# 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_test7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 Cl N2 O2'
_chemical_formula_weight         336.76

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'
Cl Cl 0.1484 0.1585 '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                   8.808(4)
_cell_length_b                   19.723(8)
_cell_length_c                   9.339(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.983(10)
_cell_angle_gamma                90.00
_cell_volume                     1580.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1120
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   SADABS

_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 SMART APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13327
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2646
_reflns_number_gt                1962
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.2000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2646
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.1094
_refine_ls_wR_factor_ref         0.3073
_refine_ls_wR_factor_gt          0.2726
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_restrained_S_all      1.245
_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
Cl1 Cl 0.24326(12) 0.47525(5) 0.56186(11) 0.0446(5) Uani 1 1 d . . .
C4 C 0.5275(5) 0.3774(2) -0.0129(4) 0.0389(10) Uani 1 1 d . . .
C5 C 0.6071(5) 0.39252(19) 0.1286(4) 0.0354(9) Uani 1 1 d . . .
C2 C 0.7007(6) 0.4543(3) -0.0942(6) 0.0560(13) Uani 1 1 d . . .
H2 H 0.7331 0.4773 -0.1690 0.067 Uiso 1 1 calc R . .
C3 C 0.5791(6) 0.4096(2) -0.1263(5) 0.0483(11) Uani 1 1 d . . .
H3 H 0.5307 0.4008 -0.2236 0.058 Uiso 1 1 calc R . .
C1 C 0.7752(6) 0.4648(2) 0.0523(6) 0.0525(12) Uani 1 1 d . . .
H1 H 0.8595 0.4943 0.0739 0.063 Uiso 1 1 calc R . .
C6 C 0.4154(4) 0.37692(18) 0.2598(4) 0.0320(9) Uani 1 1 d . . .
C10 C 0.2564(4) 0.42819(19) 0.4066(4) 0.0345(9) Uani 1 1 d . . .
C11 C 0.4019(5) 0.41335(19) 0.3843(4) 0.0344(9) Uani 1 1 d . . .
H11 H 0.4907 0.4275 0.4519 0.041 Uiso 1 1 calc R . .
C7 C 0.2846(4) 0.35631(18) 0.1563(4) 0.0340(9) Uani 1 1 d . . .
C9 C 0.1242(5) 0.40824(19) 0.3071(4) 0.0388(10) Uani 1 1 d . . .
H9 H 0.0261 0.4180 0.3231 0.047 Uiso 1 1 calc R . .
C8 C 0.1400(5) 0.3730(2) 0.1814(4) 0.0381(10) Uani 1 1 d . . .
H8 H 0.0509 0.3603 0.1127 0.046 Uiso 1 1 calc R . .
N2 N 0.2957(4) 0.31584(15) 0.0314(4) 0.0388(9) Uani 1 1 d . . .
C14 C 0.0377(5) 0.29357(19) -0.1403(4) 0.0381(10) Uani 1 1 d . . .
C12 C 0.4041(6) 0.3239(2) -0.0508(5) 0.0450(11) Uani 1 1 d . . .
C13 C 0.1703(6) 0.2664(2) -0.0222(5) 0.0459(11) Uani 1 1 d . . .
H13A H 0.1288 0.2513 0.0602 0.055 Uiso 1 1 calc R . .
H13B H 0.2144 0.2272 -0.0606 0.055 Uiso 1 1 calc R . .
C19 C -0.1008(6) 0.2586(2) -0.1732(6) 0.0583(13) Uani 1 1 d . . .
H19 H -0.1117 0.2197 -0.1202 0.070 Uiso 1 1 calc R . .
C15 C 0.0515(5) 0.3512(2) -0.2216(5) 0.0486(11) Uani 1 1 d . . .
H15 H 0.1436 0.3760 -0.2004 0.058 Uiso 1 1 calc R . .
C16 C -0.0698(6) 0.3721(3) -0.3337(6) 0.0579(13) Uani 1 1 d . . .
H16 H -0.0584 0.4106 -0.3877 0.069 Uiso 1 1 calc R . .
C17 C -0.2073(6) 0.3365(3) -0.3662(6) 0.0637(14) Uani 1 1 d . . .
H17 H -0.2879 0.3504 -0.4431 0.076 Uiso 1 1 calc R . .
C18 C -0.2256(6) 0.2800(3) -0.2843(7) 0.0684(15) Uani 1 1 d . . .
H18 H -0.3196 0.2566 -0.3028 0.082 Uiso 1 1 calc R . .
O1 O 0.5661(3) 0.36082(15) 0.2474(3) 0.0409(8) Uani 1 1 d . . .
O2 O 0.3991(5) 0.28897(19) -0.1616(4) 0.0690(11) Uani 1 1 d . . .
N1 N 0.7291(4) 0.4333(2) 0.1647(4) 0.0471(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0491(8) 0.0550(8) 0.0325(7) -0.0065(4) 0.0151(5) -0.0026(4)
C4 0.041(2) 0.042(2) 0.033(2) -0.0048(16) 0.0058(17) 0.0118(16)
C5 0.035(2) 0.042(2) 0.031(2) 0.0005(16) 0.0099(16) 0.0124(17)
C2 0.057(3) 0.069(3) 0.047(3) 0.013(2) 0.021(2) 0.015(3)
C3 0.058(3) 0.054(3) 0.035(2) 0.0018(19) 0.013(2) 0.005(2)
C1 0.049(3) 0.052(2) 0.061(3) -0.003(2) 0.021(2) -0.003(2)
C6 0.034(2) 0.0356(19) 0.0259(19) 0.0071(14) 0.0067(15) 0.0040(15)
C10 0.041(2) 0.0326(19) 0.031(2) 0.0046(16) 0.0102(16) -0.0014(15)
C11 0.035(2) 0.042(2) 0.0250(19) 0.0026(16) 0.0040(15) 0.0004(16)
C7 0.043(2) 0.0302(19) 0.0268(19) 0.0001(15) 0.0049(16) -0.0032(15)
C9 0.045(2) 0.039(2) 0.035(2) 0.0044(16) 0.0148(18) -0.0038(17)
C8 0.039(2) 0.042(2) 0.032(2) -0.0008(16) 0.0055(16) -0.0079(16)
N2 0.047(2) 0.0322(17) 0.0365(18) -0.0070(14) 0.0071(16) -0.0024(14)
C14 0.051(2) 0.0345(19) 0.030(2) -0.0093(15) 0.0117(18) -0.0070(17)
C12 0.052(3) 0.044(2) 0.039(2) -0.0078(18) 0.009(2) 0.0064(18)
C13 0.064(3) 0.033(2) 0.037(2) -0.0062(17) 0.005(2) -0.0094(19)
C19 0.062(3) 0.044(2) 0.072(3) 0.000(2) 0.021(3) -0.014(2)
C15 0.049(3) 0.051(3) 0.047(3) 0.005(2) 0.012(2) -0.009(2)
C16 0.059(3) 0.064(3) 0.052(3) 0.015(2) 0.016(2) 0.007(2)
C17 0.055(3) 0.078(4) 0.054(3) -0.007(3) 0.004(2) 0.015(3)
C18 0.049(3) 0.066(3) 0.084(4) -0.015(3) 0.000(3) -0.013(2)
O1 0.0342(16) 0.0560(17) 0.0320(15) 0.0065(12) 0.0064(12) 0.0102(12)
O2 0.082(3) 0.074(2) 0.056(2) -0.0367(18) 0.0259(19) -0.007(2)
N1 0.041(2) 0.059(2) 0.042(2) -0.0077(17) 0.0129(16) -0.0024(17)

_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
Cl1 C10 1.747(4) . ?
C4 C5 1.382(6) . ?
C4 C3 1.396(6) . ?
C4 C12 1.498(6) . ?
C5 N1 1.324(6) . ?
C5 O1 1.390(5) . ?
C2 C3 1.367(7) . ?
C2 C1 1.394(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C1 N1 1.358(6) . ?
C1 H1 0.9300 . ?
C6 C7 1.388(5) . ?
C6 C11 1.395(5) . ?
C6 O1 1.395(5) . ?
C10 C9 1.373(6) . ?
C10 C11 1.376(6) . ?
C11 H11 0.9300 . ?
C7 C8 1.385(6) . ?
C7 N2 1.435(5) . ?
C9 C8 1.398(5) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
N2 C12 1.362(6) . ?
N2 C13 1.475(5) . ?
C14 C19 1.375(6) . ?
C14 C15 1.387(6) . ?
C14 C13 1.513(6) . ?
C12 O2 1.236(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C19 C18 1.397(7) . ?
C19 H19 0.9300 . ?
C15 C16 1.380(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
C5 C4 C3 116.4(4) . . ?
C5 C4 C12 124.3(4) . . ?
C3 C4 C12 119.0(4) . . ?
N1 C5 C4 125.7(4) . . ?
N1 C5 O1 114.3(3) . . ?
C4 C5 O1 119.9(4) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N1 C1 C2 122.3(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C7 C6 C11 121.2(4) . . ?
C7 C6 O1 122.2(3) . . ?
C11 C6 O1 116.6(3) . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 Cl1 120.6(3) . . ?
C11 C10 Cl1 118.4(3) . . ?
C10 C11 C6 119.5(4) . . ?
C10 C11 H11 120.3 . . ?
C6 C11 H11 120.3 . . ?
C8 C7 C6 117.6(3) . . ?
C8 C7 N2 120.2(3) . . ?
C6 C7 N2 122.1(4) . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C7 C8 C9 121.9(4) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C12 N2 C7 125.3(3) . . ?
C12 N2 C13 116.9(3) . . ?
C7 N2 C13 117.4(3) . . ?
C19 C14 C15 118.1(4) . . ?
C19 C14 C13 119.1(4) . . ?
C15 C14 C13 122.8(4) . . ?
O2 C12 N2 120.6(4) . . ?
O2 C12 C4 118.5(4) . . ?
N2 C12 C4 120.8(3) . . ?
N2 C13 C14 114.2(3) . . ?
N2 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N2 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C19 C18 121.7(5) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 120.6(5) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.8(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 119.0(5) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C5 O1 C6 112.8(3) . . ?
C5 N1 C1 116.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         0.706
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.163
_database_code_depnum_ccdc_archive 'CCDC 994880'
#######################################################################
#
#                 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_sb0613_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 N2 O2'
_chemical_formula_weight         302.32

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   7.983(2)
_cell_length_b                   8.944(3)
_cell_length_c                   10.904(3)
_cell_angle_alpha                101.512(5)
_cell_angle_beta                 95.264(6)
_cell_angle_gamma                101.942(5)
_cell_volume                     739.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5060
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      31.91

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .19
_exptl_crystal_size_min          .17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .980
_exptl_absorpt_correction_T_max  .985
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 ?
_diffrn_reflns_number            5949
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2483
_reflns_number_gt                2259
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.1780P)²+0.7277P] 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         2483
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2157
_refine_ls_wR_factor_gt          0.2062
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_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
O3 O 1.0691(2) 1.03080(18) 0.37864(14) 0.0161(4) Uani 1 1 d . . .
N2 N 1.2811(3) 1.1567(2) 0.28355(19) 0.0204(5) Uani 1 1 d . . .
N1 N 0.7362(2) 0.9212(2) 0.23348(17) 0.0162(5) Uani 1 1 d . . .
C5 C 1.0911(3) 0.7682(3) 0.37955(19) 0.0148(5) Uani 1 1 d . . .
C10 C 0.9959(3) 0.8715(3) 0.33953(19) 0.0143(5) Uani 1 1 d . . .
C6 C 1.0192(3) 0.6040(3) 0.3408(2) 0.0175(5) Uani 1 1 d . . .
C17 C 0.9862(3) 1.1048(2) 0.1859(2) 0.0148(5) Uani 1 1 d . . .
C9 C 0.8361(3) 0.8174(3) 0.26692(19) 0.0145(5) Uani 1 1 d . . .
C12 C 1.1160(3) 1.0980(2) 0.2790(2) 0.0148(5) Uani 1 1 d . . .
C16 C 1.0399(3) 1.1809(3) 0.0912(2) 0.0190(5) Uani 1 1 d . . .
H16 H 0.9591 1.1906 0.0279 0.023 Uiso 1 1 calc R . .
C18 C 0.7980(3) 1.0544(3) 0.19239(19) 0.0153(5) Uani 1 1 d . . .
C4 C 1.2526(3) 0.8239(3) 0.4578(2) 0.0188(5) Uani 1 1 d . . .
H4 H 1.2998 0.9312 0.4838 0.023 Uiso 1 1 calc R . .
C8 C 0.7660(3) 0.6520(3) 0.2288(2) 0.0184(5) Uani 1 1 d . . .
H8 H 0.6586 0.6139 0.1792 0.022 Uiso 1 1 calc R . .
C1 C 1.1115(3) 0.5001(3) 0.3817(2) 0.0228(6) Uani 1 1 d . . .
H1 H 1.0656 0.3925 0.3577 0.027 Uiso 1 1 calc R . .
C3 C 1.3398(3) 0.7203(3) 0.4954(2) 0.0231(6) Uani 1 1 d . . .
H3 H 1.4460 0.7575 0.5467 0.028 Uiso 1 1 calc R . .
C2 C 1.2694(3) 0.5577(3) 0.4568(2) 0.0241(6) Uani 1 1 d . . .
H2 H 1.3300 0.4883 0.4824 0.029 Uiso 1 1 calc R . .
C7 C 0.8552(3) 0.5493(3) 0.2647(2) 0.0203(5) Uani 1 1 d . . .
H7 H 0.8078 0.4420 0.2389 0.024 Uiso 1 1 calc R . .
C15 C 1.2137(3) 1.2415(3) 0.0926(2) 0.0227(6) Uani 1 1 d . . .
H15 H 1.2522 1.2908 0.0296 0.027 Uiso 1 1 calc R . .
C14 C 1.3301(3) 1.2275(3) 0.1898(2) 0.0243(6) Uani 1 1 d . . .
H14 H 1.4472 1.2687 0.1906 0.029 Uiso 1 1 calc R . .
O1 O 0.7010(2) 1.1340(2) 0.16002(16) 0.0232(5) Uani 1 1 d . . .
C20 C 0.5491(3) 0.8829(3) 0.2429(2) 0.0184(5) Uani 1 1 d . . .
H20A H 0.5148 0.9788 0.2777 0.022 Uiso 1 1 calc R . .
H20B H 0.5286 0.8144 0.3014 0.022 Uiso 1 1 calc R . .
C21 C 0.4371(3) 0.8045(3) 0.1185(2) 0.0214(5) Uani 1 1 d . . .
H21 H 0.4520 0.8520 0.0505 0.026 Uiso 1 1 calc R . .
C22 C 0.3197(3) 0.6729(3) 0.1007(3) 0.0299(6) Uani 1 1 d . . .
H22 H 0.280(5) 0.596(4) 0.164(4) 0.052(10) Uiso 1 1 d . . .
H23 H 0.249(5) 0.618(4) 0.011(3) 0.040(9) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0219(8) 0.0141(8) 0.0116(8) 0.0025(6) -0.0009(6) 0.0041(6)
N2 0.0188(10) 0.0180(10) 0.0265(11) 0.0065(8) 0.0013(8) 0.0080(8)
N1 0.0148(10) 0.0198(10) 0.0154(9) 0.0062(7) -0.0003(7) 0.0062(8)
C5 0.0181(11) 0.0205(12) 0.0087(10) 0.0057(8) 0.0040(8) 0.0079(9)
C10 0.0202(11) 0.0145(11) 0.0097(10) 0.0036(8) 0.0024(8) 0.0062(9)
C6 0.0232(12) 0.0207(12) 0.0120(10) 0.0066(9) 0.0038(9) 0.0090(9)
C17 0.0178(11) 0.0113(10) 0.0159(11) 0.0024(8) 0.0014(8) 0.0058(8)
C9 0.0172(11) 0.0172(11) 0.0112(10) 0.0048(8) 0.0019(8) 0.0071(9)
C12 0.0201(11) 0.0113(10) 0.0145(10) 0.0026(8) 0.0014(8) 0.0078(8)
C16 0.0262(12) 0.0174(11) 0.0154(11) 0.0045(9) 0.0008(9) 0.0098(9)
C18 0.0188(11) 0.0157(11) 0.0124(10) 0.0034(8) -0.0019(8) 0.0076(8)
C4 0.0212(12) 0.0237(12) 0.0130(10) 0.0052(9) 0.0014(9) 0.0077(9)
C8 0.0193(11) 0.0196(12) 0.0160(11) 0.0065(9) -0.0011(8) 0.0033(9)
C1 0.0306(13) 0.0221(12) 0.0196(12) 0.0074(9) 0.0037(10) 0.0122(10)
C3 0.0211(12) 0.0351(14) 0.0174(11) 0.0104(10) 0.0000(9) 0.0127(10)
C2 0.0280(13) 0.0295(13) 0.0215(12) 0.0109(10) 0.0023(10) 0.0169(10)
C7 0.0262(12) 0.0165(11) 0.0186(11) 0.0056(9) 0.0011(9) 0.0051(9)
C15 0.0276(13) 0.0220(12) 0.0236(12) 0.0106(9) 0.0099(10) 0.0090(10)
C14 0.0185(12) 0.0243(12) 0.0326(13) 0.0095(10) 0.0068(10) 0.0061(9)
O1 0.0213(9) 0.0242(9) 0.0284(9) 0.0120(7) -0.0014(7) 0.0112(7)
C20 0.0148(11) 0.0244(12) 0.0187(11) 0.0073(9) 0.0036(8) 0.0076(9)
C21 0.0176(11) 0.0300(13) 0.0194(11) 0.0085(10) 0.0001(9) 0.0098(10)
C22 0.0229(12) 0.0329(14) 0.0311(14) 0.0047(11) -0.0042(10) 0.0063(11)

_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
O3 C10 1.386(3) . ?
O3 C12 1.387(3) . ?
N2 C12 1.306(3) . ?
N2 C14 1.352(3) . ?
N1 C18 1.369(3) . ?
N1 C9 1.421(3) . ?
N1 C20 1.480(3) . ?
C5 C4 1.415(3) . ?
C5 C10 1.419(3) . ?
C5 C6 1.422(3) . ?
C10 C9 1.376(3) . ?
C6 C1 1.412(3) . ?
C6 C7 1.420(3) . ?
C17 C16 1.398(3) . ?
C17 C12 1.402(3) . ?
C17 C18 1.489(3) . ?
C9 C8 1.429(3) . ?
C16 C15 1.379(4) . ?
C18 O1 1.228(3) . ?
C4 C3 1.370(3) . ?
C8 C7 1.366(3) . ?
C1 C2 1.378(4) . ?
C3 C2 1.408(4) . ?
C15 C14 1.387(4) . ?
C20 C21 1.507(3) . ?
C21 C22 1.311(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 O3 C12 112.31(15) . . ?
C12 N2 C14 117.1(2) . . ?
C18 N1 C9 125.56(19) . . ?
C18 N1 C20 116.64(18) . . ?
C9 N1 C20 117.79(18) . . ?
C4 C5 C10 122.0(2) . . ?
C4 C5 C6 119.6(2) . . ?
C10 C5 C6 118.4(2) . . ?
C9 C10 O3 120.92(19) . . ?
C9 C10 C5 121.9(2) . . ?
O3 C10 C5 117.14(19) . . ?
C1 C6 C7 121.8(2) . . ?
C1 C6 C5 118.9(2) . . ?
C7 C6 C5 119.2(2) . . ?
C16 C17 C12 116.6(2) . . ?
C16 C17 C18 119.30(19) . . ?
C12 C17 C18 123.59(19) . . ?
C10 C9 N1 121.9(2) . . ?
C10 C9 C8 118.9(2) . . ?
N1 C9 C8 119.22(19) . . ?
N2 C12 O3 115.75(19) . . ?
N2 C12 C17 125.2(2) . . ?
O3 C12 C17 118.98(19) . . ?
C15 C16 C17 119.3(2) . . ?
O1 C18 N1 121.4(2) . . ?
O1 C18 C17 118.79(19) . . ?
N1 C18 C17 119.86(19) . . ?
C3 C4 C5 120.2(2) . . ?
C7 C8 C9 120.7(2) . . ?
C2 C1 C6 120.2(2) . . ?
C4 C3 C2 120.4(2) . . ?
C1 C2 C3 120.7(2) . . ?
C8 C7 C6 120.9(2) . . ?
C16 C15 C14 118.7(2) . . ?
N2 C14 C15 123.0(2) . . ?
N1 C20 C21 113.79(18) . . ?
C22 C21 C20 123.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.097
_database_code_depnum_ccdc_archive 'CCDC 994881'
