# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_qy-hh181126e
_database_code_depnum_ccdc_archive 'CCDC 1975126'
loop_
_audit_author_name
_audit_author_address
HeHuan
;Sichuan university
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 N7 O12'
_chemical_formula_sum            'C20 H27 N7 O12'
_chemical_formula_weight         557.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.29096(14)
_cell_length_b                   14.5006(2)
_cell_length_c                   20.3184(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2737.38(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5984
_cell_measurement_temperature    291.6(2)
_cell_measurement_theta_max      72.3320
_cell_measurement_theta_min      3.7320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15433
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.958
_diffrn_reflns_theta_min         3.745
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -10.00   1.00    1.08    --  -36.42 -77.00 120.00   94
  2  ω   -107.00 -44.00   1.00    1.08    --  -36.42-167.00 142.00   63
  3  ω     10.00 104.00   1.00    1.08    --   36.42  77.00 -30.00   94
  4  ω     23.00  90.00   1.00    1.08    --   36.42-125.00 120.00   67
  5  ω     20.00 104.00   1.00    1.08    --   36.42  57.00-120.00   84
  6  ω     39.00 130.00   1.00    4.31    --  108.71 -30.00   0.00   91
  7  ω     39.00 109.00   1.00    4.31    --  108.71 -94.00 -90.00   70
  8  ω     41.00 135.00   1.00    4.31    --  108.71 -77.00   0.00   94
  9  ω     39.00 109.00   1.00    4.31    --  108.71 -94.00 150.00   70
 10  ω     39.00 130.00   1.00    4.31    --  108.71 -30.00 -60.00   91
 11  ω    100.00 178.00   1.00    4.31    --  108.71 111.00-180.00   78
 12  ω     39.00 130.00   1.00    4.31    --  108.71 -30.00  90.00   91
 13  ω   -106.00 -18.00   1.00    1.08    --  -36.42 -38.00   0.00   88
 14  ω    -55.00  15.00   1.00    1.08    --  -36.42  38.00 150.00   70
 15  ω    -31.00  53.00   1.00    1.08    --   36.42 -57.00 -30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0182013000
_diffrn_orient_matrix_UB_12      -0.0493148000
_diffrn_orient_matrix_UB_13      -0.0666486000
_diffrn_orient_matrix_UB_21      0.0217078000
_diffrn_orient_matrix_UB_22      -0.0938605000
_diffrn_orient_matrix_UB_23      0.0341396000
_diffrn_orient_matrix_UB_31      -0.1633419000
_diffrn_orient_matrix_UB_32      -0.0069744000
_diffrn_orient_matrix_UB_33      0.0119150000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4912
_reflns_number_total             5368
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1068P)²+0.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1492
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00Q(H00Q), C00S(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00U(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N008(H008)
2.d Idealised Me refined as rotating group:
 C00X(H00C,H00D,H00E), C00Y(H00H,H00K,H00L), C00Z(H00M,H00N,H00O), C010(H01A,
 H01B,H01C), C012(H01D,H01E,H01F), C013(H01G,H01H,H01I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O001 O 0.2849(2) 0.15524(14) 0.36328(12) 0.0530(5) Uani 1 1 d . . . . .
O002 O 0.4517(3) 0.40738(14) 0.30624(11) 0.0498(5) Uani 1 1 d . . . . .
O003 O 0.7356(2) 0.49424(14) 0.37265(11) 0.0514(5) Uani 1 1 d . . . . .
O004 O 0.3607(2) 0.49442(15) 0.42442(11) 0.0532(5) Uani 1 1 d . . . . .
O005 O 0.7413(3) 0.55816(18) 0.27244(13) 0.0689(7) Uani 1 1 d . . . . .
O006 O 0.5789(3) 0.2364(2) 0.19306(14) 0.0685(7) Uani 1 1 d . . . . .
O007 O 0.7230(3) 0.67486(16) 0.40313(12) 0.0647(6) Uani 1 1 d . . . . .
N008 N 0.4308(3) 0.26948(17) 0.45961(13) 0.0479(5) Uani 1 1 d . . . . .
H008 H 0.5178 0.2514 0.4661 0.058 Uiso 1 1 calc R . . . .
O009 O 0.2122(3) 0.2913(2) 0.50416(14) 0.0722(7) Uani 1 1 d . . . . .
N00A N 0.1938(3) 0.29923(18) 0.28102(15) 0.0539(6) Uani 1 1 d . . . . .
N00B N 0.0979(3) 0.2421(2) 0.27359(15) 0.0574(7) Uani 1 1 d . . . . .
O00C O 0.7011(3) 0.3329(2) 0.25731(17) 0.0834(9) Uani 1 1 d . . . . .
N00D N 0.3871(4) 0.3846(2) 0.19661(14) 0.0630(7) Uani 1 1 d . . . . .
O00E O 0.3910(4) 0.4952(3) 0.53351(14) 0.0868(9) Uani 1 1 d . . . . .
C00F C 0.3898(3) 0.30162(18) 0.39504(14) 0.0429(6) Uani 1 1 d . . . . .
H00F H 0.2933 0.3286 0.3977 0.052 Uiso 1 1 calc R . . . .
C00G C 0.4945(3) 0.37540(19) 0.36980(15) 0.0447(6) Uani 1 1 d . . . . .
H00G H 0.5905 0.3479 0.3662 0.054 Uiso 1 1 calc R . . . .
N00H N 0.3245(4) 0.4575(3) 0.20568(17) 0.0750(9) Uani 1 1 d . . . . .
C00I C 0.5038(3) 0.4591(2) 0.41442(15) 0.0476(6) Uani 1 1 d . . . . .
H00I H 0.5438 0.4403 0.4570 0.057 Uiso 1 1 calc R . . . .
C00J C 0.3880(3) 0.22370(18) 0.34427(15) 0.0449(6) Uani 1 1 d . . . . .
H00J H 0.4838 0.1959 0.3409 0.054 Uiso 1 1 calc R . . . .
O00K O 0.4593(5) 0.0538(2) 0.3814(3) 0.1165(16) Uani 1 1 d . . . . .
C00L C 0.4407(3) 0.3403(2) 0.25679(15) 0.0489(6) Uani 1 1 d . . . . .
O00M O 0.7692(6) 0.7404(3) 0.49816(18) 0.1161(16) Uani 1 1 d . . . . .
C00N C 0.7974(4) 0.5136(2) 0.31357(18) 0.0539(7) Uani 1 1 d . . . . .
C00O C 0.5907(4) 0.3035(2) 0.23658(15) 0.0523(7) Uani 1 1 d . . . . .
N00P N 0.0008(4) 0.1976(3) 0.2673(2) 0.0866(12) Uani 1 1 d . . . . .
C00Q C 0.5978(3) 0.53535(19) 0.38547(15) 0.0486(6) Uani 1 1 d . . . . .
H00Q H 0.5555 0.5581 0.3444 0.058 Uiso 1 1 calc R . . . .
C00R C 0.3375(3) 0.2670(2) 0.50959(17) 0.0553(7) Uani 1 1 d . . . . .
C00S C 0.3412(3) 0.26046(19) 0.27731(15) 0.0458(6) Uani 1 1 d . . . . .
H00S H 0.3449 0.2111 0.2444 0.055 Uiso 1 1 calc R . . . .
C00T C 0.3356(5) 0.0707(2) 0.3782(2) 0.0689(10) Uani 1 1 d . . . . .
C00U C 0.6206(5) 0.6149(2) 0.43319(18) 0.0625(8) Uani 1 1 d . . . . .
H00A H 0.5307 0.6472 0.4409 0.075 Uiso 1 1 calc R . . . .
H00B H 0.6568 0.5923 0.4750 0.075 Uiso 1 1 calc R . . . .
C00V C 0.7940(5) 0.7324(3) 0.44194(19) 0.0677(9) Uani 1 1 d . . . . .
C00W C 0.3150(4) 0.5054(2) 0.48767(19) 0.0615(8) Uani 1 1 d . . . . .
C00X C 0.9044(5) 0.7850(3) 0.4048(2) 0.0841(13) Uani 1 1 d . . . . .
H00C H 0.9456 0.7463 0.3715 0.126 Uiso 1 1 calc GR . . . .
H00D H 0.9786 0.8051 0.4345 0.126 Uiso 1 1 calc GR . . . .
H00E H 0.8605 0.8378 0.3846 0.126 Uiso 1 1 calc GR . . . .
C00Y C 0.9436(4) 0.4724(3) 0.3092(3) 0.0784(12) Uani 1 1 d . . . . .
H00H H 1.0009 0.4934 0.3456 0.118 Uiso 1 1 calc GR . . . .
H00K H 0.9882 0.4907 0.2687 0.118 Uiso 1 1 calc GR . . . .
H00L H 0.9362 0.4064 0.3107 0.118 Uiso 1 1 calc GR . . . .
C00Z C 0.1599(5) 0.5317(4) 0.4899(3) 0.0842(12) Uani 1 1 d . . . . .
H00M H 0.1503 0.5961 0.4801 0.126 Uiso 1 1 calc GR . . . .
H00N H 0.1222 0.5195 0.5330 0.126 Uiso 1 1 calc GR . . . .
H00O H 0.1075 0.4963 0.4579 0.126 Uiso 1 1 calc GR . . . .
C010 C 0.3972(5) 0.2352(4) 0.5741(2) 0.0889(15) Uani 1 1 d . . . . .
H01A H 0.3488 0.1798 0.5875 0.133 Uiso 1 1 calc GR . . . .
H01B H 0.3827 0.2822 0.6067 0.133 Uiso 1 1 calc GR . . . .
H01C H 0.4983 0.2231 0.5695 0.133 Uiso 1 1 calc GR . . . .
N011 N 0.2662(8) 0.5244(4) 0.2059(3) 0.133(2) Uani 1 1 d . . . . .
C012 C 0.7123(5) 0.2018(4) 0.1656(3) 0.0843(13) Uani 1 1 d . . . . .
H01D H 0.6915 0.1536 0.1346 0.126 Uiso 1 1 calc GR . . . .
H01E H 0.7716 0.1778 0.2002 0.126 Uiso 1 1 calc GR . . . .
H01F H 0.7621 0.2510 0.1436 0.126 Uiso 1 1 calc GR . . . .
C013 C 0.2122(8) 0.0049(3) 0.3871(3) 0.106(2) Uani 1 1 d . . . . .
H01G H 0.1503 0.0269 0.4215 0.159 Uiso 1 1 calc GR . . . .
H01H H 0.2487 -0.0549 0.3987 0.159 Uiso 1 1 calc GR . . . .
H01I H 0.1588 0.0006 0.3468 0.159 Uiso 1 1 calc GR . . . .


_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
O001 C00J 1.432(3) . ?
O001 C00T 1.347(4) . ?
O002 C00G 1.429(4) . ?
O002 C00L 1.402(4) . ?
O003 C00N 1.360(4) . ?
O003 C00Q 1.436(4) . ?
O004 C00I 1.439(4) . ?
O004 C00W 1.363(4) . ?
O005 C00N 1.178(4) . ?
O006 C00O 1.319(4) . ?
O006 C012 1.450(5) . ?
O007 C00U 1.426(4) . ?
O007 C00V 1.324(4) . ?
N008 H008 0.8600 . ?
N008 C00F 1.443(4) . ?
N008 C00R 1.336(4) . ?
O009 C00R 1.222(5) . ?
N00A N00B 1.226(4) . ?
N00A C00S 1.483(4) . ?
N00B N00P 1.117(5) . ?
O00C C00O 1.188(5) . ?
N00D N00H 1.221(5) . ?
N00D C00L 1.468(4) . ?
O00E C00W 1.178(5) . ?
C00F H00F 0.9800 . ?
C00F C00G 1.534(4) . ?
C00F C00J 1.530(4) . ?
C00G H00G 0.9800 . ?
C00G C00I 1.518(4) . ?
N00H N011 1.110(6) . ?
C00I H00I 0.9800 . ?
C00I C00Q 1.526(4) . ?
C00J H00J 0.9800 . ?
C00J C00S 1.524(4) . ?
O00K C00T 1.177(6) . ?
C00L C00O 1.548(5) . ?
C00L C00S 1.539(4) . ?
O00M C00V 1.171(5) . ?
C00N C00Y 1.488(5) . ?
C00Q H00Q 0.9800 . ?
C00Q C00U 1.522(4) . ?
C00R C010 1.496(5) . ?
C00S H00S 0.9800 . ?
C00T C013 1.503(7) . ?
C00U H00A 0.9700 . ?
C00U H00B 0.9700 . ?
C00V C00X 1.485(6) . ?
C00W C00Z 1.491(6) . ?
C00X H00C 0.9600 . ?
C00X H00D 0.9600 . ?
C00X H00E 0.9600 . ?
C00Y H00H 0.9600 . ?
C00Y H00K 0.9600 . ?
C00Y H00L 0.9600 . ?
C00Z H00M 0.9600 . ?
C00Z H00N 0.9600 . ?
C00Z H00O 0.9600 . ?
C010 H01A 0.9600 . ?
C010 H01B 0.9600 . ?
C010 H01C 0.9600 . ?
C012 H01D 0.9600 . ?
C012 H01E 0.9600 . ?
C012 H01F 0.9600 . ?
C013 H01G 0.9600 . ?
C013 H01H 0.9600 . ?
C013 H01I 0.9600 . ?

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
C00T O001 C00J 117.2(3) . . ?
C00L O002 C00G 116.3(2) . . ?
C00N O003 C00Q 116.8(2) . . ?
C00W O004 C00I 117.6(3) . . ?
C00O O006 C012 116.3(3) . . ?
C00V O007 C00U 117.5(3) . . ?
C00F N008 H008 119.0 . . ?
C00R N008 H008 119.0 . . ?
C00R N008 C00F 121.9(3) . . ?
N00B N00A C00S 114.1(2) . . ?
N00P N00B N00A 172.7(4) . . ?
N00H N00D C00L 114.5(3) . . ?
N008 C00F H00F 108.7 . . ?
N008 C00F C00G 111.2(2) . . ?
N008 C00F C00J 112.2(2) . . ?
C00G C00F H00F 108.7 . . ?
C00J C00F H00F 108.7 . . ?
C00J C00F C00G 107.3(2) . . ?
O002 C00G C00F 110.6(2) . . ?
O002 C00G H00G 108.6 . . ?
O002 C00G C00I 107.2(2) . . ?
C00F C00G H00G 108.6 . . ?
C00I C00G C00F 113.2(2) . . ?
C00I C00G H00G 108.6 . . ?
N011 N00H N00D 171.6(5) . . ?
O004 C00I C00G 108.4(2) . . ?
O004 C00I H00I 109.0 . . ?
O004 C00I C00Q 109.0(2) . . ?
C00G C00I H00I 109.0 . . ?
C00G C00I C00Q 112.4(3) . . ?
C00Q C00I H00I 109.0 . . ?
O001 C00J C00F 109.7(2) . . ?
O001 C00J H00J 109.9 . . ?
O001 C00J C00S 107.0(2) . . ?
C00F C00J H00J 109.9 . . ?
C00S C00J C00F 110.3(2) . . ?
C00S C00J H00J 109.9 . . ?
O002 C00L N00D 108.6(2) . . ?
O002 C00L C00O 111.3(3) . . ?
O002 C00L C00S 111.8(2) . . ?
N00D C00L C00O 103.6(3) . . ?
N00D C00L C00S 110.6(3) . . ?
C00S C00L C00O 110.6(2) . . ?
O003 C00N C00Y 110.8(3) . . ?
O005 C00N O003 123.6(3) . . ?
O005 C00N C00Y 125.6(4) . . ?
O006 C00O C00L 110.9(3) . . ?
O00C C00O O006 125.0(3) . . ?
O00C C00O C00L 124.0(3) . . ?
O003 C00Q C00I 106.2(2) . . ?
O003 C00Q H00Q 110.1 . . ?
O003 C00Q C00U 107.8(3) . . ?
C00I C00Q H00Q 110.1 . . ?
C00U C00Q C00I 112.5(3) . . ?
C00U C00Q H00Q 110.1 . . ?
N008 C00R C010 115.7(3) . . ?
O009 C00R N008 122.8(3) . . ?
O009 C00R C010 121.4(3) . . ?
N00A C00S C00J 110.5(2) . . ?
N00A C00S C00L 106.4(2) . . ?
N00A C00S H00S 110.1 . . ?
C00J C00S C00L 109.5(2) . . ?
C00J C00S H00S 110.1 . . ?
C00L C00S H00S 110.1 . . ?
O001 C00T C013 109.8(4) . . ?
O00K C00T O001 123.0(4) . . ?
O00K C00T C013 127.3(4) . . ?
O007 C00U C00Q 106.4(3) . . ?
O007 C00U H00A 110.5 . . ?
O007 C00U H00B 110.5 . . ?
C00Q C00U H00A 110.5 . . ?
C00Q C00U H00B 110.5 . . ?
H00A C00U H00B 108.6 . . ?
O007 C00V C00X 111.5(3) . . ?
O00M C00V O007 123.1(4) . . ?
O00M C00V C00X 125.5(4) . . ?
O004 C00W C00Z 111.1(4) . . ?
O00E C00W O004 123.0(3) . . ?
O00E C00W C00Z 126.0(4) . . ?
C00V C00X H00C 109.5 . . ?
C00V C00X H00D 109.5 . . ?
C00V C00X H00E 109.5 . . ?
H00C C00X H00D 109.5 . . ?
H00C C00X H00E 109.5 . . ?
H00D C00X H00E 109.5 . . ?
C00N C00Y H00H 109.5 . . ?
C00N C00Y H00K 109.5 . . ?
C00N C00Y H00L 109.5 . . ?
H00H C00Y H00K 109.5 . . ?
H00H C00Y H00L 109.5 . . ?
H00K C00Y H00L 109.5 . . ?
C00W C00Z H00M 109.5 . . ?
C00W C00Z H00N 109.5 . . ?
C00W C00Z H00O 109.5 . . ?
H00M C00Z H00N 109.5 . . ?
H00M C00Z H00O 109.5 . . ?
H00N C00Z H00O 109.5 . . ?
C00R C010 H01A 109.5 . . ?
C00R C010 H01B 109.5 . . ?
C00R C010 H01C 109.5 . . ?
H01A C010 H01B 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 109.5 . . ?
O006 C012 H01D 109.5 . . ?
O006 C012 H01E 109.5 . . ?
O006 C012 H01F 109.5 . . ?
H01D C012 H01E 109.5 . . ?
H01D C012 H01F 109.5 . . ?
H01E C012 H01F 109.5 . . ?
C00T C013 H01G 109.5 . . ?
C00T C013 H01H 109.5 . . ?
C00T C013 H01I 109.5 . . ?
H01G C013 H01H 109.5 . . ?
H01G C013 H01I 109.5 . . ?
H01H C013 H01I 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-14
_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 1.537
_oxdiff_exptl_absorpt_empirical_full_min 0.785
####################################################################### 
# 
# 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_190510_s5_hh_0405b
_database_code_depnum_ccdc_archive 'CCDC 1975127'
loop_
_audit_author_name
_audit_author_address
HeHuan
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2020-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H35 N7 O12'
_chemical_formula_sum            'C40 H35 N7 O12'
_chemical_formula_weight         805.75
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -z'

_cell_length_a                   19.7672(8)
_cell_length_b                   19.7672(8)
_cell_length_c                   23.6968(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8018.8(8)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5847
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.1160
_cell_measurement_theta_min      3.2860
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.001
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34678
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.936
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -59.70   0.7000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  178.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00   53.90   0.7000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106    0.0000  120.0000 177

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   11.20   0.7000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106   19.0000   30.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0175588000
_diffrn_orient_matrix_UB_12      -0.0392682000
_diffrn_orient_matrix_UB_13      -0.0093801000
_diffrn_orient_matrix_UB_21      -0.0297968000
_diffrn_orient_matrix_UB_22      -0.0110978000
_diffrn_orient_matrix_UB_23      0.0205728000
_diffrn_orient_matrix_UB_31      -0.0228102000
_diffrn_orient_matrix_UB_32      0.0071383000
_diffrn_orient_matrix_UB_33      -0.0196121000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5441
_reflns_number_total             10925
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 1764 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         10925
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0819
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1419P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2096
_refine_ls_wR_factor_ref         0.2662
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2A)
Uanis(C37) = Uanis(C36)
3. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_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
O1 O 0.3941(2) 0.7464(2) 0.37247(15) 0.0752(10) Uani 1 1 d . . . . .
O3 O 0.4112(3) 0.9019(3) 0.3700(2) 0.1086(15) Uani 1 1 d . . . . .
O4 O 0.5518(2) 0.8674(2) 0.24610(15) 0.0805(11) Uani 1 1 d . . . . .
O5 O 0.6151(3) 0.9961(3) 0.2570(2) 0.1039(14) Uani 1 1 d . . . . .
O6 O 0.6568(3) 0.7914(4) 0.3243(3) 0.148(2) Uani 1 1 d . . . . .
O7 O 0.4704(2) 0.6727(2) 0.41206(15) 0.0753(10) Uani 1 1 d . . . . .
O8 O 0.5828(3) 0.6882(3) 0.4475(2) 0.1157(16) Uani 1 1 d . . . . .
O9 O 0.4406(2) 0.7991(2) 0.50529(16) 0.0790(10) Uani 1 1 d . . . . .
O10 O 0.3144(3) 0.7506(3) 0.5270(2) 0.1052(14) Uani 1 1 d . . . . .
O11 O 0.5015(3) 0.7059(3) 0.5528(2) 0.0987(13) Uani 1 1 d . . . . .
O12 O 0.4642(4) 0.7427(5) 0.6292(3) 0.164(3) Uani 1 1 d . . . . .
N1 N 0.2935(3) 0.7142(4) 0.3089(3) 0.1007(16) Uani 1 1 d . . . . .
N2 N 0.2459(4) 0.6731(5) 0.3478(3) 0.115(2) Uani 1 1 d . . . . .
N3 N 0.1994(5) 0.6292(6) 0.3775(4) 0.167(4) Uani 1 1 d . . . . .
N4 N 0.3999(4) 0.8493(3) 0.2407(3) 0.0974(15) Uani 1 1 d . . . . .
N5 N 0.3620(4) 0.8116(4) 0.2009(3) 0.114(2) Uani 1 1 d . . . . .
N6 N 0.3264(7) 0.7833(6) 0.1630(4) 0.176(4) Uani 1 1 d . . . . .
N7 N 0.6086(3) 0.8640(3) 0.3597(2) 0.0751(12) Uani 1 1 d . . . . .
H7 H 0.621(3) 0.908(4) 0.378(2) 0.084(18) Uiso 1 1 d . . . . .
C1 C 0.3671(3) 0.7777(3) 0.3308(3) 0.0789(15) Uani 1 1 d . . . . .
C2 C 0.4219(3) 0.8057(3) 0.2801(2) 0.0747(14) Uani 1 1 d . . . . .
H2 H 0.4162 0.7597 0.2603 0.090 Uiso 1 1 calc R . . . .
C3 C 0.5067(3) 0.8560(3) 0.2970(2) 0.0745(15) Uani 1 1 d . . . . .
H3 H 0.5161 0.9063 0.3116 0.089 Uiso 1 1 calc R . . . .
C4 C 0.5286(3) 0.8147(3) 0.3406(2) 0.0695(14) Uani 1 1 d . . . . .
H4 H 0.5235 0.7670 0.3239 0.083 Uiso 1 1 calc R . . . .
C5 C 0.4737(3) 0.7926(3) 0.3909(2) 0.0693(14) Uani 1 1 d . . . . .
H5 H 0.4803 0.8407 0.4079 0.083 Uiso 1 1 calc R . . . .
C6 C 0.3513(5) 0.8382(5) 0.3579(3) 0.097(2) Uani 1 1 d . . . . .
C7 C 0.3997(7) 0.9595(5) 0.4035(4) 0.138(3) Uani 1 1 d . . . . .
H7A H 0.4463 0.9925 0.4246 0.206 Uiso 1 1 calc GR . . . .
H7B H 0.3567 0.9321 0.4291 0.206 Uiso 1 1 calc GR . . . .
H7C H 0.3888 0.9909 0.3784 0.206 Uiso 1 1 calc GR . . . .
C8 C 0.6022(3) 0.9392(3) 0.2297(2) 0.0739(15) Uani 1 1 d . . . . .
C9 C 0.6392(3) 0.9427(3) 0.1754(2) 0.0773(15) Uani 1 1 d . . . . .
C10 C 0.6148(5) 0.8793(4) 0.1420(3) 0.106(2) Uani 1 1 d . . . . .
H10 H 0.5746 0.8312 0.1543 0.127 Uiso 1 1 calc R . . . .
C11 C 0.6484(6) 0.8849(6) 0.0900(4) 0.139(3) Uani 1 1 d . . . . .
H11 H 0.6315 0.8409 0.0674 0.167 Uiso 1 1 calc R . . . .
C12 C 0.7076(6) 0.9569(7) 0.0719(4) 0.142(3) Uani 1 1 d . . . . .
H12 H 0.7314 0.9612 0.0372 0.170 Uiso 1 1 calc R . . . .
C13 C 0.7309(5) 1.0208(5) 0.1040(4) 0.116(3) Uani 1 1 d . . . . .
H13 H 0.7703 1.0691 0.0913 0.140 Uiso 1 1 calc R . . . .
C14 C 0.6969(4) 1.0149(4) 0.1553(3) 0.0939(18) Uani 1 1 d . . . . .
H14 H 0.7124 1.0595 0.1770 0.113 Uiso 1 1 calc R . . . .
C15 C 0.6661(4) 0.8483(4) 0.3501(3) 0.098(2) Uani 1 1 d . . . . .
C16 C 0.7425(5) 0.9029(5) 0.3759(5) 0.138(3) Uani 1 1 d . . . . .
H16A H 0.7409 0.9470 0.3913 0.207 Uiso 1 1 calc GR . . . .
H16B H 0.7827 0.9205 0.3477 0.207 Uiso 1 1 calc GR . . . .
H16C H 0.7536 0.8767 0.4055 0.207 Uiso 1 1 calc GR . . . .
C17 C 0.4835(3) 0.7456(3) 0.4360(2) 0.0696(14) Uani 1 1 d . . . . .
H17 H 0.5366 0.7746 0.4513 0.084 Uiso 1 1 calc R . . . .
C18 C 0.5226(4) 0.6487(4) 0.4222(3) 0.0821(16) Uani 1 1 d . . . . .
C19 C 0.4964(4) 0.5706(4) 0.4004(2) 0.0815(16) Uani 1 1 d . . . . .
C20 C 0.4309(4) 0.5323(4) 0.3670(3) 0.0917(18) Uani 1 1 d . . . . .
H20 H 0.4020 0.5561 0.3579 0.110 Uiso 1 1 calc R . . . .
C21 C 0.4084(5) 0.4584(5) 0.3471(4) 0.118(3) Uani 1 1 d . . . . .
H21 H 0.3647 0.4329 0.3240 0.142 Uiso 1 1 calc R . . . .
C22 C 0.4497(6) 0.4222(6) 0.3611(5) 0.136(3) Uani 1 1 d . . . . .
H22 H 0.4348 0.3727 0.3474 0.164 Uiso 1 1 calc R . . . .
C23 C 0.5135(7) 0.4605(7) 0.3959(4) 0.141(3) Uani 1 1 d . . . . .
H23 H 0.5408 0.4356 0.4068 0.169 Uiso 1 1 calc R . . . .
C24 C 0.5374(5) 0.5336(5) 0.4147(3) 0.105(2) Uani 1 1 d . . . . .
H24 H 0.5816 0.5590 0.4374 0.126 Uiso 1 1 calc R . . . .
C25 C 0.4246(3) 0.7250(3) 0.4835(2) 0.0761(15) Uani 1 1 d . . . . .
H25 H 0.3722 0.6994 0.4669 0.091 Uiso 1 1 calc R . . . .
C26 C 0.3799(4) 0.8048(4) 0.5260(2) 0.0809(16) Uani 1 1 d . . . . .
C27 C 0.4057(4) 0.8867(4) 0.5451(2) 0.0800(16) Uani 1 1 d . . . . .
C28 C 0.3513(4) 0.8989(4) 0.5714(3) 0.098(2) Uani 1 1 d . . . . .
H28 H 0.3009 0.8575 0.5769 0.117 Uiso 1 1 calc R . . . .
C29 C 0.3712(5) 0.9724(5) 0.5898(4) 0.118(2) Uani 1 1 d . . . . .
H29 H 0.3342 0.9809 0.6078 0.142 Uiso 1 1 calc R . . . .
C30 C 0.4450(6) 1.0329(5) 0.5818(4) 0.121(3) Uani 1 1 d . . . . .
H30 H 0.4584 1.0827 0.5942 0.145 Uiso 1 1 calc R . . . .
C31 C 0.4999(5) 1.0208(5) 0.5554(4) 0.117(3) Uani 1 1 d . . . . .
H31 H 0.5502 1.0622 0.5496 0.141 Uiso 1 1 calc R . . . .
C32 C 0.4795(4) 0.9468(4) 0.5376(3) 0.0949(19) Uani 1 1 d . . . . .
H32 H 0.5166 0.9380 0.5203 0.114 Uiso 1 1 calc R . . . .
C33 C 0.4259(4) 0.6730(4) 0.5288(3) 0.097(2) Uani 1 1 d . . . . .
H33A H 0.3884 0.6660 0.5580 0.116 Uiso 1 1 calc R . . . .
H33B H 0.4109 0.6221 0.5131 0.116 Uiso 1 1 calc R . . . .
C34 C 0.5152(6) 0.7378(4) 0.6037(4) 0.113(2) Uani 1 1 d . . . . .
C35 C 0.5966(7) 0.7662(5) 0.6221(4) 0.115(3) Uani 1 1 d . . . . .
C36 C 0.6177(9) 0.7997(7) 0.6748(6) 0.187(4) Uani 1 1 d . . . . .
H36 H 0.5834 0.8079 0.6966 0.224 Uiso 1 1 calc R . . . .
C37 C 0.6901(10) 0.8202(8) 0.6940(6) 0.187(4) Uani 1 1 d . . . . .
H37 H 0.7039 0.8384 0.7308 0.224 Uiso 1 1 calc R . . . .
C38 C 0.7436(11) 0.8146(12) 0.6596(10) 0.227(8) Uani 1 1 d . . . . .
H38 H 0.7941 0.8320 0.6725 0.272 Uiso 1 1 calc R . . . .
C39 C 0.7228(9) 0.7845(9) 0.6087(8) 0.198(6) Uani 1 1 d . . . . .
H39 H 0.7588 0.7811 0.5854 0.238 Uiso 1 1 calc R . . . .
C40 C 0.6486(7) 0.7585(6) 0.5900(5) 0.135(3) Uani 1 1 d . . . . .
H40 H 0.6336 0.7352 0.5547 0.162 Uiso 1 1 calc R . . . .
O2 O 0.2837(7) 0.8265(6) 0.3629(8) 0.170(6) Uani 0.74(2) 1 d . . P A 1
O2A O 0.310(2) 0.824(2) 0.398(3) 0.170(6) Uani 0.26(2) 1 d . . 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 1.406(7) . ?
O1 C5 1.435(7) . ?
O3 C6 1.258(8) . ?
O3 C7 1.496(9) . ?
O4 C3 1.448(6) . ?
O4 C8 1.320(6) . ?
O5 C8 1.210(7) . ?
O6 C15 1.211(8) . ?
O7 C17 1.446(6) . ?
O7 C18 1.356(7) . ?
O8 C18 1.207(7) . ?
O9 C25 1.431(7) . ?
O9 C26 1.351(7) . ?
O10 C26 1.199(7) . ?
O11 C33 1.416(8) . ?
O11 C34 1.326(9) . ?
O12 C34 1.220(10) . ?
N1 N2 1.276(10) . ?
N1 C1 1.461(8) . ?
N2 N3 1.139(10) . ?
N4 N5 1.204(9) . ?
N4 C2 1.475(8) . ?
N5 N6 1.106(9) . ?
N7 H7 0.89(7) . ?
N7 C4 1.454(7) . ?
N7 C15 1.339(9) . ?
C1 C2 1.524(8) . ?
C1 C6 1.520(10) . ?
C2 H2 0.9800 . ?
C2 C3 1.514(8) . ?
C3 H3 0.9800 . ?
C3 C4 1.510(8) . ?
C4 H4 0.9800 . ?
C4 C5 1.520(7) . ?
C5 H5 0.9800 . ?
C5 C17 1.492(8) . ?
C6 O2 1.242(14) . ?
C6 O2A 1.20(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.466(8) . ?
C9 C10 1.351(9) . ?
C9 C14 1.391(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(12) . ?
C12 H12 0.9300 . ?
C12 C13 1.342(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.481(11) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9800 . ?
C17 C25 1.522(8) . ?
C18 C19 1.456(9) . ?
C19 C20 1.376(9) . ?
C19 C24 1.377(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.367(12) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(13) . ?
C23 H23 0.9300 . ?
C23 C24 1.352(12) . ?
C24 H24 0.9300 . ?
C25 H25 0.9800 . ?
C25 C33 1.496(9) . ?
C26 C27 1.503(9) . ?
C27 C28 1.364(9) . ?
C27 C32 1.357(9) . ?
C28 H28 0.9300 . ?
C28 C29 1.373(11) . ?
C29 H29 0.9300 . ?
C29 C30 1.360(12) . ?
C30 H30 0.9300 . ?
C30 C31 1.372(11) . ?
C31 H31 0.9300 . ?
C31 C32 1.374(10) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.481(13) . ?
C35 C36 1.376(14) . ?
C35 C40 1.347(13) . ?
C36 H36 0.9300 . ?
C36 C37 1.355(19) . ?
C37 H37 0.9300 . ?
C37 C38 1.38(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.32(2) . ?
C39 H39 0.9300 . ?
C39 C40 1.363(15) . ?
C40 H40 0.9300 . ?

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 C5 118.1(4) . . ?
C6 O3 C7 117.2(7) . . ?
C8 O4 C3 119.2(4) . . ?
C18 O7 C17 119.3(4) . . ?
C26 O9 C25 117.7(5) . . ?
C34 O11 C33 120.1(6) . . ?
N2 N1 C1 113.1(5) . . ?
N3 N2 N1 171.4(8) . . ?
N5 N4 C2 114.1(5) . . ?
N6 N5 N4 173.0(9) . . ?
C4 N7 H7 119(4) . . ?
C15 N7 H7 117(4) . . ?
C15 N7 C4 123.8(5) . . ?
O1 C1 N1 107.7(5) . . ?
O1 C1 C2 110.8(5) . . ?
O1 C1 C6 108.8(5) . . ?
N1 C1 C2 104.7(5) . . ?
N1 C1 C6 108.6(6) . . ?
C6 C1 C2 115.8(5) . . ?
N4 C2 C1 110.3(5) . . ?
N4 C2 H2 108.1 . . ?
N4 C2 C3 109.7(5) . . ?
C1 C2 H2 108.1 . . ?
C3 C2 C1 112.5(5) . . ?
C3 C2 H2 108.1 . . ?
O4 C3 C2 106.0(4) . . ?
O4 C3 H3 110.3 . . ?
O4 C3 C4 109.5(4) . . ?
C2 C3 H3 110.3 . . ?
C4 C3 C2 110.5(4) . . ?
C4 C3 H3 110.3 . . ?
N7 C4 C3 111.2(4) . . ?
N7 C4 H4 108.9 . . ?
N7 C4 C5 109.2(4) . . ?
C3 C4 H4 108.9 . . ?
C3 C4 C5 109.6(5) . . ?
C5 C4 H4 108.9 . . ?
O1 C5 C4 110.1(4) . . ?
O1 C5 H5 108.3 . . ?
O1 C5 C17 105.3(4) . . ?
C4 C5 H5 108.3 . . ?
C17 C5 C4 116.3(5) . . ?
C17 C5 H5 108.3 . . ?
O3 C6 C1 115.0(7) . . ?
O2 C6 O3 123.5(8) . . ?
O2 C6 C1 121.3(8) . . ?
O2A C6 O3 104.2(19) . . ?
O2A C6 C1 122.2(19) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 C9 113.6(5) . . ?
O5 C8 O4 122.5(5) . . ?
O5 C8 C9 123.8(5) . . ?
C10 C9 C8 122.1(6) . . ?
C10 C9 C14 118.8(6) . . ?
C14 C9 C8 118.9(6) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(7) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.0(8) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(8) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(7) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.5(7) . . ?
C13 C14 H14 119.8 . . ?
O6 C15 N7 123.3(6) . . ?
O6 C15 C16 120.8(7) . . ?
N7 C15 C16 115.8(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O7 C17 C5 109.0(4) . . ?
O7 C17 H17 109.6 . . ?
O7 C17 C25 107.0(4) . . ?
C5 C17 H17 109.6 . . ?
C5 C17 C25 112.1(5) . . ?
C25 C17 H17 109.6 . . ?
O7 C18 C19 112.3(5) . . ?
O8 C18 O7 122.7(6) . . ?
O8 C18 C19 125.1(6) . . ?
C20 C19 C18 121.7(6) . . ?
C20 C19 C24 119.4(6) . . ?
C24 C19 C18 119.0(6) . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.7(7) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(8) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.8(8) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.3(8) . . ?
C24 C23 H23 119.4 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.2(7) . . ?
C23 C24 H24 119.9 . . ?
O9 C25 C17 104.2(4) . . ?
O9 C25 H25 108.1 . . ?
O9 C25 C33 111.9(5) . . ?
C17 C25 H25 108.1 . . ?
C33 C25 C17 116.1(5) . . ?
C33 C25 H25 108.1 . . ?
O9 C26 C27 111.2(5) . . ?
O10 C26 O9 122.7(6) . . ?
O10 C26 C27 126.1(6) . . ?
C28 C27 C26 117.1(6) . . ?
C32 C27 C26 122.8(6) . . ?
C32 C27 C28 120.1(6) . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 119.9(7) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 119.9(7) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.3(8) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 120.4 . . ?
C30 C31 C32 119.3(7) . . ?
C32 C31 H31 120.4 . . ?
C27 C32 C31 120.4(6) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
O11 C33 C25 110.4(5) . . ?
O11 C33 H33A 109.6 . . ?
O11 C33 H33B 109.6 . . ?
C25 C33 H33A 109.6 . . ?
C25 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
O11 C34 C35 112.0(8) . . ?
O12 C34 O11 120.5(9) . . ?
O12 C34 C35 127.5(9) . . ?
C36 C35 C34 117.4(11) . . ?
C40 C35 C34 122.4(9) . . ?
C40 C35 C36 120.1(11) . . ?
C35 C36 H36 121.0 . . ?
C37 C36 C35 118.0(15) . . ?
C37 C36 H36 121.0 . . ?
C36 C37 H37 119.6 . . ?
C36 C37 C38 120.9(14) . . ?
C38 C37 H37 119.6 . . ?
C37 C38 H38 120.1 . . ?
C39 C38 C37 119.8(17) . . ?
C39 C38 H38 120.1 . . ?
C38 C39 H39 119.9 . . ?
C38 C39 C40 120.1(17) . . ?
C40 C39 H39 119.9 . . ?
C35 C40 C39 120.7(12) . . ?
C35 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N4 -171.2(4) . . . . ?
O1 C1 C2 C3 -48.4(6) . . . . ?
O1 C1 C6 O3 74.3(7) . . . . ?
O1 C1 C6 O2 -111.3(13) . . . . ?
O1 C1 C6 O2A -54(3) . . . . ?
O1 C5 C17 O7 61.7(5) . . . . ?
O1 C5 C17 C25 -56.5(5) . . . . ?
O4 C3 C4 N7 66.9(5) . . . . ?
O4 C3 C4 C5 -172.2(4) . . . . ?
O4 C8 C9 C10 9.5(9) . . . . ?
O4 C8 C9 C14 -176.2(6) . . . . ?
O5 C8 C9 C10 -169.5(7) . . . . ?
O5 C8 C9 C14 4.8(9) . . . . ?
O7 C17 C25 O9 180.0(4) . . . . ?
O7 C17 C25 C33 56.4(6) . . . . ?
O7 C18 C19 C20 8.1(8) . . . . ?
O7 C18 C19 C24 -170.4(6) . . . . ?
O8 C18 C19 C20 -173.2(7) . . . . ?
O8 C18 C19 C24 8.2(10) . . . . ?
O9 C25 C33 O11 -63.5(7) . . . . ?
O9 C26 C27 C28 -174.5(5) . . . . ?
O9 C26 C27 C32 4.8(8) . . . . ?
O10 C26 C27 C28 7.4(9) . . . . ?
O10 C26 C27 C32 -173.4(7) . . . . ?
O11 C34 C35 C36 -179.2(8) . . . . ?
O11 C34 C35 C40 -0.9(11) . . . . ?
O12 C34 C35 C36 2.7(13) . . . . ?
O12 C34 C35 C40 -179.0(10) . . . . ?
N1 C1 C2 N4 72.9(6) . . . . ?
N1 C1 C2 C3 -164.3(5) . . . . ?
N1 C1 C6 O3 -168.7(6) . . . . ?
N1 C1 C6 O2 5.6(14) . . . . ?
N1 C1 C6 O2A 63(3) . . . . ?
N2 N1 C1 O1 48.2(7) . . . . ?
N2 N1 C1 C2 166.2(6) . . . . ?
N2 N1 C1 C6 -69.5(7) . . . . ?
N4 C2 C3 O4 -65.7(6) . . . . ?
N4 C2 C3 C4 175.7(4) . . . . ?
N5 N4 C2 C1 -99.5(7) . . . . ?
N5 N4 C2 C3 136.1(6) . . . . ?
N7 C4 C5 O1 177.7(4) . . . . ?
N7 C4 C5 C17 -62.6(6) . . . . ?
C1 O1 C5 C4 -55.9(6) . . . . ?
C1 O1 C5 C17 177.9(4) . . . . ?
C1 C2 C3 O4 171.1(5) . . . . ?
C1 C2 C3 C4 52.6(6) . . . . ?
C2 C1 C6 O3 -51.3(8) . . . . ?
C2 C1 C6 O2 123.0(13) . . . . ?
C2 C1 C6 O2A -179(3) . . . . ?
C2 C3 C4 N7 -176.7(4) . . . . ?
C2 C3 C4 C5 -55.8(6) . . . . ?
C3 O4 C8 O5 3.7(8) . . . . ?
C3 O4 C8 C9 -175.3(5) . . . . ?
C3 C4 C5 O1 55.7(6) . . . . ?
C3 C4 C5 C17 175.3(5) . . . . ?
C4 N7 C15 O6 0.2(12) . . . . ?
C4 N7 C15 C16 -176.4(7) . . . . ?
C4 C5 C17 O7 -60.5(6) . . . . ?
C4 C5 C17 C25 -178.7(5) . . . . ?
C5 O1 C1 N1 165.5(5) . . . . ?
C5 O1 C1 C2 51.5(6) . . . . ?
C5 O1 C1 C6 -77.0(6) . . . . ?
C5 C17 C25 O9 -60.7(6) . . . . ?
C5 C17 C25 C33 175.7(5) . . . . ?
C6 C1 C2 N4 -46.6(7) . . . . ?
C6 C1 C2 C3 76.2(7) . . . . ?
C7 O3 C6 C1 -172.2(6) . . . . ?
C7 O3 C6 O2 13.7(16) . . . . ?
C7 O3 C6 O2A -36(3) . . . . ?
C8 O4 C3 C2 125.4(5) . . . . ?
C8 O4 C3 C4 -115.4(5) . . . . ?
C8 C9 C10 C11 177.2(8) . . . . ?
C8 C9 C14 C13 -177.9(7) . . . . ?
C9 C10 C11 C12 -0.6(15) . . . . ?
C10 C9 C14 C13 -3.4(11) . . . . ?
C10 C11 C12 C13 -1.3(17) . . . . ?
C11 C12 C13 C14 0.8(16) . . . . ?
C12 C13 C14 C9 1.6(13) . . . . ?
C14 C9 C10 C11 2.8(12) . . . . ?
C15 N7 C4 C3 -113.9(6) . . . . ?
C15 N7 C4 C5 125.0(6) . . . . ?
C17 O7 C18 O8 -5.1(8) . . . . ?
C17 O7 C18 C19 173.6(5) . . . . ?
C17 C25 C33 O11 56.0(7) . . . . ?
C18 O7 C17 C5 131.4(5) . . . . ?
C18 O7 C17 C25 -107.3(5) . . . . ?
C18 C19 C20 C21 179.8(7) . . . . ?
C18 C19 C24 C23 178.8(8) . . . . ?
C19 C20 C21 C22 1.2(12) . . . . ?
C20 C19 C24 C23 0.2(11) . . . . ?
C20 C21 C22 C23 0.7(14) . . . . ?
C21 C22 C23 C24 -2.3(16) . . . . ?
C22 C23 C24 C19 1.8(15) . . . . ?
C24 C19 C20 C21 -1.7(10) . . . . ?
C25 O9 C26 O10 0.4(8) . . . . ?
C25 O9 C26 C27 -177.8(5) . . . . ?
C26 O9 C25 C17 147.7(5) . . . . ?
C26 O9 C25 C33 -86.0(6) . . . . ?
C26 C27 C28 C29 -180.0(7) . . . . ?
C26 C27 C32 C31 179.4(7) . . . . ?
C27 C28 C29 C30 0.0(12) . . . . ?
C28 C27 C32 C31 -1.3(11) . . . . ?
C28 C29 C30 C31 -0.1(14) . . . . ?
C29 C30 C31 C32 -0.5(14) . . . . ?
C30 C31 C32 C27 1.2(12) . . . . ?
C32 C27 C28 C29 0.7(11) . . . . ?
C33 O11 C34 O12 -3.8(11) . . . . ?
C33 O11 C34 C35 177.9(6) . . . . ?
C34 O11 C33 C25 105.9(7) . . . . ?
C34 C35 C36 C37 174.8(10) . . . . ?
C34 C35 C40 C39 -179.1(10) . . . . ?
C35 C36 C37 C38 6(2) . . . . ?
C36 C35 C40 C39 -0.9(16) . . . . ?
C36 C37 C38 C39 -4(3) . . . . ?
C37 C38 C39 C40 0(3) . . . . ?
C38 C39 C40 C35 3(2) . . . . ?
C40 C35 C36 C37 -3.5(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_190226_s3_yd_1
_database_code_depnum_ccdc_archive 'CCDC 1975130'
loop_
_audit_author_name
_audit_author_address
HeHuan
;Sichuan university
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H16 N6 O8, C Cl3'
_chemical_formula_sum            'C14 H16 Cl3 N6 O8'
_chemical_formula_weight         502.68
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.6304(6)
_cell_length_b                   10.8741(9)
_cell_length_c                   22.9325(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2152.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2240
_cell_measurement_theta_min      3.4780
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9826
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         3.013
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   24.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   54.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       17.0762  -99.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00   58.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       17.0762    0.0000  -60.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0207637000
_diffrn_orient_matrix_UB_12      0.0349203000
_diffrn_orient_matrix_UB_13      -0.0249130000
_diffrn_orient_matrix_UB_21      0.0300978000
_diffrn_orient_matrix_UB_22      0.0537979000
_diffrn_orient_matrix_UB_23      0.0133768000
_diffrn_orient_matrix_UB_31      0.0735829000
_diffrn_orient_matrix_UB_32      -0.0121796000
_diffrn_orient_matrix_UB_33      -0.0124854000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3366
_reflns_number_total             4407
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1108 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.030
_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)+(0.0825P)²+0.6140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1562
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl3) = Uanis(Cl3A)
Uanis(Cl1) = Uanis(Cl1A)
Uanis(Cl2) = Uanis(Cl2A)
3. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.5611(3) 0.3825(3) 0.37861(12) 0.0377(7) Uani 1 1 d . . . . .
O2 O 0.4219(4) 0.4594(3) 0.45110(13) 0.0449(8) Uani 1 1 d . . . . .
O3 O 0.4484(3) 0.1176(3) 0.38989(11) 0.0341(6) Uani 1 1 d . . . . .
O4 O 0.6594(5) 0.5344(3) 0.43438(17) 0.0583(9) Uani 1 1 d . . . . .
O5 O 0.5301(4) 0.0410(4) 0.51610(18) 0.0710(12) Uani 1 1 d . . . . .
O6 O 0.3909(4) -0.0911(3) 0.46456(14) 0.0520(9) Uani 1 1 d . . . . .
O7 O 0.4773(5) 0.2828(3) 0.25462(13) 0.0518(9) Uani 1 1 d . . . . .
O8 O 0.4100(4) 0.1022(3) 0.21355(14) 0.0564(10) Uani 1 1 d . . . . .
N1 N 0.2822(4) 0.2456(4) 0.52424(17) 0.0444(10) Uani 1 1 d . . . . .
N2 N 0.3094(4) 0.3270(5) 0.55939(19) 0.0539(12) Uani 1 1 d . . . . .
N3 N 0.3192(7) 0.3972(7) 0.5951(2) 0.094(2) Uani 1 1 d . . . . .
N4 N 0.1940(4) 0.1044(4) 0.43213(17) 0.0391(9) Uani 1 1 d . . . . .
N5 N 0.1486(4) 0.0016(4) 0.41752(18) 0.0448(10) Uani 1 1 d . . . . .
N6 N 0.0885(6) -0.0856(5) 0.4045(3) 0.0816(17) Uani 1 1 d . . . . .
C1 C 0.4049(5) 0.3362(4) 0.37057(18) 0.0341(9) Uani 1 1 d . . . . .
H1 H 0.3486 0.3903 0.3438 0.041 Uiso 1 1 calc R . . . .
C2 C 0.5580(6) 0.4649(4) 0.42264(19) 0.0426(11) Uani 1 1 d . . . . .
C3 C 0.3399(5) 0.3506(4) 0.43136(18) 0.0357(10) Uani 1 1 d . . . . .
H3 H 0.2278 0.3647 0.4303 0.043 Uiso 1 1 calc R . . . .
C4 C 0.3804(5) 0.2450(4) 0.47182(17) 0.0343(10) Uani 1 1 d . . . . .
H4 H 0.4888 0.2536 0.4839 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3600(5) 0.1196(4) 0.44233(17) 0.0334(9) Uani 1 1 d . . . . .
C6 C 0.4033(5) 0.2071(4) 0.34713(17) 0.0344(10) Uani 1 1 d . . . . .
H6 H 0.2984 0.1878 0.3336 0.041 Uiso 1 1 calc R . . . .
C7 C 0.4367(5) 0.0192(4) 0.47935(18) 0.0378(10) Uani 1 1 d . . . . .
C8 C 0.4518(8) -0.1926(5) 0.4986(3) 0.0714(17) Uani 1 1 d . . . . .
H8A H 0.5605 -0.2019 0.4908 0.107 Uiso 1 1 calc GR . . . .
H8B H 0.3985 -0.2669 0.4883 0.107 Uiso 1 1 calc GR . . . .
H8C H 0.4368 -0.1761 0.5394 0.107 Uiso 1 1 calc GR . . . .
C9 C 0.5156(5) 0.1911(4) 0.29633(18) 0.0368(10) Uani 1 1 d . . . . .
H9 H 0.6229 0.2009 0.3095 0.044 Uiso 1 1 calc R . . . .
C10 C 0.4956(8) 0.0701(5) 0.2638(2) 0.0560(14) Uani 1 1 d . . . . .
H10A H 0.5954 0.0355 0.2533 0.067 Uiso 1 1 calc R . . . .
H10B H 0.4395 0.0109 0.2874 0.067 Uiso 1 1 calc R . . . .
C11 C 0.4508(7) 0.2259(4) 0.19962(19) 0.0491(12) Uani 1 1 d . . . . .
C12 C 0.5991(9) 0.2296(7) 0.1644(3) 0.081(2) Uani 1 1 d . . . . .
H12A H 0.6290 0.3135 0.1581 0.121 Uiso 1 1 calc GR . . . .
H12B H 0.5826 0.1900 0.1275 0.121 Uiso 1 1 calc GR . . . .
H12C H 0.6796 0.1875 0.1852 0.121 Uiso 1 1 calc GR . . . .
C13 C 0.3199(10) 0.2850(7) 0.1691(3) 0.089(2) Uani 1 1 d . . . . .
H13A H 0.2311 0.2865 0.1944 0.134 Uiso 1 1 calc GR . . . .
H13B H 0.2956 0.2393 0.1345 0.134 Uiso 1 1 calc GR . . . .
H13C H 0.3477 0.3676 0.1587 0.134 Uiso 1 1 calc GR . . . .
C14 C 0.9175(8) 0.4714(8) 0.3017(3) 0.085(2) Uani 1 1 d . . . . .
Cl1 Cl 0.9623(4) 0.3238(4) 0.3319(2) 0.1334(14) Uani 0.727(3) 1 d . . P A 1
Cl2 Cl 0.9425(8) 0.4814(7) 0.22999(19) 0.170(3) Uani 0.727(3) 1 d . . P A 1
Cl3 Cl 1.0419(4) 0.5715(4) 0.34243(17) 0.1184(12) Uani 0.727(3) 1 d . . P A 1
Cl1A Cl 0.9401(12) 0.3122(10) 0.2749(6) 0.1334(14) Uani 0.273(3) 1 d . . P A 2
Cl2A Cl 0.989(3) 0.556(2) 0.2404(6) 0.170(3) Uani 0.273(3) 1 d . . P A 2
Cl3A Cl 0.9967(12) 0.4924(12) 0.3564(5) 0.1184(12) Uani 0.273(3) 1 d . . 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 1.451(5) . ?
O1 C2 1.350(5) . ?
O2 C2 1.345(6) . ?
O2 C3 1.451(5) . ?
O3 C5 1.425(5) . ?
O3 C6 1.435(5) . ?
O4 C2 1.187(6) . ?
O5 C7 1.190(5) . ?
O6 C7 1.307(6) . ?
O6 C8 1.451(6) . ?
O7 C9 1.421(5) . ?
O7 C11 1.424(6) . ?
O8 C10 1.413(6) . ?
O8 C11 1.427(6) . ?
N1 N2 1.220(6) . ?
N1 C4 1.471(5) . ?
N2 N3 1.123(7) . ?
N4 N5 1.231(6) . ?
N4 C5 1.461(5) . ?
N5 N6 1.122(6) . ?
C1 H1 0.9800 . ?
C1 C3 1.511(6) . ?
C1 C6 1.503(6) . ?
C3 H3 0.9800 . ?
C3 C4 1.517(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.532(6) . ?
C5 C7 1.534(6) . ?
C6 H6 0.9800 . ?
C6 C9 1.525(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9800 . ?
C9 C10 1.522(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.514(8) . ?
C11 C13 1.476(9) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 Cl1 1.790(8) . ?
C14 Cl2 1.661(9) . ?
C14 Cl3 1.792(9) . ?
C14 Cl1A 1.847(15) . ?
C14 Cl2A 1.79(2) . ?
C14 Cl3A 1.448(13) . ?

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
C2 O1 C1 107.9(3) . . ?
C2 O2 C3 108.1(3) . . ?
C5 O3 C6 114.9(3) . . ?
C7 O6 C8 116.6(4) . . ?
C9 O7 C11 109.2(3) . . ?
C10 O8 C11 106.6(4) . . ?
N2 N1 C4 115.6(4) . . ?
N3 N2 N1 171.8(5) . . ?
N5 N4 C5 117.3(4) . . ?
N6 N5 N4 171.0(5) . . ?
O1 C1 H1 109.4 . . ?
O1 C1 C3 101.1(3) . . ?
O1 C1 C6 112.2(3) . . ?
C3 C1 H1 109.4 . . ?
C6 C1 H1 109.4 . . ?
C6 C1 C3 115.0(4) . . ?
O2 C2 O1 110.5(4) . . ?
O4 C2 O1 125.3(5) . . ?
O4 C2 O2 124.2(4) . . ?
O2 C3 C1 101.0(3) . . ?
O2 C3 H3 111.2 . . ?
O2 C3 C4 108.3(3) . . ?
C1 C3 H3 111.2 . . ?
C1 C3 C4 113.6(3) . . ?
C4 C3 H3 111.2 . . ?
N1 C4 C3 111.3(4) . . ?
N1 C4 H4 108.6 . . ?
N1 C4 C5 107.4(3) . . ?
C3 C4 H4 108.6 . . ?
C3 C4 C5 112.2(3) . . ?
C5 C4 H4 108.6 . . ?
O3 C5 N4 112.9(3) . . ?
O3 C5 C4 108.9(3) . . ?
O3 C5 C7 103.0(3) . . ?
N4 C5 C4 106.5(3) . . ?
N4 C5 C7 115.6(4) . . ?
C4 C5 C7 109.8(3) . . ?
O3 C6 C1 112.7(3) . . ?
O3 C6 H6 108.8 . . ?
O3 C6 C9 105.8(3) . . ?
C1 C6 H6 108.8 . . ?
C1 C6 C9 112.0(3) . . ?
C9 C6 H6 108.8 . . ?
O5 C7 O6 124.9(4) . . ?
O5 C7 C5 122.9(5) . . ?
O6 C7 C5 112.3(4) . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O7 C9 C6 106.6(4) . . ?
O7 C9 H9 110.6 . . ?
O7 C9 C10 104.5(3) . . ?
C6 C9 H9 110.6 . . ?
C10 C9 C6 113.6(4) . . ?
C10 C9 H9 110.6 . . ?
O8 C10 C9 104.2(4) . . ?
O8 C10 H10A 110.9 . . ?
O8 C10 H10B 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
O7 C11 O8 104.6(3) . . ?
O7 C11 C12 109.0(5) . . ?
O7 C11 C13 110.7(5) . . ?
O8 C11 C12 110.7(5) . . ?
O8 C11 C13 109.1(5) . . ?
C13 C11 C12 112.5(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Cl1 C14 Cl3 102.3(4) . . ?
Cl2 C14 Cl1 114.4(5) . . ?
Cl2 C14 Cl3 113.5(5) . . ?
Cl2A C14 Cl1A 100.6(7) . . ?
Cl3A C14 Cl1A 112.7(8) . . ?
Cl3A C14 Cl2A 116.1(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C3 O2 32.5(4) . . . . ?
O1 C1 C3 C4 -83.3(4) . . . . ?
O1 C1 C6 O3 73.0(4) . . . . ?
O1 C1 C6 C9 -46.1(4) . . . . ?
O2 C3 C4 N1 84.1(4) . . . . ?
O2 C3 C4 C5 -155.6(3) . . . . ?
O3 C5 C7 O5 98.1(5) . . . . ?
O3 C5 C7 O6 -80.0(4) . . . . ?
O3 C6 C9 O7 -177.4(3) . . . . ?
O3 C6 C9 C10 68.0(5) . . . . ?
O7 C9 C10 O8 -15.2(5) . . . . ?
N1 C4 C5 O3 177.5(3) . . . . ?
N1 C4 C5 N4 55.5(4) . . . . ?
N1 C4 C5 C7 -70.4(4) . . . . ?
N2 N1 C4 C3 -72.1(5) . . . . ?
N2 N1 C4 C5 164.8(4) . . . . ?
N4 C5 C7 O5 -138.3(5) . . . . ?
N4 C5 C7 O6 43.5(5) . . . . ?
N5 N4 C5 O3 72.2(5) . . . . ?
N5 N4 C5 C4 -168.4(4) . . . . ?
N5 N4 C5 C7 -46.1(5) . . . . ?
C1 O1 C2 O2 11.7(5) . . . . ?
C1 O1 C2 O4 -167.1(4) . . . . ?
C1 C3 C4 N1 -164.6(3) . . . . ?
C1 C3 C4 C5 -44.3(5) . . . . ?
C1 C6 C9 O7 -54.2(4) . . . . ?
C1 C6 C9 C10 -168.8(4) . . . . ?
C2 O1 C1 C3 -27.9(4) . . . . ?
C2 O1 C1 C6 -151.0(3) . . . . ?
C2 O2 C3 C1 -27.6(4) . . . . ?
C2 O2 C3 C4 92.0(4) . . . . ?
C3 O2 C2 O1 11.0(5) . . . . ?
C3 O2 C2 O4 -170.2(4) . . . . ?
C3 C1 C6 O3 -41.8(5) . . . . ?
C3 C1 C6 C9 -160.9(3) . . . . ?
C3 C4 C5 O3 54.9(4) . . . . ?
C3 C4 C5 N4 -67.1(4) . . . . ?
C3 C4 C5 C7 167.0(3) . . . . ?
C4 C5 C7 O5 -17.8(6) . . . . ?
C4 C5 C7 O6 164.1(3) . . . . ?
C5 O3 C6 C1 55.5(5) . . . . ?
C5 O3 C6 C9 178.2(3) . . . . ?
C6 O3 C5 N4 56.4(5) . . . . ?
C6 O3 C5 C4 -61.7(4) . . . . ?
C6 O3 C5 C7 -178.3(3) . . . . ?
C6 C1 C3 O2 153.6(3) . . . . ?
C6 C1 C3 C4 37.9(5) . . . . ?
C6 C9 C10 O8 100.6(4) . . . . ?
C8 O6 C7 O5 4.4(7) . . . . ?
C8 O6 C7 C5 -177.5(4) . . . . ?
C9 O7 C11 O8 23.6(6) . . . . ?
C9 O7 C11 C12 -94.8(5) . . . . ?
C9 O7 C11 C13 141.0(5) . . . . ?
C10 O8 C11 O7 -33.7(6) . . . . ?
C10 O8 C11 C12 83.5(5) . . . . ?
C10 O8 C11 C13 -152.2(5) . . . . ?
C11 O7 C9 C6 -125.9(4) . . . . ?
C11 O7 C9 C10 -5.2(5) . . . . ?
C11 O8 C10 C9 30.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_190226_s5_yd_hh181130b
_database_code_depnum_ccdc_archive 'CCDC 1975129'
loop_
_audit_author_name
_audit_author_address
HeHuan
;Sichuan university
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H24 N10 O10'
_chemical_formula_sum            'C18 H24 N10 O10'
_chemical_formula_weight         540.47
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.6075(7)
_cell_length_b                   10.7485(9)
_cell_length_c                   33.736(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3121.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1729
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6760
_cell_measurement_theta_min      3.3290
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9470
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.980
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -60.00   0.3000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  178.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00   84.90   0.3000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       17.0762    0.0000  -90.0000 253

#__ type_ start__ end____ width___ exp.time_
  3 omega  -35.00    4.00   0.3000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       17.0762    0.0000  -90.0000 130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0422164000
_diffrn_orient_matrix_UB_12      0.0345227000
_diffrn_orient_matrix_UB_13      0.0143289000
_diffrn_orient_matrix_UB_21      -0.0198912000
_diffrn_orient_matrix_UB_22      0.0560382000
_diffrn_orient_matrix_UB_23      -0.0098938000
_diffrn_orient_matrix_UB_31      -0.0678955000
_diffrn_orient_matrix_UB_32      0.0050883000
_diffrn_orient_matrix_UB_33      0.0117704000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                3796
_reflns_number_total             5968
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1070 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0717
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1305P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2188
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C18) = Uanis(C12)
3.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.5278(4) 0.7754(3) 0.63643(9) 0.0604(8) Uani 1 1 d . . . . .
O2 O 0.6120(4) 1.0017(3) 0.59686(11) 0.0690(10) Uani 1 1 d . . . . .
O3 O 0.5717(7) 1.0994(5) 0.53949(18) 0.1144(18) Uani 1 1 d . . . . .
O4 O 0.2739(5) 1.1773(3) 0.59212(13) 0.0789(12) Uani 1 1 d . . . . .
O5 O 0.4265(8) 1.3423(5) 0.58980(15) 0.118(2) Uani 1 1 d . . . . .
O6 O 0.2194(4) 0.9399(3) 0.62754(11) 0.0655(10) Uani 1 1 d . . . . .
O7 O 0.1919(11) 0.9539(8) 0.6921(2) 0.182(4) Uani 1 1 d . . . . .
O8 O 0.7696(4) 0.8487(4) 0.50749(11) 0.0664(10) Uani 1 1 d . . . . .
O9 O 0.6062(8) 0.5290(6) 0.70049(17) 0.127(2) Uani 1 1 d . . . . .
O10 O 0.6117(8) 0.7341(5) 0.70709(14) 0.1157(18) Uani 1 1 d . . . . .
N1 N 0.5378(4) 0.7735(4) 0.52714(11) 0.0512(9) Uani 1 1 d . . . . .
H1 H 0.4424 0.7613 0.5206 0.061 Uiso 1 1 calc R . . . .
N2 N 0.6948(5) 0.5402(4) 0.54915(16) 0.0718(12) Uani 1 1 d . . . . .
N3 N 0.6525(7) 0.5170(6) 0.5146(2) 0.0936(17) Uani 1 1 d . . . . .
N4 N 0.6256(11) 0.4937(9) 0.4833(3) 0.145(3) Uani 1 1 d . . . . .
N5 N 0.7878(6) 0.6092(5) 0.62432(17) 0.0846(15) Uani 1 1 d . . . . .
N6 N 0.8820(6) 0.5227(6) 0.62074(17) 0.0887(17) Uani 1 1 d . . . . .
N7 N 0.9788(8) 0.4572(9) 0.6194(3) 0.149(3) Uani 1 1 d . . . . .
N8 N 0.3597(5) 0.6079(4) 0.64342(14) 0.0677(11) Uani 1 1 d . . . . .
N9 N 0.3293(5) 0.5088(5) 0.65857(14) 0.0692(12) Uani 1 1 d . . . . .
N10 N 0.2865(8) 0.4181(5) 0.6731(2) 0.1039(19) Uani 1 1 d . . . . .
C1 C 0.4727(6) 0.8051(4) 0.59687(12) 0.0506(11) Uani 1 1 d . . . . .
H1A H 0.3694 0.7685 0.5934 0.061 Uiso 1 1 calc R . . . .
C2 C 0.5839(5) 0.7459(4) 0.56662(14) 0.0491(10) Uani 1 1 d . . . . .
H2 H 0.6891 0.7778 0.5711 0.059 Uiso 1 1 calc R . . . .
C3 C 0.5821(5) 0.6045(4) 0.57432(15) 0.0515(11) Uani 1 1 d . . . . .
H3 H 0.4779 0.5721 0.5687 0.062 Uiso 1 1 calc R . . . .
C4 C 0.6248(5) 0.5737(5) 0.61680(18) 0.0629(13) Uani 1 1 d . . . . .
H4 H 0.6105 0.4846 0.6217 0.075 Uiso 1 1 calc R . . . .
C5 C 0.5245(6) 0.6500(5) 0.64552(15) 0.0607(12) Uani 1 1 d . . . . .
C6 C 0.4582(6) 0.9449(4) 0.59447(15) 0.0564(12) Uani 1 1 d . . . . .
H6 H 0.4080 0.9684 0.5695 0.068 Uiso 1 1 calc R . . . .
C7 C 0.3671(7) 0.9976(5) 0.62924(15) 0.0632(13) Uani 1 1 d . . . . .
H7 H 0.4185 0.9724 0.6539 0.076 Uiso 1 1 calc R . . . .
C8 C 0.3506(7) 1.1379(5) 0.62910(16) 0.0700(14) Uani 1 1 d . . . . .
H8A H 0.2894 1.1642 0.6517 0.084 Uiso 1 1 calc R . . . .
H8B H 0.4523 1.1763 0.6310 0.084 Uiso 1 1 calc R . . . .
C9 C 0.3232(8) 1.2814(5) 0.57652(19) 0.0754(15) Uani 1 1 d . . . . .
C10 C 0.2449(12) 1.3089(8) 0.5381(3) 0.125(3) Uani 1 1 d . . . . .
H10A H 0.1506 1.3540 0.5430 0.187 Uiso 1 1 calc GR . . . .
H10B H 0.2211 1.2323 0.5248 0.187 Uiso 1 1 calc GR . . . .
H10C H 0.3126 1.3581 0.5218 0.187 Uiso 1 1 calc GR . . . .
C11 C 0.1423(10) 0.9208(8) 0.6615(2) 0.104(3) Uani 1 1 d . . . . .
C12 C -0.0107(19) 0.8567(16) 0.6565(3) 0.188(4) Uani 1 1 d . . . . .
H12A H -0.0306 0.8436 0.6288 0.282 Uiso 1 1 calc GR . . . .
H12B H -0.0916 0.9074 0.6676 0.282 Uiso 1 1 calc GR . . . .
H12C H -0.0082 0.7779 0.6699 0.282 Uiso 1 1 calc GR . . . .
C13 C 0.6553(9) 1.0781(6) 0.5671(2) 0.0854(19) Uani 1 1 d . . . . .
C14 C 0.8108(10) 1.1320(9) 0.5744(3) 0.126(3) Uani 1 1 d . . . . .
H14A H 0.8118 1.1720 0.5999 0.188 Uiso 1 1 calc GR . . . .
H14B H 0.8342 1.1920 0.5542 0.188 Uiso 1 1 calc GR . . . .
H14C H 0.8873 1.0670 0.5740 0.188 Uiso 1 1 calc GR . . . .
C15 C 0.6349(5) 0.8175(5) 0.49968(14) 0.0548(11) Uani 1 1 d . . . . .
C16 C 0.5720(7) 0.8295(7) 0.45795(16) 0.0777(16) Uani 1 1 d . . . . .
H16A H 0.4693 0.7950 0.4568 0.117 Uiso 1 1 calc GR . . . .
H16B H 0.6385 0.7854 0.4399 0.117 Uiso 1 1 calc GR . . . .
H16C H 0.5684 0.9158 0.4506 0.117 Uiso 1 1 calc GR . . . .
C17 C 0.5872(8) 0.6312(7) 0.68805(19) 0.0871(19) Uani 1 1 d . . . . .
C18 C 0.6771(18) 0.7163(14) 0.7473(4) 0.188(4) Uani 1 1 d . . . . .
H18A H 0.6914 0.6291 0.7522 0.282 Uiso 1 1 calc GR . . . .
H18B H 0.6069 0.7501 0.7666 0.282 Uiso 1 1 calc GR . . . .
H18C H 0.7753 0.7582 0.7491 0.282 Uiso 1 1 calc GR . . . .


_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 1.452(5) . ?
O1 C5 1.383(6) . ?
O2 C6 1.460(6) . ?
O2 C13 1.350(8) . ?
O3 C13 1.199(9) . ?
O4 C8 1.474(7) . ?
O4 C9 1.307(7) . ?
O5 C9 1.192(8) . ?
O6 C7 1.415(6) . ?
O6 C11 1.338(8) . ?
O7 C11 1.174(10) . ?
O8 C15 1.236(6) . ?
O9 C17 1.187(8) . ?
O10 C17 1.297(8) . ?
O10 C18 1.480(14) . ?
N1 H1 0.8600 . ?
N1 C2 1.421(6) . ?
N1 C15 1.334(6) . ?
N2 N3 1.247(8) . ?
N2 C3 1.463(7) . ?
N3 N4 1.110(9) . ?
N5 N6 1.240(8) . ?
N5 C4 1.475(7) . ?
N6 N7 1.091(9) . ?
N8 N9 1.210(6) . ?
N8 C5 1.491(7) . ?
N9 N10 1.151(7) . ?
C1 H1A 0.9800 . ?
C1 C2 1.537(7) . ?
C1 C6 1.509(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.542(6) . ?
C3 H3 0.9800 . ?
C3 C4 1.516(7) . ?
C4 H4 0.9800 . ?
C4 C5 1.535(8) . ?
C5 C17 1.546(8) . ?
C6 H6 0.9800 . ?
C6 C7 1.520(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.515(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.490(11) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.496(16) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.479(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.513(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C5 O1 C1 114.3(3) . . ?
C13 O2 C6 117.6(5) . . ?
C9 O4 C8 116.2(4) . . ?
C11 O6 C7 118.5(5) . . ?
C17 O10 C18 113.9(8) . . ?
C2 N1 H1 118.3 . . ?
C15 N1 H1 118.3 . . ?
C15 N1 C2 123.4(4) . . ?
N3 N2 C3 116.4(4) . . ?
N4 N3 N2 174.9(8) . . ?
N6 N5 C4 114.3(5) . . ?
N7 N6 N5 170.7(8) . . ?
N9 N8 C5 116.9(5) . . ?
N10 N9 N8 173.8(6) . . ?
O1 C1 H1A 108.6 . . ?
O1 C1 C2 108.4(4) . . ?
O1 C1 C6 107.1(4) . . ?
C2 C1 H1A 108.6 . . ?
C6 C1 H1A 108.6 . . ?
C6 C1 C2 115.4(4) . . ?
N1 C2 C1 111.2(4) . . ?
N1 C2 H2 109.2 . . ?
N1 C2 C3 111.2(4) . . ?
C1 C2 H2 109.2 . . ?
C1 C2 C3 106.9(4) . . ?
C3 C2 H2 109.2 . . ?
N2 C3 C2 111.1(4) . . ?
N2 C3 H3 109.1 . . ?
N2 C3 C4 106.5(4) . . ?
C2 C3 H3 109.1 . . ?
C4 C3 C2 111.8(4) . . ?
C4 C3 H3 109.1 . . ?
N5 C4 C3 109.7(4) . . ?
N5 C4 H4 110.1 . . ?
N5 C4 C5 106.7(5) . . ?
C3 C4 H4 110.1 . . ?
C3 C4 C5 110.1(4) . . ?
C5 C4 H4 110.1 . . ?
O1 C5 N8 107.8(4) . . ?
O1 C5 C4 111.7(4) . . ?
O1 C5 C17 109.0(5) . . ?
N8 C5 C4 110.1(4) . . ?
N8 C5 C17 109.7(4) . . ?
C4 C5 C17 108.6(5) . . ?
O2 C6 C1 109.8(4) . . ?
O2 C6 H6 109.8 . . ?
O2 C6 C7 105.6(4) . . ?
C1 C6 H6 109.8 . . ?
C1 C6 C7 111.8(4) . . ?
C7 C6 H6 109.8 . . ?
O6 C7 C6 105.6(4) . . ?
O6 C7 H7 108.6 . . ?
O6 C7 C8 110.6(5) . . ?
C6 C7 H7 108.6 . . ?
C8 C7 C6 114.6(4) . . ?
C8 C7 H7 108.6 . . ?
O4 C8 C7 109.3(4) . . ?
O4 C8 H8A 109.8 . . ?
O4 C8 H8B 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
O4 C9 C10 111.9(6) . . ?
O5 C9 O4 124.1(6) . . ?
O5 C9 C10 123.7(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 C12 114.3(7) . . ?
O7 C11 O6 121.8(7) . . ?
O7 C11 C12 123.9(8) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 111.3(8) . . ?
O3 C13 O2 121.9(6) . . ?
O3 C13 C14 126.8(7) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O8 C15 N1 122.4(4) . . ?
O8 C15 C16 120.7(4) . . ?
N1 C15 C16 116.9(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O9 C17 O10 126.3(6) . . ?
O9 C17 C5 119.8(7) . . ?
O10 C17 C5 113.9(6) . . ?
O10 C18 H18A 109.5 . . ?
O10 C18 H18B 109.5 . . ?
O10 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -178.9(3) . . . . ?
O1 C1 C2 C3 59.6(4) . . . . ?
O1 C1 C6 O2 66.8(5) . . . . ?
O1 C1 C6 C7 -50.2(5) . . . . ?
O1 C5 C17 O9 -173.8(7) . . . . ?
O1 C5 C17 O10 7.3(8) . . . . ?
O2 C6 C7 O6 -178.5(4) . . . . ?
O2 C6 C7 C8 59.5(6) . . . . ?
O6 C7 C8 O4 -61.1(5) . . . . ?
N1 C2 C3 N2 63.3(5) . . . . ?
N1 C2 C3 C4 -177.7(4) . . . . ?
N2 C3 C4 N5 56.0(5) . . . . ?
N2 C3 C4 C5 173.2(4) . . . . ?
N3 N2 C3 C2 -81.9(6) . . . . ?
N3 N2 C3 C4 156.1(5) . . . . ?
N5 C4 C5 O1 67.6(5) . . . . ?
N5 C4 C5 N8 -172.8(4) . . . . ?
N5 C4 C5 C17 -52.7(6) . . . . ?
N6 N5 C4 C3 -96.1(6) . . . . ?
N6 N5 C4 C5 144.6(5) . . . . ?
N8 C5 C17 O9 68.4(9) . . . . ?
N8 C5 C17 O10 -110.5(6) . . . . ?
N9 N8 C5 O1 -164.5(5) . . . . ?
N9 N8 C5 C4 73.6(6) . . . . ?
N9 N8 C5 C17 -45.9(7) . . . . ?
C1 O1 C5 N8 -61.6(5) . . . . ?
C1 O1 C5 C4 59.4(5) . . . . ?
C1 O1 C5 C17 179.5(4) . . . . ?
C1 C2 C3 N2 -175.2(4) . . . . ?
C1 C2 C3 C4 -56.3(5) . . . . ?
C1 C6 C7 O6 -59.1(5) . . . . ?
C1 C6 C7 C8 178.9(5) . . . . ?
C2 N1 C15 O8 -7.0(7) . . . . ?
C2 N1 C15 C16 173.8(5) . . . . ?
C2 C1 C6 O2 -54.0(5) . . . . ?
C2 C1 C6 C7 -170.9(4) . . . . ?
C2 C3 C4 N5 -65.6(5) . . . . ?
C2 C3 C4 C5 51.6(5) . . . . ?
C3 C4 C5 O1 -51.5(5) . . . . ?
C3 C4 C5 N8 68.2(5) . . . . ?
C3 C4 C5 C17 -171.7(4) . . . . ?
C4 C5 C17 O9 -51.9(8) . . . . ?
C4 C5 C17 O10 129.2(6) . . . . ?
C5 O1 C1 C2 -64.4(5) . . . . ?
C5 O1 C1 C6 170.5(4) . . . . ?
C6 O2 C13 O3 0.0(9) . . . . ?
C6 O2 C13 C14 177.8(6) . . . . ?
C6 C1 C2 N1 -58.8(5) . . . . ?
C6 C1 C2 C3 179.7(4) . . . . ?
C6 C7 C8 O4 58.2(6) . . . . ?
C7 O6 C11 O7 2.4(13) . . . . ?
C7 O6 C11 C12 -178.7(10) . . . . ?
C8 O4 C9 O5 1.9(9) . . . . ?
C8 O4 C9 C10 176.6(6) . . . . ?
C9 O4 C8 C7 -143.1(5) . . . . ?
C11 O6 C7 C6 149.6(6) . . . . ?
C11 O6 C7 C8 -85.9(7) . . . . ?
C13 O2 C6 C1 124.0(5) . . . . ?
C13 O2 C6 C7 -115.3(5) . . . . ?
C15 N1 C2 C1 130.5(4) . . . . ?
C15 N1 C2 C3 -110.6(5) . . . . ?
C18 O10 C17 O9 3.3(13) . . . . ?
C18 O10 C17 C5 -177.9(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_190226_s4_yd_2
_database_code_depnum_ccdc_archive 'CCDC 1975131'
loop_
_audit_author_name
_audit_author_address
HeHuan
;Sichuan university
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H16 N6 O8'
_chemical_formula_sum            'C13 H16 N6 O8'
_chemical_formula_weight         384.32
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.2784(7)
_cell_length_b                   9.2019(10)
_cell_length_c                   26.166(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1752.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1361
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.1730
_cell_measurement_theta_min      3.6430
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6084
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.114
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   21.00   48.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       17.0762  -99.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   23.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -82.00  -34.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -77.0000    0.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega  -78.00  -17.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -57.0000  -90.0000 122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0073803000
_diffrn_orient_matrix_UB_12      0.0767235000
_diffrn_orient_matrix_UB_13      -0.0016163000
_diffrn_orient_matrix_UB_21      0.0083203000
_diffrn_orient_matrix_UB_22      0.0050967000
_diffrn_orient_matrix_UB_23      0.0269799000
_diffrn_orient_matrix_UB_31      0.0966986000
_diffrn_orient_matrix_UB_32      0.0055113000
_diffrn_orient_matrix_UB_33      -0.0024360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.575
_reflns_Friedel_fraction_full    0.808
_reflns_Friedel_fraction_max     0.797
_reflns_number_gt                2428
_reflns_number_total             3278
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.018
_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)+(0.0383P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0950
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O8) = Uanis(O8A)
3. Others
 Sof(H10C)=Sof(H10D)=Sof(O8A)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(O8)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.2730(3) 0.3336(3) 0.28032(8) 0.0521(6) Uani 1 1 d . . . . .
O2 O 0.4915(3) 0.4956(3) 0.26536(8) 0.0503(6) Uani 1 1 d . . . . .
O3 O 0.5912(3) 0.2703(2) 0.34651(8) 0.0430(5) Uani 1 1 d . . . . .
O4 O 0.4030(4) 0.3444(3) 0.20279(9) 0.0702(8) Uani 1 1 d . . . . .
O5 O 0.7504(4) 0.2964(3) 0.44036(10) 0.0703(8) Uani 1 1 d . . . . .
O6 O 0.9334(3) 0.4757(3) 0.41167(8) 0.0613(7) Uani 1 1 d . . . . .
O7 O 0.1475(3) 0.1351(3) 0.38284(9) 0.0560(7) Uani 1 1 d . . . . .
N1 N 0.5204(4) 0.5766(3) 0.40222(10) 0.0518(8) Uani 1 1 d . . . . .
N2 N 0.5998(4) 0.6728(3) 0.42591(11) 0.0531(7) Uani 1 1 d . . . . .
N3 N 0.6591(5) 0.7573(4) 0.45222(13) 0.0798(11) Uani 1 1 d . . . . .
N4 N 0.8488(3) 0.3936(4) 0.31506(11) 0.0512(7) Uani 1 1 d . . . . .
N5 N 0.8540(4) 0.2834(5) 0.28838(12) 0.0638(9) Uani 1 1 d . . . . .
N6 N 0.8719(5) 0.1890(5) 0.26142(15) 0.1105(17) Uani 1 1 d . . . . .
C1 C 0.3096(4) 0.3963(4) 0.33016(11) 0.0426(8) Uani 1 1 d . . . . .
H1 H 0.1954 0.4301 0.3461 0.051 Uiso 1 1 calc R . . . .
C2 C 0.3896(5) 0.3863(4) 0.24568(14) 0.0503(8) Uani 1 1 d . . . . .
C3 C 0.4343(4) 0.5255(4) 0.31679(11) 0.0441(8) Uani 1 1 d . . . . .
H3 H 0.3636 0.6161 0.3179 0.053 Uiso 1 1 calc R . . . .
C4 C 0.6005(4) 0.5369(3) 0.35161(11) 0.0422(8) Uani 1 1 d . . . . .
H4 H 0.6829 0.6140 0.3396 0.051 Uiso 1 1 calc R . . . .
C5 C 0.7048(4) 0.3912(4) 0.35486(12) 0.0414(7) Uani 1 1 d . . . . .
C6 C 0.4045(4) 0.2864(3) 0.36387(12) 0.0412(7) Uani 1 1 d . . . . .
H6 H 0.4039 0.3206 0.3993 0.049 Uiso 1 1 calc R . . . .
C7 C 0.7991(5) 0.3786(4) 0.40769(13) 0.0486(8) Uani 1 1 d . . . . .
C8 C 1.0336(6) 0.4764(6) 0.45995(14) 0.0865(15) Uani 1 1 d . . . . .
H8A H 1.1422 0.5347 0.4565 0.130 Uiso 1 1 calc GR . . . .
H8B H 1.0676 0.3787 0.4688 0.130 Uiso 1 1 calc GR . . . .
H8C H 0.9568 0.5160 0.4863 0.130 Uiso 1 1 calc GR . . . .
C9 C 0.3283(4) 0.1338(4) 0.36149(13) 0.0470(8) Uani 1 1 d . . . . .
H9 H 0.3258 0.0985 0.3262 0.056 Uiso 1 1 calc R . . . .
C10 C 0.4289(5) 0.0274(4) 0.39584(13) 0.0576(10) Uani 1 1 d . . . . .
H10A H 0.5366 -0.0135 0.3794 0.069 Uiso 0.35(2) 1 calc R . P A 1
H10B H 0.4631 0.0706 0.4283 0.069 Uiso 0.35(2) 1 calc R . P A 1
H10C H 0.5053 -0.0365 0.3754 0.069 Uiso 0.65(2) 1 calc R . P A 2
H10D H 0.5072 0.0797 0.4195 0.069 Uiso 0.65(2) 1 calc R . P A 2
C11 C 0.1169(5) -0.0074(4) 0.40348(15) 0.0615(10) Uani 1 1 d . . . . .
C12 C 0.0290(8) -0.1038(5) 0.36406(19) 0.1148(19) Uani 1 1 d . . . . .
H12A H -0.0882 -0.0643 0.3545 0.172 Uiso 1 1 calc GR . . . .
H12B H 0.0123 -0.1994 0.3780 0.172 Uiso 1 1 calc GR . . . .
H12C H 0.1067 -0.1093 0.3345 0.172 Uiso 1 1 calc GR . . . .
C13 C 0.0071(6) 0.0076(5) 0.45196(15) 0.0858(14) Uani 1 1 d . . . . .
H13A H 0.0724 0.0685 0.4756 0.129 Uiso 1 1 calc GR . . . .
H13B H -0.0110 -0.0867 0.4669 0.129 Uiso 1 1 calc GR . . . .
H13C H -0.1100 0.0504 0.4443 0.129 Uiso 1 1 calc GR . . . .
O8 O 0.286(3) -0.075(3) 0.4011(8) 0.071(3) Uani 0.35(2) 1 d . . P A 1
O8A O 0.2969(15) -0.0546(13) 0.4230(6) 0.071(3) Uani 0.65(2) 1 d . . 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 1.451(4) . ?
O1 C2 1.333(4) . ?
O2 C2 1.352(4) . ?
O2 C3 1.435(3) . ?
O3 C5 1.403(4) . ?
O3 C6 1.441(4) . ?
O4 C2 1.191(4) . ?
O5 C7 1.195(4) . ?
O6 C7 1.328(4) . ?
O6 C8 1.459(4) . ?
O7 C9 1.430(4) . ?
O7 C11 1.435(4) . ?
N1 N2 1.225(4) . ?
N1 C4 1.492(4) . ?
N2 N3 1.125(4) . ?
N4 N5 1.232(4) . ?
N4 C5 1.478(4) . ?
N5 N6 1.126(5) . ?
C1 H1 0.9800 . ?
C1 C3 1.536(5) . ?
C1 C6 1.509(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.518(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.543(4) . ?
C5 C7 1.548(4) . ?
C6 H6 0.9800 . ?
C6 C9 1.511(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9800 . ?
C9 C10 1.517(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C10 O8 1.42(2) . ?
C10 O8A 1.414(11) . ?
C11 C12 1.504(6) . ?
C11 C13 1.505(5) . ?
C11 O8 1.38(2) . ?
C11 O8A 1.472(12) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C2 O1 C1 110.5(3) . . ?
C2 O2 C3 109.9(3) . . ?
C5 O3 C6 115.2(2) . . ?
C7 O6 C8 116.0(3) . . ?
C9 O7 C11 106.4(3) . . ?
N2 N1 C4 116.2(3) . . ?
N3 N2 N1 171.9(4) . . ?
N5 N4 C5 114.1(3) . . ?
N6 N5 N4 173.3(4) . . ?
O1 C1 H1 110.6 . . ?
O1 C1 C3 102.2(2) . . ?
O1 C1 C6 110.1(3) . . ?
C3 C1 H1 110.6 . . ?
C6 C1 H1 110.6 . . ?
C6 C1 C3 112.4(2) . . ?
O1 C2 O2 111.2(3) . . ?
O4 C2 O1 125.1(4) . . ?
O4 C2 O2 123.7(3) . . ?
O2 C3 C1 103.7(2) . . ?
O2 C3 H3 110.0 . . ?
O2 C3 C4 110.2(3) . . ?
C1 C3 H3 110.0 . . ?
C4 C3 C1 112.8(3) . . ?
C4 C3 H3 110.0 . . ?
N1 C4 C3 103.8(2) . . ?
N1 C4 H4 110.2 . . ?
N1 C4 C5 110.8(2) . . ?
C3 C4 H4 110.2 . . ?
C3 C4 C5 111.4(3) . . ?
C5 C4 H4 110.2 . . ?
O3 C5 N4 108.7(2) . . ?
O3 C5 C4 113.0(2) . . ?
O3 C5 C7 110.0(3) . . ?
N4 C5 C4 107.3(3) . . ?
N4 C5 C7 108.4(2) . . ?
C4 C5 C7 109.4(3) . . ?
O3 C6 C1 108.4(2) . . ?
O3 C6 H6 109.6 . . ?
O3 C6 C9 103.8(2) . . ?
C1 C6 H6 109.6 . . ?
C1 C6 C9 115.5(3) . . ?
C9 C6 H6 109.6 . . ?
O5 C7 O6 126.0(3) . . ?
O5 C7 C5 123.7(3) . . ?
O6 C7 C5 110.2(3) . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O7 C9 C6 108.3(3) . . ?
O7 C9 H9 110.7 . . ?
O7 C9 C10 102.6(3) . . ?
C6 C9 H9 110.7 . . ?
C6 C9 C10 113.5(3) . . ?
C10 C9 H9 110.7 . . ?
C9 C10 H10A 112.2 . . ?
C9 C10 H10B 112.2 . . ?
C9 C10 H10C 110.0 . . ?
C9 C10 H10D 110.0 . . ?
H10A C10 H10B 109.8 . . ?
H10C C10 H10D 108.4 . . ?
O8 C10 C9 97.7(9) . . ?
O8 C10 H10A 112.2 . . ?
O8 C10 H10B 112.2 . . ?
O8A C10 C9 108.3(5) . . ?
O8A C10 H10C 110.0 . . ?
O8A C10 H10D 110.0 . . ?
O7 C11 C12 110.3(3) . . ?
O7 C11 C13 108.4(3) . . ?
O7 C11 O8A 105.2(5) . . ?
C12 C11 C13 114.0(3) . . ?
O8 C11 O7 105.1(10) . . ?
O8 C11 C12 94.6(10) . . ?
O8 C11 C13 123.5(9) . . ?
O8A C11 C12 116.3(7) . . ?
O8A C11 C13 101.9(7) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 O8 C10 110.9(16) . . ?
C10 O8A C11 105.8(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C3 O2 -15.3(3) . . . . ?
O1 C1 C3 C4 -134.5(3) . . . . ?
O1 C1 C6 O3 73.1(3) . . . . ?
O1 C1 C6 C9 -42.8(4) . . . . ?
O2 C3 C4 N1 176.7(2) . . . . ?
O2 C3 C4 C5 -64.0(3) . . . . ?
O3 C5 C7 O5 -15.4(4) . . . . ?
O3 C5 C7 O6 167.5(2) . . . . ?
O3 C6 C9 O7 174.4(2) . . . . ?
O3 C6 C9 C10 61.2(3) . . . . ?
O7 C9 C10 O8 40.1(10) . . . . ?
O7 C9 C10 O8A 16.9(8) . . . . ?
O7 C11 O8 C10 18.7(15) . . . . ?
O7 C11 O8A C10 -23.1(11) . . . . ?
N1 C4 C5 O3 87.5(3) . . . . ?
N1 C4 C5 N4 -152.7(2) . . . . ?
N1 C4 C5 C7 -35.3(3) . . . . ?
N2 N1 C4 C3 -135.7(3) . . . . ?
N2 N1 C4 C5 104.6(3) . . . . ?
N4 C5 C7 O5 -134.0(3) . . . . ?
N4 C5 C7 O6 48.8(3) . . . . ?
N5 N4 C5 O3 -9.1(4) . . . . ?
N5 N4 C5 C4 -131.6(3) . . . . ?
N5 N4 C5 C7 110.4(3) . . . . ?
C1 O1 C2 O2 -7.9(4) . . . . ?
C1 O1 C2 O4 172.6(3) . . . . ?
C1 C3 C4 N1 -68.0(3) . . . . ?
C1 C3 C4 C5 51.3(3) . . . . ?
C1 C6 C9 O7 -67.1(4) . . . . ?
C1 C6 C9 C10 179.7(3) . . . . ?
C2 O1 C1 C3 14.5(3) . . . . ?
C2 O1 C1 C6 -105.1(3) . . . . ?
C2 O2 C3 C1 11.9(3) . . . . ?
C2 O2 C3 C4 132.8(3) . . . . ?
C3 O2 C2 O1 -3.1(3) . . . . ?
C3 O2 C2 O4 176.4(3) . . . . ?
C3 C1 C6 O3 -40.1(3) . . . . ?
C3 C1 C6 C9 -156.0(3) . . . . ?
C3 C4 C5 O3 -27.5(3) . . . . ?
C3 C4 C5 N4 92.3(3) . . . . ?
C3 C4 C5 C7 -150.3(3) . . . . ?
C4 C5 C7 O5 109.3(4) . . . . ?
C4 C5 C7 O6 -67.8(3) . . . . ?
C5 O3 C6 C1 69.2(3) . . . . ?
C5 O3 C6 C9 -167.5(2) . . . . ?
C6 O3 C5 N4 -151.5(2) . . . . ?
C6 O3 C5 C4 -32.6(3) . . . . ?
C6 O3 C5 C7 89.9(3) . . . . ?
C6 C1 C3 O2 102.6(3) . . . . ?
C6 C1 C3 C4 -16.5(4) . . . . ?
C6 C9 C10 O8 156.7(10) . . . . ?
C6 C9 C10 O8A 133.5(8) . . . . ?
C8 O6 C7 O5 2.6(5) . . . . ?
C8 O6 C7 C5 179.6(3) . . . . ?
C9 O7 C11 C12 -91.3(4) . . . . ?
C9 O7 C11 C13 143.3(3) . . . . ?
C9 O7 C11 O8 9.5(10) . . . . ?
C9 O7 C11 O8A 34.8(7) . . . . ?
C9 C10 O8 C11 -36.6(14) . . . . ?
C9 C10 O8A C11 3.7(12) . . . . ?
C11 O7 C9 C6 -151.7(3) . . . . ?
C11 O7 C9 C10 -31.4(4) . . . . ?
C12 C11 O8 C10 131.2(12) . . . . ?
C12 C11 O8A C10 99.2(9) . . . . ?
C13 C11 O8 C10 -106.0(12) . . . . ?
C13 C11 O8A C10 -136.2(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_190419_s1_hh_yd0417a
_database_code_depnum_ccdc_archive 'CCDC 1975133'
loop_
_audit_author_name
_audit_author_address
HeHuan
;Sichuan university
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H22 N6 O11'
_chemical_formula_sum            'C17 H22 N6 O11'
_chemical_formula_weight         486.40
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.2129(4)
_cell_length_b                   40.7685(17)
_cell_length_c                   12.8563(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.320(3)
_cell_angle_gamma                90
_cell_volume                     4828.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6267
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7900
_cell_measurement_theta_min      3.3450
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35580
_diffrn_reflns_point_group_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.905
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  23.00   0.20    1.00    --  -15.63 -99.00 -90.00  240
  2  ω    -25.00   0.00   0.20    1.00    --  -15.63 -99.00-150.00  125
  3  ω    -74.00 -35.00   0.20    1.00    --  -15.63-178.00-120.00  195
  4  ω    -19.00  21.00   0.20    1.00    --   17.66-105.00  78.00  200
  5  ω     33.00  88.00   0.20    1.00    --   17.66-178.00 150.00  275
  6  ω    -43.00 -18.00   0.20    1.00    --  -15.63 105.00 179.00  125
  7  ω     40.00  69.00   0.20    1.00    --   17.66 178.00-180.00  145
  8  ω    -51.00  38.00   0.20    1.00    --   17.35 -19.00-180.00  445
  9  ω      9.00  42.00   0.20    1.00    --   17.35  38.00  60.00  165
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0589358000
_diffrn_orient_matrix_UB_12      -0.0104924000
_diffrn_orient_matrix_UB_13      0.0121406000
_diffrn_orient_matrix_UB_21      -0.0491009000
_diffrn_orient_matrix_UB_22      0.0131436000
_diffrn_orient_matrix_UB_23      -0.0079464000
_diffrn_orient_matrix_UB_31      -0.0065448000
_diffrn_orient_matrix_UB_32      -0.0043841000
_diffrn_orient_matrix_UB_33      -0.0532753000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.745
_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                11897
_reflns_number_total             16488
_reflns_odcompleteness_completeness 94.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 3926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1253
_refine_ls_number_reflns         16488
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.1049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1318
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O33) = Uanis(O33A)
Uanis(O44) = Uanis(O44A)
3. Others
 Sof(O33A)=1-FVAR(1)
 Sof(O33)=FVAR(1)
 Sof(O44A)=1-FVAR(2)
 Sof(O44)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C19(H19), C20(H20), C21(H21),
 C22(H22), C29(H29), C36(H36), C37(H37), C38(H38), C39(H39), C46(H46), C53(H53),
  C54(H54), C55(H55), C56(H56), C63(H63)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C32(H32A,H32B), C49(H49A,H49B), C66(H66A,H66B)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C), C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C41(H41A,H41B,H41C), C43(H43A,
 H43B,H43C), C45(H45A,H45B,H45C), C48(H48A,H48B,H48C), C51(H51A,H51B,H51C),
 C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C62(H62A,H62B,H62C), C65(H65A,H65B,
 H65C), C68(H68A,H68B,H68C)
;
_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 0.5404(3) 0.62963(7) 0.4560(2) 0.0479(7) Uani 1 1 d . . . . .
O2 O 0.4159(4) 0.63186(10) 0.6415(3) 0.0757(11) Uani 1 1 d . . . . .
O3 O 0.2927(4) 0.67656(10) 0.5976(3) 0.0757(11) Uani 1 1 d . . . . .
O4 O 0.5351(3) 0.70858(8) 0.2559(3) 0.0586(8) Uani 1 1 d . . . . .
O5 O 0.3165(5) 0.71350(12) 0.1858(5) 0.1158(18) Uani 1 1 d . . . . .
O6 O 0.7514(3) 0.66939(8) 0.3354(3) 0.0555(8) Uani 1 1 d . . . . .
O7 O 0.8541(5) 0.67108(12) 0.1776(4) 0.0929(13) Uani 1 1 d . . . . .
O8 O 0.7648(3) 0.59426(8) 0.2577(3) 0.0593(8) Uani 1 1 d . . . . .
O9 O 0.9992(5) 0.59711(17) 0.2954(5) 0.135(2) Uani 1 1 d . . . . .
O10 O 0.6032(4) 0.55009(9) 0.3757(3) 0.0664(9) Uani 1 1 d . . . . .
O11 O 0.7211(5) 0.50668(10) 0.4396(4) 0.0919(13) Uani 1 1 d . . . . .
N1 N 0.2894(4) 0.63575(10) 0.4066(3) 0.0541(10) Uani 1 1 d . . . . .
N2 N 0.2700(5) 0.60686(15) 0.4285(4) 0.0894(17) Uani 1 1 d . . . . .
N3 N 0.2454(9) 0.58032(19) 0.4390(7) 0.163(4) Uani 1 1 d . . . . .
N4 N 0.5480(5) 0.69932(11) 0.4831(3) 0.0629(11) Uani 1 1 d . . . . .
N5 N 0.6097(8) 0.72300(16) 0.4547(5) 0.113(2) Uani 1 1 d . . . . .
N6 N 0.6860(12) 0.7449(2) 0.4388(7) 0.189(5) Uani 1 1 d . . . . .
C1 C 0.4174(4) 0.64969(11) 0.4623(3) 0.0446(10) Uani 1 1 d . . . . .
C2 C 0.4435(5) 0.68314(11) 0.4121(4) 0.0489(11) Uani 1 1 d . . . . .
H2 H 0.3525 0.6956 0.4111 0.059 Uiso 1 1 calc R . . . .
C3 C 0.4950(4) 0.67799(10) 0.3018(3) 0.0448(10) Uani 1 1 d . . . . .
H3 H 0.4138 0.6690 0.2614 0.054 Uiso 1 1 calc R . . . .
C4 C 0.6224(4) 0.65436(11) 0.2923(4) 0.0459(10) Uani 1 1 d . . . . .
H4 H 0.6383 0.6491 0.2189 0.055 Uiso 1 1 calc R . . . .
C5 C 0.5896(4) 0.62344(11) 0.3518(3) 0.0465(10) Uani 1 1 d . . . . .
H5 H 0.5146 0.6111 0.3143 0.056 Uiso 1 1 calc R . . . .
C6 C 0.3795(5) 0.65163(12) 0.5783(4) 0.0515(11) Uani 1 1 d . . . . .
C7 C 0.2456(8) 0.68049(18) 0.7046(5) 0.092(2) Uani 1 1 d . . . . .
H7A H 0.1690 0.6964 0.7074 0.138 Uiso 1 1 calc GR . . . .
H7B H 0.3258 0.6878 0.7466 0.138 Uiso 1 1 calc GR . . . .
H7C H 0.2109 0.6599 0.7305 0.138 Uiso 1 1 calc GR . . . .
C8 C 0.4357(6) 0.72455(13) 0.1977(5) 0.0662(14) Uani 1 1 d . . . . .
C9 C 0.4897(8) 0.75620(17) 0.1619(7) 0.109(2) Uani 1 1 d . . . . .
H9A H 0.5649 0.7637 0.2080 0.163 Uiso 1 1 calc GR . . . .
H9B H 0.4117 0.7718 0.1611 0.163 Uiso 1 1 calc GR . . . .
H9C H 0.5280 0.7539 0.0930 0.163 Uiso 1 1 calc GR . . . .
C10 C 0.8621(5) 0.67587(14) 0.2691(5) 0.0656(14) Uani 1 1 d . . . . .
C11 C 0.9885(6) 0.68859(19) 0.3281(6) 0.099(2) Uani 1 1 d . . . . .
H11A H 0.9608 0.7080 0.3651 0.148 Uiso 1 1 calc GR . . . .
H11B H 1.0654 0.6937 0.2807 0.148 Uiso 1 1 calc GR . . . .
H11C H 1.0211 0.6723 0.3767 0.148 Uiso 1 1 calc GR . . . .
C12 C 0.7241(5) 0.60184(12) 0.3639(4) 0.0548(12) Uani 1 1 d . . . . .
H12 H 0.8017 0.6150 0.3957 0.066 Uiso 1 1 calc R . . . .
C13 C 0.9066(6) 0.59253(15) 0.2316(6) 0.0793(17) Uani 1 1 d . . . . .
C14 C 0.9257(8) 0.5854(2) 0.1217(6) 0.105(2) Uani 1 1 d . . . . .
H14A H 0.8651 0.5672 0.1023 0.158 Uiso 1 1 calc GR . . . .
H14B H 1.0254 0.5800 0.1089 0.158 Uiso 1 1 calc GR . . . .
H14C H 0.8991 0.6043 0.0813 0.158 Uiso 1 1 calc GR . . . .
C15 C 0.7065(6) 0.57128(14) 0.4255(5) 0.0729(16) Uani 1 1 d . . . . .
H15A H 0.7992 0.5602 0.4316 0.088 Uiso 1 1 calc R . . . .
H15B H 0.6734 0.5767 0.4949 0.088 Uiso 1 1 calc R . . . .
C16 C 0.6234(6) 0.51797(13) 0.3891(4) 0.0648(14) Uani 1 1 d . . . . .
C17 C 0.5123(9) 0.49878(18) 0.3335(8) 0.126(3) Uani 1 1 d . . . . .
H17A H 0.4184 0.5082 0.3457 0.189 Uiso 1 1 calc GR . . . .
H17B H 0.5136 0.4766 0.3582 0.189 Uiso 1 1 calc GR . . . .
H17C H 0.5323 0.4991 0.2603 0.189 Uiso 1 1 calc GR . . . .
O12 O 0.9689(3) 0.37180(7) 0.2000(2) 0.0447(7) Uani 1 1 d . . . . .
O13 O 1.0829(4) 0.36691(10) 0.3877(3) 0.0668(10) Uani 1 1 d . . . . .
O14 O 1.2128(4) 0.32356(10) 0.3427(3) 0.0744(11) Uani 1 1 d . . . . .
O15 O 0.9647(3) 0.29244(8) 0.0003(3) 0.0588(8) Uani 1 1 d . . . . .
O16 O 1.1837(6) 0.28634(12) -0.0687(5) 0.121(2) Uani 1 1 d . . . . .
O17 O 0.7533(3) 0.33289(8) 0.0800(2) 0.0509(7) Uani 1 1 d . . . . .
O18 O 0.6522(4) 0.32973(12) -0.0798(3) 0.0874(13) Uani 1 1 d . . . . .
O19 O 0.7497(3) 0.40819(8) -0.0012(2) 0.0554(8) Uani 1 1 d . . . . .
O20 O 0.5153(5) 0.40183(15) 0.0355(4) 0.1147(17) Uani 1 1 d . . . . .
O21 O 0.9411(4) 0.44838(9) 0.1254(3) 0.0678(9) Uani 1 1 d . . . . .
O22 O 0.8455(7) 0.49690(12) 0.1668(5) 0.1194(19) Uani 1 1 d . . . . .
N7 N 1.2189(4) 0.36395(11) 0.1534(3) 0.0553(10) Uani 1 1 d . . . . .
N8 N 1.2495(5) 0.39240(15) 0.1792(4) 0.0780(14) Uani 1 1 d . . . . .
N9 N 1.2873(9) 0.41809(19) 0.1956(6) 0.139(3) Uani 1 1 d . . . . .
N10 N 0.9540(5) 0.30171(11) 0.2269(3) 0.0620(11) Uani 1 1 d . . . . .
N11 N 0.8941(9) 0.27770(16) 0.1997(4) 0.110(2) Uani 1 1 d . . . . .
N12 N 0.8179(13) 0.2560(2) 0.1832(7) 0.192(5) Uani 1 1 d . . . . .
C18 C 1.0900(4) 0.35084(11) 0.2074(3) 0.0441(10) Uani 1 1 d . . . . .
C19 C 1.0590(5) 0.31763(11) 0.1573(3) 0.0477(10) Uani 1 1 d . . . . .
H19 H 1.1487 0.3047 0.1567 0.057 Uiso 1 1 calc R . . . .
C20 C 1.0084(5) 0.32286(11) 0.0466(3) 0.0445(10) Uani 1 1 d . . . . .
H20 H 1.0902 0.3315 0.0067 0.053 Uiso 1 1 calc R . . . .
C21 C 0.8835(4) 0.34692(12) 0.0368(3) 0.0472(10) Uani 1 1 d . . . . .
H21 H 0.8670 0.3521 -0.0368 0.057 Uiso 1 1 calc R . . . .
C22 C 0.9202(4) 0.37832(11) 0.0955(3) 0.0433(10) Uani 1 1 d . . . . .
H22 H 0.9975 0.3898 0.0583 0.052 Uiso 1 1 calc R . . . .
C23 C 1.1242(5) 0.34829(12) 0.3237(4) 0.0475(11) Uani 1 1 d . . . . .
C24 C 1.2560(7) 0.31866(16) 0.4508(4) 0.0829(18) Uani 1 1 d . . . . .
H24A H 1.3328 0.3028 0.4542 0.124 Uiso 1 1 calc GR . . . .
H24B H 1.1744 0.3109 0.4898 0.124 Uiso 1 1 calc GR . . . .
H24C H 1.2892 0.3391 0.4795 0.124 Uiso 1 1 calc GR . . . .
C25 C 1.0625(7) 0.27595(14) -0.0562(4) 0.0679(15) Uani 1 1 d . . . . .
C26 C 1.0065(8) 0.24430(17) -0.0929(7) 0.106(2) Uani 1 1 d . . . . .
H26A H 0.9621 0.2329 -0.0361 0.159 Uiso 1 1 calc GR . . . .
H26B H 1.0850 0.2314 -0.1199 0.159 Uiso 1 1 calc GR . . . .
H26C H 0.9358 0.2479 -0.1468 0.159 Uiso 1 1 calc GR . . . .
C27 C 0.6429(5) 0.32585(13) 0.0110(5) 0.0618(13) Uani 1 1 d . . . . .
C28 C 0.5161(6) 0.31313(18) 0.0706(5) 0.091(2) Uani 1 1 d . . . . .
H28A H 0.5448 0.2940 0.1091 0.137 Uiso 1 1 calc GR . . . .
H28B H 0.4393 0.3075 0.0231 0.137 Uiso 1 1 calc GR . . . .
H28C H 0.4828 0.3297 0.1177 0.137 Uiso 1 1 calc GR . . . .
C29 C 0.7908(5) 0.40106(12) 0.1052(3) 0.0504(11) Uani 1 1 d . . . . .
H29 H 0.7114 0.3890 0.1383 0.061 Uiso 1 1 calc R . . . .
C30 C 0.6068(6) 0.40762(15) -0.0270(5) 0.0710(15) Uani 1 1 d . . . . .
C31 C 0.5852(7) 0.41431(18) -0.1395(5) 0.092(2) Uani 1 1 d . . . . .
H31A H 0.6229 0.4356 -0.1558 0.139 Uiso 1 1 calc GR . . . .
H31B H 0.4835 0.4136 -0.1559 0.139 Uiso 1 1 calc GR . . . .
H31C H 0.6354 0.3980 -0.1795 0.139 Uiso 1 1 calc GR . . . .
C32 C 0.8181(6) 0.43201(12) 0.1655(4) 0.0596(13) Uani 1 1 d . . . . .
H32A H 0.7339 0.4462 0.1606 0.072 Uiso 1 1 calc R . . . .
H32B H 0.8341 0.4268 0.2382 0.072 Uiso 1 1 calc R . . . .
C33 C 0.9445(9) 0.48119(17) 0.1364(5) 0.0820(18) Uani 1 1 d . . . . .
C34 C 1.0889(10) 0.4946(2) 0.1058(7) 0.124(3) Uani 1 1 d . . . . .
H34A H 1.1597 0.4773 0.1075 0.185 Uiso 1 1 calc GR . . . .
H34B H 1.1170 0.5116 0.1535 0.185 Uiso 1 1 calc GR . . . .
H34C H 1.0827 0.5034 0.0367 0.185 Uiso 1 1 calc GR . . . .
O23 O 0.7595(3) 0.62176(7) 0.8499(2) 0.0490(7) Uani 1 1 d . . . . .
O24 O 1.0442(4) 0.61729(12) 0.8228(4) 0.0928(14) Uani 1 1 d . . . . .
O25 O 1.0157(3) 0.57549(11) 0.7156(3) 0.0802(12) Uani 1 1 d . . . . .
O26 O 0.4984(3) 0.54161(8) 0.7892(2) 0.0536(8) Uani 1 1 d . . . . .
O27 O 0.4729(4) 0.53510(11) 0.6171(3) 0.0819(12) Uani 1 1 d . . . . .
O28 O 0.5421(3) 0.58089(8) 0.9610(2) 0.0549(8) Uani 1 1 d . . . . .
O29 O 0.3048(5) 0.56905(13) 0.9746(3) 0.0959(14) Uani 1 1 d . . . . .
O30 O 0.4325(4) 0.65770(9) 0.9496(3) 0.0647(9) Uani 1 1 d . . . . .
O31 O 0.4086(5) 0.63552(12) 1.1094(3) 0.0875(13) Uani 1 1 d . . . . .
O32 O 0.6322(5) 0.69754(9) 0.8481(3) 0.0813(11) Uani 1 1 d . . . . .
N13 N 0.7655(4) 0.61507(11) 0.6641(3) 0.0541(10) Uani 1 1 d . . . . .
N14 N 0.8092(5) 0.64258(15) 0.6479(4) 0.0758(13) Uani 1 1 d . . . . .
N15 N 0.8424(9) 0.66817(19) 0.6246(6) 0.135(3) Uani 1 1 d . . . . .
N16 N 0.7947(4) 0.55263(12) 0.8659(3) 0.0626(11) Uani 1 1 d . . . . .
N17 N 0.7485(5) 0.52559(15) 0.8922(4) 0.0707(12) Uani 1 1 d . . . . .
N18 N 0.7172(8) 0.50150(18) 0.9276(5) 0.115(2) Uani 1 1 d . . . . .
C35 C 0.8029(4) 0.60179(12) 0.7679(3) 0.0482(11) Uani 1 1 d . . . . .
C36 C 0.7312(4) 0.56807(11) 0.7716(4) 0.0468(10) Uani 1 1 d . . . . .
H36 H 0.7572 0.5554 0.7097 0.056 Uiso 1 1 calc R . . . .
C37 C 0.5679(4) 0.57312(11) 0.7751(3) 0.0437(10) Uani 1 1 d . . . . .
H37 H 0.5360 0.5823 0.7083 0.052 Uiso 1 1 calc R . . . .
C38 C 0.5196(4) 0.59601(11) 0.8612(3) 0.0452(10) Uani 1 1 d . . . . .
H38 H 0.4162 0.6010 0.8522 0.054 Uiso 1 1 calc R . . . .
C39 C 0.6058(4) 0.62740(11) 0.8551(4) 0.0461(10) Uani 1 1 d . . . . .
H39 H 0.5757 0.6393 0.7923 0.055 Uiso 1 1 calc R . . . .
C40 C 0.9696(5) 0.59938(14) 0.7748(4) 0.0579(12) Uani 1 1 d . . . . .
C41 C 1.1698(5) 0.5691(2) 0.7164(6) 0.103(2) Uani 1 1 d . . . . .
H41A H 1.1905 0.5510 0.6709 0.155 Uiso 1 1 calc GR . . . .
H41B H 1.2006 0.5637 0.7858 0.155 Uiso 1 1 calc GR . . . .
H41C H 1.2208 0.5882 0.6930 0.155 Uiso 1 1 calc GR . . . .
C42 C 0.4592(5) 0.52467(12) 0.7020(5) 0.0569(13) Uani 1 1 d . . . . .
C43 C 0.3980(7) 0.49230(15) 0.7305(6) 0.092(2) Uani 1 1 d . . . . .
H43A H 0.4555 0.4827 0.7851 0.139 Uiso 1 1 calc GR . . . .
H43B H 0.3988 0.4781 0.6708 0.139 Uiso 1 1 calc GR . . . .
H43C H 0.3000 0.4951 0.7540 0.139 Uiso 1 1 calc GR . . . .
C44 C 0.4233(7) 0.56827(16) 1.0100(4) 0.0750(16) Uani 1 1 d . . . . .
C45 C 0.4690(9) 0.5528(2) 1.1102(5) 0.105(2) Uani 1 1 d . . . . .
H45A H 0.4735 0.5294 1.1018 0.158 Uiso 1 1 calc GR . . . .
H45B H 0.3999 0.5581 1.1633 0.158 Uiso 1 1 calc GR . . . .
H45C H 0.5629 0.5609 1.1301 0.158 Uiso 1 1 calc GR . . . .
C46 C 0.5838(5) 0.64978(12) 0.9484(4) 0.0540(12) Uani 1 1 d . . . . .
H46 H 0.6094 0.6379 1.0123 0.065 Uiso 1 1 calc R . . . .
C47 C 0.3541(6) 0.64878(16) 1.0357(5) 0.0730(16) Uani 1 1 d . . . . .
C48 C 0.1990(7) 0.6579(2) 1.0218(6) 0.110(3) Uani 1 1 d . . . . .
H48A H 0.1926 0.6792 0.9906 0.165 Uiso 1 1 calc GR . . . .
H48B H 0.1521 0.6582 1.0883 0.165 Uiso 1 1 calc GR . . . .
H48C H 0.1521 0.6421 0.9775 0.165 Uiso 1 1 calc GR . . . .
C49 C 0.6711(6) 0.68110(13) 0.9426(4) 0.0650(14) Uani 1 1 d . . . . .
H49A H 0.6500 0.6950 1.0019 0.078 Uiso 1 1 calc R . . . .
H49B H 0.7741 0.6761 0.9431 0.078 Uiso 1 1 calc R . . . .
C50 C 0.6970(12) 0.7255(2) 0.8246(6) 0.123(3) Uani 1 1 d . . . . .
C51 C 0.6441(13) 0.7403(2) 0.7266(6) 0.151(4) Uani 1 1 d . . . . .
H51A H 0.6674 0.7262 0.6693 0.226 Uiso 1 1 calc GR . . . .
H51B H 0.6897 0.7612 0.7168 0.226 Uiso 1 1 calc GR . . . .
H51C H 0.5408 0.7431 0.7299 0.226 Uiso 1 1 calc GR . . . .
O33 O 0.856(10) 0.7201(17) 0.859(4) 0.201(9) Uani 0.19(3) 1 d . . P A 1
O33A O 0.776(2) 0.7387(5) 0.8834(10) 0.201(9) Uani 0.81(3) 1 d . . P A 2
O34 O 0.7358(3) 0.37721(7) 0.5907(2) 0.0453(7) Uani 1 1 d . . . . .
O35 O 0.4537(4) 0.38104(11) 0.5663(3) 0.0863(13) Uani 1 1 d . . . . .
O36 O 0.4752(3) 0.42306(9) 0.4580(3) 0.0669(10) Uani 1 1 d . . . . .
O37 O 0.9944(3) 0.45773(7) 0.5303(2) 0.0467(7) Uani 1 1 d . . . . .
O38 O 1.0197(4) 0.46344(10) 0.3587(3) 0.0740(10) Uani 1 1 d . . . . .
O39 O 0.9561(3) 0.41840(7) 0.7025(2) 0.0470(7) Uani 1 1 d . . . . .
O40 O 1.1955(4) 0.42800(10) 0.7172(3) 0.0761(11) Uani 1 1 d . . . . .
O41 O 1.0663(3) 0.34157(8) 0.6912(3) 0.0587(9) Uani 1 1 d . . . . .
O42 O 1.0923(4) 0.36369(11) 0.8511(3) 0.0778(11) Uani 1 1 d . . . . .
O43 O 0.8620(5) 0.30170(9) 0.5895(3) 0.0747(10) Uani 1 1 d . . . . .
N19 N 0.7278(4) 0.38409(10) 0.4036(3) 0.0479(9) Uani 1 1 d . . . . .
N20 N 0.6839(5) 0.35649(13) 0.3880(4) 0.0693(12) Uani 1 1 d . . . . .
N21 N 0.6522(9) 0.33107(17) 0.3638(6) 0.133(3) Uani 1 1 d . . . . .
N22 N 0.6989(4) 0.44617(10) 0.6062(3) 0.0539(10) Uani 1 1 d . . . . .
N23 N 0.7545(5) 0.47134(11) 0.6398(3) 0.0593(11) Uani 1 1 d . . . . .
N24 N 0.7925(6) 0.49401(14) 0.6822(4) 0.0884(16) Uani 1 1 d . . . . .
C52 C 0.6913(4) 0.39739(10) 0.5084(3) 0.0410(9) Uani 1 1 d . . . . .
C53 C 0.7621(4) 0.43099(10) 0.5132(3) 0.0414(9) Uani 1 1 d . . . . .
H53 H 0.7350 0.4437 0.4514 0.050 Uiso 1 1 calc R . . . .
C54 C 0.9270(4) 0.42634(10) 0.5166(3) 0.0386(9) Uani 1 1 d . . . . .
H54 H 0.9581 0.4173 0.4497 0.046 Uiso 1 1 calc R . . . .
C55 C 0.9767(4) 0.40358(10) 0.6017(3) 0.0401(9) Uani 1 1 d . . . . .
H55 H 1.0800 0.3988 0.5924 0.048 Uiso 1 1 calc R . . . .
C56 C 0.8912(4) 0.37174(11) 0.5954(3) 0.0435(10) Uani 1 1 d . . . . .
H56 H 0.9207 0.3599 0.5327 0.052 Uiso 1 1 calc R . . . .
C57 C 0.5252(5) 0.39930(12) 0.5166(4) 0.0515(11) Uani 1 1 d . . . . .
C58 C 0.3204(5) 0.42885(16) 0.4615(5) 0.0796(17) Uani 1 1 d . . . . .
H58A H 0.2943 0.4450 0.4105 0.119 Uiso 1 1 calc GR . . . .
H58B H 0.2943 0.4366 0.5294 0.119 Uiso 1 1 calc GR . . . .
H58C H 0.2697 0.4088 0.4469 0.119 Uiso 1 1 calc GR . . . .
C59 C 1.0290(4) 0.47471(12) 0.4431(4) 0.0499(11) Uani 1 1 d . . . . .
C60 C 1.0811(6) 0.50816(13) 0.4698(5) 0.0789(17) Uani 1 1 d . . . . .
H60A H 1.0098 0.5190 0.5116 0.118 Uiso 1 1 calc GR . . . .
H60B H 1.0964 0.5204 0.4071 0.118 Uiso 1 1 calc GR . . . .
H60C H 1.1707 0.5066 0.5079 0.118 Uiso 1 1 calc GR . . . .
C61 C 1.0753(6) 0.42964(13) 0.7529(4) 0.0569(12) Uani 1 1 d . . . . .
C62 C 1.0370(7) 0.44518(17) 0.8537(4) 0.0831(18) Uani 1 1 d . . . . .
H62A H 0.9725 0.4633 0.8414 0.125 Uiso 1 1 calc GR . . . .
H62B H 1.1237 0.4530 0.8873 0.125 Uiso 1 1 calc GR . . . .
H62C H 0.9903 0.4293 0.8974 0.125 Uiso 1 1 calc GR . . . .
C63 C 0.9131(5) 0.34942(11) 0.6893(3) 0.0484(11) Uani 1 1 d . . . . .
H63 H 0.8883 0.3615 0.7527 0.058 Uiso 1 1 calc R . . . .
C64 C 1.1442(6) 0.35003(15) 0.7768(5) 0.0672(15) Uani 1 1 d . . . . .
C65 C 1.2984(6) 0.34101(19) 0.7642(5) 0.095(2) Uani 1 1 d . . . . .
H65A H 1.3050 0.3207 0.7267 0.143 Uiso 1 1 calc GR . . . .
H65B H 1.3429 0.3385 0.8315 0.143 Uiso 1 1 calc GR . . . .
H65C H 1.3476 0.3579 0.7263 0.143 Uiso 1 1 calc GR . . . .
C66 C 0.8260(6) 0.31824(13) 0.6849(4) 0.0636(13) Uani 1 1 d . . . . .
H66A H 0.8493 0.3044 0.7441 0.076 Uiso 1 1 calc R . . . .
H66B H 0.7230 0.3232 0.6865 0.076 Uiso 1 1 calc R . . . .
C67 C 0.7992(11) 0.27406(18) 0.5679(5) 0.109(3) Uani 1 1 d . . . . .
C68 C 0.8502(13) 0.2592(2) 0.4692(6) 0.148(4) Uani 1 1 d . . . . .
H68A H 0.9209 0.2734 0.4378 0.223 Uiso 1 1 calc GR . . . .
H68B H 0.7693 0.2565 0.4225 0.223 Uiso 1 1 calc GR . . . .
H68C H 0.8933 0.2383 0.4833 0.223 Uiso 1 1 calc GR . . . .
O44 O 0.729(2) 0.2589(3) 0.6308(10) 0.153(6) Uani 0.70(2) 1 d . . P B 1
O44A O 0.645(5) 0.2744(8) 0.602(3) 0.153(6) Uani 0.30(2) 1 d . . 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 1.400(5) . ?
O1 C5 1.439(5) . ?
O2 C6 1.191(6) . ?
O3 C6 1.317(6) . ?
O3 C7 1.453(6) . ?
O4 C3 1.429(5) . ?
O4 C8 1.347(6) . ?
O5 C8 1.196(7) . ?
O6 C4 1.445(5) . ?
O6 C10 1.358(6) . ?
O7 C10 1.194(7) . ?
O8 C12 1.451(6) . ?
O8 C13 1.352(6) . ?
O9 C13 1.195(7) . ?
O10 C15 1.434(7) . ?
O10 C16 1.334(6) . ?
O11 C16 1.198(6) . ?
N1 N2 1.225(7) . ?
N1 C1 1.490(5) . ?
N2 N3 1.114(8) . ?
N4 N5 1.179(7) . ?
N4 C2 1.478(6) . ?
N5 N6 1.154(10) . ?
C1 C2 1.529(6) . ?
C1 C6 1.535(6) . ?
C2 C3 1.513(6) . ?
C3 C4 1.524(6) . ?
C4 C5 1.506(7) . ?
C5 C12 1.528(6) . ?
C8 C9 1.458(8) . ?
C10 C11 1.479(8) . ?
C12 C15 1.485(8) . ?
C13 C14 1.454(9) . ?
C16 C17 1.471(9) . ?
O12 C18 1.409(5) . ?
O12 C22 1.439(5) . ?
O13 C23 1.184(5) . ?
O14 C23 1.319(6) . ?
O14 C24 1.457(6) . ?
O15 C20 1.432(5) . ?
O15 C25 1.341(6) . ?
O16 C25 1.205(7) . ?
O17 C21 1.443(5) . ?
O17 C27 1.377(6) . ?
O18 C27 1.181(6) . ?
O19 C29 1.446(5) . ?
O19 C30 1.356(6) . ?
O20 C30 1.192(7) . ?
O21 C32 1.415(6) . ?
O21 C33 1.345(8) . ?
O22 C33 1.182(8) . ?
N7 N8 1.238(7) . ?
N7 C18 1.479(6) . ?
N8 N9 1.124(7) . ?
N10 N11 1.176(7) . ?
N10 C19 1.472(6) . ?
N11 N12 1.149(9) . ?
C18 C19 1.525(7) . ?
C18 C23 1.530(6) . ?
C19 C20 1.511(6) . ?
C20 C21 1.516(6) . ?
C21 C22 1.523(7) . ?
C22 C29 1.516(6) . ?
C25 C26 1.467(8) . ?
C27 C28 1.493(8) . ?
C29 C32 1.501(7) . ?
C30 C31 1.484(9) . ?
C33 C34 1.492(11) . ?
O23 C35 1.392(5) . ?
O23 C39 1.436(5) . ?
O24 C40 1.176(6) . ?
O25 C40 1.308(6) . ?
O25 C41 1.444(6) . ?
O26 C37 1.447(5) . ?
O26 C42 1.363(6) . ?
O27 C42 1.179(6) . ?
O28 C38 1.437(5) . ?
O28 C44 1.366(6) . ?
O29 C44 1.181(7) . ?
O30 C46 1.431(5) . ?
O30 C47 1.374(7) . ?
O31 C47 1.198(7) . ?
O32 C49 1.431(6) . ?
O32 C50 1.321(8) . ?
N13 N14 1.210(7) . ?
N13 C35 1.479(6) . ?
N14 N15 1.128(8) . ?
N16 N17 1.229(7) . ?
N16 C36 1.483(6) . ?
N17 N18 1.121(7) . ?
C35 C36 1.526(6) . ?
C35 C40 1.541(6) . ?
C36 C37 1.519(6) . ?
C37 C38 1.516(6) . ?
C38 C39 1.508(6) . ?
C39 C46 1.522(6) . ?
C42 C43 1.482(8) . ?
C44 C45 1.492(9) . ?
C46 C49 1.511(7) . ?
C47 C48 1.486(9) . ?
C50 C51 1.479(11) . ?
C50 O33 1.54(9) . ?
C50 O33A 1.178(11) . ?
O34 C52 1.399(5) . ?
O34 C56 1.450(5) . ?
O35 C57 1.184(6) . ?
O36 C57 1.309(6) . ?
O36 C58 1.447(5) . ?
O37 C54 1.433(5) . ?
O37 C59 1.358(6) . ?
O38 C59 1.181(6) . ?
O39 C55 1.443(5) . ?
O39 C61 1.352(5) . ?
O40 C61 1.204(6) . ?
O41 C63 1.447(5) . ?
O41 C64 1.355(7) . ?
O42 C64 1.207(7) . ?
O43 C66 1.440(6) . ?
O43 C67 1.296(8) . ?
N19 N20 1.212(6) . ?
N19 C52 1.492(5) . ?
N20 N21 1.121(7) . ?
N22 N23 1.224(6) . ?
N22 C53 1.469(6) . ?
N23 N24 1.128(6) . ?
C52 C53 1.518(6) . ?
C52 C57 1.536(6) . ?
C53 C54 1.531(5) . ?
C54 C55 1.504(6) . ?
C55 C56 1.520(6) . ?
C56 C63 1.524(6) . ?
C59 C60 1.485(7) . ?
C61 C62 1.486(8) . ?
C63 C66 1.504(7) . ?
C64 C65 1.478(8) . ?
C67 C68 1.484(11) . ?
C67 O44 1.207(12) . ?
C67 O44A 1.49(4) . ?

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 C5 114.5(3) . . ?
C6 O3 C7 116.6(4) . . ?
C8 O4 C3 118.3(4) . . ?
C10 O6 C4 117.4(4) . . ?
C13 O8 C12 120.0(4) . . ?
C16 O10 C15 116.2(4) . . ?
N2 N1 C1 111.8(4) . . ?
N3 N2 N1 172.9(6) . . ?
N5 N4 C2 119.2(5) . . ?
N6 N5 N4 169.1(9) . . ?
O1 C1 N1 112.8(4) . . ?
O1 C1 C2 111.6(4) . . ?
O1 C1 C6 106.0(3) . . ?
N1 C1 C2 105.2(3) . . ?
N1 C1 C6 107.7(4) . . ?
C2 C1 C6 113.7(4) . . ?
N4 C2 C1 103.9(3) . . ?
N4 C2 C3 115.7(4) . . ?
C3 C2 C1 108.8(4) . . ?
O4 C3 C2 110.4(4) . . ?
O4 C3 C4 108.5(3) . . ?
C2 C3 C4 114.1(3) . . ?
O6 C4 C3 109.5(4) . . ?
O6 C4 C5 109.1(3) . . ?
C5 C4 C3 109.3(4) . . ?
O1 C5 C4 113.1(4) . . ?
O1 C5 C12 105.4(3) . . ?
C4 C5 C12 111.7(4) . . ?
O2 C6 O3 124.2(5) . . ?
O2 C6 C1 124.2(4) . . ?
O3 C6 C1 111.3(4) . . ?
O4 C8 C9 111.8(5) . . ?
O5 C8 O4 120.7(5) . . ?
O5 C8 C9 127.4(5) . . ?
O6 C10 C11 109.8(6) . . ?
O7 C10 O6 122.9(5) . . ?
O7 C10 C11 127.3(6) . . ?
O8 C12 C5 103.9(3) . . ?
O8 C12 C15 110.6(4) . . ?
C15 C12 C5 116.5(4) . . ?
O8 C13 C14 112.0(5) . . ?
O9 C13 O8 120.5(6) . . ?
O9 C13 C14 127.5(6) . . ?
O10 C15 C12 110.0(4) . . ?
O10 C16 C17 111.3(5) . . ?
O11 C16 O10 123.4(5) . . ?
O11 C16 C17 125.3(6) . . ?
C18 O12 C22 114.7(3) . . ?
C23 O14 C24 116.5(4) . . ?
C25 O15 C20 118.1(4) . . ?
C27 O17 C21 116.6(4) . . ?
C30 O19 C29 118.5(4) . . ?
C33 O21 C32 116.7(5) . . ?
N8 N7 C18 113.3(4) . . ?
N9 N8 N7 173.4(6) . . ?
N11 N10 C19 119.7(5) . . ?
N12 N11 N10 169.0(9) . . ?
O12 C18 N7 112.8(4) . . ?
O12 C18 C19 111.3(3) . . ?
O12 C18 C23 105.4(3) . . ?
N7 C18 C19 105.8(3) . . ?
N7 C18 C23 108.8(3) . . ?
C19 C18 C23 112.9(4) . . ?
N10 C19 C18 104.9(4) . . ?
N10 C19 C20 115.7(4) . . ?
C20 C19 C18 109.2(4) . . ?
O15 C20 C19 110.7(4) . . ?
O15 C20 C21 108.4(3) . . ?
C19 C20 C21 113.5(4) . . ?
O17 C21 C20 110.1(4) . . ?
O17 C21 C22 109.0(3) . . ?
C20 C21 C22 109.7(3) . . ?
O12 C22 C21 112.0(4) . . ?
O12 C22 C29 106.1(3) . . ?
C29 C22 C21 112.5(4) . . ?
O13 C23 O14 124.2(4) . . ?
O13 C23 C18 124.8(4) . . ?
O14 C23 C18 110.9(4) . . ?
O15 C25 C26 112.3(6) . . ?
O16 C25 O15 121.4(5) . . ?
O16 C25 C26 126.2(6) . . ?
O17 C27 C28 108.6(5) . . ?
O18 C27 O17 123.5(5) . . ?
O18 C27 C28 127.9(5) . . ?
O19 C29 C22 104.3(3) . . ?
O19 C29 C32 111.2(4) . . ?
C32 C29 C22 115.3(4) . . ?
O19 C30 C31 111.1(5) . . ?
O20 C30 O19 121.8(6) . . ?
O20 C30 C31 127.1(5) . . ?
O21 C32 C29 109.9(4) . . ?
O21 C33 C34 110.8(7) . . ?
O22 C33 O21 123.8(7) . . ?
O22 C33 C34 125.4(7) . . ?
C35 O23 C39 114.6(3) . . ?
C40 O25 C41 117.0(4) . . ?
C42 O26 C37 117.6(4) . . ?
C44 O28 C38 117.5(4) . . ?
C47 O30 C46 117.7(4) . . ?
C50 O32 C49 119.1(5) . . ?
N14 N13 C35 114.7(4) . . ?
N15 N14 N13 173.6(6) . . ?
N17 N16 C36 118.0(4) . . ?
N18 N17 N16 170.9(6) . . ?
O23 C35 N13 113.8(4) . . ?
O23 C35 C36 112.2(4) . . ?
O23 C35 C40 106.5(3) . . ?
N13 C35 C36 105.0(3) . . ?
N13 C35 C40 107.6(4) . . ?
C36 C35 C40 111.8(4) . . ?
N16 C36 C35 103.9(3) . . ?
N16 C36 C37 114.8(4) . . ?
C37 C36 C35 107.9(3) . . ?
O26 C37 C36 108.8(3) . . ?
O26 C37 C38 108.9(4) . . ?
C38 C37 C36 113.6(3) . . ?
O28 C38 C37 110.2(4) . . ?
O28 C38 C39 109.7(3) . . ?
C39 C38 C37 109.1(4) . . ?
O23 C39 C38 112.7(4) . . ?
O23 C39 C46 105.6(3) . . ?
C38 C39 C46 113.3(4) . . ?
O24 C40 O25 125.2(4) . . ?
O24 C40 C35 124.8(5) . . ?
O25 C40 C35 109.9(4) . . ?
O26 C42 C43 110.3(5) . . ?
O27 C42 O26 123.3(5) . . ?
O27 C42 C43 126.4(5) . . ?
O28 C44 C45 109.5(5) . . ?
O29 C44 O28 123.6(6) . . ?
O29 C44 C45 126.8(6) . . ?
O30 C46 C39 106.1(3) . . ?
O30 C46 C49 109.2(4) . . ?
C49 C46 C39 113.2(4) . . ?
O30 C47 C48 110.3(6) . . ?
O31 C47 O30 122.4(5) . . ?
O31 C47 C48 127.3(6) . . ?
O32 C49 C46 107.9(4) . . ?
O32 C50 C51 113.6(7) . . ?
O32 C50 O33 104(2) . . ?
C51 C50 O33 127(2) . . ?
O33A C50 O32 121.8(9) . . ?
O33A C50 C51 124.0(10) . . ?
C52 O34 C56 114.0(3) . . ?
C57 O36 C58 116.5(4) . . ?
C59 O37 C54 117.2(3) . . ?
C61 O39 C55 117.5(4) . . ?
C64 O41 C63 118.0(4) . . ?
C67 O43 C66 119.0(5) . . ?
N20 N19 C52 114.2(4) . . ?
N21 N20 N19 172.3(6) . . ?
N23 N22 C53 118.2(4) . . ?
N24 N23 N22 170.2(6) . . ?
O34 C52 N19 113.7(3) . . ?
O34 C52 C53 112.1(3) . . ?
O34 C52 C57 105.4(3) . . ?
N19 C52 C53 105.4(3) . . ?
N19 C52 C57 108.0(3) . . ?
C53 C52 C57 112.3(4) . . ?
N22 C53 C52 103.9(3) . . ?
N22 C53 C54 115.3(3) . . ?
C52 C53 C54 108.4(3) . . ?
O37 C54 C53 108.8(3) . . ?
O37 C54 C55 109.4(3) . . ?
C55 C54 C53 113.2(3) . . ?
O39 C55 C54 110.7(3) . . ?
O39 C55 C56 109.6(3) . . ?
C54 C55 C56 109.4(3) . . ?
O34 C56 C55 112.4(3) . . ?
O34 C56 C63 104.6(3) . . ?
C55 C56 C63 113.6(3) . . ?
O35 C57 O36 125.5(4) . . ?
O35 C57 C52 124.2(5) . . ?
O36 C57 C52 110.2(4) . . ?
O37 C59 C60 110.7(5) . . ?
O38 C59 O37 123.0(4) . . ?
O38 C59 C60 126.3(5) . . ?
O39 C61 C62 111.5(5) . . ?
O40 C61 O39 123.0(5) . . ?
O40 C61 C62 125.4(4) . . ?
O41 C63 C56 105.7(3) . . ?
O41 C63 C66 109.5(4) . . ?
C66 C63 C56 114.0(4) . . ?
O41 C64 C65 110.7(6) . . ?
O42 C64 O41 123.4(5) . . ?
O42 C64 C65 125.9(6) . . ?
O43 C66 C63 107.6(4) . . ?
O43 C67 C68 113.2(7) . . ?
O43 C67 O44A 110.7(12) . . ?
C68 C67 O44A 124.3(14) . . ?
O44 C67 O43 122.7(8) . . ?
O44 C67 C68 122.5(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N4 -69.5(4) . . . . ?
O1 C1 C2 C3 54.4(4) . . . . ?
O1 C1 C6 O2 -22.3(6) . . . . ?
O1 C1 C6 O3 162.4(4) . . . . ?
O1 C5 C12 O8 176.2(3) . . . . ?
O1 C5 C12 C15 54.3(5) . . . . ?
O4 C3 C4 O6 53.5(4) . . . . ?
O4 C3 C4 C5 173.0(3) . . . . ?
O6 C4 C5 O1 70.0(4) . . . . ?
O6 C4 C5 C12 -48.6(5) . . . . ?
O8 C12 C15 O10 -55.8(5) . . . . ?
N1 C1 C2 N4 167.8(4) . . . . ?
N1 C1 C2 C3 -68.3(4) . . . . ?
N1 C1 C6 O2 98.7(5) . . . . ?
N1 C1 C6 O3 -76.6(5) . . . . ?
N2 N1 C1 O1 47.9(6) . . . . ?
N2 N1 C1 C2 169.7(5) . . . . ?
N2 N1 C1 C6 -68.7(5) . . . . ?
N4 C2 C3 O4 -57.4(5) . . . . ?
N4 C2 C3 C4 65.1(5) . . . . ?
N5 N4 C2 C1 165.7(6) . . . . ?
N5 N4 C2 C3 46.4(7) . . . . ?
C1 O1 C5 C4 56.9(4) . . . . ?
C1 O1 C5 C12 179.1(4) . . . . ?
C1 C2 C3 O4 -173.9(3) . . . . ?
C1 C2 C3 C4 -51.4(5) . . . . ?
C2 N4 N5 N6 -158(5) . . . . ?
C2 C1 C6 O2 -145.2(5) . . . . ?
C2 C1 C6 O3 39.5(5) . . . . ?
C2 C3 C4 O6 -70.1(5) . . . . ?
C2 C3 C4 C5 49.4(5) . . . . ?
C3 O4 C8 O5 0.7(8) . . . . ?
C3 O4 C8 C9 176.4(5) . . . . ?
C3 C4 C5 O1 -49.7(4) . . . . ?
C3 C4 C5 C12 -168.3(3) . . . . ?
C4 O6 C10 O7 3.5(7) . . . . ?
C4 O6 C10 C11 -175.4(5) . . . . ?
C4 C5 C12 O8 -60.6(4) . . . . ?
C4 C5 C12 C15 177.4(4) . . . . ?
C5 O1 C1 N1 59.6(5) . . . . ?
C5 O1 C1 C2 -58.6(4) . . . . ?
C5 O1 C1 C6 177.2(3) . . . . ?
C5 C12 C15 O10 62.6(6) . . . . ?
C6 C1 C2 N4 50.3(4) . . . . ?
C6 C1 C2 C3 174.1(3) . . . . ?
C7 O3 C6 O2 3.1(8) . . . . ?
C7 O3 C6 C1 178.4(5) . . . . ?
C8 O4 C3 C2 -95.0(5) . . . . ?
C8 O4 C3 C4 139.2(4) . . . . ?
C10 O6 C4 C3 -115.1(4) . . . . ?
C10 O6 C4 C5 125.3(4) . . . . ?
C12 O8 C13 O9 0.2(9) . . . . ?
C12 O8 C13 C14 -178.8(5) . . . . ?
C13 O8 C12 C5 142.7(4) . . . . ?
C13 O8 C12 C15 -91.5(5) . . . . ?
C15 O10 C16 O11 0.1(8) . . . . ?
C15 O10 C16 C17 -179.2(6) . . . . ?
C16 O10 C15 C12 149.4(5) . . . . ?
O12 C18 C19 N10 -70.0(4) . . . . ?
O12 C18 C19 C20 54.7(4) . . . . ?
O12 C18 C23 O13 -18.4(6) . . . . ?
O12 C18 C23 O14 165.2(4) . . . . ?
O12 C22 C29 O19 177.4(3) . . . . ?
O12 C22 C29 C32 55.2(5) . . . . ?
O15 C20 C21 O17 54.0(4) . . . . ?
O15 C20 C21 C22 173.9(3) . . . . ?
O17 C21 C22 O12 70.1(4) . . . . ?
O17 C21 C22 C29 -49.3(5) . . . . ?
O19 C29 C32 O21 -66.0(5) . . . . ?
N7 C18 C19 N10 167.2(4) . . . . ?
N7 C18 C19 C20 -68.1(4) . . . . ?
N7 C18 C23 O13 102.8(5) . . . . ?
N7 C18 C23 O14 -73.6(5) . . . . ?
N8 N7 C18 O12 51.8(5) . . . . ?
N8 N7 C18 C19 173.7(4) . . . . ?
N8 N7 C18 C23 -64.8(5) . . . . ?
N10 C19 C20 O15 -56.3(5) . . . . ?
N10 C19 C20 C21 65.8(5) . . . . ?
N11 N10 C19 C18 168.8(6) . . . . ?
N11 N10 C19 C20 48.4(7) . . . . ?
C18 O12 C22 C21 56.9(4) . . . . ?
C18 O12 C22 C29 -180.0(4) . . . . ?
C18 C19 C20 O15 -174.4(3) . . . . ?
C18 C19 C20 C21 -52.2(5) . . . . ?
C19 N10 N11 N12 -150(5) . . . . ?
C19 C18 C23 O13 -140.1(5) . . . . ?
C19 C18 C23 O14 43.5(5) . . . . ?
C19 C20 C21 O17 -69.4(5) . . . . ?
C19 C20 C21 C22 50.5(5) . . . . ?
C20 O15 C25 O16 -0.6(8) . . . . ?
C20 O15 C25 C26 176.1(5) . . . . ?
C20 C21 C22 O12 -50.5(4) . . . . ?
C20 C21 C22 C29 -169.9(3) . . . . ?
C21 O17 C27 O18 2.5(7) . . . . ?
C21 O17 C27 C28 -177.4(4) . . . . ?
C21 C22 C29 O19 -59.8(4) . . . . ?
C21 C22 C29 C32 178.0(4) . . . . ?
C22 O12 C18 N7 59.9(5) . . . . ?
C22 O12 C18 C19 -58.8(4) . . . . ?
C22 O12 C18 C23 178.5(3) . . . . ?
C22 C29 C32 O21 52.4(5) . . . . ?
C23 C18 C19 N10 48.4(5) . . . . ?
C23 C18 C19 C20 173.0(3) . . . . ?
C24 O14 C23 O13 2.7(7) . . . . ?
C24 O14 C23 C18 179.1(4) . . . . ?
C25 O15 C20 C19 -94.7(5) . . . . ?
C25 O15 C20 C21 140.2(4) . . . . ?
C27 O17 C21 C20 -112.6(4) . . . . ?
C27 O17 C21 C22 127.1(4) . . . . ?
C29 O19 C30 O20 0.9(8) . . . . ?
C29 O19 C30 C31 -178.0(5) . . . . ?
C30 O19 C29 C22 136.2(4) . . . . ?
C30 O19 C29 C32 -99.0(5) . . . . ?
C32 O21 C33 O22 -8.4(9) . . . . ?
C32 O21 C33 C34 171.3(5) . . . . ?
C33 O21 C32 C29 151.8(4) . . . . ?
O23 C35 C36 N16 -67.3(4) . . . . ?
O23 C35 C36 C37 54.9(4) . . . . ?
O23 C35 C40 O24 -16.9(7) . . . . ?
O23 C35 C40 O25 165.9(4) . . . . ?
O23 C39 C46 O30 175.5(4) . . . . ?
O23 C39 C46 C49 55.8(5) . . . . ?
O26 C37 C38 O28 52.3(4) . . . . ?
O26 C37 C38 C39 172.9(3) . . . . ?
O28 C38 C39 O23 70.2(4) . . . . ?
O28 C38 C39 C46 -49.6(5) . . . . ?
O30 C46 C49 O32 -60.9(5) . . . . ?
N13 C35 C36 N16 168.7(3) . . . . ?
N13 C35 C36 C37 -69.1(4) . . . . ?
N13 C35 C40 O24 105.4(6) . . . . ?
N13 C35 C40 O25 -71.8(5) . . . . ?
N14 N13 C35 O23 54.4(5) . . . . ?
N14 N13 C35 C36 177.5(4) . . . . ?
N14 N13 C35 C40 -63.3(5) . . . . ?
N16 C36 C37 O26 -59.1(5) . . . . ?
N16 C36 C37 C38 62.3(5) . . . . ?
N17 N16 C36 C35 175.3(4) . . . . ?
N17 N16 C36 C37 57.8(6) . . . . ?
C35 O23 C39 C38 56.4(5) . . . . ?
C35 O23 C39 C46 -179.4(4) . . . . ?
C35 C36 C37 O26 -174.3(3) . . . . ?
C35 C36 C37 C38 -52.9(5) . . . . ?
C36 C35 C40 O24 -139.8(6) . . . . ?
C36 C35 C40 O25 43.1(6) . . . . ?
C36 C37 C38 O28 -69.0(5) . . . . ?
C36 C37 C38 C39 51.5(5) . . . . ?
C37 O26 C42 O27 -3.7(6) . . . . ?
C37 O26 C42 C43 176.7(4) . . . . ?
C37 C38 C39 O23 -50.7(4) . . . . ?
C37 C38 C39 C46 -170.5(3) . . . . ?
C38 O28 C44 O29 0.4(8) . . . . ?
C38 O28 C44 C45 178.3(5) . . . . ?
C38 C39 C46 O30 -60.7(5) . . . . ?
C38 C39 C46 C49 179.6(4) . . . . ?
C39 O23 C35 N13 60.6(5) . . . . ?
C39 O23 C35 C36 -58.4(5) . . . . ?
C39 O23 C35 C40 178.9(4) . . . . ?
C39 C46 C49 O32 57.1(5) . . . . ?
C40 C35 C36 N16 52.3(5) . . . . ?
C40 C35 C36 C37 174.5(4) . . . . ?
C41 O25 C40 O24 5.3(9) . . . . ?
C41 O25 C40 C35 -177.6(5) . . . . ?
C42 O26 C37 C36 -91.1(4) . . . . ?
C42 O26 C37 C38 144.7(4) . . . . ?
C44 O28 C38 C37 -102.8(5) . . . . ?
C44 O28 C38 C39 137.0(4) . . . . ?
C46 O30 C47 O31 1.8(8) . . . . ?
C46 O30 C47 C48 -178.0(5) . . . . ?
C47 O30 C46 C39 119.6(4) . . . . ?
C47 O30 C46 C49 -118.1(5) . . . . ?
C49 O32 C50 C51 -178.4(7) . . . . ?
C49 O32 C50 O33 39(3) . . . . ?
C49 O32 C50 O33A -7(2) . . . . ?
C50 O32 C49 C46 -178.7(6) . . . . ?
O34 C52 C53 N22 -67.6(4) . . . . ?
O34 C52 C53 C54 55.4(4) . . . . ?
O34 C52 C57 O35 -16.1(6) . . . . ?
O34 C52 C57 O36 166.2(4) . . . . ?
O34 C56 C63 O41 175.9(3) . . . . ?
O34 C56 C63 C66 55.6(5) . . . . ?
O37 C54 C55 O39 52.0(4) . . . . ?
O37 C54 C55 C56 172.9(3) . . . . ?
O39 C55 C56 O34 70.6(4) . . . . ?
O39 C55 C56 C63 -48.0(5) . . . . ?
O41 C63 C66 O43 -62.2(5) . . . . ?
N19 C52 C53 N22 168.2(3) . . . . ?
N19 C52 C53 C54 -68.7(4) . . . . ?
N19 C52 C57 O35 105.8(6) . . . . ?
N19 C52 C57 O36 -71.9(5) . . . . ?
N20 N19 C52 O34 54.1(5) . . . . ?
N20 N19 C52 C53 177.2(4) . . . . ?
N20 N19 C52 C57 -62.5(5) . . . . ?
N22 C53 C54 O37 -59.0(4) . . . . ?
N22 C53 C54 C55 62.8(5) . . . . ?
N23 N22 C53 C52 167.6(4) . . . . ?
N23 N22 C53 C54 49.1(6) . . . . ?
C52 O34 C56 C55 56.4(4) . . . . ?
C52 O34 C56 C63 -179.9(3) . . . . ?
C52 C53 C54 O37 -175.0(3) . . . . ?
C52 C53 C54 C55 -53.2(4) . . . . ?
C53 C52 C57 O35 -138.4(5) . . . . ?
C53 C52 C57 O36 43.9(5) . . . . ?
C53 C54 C55 O39 -69.5(4) . . . . ?
C53 C54 C55 C56 51.4(4) . . . . ?
C54 O37 C59 O38 -7.9(6) . . . . ?
C54 O37 C59 C60 173.2(4) . . . . ?
C54 C55 C56 O34 -51.0(4) . . . . ?
C54 C55 C56 C63 -169.5(3) . . . . ?
C55 O39 C61 O40 0.6(7) . . . . ?
C55 O39 C61 C62 178.1(4) . . . . ?
C55 C56 C63 O41 -61.2(5) . . . . ?
C55 C56 C63 C66 178.6(4) . . . . ?
C56 O34 C52 N19 60.7(4) . . . . ?
C56 O34 C52 C53 -58.7(4) . . . . ?
C56 O34 C52 C57 178.9(3) . . . . ?
C56 C63 C66 O43 55.9(5) . . . . ?
C57 C52 C53 N22 50.8(4) . . . . ?
C57 C52 C53 C54 173.9(3) . . . . ?
C58 O36 C57 O35 5.2(8) . . . . ?
C58 O36 C57 C52 -177.2(4) . . . . ?
C59 O37 C54 C53 -90.3(4) . . . . ?
C59 O37 C54 C55 145.6(3) . . . . ?
C61 O39 C55 C54 -105.3(4) . . . . ?
C61 O39 C55 C56 133.9(4) . . . . ?
C63 O41 C64 O42 0.0(7) . . . . ?
C63 O41 C64 C65 -178.5(4) . . . . ?
C64 O41 C63 C56 120.5(4) . . . . ?
C64 O41 C63 C66 -116.3(4) . . . . ?
C66 O43 C67 C68 -178.1(7) . . . . ?
C66 O43 C67 O44 -12.0(17) . . . . ?
C66 O43 C67 O44A 37.1(18) . . . . ?
C67 O43 C66 C63 -179.6(6) . . . . ?

_olex2_date_sample_data_collection 2009-06-13
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.920
####################################################################### 
# 
# 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_190419_s2_hh_hh190410a
_database_code_depnum_ccdc_archive 'CCDC 1975128'
loop_
_audit_author_name
_audit_author_address
HeHuan
;Sichuan university
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C35 H31 F3 N8 O11, 2(C H4 O)'
_chemical_formula_sum            'C37 H39 F3 N8 O13'
_chemical_formula_weight         860.76
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.9906(4)
_cell_length_b                   11.1438(4)
_cell_length_c                   14.8377(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.257(4)
_cell_angle_gamma                90
_cell_volume                     2090.74(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.5710
_cell_measurement_theta_min      3.3610
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9421
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.995
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762    0.0000  -90.0000 117

#__ type_ start__ end____ width___ exp.time_
  3 omega  -43.00   22.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762  -38.0000   60.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0396461000
_diffrn_orient_matrix_UB_12      -0.0120034000
_diffrn_orient_matrix_UB_13      -0.0405586000
_diffrn_orient_matrix_UB_21      0.0149665000
_diffrn_orient_matrix_UB_22      0.0522108000
_diffrn_orient_matrix_UB_23      -0.0211575000
_diffrn_orient_matrix_UB_31      0.0367446000
_diffrn_orient_matrix_UB_32      -0.0343771000
_diffrn_orient_matrix_UB_33      -0.0179004000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.654
_reflns_Friedel_fraction_max     0.620
_reflns_number_gt                5124
_reflns_number_total             7012
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         7012
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+0.4621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1378
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
3. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C20(H20)
4.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
4.c Aromatic/amide H refined with riding coordinates:
 N7(H7), N8(H8), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
4.e Idealised tetrahedral OH refined as rotating group:
 O13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.6894(2) 0.4332(3) 0.28262(19) 0.0409(7) Uani 1 1 d . . . . .
O2 O 0.5017(3) 0.2180(4) 0.2486(3) 0.0778(11) Uani 1 1 d . . . . .
O3 O 0.6701(3) 0.2027(3) 0.2395(3) 0.0756(11) Uani 1 1 d . . . . .
O4 O 0.5634(3) 0.6957(3) 0.5521(2) 0.0714(11) Uani 1 1 d . . . . .
O5 O 0.5625(3) 0.8479(3) 0.3196(3) 0.0874(14) Uani 1 1 d . . . . .
O6 O 0.7261(2) 0.6449(3) 0.18911(19) 0.0420(7) Uani 1 1 d . . . . .
O7 O 0.8256(3) 0.8079(4) 0.1868(3) 0.0923(14) Uani 1 1 d . . . . .
O8 O 0.9703(2) 0.5757(3) 0.2274(2) 0.0484(8) Uani 1 1 d . . . . .
O9 O 1.0390(3) 0.5816(4) 0.3796(2) 0.0697(11) Uani 1 1 d . . . . .
O10 O 0.9210(2) 0.3605(3) 0.1459(3) 0.0630(10) Uani 1 1 d . . . . .
O11 O 0.8036(3) 0.2311(5) 0.0699(3) 0.1023(17) Uani 1 1 d . . . . .
N1 N 0.6974(3) 0.3148(3) 0.4197(3) 0.0483(9) Uani 1 1 d . . . . .
N2 N 0.7816(4) 0.2690(4) 0.4116(3) 0.0550(10) Uani 1 1 d . . . . .
N3 N 0.8607(4) 0.2269(5) 0.4139(4) 0.0873(16) Uani 1 1 d . . . . .
N4 N 0.4658(3) 0.4670(4) 0.2705(3) 0.0539(10) Uani 1 1 d . . . . .
N5 N 0.3771(3) 0.4248(4) 0.2596(3) 0.0623(11) Uani 1 1 d . . . . .
N6 N 0.2925(4) 0.3921(6) 0.2400(4) 0.0968(19) Uani 1 1 d . . . . .
N7 N 0.6323(3) 0.5294(3) 0.5039(2) 0.0431(9) Uani 1 1 d . . . . .
H7 H 0.6744 0.4694 0.5189 0.052 Uiso 1 1 calc R . . . .
N8 N 0.6906(3) 0.7263(3) 0.4005(2) 0.0409(8) Uani 1 1 d . . . . .
H8 H 0.7497 0.7235 0.4410 0.049 Uiso 1 1 calc R . . . .
C1 C 0.6309(3) 0.3607(4) 0.3313(3) 0.0401(10) Uani 1 1 d . . . . .
C2 C 0.5411(3) 0.4297(4) 0.3575(3) 0.0408(10) Uani 1 1 d . . . . .
H2 H 0.5054 0.3799 0.3955 0.049 Uiso 1 1 calc R . . . .
C3 C 0.5799(3) 0.5480(4) 0.4075(3) 0.0380(9) Uani 1 1 d . . . . .
H3 H 0.5170 0.5968 0.4069 0.046 Uiso 1 1 calc R . . . .
C4 C 0.6475(3) 0.6177(4) 0.3524(3) 0.0369(9) Uani 1 1 d . . . . .
H4 H 0.6013 0.6414 0.2931 0.044 Uiso 1 1 calc R . . . .
C5 C 0.7355(3) 0.5389(4) 0.3314(3) 0.0366(9) Uani 1 1 d . . . . .
H5 H 0.7833 0.5150 0.3898 0.044 Uiso 1 1 calc R . . . .
C6 C 0.5914(5) 0.2524(4) 0.2673(3) 0.0552(13) Uani 1 1 d . . . . .
C7 C 0.6443(7) 0.0936(7) 0.1863(5) 0.111(3) Uani 1 1 d . . . . .
H7A H 0.6127 0.1135 0.1230 0.166 Uiso 1 1 calc GR . . . .
H7B H 0.5955 0.0469 0.2115 0.166 Uiso 1 1 calc GR . . . .
H7C H 0.7076 0.0480 0.1889 0.166 Uiso 1 1 calc GR . . . .
C8 C 0.6157(4) 0.6050(5) 0.5704(3) 0.0504(12) Uani 1 1 d . . . . .
C9 C 0.6646(5) 0.5663(6) 0.6677(3) 0.0712(16) Uani 1 1 d . . . . .
H9A H 0.6127 0.5255 0.6932 0.107 Uiso 1 1 calc GR . . . .
H9B H 0.6898 0.6355 0.7048 0.107 Uiso 1 1 calc GR . . . .
H9C H 0.7227 0.5131 0.6675 0.107 Uiso 1 1 calc GR . . . .
C10 C 0.6396(4) 0.8296(4) 0.3825(4) 0.0493(12) Uani 1 1 d . . . . .
C11 C 0.6820(5) 0.9318(5) 0.4456(5) 0.0689(16) Uani 1 1 d . . . . .
C12 C 0.7995(3) 0.5990(4) 0.2699(3) 0.0392(10) Uani 1 1 d . . . . .
H12 H 0.8387 0.6665 0.3038 0.047 Uiso 1 1 calc R . . . .
C13 C 0.7449(4) 0.7552(4) 0.1575(3) 0.0526(12) Uani 1 1 d . . . . .
C14 C 0.6561(4) 0.7998(4) 0.0843(3) 0.0467(11) Uani 1 1 d . . . . .
C15 C 0.6742(5) 0.8908(5) 0.0273(4) 0.0655(14) Uani 1 1 d . . . . .
H15 H 0.7426 0.9193 0.0324 0.079 Uiso 1 1 calc R . . . .
C16 C 0.5915(5) 0.9404(6) -0.0376(4) 0.0732(16) Uani 1 1 d . . . . .
H16 H 0.6046 1.0018 -0.0760 0.088 Uiso 1 1 calc R . . . .
C17 C 0.4927(6) 0.9005(7) -0.0454(4) 0.0832(19) Uani 1 1 d . . . . .
H17 H 0.4374 0.9355 -0.0884 0.100 Uiso 1 1 calc R . . . .
C18 C 0.4725(4) 0.8091(7) 0.0090(5) 0.0823(19) Uani 1 1 d . . . . .
H18 H 0.4037 0.7811 0.0021 0.099 Uiso 1 1 calc R . . . .
C19 C 0.5544(4) 0.7570(5) 0.0752(4) 0.0632(14) Uani 1 1 d . . . . .
H19 H 0.5407 0.6947 0.1124 0.076 Uiso 1 1 calc R . . . .
C20 C 0.8790(3) 0.5115(4) 0.2426(3) 0.0433(11) Uani 1 1 d . . . . .
H20 H 0.9026 0.4545 0.2935 0.052 Uiso 1 1 calc R . . . .
C21 C 1.0471(3) 0.5992(5) 0.3017(3) 0.0478(11) Uani 1 1 d . . . . .
C22 C 1.1424(3) 0.6507(4) 0.2769(3) 0.0486(11) Uani 1 1 d . . . . .
C23 C 1.2273(4) 0.6853(5) 0.3480(4) 0.0615(14) Uani 1 1 d . . . . .
H23 H 1.2226 0.6777 0.4094 0.074 Uiso 1 1 calc R . . . .
C24 C 1.3176(4) 0.7304(6) 0.3280(5) 0.0731(17) Uani 1 1 d . . . . .
H24 H 1.3739 0.7537 0.3756 0.088 Uiso 1 1 calc R . . . .
C25 C 1.3247(4) 0.7410(6) 0.2383(5) 0.0815(19) Uani 1 1 d . . . . .
H25 H 1.3863 0.7715 0.2252 0.098 Uiso 1 1 calc R . . . .
C26 C 1.2426(4) 0.7074(6) 0.1667(4) 0.0781(18) Uani 1 1 d . . . . .
H26 H 1.2489 0.7146 0.1058 0.094 Uiso 1 1 calc R . . . .
C27 C 1.1497(4) 0.6623(5) 0.1858(4) 0.0625(14) Uani 1 1 d . . . . .
H27 H 1.0933 0.6403 0.1378 0.075 Uiso 1 1 calc R . . . .
C28 C 0.8374(3) 0.4421(5) 0.1552(4) 0.0557(13) Uani 1 1 d . . . . .
H28A H 0.7743 0.3979 0.1593 0.067 Uiso 1 1 calc R . . . .
H28B H 0.8201 0.4958 0.1025 0.067 Uiso 1 1 calc R . . . .
C29 C 0.8934(4) 0.2586(5) 0.1023(4) 0.0613(14) Uani 1 1 d . . . . .
C30 C 0.9868(4) 0.1817(6) 0.0985(4) 0.0637(14) Uani 1 1 d . . . . .
C31 C 0.9738(6) 0.0594(7) 0.0907(6) 0.109(3) Uani 1 1 d . . . . .
H31 H 0.9073 0.0259 0.0862 0.131 Uiso 1 1 calc R . . . .
C32 C 1.0594(8) -0.0140(8) 0.0893(7) 0.131(3) Uani 1 1 d . . . . .
H32 H 1.0508 -0.0968 0.0867 0.158 Uiso 1 1 calc R . . . .
C33 C 1.1561(7) 0.0348(9) 0.0917(5) 0.109(3) Uani 1 1 d . . . . .
H33 H 1.2132 -0.0143 0.0887 0.130 Uiso 1 1 calc R . . . .
C34 C 1.1686(5) 0.1561(8) 0.0985(4) 0.088(2) Uani 1 1 d . . . . .
H34 H 1.2347 0.1895 0.1006 0.105 Uiso 1 1 calc R . . . .
C35 C 1.0845(5) 0.2300(6) 0.1024(4) 0.0742(16) Uani 1 1 d . . . . .
H35 H 1.0943 0.3126 0.1076 0.089 Uiso 1 1 calc R . . . .
F1 F 0.7619(6) 0.9060(7) 0.5162(7) 0.110(3) Uani 0.634(5) 1 d . . P A 1
F2 F 0.6116(6) 0.9754(8) 0.4899(7) 0.129(3) Uani 0.634(5) 1 d . . P A 1
F3 F 0.7141(11) 1.0221(7) 0.4013(6) 0.146(4) Uani 0.634(5) 1 d . . P A 1
F1A F 0.7816(11) 0.9534(14) 0.4482(13) 0.110(3) Uani 0.366(5) 1 d . . P A 2
F2A F 0.6857(15) 0.9157(15) 0.5277(15) 0.129(3) Uani 0.366(5) 1 d . . P A 2
F3A F 0.6336(19) 1.0313(14) 0.4176(12) 0.146(4) Uani 0.366(5) 1 d . . P A 2
O12 O 0.8625(4) 0.6886(6) 0.5555(4) 0.1143(19) Uani 1 1 d . . . . .
H12A H 0.891(5) 0.629(7) 0.520(4) 0.09(2) Uiso 1 1 d . . . . .
C36 C 0.9009(6) 0.7416(10) 0.6413(5) 0.125(3) Uani 1 1 d . . . . .
H36A H 0.9533 0.8004 0.6365 0.188 Uiso 1 1 calc GR . . . .
H36B H 0.9321 0.6812 0.6854 0.188 Uiso 1 1 calc GR . . . .
H36C H 0.8438 0.7797 0.6615 0.188 Uiso 1 1 calc GR . . . .
O13 O 0.9588(4) 0.4784(5) 0.5256(4) 0.1062(16) Uani 1 1 d . . . . .
H13 H 0.9103 0.5189 0.5365 0.159 Uiso 1 1 calc GR . . . .
C37 C 1.0064(7) 0.4106(10) 0.6056(7) 0.141(4) Uani 1 1 d . . . . .
H37A H 1.0448 0.3444 0.5879 0.211 Uiso 1 1 calc GR . . . .
H37B H 0.9525 0.3807 0.6344 0.211 Uiso 1 1 calc GR . . . .
H37C H 1.0540 0.4609 0.6485 0.211 Uiso 1 1 calc GR . . . .


_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 1.415(5) . ?
O1 C5 1.440(5) . ?
O2 C6 1.197(6) . ?
O3 C6 1.310(6) . ?
O3 C7 1.447(8) . ?
O4 C8 1.213(6) . ?
O5 C10 1.219(6) . ?
O6 C12 1.444(5) . ?
O6 C13 1.358(5) . ?
O7 C13 1.193(6) . ?
O8 C20 1.446(5) . ?
O8 C21 1.332(5) . ?
O9 C21 1.201(5) . ?
O10 C28 1.447(6) . ?
O10 C29 1.315(6) . ?
O11 C29 1.195(6) . ?
N1 N2 1.238(5) . ?
N1 C1 1.486(6) . ?
N2 N3 1.123(6) . ?
N4 N5 1.221(5) . ?
N4 C2 1.489(6) . ?
N5 N6 1.130(6) . ?
N7 C3 1.451(5) . ?
N7 C8 1.353(6) . ?
N8 C4 1.450(5) . ?
N8 C10 1.325(6) . ?
C1 C2 1.521(6) . ?
C1 C6 1.549(6) . ?
C2 C3 1.540(6) . ?
C3 C4 1.541(6) . ?
C4 C5 1.529(6) . ?
C5 C12 1.523(6) . ?
C8 C9 1.501(7) . ?
C10 C11 1.496(8) . ?
C11 F1 1.327(9) . ?
C11 F2 1.335(9) . ?
C11 F3 1.321(10) . ?
C11 F1A 1.308(17) . ?
C11 F2A 1.22(2) . ?
C11 F3A 1.30(2) . ?
C12 C20 1.540(6) . ?
C13 C14 1.477(6) . ?
C14 C15 1.376(7) . ?
C14 C19 1.382(6) . ?
C15 C16 1.383(8) . ?
C16 C17 1.338(9) . ?
C17 C18 1.362(9) . ?
C18 C19 1.398(8) . ?
C20 C28 1.500(6) . ?
C21 C22 1.485(6) . ?
C22 C23 1.395(7) . ?
C22 C27 1.382(7) . ?
C23 C24 1.370(7) . ?
C24 C25 1.359(9) . ?
C25 C26 1.373(8) . ?
C26 C27 1.395(7) . ?
C29 C30 1.497(8) . ?
C30 C31 1.375(9) . ?
C30 C35 1.367(8) . ?
C31 C32 1.384(10) . ?
C32 C33 1.362(11) . ?
C33 C34 1.362(11) . ?
C34 C35 1.380(8) . ?
O12 C36 1.389(8) . ?
O13 C37 1.424(9) . ?

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 C5 114.9(3) . . ?
C6 O3 C7 115.3(5) . . ?
C13 O6 C12 118.1(3) . . ?
C21 O8 C20 116.9(3) . . ?
C29 O10 C28 117.7(4) . . ?
N2 N1 C1 113.8(4) . . ?
N3 N2 N1 172.9(5) . . ?
N5 N4 C2 114.8(4) . . ?
N6 N5 N4 172.1(6) . . ?
C8 N7 C3 120.9(4) . . ?
C10 N8 C4 120.5(4) . . ?
O1 C1 N1 112.1(3) . . ?
O1 C1 C2 112.0(3) . . ?
O1 C1 C6 105.9(3) . . ?
N1 C1 C2 105.8(3) . . ?
N1 C1 C6 108.5(4) . . ?
C2 C1 C6 112.6(4) . . ?
N4 C2 C1 108.0(3) . . ?
N4 C2 C3 104.8(4) . . ?
C1 C2 C3 111.8(3) . . ?
N7 C3 C2 112.3(3) . . ?
N7 C3 C4 113.6(3) . . ?
C2 C3 C4 109.8(3) . . ?
N8 C4 C3 111.2(3) . . ?
N8 C4 C5 110.9(3) . . ?
C5 C4 C3 111.2(3) . . ?
O1 C5 C4 109.2(3) . . ?
O1 C5 C12 106.2(3) . . ?
C12 C5 C4 114.0(3) . . ?
O2 C6 O3 125.5(5) . . ?
O2 C6 C1 124.1(5) . . ?
O3 C6 C1 110.4(4) . . ?
O4 C8 N7 122.0(4) . . ?
O4 C8 C9 123.2(4) . . ?
N7 C8 C9 114.8(4) . . ?
O5 C10 N8 125.7(5) . . ?
O5 C10 C11 118.1(5) . . ?
N8 C10 C11 116.1(5) . . ?
F1 C11 C10 116.0(6) . . ?
F1 C11 F2 101.0(8) . . ?
F2 C11 C10 113.0(5) . . ?
F3 C11 C10 112.5(6) . . ?
F3 C11 F1 106.1(7) . . ?
F3 C11 F2 107.4(8) . . ?
F1A C11 C10 112.3(7) . . ?
F2A C11 C10 115.9(8) . . ?
F2A C11 F1A 100.6(11) . . ?
F2A C11 F3A 110.5(13) . . ?
F3A C11 C10 111.7(9) . . ?
F3A C11 F1A 104.8(11) . . ?
O6 C12 C5 107.8(3) . . ?
O6 C12 C20 111.2(3) . . ?
C5 C12 C20 111.7(4) . . ?
O6 C13 C14 112.7(4) . . ?
O7 C13 O6 122.2(5) . . ?
O7 C13 C14 125.1(4) . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 C19 119.2(5) . . ?
C19 C14 C13 121.6(4) . . ?
C14 C15 C16 120.5(5) . . ?
C17 C16 C15 120.3(6) . . ?
C16 C17 C18 120.6(6) . . ?
C17 C18 C19 120.5(6) . . ?
C14 C19 C18 118.9(5) . . ?
O8 C20 C12 110.5(4) . . ?
O8 C20 C28 105.4(3) . . ?
C28 C20 C12 115.0(4) . . ?
O8 C21 C22 112.3(4) . . ?
O9 C21 O8 123.4(4) . . ?
O9 C21 C22 124.3(4) . . ?
C23 C22 C21 118.6(4) . . ?
C27 C22 C21 121.8(4) . . ?
C27 C22 C23 119.6(4) . . ?
C24 C23 C22 120.3(5) . . ?
C25 C24 C23 119.8(5) . . ?
C24 C25 C26 121.2(5) . . ?
C25 C26 C27 119.7(6) . . ?
C22 C27 C26 119.3(5) . . ?
O10 C28 C20 106.1(4) . . ?
O10 C29 C30 112.4(4) . . ?
O11 C29 O10 123.3(5) . . ?
O11 C29 C30 124.3(5) . . ?
C31 C30 C29 119.0(6) . . ?
C35 C30 C29 121.8(5) . . ?
C35 C30 C31 119.2(6) . . ?
C30 C31 C32 120.2(7) . . ?
C33 C32 C31 120.2(8) . . ?
C32 C33 C34 119.4(7) . . ?
C33 C34 C35 120.9(8) . . ?
C30 C35 C34 120.0(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N4 63.4(4) . . . . ?
O1 C1 C2 C3 -51.4(5) . . . . ?
O1 C1 C6 O2 -130.7(5) . . . . ?
O1 C1 C6 O3 51.3(5) . . . . ?
O1 C5 C12 O6 68.7(4) . . . . ?
O1 C5 C12 C20 -53.8(4) . . . . ?
O5 C10 C11 F1 176.2(8) . . . . ?
O5 C10 C11 F2 60.3(9) . . . . ?
O5 C10 C11 F3 -61.4(10) . . . . ?
O5 C10 C11 F1A -123.2(11) . . . . ?
O5 C10 C11 F2A 122.0(13) . . . . ?
O5 C10 C11 F3A -5.8(13) . . . . ?
O6 C12 C20 O8 88.5(4) . . . . ?
O6 C12 C20 C28 -30.7(5) . . . . ?
O6 C13 C14 C15 -161.0(4) . . . . ?
O6 C13 C14 C19 22.7(7) . . . . ?
O7 C13 C14 C15 18.7(8) . . . . ?
O7 C13 C14 C19 -157.6(6) . . . . ?
O8 C20 C28 O10 61.8(5) . . . . ?
O8 C21 C22 C23 176.8(4) . . . . ?
O8 C21 C22 C27 -4.7(7) . . . . ?
O9 C21 C22 C23 -2.4(8) . . . . ?
O9 C21 C22 C27 176.1(5) . . . . ?
O10 C29 C30 C31 154.1(6) . . . . ?
O10 C29 C30 C35 -26.2(7) . . . . ?
O11 C29 C30 C31 -25.6(10) . . . . ?
O11 C29 C30 C35 154.1(6) . . . . ?
N1 C1 C2 N4 -174.2(3) . . . . ?
N1 C1 C2 C3 71.0(4) . . . . ?
N1 C1 C6 O2 108.9(5) . . . . ?
N1 C1 C6 O3 -69.2(5) . . . . ?
N2 N1 C1 O1 -49.0(5) . . . . ?
N2 N1 C1 C2 -171.4(4) . . . . ?
N2 N1 C1 C6 67.5(5) . . . . ?
N4 C2 C3 N7 165.0(3) . . . . ?
N4 C2 C3 C4 -67.6(4) . . . . ?
N5 N4 C2 C1 117.4(4) . . . . ?
N5 N4 C2 C3 -123.2(4) . . . . ?
N7 C3 C4 N8 -49.8(5) . . . . ?
N7 C3 C4 C5 74.3(4) . . . . ?
N8 C4 C5 O1 -179.2(3) . . . . ?
N8 C4 C5 C12 -60.7(4) . . . . ?
N8 C10 C11 F1 -4.1(9) . . . . ?
N8 C10 C11 F2 -120.0(8) . . . . ?
N8 C10 C11 F3 118.3(9) . . . . ?
N8 C10 C11 F1A 56.5(11) . . . . ?
N8 C10 C11 F2A -58.3(13) . . . . ?
N8 C10 C11 F3A 173.9(11) . . . . ?
C1 O1 C5 C4 -60.0(4) . . . . ?
C1 O1 C5 C12 176.7(3) . . . . ?
C1 C2 C3 N7 -78.2(4) . . . . ?
C1 C2 C3 C4 49.2(4) . . . . ?
C2 C1 C6 O2 -7.9(6) . . . . ?
C2 C1 C6 O3 174.0(4) . . . . ?
C2 C3 C4 N8 -176.5(3) . . . . ?
C2 C3 C4 C5 -52.4(4) . . . . ?
C3 N7 C8 O4 -5.6(7) . . . . ?
C3 N7 C8 C9 172.9(4) . . . . ?
C3 C4 C5 O1 56.5(4) . . . . ?
C3 C4 C5 C12 175.0(3) . . . . ?
C4 N8 C10 O5 -9.2(7) . . . . ?
C4 N8 C10 C11 171.1(4) . . . . ?
C4 C5 C12 O6 -51.5(4) . . . . ?
C4 C5 C12 C20 -174.0(3) . . . . ?
C5 O1 C1 N1 -60.8(4) . . . . ?
C5 O1 C1 C2 58.0(4) . . . . ?
C5 O1 C1 C6 -178.8(3) . . . . ?
C5 C12 C20 O8 -151.0(3) . . . . ?
C5 C12 C20 C28 89.8(5) . . . . ?
C6 C1 C2 N4 -55.9(5) . . . . ?
C6 C1 C2 C3 -170.7(3) . . . . ?
C7 O3 C6 O2 -3.6(8) . . . . ?
C7 O3 C6 C1 174.5(5) . . . . ?
C8 N7 C3 C2 -139.2(4) . . . . ?
C8 N7 C3 C4 95.4(4) . . . . ?
C10 N8 C4 C3 -93.0(5) . . . . ?
C10 N8 C4 C5 142.7(4) . . . . ?
C12 O6 C13 O7 9.4(7) . . . . ?
C12 O6 C13 C14 -170.9(4) . . . . ?
C12 C20 C28 O10 -176.2(4) . . . . ?
C13 O6 C12 C5 138.3(4) . . . . ?
C13 O6 C12 C20 -98.9(4) . . . . ?
C13 C14 C15 C16 -175.5(5) . . . . ?
C13 C14 C19 C18 175.3(5) . . . . ?
C14 C15 C16 C17 0.2(9) . . . . ?
C15 C14 C19 C18 -1.0(8) . . . . ?
C15 C16 C17 C18 -1.3(10) . . . . ?
C16 C17 C18 C19 1.2(10) . . . . ?
C17 C18 C19 C14 -0.1(10) . . . . ?
C19 C14 C15 C16 0.9(8) . . . . ?
C20 O8 C21 O9 -8.4(7) . . . . ?
C20 O8 C21 C22 172.4(4) . . . . ?
C21 O8 C20 C12 84.5(5) . . . . ?
C21 O8 C20 C28 -150.6(4) . . . . ?
C21 C22 C23 C24 178.4(5) . . . . ?
C21 C22 C27 C26 -177.7(5) . . . . ?
C22 C23 C24 C25 -0.3(9) . . . . ?
C23 C22 C27 C26 0.7(8) . . . . ?
C23 C24 C25 C26 0.1(10) . . . . ?
C24 C25 C26 C27 0.5(11) . . . . ?
C25 C26 C27 C22 -0.9(10) . . . . ?
C27 C22 C23 C24 -0.1(8) . . . . ?
C28 O10 C29 O11 0.6(8) . . . . ?
C28 O10 C29 C30 -179.2(4) . . . . ?
C29 O10 C28 C20 151.1(4) . . . . ?
C29 C30 C31 C32 -178.5(7) . . . . ?
C29 C30 C35 C34 -179.9(5) . . . . ?
C30 C31 C32 C33 -2.8(14) . . . . ?
C31 C30 C35 C34 -0.1(10) . . . . ?
C31 C32 C33 C34 2.1(14) . . . . ?
C32 C33 C34 C35 -0.4(13) . . . . ?
C33 C34 C35 C30 -0.6(10) . . . . ?
C35 C30 C31 C32 1.8(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_190419_s2_hh_yd0417b
_database_code_depnum_ccdc_archive 'CCDC 1975134'
loop_
_audit_author_name
_audit_author_address
HeHuan
;Sichuan university
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H22 N6 O11'
_chemical_formula_sum            'C17 H22 N6 O11'
_chemical_formula_weight         486.40
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.7778(5)
_cell_length_b                   13.2995(10)
_cell_length_c                   11.4128(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.458(5)
_cell_angle_gamma                90
_cell_volume                     1180.18(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1527
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3780
_cell_measurement_theta_min      3.4800
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5262
_diffrn_reflns_point_group_measured_fraction_full 0.682
_diffrn_reflns_point_group_measured_fraction_max 0.669
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.035
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   15.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   38.0000   30.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -80.00  -41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  178.0000   30.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0853317000
_diffrn_orient_matrix_UB_12      0.0118794000
_diffrn_orient_matrix_UB_13      0.0185984000
_diffrn_orient_matrix_UB_21      0.0321979000
_diffrn_orient_matrix_UB_22      -0.0353351000
_diffrn_orient_matrix_UB_23      -0.0404735000
_diffrn_orient_matrix_UB_31      0.0031759000
_diffrn_orient_matrix_UB_32      0.0380842000
_diffrn_orient_matrix_UB_33      -0.0434049000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.282
_reflns_Friedel_fraction_full    0.334
_reflns_Friedel_fraction_max     0.308
_reflns_number_gt                2434
_reflns_number_total             3233
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 516 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.0116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.2924(3) 0.06382(19) 0.66418(17) 0.0379(5) Uani 1 1 d . . . . .
O2 O 0.0244(4) -0.0708(3) 0.6792(3) 0.0722(9) Uani 1 1 d . . . . .
O3 O 0.1556(4) -0.1412(2) 0.8356(2) 0.0638(8) Uani 1 1 d . . . . .
O4 O 0.4534(3) 0.0851(2) 1.00919(17) 0.0429(6) Uani 1 1 d . . . . .
O5 O 0.2227(3) 0.1159(3) 1.1161(2) 0.0690(9) Uani 1 1 d . . . . .
O6 O 0.4578(3) 0.21396(18) 0.81934(17) 0.0404(6) Uani 1 1 d . . . . .
O7 O 0.4195(4) 0.3203(3) 0.9688(2) 0.0741(9) Uani 1 1 d . . . . .
O8 O 0.1095(3) 0.3065(2) 0.7150(2) 0.0478(6) Uani 1 1 d . . . . .
O9 O 0.3077(5) 0.4180(3) 0.6628(4) 0.1137(14) Uani 1 1 d . . . . .
O10 O -0.0744(3) 0.1735(2) 0.56809(18) 0.0533(7) Uani 1 1 d . . . . .
O11 O -0.1614(3) 0.1859(3) 0.3831(2) 0.0798(11) Uani 1 1 d . . . . .
N1 N 0.4145(4) -0.0944(3) 0.6438(3) 0.0521(8) Uani 1 1 d . . . . .
N2 N 0.3514(4) -0.0940(3) 0.5434(3) 0.0601(9) Uani 1 1 d . . . . .
N3 N 0.3077(5) -0.0998(4) 0.4482(3) 0.0964(15) Uani 1 1 d . . . . .
N4 N 0.6014(3) 0.0179(3) 0.7938(2) 0.0477(8) Uani 1 1 d . . . . .
N5 N 0.7165(4) 0.0307(3) 0.8646(3) 0.0573(10) Uani 1 1 d . . . . .
N6 N 0.8371(5) 0.0469(5) 0.9177(3) 0.110(2) Uani 1 1 d . . . . .
C1 C 0.3196(4) -0.0285(3) 0.7229(3) 0.0384(8) Uani 1 1 d . . . . .
C2 C 0.4313(4) -0.0131(3) 0.8346(3) 0.0377(8) Uani 1 1 d . . . . .
H2 H 0.4415 -0.0766 0.8777 0.045 Uiso 1 1 calc R . . . .
C3 C 0.3419(4) 0.0647(3) 0.9093(2) 0.0345(8) Uani 1 1 d . . . . .
H3 H 0.2344 0.0357 0.9370 0.041 Uiso 1 1 calc R . . . .
C4 C 0.3010(4) 0.1617(3) 0.8452(3) 0.0353(8) Uani 1 1 d . . . . .
H4 H 0.2294 0.2044 0.8941 0.042 Uiso 1 1 calc R . . . .
C5 C 0.2052(4) 0.1390(3) 0.7299(3) 0.0363(8) Uani 1 1 d . . . . .
H5 H 0.0893 0.1151 0.7468 0.044 Uiso 1 1 calc R . . . .
C6 C 0.1457(5) -0.0805(3) 0.7432(3) 0.0510(9) Uani 1 1 d . . . . .
C7 C 0.0062(6) -0.2068(4) 0.8521(4) 0.0860(15) Uani 1 1 d . . . . .
H7A H -0.0266 -0.2375 0.7788 0.129 Uiso 1 1 calc GR . . . .
H7B H -0.0880 -0.1677 0.8802 0.129 Uiso 1 1 calc GR . . . .
H7C H 0.0355 -0.2582 0.9083 0.129 Uiso 1 1 calc GR . . . .
C8 C 0.3737(5) 0.1150(3) 1.1087(3) 0.0478(9) Uani 1 1 d . . . . .
C9 C 0.5018(6) 0.1439(4) 1.2016(3) 0.0794(15) Uani 1 1 d . . . . .
H9A H 0.5437 0.0846 1.2408 0.119 Uiso 1 1 calc GR . . . .
H9B H 0.4484 0.1873 1.2572 0.119 Uiso 1 1 calc GR . . . .
H9C H 0.5961 0.1785 1.1668 0.119 Uiso 1 1 calc GR . . . .
C10 C 0.5038(5) 0.2913(3) 0.8896(3) 0.0501(10) Uani 1 1 d . . . . .
C11 C 0.6709(6) 0.3334(4) 0.8546(4) 0.0762(14) Uani 1 1 d . . . . .
H11A H 0.7448 0.2798 0.8304 0.114 Uiso 1 1 calc GR . . . .
H11B H 0.7237 0.3682 0.9199 0.114 Uiso 1 1 calc GR . . . .
H11C H 0.6528 0.3795 0.7907 0.114 Uiso 1 1 calc GR . . . .
C12 C 0.1915(4) 0.2293(3) 0.6489(3) 0.0418(8) Uani 1 1 d . . . . .
H12 H 0.3076 0.2517 0.6300 0.050 Uiso 1 1 calc R . . . .
C13 C 0.1789(6) 0.4002(3) 0.7137(4) 0.0658(12) Uani 1 1 d . . . . .
C14 C 0.0767(7) 0.4713(4) 0.7816(5) 0.0961(18) Uani 1 1 d . . . . .
H14A H -0.0434 0.4574 0.7689 0.144 Uiso 1 1 calc GR . . . .
H14B H 0.1008 0.5387 0.7568 0.144 Uiso 1 1 calc GR . . . .
H14C H 0.1059 0.4644 0.8634 0.144 Uiso 1 1 calc GR . . . .
C15 C 0.0907(4) 0.2106(3) 0.5363(3) 0.0507(10) Uani 1 1 d . . . . .
H15A H 0.0784 0.2724 0.4919 0.061 Uiso 1 1 calc R . . . .
H15B H 0.1492 0.1615 0.4887 0.061 Uiso 1 1 calc R . . . .
C16 C -0.1903(5) 0.1635(3) 0.4817(3) 0.0521(10) Uani 1 1 d . . . . .
C17 C -0.3564(5) 0.1251(5) 0.5241(3) 0.0809(17) Uani 1 1 d . . . . .
H17A H -0.3478 0.0540 0.5373 0.121 Uiso 1 1 calc GR . . . .
H17B H -0.4455 0.1384 0.4665 0.121 Uiso 1 1 calc GR . . . .
H17C H -0.3833 0.1582 0.5962 0.121 Uiso 1 1 calc GR . . . .


_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 1.412(4) . ?
O1 C5 1.432(4) . ?
O2 C6 1.186(4) . ?
O3 C6 1.328(5) . ?
O3 C7 1.470(5) . ?
O4 C3 1.441(3) . ?
O4 C8 1.367(4) . ?
O5 C8 1.180(4) . ?
O6 C4 1.440(4) . ?
O6 C10 1.347(4) . ?
O7 C10 1.194(4) . ?
O8 C12 1.434(4) . ?
O8 C13 1.358(5) . ?
O9 C13 1.194(5) . ?
O10 C15 1.431(4) . ?
O10 C16 1.326(4) . ?
O11 C16 1.191(4) . ?
N1 N2 1.235(4) . ?
N1 C1 1.470(4) . ?
N2 N3 1.133(4) . ?
N4 N5 1.203(4) . ?
N4 C2 1.473(4) . ?
N5 N6 1.124(4) . ?
C1 C2 1.538(4) . ?
C1 C6 1.543(5) . ?
C2 C3 1.519(5) . ?
C3 C4 1.514(5) . ?
C4 C5 1.526(4) . ?
C5 C12 1.517(5) . ?
C8 C9 1.487(5) . ?
C10 C11 1.480(5) . ?
C12 C15 1.509(4) . ?
C13 C14 1.469(6) . ?
C16 C17 1.482(5) . ?

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 C5 115.2(2) . . ?
C6 O3 C7 115.7(3) . . ?
C8 O4 C3 115.8(2) . . ?
C10 O6 C4 117.4(3) . . ?
C13 O8 C12 118.0(3) . . ?
C16 O10 C15 116.3(2) . . ?
N2 N1 C1 111.9(3) . . ?
N3 N2 N1 172.8(4) . . ?
N5 N4 C2 119.1(3) . . ?
N6 N5 N4 170.3(4) . . ?
O1 C1 N1 107.4(2) . . ?
O1 C1 C2 110.6(3) . . ?
O1 C1 C6 109.9(3) . . ?
N1 C1 C2 107.9(3) . . ?
N1 C1 C6 106.3(3) . . ?
C2 C1 C6 114.4(3) . . ?
N4 C2 C1 105.5(2) . . ?
N4 C2 C3 114.5(3) . . ?
C3 C2 C1 107.4(2) . . ?
O4 C3 C2 107.3(2) . . ?
O4 C3 C4 109.6(3) . . ?
C4 C3 C2 113.8(2) . . ?
O6 C4 C3 110.0(2) . . ?
O6 C4 C5 108.4(2) . . ?
C3 C4 C5 109.9(3) . . ?
O1 C5 C4 111.3(2) . . ?
O1 C5 C12 105.1(2) . . ?
C12 C5 C4 113.2(3) . . ?
O2 C6 O3 125.8(4) . . ?
O2 C6 C1 123.0(4) . . ?
O3 C6 C1 111.0(3) . . ?
O4 C8 C9 111.0(3) . . ?
O5 C8 O4 122.4(3) . . ?
O5 C8 C9 126.6(3) . . ?
O6 C10 C11 110.5(3) . . ?
O7 C10 O6 123.7(3) . . ?
O7 C10 C11 125.9(4) . . ?
O8 C12 C5 105.8(2) . . ?
O8 C12 C15 109.7(3) . . ?
C15 C12 C5 114.5(3) . . ?
O8 C13 C14 111.4(4) . . ?
O9 C13 O8 121.7(4) . . ?
O9 C13 C14 126.9(5) . . ?
O10 C15 C12 107.0(2) . . ?
O10 C16 C17 111.9(3) . . ?
O11 C16 O10 122.4(3) . . ?
O11 C16 C17 125.6(3) . . ?

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 N4 -66.3(3) . . . . ?
O1 C1 C2 C3 56.3(3) . . . . ?
O1 C1 C6 O2 30.3(5) . . . . ?
O1 C1 C6 O3 -153.8(3) . . . . ?
O1 C5 C12 O8 -178.1(2) . . . . ?
O1 C5 C12 C15 61.0(3) . . . . ?
O4 C3 C4 O6 52.4(3) . . . . ?
O4 C3 C4 C5 171.7(2) . . . . ?
O6 C4 C5 O1 70.2(3) . . . . ?
O6 C4 C5 C12 -47.9(3) . . . . ?
O8 C12 C15 O10 -63.7(4) . . . . ?
N1 C1 C2 N4 50.9(4) . . . . ?
N1 C1 C2 C3 173.5(3) . . . . ?
N1 C1 C6 O2 -85.6(5) . . . . ?
N1 C1 C6 O3 90.3(3) . . . . ?
N2 N1 C1 O1 -46.7(4) . . . . ?
N2 N1 C1 C2 -166.0(3) . . . . ?
N2 N1 C1 C6 70.8(4) . . . . ?
N4 C2 C3 O4 -58.5(3) . . . . ?
N4 C2 C3 C4 62.9(3) . . . . ?
N5 N4 C2 C1 -176.8(3) . . . . ?
N5 N4 C2 C3 65.3(4) . . . . ?
C1 O1 C5 C4 57.3(3) . . . . ?
C1 O1 C5 C12 -179.9(3) . . . . ?
C1 C2 C3 O4 -175.3(2) . . . . ?
C1 C2 C3 C4 -53.9(3) . . . . ?
C2 C1 C6 O2 155.5(4) . . . . ?
C2 C1 C6 O3 -28.6(4) . . . . ?
C2 C3 C4 O6 -67.7(3) . . . . ?
C2 C3 C4 C5 51.6(3) . . . . ?
C3 O4 C8 O5 6.3(5) . . . . ?
C3 O4 C8 C9 -174.2(3) . . . . ?
C3 C4 C5 O1 -50.1(3) . . . . ?
C3 C4 C5 C12 -168.2(3) . . . . ?
C4 O6 C10 O7 -2.4(5) . . . . ?
C4 O6 C10 C11 177.4(3) . . . . ?
C4 C5 C12 O8 -56.5(3) . . . . ?
C4 C5 C12 C15 -177.4(3) . . . . ?
C5 O1 C1 N1 -178.3(2) . . . . ?
C5 O1 C1 C2 -60.8(3) . . . . ?
C5 O1 C1 C6 66.5(3) . . . . ?
C5 C12 C15 O10 55.0(4) . . . . ?
C6 C1 C2 N4 168.9(3) . . . . ?
C6 C1 C2 C3 -68.5(4) . . . . ?
C7 O3 C6 O2 5.1(6) . . . . ?
C7 O3 C6 C1 -170.6(3) . . . . ?
C8 O4 C3 C2 -151.9(3) . . . . ?
C8 O4 C3 C4 84.1(3) . . . . ?
C10 O6 C4 C3 -100.8(3) . . . . ?
C10 O6 C4 C5 139.0(3) . . . . ?
C12 O8 C13 O9 -2.6(6) . . . . ?
C12 O8 C13 C14 177.9(4) . . . . ?
C13 O8 C12 C5 133.3(3) . . . . ?
C13 O8 C12 C15 -102.7(4) . . . . ?
C15 O10 C16 O11 -1.6(6) . . . . ?
C15 O10 C16 C17 -179.8(4) . . . . ?
C16 O10 C15 C12 172.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_190321_s2_hh
_database_code_depnum_ccdc_archive 'CCDC 1975132'
loop_
_audit_author_name
_audit_author_address
HeHuan
;Sichuan university
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2020-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 N7 O12'
_chemical_formula_sum            'C20 H27 N7 O12'
_chemical_formula_weight         557.48
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.6273(12)
_cell_length_b                   8.8714(10)
_cell_length_c                   16.549(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.469(11)
_cell_angle_gamma                90
_cell_volume                     1385.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1235
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.1530
_cell_measurement_theta_min      3.7500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             584
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6381
_diffrn_reflns_point_group_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.615
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.087
_diffrn_reflns_theta_min         2.969
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -78.50    2.00   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -57.0000  -60.0000 115

#__ type_ start__ end____ width___ exp.time_
  2 omega  -82.00   10.40   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -77.0000 -150.0000 132

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   11.60   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       16.9200   95.0000 -179.0000 38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0681832000
_diffrn_orient_matrix_UB_12      -0.0145052000
_diffrn_orient_matrix_UB_13      0.0242412000
_diffrn_orient_matrix_UB_21      0.0316800000
_diffrn_orient_matrix_UB_22      0.0257861000
_diffrn_orient_matrix_UB_23      -0.0326221000
_diffrn_orient_matrix_UB_31      0.0023745000
_diffrn_orient_matrix_UB_32      0.0743059000
_diffrn_orient_matrix_UB_33      0.0160684000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.350
_reflns_Friedel_fraction_full    0.476
_reflns_Friedel_fraction_max     0.340
_reflns_number_gt                2348
_reflns_number_total             4555
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4555
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1215
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19-C20 = C19A-C20A
 1.55 with sigma of 0.02
 O11-C19 = O11A-C19A
 1.38 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19) = Uanis(C19A)
Uanis(O12) = Uanis(O12A)
Uanis(C20) = Uanis(C20A)
Uanis(O11) = Uanis(O11A)
Uanis(O2) = Uanis(O2A)
Uanis(O5) = Uanis(O5A)
4. Others
 Sof(O12A)=Sof(C19A)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(O12)=Sof(C19)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
 Sof(H18C)=Sof(H18D)=Sof(O11A)=1-FVAR(2)
 Sof(H18A)=Sof(H18B)=Sof(O11)=FVAR(2)
 Sof(O2A)=1-FVAR(3)
 Sof(O2)=FVAR(3)
 Sof(O5A)=1-FVAR(4)
 Sof(O5)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18(H18C,H18D)
5.c Aromatic/amide H refined with riding coordinates:
 N7(H7)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.2609(3) 0.3491(4) 0.23086(17) 0.0558(8) Uani 1 1 d . . . . .
O3 O -0.0792(4) 0.4849(5) 0.1609(2) 0.1056(15) Uani 1 1 d . . . . .
O4 O 0.1924(3) 0.5038(3) 0.4550(2) 0.0650(9) Uani 1 1 d . . . . .
O6 O 0.5647(4) 0.5707(4) 0.4701(2) 0.0761(10) Uani 1 1 d . . . . .
O7 O 0.5418(3) 0.4456(4) 0.2668(2) 0.0661(9) Uani 1 1 d . . . . .
O8 O 0.7592(4) 0.4117(5) 0.3437(3) 0.0914(12) Uani 1 1 d . . . . .
O9 O 0.4486(4) 0.0553(5) 0.2157(2) 0.0755(11) Uani 1 1 d . . . . .
O10 O 0.3347(5) 0.0476(7) 0.0852(3) 0.142(2) Uani 1 1 d . . . . .
N1 N 0.0557(5) 0.2137(5) 0.2532(3) 0.0675(12) Uani 1 1 d . . . . .
N2 N 0.0381(5) 0.1292(7) 0.1931(4) 0.0823(15) Uani 1 1 d . . . . .
N3 N 0.0161(7) 0.0425(9) 0.1431(4) 0.144(3) Uani 1 1 d . . . . .
N4 N 0.1512(5) 0.6122(5) 0.2943(3) 0.0712(13) Uani 1 1 d . . . . .
N5 N 0.0714(6) 0.7151(6) 0.2967(3) 0.0751(14) Uani 1 1 d . . . . .
N6 N 0.0104(7) 0.8208(7) 0.2941(5) 0.133(3) Uani 1 1 d . . . . .
N7 N 0.4505(4) 0.3479(4) 0.4486(2) 0.0571(10) Uani 1 1 d . . . . .
H7 H 0.4455 0.2563 0.4649 0.068 Uiso 1 1 calc R . . . .
C1 C 0.1194(5) 0.3634(6) 0.2384(3) 0.0577(13) Uani 1 1 d . . . . .
C2 C 0.1040(5) 0.4601(5) 0.3115(3) 0.0543(12) Uani 1 1 d . . . . .
H2 H 0.0053 0.4618 0.3184 0.065 Uiso 1 1 calc R . . . .
C3 C 0.2005(5) 0.4030(5) 0.3888(3) 0.0528(12) Uani 1 1 d . . . . .
H3 H 0.1708 0.3018 0.4021 0.063 Uiso 1 1 calc R . . . .
C4 C 0.3523(4) 0.3986(5) 0.3758(2) 0.0483(11) Uani 1 1 d . . . . .
H4 H 0.3795 0.5006 0.3624 0.058 Uiso 1 1 calc R . . . .
C5 C 0.3572(4) 0.2970(5) 0.3028(3) 0.0494(11) Uani 1 1 d . . . . .
H5 H 0.3305 0.1945 0.3158 0.059 Uiso 1 1 calc R . . . .
C6 C 0.0403(6) 0.4265(8) 0.1551(4) 0.0882(19) Uani 1 1 d . . . . .
C7 C -0.1607(8) 0.5509(12) 0.0824(5) 0.171(4) Uani 1 1 d . . . . .
H7A H -0.1581 0.6589 0.0861 0.257 Uiso 1 1 calc GR . . . .
H7B H -0.2573 0.5171 0.0737 0.257 Uiso 1 1 calc GR . . . .
H7C H -0.1190 0.5191 0.0372 0.257 Uiso 1 1 calc GR . . . .
C8 C 0.1314(7) 0.4549(7) 0.5157(3) 0.0707(15) Uani 1 1 d . . . . .
C9 C 0.1351(8) 0.5727(7) 0.5800(4) 0.110(2) Uani 1 1 d . . . . .
H9A H 0.0593 0.6431 0.5625 0.166 Uiso 1 1 calc GR . . . .
H9B H 0.2242 0.6248 0.5882 0.166 Uiso 1 1 calc GR . . . .
H9C H 0.1241 0.5262 0.6307 0.166 Uiso 1 1 calc GR . . . .
C10 C 0.5497(5) 0.4405(6) 0.4916(3) 0.0597(13) Uani 1 1 d . . . . .
C11 C 0.6411(7) 0.3738(7) 0.5670(3) 0.098(2) Uani 1 1 d . . . . .
H11A H 0.6394 0.4380 0.6135 0.146 Uiso 1 1 calc GR . . . .
H11B H 0.7366 0.3648 0.5587 0.146 Uiso 1 1 calc GR . . . .
H11C H 0.6057 0.2759 0.5772 0.146 Uiso 1 1 calc GR . . . .
C12 C 0.5025(5) 0.2931(6) 0.2802(3) 0.0559(13) Uani 1 1 d . . . . .
H12 H 0.5711 0.2501 0.3262 0.067 Uiso 1 1 calc R . . . .
C13 C 0.6717(6) 0.4925(8) 0.3066(4) 0.0785(17) Uani 1 1 d . . . . .
C14 C 0.6867(7) 0.6568(8) 0.2977(5) 0.108(2) Uani 1 1 d . . . . .
H14A H 0.6021 0.7062 0.3064 0.162 Uiso 1 1 calc GR . . . .
H14B H 0.7014 0.6791 0.2433 0.162 Uiso 1 1 calc GR . . . .
H14C H 0.7663 0.6920 0.3377 0.162 Uiso 1 1 calc GR . . . .
C15 C 0.5068(5) 0.2041(6) 0.2020(3) 0.0646(14) Uani 1 1 d . . . . .
H15 H 0.4484 0.2533 0.1540 0.078 Uiso 1 1 calc R . . . .
C16 C 0.3699(7) -0.0114(10) 0.1523(4) 0.101(2) Uani 1 1 d . . . . .
C17 C 0.3272(7) -0.1673(9) 0.1722(4) 0.114(2) Uani 1 1 d . . . . .
H17A H 0.3092 -0.1692 0.2272 0.171 Uiso 1 1 calc GR . . . .
H17B H 0.4022 -0.2366 0.1682 0.171 Uiso 1 1 calc GR . . . .
H17C H 0.2429 -0.1960 0.1339 0.171 Uiso 1 1 calc GR . . . .
C18 C 0.6559(6) 0.1828(8) 0.1891(4) 0.093(2) Uani 1 1 d . . . . .
H18A H 0.7111 0.2734 0.2046 0.111 Uiso 0.609(8) 1 calc R . P A 1
H18B H 0.7010 0.0998 0.2225 0.111 Uiso 0.609(8) 1 calc R . P A 1
H18C H 0.7187 0.1647 0.2417 0.111 Uiso 0.391(8) 1 calc R . P A 2
H18D H 0.6873 0.2737 0.1655 0.111 Uiso 0.391(8) 1 calc R . P A 2
O2 O 0.090(3) 0.487(5) 0.1100(16) 0.125(5) Uani 0.30(2) 1 d . . P B 1
O5 O 0.141(3) 0.331(4) 0.5276(19) 0.107(5) Uani 0.37(3) 1 d . . P C 1
O11 O 0.6469(8) 0.1507(10) 0.1025(6) 0.087(2) Uani 0.609(8) 1 d D . P A 1
O12 O 0.6842(11) -0.0862(11) 0.1422(6) 0.129(3) Uani 0.595(6) 1 d . . P A 1
C19 C 0.6657(14) 0.0048(16) 0.0910(10) 0.089(4) Uani 0.595(6) 1 d D . P A 1
C20 C 0.654(9) -0.028(5) -0.001(2) 0.131(10) Uani 0.595(6) 1 d D . P A 1
H20A H 0.7108 0.0430 -0.0236 0.196 Uiso 0.595(6) 1 calc GR . P A 1
H20B H 0.5567 -0.0184 -0.0285 0.196 Uiso 0.595(6) 1 calc GR . P A 1
H20C H 0.6864 -0.1282 -0.0077 0.196 Uiso 0.595(6) 1 calc GR . P A 1
O2A O 0.0799(11) 0.392(2) 0.0889(7) 0.125(5) Uani 0.70(2) 1 d . . P B 2
O5A O 0.067(3) 0.333(2) 0.5142(10) 0.107(5) Uani 0.63(3) 1 d . . P C 2
O11A O 0.6631(15) 0.050(2) 0.1314(9) 0.087(2) Uani 0.391(8) 1 d D . P A 2
O12A O 0.6363(15) 0.2280(16) 0.0365(8) 0.129(3) Uani 0.405(6) 1 d . . P A 2
C19A C 0.6479(19) 0.102(3) 0.0514(11) 0.089(4) Uani 0.405(6) 1 d D . P A 2
C20A C 0.625(13) -0.031(7) -0.010(3) 0.131(10) Uani 0.405(6) 1 d D . P A 2
H20D H 0.5935 0.0064 -0.0646 0.196 Uiso 0.405(6) 1 calc GR . P A 2
H20E H 0.5544 -0.0976 0.0042 0.196 Uiso 0.405(6) 1 calc GR . P A 2
H20F H 0.7124 -0.0849 -0.0062 0.196 Uiso 0.405(6) 1 calc GR . 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 1.398(5) . ?
O1 C5 1.433(5) . ?
O3 C6 1.282(6) . ?
O3 C7 1.497(7) . ?
O4 C3 1.428(5) . ?
O4 C8 1.332(6) . ?
O6 C10 1.225(6) . ?
O7 C12 1.434(6) . ?
O7 C13 1.357(6) . ?
O8 C13 1.181(6) . ?
O9 C15 1.470(6) . ?
O9 C16 1.307(7) . ?
O10 C16 1.214(7) . ?
N1 N2 1.230(7) . ?
N1 C1 1.503(6) . ?
N2 N3 1.118(7) . ?
N4 N5 1.199(6) . ?
N4 C2 1.469(6) . ?
N5 N6 1.103(7) . ?
N7 C4 1.446(5) . ?
N7 C10 1.351(6) . ?
C1 C2 1.514(6) . ?
C1 C6 1.541(7) . ?
C2 C3 1.511(6) . ?
C3 C4 1.519(6) . ?
C4 C5 1.516(6) . ?
C5 C12 1.519(6) . ?
C6 O2 1.10(3) . ?
C6 O2A 1.269(15) . ?
C8 C9 1.487(7) . ?
C8 O5 1.12(4) . ?
C8 O5A 1.24(2) . ?
C10 C11 1.499(7) . ?
C12 C15 1.524(6) . ?
C13 C14 1.474(8) . ?
C15 C18 1.505(7) . ?
C16 C17 1.498(10) . ?
C18 O11 1.446(10) . ?
C18 O11A 1.529(16) . ?
O11 C19 1.325(15) . ?
O12 C19 1.158(16) . ?
C19 C20 1.53(2) . ?
O11A C19A 1.383(19) . ?
O12A C19A 1.15(2) . ?
C19A C20A 1.54(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 115.8(3) . . ?
C6 O3 C7 114.7(5) . . ?
C8 O4 C3 118.3(4) . . ?
C13 O7 C12 117.4(4) . . ?
C16 O9 C15 117.4(5) . . ?
N2 N1 C1 113.7(4) . . ?
N3 N2 N1 173.0(7) . . ?
N5 N4 C2 117.9(4) . . ?
N6 N5 N4 170.4(6) . . ?
C10 N7 C4 121.7(4) . . ?
O1 C1 N1 111.8(4) . . ?
O1 C1 C2 112.0(4) . . ?
O1 C1 C6 105.7(4) . . ?
N1 C1 C2 105.2(4) . . ?
N1 C1 C6 108.8(4) . . ?
C2 C1 C6 113.5(5) . . ?
N4 C2 C1 106.4(4) . . ?
N4 C2 C3 108.1(4) . . ?
C3 C2 C1 110.2(4) . . ?
O4 C3 C2 108.7(4) . . ?
O4 C3 C4 109.0(4) . . ?
C2 C3 C4 109.6(3) . . ?
N7 C4 C3 112.2(3) . . ?
N7 C4 C5 111.1(4) . . ?
C5 C4 C3 108.1(3) . . ?
O1 C5 C4 110.7(3) . . ?
O1 C5 C12 106.1(3) . . ?
C4 C5 C12 112.7(4) . . ?
O3 C6 C1 111.8(5) . . ?
O2 C6 O3 111.5(16) . . ?
O2 C6 C1 125.4(16) . . ?
O2A C6 O3 126.2(6) . . ?
O2A C6 C1 120.3(7) . . ?
O4 C8 C9 111.0(5) . . ?
O5 C8 O4 114.9(15) . . ?
O5 C8 C9 125.1(16) . . ?
O5A C8 O4 124.1(8) . . ?
O5A C8 C9 124.4(8) . . ?
O6 C10 N7 122.2(4) . . ?
O6 C10 C11 122.0(5) . . ?
N7 C10 C11 115.8(5) . . ?
O7 C12 C5 107.5(4) . . ?
O7 C12 C15 107.7(4) . . ?
C5 C12 C15 113.7(4) . . ?
O7 C13 C14 110.7(6) . . ?
O8 C13 O7 124.0(6) . . ?
O8 C13 C14 125.3(6) . . ?
O9 C15 C12 105.0(4) . . ?
O9 C15 C18 108.2(5) . . ?
C18 C15 C12 111.9(4) . . ?
O9 C16 C17 112.5(7) . . ?
O10 C16 O9 123.5(8) . . ?
O10 C16 C17 124.0(7) . . ?
C15 C18 O11A 110.4(7) . . ?
O11 C18 C15 107.2(5) . . ?
C19 O11 C18 110.6(11) . . ?
O11 C19 C20 110(2) . . ?
O12 C19 O11 125.5(14) . . ?
O12 C19 C20 124(2) . . ?
C19A O11A C18 109.2(17) . . ?
O11A C19A C20A 110(3) . . ?
O12A C19A O11A 121(2) . . ?
O12A C19A C20A 128(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
