# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_7060-11161_lia501
_audit_block_doi                 10.5517/ccdc.csd.cc26yb8s
_database_code_depnum_ccdc_archive 'CCDC 2053975'
loop_
_audit_author_name
_audit_author_address
'Anastasiya Agafonova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2021-01-05 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_audit_creation_date             2020-12-23
_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        
'methyl 5-amino-4-cyano-3-phenyl-1H-pyrrole-2-carboxylate'
_chemical_formula_moiety         'C13 H11 N3 O2'
_chemical_formula_sum            'C13 H11 N3 O2'
_chemical_formula_weight         241.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H11 N5 O3'
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                   7.2529(3)
_cell_length_b                   12.9297(5)
_cell_length_c                   13.0243(5)
_cell_angle_alpha                85.469(3)
_cell_angle_beta                 82.621(3)
_cell_angle_gamma                73.765(3)
_cell_volume                     1161.78(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9216
_cell_measurement_temperature    99.99(13)
_cell_measurement_theta_max      75.9070
_cell_measurement_theta_min      3.5340
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16032
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        62.490
_diffrn_reflns_theta_max         62.490
_diffrn_reflns_theta_min         3.425
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00 105.00   1.00    3.50    --   40.38  38.00  60.00   88
  2  ω     82.00 176.00   1.00    8.00    --  113.00  30.00   0.00   94
  3  ω    125.00 176.00   1.00    8.00    --  113.00  77.00 -60.00   51
  4  ω    151.00 177.00   1.00    8.00    --  113.00  15.00-120.00   26
  5  ω    119.00 176.00   1.00    8.00    --  113.00 112.00-120.00   57
  6  ω    107.00 177.00   1.00    8.00    --  113.00  61.00 -90.00   70
  7  ω     97.00 128.00   1.00    3.50    --   40.38 178.00-120.00   31
  8  ω     83.00 110.00   1.00    3.50    --   40.38 178.00-180.00   27
  9  ω     85.00 165.00   1.00    8.00    --  113.00  61.00  30.00   80
 10  ω    103.00 139.00   1.00    8.00    --  113.00 -61.00 -60.00   36
 11  ω     83.00 109.00   1.00    8.00    --  113.00 -95.00-120.00   26
 12  ω     49.00 110.00   1.00    8.00    --  113.00-112.00-180.00   61
 13  ω     39.00 131.00   1.00    8.00    --  113.00 -45.00-180.00   92
 14  ω     75.00 115.00   1.00    8.00    --  113.00-112.00   0.00   40
 15  ω     82.00 108.00   1.00    8.00    --  113.00 -95.00   0.00   26
 16  ω     42.00 100.00   1.00    8.00    --  113.00 -61.00 -60.00   58
 17  ω     32.00 106.00   1.00    8.00    --  113.00 -95.00-150.00   74
 18  ω     35.00 113.00   1.00    8.00    --  113.00-112.00 120.00   78
 19  ω   -103.00 -15.00   1.00    3.50    --  -40.38 -38.00-180.00   88
 20  ω   -126.00 -48.00   1.00    3.50    --  -40.38-178.00-150.00   78
 21  ω   -109.00 -14.00   1.00    3.50    --  -40.38 -38.00  90.00   95
 22  ω     83.00 110.00   1.00    8.00    --  113.00  65.00  -2.00   27
 23  ω    -67.00  -5.00   1.00    3.50    --  -40.38  38.00 -60.00   62
 24  ω    -91.00 -41.00   1.00    3.50    --  -40.38 -57.00 -30.00   50
 25  ω    -69.00  31.00   1.00    3.50    --  -40.38  57.00 150.00  100
 26  ω    -39.00 -11.00   1.00    3.50    --  -40.38 -57.00 -30.00   28
 27  ω      7.00  32.00   1.00    3.50    --   44.00  88.00-118.93   25
 28  ω     12.00  37.00   1.00    3.50    --   48.00  84.00  93.74   25
 29  ω     12.00  37.00   1.00    3.50    --   48.00  84.00  37.94   25
 30  ω     22.00  48.00   1.00    3.50    --   56.00  77.00 163.53   26
 31  ω     25.00  54.00   1.00    3.50    --   56.00  76.00 -28.69   29
 32  ω     28.00  54.00   1.00    3.50    --   60.00  76.00 122.98   26
 33  ω     31.00  59.00   1.00    3.50    --   64.00  76.00 -78.47   28
 34  ω     35.00  61.00   1.00    3.50    --   68.00  77.00  67.47   26
 35  ω     35.00  60.00   1.00    3.50    --   68.00  75.00  12.15   25
 36  ω     38.00  74.00   1.00    3.50    --   68.00  74.00-138.51   36
 37  ω    102.00 128.00   1.00    3.50    --   72.00  76.00 160.63   26
 38  ω     39.00  65.00   1.00    3.50    --   72.00  76.00 160.63   26
 39  ω    101.00 127.00   1.00    3.50    --   76.00  70.00-174.26   26
 40  ω     44.00  70.00   1.00    3.50    --   76.00  70.00-174.26   26
 41  ω     52.00  78.00   1.00    8.00    --   84.00  69.00 -44.85   26
 42  ω    126.00 152.00   1.00    8.00    --   84.00  75.00   4.10   26
 43  ω     52.00  78.00   1.00    8.00    --   84.00  75.00   4.10   26
 44  ω     56.00  82.00   1.00    8.00    --   88.00  72.00 109.67   26
 45  ω    133.00 161.00   1.00    8.00    --   88.00  61.00 -53.27   28
 46  ω     58.00  88.00   1.00    8.00    --   88.00  61.00 -53.27   30
 47  ω     90.00 154.00   1.00    8.00    --   88.00  70.00 178.00   64
 48  ω     56.00  83.00   1.00    8.00    --   88.00  70.00 178.00   27
 49  ω     61.00  87.00   1.00    8.00    --   92.00  64.00  66.87   26
 50  ω     64.00  92.00   1.00    8.00    --   92.00  58.00 -83.94   28
 51  ω     59.00  85.00   1.00    8.00    --   92.00  73.00 -21.79   26
 52  ω     61.00  87.00   1.00    8.00    --   92.00  64.00 144.75   26
 53  ω     64.00  94.00   1.00    8.00    --   96.00  73.00  68.72   30
 54  ω     79.00 106.00   1.00    8.00    --  113.00  77.00  30.00   27
 55  ω     79.00 105.00   1.00    8.00    --  113.00  77.00   0.00   26
 56  ω     79.00 111.00   1.00    8.00    --  113.00  77.00-180.00   32
 57  ω     79.00 104.00   1.00    8.00    --  113.00  77.00 -30.00   25
 58  ω     86.00 113.00   1.00    8.00    --  113.00  61.00-150.00   27
 59  ω     79.00 168.00   1.00    8.00    --  113.00  77.00  90.00   89
 60  ω     86.00 112.00   1.00    8.00    --  113.00  45.00 -90.00   26
 61  ω    112.00 137.00   1.00    8.00    --  113.00  77.00-150.00   25
 62  ω     84.00 111.00   1.00    8.00    --  113.00  61.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1167395000
_diffrn_orient_matrix_UB_12      0.1146150000
_diffrn_orient_matrix_UB_13      0.0302611000
_diffrn_orient_matrix_UB_21      0.1263028000
_diffrn_orient_matrix_UB_22      0.0478876000
_diffrn_orient_matrix_UB_23      -0.0840491000
_diffrn_orient_matrix_UB_31      -0.1413288000
_diffrn_orient_matrix_UB_32      0.0014493000
_diffrn_orient_matrix_UB_33      -0.0792149000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3304
_reflns_number_total             3695
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.019
_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)+(0.0490P)²+0.4865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0920
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N1'(H1'), C13(H13), C9'(H9'), C9(H9), C10'(H10'), C13'(H13'),
 C12(H12), C10(H10), C12'(H12'), C11(H11), C11'(H11')
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N2'(H2'A,H2'B)
2.c Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.05784(15) 0.54774(8) 0.64451(8) 0.0195(2) Uani 1 1 d . . . . .
O2 O 0.03667(15) 0.47685(8) 0.79922(7) 0.0190(2) Uani 1 1 d . . . . .
O2' O 0.81973(16) 0.20476(8) 0.47388(8) 0.0224(3) Uani 1 1 d . . . . .
O1' O 0.65771(16) 0.36081(8) 0.54644(8) 0.0226(3) Uani 1 1 d . . . . .
N1 N 0.16224(17) 0.36028(9) 0.54956(9) 0.0156(3) Uani 1 1 d . . . . .
H1 H 0.113780 0.411054 0.506016 0.019 Uiso 1 1 calc R . . . .
N1' N 0.55581(18) 0.45275(10) 0.35461(9) 0.0170(3) Uani 1 1 d . . . . .
H1' H 0.515276 0.496880 0.403896 0.020 Uiso 1 1 calc R . . . .
N2 N 0.30686(18) 0.23045(10) 0.42529(9) 0.0191(3) Uani 1 1 d . . . . .
H2A H 0.262490 0.275226 0.376082 0.023 Uiso 1 1 calc R . . . .
H2B H 0.375552 0.166228 0.411428 0.023 Uiso 1 1 calc R . . . .
N3 N 0.5018(2) 0.00142(10) 0.62651(10) 0.0229(3) Uani 1 1 d . . . . .
N2' N 0.40852(19) 0.57327(10) 0.22464(10) 0.0208(3) Uani 1 1 d . . . . .
H2'A H 0.358771 0.622478 0.268639 0.025 Uiso 1 1 calc R . . . .
H2'B H 0.387783 0.585826 0.160698 0.025 Uiso 1 1 calc R . . . .
N3' N 0.6279(2) 0.37215(11) 0.00306(10) 0.0255(3) Uani 1 1 d . . . . .
C3 C 0.2393(2) 0.27222(11) 0.70052(11) 0.0148(3) Uani 1 1 d . . . . .
C1 C 0.2689(2) 0.26083(11) 0.52380(11) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.3205(2) 0.20262(11) 0.61622(11) 0.0149(3) Uani 1 1 d . . . . .
C1' C 0.5189(2) 0.47658(12) 0.25584(11) 0.0166(3) Uani 1 1 d . . . . .
C8' C 0.8114(2) 0.19118(11) 0.24079(10) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.4201(2) 0.09166(12) 0.62283(11) 0.0161(3) Uani 1 1 d . . . . .
C6' C 0.7130(2) 0.30655(12) 0.46989(11) 0.0166(3) Uani 1 1 d . . . . .
C8 C 0.2628(2) 0.23819(11) 0.81032(11) 0.0153(3) Uani 1 1 d . . . . .
C2' C 0.6089(2) 0.38354(12) 0.20030(11) 0.0161(3) Uani 1 1 d . . . . .
C13 C 0.4466(2) 0.18721(11) 0.83845(11) 0.0170(3) Uani 1 1 d . . . . .
H13 H 0.553095 0.178138 0.788565 0.020 Uiso 1 1 calc R . . . .
C9' C 0.9988(2) 0.14303(12) 0.26493(11) 0.0174(3) Uani 1 1 d . . . . .
H9' H 1.057832 0.179439 0.303641 0.021 Uiso 1 1 calc R . . . .
C9 C 0.1045(2) 0.25101(11) 0.88602(11) 0.0172(3) Uani 1 1 d . . . . .
H9 H -0.018999 0.285652 0.868787 0.021 Uiso 1 1 calc R . . . .
C10' C 1.0977(2) 0.04114(12) 0.23160(11) 0.0195(3) Uani 1 1 d . . . . .
H10' H 1.223145 0.009675 0.247651 0.023 Uiso 1 1 calc R . . . .
C13' C 0.7258(2) 0.13507(12) 0.18263(11) 0.0184(3) Uani 1 1 d . . . . .
H13' H 0.601212 0.166671 0.165385 0.022 Uiso 1 1 calc R . . . .
C6 C 0.0309(2) 0.47248(11) 0.69801(11) 0.0151(3) Uani 1 1 d . . . . .
C4' C 0.6687(2) 0.34688(11) 0.36652(11) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.1411(2) 0.36966(12) 0.65679(11) 0.0160(3) Uani 1 1 d . . . . .
C5' C 0.6187(2) 0.37698(11) 0.09148(12) 0.0178(3) Uani 1 1 d . . . . .
C3' C 0.7041(2) 0.30141(11) 0.27100(11) 0.0155(3) Uani 1 1 d . . . . .
C12 C 0.4730(2) 0.14982(12) 0.93970(12) 0.0205(3) Uani 1 1 d . . . . .
H12 H 0.596707 0.116860 0.957633 0.025 Uiso 1 1 calc R . . . .
C10 C 0.1311(2) 0.21215(12) 0.98699(11) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.024861 0.219991 1.036926 0.023 Uiso 1 1 calc R . . . .
C12' C 0.8242(2) 0.03279(12) 0.15027(12) 0.0211(3) Uani 1 1 d . . . . .
H12' H 0.765109 -0.004341 0.112354 0.025 Uiso 1 1 calc R . . . .
C11 C 0.3149(2) 0.16167(12) 1.01405(11) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.331824 0.135906 1.081881 0.025 Uiso 1 1 calc R . . . .
C11' C 1.0106(2) -0.01403(12) 0.17443(12) 0.0216(3) Uani 1 1 d . . . . .
H11' H 1.077236 -0.082465 0.152329 0.026 Uiso 1 1 calc R . . . .
C7' C 0.8711(2) 0.15957(13) 0.57460(11) 0.0232(3) Uani 1 1 d . . . . .
H7'A H 0.966582 0.091370 0.566904 0.035 Uiso 1 1 calc GR . . . .
H7'B H 0.758344 0.149414 0.616785 0.035 Uiso 1 1 calc GR . . . .
H7'C H 0.922673 0.207867 0.607082 0.035 Uiso 1 1 calc GR . . . .
C7 C -0.0802(2) 0.57421(12) 0.84734(12) 0.0218(3) Uani 1 1 d . . . . .
H7A H -0.039570 0.634915 0.815448 0.033 Uiso 1 1 calc GR . . . .
H7B H -0.065144 0.568732 0.919906 0.033 Uiso 1 1 calc GR . . . .
H7C H -0.213419 0.583681 0.838652 0.033 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2266(17) . ?
O2 C6 1.3304(17) . ?
O2 C7 1.4448(17) . ?
O2' C6' 1.3281(18) . ?
O2' C7' 1.4435(17) . ?
O1' C6' 1.2238(18) . ?
N1 C1 1.3451(18) . ?
N1 C4 1.3965(19) . ?
N1' C1' 1.3422(19) . ?
N1' C4' 1.3931(19) . ?
N2 C1 1.3434(19) . ?
N3 C5 1.1519(19) . ?
N2' C1' 1.3462(19) . ?
N3' C5' 1.151(2) . ?
C3 C2 1.434(2) . ?
C3 C8 1.480(2) . ?
C3 C4 1.381(2) . ?
C1 C2 1.404(2) . ?
C2 C5 1.416(2) . ?
C1' C2' 1.405(2) . ?
C8' C9' 1.393(2) . ?
C8' C13' 1.395(2) . ?
C8' C3' 1.477(2) . ?
C6' C4' 1.447(2) . ?
C8 C13 1.394(2) . ?
C8 C9 1.395(2) . ?
C2' C5' 1.418(2) . ?
C2' C3' 1.432(2) . ?
C13 C12 1.386(2) . ?
C9' C10' 1.386(2) . ?
C9 C10 1.388(2) . ?
C10' C11' 1.386(2) . ?
C13' C12' 1.385(2) . ?
C6 C4 1.450(2) . ?
C4' C3' 1.381(2) . ?
C12 C11 1.384(2) . ?
C10 C11 1.388(2) . ?
C12' C11' 1.383(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
C6 O2 C7 116.48(11) . . ?
C6' O2' C7' 116.53(11) . . ?
C1 N1 C4 110.62(12) . . ?
C1' N1' C4' 110.85(12) . . ?
C2 C3 C8 123.42(12) . . ?
C4 C3 C2 106.21(12) . . ?
C4 C3 C8 130.37(13) . . ?
N1 C1 C2 107.16(12) . . ?
N2 C1 N1 122.32(13) . . ?
N2 C1 C2 130.50(13) . . ?
C1 C2 C3 108.06(12) . . ?
C1 C2 C5 124.51(13) . . ?
C5 C2 C3 127.19(13) . . ?
N1' C1' N2' 122.44(13) . . ?
N1' C1' C2' 107.05(12) . . ?
N2' C1' C2' 130.48(14) . . ?
C9' C8' C13' 118.81(13) . . ?
C9' C8' C3' 122.02(13) . . ?
C13' C8' C3' 119.11(13) . . ?
N3 C5 C2 178.90(15) . . ?
O2' C6' C4' 113.55(12) . . ?
O1' C6' O2' 123.08(13) . . ?
O1' C6' C4' 123.38(13) . . ?
C13 C8 C3 119.37(13) . . ?
C13 C8 C9 118.82(13) . . ?
C9 C8 C3 121.74(13) . . ?
C1' C2' C5' 125.19(13) . . ?
C1' C2' C3' 108.03(13) . . ?
C5' C2' C3' 126.50(13) . . ?
C12 C13 C8 120.97(14) . . ?
C10' C9' C8' 120.36(14) . . ?
C10 C9 C8 120.10(14) . . ?
C11' C10' C9' 120.25(14) . . ?
C12' C13' C8' 120.74(14) . . ?
O1 C6 O2 123.63(13) . . ?
O1 C6 C4 123.15(13) . . ?
O2 C6 C4 113.22(12) . . ?
N1' C4' C6' 117.77(13) . . ?
C3' C4' N1' 107.88(12) . . ?
C3' C4' C6' 134.22(13) . . ?
N1 C4 C6 117.89(12) . . ?
C3 C4 N1 107.95(12) . . ?
C3 C4 C6 134.15(13) . . ?
N3' C5' C2' 179.36(17) . . ?
C2' C3' C8' 123.54(13) . . ?
C4' C3' C8' 130.25(13) . . ?
C4' C3' C2' 106.20(12) . . ?
C11 C12 C13 119.83(14) . . ?
C9 C10 C11 120.53(14) . . ?
C11' C12' C13' 119.89(14) . . ?
C12 C11 C10 119.75(14) . . ?
C12' C11' C10' 119.94(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.103
_oxdiff_exptl_absorpt_empirical_full_min 0.538
