# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_131224a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40

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   P2(1)/n

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                   15.3627(13)
_cell_length_b                   9.0461(8)
_cell_length_c                   15.4985(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.3850(10)
_cell_angle_gamma                90.00
_cell_volume                     2055.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6559
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9900
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17428
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.67
_reflns_number_total             4777
_reflns_number_gt                3522
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_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)+(0.1179P)²+0.0000P] 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       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4777
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1573
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.500 156 45 ' '
2 0.000 0.500 0.000 156 45 ' '

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 0.66163(8) 0.83021(13) 0.23651(8) 0.0410(3) Uani 1 1 d . . .
C2 C 0.57388(9) 0.79234(16) 0.18406(10) 0.0524(3) Uani 1 1 d . . .
H2 H 0.5310 0.7633 0.2122 0.063 Uiso 1 1 calc R . .
C3 C 0.54977(9) 0.79736(16) 0.09095(9) 0.0540(4) Uani 1 1 d . . .
H3 H 0.4907 0.7717 0.0573 0.065 Uiso 1 1 calc R . .
C4 C 0.61176(10) 0.83982(15) 0.04647(9) 0.0507(3) Uani 1 1 d . . .
C5 C 0.70026(9) 0.87202(14) 0.09953(8) 0.0466(3) Uani 1 1 d . . .
H5 H 0.7434 0.8974 0.0709 0.056 Uiso 1 1 calc R . .
C6 C 0.72682(8) 0.86788(12) 0.19360(8) 0.0395(3) Uani 1 1 d . . .
C7 C 0.82305(8) 0.91231(14) 0.24873(8) 0.0415(3) Uani 1 1 d . . .
H7 H 0.8259 1.0204 0.2462 0.050 Uiso 1 1 calc R . .
C8 C 0.84202(8) 0.87060(15) 0.34816(8) 0.0468(3) Uani 1 1 d . . .
H8A H 0.8538 0.7653 0.3553 0.056 Uiso 1 1 calc R . .
H8B H 0.8962 0.9221 0.3839 0.056 Uiso 1 1 calc R . .
C9 C 0.76208(8) 0.90970(14) 0.38292(8) 0.0437(3) Uani 1 1 d . . .
H9 H 0.7487 1.0154 0.3731 0.052 Uiso 1 1 calc R . .
C10 C 0.78492(8) 0.87669(14) 0.48270(8) 0.0453(3) Uani 1 1 d . . .
C11 C 0.83709(10) 0.97866(17) 0.54355(9) 0.0570(4) Uani 1 1 d . . .
H11 H 0.8556 1.0651 0.5217 0.068 Uiso 1 1 calc R . .
C12 C 0.86204(12) 0.9545(2) 0.63578(10) 0.0690(4) Uani 1 1 d . . .
H12 H 0.8963 1.0250 0.6752 0.083 Uiso 1 1 calc R . .
C13 C 0.83659(11) 0.8280(2) 0.66900(10) 0.0652(4) Uani 1 1 d . . .
H13 H 0.8534 0.8105 0.7309 0.078 Uiso 1 1 calc R . .
C14 C 0.78539(10) 0.72626(18) 0.60887(10) 0.0566(4) Uani 1 1 d . . .
C15 C 0.75882(9) 0.74838(16) 0.51565(9) 0.0497(3) Uani 1 1 d . . .
H15 H 0.7242 0.6779 0.4765 0.060 Uiso 1 1 calc R . .
C16 C 0.89678(8) 0.85312(14) 0.21109(8) 0.0434(3) Uani 1 1 d . . .
C17 C 0.92598(9) 0.70805(16) 0.22439(9) 0.0527(3) Uani 1 1 d . . .
H17 H 0.8971 0.6428 0.2533 0.063 Uiso 1 1 calc R . .
C18 C 0.99804(11) 0.6585(2) 0.19501(11) 0.0683(5) Uani 1 1 d . . .
H18 H 1.0180 0.5612 0.2056 0.082 Uiso 1 1 calc R . .
C19 C 1.03954(11) 0.7531(2) 0.15046(12) 0.0753(5) Uani 1 1 d . . .
H19 H 1.0882 0.7202 0.1315 0.090 Uiso 1 1 calc R . .
C20 C 1.00962(11) 0.8954(2) 0.13388(11) 0.0720(5) Uani 1 1 d . . .
H20 H 1.0368 0.9584 0.1020 0.086 Uiso 1 1 calc R . .
C21 C 0.93877(9) 0.94641(17) 0.16445(9) 0.0557(4) Uani 1 1 d . . .
H21 H 0.9193 1.0439 0.1536 0.067 Uiso 1 1 calc R . .
C22 C 0.58479(12) 0.85413(19) -0.05528(10) 0.0669(4) Uani 1 1 d . . .
H22A H 0.5588 0.9501 -0.0728 0.100 Uiso 1 1 calc R . .
H22B H 0.5407 0.7794 -0.0823 0.100 Uiso 1 1 calc R . .
H22C H 0.6377 0.8420 -0.0753 0.100 Uiso 1 1 calc R . .
N1 N 0.68336(7) 0.82504(13) 0.33101(7) 0.0475(3) Uani 1 1 d . . .
N2 N 0.75813(11) 0.5884(2) 0.64290(11) 0.0751(4) Uani 1 1 d . . .
O1 O 0.70921(11) 0.50308(16) 0.58992(10) 0.0911(4) Uani 1 1 d . . .
O2 O 0.78606(14) 0.5632(2) 0.72387(10) 0.1267(6) Uani 1 1 d . . .
H1 H 0.6340(12) 0.8280(18) 0.3489(11) 0.062(5) 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
C1 C2 1.3931(18) . ?
C1 C6 1.3998(18) . ?
C1 N1 1.4024(16) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3933(19) . ?
C4 C22 1.5115(19) . ?
C5 C6 1.3921(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.5238(16) . ?
C7 C16 1.5182(17) . ?
C7 C8 1.5276(17) . ?
C7 H7 0.9800 . ?
C8 C9 1.5229(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.4542(16) . ?
C9 C10 1.5098(17) . ?
C9 H9 0.9800 . ?
C10 C15 1.375(2) . ?
C10 C11 1.3896(19) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.3935(19) . ?
C14 N2 1.463(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.3822(19) . ?
C16 C21 1.3891(19) . ?
C17 C18 1.391(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 H1 0.882(18) . ?
N2 O1 1.211(2) . ?
N2 O2 1.2203(19) . ?

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 C6 119.18(12) . . ?
C2 C1 N1 119.21(12) . . ?
C6 C1 N1 121.57(10) . . ?
C3 C2 C1 120.87(13) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.31(11) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 117.29(12) . . ?
C3 C4 C22 121.84(12) . . ?
C5 C4 C22 120.86(13) . . ?
C6 C5 C4 122.79(13) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C1 118.47(10) . . ?
C5 C6 C7 120.78(11) . . ?
C1 C6 C7 120.65(10) . . ?
C16 C7 C6 113.69(9) . . ?
C16 C7 C8 111.17(9) . . ?
C6 C7 C8 111.17(10) . . ?
C16 C7 H7 106.8 . . ?
C6 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
C9 C8 C7 111.63(9) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C10 111.27(11) . . ?
N1 C9 C8 107.89(10) . . ?
C10 C9 C8 110.57(9) . . ?
N1 C9 H9 109.0 . . ?
C10 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
C15 C10 C11 118.77(12) . . ?
C15 C10 C9 122.89(11) . . ?
C11 C10 C9 118.31(13) . . ?
C12 C11 C10 121.50(15) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 120.15(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 118.50(14) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 122.47(15) . . ?
C13 C14 N2 119.53(14) . . ?
C15 C14 N2 117.99(15) . . ?
C10 C15 C14 118.60(13) . . ?
C10 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C21 118.29(13) . . ?
C17 C16 C7 121.58(11) . . ?
C21 C16 C7 120.10(12) . . ?
C16 C17 C18 120.77(14) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.95(16) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.16(15) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.19(16) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 120.58(16) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 C9 117.34(10) . . ?
C1 N1 H1 111.6(11) . . ?
C9 N1 H1 117.5(11) . . ?
O1 N2 O2 122.33(18) . . ?
O1 N2 C14 119.03(14) . . ?
O2 N2 C14 118.63(18) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.67
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 993488'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_140106d_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.226(5)
_cell_length_b                   9.609(5)
_cell_length_c                   12.006(7)
_cell_angle_alpha                84.063(13)
_cell_angle_beta                 72.757(12)
_cell_angle_gamma                69.008(12)
_cell_volume                     949.1(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2565
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5655
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3670
_reflns_number_gt                2733
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_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)+(0.1530P)²+0.0315P] 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         3670
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.2167
_refine_ls_wR_factor_gt          0.1817
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.8425(2) 0.6496(2) 0.61006(16) 0.0440(5) Uani 1 1 d . . .
H1 H 0.9394 0.6550 0.6143 0.053 Uiso 1 1 calc R . .
C2 C 0.8015(2) 0.6786(2) 0.50614(17) 0.0490(5) Uani 1 1 d . . .
C3 C 0.6606(3) 0.6715(3) 0.49432(19) 0.0594(6) Uani 1 1 d . . .
H3 H 0.6363 0.6899 0.4232 0.071 Uiso 1 1 calc R . .
C4 C 0.5558(3) 0.6356(3) 0.5929(2) 0.0638(6) Uani 1 1 d . . .
H4 H 0.4589 0.6310 0.5879 0.077 Uiso 1 1 calc R . .
C5 C 0.5930(2) 0.6064(3) 0.69849(19) 0.0550(5) Uani 1 1 d . . .
H5 H 0.5209 0.5828 0.7634 0.066 Uiso 1 1 calc R . .
C6 C 0.7380(2) 0.6122(2) 0.70836(17) 0.0439(5) Uani 1 1 d . . .
C7 C 0.7815(2) 0.5791(2) 0.82212(16) 0.0431(5) Uani 1 1 d . . .
H7 H 0.8942 0.5720 0.8075 0.052 Uiso 1 1 calc R . .
C8 C 0.6755(2) 0.6977(2) 0.91606(17) 0.0476(5) Uani 1 1 d . . .
H8A H 0.5649 0.6993 0.9374 0.057 Uiso 1 1 calc R . .
H8B H 0.6763 0.7951 0.8858 0.057 Uiso 1 1 calc R . .
C9 C 0.7387(2) 0.66380(19) 1.02400(16) 0.0406(4) Uani 1 1 d . . .
H9 H 0.8405 0.6836 1.0029 0.049 Uiso 1 1 calc R . .
C10 C 0.6230(2) 0.76898(19) 1.12417(16) 0.0427(5) Uani 1 1 d . . .
C11 C 0.6589(3) 0.8837(2) 1.1559(2) 0.0575(6) Uani 1 1 d . . .
H11 H 0.7553 0.8982 1.1153 0.069 Uiso 1 1 calc R . .
C12 C 0.5530(4) 0.9782(3) 1.2480(3) 0.0783(8) Uani 1 1 d . . .
H12 H 0.5787 1.0554 1.2684 0.094 Uiso 1 1 calc R . .
C13 C 0.4109(4) 0.9579(3) 1.3089(2) 0.0800(9) Uani 1 1 d . . .
H13 H 0.3404 1.0211 1.3706 0.096 Uiso 1 1 calc R . .
C14 C 0.3730(3) 0.8450(3) 1.2788(2) 0.0781(8) Uani 1 1 d . . .
H14 H 0.2771 0.8306 1.3206 0.094 Uiso 1 1 calc R . .
C15 C 0.4771(2) 0.7516(2) 1.1861(2) 0.0601(6) Uani 1 1 d . . .
H15 H 0.4490 0.6763 1.1651 0.072 Uiso 1 1 calc R . .
C16 C 0.77799(18) 0.49852(19) 1.05740(15) 0.0373(4) Uani 1 1 d . . .
C17 C 0.8048(2) 0.4502(2) 1.16504(16) 0.0416(5) Uani 1 1 d . . .
H17 H 0.7950 0.5198 1.2177 0.050 Uiso 1 1 calc R . .
C18 C 0.8462(2) 0.2995(2) 1.19626(17) 0.0451(5) Uani 1 1 d . . .
C19 C 0.8615(2) 0.1944(2) 1.11857(19) 0.0520(5) Uani 1 1 d . . .
H19 H 0.8891 0.0939 1.1382 0.062 Uiso 1 1 calc R . .
C20 C 0.8347(2) 0.2423(2) 1.01045(18) 0.0514(5) Uani 1 1 d . . .
H20 H 0.8436 0.1724 0.9584 0.062 Uiso 1 1 calc R . .
C21 C 0.7947(2) 0.3927(2) 0.97773(16) 0.0416(5) Uani 1 1 d . . .
C22 C 0.9126(4) 0.1135(3) 1.3413(3) 0.0896(9) Uani 1 1 d . . .
H22A H 0.8305 0.0755 1.3389 0.134 Uiso 1 1 calc R . .
H22B H 0.9226 0.1058 1.4192 0.134 Uiso 1 1 calc R . .
H22C H 1.0140 0.0566 1.2892 0.134 Uiso 1 1 calc R . .
N1 N 0.9133(2) 0.7201(2) 0.40382(16) 0.0605(5) Uani 1 1 d . . .
N2 N 0.7667(2) 0.43540(19) 0.86834(15) 0.0482(4) Uani 1 1 d . . .
O1 O 0.8941(2) 0.7189(3) 0.30844(15) 0.0925(7) Uani 1 1 d . . .
O2 O 1.0243(3) 0.7491(3) 0.41771(16) 0.0939(7) Uani 1 1 d . . .
O3 O 0.86930(19) 0.26604(17) 1.30633(14) 0.0609(5) Uani 1 1 d . . .
H2 H 0.826(3) 0.361(3) 0.815(2) 0.057(6) 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
C1 C2 1.382(3) . ?
C1 C6 1.392(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(3) . ?
C2 N1 1.474(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.507(3) . ?
C7 N2 1.471(3) . ?
C7 C8 1.530(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.533(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.525(3) . ?
C9 C16 1.535(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.376(3) . ?
C10 C15 1.391(3) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.389(3) . ?
C16 C21 1.405(3) . ?
C17 C18 1.400(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C18 O3 1.388(2) . ?
C19 C20 1.394(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.402(3) . ?
C20 H20 0.9300 . ?
C21 N2 1.405(3) . ?
C22 O3 1.427(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 O1 1.211(3) . ?
N1 O2 1.212(3) . ?
N2 H2 0.91(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 C6 119.63(18) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C3 C2 C1 122.8(2) . . ?
C3 C2 N1 118.6(2) . . ?
C1 C2 N1 118.50(19) . . ?
C2 C3 C4 117.4(2) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.36(18) . . ?
C1 C6 C7 120.30(16) . . ?
C5 C6 C7 121.33(17) . . ?
N2 C7 C6 109.97(15) . . ?
N2 C7 C8 107.81(16) . . ?
C6 C7 C8 113.62(15) . . ?
N2 C7 H7 108.4 . . ?
C6 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C7 C8 C9 110.13(15) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 110.94(14) . . ?
C10 C9 C16 113.27(15) . . ?
C8 C9 C16 111.34(15) . . ?
C10 C9 H9 107.0 . . ?
C8 C9 H9 107.0 . . ?
C16 C9 H9 107.0 . . ?
C11 C10 C15 118.00(19) . . ?
C11 C10 C9 121.34(18) . . ?
C15 C10 C9 120.66(17) . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 C21 118.88(17) . . ?
C17 C16 C9 120.46(15) . . ?
C21 C16 C9 120.60(17) . . ?
C16 C17 C18 121.68(17) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 O3 124.20(18) . . ?
C19 C18 C17 119.83(18) . . ?
O3 C18 C17 115.97(17) . . ?
C18 C19 C20 118.71(18) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C21 122.00(18) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C20 C21 N2 119.75(17) . . ?
C20 C21 C16 118.88(18) . . ?
N2 C21 C16 121.34(17) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 N1 O2 122.4(2) . . ?
O1 N1 C2 118.8(2) . . ?
O2 N1 C2 118.80(19) . . ?
C21 N2 C7 116.78(15) . . ?
C21 N2 H2 111.2(14) . . ?
C7 N2 H2 111.5(15) . . ?
C18 O3 C22 117.75(18) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 993489'
