0.118300 0.038 Uiso 1 1 calc R U . . .
C11B C 0.08794(11) 1.2518(3) 0.0486(2) 0.0317(6) Uani 1 1 d . . . . .
H11B H 0.070957 1.323620 0.096615 0.038 Uiso 1 1 calc R U . . .
C12B C 0.13105(11) 1.2902(3) -0.0341(2) 0.0310(6) Uani 1 1 d . . . . .
H12B H 0.144211 1.388033 -0.041853 0.037 Uiso 1 1 calc R U . . .
C13B C 0.15513(11) 1.1850(3) -0.1059(2) 0.0273(5) Uani 1 1 d . . . . .
H13B H 0.184285 1.211610 -0.163475 0.033 Uiso 1 1 calc R U . . .
C14B C 0.26582(10) 0.9381(3) -0.0757(2) 0.0250(5) Uani 1 1 d . . . . .
H14C H 0.256864 1.031839 -0.039131 0.030 Uiso 1 1 calc R U . . .
H14D H 0.284849 0.956520 -0.153726 0.030 Uiso 1 1 calc R U . . .
C15B C 0.30860(10) 0.8574(3) 0.00728(19) 0.0230(5) Uani 1 1 d . . . . .
H15C H 0.350995 0.874354 -0.018182 0.028 Uiso 1 1 calc R U . . .
H15D H 0.298585 0.753009 -0.000600 0.028 Uiso 1 1 calc R U . . .
C16B C 0.24315(11) 0.8740(3) 0.1842(2) 0.0347(6) Uani 1 1 d . . . . .
H16D H 0.243177 0.903380 0.269162 0.052 Uiso 1 1 calc R U . . .
H16E H 0.231823 0.771352 0.177129 0.052 Uiso 1 1 calc R U . . .
H16F H 0.213526 0.929919 0.136707 0.052 Uiso 1 1 calc R U . . .
C17B C 0.35205(11) 0.8234(3) 0.2131(2) 0.0327(6) Uani 1 1 d . . . . .
H17D H 0.351881 0.857561 0.296775 0.049 Uiso 1 1 calc R U . . .
H17E H 0.392637 0.842257 0.181538 0.049 Uiso 1 1 calc R U . . .
H17F H 0.342253 0.719792 0.210394 0.049 Uiso 1 1 calc R U . . .
O2B O 0.28019(7) 1.38808(19) -0.05293(13) 0.0276(4) Uani 1 1 d . . . . .
H2B H 0.303564 1.351177 -0.101411 0.033 Uiso 1 1 calc R U . . .
O3B O 0.28747(7) 1.49790(18) 0.12271(14) 0.0293(4) Uani 1 1 d . . . . .
O4B O 0.40021(7) 1.34112(17) 0.31364(13) 0.0250(4) Uani 1 1 d . . . . .
O5B O 0.33292(7) 1.16518(17) 0.25923(12) 0.0228(4) Uani 1 1 d . . . . .
O6B O 0.46757(8) 1.0547(2) 0.24167(16) 0.0384(5) Uani 1 1 d . . . . .
O7B O 0.54782(7) 1.09900(18) 0.12832(15) 0.0321(4) Uani 1 1 d . . . . .
H7B H 0.560223 1.023168 0.160827 0.038 Uiso 1 1 calc R U . . .
O8B O 0.36797(7) 1.14837(16) 0.04234(12) 0.0219(4) Uani 1 1 d . . . . .
H8B H 0.378449 1.150815 -0.029619 0.026 Uiso 1 1 calc R U . . .
C18B C 0.31254(10) 1.4348(2) 0.04410(19) 0.0204(5) Uani 1 1 d . . . . .
C19B C 0.38023(10) 1.4097(2) 0.04977(18) 0.0202(5) Uani 1 1 d . . . . .
H19C H 0.401541 1.488544 0.096857 0.024 Uiso 1 1 calc R U . . .
H19D H 0.395174 1.413396 -0.033164 0.024 Uiso 1 1 calc R U . . .
C20B C 0.39710(10) 1.2647(2) 0.10738(18) 0.0182(5) Uani 1 1 d . . . . .
C21B C 0.37460(10) 1.2549(2) 0.23785(18) 0.0189(5) Uani 1 1 d . . . . .
C22B C 0.46691(10) 1.2565(2) 0.10613(19) 0.0213(5) Uani 1 1 d . . . . .
H22C H 0.479058 1.258442 0.021188 0.026 Uiso 1 1 calc R U . . .
H22D H 0.485612 1.343145 0.146876 0.026 Uiso 1 1 calc R U . . .
C23B C 0.49238(10) 1.1260(3) 0.1660(2) 0.0231(5) Uani 1 1 d . . . . .


_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 C14A 1.425(3) . ?
O1A C7A 1.438(3) . ?
N1A C16A 1.489(3) . ?
N1A C17A 1.492(3) . ?
N1A C15A 1.498(3) . ?
N1A H1A 1.0000 . ?
C1A C2A 1.386(3) . ?
C1A C6A 1.390(3) . ?
C1A H1AA 0.9500 . ?
C2A C3A 1.386(3) . ?
C2A H2AA 0.9500 . ?
C3A C4A 1.385(3) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.380(3) . ?
C4A H4AA 0.9500 . ?
C5A C6A 1.391(3) . ?
C5A H5AA 0.9500 . ?
C6A C7A 1.512(3) . ?
C7A C8A 1.523(3) . ?
C7A H7AA 1.0000 . ?
C8A C13A 1.386(3) . ?
C8A C9A 1.398(3) . ?
C9A C10A 1.385(4) . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.377(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.379(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.382(4) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.514(3) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
O2A C18A 1.319(3) . ?
O2A H2A 0.8400 . ?
O3A C18A 1.212(3) . ?
O4A C21A 1.258(3) . ?
O5A C21A 1.251(3) . ?
O6A C23A 1.212(3) . ?
O7A C23A 1.319(3) . ?
O7A H7A 0.8400 . ?
O8A C20A 1.408(3) . ?
O8A H8A 0.8400 . ?
C18A C19A 1.511(3) . ?
C19A C20A 1.548(3) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A C22A 1.529(3) . ?
C20A C21A 1.548(3) . ?
C22A C23A 1.503(3) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
O1B C14B 1.427(3) . ?
O1B C7B 1.435(3) . ?
N1B C17B 1.491(3) . ?
N1B C16B 1.492(3) . ?
N1B C15B 1.507(3) . ?
N1B H1B 1.0000 . ?
C1B C6B 1.384(3) . ?
C1B C2B 1.389(3) . ?
C1B H1BB 0.9500 . ?
C2B C3B 1.378(3) . ?
C2B H2BB 0.9500 . ?
C3B C4B 1.378(4) . ?
C3B H3BB 0.9500 . ?
C4B C5B 1.385(3) . ?
C4B H4BB 0.9500 . ?
C5B C6B 1.392(3) . ?
C5B H5BB 0.9500 . ?
C6B C7B 1.517(3) . ?
C7B C8B 1.531(3) . ?
C7B H7BB 1.0000 . ?
C8B C13B 1.380(3) . ?
C8B C9B 1.390(3) . ?
C9B C10B 1.381(3) . ?
C9B H9BB 0.9500 . ?
C10B C11B 1.378(4) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.384(3) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.393(3) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.502(3) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
O2B C18B 1.324(3) . ?
O2B H2B 0.8400 . ?
O3B C18B 1.212(2) . ?
O4B C21B 1.259(3) . ?
O5B C21B 1.246(3) . ?
O6B C23B 1.207(3) . ?
O7B C23B 1.333(3) . ?
O7B H7B 0.8400 . ?
O8B C20B 1.415(3) . ?
O8B H8B 0.8400 . ?
C18B C19B 1.507(3) . ?
C19B C20B 1.542(3) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B C22B 1.533(3) . ?
C20B C21B 1.551(3) . ?
C22B C23B 1.496(3) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?

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
C14A O1A C7A 110.66(16) . . ?
C16A N1A C17A 110.44(18) . . ?
C16A N1A C15A 112.39(17) . . ?
C17A N1A C15A 109.93(18) . . ?
C16A N1A H1A 108.0 . . ?
C17A N1A H1A 108.0 . . ?
C15A N1A H1A 108.0 . . ?
C2A C1A C6A 120.8(2) . . ?
C2A C1A H1AA 119.6 . . ?
C6A C1A H1AA 119.6 . . ?
C3A C2A C1A 120.1(2) . . ?
C3A C2A H2AA 120.0 . . ?
C1A C2A H2AA 120.0 . . ?
C4A C3A C2A 119.7(2) . . ?
C4A C3A H3AA 120.1 . . ?
C2A C3A H3AA 120.1 . . ?
C5A C4A C3A 119.8(2) . . ?
C5A C4A H4AA 120.1 . . ?
C3A C4A H4AA 120.1 . . ?
C4A C5A C6A 121.3(2) . . ?
C4A C5A H5AA 119.3 . . ?
C6A C5A H5AA 119.3 . . ?
C1A C6A C5A 118.2(2) . . ?
C1A C6A C7A 123.2(2) . . ?
C5A C6A C7A 118.41(19) . . ?
O1A C7A C6A 108.22(18) . . ?
O1A C7A C8A 111.38(17) . . ?
C6A C7A C8A 112.33(18) . . ?
O1A C7A H7AA 108.3 . . ?
C6A C7A H7AA 108.3 . . ?
C8A C7A H7AA 108.3 . . ?
C13A C8A C9A 118.9(2) . . ?
C13A C8A C7A 119.9(2) . . ?
C9A C8A C7A 121.1(2) . . ?
C10A C9A C8A 120.1(2) . . ?
C10A C9A H9AA 119.9 . . ?
C8A C9A H9AA 119.9 . . ?
C11A C10A C9A 120.2(2) . . ?
C11A C10A H10A 119.9 . . ?
C9A C10A H10A 119.9 . . ?
C10A C11A C12A 120.0(2) . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A C13A 120.2(2) . . ?
C11A C12A H12A 119.9 . . ?
C13A C12A H12A 119.9 . . ?
C12A C13A C8A 120.5(2) . . ?
C12A C13A H13A 119.8 . . ?
C8A C13A H13A 119.8 . . ?
O1A C14A C15A 108.71(18) . . ?
O1A C14A H14A 109.9 . . ?
C15A C14A H14A 109.9 . . ?
O1A C14A H14B 109.9 . . ?
C15A C14A H14B 109.9 . . ?
H14A C14A H14B 108.3 . . ?
N1A C15A C14A 112.99(19) . . ?
N1A C15A H15A 109.0 . . ?
C14A C15A H15A 109.0 . . ?
N1A C15A H15B 109.0 . . ?
C14A C15A H15B 109.0 . . ?
H15A C15A H15B 107.8 . . ?
N1A C16A H16A 109.5 . . ?
N1A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
N1A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N1A C17A H17A 109.5 . . ?
N1A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
N1A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C18A O2A H2A 109.5 . . ?
C23A O7A H7A 109.5 . . ?
C20A O8A H8A 109.5 . . ?
O3A C18A O2A 120.2(2) . . ?
O3A C18A C19A 122.4(2) . . ?
O2A C18A C19A 117.46(19) . . ?
C18A C19A C20A 113.38(17) . . ?
C18A C19A H19A 108.9 . . ?
C20A C19A H19A 108.9 . . ?
C18A C19A H19B 108.9 . . ?
C20A C19A H19B 108.9 . . ?
H19A C19A H19B 107.7 . . ?
O8A C20A C22A 111.27(18) . . ?
O8A C20A C21A 106.78(17) . . ?
C22A C20A C21A 111.18(17) . . ?
O8A C20A C19A 110.76(17) . . ?
C22A C20A C19A 106.94(17) . . ?
C21A C20A C19A 109.96(17) . . ?
O5A C21A O4A 125.19(19) . . ?
O5A C21A C20A 118.29(19) . . ?
O4A C21A C20A 116.51(19) . . ?
C23A C22A C20A 114.11(18) . . ?
C23A C22A H22A 108.7 . . ?
C20A C22A H22A 108.7 . . ?
C23A C22A H22B 108.7 . . ?
C20A C22A H22B 108.7 . . ?
H22A C22A H22B 107.6 . . ?
O6A C23A O7A 123.0(2) . . ?
O6A C23A C22A 125.0(2) . . ?
O7A C23A C22A 112.04(19) . . ?
C14B O1B C7B 112.97(17) . . ?
C17B N1B C16B 110.61(19) . . ?
C17B N1B C15B 109.97(17) . . ?
C16B N1B C15B 112.17(17) . . ?
C17B N1B H1B 108.0 . . ?
C16B N1B H1B 108.0 . . ?
C15B N1B H1B 108.0 . . ?
C6B C1B C2B 120.6(2) . . ?
C6B C1B H1BB 119.7 . . ?
C2B C1B H1BB 119.7 . . ?
C3B C2B C1B 120.6(2) . . ?
C3B C2B H2BB 119.7 . . ?
C1B C2B H2BB 119.7 . . ?
C2B C3B C4B 119.5(2) . . ?
C2B C3B H3BB 120.3 . . ?
C4B C3B H3BB 120.3 . . ?
C3B C4B C5B 119.9(2) . . ?
C3B C4B H4BB 120.0 . . ?
C5B C4B H4BB 120.0 . . ?
C4B C5B C6B 121.2(2) . . ?
C4B C5B H5BB 119.4 . . ?
C6B C5B H5BB 119.4 . . ?
C1B C6B C5B 118.1(2) . . ?
C1B C6B C7B 122.7(2) . . ?
C5B C6B C7B 119.1(2) . . ?
O1B C7B C6B 108.64(18) . . ?
O1B C7B C8B 109.92(17) . . ?
C6B C7B C8B 111.69(18) . . ?
O1B C7B H7BB 108.8 . . ?
C6B C7B H7BB 108.8 . . ?
C8B C7B H7BB 108.8 . . ?
C13B C8B C9B 118.9(2) . . ?
C13B C8B C7B 121.3(2) . . ?
C9B C8B C7B 119.8(2) . . ?
C10B C9B C8B 121.1(2) . . ?
C10B C9B H9BB 119.5 . . ?
C8B C9B H9BB 119.5 . . ?
C11B C10B C9B 119.7(2) . . ?
C11B C10B H10B 120.2 . . ?
C9B C10B H10B 120.2 . . ?
C10B C11B C12B 120.1(2) . . ?
C10B C11B H11B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C11B C12B C13B 119.9(2) . . ?
C11B C12B H12B 120.1 . . ?
C13B C12B H12B 120.1 . . ?
C8B C13B C12B 120.4(2) . . ?
C8B C13B H13B 119.8 . . ?
C12B C13B H13B 119.8 . . ?
O1B C14B C15B 108.36(19) . . ?
O1B C14B H14C 110.0 . . ?
C15B C14B H14C 110.0 . . ?
O1B C14B H14D 110.0 . . ?
C15B C14B H14D 110.0 . . ?
H14C C14B H14D 108.4 . . ?
C14B C15B N1B 113.17(18) . . ?
C14B C15B H15C 108.9 . . ?
N1B C15B H15C 108.9 . . ?
C14B C15B H15D 108.9 . . ?
N1B C15B H15D 108.9 . . ?
H15C C15B H15D 107.8 . . ?
N1B C16B H16D 109.5 . . ?
N1B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
N1B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N1B C17B H17D 109.5 . . ?
N1B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
N1B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C18B O2B H2B 109.5 . . ?
C23B O7B H7B 109.5 . . ?
C20B O8B H8B 109.5 . . ?
O3B C18B O2B 119.7(2) . . ?
O3B C18B C19B 122.8(2) . . ?
O2B C18B C19B 117.56(18) . . ?
C18B C19B C20B 113.63(18) . . ?
C18B C19B H19C 108.8 . . ?
C20B C19B H19C 108.8 . . ?
C18B C19B H19D 108.8 . . ?
C20B C19B H19D 108.8 . . ?
H19C C19B H19D 107.7 . . ?
O8B C20B C22B 110.94(17) . . ?
O8B C20B C19B 110.85(16) . . ?
C22B C20B C19B 106.89(17) . . ?
O8B C20B C21B 106.48(17) . . ?
C22B C20B C21B 111.33(17) . . ?
C19B C20B C21B 110.40(17) . . ?
O5B C21B O4B 125.4(2) . . ?
O5B C21B C20B 118.39(19) . . ?
O4B C21B C20B 116.17(19) . . ?
C23B C22B C20B 114.62(18) . . ?
C23B C22B H22C 108.6 . . ?
C20B C22B H22C 108.6 . . ?
C23B C22B H22D 108.6 . . ?
C20B C22B H22D 108.6 . . ?
H22C C22B H22D 107.6 . . ?
O6B C23B O7B 123.0(2) . . ?
O6B C23B C22B 125.3(2) . . ?
O7B C23B C22B 111.61(19) . . ?

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
C6A C1A C2A C3A 0.0(4) . . . . ?
C1A C2A C3A C4A 0.8(4) . . . . ?
C2A C3A C4A C5A -0.1(4) . . . . ?
C3A C4A C5A C6A -1.4(4) . . . . ?
C2A C1A C6A C5A -1.4(4) . . . . ?
C2A C1A C6A C7A 174.8(2) . . . . ?
C4A C5A C6A C1A 2.2(3) . . . . ?
C4A C5A C6A C7A -174.3(2) . . . . ?
C14A O1A C7A C6A 166.59(17) . . . . ?
C14A O1A C7A C8A -69.5(2) . . . . ?
C1A C6A C7A O1A 41.1(3) . . . . ?
C5A C6A C7A O1A -142.7(2) . . . . ?
C1A C6A C7A C8A -82.3(3) . . . . ?
C5A C6A C7A C8A 94.0(2) . . . . ?
O1A C7A C8A C13A 126.8(2) . . . . ?
C6A C7A C8A C13A -111.6(2) . . . . ?
O1A C7A C8A C9A -51.7(3) . . . . ?
C6A C7A C8A C9A 69.9(3) . . . . ?
C13A C8A C9A C10A -1.7(3) . . . . ?
C7A C8A C9A C10A 176.8(2) . . . . ?
C8A C9A C10A C11A 1.9(4) . . . . ?
C9A C10A C11A C12A 0.2(4) . . . . ?
C10A C11A C12A C13A -2.4(4) . . . . ?
C11A C12A C13A C8A 2.6(4) . . . . ?
C9A C8A C13A C12A -0.5(3) . . . . ?
C7A C8A C13A C12A -179.1(2) . . . . ?
C7A O1A C14A C15A -177.52(17) . . . . ?
C16A N1A C15A C14A 61.5(2) . . . . ?
C17A N1A C15A C14A -175.03(19) . . . . ?
O1A C14A C15A N1A -92.8(2) . . . . ?
O3A C18A C19A C20A 89.7(3) . . . . ?
O2A C18A C19A C20A -91.3(2) . . . . ?
C18A C19A C20A O8A 63.3(2) . . . . ?
C18A C19A C20A C22A -175.26(17) . . . . ?
C18A C19A C20A C21A -54.4(2) . . . . ?
O8A C20A C21A O5A -6.8(3) . . . . ?
C22A C20A C21A O5A -128.4(2) . . . . ?
C19A C20A C21A O5A 113.4(2) . . . . ?
O8A C20A C21A O4A 173.41(18) . . . . ?
C22A C20A C21A O4A 51.9(3) . . . . ?
C19A C20A C21A O4A -66.4(2) . . . . ?
O8A C20A C22A C23A -61.3(2) . . . . ?
C21A C20A C22A C23A 57.5(2) . . . . ?
C19A C20A C22A C23A 177.59(18) . . . . ?
C20A C22A C23A O6A -25.9(3) . . . . ?
C20A C22A C23A O7A 155.90(19) . . . . ?
C6B C1B C2B C3B -0.3(4) . . . . ?
C1B C2B C3B C4B -1.0(4) . . . . ?
C2B C3B C4B C5B 1.1(4) . . . . ?
C3B C4B C5B C6B 0.1(3) . . . . ?
C2B C1B C6B C5B 1.4(3) . . . . ?
C2B C1B C6B C7B 179.8(2) . . . . ?
C4B C5B C6B C1B -1.4(3) . . . . ?
C4B C5B C6B C7B -179.8(2) . . . . ?
C14B O1B C7B C6B 163.34(17) . . . . ?
C14B O1B C7B C8B -74.2(2) . . . . ?
C1B C6B C7B O1B -0.9(3) . . . . ?
C5B C6B C7B O1B 177.40(18) . . . . ?
C1B C6B C7B C8B -122.3(2) . . . . ?
C5B C6B C7B C8B 56.0(3) . . . . ?
O1B C7B C8B C13B 100.1(2) . . . . ?
C6B C7B C8B C13B -139.2(2) . . . . ?
O1B C7B C8B C9B -76.7(3) . . . . ?
C6B C7B C8B C9B 43.9(3) . . . . ?
C13B C8B C9B C10B 0.9(4) . . . . ?
C7B C8B C9B C10B 177.9(2) . . . . ?
C8B C9B C10B C11B -0.8(4) . . . . ?
C9B C10B C11B C12B -0.3(4) . . . . ?
C10B C11B C12B C13B 1.1(4) . . . . ?
C9B C8B C13B C12B -0.1(3) . . . . ?
C7B C8B C13B C12B -177.0(2) . . . . ?
C11B C12B C13B C8B -0.9(4) . . . . ?
C7B O1B C14B C15B 176.75(17) . . . . ?
O1B C14B C15B N1B -95.3(2) . . . . ?
C17B N1B C15B C14B -176.1(2) . . . . ?
C16B N1B C15B C14B 60.3(3) . . . . ?
O3B C18B C19B C20B 92.5(3) . . . . ?
O2B C18B C19B C20B -89.1(2) . . . . ?
C18B C19B C20B O8B 59.0(2) . . . . ?
C18B C19B C20B C22B -179.97(17) . . . . ?
C18B C19B C20B C21B -58.7(2) . . . . ?
O8B C20B C21B O5B -7.7(3) . . . . ?
C22B C20B C21B O5B -128.7(2) . . . . ?
C19B C20B C21B O5B 112.7(2) . . . . ?
O8B C20B C21B O4B 173.05(18) . . . . ?
C22B C20B C21B O4B 52.0(3) . . . . ?
C19B C20B C21B O4B -66.5(2) . . . . ?
O8B C20B C22B C23B -62.7(2) . . . . ?
C19B C20B C22B C23B 176.37(17) . . . . ?
C21B C20B C22B C23B 55.7(2) . . . . ?
C20B C22B C23B O6B -23.1(3) . . . . ?
C20B C22B C23B O7B 158.95(18) . . . . ?

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
N1A H1A O5A 1.00 1.96 2.836(3) 144.8 . yes
N1A H1A O8A 1.00 2.09 2.888(2) 134.9 . yes
C7A H7AA O3B 1.00 2.47 3.417(3) 158.2 2_676 yes
C14A H14A O8A 0.99 2.63 3.111(3) 110.1 . yes
C14A H14B O3B 0.99 2.54 3.448(3) 152.2 2_676 yes
C15A H15B O7A 0.99 2.45 3.397(3) 160.9 2_666 yes
C16A H16A O2B 0.98 2.55 3.447(3) 151.7 2_675 yes
C16A H16C O1A 0.98 2.61 3.112(3) 111.6 . yes
C17A H17B O6A 0.98 2.58 3.228(3) 123.9 . yes
C17A H17C O3A 0.98 2.52 3.417(3) 151.5 1_545 yes
O2A H2A O5B 0.84 1.79 2.594(2) 160.1 2_676 yes
O7A H7A O4B 0.84 1.76 2.569(2) 160.2 1_545 yes
O8A H8A O4B 0.84 1.82 2.657(2) 172.4 2_676 yes
C22A H22B O6B 0.99 2.42 3.410(3) 178.8 . yes
N1B H1B O5B 1.00 1.97 2.835(3) 143.8 . yes
N1B H1B O8B 1.00 2.09 2.867(3) 133.3 . yes
C14B H14D O3A 0.99 2.41 3.350(3) 158.4 2_675 yes
C15B H15C O7B 0.99 2.58 3.557(3) 168.0 2_675 yes
C16B H16F O1B 0.98 2.66 3.142(3) 110.8 . yes
C17B H17E O6B 0.98 2.59 3.265(3) 126.2 . yes
C17B H17F O3B 0.98 2.52 3.424(3) 153.3 1_545 yes
O2B H2B O5A 0.84 1.77 2.578(2) 159.4 2_675 yes
O7B H7B O4A 0.84 1.77 2.579(2) 161.0 . yes
O8B H8B O4A 0.84 1.81 2.647(2) 174.8 2_675 yes
C22B H22D O6A 0.99 2.47 3.464(3) 177.9 1_565 yes

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.053


# start Validation Reply Form
_vrf_PLAT155_123Ka               
;
PROBLEM: The Triclinic Unitcell is NOT Reduced .......... Please Do !
RESPONSE: ... Non-standard triclinic cell is a distortion of the parent
monoclinic in form I. It is retained for the purpose of comparing 
these crystal structures.
;
_vrf_PLAT480_123Ka               
;
PROBLEM: Long H...A H-Bond Reported H14A ..O8A . 2.63 Ang.
RESPONSE: ... Retained for comparing structures.
;
_vrf_PLAT911_123Ka               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 130 Report
RESPONSE: ... Twin data processing losses.
;
# end Validation Reply Form


####################################################################### 
# 
# 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_218k
_database_code_depnum_ccdc_archive 'CCDC 2012785'
loop_
_audit_author_name
_audit_author_address
'Kunlin Wang'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2-(Benzhydryloxy)-N,N-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate
;
_chemical_name_common            'Diphenhydramine citrate salt'
_chemical_melting_point          424
_chemical_formula_moiety         'C17 H22 N O, C6 H7 O7'
_chemical_formula_sum            'C23 H29 N O8'
_chemical_formula_weight         447.47

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   21.229(3)
_cell_length_b                   9.6695(9)
_cell_length_c                   11.1075(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.327(4)
_cell_angle_gamma                90
_cell_volume                     2279.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    218(2)
_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      30.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   0.6778
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6778
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS-2016/2, (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      218(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   normal
_diffrn_measurement_device_type  'Bruker-AXS PHOTON-II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24328
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.879
_diffrn_reflns_theta_max         30.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6900
_reflns_number_gt                5694
_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       'SMART, Bruker'
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.7187P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6900
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_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 0.77949(4) 0.36246(8) 0.57718(7) 0.02886(17) Uani 1 1 d . . . . .
N1 N 0.69036(5) 0.41861(10) 0.34076(8) 0.0304(2) Uani 1 1 d . . . . .
H1 H 0.678401 0.517506 0.337177 0.036 Uiso 1 1 calc R U . . .
C1 C 0.88767(6) 0.21022(13) 0.62736(11) 0.0373(3) Uani 1 1 d . . . . .
H1A H 0.863173 0.188837 0.558265 0.045 Uiso 1 1 calc R U . . .
C2 C 0.93762(7) 0.12442(15) 0.66237(14) 0.0462(3) Uani 1 1 d . . . . .
H2A H 0.946789 0.045757 0.616250 0.055 Uiso 1 1 calc R U . . .
C3 C 0.97364(6) 0.15383(16) 0.76388(14) 0.0460(3) Uani 1 1 d . . . . .
H3A H 1.007450 0.095972 0.786608 0.055 Uiso 1 1 calc R U . . .
C4 C 0.95987(7) 0.26801(16) 0.83158(13) 0.0465(3) Uani 1 1 d . . . . .
H4A H 0.984108 0.288221 0.901268 0.056 Uiso 1 1 calc R U . . .
C5 C 0.91033(6) 0.35353(14) 0.79742(11) 0.0387(3) Uani 1 1 d . . . . .
H5A H 0.900998 0.431057 0.844849 0.046 Uiso 1 1 calc R U . . .
C6 C 0.87413(5) 0.32672(11) 0.69417(10) 0.0279(2) Uani 1 1 d . . . . .
C7 C 0.82407(5) 0.43000(12) 0.65681(10) 0.0287(2) Uani 1 1 d . . . . .
H7A H 0.801994 0.461642 0.729363 0.034 Uiso 1 1 calc R U . . .
C8 C 0.85238(5) 0.55447(12) 0.59483(11) 0.0324(2) Uani 1 1 d . . . . .
C9 C 0.89216(8) 0.53633(14) 0.49900(12) 0.0448(3) Uani 1 1 d . . . . .
H9A H 0.903434 0.446399 0.475668 0.054 Uiso 1 1 calc R U . . .
C10 C 0.91557(9) 0.64877(18) 0.43708(15) 0.0579(4) Uani 1 1 d . . . . .
H10A H 0.942434 0.635246 0.372023 0.069 Uiso 1 1 calc R U . . .
C11 C 0.89927(8) 0.77991(17) 0.4713(2) 0.0698(6) Uani 1 1 d . . . . .
H11A H 0.915069 0.856559 0.429626 0.084 Uiso 1 1 calc R U . . .
C12 C 0.86016(8) 0.79983(16) 0.5659(3) 0.0815(7) Uani 1 1 d . . . . .
H12A H 0.848986 0.890083 0.588462 0.098 Uiso 1 1 calc R U . . .
C13 C 0.83674(7) 0.68685(15) 0.62910(19) 0.0568(4) Uani 1 1 d . . . . .
H13A H 0.810380 0.701044 0.694812 0.068 Uiso 1 1 calc R U . . .
C14 C 0.72365(5) 0.44265(12) 0.55862(10) 0.0294(2) Uani 1 1 d . . . . .
H14A H 0.734489 0.535063 0.529364 0.035 Uiso 1 1 calc R U . . .
H14B H 0.701530 0.452748 0.634583 0.035 Uiso 1 1 calc R U . . .
C15 C 0.68202(5) 0.36936(12) 0.46696(10) 0.0299(2) Uani 1 1 d . . . . .
H15A H 0.691035 0.270024 0.470483 0.036 Uiso 1 1 calc R U . . .
H15B H 0.637913 0.382455 0.488500 0.036 Uiso 1 1 calc R U . . .
C16 C 0.75642(7) 0.40620(19) 0.30127(12) 0.0499(4) Uani 1 1 d . . . . .
H16A H 0.770033 0.310762 0.308746 0.075 Uiso 1 1 calc R U . . .
H16B H 0.783413 0.464541 0.351313 0.075 Uiso 1 1 calc R U . . .
H16C H 0.758996 0.435179 0.217919 0.075 Uiso 1 1 calc R U . . .
C17 C 0.64724(8) 0.34081(15) 0.25757(14) 0.0508(4) Uani 1 1 d . . . . .
H17A H 0.651976 0.374620 0.176059 0.076 Uiso 1 1 calc R U . . .
H17B H 0.604042 0.353971 0.281756 0.076 Uiso 1 1 calc R U . . .
H17C H 0.657629 0.243166 0.260715 0.076 Uiso 1 1 calc R U . . .
O2 O 0.71808(4) 0.91277(11) 0.53275(7) 0.0383(2) Uani 1 1 d . . . . .
H2 H 0.695452 0.874886 0.582993 0.046 Uiso 1 1 calc R U . . .
O3 O 0.70628(5) 1.01849(11) 0.35940(8) 0.0425(2) Uani 1 1 d . . . . .
O4 O 0.59819(4) 0.84315(8) 0.17519(6) 0.03054(18) Uani 1 1 d . . . . .
O5 O 0.66683(4) 0.67897(8) 0.22691(6) 0.02757(16) Uani 1 1 d . . . . .
O6 O 0.53042(5) 0.55421(12) 0.24959(11) 0.0616(3) Uani 1 1 d . . . . .
O7 O 0.44955(5) 0.58335(10) 0.36805(10) 0.0474(3) Uani 1 1 d . . . . .
H7 H 0.439256 0.506453 0.340842 0.057 Uiso 1 1 calc R U . . .
O8 O 0.63124(4) 0.66252(8) 0.44559(6) 0.02673(16) Uani 1 1 d . . . . .
H8 H 0.621023 0.665828 0.517207 0.032 Uiso 1 1 calc R U . . .
C18 C 0.68322(5) 0.95131(11) 0.43893(9) 0.0255(2) Uani 1 1 d . . . . .
C19 C 0.61423(5) 0.91224(10) 0.43689(8) 0.02219(18) Uani 1 1 d . . . . .
H19A H 0.590461 0.982532 0.391375 0.027 Uiso 1 1 calc R U . . .
H19B H 0.599152 0.912998 0.519617 0.027 Uiso 1 1 calc R U . . .
C20 C 0.60018(4) 0.76865(9) 0.38058(8) 0.01946(17) Uani 1 1 d . . . . .
C21 C 0.62400(5) 0.76227(10) 0.25002(8) 0.02089(18) Uani 1 1 d . . . . .
C22 C 0.52833(5) 0.75089(11) 0.38225(9) 0.0261(2) Uani 1 1 d . . . . .
H22A H 0.514823 0.754776 0.465949 0.031 Uiso 1 1 calc R U . . .
H22B H 0.508688 0.828805 0.339251 0.031 Uiso 1 1 calc R U . . .
C23 C 0.50460(5) 0.61841(12) 0.32661(10) 0.0291(2) Uani 1 1 d . . . . .


_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 C14 1.4274(13) . ?
O1 C7 1.4372(13) . ?
N1 C16 1.4838(17) . ?
N1 C17 1.4895(16) . ?
N1 C15 1.4948(14) . ?
N1 H1 0.9900 . ?
C1 C6 1.3828(17) . ?
C1 C2 1.3946(18) . ?
C1 H1A 0.9400 . ?
C2 C3 1.377(2) . ?
C2 H2A 0.9400 . ?
C3 C4 1.371(2) . ?
C3 H3A 0.9400 . ?
C4 C5 1.3840(19) . ?
C4 H4A 0.9400 . ?
C5 C6 1.3900(16) . ?
C5 H5A 0.9400 . ?
C6 C7 1.5096(15) . ?
C7 C8 1.5175(16) . ?
C7 H7A 0.9900 . ?
C8 C13 1.3782(18) . ?
C8 C9 1.385(2) . ?
C9 C10 1.385(2) . ?
C9 H9A 0.9400 . ?
C10 C11 1.371(3) . ?
C10 H10A 0.9400 . ?
C11 C12 1.367(3) . ?
C11 H11A 0.9400 . ?
C12 C13 1.396(3) . ?
C12 H12A 0.9400 . ?
C13 H13A 0.9400 . ?
C14 C15 1.5095(15) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
O2 C18 1.3179(13) . ?
O2 H2 0.8300 . ?
O3 C18 1.2092(13) . ?
O4 C21 1.2576(12) . ?
O5 C21 1.2459(12) . ?
O6 C23 1.1997(15) . ?
O7 C23 1.3106(14) . ?
O7 H7 0.8300 . ?
O8 C20 1.4097(11) . ?
O8 H8 0.8300 . ?
C18 C19 1.5122(14) . ?
C19 C20 1.5490(13) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C22 1.5353(14) . ?
C20 C21 1.5481(13) . ?
C22 C23 1.5041(15) . ?
C22 H22A 0.9800 . ?
C22 H22B 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
C14 O1 C7 112.01(8) . . ?
C16 N1 C17 110.32(11) . . ?
C16 N1 C15 112.63(9) . . ?
C17 N1 C15 109.65(10) . . ?
C16 N1 H1 108.0 . . ?
C17 N1 H1 108.0 . . ?
C15 N1 H1 108.0 . . ?
C6 C1 C2 120.07(12) . . ?
C6 C1 H1A 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C3 C2 C1 120.64(13) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C4 C3 C2 119.60(12) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.07(13) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 121.12(13) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 118.49(11) . . ?
C1 C6 C7 123.03(10) . . ?
C5 C6 C7 118.40(10) . . ?
O1 C7 C6 108.54(9) . . ?
O1 C7 C8 110.08(9) . . ?
C6 C7 C8 111.45(9) . . ?
O1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C13 C8 C9 119.01(13) . . ?
C13 C8 C7 120.72(13) . . ?
C9 C8 C7 120.21(10) . . ?
C10 C9 C8 120.96(14) . . ?
C10 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C11 C10 C9 119.51(18) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C12 C11 C10 120.34(15) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 120.38(16) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C8 C13 C12 119.79(17) . . ?
C8 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
O1 C14 C15 108.28(9) . . ?
O1 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
O1 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
N1 C15 C14 113.75(9) . . ?
N1 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
N1 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 O2 H2 109.5 . . ?
C23 O7 H7 109.5 . . ?
C20 O8 H8 109.5 . . ?
O3 C18 O2 120.00(10) . . ?
O3 C18 C19 122.12(10) . . ?
O2 C18 C19 117.85(9) . . ?
C18 C19 C20 114.04(8) . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
O8 C20 C22 111.43(8) . . ?
O8 C20 C21 106.96(7) . . ?
C22 C20 C21 110.67(8) . . ?
O8 C20 C19 111.24(7) . . ?
C22 C20 C19 106.11(8) . . ?
C21 C20 C19 110.49(8) . . ?
O5 C21 O4 125.08(9) . . ?
O5 C21 C20 118.33(8) . . ?
O4 C21 C20 116.58(8) . . ?
C23 C22 C20 114.44(9) . . ?
C23 C22 H22A 108.7 . . ?
C20 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C20 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
O6 C23 O7 122.84(11) . . ?
O6 C23 C22 125.42(10) . . ?
O7 C23 C22 111.65(9) . . ?

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
C6 C1 C2 C3 0.5(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C2 C1 C6 C5 -1.51(19) . . . . ?
C2 C1 C6 C7 175.27(12) . . . . ?
C4 C5 C6 C1 1.59(19) . . . . ?
C4 C5 C6 C7 -175.34(12) . . . . ?
C14 O1 C7 C6 167.14(9) . . . . ?
C14 O1 C7 C8 -70.64(11) . . . . ?
C1 C6 C7 O1 22.99(15) . . . . ?
C5 C6 C7 O1 -160.23(10) . . . . ?
C1 C6 C7 C8 -98.39(13) . . . . ?
C5 C6 C7 C8 78.39(13) . . . . ?
O1 C7 C8 C13 108.58(13) . . . . ?
C6 C7 C8 C13 -130.94(13) . . . . ?
O1 C7 C8 C9 -68.41(14) . . . . ?
C6 C7 C8 C9 52.07(14) . . . . ?
C13 C8 C9 C10 -0.7(2) . . . . ?
C7 C8 C9 C10 176.32(13) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C9 C8 C13 C12 1.1(2) . . . . ?
C7 C8 C13 C12 -175.93(15) . . . . ?
C11 C12 C13 C8 -1.0(3) . . . . ?
C7 O1 C14 C15 175.68(9) . . . . ?
C16 N1 C15 C14 57.00(14) . . . . ?
C17 N1 C15 C14 -179.75(10) . . . . ?
O1 C14 C15 N1 -94.36(11) . . . . ?
O3 C18 C19 C20 93.51(12) . . . . ?
O2 C18 C19 C20 -88.22(11) . . . . ?
C18 C19 C20 O8 60.84(10) . . . . ?
C18 C19 C20 C22 -177.81(8) . . . . ?
C18 C19 C20 C21 -57.80(10) . . . . ?
O8 C20 C21 O5 -5.18(12) . . . . ?
C22 C20 C21 O5 -126.74(10) . . . . ?
C19 C20 C21 O5 116.03(10) . . . . ?
O8 C20 C21 O4 175.02(9) . . . . ?
C22 C20 C21 O4 53.46(12) . . . . ?
C19 C20 C21 O4 -63.77(11) . . . . ?
O8 C20 C22 C23 -60.87(11) . . . . ?
C21 C20 C22 C23 58.01(11) . . . . ?
C19 C20 C22 C23 177.90(8) . . . . ?
C20 C22 C23 O6 -27.06(18) . . . . ?
C20 C22 C23 O7 156.28(10) . . . . ?

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
N1 H1 O5 0.99 2.00 2.8561(12) 143.9 . yes
N1 H1 O8 0.99 2.12 2.9260(12) 137.9 . yes
C7 H7A O3 0.99 2.53 3.4387(14) 153.0 4_576 yes
C14 H14B O3 0.98 2.51 3.3906(14) 149.1 4_576 yes
C15 H15B O7 0.98 2.50 3.4068(15) 154.4 3_666 yes
C16 H16C O2 0.97 2.66 3.5369(17) 150.9 4_575 yes
C17 H17B O6 0.97 2.51 3.226(2) 130.7 . yes
C17 H17C O3 0.97 2.63 3.5353(18) 154.8 1_545 yes
O2 H2 O5 0.83 1.80 2.5943(11) 159.6 4_576 yes
O7 H7 O4 0.83 1.77 2.5748(12) 161.3 2_645 yes
O8 H8 O4 0.83 1.83 2.6613(10) 175.1 4_576 yes
C22 H22B O6 0.98 2.53 3.4954(15) 170.5 2_655 yes

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.312
_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_148k
_database_code_depnum_ccdc_archive 'CCDC 2012786'
loop_
_audit_author_name
_audit_author_address
'Kunlin Wang'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2-(Benzhydryloxy)-N,N-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate
;
_chemical_name_common            'Diphenhydramine citrate salt'
_chemical_melting_point          424
_chemical_formula_moiety         'C17 H22 N O, C6 H7 O7'
_chemical_formula_sum            'C23 H29 N O8'
_chemical_formula_weight         447.47

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   21.833(19)
_cell_length_b                   9.359(7)
_cell_length_c                   11.086(9)
_cell_angle_alpha                90.328(17)
_cell_angle_beta                 92.39(2)
_cell_angle_gamma                91.79(2)
_cell_volume                     2262(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    148(2)
_cell_measurement_reflns_used    2982
_cell_measurement_theta_min      2.402
_cell_measurement_theta_max      28.266

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   0.729224
_exptl_transmission_factor_max   0.862105
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.729224
_exptl_absorpt_correction_T_max  0.862105
_exptl_absorpt_process_details   TWINABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      148(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker-AXS PHOTON-II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11231
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.097
_diffrn_reflns_theta_max         28.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             11231
_reflns_number_gt                7602
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'SMART, Bruker'
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;Refined as a 2-component twin. Form I is in space group P2(1)/c. Below 
 ~148K Form II is found as a twin by non-merohedry. The transformation
 from point group 2/m to -1 necessitates either a rotation or mirror 
 twin symmetry element. The twin law found by Cell_Now is found below: 

 Cell_Now indexing based on the conventional triclinic cell:

 -----------------------------------------------------------------------------

 Cell for domain  1:    9.409   11.079   21.757    87.55    87.86    89.97

 Figure of merit: 0.488   %(0.1):  50.2   %(0.2):  69.5   %(0.3):  81.4

 Orientation matrix: -0.01777660  0.05577662 -0.03625159
                     -0.04624460  0.05899379  0.02794085
                      0.09411280  0.03963453  0.00493999

 Percentages of reflections in this domain not consistent with lattice types:
 A: 49.0,  B: 47.5,  C: 48.2,  I: 49.8,  F: 72.4,  O: 69.6  and  R: 65.3%

 Percentages of reflections in this domain that do not have:
 h=2n: 54.6,  k=2n: 48.7,  l=2n: 49.8,  h=3n: 69.7,  k=3n: 66.0,  l=3n: 66.5%

 RLATT color-coding employed in file: vgy_143A.p4p
 White: indexed for first domain
 Red: not yet indexed

  1078 reflections within tolerance assigned to domain  1,
  1078 of them exclusively;   339 reflections not yet assigned to a domain

 ----------------------------------------------------------------------------

 Cell for domain  2:    9.409   11.079   21.757    87.55    87.86    89.97

 Figure of merit: 0.400   %(0.1):  28.6   %(0.2):  56.6   %(0.3):  73.7

 Orientation matrix: -0.02292793 -0.05574464  0.03637794
                     -0.04159017 -0.05929166 -0.02771567
                      0.09516490 -0.03923301 -0.00526870

 Rotated from first domain by 179.9 degrees about
 reciprocal axis  1.000  0.003  0.076  and real axis  1.000  0.002 -0.002

 Twin law to convert hkl from first to      1.000   0.004  -0.004
 this domain (SHELXL TWIN matrix):          0.007  -1.000  -0.001
                                            0.153   0.004  -1.000

 RLATT color-coding employed in file: vgy_143B.p4p
 White: indexed for first domain
 Green: current domain (but not in a previous domain)
 Red: not yet indexed

   875 reflections within tolerance assigned to domain  2,
   224 of them exclusively;   115 reflections not yet assigned to a domain

 ----------------------------------------------------------------------------
 Final conventional triclinic cell from SAINT:

 Orientation ('UB') matrix (Component 1.1(1)):
   0.0178252  -0.0559467  -0.0364744
   0.0464595  -0.0589846   0.0278257
  -0.0948595  -0.0401565   0.0051703

 Orientation ('UB') matrix (Component 1.2(2)):
   0.0228460   0.0557897   0.0366357
   0.0423939   0.0598450  -0.0276289
  -0.0956836   0.0390878  -0.0050842

         A         B         C     Alpha      Beta     Gamma           Vol
    9.3400   11.0403   21.6934    92.613    91.746    90.342       2233.51
    0.0003    0.0004    0.0008     0.001     0.001     0.001          0.23
 Corrected for goodness of fit:
    0.0030    0.0035    0.0073     0.011     0.011     0.012          2.02

 ----------------------------------------------------------------------------
 Final merging statistics from TWINABS:


 Statistics for singles of twin component  1
 -------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1    0.0  0.0770   1.585 - 1.909   0.949 - 1.066   1.437     762     611
    2   15.7  0.0746   0.760 - 0.816   0.947 - 1.075   1.227     114      78
    3   15.7  0.0681   0.708 - 0.783   0.917 - 1.059   1.295    2310    1436
    4   15.7  0.0655   0.774 - 0.919   0.917 - 1.057   1.370    2462    1226
    5   15.7  0.0688   0.751 - 0.862   0.939 - 1.059   1.360     320     197
    6   15.7  0.0627   0.824 - 0.991   0.928 - 1.055   1.259     754     449

   All scans  0.0705   0.708 - 1.909   0.917 - 1.075   1.325    6722    3997


 Statistics for all composite reflections
 ----------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1    0.0  0.0874   1.585 - 1.909   0.947 - 1.083   1.437    5938    4550
    2   15.7  0.0723   0.759 - 0.820   0.917 - 1.080   1.227    5892    4041
    3   15.7  0.0679   0.708 - 0.783   0.917 - 1.053   1.295    4564    3383
    4   15.7  0.0719   0.774 - 0.919   0.916 - 1.058   1.370    3899    2881
    5   15.7  0.0782   0.751 - 0.862   0.938 - 1.067   1.360    4863    3389
    6   15.7  0.0745   0.881 - 0.991   0.916 - 1.063   1.259    4556    3378

   All scans  0.0788   0.708 - 1.909   0.916 - 1.083   1.325   29712   21622


 Statistics for all single and composite reflections
 ---------------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1    0.0  0.0882   1.585 - 1.909   0.947 - 1.083   1.437    7391    5650
    2   15.7  0.0727   0.759 - 0.820   0.917 - 1.080   1.227    6103    4180
    3   15.7  0.0693   0.708 - 0.783   0.916 - 1.059   1.295    9194    5741
    4   15.7  0.0707   0.774 - 0.919   0.916 - 1.058   1.370    8819    5233
    5   15.7  0.0776   0.751 - 0.862   0.938 - 1.067   1.360    5494    3723
    6   15.7  0.0724   0.823 - 0.991   0.916 - 1.063   1.259    6030    4196

   All scans  0.0787   0.708 - 1.909   0.916 - 1.083   1.325   43031   28723

 su = K * Sqrt[ sigma^2(I) + (g)^2 ]  where sigma(I) is estimated by SAINT

 The above statistics are based on all non-rejected data, ignoring
 reflections without equivalents when estimating R(int) and K.

 ============================================================================

 PART 3 - Output Postscript diagnostics and corrected data

 Diagnostic plots written to Postscript file 17274_148K.eps


 The R(int) and R(sigma) plots are based on all singles and composites,
 <|E^2-1|> is calculated for all individual contributions from domain 1
 assuming SAINT partitioning and the chi^2 and spatial plots show only
 those single and composite reflections actually fitted.


 HKLF 5 dataset constructed from all observations involving domain 1
   21378 Corrected reflections written to file 17274_148K.hkl
 Reflections merged according to point-group -1    
 Single reflections that also occur in composites omitted
 Minimum and maximum apparent transmission:  0.729224  0.862105
 Additional spherical absorption correction applied with mu*r =  0.1000

 The non-standard triclinic unit cell was adopted for calculations to mirror
 the axes used in the parent Form I crystal structure. End of notes on 
 twinning.

 ============================================================================,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1750P)²+18.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11231
_refine_ls_number_parameters     592
_refine_ls_number_restraints     518
_refine_ls_R_factor_all          0.1762
_refine_ls_R_factor_gt           0.1363
_refine_ls_wR_factor_ref         0.3834
_refine_ls_wR_factor_gt          0.3543
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.946
_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 0.7790(2) 0.3987(6) 0.5851(4) 0.0319(12) Uani 1 1 d D . . . .
N1A N 0.6840(3) 0.4266(8) 0.3535(5) 0.0315(14) Uani 1 1 d D . . . .
H1A H 0.673489 0.529653 0.348935 0.038 Uiso 1 1 calc R U . . .
C1A C 0.8983(4) 0.2921(12) 0.6237(8) 0.053(3) Uani 1 1 d D . . . .
H1AA H 0.880044 0.278284 0.545057 0.063 Uiso 1 1 calc R U . . .
C2A C 0.9519(4) 0.2215(12) 0.6577(8) 0.051(2) Uani 1 1 d D . . . .
H2AA H 0.972666 0.169418 0.598942 0.061 Uiso 1 1 calc R U . . .
C3A C 0.9751(4) 0.2267(9) 0.7765(7) 0.0386(18) Uani 1 1 d D . . . .
H3AA H 1.008492 0.169769 0.801798 0.046 Uiso 1 1 calc R U . . .
C4A C 0.9487(4) 0.3155(8) 0.8556(7) 0.0330(15) Uani 1 1 d D . . . .
H4AA H 0.965419 0.325566 0.935753 0.040 Uiso 1 1 calc R U . . .
C5A C 0.8988(3) 0.3894(8) 0.8206(6) 0.0291(14) Uani 1 1 d D . . . .
H5AA H 0.880954 0.449748 0.877822 0.035 Uiso 1 1 calc R U . . .
C6A C 0.8724(3) 0.3806(9) 0.7037(6) 0.0322(16) Uani 1 1 d D . . . .
C7A C 0.8197(3) 0.4765(8) 0.6681(6) 0.0282(14) Uani 1 1 d D . . . .
H7AA H 0.797001 0.498592 0.742068 0.034 Uiso 1 1 calc R U . . .
C8A C 0.8432(3) 0.6190(9) 0.6138(7) 0.0329(15) Uani 1 1 d D . . . .
C9A C 0.8687(4) 0.6230(11) 0.5013(7) 0.047(2) Uani 1 1 d D . . . .
H9AA H 0.873929 0.537183 0.457196 0.056 Uiso 1 1 calc R U . . .
C10A C 0.8866(5) 0.7545(12) 0.4539(8) 0.056(2) Uani 1 1 d D . . . .
H10A H 0.904451 0.757425 0.377246 0.067 Uiso 1 1 calc R U . . .
C11A C 0.8789(5) 0.8823(12) 0.5162(9) 0.056(2) Uani 1 1 d D . . . .
H11A H 0.890598 0.971838 0.482791 0.068 Uiso 1 1 calc R U . . .
C12A C 0.8541(4) 0.8740(11) 0.6266(9) 0.047(2) Uani 1 1 d D . . . .
H12A H 0.849834 0.959381 0.671881 0.056 Uiso 1 1 calc R U . . .
C13A C 0.8348(4) 0.7445(9) 0.6751(7) 0.0388(17) Uani 1 1 d D . . . .
H13A H 0.815828 0.742709 0.750620 0.047 Uiso 1 1 calc R U . . .
C14A C 0.7223(3) 0.4679(9) 0.5694(6) 0.0281(15) Uani 1 1 d D . . . .
H14A H 0.729333 0.565168 0.537066 0.034 Uiso 1 1 calc R U . . .
H14B H 0.702794 0.476716 0.648052 0.034 Uiso 1 1 calc R U . . .
C15A C 0.6806(3) 0.3806(9) 0.4822(6) 0.0272(15) Uani 1 1 d D . . . .
H15A H 0.691628 0.278954 0.487927 0.033 Uiso 1 1 calc R U . . .
H15B H 0.637772 0.387670 0.506943 0.033 Uiso 1 1 calc R U . . .
C16A C 0.7469(4) 0.4123(11) 0.3096(7) 0.041(2) Uani 1 1 d D . . . .
H16A H 0.748344 0.447743 0.226713 0.061 Uiso 1 1 calc R U . . .
H16B H 0.757788 0.311509 0.311284 0.061 Uiso 1 1 calc R U . . .
H16C H 0.776097 0.468260 0.361816 0.061 Uiso 1 1 calc R U . . .
C17A C 0.6383(4) 0.3428(11) 0.2757(7) 0.044(2) Uani 1 1 d D . . . .
H17A H 0.636419 0.383691 0.194438 0.065 Uiso 1 1 calc R U . . .
H17B H 0.597820 0.346635 0.310427 0.065 Uiso 1 1 calc R U . . .
H17C H 0.650561 0.243184 0.270994 0.065 Uiso 1 1 calc R U . . .
O2A O 0.7168(3) 0.9293(7) 0.5447(4) 0.0377(14) Uani 1 1 d D . . . .
H2A H 0.695487 0.879019 0.590582 0.045 Uiso 1 1 calc R U . . .
O3A O 0.7060(3) 1.0325(7) 0.3679(4) 0.0365(14) Uani 1 1 d D . . . .
O4A O 0.5987(2) 0.8591(6) 0.1830(4) 0.0300(12) Uani 1 1 d D . . . .
O5A O 0.6636(2) 0.6924(6) 0.2383(4) 0.0264(11) Uani 1 1 d D . . . .
O6A O 0.5285(3) 0.5622(7) 0.2481(5) 0.0432(15) Uani 1 1 d D . . . .
O7A O 0.4485(3) 0.5910(7) 0.3617(6) 0.0428(15) Uani 1 1 d D . . . .
H7A H 0.439018 0.507598 0.337754 0.051 Uiso 1 1 calc R U . . .
O8A O 0.6257(2) 0.6693(6) 0.4530(4) 0.0262(11) Uani 1 1 d DG . . . .
H8A H 0.613334 0.669289 0.523782 0.031 Uiso 1 1 calc R U . . .
C18A C 0.6828(3) 0.9670(8) 0.4499(5) 0.0274(15) Uani 1 1 d D . . . .
C19A C 0.6150(3) 0.9281(8) 0.4479(6) 0.0253(14) Uani 1 1 d D . . . .
H19A H 0.592327 1.003177 0.404103 0.030 Uiso 1 1 calc R U . . .
H19B H 0.601279 0.926648 0.531892 0.030 Uiso 1 1 calc R U . . .
C20A C 0.5981(3) 0.7804(7) 0.3872(5) 0.0215(13) Uani 1 1 d D . . . .
C21A C 0.6225(3) 0.7771(7) 0.2583(5) 0.0220(13) Uani 1 1 d D . . . .
C22A C 0.5280(3) 0.7636(8) 0.3860(6) 0.0261(14) Uani 1 1 d D . . . .
H22A H 0.514771 0.763843 0.470283 0.031 Uiso 1 1 calc R U . . .
H22B H 0.510051 0.846964 0.344818 0.031 Uiso 1 1 calc R U . . .
C23A C 0.5032(3) 0.6285(8) 0.3237(6) 0.0268(14) Uani 1 1 d D . . . .
O1B O 0.2126(3) 0.8513(6) -0.0917(5) 0.0345(12) Uani 1 1 d D . . . .
N1B N 0.3075(3) 0.8997(7) 0.1413(5) 0.0301(13) Uani 1 1 d D . . . .
H1B H 0.317963 1.004286 0.147801 0.036 Uiso 1 1 calc R U . . .
C1B C 0.1198(4) 0.6700(9) -0.1801(8) 0.0435(19) Uani 1 1 d D . . . .
H1BB H 0.152267 0.638581 -0.128134 0.052 Uiso 1 1 calc R U . . .
C2B C 0.0745(4) 0.5707(10) -0.2226(10) 0.054(2) Uani 1 1 d D . . . .
H2BB H 0.076555 0.473121 -0.199924 0.065 Uiso 1 1 calc R U . . .
C3B C 0.0268(4) 0.6151(10) -0.2974(7) 0.0423(18) Uani 1 1 d D . . . .
H3BB H -0.003251 0.548347 -0.329688 0.051 Uiso 1 1 calc R U . . .
C4B C 0.0237(4) 0.7611(10) -0.3248(7) 0.0437(19) Uani 1 1 d D . . . .
H4BB H -0.009478 0.793518 -0.374362 0.052 Uiso 1 1 calc R U . . .
C5B C 0.0677(4) 0.8570(9) -0.2814(7) 0.0375(17) Uani 1 1 d D . . . .
H5BB H 0.064153 0.955805 -0.298409 0.045 Uiso 1 1 calc R U . . .
C6B C 0.1184(4) 0.8096(9) -0.2112(6) 0.0336(15) Uani 1 1 d D . . . .
C7B C 0.1667(4) 0.9217(8) -0.1661(6) 0.0355(16) Uani 1 1 d D . . . .
H7BB H 0.186933 0.964134 -0.237484 0.043 Uiso 1 1 calc R U . . .
C8B C 0.1391(4) 1.0429(8) -0.0938(6) 0.0335(15) Uani 1 1 d D . . . .
C9B C 0.0962(5) 1.0041(10) -0.0087(7) 0.045(2) Uani 1 1 d D . . . .
H9BB H 0.083980 0.906646 0.001023 0.054 Uiso 1 1 calc R U . . .
C10B C 0.0718(5) 1.1098(10) 0.0615(7) 0.048(2) Uani 1 1 d D . . . .
H10B H 0.042452 1.084172 0.119058 0.057 Uiso 1 1 calc R U . . .
C11B C 0.0897(4) 1.2537(11) 0.0487(8) 0.050(2) Uani 1 1 d D . . . .
H11B H 0.073277 1.325333 0.097850 0.059 Uiso 1 1 calc R U . . .
C12B C 0.1314(4) 1.2892(11) -0.0362(8) 0.048(2) Uani 1 1 d D . . . .
H12B H 0.143724 1.386758 -0.045157 0.058 Uiso 1 1 calc R U . . .
C13B C 0.1565(4) 1.1861(9) -0.1100(7) 0.0392(17) Uani 1 1 d D . . . .
H13B H 0.184603 1.212935 -0.169633 0.047 Uiso 1 1 calc R U . . .
C14B C 0.2675(4) 0.9360(9) -0.0730(6) 0.0340(17) Uani 1 1 d D . . . .
H14C H 0.258102 1.029294 -0.036650 0.041 Uiso 1 1 calc R U . . .
H14D H 0.286699 0.953866 -0.151005 0.041 Uiso 1 1 calc R U . . .
C15B C 0.3110(4) 0.8556(9) 0.0113(6) 0.0344(17) Uani 1 1 d D . . . .
H15C H 0.301168 0.751880 0.003717 0.041 Uiso 1 1 calc R U . . .
H15D H 0.353489 0.872389 -0.014292 0.041 Uiso 1 1 calc R U . . .
C16B C 0.2446(4) 0.8751(11) 0.1861(7) 0.042(2) Uani 1 1 d D . . . .
H16D H 0.243490 0.909732 0.269530 0.063 Uiso 1 1 calc R U . . .
H16E H 0.233951 0.772672 0.183022 0.063 Uiso 1 1 calc R U . . .
H16F H 0.215171 0.926895 0.135103 0.063 Uiso 1 1 calc R U . . .
C17B C 0.3530(4) 0.8219(10) 0.2191(8) 0.044(2) Uani 1 1 d D . . . .
H17D H 0.354569 0.862834 0.300778 0.065 Uiso 1 1 calc R U . . .
H17E H 0.393564 0.831386 0.185007 0.065 Uiso 1 1 calc R U . . .
H17F H 0.340497 0.720531 0.222450 0.065 Uiso 1 1 calc R U . . .
O2B O 0.2815(2) 1.3876(7) -0.0502(4) 0.0334(13) Uani 1 1 d D . . . .
H2B H 0.301618 1.327322 -0.086971 0.040 Uiso 1 1 calc R U . . .
O3B O 0.2897(3) 1.4983(7) 0.1241(5) 0.0385(14) Uani 1 1 d D . . . .
O4B O 0.4008(3) 1.3389(6) 0.3143(4) 0.0305(12) Uani 1 1 d D . . . .
O5B O 0.3339(2) 1.1647(6) 0.2614(4) 0.0268(11) Uani 1 1 d D . . . .
O6B O 0.4676(3) 1.0536(8) 0.2433(6) 0.0458(16) Uani 1 1 d D . . . .
O7B O 0.5474(3) 1.0951(7) 0.1290(5) 0.0399(14) Uani 1 1 d D . . . .
H7B H 0.560485 1.021730 0.163556 0.048 Uiso 1 1 calc R U . . .
O8B O 0.3680(2) 1.1495(6) 0.0438(4) 0.0265(11) Uani 1 1 d D . . . .
H8B H 0.378014 1.153603 -0.028523 0.032 Uiso 1 1 calc R U . . .
C18B C 0.3139(3) 1.4343(8) 0.0467(5) 0.0248(13) Uani 1 1 d D . . . .
C19B C 0.3820(3) 1.4090(7) 0.0520(5) 0.0235(13) Uani 1 1 d D . . . .
H19C H 0.403349 1.487197 0.099098 0.028 Uiso 1 1 calc R U . . .
H19D H 0.397140 1.411698 -0.030869 0.028 Uiso 1 1 calc R U . . .
C20B C 0.3981(3) 1.2632(7) 0.1105(5) 0.0222(13) Uani 1 1 d D . . . .
C21B C 0.3752(3) 1.2537(8) 0.2405(5) 0.0235(13) Uani 1 1 d D . . . .
C22B C 0.4674(3) 1.2543(8) 0.1089(6) 0.0271(14) Uani 1 1 d D . . . .
H22C H 0.479539 1.255222 0.023909 0.033 Uiso 1 1 calc R U . . .
H22D H 0.486057 1.340822 0.149056 0.033 Uiso 1 1 calc R U . . .
C23B C 0.4933(3) 1.1247(8) 0.1694(6) 0.0266(14) Uani 1 1 d D . . . .


_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 C14A 1.420(8) . ?
O1A C7A 1.432(8) . ?
N1A C16A 1.485(9) . ?
N1A C17A 1.493(9) . ?
N1A C15A 1.497(8) . ?
N1A H1A 1.0000 . ?
C1A C6A 1.361(10) . ?
C1A C2A 1.401(11) . ?
C1A H1AA 0.9500 . ?
C2A C3A 1.391(11) . ?
C2A H2AA 0.9500 . ?
C3A C4A 1.362(11) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.354(10) . ?
C4A H4AA 0.9500 . ?
C5A C6A 1.397(9) . ?
C5A H5AA 0.9500 . ?
C6A C7A 1.521(10) . ?
C7A C8A 1.548(10) . ?
C7A H7AA 1.0000 . ?
C8A C13A 1.375(11) . ?
C8A C9A 1.387(10) . ?
C9A C10A 1.392(12) . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.396(14) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.360(12) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.389(12) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.517(9) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
O2A C18A 1.318(8) . ?
O2A H2A 0.8400 . ?
O3A C18A 1.218(7) . ?
O4A C21A 1.246(8) . ?
O5A C21A 1.242(8) . ?
O6A C23A 1.203(8) . ?
O7A C23A 1.320(8) . ?
O7A H7A 0.8400 . ?
O8A C20A 1.410(8) . ?
O8A H8A 0.8400 . ?
C18A C19A 1.512(9) . ?
C19A C20A 1.561(8) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A C22A 1.533(8) . ?
C20A C21A 1.545(7) . ?
C22A C23A 1.511(9) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
O1B C14B 1.422(8) . ?
O1B C7B 1.449(9) . ?
N1B C16B 1.490(9) . ?
N1B C17B 1.496(10) . ?
N1B C15B 1.503(9) . ?
N1B H1B 1.0000 . ?
C1B C6B 1.354(11) . ?
C1B C2B 1.401(12) . ?
C1B H1BB 0.9500 . ?
C2B C3B 1.379(12) . ?
C2B H2BB 0.9500 . ?
C3B C4B 1.404(12) . ?
C3B H3BB 0.9500 . ?
C4B C5B 1.364(11) . ?
C4B H4BB 0.9500 . ?
C5B C6B 1.411(10) . ?
C5B H5BB 0.9500 . ?
C6B C7B 1.531(10) . ?
C7B C8B 1.538(10) . ?
C7B H7BB 1.0000 . ?
C8B C13B 1.397(11) . ?
C8B C9B 1.398(10) . ?
C9B C10B 1.388(12) . ?
C9B H9BB 0.9500 . ?
C10B C11B 1.400(13) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.372(13) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.400(12) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.523(10) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
O2B C18B 1.325(8) . ?
O2B H2B 0.8400 . ?
O3B C18B 1.194(8) . ?
O4B C21B 1.242(8) . ?
O5B C21B 1.238(8) . ?
O6B C23B 1.204(8) . ?
O7B C23B 1.317(8) . ?
O7B H7B 0.8400 . ?
O8B C20B 1.420(7) . ?
O8B H8B 0.8400 . ?
C18B C19B 1.511(9) . ?
C19B C20B 1.558(9) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B C22B 1.518(9) . ?
C20B C21B 1.547(8) . ?
C22B C23B 1.504(9) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?

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
C14A O1A C7A 111.0(5) . . ?
C16A N1A C17A 110.9(6) . . ?
C16A N1A C15A 111.2(6) . . ?
C17A N1A C15A 110.3(6) . . ?
C16A N1A H1A 108.1 . . ?
C17A N1A H1A 108.1 . . ?
C15A N1A H1A 108.1 . . ?
C6A C1A C2A 119.8(7) . . ?
C6A C1A H1AA 120.1 . . ?
C2A C1A H1AA 120.1 . . ?
C3A C2A C1A 120.8(8) . . ?
C3A C2A H2AA 119.6 . . ?
C1A C2A H2AA 119.6 . . ?
C4A C3A C2A 118.2(7) . . ?
C4A C3A H3AA 120.9 . . ?
C2A C3A H3AA 120.9 . . ?
C5A C4A C3A 120.4(7) . . ?
C5A C4A H4AA 119.8 . . ?
C3A C4A H4AA 119.8 . . ?
C4A C5A C6A 122.6(7) . . ?
C4A C5A H5AA 118.7 . . ?
C6A C5A H5AA 118.7 . . ?
C1A C6A C5A 117.6(7) . . ?
C1A C6A C7A 122.7(6) . . ?
C5A C6A C7A 119.5(6) . . ?
O1A C7A C6A 108.1(6) . . ?
O1A C7A C8A 111.8(5) . . ?
C6A C7A C8A 111.5(6) . . ?
O1A C7A H7AA 108.5 . . ?
C6A C7A H7AA 108.5 . . ?
C8A C7A H7AA 108.5 . . ?
C13A C8A C9A 119.6(8) . . ?
C13A C8A C7A 119.0(6) . . ?
C9A C8A C7A 121.2(7) . . ?
C8A C9A C10A 119.0(8) . . ?
C8A C9A H9AA 120.5 . . ?
C10A C9A H9AA 120.5 . . ?
C9A C10A C11A 121.7(8) . . ?
C9A C10A H10A 119.2 . . ?
C11A C10A H10A 119.2 . . ?
C12A C11A C10A 117.6(9) . . ?
C12A C11A H11A 121.2 . . ?
C10A C11A H11A 121.2 . . ?
C11A C12A C13A 122.0(10) . . ?
C11A C12A H12A 119.0 . . ?
C13A C12A H12A 119.0 . . ?
C8A C13A C12A 120.0(7) . . ?
C8A C13A H13A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
O1A C14A C15A 108.9(6) . . ?
O1A C14A H14A 109.9 . . ?
C15A C14A H14A 109.9 . . ?
O1A C14A H14B 109.9 . . ?
C15A C14A H14B 109.9 . . ?
H14A C14A H14B 108.3 . . ?
N1A C15A C14A 113.9(6) . . ?
N1A C15A H15A 108.8 . . ?
C14A C15A H15A 108.8 . . ?
N1A C15A H15B 108.8 . . ?
C14A C15A H15B 108.8 . . ?
H15A C15A H15B 107.7 . . ?
N1A C16A H16A 109.5 . . ?
N1A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
N1A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N1A C17A H17A 109.5 . . ?
N1A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
N1A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C18A O2A H2A 109.5 . . ?
C23A O7A H7A 109.5 . . ?
C20A O8A H8A 109.5 . . ?
O3A C18A O2A 120.0(6) . . ?
O3A C18A C19A 122.0(6) . . ?
O2A C18A C19A 118.0(6) . . ?
C18A C19A C20A 113.8(6) . . ?
C18A C19A H19A 108.8 . . ?
C20A C19A H19A 108.8 . . ?
C18A C19A H19B 108.8 . . ?
C20A C19A H19B 108.8 . . ?
H19A C19A H19B 107.7 . . ?
O8A C20A C22A 110.7(5) . . ?
O8A C20A C21A 107.7(5) . . ?
C22A C20A C21A 111.8(5) . . ?
O8A C20A C19A 110.4(5) . . ?
C22A C20A C19A 106.5(5) . . ?
C21A C20A C19A 109.7(5) . . ?
O5A C21A O4A 125.6(5) . . ?
O5A C21A C20A 117.4(5) . . ?
O4A C21A C20A 117.0(5) . . ?
C23A C22A C20A 113.7(5) . . ?
C23A C22A H22A 108.8 . . ?
C20A C22A H22A 108.8 . . ?
C23A C22A H22B 108.8 . . ?
C20A C22A H22B 108.8 . . ?
H22A C22A H22B 107.7 . . ?
O6A C23A O7A 122.9(7) . . ?
O6A C23A C22A 125.8(6) . . ?
O7A C23A C22A 111.3(6) . . ?
C14B O1B C7B 112.7(6) . . ?
C16B N1B C17B 109.9(6) . . ?
C16B N1B C15B 111.7(6) . . ?
C17B N1B C15B 110.8(6) . . ?
C16B N1B H1B 108.1 . . ?
C17B N1B H1B 108.1 . . ?
C15B N1B H1B 108.1 . . ?
C6B C1B C2B 121.7(8) . . ?
C6B C1B H1BB 119.1 . . ?
C2B C1B H1BB 119.1 . . ?
C3B C2B C1B 119.7(9) . . ?
C3B C2B H2BB 120.2 . . ?
C1B C2B H2BB 120.2 . . ?
C2B C3B C4B 118.6(8) . . ?
C2B C3B H3BB 120.7 . . ?
C4B C3B H3BB 120.7 . . ?
C5B C4B C3B 121.0(8) . . ?
C5B C4B H4BB 119.5 . . ?
C3B C4B H4BB 119.5 . . ?
C4B C5B C6B 120.1(8) . . ?
C4B C5B H5BB 119.9 . . ?
C6B C5B H5BB 119.9 . . ?
C1B C6B C5B 118.6(8) . . ?
C1B C6B C7B 123.4(7) . . ?
C5B C6B C7B 117.9(7) . . ?
O1B C7B C6B 108.6(6) . . ?
O1B C7B C8B 109.8(6) . . ?
C6B C7B C8B 112.6(6) . . ?
O1B C7B H7BB 108.6 . . ?
C6B C7B H7BB 108.6 . . ?
C8B C7B H7BB 108.6 . . ?
C13B C8B C9B 120.8(8) . . ?
C13B C8B C7B 121.9(7) . . ?
C9B C8B C7B 117.3(7) . . ?
C10B C9B C8B 119.1(8) . . ?
C10B C9B H9BB 120.5 . . ?
C8B C9B H9BB 120.5 . . ?
C9B C10B C11B 121.1(9) . . ?
C9B C10B H10B 119.5 . . ?
C11B C10B H10B 119.5 . . ?
C12B C11B C10B 118.7(9) . . ?
C12B C11B H11B 120.6 . . ?
C10B C11B H11B 120.6 . . ?
C11B C12B C13B 122.0(9) . . ?
C11B C12B H12B 119.0 . . ?
C13B C12B H12B 119.0 . . ?
C8B C13B C12B 118.3(8) . . ?
C8B C13B H13B 120.8 . . ?
C12B C13B H13B 120.8 . . ?
O1B C14B C15B 108.3(6) . . ?
O1B C14B H14C 110.0 . . ?
C15B C14B H14C 110.0 . . ?
O1B C14B H14D 110.0 . . ?
C15B C14B H14D 110.0 . . ?
H14C C14B H14D 108.4 . . ?
N1B C15B C14B 113.2(7) . . ?
N1B C15B H15C 108.9 . . ?
C14B C15B H15C 108.9 . . ?
N1B C15B H15D 108.9 . . ?
C14B C15B H15D 108.9 . . ?
H15C C15B H15D 107.8 . . ?
N1B C16B H16D 109.5 . . ?
N1B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
N1B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N1B C17B H17D 109.5 . . ?
N1B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
N1B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C18B O2B H2B 109.5 . . ?
C23B O7B H7B 109.5 . . ?
C20B O8B H8B 109.5 . . ?
O3B C18B O2B 120.2(7) . . ?
O3B C18B C19B 122.1(6) . . ?
O2B C18B C19B 117.6(6) . . ?
C18B C19B C20B 112.8(5) . . ?
C18B C19B H19C 109.0 . . ?
C20B C19B H19C 109.0 . . ?
C18B C19B H19D 109.0 . . ?
C20B C19B H19D 109.0 . . ?
H19C C19B H19D 107.8 . . ?
O8B C20B C22B 111.7(6) . . ?
O8B C20B C21B 106.7(5) . . ?
C22B C20B C21B 111.5(5) . . ?
O8B C20B C19B 109.9(5) . . ?
C22B C20B C19B 106.2(5) . . ?
C21B C20B C19B 111.0(5) . . ?
O5B C21B O4B 126.4(6) . . ?
O5B C21B C20B 118.3(5) . . ?
O4B C21B C20B 115.3(6) . . ?
C23B C22B C20B 114.9(6) . . ?
C23B C22B H22C 108.5 . . ?
C20B C22B H22C 108.5 . . ?
C23B C22B H22D 108.5 . . ?
C20B C22B H22D 108.5 . . ?
H22C C22B H22D 107.5 . . ?
O6B C23B O7B 123.6(7) . . ?
O6B C23B C22B 124.7(6) . . ?
O7B C23B C22B 111.6(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A C3A 7.8(18) . . . . ?
C1A C2A C3A C4A -7.6(16) . . . . ?
C2A C3A C4A C5A 4.1(13) . . . . ?
C3A C4A C5A C6A -0.8(12) . . . . ?
C2A C1A C6A C5A -4.2(15) . . . . ?
C2A C1A C6A C7A 171.2(10) . . . . ?
C4A C5A C6A C1A 0.8(13) . . . . ?
C4A C5A C6A C7A -174.8(7) . . . . ?
C14A O1A C7A C6A 166.7(6) . . . . ?
C14A O1A C7A C8A -70.2(7) . . . . ?
C1A C6A C7A O1A 38.9(11) . . . . ?
C5A C6A C7A O1A -145.7(7) . . . . ?
C1A C6A C7A C8A -84.3(10) . . . . ?
C5A C6A C7A C8A 91.0(8) . . . . ?
O1A C7A C8A C13A 124.6(7) . . . . ?
C6A C7A C8A C13A -114.3(8) . . . . ?
O1A C7A C8A C9A -51.1(10) . . . . ?
C6A C7A C8A C9A 70.0(9) . . . . ?
C13A C8A C9A C10A 1.4(13) . . . . ?
C7A C8A C9A C10A 177.0(8) . . . . ?
C8A C9A C10A C11A -0.6(15) . . . . ?
C9A C10A C11A C12A 1.0(16) . . . . ?
C10A C11A C12A C13A -2.3(15) . . . . ?
C9A C8A C13A C12A -2.6(13) . . . . ?
C7A C8A C13A C12A -178.3(8) . . . . ?
C11A C12A C13A C8A 3.1(14) . . . . ?
C7A O1A C14A C15A -179.3(5) . . . . ?
C16A N1A C15A C14A 60.9(9) . . . . ?
C17A N1A C15A C14A -175.6(7) . . . . ?
O1A C14A C15A N1A -93.3(7) . . . . ?
O3A C18A C19A C20A 89.6(9) . . . . ?
O2A C18A C19A C20A -91.1(8) . . . . ?
C18A C19A C20A O8A 63.3(7) . . . . ?
C18A C19A C20A C22A -176.4(5) . . . . ?
C18A C19A C20A C21A -55.3(7) . . . . ?
O8A C20A C21A O5A -6.2(8) . . . . ?
C22A C20A C21A O5A -128.1(7) . . . . ?
C19A C20A C21A O5A 114.0(7) . . . . ?
O8A C20A C21A O4A 173.3(6) . . . . ?
C22A C20A C21A O4A 51.4(9) . . . . ?
C19A C20A C21A O4A -66.5(8) . . . . ?
O8A C20A C22A C23A -63.0(7) . . . . ?
C21A C20A C22A C23A 57.1(8) . . . . ?
C19A C20A C22A C23A 176.9(6) . . . . ?
C20A C22A C23A O6A -24.1(11) . . . . ?
C20A C22A C23A O7A 156.6(6) . . . . ?
C6B C1B C2B C3B -0.4(15) . . . . ?
C1B C2B C3B C4B -2.7(15) . . . . ?
C2B C3B C4B C5B 1.8(14) . . . . ?
C3B C4B C5B C6B 2.2(13) . . . . ?
C2B C1B C6B C5B 4.4(14) . . . . ?
C2B C1B C6B C7B 179.6(8) . . . . ?
C4B C5B C6B C1B -5.3(12) . . . . ?
C4B C5B C6B C7B 179.3(7) . . . . ?
C14B O1B C7B C6B 163.7(6) . . . . ?
C14B O1B C7B C8B -72.8(7) . . . . ?
C1B C6B C7B O1B 2.0(10) . . . . ?
C5B C6B C7B O1B 177.2(6) . . . . ?
C1B C6B C7B C8B -119.7(9) . . . . ?
C5B C6B C7B C8B 55.5(9) . . . . ?
O1B C7B C8B C13B 102.0(8) . . . . ?
C6B C7B C8B C13B -136.9(7) . . . . ?
O1B C7B C8B C9B -76.9(9) . . . . ?
C6B C7B C8B C9B 44.2(9) . . . . ?
C13B C8B C9B C10B -1.1(13) . . . . ?
C7B C8B C9B C10B 177.8(8) . . . . ?
C8B C9B C10B C11B -0.4(14) . . . . ?
C9B C10B C11B C12B 1.0(14) . . . . ?
C10B C11B C12B C13B 0.0(14) . . . . ?
C9B C8B C13B C12B 2.1(12) . . . . ?
C7B C8B C13B C12B -176.8(7) . . . . ?
C11B C12B C13B C8B -1.5(13) . . . . ?
C7B O1B C14B C15B 177.0(6) . . . . ?
C16B N1B C15B C14B 59.5(9) . . . . ?
C17B N1B C15B C14B -177.6(7) . . . . ?
O1B C14B C15B N1B -95.5(8) . . . . ?
O3B C18B C19B C20B 93.4(8) . . . . ?
O2B C18B C19B C20B -89.2(7) . . . . ?
C18B C19B C20B O8B 59.0(7) . . . . ?
C18B C19B C20B C22B 179.9(5) . . . . ?
C18B C19B C20B C21B -58.7(7) . . . . ?
O8B C20B C21B O5B -5.9(8) . . . . ?
C22B C20B C21B O5B -128.1(7) . . . . ?
C19B C20B C21B O5B 113.8(7) . . . . ?
O8B C20B C21B O4B 174.4(6) . . . . ?
C22B C20B C21B O4B 52.2(8) . . . . ?
C19B C20B C21B O4B -66.0(8) . . . . ?
O8B C20B C22B C23B -64.2(7) . . . . ?
C21B C20B C22B C23B 55.1(8) . . . . ?
C19B C20B C22B C23B 176.1(5) . . . . ?
C20B C22B C23B O6B -21.1(10) . . . . ?
C20B C22B C23B O7B 157.0(6) . . . . ?

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
N1A H1A O5A 1.00 1.97 2.842(9) 143.9 . yes
N1A H1A O8A 1.00 2.07 2.876(9) 135.8 . yes
C7A H7AA O3B 1.00 2.45 3.400(9) 157.6 2_676 yes
C14A H14A O8A 0.99 2.63 3.116(9) 110.5 . yes
C14A H14B O3B 0.99 2.53 3.432(9) 150.9 2_676 yes
C15A H15B O7A 0.99 2.44 3.386(9) 159.4 2_666 yes
C16A H16A O2B 0.98 2.57 3.485(10) 154.9 2_675 yes
C16A H16C O1A 0.98 2.56 3.110(10) 115.3 . yes
C17A H17B O6A 0.98 2.64 3.210(12) 117.5 . yes
C17A H17C O3A 0.98 2.56 3.441(12) 149.1 1_545 yes
O2A H2A O5B 0.84 1.83 2.604(7) 152.3 2_676 yes
O7A H7A O4B 0.84 1.78 2.592(8) 163.3 1_545 yes
O8A H8A O4B 0.84 1.84 2.667(6) 170.6 2_676 yes
C22A H22B O6B 0.99 2.43 3.423(10) 179.0 . yes
N1B H1B O5B 1.00 1.97 2.841(9) 144.3 . yes
N1B H1B O8B 1.00 2.10 2.888(8) 134.4 . yes
C14B H14D O3A 0.99 2.42 3.357(9) 157.7 2_675 yes
C15B H15D O7B 0.99 2.57 3.537(10) 166.8 2_675 yes
C16B H16F O1B 0.98 2.61 3.134(10) 113.9 . yes
C17B H17E O6B 0.98 2.65 3.261(12) 120.4 . yes
C17B H17F O3B 0.98 2.54 3.431(12) 150.4 1_545 yes
O2B H2B O5A 0.84 1.88 2.568(7) 138.1 2_675 yes
O7B H7B O4A 0.84 1.77 2.570(8) 158.8 . yes
O8B H8B O4A 0.84 1.81 2.647(6) 173.5 2_675 yes
C22B H22D O6A 0.99 2.47 3.464(10) 177.5 1_565 yes

_refine_diff_density_max         0.906
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.128


# start Validation Reply Form
_vrf_DIFMX02_148k                
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: ...Twin structure in phase transition.
;
_vrf_PLAT029_148k                
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.974 Why?
RESPONSE: ...Twin structure in phase transition.
;
_vrf_PLAT082_148k                
;
PROBLEM: High R1 Value .................................. 0.14 Report
RESPONSE: ...Twin structure in phase transition.
;
_vrf_PLAT155_148k                
;
PROBLEM: The Triclinic Unitcell is NOT Reduced .......... Please Do !
RESPONSE: ... Non-standard triclinic cell is a distortion of the parent
monoclinic in form I. It is retained for the purpose of comparing 
these crystal structures.
;
_vrf_PLAT250_148k                
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.7 Note
RESPONSE: ...Twin structure in phase transition.
;
_vrf_PLAT480_148k                
;
PROBLEM: Long H...A H-Bond Reported H14A ..O8A . 2.63 Ang.
RESPONSE: ...Retained for comparing structures.
;
_vrf_PLAT906_148k                
;
PROBLEM: Large K Value in the Analysis of Variance ...... 4.940 Check
RESPONSE: ...Twin structure in phase transition.
;
_vrf_PLAT911_148k                
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 213 Report
RESPONSE: ...Twin structure in phase transition.
;
# end Validation Reply Form


