# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mo_120560lt_0m
_database_code_depnum_ccdc_archive 'CCDC 891457'
_audit_update_record             
;
2016-01-02 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'methyl 3,4,4-trimethyl-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N3 O2'
_chemical_formula_weight         271.32

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_hall  '-P 2ac 2ab'

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

_cell_length_a                   8.2166(6)
_cell_length_b                   15.0686(10)
_cell_length_c                   22.6298(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2801.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4144
_cell_measurement_theta_min      2.8495
_cell_measurement_theta_max      26.2601

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7938
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19670
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.48
_reflns_number_total             2893
_reflns_number_gt                2310
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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)+(0.0546P)²+1.7616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2893
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_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
O1 O 0.87157(14) 0.61334(7) 0.50755(5) 0.0224(3) Uani 1 1 d . . .
O2 O 0.79312(14) 0.71303(7) 0.43972(6) 0.0235(3) Uani 1 1 d . . .
N1 N 0.35481(15) 0.38108(8) 0.36856(6) 0.0160(3) Uani 1 1 d . . .
N2 N 0.24297(17) 0.25495(9) 0.33947(6) 0.0207(3) Uani 1 1 d . . .
N3 N 0.32385(15) 0.55471(9) 0.33611(6) 0.0171(3) Uani 1 1 d . . .
H3 H 0.3378 0.6032 0.3150 0.021 Uiso 1 1 calc R . .
C1 C 0.9864(2) 0.67809(12) 0.52926(8) 0.0250(4) Uani 1 1 d . . .
H1A H 1.0675 0.6906 0.4986 0.038 Uiso 1 1 calc R . .
H1B H 1.0409 0.6548 0.5645 0.038 Uiso 1 1 calc R . .
H1C H 0.9287 0.7329 0.5394 0.038 Uiso 1 1 calc R . .
C2 C 0.78136(18) 0.63987(10) 0.46150(7) 0.0175(3) Uani 1 1 d . . .
C3 C 0.66776(18) 0.57028(10) 0.44043(7) 0.0165(3) Uani 1 1 d . . .
C4 C 0.54858(18) 0.59494(10) 0.39999(7) 0.0165(3) Uani 1 1 d . . .
H4 H 0.5412 0.6550 0.3875 0.020 Uiso 1 1 calc R . .
C5 C 0.43964(18) 0.53234(10) 0.37752(7) 0.0157(3) Uani 1 1 d . . .
C6 C 0.45998(18) 0.44363(10) 0.39523(7) 0.0155(3) Uani 1 1 d . . .
C7 C 0.22230(19) 0.40379(11) 0.33381(7) 0.0168(3) Uani 1 1 d . . .
C8 C 0.1538(2) 0.32548(11) 0.31677(7) 0.0204(4) Uani 1 1 d . . .
C9 C 0.0048(2) 0.30695(13) 0.28053(9) 0.0340(5) Uani 1 1 d . . .
H9A H -0.0876 0.3401 0.2967 0.051 Uiso 1 1 calc R . .
H9B H -0.0193 0.2433 0.2816 0.051 Uiso 1 1 calc R . .
H9C H 0.0240 0.3253 0.2396 0.051 Uiso 1 1 calc R . .
C10 C 0.57788(19) 0.41890(10) 0.43585(7) 0.0179(3) Uani 1 1 d . . .
H10 H 0.5876 0.3586 0.4477 0.022 Uiso 1 1 calc R . .
C11 C 0.68148(19) 0.48243(10) 0.45914(7) 0.0182(3) Uani 1 1 d . . .
H11 H 0.7611 0.4663 0.4876 0.022 Uiso 1 1 calc R . .
C12 C 0.36200(19) 0.29088(10) 0.37000(7) 0.0182(3) Uani 1 1 d . . .
H12 H 0.4429 0.2580 0.3905 0.022 Uiso 1 1 calc R . .
C13 C 0.17786(19) 0.50052(10) 0.32588(7) 0.0181(3) Uani 1 1 d . . .
C14 C 0.0430(2) 0.52648(12) 0.36954(9) 0.0270(4) Uani 1 1 d . . .
H14A H 0.0803 0.5156 0.4100 0.040 Uiso 1 1 calc R . .
H14B H -0.0544 0.4909 0.3617 0.040 Uiso 1 1 calc R . .
H14C H 0.0171 0.5896 0.3648 0.040 Uiso 1 1 calc R . .
C15 C 0.1232(2) 0.51975(12) 0.26246(8) 0.0265(4) Uani 1 1 d . . .
H15A H 0.1091 0.5839 0.2573 0.040 Uiso 1 1 calc R . .
H15B H 0.0198 0.4896 0.2547 0.040 Uiso 1 1 calc R . .
H15C H 0.2059 0.4981 0.2348 0.040 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.340(2) . ?
O1 C1 1.4434(19) . ?
O2 C2 1.2113(19) . ?
N1 C12 1.361(2) . ?
N1 C7 1.386(2) . ?
N1 C6 1.414(2) . ?
N2 C12 1.314(2) . ?
N2 C8 1.389(2) . ?
N3 C5 1.377(2) . ?
N3 C13 1.469(2) . ?
N3 H3 0.8800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.483(2) . ?
C3 C4 1.391(2) . ?
C3 C11 1.394(2) . ?
C4 C5 1.396(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(2) . ?
C6 C10 1.386(2) . ?
C7 C8 1.363(2) . ?
C7 C13 1.513(2) . ?
C8 C9 1.499(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C15 1.531(2) . ?
C13 C14 1.535(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 O1 C1 115.12(13) . . ?
C12 N1 C7 107.12(13) . . ?
C12 N1 C6 128.98(14) . . ?
C7 N1 C6 123.89(13) . . ?
C12 N2 C8 105.78(13) . . ?
C5 N3 C13 122.34(13) . . ?
C5 N3 H3 118.8 . . ?
C13 N3 H3 118.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.94(15) . . ?
O2 C2 C3 124.27(15) . . ?
O1 C2 C3 112.79(13) . . ?
C4 C3 C11 120.69(14) . . ?
C4 C3 C2 117.76(14) . . ?
C11 C3 C2 121.52(14) . . ?
C3 C4 C5 120.69(14) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N3 C5 C4 121.69(14) . . ?
N3 C5 C6 120.59(14) . . ?
C4 C5 C6 117.54(14) . . ?
C10 C6 C5 121.86(14) . . ?
C10 C6 N1 122.06(14) . . ?
C5 C6 N1 116.08(14) . . ?
C8 C7 N1 105.74(14) . . ?
C8 C7 C13 134.47(14) . . ?
N1 C7 C13 119.65(14) . . ?
C7 C8 N2 109.85(14) . . ?
C7 C8 C9 130.77(15) . . ?
N2 C8 C9 119.36(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C6 119.72(15) . . ?
C11 C10 H10 120.1 . . ?
C6 C10 H10 120.1 . . ?
C10 C11 C3 119.39(15) . . ?
C10 C11 H11 120.3 . . ?
C3 C11 H11 120.3 . . ?
N2 C12 N1 111.51(14) . . ?
N2 C12 H12 124.2 . . ?
N1 C12 H12 124.2 . . ?
N3 C13 C7 108.64(12) . . ?
N3 C13 C15 106.36(13) . . ?
C7 C13 C15 111.35(14) . . ?
N3 C13 C14 110.25(13) . . ?
C7 C13 C14 110.08(13) . . ?
C15 C13 C14 110.09(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_mo_120626lt_0m
_database_code_depnum_ccdc_archive 'CCDC 891458'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'methyl (Z)-4-(1H-imidazol-1-yl)-3-((methoxy(phenyl)methylene)amino)benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N3 O3'
_chemical_formula_weight         335.36

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   'P 1 21/n 1'
_symmetry_space_group_name_hall  '-P 2yn'

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

_cell_length_a                   11.587(2)
_cell_length_b                   10.3387(17)
_cell_length_c                   14.091(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.378(4)
_cell_angle_gamma                90.00
_cell_volume                     1654.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3937
_cell_measurement_theta_min      2.4606
_cell_measurement_theta_max      26.2291

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6285
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            11817
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         26.52
_reflns_number_total             3378
_reflns_number_gt                2535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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)+(0.0581P)²+0.1909P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3378
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_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
O1 O 0.48179(9) 0.16910(11) 0.56358(9) 0.0296(3) Uani 1 1 d . . .
O2 O 0.43371(9) 0.01644(11) 0.66219(9) 0.0329(3) Uani 1 1 d . . .
O3 O 1.09275(9) 0.23398(10) 0.60418(8) 0.0236(3) Uani 1 1 d . . .
N1 N 0.91847(10) 0.22745(12) 0.65562(10) 0.0206(3) Uani 1 1 d . . .
N2 N 0.98235(10) 0.09302(12) 0.84212(9) 0.0209(3) Uani 1 1 d . . .
N3 N 1.14523(11) 0.00790(14) 0.92992(10) 0.0288(3) Uani 1 1 d . . .
C1 C 0.36020(14) 0.17049(19) 0.51199(14) 0.0351(4) Uani 1 1 d . . .
H1A H 0.3405 0.0865 0.4807 0.053 Uiso 1 1 calc R . .
H1B H 0.3498 0.2386 0.4627 0.053 Uiso 1 1 calc R . .
H1C H 0.3083 0.1873 0.5577 0.053 Uiso 1 1 calc R . .
C2 C 0.50650(13) 0.08683(15) 0.63820(12) 0.0230(4) Uani 1 1 d . . .
C3 C 0.63232(12) 0.09226(15) 0.68863(12) 0.0213(3) Uani 1 1 d . . .
C4 C 0.71693(13) 0.16140(15) 0.65118(12) 0.0212(3) Uani 1 1 d . . .
H4 H 0.6940 0.2095 0.5931 0.025 Uiso 1 1 calc R . .
C5 C 0.83493(13) 0.16050(14) 0.69842(12) 0.0198(3) Uani 1 1 d . . .
C6 C 1.00707(12) 0.16768(15) 0.63504(11) 0.0202(3) Uani 1 1 d . . .
C7 C 1.03344(13) 0.02677(15) 0.64176(11) 0.0206(3) Uani 1 1 d . . .
C8 C 1.14746(13) -0.01591(16) 0.67904(12) 0.0260(4) Uani 1 1 d . . .
H8 H 1.2097 0.0448 0.6957 0.031 Uiso 1 1 calc R . .
C9 C 1.16976(15) -0.14672(16) 0.69176(13) 0.0315(4) Uani 1 1 d . . .
H9 H 1.2474 -0.1755 0.7179 0.038 Uiso 1 1 calc R . .
C10 C 1.07990(15) -0.23626(17) 0.66671(13) 0.0320(4) Uani 1 1 d . . .
H10 H 1.0957 -0.3260 0.6764 0.038 Uiso 1 1 calc R . .
C11 C 0.66409(13) 0.02505(15) 0.77497(12) 0.0238(4) Uani 1 1 d . . .
H11 H 0.6071 -0.0245 0.7991 0.029 Uiso 1 1 calc R . .
C12 C 0.77879(13) 0.03040(15) 0.82578(12) 0.0238(4) Uani 1 1 d . . .
H12 H 0.7997 -0.0116 0.8867 0.029 Uiso 1 1 calc R . .
C13 C 0.86419(12) 0.09729(15) 0.78797(11) 0.0202(3) Uani 1 1 d . . .
C14 C 1.03712(14) -0.01464(17) 0.88451(12) 0.0260(4) Uani 1 1 d . . .
H14 H 1.0009 -0.0974 0.8815 0.031 Uiso 1 1 calc R . .
C15 C 1.16099(14) 0.13844(17) 0.91629(12) 0.0271(4) Uani 1 1 d . . .
H15 H 1.2315 0.1843 0.9413 0.032 Uiso 1 1 calc R . .
C16 C 1.06266(13) 0.19301(16) 0.86246(12) 0.0244(4) Uani 1 1 d . . .
H16 H 1.0516 0.2809 0.8430 0.029 Uiso 1 1 calc R . .
C17 C 1.07906(14) 0.37255(16) 0.59738(13) 0.0291(4) Uani 1 1 d . . .
H17A H 1.0064 0.3936 0.5514 0.044 Uiso 1 1 calc R . .
H17B H 1.1464 0.4103 0.5749 0.044 Uiso 1 1 calc R . .
H17C H 1.0750 0.4078 0.6612 0.044 Uiso 1 1 calc R . .
C18 C 0.94366(13) -0.06387(15) 0.61493(12) 0.0242(4) Uani 1 1 d . . .
H18 H 0.8661 -0.0356 0.5879 0.029 Uiso 1 1 calc R . .
C19 C 0.96694(14) -0.19446(16) 0.62745(13) 0.0289(4) Uani 1 1 d . . .
H19 H 0.9054 -0.2557 0.6091 0.035 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.339(2) . ?
O1 C1 1.4525(18) . ?
O2 C2 1.2115(19) . ?
O3 C6 1.3472(18) . ?
O3 C17 1.4424(19) . ?
N1 C6 1.2796(19) . ?
N1 C5 1.4178(19) . ?
N2 C14 1.360(2) . ?
N2 C16 1.383(2) . ?
N2 C13 1.4306(18) . ?
N3 C14 1.310(2) . ?
N3 C15 1.380(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.492(2) . ?
C3 C11 1.386(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C13 1.402(2) . ?
C6 C7 1.488(2) . ?
C7 C8 1.394(2) . ?
C7 C18 1.396(2) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C19 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.360(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.381(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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 O1 C1 115.81(12) . . ?
C6 O3 C17 116.64(12) . . ?
C6 N1 C5 120.42(13) . . ?
C14 N2 C16 106.52(13) . . ?
C14 N2 C13 125.05(13) . . ?
C16 N2 C13 128.44(13) . . ?
C14 N3 C15 104.23(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.23(15) . . ?
O2 C2 C3 123.95(15) . . ?
O1 C2 C3 112.81(13) . . ?
C11 C3 C4 120.20(14) . . ?
C11 C3 C2 117.68(13) . . ?
C4 C3 C2 122.12(14) . . ?
C5 C4 C3 120.64(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C13 118.16(13) . . ?
C4 C5 N1 118.69(14) . . ?
C13 C5 N1 123.11(13) . . ?
N1 C6 O3 120.18(14) . . ?
N1 C6 C7 128.49(14) . . ?
O3 C6 C7 111.32(12) . . ?
C8 C7 C18 119.35(15) . . ?
C8 C7 C6 120.10(14) . . ?
C18 C7 C6 120.49(13) . . ?
C9 C8 C7 119.86(15) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.58(15) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C19 C10 C9 119.76(16) . . ?
C19 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C3 119.79(14) . . ?
C12 C11 H11 120.1 . . ?
C3 C11 H11 120.1 . . ?
C11 C12 C13 120.27(15) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C5 120.71(14) . . ?
C12 C13 N2 117.19(14) . . ?
C5 C13 N2 122.04(13) . . ?
N3 C14 N2 112.79(15) . . ?
N3 C14 H14 123.6 . . ?
N2 C14 H14 123.6 . . ?
C16 C15 N3 111.33(15) . . ?
C16 C15 H15 124.3 . . ?
N3 C15 H15 124.3 . . ?
C15 C16 N2 105.12(15) . . ?
C15 C16 H16 127.4 . . ?
N2 C16 H16 127.4 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C7 120.35(15) . . ?
C19 C18 H18 119.8 . . ?
C7 C18 H18 119.8 . . ?
C18 C19 C10 120.07(15) . . ?
C18 C19 H19 120.0 . . ?
C10 C19 H19 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.52
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.070
