# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_9755
_audit_block_doi                 10.5517/ccdc.csd.cc2c632s
_database_code_depnum_ccdc_archive 'CCDC 2180604'
loop_
_audit_author_name
_audit_author_address
D-ribose
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2022-06-19
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O4, H2 O'
_chemical_formula_sum            'C21 H24 N2 O5'
_chemical_formula_weight         384.42
_chemical_absolute_configuration unk
_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      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                   6.4858(3)
_cell_length_b                   10.2602(5)
_cell_length_c                   14.1368(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.740(4)
_cell_angle_gamma                90
_cell_volume                     934.24(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4202
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      71.2580
_cell_measurement_theta_min      5.3250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5076
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.458
_diffrn_reflns_theta_min         3.148
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00   7.00   0.50    0.50    --   42.30 -82.00 120.00   80
  2  ω     39.00  67.00   0.50    0.50    --   42.30 -57.00  60.00   56
  3  ω    -33.00  14.00   0.50    0.50    --   42.30 -57.00  60.00   94
  4  ω     98.00 127.00   0.50    0.50    --   42.30  77.00  90.00   58
  5  ω     18.00  85.00   0.50    0.50    --   42.30 -82.00 120.00  134
  6  ω     80.00 131.00   0.50    0.50    --   42.30  77.00 150.00  102
  7  ω    166.00 191.00   0.50    0.50    --  101.60  38.00  60.00   50
  8  ω     78.00 104.00   0.50    0.50    --  101.60  38.00  60.00   52
  9  ω     12.00  51.00   0.50    0.50    --  101.60 -63.00  60.00   78
 10  ω     79.00 124.00   0.50    0.50    --  101.60 -50.00  90.00   90
 11  ω     20.00  71.00   0.50    0.50    --  101.60 -50.00  90.00  102
 12  ω     24.00 139.00   0.50    0.50    --  101.60 -82.00-120.00  230
 13  ω     33.00  92.00   0.50    0.50    --  101.60 -77.00  60.00  118
 14  ω     57.00 127.00   0.50    0.50    --  101.60 -63.00  60.00  140
 15  ω    153.00 190.00   0.50    0.50    --  101.60  12.00  60.00   74
 16  ω     17.00 137.00   0.50    0.50    --  101.60  12.00  60.00  240
 17  ω     61.00  86.00   0.50    0.50    --   42.30 -38.00  90.00   50
 18  ω     86.00 112.00   0.50    0.50    --   42.30  77.00-180.00   52
 19  ω     80.00 105.00   0.50    0.50    --   42.30  77.00  90.00   50
 20  ω     85.00 114.00   0.50    0.50    --   42.30  77.00  60.00   58
 21  ω    -10.00  49.00   0.50    0.50    --   42.30 -38.00  90.00  118
 22  ω     14.00  31.00   0.50    0.50    --   42.30 -82.00  30.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2202366000
_diffrn_orient_matrix_UB_12      -0.0490960000
_diffrn_orient_matrix_UB_13      -0.0349885000
_diffrn_orient_matrix_UB_21      -0.0432830000
_diffrn_orient_matrix_UB_22      0.1261434000
_diffrn_orient_matrix_UB_23      -0.0581296000
_diffrn_orient_matrix_UB_31      0.0825743000
_diffrn_orient_matrix_UB_32      -0.0651760000
_diffrn_orient_matrix_UB_33      -0.0861978000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_full    0.664
_reflns_Friedel_fraction_max     0.626
_reflns_number_gt                2825
_reflns_number_total             2956
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 969 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.0082(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.195
_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)+(0.0570P)²+1.0567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1470
_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 O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2A), C2(H2B), C3(H3A), C4(H4A), C5(H5), C7(H7), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_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 0.7323(5) 0.7223(4) 0.2915(2) 0.0306(8) Uani 1 1 d . . . . .
O2 O 0.3575(5) 0.6885(3) 0.4569(2) 0.0285(8) Uani 1 1 d . . . . .
H2 H 0.293521 0.621361 0.465364 0.043 Uiso 1 1 calc R U . . .
O3 O 0.7509(5) 0.6866(4) 0.5793(2) 0.0277(8) Uani 1 1 d . . . . .
O4 O 0.8296(5) 0.9564(3) 0.5303(2) 0.0303(8) Uani 1 1 d . . . . .
H4 H 0.934288 0.949065 0.503312 0.045 Uiso 1 1 calc R U . . .
O5 O 1.1202(5) 0.9222(4) 0.4130(3) 0.0412(10) Uani 1 1 d G . . . .
H5A H 1.194282 0.989626 0.408126 0.062 Uiso 1 1 d G U . . .
H5B H 1.198253 0.855568 0.421536 0.062 Uiso 1 1 d G U . . .
N1 N 0.8535(6) 0.3074(4) 0.3124(3) 0.0293(9) Uani 1 1 d . . . . .
H1A H 0.975631 0.280311 0.333765 0.035 Uiso 1 1 calc R U . . .
N2 N 0.4276(6) 0.6404(5) -0.0013(3) 0.0338(10) Uani 1 1 d . . . . .
H2A H 0.470486 0.634298 -0.056379 0.041 Uiso 1 1 calc R U . . .
C1 C 0.5190(7) 0.3137(5) 0.2491(3) 0.0228(10) Uani 1 1 d . . . . .
C2 C 0.3316(8) 0.2591(5) 0.2085(3) 0.0275(10) Uani 1 1 d . . . . .
H2B H 0.218037 0.311977 0.189089 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3176(9) 0.1253(5) 0.1975(4) 0.0333(12) Uani 1 1 d . . . . .
H3A H 0.193305 0.088275 0.170735 0.040 Uiso 1 1 calc R U . . .
C4 C 0.4883(9) 0.0446(5) 0.2261(3) 0.0361(13) Uani 1 1 d . . . . .
H4A H 0.474869 -0.045117 0.218100 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6746(9) 0.0953(5) 0.2655(3) 0.0345(12) Uani 1 1 d . . . . .
H5 H 0.787466 0.041379 0.284072 0.041 Uiso 1 1 calc R U . . .
C6 C 0.6894(7) 0.2296(5) 0.2770(3) 0.0268(10) Uani 1 1 d . . . . .
C7 C 0.7903(7) 0.4356(5) 0.3080(3) 0.0274(10) Uani 1 1 d . . . . .
H7 H 0.874715 0.506067 0.327939 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5866(7) 0.4455(5) 0.2705(3) 0.0232(10) Uani 1 1 d . . . . .
C9 C 0.4503(7) 0.5649(5) 0.2571(3) 0.0230(10) Uani 1 1 d . . . . .
H9 H 0.317087 0.541730 0.278954 0.028 Uiso 1 1 calc R U . . .
C10 C 0.5344(6) 0.6823(5) 0.3165(3) 0.0223(9) Uani 1 1 d . . . . .
H10 H 0.437326 0.754738 0.302294 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5517(7) 0.6564(5) 0.4245(3) 0.0235(10) Uani 1 1 d . . . . .
H11 H 0.578959 0.563403 0.435814 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7200(7) 0.7345(4) 0.4828(3) 0.0208(9) Uani 1 1 d . . . . .
H12 H 0.849848 0.723361 0.454548 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6672(7) 0.8789(5) 0.4822(3) 0.0275(11) Uani 1 1 d . . . . .
H13A H 0.639083 0.908442 0.416780 0.033 Uiso 1 1 calc R U . . .
H13B H 0.541969 0.891441 0.512475 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4040(7) 0.6069(5) 0.1545(3) 0.0246(10) Uani 1 1 d . . . . .
C15 C 0.5104(8) 0.5755(5) 0.0793(3) 0.0319(11) Uani 1 1 d . . . . .
H15 H 0.622404 0.518447 0.082454 0.038 Uiso 1 1 calc R U . . .
C16 C 0.2653(7) 0.7168(5) 0.0202(3) 0.0261(10) Uani 1 1 d . . . . .
C17 C 0.2463(6) 0.6988(5) 0.1180(3) 0.0226(9) Uani 1 1 d . . . . .
C18 C 0.0917(7) 0.7678(5) 0.1583(3) 0.0264(10) Uani 1 1 d . . . . .
H18 H 0.075831 0.757703 0.222442 0.032 Uiso 1 1 calc R U . . .
C19 C -0.0362(8) 0.8507(6) 0.1020(4) 0.0327(11) Uani 1 1 d . . . . .
H19 H -0.139377 0.896229 0.128427 0.039 Uiso 1 1 calc R U . . .
C20 C -0.0134(8) 0.8678(6) 0.0049(4) 0.0333(11) Uani 1 1 d . . . . .
H20 H -0.100719 0.925236 -0.031557 0.040 Uiso 1 1 calc R U . . .
C21 C 0.1359(8) 0.8008(6) -0.0368(3) 0.0327(11) Uani 1 1 d . . . . .
H21 H 0.150041 0.811335 -0.101077 0.039 Uiso 1 1 calc R U . . .
H3 H 0.633(8) 0.692(5) 0.606(3) 0.021(12) Uiso 1 1 d . . . . .
H1 H 0.724(10) 0.721(8) 0.237(5) 0.06(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.431(5) . ?
O1 H1 0.77(7) . ?
O2 H2 0.8200 . ?
O2 C11 1.429(5) . ?
O3 C12 1.442(5) . ?
O3 H3 0.89(5) . ?
O4 H4 0.8200 . ?
O4 C13 1.426(6) . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8505 . ?
N1 H1A 0.8600 . ?
N1 C6 1.377(6) . ?
N1 C7 1.378(6) . ?
N2 H2A 0.8600 . ?
N2 C15 1.373(6) . ?
N2 C16 1.374(6) . ?
C1 C2 1.399(7) . ?
C1 C6 1.421(7) . ?
C1 C8 1.443(7) . ?
C2 H2B 0.9300 . ?
C2 C3 1.383(7) . ?
C3 H3A 0.9300 . ?
C3 C4 1.403(8) . ?
C4 H4A 0.9300 . ?
C4 C5 1.373(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(6) . ?
C8 C9 1.509(7) . ?
C9 H9 0.9800 . ?
C9 C10 1.532(6) . ?
C9 C14 1.510(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.540(6) . ?
C11 H11 0.9800 . ?
C11 C12 1.517(6) . ?
C12 H12 0.9800 . ?
C12 C13 1.521(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.372(7) . ?
C14 C17 1.441(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.414(6) . ?
C16 C21 1.392(7) . ?
C17 C18 1.402(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.408(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(8) . ?
C21 H21 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
C10 O1 H1 107(5) . . ?
C11 O2 H2 109.5 . . ?
C12 O3 H3 111(3) . . ?
C13 O4 H4 109.5 . . ?
H5A O5 H5B 109.5 . . ?
C6 N1 H1A 125.5 . . ?
C6 N1 C7 108.9(4) . . ?
C7 N1 H1A 125.5 . . ?
C15 N2 H2A 125.4 . . ?
C15 N2 C16 109.2(4) . . ?
C16 N2 H2A 125.4 . . ?
C2 C1 C6 118.7(4) . . ?
C2 C1 C8 133.6(4) . . ?
C6 C1 C8 107.7(4) . . ?
C1 C2 H2B 120.5 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2B 120.5 . . ?
C2 C3 H3A 119.5 . . ?
C2 C3 C4 120.9(5) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 C3 121.4(5) . . ?
C5 C4 H4A 119.3 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 117.9(5) . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C1 107.0(4) . . ?
N1 C6 C5 131.1(5) . . ?
C5 C6 C1 121.9(5) . . ?
N1 C7 H7 124.5 . . ?
C8 C7 N1 110.9(4) . . ?
C8 C7 H7 124.5 . . ?
C1 C8 C9 125.1(4) . . ?
C7 C8 C1 105.5(4) . . ?
C7 C8 C9 129.3(4) . . ?
C8 C9 H9 106.8 . . ?
C8 C9 C10 113.8(4) . . ?
C8 C9 C14 113.5(4) . . ?
C10 C9 H9 106.8 . . ?
C14 C9 H9 106.8 . . ?
C14 C9 C10 108.7(4) . . ?
O1 C10 C9 111.2(4) . . ?
O1 C10 H10 107.7 . . ?
O1 C10 C11 109.4(3) . . ?
C9 C10 H10 107.7 . . ?
C9 C10 C11 112.8(4) . . ?
C11 C10 H10 107.7 . . ?
O2 C11 C10 108.3(3) . . ?
O2 C11 H11 108.7 . . ?
O2 C11 C12 108.0(3) . . ?
C10 C11 H11 108.7 . . ?
C12 C11 C10 114.3(4) . . ?
C12 C11 H11 108.7 . . ?
O3 C12 C11 110.2(4) . . ?
O3 C12 H12 108.4 . . ?
O3 C12 C13 110.1(4) . . ?
C11 C12 H12 108.4 . . ?
C11 C12 C13 111.4(4) . . ?
C13 C12 H12 108.4 . . ?
O4 C13 C12 112.8(4) . . ?
O4 C13 H13A 109.0 . . ?
O4 C13 H13B 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C9 128.0(4) . . ?
C15 C14 C17 106.1(4) . . ?
C17 C14 C9 125.7(4) . . ?
N2 C15 H15 124.9 . . ?
C14 C15 N2 110.2(4) . . ?
C14 C15 H15 124.9 . . ?
N2 C16 C17 107.3(4) . . ?
N2 C16 C21 130.6(4) . . ?
C21 C16 C17 122.1(4) . . ?
C16 C17 C14 107.2(4) . . ?
C18 C17 C14 134.1(4) . . ?
C18 C17 C16 118.7(4) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.2(4) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.1(5) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 H21 121.0 . . ?
C20 C21 C16 117.9(5) . . ?
C20 C21 H21 121.0 . . ?

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
O1 C10 C11 O2 148.0(4) . . . . ?
O1 C10 C11 C12 27.5(5) . . . . ?
O2 C11 C12 O3 70.2(4) . . . . ?
O2 C11 C12 C13 -52.3(5) . . . . ?
O3 C12 C13 O4 62.0(5) . . . . ?
N1 C7 C8 C1 -0.6(5) . . . . ?
N1 C7 C8 C9 176.5(4) . . . . ?
N2 C16 C17 C14 -0.5(5) . . . . ?
N2 C16 C17 C18 179.3(4) . . . . ?
N2 C16 C21 C20 -178.7(5) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C1 C8 C9 C10 159.2(4) . . . . ?
C1 C8 C9 C14 -75.8(6) . . . . ?
C2 C1 C6 N1 178.7(4) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
C2 C1 C8 C7 -178.5(5) . . . . ?
C2 C1 C8 C9 4.2(8) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C4 C5 C6 N1 -178.9(4) . . . . ?
C4 C5 C6 C1 0.0(7) . . . . ?
C6 N1 C7 C8 0.1(6) . . . . ?
C6 C1 C2 C3 0.6(7) . . . . ?
C6 C1 C8 C7 0.8(5) . . . . ?
C6 C1 C8 C9 -176.5(4) . . . . ?
C7 N1 C6 C1 0.4(5) . . . . ?
C7 N1 C6 C5 179.5(5) . . . . ?
C7 C8 C9 C10 -17.4(7) . . . . ?
C7 C8 C9 C14 107.7(5) . . . . ?
C8 C1 C2 C3 179.8(5) . . . . ?
C8 C1 C6 N1 -0.7(5) . . . . ?
C8 C1 C6 C5 -179.9(4) . . . . ?
C8 C9 C10 O1 61.1(5) . . . . ?
C8 C9 C10 C11 -62.2(5) . . . . ?
C8 C9 C14 C15 -19.6(7) . . . . ?
C8 C9 C14 C17 166.2(4) . . . . ?
C9 C10 C11 O2 -87.7(5) . . . . ?
C9 C10 C11 C12 151.9(4) . . . . ?
C9 C14 C15 N2 -175.8(5) . . . . ?
C9 C14 C17 C16 176.0(4) . . . . ?
C9 C14 C17 C18 -3.7(9) . . . . ?
C10 C9 C14 C15 108.2(6) . . . . ?
C10 C9 C14 C17 -66.0(6) . . . . ?
C10 C11 C12 O3 -169.2(4) . . . . ?
C10 C11 C12 C13 68.3(5) . . . . ?
C11 C12 C13 O4 -175.5(4) . . . . ?
C14 C9 C10 O1 -66.5(5) . . . . ?
C14 C9 C10 C11 170.2(4) . . . . ?
C14 C17 C18 C19 179.6(5) . . . . ?
C15 N2 C16 C17 0.0(6) . . . . ?
C15 N2 C16 C21 179.1(5) . . . . ?
C15 C14 C17 C16 0.7(5) . . . . ?
C15 C14 C17 C18 -179.0(5) . . . . ?
C16 N2 C15 C14 0.4(6) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C17 C14 C15 N2 -0.7(6) . . . . ?
C17 C16 C21 C20 0.2(7) . . . . ?
C17 C18 C19 C20 -0.4(8) . . . . ?
C18 C19 C20 C21 0.8(8) . . . . ?
C19 C20 C21 C16 -0.7(8) . . . . ?
C21 C16 C17 C14 -179.6(5) . . . . ?
C21 C16 C17 C18 0.1(7) . . . . ?

_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 2.623
_oxdiff_exptl_absorpt_empirical_full_min 0.481
