# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_TMP_DLA_a
_database_code_depnum_ccdc_archive 'CCDC 2241034'
loop_
_audit_author_name
_audit_author_address
'Qixuan Zheng'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_TMP_DLA_a           
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.87 Note  
RESPONSE: Due a truncated data collection along with modeling disorder 
          within the structure.
;
_vrf_PLAT340_TMP_DLA_a           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00436 Ang.  
RESPONSE: Due to the low data to parameter ratio.
;
_vrf_PLAT480_TMP_DLA_a           
;
PROBLEM: Long H...A H-Bond Reported H1       ..O7       .       2.65 Ang.  
RESPONSE: These distance were included for further analysis. 
;
_vrf_PLAT911_TMP_DLA_a           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report
RESPONSE: These reflection were omitted due to the data collection strategy.
;
_vrf_PLAT915_TMP_DLA_a           
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         59 %     
RESPONSE: Due to a truncated data collection.
;
# end Validation Reply Form

_audit_creation_date             2021-12-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
Qixuan.Zheng@ttu.edu
daniel.unruh@ttu.edu
kristin.hutchins@ttu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N4 O3, C3 H5 O3'
_chemical_formula_sum            'C17 H24 N4 O6'
_chemical_formula_weight         380.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C35  H35  N35  O35  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.09750(10)
_cell_length_b                   36.4142(5)
_cell_length_c                   10.00430(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.2640(10)
_cell_angle_gamma                90
_cell_volume                     1849.18(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2290
_cell_measurement_theta_min      4.5810
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 23 2 0.0125
3 1 -1 0.0653
-3 -13 0 0.0667
0 1 -2 0.0112
0 -1 2 0.0093
2 10 -4 0.0384
0 -24 1 0.0142
-2 -18 0 0.0494
0 -17 -5 0.0118

_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.021
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1317 22.6510 1.8062 -0.5044 0.7338 0.4551
3.3058 0.5298 -0.8270 0.2323 -0.3365 0.9126
-2.6884 -13.4082 -0.3822 0.1057 -0.1548 -0.9823
-0.0013 1.0148 -1.9977 0.2809 0.1354 -0.0087
0.0013 -1.0148 1.9977 -0.2809 -0.1354 0.0087
2.1831 10.2160 -4.3658 0.6047 0.3295 0.7251
0.0614 -23.5260 0.6011 0.1690 -0.9071 -0.3856
-2.1556 -17.9236 0.2667 0.0786 -0.4175 -0.9053
0.1552 -16.6460 -4.6093 0.8592 -0.4090 -0.3075

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18312
_diffrn_reflns_point_group_measured_fraction_full 0.836
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.207
_diffrn_reflns_theta_min         2.427
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  25.00   0.50    6.91    --  -47.76  90.00 -15.00  202
  2  ω    -20.00  77.00   0.50    6.91    --   47.76 -90.00-130.00  194
  3  ω   -163.00 -79.00   0.50   25.00    --  -91.75 -90.00-130.00  168
  4  ω    -79.00 -19.00   0.50   25.00    --  -91.75  90.00 -15.00  120
  5  ω     35.00 105.00   0.50   25.00    --  107.31 -90.00-130.00  140
  6  ω    101.00 178.00   0.50   25.00    --  107.31  90.00 -15.00  154
  7  ω   -120.00 -73.00   0.50    6.91    --  -47.76-125.00   0.00   94
  8  ω   -120.00 -73.00   0.50    6.91    --  -47.76-125.00  30.00   94
  9  ω   -120.00 -73.00   0.50    6.91    --  -47.76-125.00 -30.00   94
 10  ω    -25.00  28.00   0.50    6.91    --  -47.76  19.00 -90.00  106
 11  ω    -85.00 -19.00   0.50   25.00    --  -91.75 125.00   0.00  132
 12  ω    -64.00 -19.00   0.50   25.00    --  -91.75  57.00 -30.00   90
 13  ω    -64.00 -19.00   0.50   25.00    --  -91.75  57.00 -60.00   90
 14  ω    -64.00 -19.00   0.50   25.00    --  -91.75  57.00   0.00   90
 15  ω    -64.00 -19.00   0.50   25.00    --  -91.75  57.00-180.00   90
 16  ω    -82.00 -37.00   0.50   25.00    --  -91.75 125.00 120.00   90
 17  ω     96.00 167.00   0.50   25.00    --  107.31  19.00 -90.00  142
 18  ω     35.00  62.00   0.50   25.00    --  107.31 -57.00 120.00   54
 19  ω     82.00 107.00   0.50   25.00    --  107.31 -77.00  30.00   50
 20  ω     37.00  67.00   0.50   25.00    --  107.31 -57.00  30.00   60
 21  ω     37.00 107.00   0.50   25.00    --  107.31 -77.00-120.00  140
 22  ω    100.00 169.00   0.50   25.00    --  107.31 125.00  60.00  138
 23  ω     35.00  68.00   0.50   25.00    --  107.31 -57.00  60.00   66
 24  ω     36.00  66.00   0.50   25.00    --  107.31 -57.00  90.00   60
 25  ω     36.00  68.00   0.50   25.00    --  107.31 -77.00  30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0354371000
_diffrn_orient_matrix_UB_12      -0.0108238000
_diffrn_orient_matrix_UB_13      -0.1461196000
_diffrn_orient_matrix_UB_21      -0.1199596000
_diffrn_orient_matrix_UB_22      0.0369927000
_diffrn_orient_matrix_UB_23      -0.0489027000
_diffrn_orient_matrix_UB_31      0.2765179000
_diffrn_orient_matrix_UB_32      0.0174453000
_diffrn_orient_matrix_UB_33      0.0130164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.592
_reflns_number_gt                5538
_reflns_number_total             6107
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         6107
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+0.1770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0945
_refine_special_details          
'The pyruvic acid molecule (O10<O12 and C32<C34) was positionally disordered over two sites (A and B). The site occupancies for these sites were constrained to 0.5 and the rigid bond restraint RIGU was also applied to the disordered sites.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.1(2)
 -0.1(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Rigid body (RIGU) restrains
 O10A, O11A, O12A, C32A, C33A, C34A, O10B, O11B, O12B, C32B, C33B, C34B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: O10A(0.5) O11A(0.5) O12A(0.5) H12A(0.5) C32A(0.5) C33A(0.5)
 H33A(0.5) C34A(0.5) H34A(0.5) H34B(0.5) H34C(0.5) O10B(0.5) O11B(0.5)
 O12B(0.5) H12B(0.5) C32B(0.5) C33B(0.5) H33B(0.5) C34B(0.5) H34D(0.5)
 H34E(0.5) H34F(0.5)
5.a Ternary CH refined with riding coordinates:
 C30(H30), C33A(H33A), C33B(H33B)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C24(H24A,H24B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C12(H12), N5(H5), C18(H18), C20(H20), C26(H26)
5.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B), N6(H6A,H6B), N8(H8D,H8E)
5.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C21(H21A,H21B,H21C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C34A(H34A,H34B,
 H34C), C34B(H34D,H34E,H34F)
5.f Idealised tetrahedral OH refined as rotating group:
 O9(H9), O12A(H12A), O12B(H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.3817(4) 0.69841(7) 0.3166(2) 0.0281(5) Uani 1 1 d . . . . .
O2 O -0.0267(4) 0.74467(6) 0.4369(2) 0.0265(5) Uani 1 1 d . . . . .
O3 O 0.3271(4) 0.72193(7) 0.6340(2) 0.0282(5) Uani 1 1 d . . . . .
N1 N 0.4143(5) 0.55484(7) 0.3648(2) 0.0210(5) Uani 1 1 d . . . . .
H1 H 0.450546 0.558553 0.281517 0.025 Uiso 1 1 calc R U . . .
N2 N 0.7227(5) 0.50897(7) 0.3836(2) 0.0218(5) Uani 1 1 d . . . . .
H2A H 0.808935 0.491399 0.429281 0.026 Uiso 1 1 calc R U . . .
H2B H 0.760147 0.514175 0.301596 0.026 Uiso 1 1 calc R U . . .
N3 N 0.4775(5) 0.51991(7) 0.5634(2) 0.0213(5) Uani 1 1 d . . . . .
N4 N 0.2368(5) 0.53234(8) 0.7389(3) 0.0274(6) Uani 1 1 d . . . . .
H4A H 0.317192 0.513854 0.781962 0.033 Uiso 1 1 calc R U . . .
H4B H 0.118403 0.545199 0.777340 0.033 Uiso 1 1 calc R U . . .
C1 C -0.2126(6) 0.68386(9) 0.4163(3) 0.0223(6) Uani 1 1 d . . . . .
C2 C -0.0306(6) 0.70859(9) 0.4792(3) 0.0230(6) Uani 1 1 d . . . . .
C3 C 0.1552(6) 0.69605(9) 0.5807(3) 0.0235(6) Uani 1 1 d . . . . .
C4 C 0.1523(6) 0.65947(9) 0.6221(3) 0.0222(6) Uani 1 1 d . . . . .
H4 H 0.276325 0.651149 0.692271 0.027 Uiso 1 1 calc R U . . .
C5 C -0.0317(5) 0.63523(9) 0.5609(3) 0.0210(6) Uani 1 1 d . . . . .
C6 C -0.2138(6) 0.64724(9) 0.4569(3) 0.0216(6) Uani 1 1 d . . . . .
H6 H -0.337641 0.630522 0.414229 0.026 Uiso 1 1 calc R U . . .
C7 C -0.5815(6) 0.67492(10) 0.2558(3) 0.0283(7) Uani 1 1 d . . . . .
H7A H -0.685584 0.688237 0.184192 0.042 Uiso 1 1 calc R U . . .
H7B H -0.696622 0.666957 0.323525 0.042 Uiso 1 1 calc R U . . .
H7C H -0.499842 0.653398 0.217901 0.042 Uiso 1 1 calc R U . . .
C8 C -0.1365(7) 0.76926(10) 0.5297(4) 0.0320(7) Uani 1 1 d . . . . .
H8A H -0.107421 0.794702 0.502806 0.048 Uiso 1 1 calc R U . . .
H8B H -0.050719 0.765120 0.620204 0.048 Uiso 1 1 calc R U . . .
H8C H -0.325974 0.764681 0.529353 0.048 Uiso 1 1 calc R U . . .
C9 C 0.5018(6) 0.71120(10) 0.7468(3) 0.0319(8) Uani 1 1 d . . . . .
H9A H 0.609511 0.690435 0.721856 0.048 Uiso 1 1 calc R U . . .
H9B H 0.399303 0.703914 0.820685 0.048 Uiso 1 1 calc R U . . .
H9C H 0.616674 0.731867 0.775414 0.048 Uiso 1 1 calc R U . . .
C10 C -0.0308(5) 0.59563(8) 0.6082(3) 0.0210(6) Uani 1 1 d . . . . .
H10A H -0.208972 0.585171 0.586739 0.025 Uiso 1 1 calc R U . . .
H10B H 0.007576 0.595181 0.706979 0.025 Uiso 1 1 calc R U . . .
C11 C 0.1680(5) 0.57147(8) 0.5459(3) 0.0203(6) Uani 1 1 d . . . . .
C12 C 0.2359(5) 0.57644(9) 0.4192(3) 0.0209(6) Uani 1 1 d . . . . .
H12 H 0.155226 0.595801 0.366652 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5373(5) 0.52751(9) 0.4381(3) 0.0200(6) Uani 1 1 d . . . . .
C14 C 0.2942(6) 0.54082(9) 0.6159(3) 0.0216(6) Uani 1 1 d . . . . .
O4 O 1.3795(4) 0.30111(7) 1.1836(2) 0.0319(5) Uani 1 1 d . . . . .
O5 O 1.0237(4) 0.25557(6) 1.0618(2) 0.0284(5) Uani 1 1 d . . . . .
O6 O 0.6734(4) 0.27842(6) 0.8658(2) 0.0282(5) Uani 1 1 d . . . . .
N5 N 0.5769(6) 0.44554(7) 1.1298(2) 0.0277(6) Uani 1 1 d . . . . .
H5 H 0.532524 0.441773 1.211619 0.033 Uiso 1 1 calc R U . . .
N6 N 0.2802(5) 0.49304(8) 1.1077(3) 0.0271(6) Uani 1 1 d . . . . .
H6A H 0.202233 0.511264 1.061909 0.033 Uiso 1 1 calc R U . . .
H6B H 0.235984 0.487821 1.188539 0.033 Uiso 1 1 calc R U . . .
N7 N 0.5340(5) 0.48092(7) 0.9325(2) 0.0193(5) Uani 1 1 d . . . . .
N8 N 0.7795(5) 0.46785(8) 0.7587(3) 0.0256(6) Uani 1 1 d . . . . .
H8D H 0.704437 0.486687 0.715367 0.031 Uiso 1 1 calc R U . . .
H8E H 0.896915 0.454572 0.721163 0.031 Uiso 1 1 calc R U . . .
C15 C 1.2114(6) 0.31593(9) 1.0833(3) 0.0256(7) Uani 1 1 d . . . . .
C16 C 1.0287(6) 0.29157(8) 1.0211(3) 0.0231(6) Uani 1 1 d . . . . .
C17 C 0.8447(6) 0.30414(8) 0.9190(3) 0.0241(6) Uani 1 1 d . . . . .
C18 C 0.8470(6) 0.34056(9) 0.8789(4) 0.0287(7) Uani 1 1 d . . . . .
H18 H 0.722468 0.348995 0.809188 0.034 Uiso 1 1 calc R U . . .
C19 C 1.0325(6) 0.36498(9) 0.9411(4) 0.0309(8) Uani 1 1 d . . . . .
C20 C 1.2126(6) 0.35260(9) 1.0433(4) 0.0295(7) Uani 1 1 d . . . . .
H20 H 1.337407 0.369157 1.086280 0.035 Uiso 1 1 calc R U . . .
C21 C 1.5807(7) 0.32440(11) 1.2460(3) 0.0336(8) Uani 1 1 d . . . . .
H21A H 1.692621 0.333282 1.178299 0.050 Uiso 1 1 calc R U . . .
H21B H 1.688051 0.310527 1.314919 0.050 Uiso 1 1 calc R U . . .
H21C H 1.499288 0.345364 1.287720 0.050 Uiso 1 1 calc R U . . .
C22 C 1.1380(7) 0.23112(9) 0.9697(4) 0.0313(7) Uani 1 1 d . . . . .
H22A H 1.048839 0.234385 0.879492 0.047 Uiso 1 1 calc R U . . .
H22B H 1.116965 0.205665 0.998721 0.047 Uiso 1 1 calc R U . . .
H22C H 1.325807 0.236692 0.968399 0.047 Uiso 1 1 calc R U . . .
C23 C 0.4971(6) 0.28913(10) 0.7534(4) 0.0324(8) Uani 1 1 d . . . . .
H23A H 0.598045 0.299358 0.683335 0.049 Uiso 1 1 calc R U . . .
H23B H 0.374667 0.307737 0.781581 0.049 Uiso 1 1 calc R U . . .
H23C H 0.397682 0.267661 0.718048 0.049 Uiso 1 1 calc R U . . .
C24 C 1.0317(6) 0.40422(9) 0.8933(4) 0.0343(8) Uani 1 1 d . . . . .
H24A H 0.993942 0.404469 0.794422 0.041 Uiso 1 1 calc R U . . .
H24B H 1.209886 0.414676 0.914643 0.041 Uiso 1 1 calc R U . . .
C25 C 0.8333(6) 0.42861(9) 0.9542(3) 0.0251(7) Uani 1 1 d . . . . .
C26 C 0.7593(6) 0.42334(9) 1.0778(3) 0.0298(7) Uani 1 1 d . . . . .
H26 H 0.835117 0.403727 1.130742 0.036 Uiso 1 1 calc R U . . .
C27 C 0.4653(6) 0.47334(8) 1.0545(3) 0.0212(6) Uani 1 1 d . . . . .
C28 C 0.7153(6) 0.45943(8) 0.8811(3) 0.0206(6) Uani 1 1 d . . . . .
O7 O 0.8837(4) 0.54921(7) 0.1575(2) 0.0296(5) Uani 1 1 d . . . . .
O8 O 0.4912(4) 0.57680(7) 0.1199(2) 0.0272(5) Uani 1 1 d . . . . .
O9 O 1.0620(4) 0.57639(8) -0.0634(2) 0.0368(6) Uani 1 1 d . . . . .
H9 H 1.168696 0.580561 0.003940 0.055 Uiso 1 1 calc R U . . .
C29 C 0.7239(6) 0.56932(8) 0.0911(3) 0.0209(6) Uani 1 1 d . . . . .
C30 C 0.8067(5) 0.58741(8) -0.0360(3) 0.0246(6) Uani 1 1 d . . . . .
H30 H 0.680864 0.579166 -0.112678 0.029 Uiso 1 1 calc R U . . .
C31 C 0.7888(10) 0.62883(11) -0.0278(5) 0.0570(12) Uani 1 1 d . . . . .
H31A H 0.896280 0.637509 0.052222 0.086 Uiso 1 1 calc R U . . .
H31B H 0.604901 0.636063 -0.022260 0.086 Uiso 1 1 calc R U . . .
H31C H 0.853565 0.639748 -0.108054 0.086 Uiso 1 1 calc R U . . .
O10A O 0.4976(9) 0.42019(14) 0.3645(4) 0.0217(9) Uani 0.5 1 d . . P A 1
O11A O 0.132(3) 0.4539(5) 0.3444(13) 0.0239(16) Uani 0.5 1 d . . P A 1
O12A O -0.0688(8) 0.41868(14) 0.5517(4) 0.0263(9) Uani 0.5 1 d . . P A 1
H12A H -0.186698 0.425145 0.492103 0.039 Uiso 0.5 1 calc R U P A 1
C32A C 0.2656(11) 0.42849(17) 0.3930(6) 0.0175(9) Uani 0.5 1 d . . P A 1
C33A C 0.1406(10) 0.40164(15) 0.4904(5) 0.0212(10) Uani 0.5 1 d . . P A 1
H33A H 0.065875 0.380333 0.436565 0.025 Uiso 0.5 1 calc R U P A 1
C34A C 0.3348(10) 0.38678(16) 0.6008(5) 0.0264(11) Uani 0.5 1 d . . P A 1
H34A H 0.400593 0.406970 0.659419 0.040 Uiso 0.5 1 calc R U P A 1
H34B H 0.482606 0.375172 0.560971 0.040 Uiso 0.5 1 calc R U P A 1
H34C H 0.246972 0.368594 0.653500 0.040 Uiso 0.5 1 calc R U P A 1
O10B O 0.189(3) 0.4545(5) 0.3285(15) 0.029(2) Uani 0.5 1 d . . P B 2
O11B O -0.0024(6) 0.44758(10) 0.5192(3) 0.0216(7) Uani 0.5 1 d . . P B 2
O12B O 0.5789(8) 0.40747(14) 0.4038(4) 0.0269(9) Uani 0.5 1 d . . P B 2
H12B H 0.715746 0.418242 0.436419 0.040 Uiso 0.5 1 calc R U P B 2
C32B C 0.1750(10) 0.44044(14) 0.4422(5) 0.0184(8) Uani 0.5 1 d . . P B 2
C33B C 0.3773(10) 0.41159(14) 0.4913(5) 0.0223(9) Uani 0.5 1 d . . P B 2
H33B H 0.459398 0.418955 0.581958 0.027 Uiso 0.5 1 calc R U P B 2
C34B C 0.2380(13) 0.37458(19) 0.5035(7) 0.0322(13) Uani 0.5 1 d . . P B 2
H34D H 0.155144 0.367215 0.415284 0.048 Uiso 0.5 1 calc R U P B 2
H34E H 0.102744 0.376914 0.566573 0.048 Uiso 0.5 1 calc R U P B 2
H34F H 0.366895 0.355960 0.536391 0.048 Uiso 0.5 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.364(4) . ?
O1 C7 1.423(4) . ?
O2 C2 1.381(4) . ?
O2 C8 1.439(4) . ?
O3 C3 1.362(4) . ?
O3 C9 1.427(4) . ?
N1 H1 0.8800 . ?
N1 C12 1.354(4) . ?
N1 C13 1.356(4) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C13 1.320(4) . ?
N3 C13 1.345(4) . ?
N3 C14 1.349(4) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C14 1.327(4) . ?
C1 C2 1.400(4) . ?
C1 C6 1.394(5) . ?
C2 C3 1.400(4) . ?
C3 C4 1.395(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(4) . ?
C5 C6 1.399(4) . ?
C5 C10 1.517(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.518(4) . ?
C11 C12 1.357(4) . ?
C11 C14 1.438(4) . ?
C12 H12 0.9500 . ?
O4 C15 1.369(4) . ?
O4 C21 1.430(4) . ?
O5 C16 1.374(4) . ?
O5 C22 1.442(4) . ?
O6 C17 1.356(4) . ?
O6 C23 1.428(4) . ?
N5 H5 0.8800 . ?
N5 C26 1.370(5) . ?
N5 C27 1.355(4) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C27 1.334(4) . ?
N7 C27 1.330(4) . ?
N7 C28 1.348(4) . ?
N8 H8D 0.8800 . ?
N8 H8E 0.8800 . ?
N8 C28 1.332(4) . ?
C15 C16 1.391(4) . ?
C15 C20 1.394(5) . ?
C16 C17 1.399(4) . ?
C17 C18 1.386(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.401(4) . ?
C19 C20 1.386(5) . ?
C19 C24 1.507(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.515(4) . ?
C25 C26 1.340(5) . ?
C25 C28 1.441(4) . ?
C26 H26 0.9500 . ?
O7 C29 1.241(4) . ?
O8 C29 1.275(4) . ?
O9 H9 0.8400 . ?
O9 C30 1.413(3) . ?
C29 C30 1.525(4) . ?
C30 H30 1.0000 . ?
C30 C31 1.514(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O10A C32A 1.278(8) . ?
O11A C32A 1.223(13) . ?
O12A H12A 0.8400 . ?
O12A C33A 1.421(7) . ?
C32A C33A 1.557(8) . ?
C33A H33A 1.0000 . ?
C33A C34A 1.514(7) . ?
C34A H34A 0.9800 . ?
C34A H34B 0.9800 . ?
C34A H34C 0.9800 . ?
O10B C32B 1.256(11) . ?
O11B C32B 1.267(7) . ?
O12B H12B 0.8400 . ?
O12B C33B 1.418(6) . ?
C32B C33B 1.522(7) . ?
C33B H33B 1.0000 . ?
C33B C34B 1.533(8) . ?
C34B H34D 0.9800 . ?
C34B H34E 0.9800 . ?
C34B H34F 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 C7 117.3(3) . . ?
C2 O2 C8 112.1(2) . . ?
C3 O3 C9 116.9(3) . . ?
C12 N1 H1 119.9 . . ?
C12 N1 C13 120.2(2) . . ?
C13 N1 H1 119.9 . . ?
H2A N2 H2B 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
C13 N3 C14 118.1(2) . . ?
H4A N4 H4B 120.0 . . ?
C14 N4 H4A 120.0 . . ?
C14 N4 H4B 120.0 . . ?
O1 C1 C2 115.3(3) . . ?
O1 C1 C6 124.4(3) . . ?
C6 C1 C2 120.3(3) . . ?
O2 C2 C1 120.1(3) . . ?
O2 C2 C3 120.3(3) . . ?
C3 C2 C1 119.5(3) . . ?
O3 C3 C2 115.2(3) . . ?
O3 C3 C4 124.6(3) . . ?
C4 C3 C2 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 C10 118.9(3) . . ?
C6 C5 C10 120.8(3) . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 108.8 . . ?
C5 C10 H10B 108.8 . . ?
C5 C10 C11 113.9(2) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C12 C11 C10 122.9(3) . . ?
C12 C11 C14 114.7(3) . . ?
C14 C11 C10 122.4(2) . . ?
N1 C12 C11 122.4(3) . . ?
N1 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N2 C13 N1 117.7(2) . . ?
N2 C13 N3 120.8(3) . . ?
N3 C13 N1 121.5(3) . . ?
N3 C14 C11 122.9(2) . . ?
N4 C14 N3 116.7(3) . . ?
N4 C14 C11 120.4(3) . . ?
C15 O4 C21 117.5(3) . . ?
C16 O5 C22 112.4(2) . . ?
C17 O6 C23 117.2(3) . . ?
C26 N5 H5 120.2 . . ?
C27 N5 H5 120.2 . . ?
C27 N5 C26 119.7(3) . . ?
H6A N6 H6B 120.0 . . ?
C27 N6 H6A 120.0 . . ?
C27 N6 H6B 120.0 . . ?
C27 N7 C28 118.5(2) . . ?
H8D N8 H8E 120.0 . . ?
C28 N8 H8D 120.0 . . ?
C28 N8 H8E 120.0 . . ?
O4 C15 C16 115.1(3) . . ?
O4 C15 C20 124.7(3) . . ?
C16 C15 C20 120.2(3) . . ?
O5 C16 C15 120.4(3) . . ?
O5 C16 C17 120.0(3) . . ?
C15 C16 C17 119.6(3) . . ?
O6 C17 C16 115.1(3) . . ?
O6 C17 C18 124.7(3) . . ?
C18 C17 C16 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C24 118.6(3) . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 C24 121.7(3) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 108.7 . . ?
C19 C24 H24B 108.7 . . ?
C19 C24 C25 114.2(3) . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C26 C25 C24 122.8(3) . . ?
C26 C25 C28 116.1(3) . . ?
C28 C25 C24 121.0(3) . . ?
N5 C26 H26 119.2 . . ?
C25 C26 N5 121.6(3) . . ?
C25 C26 H26 119.2 . . ?
N6 C27 N5 117.2(3) . . ?
N7 C27 N5 122.2(3) . . ?
N7 C27 N6 120.7(3) . . ?
N7 C28 C25 121.9(3) . . ?
N8 C28 N7 116.8(3) . . ?
N8 C28 C25 121.3(3) . . ?
C30 O9 H9 109.5 . . ?
O7 C29 O8 125.7(3) . . ?
O7 C29 C30 118.8(2) . . ?
O8 C29 C30 115.5(2) . . ?
O9 C30 C29 111.7(2) . . ?
O9 C30 H30 107.6 . . ?
O9 C30 C31 110.8(3) . . ?
C29 C30 H30 107.6 . . ?
C31 C30 C29 111.3(2) . . ?
C31 C30 H30 107.6 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33A O12A H12A 109.5 . . ?
O10A C32A C33A 115.5(5) . . ?
O11A C32A O10A 125.6(7) . . ?
O11A C32A C33A 118.7(7) . . ?
O12A C33A C32A 111.2(5) . . ?
O12A C33A H33A 107.9 . . ?
O12A C33A C34A 108.0(4) . . ?
C32A C33A H33A 107.9 . . ?
C34A C33A C32A 113.8(4) . . ?
C34A C33A H33A 107.9 . . ?
C33A C34A H34A 109.5 . . ?
C33A C34A H34B 109.5 . . ?
C33A C34A H34C 109.5 . . ?
H34A C34A H34B 109.5 . . ?
H34A C34A H34C 109.5 . . ?
H34B C34A H34C 109.5 . . ?
C33B O12B H12B 109.5 . . ?
O10B C32B O11B 124.8(7) . . ?
O10B C32B C33B 118.7(6) . . ?
O11B C32B C33B 116.5(4) . . ?
O12B C33B C32B 112.4(4) . . ?
O12B C33B H33B 108.8 . . ?
O12B C33B C34B 108.9(4) . . ?
C32B C33B H33B 108.8 . . ?
C32B C33B C34B 109.1(4) . . ?
C34B C33B H33B 108.8 . . ?
C33B C34B H34D 109.5 . . ?
C33B C34B H34E 109.5 . . ?
C33B C34B H34F 109.5 . . ?
H34D C34B H34E 109.5 . . ?
H34D C34B H34F 109.5 . . ?
H34E C34B H34F 109.5 . . ?

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 O7 0.88 2.65 3.314(3) 132.8 . yes
N1 H1 O8 0.88 1.78 2.640(3) 166.0 . yes
N2 H2A O11A 0.88 2.36 2.947(12) 124.5 1_655 yes
N2 H2A O10B 0.88 2.63 3.183(11) 121.5 1_655 yes
N2 H2A O11B 0.88 2.03 2.907(4) 174.4 1_655 yes
N2 H2B O7 0.88 2.07 2.878(3) 152.8 . yes
N4 H4A N7 0.88 2.15 3.002(4) 163.0 . yes
N4 H4B O9 0.88 2.00 2.758(4) 143.7 1_456 yes
N5 H5 O10A 0.88 1.74 2.590(5) 160.5 1_556 yes
N5 H5 O11A 0.88 2.57 3.276(9) 137.5 1_556 yes
N5 H5 O10B 0.88 2.24 2.947(9) 137.1 1_556 yes
N5 H5 O12B 0.88 2.29 3.071(5) 148.4 1_556 yes
N6 H6A O7 0.88 2.40 2.950(3) 121.1 1_456 yes
N6 H6B O11A 0.88 2.09 2.921(9) 156.2 1_556 yes
N6 H6B O10B 0.88 1.88 2.693(10) 152.0 1_556 yes
N8 H8D N3 0.88 2.19 3.038(4) 162.0 . yes
N8 H8E O12A 0.88 2.16 2.896(5) 140.7 1_655 yes
N8 H8E O11B 0.88 2.15 2.831(4) 134.3 1_655 yes
O9 H9 O8 0.84 1.93 2.723(3) 157.4 1_655 yes
O12A H12A O10A 0.84 1.97 2.763(7) 157.4 1_455 yes
O12B H12B O11B 0.84 1.92 2.751(5) 172.5 1_655 yes

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 -1.6(4) . . . . ?
O1 C1 C2 C3 -178.5(2) . . . . ?
O1 C1 C6 C5 -179.8(3) . . . . ?
O2 C2 C3 O3 1.8(4) . . . . ?
O2 C2 C3 C4 -179.3(3) . . . . ?
O3 C3 C4 C5 -180.0(3) . . . . ?
C1 C2 C3 O3 178.7(3) . . . . ?
C1 C2 C3 C4 -2.4(4) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C3 C4 C5 C10 -179.9(3) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C4 C5 C10 C11 -83.1(3) . . . . ?
C5 C10 C11 C12 -32.8(4) . . . . ?
C5 C10 C11 C14 148.9(3) . . . . ?
C6 C1 C2 O2 178.7(3) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
C6 C5 C10 C11 96.6(3) . . . . ?
C7 O1 C1 C2 -175.9(3) . . . . ?
C7 O1 C1 C6 3.8(4) . . . . ?
C8 O2 C2 C1 105.9(3) . . . . ?
C8 O2 C2 C3 -77.2(3) . . . . ?
C9 O3 C3 C2 173.8(3) . . . . ?
C9 O3 C3 C4 -5.1(4) . . . . ?
C10 C5 C6 C1 179.3(3) . . . . ?
C10 C11 C12 N1 179.7(3) . . . . ?
C10 C11 C14 N3 -177.7(3) . . . . ?
C10 C11 C14 N4 0.8(4) . . . . ?
C12 N1 C13 N2 -175.3(3) . . . . ?
C12 N1 C13 N3 3.2(4) . . . . ?
C12 C11 C14 N3 3.8(4) . . . . ?
C12 C11 C14 N4 -177.6(3) . . . . ?
C13 N1 C12 C11 -1.5(4) . . . . ?
C13 N3 C14 N4 179.1(3) . . . . ?
C13 N3 C14 C11 -2.3(4) . . . . ?
C14 N3 C13 N1 -1.3(4) . . . . ?
C14 N3 C13 N2 177.2(3) . . . . ?
C14 C11 C12 N1 -1.9(4) . . . . ?
O4 C15 C16 O5 0.5(4) . . . . ?
O4 C15 C16 C17 178.8(3) . . . . ?
O4 C15 C20 C19 -179.5(3) . . . . ?
O5 C16 C17 O6 -1.0(4) . . . . ?
O5 C16 C17 C18 179.1(3) . . . . ?
O6 C17 C18 C19 179.8(3) . . . . ?
C15 C16 C17 O6 -179.3(3) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C16 C15 C20 C19 -0.2(5) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C17 C18 C19 C24 179.0(3) . . . . ?
C18 C19 C20 C15 0.7(5) . . . . ?
C18 C19 C24 C25 83.2(4) . . . . ?
C19 C24 C25 C26 30.7(4) . . . . ?
C19 C24 C25 C28 -150.1(3) . . . . ?
C20 C15 C16 O5 -178.8(3) . . . . ?
C20 C15 C16 C17 -0.5(5) . . . . ?
C20 C19 C24 C25 -97.4(4) . . . . ?
C21 O4 C15 C16 176.7(3) . . . . ?
C21 O4 C15 C20 -4.0(4) . . . . ?
C22 O5 C16 C15 -104.1(3) . . . . ?
C22 O5 C16 C17 77.6(3) . . . . ?
C23 O6 C17 C16 -174.6(3) . . . . ?
C23 O6 C17 C18 5.3(5) . . . . ?
C24 C19 C20 C15 -178.7(3) . . . . ?
C24 C25 C26 N5 -179.2(3) . . . . ?
C24 C25 C28 N7 178.5(3) . . . . ?
C24 C25 C28 N8 -1.1(4) . . . . ?
C26 N5 C27 N6 177.0(3) . . . . ?
C26 N5 C27 N7 -2.7(4) . . . . ?
C26 C25 C28 N7 -2.2(4) . . . . ?
C26 C25 C28 N8 178.2(3) . . . . ?
C27 N5 C26 C25 0.8(5) . . . . ?
C27 N7 C28 N8 -179.9(3) . . . . ?
C27 N7 C28 C25 0.5(4) . . . . ?
C28 N7 C27 N5 2.0(4) . . . . ?
C28 N7 C27 N6 -177.7(3) . . . . ?
C28 C25 C26 N5 1.5(5) . . . . ?
O7 C29 C30 O9 3.1(4) . . . . ?
O7 C29 C30 C31 -121.2(3) . . . . ?
O8 C29 C30 O9 -177.4(3) . . . . ?
O8 C29 C30 C31 58.2(4) . . . . ?
O10A C32A C33A O12A 160.0(5) . . . . ?
O10A C32A C33A C34A 37.8(7) . . . . ?
O11A C32A C33A O12A -24.3(12) . . . . ?
O11A C32A C33A C34A -146.5(12) . . . . ?
O10B C32B C33B O12B 6.8(13) . . . . ?
O10B C32B C33B C34B -114.1(13) . . . . ?
O11B C32B C33B O12B -175.5(4) . . . . ?
O11B C32B C33B C34B 63.6(6) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.735
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.1(2)
2 -0.1(2)
####################################################################### 
# 
# 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_TMP_DLA_b
_database_code_depnum_ccdc_archive 'CCDC 2241035'
loop_
_audit_author_name
_audit_author_address
'Qixuan Zheng'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_TMP_DLA_b           
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.70 Note  
RESPONSE: This is due to the space group (P1) and number of disordered sites
within the structure.
;
_vrf_PLAT250_TMP_DLA_b           
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note  
RESPONSE: There is some slight disorder about the methoxy groups within
the structure that were not modeled as positionally disorsered.
;
_vrf_PLAT340_TMP_DLA_b           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00459 Ang.  
RESPONSE: This is due to a poor data to parameter ratio and weak
diffraction of high angle data.
;
_vrf_PLAT911_TMP_DLA_b           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
RESPONSE: These inconsistant reflections were omitted during the absorption
correction.
;
_vrf_PLAT915_TMP_DLA_b           
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         80 %     
RESPONSE: This is due to a poor data collection strategy, although the
data is still sufficient for our studies.
;
# end Validation Reply Form

_audit_creation_date             2022-10-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N4 O3, C3 H5 O3'
_chemical_formula_sum            'C17 H24 N4 O6'
_chemical_formula_weight         380.40
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36  H36  N8  O8  '
_chemical_oxdiff_usercomment     'TMP + DLA'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.06945(11)
_cell_length_b                   9.75039(14)
_cell_length_c                   19.4424(3)
_cell_angle_alpha                85.4911(12)
_cell_angle_beta                 88.8333(15)
_cell_angle_gamma                77.8317(15)
_cell_volume                     936.52(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21583
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7300
_cell_measurement_theta_min      2.2510
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             404
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -6 0 0.0285
-3 0 0 0.0686
0 6 0 0.0302
3 -3 0 0.0505
0 0 -13 0.0281
0 0 13 0.0169
1 1 12 0.0246
1 -3 10 0.0299
-1 3 11 0.0281
0 3 11 0.0209

_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.046
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.5079 -6.3002 -0.0238 0.8777 0.2601 0.4024
-3.2228 -0.0627 -0.0237 -0.4260 -0.1272 0.8957
0.4285 6.2897 0.0232 -0.8869 -0.2628 -0.3800
2.6377 -2.6242 0.0109 0.7505 0.2232 -0.6220
0.1205 -0.3210 -12.5979 0.2840 -0.9571 -0.0575
-0.2604 0.1939 12.5527 -0.2831 0.9537 0.1014
0.5737 0.9391 12.4589 -0.2805 0.9462 -0.1610
0.5742 -2.8873 10.2026 0.3334 0.9427 -0.0089
-0.5243 2.5080 11.4996 -0.6479 0.7580 0.0753
0.2596 3.1792 11.3685 -0.6404 0.7490 -0.1702

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37542
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.883
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -63.00   0.50    1.26    --  -47.76-140.00  73.00  114
  2  ω   -120.00 -70.00   0.50    1.26    --  -47.76-130.00-113.00  100
  3  ω    -90.00 -16.00   0.50    1.26    --  -47.76 130.00 -41.00  148
  4  ω     43.00 104.00   0.50    1.26    --   47.76-140.00  73.00  122
  5  ω     37.00  98.00   0.50    1.26    --   47.76-130.00-113.00  122
  6  ω   -163.00 -70.00   0.50    5.04    --  -91.75-130.00-113.00  186
  7  ω   -156.00 -63.00   0.50    5.04    --  -91.75-140.00  73.00  186
  8  ω     85.00 173.00   0.50    5.04    --  107.31 140.00 132.00  176
  9  ω     92.00 178.00   0.50    5.04    --  107.31 130.00 -41.00  172
 10  ω     37.00 116.00   0.50    5.04    --  107.31-130.00-113.00  158
 11  ω     43.00 123.00   0.50    5.04    --  107.31-140.00  73.00  160
 12  ω    -54.00 -27.00   0.50    1.26    --   10.00 153.00  40.83   54
 13  ω      4.00  34.00   0.50    1.26    --   34.00  93.00  53.43   60
 14  ω      2.00  29.00   0.50    1.26    --   34.00  96.00 104.74   54
 15  ω   -121.00 -34.00   0.50    1.26    --  -47.76 -38.00 120.00  174
 16  ω   -120.00 -25.00   0.50    1.26    --  -47.76 -77.00 -30.00  190
 17  ω    -97.00 -21.00   0.50    1.26    --  -47.76 140.00 132.00  152
 18  ω   -120.00 -73.00   0.50    1.26    --  -47.76-125.00-180.00   94
 19  ω     25.00 121.00   0.50    1.26    --   47.76  77.00 120.00  192
 20  ω     33.00 120.00   0.50    1.26    --   47.76  57.00 -60.00  174
 21  ω     25.00 121.00   0.50    1.26    --   47.76  77.00 -30.00  192
 22  ω     36.00 121.00   0.50    1.26    --   47.76  38.00-120.00  170
 23  ω     25.00 121.00   0.50    1.26    --   47.76  77.00 -60.00  192
 24  ω     36.00 121.00   0.50    1.26    --   47.76  38.00 -60.00  170
 25  ω     28.00 122.00   0.50    1.26    --   50.00  75.00  44.40  188
 26  ω     31.00 126.00   0.50    1.26    --   54.00  77.00-117.00  190
 27  ω     32.00 126.00   0.50    1.26    --   54.00  75.00  77.25  188
 28  ω     33.00 126.00   0.50    1.26    --   54.00  72.00  65.42  186
 29  ω     32.00 126.00   0.50    1.26    --   54.00  76.00-151.27  188
 30  ω   -131.00 -36.00   0.50    1.26    --  -58.00 -74.00-141.81  190
 31  ω     37.00 131.00   0.50    1.26    --   58.00  74.00-169.50  188
 32  ω   -135.00 -45.00   0.50    1.26    --  -62.00 -63.00 -45.81  180
 33  ω   -135.00 -44.00   0.50    1.26    --  -62.00 -65.00-177.54  182
 34  ω   -135.00 -43.00   0.50    1.26    --  -62.00 -67.00-149.23  184
 35  ω     39.00 135.00   0.50    1.26    --   62.00  77.00 154.31  192
 36  ω   -139.00 -49.00   0.50    1.26    --  -66.00 -62.00 -20.03  180
 37  ω     44.00 139.00   0.50    1.26    --   66.00  75.00 149.00  190
 38  ω     43.00 139.00   0.50    1.26    --   66.00  77.00 -66.62  192
 39  ω   -143.00 -52.00   0.50    5.04    --  -70.00 -65.00 134.70  182
 40  ω   -142.00 -54.00   0.50    5.04    --  -70.00 -60.00  44.91  176
 41  ω   -142.00 -55.00   0.50    5.04    --  -70.00 -57.00 -68.23  174
 42  ω     47.00  73.00   0.50    1.26    --   70.00  77.00 128.59   52
 43  ω    -85.00 -54.00   0.50    5.04    --  -70.00 -62.00  29.04   62
 44  ω    -81.00 -55.00   0.50    5.04    --  -70.00 -60.00 168.05   52
 45  ω    -80.00 -54.00   0.50    5.04    --  -70.00 -59.00 138.78   52
 46  ω    -83.00 -57.00   0.50    5.04    --  -74.00 -63.00  14.13   52
 47  ω    -81.00 -56.00   0.50    5.04    --  -74.00 -65.00 -43.64   50
 48  ω    -81.00 -55.00   0.50    5.04    --  -74.00 -67.00-109.23   52
 49  ω    -82.00 -57.00   0.50    5.04    --  -74.00 -62.00 -18.24   50
 50  ω    -83.00 -57.00   0.50    5.04    --  -74.00 -63.00-132.60   52
 51  ω    -89.00 -63.00   0.50    5.04    --  -78.00 -60.00  40.92   52
 52  ω    -94.00 -68.00   0.50    5.04    --  -78.00 -58.00-160.38   52
 53  ω    -88.00 -62.00   0.50    5.04    --  -78.00 -65.00 113.17   52
 54  ω    -89.00 -63.00   0.50    5.04    --  -78.00 -57.00 172.42   52
 55  ω    -83.00 -57.00   0.50    5.04    --  -78.00 -72.00 110.65   52
 56  ω    -87.00 -61.00   0.50    5.04    --  -78.00 -62.00 129.02   52
 57  ω    -92.00 -66.00   0.50    5.04    --  -82.00 -62.00  31.93   52
 58  ω    -92.00 -67.00   0.50    5.04    --  -82.00 -57.00 158.42   50
 59  ω    -92.00 -67.00   0.50    5.04    --  -82.00 -58.00-149.09   50
 60  ω    -91.00 -65.00   0.50    5.04    --  -82.00 -64.00 -17.40   52
 61  ω    -92.00 -66.00   0.50    5.04    --  -82.00 -62.00 123.86   52
 62  ω    -86.00 -61.00   0.50    5.04    --  -82.00 -72.00 -92.50   50
 63  ω   -155.00-124.00   0.50    5.04    --  -86.00 -76.00 105.45   62
 64  ω   -117.00 -63.00   0.50    5.04    --  -86.00 -76.00 105.45  108
 65  ω    -97.00 -71.00   0.50    5.04    --  -91.75 -73.00  10.23   52
 66  ω   -163.00-105.00   0.50    5.04    --  -91.75 -73.00  10.23  116
 67  ω   -106.00 -71.00   0.50    5.04    --  -91.75 -77.00 -30.00   70
 68  ω   -163.00 -69.00   0.50    5.04    --  -91.75 -77.00   0.00  188
 69  ω   -142.00-116.00   0.50    5.04    --  -91.75 -77.00 -66.97   52
 70  ω   -160.00-135.00   0.50    5.04    --  -91.75 -77.00 -30.00   50
 71  ω   -122.00 -69.00   0.50    5.04    --  -91.75 -77.00  60.00  106
 72  ω   -162.00-136.00   0.50    5.04    --  -91.75 -68.00 -90.17   52
 73  ω   -152.00-126.00   0.50    5.04    --  -91.75 -65.00 -28.98   52
 74  ω   -130.00 -80.00   0.50    5.04    --  -91.75 -57.00-150.00  100
 75  ω   -104.00 -73.00   0.50    5.04    --  -91.75 -66.00 118.34   62
 76  ω   -119.00 -73.00   0.50    5.04    --  -91.75 -68.00-169.54   92
 77  ω   -143.00-117.00   0.50    5.04    --  -91.75 -66.00 118.34   52
 78  ω   -113.00 -87.00   0.50    5.04    --  -91.75 -57.00 150.00   52
 79  ω   -163.00-129.00   0.50    5.04    --  -91.75 -68.00-169.54   68
 80  ω   -121.00 -69.00   0.50    5.04    --  -91.75 -77.00  90.00  104
 81  ω   -162.00-127.00   0.50    5.04    --  -91.75 -77.00  90.00   70
 82  ω    -99.00 -73.00   0.50    5.04    --  -91.75 -68.00 -90.17   52
 83  ω    -95.00 -69.00   0.50    5.04    --  -91.75 -76.00 123.07   52
 84  ω   -109.00 -74.00   0.50    5.04    --  -91.75 -63.00 -38.96   70
 85  ω   -163.00-113.00   0.50    5.04    --  -91.75 -63.00 -38.96  100
 86  ω   -154.00 -74.00   0.50    5.04    --  -91.75 -63.00-126.69  160
 87  ω   -163.00 -75.00   0.50    5.04    --  -91.75 -62.00  58.05  176
 88  ω   -104.00 -76.00   0.50    5.04    --  -91.75 -77.00-180.00   56
 89  ω   -161.00-109.00   0.50    5.04    --  -91.75 -77.00-180.00  104
 90  ω   -106.00 -69.00   0.50    5.04    --  -91.75 -77.00 -66.97   74
 91  ω   -112.00 -75.00   0.50    5.04    --  -91.75 -61.00-118.67   74
 92  ω   -106.00 -72.00   0.50    5.04    --  -91.75 -70.00 -97.26   68
 93  ω   -111.00 -73.00   0.50    5.04    --  -91.75 -71.00 -54.15   76
 94  ω   -154.00-119.00   0.50    5.04    --  -91.75 -70.00 -97.26   70
 95  ω    -99.00 -71.00   0.50    5.04    --  -91.75 -73.00 143.15   56
 96  ω   -162.00 -72.00   0.50    5.04    --  -91.75 -73.00  42.72  180
 97  ω   -163.00-107.00   0.50    5.04    --  -91.75 -73.00 143.15  112
 98  ω   -158.00-133.00   0.50    5.04    --  -91.75 -57.00 150.00   50
 99  ω   -162.00-121.00   0.50    5.04    --  -91.75 -71.00 -54.15   82
100  ω   -103.00 -77.00   0.50    5.04    --  -91.75 -65.00 -28.98   52
101  ω     35.00 103.00   0.50    5.04    --  107.31 -99.00-180.00  136
102  ω     35.00 107.00   0.50    5.04    --  107.31 -77.00  30.00  144
103  ω    144.00 177.00   0.50    5.04    --  107.31 125.00  90.00   66
104  ω     37.00  68.00   0.50    5.04    --  107.31 -57.00-150.00   62
105  ω     67.00 106.00   0.50    5.04    --  107.31 -99.00 -90.00   78
106  ω     38.00  64.00   0.50    5.04    --  107.31 -99.00 -90.00   52
107  ω     80.00 106.00   0.50    5.04    --  107.31 -99.00 -60.00   52
108  ω     35.00  71.00   0.50    5.04    --  107.31 -99.00 -60.00   72
109  ω     79.00 105.00   0.50    5.04    --  107.31 -99.00-120.00   52
110  ω     35.00  67.00   0.50    5.04    --  107.31 -57.00 -30.00   64
111  ω     79.00 104.00   0.50    5.04    --  107.31 -77.00  60.00   50
112  ω     73.00 101.00   0.50    5.04    --  107.31 -77.00  90.00   56
113  ω     36.00  68.00   0.50    5.04    --  107.31 -77.00  90.00   64
114  ω     46.00  75.00   0.50    5.04    --  107.31 -77.00  60.00   58
115  ω     36.00  68.00   0.50    5.04    --  107.31 -57.00 -90.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1352285000
_diffrn_orient_matrix_UB_12      -0.1501558000
_diffrn_orient_matrix_UB_13      -0.0174268000
_diffrn_orient_matrix_UB_21      0.0397556000
_diffrn_orient_matrix_UB_22      -0.0447778000
_diffrn_orient_matrix_UB_23      0.0774935000
_diffrn_orient_matrix_UB_31      -0.2771510000
_diffrn_orient_matrix_UB_32      -0.0415385000
_diffrn_orient_matrix_UB_33      0.0029714000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.796
_reflns_number_gt                6183
_reflns_number_total             6872
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2572 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         6872
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0733P)²+0.0824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1156
_refine_special_details          
'In the structure the pyruvic molecule (O10 < O12 and C32 < C34) was positionally disordered over two sites (A and B). The site occupancies for the A and B sites refined to 0.71 and 0.29, respectively. To help maintain reasonable ADP values, the rigid bond restraint RIGU was applied to the disordered sites.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 O10A, O11A, O12A, C32A, C33A, C34A, O10B, O11B, O12B, C32B, C33B, C34B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(O10B)=Sof(O11B)=Sof(O12B)=Sof(H12B)=Sof(C32B)=Sof(C33B)=Sof(H33B)=
 Sof(C34B)=Sof(H34D)=Sof(H34E)=Sof(H34F)=1-FVAR(1)
 Sof(O10A)=Sof(O11A)=Sof(O12A)=Sof(H12A)=Sof(C32A)=Sof(C33A)=Sof(H33A)=
 Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C30(H30), C33A(H33A), C33B(H33B)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 N5(H5), C4(H4), C6(H6), C14(H14), N1(H1), C18(H18), C20(H20), C28(H28)
4.d X=CH2 refined with riding coordinates:
 N8(H8A,H8B), N6(H6A,H6B), N4(H4A,H4B), N2(H2A,H2B)
4.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8C,H8D,H8E), C9(H9A,H9B,H9C), C21(H21A,H21B,H21C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C34A(H34A,H34B,
 H34C), C34B(H34D,H34E,H34F)
4.f Idealised tetrahedral OH refined as rotating group:
 O9(H9), O12A(H12A), O12B(H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.4011(5) 0.9264(2) 0.88648(12) 0.0344(5) Uani 1 1 d . . . . .
O2 O -0.0399(5) 0.7742(2) 0.97848(12) 0.0327(5) Uani 1 1 d . . . . .
O3 O 0.3767(5) 0.5815(2) 0.93731(11) 0.0309(5) Uani 1 1 d . . . . .
N7 N 0.4973(5) 0.6928(2) 0.55002(13) 0.0239(5) Uani 1 1 d . . . . .
N5 N 0.4431(5) 0.8834(2) 0.61968(14) 0.0242(5) Uani 1 1 d . . . . .
H5 H 0.476656 0.966101 0.626791 0.029 Uiso 1 1 calc R U . . .
N8 N 0.2378(6) 0.5286(2) 0.57022(14) 0.0256(6) Uani 1 1 d . . . . .
H8A H 0.307314 0.489946 0.532715 0.031 Uiso 1 1 calc R U . . .
H8B H 0.118257 0.492067 0.594772 0.031 Uiso 1 1 calc R U . . .
N6 N 0.7434(5) 0.8670(2) 0.52954(14) 0.0264(6) Uani 1 1 d . . . . .
H6A H 0.824417 0.823732 0.494398 0.032 Uiso 1 1 calc R U . . .
H6B H 0.783636 0.946045 0.540452 0.032 Uiso 1 1 calc R U . . .
C1 C -0.2074(7) 0.8216(3) 0.86154(17) 0.0272(7) Uani 1 1 d . . . . .
C2 C -0.0163(7) 0.7496(3) 0.90992(16) 0.0275(7) Uani 1 1 d . . . . .
C3 C 0.1957(6) 0.6447(3) 0.88746(16) 0.0259(7) Uani 1 1 d . . . . .
C4 C 0.2078(7) 0.6094(3) 0.81950(17) 0.0249(6) Uani 1 1 d . . . . .
H4 H 0.350888 0.537881 0.804892 0.030 Uiso 1 1 calc R U . . .
C5 C 0.0096(6) 0.6789(3) 0.77252(16) 0.0237(6) Uani 1 1 d . . . . .
C6 C -0.1953(7) 0.7862(3) 0.79340(17) 0.0263(7) Uani 1 1 d . . . . .
H6 H -0.326959 0.835467 0.761200 0.032 Uiso 1 1 calc R U . . .
C7 C -0.6101(7) 0.9953(3) 0.84027(18) 0.0336(7) Uani 1 1 d . . . . .
H7A H -0.530612 1.035822 0.799196 0.050 Uiso 1 1 calc R U . . .
H7B H -0.730931 1.070407 0.863147 0.050 Uiso 1 1 calc R U . . .
H7C H -0.712562 0.927168 0.826650 0.050 Uiso 1 1 calc R U . . .
C8 C 0.0675(10) 0.8902(4) 0.9970(2) 0.0482(9) Uani 1 1 d . . . . .
H8C H -0.032224 0.977217 0.972929 0.072 Uiso 1 1 calc R U . . .
H8D H 0.258423 0.875671 0.983850 0.072 Uiso 1 1 calc R U . . .
H8E H 0.049892 0.897452 1.046946 0.072 Uiso 1 1 calc R U . . .
C9 C 0.6007(7) 0.4770(3) 0.91682(18) 0.0324(7) Uani 1 1 d . . . . .
H9A H 0.706071 0.519214 0.881479 0.049 Uiso 1 1 calc R U . . .
H9B H 0.534453 0.400254 0.898016 0.049 Uiso 1 1 calc R U . . .
H9C H 0.714982 0.439947 0.956930 0.049 Uiso 1 1 calc R U . . .
C10 C 0.0226(7) 0.6349(3) 0.69935(16) 0.0244(6) Uani 1 1 d . . . . .
H10A H 0.087311 0.531590 0.700523 0.029 Uiso 1 1 calc R U . . .
H10B H -0.162019 0.657515 0.680047 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2035(6) 0.7040(3) 0.65179(15) 0.0211(6) Uani 1 1 d . . . . .
C12 C 0.3136(6) 0.6420(3) 0.58981(15) 0.0216(6) Uani 1 1 d . . . . .
C13 C 0.5610(6) 0.8132(3) 0.56598(16) 0.0217(6) Uani 1 1 d . . . . .
C14 C 0.2731(6) 0.8268(3) 0.66265(16) 0.0226(6) Uani 1 1 d . . . . .
H14 H 0.200822 0.875079 0.701623 0.027 Uiso 1 1 calc R U . . .
O4 O 0.6240(5) 0.4381(2) 1.08505(11) 0.0348(6) Uani 1 1 d . . . . .
O5 O 0.9959(5) 0.2231(2) 1.04553(12) 0.0361(5) Uani 1 1 d . . . . .
O6 O 1.3768(5) 0.0770(3) 1.13254(14) 0.0424(6) Uani 1 1 d . . . . .
N3 N 0.5331(5) 0.3357(2) 1.47146(13) 0.0251(6) Uani 1 1 d . . . . .
N1 N 0.5704(6) 0.1447(3) 1.40229(14) 0.0315(6) Uani 1 1 d . . . . .
H1 H 0.528124 0.064009 1.395088 0.038 Uiso 1 1 calc R U . . .
N4 N 0.7913(6) 0.4994(3) 1.44751(15) 0.0299(6) Uani 1 1 d . . . . .
H4A H 0.723937 0.540088 1.484684 0.036 Uiso 1 1 calc R U . . .
H4B H 0.909564 0.534708 1.421849 0.036 Uiso 1 1 calc R U . . .
N2 N 0.2792(6) 0.1658(3) 1.49490(14) 0.0282(6) Uani 1 1 d . . . . .
H2A H 0.202995 0.210695 1.530116 0.034 Uiso 1 1 calc R U . . .
H2B H 0.233962 0.087396 1.484915 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8070(7) 0.3721(3) 1.13372(17) 0.0318(7) Uani 1 1 d . . . . .
C16 C 1.0049(7) 0.2607(3) 1.11159(17) 0.0301(7) Uani 1 1 d . . . . .
C17 C 1.1993(7) 0.1872(3) 1.15841(18) 0.0330(7) Uani 1 1 d . . . . .
C18 C 1.2022(7) 0.2261(4) 1.22574(18) 0.0374(8) Uani 1 1 d . . . . .
H18 H 1.336851 0.176435 1.257048 0.045 Uiso 1 1 calc R U . . .
C19 C 1.0085(7) 0.3373(4) 1.24695(17) 0.0367(8) Uani 1 1 d . . . . .
C20 C 0.8087(7) 0.4101(4) 1.20113(18) 0.0347(8) Uani 1 1 d . . . . .
H20 H 0.674302 0.485475 1.216065 0.042 Uiso 1 1 calc R U . . .
C21 C 0.4179(8) 0.5516(4) 1.10585(19) 0.0422(9) Uani 1 1 d . . . . .
H21A H 0.295452 0.587584 1.067142 0.063 Uiso 1 1 calc R U . . .
H21B H 0.500717 0.627053 1.119987 0.063 Uiso 1 1 calc R U . . .
H21C H 0.316189 0.517825 1.144673 0.063 Uiso 1 1 calc R U . . .
C22 C 1.2105(8) 0.2554(4) 1.00251(17) 0.0426(8) Uani 1 1 d . . . . .
H22A H 1.180312 0.236257 0.954888 0.064 Uiso 1 1 calc R U . . .
H22B H 1.382584 0.197024 1.018955 0.064 Uiso 1 1 calc R U . . .
H22C H 1.215593 0.354964 1.004236 0.064 Uiso 1 1 calc R U . . .
C23 C 1.6026(9) 0.0099(4) 1.1751(2) 0.0477(10) Uani 1 1 d . . . . .
H23A H 1.716572 -0.065357 1.150816 0.072 Uiso 1 1 calc R U . . .
H23B H 1.537244 -0.030020 1.218377 0.072 Uiso 1 1 calc R U . . .
H23C H 1.708044 0.079345 1.185209 0.072 Uiso 1 1 calc R U . . .
C24 C 1.0042(8) 0.3839(4) 1.31968(18) 0.0381(8) Uani 1 1 d . . . . .
H24A H 1.189976 0.359024 1.338282 0.046 Uiso 1 1 calc R U . . .
H24B H 0.945219 0.487628 1.317830 0.046 Uiso 1 1 calc R U . . .
C25 C 0.8199(7) 0.3187(4) 1.36860(17) 0.0319(7) Uani 1 1 d . . . . .
C26 C 0.7147(7) 0.3847(3) 1.43014(16) 0.0283(7) Uani 1 1 d . . . . .
C27 C 0.4623(6) 0.2165(3) 1.45686(15) 0.0256(7) Uani 1 1 d . . . . .
C28 C 0.7436(7) 0.1978(4) 1.35889(17) 0.0342(8) Uani 1 1 d . . . . .
H28 H 0.813360 0.147673 1.320258 0.041 Uiso 1 1 calc R U . . .
O7 O -0.4959(5) 1.1272(2) 0.66102(13) 0.0301(5) Uani 1 1 d . . . . .
O8 O -0.1116(5) 1.0915(2) 0.60048(12) 0.0305(5) Uani 1 1 d . . . . .
O9 O 0.0358(5) 1.3180(2) 0.64274(13) 0.0333(5) Uani 1 1 d . . . . .
H9 H 0.167634 1.255251 0.656857 0.050 Uiso 1 1 calc R U . . .
C29 C -0.2728(7) 1.1575(3) 0.64081(17) 0.0251(6) Uani 1 1 d . . . . .
C30 C -0.2052(6) 1.2866(3) 0.67111(17) 0.0278(7) Uani 1 1 d . . . . .
H30 H -0.354773 1.368797 0.658262 0.033 Uiso 1 1 calc R U . . .
C31 C -0.1948(9) 1.2674(4) 0.7492(2) 0.0435(9) Uani 1 1 d . . . . .
H31A H -0.056143 1.184320 0.763490 0.065 Uiso 1 1 calc R U . . .
H31B H -0.370725 1.254682 0.767218 0.065 Uiso 1 1 calc R U . . .
H31C H -0.150937 1.350826 0.767348 0.065 Uiso 1 1 calc R U . . .
O10A O 0.134(2) 0.9329(11) 0.4301(6) 0.0281(14) Uani 0.709(5) 1 d . . P A 1
O11A O 0.4761(7) 0.9195(4) 0.35550(19) 0.0284(8) Uani 0.709(5) 1 d . . P A 1
O12A O -0.0572(7) 0.7294(3) 0.3699(2) 0.0312(9) Uani 0.709(5) 1 d . . P A 1
H12A H -0.208551 0.784854 0.368462 0.047 Uiso 0.709(5) 1 calc R U P A 1
C32A C 0.2559(9) 0.8886(4) 0.3780(2) 0.0226(9) Uani 0.709(5) 1 d . . P A 1
C33A C 0.1349(9) 0.7938(4) 0.3324(2) 0.0266(9) Uani 0.709(5) 1 d . . P A 1
H33A H 0.037928 0.855417 0.293308 0.032 Uiso 0.709(5) 1 calc R U P A 1
C34A C 0.3433(10) 0.6799(5) 0.3018(3) 0.0343(11) Uani 0.709(5) 1 d . . P A 1
H34A H 0.435744 0.614878 0.338976 0.051 Uiso 0.709(5) 1 calc R U P A 1
H34B H 0.475235 0.722753 0.275121 0.051 Uiso 0.709(5) 1 calc R U P A 1
H34C H 0.254055 0.628228 0.271444 0.051 Uiso 0.709(5) 1 calc R U P A 1
O10B O 0.199(6) 0.938(3) 0.4250(16) 0.033(4) Uani 0.291(5) 1 d . . P A 2
O11B O 0.0019(15) 0.7568(7) 0.4139(4) 0.0237(17) Uani 0.291(5) 1 d . . P A 2
O12B O 0.5697(18) 0.8626(10) 0.3291(5) 0.031(2) Uani 0.291(5) 1 d . . P A 2
H12B H 0.695720 0.829460 0.356973 0.047 Uiso 0.291(5) 1 calc R U P A 2
C32B C 0.180(2) 0.8291(9) 0.3978(5) 0.0184(17) Uani 0.291(5) 1 d . . P A 2
C33B C 0.362(2) 0.7830(9) 0.3386(5) 0.0232(18) Uani 0.291(5) 1 d . . P A 2
H33B H 0.449804 0.681549 0.348432 0.028 Uiso 0.291(5) 1 calc R U P A 2
C34B C 0.208(2) 0.7988(11) 0.2703(6) 0.028(2) Uani 0.291(5) 1 d . . P A 2
H34D H 0.063598 0.745788 0.275151 0.041 Uiso 0.291(5) 1 calc R U P A 2
H34E H 0.332197 0.762326 0.233564 0.041 Uiso 0.291(5) 1 calc R U P A 2
H34F H 0.129370 0.898474 0.258548 0.041 Uiso 0.291(5) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.370(4) . ?
O1 C7 1.423(4) . ?
O2 C2 1.371(4) . ?
O2 C8 1.427(4) . ?
O3 C3 1.365(4) . ?
O3 C9 1.430(4) . ?
N7 C12 1.347(4) . ?
N7 C13 1.342(4) . ?
N5 H5 0.8800 . ?
N5 C13 1.353(4) . ?
N5 C14 1.358(4) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C12 1.330(4) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C13 1.323(4) . ?
C1 C2 1.401(5) . ?
C1 C6 1.392(4) . ?
C2 C3 1.407(4) . ?
C3 C4 1.388(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(4) . ?
C5 C6 1.390(4) . ?
C5 C10 1.514(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.509(4) . ?
C11 C12 1.440(4) . ?
C11 C14 1.350(4) . ?
C14 H14 0.9500 . ?
O4 C15 1.363(4) . ?
O4 C21 1.430(4) . ?
O5 C16 1.368(4) . ?
O5 C22 1.431(4) . ?
O6 C17 1.370(4) . ?
O6 C23 1.435(5) . ?
N3 C26 1.347(4) . ?
N3 C27 1.339(4) . ?
N1 H1 0.8800 . ?
N1 C27 1.359(4) . ?
N1 C28 1.358(5) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C26 1.328(4) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C27 1.327(4) . ?
C15 C16 1.403(5) . ?
C15 C20 1.391(5) . ?
C16 C17 1.397(5) . ?
C17 C18 1.392(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(5) . ?
C19 C20 1.399(5) . ?
C19 C24 1.518(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.517(5) . ?
C25 C26 1.443(5) . ?
C25 C28 1.343(5) . ?
C28 H28 0.9500 . ?
O7 C29 1.275(4) . ?
O8 C29 1.236(4) . ?
O9 H9 0.8400 . ?
O9 C30 1.412(4) . ?
C29 C30 1.534(4) . ?
C30 H30 1.0000 . ?
C30 C31 1.515(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O10A C32A 1.235(10) . ?
O11A C32A 1.276(6) . ?
O12A H12A 0.8400 . ?
O12A C33A 1.425(5) . ?
C32A C33A 1.552(6) . ?
C33A H33A 1.0000 . ?
C33A C34A 1.512(6) . ?
C34A H34A 0.9800 . ?
C34A H34B 0.9800 . ?
C34A H34C 0.9800 . ?
O10B C32B 1.25(2) . ?
O11B C32B 1.278(14) . ?
O12B H12B 0.8400 . ?
O12B C33B 1.434(12) . ?
C32B C33B 1.499(14) . ?
C33B H33B 1.0000 . ?
C33B C34B 1.536(14) . ?
C34B H34D 0.9800 . ?
C34B H34E 0.9800 . ?
C34B H34F 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 C7 117.0(3) . . ?
C2 O2 C8 114.9(3) . . ?
C3 O3 C9 117.3(2) . . ?
C13 N7 C12 117.9(3) . . ?
C13 N5 H5 119.9 . . ?
C13 N5 C14 120.2(2) . . ?
C14 N5 H5 119.9 . . ?
H8A N8 H8B 120.0 . . ?
C12 N8 H8A 120.0 . . ?
C12 N8 H8B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C13 N6 H6A 120.0 . . ?
C13 N6 H6B 120.0 . . ?
O1 C1 C2 115.3(3) . . ?
O1 C1 C6 123.9(3) . . ?
C6 C1 C2 120.9(3) . . ?
O2 C2 C1 121.5(3) . . ?
O2 C2 C3 119.9(3) . . ?
C1 C2 C3 118.5(3) . . ?
O3 C3 C2 115.0(3) . . ?
O3 C3 C4 124.5(3) . . ?
C4 C3 C2 120.5(3) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C10 119.0(3) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 C10 121.1(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8C 109.5 . . ?
O2 C8 H8D 109.5 . . ?
O2 C8 H8E 109.5 . . ?
H8C C8 H8D 109.5 . . ?
H8C C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 108.7 . . ?
C5 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C5 114.4(2) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C12 C11 C10 121.3(2) . . ?
C14 C11 C10 123.9(3) . . ?
C14 C11 C12 114.8(3) . . ?
N7 C12 C11 122.8(2) . . ?
N8 C12 N7 117.1(3) . . ?
N8 C12 C11 120.1(3) . . ?
N7 C13 N5 121.5(3) . . ?
N6 C13 N7 120.7(3) . . ?
N6 C13 N5 117.7(2) . . ?
N5 C14 H14 118.9 . . ?
C11 C14 N5 122.1(3) . . ?
C11 C14 H14 118.9 . . ?
C15 O4 C21 117.2(3) . . ?
C16 O5 C22 113.7(3) . . ?
C17 O6 C23 117.0(3) . . ?
C27 N3 C26 118.3(3) . . ?
C27 N1 H1 120.1 . . ?
C28 N1 H1 120.1 . . ?
C28 N1 C27 119.9(3) . . ?
H4A N4 H4B 120.0 . . ?
C26 N4 H4A 120.0 . . ?
C26 N4 H4B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C27 N2 H2A 120.0 . . ?
C27 N2 H2B 120.0 . . ?
O4 C15 C16 115.6(3) . . ?
O4 C15 C20 124.2(3) . . ?
C20 C15 C16 120.2(3) . . ?
O5 C16 C15 119.2(3) . . ?
O5 C16 C17 121.6(3) . . ?
C17 C16 C15 119.2(3) . . ?
O6 C17 C16 114.7(3) . . ?
O6 C17 C18 124.7(3) . . ?
C18 C17 C16 120.6(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 C24 121.8(3) . . ?
C20 C19 C24 118.0(3) . . ?
C15 C20 C19 119.9(3) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 108.8 . . ?
C19 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C19 113.7(3) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C26 C25 C24 121.0(3) . . ?
C28 C25 C24 123.8(3) . . ?
C28 C25 C26 115.2(3) . . ?
N3 C26 C25 122.3(3) . . ?
N4 C26 N3 117.2(3) . . ?
N4 C26 C25 120.5(3) . . ?
N3 C27 N1 121.6(3) . . ?
N2 C27 N3 120.6(3) . . ?
N2 C27 N1 117.7(3) . . ?
N1 C28 H28 118.8 . . ?
C25 C28 N1 122.4(3) . . ?
C25 C28 H28 118.8 . . ?
C30 O9 H9 109.5 . . ?
O7 C29 C30 115.3(3) . . ?
O8 C29 O7 125.5(3) . . ?
O8 C29 C30 119.2(3) . . ?
O9 C30 C29 111.6(3) . . ?
O9 C30 H30 107.5 . . ?
O9 C30 C31 111.8(3) . . ?
C29 C30 H30 107.5 . . ?
C31 C30 C29 110.9(2) . . ?
C31 C30 H30 107.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33A O12A H12A 109.5 . . ?
O10A C32A O11A 125.1(6) . . ?
O10A C32A C33A 119.9(5) . . ?
O11A C32A C33A 114.9(4) . . ?
O12A C33A C32A 111.2(4) . . ?
O12A C33A H33A 107.6 . . ?
O12A C33A C34A 108.5(3) . . ?
C32A C33A H33A 107.6 . . ?
C34A C33A C32A 114.0(4) . . ?
C34A C33A H33A 107.6 . . ?
C33A C34A H34A 109.5 . . ?
C33A C34A H34B 109.5 . . ?
C33A C34A H34C 109.5 . . ?
H34A C34A H34B 109.5 . . ?
H34A C34A H34C 109.5 . . ?
H34B C34A H34C 109.5 . . ?
C33B O12B H12B 109.5 . . ?
O10B C32B O11B 124.4(13) . . ?
O10B C32B C33B 119.1(13) . . ?
O11B C32B C33B 116.3(8) . . ?
O12B C33B C32B 111.7(9) . . ?
O12B C33B H33B 108.5 . . ?
O12B C33B C34B 107.5(8) . . ?
C32B C33B H33B 108.5 . . ?
C32B C33B C34B 112.2(8) . . ?
C34B C33B H33B 108.5 . . ?
C33B C34B H34D 109.5 . . ?
C33B C34B H34E 109.5 . . ?
C33B C34B H34F 109.5 . . ?
H34D C34B H34E 109.5 . . ?
H34D C34B H34F 109.5 . . ?
H34E C34B H34F 109.5 . . ?

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
N5 H5 O7 0.88 1.79 2.648(3) 165.9 1_655 yes
N5 H5 O8 0.88 2.65 3.336(3) 135.1 1_655 yes
N8 H8A N3 0.88 2.12 2.954(4) 158.2 1_554 yes
N8 H8B O9 0.88 1.99 2.761(3) 145.6 1_545 yes
N6 H6A O10A 0.88 2.36 2.873(9) 117.4 1_655 yes
N6 H6A O10B 0.88 2.69 3.20(2) 117.9 1_655 yes
N6 H6A O11B 0.88 1.88 2.755(8) 171.9 1_655 yes
N6 H6B O8 0.88 2.06 2.903(3) 159.2 1_655 yes
N1 H1 O10A 0.88 2.64 3.341(8) 137.1 1_546 yes
N1 H1 O11A 0.88 1.73 2.579(4) 162.3 1_546 yes
N1 H1 O10B 0.88 2.31 3.036(19) 139.8 1_546 yes
N1 H1 O12B 0.88 2.40 3.196(11) 150.6 1_546 yes
N4 H4A N7 0.88 2.16 3.006(4) 160.9 1_556 yes
N4 H4B O12A 0.88 2.12 2.835(4) 138.5 1_656 yes
N4 H4B O11B 0.88 2.30 2.950(7) 130.4 1_656 yes
N2 H2A O8 0.88 2.49 2.978(4) 115.5 1_546 yes
N2 H2A O9 0.88 2.55 3.427(4) 171.8 1_546 yes
N2 H2B O10A 0.88 2.07 2.914(8) 161.7 1_546 yes
N2 H2B O10B 0.88 1.97 2.80(2) 155.3 1_546 yes
O9 H9 O7 0.84 1.89 2.701(3) 162.2 1_655 yes
O12A H12A O11A 0.84 1.85 2.685(5) 172.5 1_455 yes
O12B H12B O11B 0.84 1.90 2.741(10) 175.1 1_655 yes

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 6.0(4) . . . . ?
O1 C1 C2 C3 -177.3(3) . . . . ?
O1 C1 C6 C5 179.6(3) . . . . ?
O2 C2 C3 O3 -4.6(4) . . . . ?
O2 C2 C3 C4 173.9(3) . . . . ?
O3 C3 C4 C5 178.9(3) . . . . ?
C1 C2 C3 O3 178.6(3) . . . . ?
C1 C2 C3 C4 -2.8(4) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 1.9(4) . . . . ?
C3 C4 C5 C10 -178.0(3) . . . . ?
C4 C5 C6 C1 -1.9(4) . . . . ?
C4 C5 C10 C11 -84.9(3) . . . . ?
C5 C10 C11 C12 158.1(3) . . . . ?
C5 C10 C11 C14 -22.6(4) . . . . ?
C6 C1 C2 O2 -173.8(3) . . . . ?
C6 C1 C2 C3 2.8(5) . . . . ?
C6 C5 C10 C11 95.2(3) . . . . ?
C7 O1 C1 C2 -175.6(3) . . . . ?
C7 O1 C1 C6 4.3(5) . . . . ?
C8 O2 C2 C1 -84.9(4) . . . . ?
C8 O2 C2 C3 98.5(4) . . . . ?
C9 O3 C3 C2 -178.2(3) . . . . ?
C9 O3 C3 C4 3.3(4) . . . . ?
C10 C5 C6 C1 178.0(3) . . . . ?
C10 C11 C12 N7 -172.9(3) . . . . ?
C10 C11 C12 N8 6.0(4) . . . . ?
C10 C11 C14 N5 178.0(3) . . . . ?
C12 N7 C13 N5 -0.9(4) . . . . ?
C12 N7 C13 N6 178.8(3) . . . . ?
C12 C11 C14 N5 -2.7(4) . . . . ?
C13 N7 C12 N8 175.1(3) . . . . ?
C13 N7 C12 C11 -6.0(4) . . . . ?
C13 N5 C14 C11 -3.7(4) . . . . ?
C14 N5 C13 N7 5.7(4) . . . . ?
C14 N5 C13 N6 -174.0(3) . . . . ?
C14 C11 C12 N7 7.7(4) . . . . ?
C14 C11 C12 N8 -173.4(3) . . . . ?
O4 C15 C16 O5 -2.4(5) . . . . ?
O4 C15 C16 C17 -179.7(3) . . . . ?
O4 C15 C20 C19 -178.8(3) . . . . ?
O5 C16 C17 O6 0.3(5) . . . . ?
O5 C16 C17 C18 -179.0(3) . . . . ?
O6 C17 C18 C19 -178.3(3) . . . . ?
C15 C16 C17 O6 177.6(3) . . . . ?
C15 C16 C17 C18 -1.8(5) . . . . ?
C16 C15 C20 C19 0.1(6) . . . . ?
C16 C17 C18 C19 1.0(5) . . . . ?
C17 C18 C19 C20 0.4(6) . . . . ?
C17 C18 C19 C24 -179.7(4) . . . . ?
C18 C19 C20 C15 -1.0(6) . . . . ?
C18 C19 C24 C25 -94.5(4) . . . . ?
C19 C24 C25 C26 -157.5(3) . . . . ?
C19 C24 C25 C28 22.8(5) . . . . ?
C20 C15 C16 O5 178.5(3) . . . . ?
C20 C15 C16 C17 1.2(5) . . . . ?
C20 C19 C24 C25 85.4(4) . . . . ?
C21 O4 C15 C16 179.5(3) . . . . ?
C21 O4 C15 C20 -1.5(5) . . . . ?
C22 O5 C16 C15 110.7(3) . . . . ?
C22 O5 C16 C17 -72.0(4) . . . . ?
C23 O6 C17 C16 171.7(3) . . . . ?
C23 O6 C17 C18 -9.0(5) . . . . ?
C24 C19 C20 C15 179.1(3) . . . . ?
C24 C25 C26 N3 174.3(3) . . . . ?
C24 C25 C26 N4 -4.4(5) . . . . ?
C24 C25 C28 N1 -177.5(3) . . . . ?
C26 N3 C27 N1 0.5(4) . . . . ?
C26 N3 C27 N2 -178.2(3) . . . . ?
C26 C25 C28 N1 2.7(5) . . . . ?
C27 N3 C26 N4 -176.9(3) . . . . ?
C27 N3 C26 C25 4.3(4) . . . . ?
C27 N1 C28 C25 1.7(5) . . . . ?
C28 N1 C27 N3 -3.6(4) . . . . ?
C28 N1 C27 N2 175.2(3) . . . . ?
C28 C25 C26 N3 -5.9(4) . . . . ?
C28 C25 C26 N4 175.3(3) . . . . ?
O7 C29 C30 O9 -176.2(3) . . . . ?
O7 C29 C30 C31 58.5(4) . . . . ?
O8 C29 C30 O9 4.5(4) . . . . ?
O8 C29 C30 C31 -120.7(3) . . . . ?
O10A C32A C33A O12A -20.9(9) . . . . ?
O10A C32A C33A C34A -144.0(9) . . . . ?
O11A C32A C33A O12A 162.1(3) . . . . ?
O11A C32A C33A C34A 39.0(5) . . . . ?
O10B C32B C33B O12B 10(2) . . . . ?
O10B C32B C33B C34B -111(2) . . . . ?
O11B C32B C33B O12B -174.5(7) . . . . ?
O11B C32B C33B C34B 64.8(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   2790
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.594
_oxdiff_exptl_absorpt_empirical_full_min 0.486
####################################################################### 
# 
# 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_TMP_LLA_a
_database_code_depnum_ccdc_archive 'CCDC 2241036'
loop_
_audit_author_name
_audit_author_address
'Qixuan Zheng'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_TMP_LLA_a           
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       7.02 Note  
RESPONSE: Due to the number of disordered sites in this structure.
;
_vrf_PLAT250_TMP_LLA_a           
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note  
RESPONSE: Due to slight disorder about pyruvic molecules.
;
# end Validation Reply Form

_audit_creation_date             2022-01-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C14 H19 N4 O3), 4(C3 H5 O3)'
_chemical_formula_sum            'C68 H96 N16 O24'
_chemical_formula_weight         1521.60
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C90  H90  N9  O15  '
_chemical_oxdiff_usercomment     'TMP + LLA'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.07320(10)
_cell_length_b                   36.4013(3)
_cell_length_c                   10.05470(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.3650(10)
_cell_angle_gamma                90
_cell_volume                     1848.68(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    26744
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.8600
_cell_measurement_theta_min      2.4040
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -2 0.0402
2 1 2 0.0431
0 1 2 0.0402
-2 -1 -1 0.0455
0 23 -2 0.0075
0 -23 2 0.0187
3 -3 -3 0.0654
0 -20 -3 0.0268
1 16 4 0.0317
-1 21 2 0.0318
1 -21 1 0.0302

_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.026
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0006 -1.0083 -1.9987 0.2707 -0.0283 -0.1496
1.9997 1.0036 1.9982 -0.0316 -0.0178 0.7084
0.0006 1.0083 1.9987 -0.2707 0.0283 0.1496
-1.9994 -0.9991 -0.9989 -0.1036 0.0109 -0.6354
0.1635 22.8739 -1.6245 0.2330 0.9724 0.0090
-0.1635 -22.8739 1.6245 -0.2330 -0.9724 -0.0090
3.0085 -3.2742 -3.0430 0.7724 -0.1857 0.6074
-0.3144 -19.7413 -3.4574 0.4358 -0.8008 -0.4108
1.3400 16.2034 3.6735 -0.3414 0.6265 0.7006
-1.1486 20.5737 2.4630 -0.4764 0.8766 -0.0678
1.2749 -21.0064 1.3489 -0.0243 -0.9248 0.3797

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            46670
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.044
_diffrn_reflns_theta_min         2.428
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -74.00   0.50    2.29    --  -47.76-124.00-129.00   92
  2  ω   -120.00 -57.00   0.50    2.29    --  -47.76-148.00  66.00  126
  3  ω    -85.00 -12.00   0.50    2.29    --  -47.76 124.00 -50.00  146
  4  ω   -102.00 -25.00   0.50    2.29    --  -47.76 148.00 114.00  154
  5  ω     34.00  95.00   0.50    2.29    --   47.76-124.00-129.00  122
  6  ω     47.00 109.00   0.50    2.29    --   47.76-148.00  66.00  124
  7  ω   -102.00 -25.00   0.50    9.18    --  -91.75 148.00 114.00  154
  8  ω   -163.00 -74.00   0.50    9.18    --  -91.75-124.00-129.00  178
  9  ω    -85.00 -19.00   0.50    9.18    --  -91.75 124.00 -50.00  132
 10  ω     35.00 110.00   0.50    9.18    --  107.31-124.00-129.00  150
 11  ω     79.00 167.00   0.50    9.18    --  107.31 148.00 114.00  176
 12  ω     96.00 178.00   0.50    9.18    --  107.31 124.00 -50.00  164
 13  ω     47.00 128.00   0.50    9.18    --  107.31-148.00  66.00  162
 14  ω    -25.00  28.00   0.50    2.29    --  -47.76  19.00 -30.00  106
 15  ω    -25.00  28.00   0.50    2.29    --  -47.76  19.00  60.00  106
 16  ω   -120.00 -73.00   0.50    2.29    --  -47.76-125.00  60.00   94
 17  ω   -120.00 -33.00   0.50    2.29    --  -47.76 -57.00-180.00  174
 18  ω    -25.00  28.00   0.50    2.29    --  -47.76  19.00 150.00  106
 19  ω    -64.00 -19.00   0.50    9.18    --  -91.75  57.00-180.00   90
 20  ω   -165.00 -78.00   0.50    9.18    --  -91.75 -38.00 120.00  174
 21  ω    -64.00 -19.00   0.50    9.18    --  -91.75  57.00 120.00   90
 22  ω   -165.00 -78.00   0.50    9.18    --  -91.75 -38.00  30.00  174
 23  ω    -64.00 -19.00   0.50    9.18    --  -91.75  57.00 150.00   90
 24  ω   -165.00 -78.00   0.50    9.18    --  -91.75 -38.00 -60.00  174
 25  ω    -64.00 -19.00   0.50    9.18    --  -91.75  57.00 -90.00   90
 26  ω   -150.00 -57.00   0.50    9.18    --  -91.75-148.00  66.00  186
 27  ω    -64.00 -19.00   0.50    9.18    --  -91.75  57.00 -60.00   90
 28  ω    -64.00 -19.00   0.50    9.18    --  -91.75  57.00 -30.00   90
 29  ω     35.00 106.00   0.50    9.18    --  107.31 -99.00-120.00  142
 30  ω     35.00  68.00   0.50    9.18    --  107.31 -57.00  30.00   66
 31  ω     35.00 106.00   0.50    9.18    --  107.31 -99.00 150.00  142
 32  ω     94.00 178.00   0.50    9.18    --  107.31  38.00 -60.00  168
 33  ω     35.00 106.00   0.50    9.18    --  107.31 -99.00 -60.00  142
 34  ω     35.00 111.00   0.50    9.18    --  107.31-125.00 -90.00  152
 35  ω     95.00 178.00   0.50    9.18    --  107.31  19.00 -90.00  166
 36  ω     35.00  68.00   0.50    9.18    --  107.31 -57.00   0.00   66
 37  ω     94.00 178.00   0.50    9.18    --  107.31  38.00  30.00  168
 38  ω     35.00 106.00   0.50    9.18    --  107.31 -99.00  90.00  142
 39  ω   -120.00 -33.00   0.50    2.29    --  -47.76 -57.00  60.00  174
 40  ω   -120.00 -33.00   0.50    2.29    --  -47.76 -57.00  90.00  174
 41  ω   -120.00 -33.00   0.50    2.29    --  -47.76 -57.00 -60.00  174
 42  ω   -120.00 -25.00   0.50    2.29    --  -47.76 -77.00 -90.00  190
 43  ω   -120.00 -25.00   0.50    2.29    --  -47.76 -77.00  30.00  190
 44  ω   -121.00 -34.00   0.50    2.29    --  -47.76 -38.00 -60.00  174
 45  ω   -120.00 -25.00   0.50    2.29    --  -47.76 -77.00-120.00  190
 46  ω   -121.00 -34.00   0.50    2.29    --  -47.76 -38.00  90.00  174
 47  ω   -120.00 -25.00   0.50    2.29    --  -47.76 -77.00-180.00  190
 48  ω   -121.00 -34.00   0.50    2.29    --  -47.76 -38.00-180.00  174
 49  ω     25.00 121.00   0.50    2.29    --   47.76  77.00 -30.00  192
 50  ω   -163.00-134.00   0.50    9.18    --  -91.75 -77.00 -90.00   58
 51  ω   -163.00 -77.00   0.50    9.18    --  -91.75 -57.00  90.00  172
 52  ω   -165.00 -78.00   0.50    9.18    --  -91.75 -38.00-180.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1195583000
_diffrn_orient_matrix_UB_12      -0.0002791000
_diffrn_orient_matrix_UB_13      -0.1353293000
_diffrn_orient_matrix_UB_21      -0.0229899000
_diffrn_orient_matrix_UB_22      0.0421738000
_diffrn_orient_matrix_UB_23      -0.0070866000
_diffrn_orient_matrix_UB_31      0.2795770000
_diffrn_orient_matrix_UB_32      0.0035779000
_diffrn_orient_matrix_UB_33      0.0729607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                6982
_reflns_number_total             7459
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 3123 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         7459
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.4341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0886
_refine_special_details          
'The pyruvic acid molecule (O10<O12 and C32<C34) was positionally disordered over two sites (A and B). The site occupancies for the A and B sites refined to 0.63 and 0.37, respectively. The rigid bond restraint RIGU was also applied to the disordered sites.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 O10A, O11A, O12A, C32A, C33A, C34A, O10B, O11B, O12B, C32B, C33B, C34B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(O10B)=Sof(O11B)=Sof(O12B)=Sof(H12B)=Sof(C32B)=Sof(C33B)=Sof(H33B)=
 Sof(C34B)=Sof(H34D)=Sof(H34E)=Sof(H34F)=1-FVAR(1)
 Sof(O10A)=Sof(O11A)=Sof(O12A)=Sof(H12A)=Sof(C32A)=Sof(C33A)=Sof(H33A)=
 Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C30(H30), C33A(H33A), C33B(H33B)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C12(H12), N5(H5), C18(H18), C20(H20), C26(H26)
4.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B), N6(H6A,H6B), N8(H8D,H8E)
4.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C21(H21A,H21B,H21C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C34A(H34A,H34B,
 H34C), C34B(H34D,H34E,H34F)
4.f Idealised tetrahedral OH refined as rotating group:
 O9(H9), O12A(H12A), O12B(H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.3802(4) 0.30160(6) 0.6841(2) 0.0258(5) Uani 1 1 d . . . . .
O2 O 1.0242(4) 0.25525(6) 0.5638(2) 0.0256(5) Uani 1 1 d . . . . .
O3 O 0.6699(4) 0.27789(6) 0.3676(2) 0.0263(5) Uani 1 1 d . . . . .
N1 N 0.5870(5) 0.44508(6) 0.6362(2) 0.0188(5) Uani 1 1 d . . . . .
H1 H 0.551502 0.441380 0.719121 0.023 Uiso 1 1 calc R U . . .
N2 N 0.2771(5) 0.49108(7) 0.6190(2) 0.0208(5) Uani 1 1 d . . . . .
H2A H 0.190699 0.508837 0.574399 0.025 Uiso 1 1 calc R U . . .
H2B H 0.240364 0.485689 0.700574 0.025 Uiso 1 1 calc R U . . .
N3 N 0.5218(5) 0.48022(6) 0.4394(2) 0.0192(5) Uani 1 1 d . . . . .
N4 N 0.7620(5) 0.46787(7) 0.2641(2) 0.0245(5) Uani 1 1 d . . . . .
H4A H 0.681709 0.486465 0.221606 0.029 Uiso 1 1 calc R U . . .
H4B H 0.880214 0.454964 0.225519 0.029 Uiso 1 1 calc R U . . .
C1 C 1.2123(6) 0.31591(8) 0.5842(3) 0.0199(6) Uani 1 1 d . . . . .
C2 C 1.0285(6) 0.29135(8) 0.5216(3) 0.0209(6) Uani 1 1 d . . . . .
C3 C 0.8434(6) 0.30391(8) 0.4200(3) 0.0214(6) Uani 1 1 d . . . . .
C4 C 0.8449(6) 0.34049(8) 0.3794(3) 0.0199(6) Uani 1 1 d . . . . .
H4 H 0.719120 0.348840 0.310044 0.024 Uiso 1 1 calc R U . . .
C5 C 1.0303(5) 0.36481(8) 0.4403(3) 0.0188(6) Uani 1 1 d . . . . .
C6 C 1.2128(6) 0.35276(8) 0.5434(3) 0.0195(6) Uani 1 1 d . . . . .
H6 H 1.337199 0.369497 0.586054 0.023 Uiso 1 1 calc R U . . .
C7 C 1.5796(6) 0.32516(9) 0.7457(3) 0.0261(6) Uani 1 1 d . . . . .
H7A H 1.681689 0.311969 0.818260 0.039 Uiso 1 1 calc R U . . .
H7B H 1.496537 0.346817 0.781870 0.039 Uiso 1 1 calc R U . . .
H7C H 1.697976 0.332907 0.679316 0.039 Uiso 1 1 calc R U . . .
C8 C 1.1347(7) 0.23062(9) 0.4719(3) 0.0309(7) Uani 1 1 d . . . . .
H8A H 1.110085 0.205192 0.500275 0.046 Uiso 1 1 calc R U . . .
H8B H 1.324120 0.235679 0.470493 0.046 Uiso 1 1 calc R U . . .
H8C H 1.045031 0.234204 0.382172 0.046 Uiso 1 1 calc R U . . .
C9 C 0.4943(7) 0.28856(10) 0.2549(3) 0.0305(7) Uani 1 1 d . . . . .
H9A H 0.382459 0.308878 0.280093 0.046 Uiso 1 1 calc R U . . .
H9B H 0.382496 0.267644 0.224893 0.046 Uiso 1 1 calc R U . . .
H9C H 0.597552 0.296464 0.182362 0.046 Uiso 1 1 calc R U . . .
C10 C 1.0290(6) 0.40422(7) 0.3929(3) 0.0194(6) Uani 1 1 d . . . . .
H10A H 0.987712 0.404606 0.294682 0.023 Uiso 1 1 calc R U . . .
H10B H 1.208623 0.414633 0.412994 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8314(5) 0.42854(7) 0.4560(2) 0.0169(5) Uani 1 1 d . . . . .
C12 C 0.7652(5) 0.42343(8) 0.5821(2) 0.0184(5) Uani 1 1 d . . . . .
H12 H 0.846577 0.404028 0.634088 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4624(5) 0.47250(8) 0.5635(3) 0.0187(6) Uani 1 1 d . . . . .
C14 C 0.7050(6) 0.45931(8) 0.3860(3) 0.0188(6) Uani 1 1 d . . . . .
O4 O -0.3805(5) 0.69839(6) -0.1837(2) 0.0317(5) Uani 1 1 d . . . . .
O5 O -0.0232(4) 0.74418(6) -0.0631(2) 0.0289(5) Uani 1 1 d . . . . .
O6 O 0.3273(4) 0.72167(6) 0.1342(2) 0.0295(5) Uani 1 1 d . . . . .
N5 N 0.4150(6) 0.55433(7) -0.1265(2) 0.0284(6) Uani 1 1 d . . . . .
H5 H 0.457208 0.558099 -0.208289 0.034 Uiso 1 1 calc R U . . .
N6 N 0.7146(6) 0.50712(7) -0.1051(2) 0.0270(6) Uani 1 1 d . . . . .
H6A H 0.795297 0.489084 -0.059365 0.032 Uiso 1 1 calc R U . . .
H6B H 0.756638 0.512249 -0.185966 0.032 Uiso 1 1 calc R U . . .
N7 N 0.4636(5) 0.51912(6) 0.0706(2) 0.0208(5) Uani 1 1 d . . . . .
N8 N 0.2209(5) 0.53251(8) 0.2446(2) 0.0261(6) Uani 1 1 d . . . . .
H8D H 0.297862 0.513839 0.288191 0.031 Uiso 1 1 calc R U . . .
H8E H 0.103325 0.545838 0.282039 0.031 Uiso 1 1 calc R U . . .
C15 C -0.2129(6) 0.68375(9) -0.0834(3) 0.0252(6) Uani 1 1 d . . . . .
C16 C -0.0288(6) 0.70832(8) -0.0214(3) 0.0242(6) Uani 1 1 d . . . . .
C17 C 0.1552(6) 0.69594(8) 0.0809(3) 0.0246(6) Uani 1 1 d . . . . .
C18 C 0.1503(6) 0.65956(8) 0.1233(3) 0.0268(7) Uani 1 1 d . . . . .
H18 H 0.273712 0.651252 0.193765 0.032 Uiso 1 1 calc R U . . .
C19 C -0.0367(6) 0.63535(9) 0.0620(3) 0.0276(7) Uani 1 1 d . . . . .
C20 C -0.2166(6) 0.64729(8) -0.0415(3) 0.0267(6) Uani 1 1 d . . . . .
H20 H -0.342162 0.630622 -0.083628 0.032 Uiso 1 1 calc R U . . .
C21 C -0.5806(7) 0.67488(10) -0.2459(3) 0.0334(8) Uani 1 1 d . . . . .
H21A H -0.695286 0.666325 -0.179099 0.050 Uiso 1 1 calc R U . . .
H21B H -0.497407 0.653717 -0.285384 0.050 Uiso 1 1 calc R U . . .
H21C H -0.686587 0.688465 -0.316126 0.050 Uiso 1 1 calc R U . . .
C22 C -0.1366(7) 0.76891(9) 0.0280(3) 0.0327(7) Uani 1 1 d . . . . .
H22A H -0.049923 0.765289 0.118337 0.049 Uiso 1 1 calc R U . . .
H22B H -0.326487 0.763938 0.027785 0.049 Uiso 1 1 calc R U . . .
H22C H -0.110445 0.794329 -0.000083 0.049 Uiso 1 1 calc R U . . .
C23 C 0.5034(7) 0.71117(10) 0.2466(3) 0.0332(8) Uani 1 1 d . . . . .
H23A H 0.401093 0.701899 0.317471 0.050 Uiso 1 1 calc R U . . .
H23B H 0.607640 0.732524 0.279520 0.050 Uiso 1 1 calc R U . . .
H23C H 0.622623 0.691873 0.220076 0.050 Uiso 1 1 calc R U . . .
C24 C -0.0366(7) 0.59600(8) 0.1109(3) 0.0308(7) Uani 1 1 d . . . . .
H24A H 0.002631 0.595900 0.209247 0.037 Uiso 1 1 calc R U . . .
H24B H -0.216015 0.585575 0.090261 0.037 Uiso 1 1 calc R U . . .
C25 C 0.1614(6) 0.57153(8) 0.0502(3) 0.0247(6) Uani 1 1 d . . . . .
C26 C 0.2334(7) 0.57645(8) -0.0735(3) 0.0282(7) Uani 1 1 d . . . . .
H26 H 0.155598 0.595969 -0.126246 0.034 Uiso 1 1 calc R U . . .
C27 C 0.5294(6) 0.52658(8) -0.0520(3) 0.0214(6) Uani 1 1 d . . . . .
C28 C 0.2823(6) 0.54061(8) 0.1219(3) 0.0208(6) Uani 1 1 d . . . . .
O7 O 0.1160(4) 0.45115(6) 0.8438(2) 0.0278(5) Uani 1 1 d . . . . .
O8 O 0.5082(4) 0.42294(6) 0.88047(19) 0.0240(4) Uani 1 1 d . . . . .
O9 O -0.0626(4) 0.42457(8) 1.06511(19) 0.0326(5) Uani 1 1 d . . . . .
H9 H -0.172015 0.420208 0.999048 0.049 Uiso 1 1 calc R U . . .
C29 C 0.2750(5) 0.43086(8) 0.9094(3) 0.0197(5) Uani 1 1 d . . . . .
C30 C 0.1921(5) 0.41324(7) 1.0365(2) 0.0218(5) Uani 1 1 d . . . . .
H30 H 0.320957 0.421197 1.112323 0.026 Uiso 1 1 calc R U . . .
C31 C 0.2042(9) 0.37150(9) 1.0277(4) 0.0481(10) Uani 1 1 d . . . . .
H31A H 0.088760 0.363084 0.950107 0.072 Uiso 1 1 calc R U . . .
H31B H 0.144926 0.360738 1.109168 0.072 Uiso 1 1 calc R U . . .
H31C H 0.386660 0.363830 1.018293 0.072 Uiso 1 1 calc R U . . .
O10A O 0.4991(7) 0.57899(11) 0.6388(3) 0.0226(8) Uani 0.633(4) 1 d . . P A 1
O11A O 0.869(3) 0.5454(4) 0.6599(12) 0.0276(15) Uani 0.633(4) 1 d . . P A 1
O12A O 1.0669(7) 0.58087(12) 0.4525(3) 0.0335(9) Uani 0.633(4) 1 d . . P A 1
H12A H 1.197272 0.578125 0.509502 0.050 Uiso 0.633(4) 1 calc R U P A 1
C32A C 0.7310(9) 0.57095(13) 0.6092(4) 0.0195(9) Uani 0.633(4) 1 d . . P A 1
C33A C 0.8551(8) 0.59827(13) 0.5136(4) 0.0294(10) Uani 0.633(4) 1 d . . P A 1
H33A H 0.932913 0.619087 0.569097 0.035 Uiso 0.633(4) 1 calc R U P A 1
C34A C 0.6626(9) 0.61426(14) 0.4070(5) 0.0375(12) Uani 0.633(4) 1 d . . P A 1
H34A H 0.590775 0.594619 0.347551 0.056 Uiso 0.633(4) 1 calc R U P A 1
H34B H 0.753405 0.632349 0.355318 0.056 Uiso 0.633(4) 1 calc R U P A 1
H34C H 0.517896 0.626261 0.448371 0.056 Uiso 0.633(4) 1 calc R U P A 1
O10B O 0.815(4) 0.5462(8) 0.674(2) 0.030(3) Uani 0.367(4) 1 d . . P A 2
O11B O 1.0032(10) 0.55233(14) 0.4842(5) 0.0258(13) Uani 0.367(4) 1 d . . P A 2
O12B O 0.4216(12) 0.5921(2) 0.6015(7) 0.0311(14) Uani 0.367(4) 1 d . . P A 2
H12B H 0.291264 0.578868 0.575429 0.047 Uiso 0.367(4) 1 calc R U P A 2
C32B C 0.8248(15) 0.5593(2) 0.5618(7) 0.0223(14) Uani 0.367(4) 1 d . . P A 2
C33B C 0.6222(13) 0.58799(19) 0.5131(7) 0.0240(14) Uani 0.367(4) 1 d . . P A 2
H33B H 0.537629 0.580330 0.423613 0.029 Uiso 0.367(4) 1 calc R U P A 2
C34B C 0.7680(17) 0.6251(2) 0.4977(9) 0.0303(18) Uani 0.367(4) 1 d . . P A 2
H34D H 0.860587 0.632217 0.583827 0.045 Uiso 0.367(4) 1 calc R U P A 2
H34E H 0.638822 0.644159 0.468233 0.045 Uiso 0.367(4) 1 calc R U P A 2
H34F H 0.896472 0.622445 0.431389 0.045 Uiso 0.367(4) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.359(3) . ?
O1 C7 1.423(4) . ?
O2 C2 1.382(3) . ?
O2 C8 1.439(4) . ?
O3 C3 1.365(3) . ?
O3 C9 1.428(4) . ?
N1 H1 0.8800 . ?
N1 C12 1.351(4) . ?
N1 C13 1.358(4) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C13 1.323(4) . ?
N3 C13 1.341(3) . ?
N3 C14 1.351(4) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C14 1.322(3) . ?
C1 C2 1.398(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.398(4) . ?
C3 C4 1.393(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(4) . ?
C5 C6 1.395(4) . ?
C5 C10 1.512(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(4) . ?
C11 C12 1.354(3) . ?
C11 C14 1.441(4) . ?
C12 H12 0.9500 . ?
O4 C15 1.365(4) . ?
O4 C21 1.427(4) . ?
O5 C16 1.372(4) . ?
O5 C22 1.442(4) . ?
O6 C17 1.356(4) . ?
O6 C23 1.426(4) . ?
N5 H5 0.8800 . ?
N5 C26 1.368(4) . ?
N5 C27 1.356(4) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C27 1.328(4) . ?
N7 C27 1.334(3) . ?
N7 C28 1.346(4) . ?
N8 H8D 0.8800 . ?
N8 H8E 0.8800 . ?
N8 C28 1.334(4) . ?
C15 C16 1.397(4) . ?
C15 C20 1.394(5) . ?
C16 C17 1.398(4) . ?
C17 C18 1.392(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(4) . ?
C19 C20 1.388(4) . ?
C19 C24 1.515(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.513(4) . ?
C25 C26 1.341(4) . ?
C25 C28 1.442(4) . ?
C26 H26 0.9500 . ?
O7 C29 1.238(3) . ?
O8 C29 1.277(3) . ?
O9 H9 0.8400 . ?
O9 C30 1.411(3) . ?
C29 C30 1.524(3) . ?
C30 H30 1.0000 . ?
C30 C31 1.524(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O10A C32A 1.274(6) . ?
O11A C32A 1.246(12) . ?
O12A H12A 0.8400 . ?
O12A C33A 1.434(5) . ?
C32A C33A 1.556(6) . ?
C33A H33A 1.0000 . ?
C33A C34A 1.499(6) . ?
C34A H34A 0.9800 . ?
C34A H34B 0.9800 . ?
C34A H34C 0.9800 . ?
O10B C32B 1.232(19) . ?
O11B C32B 1.275(10) . ?
O12B H12B 0.8400 . ?
O12B C33B 1.420(8) . ?
C32B C33B 1.513(10) . ?
C33B H33B 1.0000 . ?
C33B C34B 1.556(11) . ?
C34B H34D 0.9800 . ?
C34B H34E 0.9800 . ?
C34B H34F 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 C7 117.5(2) . . ?
C2 O2 C8 112.1(2) . . ?
C3 O3 C9 116.7(2) . . ?
C12 N1 H1 119.8 . . ?
C12 N1 C13 120.5(2) . . ?
C13 N1 H1 119.8 . . ?
H2A N2 H2B 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
C13 N3 C14 118.3(2) . . ?
H4A N4 H4B 120.0 . . ?
C14 N4 H4A 120.0 . . ?
C14 N4 H4B 120.0 . . ?
O1 C1 C2 115.7(2) . . ?
O1 C1 C6 124.4(3) . . ?
C2 C1 C6 120.0(3) . . ?
O2 C2 C1 119.9(3) . . ?
O2 C2 C3 120.4(3) . . ?
C1 C2 C3 119.6(3) . . ?
O3 C3 C2 114.8(2) . . ?
O3 C3 C4 124.8(3) . . ?
C4 C3 C2 120.3(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 C10 118.8(2) . . ?
C6 C5 C10 121.1(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 108.8 . . ?
C5 C10 H10B 108.8 . . ?
C5 C10 C11 113.9(2) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C12 C11 C10 122.8(2) . . ?
C12 C11 C14 115.2(2) . . ?
C14 C11 C10 121.9(2) . . ?
N1 C12 C11 122.1(3) . . ?
N1 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
N2 C13 N1 117.5(2) . . ?
N2 C13 N3 121.1(3) . . ?
N3 C13 N1 121.4(2) . . ?
N3 C14 C11 122.4(2) . . ?
N4 C14 N3 117.0(3) . . ?
N4 C14 C11 120.7(3) . . ?
C15 O4 C21 117.3(3) . . ?
C16 O5 C22 112.3(2) . . ?
C17 O6 C23 117.4(2) . . ?
C26 N5 H5 120.2 . . ?
C27 N5 H5 120.2 . . ?
C27 N5 C26 119.5(2) . . ?
H6A N6 H6B 120.0 . . ?
C27 N6 H6A 120.0 . . ?
C27 N6 H6B 120.0 . . ?
C27 N7 C28 118.3(2) . . ?
H8D N8 H8E 120.0 . . ?
C28 N8 H8D 120.0 . . ?
C28 N8 H8E 120.0 . . ?
O4 C15 C16 115.1(3) . . ?
O4 C15 C20 124.8(3) . . ?
C20 C15 C16 120.1(3) . . ?
O5 C16 C15 120.3(3) . . ?
O5 C16 C17 120.0(3) . . ?
C15 C16 C17 119.7(3) . . ?
O6 C17 C16 115.4(3) . . ?
O6 C17 C18 124.4(3) . . ?
C18 C17 C16 120.1(3) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C24 118.3(3) . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 C24 121.3(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 108.8 . . ?
C19 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C19 113.9(3) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C26 C25 C24 123.0(3) . . ?
C26 C25 C28 115.3(3) . . ?
C28 C25 C24 121.7(3) . . ?
N5 C26 H26 118.9 . . ?
C25 C26 N5 122.3(3) . . ?
C25 C26 H26 118.9 . . ?
N6 C27 N5 117.3(3) . . ?
N6 C27 N7 120.7(3) . . ?
N7 C27 N5 122.1(3) . . ?
N7 C28 C25 122.4(3) . . ?
N8 C28 N7 117.0(3) . . ?
N8 C28 C25 120.6(3) . . ?
C30 O9 H9 109.5 . . ?
O7 C29 O8 125.8(2) . . ?
O7 C29 C30 118.7(2) . . ?
O8 C29 C30 115.5(2) . . ?
O9 C30 C29 112.2(2) . . ?
O9 C30 H30 107.8 . . ?
O9 C30 C31 110.2(3) . . ?
C29 C30 H30 107.8 . . ?
C31 C30 C29 110.8(2) . . ?
C31 C30 H30 107.8 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33A O12A H12A 109.5 . . ?
O10A C32A C33A 115.7(4) . . ?
O11A C32A O10A 124.9(6) . . ?
O11A C32A C33A 119.1(6) . . ?
O12A C33A C32A 110.2(4) . . ?
O12A C33A H33A 107.5 . . ?
O12A C33A C34A 109.2(4) . . ?
C32A C33A H33A 107.5 . . ?
C34A C33A C32A 114.6(4) . . ?
C34A C33A H33A 107.5 . . ?
C33A C34A H34A 109.5 . . ?
C33A C34A H34B 109.5 . . ?
C33A C34A H34C 109.5 . . ?
H34A C34A H34B 109.5 . . ?
H34A C34A H34C 109.5 . . ?
H34B C34A H34C 109.5 . . ?
C33B O12B H12B 109.5 . . ?
O10B C32B O11B 125.2(10) . . ?
O10B C32B C33B 118.6(10) . . ?
O11B C32B C33B 116.1(6) . . ?
O12B C33B C32B 112.0(6) . . ?
O12B C33B H33B 108.7 . . ?
O12B C33B C34B 110.2(6) . . ?
C32B C33B H33B 108.7 . . ?
C32B C33B C34B 108.4(6) . . ?
C34B C33B H33B 108.7 . . ?
C33B C34B H34D 109.5 . . ?
C33B C34B H34E 109.5 . . ?
C33B C34B H34F 109.5 . . ?
H34D C34B H34E 109.5 . . ?
H34D C34B H34F 109.5 . . ?
H34E C34B H34F 109.5 . . ?

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 O7 0.88 2.66 3.324(3) 132.7 . yes
N1 H1 O8 0.88 1.79 2.651(3) 166.1 . yes
N2 H2B O7 0.88 2.05 2.869(3) 153.5 . yes
N4 H4A N7 0.88 2.15 3.001(4) 162.2 . yes
N8 H8D N3 0.88 2.19 3.038(3) 163.0 . yes

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 0.8(4) . . . . ?
O1 C1 C2 C3 178.3(2) . . . . ?
O1 C1 C6 C5 -179.4(2) . . . . ?
O2 C2 C3 O3 -1.2(4) . . . . ?
O2 C2 C3 C4 178.7(3) . . . . ?
O3 C3 C4 C5 179.7(2) . . . . ?
C1 C2 C3 O3 -178.7(2) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 C10 179.3(2) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C4 C5 C10 C11 83.8(3) . . . . ?
C5 C10 C11 C12 32.2(4) . . . . ?
C5 C10 C11 C14 -149.1(3) . . . . ?
C6 C1 C2 O2 -178.5(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C6 C5 C10 C11 -96.0(3) . . . . ?
C7 O1 C1 C2 176.7(2) . . . . ?
C7 O1 C1 C6 -4.0(4) . . . . ?
C8 O2 C2 C1 -105.6(3) . . . . ?
C8 O2 C2 C3 76.9(3) . . . . ?
C9 O3 C3 C2 -174.0(3) . . . . ?
C9 O3 C3 C4 6.0(4) . . . . ?
C10 C5 C6 C1 -179.0(2) . . . . ?
C10 C11 C12 N1 -179.3(3) . . . . ?
C10 C11 C14 N3 177.5(3) . . . . ?
C10 C11 C14 N4 -1.4(4) . . . . ?
C12 N1 C13 N2 175.5(3) . . . . ?
C12 N1 C13 N3 -3.7(4) . . . . ?
C12 C11 C14 N3 -3.8(4) . . . . ?
C12 C11 C14 N4 177.4(3) . . . . ?
C13 N1 C12 C11 1.6(4) . . . . ?
C13 N3 C14 N4 -179.2(3) . . . . ?
C13 N3 C14 C11 1.9(4) . . . . ?
C14 N3 C13 N1 1.8(4) . . . . ?
C14 N3 C13 N2 -177.3(3) . . . . ?
C14 C11 C12 N1 1.9(4) . . . . ?
O4 C15 C16 O5 -0.7(4) . . . . ?
O4 C15 C16 C17 -178.8(3) . . . . ?
O4 C15 C20 C19 -179.9(3) . . . . ?
O5 C16 C17 O6 1.3(4) . . . . ?
O5 C16 C17 C18 -179.9(3) . . . . ?
O6 C17 C18 C19 179.6(3) . . . . ?
C15 C16 C17 O6 179.4(3) . . . . ?
C15 C16 C17 C18 -1.8(5) . . . . ?
C16 C15 C20 C19 -0.1(5) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C17 C18 C19 C24 -179.9(3) . . . . ?
C18 C19 C20 C15 -0.7(5) . . . . ?
C18 C19 C24 C25 -83.5(4) . . . . ?
C19 C24 C25 C26 -31.1(4) . . . . ?
C19 C24 C25 C28 150.2(3) . . . . ?
C20 C15 C16 O5 179.5(3) . . . . ?
C20 C15 C16 C17 1.4(5) . . . . ?
C20 C19 C24 C25 96.3(3) . . . . ?
C21 O4 C15 C16 -177.0(3) . . . . ?
C21 O4 C15 C20 2.7(4) . . . . ?
C22 O5 C16 C15 104.7(3) . . . . ?
C22 O5 C16 C17 -77.2(3) . . . . ?
C23 O6 C17 C16 174.6(3) . . . . ?
C23 O6 C17 C18 -4.1(5) . . . . ?
C24 C19 C20 C15 179.5(3) . . . . ?
C24 C25 C26 N5 179.2(3) . . . . ?
C24 C25 C28 N7 -178.3(3) . . . . ?
C24 C25 C28 N8 0.5(4) . . . . ?
C26 N5 C27 N6 -176.5(3) . . . . ?
C26 N5 C27 N7 2.5(4) . . . . ?
C26 C25 C28 N7 2.8(4) . . . . ?
C26 C25 C28 N8 -178.4(3) . . . . ?
C27 N5 C26 C25 -0.6(5) . . . . ?
C27 N7 C28 N8 -179.9(3) . . . . ?
C27 N7 C28 C25 -1.1(4) . . . . ?
C28 N7 C27 N5 -1.7(4) . . . . ?
C28 N7 C27 N6 177.4(3) . . . . ?
C28 C25 C26 N5 -1.9(4) . . . . ?
O7 C29 C30 O9 -2.8(4) . . . . ?
O7 C29 C30 C31 120.9(3) . . . . ?
O8 C29 C30 O9 177.3(2) . . . . ?
O8 C29 C30 C31 -59.0(4) . . . . ?
O10A C32A C33A O12A -160.4(4) . . . . ?
O10A C32A C33A C34A -36.8(6) . . . . ?
O11A C32A C33A O12A 25.9(11) . . . . ?
O11A C32A C33A C34A 149.5(10) . . . . ?
O10B C32B C33B O12B -8(2) . . . . ?
O10B C32B C33B C34B 114(2) . . . . ?
O11B C32B C33B O12B 175.9(6) . . . . ?
O11B C32B C33B C34B -62.2(8) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   2169
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.667
####################################################################### 
# 
# 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_TMP_LLA_b
_database_code_depnum_ccdc_archive 'CCDC 2241037'
loop_
_audit_author_name
_audit_author_address
'Qixuan Zheng'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_TMP_LLA_b           
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.55 Note  
RESPONSE: This is due to the space group (P1) and number
of disordered sites within the structure.
;
_vrf_PLAT250_TMP_LLA_b           
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note  
RESPONSE: There is some slight disorder about the methoxy 
groups within the structure that were not modeled as 
positionally disordered.
;
_vrf_PLAT340_TMP_LLA_b           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00505 Ang.  
RESPONSE: This is due to both the poor data to parameter ratio 
and weak diffraction of high angle data.
;
_vrf_PLAT911_TMP_LLA_b           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         36 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
_vrf_PLAT915_TMP_LLA_b           
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         79 %     
RESPONSE: For thin plates it is hard to obtain high Friedel Pair Coverage
in P1.
;
# end Validation Reply Form

_audit_creation_date             2022-08-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N4 O3, C3 H5 O3'
_chemical_formula_sum            'C17 H24 N4 O6'
_chemical_formula_weight         380.40
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     TMP+LLA2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.06650(10)
_cell_length_b                   9.7541(2)
_cell_length_c                   19.4423(3)
_cell_angle_alpha                85.388(2)
_cell_angle_beta                 88.8410(10)
_cell_angle_gamma                77.804(2)
_cell_volume                     936.09(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    31700
_cell_measurement_temperature    99.96(12)
_cell_measurement_theta_max      74.8220
_cell_measurement_theta_min      2.2470
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             404
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 1 -8 0.0437
0 6 0 0.0658
-3 -1 8 0.0476
1 -6 -3 0.0637
0 6 0 0.0657
3 2 -3 0.0555
3 2 2 0.0628
-3 0 -2 0.0621
1 1 12 0.0386
2 1 -10 0.0371
-1 -6 4 0.0753
-1 0 12 0.0307
0 -3 -12 0.0387
1 3 -11 0.0377
0 -1 -12 0.0298
2 -4 -4 0.0547
0 -6 2 0.0653
3 3 5 0.0621
2 -2 6 0.0579
-3 -2 -6 0.0647
-2 -1 -11 0.0445
1 3 11 0.0475
-1 1 -12 0.0365
0 2 12 0.0383
0 2 -11 0.0362
0 -3 -11 0.0419
0 -1 -13 0.0300
-2 4 5 0.0718

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.063
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.5341 1.3506 -7.7441 -0.2222 -0.9285 -0.2974
0.1382 6.2327 0.4103 0.0444 0.1819 -0.9823
-2.5361 -0.7112 7.8366 0.2282 0.9534 0.1972
0.6274 -5.7524 -2.7402 -0.1109 -0.4597 0.8811
0.0179 6.1549 -0.4662 -0.0334 0.1842 -0.9823
3.1501 1.5981 -3.2615 0.1760 -0.9456 -0.2735
3.2574 1.7345 1.8385 0.5521 -0.8021 -0.2276
-3.1735 -0.0502 -2.1807 -0.5662 0.8231 -0.0435
0.5388 0.6491 12.4887 0.9567 0.2838 0.0645
1.7855 0.5105 -10.4506 -0.5111 -0.8347 -0.2050
-1.1115 -5.6751 4.3235 0.1655 0.2689 0.9488
-0.5216 0.0206 12.4076 0.8138 0.5600 0.1555
0.2287 -2.8291 -11.5006 -0.7861 -0.5405 0.2998
0.7020 2.7067 -10.8219 -0.6789 -0.4676 -0.5660
0.4564 -0.7473 -12.4252 -0.8231 -0.5664 -0.0409
1.9563 -3.9069 -3.8939 -0.0214 -0.8123 0.5829
0.0688 -5.9413 2.3658 0.1795 -0.1386 0.9739
2.9418 2.7549 5.1223 0.7440 -0.5700 -0.3487
2.2909 -2.3736 5.6789 0.7014 -0.5381 0.4674
-2.9746 -1.7373 -5.5715 -0.7806 0.5982 0.1811
-1.7892 -0.6438 -10.6789 -0.9902 0.1299 -0.0507
1.0498 2.8713 11.3063 0.9380 0.1741 -0.2998
-0.7130 0.6507 -12.0363 -0.9477 -0.1763 -0.2660
0.0187 2.1549 12.1402 0.8639 0.4694 -0.1827
0.0846 2.1438 -11.4800 -0.8054 -0.3337 -0.4898
-0.4434 -3.2022 -11.3603 -0.8631 -0.3583 0.3560
-0.2697 -1.3194 -12.5066 -0.9228 -0.3828 0.0435
-1.7050 4.2367 4.5597 0.1011 0.7743 -0.6246

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            54448
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.908
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -35.00   0.50    1.26    --  -47.88 170.00  32.00  166
  2  ω    -82.00  -6.00   0.50    1.26    --  -47.88 115.00-109.00  152
  3  ω   -120.00 -45.00   0.50    1.26    --  -47.88-170.00  17.00  150
  4  ω     27.00  91.00   0.50    1.26    --   47.88-115.00 160.00  128
  5  ω     57.00 122.00   0.50    1.26    --   47.88-170.00  17.00  130
  6  ω     67.00 120.00   0.50    1.26    --   47.88 170.00  32.00  106
  7  ω   -118.00 -35.00   0.50    5.06    --  -91.75 170.00  32.00  166
  8  ω   -163.00 -80.00   0.50    5.06    --  -91.75-115.00 160.00  166
  9  ω   -134.00 -45.00   0.50    5.06    --  -91.75-170.00  17.00  178
 10  ω    -83.00 -19.00   0.50    5.06    --  -91.75 115.00-109.00  128
 11  ω     67.00 151.00   0.50    5.06    --  107.81 170.00  32.00  168
 12  ω     57.00 144.00   0.50    5.06    --  107.81-170.00  17.00  174
 13  ω    101.00 178.00   0.50    5.06    --  107.81 115.00-109.00  154
 14  ω     35.00 109.00   0.50    5.06    --  107.81-115.00 160.00  148
 15  ω    -11.00  23.00   0.50    1.26    --   22.00  99.00 127.69   68
 16  ω    -12.00  18.00   0.50    1.26    --   22.00 101.00 169.76   60
 17  ω      4.00  39.00   0.50    1.26    --   34.00  92.00 119.98   70
 18  ω     17.00  43.00   0.50    1.26    --   46.00  90.00-137.47   52
 19  ω   -120.00 -25.00   0.50    1.26    --  -47.88 -77.00  30.00  190
 20  ω   -120.00 -25.00   0.50    1.26    --  -47.88 -77.00-120.00  190
 21  ω   -120.00 -25.00   0.50    1.26    --  -47.88 -77.00  60.00  190
 22  ω     25.00 121.00   0.50    1.26    --   47.88  77.00   0.00  192
 23  ω     25.00 121.00   0.50    1.26    --   47.88  77.00 -30.00  192
 24  ω     36.00 121.00   0.50    1.26    --   47.88  38.00  90.00  170
 25  ω     36.00 121.00   0.50    1.26    --   47.88  38.00 -60.00  170
 26  ω     36.00 121.00   0.50    1.26    --   47.88  38.00   0.00  170
 27  ω     25.00 121.00   0.50    1.26    --   47.88  77.00-180.00  192
 28  ω     35.00 123.00   0.50    1.26    --   47.88  19.00 -90.00  176
 29  ω     33.00 126.00   0.50    1.26    --   54.00  74.00 141.32  186
 30  ω     36.00 131.00   0.50    1.26    --   58.00  75.00 -39.67  190
 31  ω     36.00 131.00   0.50    1.26    --   58.00  76.00 112.13  190
 32  ω     41.00 135.00   0.50    1.26    --   62.00  73.00  98.11  188
 33  ω     41.00 135.00   0.50    1.26    --   62.00  74.00-121.91  188
 34  ω   -139.00 -47.00   0.50    1.26    --  -66.00 -68.00 176.86  184
 35  ω   -139.00 -48.00   0.50    1.26    --  -66.00 -65.00  83.24  182
 36  ω   -139.00 -43.00   0.50    1.26    --  -66.00 -76.00 145.34  192
 37  ω   -139.00 -47.00   0.50    1.26    --  -66.00 -68.00 -75.72  184
 38  ω     43.00 139.00   0.50    1.26    --   66.00  77.00  52.50  192
 39  ω     43.00 139.00   0.50    1.26    --   66.00  77.00 -96.78  192
 40  ω     43.00 139.00   0.50    1.26    --   66.00  77.00-165.55  192
 41  ω   -143.00 -52.00   0.50    5.06    --  -70.00 -66.00  65.71  182
 42  ω   -146.00 -53.00   0.50    5.06    --  -74.00 -73.00  44.60  186
 43  ω   -146.00 -52.00   0.50    5.06    --  -74.00 -74.00 122.66  188
 44  ω   -146.00 -52.00   0.50    5.06    --  -74.00 -74.00  11.31  188
 45  ω   -146.00 -55.00   0.50    5.06    --  -74.00 -67.00 125.29  182
 46  ω   -146.00 -55.00   0.50    5.06    --  -74.00 -67.00 119.96  182
 47  ω   -146.00 -56.00   0.50    5.06    --  -74.00 -65.00-157.02  180
 48  ω   -146.00 -56.00   0.50    5.06    --  -74.00 -64.00 178.60  180
 49  ω   -151.00 -60.00   0.50    5.06    --  -78.00 -64.00 160.69  182
 50  ω   -151.00 -57.00   0.50    5.06    --  -78.00 -73.00-106.88  188
 51  ω   -151.00 -56.00   0.50    5.06    --  -78.00 -74.00  -7.97  190
 52  ω   -154.00 -65.00   0.50    5.06    --  -82.00 -62.00 -85.51  178
 53  ω   -154.00 -64.00   0.50    5.06    --  -82.00 -66.00  60.08  180
 54  ω   -154.00 -62.00   0.50    5.06    --  -82.00 -70.00 145.97  184
 55  ω   -154.00 -60.00   0.50    5.06    --  -82.00 -74.00 -29.24  188
 56  ω   -159.00 -64.00   0.50    5.06    --  -86.00 -74.00  48.26  190
 57  ω   -162.00 -67.00   0.50    5.06    --  -90.00 -76.00 116.35  190
 58  ω   -162.00 -73.00   0.50    5.06    --  -90.00 -63.00-164.51  178
 59  ω   -163.00 -70.00   0.50    5.06    --  -91.75 -74.00 134.69  186
 60  ω   -163.00 -70.00   0.50    5.06    --  -91.75 -74.00  12.30  186
 61  ω   -163.00 -73.00   0.50    5.06    --  -91.75 -67.00 -11.89  180
 62  ω   -163.00 -72.00   0.50    5.06    --  -91.75 -69.00-173.47  182
 63  ω   -163.00 -69.00   0.50    5.06    --  -91.75 -76.00-100.58  188
 64  ω   -163.00 -69.00   0.50    5.06    --  -91.75 -76.00 132.41  188
 65  ω   -163.00 -69.00   0.50    5.06    --  -91.75 -77.00  30.00  188
 66  ω   -163.00 -69.00   0.50    5.06    --  -91.75 -77.00 -11.29  188
 67  ω   -163.00 -70.00   0.50    5.06    --  -91.75 -74.00 -46.15  186
 68  ω   -163.00 -71.00   0.50    5.06    --  -91.75 -71.00  89.43  184
 69  ω   -163.00 -71.00   0.50    5.06    --  -91.75 -72.00  36.54  184
 70  ω   -163.00 -73.00   0.50    5.06    --  -91.75 -66.00-123.87  180
 71  ω   -163.00 -71.00   0.50    5.06    --  -91.75 -72.00  69.41  184
 72  ω   -163.00 -74.00   0.50    5.06    --  -91.75 -63.00 -42.80  178
 73  ω    -85.00 -19.00   0.50    5.06    --  -91.75 125.00 -30.00  132
 74  ω   -163.00 -75.00   0.50    5.06    --  -91.75 -61.00 -95.64  176
 75  ω   -163.00 -69.00   0.50    5.06    --  -91.75 -77.00 -60.00  188
 76  ω   -163.00 -74.00   0.50    5.06    --  -91.75 -64.00-144.75  178
 77  ω   -163.00 -69.00   0.50    5.06    --  -91.75 -77.00-120.00  188
 78  ω   -163.00 -72.00   0.50    5.06    --  -91.75 -70.00 161.95  182
 79  ω    -64.00 -19.00   0.50    5.06    --  -91.75  57.00  90.00   90
 80  ω   -163.00 -74.00   0.50    5.06    --  -91.75 -65.00  91.99  178
 81  ω     35.00 112.00   0.50    5.06    --  107.81-125.00-120.00  154
 82  ω     35.00  68.00   0.50    5.06    --  107.81 -57.00-150.00   66
 83  ω     35.00 106.00   0.50    5.06    --  107.81 -99.00 -30.00  142
 84  ω     35.00 107.00   0.50    5.06    --  107.81-104.00 -53.90  144
 85  ω     35.00 106.00   0.50    5.06    --  107.81 -99.00  30.00  142
 86  ω     35.00 106.00   0.50    5.06    --  107.81 -99.00  90.00  142
 87  ω     35.00 107.00   0.50    5.06    --  107.81 -77.00 150.00  144
 88  ω     35.00 106.00   0.50    5.06    --  107.81 -99.00-120.00  142
 89  ω     35.00  68.00   0.50    5.06    --  107.81 -57.00  30.00   66
 90  ω   -120.00 -25.00   0.50    1.26    --  -47.88 -77.00 -90.00  190
 91  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00 -30.00  288
 92  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00  60.00  288
 93  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00 -60.00  288
 94  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00  90.00  288
 95  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00 -90.00  288
 96  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00   0.00  288
 97  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00 120.00  288
 98  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00  30.00  288
 99  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00-180.00  288
100  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00-150.00  288
101  ω    -24.00 120.00   0.50    1.26    --   47.88   0.00-120.00  288
102  ω   -131.00 -35.00   0.50    1.26    --  -58.00 -76.00 -50.93  192
103  ω   -131.00 -35.00   0.50    1.26    --  -58.00 -77.00 -52.77  192
104  ω   -135.00 -45.00   0.50    1.26    --  -62.00 -61.00 140.41  180
105  ω   -135.00 -43.00   0.50    1.26    --  -62.00 -67.00 -91.50  184
106  ω     39.00 135.00   0.50    1.26    --   62.00  77.00  50.72  192
107  ω     40.00 135.00   0.50    1.26    --   62.00  75.00  25.42  190
108  ω   -139.00 -47.00   0.50    1.26    --  -66.00 -68.00 -68.45  184
109  ω   -139.00 -48.00   0.50    1.26    --  -66.00 -64.00-114.04  182
110  ω     43.00 139.00   0.50    1.26    --   66.00  77.00  20.12  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1296234000
_diffrn_orient_matrix_UB_12      -0.0004282000
_diffrn_orient_matrix_UB_13      0.0710351000
_diffrn_orient_matrix_UB_21      -0.2827043000
_diffrn_orient_matrix_UB_22      0.0332713000
_diffrn_orient_matrix_UB_23      0.0331953000
_diffrn_orient_matrix_UB_31      0.0072179000
_diffrn_orient_matrix_UB_32      -0.1586279000
_diffrn_orient_matrix_UB_33      0.0130990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.786
_reflns_number_gt                6060
_reflns_number_total             6761
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         6761
_refine_ls_number_restraints     231
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0874P)²+0.0831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1243
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.1(2)
 -0.1(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Uiso/Uaniso restraints and constraints
O10B \\sim O12A \\sim O10A \\sim C33A \\sim C34A \\sim C32A \\sim O11B \\sim
O12B \\sim C33B \\sim C32B \\sim C34B: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
O10B \\sim O12A \\sim O10A \\sim C33A \\sim C34A \\sim C32A \\sim O11B \\sim
O12B \\sim C33B \\sim C32B \\sim C34B \\sim O11A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 O10B, O12A, O10A, C33A, C34A, C32A, O11B, O12B, C33B, C32B, C34B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O10B, O12A, O10A, C33A, C34A, C32A, O11B, O12B, C33B, C32B, C34B, O11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O10B)=Sof(O11B)=Sof(O12B)=Sof(H12B)=Sof(C33B)=Sof(H33B)=Sof(C32B)=
 Sof(C34B)=Sof(H34A)=Sof(H34B)=Sof(H34C)=1-FVAR(1)
 Sof(O12A)=Sof(H12A)=Sof(O10A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34D)=
 Sof(H34E)=Sof(H34F)=Sof(C32A)=Sof(O11A)=FVAR(1)
6.a Rotating group:
 N8(H8A,H8B)
6.b Ternary CH refined with riding coordinates:
 C30(H30), C33A(H33A), C33B(H33B)
6.c Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C10(H10A,H10B)
6.d Aromatic/amide H refined with riding coordinates:
 N5(H5), C18(H18), N1(H1), C20(H20), C28(H28), C14(H14), C4(H4), C2(H2)
6.e X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N4(H4A,H4B), N2(H2A,H2B)
6.f Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C),
 C8(H8C,H8D,H8E), C31(H31A,H31B,H31C), C22(H22A,H22B,H22C), C34A(H34D,H34E,
 H34F), C34B(H34A,H34B,H34C)
6.g Idealised tetrahedral OH refined as rotating group:
 O9(H9), O12A(H12A), O12B(H12B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O6 O 0.1224(4) 0.9329(3) 0.06273(12) 0.0348(6) Uani 1 1 d . . . . .
O8 O 0.9964(4) 0.3871(3) 0.33912(13) 0.0327(6) Uani 1 1 d . . . . .
O9 O 0.4619(4) 0.1963(3) 0.35741(14) 0.0354(6) Uani 1 1 d . . . . .
H9 H 0.329543 0.257892 0.342339 0.053 Uiso 1 1 calc R U . . .
O10B O 0.297(4) 0.582(3) 0.5764(17) 0.028(4) Uani 0.281(5) 1 d . U P A 2
O4 O 0.9001(4) 0.5878(3) 0.11379(13) 0.0368(6) Uani 1 1 d . . . . .
O7 O 0.6100(4) 0.4228(3) 0.39973(13) 0.0333(6) Uani 1 1 d . . . . .
O2 O 0.5031(5) 0.2918(3) 0.95431(13) 0.0384(6) Uani 1 1 d . . . . .
N7 N 0.0023(5) 0.8214(3) 0.45018(14) 0.0258(6) Uani 1 1 d . . . . .
N6 N -0.2459(5) 0.6471(3) 0.47060(15) 0.0285(6) Uani 1 1 d . . . . .
H6A H -0.328315 0.690529 0.505502 0.034 Uiso 1 1 calc R U . . .
H6B H -0.285725 0.567989 0.459685 0.034 Uiso 1 1 calc R U . . .
N8 N 0.2622(5) 0.9852(3) 0.42996(14) 0.0270(6) Uani 1 1 d . . . . .
H8A H 0.278155 1.043203 0.393648 0.032 Uiso 1 1 d R U . . .
H8B H 0.139565 1.028470 0.458159 0.032 Uiso 1 1 d R U . . .
O5 O 0.5390(5) 0.7405(3) 0.02187(12) 0.0351(6) Uani 1 1 d . . . . .
O3 O 0.1219(5) 0.4368(3) 0.86721(15) 0.0461(7) Uani 1 1 d . . . . .
O1 O 0.8747(5) 0.0767(3) 0.91487(12) 0.0376(6) Uani 1 1 d . . . . .
N5 N 0.0551(5) 0.6306(3) 0.38054(14) 0.0260(6) Uani 1 1 d . . . . .
H5 H 0.019909 0.548437 0.373241 0.031 Uiso 1 1 calc R U . . .
C29 C 0.7717(6) 0.3560(4) 0.35942(18) 0.0270(7) Uani 1 1 d . . . . .
C18 C 0.2903(6) 0.9046(4) 0.18052(17) 0.0269(7) Uani 1 1 d . . . . .
H18 H 0.145879 0.975408 0.195059 0.032 Uiso 1 1 calc R U . . .
N1 N 0.9269(6) 0.3688(3) 0.59762(14) 0.0326(7) Uani 1 1 d . . . . .
H1 H 0.967644 0.449980 0.604451 0.039 Uiso 1 1 calc R U . . .
C26 C 0.1861(5) 0.8724(4) 0.41024(16) 0.0232(7) Uani 1 1 d . . . . .
N4 N 0.7068(5) 0.0145(3) 0.55258(15) 0.0322(7) Uani 1 1 d . . . . .
H4A H 0.773769 -0.026105 0.515374 0.039 Uiso 1 1 calc R U . . .
H4B H 0.588817 -0.020917 0.578348 0.039 Uiso 1 1 calc R U . . .
N3 N 0.9649(5) 0.1790(3) 0.52865(14) 0.0281(6) Uani 1 1 d . . . . .
C25 C 0.2955(6) 0.8102(4) 0.34840(16) 0.0243(7) Uani 1 1 d . . . . .
C17 C 0.3046(6) 0.8697(4) 0.11288(17) 0.0285(7) Uani 1 1 d . . . . .
N2 N 1.2189(5) 0.3483(3) 0.50529(15) 0.0303(6) Uani 1 1 d . . . . .
H2A H 1.294126 0.304321 0.469761 0.036 Uiso 1 1 calc R U . . .
H2B H 1.264594 0.426395 0.515567 0.036 Uiso 1 1 calc R U . . .
C24 C 0.4757(6) 0.8798(4) 0.30050(17) 0.0263(7) Uani 1 1 d . . . . .
H24A H 0.409485 0.983005 0.299007 0.032 Uiso 1 1 calc R U . . .
H24B H 0.660448 0.858040 0.319838 0.032 Uiso 1 1 calc R U . . .
C27 C -0.0608(6) 0.7010(4) 0.43426(17) 0.0248(7) Uani 1 1 d . . . . .
C20 C 0.6931(6) 0.7284(4) 0.20665(18) 0.0284(7) Uani 1 1 d . . . . .
H20 H 0.824491 0.678730 0.238912 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4895(6) 0.8352(4) 0.22767(17) 0.0269(7) Uani 1 1 d . . . . .
C28 C 0.2277(6) 0.6878(4) 0.33753(17) 0.0259(7) Uani 1 1 d . . . . .
H28 H 0.301745 0.639420 0.298768 0.031 Uiso 1 1 calc R U . . .
O12A O 0.5565(6) 0.7846(4) 0.6305(2) 0.0355(10) Uani 0.719(5) 1 d . U P A 1
H12A H 0.708643 0.729759 0.632694 0.053 Uiso 0.719(5) 1 calc R U P A 1
O10A O 0.0217(7) 0.5952(4) 0.6440(2) 0.0300(8) Uani 0.719(5) 1 d . U P A 1
C6 C 0.4926(7) 0.2531(4) 0.88849(18) 0.0335(8) Uani 1 1 d . . . . .
C30 C 0.7049(6) 0.2285(4) 0.32922(19) 0.0313(7) Uani 1 1 d . . . . .
H30 H 0.854458 0.146241 0.342288 0.038 Uiso 1 1 calc R U . . .
C15 C 0.7066(6) 0.6933(4) 0.13862(18) 0.0291(7) Uani 1 1 d . . . . .
C5 C 0.2989(7) 0.3260(4) 0.84138(19) 0.0350(8) Uani 1 1 d . . . . .
C23 C -0.1012(7) 1.0378(4) 0.08340(18) 0.0358(8) Uani 1 1 d . . . . .
H23A H -0.212833 1.077396 0.043079 0.054 Uiso 1 1 calc R U . . .
H23B H -0.033994 1.112777 0.103514 0.054 Uiso 1 1 calc R U . . .
H23C H -0.209855 0.995019 0.117739 0.054 Uiso 1 1 calc R U . . .
C16 C 0.5143(6) 0.7646(4) 0.09025(17) 0.0288(7) Uani 1 1 d . . . . .
C13 C 1.0360(6) 0.2967(4) 0.54350(16) 0.0278(7) Uani 1 1 d . . . . .
C3 C 0.4896(7) 0.1756(5) 0.75307(18) 0.0377(9) Uani 1 1 d . . . . .
C14 C 0.7542(6) 0.3152(4) 0.64141(17) 0.0358(9) Uani 1 1 d . . . . .
H14 H 0.685323 0.364772 0.680248 0.043 Uiso 1 1 calc R U . . .
C1 C 0.6908(7) 0.1416(4) 0.86639(18) 0.0331(8) Uani 1 1 d . . . . .
C4 C 0.2947(7) 0.2883(5) 0.77416(19) 0.0386(9) Uani 1 1 d . . . . .
H4 H 0.160560 0.338721 0.742808 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7838(6) 0.1292(4) 0.56987(17) 0.0310(8) Uani 1 1 d . . . . .
C21 C 1.1087(7) 0.5193(4) 0.16003(19) 0.0374(8) Uani 1 1 d . . . . .
H21A H 1.230320 0.444353 0.137245 0.056 Uiso 1 1 calc R U . . .
H21B H 1.029242 0.478532 0.201077 0.056 Uiso 1 1 calc R U . . .
H21C H 1.210654 0.587556 0.173704 0.056 Uiso 1 1 calc R U . . .
C11 C 0.6782(6) 0.1945(4) 0.63142(17) 0.0333(8) Uani 1 1 d . . . . .
C7 C 1.0800(8) -0.0371(5) 0.8943(2) 0.0428(10) Uani 1 1 d . . . . .
H7A H 1.182809 -0.003580 0.855629 0.064 Uiso 1 1 calc R U . . .
H7B H 0.996365 -0.112081 0.880037 0.064 Uiso 1 1 calc R U . . .
H7C H 1.201644 -0.073573 0.933175 0.064 Uiso 1 1 calc R U . . .
C9 C -0.1057(8) 0.5047(5) 0.8244(3) 0.0509(11) Uani 1 1 d . . . . .
H9A H -0.040356 0.542207 0.780540 0.076 Uiso 1 1 calc R U . . .
H9B H -0.216492 0.581749 0.848138 0.076 Uiso 1 1 calc R U . . .
H9C H -0.214574 0.436077 0.815485 0.076 Uiso 1 1 calc R U . . .
C10 C 0.4937(7) 0.1299(5) 0.68038(18) 0.0399(10) Uani 1 1 d . . . . .
H10A H 0.307749 0.155476 0.661789 0.048 Uiso 1 1 calc R U . . .
H10B H 0.551645 0.026216 0.682130 0.048 Uiso 1 1 calc R U . . .
C8 C 0.2874(8) 0.2578(5) 0.99796(18) 0.0466(10) Uani 1 1 d . . . . .
H8C H 0.114589 0.316455 0.982062 0.070 Uiso 1 1 calc R U . . .
H8D H 0.319088 0.275446 1.045691 0.070 Uiso 1 1 calc R U . . .
H8E H 0.282400 0.158333 0.995667 0.070 Uiso 1 1 calc R U . . .
C2 C 0.6885(7) 0.1038(4) 0.79910(18) 0.0358(9) Uani 1 1 d . . . . .
H2 H 0.823340 0.028539 0.784322 0.043 Uiso 1 1 calc R U . . .
C31 C 0.6940(8) 0.2460(5) 0.2513(2) 0.0475(10) Uani 1 1 d . . . . .
H31A H 0.646834 0.162870 0.233774 0.071 Uiso 1 1 calc R U . . .
H31B H 0.870802 0.256685 0.233007 0.071 Uiso 1 1 calc R U . . .
H31C H 0.557316 0.329784 0.236636 0.071 Uiso 1 1 calc R U . . .
C22 C 0.4332(9) 0.6242(5) 0.0033(2) 0.0508(10) Uani 1 1 d . . . . .
H22A H 0.452419 0.616799 -0.046608 0.076 Uiso 1 1 calc R U . . .
H22B H 0.241805 0.638572 0.016049 0.076 Uiso 1 1 calc R U . . .
H22C H 0.532827 0.537453 0.027665 0.076 Uiso 1 1 calc R U . . .
C33A C 0.3631(9) 0.7196(6) 0.6676(3) 0.0321(11) Uani 0.719(5) 1 d . U P A 1
H33A H 0.460122 0.657487 0.706634 0.039 Uiso 0.719(5) 1 calc R U P A 1
C34A C 0.1551(9) 0.8335(6) 0.6987(3) 0.0385(12) Uani 0.719(5) 1 d . U P A 1
H34D H 0.244553 0.882696 0.730144 0.058 Uiso 0.719(5) 1 calc R U P A 1
H34E H 0.020135 0.790859 0.724180 0.058 Uiso 0.719(5) 1 calc R U P A 1
H34F H 0.066147 0.900690 0.661731 0.058 Uiso 0.719(5) 1 calc R U P A 1
C32A C 0.2427(9) 0.6256(6) 0.6223(3) 0.0259(11) Uani 0.719(5) 1 d . U P A 1
O11B O 0.4972(15) 0.7578(10) 0.5861(4) 0.030(2) Uani 0.281(5) 1 d . U P A 2
O12B O -0.0703(18) 0.6519(13) 0.6718(5) 0.035(2) Uani 0.281(5) 1 d . U P A 2
H12B H -0.180283 0.672352 0.638883 0.053 Uiso 0.281(5) 1 calc R U P A 2
C33B C 0.133(2) 0.7332(14) 0.6620(5) 0.029(2) Uani 0.281(5) 1 d . U P A 2
H33B H 0.043948 0.834375 0.651927 0.034 Uiso 0.281(5) 1 calc R U P A 2
C32B C 0.321(2) 0.6851(16) 0.6017(6) 0.029(2) Uani 0.281(5) 1 d . U P A 2
C34B C 0.292(2) 0.7176(14) 0.7292(6) 0.028(3) Uani 0.281(5) 1 d . U P A 2
H34A H 0.168374 0.748417 0.767051 0.043 Uiso 0.281(5) 1 calc R U P A 2
H34B H 0.428483 0.775546 0.724438 0.043 Uiso 0.281(5) 1 calc R U P A 2
H34C H 0.381081 0.618775 0.739338 0.043 Uiso 0.281(5) 1 calc R U P A 2
O11A O 0.3684(16) 0.5791(13) 0.5699(7) 0.0315(17) Uani 0.719(5) 1 d . U P A 1


_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
O6 C17 1.372(4) . ?
O6 C23 1.432(4) . ?
O8 C29 1.286(4) . ?
O9 H9 0.8400 . ?
O9 C30 1.423(4) . ?
O10B C32B 1.19(3) . ?
O4 C15 1.374(4) . ?
O4 C21 1.420(5) . ?
O7 C29 1.241(4) . ?
O2 C6 1.368(4) . ?
O2 C8 1.447(4) . ?
N7 C26 1.349(4) . ?
N7 C27 1.341(4) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C27 1.333(4) . ?
N8 H8A 0.8821 . ?
N8 H8B 0.8818 . ?
N8 C26 1.326(4) . ?
O5 C16 1.367(4) . ?
O5 C22 1.426(5) . ?
O3 C5 1.373(4) . ?
O3 C9 1.445(5) . ?
O1 C1 1.359(4) . ?
O1 C7 1.428(5) . ?
N5 H5 0.8800 . ?
N5 C27 1.352(4) . ?
N5 C28 1.370(4) . ?
C29 C30 1.519(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.381(5) . ?
C18 C19 1.402(5) . ?
N1 H1 0.8800 . ?
N1 C13 1.356(4) . ?
N1 C14 1.362(5) . ?
C26 C25 1.439(5) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C12 1.329(5) . ?
N3 C13 1.328(5) . ?
N3 C12 1.348(4) . ?
C25 C24 1.512(4) . ?
C25 C28 1.343(5) . ?
C17 C16 1.403(5) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C13 1.332(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C19 1.510(5) . ?
C20 H20 0.9500 . ?
C20 C19 1.383(5) . ?
C20 C15 1.390(5) . ?
C28 H28 0.9500 . ?
O12A H12A 0.8400 . ?
O12A C33A 1.429(6) . ?
O10A C32A 1.274(7) . ?
C6 C5 1.394(5) . ?
C6 C1 1.404(5) . ?
C30 H30 1.0000 . ?
C30 C31 1.511(6) . ?
C15 C16 1.401(5) . ?
C5 C4 1.388(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C3 C4 1.397(6) . ?
C3 C10 1.514(5) . ?
C3 C2 1.394(5) . ?
C14 H14 0.9500 . ?
C14 C11 1.343(6) . ?
C1 C2 1.388(5) . ?
C4 H4 0.9500 . ?
C12 C11 1.441(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C11 C10 1.515(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C2 H2 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C33A H33A 1.0000 . ?
C33A C34A 1.516(7) . ?
C33A C32A 1.541(7) . ?
C34A H34D 0.9800 . ?
C34A H34E 0.9800 . ?
C34A H34F 0.9800 . ?
C32A O11A 1.255(12) . ?
O11B C32B 1.269(18) . ?
O12B H12B 0.8400 . ?
O12B C33B 1.428(14) . ?
C33B H33B 1.0000 . ?
C33B C32B 1.536(16) . ?
C33B C34B 1.530(15) . ?
C34B H34A 0.9800 . ?
C34B H34B 0.9800 . ?
C34B H34C 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
C17 O6 C23 117.0(3) . . ?
C30 O9 H9 109.5 . . ?
C15 O4 C21 116.9(3) . . ?
C6 O2 C8 113.1(3) . . ?
C27 N7 C26 117.9(3) . . ?
H6A N6 H6B 120.0 . . ?
C27 N6 H6A 120.0 . . ?
C27 N6 H6B 120.0 . . ?
H8A N8 H8B 109.1 . . ?
C26 N8 H8A 109.9 . . ?
C26 N8 H8B 109.3 . . ?
C16 O5 C22 114.8(3) . . ?
C5 O3 C9 117.0(3) . . ?
C1 O1 C7 117.2(3) . . ?
C27 N5 H5 120.2 . . ?
C27 N5 C28 119.7(3) . . ?
C28 N5 H5 120.2 . . ?
O8 C29 C30 115.4(3) . . ?
O7 C29 O8 125.1(3) . . ?
O7 C29 C30 119.6(3) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C13 N1 H1 120.1 . . ?
C13 N1 C14 119.8(3) . . ?
C14 N1 H1 120.1 . . ?
N7 C26 C25 122.6(3) . . ?
N8 C26 N7 117.0(3) . . ?
N8 C26 C25 120.4(3) . . ?
H4A N4 H4B 120.0 . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
C13 N3 C12 118.5(3) . . ?
C26 C25 C24 121.1(3) . . ?
C28 C25 C26 115.2(3) . . ?
C28 C25 C24 123.7(3) . . ?
O6 C17 C18 124.2(3) . . ?
O6 C17 C16 114.6(3) . . ?
C18 C17 C16 121.2(3) . . ?
H2A N2 H2B 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C19 C24 C25 114.3(3) . . ?
C19 C24 H24A 108.7 . . ?
C19 C24 H24B 108.7 . . ?
N7 C27 N5 122.0(3) . . ?
N6 C27 N7 120.8(3) . . ?
N6 C27 N5 117.2(3) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C15 120.4(3) . . ?
C15 C20 H20 119.8 . . ?
C18 C19 C24 118.7(3) . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 C24 121.7(3) . . ?
N5 C28 H28 118.9 . . ?
C25 C28 N5 122.1(3) . . ?
C25 C28 H28 118.9 . . ?
C33A O12A H12A 109.5 . . ?
O2 C6 C5 121.9(3) . . ?
O2 C6 C1 119.2(3) . . ?
C5 C6 C1 118.8(3) . . ?
O9 C30 C29 111.8(3) . . ?
O9 C30 H30 107.3 . . ?
O9 C30 C31 111.1(3) . . ?
C29 C30 H30 107.3 . . ?
C31 C30 C29 111.8(3) . . ?
C31 C30 H30 107.3 . . ?
O4 C15 C20 124.0(3) . . ?
O4 C15 C16 115.2(3) . . ?
C20 C15 C16 120.8(3) . . ?
O3 C5 C6 114.2(3) . . ?
O3 C5 C4 124.3(3) . . ?
C4 C5 C6 121.4(3) . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O5 C16 C17 120.3(3) . . ?
O5 C16 C15 121.4(3) . . ?
C15 C16 C17 118.1(3) . . ?
N3 C13 N1 121.8(3) . . ?
N3 C13 N2 120.7(3) . . ?
N2 C13 N1 117.5(3) . . ?
C4 C3 C10 121.4(3) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 C10 118.6(3) . . ?
N1 C14 H14 119.0 . . ?
C11 C14 N1 122.1(3) . . ?
C11 C14 H14 119.0 . . ?
O1 C1 C6 115.5(3) . . ?
O1 C1 C2 124.4(3) . . ?
C2 C1 C6 120.1(3) . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N4 C12 N3 117.6(3) . . ?
N4 C12 C11 120.2(3) . . ?
N3 C12 C11 122.2(3) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C11 C12 115.3(3) . . ?
C14 C11 C10 123.3(3) . . ?
C12 C11 C10 121.4(4) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 C11 114.0(3) . . ?
C3 C10 H10A 108.7 . . ?
C3 C10 H10B 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
O2 C8 H8C 109.5 . . ?
O2 C8 H8D 109.5 . . ?
O2 C8 H8E 109.5 . . ?
H8C C8 H8D 109.5 . . ?
H8C C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O12A C33A H33A 107.4 . . ?
O12A C33A C34A 108.3(4) . . ?
O12A C33A C32A 111.7(4) . . ?
C34A C33A H33A 107.4 . . ?
C34A C33A C32A 114.2(4) . . ?
C32A C33A H33A 107.4 . . ?
C33A C34A H34D 109.5 . . ?
C33A C34A H34E 109.5 . . ?
C33A C34A H34F 109.5 . . ?
H34D C34A H34E 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?
O10A C32A C33A 115.4(5) . . ?
O11A C32A O10A 124.5(6) . . ?
O11A C32A C33A 120.0(6) . . ?
C33B O12B H12B 109.5 . . ?
O12B C33B H33B 108.9 . . ?
O12B C33B C32B 111.3(11) . . ?
O12B C33B C34B 107.9(9) . . ?
C32B C33B H33B 108.9 . . ?
C34B C33B H33B 108.9 . . ?
C34B C33B C32B 110.8(9) . . ?
O10B C32B O11B 126.4(16) . . ?
O10B C32B C33B 117.8(17) . . ?
O11B C32B C33B 115.7(11) . . ?
C33B C34B H34A 109.5 . . ?
C33B C34B H34B 109.5 . . ?
C33B C34B H34C 109.5 . . ?
H34A C34B H34B 109.5 . . ?
H34A C34B H34C 109.5 . . ?
H34B C34B H34C 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
O6 C17 C16 O5 5.6(5) . . . . ?
O6 C17 C16 C15 -179.0(3) . . . . ?
O8 C29 C30 O9 176.5(3) . . . . ?
O8 C29 C30 C31 -58.3(4) . . . . ?
O4 C15 C16 O5 -7.2(5) . . . . ?
O4 C15 C16 C17 177.5(3) . . . . ?
O7 C29 C30 O9 -4.8(4) . . . . ?
O7 C29 C30 C31 120.5(4) . . . . ?
O2 C6 C5 O3 -0.7(5) . . . . ?
O2 C6 C5 C4 178.2(3) . . . . ?
O2 C6 C1 O1 2.6(5) . . . . ?
O2 C6 C1 C2 -177.9(3) . . . . ?
N7 C26 C25 C24 172.7(3) . . . . ?
N7 C26 C25 C28 -7.8(4) . . . . ?
N8 C26 C25 C24 -6.6(5) . . . . ?
N8 C26 C25 C28 172.9(3) . . . . ?
O3 C5 C4 C3 178.4(4) . . . . ?
O1 C1 C2 C3 179.2(3) . . . . ?
C18 C17 C16 O5 -174.0(3) . . . . ?
C18 C17 C16 C15 1.4(5) . . . . ?
N1 C14 C11 C12 -2.3(5) . . . . ?
N1 C14 C11 C10 178.0(3) . . . . ?
C26 N7 C27 N6 -178.3(3) . . . . ?
C26 N7 C27 N5 0.6(4) . . . . ?
C26 C25 C24 C19 -158.4(3) . . . . ?
C26 C25 C28 N5 3.3(5) . . . . ?
N4 C12 C11 C14 -175.5(3) . . . . ?
N4 C12 C11 C10 4.3(5) . . . . ?
N3 C12 C11 C14 5.7(5) . . . . ?
N3 C12 C11 C10 -174.6(3) . . . . ?
C25 C24 C19 C18 85.2(4) . . . . ?
C25 C24 C19 C20 -94.9(4) . . . . ?
C17 C18 C19 C24 177.4(3) . . . . ?
C17 C18 C19 C20 -2.5(5) . . . . ?
C24 C25 C28 N5 -177.3(3) . . . . ?
C27 N7 C26 N8 -174.7(3) . . . . ?
C27 N7 C26 C25 6.0(4) . . . . ?
C27 N5 C28 C25 2.8(5) . . . . ?
C20 C15 C16 O5 173.7(3) . . . . ?
C20 C15 C16 C17 -1.6(5) . . . . ?
C19 C18 C17 O6 -178.9(3) . . . . ?
C19 C18 C17 C16 0.6(5) . . . . ?
C19 C20 C15 O4 -179.3(3) . . . . ?
C19 C20 C15 C16 -0.3(5) . . . . ?
C28 N5 C27 N7 -4.9(4) . . . . ?
C28 N5 C27 N6 173.9(3) . . . . ?
C28 C25 C24 C19 22.2(5) . . . . ?
O12A C33A C32A O10A -161.6(4) . . . . ?
O12A C33A C32A O11A 21.8(9) . . . . ?
C6 C5 C4 C3 -0.4(6) . . . . ?
C6 C1 C2 C3 -0.2(6) . . . . ?
C15 C20 C19 C18 2.4(5) . . . . ?
C15 C20 C19 C24 -177.5(3) . . . . ?
C5 C6 C1 O1 179.2(3) . . . . ?
C5 C6 C1 C2 -1.3(5) . . . . ?
C23 O6 C17 C18 -2.5(5) . . . . ?
C23 O6 C17 C16 177.9(3) . . . . ?
C13 N1 C14 C11 -2.7(5) . . . . ?
C13 N3 C12 N4 177.3(3) . . . . ?
C13 N3 C12 C11 -3.8(4) . . . . ?
C14 N1 C13 N3 4.9(5) . . . . ?
C14 N1 C13 N2 -175.1(3) . . . . ?
C14 C11 C10 C3 -23.0(5) . . . . ?
C1 C6 C5 O3 -177.3(3) . . . . ?
C1 C6 C5 C4 1.6(5) . . . . ?
C4 C3 C10 C11 94.2(4) . . . . ?
C4 C3 C2 C1 1.4(6) . . . . ?
C12 N3 C13 N1 -1.6(5) . . . . ?
C12 N3 C13 N2 178.4(3) . . . . ?
C12 C11 C10 C3 157.3(3) . . . . ?
C21 O4 C15 C20 -5.0(5) . . . . ?
C21 O4 C15 C16 176.0(3) . . . . ?
C7 O1 C1 C6 -179.8(3) . . . . ?
C7 O1 C1 C2 0.7(6) . . . . ?
C9 O3 C5 C6 -171.8(3) . . . . ?
C9 O3 C5 C4 9.4(5) . . . . ?
C10 C3 C4 C5 179.8(4) . . . . ?
C10 C3 C2 C1 -179.5(4) . . . . ?
C8 O2 C6 C5 73.1(4) . . . . ?
C8 O2 C6 C1 -110.3(4) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C2 C3 C10 C11 -84.8(5) . . . . ?
C22 O5 C16 C17 -99.5(4) . . . . ?
C22 O5 C16 C15 85.3(4) . . . . ?
C34A C33A C32A O10A -38.2(6) . . . . ?
C34A C33A C32A O11A 145.2(8) . . . . ?
O12B C33B C32B O10B -8(2) . . . . ?
O12B C33B C32B O11B 175.3(10) . . . . ?
C34B C33B C32B O10B 112(2) . . . . ?
C34B C33B C32B O11B -64.7(14) . . . . ?

_olex2_exptl_crystal_mounting_method 'Crystal was mounted on a 20 um nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.742
_oxdiff_exptl_absorpt_empirical_full_min 0.495
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.1(2)
2 -0.1(2)
# END of CIF

