# Electronic Supplementary Material (ESI) for Green 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_20190478
_database_code_depnum_ccdc_archive 'CCDC 1923193'
loop_
_audit_author_name
_audit_author_address
'Guangmiao Gu'
;University
China
;
_audit_update_record             
;
2019-06-15 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N O4'
_chemical_formula_sum            'C22 H23 N O4'
_chemical_formula_weight         365.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
_chemical_oxdiff_usercomment     1
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                   13.2745(8)
_cell_length_b                   7.8001(2)
_cell_length_c                   24.2247(14)
_cell_angle_alpha                90
_cell_angle_beta                 129.278(10)
_cell_angle_gamma                90
_cell_volume                     1941.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1390
_cell_measurement_theta_min      4.2860
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7250
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.880
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   14.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   69.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   62.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   15.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
 10 omega  -30.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega   58.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  159.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
 13 omega   93.00  163.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega  152.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   88.00  163.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
 17 omega  147.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  101.00  132.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 20 omega  125.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0366997000
_diffrn_orient_matrix_UB_12      -0.0683542000
_diffrn_orient_matrix_UB_13      -0.0448469000
_diffrn_orient_matrix_UB_21      -0.1389885000
_diffrn_orient_matrix_UB_22      -0.0703114000
_diffrn_orient_matrix_UB_23      -0.0554874000
_diffrn_orient_matrix_UB_31      -0.0425222000
_diffrn_orient_matrix_UB_32      0.1714972000
_diffrn_orient_matrix_UB_33      -0.0407323000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2728
_reflns_number_total             3471
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.040
_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)+(0.0660P)²+0.3745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1387
_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
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.1445(2) 0.8882(3) 0.50465(11) 0.0499(5) Uani 1 1 d . . . . .
H1 H 0.0645 0.9399 0.4702 0.060 Uiso 1 1 calc R . . . .
C2 C 0.1834(2) 0.8520(3) 0.57116(12) 0.0620(6) Uani 1 1 d . . . . .
H2 H 0.1295 0.8815 0.5818 0.074 Uiso 1 1 calc R . . . .
C3 C 0.3018(3) 0.7720(4) 0.62276(12) 0.0671(6) Uani 1 1 d . . . . .
H3 H 0.3245 0.7470 0.6669 0.081 Uiso 1 1 calc R . . . .
C4 C 0.3861(2) 0.7289(3) 0.61026(10) 0.0580(5) Uani 1 1 d . . . . .
H4 H 0.4653 0.6758 0.6450 0.070 Uiso 1 1 calc R . . . .
C5 C 0.34786(18) 0.7680(2) 0.54319(9) 0.0433(4) Uani 1 1 d . . . . .
C6 C 0.22752(17) 0.8459(2) 0.48955(9) 0.0405(4) Uani 1 1 d . . . . .
C7 C 0.22243(16) 0.8647(2) 0.42907(9) 0.0375(4) Uani 1 1 d . . . . .
C8 C 0.33589(16) 0.8008(2) 0.44729(9) 0.0373(4) Uani 1 1 d . . . . .
C9 C 0.37824(16) 0.7883(2) 0.40380(9) 0.0381(4) Uani 1 1 d . . . . .
C10 C 0.49993(18) 0.8448(3) 0.42875(10) 0.0475(4) Uani 1 1 d . . . . .
H10 H 0.5562 0.8945 0.4737 0.057 Uiso 1 1 calc R . . . .
C11 C 0.5386(2) 0.8282(3) 0.38792(12) 0.0577(5) Uani 1 1 d . . . . .
H11 H 0.6202 0.8668 0.4053 0.069 Uiso 1 1 calc R . . . .
C12 C 0.4555(2) 0.7540(4) 0.32109(11) 0.0631(6) Uani 1 1 d . . . . .
H12 H 0.4821 0.7403 0.2939 0.076 Uiso 1 1 calc R . . . .
C13 C 0.3340(2) 0.7005(3) 0.29485(10) 0.0583(6) Uani 1 1 d . . . . .
H13 H 0.2777 0.6530 0.2494 0.070 Uiso 1 1 calc R . . . .
C14 C 0.29476(17) 0.7168(3) 0.33559(9) 0.0450(4) Uani 1 1 d . . . . .
H14 H 0.2123 0.6799 0.3175 0.054 Uiso 1 1 calc R . . . .
C15 C 0.11646(16) 0.9532(2) 0.35961(9) 0.0418(4) Uani 1 1 d . . . . .
H15 H 0.1537 0.9803 0.3363 0.050 Uiso 1 1 calc R . . . .
C16 C 0.07494(17) 1.1237(3) 0.37087(9) 0.0434(4) Uani 1 1 d . . . . .
C17 C 0.1493(3) 1.3962(3) 0.42652(16) 0.0695(7) Uani 1 1 d . . . . .
H17A H 0.0731 1.4410 0.3814 0.083 Uiso 1 1 calc R . . . .
H17B H 0.2221 1.4709 0.4433 0.083 Uiso 1 1 calc R . . . .
C18 C 0.1261(3) 1.3974(4) 0.47908(17) 0.0834(8) Uani 1 1 d . . . . .
H18A H 0.0520 1.3273 0.4618 0.125 Uiso 1 1 calc GR . . . .
H18B H 0.1101 1.5128 0.4855 0.125 Uiso 1 1 calc GR . . . .
H18C H 0.2013 1.3530 0.5238 0.125 Uiso 1 1 calc GR . . . .
C19 C -0.00529(19) 0.8476(3) 0.30663(10) 0.0522(5) Uani 1 1 d . . . . .
C20 C -0.1697(3) 0.6771(5) 0.28964(17) 0.0987(11) Uani 1 1 d . . . . .
H20A H -0.2253 0.7329 0.2434 0.118 Uiso 1 1 calc R . . . .
H20B H -0.1523 0.5615 0.2829 0.118 Uiso 1 1 calc R . . . .
C21 C -0.2337(4) 0.6712(7) 0.3191(3) 0.157(2) Uani 1 1 d . . . . .
H21A H -0.3128 0.6066 0.2881 0.236 Uiso 1 1 calc GR . . . .
H21B H -0.2536 0.7856 0.3240 0.236 Uiso 1 1 calc GR . . . .
H21C H -0.1781 0.6172 0.3650 0.236 Uiso 1 1 calc GR . . . .
C22 C 0.5447(2) 0.6732(3) 0.56060(11) 0.0578(5) Uani 1 1 d . . . . .
H22A H 0.6055 0.7614 0.5915 0.087 Uiso 1 1 calc GR . . . .
H22B H 0.5629 0.6333 0.5302 0.087 Uiso 1 1 calc GR . . . .
H22C H 0.5524 0.5795 0.5888 0.087 Uiso 1 1 calc GR . . . .
N1 N 0.41334(14) 0.7415(2) 0.51718(8) 0.0419(4) Uani 1 1 d . . . . .
O1 O -0.03515(13) 1.1615(2) 0.34276(9) 0.0644(4) Uani 1 1 d . . . . .
O2 O 0.17712(13) 1.22361(18) 0.41543(8) 0.0543(4) Uani 1 1 d . . . . .
O3 O -0.05669(19) 0.8385(3) 0.24482(9) 0.0923(7) Uani 1 1 d . . . . .
O4 O -0.04826(16) 0.7708(3) 0.33672(9) 0.0732(5) Uani 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
C1 H1 0.9300 . ?
C1 C2 1.375(3) . ?
C1 C6 1.402(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(3) . ?
C5 C6 1.408(3) . ?
C5 N1 1.374(2) . ?
C6 C7 1.431(2) . ?
C7 C8 1.368(2) . ?
C7 C15 1.513(2) . ?
C8 C9 1.478(2) . ?
C8 N1 1.390(2) . ?
C9 C10 1.390(3) . ?
C9 C14 1.397(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9800 . ?
C15 C16 1.529(3) . ?
C15 C19 1.521(3) . ?
C16 O1 1.194(2) . ?
C16 O2 1.326(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.487(4) . ?
C17 O2 1.465(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O3 1.191(3) . ?
C19 O4 1.320(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.414(5) . ?
C20 O4 1.451(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 N1 1.452(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
C2 C1 H1 120.5 . . ?
C2 C1 C6 118.94(19) . . ?
C6 C1 H1 120.5 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.2(2) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 C6 122.21(19) . . ?
N1 C5 C4 129.18(18) . . ?
N1 C5 C6 108.61(15) . . ?
C1 C6 C5 118.72(17) . . ?
C1 C6 C7 135.03(17) . . ?
C5 C6 C7 106.24(16) . . ?
C6 C7 C15 126.39(16) . . ?
C8 C7 C6 107.68(15) . . ?
C8 C7 C15 125.72(16) . . ?
C7 C8 C9 129.19(16) . . ?
C7 C8 N1 109.18(15) . . ?
N1 C8 C9 121.63(15) . . ?
C10 C9 C8 122.06(16) . . ?
C10 C9 C14 118.31(17) . . ?
C14 C9 C8 119.63(16) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.06(18) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.77(19) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.32(19) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.39(18) . . ?
C13 C14 H14 119.8 . . ?
C7 C15 H15 106.6 . . ?
C7 C15 C16 112.64(14) . . ?
C7 C15 C19 115.73(16) . . ?
C16 C15 H15 106.6 . . ?
C19 C15 H15 106.6 . . ?
C19 C15 C16 108.15(15) . . ?
O1 C16 C15 124.20(18) . . ?
O1 C16 O2 124.82(19) . . ?
O2 C16 C15 110.98(15) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
O2 C17 H17A 109.2 . . ?
O2 C17 H17B 109.2 . . ?
O2 C17 C18 112.1(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 C15 123.4(2) . . ?
O3 C19 O4 124.3(2) . . ?
O4 C19 C15 112.32(16) . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C21 C20 O4 110.1(3) . . ?
O4 C20 H20A 109.6 . . ?
O4 C20 H20B 109.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
C5 N1 C8 108.29(14) . . ?
C5 N1 C22 122.74(16) . . ?
C8 N1 C22 128.85(16) . . ?
C16 O2 C17 116.27(16) . . ?
C19 O4 C20 116.6(2) . . ?

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
C1 C2 C3 C4 1.3(4) . . . . ?
C1 C6 C7 C8 178.7(2) . . . . ?
C1 C6 C7 C15 3.7(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C6 C7 -179.0(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C3 C4 C5 N1 179.0(2) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 -179.65(19) . . . . ?
C4 C5 N1 C8 179.7(2) . . . . ?
C4 C5 N1 C22 -4.0(3) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C5 C6 C7 C15 -175.37(17) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
C6 C5 N1 C8 -0.4(2) . . . . ?
C6 C5 N1 C22 175.93(18) . . . . ?
C6 C7 C8 C9 179.30(17) . . . . ?
C6 C7 C8 N1 0.1(2) . . . . ?
C6 C7 C15 C16 44.1(2) . . . . ?
C6 C7 C15 C19 -81.0(2) . . . . ?
C7 C8 C9 C10 130.7(2) . . . . ?
C7 C8 C9 C14 -49.7(3) . . . . ?
C7 C8 N1 C5 0.2(2) . . . . ?
C7 C8 N1 C22 -175.83(19) . . . . ?
C7 C15 C16 O1 -128.1(2) . . . . ?
C7 C15 C16 O2 52.4(2) . . . . ?
C7 C15 C19 O3 -133.9(2) . . . . ?
C7 C15 C19 O4 47.4(2) . . . . ?
C8 C7 C15 C16 -130.11(18) . . . . ?
C8 C7 C15 C19 104.8(2) . . . . ?
C8 C9 C10 C11 178.45(19) . . . . ?
C8 C9 C14 C13 -178.47(19) . . . . ?
C9 C8 N1 C5 -179.12(16) . . . . ?
C9 C8 N1 C22 4.9(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C9 C14 C13 1.1(3) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
C11 C12 C13 C14 -1.5(4) . . . . ?
C12 C13 C14 C9 0.2(3) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C15 C7 C8 C9 -5.6(3) . . . . ?
C15 C7 C8 N1 175.19(16) . . . . ?
C15 C16 O2 C17 175.57(17) . . . . ?
C15 C19 O4 C20 175.5(2) . . . . ?
C16 C15 C19 O3 98.7(2) . . . . ?
C16 C15 C19 O4 -80.0(2) . . . . ?
C18 C17 O2 C16 81.3(3) . . . . ?
C19 C15 C16 O1 1.1(3) . . . . ?
C19 C15 C16 O2 -178.47(16) . . . . ?
C21 C20 O4 C19 -152.9(4) . . . . ?
N1 C5 C6 C1 -178.82(17) . . . . ?
N1 C5 C6 C7 0.4(2) . . . . ?
N1 C8 C9 C10 -50.1(3) . . . . ?
N1 C8 C9 C14 129.40(18) . . . . ?
O1 C16 O2 C17 -4.0(3) . . . . ?
O3 C19 O4 C20 -3.2(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
