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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20230358_auto
_database_code_depnum_ccdc_archive 'CCDC 2253282'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2023-04-01 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-03-24
_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         'C15 H22 N2 O7'
_chemical_formula_sum            'C15 H22 N2 O7'
_chemical_formula_weight         342.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N3O4
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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.24888(18)
_cell_length_b                   8.64551(16)
_cell_length_c                   24.3498(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1736.52(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7994
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0810
_cell_measurement_theta_min      5.4190
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.400
_diffrn_reflns_theta_min         3.630
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -35.00   1.00    1.00    --  -33.50 178.00-180.00   54
  2  ω   -103.00 -11.00   1.00    1.00    --  -33.50 -37.00 150.00   92
  3  ω    -90.00 -40.00   1.00    1.00    --  -33.50 178.00   0.00   50
  4  ω    -69.00 -43.00   1.00    1.00    --  -33.50 -65.00  60.89   26
  5  ω    -53.00  -4.00   1.00    1.00    --  -33.50 -19.00   0.00   49
  6  ω   -105.00 -35.00   1.00    1.00    --  -33.50 178.00 -60.00   70
  7  ω    -88.00 -27.00   1.00    1.00    --  -33.50 -37.00  90.00   61
  8  ω   -105.00 -36.00   1.00    1.00    --  -33.50 178.00-120.00   69
  9  ω     61.00  87.00   1.00    1.00    --   36.47 178.00 -90.00   26
 10  ω     -2.00  24.00   1.00    1.00    --   36.47  95.00 139.57   26
 11  ω     68.00 108.00   1.00    1.00    --   36.47 178.00   0.00   40
 12  ω     88.00 114.00   1.00    5.00    --  108.00  45.00 150.00   26
 13  ω     88.00 119.00   1.00    5.00    --  108.00  45.00  60.00   31
 14  ω    108.00 144.00   1.00    5.00    --  108.00 111.00-150.00   36
 15  ω    140.00 166.00   1.00    5.00    --  108.00  30.00 150.00   26
 16  ω     85.00 119.00   1.00    5.00    --  108.00  30.00 150.00   34
 17  ω     88.00 114.00   1.00    5.00    --  108.00  61.00 150.00   26
 18  ω     53.00 101.00   1.00    5.00    --  108.00-111.00  30.00   48
 19  ω     88.00 114.00   1.00    5.00    --  108.00  61.00  60.00   26
 20  ω     37.00  99.00   1.00    5.00    --  108.00 -30.00 -30.00   62
 21  ω    122.00 178.00   1.00    5.00    --  108.00  30.00-180.00   56
 22  ω    122.00 176.00   1.00    5.00    --  108.00  61.00  60.00   54
 23  ω     53.00 104.00   1.00    5.00    --  108.00 -77.00-120.00   51
 24  ω     88.00 114.00   1.00    5.00    --  108.00  61.00 120.00   26
 25  ω     47.00 106.00   1.00    5.00    --  108.00 -94.00  30.00   59
 26  ω     88.00 114.00   1.00    5.00    --  108.00  45.00  90.00   26
 27  ω     83.00 108.00   1.00    5.00    --  108.00  30.00  60.00   25
 28  ω     88.00 132.00   1.00    5.00    --  108.00  45.00 120.00   44
 29  ω     52.00  78.00   1.00    5.00    --  108.00 -45.00   0.00   26
 30  ω    148.00 175.00   1.00    5.00    --  108.00 111.00-150.00   27
 31  ω    118.00 144.00   1.00    5.00    --  108.00 -15.00 150.00   26
 32  ω     82.00 117.00   1.00    5.00    --  108.00  30.00-180.00   35
 33  ω     56.00  98.00   1.00    5.00    --  108.00-111.00   0.00   42
 34  ω     93.00 118.00   1.00    5.00    --  108.00 -61.00-150.00   25
 35  ω     85.00 128.00   1.00    5.00    --  108.00 -45.00-150.00   43
 36  ω     40.00  66.00   1.00    5.00    --  108.00 -61.00-150.00   26
 37  ω    104.00 173.00   1.00    5.00    --  108.00  77.00 120.00   69
 38  ω     47.00  94.00   1.00    5.00    --  108.00 -15.00 150.00   47
 39  ω    152.00 177.00   1.00    5.00    --  108.00  77.00 -30.00   25
 40  ω    128.00 174.00   1.00    5.00    --  108.00  61.00  90.00   46
 41  ω     82.00 113.00   1.00    5.00    --  108.00  30.00  90.00   31
 42  ω     88.00 114.00   1.00    5.00    --  108.00  30.00 120.00   26
 43  ω     69.00  95.00   1.00    5.00    --  108.00 178.00  30.00   26
 44  ω     82.00 108.00   1.00    5.00    --  108.00  30.00-150.00   26
 45  ω    115.00 141.00   1.00    5.00    --  108.00  30.00-150.00   26
 46  ω     84.00 171.00   1.00    5.00    --  108.00  30.00-120.00   87
 47  ω    119.00 145.00   1.00    5.00    --  108.00  77.00 -30.00   26
 48  ω     88.00 114.00   1.00    5.00    --  108.00  61.00  90.00   26
 49  ω     56.00 101.00   1.00    5.00    --  108.00 -82.00  33.50   45
 50  ω     39.00  64.00   1.00    5.00    --  108.00 -45.00-150.00   25
 51  ω     40.00 108.00   1.00    5.00    --  108.00-111.00 -60.00   68
 52  ω    122.00 148.00   1.00    5.00    --  108.00 111.00-120.00   26
 53  ω    117.00 163.00   1.00    5.00    --  108.00  77.00  30.00   46
 54  ω     88.00 114.00   1.00    5.00    --  108.00  61.00-180.00   26
 55  ω     67.00 105.00   1.00    5.00    --  108.00 -82.00 179.36   38
 56  ω     70.00 103.00   1.00    5.00    --  108.00 -66.00  25.82   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268263000
_diffrn_orient_matrix_UB_12      0.0018154000
_diffrn_orient_matrix_UB_13      0.0626137000
_diffrn_orient_matrix_UB_21      -0.1034292000
_diffrn_orient_matrix_UB_22      0.1477928000
_diffrn_orient_matrix_UB_23      0.0045517000
_diffrn_orient_matrix_UB_31      -0.1531795000
_diffrn_orient_matrix_UB_32      -0.0994984000
_diffrn_orient_matrix_UB_33      0.0078883000
_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         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3117
_reflns_number_total             3330
_reflns_odcompleteness_completeness 94.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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         0.245
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1238 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.039
_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)+(0.0766P)²+0.1178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1-O1
 0.9 with sigma of 0.02
 C12A-C13A
 1.54 with sigma of 0.02
 C12-C13
 1.65 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(O5) = Uanis(O5A)
4. Others
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=
 Sof(O5A)=1-FVAR(1)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(O5)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C12(H12A,H12B), C12A(H12C,H12D)
5.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C13A(H13D,H13E,
 H13F), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.2520(3) -0.0719(2) 0.55790(9) 0.0463(5) Uani 1 1 d . . . . .
C2 C 0.3665(4) -0.2098(3) 0.55584(12) 0.0579(6) Uani 1 1 d . . . . .
H2A H 0.3227 -0.2964 0.5764 0.070 Uiso 1 1 calc R . . . .
H2B H 0.3854 -0.2421 0.5182 0.070 Uiso 1 1 calc R . . . .
C3 C 0.5210(4) -0.1512(4) 0.58188(15) 0.0678(7) Uani 1 1 d . . . . .
H3A H 0.5812 -0.0859 0.5567 0.081 Uiso 1 1 calc R . . . .
H3B H 0.5896 -0.2362 0.5936 0.081 Uiso 1 1 calc R . . . .
C4 C 0.4596(4) -0.0591(4) 0.63081(13) 0.0651(7) Uani 1 1 d . . . . .
H4A H 0.5417 0.0126 0.6436 0.078 Uiso 1 1 calc R . . . .
H4B H 0.4299 -0.1274 0.6608 0.078 Uiso 1 1 calc R . . . .
C5 C 0.3097(3) 0.0288(3) 0.60900(9) 0.0476(5) Uani 1 1 d . . . . .
C6 C 0.3512(3) 0.1842(3) 0.58363(10) 0.0463(5) Uani 1 1 d . . . . .
C7 C 0.3294(3) 0.1802(2) 0.52866(10) 0.0434(5) Uani 1 1 d . . . . .
C8 C 0.3493(4) 0.3044(3) 0.48685(11) 0.0573(6) Uani 1 1 d . . . . .
H8A H 0.4459 0.2856 0.4659 0.086 Uiso 1 1 calc GR . . . .
H8B H 0.3578 0.4028 0.5049 0.086 Uiso 1 1 calc GR . . . .
H8C H 0.2572 0.3050 0.4628 0.086 Uiso 1 1 calc GR . . . .
C9 C 0.1729(4) 0.0378(3) 0.65077(10) 0.0561(6) Uani 1 1 d . . . . .
C10 C -0.0760(6) 0.1559(6) 0.67173(19) 0.0985(13) Uani 1 1 d . . . . .
H10A H -0.0484 0.1949 0.7074 0.148 Uiso 1 1 calc GR . . . .
H10B H -0.1217 0.0542 0.6753 0.148 Uiso 1 1 calc GR . . . .
H10C H -0.1537 0.2234 0.6548 0.148 Uiso 1 1 calc GR . . . .
C11 C 0.4086(3) 0.3148(3) 0.61438(11) 0.0532(6) Uani 1 1 d . . . . .
C12 C 0.4870(7) 0.3996(5) 0.70420(18) 0.0772(12) Uani 0.819(6) 1 d D . P A 1
H12A H 0.5686 0.4573 0.6841 0.093 Uiso 0.819(6) 1 calc R . P A 1
H12B H 0.5393 0.3516 0.7355 0.093 Uiso 0.819(6) 1 calc R . P A 1
C12A C 0.387(3) 0.436(3) 0.7020(9) 0.0772(12) Uani 0.181(6) 1 d D . P A 2
H12C H 0.3193 0.4220 0.7343 0.093 Uiso 0.181(6) 1 calc R . P A 2
H12D H 0.3564 0.5332 0.6853 0.093 Uiso 0.181(6) 1 calc R . P A 2
C13 C 0.3598(9) 0.5065(8) 0.7236(3) 0.116(2) Uani 0.819(6) 1 d D . P A 1
H13A H 0.2804 0.4499 0.7442 0.174 Uiso 0.819(6) 1 calc GR . P A 1
H13B H 0.3087 0.5549 0.6926 0.174 Uiso 0.819(6) 1 calc GR . P A 1
H13C H 0.4077 0.5844 0.7466 0.174 Uiso 0.819(6) 1 calc GR . P A 1
C13A C 0.561(3) 0.447(4) 0.7204(13) 0.116(2) Uani 0.181(6) 1 d D . P A 2
H13D H 0.5912 0.3533 0.7390 0.174 Uiso 0.181(6) 1 calc GR . P A 2
H13E H 0.5732 0.5331 0.7448 0.174 Uiso 0.181(6) 1 calc GR . P A 2
H13F H 0.6296 0.4610 0.6889 0.174 Uiso 0.181(6) 1 calc GR . P A 2
C14 C 0.3763(3) -0.0427(3) 0.42666(11) 0.0526(6) Uani 1 1 d . . . . .
C15 C 0.4418(8) -0.1044(8) 0.33514(18) 0.122(2) Uani 1 1 d . . . . .
H15A H 0.5424 -0.0534 0.3432 0.183 Uiso 1 1 calc GR . . . .
H15B H 0.4056 -0.0751 0.2991 0.183 Uiso 1 1 calc GR . . . .
H15C H 0.4572 -0.2144 0.3365 0.183 Uiso 1 1 calc GR . . . .
N1 N 0.2772(3) 0.0376(2) 0.51279(8) 0.0492(5) Uani 1 1 d . . . . .
N2 N 0.2504(3) -0.0041(3) 0.45928(8) 0.0491(4) Uani 1 1 d . . . . .
H2 H 0.159(4) 0.006(3) 0.4441(11) 0.038(6) Uiso 1 1 d . . . . .
O1 O 0.0877(2) -0.1127(2) 0.55920(9) 0.0600(5) Uani 1 1 d D . . . .
H1 H 0.084(6) -0.214(3) 0.5563(18) 0.087(13) Uiso 1 1 d D . . . .
O2 O 0.1574(4) -0.0466(3) 0.68952(10) 0.0839(7) Uani 1 1 d . . . . .
O3 O 0.0671(3) 0.1484(3) 0.63834(8) 0.0652(5) Uani 1 1 d . . . . .
O4 O 0.4525(3) 0.4390(2) 0.59582(8) 0.0610(5) Uani 1 1 d . . . . .
O5 O 0.4199(5) 0.2813(3) 0.66918(12) 0.0656(9) Uani 0.819(6) 1 d . . P A 1
O5A O 0.350(2) 0.3156(19) 0.6646(6) 0.0656(9) Uani 0.181(6) 1 d . . P A 2
O6 O 0.5138(3) -0.0610(3) 0.44096(11) 0.0709(6) Uani 1 1 d . . . . .
O7 O 0.3220(3) -0.0598(3) 0.37512(8) 0.0707(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.522(4) . ?
C1 C5 1.591(3) . ?
C1 N1 1.465(3) . ?
C1 O1 1.401(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.520(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.546(4) . ?
C5 C6 1.519(3) . ?
C5 C9 1.521(4) . ?
C6 C7 1.351(3) . ?
C6 C11 1.435(3) . ?
C7 C8 1.489(3) . ?
C7 N1 1.362(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O2 1.199(3) . ?
C9 O3 1.329(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 O3 1.435(4) . ?
C11 O4 1.220(3) . ?
C11 O5 1.369(4) . ?
C11 O5A 1.314(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.476(8) . ?
C12 O5 1.442(5) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A C13A 1.51(2) . ?
C12A O5A 1.41(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C14 N2 1.349(4) . ?
C14 O6 1.197(4) . ?
C14 O7 1.341(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 O7 1.439(4) . ?
N1 N2 1.370(3) . ?
N2 H2 0.84(3) . ?
O1 H1 0.88(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
C2 C1 C5 105.6(2) . . ?
N1 C1 C2 113.2(2) . . ?
N1 C1 C5 100.99(17) . . ?
O1 C1 C2 113.8(2) . . ?
O1 C1 C5 114.2(2) . . ?
O1 C1 N1 108.5(2) . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.3(2) . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C2 C3 C4 102.9(3) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C3 C4 C5 104.8(2) . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C4 C5 C1 103.8(2) . . ?
C6 C5 C1 103.50(17) . . ?
C6 C5 C4 113.2(2) . . ?
C6 C5 C9 113.2(2) . . ?
C9 C5 C1 109.21(19) . . ?
C9 C5 C4 112.9(2) . . ?
C7 C6 C5 110.5(2) . . ?
C7 C6 C11 125.5(2) . . ?
C11 C6 C5 124.0(2) . . ?
C6 C7 C8 130.1(2) . . ?
C6 C7 N1 110.3(2) . . ?
N1 C7 C8 119.6(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C5 125.0(3) . . ?
O2 C9 O3 123.2(3) . . ?
O3 C9 C5 111.8(2) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
O4 C11 C6 126.7(2) . . ?
O4 C11 O5 121.8(3) . . ?
O4 C11 O5A 116.7(7) . . ?
O5 C11 C6 111.4(2) . . ?
O5A C11 C6 111.6(7) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
O5 C12 H12A 109.4 . . ?
O5 C12 H12B 109.4 . . ?
O5 C12 C13 111.1(5) . . ?
H12C C12A H12D 107.4 . . ?
C13A C12A H12C 108.2 . . ?
C13A C12A H12D 108.2 . . ?
O5A C12A H12C 108.2 . . ?
O5A C12A H12D 108.2 . . ?
O5A C12A C13A 116(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O6 C14 N2 126.2(3) . . ?
O6 C14 O7 125.0(3) . . ?
O7 C14 N2 108.8(2) . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O7 C15 H15A 109.5 . . ?
O7 C15 H15B 109.5 . . ?
O7 C15 H15C 109.5 . . ?
C7 N1 C1 114.65(19) . . ?
C7 N1 N2 124.0(2) . . ?
N2 N1 C1 121.35(19) . . ?
C14 N2 N1 120.1(2) . . ?
C14 N2 H2 117.0(18) . . ?
N1 N2 H2 122.3(18) . . ?
C1 O1 H1 106(3) . . ?
C9 O3 C10 116.3(3) . . ?
C11 O5 C12 116.9(3) . . ?
C11 O5A C12A 121.7(16) . . ?
C14 O7 C15 115.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O4 0.84(3) 2.02(3) 2.856(3) 172(3) 3_456
O1 H1 O6 0.88(2) 2.03(3) 2.885(3) 164(4) 3_446

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
C1 C2 C3 C4 42.3(3) . . . . ?
C1 C5 C6 C7 -1.7(3) . . . . ?
C1 C5 C6 C11 179.5(2) . . . . ?
C1 C5 C9 O2 94.6(3) . . . . ?
C1 C5 C9 O3 -83.2(3) . . . . ?
C1 N1 N2 C14 -100.2(3) . . . . ?
C2 C1 C5 C4 2.2(3) . . . . ?
C2 C1 C5 C6 120.7(2) . . . . ?
C2 C1 C5 C9 -118.5(2) . . . . ?
C2 C1 N1 C7 -115.4(2) . . . . ?
C2 C1 N1 N2 64.2(3) . . . . ?
C2 C3 C4 C5 -41.0(3) . . . . ?
C3 C4 C5 C1 23.5(3) . . . . ?
C3 C4 C5 C6 -88.0(3) . . . . ?
C3 C4 C5 C9 141.7(2) . . . . ?
C4 C5 C6 C7 110.1(2) . . . . ?
C4 C5 C6 C11 -68.7(3) . . . . ?
C4 C5 C9 O2 -20.4(4) . . . . ?
C4 C5 C9 O3 161.8(2) . . . . ?
C5 C1 C2 C3 -27.2(3) . . . . ?
C5 C1 N1 C7 -3.0(3) . . . . ?
C5 C1 N1 N2 176.5(2) . . . . ?
C5 C6 C7 C8 177.9(3) . . . . ?
C5 C6 C7 N1 -0.1(3) . . . . ?
C5 C6 C11 O4 175.4(3) . . . . ?
C5 C6 C11 O5 -0.4(4) . . . . ?
C5 C6 C11 O5A -30.8(10) . . . . ?
C5 C9 O3 C10 173.5(3) . . . . ?
C6 C5 C9 O2 -150.7(3) . . . . ?
C6 C5 C9 O3 31.5(3) . . . . ?
C6 C7 N1 C1 2.2(3) . . . . ?
C6 C7 N1 N2 -177.4(2) . . . . ?
C6 C11 O5 C12 175.8(4) . . . . ?
C6 C11 O5A C12A -178.3(16) . . . . ?
C7 C6 C11 O4 -3.2(5) . . . . ?
C7 C6 C11 O5 -179.0(3) . . . . ?
C7 C6 C11 O5A 150.6(9) . . . . ?
C7 N1 N2 C14 79.3(3) . . . . ?
C8 C7 N1 C1 -176.1(2) . . . . ?
C8 C7 N1 N2 4.3(4) . . . . ?
C9 C5 C6 C7 -119.8(2) . . . . ?
C9 C5 C6 C11 61.4(3) . . . . ?
C11 C6 C7 C8 -3.3(4) . . . . ?
C11 C6 C7 N1 178.6(2) . . . . ?
C13 C12 O5 C11 87.8(6) . . . . ?
C13A C12A O5A C11 -66(3) . . . . ?
N1 C1 C2 C3 82.3(3) . . . . ?
N1 C1 C5 C4 -115.9(2) . . . . ?
N1 C1 C5 C6 2.6(2) . . . . ?
N1 C1 C5 C9 123.5(2) . . . . ?
N2 C14 O7 C15 -178.8(4) . . . . ?
O1 C1 C2 C3 -153.2(2) . . . . ?
O1 C1 C5 C4 127.9(2) . . . . ?
O1 C1 C5 C6 -113.6(2) . . . . ?
O1 C1 C5 C9 7.2(3) . . . . ?
O1 C1 N1 C7 117.3(2) . . . . ?
O1 C1 N1 N2 -63.1(3) . . . . ?
O2 C9 O3 C10 -4.4(5) . . . . ?
O4 C11 O5 C12 -0.3(6) . . . . ?
O4 C11 O5A C12A -22(2) . . . . ?
O6 C14 N2 N1 8.6(4) . . . . ?
O6 C14 O7 C15 0.3(5) . . . . ?
O7 C14 N2 N1 -172.4(2) . . . . ?

_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 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.929
####################################################################### 
# 
# 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_20230339
_database_code_depnum_ccdc_archive 'CCDC 2253283'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2023-04-01 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-03-17
_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         'C32 H48 N4 O14'
_chemical_formula_sum            'C32 H48 N4 O14'
_chemical_formula_weight         712.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N3O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4928(9)
_cell_length_b                   9.8026(9)
_cell_length_c                   11.3802(8)
_cell_angle_alpha                102.528(7)
_cell_angle_beta                 110.036(8)
_cell_angle_gamma                102.007(8)
_cell_volume                     924.02(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1960
_cell_measurement_theta_min      4.3290
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6573
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.583
_diffrn_reflns_theta_min         4.355
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  90.00   73
  2  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  30.00   73
  3  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -30.00   93
  4  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00-120.00   93
  5  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00 120.00   87
  6  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00-150.00   98
  7  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00-150.00   75
  8  ω     61.00 110.00   1.00    1.00    --   36.47 178.00  60.00   49
  9  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00  60.00   75
 10  ω     40.00 109.00   1.00    1.00    --  108.00-111.00 -90.00   69
 11  ω     66.00 104.00   1.00    1.00    --  108.00 178.00  30.00   38
 12  ω     88.00 178.00   1.00    1.00    --  108.00  45.00 150.00   90
 13  ω     49.00 128.00   1.00    1.00    --  108.00 -45.00  60.00   79
 14  ω     88.00 176.00   1.00    1.00    --  108.00  45.00  90.00   88
 15  ω     42.00 103.00   1.00    1.00    --  108.00 -94.00  30.00   61
 16  ω     95.00 136.00   1.00    1.00    --  108.00 -77.00  90.00   41
 17  ω    128.00 169.00   1.00    1.00    --  108.00  45.00   0.00   41
 18  ω     39.00  99.00   1.00    1.00    --  108.00 -94.00  90.00   60
 19  ω    110.00 176.00   1.00    1.00    --  108.00 111.00  30.00   66
 20  ω    133.00 175.00   1.00    1.00    --  108.00  74.00 123.00   42
 21  ω    126.00 177.00   1.00    1.00    --  108.00  77.00-180.00   51
 22  ω     80.00 106.00   1.00    1.00    --  108.00 -94.00 120.00   26
 23  ω     38.00 100.00   1.00    1.00    --  108.00 -94.00 -30.00   62
 24  ω    153.00 178.00   1.00    1.00    --  108.00  45.00-120.00   25
 25  ω     88.00 133.00   1.00    1.00    --  108.00  45.00-120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054249000
_diffrn_orient_matrix_UB_12      0.1529011000
_diffrn_orient_matrix_UB_13      0.0649778000
_diffrn_orient_matrix_UB_21      0.1679945000
_diffrn_orient_matrix_UB_22      0.0353919000
_diffrn_orient_matrix_UB_23      0.1048260000
_diffrn_orient_matrix_UB_31      0.0686483000
_diffrn_orient_matrix_UB_32      0.0632519000
_diffrn_orient_matrix_UB_33      -0.0884148000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2472
_reflns_number_total             3435
_reflns_odcompleteness_completeness 99.55
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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         0.219
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0076(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.063
_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)+(0.0664P)²+0.2851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C9-C10
 1.56 with sigma of 0.02
 C10A-C9A
 1.56 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
4. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C11(H11A,H11B)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.8542(3) 0.8786(3) 0.8989(2) 0.0452(6) Uani 1 1 d . . . . .
C2 C 0.9268(3) 1.0036(3) 0.8538(2) 0.0443(6) Uani 1 1 d . . . . .
C3 C 0.7828(3) 1.0443(3) 0.7799(2) 0.0467(6) Uani 1 1 d . . . . .
C4 C 0.6687(3) 0.9982(3) 0.8204(2) 0.0488(6) Uani 1 1 d . . . . .
C5 C 0.5142(3) 1.0282(4) 0.7937(3) 0.0645(8) Uani 1 1 d . . . . .
H5A H 0.4453 0.9550 0.8101 0.097 Uiso 1 1 calc GR . . . .
H5B H 0.4670 1.0251 0.7035 0.097 Uiso 1 1 calc GR . . . .
H5C H 0.5312 1.1235 0.8505 0.097 Uiso 1 1 calc GR . . . .
C6 C 1.0110(3) 0.9536(3) 0.7673(2) 0.0486(6) Uani 1 1 d . . . . .
C7 C 0.9757(4) 0.8235(4) 0.5543(3) 0.0823(10) Uani 1 1 d . . . . .
H7A H 0.8958 0.7892 0.4661 0.123 Uiso 1 1 calc GR . . . .
H7B H 1.0145 0.7446 0.5739 0.123 Uiso 1 1 calc GR . . . .
H7C H 1.0608 0.9025 0.5620 0.123 Uiso 1 1 calc GR . . . .
C8 C 0.7933(3) 1.1415(3) 0.7016(3) 0.0544(6) Uani 1 1 d . . . . .
C9 C 0.6717(10) 1.2823(9) 0.5786(9) 0.078(2) Uani 0.632(6) 1 d D U P A 1
H9A H 0.6868 1.2459 0.4989 0.093 Uiso 0.632(6) 1 calc R . P A 1
H9B H 0.7598 1.3689 0.6370 0.093 Uiso 0.632(6) 1 calc R . P A 1
C9A C 0.632(2) 1.2349(16) 0.5410(18) 0.078(2) Uani 0.368(6) 1 d D U P A 2
H9AA H 0.5273 1.1891 0.4717 0.093 Uiso 0.368(6) 1 calc R . P A 2
H9AB H 0.7095 1.2309 0.5032 0.093 Uiso 0.368(6) 1 calc R . P A 2
C10 C 0.5194(8) 1.3169(8) 0.5472(7) 0.0981(19) Uani 0.632(6) 1 d D . P A 1
H10A H 0.5151 1.3822 0.4952 0.147 Uiso 0.632(6) 1 calc GR . P A 1
H10B H 0.5122 1.3629 0.6276 0.147 Uiso 0.632(6) 1 calc GR . P A 1
H10C H 0.4332 1.2278 0.4988 0.147 Uiso 0.632(6) 1 calc GR . P A 1
C10A C 0.6543(15) 1.3906(14) 0.6156(12) 0.0981(19) Uani 0.368(6) 1 d D . P A 2
H10D H 0.6563 1.4513 0.5600 0.147 Uiso 0.368(6) 1 calc GR . P A 2
H10E H 0.7520 1.4271 0.6924 0.147 Uiso 0.368(6) 1 calc GR . P A 2
H10F H 0.5687 1.3925 0.6419 0.147 Uiso 0.368(6) 1 calc GR . P A 2
C11 C 1.0377(3) 1.1392(3) 0.9749(2) 0.0464(6) Uani 1 1 d . . . . .
H11A H 1.1041 1.2008 0.9460 0.056 Uiso 1 1 calc R . . . .
H11B H 0.9720 1.1941 0.9983 0.056 Uiso 1 1 calc R . . . .
C12 C 0.4935(3) 0.7205(3) 0.8597(3) 0.0539(6) Uani 1 1 d . . . . .
C13 C 0.2655(3) 0.5451(3) 0.8583(3) 0.0603(7) Uani 1 1 d . . . . .
C14 C 0.3035(4) 0.4079(3) 0.8088(3) 0.0722(9) Uani 1 1 d . . . . .
H14A H 0.3362 0.4151 0.7388 0.108 Uiso 1 1 calc GR . . . .
H14B H 0.2115 0.3243 0.7767 0.108 Uiso 1 1 calc GR . . . .
H14C H 0.3869 0.3969 0.8794 0.108 Uiso 1 1 calc GR . . . .
C15 C 0.2136(4) 0.5377(4) 0.9692(4) 0.0854(11) Uani 1 1 d . . . . .
H15A H 0.2902 0.5140 1.0355 0.128 Uiso 1 1 calc GR . . . .
H15B H 0.1135 0.4633 0.9353 0.128 Uiso 1 1 calc GR . . . .
H15C H 0.2040 0.6310 1.0072 0.128 Uiso 1 1 calc GR . . . .
C16 C 0.1463(4) 0.5777(4) 0.7501(4) 0.0996(13) Uani 1 1 d . . . . .
H16A H 0.1320 0.6696 0.7852 0.149 Uiso 1 1 calc GR . . . .
H16B H 0.0477 0.5008 0.7140 0.149 Uiso 1 1 calc GR . . . .
H16C H 0.1832 0.5835 0.6821 0.149 Uiso 1 1 calc GR . . . .
N1 N 0.7183(2) 0.9216(2) 0.9074(2) 0.0482(5) Uani 1 1 d . . . . .
N2 N 0.6173(3) 0.8402(3) 0.9465(2) 0.0545(6) Uani 1 1 d . . . . .
H2 H 0.638(3) 0.862(3) 1.029(3) 0.060(8) Uiso 1 1 d . . . . .
O1 O 0.8035(2) 0.73633(19) 0.80638(17) 0.0582(5) Uani 1 1 d . . . . .
H1 H 0.7231 0.7269 0.7434 0.087 Uiso 1 1 calc GR . . . .
O2 O 1.1500(2) 0.9806(3) 0.80299(19) 0.0705(6) Uani 1 1 d . . . . .
O3 O 0.9095(2) 0.8750(2) 0.64568(17) 0.0633(5) Uani 1 1 d . . . . .
O4 O 0.9124(2) 1.1940(2) 0.6891(2) 0.0710(6) Uani 1 1 d . . . . .
O5 O 0.6574(2) 1.1675(3) 0.6439(2) 0.0812(7) Uani 1 1 d . . . . .
O6 O 0.4639(2) 0.6732(2) 0.74425(19) 0.0708(6) Uani 1 1 d . . . . .
O7 O 0.4123(2) 0.6712(2) 0.92575(18) 0.0609(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.551(3) . ?
C1 C11 1.522(3) 2_777 ?
C1 N1 1.464(3) . ?
C1 O1 1.422(3) . ?
C2 C3 1.522(3) . ?
C2 C6 1.530(3) . ?
C2 C11 1.550(3) . ?
C3 C4 1.348(3) . ?
C3 C8 1.450(3) . ?
C4 C5 1.498(4) . ?
C4 N1 1.384(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O2 1.190(3) . ?
C6 O3 1.324(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 O3 1.443(3) . ?
C8 O4 1.210(3) . ?
C8 O5 1.337(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.495(10) . ?
C9 O5 1.486(10) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.509(15) . ?
C9A O5 1.44(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
C11 C1 1.522(3) 2_777 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.364(3) . ?
C12 O6 1.204(3) . ?
C12 O7 1.338(3) . ?
C13 C14 1.506(4) . ?
C13 C15 1.515(4) . ?
C13 C16 1.505(4) . ?
C13 O7 1.482(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.372(3) . ?
N2 H2 0.85(3) . ?
O1 H1 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C2 116.2(2) 2_777 . ?
N1 C1 C2 99.69(19) . . ?
N1 C1 C11 114.45(19) . 2_777 ?
O1 C1 C2 113.76(19) . . ?
O1 C1 C11 102.8(2) . 2_777 ?
O1 C1 N1 110.33(19) . . ?
C3 C2 C1 102.11(19) . . ?
C3 C2 C6 112.77(19) . . ?
C3 C2 C11 107.4(2) . . ?
C6 C2 C1 112.3(2) . . ?
C6 C2 C11 111.59(19) . . ?
C11 C2 C1 110.15(19) . . ?
C4 C3 C2 108.6(2) . . ?
C4 C3 C8 129.9(2) . . ?
C8 C3 C2 120.4(2) . . ?
C3 C4 C5 130.2(2) . . ?
C3 C4 N1 109.6(2) . . ?
N1 C4 C5 120.0(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 C2 125.2(2) . . ?
O2 C6 O3 123.3(2) . . ?
O3 C6 C2 111.5(2) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
O4 C8 C3 123.7(3) . . ?
O4 C8 O5 123.1(2) . . ?
O5 C8 C3 113.2(2) . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
O5 C9 H9A 110.8 . . ?
O5 C9 H9B 110.8 . . ?
O5 C9 C10 104.9(7) . . ?
H9AA C9A H9AB 109.3 . . ?
C10A C9A H9AA 111.5 . . ?
C10A C9A H9AB 111.5 . . ?
O5 C9A H9AA 111.5 . . ?
O5 C9A H9AB 111.5 . . ?
O5 C9A C10A 101.4(12) . . ?
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 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C1 C11 C2 121.1(2) 2_777 . ?
C1 C11 H11A 107.1 2_777 . ?
C1 C11 H11B 107.1 2_777 . ?
C2 C11 H11A 107.1 . . ?
C2 C11 H11B 107.1 . . ?
H11A C11 H11B 106.8 . . ?
O6 C12 N2 124.6(2) . . ?
O6 C12 O7 127.7(2) . . ?
O7 C12 N2 107.7(2) . . ?
C14 C13 C15 110.9(3) . . ?
C16 C13 C14 112.6(3) . . ?
C16 C13 C15 111.3(3) . . ?
O7 C13 C14 109.5(2) . . ?
O7 C13 C15 101.8(2) . . ?
O7 C13 C16 110.1(2) . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 N1 C1 110.93(19) . . ?
N2 N1 C1 120.4(2) . . ?
N2 N1 C4 122.3(2) . . ?
C12 N2 N1 122.0(2) . . ?
C12 N2 H2 120.1(19) . . ?
N1 N2 H2 117.8(19) . . ?
C1 O1 H1 109.5 . . ?
C6 O3 C7 116.5(2) . . ?
C8 O5 C9 113.7(4) . . ?
C8 O5 C9A 122.0(8) . . ?
C12 O7 C13 121.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.85(3) 2.21(3) 2.826(3) 129(2) 2_777
O1 H1 O6 0.82 2.41 2.949(3) 124.0 .

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
C1 C2 C3 C4 21.0(3) . . . . ?
C1 C2 C3 C8 -169.6(2) . . . . ?
C1 C2 C6 O2 -102.6(3) . . . . ?
C1 C2 C6 O3 77.4(3) . . . . ?
C1 C2 C11 C1 39.7(3) . . . 2_777 ?
C1 N1 N2 C12 -86.0(3) . . . . ?
C2 C1 N1 C4 28.1(2) . . . . ?
C2 C1 N1 N2 -179.3(2) . . . . ?
C2 C3 C4 C5 170.5(3) . . . . ?
C2 C3 C4 N1 -4.1(3) . . . . ?
C2 C3 C8 O4 0.7(4) . . . . ?
C2 C3 C8 O5 -179.5(2) . . . . ?
C2 C6 O3 C7 179.1(2) . . . . ?
C3 C2 C6 O2 142.7(3) . . . . ?
C3 C2 C6 O3 -37.4(3) . . . . ?
C3 C2 C11 C1 150.2(2) . . . 2_777 ?
C3 C4 N1 C1 -16.3(3) . . . . ?
C3 C4 N1 N2 -168.3(2) . . . . ?
C3 C8 O5 C9 172.1(4) . . . . ?
C3 C8 O5 C9A -166.8(7) . . . . ?
C4 C3 C8 O4 167.5(3) . . . . ?
C4 C3 C8 O5 -12.6(4) . . . . ?
C4 N1 N2 C12 63.5(4) . . . . ?
C5 C4 N1 C1 168.5(2) . . . . ?
C5 C4 N1 N2 16.4(4) . . . . ?
C6 C2 C3 C4 141.8(2) . . . . ?
C6 C2 C3 C8 -48.8(3) . . . . ?
C6 C2 C11 C1 -85.8(3) . . . 2_777 ?
C8 C3 C4 C5 2.4(5) . . . . ?
C8 C3 C4 N1 -172.2(3) . . . . ?
C10 C9 O5 C8 -168.1(5) . . . . ?
C10A C9A O5 C8 -101.8(12) . . . . ?
C11 C1 C2 C3 -151.4(2) 2_777 . . . ?
C11 C1 C2 C6 87.5(3) 2_777 . . . ?
C11 C1 C2 C11 -37.6(3) 2_777 . . . ?
C11 C1 N1 C4 152.7(2) 2_777 . . . ?
C11 C1 N1 N2 -54.6(3) 2_777 . . . ?
C11 C2 C3 C4 -94.9(2) . . . . ?
C11 C2 C3 C8 74.5(3) . . . . ?
C11 C2 C6 O2 21.7(4) . . . . ?
C11 C2 C6 O3 -158.4(2) . . . . ?
C14 C13 O7 C12 65.9(3) . . . . ?
C15 C13 O7 C12 -176.6(3) . . . . ?
C16 C13 O7 C12 -58.4(4) . . . . ?
N1 C1 C2 C3 -28.0(2) . . . . ?
N1 C1 C2 C6 -149.03(19) . . . . ?
N1 C1 C2 C11 85.9(2) . . . . ?
N2 C12 O7 C13 177.3(2) . . . . ?
O1 C1 C2 C3 89.4(2) . . . . ?
O1 C1 C2 C6 -31.6(3) . . . . ?
O1 C1 C2 C11 -156.7(2) . . . . ?
O1 C1 N1 C4 -91.9(2) . . . . ?
O1 C1 N1 N2 60.8(3) . . . . ?
O2 C6 O3 C7 -1.0(4) . . . . ?
O4 C8 O5 C9 -8.0(6) . . . . ?
O4 C8 O5 C9A 13.1(8) . . . . ?
O6 C12 N2 N1 2.1(5) . . . . ?
O6 C12 O7 C13 -0.9(5) . . . . ?
O7 C12 N2 N1 -176.1(2) . . . . ?

_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 1.848
_oxdiff_exptl_absorpt_empirical_full_min 0.890
