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

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

data_p20190605b
_database_code_depnum_ccdc_archive 'CCDC 1922302'
loop_
_audit_author_name
_audit_author_address
'dimethylcyclopentyl pyridine'
;The cambrige crystallographic Data centure
China
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;
_audit_creation_date             2019-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3 N2 O6, C7 H4 N2 O6, C12 H18 N'
_chemical_formula_sum            'C26 H25 N5 O12'
_chemical_formula_weight         599.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H21N3O6
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                   10.03310(10)
_cell_length_b                   11.89880(10)
_cell_length_c                   13.4124(2)
_cell_angle_alpha                108.0000(10)
_cell_angle_beta                 99.4130(10)
_cell_angle_gamma                106.6790(10)
_cell_volume                     1401.73(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19514
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      79.0890
_cell_measurement_theta_min      4.1980
_shelx_estimated_absorpt_T_max   0.843
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34190
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.542
_diffrn_reflns_theta_min         3.606
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  94.00   0.50    0.50    --    5.00  57.00-120.00  236
  2  ω    -84.00  39.00   0.50    0.50    --  -50.10  72.00  30.00  246
  3  ω    -82.00  39.00   0.50    0.50    --  -50.10  38.00-120.00  242
  4  ω   -140.00 -21.00   0.50    0.50    --  -50.10 -52.00  51.64  238
  5  ω   -140.00 -17.00   0.50    0.50    --  -50.10 -72.00 120.00  246
  6  ω   -140.00 -17.00   0.50    0.50    --  -50.10 -33.00 -50.17  246
  7  ω   -199.00 -81.00   0.50    0.50    -- -110.00 -57.00 -90.00  236
  8  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00  60.00  244
  9  ω   -161.00 -21.00   0.50    0.50    -- -110.00  19.00  60.00  280
 10  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -60.00  244
 11  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00  90.00  244
 12  ω   -199.00 -80.00   0.50    0.50    -- -110.00 -64.00  64.12  238
 13  ω   -139.00 -21.00   0.50    0.50    -- -110.00  57.00 120.00  236
 14  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00-150.00  244
 15  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00-180.00  244
 16  ω   -199.00 -59.00   0.50    0.50    -- -110.00 -19.00 -30.00  280
 17  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -90.00  244
 18  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00   0.00  244
 19  ω   -139.00 -21.00   0.50    0.50    -- -110.00  57.00-180.00  236
 20  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -30.00  244
 21  ω   -199.00 -81.00   0.50    0.50    -- -110.00 -46.00-113.60  236
 22  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 120.00  244
 23  ω   -199.00 -79.00   0.50    0.50    -- -110.00 -67.00 152.66  240
 24  ω   -140.00 -20.00   0.50    0.50    --  -50.10 -63.00 147.48  240
 25  ω    -80.00  39.00   0.50    0.50    --  -50.10  57.00 -30.00  238
 26  ω   -140.00 -21.00   0.50    0.50    --  -50.10 -57.00-150.00  238
 27  ω   -140.00 -21.00   0.50    0.50    --  -50.10 -60.00 -74.49  238
 28  ω   -199.00 -79.00   0.50    0.50    -- -110.00 -38.00-180.00  240
 29  ω   -199.00-146.00   0.50    0.50    -- -110.00 -38.00 -60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0428342000
_diffrn_orient_matrix_UB_12      0.0385680000
_diffrn_orient_matrix_UB_13      -0.0931590000
_diffrn_orient_matrix_UB_21      0.0740172000
_diffrn_orient_matrix_UB_22      0.1389523000
_diffrn_orient_matrix_UB_23      0.0798995000
_diffrn_orient_matrix_UB_31      0.1432261000
_diffrn_orient_matrix_UB_32      -0.0222050000
_diffrn_orient_matrix_UB_33      0.0271012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5241
_reflns_number_total             5893
_reflns_odcompleteness_completeness 97.93
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0052(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5893
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.093
_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)+(0.0970P)²+0.2560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.1816
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C17(H17), C19(H19), C22(H22),
 C24(H24), C26(H26)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7A)
;
_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 0.30768(15) 0.31261(14) 0.36741(11) 0.0756(4) Uani 1 1 d . . . . .
O2 O 0.34737(14) 0.43911(12) 0.53986(11) 0.0687(3) Uani 1 1 d . . . . .
O3 O 0.6658(3) 0.3891(2) 0.82849(14) 0.1172(7) Uani 1 1 d . . . . .
O4 O 0.7501(3) 0.2435(3) 0.79015(18) 0.1539(11) Uani 1 1 d . . . . .
O5 O 0.68938(18) -0.00687(15) 0.41849(17) 0.0978(5) Uani 1 1 d . . . . .
O6 O 0.5520(3) 0.0105(3) 0.29198(18) 0.1405(9) Uani 1 1 d . . . . .
O7 O 0.18918(13) 0.55116(12) 0.48826(10) 0.0634(3) Uani 1 1 d . . . . .
H7A H 0.238950 0.515010 0.509980 0.095 Uiso 1 1 calc GR . . . .
O8 O 0.19672(19) 0.63298(17) 0.66343(12) 0.0909(5) Uani 1 1 d . . . . .
O9 O -0.0058(2) 0.9659(2) 0.77162(13) 0.1105(6) Uani 1 1 d . . . . .
O10 O -0.1238(2) 1.01249(16) 0.65181(14) 0.0958(5) Uani 1 1 d . . . . .
O11 O -0.2062(2) 0.7727(2) 0.26972(14) 0.1144(7) Uani 1 1 d . . . . .
O12 O -0.0915(2) 0.64873(18) 0.22309(12) 0.1023(6) Uani 1 1 d . . . . .
N1 N 0.17638(17) 0.33487(14) 0.19138(11) 0.0602(3) Uani 1 1 d . . . . .
N2 N 0.6812(2) 0.30231(19) 0.76347(15) 0.0834(5) Uani 1 1 d . . . . .
N3 N 0.60945(19) 0.04042(16) 0.38571(17) 0.0754(5) Uani 1 1 d . . . . .
N4 N -0.05371(19) 0.95291(15) 0.67827(14) 0.0727(4) Uani 1 1 d . . . . .
N5 N -0.1250(2) 0.72070(17) 0.29126(13) 0.0742(4) Uani 1 1 d . . . . .
C1 C 0.2047(2) 0.29429(18) 0.09525(13) 0.0660(4) Uani 1 1 d . . . . .
C2 C 0.1170(3) 0.2986(3) 0.00737(16) 0.0893(7) Uani 1 1 d . . . . .
H2 H 0.132756 0.271490 -0.061046 0.107 Uiso 1 1 calc R . . . .
C3 C 0.0064(3) 0.3429(3) 0.02022(19) 0.0981(8) Uani 1 1 d . . . . .
H3 H -0.052021 0.346133 -0.039493 0.118 Uiso 1 1 calc R . . . .
C4 C -0.0190(3) 0.3825(2) 0.1210(2) 0.0877(6) Uani 1 1 d . . . . .
H4 H -0.094842 0.411284 0.129865 0.105 Uiso 1 1 calc R . . . .
C5 C 0.0694(2) 0.37858(19) 0.20660(17) 0.0730(5) Uani 1 1 d . . . . .
H5 H 0.055758 0.406117 0.275732 0.088 Uiso 1 1 calc R . . . .
C6 C 0.3249(2) 0.2431(2) 0.08894(16) 0.0792(6) Uani 1 1 d . . . . .
H6 H 0.372410 0.254481 0.163128 0.095 Uiso 1 1 calc R . . . .
C7 C 0.4415(3) 0.3094(3) 0.0432(2) 0.0965(7) Uani 1 1 d . . . . .
H7 H 0.393304 0.328537 -0.015718 0.116 Uiso 1 1 calc R . . . .
C8 C 0.4935(5) 0.2013(4) -0.0078(4) 0.1577(16) Uani 1 1 d . . . . .
H8A H 0.535407 0.214267 -0.065488 0.189 Uiso 1 1 calc R . . . .
H8B H 0.565966 0.196801 0.046804 0.189 Uiso 1 1 calc R . . . .
C9 C 0.3682(7) 0.0877(4) -0.0509(5) 0.186(2) Uani 1 1 d . . . . .
H9A H 0.396517 0.015984 -0.052202 0.223 Uiso 1 1 calc R . . . .
H9B H 0.319749 0.073102 -0.125007 0.223 Uiso 1 1 calc R . . . .
C10 C 0.2696(4) 0.1010(3) 0.0185(3) 0.1068(8) Uani 1 1 d . . . . .
H10 H 0.173532 0.079239 -0.029389 0.128 Uiso 1 1 calc R . . . .
C11 C 0.5580(4) 0.4268(4) 0.1207(4) 0.1497(14) Uani 1 1 d . . . . .
H11A H 0.520590 0.494068 0.139061 0.225 Uiso 1 1 calc GR . . . .
H11B H 0.634833 0.448724 0.087985 0.225 Uiso 1 1 calc GR . . . .
H11C H 0.594428 0.414347 0.185660 0.225 Uiso 1 1 calc GR . . . .
C12 C 0.2553(8) 0.0179(5) 0.0783(5) 0.215(3) Uani 1 1 d . . . . .
H12A H 0.348948 0.033218 0.122657 0.322 Uiso 1 1 calc GR . . . .
H12B H 0.214164 -0.068643 0.027919 0.322 Uiso 1 1 calc GR . . . .
H12C H 0.193213 0.033772 0.124103 0.322 Uiso 1 1 calc GR . . . .
C13 C 0.36472(16) 0.35328(15) 0.46668(13) 0.0543(4) Uani 1 1 d . . . . .
C14 C 0.46231(15) 0.29042(14) 0.50513(12) 0.0499(3) Uani 1 1 d . . . . .
C15 C 0.52549(17) 0.32582(15) 0.61517(13) 0.0546(4) Uani 1 1 d . . . . .
H15 H 0.508595 0.388956 0.666972 0.066 Uiso 1 1 calc R . . . .
C16 C 0.61415(17) 0.26576(16) 0.64684(14) 0.0589(4) Uani 1 1 d . . . . .
C17 C 0.64322(17) 0.17185(16) 0.57373(15) 0.0597(4) Uani 1 1 d . . . . .
H17 H 0.703149 0.132503 0.596598 0.072 Uiso 1 1 calc R . . . .
C18 C 0.57915(17) 0.13966(15) 0.46571(15) 0.0564(4) Uani 1 1 d . . . . .
C19 C 0.48901(17) 0.19575(15) 0.42943(13) 0.0541(4) Uani 1 1 d . . . . .
H19 H 0.446676 0.170462 0.355223 0.065 Uiso 1 1 calc R . . . .
C20 C 0.16224(18) 0.62464(16) 0.57080(15) 0.0596(4) Uani 1 1 d . . . . .
C21 C 0.07660(16) 0.69983(14) 0.53927(13) 0.0527(3) Uani 1 1 d . . . . .
C22 C 0.05374(17) 0.79144(15) 0.62058(14) 0.0553(4) Uani 1 1 d . . . . .
H22 H 0.093095 0.808084 0.693677 0.066 Uiso 1 1 calc R . . . .
C23 C -0.02802(17) 0.85743(15) 0.59162(14) 0.0553(4) Uani 1 1 d . . . . .
C24 C -0.08849(17) 0.83726(15) 0.48524(14) 0.0567(4) Uani 1 1 d . . . . .
H24 H -0.143838 0.882528 0.467242 0.068 Uiso 1 1 calc R . . . .
C25 C -0.06262(17) 0.74614(15) 0.40651(13) 0.0552(4) Uani 1 1 d . . . . .
C26 C 0.01852(17) 0.67751(14) 0.43089(13) 0.0543(4) Uani 1 1 d . . . . .
H26 H 0.034078 0.617139 0.375485 0.065 Uiso 1 1 calc R . . . .
H1 H 0.230(3) 0.331(2) 0.251(2) 0.085(7) 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 C13 1.236(2) . ?
O2 C13 1.255(2) . ?
O3 N2 1.196(3) . ?
O4 N2 1.203(3) . ?
O5 N3 1.204(2) . ?
O6 N3 1.186(3) . ?
O7 H7A 0.8200 . ?
O7 C20 1.303(2) . ?
O8 C20 1.199(2) . ?
O9 N4 1.210(2) . ?
O10 N4 1.218(2) . ?
O11 N5 1.206(2) . ?
O12 N5 1.210(2) . ?
N1 C1 1.338(2) . ?
N1 C5 1.339(2) . ?
N1 H1 0.91(3) . ?
N2 C16 1.468(2) . ?
N3 C18 1.472(2) . ?
N4 C23 1.469(2) . ?
N5 C25 1.469(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.501(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.353(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9800 . ?
C6 C7 1.540(3) . ?
C6 C10 1.537(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(4) . ?
C7 C11 1.472(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.430(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.474(5) . ?
C10 H10 0.9800 . ?
C10 C12 1.446(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.509(2) . ?
C14 C15 1.384(2) . ?
C14 C19 1.388(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(2) . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.367(3) . ?
C18 C19 1.380(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.508(2) . ?
C21 C22 1.386(2) . ?
C21 C26 1.385(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(2) . ?
C23 C24 1.372(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.379(2) . ?
C25 C26 1.377(2) . ?
C26 H26 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
C20 O7 H7A 109.5 . . ?
C1 N1 C5 124.30(16) . . ?
C1 N1 H1 119.7(15) . . ?
C5 N1 H1 116.0(15) . . ?
O3 N2 O4 122.3(2) . . ?
O3 N2 C16 119.17(18) . . ?
O4 N2 C16 118.5(2) . . ?
O5 N3 C18 118.7(2) . . ?
O6 N3 O5 123.5(2) . . ?
O6 N3 C18 117.80(18) . . ?
O9 N4 O10 124.07(17) . . ?
O9 N4 C23 117.75(16) . . ?
O10 N4 C23 118.17(17) . . ?
O11 N5 O12 123.58(18) . . ?
O11 N5 C25 118.39(17) . . ?
O12 N5 C25 118.02(16) . . ?
N1 C1 C2 116.88(18) . . ?
N1 C1 C6 118.74(16) . . ?
C2 C1 C6 124.35(17) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.26(19) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 119.71(19) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 H6 107.7 . . ?
C1 C6 C7 114.43(19) . . ?
C1 C6 C10 112.6(2) . . ?
C7 C6 H6 107.7 . . ?
C10 C6 H6 107.7 . . ?
C10 C6 C7 106.6(2) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 C6 100.7(2) . . ?
C8 C7 H7 108.2 . . ?
C11 C7 C6 117.0(3) . . ?
C11 C7 H7 108.2 . . ?
C11 C7 C8 114.2(3) . . ?
C7 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 C7 106.1(3) . . ?
C9 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C8 C9 C10 108.8(3) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C6 C10 H10 107.5 . . ?
C9 C10 C6 105.1(3) . . ?
C9 C10 H10 107.5 . . ?
C12 C10 C6 115.3(3) . . ?
C12 C10 C9 113.7(3) . . ?
C12 C10 H10 107.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 O2 127.15(15) . . ?
O1 C13 C14 116.79(15) . . ?
O2 C13 C14 116.02(14) . . ?
C15 C14 C13 120.78(14) . . ?
C15 C14 C19 119.45(14) . . ?
C19 C14 C13 119.77(14) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.89(15) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 N2 119.31(17) . . ?
C17 C16 N2 117.64(16) . . ?
C17 C16 C15 123.05(16) . . ?
C16 C17 H17 121.8 . . ?
C18 C17 C16 116.37(15) . . ?
C18 C17 H17 121.8 . . ?
C17 C18 N3 117.53(16) . . ?
C17 C18 C19 123.09(15) . . ?
C19 C18 N3 119.38(17) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 C14 119.15(15) . . ?
C18 C19 H19 120.4 . . ?
O7 C20 C21 113.27(15) . . ?
O8 C20 O7 125.74(16) . . ?
O8 C20 C21 120.97(16) . . ?
C22 C21 C20 119.12(15) . . ?
C26 C21 C20 121.28(14) . . ?
C26 C21 C22 119.59(14) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.07(15) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 N4 118.72(16) . . ?
C24 C23 N4 118.19(15) . . ?
C24 C23 C22 123.08(15) . . ?
C23 C24 H24 121.9 . . ?
C23 C24 C25 116.28(15) . . ?
C25 C24 H24 121.9 . . ?
C24 C25 N5 118.51(15) . . ?
C26 C25 N5 118.45(15) . . ?
C26 C25 C24 123.04(16) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 C21 118.93(15) . . ?
C25 C26 H26 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C15 -177.03(15) . . . . ?
O1 C13 C14 C19 2.8(2) . . . . ?
O2 C13 C14 C15 1.0(2) . . . . ?
O2 C13 C14 C19 -179.10(14) . . . . ?
O3 N2 C16 C15 -5.0(3) . . . . ?
O3 N2 C16 C17 175.1(2) . . . . ?
O4 N2 C16 C15 175.0(2) . . . . ?
O4 N2 C16 C17 -4.9(3) . . . . ?
O5 N3 C18 C17 -0.6(3) . . . . ?
O5 N3 C18 C19 179.32(16) . . . . ?
O6 N3 C18 C17 178.6(2) . . . . ?
O6 N3 C18 C19 -1.5(3) . . . . ?
O7 C20 C21 C22 -173.23(14) . . . . ?
O7 C20 C21 C26 7.9(2) . . . . ?
O8 C20 C21 C22 8.3(3) . . . . ?
O8 C20 C21 C26 -170.58(17) . . . . ?
O9 N4 C23 C22 -2.6(3) . . . . ?
O9 N4 C23 C24 176.59(19) . . . . ?
O10 N4 C23 C22 178.57(17) . . . . ?
O10 N4 C23 C24 -2.2(3) . . . . ?
O11 N5 C25 C24 -6.1(3) . . . . ?
O11 N5 C25 C26 173.65(19) . . . . ?
O12 N5 C25 C24 173.71(18) . . . . ?
O12 N5 C25 C26 -6.5(3) . . . . ?
N1 C1 C2 C3 -0.1(4) . . . . ?
N1 C1 C6 C7 -124.4(2) . . . . ?
N1 C1 C6 C10 113.8(2) . . . . ?
N2 C16 C17 C18 179.92(15) . . . . ?
N3 C18 C19 C14 -179.16(14) . . . . ?
N4 C23 C24 C25 -179.50(14) . . . . ?
N5 C25 C26 C21 -179.35(14) . . . . ?
C1 N1 C5 C4 0.5(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C6 C7 C8 -151.4(3) . . . . ?
C1 C6 C7 C11 84.2(3) . . . . ?
C1 C6 C10 C9 134.9(3) . . . . ?
C1 C6 C10 C12 -99.1(4) . . . . ?
C2 C1 C6 C7 58.0(3) . . . . ?
C2 C1 C6 C10 -63.9(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 N1 -1.1(4) . . . . ?
C5 N1 C1 C2 0.1(3) . . . . ?
C5 N1 C1 C6 -177.76(19) . . . . ?
C6 C1 C2 C3 177.6(2) . . . . ?
C6 C7 C8 C9 35.7(5) . . . . ?
C7 C6 C10 C9 8.7(4) . . . . ?
C7 C6 C10 C12 134.6(4) . . . . ?
C7 C8 C9 C10 -32.4(6) . . . . ?
C8 C9 C10 C6 14.5(5) . . . . ?
C8 C9 C10 C12 -112.4(5) . . . . ?
C10 C6 C7 C8 -26.3(3) . . . . ?
C10 C6 C7 C11 -150.7(3) . . . . ?
C11 C7 C8 C9 161.9(4) . . . . ?
C13 C14 C15 C16 179.99(14) . . . . ?
C13 C14 C19 C18 179.61(13) . . . . ?
C14 C15 C16 N2 -179.76(15) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C14 C19 C18 -0.5(2) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 N3 179.43(14) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?
C17 C18 C19 C14 0.7(2) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
C20 C21 C22 C23 -178.12(14) . . . . ?
C20 C21 C26 C25 177.99(14) . . . . ?
C21 C22 C23 N4 179.02(14) . . . . ?
C21 C22 C23 C24 -0.2(2) . . . . ?
C22 C21 C26 C25 -0.9(2) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C23 C24 C25 N5 179.95(14) . . . . ?
C23 C24 C25 C26 0.2(2) . . . . ?
C24 C25 C26 C21 0.4(2) . . . . ?
C26 C21 C22 C23 0.8(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 3.109
_oxdiff_exptl_absorpt_empirical_full_min 0.648
