# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_qq

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 Cl N2 O2'
_chemical_formula_weight         302.75

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           ?
_symmetry_space_group_name_H-M   ?

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                   13.476(5)
_cell_length_b                   6.865(3)
_cell_length_c                   17.826(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.273(7)
_cell_angle_gamma                90.00
_cell_volume                     1598.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            9688
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         26.17
_reflns_number_total             3163
_reflns_number_gt                1482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0807P)²+1.2154P] 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         3163
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1645
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2409
_refine_ls_wR_factor_gt          0.1934
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 1.04699(13) 0.8854(3) 0.13517(10) 0.1483(8) Uani 1 1 d . . .
O2 O 0.6845(3) -0.1537(5) 0.13146(18) 0.1124(12) Uani 1 1 d . . .
O1 O 0.5739(3) -0.3963(5) 0.08853(18) 0.1002(11) Uani 1 1 d . . .
N1 N 0.5456(3) -0.2637(6) -0.0615(2) 0.0792(10) Uani 1 1 d . . .
C12 C 0.6085(3) -0.1695(7) 0.0001(2) 0.0851(13) Uani 1 1 d . . .
C1 C 0.9638(3) 0.6934(7) 0.1033(3) 0.0811(12) Uani 1 1 d . . .
C11 C 0.5417(4) -0.1651(8) -0.1263(3) 0.0930(14) Uani 1 1 d . . .
H11 H 0.5038 -0.1991 -0.1756 0.112 Uiso 1 1 calc R . .
C2 C 0.9137(4) 0.6804(7) 0.0267(3) 0.0890(13) Uani 1 1 d . . .
H2 H 0.9245 0.7732 -0.0085 0.107 Uiso 1 1 calc R . .
C14 C 0.6197(4) -0.2527(8) 0.0765(3) 0.0879(13) Uani 1 1 d . . .
C9 C 0.6443(4) -0.0075(9) -0.0277(3) 0.124(2) Uani 1 1 d . . .
C10 C 0.6029(4) -0.0055(8) -0.1080(3) 0.1113(18) Uani 1 1 d . . .
C3 C 0.8485(4) 0.5311(9) 0.0030(3) 0.1184(19) Uani 1 1 d . . .
H3 H 0.8135 0.5218 -0.0488 0.142 Uiso 1 1 calc R . .
C6 C 0.9488(4) 0.5592(8) 0.1552(3) 0.1026(15) Uani 1 1 d . . .
H6 H 0.9829 0.5695 0.2072 0.123 Uiso 1 1 calc R . .
C16 C 0.7868(5) -0.1301(11) 0.2589(3) 0.155(3) Uani 1 1 d . . .
H16A H 0.8456 -0.1540 0.2389 0.233 Uiso 1 1 calc R . .
H16B H 0.7993 -0.1792 0.3108 0.233 Uiso 1 1 calc R . .
H16C H 0.7739 0.0074 0.2589 0.233 Uiso 1 1 calc R . .
C5 C 0.8835(6) 0.4100(9) 0.1299(3) 0.163(3) Uani 1 1 d . . .
H5 H 0.8727 0.3171 0.1650 0.195 Uiso 1 1 calc R . .
C15 C 0.6978(5) -0.2284(10) 0.2103(3) 0.147(3) Uani 1 1 d . . .
H15A H 0.6373 -0.2016 0.2289 0.176 Uiso 1 1 calc R . .
H15B H 0.7088 -0.3681 0.2113 0.176 Uiso 1 1 calc R . .
N2 N 0.6315(6) 0.2534(12) -0.2027(4) 0.230(4) Uani 1 1 d . . .
C13 C 0.6196(5) 0.1361(11) -0.1607(4) 0.158(3) Uani 1 1 d . . .
C7 C 0.7796(6) 0.1405(10) 0.0154(4) 0.175(4) Uani 1 1 d . . .
H7A H 0.7815 0.1120 -0.0376 0.210 Uiso 1 1 calc R . .
H7B H 0.8029 0.0318 0.0500 0.210 Uiso 1 1 calc R . .
C4 C 0.8335(6) 0.3941(10) 0.0541(4) 0.177(4) Uani 1 1 d . . .
C8 C 0.6974(4) 0.2257(12) 0.0235(4) 0.154(3) Uani 1 1 d . . .
H8A H 0.6789 0.3444 -0.0062 0.185 Uiso 1 1 calc R . .
H8B H 0.6912 0.2384 0.0763 0.185 Uiso 1 1 calc R . .
H1 H 0.507(3) -0.381(7) -0.059(2) 0.098(15) 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
Cl1 0.1562(14) 0.1555(16) 0.1412(13) -0.0469(11) 0.0518(11) -0.0825(12)
O2 0.134(3) 0.112(3) 0.076(2) -0.0018(18) -0.0028(19) -0.049(2)
O1 0.123(3) 0.085(2) 0.087(2) 0.0007(17) 0.0157(18) -0.034(2)
N1 0.084(2) 0.076(3) 0.076(2) -0.011(2) 0.0148(19) -0.016(2)
C12 0.093(3) 0.079(3) 0.075(3) 0.002(2) 0.006(2) -0.028(2)
C1 0.077(3) 0.075(3) 0.092(3) -0.014(3) 0.021(2) -0.004(2)
C11 0.092(3) 0.108(4) 0.072(3) -0.005(3) 0.006(2) -0.018(3)
C2 0.105(3) 0.079(3) 0.085(3) 0.004(3) 0.027(3) -0.001(3)
C14 0.098(3) 0.082(3) 0.077(3) -0.004(3) 0.011(2) -0.019(3)
C9 0.145(5) 0.119(4) 0.084(3) 0.010(3) -0.021(3) -0.075(4)
C10 0.125(4) 0.113(4) 0.079(3) 0.017(3) -0.008(3) -0.049(4)
C3 0.141(5) 0.113(4) 0.082(3) 0.002(3) -0.008(3) -0.039(4)
C6 0.113(4) 0.103(4) 0.080(3) -0.003(3) 0.001(3) -0.014(3)
C16 0.147(5) 0.206(7) 0.096(4) -0.035(4) -0.003(4) 0.002(5)
C5 0.250(8) 0.117(5) 0.091(4) 0.017(3) -0.017(4) -0.090(5)
C15 0.176(6) 0.169(6) 0.077(4) 0.004(4) -0.001(4) -0.066(5)
N2 0.262(8) 0.254(8) 0.123(5) 0.084(5) -0.049(5) -0.141(7)
C13 0.177(6) 0.174(7) 0.093(4) 0.042(4) -0.024(4) -0.087(5)
C7 0.227(8) 0.189(7) 0.130(5) 0.042(5) 0.081(5) 0.143(7)
C4 0.259(9) 0.140(6) 0.099(4) 0.006(4) -0.019(5) -0.131(6)
C8 0.116(4) 0.239(8) 0.115(4) 0.038(5) 0.043(4) 0.069(5)

_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 C1 1.733(4) . ?
O2 C14 1.327(5) . ?
O2 C15 1.465(6) . ?
O1 C14 1.210(5) . ?
N1 C11 1.328(5) . ?
N1 C12 1.373(5) . ?
N1 H1 0.96(5) . ?
C12 C9 1.354(6) . ?
C12 C14 1.450(6) . ?
C1 C6 1.355(6) . ?
C1 C2 1.369(6) . ?
C11 C10 1.362(6) . ?
C11 H11 0.9300 . ?
C2 C3 1.349(6) . ?
C2 H2 0.9300 . ?
C9 C10 1.403(7) . ?
C9 C8 1.894(9) . ?
C10 C13 1.407(8) . ?
C3 C4 1.359(7) . ?
C3 H3 0.9300 . ?
C6 C5 1.354(7) . ?
C6 H6 0.9300 . ?
C16 C15 1.459(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C5 C4 1.358(8) . ?
C5 H5 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N2 C13 1.137(7) . ?
C7 C8 1.292(7) . ?
C7 C4 1.946(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O2 C15 115.6(4) . . ?
C11 N1 C12 109.9(4) . . ?
C11 N1 H1 124(3) . . ?
C12 N1 H1 126(3) . . ?
C9 C12 N1 107.4(4) . . ?
C9 C12 C14 134.7(4) . . ?
N1 C12 C14 117.8(4) . . ?
C6 C1 C2 121.2(4) . . ?
C6 C1 Cl1 119.1(4) . . ?
C2 C1 Cl1 119.8(4) . . ?
N1 C11 C10 108.1(4) . . ?
N1 C11 H11 126.0 . . ?
C10 C11 H11 126.0 . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
O1 C14 O2 123.9(4) . . ?
O1 C14 C12 123.2(4) . . ?
O2 C14 C12 112.9(4) . . ?
C12 C9 C10 107.1(4) . . ?
C12 C9 C8 130.1(5) . . ?
C10 C9 C8 119.4(4) . . ?
C11 C10 C9 107.5(4) . . ?
C11 C10 C13 125.7(5) . . ?
C9 C10 C13 126.8(5) . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C6 C1 118.7(5) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C16 C15 O2 107.2(5) . . ?
C16 C15 H15A 110.3 . . ?
O2 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
O2 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
N2 C13 C10 178.3(11) . . ?
C8 C7 C4 79.1(6) . . ?
C8 C7 H7A 115.4 . . ?
C4 C7 H7A 115.4 . . ?
C8 C7 H7B 115.4 . . ?
C4 C7 H7B 115.4 . . ?
H7A C7 H7B 112.4 . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 C7 118.4(5) . . ?
C3 C4 C7 119.0(5) . . ?
C7 C8 C9 78.2(6) . . ?
C7 C8 H8A 115.5 . . ?
C9 C8 H8A 115.5 . . ?
C7 C8 H8B 115.5 . . ?
C9 C8 H8B 115.5 . . ?
H8A C8 H8B 112.5 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.17
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 968815'
#######################################################################
#
#                 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_p21c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32

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           ?
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  -p2ybc

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                   8.8199(8)
_cell_length_b                   12.7684(12)
_cell_length_c                   13.8563(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.733(2)
_cell_angle_gamma                90.00
_cell_volume                     1559.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            9735
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         26.04
_reflns_number_total             3070
_reflns_number_gt                2132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0527P)²+0.2760P] 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         3070
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C8 C 0.53897(19) 0.41499(14) 0.87036(13) 0.0419(4) Uani 1 1 d . . .
H8 H 0.5339 0.3543 0.9072 0.050 Uiso 1 1 calc R . .
C7 C 0.66624(19) 0.43054(16) 0.82486(14) 0.0478(5) Uani 1 1 d . . .
H7 H 0.6706 0.4901 0.7865 0.057 Uiso 1 1 calc R . .
C9 C 0.40598(18) 0.48198(13) 0.86946(12) 0.0382(4) Uani 1 1 d . . .
N1 N 0.18175(17) 0.55194(13) 0.90557(12) 0.0466(4) Uani 1 1 d . . .
C11 C 0.2359(2) 0.61149(15) 0.83575(14) 0.0501(5) Uani 1 1 d . . .
H11 H 0.1883 0.6699 0.8085 0.060 Uiso 1 1 calc R . .
C12 C 0.28096(18) 0.47180(14) 0.92740(12) 0.0389(4) Uani 1 1 d . . .
C10 C 0.3748(2) 0.57175(15) 0.81062(13) 0.0449(5) Uani 1 1 d . . .
O1 O 0.9552(2) 0.12231(15) 0.93861(15) 0.0969(6) Uani 1 1 d . . .
N2 N 0.5417(2) 0.64588(18) 0.67817(16) 0.0840(7) Uani 1 1 d . . .
C17 C 0.4665(2) 0.61369(17) 0.73688(16) 0.0559(6) Uani 1 1 d . . .
C13 C 0.23702(19) 0.39610(14) 0.99993(13) 0.0425(4) Uani 1 1 d . . .
O2 O 0.11761(14) 0.39972(11) 1.04088(10) 0.0567(4) Uani 1 1 d . . .
O3 O 0.33982(14) 0.32173(10) 1.01609(9) 0.0518(4) Uani 1 1 d . . .
C14 C 0.2997(2) 0.24015(17) 1.08316(16) 0.0633(6) Uani 1 1 d . . .
H14A H 0.2076 0.2051 1.0608 0.076 Uiso 1 1 calc R . .
H14B H 0.2826 0.2699 1.1463 0.076 Uiso 1 1 calc R . .
C15 C 0.4282(3) 0.16436(19) 1.08885(19) 0.0837(8) Uani 1 1 d . . .
H15A H 0.4049 0.1092 1.1330 0.126 Uiso 1 1 calc R . .
H15B H 0.5186 0.1999 1.1111 0.126 Uiso 1 1 calc R . .
H15C H 0.4438 0.1353 1.0260 0.126 Uiso 1 1 calc R . .
C16 C 0.8328(4) 0.0905(3) 0.9962(2) 0.1168(11) Uani 1 1 d . . .
H16A H 0.8588 0.0263 1.0288 0.175 Uiso 1 1 calc R . .
H16B H 0.7439 0.0799 0.9558 0.175 Uiso 1 1 calc R . .
H16C H 0.8131 0.1438 1.0431 0.175 Uiso 1 1 calc R . .
H1N H 0.090(2) 0.5582(15) 0.9343(14) 0.059(6) Uiso 1 1 d . . .
C6 C 0.8014(2) 0.36389(16) 0.82843(14) 0.0482(5) Uani 1 1 d . . .
C1 C 0.8091(2) 0.27328(17) 0.88437(15) 0.0542(5) Uani 1 1 d . . .
H1 H 0.7267 0.2535 0.9205 0.065 Uiso 1 1 calc R . .
C5 C 0.9264(2) 0.39154(19) 0.77546(16) 0.0630(6) Uani 1 1 d . . .
H5 H 0.9230 0.4516 0.7375 0.076 Uiso 1 1 calc R . .
C4 C 1.0557(2) 0.3306(2) 0.7786(2) 0.0765(8) Uani 1 1 d . . .
H4 H 1.1391 0.3505 0.7435 0.092 Uiso 1 1 calc R . .
C2 C 0.9390(2) 0.21264(19) 0.88629(17) 0.0659(6) Uani 1 1 d . . .
C3 C 1.0624(2) 0.2414(2) 0.83263(19) 0.0761(8) Uani 1 1 d . . .
H3 H 1.1492 0.2001 0.8335 0.091 Uiso 1 1 calc R . .

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
C8 0.0365(9) 0.0416(11) 0.0477(11) -0.0011(9) 0.0049(8) 0.0036(8)
C7 0.0387(10) 0.0494(12) 0.0556(12) -0.0001(9) 0.0060(9) 0.0029(9)
C9 0.0335(9) 0.0393(11) 0.0419(10) -0.0036(8) 0.0009(8) -0.0008(8)
N1 0.0345(8) 0.0506(10) 0.0552(10) 0.0034(8) 0.0088(8) 0.0080(8)
C11 0.0440(11) 0.0474(12) 0.0590(12) 0.0103(10) 0.0028(9) 0.0062(9)
C12 0.0336(9) 0.0398(11) 0.0435(10) -0.0003(8) 0.0025(8) 0.0028(8)
C10 0.0386(10) 0.0474(12) 0.0490(11) 0.0044(9) 0.0047(8) 0.0006(8)
O1 0.0715(12) 0.0935(14) 0.1253(16) 0.0051(12) -0.0037(11) 0.0418(11)
N2 0.0658(12) 0.0968(16) 0.0907(15) 0.0399(13) 0.0228(11) 0.0052(11)
C17 0.0470(11) 0.0573(14) 0.0635(14) 0.0142(11) 0.0048(10) 0.0058(10)
C13 0.0354(9) 0.0459(11) 0.0463(11) -0.0033(9) 0.0046(8) 0.0014(9)
O2 0.0400(7) 0.0680(10) 0.0631(9) 0.0067(7) 0.0178(6) 0.0061(7)
O3 0.0449(7) 0.0526(9) 0.0588(9) 0.0157(7) 0.0135(6) 0.0092(6)
C14 0.0629(14) 0.0635(15) 0.0640(14) 0.0214(12) 0.0105(11) 0.0009(11)
C15 0.0951(19) 0.0681(17) 0.0882(19) 0.0258(14) 0.0077(15) 0.0169(14)
C16 0.109(2) 0.099(2) 0.142(3) 0.037(2) 0.001(2) 0.047(2)
C6 0.0359(10) 0.0571(13) 0.0516(12) -0.0160(10) 0.0029(8) 0.0034(9)
C1 0.0368(10) 0.0649(14) 0.0609(13) -0.0119(11) 0.0015(9) 0.0102(10)
C5 0.0445(11) 0.0779(16) 0.0673(14) -0.0204(12) 0.0145(10) -0.0020(11)
C4 0.0412(12) 0.103(2) 0.0865(18) -0.0389(16) 0.0181(12) -0.0008(13)
C2 0.0495(13) 0.0711(16) 0.0764(15) -0.0211(13) -0.0096(11) 0.0221(12)
C3 0.0369(12) 0.100(2) 0.0911(19) -0.0441(17) -0.0014(12) 0.0222(13)

_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
C8 C7 1.319(2) . ?
C8 C9 1.451(2) . ?
C8 H8 0.9300 . ?
C7 C6 1.464(3) . ?
C7 H7 0.9300 . ?
C9 C12 1.390(2) . ?
C9 C10 1.429(2) . ?
N1 C11 1.330(2) . ?
N1 C12 1.374(2) . ?
N1 H1N 0.91(2) . ?
C11 C10 1.380(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.455(2) . ?
C10 C17 1.427(3) . ?
O1 C2 1.367(3) . ?
O1 C16 1.421(3) . ?
N2 C17 1.141(2) . ?
C13 O2 1.212(2) . ?
C13 O3 1.327(2) . ?
O3 C14 1.447(2) . ?
C14 C15 1.490(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C6 C5 1.388(3) . ?
C6 C1 1.393(3) . ?
C1 C2 1.382(3) . ?
C1 H1 0.9300 . ?
C5 C4 1.380(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.362(4) . ?
C4 H4 0.9300 . ?
C2 C3 1.386(3) . ?
C3 H3 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
C7 C8 C9 127.33(18) . . ?
C7 C8 H8 116.3 . . ?
C9 C8 H8 116.3 . . ?
C8 C7 C6 126.88(19) . . ?
C8 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
C12 C9 C10 105.21(15) . . ?
C12 C9 C8 126.53(16) . . ?
C10 C9 C8 128.27(16) . . ?
C11 N1 C12 110.22(15) . . ?
C11 N1 H1N 127.5(12) . . ?
C12 N1 H1N 122.2(12) . . ?
N1 C11 C10 108.31(17) . . ?
N1 C11 H11 125.8 . . ?
C10 C11 H11 125.8 . . ?
N1 C12 C9 108.32(15) . . ?
N1 C12 C13 117.74(15) . . ?
C9 C12 C13 133.91(16) . . ?
C11 C10 C17 124.72(18) . . ?
C11 C10 C9 107.94(16) . . ?
C17 C10 C9 127.33(17) . . ?
C2 O1 C16 118.05(19) . . ?
N2 C17 C10 178.8(2) . . ?
O2 C13 O3 123.17(17) . . ?
O2 C13 C12 123.45(17) . . ?
O3 C13 C12 113.38(15) . . ?
C13 O3 C14 116.39(14) . . ?
O3 C14 C15 107.53(18) . . ?
O3 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C6 C1 118.64(18) . . ?
C5 C6 C7 119.5(2) . . ?
C1 C6 C7 121.83(18) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O1 C2 C1 123.8(2) . . ?
O1 C2 C3 115.9(2) . . ?
C1 C2 C3 120.3(2) . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 968816'
