# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_ayoub1
_database_code_depnum_ccdc_archive 'CCDC 1848784'
loop_
_audit_author_name
_audit_author_address
'Carsten Strohmann'
;Technische Universitat Dortmund
Germany
;
_audit_update_record             
;
2020-08-11 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N2 O2'
_chemical_formula_weight         380.43

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.115(6)
_cell_length_b                   22.716(8)
_cell_length_c                   8.414(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.49(5)
_cell_angle_gamma                90.00
_cell_volume                     1887.6(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4045
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4225
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3292
_reflns_number_gt                2232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.7118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3292
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40931(18) 0.13963(10) 0.6674(2) 0.0393(5) Uani 1 1 d . . .
N2 N 0.05254(18) 0.12479(9) 0.6084(2) 0.0377(5) Uani 1 1 d . . .
O1 O 0.61165(17) 0.15806(9) 0.5961(2) 0.0588(6) Uani 1 1 d . . .
O2 O 0.01302(18) 0.05381(9) 0.7852(2) 0.0554(5) Uani 1 1 d . . .
C1 C 0.0885(2) 0.08085(11) 0.7171(3) 0.0388(6) Uani 1 1 d . . .
C2 C 0.2391(2) 0.07099(14) 0.7409(3) 0.0442(7) Uani 1 1 d . . .
H2a H 0.281(2) 0.0844(11) 0.856(3) 0.041(7) Uiso 1 1 d . . .
H2b H 0.259(3) 0.0287(14) 0.736(3) 0.054(8) Uiso 1 1 d . . .
C3 C 0.2842(2) 0.10683(11) 0.6072(3) 0.0360(6) Uani 1 1 d . . .
C4 C 0.3224(2) 0.06992(11) 0.4756(3) 0.0372(6) Uani 1 1 d . . .
C5 C 0.2485(3) 0.02714(12) 0.3789(3) 0.0457(7) Uani 1 1 d . . .
H5 H 0.159(3) 0.0132(13) 0.393(3) 0.055(8) Uiso 1 1 d . . .
C6 C 0.3044(3) 0.00087(14) 0.2611(4) 0.0554(8) Uani 1 1 d . . .
H6 H 0.253(3) -0.0278(14) 0.192(4) 0.065(9) Uiso 1 1 d . . .
C7 C 0.4322(3) 0.01750(14) 0.2398(4) 0.0568(8) Uani 1 1 d . . .
H7 H 0.464(3) -0.0009(13) 0.152(4) 0.062(9) Uiso 1 1 d . . .
C8 C 0.5066(3) 0.05969(14) 0.3380(3) 0.0492(7) Uani 1 1 d . . .
H8 H 0.595(3) 0.0720(12) 0.324(3) 0.046(7) Uiso 1 1 d . . .
C9 C 0.4503(2) 0.08527(11) 0.4562(3) 0.0372(6) Uani 1 1 d . . .
C10 C 0.5050(2) 0.13112(12) 0.5766(3) 0.0400(6) Uani 1 1 d . . .
C11 C 0.4073(3) 0.19043(13) 0.7694(3) 0.0466(7) Uani 1 1 d . . .
H111 H 0.390(3) 0.1798(13) 0.879(4) 0.062(8) Uiso 1 1 d . . .
H112 H 0.498(3) 0.2089(13) 0.796(3) 0.062(8) Uiso 1 1 d . . .
C12 C 0.3036(2) 0.23389(12) 0.6843(3) 0.0404(6) Uani 1 1 d . . .
C13 C 0.3237(3) 0.29378(14) 0.7099(4) 0.0516(7) Uani 1 1 d . . .
H13 H 0.406(3) 0.3079(15) 0.788(4) 0.075(10) Uiso 1 1 d . . .
C14 C 0.2306(3) 0.33413(15) 0.6320(4) 0.0589(8) Uani 1 1 d . . .
H14 H 0.243(3) 0.3763(15) 0.649(3) 0.056(8) Uiso 1 1 d . . .
C15 C 0.1174(3) 0.31487(14) 0.5225(4) 0.0556(8) Uani 1 1 d . . .
H15 H 0.053(3) 0.3406(14) 0.465(3) 0.061(9) Uiso 1 1 d . . .
C16 C 0.0980(3) 0.25525(13) 0.4918(3) 0.0479(7) Uani 1 1 d . . .
H16 H 0.020(3) 0.2413(12) 0.406(3) 0.045(7) Uiso 1 1 d . . .
C17 C 0.1886(2) 0.21403(11) 0.5741(3) 0.0383(6) Uani 1 1 d . . .
C18 C 0.1625(2) 0.14901(11) 0.5382(3) 0.0336(6) Uani 1 1 d . . .
H18 H 0.1362(19) 0.1447(9) 0.419(2) 0.017(5) Uiso 1 1 d . . .
C19 C -0.0872(2) 0.14555(14) 0.5598(3) 0.0427(6) Uani 1 1 d . . .
H191 H -0.093(2) 0.1876(13) 0.595(3) 0.044(7) Uiso 1 1 d . . .
H192 H -0.140(2) 0.1211(12) 0.619(3) 0.041(7) Uiso 1 1 d . . .
C20 C -0.1441(2) 0.14176(12) 0.3796(3) 0.0417(6) Uani 1 1 d . . .
C21 C -0.2269(3) 0.18598(14) 0.2994(4) 0.0509(7) Uani 1 1 d . . .
H21 H -0.245(2) 0.2209(12) 0.366(3) 0.046(7) Uiso 1 1 d . . .
C22 C -0.2801(3) 0.18284(16) 0.1345(4) 0.0622(8) Uani 1 1 d . . .
H22 H -0.333(4) 0.2157(17) 0.080(4) 0.089(11) Uiso 1 1 d . . .
C23 C -0.2506(3) 0.13563(17) 0.0459(4) 0.0701(10) Uani 1 1 d . . .
H23 H -0.284(3) 0.1326(14) -0.072(4) 0.071(9) Uiso 1 1 d . . .
C24 C -0.1683(3) 0.09093(17) 0.1242(4) 0.0653(9) Uani 1 1 d . . .
H24 H -0.147(3) 0.0584(16) 0.067(4) 0.075(10) Uiso 1 1 d . . .
C25 C -0.1165(3) 0.09433(14) 0.2892(4) 0.0513(7) Uani 1 1 d . . .
H25 H -0.062(3) 0.0646(13) 0.342(3) 0.057(8) 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
N1 C10 1.370(3) . ?
N1 C11 1.441(3) . ?
N1 C3 1.461(3) . ?
N2 C1 1.350(3) . ?
N2 C19 1.462(3) . ?
N2 C18 1.474(3) . ?
O1 C10 1.220(3) . ?
O2 C1 1.215(3) . ?
C1 C2 1.510(3) . ?
C2 C3 1.536(4) . ?
C3 C4 1.504(3) . ?
C3 C18 1.569(3) . ?
C4 C5 1.379(4) . ?
C4 C9 1.383(3) . ?
C5 C6 1.378(4) . ?
C6 C7 1.395(4) . ?
C7 C8 1.378(4) . ?
C8 C9 1.377(4) . ?
C9 C10 1.474(4) . ?
C11 C12 1.504(4) . ?
C12 C13 1.386(4) . ?
C12 C17 1.396(4) . ?
C13 C14 1.375(5) . ?
C14 C15 1.376(5) . ?
C15 C16 1.385(4) . ?
C16 C17 1.386(4) . ?
C17 C18 1.519(4) . ?
C19 C20 1.504(4) . ?
C20 C25 1.382(4) . ?
C20 C21 1.386(4) . ?
C21 C22 1.377(4) . ?
C22 C23 1.375(5) . ?
C23 C24 1.386(5) . ?
C24 C25 1.376(4) . ?

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
C10 N1 C11 123.2(2) . . ?
C10 N1 C3 113.44(19) . . ?
C11 N1 C3 119.47(19) . . ?
C1 N2 C19 122.0(2) . . ?
C1 N2 C18 115.57(19) . . ?
C19 N2 C18 122.4(2) . . ?
O2 C1 N2 126.0(2) . . ?
O2 C1 C2 125.5(2) . . ?
N2 C1 C2 108.4(2) . . ?
C1 C2 C3 106.0(2) . . ?
N1 C3 C4 101.45(18) . . ?
N1 C3 C2 112.9(2) . . ?
C4 C3 C2 114.1(2) . . ?
N1 C3 C18 111.6(2) . . ?
C4 C3 C18 112.0(2) . . ?
C2 C3 C18 105.12(19) . . ?
C5 C4 C9 120.6(2) . . ?
C5 C4 C3 129.4(2) . . ?
C9 C4 C3 110.0(2) . . ?
C6 C5 C4 118.4(3) . . ?
C5 C6 C7 120.7(3) . . ?
C8 C7 C6 120.8(3) . . ?
C9 C8 C7 118.0(3) . . ?
C8 C9 C4 121.5(2) . . ?
C8 C9 C10 129.9(2) . . ?
C4 C9 C10 108.6(2) . . ?
O1 C10 N1 124.4(2) . . ?
O1 C10 C9 129.5(2) . . ?
N1 C10 C9 106.1(2) . . ?
N1 C11 C12 109.9(2) . . ?
C13 C12 C17 119.6(3) . . ?
C13 C12 C11 120.5(2) . . ?
C17 C12 C11 119.9(2) . . ?
C14 C13 C12 121.2(3) . . ?
C13 C14 C15 119.5(3) . . ?
C14 C15 C16 120.0(3) . . ?
C15 C16 C17 121.0(3) . . ?
C16 C17 C12 118.6(3) . . ?
C16 C17 C18 119.3(2) . . ?
C12 C17 C18 122.0(2) . . ?
N2 C18 C17 113.37(19) . . ?
N2 C18 C3 102.92(18) . . ?
C17 C18 C3 115.53(19) . . ?
N2 C19 C20 113.5(2) . . ?
C25 C20 C21 118.0(3) . . ?
C25 C20 C19 121.4(2) . . ?
C21 C20 C19 120.6(3) . . ?
C22 C21 C20 121.1(3) . . ?
C23 C22 C21 120.2(3) . . ?
C22 C23 C24 119.5(3) . . ?
C25 C24 C23 119.8(3) . . ?
C24 C25 C20 121.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_mk010707
_database_code_depnum_ccdc_archive 'CCDC 2022086'
loop_
_audit_author_name
_audit_author_address
'Carsten Strohmann'
;Technische Universitat Dortmund
Germany
;
_audit_update_record             
;
2020-08-11 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 N2 O4'
_chemical_formula_weight         454.51

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4505(17)
_cell_length_b                   19.920(4)
_cell_length_c                   13.650(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.14(3)
_cell_angle_gamma                90.00
_cell_volume                     2291.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    20112
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.00

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20461
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4679
_reflns_number_gt                3827
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.3838P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4679
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.63205(18) 0.63735(8) 0.90895(13) 0.0522(4) Uani 1 1 d . . .
H1A H 0.6576 0.6716 0.8611 0.078 Uiso 1 1 calc R . .
H1B H 0.7000 0.5980 0.9020 0.078 Uiso 1 1 calc R . .
H1C H 0.6500 0.6556 0.9755 0.078 Uiso 1 1 calc R . .
C2 C 0.0244(2) 0.55168(8) 0.87849(15) 0.0601(4) Uani 1 1 d . . .
H2A H -0.0232 0.5640 0.9394 0.090 Uiso 1 1 calc R . .
H2B H 0.0272 0.5027 0.8725 0.090 Uiso 1 1 calc R . .
H2C H -0.0392 0.5706 0.8222 0.090 Uiso 1 1 calc R . .
C3 C 0.35909(16) 0.66749(6) 0.90116(9) 0.0381(3) Uani 1 1 d . . .
C4 C 0.20102(17) 0.64528(6) 0.89435(10) 0.0388(3) Uani 1 1 d . . .
C5 C 0.07958(17) 0.69109(7) 0.90429(10) 0.0417(3) Uani 1 1 d . . .
H5 H -0.0273 0.6760 0.8989 0.050 Uiso 1 1 calc R . .
C6 C 0.11167(17) 0.75937(7) 0.92218(10) 0.0400(3) Uani 1 1 d . . .
C7 C 0.26906(16) 0.78113(6) 0.92910(9) 0.0369(3) Uani 1 1 d . . .
C8 C 0.39151(16) 0.73482(6) 0.91749(9) 0.0375(3) Uani 1 1 d . . .
H8 H 0.4984 0.7499 0.9209 0.045 Uiso 1 1 calc R . .
C9 C -0.02309(18) 0.80737(7) 0.93730(11) 0.0456(3) Uani 1 1 d . . .
H9A H -0.0045 0.8286 1.0027 0.055 Uiso 1 1 calc R . .
H9B H -0.1230 0.7814 0.9373 0.055 Uiso 1 1 calc R . .
C10 C -0.04398(18) 0.86296(7) 0.85921(12) 0.0484(3) Uani 1 1 d . . .
H10A H -0.1173 0.8467 0.8045 0.058 Uiso 1 1 calc R . .
H10B H -0.0940 0.9024 0.8886 0.058 Uiso 1 1 calc R . .
C11 C 0.11786(19) 0.88910(7) 0.72070(11) 0.0457(3) Uani 1 1 d . . .
C12 C 0.27852(19) 0.91621(7) 0.70928(10) 0.0431(3) Uani 1 1 d . . .
C13 C 0.3537(2) 0.93159(7) 0.62447(11) 0.0525(4) Uani 1 1 d . . .
H13 H 0.3013 0.9252 0.5612 0.063 Uiso 1 1 calc R . .
C14 C 0.5071(2) 0.95646(8) 0.63527(12) 0.0548(4) Uani 1 1 d . . .
H14 H 0.5604 0.9676 0.5785 0.066 Uiso 1 1 calc R . .
C15 C 0.5842(2) 0.96533(8) 0.72781(12) 0.0516(4) Uani 1 1 d . . .
H15 H 0.6897 0.9822 0.7335 0.062 Uiso 1 1 calc R . .
C16 C 0.50850(19) 0.94977(7) 0.81232(11) 0.0454(3) Uani 1 1 d . . .
H16 H 0.5615 0.9554 0.8756 0.054 Uiso 1 1 calc R . .
C17 C 0.35396(17) 0.92585(6) 0.80207(10) 0.0397(3) Uani 1 1 d . . .
C18 C 0.24325(16) 0.90774(6) 0.87989(9) 0.0383(3) Uani 1 1 d . . .
C19 C 0.31531(17) 0.85308(6) 0.95303(9) 0.0374(3) Uani 1 1 d . . .
H19 H 0.4335 0.8564 0.9546 0.045 Uiso 1 1 calc R . .
C20 C 0.19824(18) 0.93706(7) 1.04913(10) 0.0424(3) Uani 1 1 d . . .
C21 C 0.20345(18) 0.96652(7) 0.94762(10) 0.0432(3) Uani 1 1 d . . .
H21A H 0.2858 1.0018 0.9471 0.052 Uiso 1 1 calc R . .
H21B H 0.0996 0.9865 0.9257 0.052 Uiso 1 1 calc R . .
C22 C 0.29877(19) 0.83536(8) 1.13841(10) 0.0483(3) Uani 1 1 d . . .
H22A H 0.2316 0.7946 1.1348 0.058 Uiso 1 1 calc R . .
H22B H 0.2712 0.8618 1.1962 0.058 Uiso 1 1 calc R . .
C23 C 0.47145(19) 0.81503(7) 1.15120(10) 0.0432(3) Uani 1 1 d . . .
C24 C 0.5147(2) 0.74783(8) 1.16207(11) 0.0507(4) Uani 1 1 d . . .
H24 H 0.4347 0.7144 1.1635 0.061 Uiso 1 1 calc R . .
C25 C 0.6731(2) 0.72912(8) 1.17085(12) 0.0580(4) Uani 1 1 d . . .
H25 H 0.7007 0.6831 1.1785 0.070 Uiso 1 1 calc R . .
C26 C 0.7907(2) 0.77684(9) 1.16853(12) 0.0587(4) Uani 1 1 d . . .
H26 H 0.8992 0.7638 1.1739 0.070 Uiso 1 1 calc R . .
C27 C 0.7497(2) 0.84422(9) 1.15828(12) 0.0571(4) Uani 1 1 d . . .
H27 H 0.8303 0.8774 1.1570 0.068 Uiso 1 1 calc R . .
C28 C 0.5912(2) 0.86305(8) 1.14997(11) 0.0496(4) Uani 1 1 d . . .
H28 H 0.5641 0.9092 1.1434 0.060 Uiso 1 1 calc R . .
N1 N 0.26592(15) 0.87542(6) 1.04908(8) 0.0421(3) Uani 1 1 d . . .
N2 N 0.10294(14) 0.88406(6) 0.81990(9) 0.0419(3) Uani 1 1 d . . .
O1 O 0.47039(12) 0.61825(5) 0.89196(8) 0.0469(3) Uani 1 1 d . . .
O2 O 0.18166(13) 0.57752(5) 0.88041(8) 0.0476(3) Uani 1 1 d . . .
O3 O 0.14455(14) 0.96442(6) 1.12058(8) 0.0539(3) Uani 1 1 d . . .
O4 O 0.01509(16) 0.87409(6) 0.65604(9) 0.0612(3) 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 O1 1.4209(18) . ?
C2 O2 1.4239(19) . ?
C3 O1 1.3709(16) . ?
C3 C8 1.3837(18) . ?
C3 C4 1.4038(19) . ?
C4 O2 1.3712(16) . ?
C4 C5 1.3872(19) . ?
C5 C6 1.4048(19) . ?
C6 C7 1.396(2) . ?
C6 C9 1.5125(19) . ?
C7 C8 1.4038(18) . ?
C7 C19 1.5150(18) . ?
C9 C10 1.538(2) . ?
C10 N2 1.450(2) . ?
C11 O4 1.2296(18) . ?
C11 N2 1.373(2) . ?
C11 C12 1.480(2) . ?
C12 C17 1.3895(19) . ?
C12 C13 1.394(2) . ?
C13 C14 1.386(3) . ?
C14 C15 1.390(2) . ?
C15 C16 1.394(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.509(2) . ?
C18 N2 1.4691(17) . ?
C18 C21 1.5439(18) . ?
C18 C19 1.5700(18) . ?
C19 N1 1.4730(17) . ?
C20 O3 1.2321(18) . ?
C20 N1 1.3546(18) . ?
C20 C21 1.508(2) . ?
C22 N1 1.4669(18) . ?
C22 C23 1.512(2) . ?
C23 C24 1.393(2) . ?
C23 C28 1.394(2) . ?
C24 C25 1.386(2) . ?
C25 C26 1.378(3) . ?
C26 C27 1.391(2) . ?
C27 C28 1.388(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
O1 C3 C8 125.38(13) . . ?
O1 C3 C4 115.11(12) . . ?
C8 C3 C4 119.51(12) . . ?
O2 C4 C5 125.41(13) . . ?
O2 C4 C3 115.01(11) . . ?
C5 C4 C3 119.56(12) . . ?
C4 C5 C6 121.27(13) . . ?
C7 C6 C5 118.92(12) . . ?
C7 C6 C9 121.18(12) . . ?
C5 C6 C9 119.87(13) . . ?
C6 C7 C8 119.67(12) . . ?
C6 C7 C19 122.56(12) . . ?
C8 C7 C19 117.73(12) . . ?
C3 C8 C7 121.07(13) . . ?
C6 C9 C10 114.23(13) . . ?
N2 C10 C9 113.99(12) . . ?
O4 C11 N2 125.44(16) . . ?
O4 C11 C12 128.24(15) . . ?
N2 C11 C12 106.32(12) . . ?
C17 C12 C13 121.33(15) . . ?
C17 C12 C11 108.56(13) . . ?
C13 C12 C11 130.10(14) . . ?
C14 C13 C12 117.98(14) . . ?
C13 C14 C15 121.05(15) . . ?
C14 C15 C16 120.70(16) . . ?
C17 C16 C15 118.55(14) . . ?
C16 C17 C12 120.38(14) . . ?
C16 C17 C18 129.64(12) . . ?
C12 C17 C18 109.98(12) . . ?
N2 C18 C17 101.59(11) . . ?
N2 C18 C21 112.04(12) . . ?
C17 C18 C21 114.40(11) . . ?
N2 C18 C19 113.09(11) . . ?
C17 C18 C19 112.44(11) . . ?
C21 C18 C19 103.68(10) . . ?
N1 C19 C7 113.10(11) . . ?
N1 C19 C18 103.57(10) . . ?
C7 C19 C18 115.90(11) . . ?
O3 C20 N1 125.52(14) . . ?
O3 C20 C21 126.30(13) . . ?
N1 C20 C21 108.17(12) . . ?
C20 C21 C18 106.09(11) . . ?
N1 C22 C23 111.39(12) . . ?
C24 C23 C28 118.40(15) . . ?
C24 C23 C22 120.90(14) . . ?
C28 C23 C22 120.68(13) . . ?
C25 C24 C23 120.81(16) . . ?
C26 C25 C24 120.42(15) . . ?
C25 C26 C27 119.56(17) . . ?
C28 C27 C26 120.08(17) . . ?
C27 C28 C23 120.73(15) . . ?
C20 N1 C22 123.17(12) . . ?
C20 N1 C19 114.90(11) . . ?
C22 N1 C19 121.79(11) . . ?
C11 N2 C10 121.90(13) . . ?
C11 N2 C18 113.48(13) . . ?
C10 N2 C18 124.40(12) . . ?
C3 O1 C1 116.83(11) . . ?
C4 O2 C2 117.40(11) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
