# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_DM41_0ma
_database_code_depnum_ccdc_archive 'CCDC 2125168'
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry Polish Academy of Science
Poland
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N2 O2'
_chemical_formula_sum            'C22 H22 N2 O2'
_chemical_formula_weight         346.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   9.4752(2)
_cell_length_b                   13.0433(4)
_cell_length_c                   14.6294(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.573(2)
_cell_angle_gamma                90
_cell_volume                     1764.66(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2465
_cell_measurement_theta_min      4.59
_cell_measurement_theta_max      68.51

_exptl_crystal_description       cubes
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.184
_exptl_absorpt_coefficient_mu    0.668
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7890
_exptl_absorpt_correction_T_max  0.8870
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51710
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.591
_diffrn_reflns_theta_max         68.511
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3195
_reflns_number_gt                2465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0915P)²+0.6763P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3195
_refine_ls_number_parameters     280
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1801
_refine_ls_wR_factor_gt          0.1695
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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 1.09503(17) 0.75076(14) 0.13373(13) 0.0660(5) Uani 1 1 d . . . . .
O2 O 0.54193(18) 0.66592(15) 0.24989(13) 0.0715(6) Uani 1 1 d . . . . .
N1 N 0.55976(19) 0.75350(14) 0.12004(12) 0.0473(5) Uani 1 1 d . . . . .
N2 N 1.06335(18) 0.62371(14) 0.23155(12) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.4193(3) 0.7900(2) 0.09673(18) 0.0584(6) Uani 1 1 d . . . . .
C2 C 0.4037(3) 0.8411(2) 0.01498(19) 0.0648(7) Uani 1 1 d . . . . .
C3 C 0.5354(3) 0.8365(2) -0.01490(18) 0.0582(6) Uani 1 1 d . . . . .
C4 C 0.6323(2) 0.78200(17) 0.05125(14) 0.0452(5) Uani 1 1 d . . . . .
C5 C 0.7819(2) 0.75822(17) 0.06177(15) 0.0455(5) Uani 1 1 d . . . . .
C6 C 0.8520(2) 0.71034(16) 0.14304(14) 0.0414(5) Uani 1 1 d . . . . .
C7 C 1.0105(2) 0.69888(17) 0.16544(15) 0.0465(5) Uani 1 1 d . . . . .
C8 C 1.2060(3) 0.5937(2) 0.26097(18) 0.0584(6) Uani 1 1 d . . . . .
C9 C 1.2093(3) 0.5104(2) 0.31588(18) 0.0648(7) Uani 1 1 d . . . . .
H9 H 1.2919 0.4747 0.3449 0.078 Uiso 1 1 calc R U . . .
C10 C 1.0668(3) 0.4863(2) 0.32208(19) 0.0621(7) Uani 1 1 d . . . . .
C11 C 0.9763(2) 0.55733(17) 0.26959(15) 0.0487(5) Uani 1 1 d . . . . .
C12 C 0.8246(2) 0.57441(18) 0.25331(14) 0.0484(6) Uani 1 1 d . . . . .
C13 C 0.7680(2) 0.65874(17) 0.20174(14) 0.0444(5) Uani 1 1 d . . . . .
C14 C 0.6162(2) 0.68880(18) 0.19511(15) 0.0493(6) Uani 1 1 d . . . . .
C15 C 0.7341(3) 0.4893(2) 0.2803(2) 0.0679(8) Uani 1 1 d D . . . .
C16A C 0.6277(5) 0.4484(4) 0.2028(3) 0.0524(11) Uani 0.5 1 d D . P . .
H16A H 0.5765 0.5048 0.1669 0.063 Uiso 0.5 1 calc R U P . .
H16B H 0.5578 0.4084 0.2271 0.063 Uiso 0.5 1 calc R U P . .
C17A C 0.6944(7) 0.3811(4) 0.1382(5) 0.0655(14) Uani 0.5 1 d D . P . .
H17A H 0.6173 0.3414 0.0997 0.079 Uiso 0.5 1 calc R U P . .
H17B H 0.7593 0.3330 0.1770 0.079 Uiso 0.5 1 calc R U P . .
C18 C 0.7851(4) 0.4380(4) 0.0679(4) 0.1217(19) Uani 1 1 d D . . . .
C19 C 0.7157(4) 0.5190(3) -0.0032(4) 0.1222(17) Uani 1 1 d . . . . .
H19A H 0.6434 0.4872 -0.0521 0.147 Uiso 1 1 calc R U . . .
H19B H 0.6680 0.5703 0.0275 0.147 Uiso 1 1 calc R U . . .
C20 C 0.8294(4) 0.5696(3) -0.0457(3) 0.1072(13) Uani 1 1 d . . . . .
H20A H 0.9168 0.5761 0.0028 0.129 Uiso 1 1 calc R U . . .
H20B H 0.8511 0.5240 -0.0932 0.129 Uiso 1 1 calc R U . . .
C21 C 0.7945(4) 0.6726(3) -0.0891(2) 0.1139(15) Uani 1 1 d . . . . .
H21A H 0.6908 0.6761 -0.1129 0.137 Uiso 1 1 calc R U . . .
H21B H 0.8396 0.6777 -0.1425 0.137 Uiso 1 1 calc R U . . .
C22 C 0.8421(3) 0.7698(2) -0.02417(18) 0.0683(8) Uani 1 1 d . . . . .
H22A H 0.9467 0.7742 -0.0070 0.082 Uiso 1 1 calc R U . . .
H22B H 0.8053 0.8320 -0.0573 0.082 Uiso 1 1 calc R U . . .
H1 H 0.348(3) 0.773(2) 0.1350(19) 0.071(8) Uiso 1 1 d . . . . .
H2 H 0.313(3) 0.875(2) -0.019(2) 0.075(8) Uiso 1 1 d . . . . .
H3 H 0.553(3) 0.867(2) -0.073(2) 0.072(8) Uiso 1 1 d . . . . .
H8 H 1.282(3) 0.630(2) 0.2425(18) 0.072(8) Uiso 1 1 d . . . . .
H10 H 1.027(3) 0.428(3) 0.355(2) 0.094(10) Uiso 1 1 d . . . . .
C16B C 0.7119(10) 0.3996(7) 0.1937(6) 0.102(2) Uiso 0.5 1 d D . P . .
H16C H 0.8037 0.3645 0.1997 0.122 Uiso 0.5 1 calc R U P . .
H16D H 0.6434 0.3495 0.2070 0.122 Uiso 0.5 1 calc R U P . .
H15A H 0.798(3) 0.444(2) 0.3244(19) 0.070(8) Uiso 1 1 d . . . . .
H15B H 0.659(4) 0.517(3) 0.324(3) 0.136(14) Uiso 1 1 d . . . . .
C17B C 0.6635(8) 0.4289(7) 0.0950(6) 0.099(2) Uiso 0.5 1 d D . P . .
H17C H 0.6028 0.3763 0.0596 0.119 Uiso 0.5 1 calc R U P . .
H17D H 0.6109 0.4932 0.0886 0.119 Uiso 0.5 1 calc R U P . .
H18B H 0.811(4) 0.387(3) 0.033(3) 0.121(13) Uiso 1 1 d . . . . .
H18A H 0.882(4) 0.474(3) 0.110(3) 0.116(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.215(3) . ?
O2 C14 1.213(3) . ?
N1 C1 1.384(3) . ?
N1 C4 1.387(3) . ?
N1 C14 1.396(3) . ?
N2 C8 1.383(3) . ?
N2 C7 1.392(3) . ?
N2 C11 1.393(3) . ?
C1 C2 1.349(4) . ?
C1 H1 0.99(3) . ?
C2 C3 1.410(4) . ?
C2 H2 1.00(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.99(3) . ?
C4 C5 1.426(3) . ?
C5 C6 1.379(3) . ?
C5 C22 1.497(3) . ?
C6 C13 1.457(3) . ?
C6 C7 1.473(3) . ?
C8 C9 1.348(4) . ?
C8 H8 0.95(3) . ?
C9 C10 1.408(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10 1.02(3) . ?
C11 C12 1.422(3) . ?
C12 C13 1.375(3) . ?
C12 C15 1.507(3) . ?
C13 C14 1.473(3) . ?
C15 C16A 1.445(5) . ?
C15 C16B 1.703(9) . ?
C15 H15A 0.98(3) . ?
C15 H15B 1.12(4) . ?
C16A C17A 1.524(7) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C17A C18 1.653(7) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18 C17B 1.303(8) . ?
C18 C19 1.527(7) . ?
C18 H18B 0.90(4) . ?
C18 H18A 1.09(4) . ?
C19 C20 1.508(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.491(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.590(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C16B C17B 1.468(10) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?

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 C4 109.30(19) . . ?
C1 N1 C14 125.81(19) . . ?
C4 N1 C14 124.55(18) . . ?
C8 N2 C7 126.5(2) . . ?
C8 N2 C11 108.9(2) . . ?
C7 N2 C11 124.12(18) . . ?
C2 C1 N1 107.6(2) . . ?
C2 C1 H1 130.8(16) . . ?
N1 C1 H1 121.4(16) . . ?
C1 C2 C3 108.7(2) . . ?
C1 C2 H2 125.1(16) . . ?
C3 C2 H2 126.2(16) . . ?
C4 C3 C2 107.7(2) . . ?
C4 C3 H3 127.0(16) . . ?
C2 C3 H3 125.4(16) . . ?
C3 C4 N1 106.75(19) . . ?
C3 C4 C5 133.0(2) . . ?
N1 C4 C5 120.09(19) . . ?
C6 C5 C4 118.18(19) . . ?
C6 C5 C22 124.8(2) . . ?
C4 C5 C22 116.0(2) . . ?
C5 C6 C13 119.68(18) . . ?
C5 C6 C7 120.93(19) . . ?
C13 C6 C7 118.91(18) . . ?
O1 C7 N2 119.4(2) . . ?
O1 C7 C6 125.7(2) . . ?
N2 C7 C6 114.90(18) . . ?
C9 C8 N2 108.0(2) . . ?
C9 C8 H8 130.9(17) . . ?
N2 C8 H8 121.1(17) . . ?
C8 C9 C10 108.7(2) . . ?
C8 C9 H9 125.7 . . ?
C10 C9 H9 125.7 . . ?
C11 C10 C9 107.7(2) . . ?
C11 C10 H10 121.0(18) . . ?
C9 C10 H10 131.3(18) . . ?
C10 C11 N2 106.8(2) . . ?
C10 C11 C12 133.1(2) . . ?
N2 C11 C12 120.04(19) . . ?
C13 C12 C11 118.5(2) . . ?
C13 C12 C15 123.8(2) . . ?
C11 C12 C15 116.9(2) . . ?
C12 C13 C6 119.66(19) . . ?
C12 C13 C14 120.5(2) . . ?
C6 C13 C14 119.29(19) . . ?
O2 C14 N1 119.3(2) . . ?
O2 C14 C13 126.1(2) . . ?
N1 C14 C13 114.46(18) . . ?
C16A C15 C12 114.0(3) . . ?
C16A C15 C16B 37.9(3) . . ?
C12 C15 C16B 107.2(4) . . ?
C16A C15 H15A 121.1(16) . . ?
C12 C15 H15A 108.3(15) . . ?
C16B C15 H15A 91.8(16) . . ?
C16A C15 H15B 98(2) . . ?
C12 C15 H15B 112(2) . . ?
C16B C15 H15B 131(2) . . ?
H15A C15 H15B 101(3) . . ?
C15 C16A C17A 112.7(4) . . ?
C15 C16A H16A 109.1 . . ?
C17A C16A H16A 109.1 . . ?
C15 C16A H16B 109.1 . . ?
C17A C16A H16B 109.1 . . ?
H16A C16A H16B 107.8 . . ?
C16A C17A C18 118.0(4) . . ?
C16A C17A H17A 107.8 . . ?
C18 C17A H17A 107.8 . . ?
C16A C17A H17B 107.8 . . ?
C18 C17A H17B 107.8 . . ?
H17A C17A H17B 107.1 . . ?
C17B C18 C19 89.6(5) . . ?
C17B C18 C17A 32.4(4) . . ?
C19 C18 C17A 122.0(4) . . ?
C17B C18 H18B 118(3) . . ?
C19 C18 H18B 105(3) . . ?
C17A C18 H18B 105(3) . . ?
C17B C18 H18A 123.8(19) . . ?
C19 C18 H18A 106(2) . . ?
C17A C18 H18A 109.3(19) . . ?
H18B C18 H18A 110(3) . . ?
C20 C19 C18 110.1(3) . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
C21 C20 C19 117.3(3) . . ?
C21 C20 H20A 108.0 . . ?
C19 C20 H20A 108.0 . . ?
C21 C20 H20B 108.0 . . ?
C19 C20 H20B 108.0 . . ?
H20A C20 H20B 107.2 . . ?
C20 C21 C22 117.1(3) . . ?
C20 C21 H21A 108.0 . . ?
C22 C21 H21A 108.0 . . ?
C20 C21 H21B 108.0 . . ?
C22 C21 H21B 108.0 . . ?
H21A C21 H21B 107.3 . . ?
C5 C22 C21 108.1(2) . . ?
C5 C22 H22A 110.1 . . ?
C21 C22 H22A 110.1 . . ?
C5 C22 H22B 110.1 . . ?
C21 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
C17B C16B C15 121.0(7) . . ?
C17B C16B H16C 107.1 . . ?
C15 C16B H16C 107.1 . . ?
C17B C16B H16D 107.1 . . ?
C15 C16B H16D 107.1 . . ?
H16C C16B H16D 106.8 . . ?
C18 C17B C16B 102.5(7) . . ?
C18 C17B H17C 111.3 . . ?
C16B C17B H17C 111.3 . . ?
C18 C17B H17D 111.3 . . ?
C16B C17B H17D 111.3 . . ?
H17C C17B H17D 109.2 . . ?

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
C4 N1 C1 C2 -0.3(3) . . . . ?
C14 N1 C1 C2 -173.9(2) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 N1 0.3(3) . . . . ?
C2 C3 C4 C5 -175.6(2) . . . . ?
C1 N1 C4 C3 0.0(3) . . . . ?
C14 N1 C4 C3 173.6(2) . . . . ?
C1 N1 C4 C5 176.5(2) . . . . ?
C14 N1 C4 C5 -9.8(3) . . . . ?
C3 C4 C5 C6 173.0(2) . . . . ?
N1 C4 C5 C6 -2.5(3) . . . . ?
C3 C4 C5 C22 -18.1(4) . . . . ?
N1 C4 C5 C22 166.4(2) . . . . ?
C4 C5 C6 C13 18.1(3) . . . . ?
C22 C5 C6 C13 -149.7(2) . . . . ?
C4 C5 C6 C7 -169.85(19) . . . . ?
C22 C5 C6 C7 22.3(3) . . . . ?
C8 N2 C7 O1 -6.2(4) . . . . ?
C11 N2 C7 O1 -177.3(2) . . . . ?
C8 N2 C7 C6 176.1(2) . . . . ?
C11 N2 C7 C6 5.0(3) . . . . ?
C5 C6 C7 O1 21.7(3) . . . . ?
C13 C6 C7 O1 -166.3(2) . . . . ?
C5 C6 C7 N2 -160.8(2) . . . . ?
C13 C6 C7 N2 11.2(3) . . . . ?
C7 N2 C8 C9 -172.0(2) . . . . ?
C11 N2 C8 C9 0.2(3) . . . . ?
N2 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 N2 0.2(3) . . . . ?
C9 C10 C11 C12 -176.7(2) . . . . ?
C8 N2 C11 C10 -0.3(3) . . . . ?
C7 N2 C11 C10 172.2(2) . . . . ?
C8 N2 C11 C12 177.2(2) . . . . ?
C7 N2 C11 C12 -10.3(3) . . . . ?
C10 C11 C12 C13 175.0(2) . . . . ?
N2 C11 C12 C13 -1.7(3) . . . . ?
C10 C11 C12 C15 -14.9(4) . . . . ?
N2 C11 C12 C15 168.5(2) . . . . ?
C11 C12 C13 C6 17.9(3) . . . . ?
C15 C12 C13 C6 -151.5(2) . . . . ?
C11 C12 C13 C14 -170.5(2) . . . . ?
C15 C12 C13 C14 20.0(3) . . . . ?
C5 C6 C13 C12 149.1(2) . . . . ?
C7 C6 C13 C12 -23.1(3) . . . . ?
C5 C6 C13 C14 -22.6(3) . . . . ?
C7 C6 C13 C14 165.22(19) . . . . ?
C1 N1 C14 O2 -5.0(4) . . . . ?
C4 N1 C14 O2 -177.6(2) . . . . ?
C1 N1 C14 C13 177.9(2) . . . . ?
C4 N1 C14 C13 5.3(3) . . . . ?
C12 C13 C14 O2 22.0(4) . . . . ?
C6 C13 C14 O2 -166.4(2) . . . . ?
C12 C13 C14 N1 -161.1(2) . . . . ?
C6 C13 C14 N1 10.5(3) . . . . ?
C13 C12 C15 C16A 50.5(4) . . . . ?
C11 C12 C15 C16A -119.1(3) . . . . ?
C13 C12 C15 C16B 90.4(4) . . . . ?
C11 C12 C15 C16B -79.1(4) . . . . ?
C12 C15 C16A C17A 74.0(4) . . . . ?
C16B C15 C16A C17A -13.5(5) . . . . ?
C15 C16A C17A C18 -73.8(6) . . . . ?
C16A C17A C18 C17B -57.6(8) . . . . ?
C16A C17A C18 C19 -57.7(6) . . . . ?
C17B C18 C19 C20 170.5(4) . . . . ?
C17A C18 C19 C20 170.6(4) . . . . ?
C18 C19 C20 C21 -158.8(3) . . . . ?
C19 C20 C21 C22 92.1(4) . . . . ?
C6 C5 C22 C21 89.8(3) . . . . ?
C4 C5 C22 C21 -78.3(3) . . . . ?
C20 C21 C22 C5 -53.7(4) . . . . ?
C16A C15 C16B C17B 57.3(7) . . . . ?
C12 C15 C16B C17B -49.8(8) . . . . ?
C19 C18 C17B C16B -150.3(6) . . . . ?
C17A C18 C17B C16B 29.8(6) . . . . ?
C15 C16B C17B C18 95.4(8) . . . . ?

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
C10 H10 O1 1.02(3) 2.61(3) 3.555(3) 155(2) 2_745
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C10 H10 O1 1.02(3) 2.61(3) 3.555(3) 155(2) 2_745
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C10 H10 O1 1.02(3) 2.61(3) 3.555(3) 155(2) 2_745
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655
C10 H10 O1 1.02(3) 2.61(3) 3.555(3) 155(2) 2_745
C1 H1 O1 0.99(3) 2.41(3) 3.274(3) 145(2) 1_455
C3 H3 O2 0.99(3) 2.60(3) 3.455(3) 145(2) 4_575
C8 H8 O2 0.95(3) 2.49(3) 3.357(3) 152(2) 1_655

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.043

_shelxl_version_number           2014-3



