# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_psu-863(xr-1)
_database_code_depnum_ccdc_archive 'CCDC 2102039'
loop_
_audit_author_name
_audit_author_address
'Aleksandr Rubtsov'
;Perm State University
Russia
;
_audit_update_record             
;
2021-08-07 deposited with the CCDC.	2021-10-04 downloaded from the CCDC.
;
_audit_creation_date             2021-06-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'methyl (E)-3-(3,5-diphenyl-1H-pyrrol-2-yl)acrylate'
_chemical_formula_moiety         'C20 H17 N O'
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_chemical_absolute_configuration unk
_chemical_melting_point          470
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      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                   12.982(4)
_cell_length_b                   7.0971(18)
_cell_length_c                   17.255(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.75(3)
_cell_angle_gamma                90
_cell_volume                     1561.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2065
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.0770
_cell_measurement_theta_min      3.6420
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8369
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.711
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         3.112
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   71.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509   57.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -56.00   36.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509  -57.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega -107.00  -81.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978 -178.0000   60.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0027152000
_diffrn_orient_matrix_UB_12      0.0099555000
_diffrn_orient_matrix_UB_13      -0.0404391000
_diffrn_orient_matrix_UB_21      -0.0553426000
_diffrn_orient_matrix_UB_22      -0.0087680000
_diffrn_orient_matrix_UB_23      -0.0098579000
_diffrn_orient_matrix_UB_31      -0.0049084000
_diffrn_orient_matrix_UB_32      0.0991643000
_diffrn_orient_matrix_UB_33      0.0031746000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.549
_reflns_Friedel_fraction_full    0.728
_reflns_Friedel_fraction_max     0.545
_reflns_number_gt                3828
_reflns_number_total             6210
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.050

_refine_ls_extinction_coef       0.017(2)
_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   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.016
_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)+(0.0628P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1644
_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:
 C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C2A(H2A), C5A(H5A), C6A(H6A),
  C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4799(2) 0.5613(6) 0.98739(16) 0.0806(10) Uani 1 1 d . . . . .
N1 N 0.6932(3) 0.6978(5) 0.77136(19) 0.0542(9) Uani 1 1 d . . . . .
H1 H 0.724(3) 0.684(6) 0.822(2) 0.054(11) Uiso 1 1 d . . . . .
C1 C 0.7482(3) 0.7290(6) 0.7121(2) 0.0520(10) Uani 1 1 d . . . . .
C2 C 0.6768(3) 0.7462(6) 0.6439(2) 0.0569(10) Uani 1 1 d . . . . .
H2 H 0.692508 0.768509 0.594264 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5749(3) 0.7249(5) 0.66057(19) 0.0501(9) Uani 1 1 d . . . . .
C4 C 0.5880(3) 0.6972(6) 0.74213(19) 0.0502(9) Uani 1 1 d . . . . .
C5 C 0.5110(3) 0.6796(6) 0.79236(19) 0.0508(9) Uani 1 1 d . . . . .
H5 H 0.441633 0.705790 0.770000 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5312(3) 0.6287(6) 0.8683(2) 0.0570(11) Uani 1 1 d . . . . .
H6 H 0.600354 0.600318 0.890477 0.068 Uiso 1 1 calc R U . . .
C7 C 0.4540(3) 0.6144(6) 0.9187(2) 0.0553(10) Uani 1 1 d . . . . .
C8 C 0.3423(3) 0.6607(8) 0.8888(2) 0.0714(12) Uani 1 1 d . . . . .
H8A H 0.309960 0.560023 0.855770 0.107 Uiso 1 1 calc R U . . .
H8B H 0.337786 0.775163 0.858695 0.107 Uiso 1 1 calc R U . . .
H8C H 0.306885 0.676775 0.932432 0.107 Uiso 1 1 calc R U . . .
C9 C 0.4770(3) 0.7248(5) 0.60262(19) 0.0488(9) Uani 1 1 d . . . . .
C10 C 0.3926(3) 0.6115(6) 0.6108(2) 0.0550(10) Uani 1 1 d . . . . .
H10 H 0.396830 0.536742 0.655581 0.066 Uiso 1 1 calc R U . . .
C11 C 0.3028(3) 0.6076(6) 0.5540(2) 0.0643(11) Uani 1 1 d . . . . .
H11 H 0.246383 0.532581 0.560672 0.077 Uiso 1 1 calc R U . . .
C12 C 0.2975(3) 0.7152(7) 0.4877(2) 0.0674(12) Uani 1 1 d . . . . .
H12 H 0.237641 0.710729 0.448591 0.081 Uiso 1 1 calc R U . . .
C13 C 0.3791(4) 0.8295(6) 0.4781(2) 0.0610(11) Uani 1 1 d . . . . .
H13 H 0.374240 0.903336 0.433070 0.073 Uiso 1 1 calc R U . . .
C14 C 0.4682(3) 0.8349(6) 0.5352(2) 0.0577(10) Uani 1 1 d . . . . .
H14 H 0.523378 0.913165 0.528582 0.069 Uiso 1 1 calc R U . . .
C15 C 0.8624(3) 0.7392(6) 0.7257(2) 0.0554(10) Uani 1 1 d . . . . .
C16 C 0.9119(4) 0.8224(7) 0.6694(2) 0.0680(12) Uani 1 1 d . . . . .
H16 H 0.871463 0.868374 0.623072 0.082 Uiso 1 1 calc R U . . .
C17 C 1.0193(4) 0.8381(7) 0.6809(3) 0.0763(13) Uani 1 1 d . . . . .
H17 H 1.050895 0.892809 0.642339 0.092 Uiso 1 1 calc R U . . .
C18 C 1.0792(4) 0.7732(8) 0.7491(3) 0.0776(14) Uani 1 1 d . . . . .
H18 H 1.151808 0.785322 0.757507 0.093 Uiso 1 1 calc R U . . .
C19 C 1.0318(3) 0.6892(8) 0.8056(3) 0.0781(14) Uani 1 1 d . . . . .
H19 H 1.072605 0.643582 0.851832 0.094 Uiso 1 1 calc R U . . .
C20 C 0.9243(3) 0.6728(7) 0.7937(2) 0.0677(12) Uani 1 1 d . . . . .
H20 H 0.893141 0.616209 0.832192 0.081 Uiso 1 1 calc R U . . .
O1A O 0.7931(2) 0.6575(7) -0.05970(16) 0.0932(12) Uani 1 1 d . . . . .
N1A N 0.5640(2) 0.6597(5) 0.15421(18) 0.0505(8) Uani 1 1 d . . . . .
H1A H 0.538(3) 0.641(6) 0.102(2) 0.057(11) Uiso 1 1 d . . . . .
C1A C 0.5066(3) 0.6634(6) 0.21366(19) 0.0483(9) Uani 1 1 d . . . . .
C2A C 0.5762(3) 0.6697(6) 0.28325(19) 0.0519(9) Uani 1 1 d . . . . .
H2A H 0.558852 0.671277 0.333172 0.062 Uiso 1 1 calc R U . . .
C3A C 0.6786(3) 0.6735(6) 0.26720(18) 0.0479(9) Uani 1 1 d . . . . .
C4A C 0.6692(3) 0.6661(5) 0.18549(18) 0.0474(9) Uani 1 1 d . . . . .
C5A C 0.7482(3) 0.6588(6) 0.1376(2) 0.0538(9) Uani 1 1 d . . . . .
H5A H 0.817101 0.647077 0.164096 0.065 Uiso 1 1 calc R U . . .
C6A C 0.7336(3) 0.6670(7) 0.0592(2) 0.0584(10) Uani 1 1 d . . . . .
H6A H 0.665191 0.683094 0.032154 0.070 Uiso 1 1 calc R U . . .
C7A C 0.8152(3) 0.6529(8) 0.0125(2) 0.0679(12) Uani 1 1 d . . . . .
C8A C 0.9259(3) 0.6354(12) 0.0493(3) 0.110(2) Uani 1 1 d . . . . .
H8AA H 0.938468 0.512274 0.072145 0.165 Uiso 1 1 calc R U . . .
H8AB H 0.943062 0.729079 0.089844 0.165 Uiso 1 1 calc R U . . .
H8AC H 0.968679 0.653508 0.010191 0.165 Uiso 1 1 calc R U . . .
C9A C 0.7730(3) 0.6965(5) 0.3276(2) 0.0496(9) Uani 1 1 d . . . . .
C10A C 0.8571(3) 0.8063(6) 0.3167(2) 0.0639(12) Uani 1 1 d . . . . .
H10A H 0.856036 0.864656 0.268322 0.077 Uiso 1 1 calc R U . . .
C11A C 0.9422(4) 0.8305(7) 0.3762(3) 0.0760(14) Uani 1 1 d . . . . .
H11A H 0.997605 0.906475 0.368222 0.091 Uiso 1 1 calc R U . . .
C12A C 0.9457(4) 0.7429(8) 0.4474(3) 0.0748(14) Uani 1 1 d . . . . .
H12A H 1.004056 0.757401 0.487312 0.090 Uiso 1 1 calc R U . . .
C13A C 0.8629(3) 0.6336(7) 0.4599(2) 0.0671(12) Uani 1 1 d . . . . .
H13A H 0.864769 0.575676 0.508452 0.081 Uiso 1 1 calc R U . . .
C14A C 0.7775(3) 0.6101(6) 0.4006(2) 0.0565(10) Uani 1 1 d . . . . .
H14A H 0.721827 0.535472 0.409325 0.068 Uiso 1 1 calc R U . . .
C15A C 0.3927(3) 0.6662(6) 0.1991(2) 0.0526(9) Uani 1 1 d . . . . .
C16A C 0.3422(3) 0.7033(7) 0.2615(2) 0.0652(12) Uani 1 1 d . . . . .
H16A H 0.382287 0.723080 0.311388 0.078 Uiso 1 1 calc R U . . .
C17A C 0.2347(3) 0.7120(8) 0.2520(3) 0.0755(14) Uani 1 1 d . . . . .
H17A H 0.202894 0.738337 0.294781 0.091 Uiso 1 1 calc R U . . .
C18A C 0.1755(4) 0.6815(9) 0.1794(3) 0.0843(15) Uani 1 1 d . . . . .
H18A H 0.102727 0.685565 0.172075 0.101 Uiso 1 1 calc R U . . .
C19A C 0.2244(4) 0.6449(10) 0.1171(3) 0.0987(19) Uani 1 1 d . . . . .
H19A H 0.183959 0.625370 0.067309 0.118 Uiso 1 1 calc R U . . .
C20A C 0.3322(3) 0.6362(8) 0.1266(2) 0.0752(14) Uani 1 1 d . . . . .
H20A H 0.363596 0.609856 0.083547 0.090 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
O1 C7 1.229(4) . ?
N1 H1 0.90(3) . ?
N1 C1 1.370(5) . ?
N1 C4 1.365(5) . ?
C1 C2 1.361(5) . ?
C1 C15 1.459(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.413(5) . ?
C3 C4 1.400(4) . ?
C3 C9 1.463(5) . ?
C4 C5 1.446(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.337(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.449(5) . ?
C7 C8 1.482(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.387(5) . ?
C9 C14 1.388(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(5) . ?
C15 C20 1.376(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.364(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(5) . ?
C20 H20 0.9300 . ?
O1A C7A 1.226(4) . ?
N1A H1A 0.91(3) . ?
N1A C1A 1.376(4) . ?
N1A C4A 1.373(4) . ?
C1A C2A 1.362(4) . ?
C1A C15A 1.453(5) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.408(5) . ?
C3A C4A 1.393(4) . ?
C3A C9A 1.462(5) . ?
C4A C5A 1.432(5) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.331(5) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.449(5) . ?
C7A C8A 1.464(6) . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C9A C10A 1.383(5) . ?
C9A C14A 1.394(5) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.371(5) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.370(6) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.375(7) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.371(5) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.386(5) . ?
C15A C20A 1.365(5) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.376(6) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.359(6) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.371(6) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.379(6) . ?
C20A H20A 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 N1 H1 123(2) . . ?
C4 N1 H1 127(2) . . ?
C4 N1 C1 110.5(3) . . ?
N1 C1 C15 122.9(3) . . ?
C2 C1 N1 107.1(3) . . ?
C2 C1 C15 130.0(4) . . ?
C1 C2 H2 125.5 . . ?
C1 C2 C3 109.1(3) . . ?
C3 C2 H2 125.5 . . ?
C2 C3 C9 126.0(3) . . ?
C4 C3 C2 106.1(3) . . ?
C4 C3 C9 127.9(3) . . ?
N1 C4 C3 107.3(3) . . ?
N1 C4 C5 122.4(3) . . ?
C3 C4 C5 130.3(3) . . ?
C4 C5 H5 117.3 . . ?
C6 C5 C4 125.4(3) . . ?
C6 C5 H5 117.3 . . ?
C5 C6 H6 117.4 . . ?
C5 C6 C7 125.2(4) . . ?
C7 C6 H6 117.4 . . ?
O1 C7 C6 120.3(4) . . ?
O1 C7 C8 118.6(4) . . ?
C6 C7 C8 121.1(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C3 122.1(3) . . ?
C10 C9 C14 117.9(3) . . ?
C14 C9 C3 119.9(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.3(4) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(4) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(4) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C1 119.7(4) . . ?
C20 C15 C1 122.3(4) . . ?
C20 C15 C16 118.0(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.4(4) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(5) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.7(5) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(5) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.8(4) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C1A N1A H1A 126(2) . . ?
C4A N1A H1A 123(2) . . ?
C4A N1A C1A 110.1(3) . . ?
N1A C1A C15A 123.1(3) . . ?
C2A C1A N1A 107.2(3) . . ?
C2A C1A C15A 129.6(3) . . ?
C1A C2A H2A 125.6 . . ?
C1A C2A C3A 108.8(3) . . ?
C3A C2A H2A 125.6 . . ?
C2A C3A C9A 124.0(3) . . ?
C4A C3A C2A 106.9(3) . . ?
C4A C3A C9A 129.0(3) . . ?
N1A C4A C3A 107.0(3) . . ?
N1A C4A C5A 122.6(3) . . ?
C3A C4A C5A 130.4(3) . . ?
C4A C5A H5A 116.4 . . ?
C6A C5A C4A 127.1(3) . . ?
C6A C5A H5A 116.4 . . ?
C5A C6A H6A 117.2 . . ?
C5A C6A C7A 125.6(4) . . ?
C7A C6A H6A 117.2 . . ?
O1A C7A C6A 120.5(4) . . ?
O1A C7A C8A 117.9(4) . . ?
C6A C7A C8A 121.6(4) . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C10A C9A C3A 123.0(3) . . ?
C10A C9A C14A 118.0(3) . . ?
C14A C9A C3A 118.9(3) . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A C9A 121.0(4) . . ?
C11A C10A H10A 119.5 . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A C10A 120.1(4) . . ?
C12A C11A H11A 119.9 . . ?
C11A C12A H12A 120.0 . . ?
C11A C12A C13A 120.0(4) . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A C12A 120.0(4) . . ?
C14A C13A H13A 120.0 . . ?
C9A C14A H14A 119.6 . . ?
C13A C14A C9A 120.8(4) . . ?
C13A C14A H14A 119.6 . . ?
C16A C15A C1A 118.8(3) . . ?
C20A C15A C1A 123.3(4) . . ?
C20A C15A C16A 117.9(4) . . ?
C15A C16A H16A 118.9 . . ?
C17A C16A C15A 122.1(4) . . ?
C17A C16A H16A 118.9 . . ?
C16A C17A H17A 120.3 . . ?
C18A C17A C16A 119.3(4) . . ?
C18A C17A H17A 120.3 . . ?
C17A C18A H18A 120.4 . . ?
C17A C18A C19A 119.2(4) . . ?
C19A C18A H18A 120.4 . . ?
C18A C19A H19A 119.2 . . ?
C18A C19A C20A 121.6(4) . . ?
C20A C19A H19A 119.2 . . ?
C15A C20A C19A 119.9(4) . . ?
C15A C20A H20A 120.0 . . ?
C19A C20A H20A 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1A 0.90(3) 2.08(3) 2.975(4) 178(4) 1_556 yes
N1A H1A O1 0.91(3) 2.06(4) 2.965(4) 172(4) 1_554 yes

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
N1 C1 C2 C3 -0.2(5) . . . . ?
N1 C1 C15 C16 -161.8(4) . . . . ?
N1 C1 C15 C20 16.7(6) . . . . ?
N1 C4 C5 C6 -12.8(6) . . . . ?
C1 N1 C4 C3 1.3(4) . . . . ?
C1 N1 C4 C5 -175.9(4) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C2 C3 C9 -176.8(4) . . . . ?
C1 C15 C16 C17 178.7(4) . . . . ?
C1 C15 C20 C19 -178.3(4) . . . . ?
C2 C1 C15 C16 18.3(7) . . . . ?
C2 C1 C15 C20 -163.2(5) . . . . ?
C2 C3 C4 N1 -1.4(4) . . . . ?
C2 C3 C4 C5 175.5(4) . . . . ?
C2 C3 C9 C10 144.4(4) . . . . ?
C2 C3 C9 C14 -32.8(6) . . . . ?
C3 C4 C5 C6 170.7(4) . . . . ?
C3 C9 C10 C11 -177.2(4) . . . . ?
C3 C9 C14 C13 176.6(4) . . . . ?
C4 N1 C1 C2 -0.7(5) . . . . ?
C4 N1 C1 C15 179.3(4) . . . . ?
C4 C3 C9 C10 -32.9(6) . . . . ?
C4 C3 C9 C14 149.8(4) . . . . ?
C4 C5 C6 C7 178.9(4) . . . . ?
C5 C6 C7 O1 178.0(4) . . . . ?
C5 C6 C7 C8 -1.2(7) . . . . ?
C9 C3 C4 N1 176.4(4) . . . . ?
C9 C3 C4 C5 -6.7(7) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C9 C14 C13 -0.8(6) . . . . ?
C10 C11 C12 C13 -1.5(7) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C12 C13 C14 C9 0.3(6) . . . . ?
C14 C9 C10 C11 0.1(6) . . . . ?
C15 C1 C2 C3 179.8(4) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
C16 C15 C20 C19 0.2(7) . . . . ?
C16 C17 C18 C19 1.1(8) . . . . ?
C17 C18 C19 C20 -0.7(8) . . . . ?
C18 C19 C20 C15 0.1(8) . . . . ?
C20 C15 C16 C17 0.1(7) . . . . ?
N1A C1A C2A C3A 1.1(5) . . . . ?
N1A C1A C15A C16A -168.7(4) . . . . ?
N1A C1A C15A C20A 10.5(6) . . . . ?
N1A C4A C5A C6A 8.3(7) . . . . ?
C1A N1A C4A C3A 0.2(4) . . . . ?
C1A N1A C4A C5A 178.2(4) . . . . ?
C1A C2A C3A C4A -1.0(5) . . . . ?
C1A C2A C3A C9A 174.6(4) . . . . ?
C1A C15A C16A C17A 178.7(4) . . . . ?
C1A C15A C20A C19A -178.7(5) . . . . ?
C2A C1A C15A C16A 9.0(7) . . . . ?
C2A C1A C15A C20A -171.8(5) . . . . ?
C2A C3A C4A N1A 0.5(4) . . . . ?
C2A C3A C4A C5A -177.3(4) . . . . ?
C2A C3A C9A C10A -139.9(4) . . . . ?
C2A C3A C9A C14A 37.6(6) . . . . ?
C3A C4A C5A C6A -174.2(4) . . . . ?
C3A C9A C10A C11A 177.1(4) . . . . ?
C3A C9A C14A C13A -177.6(4) . . . . ?
C4A N1A C1A C2A -0.8(4) . . . . ?
C4A N1A C1A C15A 177.4(3) . . . . ?
C4A C3A C9A C10A 34.7(6) . . . . ?
C4A C3A C9A C14A -147.8(4) . . . . ?
C4A C5A C6A C7A -177.8(5) . . . . ?
C5A C6A C7A O1A 178.2(5) . . . . ?
C5A C6A C7A C8A -2.6(8) . . . . ?
C9A C3A C4A N1A -174.8(4) . . . . ?
C9A C3A C4A C5A 7.4(7) . . . . ?
C9A C10A C11A C12A 1.1(7) . . . . ?
C10A C9A C14A C13A 0.0(6) . . . . ?
C10A C11A C12A C13A -1.3(8) . . . . ?
C11A C12A C13A C14A 1.0(8) . . . . ?
C12A C13A C14A C9A -0.3(7) . . . . ?
C14A C9A C10A C11A -0.4(6) . . . . ?
C15A C1A C2A C3A -176.9(4) . . . . ?
C15A C16A C17A C18A 0.6(8) . . . . ?
C16A C15A C20A C19A 0.5(8) . . . . ?
C16A C17A C18A C19A -0.7(9) . . . . ?
C17A C18A C19A C20A 0.7(10) . . . . ?
C18A C19A C20A C15A -0.6(10) . . . . ?
C20A C15A C16A C17A -0.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
