# 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_20230221a
_database_code_depnum_ccdc_archive 'CCDC 2246700'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2023-03-07 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_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 H23 N3 O8'
_chemical_formula_sum            'C20 H23 N3 O8'
_chemical_formula_weight         433.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3N2O2
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   21.0745(7)
_cell_length_b                   12.0391(4)
_cell_length_c                   9.3014(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.027(3)
_cell_angle_gamma                90
_cell_volume                     2256.50(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4651
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4080
_cell_measurement_theta_min      4.2740
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11094
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.853
_diffrn_reflns_theta_min         4.278
_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 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  16.00   1.00    1.00    --    0.00 -57.00-180.00   32
  2  ω   -106.00 -80.00   1.00    3.00    --  -33.50 -19.00 -90.00   26
  3  ω    -31.00  10.00   1.00    3.00    --  -33.50  37.00 -90.00   41
  4  ω    -59.00 -25.00   1.00    3.00    --  -33.50 -19.00 -90.00   34
  5  ω    -71.00 -45.00   1.00    3.00    --  -33.50 178.00-120.00   26
  6  ω   -108.00 -82.00   1.00    3.00    --  -33.50 178.00-120.00   26
  7  ω     59.00  91.00   1.00    3.00    --   36.47 178.00-120.00   32
  8  ω     59.00 110.00   1.00    3.00    --   36.47 178.00-150.00   51
  9  ω     33.00  74.00   1.00    3.00    --   36.47  57.00  30.00   41
 10  ω     -3.00  22.00   1.00    3.00    --   36.47 100.00-136.80   25
 11  ω      9.00  49.00   1.00    3.00    --   36.47  77.00  30.00   40
 12  ω     21.00  47.00   1.00    3.00    --   36.47  37.00  30.00   26
 13  ω     12.00  47.00   1.00    3.00    --   36.47  77.00 -30.00   35
 14  ω     57.00 107.00   1.00    3.00    --   36.47 178.00   0.00   50
 15  ω     29.00  68.00   1.00    3.00    --   36.47  57.00 -60.00   39
 16  ω     49.00  94.00   1.00    3.00    --   36.47  57.00 120.00   45
 17  ω     54.00 105.00   1.00    3.00    --   36.47  77.00  30.00   51
 18  ω     -3.00  23.00   1.00    3.00    --   36.47 -99.00  30.00   26
 19  ω     80.00 105.00   1.00    3.00    --   36.47  57.00 -60.00   25
 20  ω     23.00  77.00   1.00    3.00    --   36.47 -99.00-180.00   54
 21  ω      1.00  40.00   1.00    3.00    --   36.47  19.00 -60.00   39
 22  ω     50.00  76.00   1.00    3.00    --   36.47  57.00  60.00   26
 23  ω     20.00  46.00   1.00    3.00    --   36.47  77.00 -60.00   26
 24  ω      1.00  27.00   1.00    3.00    --   36.47  95.00 -61.91   26
 25  ω     -8.00  17.00   1.00    3.00    --   36.47 106.00  93.56   25
 26  ω      0.00  76.00   1.00    3.00    --   36.47  19.00  60.00   76
 27  ω     68.00 104.00   1.00    3.00    --   36.47  57.00 -90.00   36
 28  ω     40.00  66.00   1.00    3.00    --   36.47  57.00-180.00   26
 29  ω     18.00  46.00   1.00    3.00    --   36.47  57.00  60.00   28
 30  ω     80.00 160.00   1.00   13.00    --  108.00  77.00-180.00   80
 31  ω     82.00 108.00   1.00   13.00    --  108.00  30.00  30.00   26
 32  ω     79.00 105.00   1.00   13.00    --  108.00  77.00   0.00   26
 33  ω     82.00 110.00   1.00   13.00    --  108.00  30.00  60.00   28
 34  ω     84.00 110.00   1.00   13.00    --  108.00  30.00  90.00   26
 35  ω    117.00 176.00   1.00   13.00    --  108.00  77.00  60.00   59
 36  ω     79.00 106.00   1.00   13.00    --  108.00  77.00  60.00   27
 37  ω     37.00 108.00   1.00   13.00    --  108.00-111.00  90.00   71
 38  ω     88.00 114.00   1.00   13.00    --  108.00  45.00  90.00   26
 39  ω    137.00 163.00   1.00   13.00    --  108.00  61.00   0.00   26
 40  ω    144.00 170.00   1.00   13.00    --  108.00  77.00  90.00   26
 41  ω     79.00 105.00   1.00   13.00    --  108.00  77.00  90.00   26
 42  ω     82.00 108.00   1.00   13.00    --  108.00  30.00 150.00   26
 43  ω    110.00 176.00   1.00   13.00    --  108.00  77.00 150.00   66
 44  ω     79.00 105.00   1.00   13.00    --  108.00  77.00 150.00   26
 45  ω    111.00 176.00   1.00   13.00    --  108.00  77.00  30.00   65
 46  ω     41.00 121.00   1.00   13.00    --  108.00 -61.00  60.00   80
 47  ω     88.00 114.00   1.00   13.00    --  108.00  45.00  60.00   26
 48  ω     79.00 105.00   1.00   13.00    --  108.00  77.00  30.00   26
 49  ω     88.00 114.00   1.00   13.00    --  108.00  61.00  60.00   26
 50  ω     79.00 105.00   1.00   13.00    --  108.00  77.00 120.00   26
 51  ω     88.00 114.00   1.00   13.00    --  108.00  45.00 120.00   26
 52  ω     80.00 155.00   1.00   13.00    --  108.00  77.00 -60.00   75
 53  ω     88.00 119.00   1.00   13.00    --  108.00  61.00  30.00   31
 54  ω     84.00 169.00   1.00   13.00    --  108.00  30.00 120.00   85
 55  ω     88.00 114.00   1.00   13.00    --  108.00  61.00 120.00   26
 56  ω     91.00 117.00   1.00   13.00    --  108.00  61.00 -30.00   26
 57  ω     93.00 144.00   1.00   13.00    --  108.00  45.00 -30.00   51
 58  ω     84.00 110.00   1.00   13.00    --  108.00  30.00   0.00   26
 59  ω     88.00 114.00   1.00   13.00    --  108.00  61.00  90.00   26
 60  ω     79.00 104.00   1.00   13.00    --  108.00  77.00 -30.00   25
 61  ω     88.00 114.00   1.00   13.00    --  108.00  61.00   0.00   26
 62  ω     70.00 109.00   1.00   13.00    --  108.00 -94.00 150.00   39
;
_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      -0.0478029582
_diffrn_orient_matrix_UB_12      -0.0061207369
_diffrn_orient_matrix_UB_13      -0.1607290851
_diffrn_orient_matrix_UB_21      0.0595205248
_diffrn_orient_matrix_UB_22      -0.0142437450
_diffrn_orient_matrix_UB_23      -0.0628819169
_diffrn_orient_matrix_UB_31      -0.0043670009
_diffrn_orient_matrix_UB_32      -0.1269871787
_diffrn_orient_matrix_UB_33      0.0147813204
_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         0.674
_reflns_Friedel_fraction_full    0.766
_reflns_Friedel_fraction_max     0.739
_reflns_number_gt                3483
_reflns_number_total             3802
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.200
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3802
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.048
_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)+(0.0693P)²+0.2933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1161
_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. Restrained distances
 N3-H3
 0.87 with sigma of 0.02
 C7A-C6
 1.54 with sigma of 0.02
 C14-C15
 1.6 with sigma of 0.02
 C19-C20
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C12A)
Uanis(C11) = Uanis(C11A)
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(C7) = Uanis(C7A)
4. Others
 Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=Sof(H9A)=
 Sof(C8A)=Sof(H8A)=1-FVAR(1)
 Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=Sof(C10)=Sof(H10)=Sof(C9)=Sof(H9)=Sof(C8)=
 Sof(H8)=FVAR(1)
 Sof(C7A)=1-FVAR(2)
 Sof(C7)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C9(H9), C8(H8), C12A(H12A), C11A(H11A),
 C10A(H10A), C9A(H9A), C8A(H8A)
5.c Fitted hexagon refined as free rotating group:
 C12(C11,C10,C9,C8,C7), C7A(C12A,C11A,C10A,C9A,C8A)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_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
C1 C 0.74115(15) 0.2363(3) 0.2336(3) 0.0548(7) Uani 1 1 d . . . . .
C2 C 0.70638(13) 0.1646(2) 0.0938(3) 0.0503(6) Uani 1 1 d . . . . .
C3 C 0.75822(13) 0.1631(2) 0.0105(3) 0.0479(6) Uani 1 1 d . . . . .
C4 C 0.81282(13) 0.2190(3) 0.0877(3) 0.0503(6) Uani 1 1 d . . . . .
C5 C 0.87637(15) 0.2435(3) 0.0562(4) 0.0683(9) Uani 1 1 d . . . . .
H5A H 0.8788 0.2018 -0.0301 0.102 Uiso 1 1 calc GR . . . .
H5B H 0.9127 0.2230 0.1416 0.102 Uiso 1 1 calc GR . . . .
H5C H 0.8788 0.3214 0.0367 0.102 Uiso 1 1 calc GR . . . .
C6 C 0.63847(14) 0.3217(3) -0.0219(3) 0.0559(7) Uani 1 1 d D . . . .
C12 C 0.57632(19) 0.4695(4) -0.1913(7) 0.0844(17) Uani 0.662(5) 1 d . . P A 1
H12 H 0.6158 0.5095 -0.1653 0.101 Uiso 0.662(5) 1 calc R . P A 1
C11 C 0.5199(2) 0.5138(4) -0.2929(6) 0.112(3) Uani 0.662(5) 1 d G . P A 1
H11 H 0.5216 0.5834 -0.3348 0.134 Uiso 0.662(5) 1 calc R . P A 1
C10 C 0.4609(2) 0.4539(5) -0.3318(6) 0.101(2) Uani 0.662(5) 1 d G . P A 1
H10 H 0.4232 0.4836 -0.3998 0.122 Uiso 0.662(5) 1 calc R . P A 1
C9 C 0.4583(2) 0.3498(5) -0.2692(7) 0.119(3) Uani 0.662(5) 1 d G . P A 1
H9 H 0.4189 0.3098 -0.2952 0.143 Uiso 0.662(5) 1 calc R . P A 1
C8 C 0.5147(3) 0.3056(4) -0.1676(7) 0.082(2) Uani 0.662(5) 1 d G . P A 1
H8 H 0.5130 0.2359 -0.1257 0.099 Uiso 0.662(5) 1 calc R . P A 1
C7 C 0.5737(2) 0.3654(4) -0.1287(6) 0.0640(11) Uani 0.70(3) 1 d G . P A 1
C13 C 0.69271(15) 0.0488(3) 0.1465(3) 0.0560(7) Uani 1 1 d . . . . .
C14 C 0.7425(2) -0.1052(3) 0.2912(4) 0.0764(10) Uani 1 1 d D . . . .
H14A H 0.7205 -0.1541 0.2088 0.092 Uiso 1 1 calc R . . . .
H14B H 0.7167 -0.1036 0.3622 0.092 Uiso 1 1 calc R . . . .
C15 C 0.8107(2) -0.1459(4) 0.3662(4) 0.0823(11) Uani 1 1 d D . . . .
H15A H 0.8320 -0.0970 0.4476 0.123 Uiso 1 1 calc GR . . . .
H15B H 0.8356 -0.1476 0.2949 0.123 Uiso 1 1 calc GR . . . .
H15C H 0.8085 -0.2193 0.4047 0.123 Uiso 1 1 calc GR . . . .
C16 C 0.74410(14) 0.1035(2) -0.1324(3) 0.0504(6) Uani 1 1 d . . . . .
C17 C 0.7768(3) 0.0627(4) -0.3483(4) 0.0829(12) Uani 1 1 d . . . . .
H17A H 0.7853 -0.0152 -0.3298 0.124 Uiso 1 1 calc GR . . . .
H17B H 0.8057 0.0915 -0.4021 0.124 Uiso 1 1 calc GR . . . .
H17C H 0.7315 0.0733 -0.4071 0.124 Uiso 1 1 calc GR . . . .
C18 C 0.88268(14) 0.3020(3) 0.4516(3) 0.0543(7) Uani 1 1 d . . . . .
C19 C 0.9563(2) 0.3720(5) 0.6758(4) 0.0877(13) Uani 1 1 d D . . . .
H19A H 0.9891 0.3169 0.6702 0.105 Uiso 1 1 calc R . . . .
H19B H 0.9323 0.3446 0.7430 0.105 Uiso 1 1 calc R . . . .
C20 C 0.9894(2) 0.4791(5) 0.7326(6) 0.112(2) Uani 1 1 d D . . . .
H20A H 1.0201 0.4682 0.8305 0.169 Uiso 1 1 calc GR . . . .
H20B H 0.9566 0.5327 0.7388 0.169 Uiso 1 1 calc GR . . . .
H20C H 1.0128 0.5056 0.6650 0.169 Uiso 1 1 calc GR . . . .
N1 N 0.80362(12) 0.2588(2) 0.2212(3) 0.0559(6) Uani 1 1 d . . . . .
N2 N 0.84558(14) 0.3350(2) 0.3126(3) 0.0631(7) Uani 1 1 d . . . . .
H2 H 0.835(2) 0.405(5) 0.299(5) 0.090(14) Uiso 1 1 d . . . . .
N3 N 0.64342(12) 0.2128(2) 0.0110(3) 0.0569(6) Uani 1 1 d D . . . .
H3 H 0.6114(14) 0.170(3) -0.028(4) 0.056(9) Uiso 1 1 d D . . . .
O1 O 0.71990(13) 0.2634(2) 0.3338(3) 0.0735(7) Uani 1 1 d . . . . .
O2 O 0.68545(11) 0.3846(2) 0.0263(3) 0.0683(6) Uani 1 1 d . . . . .
O3 O 0.63894(12) 0.0069(2) 0.1103(3) 0.0803(7) Uani 1 1 d . . . . .
O4 O 0.74753(11) 0.0058(2) 0.2349(3) 0.0645(6) Uani 1 1 d . . . . .
O5 O 0.69528(11) 0.0472(2) -0.1796(2) 0.0618(5) Uani 1 1 d . . . . .
O6 O 0.78880(12) 0.1209(2) -0.2058(2) 0.0658(6) Uani 1 1 d . . . . .
O7 O 0.89112(14) 0.2083(2) 0.4951(3) 0.0797(7) Uani 1 1 d . . . . .
O8 O 0.91097(11) 0.3920(2) 0.5280(2) 0.0676(6) Uani 1 1 d . . . . .
C7A C 0.5721(5) 0.3559(9) -0.1063(16) 0.0640(11) Uani 0.30(3) 1 d D . P A 2
C12A C 0.5545(4) 0.4656(8) -0.0920(13) 0.0844(17) Uani 0.338(5) 1 d G . P A 2
H12A H 0.5846 0.5137 -0.0288 0.101 Uiso 0.338(5) 1 calc R . P A 2
C11A C 0.4918(5) 0.5036(8) -0.1720(14) 0.112(3) Uani 0.338(5) 1 d G . P A 2
H11A H 0.4800 0.5771 -0.1623 0.134 Uiso 0.338(5) 1 calc R . P A 2
C10A C 0.4467(4) 0.4318(11) -0.2664(13) 0.101(2) Uani 0.338(5) 1 d G . P A 2
H10A H 0.4048 0.4572 -0.3199 0.122 Uiso 0.338(5) 1 calc R . P A 2
C9A C 0.4643(6) 0.3220(10) -0.2808(14) 0.119(3) Uani 0.338(5) 1 d G . P A 2
H9A H 0.4342 0.2739 -0.3439 0.143 Uiso 0.338(5) 1 calc R . P A 2
C8A C 0.5270(7) 0.2840(8) -0.2007(18) 0.082(2) Uani 0.338(5) 1 d G . P A 2
H8A H 0.5388 0.2106 -0.2104 0.099 Uiso 0.338(5) 1 calc R . 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
C1 C2 1.554(4) . ?
C1 N1 1.381(4) . ?
C1 O1 1.192(4) . ?
C2 C3 1.513(4) . ?
C2 C13 1.532(4) . ?
C2 N3 1.447(4) . ?
C3 C4 1.345(4) . ?
C3 C16 1.463(4) . ?
C4 C5 1.482(4) . ?
C4 N1 1.396(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.527(4) . ?
C6 N3 1.344(4) . ?
C6 O2 1.222(4) . ?
C6 C7A 1.449(9) . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C12 C7 1.3900 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C7 1.3900 . ?
C13 O3 1.195(4) . ?
C13 O4 1.312(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.485(6) . ?
C14 O4 1.450(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O5 1.203(4) . ?
C16 O6 1.331(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 O6 1.455(4) . ?
C18 N2 1.360(4) . ?
C18 O7 1.194(4) . ?
C18 O8 1.337(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.488(7) . ?
C19 O8 1.446(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.381(3) . ?
N2 H2 0.87(6) . ?
N3 H3 0.85(2) . ?
C7A C12A 1.3900 . ?
C7A C8A 1.3900 . ?
C12A H12A 0.9300 . ?
C12A C11A 1.3900 . ?
C11A H11A 0.9300 . ?
C11A C10A 1.3900 . ?
C10A H10A 0.9300 . ?
C10A C9A 1.3900 . ?
C9A H9A 0.9300 . ?
C9A C8A 1.3900 . ?
C8A H8A 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
N1 C1 C2 105.5(2) . . ?
O1 C1 C2 127.8(3) . . ?
O1 C1 N1 126.7(3) . . ?
C3 C2 C1 101.6(2) . . ?
C3 C2 C13 112.6(2) . . ?
C13 C2 C1 109.0(2) . . ?
N3 C2 C1 110.9(2) . . ?
N3 C2 C3 114.8(2) . . ?
N3 C2 C13 107.9(2) . . ?
C4 C3 C2 110.7(2) . . ?
C4 C3 C16 130.2(3) . . ?
C16 C3 C2 119.1(2) . . ?
C3 C4 C5 132.5(3) . . ?
C3 C4 N1 109.0(3) . . ?
N1 C4 C5 118.5(3) . . ?
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 . . ?
N3 C6 C7 118.6(3) . . ?
N3 C6 C7A 113.5(6) . . ?
O2 C6 C7 119.9(3) . . ?
O2 C6 N3 121.3(3) . . ?
O2 C6 C7A 125.0(6) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C7 120.0 . . ?
C7 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C12 C7 C6 116.5(3) . . ?
C8 C7 C6 123.5(3) . . ?
C8 C7 C12 120.0 . . ?
O3 C13 C2 123.0(3) . . ?
O3 C13 O4 126.7(3) . . ?
O4 C13 C2 110.2(3) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
O4 C14 H14A 110.1 . . ?
O4 C14 H14B 110.1 . . ?
O4 C14 C15 108.1(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C3 122.2(3) . . ?
O5 C16 O6 124.1(3) . . ?
O6 C16 C3 113.7(2) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
O7 C18 N2 125.8(3) . . ?
O7 C18 O8 126.0(3) . . ?
O8 C18 N2 108.1(3) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
O8 C19 H19A 110.2 . . ?
O8 C19 H19B 110.2 . . ?
O8 C19 C20 107.6(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C4 113.0(2) . . ?
N2 N1 C1 122.2(3) . . ?
N2 N1 C4 123.0(3) . . ?
C18 N2 N1 118.5(3) . . ?
C18 N2 H2 118(3) . . ?
N1 N2 H2 118(3) . . ?
C2 N3 H3 118(2) . . ?
C6 N3 C2 120.7(2) . . ?
C6 N3 H3 120(2) . . ?
C13 O4 C14 116.4(3) . . ?
C16 O6 C17 115.5(3) . . ?
C18 O8 C19 116.0(3) . . ?
C12A C7A C6 117.4(8) . . ?
C12A C7A C8A 120.0 . . ?
C8A C7A C6 122.6(8) . . ?
C7A C12A H12A 120.0 . . ?
C11A C12A C7A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C9A C8A H8A 120.0 . . ?

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 O5 0.87(6) 2.04(6) 2.859(4) 156(4) 4_655

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 1.7(3) . . . . ?
C1 C2 C3 C16 -179.3(2) . . . . ?
C1 C2 C13 O3 126.3(3) . . . . ?
C1 C2 C13 O4 -53.3(3) . . . . ?
C1 C2 N3 C6 46.9(4) . . . . ?
C1 N1 N2 C18 82.7(4) . . . . ?
C2 C1 N1 C4 4.5(3) . . . . ?
C2 C1 N1 N2 169.7(3) . . . . ?
C2 C3 C4 C5 -179.1(3) . . . . ?
C2 C3 C4 N1 0.9(3) . . . . ?
C2 C3 C16 O5 -6.9(4) . . . . ?
C2 C3 C16 O6 170.9(3) . . . . ?
C2 C13 O4 C14 -178.7(3) . . . . ?
C3 C2 C13 O3 -121.8(3) . . . . ?
C3 C2 C13 O4 58.5(3) . . . . ?
C3 C2 N3 C6 -67.4(3) . . . . ?
C3 C4 N1 C1 -3.6(3) . . . . ?
C3 C4 N1 N2 -168.6(3) . . . . ?
C3 C16 O6 C17 179.7(3) . . . . ?
C4 C3 C16 O5 171.9(3) . . . . ?
C4 C3 C16 O6 -10.3(4) . . . . ?
C4 N1 N2 C18 -113.5(3) . . . . ?
C5 C4 N1 C1 176.4(3) . . . . ?
C5 C4 N1 N2 11.3(4) . . . . ?
C6 C7A C12A C11A 179.1(12) . . . . ?
C6 C7A C8A C9A -179.0(13) . . . . ?
C12 C11 C10 C9 0.0 . . . . ?
C11 C12 C7 C6 178.2(5) . . . . ?
C11 C12 C7 C8 0.0 . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C9 C8 C7 C6 -178.1(5) . . . . ?
C9 C8 C7 C12 0.0 . . . . ?
C7 C6 N3 C2 171.1(3) . . . . ?
C7 C12 C11 C10 0.0 . . . . ?
C13 C2 C3 C4 -114.7(3) . . . . ?
C13 C2 C3 C16 64.3(3) . . . . ?
C13 C2 N3 C6 166.2(3) . . . . ?
C15 C14 O4 C13 170.6(3) . . . . ?
C16 C3 C4 C5 2.0(5) . . . . ?
C16 C3 C4 N1 -178.0(3) . . . . ?
C20 C19 O8 C18 172.1(4) . . . . ?
N1 C1 C2 C3 -3.6(3) . . . . ?
N1 C1 C2 C13 115.4(3) . . . . ?
N1 C1 C2 N3 -126.0(3) . . . . ?
N2 C18 O8 C19 -175.9(3) . . . . ?
N3 C2 C3 C4 121.4(3) . . . . ?
N3 C2 C3 C16 -59.6(4) . . . . ?
N3 C2 C13 O3 5.8(4) . . . . ?
N3 C2 C13 O4 -173.8(2) . . . . ?
N3 C6 C7 C12 -163.1(3) . . . . ?
N3 C6 C7 C8 15.0(6) . . . . ?
N3 C6 C7A C12A 153.4(7) . . . . ?
N3 C6 C7A C8A -27.6(10) . . . . ?
O1 C1 C2 C3 178.9(3) . . . . ?
O1 C1 C2 C13 -62.1(4) . . . . ?
O1 C1 C2 N3 56.5(4) . . . . ?
O1 C1 N1 C4 -177.9(3) . . . . ?
O1 C1 N1 N2 -12.7(5) . . . . ?
O2 C6 C7 C12 13.6(5) . . . . ?
O2 C6 C7 C8 -168.3(4) . . . . ?
O2 C6 N3 C2 -5.5(4) . . . . ?
O2 C6 C7A C12A -21.4(12) . . . . ?
O2 C6 C7A C8A 157.6(6) . . . . ?
O3 C13 O4 C14 1.6(5) . . . . ?
O5 C16 O6 C17 -2.5(4) . . . . ?
O7 C18 N2 N1 13.1(5) . . . . ?
O7 C18 O8 C19 0.7(5) . . . . ?
O8 C18 N2 N1 -170.3(3) . . . . ?
C7A C6 N3 C2 179.5(7) . . . . ?
C7A C12A C11A C10A 0.0 . . . . ?
C12A C7A C8A C9A 0.0 . . . . ?
C12A C11A C10A C9A 0.0 . . . . ?
C11A C10A C9A C8A 0.0 . . . . ?
C10A C9A C8A C7A 0.0 . . . . ?
C8A C7A C12A C11A 0.0 . . . . ?

_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 1.278
_oxdiff_exptl_absorpt_empirical_full_min 0.888
