# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_pas-22
_audit_block_doi                 10.5517/ccdc.csd.cc2bxfrg
_database_code_depnum_ccdc_archive 'CCDC 2172286'
loop_
_audit_author_name
_audit_author_address
'Alexander Koronatov'
;SPbSU
Russia
;
_audit_update_record             
;
2022-05-12 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2022-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'methyl 2-acetoxy-3-(4-nitrophenyl)-3-(5-phenyl-1H-pyrrol-2-yl)acrylate'
_chemical_formula_moiety         'C22 H18 N2 O7'
_chemical_formula_sum            'C22 H18 N2 O7'
_chemical_formula_weight         422.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H18 N2 O7 '
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4249(3)
_cell_length_b                   13.8287(3)
_cell_length_c                   13.7118(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.515(2)
_cell_angle_gamma                90
_cell_volume                     1959.75(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7246
_cell_measurement_temperature    99.94(18)
_cell_measurement_theta_max      70.2420
_cell_measurement_theta_min      3.1980
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_preparation       'slow evaporation of solution (CHCl3/hexane)'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.491
_diffrn_reflns_theta_min         4.278
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.94(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  26.00   0.50    0.46    --  -38.95  67.00  41.00  178
  2  ω    -50.00 -19.00   0.50    0.46    --  -38.95 -67.00 -93.00   62
  3  ω    -97.00 -57.00   0.50    0.46    --  -38.95 -67.00 -93.00   80
  4  ω     58.00 102.00   0.50    0.46    --   38.95  67.00  41.00   88
  5  ω     37.00 124.00   0.50    1.85    --  100.00 -67.00 -93.00  174
  6  ω     77.00 149.00   0.50    1.85    --  100.00  67.00  41.00  144
  7  ω   -103.00 -59.00   0.50    0.46    --  -38.95 -54.00 -90.00   88
  8  ω    -62.00 -35.00   0.50    0.46    --  -38.95  77.00 120.00   54
  9  ω    -68.00 -14.00   0.50    0.46    --  -38.95 138.00 150.00  108
 10  ω    -97.00 -30.00   0.50    0.46    --  -38.95 138.00-180.00  134
 11  ω    -93.00 -21.00   0.50    0.46    --  -38.95 138.00  30.00  144
 12  ω    -17.00  13.00   0.50    0.46    --  -38.95  77.00 120.00   60
 13  ω    -44.00 -19.00   0.50    0.46    --  -38.95 -54.00 -90.00   50
 14  ω     56.00  95.00   0.50    0.46    --   38.95  43.00  30.00   78
 15  ω    -22.00   3.00   0.50    0.46    --   38.95 -67.00 -93.00   50
 16  ω     29.00  54.00   0.50    0.46    --   38.95  43.00  30.00   50
 17  ω     73.00  98.00   0.50    0.46    --   38.95  32.00  30.00   50
 18  ω    -29.00  50.00   0.50    0.46    --   38.95 -32.00 120.00  158
 19  ω     87.00 113.00   0.50    1.85    --  100.00 -15.00  60.00   52
 20  ω     25.00  51.00   0.50    1.85    --  100.00 -15.00  60.00   52
 21  ω    101.00 127.00   0.50    1.85    --  100.00 -77.00 120.00   52
 22  ω     71.00 101.00   0.50    1.85    --  100.00  15.00-180.00   60
 23  ω     49.00 113.00   0.50    1.85    --  100.00 -30.00  60.00  128
 24  ω     39.00  66.00   0.50    1.85    --  100.00 -77.00 120.00   54
 25  ω     80.00 155.00   0.50    1.85    --  100.00  61.00   0.00  150
 26  ω     88.00 113.00   0.50    1.85    --  100.00 -61.00  60.00   50
 27  ω     52.00  77.00   0.50    1.85    --  100.00 -61.00  60.00   50
 28  ω     76.00 157.00   0.50    1.85    --  100.00  69.00  60.00  162
 29  ω     77.00 103.00   0.50    1.85    --  100.00-111.00 -90.00   52
 30  ω     36.00 108.00   0.50    1.85    --  100.00 -30.00-150.00  144
 31  ω     76.00 149.00   0.50    1.85    --  100.00  69.00 -30.00  146
 32  ω    106.00 136.00   0.50    1.85    --  100.00  15.00-180.00   60
 33  ω     65.00 107.00   0.50    1.85    --  100.00-111.00-150.00   84
 34  ω     33.00  79.00   0.50    1.85    --  100.00-111.00  60.00   92
 35  ω     31.00  83.00   0.50    1.85    --  100.00 -15.00-120.00  104
 36  ω     94.00 119.00   0.50    1.85    --  100.00 -15.00-120.00   50
 37  ω     72.00  97.00   0.50    1.85    --  100.00 -53.00 -30.00   50
 38  ω     66.00 101.00   0.50    1.85    --  100.00-111.00   0.00   70
 39  ω     31.00  63.00   0.50    1.85    --  100.00-111.00 -90.00   64
 40  ω     49.00  81.00   0.50    1.85    --  100.00 -37.00  30.00   64
 41  ω     53.00  94.00   0.50    0.46    --   38.95   0.00 150.00   82
 42  ω    -59.00 -31.00   0.50    0.46    --  -38.95 -43.00 120.00   56
 43  ω      0.00  27.00   0.50    0.46    --  -38.95  21.00  60.00   54
 44  ω    -57.00 -15.00   0.50    0.46    --  -38.95  21.00  60.00   84
 45  ω   -105.00 -80.00   0.50    0.46    --  -38.95 -43.00 150.00   50
 46  ω    -66.00 -25.00   0.50    0.46    --  -38.95 -43.00 150.00   82
 47  ω   -103.00 -87.50   0.50    0.46    --  -38.95 -43.00 120.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0222170000
_diffrn_orient_matrix_UB_12      -0.0768469000
_diffrn_orient_matrix_UB_13      0.0774352000
_diffrn_orient_matrix_UB_21      0.1197655000
_diffrn_orient_matrix_UB_22      0.0373014000
_diffrn_orient_matrix_UB_23      0.0673135000
_diffrn_orient_matrix_UB_31      -0.0858153000
_diffrn_orient_matrix_UB_32      0.0715373000
_diffrn_orient_matrix_UB_33      0.0481754000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3212
_reflns_number_total             3732
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.046
_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)+(0.0504P)²+0.6253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N008(H008), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
2.b Idealised Me refined as rotating group:
 C00U(H00A,H00B,H00C), C00V(H00D,H00E,H00F)
;
_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
O001 O 0.32348(10) 0.61360(7) 0.45090(7) 0.0197(2) Uani 1 1 d . . . . .
O002 O 0.11528(10) 0.51714(8) 0.38722(7) 0.0227(2) Uani 1 1 d . . . . .
O003 O 0.16887(10) 0.49831(8) 0.23440(7) 0.0237(2) Uani 1 1 d . . . . .
O004 O 0.37090(10) 0.45418(7) 0.47367(7) 0.0226(2) Uani 1 1 d . . . . .
O005 O 0.32386(11) 0.55425(8) 0.59521(7) 0.0232(2) Uani 1 1 d . . . . .
O006 O 0.21493(12) 0.62016(9) -0.17618(8) 0.0318(3) Uani 1 1 d . . . . .
O007 O 0.05732(12) 0.71227(10) -0.14488(8) 0.0364(3) Uani 1 1 d . . . . .
N008 N 0.53104(12) 0.73061(9) 0.41344(9) 0.0191(3) Uani 1 1 d . . . . .
H008 H 0.523935 0.690049 0.459966 0.023 Uiso 1 1 calc R U . . .
N009 N 0.15774(13) 0.66696(10) -0.11908(9) 0.0259(3) Uani 1 1 d . . . . .
C00A C 0.61738(14) 0.80538(11) 0.41912(11) 0.0196(3) Uani 1 1 d . . . . .
C00B C 0.30580(14) 0.66534(10) 0.18207(10) 0.0195(3) Uani 1 1 d . . . . .
C00C C 0.18854(14) 0.53412(10) 0.31511(10) 0.0195(3) Uani 1 1 d . . . . .
C00D C 0.34199(13) 0.53097(10) 0.50458(10) 0.0183(3) Uani 1 1 d . . . . .
C00E C 0.35388(14) 0.66214(10) 0.28986(10) 0.0188(3) Uani 1 1 d . . . . .
C00F C 0.29502(14) 0.60276(10) 0.34877(10) 0.0188(3) Uani 1 1 d . . . . .
C00G C 0.45677(14) 0.72947(11) 0.32225(10) 0.0192(3) Uani 1 1 d . . . . .
C00H C 0.21157(15) 0.66843(11) -0.01462(10) 0.0215(3) Uani 1 1 d . . . . .
C00I C 0.33060(15) 0.62535(11) 0.01412(11) 0.0228(3) Uani 1 1 d . . . . .
H00I H 0.377263 0.597305 -0.031874 0.027 Uiso 1 1 calc R U . . .
C00J C 0.37812(14) 0.62528(11) 0.11353(11) 0.0216(3) Uani 1 1 d . . . . .
H00J H 0.458742 0.598344 0.134562 0.026 Uiso 1 1 calc R U . . .
C00K C 0.49785(14) 0.80730(11) 0.26997(11) 0.0218(3) Uani 1 1 d . . . . .
H00K H 0.465073 0.824815 0.206062 0.026 Uiso 1 1 calc R U . . .
C00L C 0.18794(15) 0.71001(11) 0.15003(11) 0.0223(3) Uani 1 1 d . . . . .
H00L H 0.140859 0.738436 0.195534 0.027 Uiso 1 1 calc R U . . .
C00M C 0.59691(14) 0.85455(11) 0.33018(11) 0.0221(3) Uani 1 1 d . . . . .
H00M H 0.641273 0.909237 0.313606 0.026 Uiso 1 1 calc R U . . .
C00N C 0.14052(15) 0.71235(11) 0.05094(11) 0.0228(3) Uani 1 1 d . . . . .
H00N H 0.062526 0.742839 0.029098 0.027 Uiso 1 1 calc R U . . .
C00O C 0.70858(14) 0.82454(10) 0.50764(11) 0.0203(3) Uani 1 1 d . . . . .
C00P C 0.80325(14) 0.89647(11) 0.50597(11) 0.0234(3) Uani 1 1 d . . . . .
H00P H 0.809098 0.930574 0.448258 0.028 Uiso 1 1 calc R U . . .
C00Q C 0.70265(15) 0.77416(11) 0.59544(11) 0.0243(3) Uani 1 1 d . . . . .
H00Q H 0.640303 0.726434 0.597908 0.029 Uiso 1 1 calc R U . . .
C00R C 0.88132(15) 0.86596(12) 0.67661(11) 0.0255(3) Uani 1 1 d . . . . .
H00R H 0.938661 0.879795 0.732687 0.031 Uiso 1 1 calc R U . . .
C00S C 0.88828(15) 0.91695(12) 0.59015(12) 0.0266(3) Uani 1 1 d . . . . .
H00S H 0.950263 0.965105 0.588607 0.032 Uiso 1 1 calc R U . . .
C00T C 0.78894(16) 0.79463(12) 0.67905(11) 0.0266(3) Uani 1 1 d . . . . .
H00T H 0.784462 0.760224 0.736786 0.032 Uiso 1 1 calc R U . . .
C00U C 0.01919(16) 0.44115(12) 0.36659(12) 0.0275(3) Uani 1 1 d . . . . .
H00A H -0.039494 0.457973 0.309206 0.041 Uiso 1 1 calc R U . . .
H00B H -0.028038 0.433917 0.421737 0.041 Uiso 1 1 calc R U . . .
H00C H 0.061655 0.381379 0.355202 0.041 Uiso 1 1 calc R U . . .
C00V C 0.34401(18) 0.47622(12) 0.66618(11) 0.0296(4) Uani 1 1 d . . . . .
H00D H 0.294684 0.420777 0.641442 0.044 Uiso 1 1 calc R U . . .
H00E H 0.316484 0.496476 0.727113 0.044 Uiso 1 1 calc R U . . .
H00F H 0.434203 0.459723 0.676979 0.044 Uiso 1 1 calc R U . . .


_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
O001 C00D 1.3593(17) . ?
O001 C00F 1.4010(17) . ?
O002 C00C 1.3467(18) . ?
O002 C00U 1.4539(18) . ?
O003 C00C 1.2052(18) . ?
O004 C00D 1.1964(18) . ?
O005 C00D 1.3210(17) . ?
O005 C00V 1.4499(18) . ?
O006 N009 1.2286(18) . ?
O007 N009 1.2316(18) . ?
N008 H008 0.8600 . ?
N008 C00A 1.3663(19) . ?
N008 C00G 1.3820(18) . ?
N009 C00H 1.4686(18) . ?
C00A C00M 1.388(2) . ?
C00A C00O 1.465(2) . ?
C00B C00E 1.4980(19) . ?
C00B C00J 1.394(2) . ?
C00B C00L 1.394(2) . ?
C00C C00F 1.487(2) . ?
C00E C00F 1.354(2) . ?
C00E C00G 1.446(2) . ?
C00G C00K 1.391(2) . ?
C00H C00I 1.386(2) . ?
C00H C00N 1.378(2) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.388(2) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00M 1.397(2) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.384(2) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O C00P 1.404(2) . ?
C00O C00Q 1.399(2) . ?
C00P H00P 0.9300 . ?
C00P C00S 1.389(2) . ?
C00Q H00Q 0.9300 . ?
C00Q C00T 1.391(2) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.389(2) . ?
C00R C00T 1.382(2) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U H00A 0.9600 . ?
C00U H00B 0.9600 . ?
C00U H00C 0.9600 . ?
C00V H00D 0.9600 . ?
C00V H00E 0.9600 . ?
C00V H00F 0.9600 . ?

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
C00D O001 C00F 116.61(11) . . ?
C00C O002 C00U 115.19(12) . . ?
C00D O005 C00V 115.09(12) . . ?
C00A N008 H008 124.8 . . ?
C00A N008 C00G 110.32(12) . . ?
C00G N008 H008 124.8 . . ?
O006 N009 O007 123.37(13) . . ?
O006 N009 C00H 118.26(13) . . ?
O007 N009 C00H 118.37(13) . . ?
N008 C00A C00M 107.22(12) . . ?
N008 C00A C00O 122.38(13) . . ?
C00M C00A C00O 130.39(14) . . ?
C00J C00B C00E 120.84(13) . . ?
C00L C00B C00E 119.44(13) . . ?
C00L C00B C00J 119.72(14) . . ?
O002 C00C C00F 110.81(12) . . ?
O003 C00C O002 123.91(13) . . ?
O003 C00C C00F 125.28(13) . . ?
O004 C00D O001 125.37(13) . . ?
O004 C00D O005 128.55(13) . . ?
O005 C00D O001 106.07(12) . . ?
C00F C00E C00B 119.17(13) . . ?
C00F C00E C00G 125.68(13) . . ?
C00G C00E C00B 115.03(12) . . ?
O001 C00F C00C 115.49(12) . . ?
C00E C00F O001 118.57(13) . . ?
C00E C00F C00C 125.45(13) . . ?
N008 C00G C00E 126.21(13) . . ?
N008 C00G C00K 106.47(13) . . ?
C00K C00G C00E 127.29(13) . . ?
C00I C00H N009 119.01(13) . . ?
C00N C00H N009 118.21(14) . . ?
C00N C00H C00I 122.78(14) . . ?
C00H C00I H00I 121.0 . . ?
C00H C00I C00J 118.07(14) . . ?
C00J C00I H00I 121.0 . . ?
C00B C00J H00J 119.8 . . ?
C00I C00J C00B 120.44(14) . . ?
C00I C00J H00J 119.8 . . ?
C00G C00K H00K 125.9 . . ?
C00G C00K C00M 108.11(13) . . ?
C00M C00K H00K 125.9 . . ?
C00B C00L H00L 119.8 . . ?
C00N C00L C00B 120.44(14) . . ?
C00N C00L H00L 119.8 . . ?
C00A C00M C00K 107.87(13) . . ?
C00A C00M H00M 126.1 . . ?
C00K C00M H00M 126.1 . . ?
C00H C00N C00L 118.46(14) . . ?
C00H C00N H00N 120.8 . . ?
C00L C00N H00N 120.8 . . ?
C00P C00O C00A 119.75(13) . . ?
C00Q C00O C00A 121.74(14) . . ?
C00Q C00O C00P 118.50(14) . . ?
C00O C00P H00P 119.9 . . ?
C00S C00P C00O 120.29(14) . . ?
C00S C00P H00P 119.9 . . ?
C00O C00Q H00Q 119.6 . . ?
C00T C00Q C00O 120.75(15) . . ?
C00T C00Q H00Q 119.6 . . ?
C00S C00R H00R 120.1 . . ?
C00T C00R H00R 120.1 . . ?
C00T C00R C00S 119.82(14) . . ?
C00P C00S H00S 119.8 . . ?
C00R C00S C00P 120.43(15) . . ?
C00R C00S H00S 119.8 . . ?
C00Q C00T H00T 119.9 . . ?
C00R C00T C00Q 120.20(15) . . ?
C00R C00T H00T 119.9 . . ?
O002 C00U H00A 109.5 . . ?
O002 C00U H00B 109.5 . . ?
O002 C00U H00C 109.5 . . ?
H00A C00U H00B 109.5 . . ?
H00A C00U H00C 109.5 . . ?
H00B C00U H00C 109.5 . . ?
O005 C00V H00D 109.5 . . ?
O005 C00V H00E 109.5 . . ?
O005 C00V H00F 109.5 . . ?
H00D C00V H00E 109.5 . . ?
H00D C00V H00F 109.5 . . ?
H00E C00V H00F 109.5 . . ?

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
O002 C00C C00F O001 18.14(17) . . . . ?
O002 C00C C00F C00E -153.68(14) . . . . ?
O003 C00C C00F O001 -162.19(14) . . . . ?
O003 C00C C00F C00E 26.0(2) . . . . ?
O006 N009 C00H C00I 6.3(2) . . . . ?
O006 N009 C00H C00N -173.31(13) . . . . ?
O007 N009 C00H C00I -174.09(14) . . . . ?
O007 N009 C00H C00N 6.3(2) . . . . ?
N008 C00A C00M C00K -0.87(17) . . . . ?
N008 C00A C00O C00P 173.85(13) . . . . ?
N008 C00A C00O C00Q -7.5(2) . . . . ?
N008 C00G C00K C00M 0.15(17) . . . . ?
N009 C00H C00I C00J -178.31(13) . . . . ?
N009 C00H C00N C00L 177.04(13) . . . . ?
C00A N008 C00G C00E -178.78(14) . . . . ?
C00A N008 C00G C00K -0.71(16) . . . . ?
C00A C00O C00P C00S 178.42(14) . . . . ?
C00A C00O C00Q C00T -178.95(14) . . . . ?
C00B C00E C00F O001 -167.88(12) . . . . ?
C00B C00E C00F C00C 3.7(2) . . . . ?
C00B C00E C00G N008 -169.13(13) . . . . ?
C00B C00E C00G C00K 13.2(2) . . . . ?
C00B C00L C00N C00H 0.9(2) . . . . ?
C00D O001 C00F C00C 50.46(16) . . . . ?
C00D O001 C00F C00E -137.12(14) . . . . ?
C00E C00B C00J C00I 177.57(13) . . . . ?
C00E C00B C00L C00N -178.86(13) . . . . ?
C00E C00G C00K C00M 178.19(14) . . . . ?
C00F O001 C00D O004 21.6(2) . . . . ?
C00F O001 C00D O005 -159.49(11) . . . . ?
C00F C00E C00G N008 14.9(2) . . . . ?
C00F C00E C00G C00K -162.77(15) . . . . ?
C00G N008 C00A C00M 0.98(16) . . . . ?
C00G N008 C00A C00O 179.78(13) . . . . ?
C00G C00E C00F O001 7.9(2) . . . . ?
C00G C00E C00F C00C 179.54(14) . . . . ?
C00G C00K C00M C00A 0.44(18) . . . . ?
C00H C00I C00J C00B 1.7(2) . . . . ?
C00I C00H C00N C00L -2.5(2) . . . . ?
C00J C00B C00E C00F -108.56(16) . . . . ?
C00J C00B C00E C00G 75.19(17) . . . . ?
C00J C00B C00L C00N 1.9(2) . . . . ?
C00L C00B C00E C00F 72.21(18) . . . . ?
C00L C00B C00E C00G -104.04(16) . . . . ?
C00L C00B C00J C00I -3.2(2) . . . . ?
C00M C00A C00O C00P -7.7(2) . . . . ?
C00M C00A C00O C00Q 171.03(15) . . . . ?
C00N C00H C00I C00J 1.2(2) . . . . ?
C00O C00A C00M C00K -179.53(15) . . . . ?
C00O C00P C00S C00R 0.6(2) . . . . ?
C00O C00Q C00T C00R 0.6(2) . . . . ?
C00P C00O C00Q C00T -0.2(2) . . . . ?
C00Q C00O C00P C00S -0.3(2) . . . . ?
C00S C00R C00T C00Q -0.3(2) . . . . ?
C00T C00R C00S C00P -0.2(2) . . . . ?
C00U O002 C00C O003 8.3(2) . . . . ?
C00U O002 C00C C00F -172.05(12) . . . . ?
C00V O005 C00D O001 -177.77(12) . . . . ?
C00V O005 C00D O004 1.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.891
####################################################################### 
# 
# 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_rnv36a
_audit_block_doi                 10.5517/ccdc.csd.cc2cshf3
_database_code_depnum_ccdc_archive 'CCDC 2198285'
loop_
_audit_author_name
_audit_author_address
'Alexander Koronatov'
;Technion, Israel Institute of Technology
Israel
;
_audit_update_record             
;
2022-08-11 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2017-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N2 O6'
_chemical_formula_sum            'C21 H14 N2 O6'
_chemical_formula_weight         390.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H25 Cl N2 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   8.1668(3)
_cell_length_b                   9.5156(5)
_cell_length_c                   12.1149(7)
_cell_angle_alpha                101.349(5)
_cell_angle_beta                 103.088(4)
_cell_angle_gamma                91.725(4)
_cell_volume                     896.33(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6000
_cell_measurement_theta_min      3.0750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tables
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14733
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.750
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -66.00   43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   19.0000 -120.0000 109

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00  -49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega  -93.00    8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  178.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega   65.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -164.0000  149.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega  -75.00   -4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000   30.0000 71

#__ type_ start__ end____ width___ exp.time_
  9 omega    1.00   50.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega  -90.00  -48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega  -33.00   -1.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega  -84.00    8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 13 omega   28.00   53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega  -47.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 15 omega   26.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -90.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0053566000
_diffrn_orient_matrix_UB_12      0.0076389000
_diffrn_orient_matrix_UB_13      -0.0577545000
_diffrn_orient_matrix_UB_21      0.0083062000
_diffrn_orient_matrix_UB_22      0.0758747000
_diffrn_orient_matrix_UB_23      0.0188133000
_diffrn_orient_matrix_UB_31      0.0888937000
_diffrn_orient_matrix_UB_32      -0.0006296000
_diffrn_orient_matrix_UB_33      0.0094269000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3467
_reflns_number_total             4101
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    ?
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.022
_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)+(0.0343P)²+0.3568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C21(H21), C20(H20), C18(H18), C5(H5), C6(H6), C13(H13), C9(H9),
 C11(H11), C12(H12), C10(H10)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.25683(10) 0.10691(9) 0.55322(7) 0.01566(18) Uani 1 1 d . . . . .
O4 O 0.19577(10) 0.04084(9) 0.33365(7) 0.01806(19) Uani 1 1 d . . . . .
O2 O 0.44678(11) 0.09297(10) 0.71135(8) 0.0223(2) Uani 1 1 d . . . . .
C16 C -0.15292(14) 0.28427(12) 0.49652(10) 0.0149(2) Uani 1 1 d . . . . .
N1 N 0.22620(12) 0.23351(11) 0.73068(9) 0.0152(2) Uani 1 1 d . . . . .
O3 O -0.07999(10) 0.07715(9) 0.31084(7) 0.01909(19) Uani 1 1 d . . . . .
C3 C 0.00952(14) 0.23449(12) 0.55504(10) 0.0145(2) Uani 1 1 d . . . . .
C19 C -0.45201(14) 0.37260(13) 0.38649(10) 0.0159(2) Uani 1 1 d . . . . .
C17 C -0.30376(15) 0.24096(13) 0.52015(11) 0.0170(2) Uani 1 1 d . . . . .
H17 H -0.3028 0.1832 0.5739 0.020 Uiso 1 1 calc R . . . .
N2 N -0.61266(13) 0.41691(11) 0.32578(9) 0.0203(2) Uani 1 1 d . . . . .
C21 C -0.15398(14) 0.37347(13) 0.41776(11) 0.0159(2) Uani 1 1 d . . . . .
H21 H -0.0530 0.4026 0.4027 0.019 Uiso 1 1 calc R . . . .
C20 C -0.30386(15) 0.41898(12) 0.36186(11) 0.0163(2) Uani 1 1 d . . . . .
H20 H -0.3054 0.4787 0.3095 0.020 Uiso 1 1 calc R . . . .
C2 C 0.07072(14) 0.27990(13) 0.67788(11) 0.0158(2) Uani 1 1 d . . . . .
C4 C 0.10435(14) 0.14879(13) 0.49711(10) 0.0149(2) Uani 1 1 d . . . . .
C14 C 0.06127(14) 0.08600(12) 0.37122(10) 0.0150(2) Uani 1 1 d . . . . .
C18 C -0.45493(15) 0.28391(13) 0.46358(11) 0.0179(3) Uani 1 1 d . . . . .
H18 H -0.5564 0.2536 0.4773 0.021 Uiso 1 1 calc R . . . .
O6 O -0.60865(12) 0.50006(12) 0.26093(9) 0.0334(3) Uani 1 1 d . . . . .
C1 C 0.31919(14) 0.14055(13) 0.67026(11) 0.0163(2) Uani 1 1 d . . . . .
O5 O -0.74412(11) 0.37007(11) 0.34321(10) 0.0310(2) Uani 1 1 d . . . . .
C7 C 0.25865(15) 0.28517(13) 0.85044(11) 0.0180(2) Uani 1 1 d . . . . .
C5 C 0.00956(16) 0.36138(14) 0.76393(11) 0.0202(3) Uani 1 1 d . . . . .
H5 H -0.0902 0.4071 0.7542 0.024 Uiso 1 1 calc R . . . .
C8 C 0.40818(16) 0.25720(13) 0.93542(11) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.12615(16) 0.36309(14) 0.87029(11) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.1145 0.4101 0.9427 0.026 Uiso 1 1 calc R . . . .
C13 C 0.57163(17) 0.29959(15) 0.93166(12) 0.0250(3) Uani 1 1 d . . . . .
H13 H 0.5888 0.3463 0.8742 0.030 Uiso 1 1 calc R . . . .
C15 C 0.16415(16) -0.01251(15) 0.20979(11) 0.0223(3) Uani 1 1 d . . . . .
H15A H 0.1292 0.0637 0.1705 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.0769 -0.0896 0.1863 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.2654 -0.0471 0.1904 0.033 Uiso 1 1 calc GR . . . .
C9 C 0.38514(18) 0.19033(15) 1.02336(12) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.2766 0.1634 1.0275 0.032 Uiso 1 1 calc R . . . .
C11 C 0.68422(19) 0.20330(15) 1.09981(12) 0.0296(3) Uani 1 1 d . . . . .
H11 H 0.7766 0.1841 1.1540 0.036 Uiso 1 1 calc R . . . .
C12 C 0.70830(17) 0.27192(15) 1.01381(12) 0.0278(3) Uani 1 1 d . . . . .
H12 H 0.8171 0.2998 1.0109 0.033 Uiso 1 1 calc R . . . .
C10 C 0.5231(2) 0.16332(17) 1.10525(12) 0.0327(3) Uani 1 1 d . . . . .
H10 H 0.5067 0.1182 1.1638 0.039 Uiso 1 1 calc R . . . .


_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 C4 1.3874(13) . ?
O1 C1 1.3626(15) . ?
O4 C14 1.3328(14) . ?
O4 C15 1.4467(15) . ?
O2 C1 1.1920(14) . ?
C16 C3 1.4937(15) . ?
C16 C17 1.3946(16) . ?
C16 C21 1.3952(16) . ?
N1 C2 1.4118(14) . ?
N1 C1 1.3901(15) . ?
N1 C7 1.3980(16) . ?
O3 C14 1.2086(14) . ?
C3 C2 1.4311(17) . ?
C3 C4 1.3477(17) . ?
C19 N2 1.4692(15) . ?
C19 C20 1.3896(16) . ?
C19 C18 1.3799(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.3850(16) . ?
N2 O6 1.2244(14) . ?
N2 O5 1.2275(14) . ?
C21 H21 0.9300 . ?
C21 C20 1.3843(16) . ?
C20 H20 0.9300 . ?
C2 C5 1.3706(17) . ?
C4 C14 1.4807(17) . ?
C18 H18 0.9300 . ?
C7 C8 1.4764(17) . ?
C7 C6 1.3691(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.4151(18) . ?
C8 C13 1.3960(18) . ?
C8 C9 1.3877(18) . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.3868(18) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C10 1.390(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(2) . ?
C11 C10 1.378(2) . ?
C12 H12 0.9300 . ?
C10 H10 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
C1 O1 C4 123.91(9) . . ?
C14 O4 C15 114.69(9) . . ?
C17 C16 C3 119.99(10) . . ?
C17 C16 C21 119.96(11) . . ?
C21 C16 C3 120.04(10) . . ?
C1 N1 C2 123.34(10) . . ?
C1 N1 C7 127.46(10) . . ?
C7 N1 C2 108.95(10) . . ?
C2 C3 C16 119.56(10) . . ?
C4 C3 C16 122.94(11) . . ?
C4 C3 C2 117.50(10) . . ?
C20 C19 N2 118.63(10) . . ?
C18 C19 N2 118.61(10) . . ?
C18 C19 C20 122.75(11) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.02(11) . . ?
C18 C17 H17 120.0 . . ?
O6 N2 C19 118.24(10) . . ?
O6 N2 O5 123.16(11) . . ?
O5 N2 C19 118.60(10) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.64(11) . . ?
C20 C21 H21 119.7 . . ?
C19 C20 H20 121.0 . . ?
C21 C20 C19 117.90(11) . . ?
C21 C20 H20 121.0 . . ?
N1 C2 C3 118.38(10) . . ?
C5 C2 N1 107.45(11) . . ?
C5 C2 C3 134.15(11) . . ?
O1 C4 C14 112.13(10) . . ?
C3 C4 O1 121.79(11) . . ?
C3 C4 C14 126.07(10) . . ?
O4 C14 C4 112.04(10) . . ?
O3 C14 O4 124.68(11) . . ?
O3 C14 C4 123.29(11) . . ?
C19 C18 C17 118.71(11) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
O1 C1 N1 114.80(10) . . ?
O2 C1 O1 119.16(11) . . ?
O2 C1 N1 126.01(11) . . ?
N1 C7 C8 125.00(11) . . ?
C6 C7 N1 106.47(11) . . ?
C6 C7 C8 128.52(12) . . ?
C2 C5 H5 126.3 . . ?
C2 C5 C6 107.38(11) . . ?
C6 C5 H5 126.3 . . ?
C13 C8 C7 121.90(11) . . ?
C9 C8 C7 118.96(12) . . ?
C9 C8 C13 119.12(12) . . ?
C7 C6 C5 109.73(12) . . ?
C7 C6 H6 125.1 . . ?
C5 C6 H6 125.1 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.89(13) . . ?
C12 C13 H13 120.1 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.45(13) . . ?
C10 C9 H9 119.8 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.89(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.55(13) . . ?
C11 C12 H12 119.7 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.09(13) . . ?
C11 C10 H10 120.0 . . ?

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 C4 C14 O4 -18.97(13) . . . . ?
O1 C4 C14 O3 160.84(11) . . . . ?
C16 C3 C2 N1 -178.80(10) . . . . ?
C16 C3 C2 C5 2.8(2) . . . . ?
C16 C3 C4 O1 178.41(10) . . . . ?
C16 C3 C4 C14 -3.08(18) . . . . ?
C16 C17 C18 C19 -1.65(18) . . . . ?
C16 C21 C20 C19 -0.22(18) . . . . ?
N1 C2 C5 C6 -1.03(14) . . . . ?
N1 C7 C8 C13 60.18(18) . . . . ?
N1 C7 C8 C9 -121.60(14) . . . . ?
N1 C7 C6 C5 0.00(14) . . . . ?
C3 C16 C17 C18 -178.26(11) . . . . ?
C3 C16 C21 C20 179.22(11) . . . . ?
C3 C2 C5 C6 177.50(13) . . . . ?
C3 C4 C14 O4 162.40(11) . . . . ?
C3 C4 C14 O3 -17.79(19) . . . . ?
C17 C16 C3 C2 -65.41(15) . . . . ?
C17 C16 C3 C4 115.38(13) . . . . ?
C17 C16 C21 C20 -0.45(18) . . . . ?
N2 C19 C20 C21 -178.49(11) . . . . ?
N2 C19 C18 C17 179.43(11) . . . . ?
C21 C16 C3 C2 114.92(13) . . . . ?
C21 C16 C3 C4 -64.29(16) . . . . ?
C21 C16 C17 C18 1.41(18) . . . . ?
C20 C19 N2 O6 -4.29(17) . . . . ?
C20 C19 N2 O5 176.39(11) . . . . ?
C20 C19 C18 C17 0.99(19) . . . . ?
C2 N1 C1 O1 5.70(16) . . . . ?
C2 N1 C1 O2 -176.32(12) . . . . ?
C2 N1 C7 C8 178.99(11) . . . . ?
C2 N1 C7 C6 -0.64(13) . . . . ?
C2 C3 C4 O1 -0.81(16) . . . . ?
C2 C3 C4 C14 177.70(10) . . . . ?
C2 C5 C6 C7 0.66(15) . . . . ?
C4 O1 C1 O2 175.76(11) . . . . ?
C4 O1 C1 N1 -6.10(15) . . . . ?
C4 C3 C2 N1 0.45(16) . . . . ?
C4 C3 C2 C5 -177.95(13) . . . . ?
C18 C19 N2 O6 177.21(12) . . . . ?
C18 C19 N2 O5 -2.12(17) . . . . ?
C18 C19 C20 C21 -0.05(18) . . . . ?
C1 O1 C4 C3 3.93(16) . . . . ?
C1 O1 C4 C14 -174.77(10) . . . . ?
C1 N1 C2 C3 -3.09(16) . . . . ?
C1 N1 C2 C5 175.71(11) . . . . ?
C1 N1 C7 C8 4.61(19) . . . . ?
C1 N1 C7 C6 -175.02(11) . . . . ?
C7 N1 C2 C3 -177.74(10) . . . . ?
C7 N1 C2 C5 1.06(13) . . . . ?
C7 N1 C1 O1 179.33(10) . . . . ?
C7 N1 C1 O2 -2.7(2) . . . . ?
C7 C8 C13 C12 179.55(12) . . . . ?
C7 C8 C9 C10 -179.55(13) . . . . ?
C8 C7 C6 C5 -179.61(12) . . . . ?
C8 C13 C12 C11 -0.3(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C6 C7 C8 C13 -120.28(15) . . . . ?
C6 C7 C8 C9 57.94(19) . . . . ?
C13 C8 C9 C10 -1.3(2) . . . . ?
C15 O4 C14 O3 4.30(17) . . . . ?
C15 O4 C14 C4 -175.89(9) . . . . ?
C9 C8 C13 C12 1.3(2) . . . . ?
C12 C11 C10 C9 0.9(2) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
