Supplementary Material for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177

_publ_contact_author_name        'George Weaver'
_publ_contact_author_address     
;
Department of Chemistry
Loughborough University
Loughborough
Leics
LE11 3TU
UNITED KINGDOM

;

_publ_section_title              
;
Radical Reactions with 3H-Quinazolin-4-ones: Synthesis
of Deoxyvasicinone, Mackinazolinone, Luotonin A, Rutaecarpine and
Tryptanthrin
;
_publ_contact_author_email       G.W.WEAVER@LBORO.AC.UK
loop_
_publ_author_name
G.Weaver
W.R.Bowman
M.R.J.Elsegood
T.Stein

data_30
_database_code_depnum_ccdc_archive 'CCDC 622451'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2 O S'
_chemical_formula_sum            'C16 H14 N2 O S'
_chemical_formula_weight         282.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc
_symmetry_space_group_name_Hall  'C -2yc'

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

_cell_length_a                   4.6405(7)
_cell_length_b                   25.329(4)
_cell_length_c                   12.1910(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.047(2)
_cell_angle_gamma                90.00
_cell_volume                     1422.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2505
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.77

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'SADABS v2.10, Sheldrick, G.M. (2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5350
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         28.73
_reflns_number_total             3005
_reflns_number_gt                2351
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. 1339 Friedel pairs.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1005P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_atom_sites_solution_hydrogens   'geom except H(2) coords freely refined'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(13)
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     184
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
N1 N 0.5300(6) 0.19362(12) 0.6679(2) 0.0236(7) Uani 1 1 d . . .
C1 C 0.4066(7) 0.21118(14) 0.5651(3) 0.0240(7) Uani 1 1 d . . .
S1 S 0.1436(2) 0.17829(4) 0.48714(9) 0.0331(3) Uani 1 1 d . . .
N2 N 0.5072(6) 0.25707(12) 0.5303(2) 0.0260(6) Uani 1 1 d . . .
H2 H 0.429(9) 0.2667(16) 0.467(4) 0.031 Uiso 1 1 d . . .
C2 C 0.7275(8) 0.28714(14) 0.5880(3) 0.0238(7) Uani 1 1 d . . .
C3 C 0.8156(9) 0.33469(15) 0.5442(3) 0.0329(9) Uani 1 1 d . . .
H3 H 0.7257 0.3472 0.4749 0.039 Uiso 1 1 calc R . .
C4 C 1.0351(9) 0.36289(16) 0.6036(4) 0.0364(9) Uani 1 1 d . . .
H4 H 1.0961 0.3954 0.5750 0.044 Uiso 1 1 calc R . .
C5 C 1.1700(9) 0.34463(16) 0.7053(3) 0.0353(9) Uani 1 1 d . . .
H5 H 1.3229 0.3644 0.7448 0.042 Uiso 1 1 calc R . .
C6 C 1.0816(8) 0.29799(15) 0.7483(3) 0.0284(8) Uani 1 1 d . . .
H6 H 1.1726 0.2856 0.8176 0.034 Uiso 1 1 calc R . .
C7 C 0.8576(8) 0.26890(13) 0.6899(3) 0.0236(7) Uani 1 1 d . . .
C8 C 0.7576(8) 0.21945(14) 0.7327(3) 0.0242(7) Uani 1 1 d . . .
O1 O 0.8619(6) 0.19952(10) 0.8208(2) 0.0320(6) Uani 1 1 d . . .
C9 C 0.4292(8) 0.14396(14) 0.7137(3) 0.0275(8) Uani 1 1 d . . .
H9A H 0.2224 0.1383 0.6852 0.033 Uiso 1 1 calc R . .
H9B H 0.4439 0.1469 0.7951 0.033 Uiso 1 1 calc R . .
C10 C 0.6053(9) 0.09659(15) 0.6836(4) 0.0353(9) Uani 1 1 d . . .
H10A H 0.5779 0.0917 0.6024 0.042 Uiso 1 1 calc R . .
H10B H 0.8140 0.1032 0.7070 0.042 Uiso 1 1 calc R . .
C11 C 0.5129(9) 0.04717(15) 0.7388(3) 0.0343(9) Uani 1 1 d . . .
C12 C 0.2967(11) 0.01529(17) 0.6871(5) 0.0504(12) Uani 1 1 d . . .
H12 H 0.2055 0.0241 0.6154 0.061 Uiso 1 1 calc R . .
C13 C 0.2124(16) -0.0295(2) 0.7395(6) 0.0722(18) Uani 1 1 d . . .
H13 H 0.0636 -0.0513 0.7031 0.087 Uiso 1 1 calc R . .
C14 C 0.3406(16) -0.0432(2) 0.8437(7) 0.075(2) Uani 1 1 d . . .
H14 H 0.2828 -0.0743 0.8788 0.090 Uiso 1 1 calc R . .
C15 C 0.5500(16) -0.0116(3) 0.8949(6) 0.079(2) Uani 1 1 d . . .
H15 H 0.6379 -0.0202 0.9672 0.095 Uiso 1 1 calc R . .
C16 C 0.6382(13) 0.0335(2) 0.8429(5) 0.0619(14) Uani 1 1 d . . .
H16 H 0.7869 0.0551 0.8798 0.074 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
N1 0.0249(15) 0.0266(16) 0.0187(15) -0.0018(11) 0.0007(12) -0.0008(11)
C1 0.0256(19) 0.0262(19) 0.0195(16) -0.0042(13) -0.0003(14) 0.0036(14)
S1 0.0314(4) 0.0360(5) 0.0289(4) -0.0071(4) -0.0086(3) -0.0029(4)
N2 0.0302(17) 0.0293(16) 0.0168(13) 0.0002(12) -0.0039(13) 0.0004(12)
C2 0.0278(18) 0.0225(17) 0.0203(16) -0.0038(13) 0.0002(14) -0.0012(14)
C3 0.041(2) 0.030(2) 0.0279(18) 0.0025(15) 0.0048(16) 0.0013(16)
C4 0.043(2) 0.029(2) 0.038(2) 0.0016(16) 0.0071(18) -0.0071(17)
C5 0.038(2) 0.034(2) 0.033(2) -0.0062(17) 0.0019(18) -0.0114(17)
C6 0.035(2) 0.0279(19) 0.0213(18) -0.0070(15) -0.0018(16) -0.0004(16)
C7 0.0281(18) 0.0245(17) 0.0175(15) -0.0046(13) -0.0002(13) 0.0004(14)
C8 0.0306(19) 0.0234(17) 0.0173(15) -0.0061(14) -0.0018(14) 0.0009(14)
O1 0.0464(16) 0.0285(13) 0.0178(12) 0.0000(10) -0.0088(11) -0.0010(12)
C9 0.0308(19) 0.0271(19) 0.0247(17) -0.0007(14) 0.0038(15) -0.0059(14)
C10 0.037(2) 0.030(2) 0.041(2) 0.0020(16) 0.0136(18) -0.0050(16)
C11 0.039(2) 0.0279(19) 0.038(2) 0.0020(16) 0.0134(18) 0.0005(15)
C12 0.061(3) 0.037(2) 0.055(3) -0.004(2) 0.010(2) -0.014(2)
C13 0.094(4) 0.042(3) 0.085(5) -0.006(3) 0.028(4) -0.032(3)
C14 0.091(5) 0.034(3) 0.111(6) 0.026(3) 0.050(4) 0.007(3)
C15 0.083(4) 0.086(5) 0.070(4) 0.049(4) 0.020(3) 0.012(4)
C16 0.059(3) 0.072(4) 0.053(3) 0.023(3) 0.001(2) -0.010(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.386(4) . ?
N1 C8 1.400(4) . ?
N1 C9 1.475(4) . ?
C1 N2 1.341(5) . ?
C1 S1 1.674(4) . ?
N2 C2 1.394(4) . ?
C2 C7 1.392(5) . ?
C2 C3 1.398(5) . ?
C3 C4 1.375(6) . ?
C4 C5 1.398(6) . ?
C5 C6 1.375(6) . ?
C6 C7 1.396(5) . ?
C7 C8 1.455(5) . ?
C8 O1 1.231(4) . ?
C9 C10 1.521(5) . ?
C10 C11 1.508(5) . ?
C11 C16 1.373(7) . ?
C11 C12 1.379(6) . ?
C12 C13 1.382(7) . ?
C13 C14 1.379(10) . ?
C14 C15 1.351(11) . ?
C15 C16 1.393(8) . ?

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
C1 N1 C8 124.0(3) . . ?
C1 N1 C9 120.0(3) . . ?
C8 N1 C9 116.0(3) . . ?
N2 C1 N1 116.3(3) . . ?
N2 C1 S1 120.6(3) . . ?
N1 C1 S1 123.1(3) . . ?
C1 N2 C2 125.2(3) . . ?
C7 C2 N2 118.6(3) . . ?
C7 C2 C3 120.8(3) . . ?
N2 C2 C3 120.6(3) . . ?
C4 C3 C2 118.6(4) . . ?
C3 C4 C5 121.2(4) . . ?
C6 C5 C4 120.0(4) . . ?
C5 C6 C7 119.8(3) . . ?
C2 C7 C6 119.6(3) . . ?
C2 C7 C8 118.9(3) . . ?
C6 C7 C8 121.4(3) . . ?
O1 C8 N1 119.2(3) . . ?
O1 C8 C7 123.9(3) . . ?
N1 C8 C7 116.9(3) . . ?
N1 C9 C10 112.1(3) . . ?
C11 C10 C9 110.9(3) . . ?
C16 C11 C12 118.5(4) . . ?
C16 C11 C10 120.7(4) . . ?
C12 C11 C10 120.8(4) . . ?
C11 C12 C13 120.1(5) . . ?
C14 C13 C12 121.2(6) . . ?
C15 C14 C13 118.7(5) . . ?
C14 C15 C16 120.7(6) . . ?
C11 C16 C15 120.8(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 N2 -3.2(5) . . . . ?
C9 N1 C1 N2 179.0(3) . . . . ?
C8 N1 C1 S1 177.5(3) . . . . ?
C9 N1 C1 S1 -0.4(4) . . . . ?
N1 C1 N2 C2 1.6(5) . . . . ?
S1 C1 N2 C2 -179.1(3) . . . . ?
C1 N2 C2 C7 0.2(5) . . . . ?
C1 N2 C2 C3 -179.8(3) . . . . ?
C7 C2 C3 C4 0.5(6) . . . . ?
N2 C2 C3 C4 -179.6(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
N2 C2 C7 C6 179.1(3) . . . . ?
C3 C2 C7 C6 -1.0(5) . . . . ?
N2 C2 C7 C8 -0.4(5) . . . . ?
C3 C2 C7 C8 179.5(3) . . . . ?
C5 C6 C7 C2 0.6(5) . . . . ?
C5 C6 C7 C8 -179.9(3) . . . . ?
C1 N1 C8 O1 -176.7(3) . . . . ?
C9 N1 C8 O1 1.2(5) . . . . ?
C1 N1 C8 C7 2.9(5) . . . . ?
C9 N1 C8 C7 -179.1(3) . . . . ?
C2 C7 C8 O1 178.6(4) . . . . ?
C6 C7 C8 O1 -0.9(6) . . . . ?
C2 C7 C8 N1 -1.0(5) . . . . ?
C6 C7 C8 N1 179.5(3) . . . . ?
C1 N1 C9 C10 91.5(4) . . . . ?
C8 N1 C9 C10 -86.5(4) . . . . ?
N1 C9 C10 C11 175.5(3) . . . . ?
C9 C10 C11 C16 -88.1(5) . . . . ?
C9 C10 C11 C12 90.5(5) . . . . ?
C16 C11 C12 C13 -0.6(7) . . . . ?
C10 C11 C12 C13 -179.2(4) . . . . ?
C11 C12 C13 C14 0.2(9) . . . . ?
C12 C13 C14 C15 0.6(10) . . . . ?
C13 C14 C15 C16 -1.0(10) . . . . ?
C12 C11 C16 C15 0.3(8) . . . . ?
C10 C11 C16 C15 178.9(5) . . . . ?
C14 C15 C16 C11 0.6(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.85(5) 1.97(5) 2.787(4) 162(4) 4_454

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.052

#===END

data_50
_database_code_depnum_ccdc_archive 'CCDC 622452'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 N2 O3, C H Cl3'
_chemical_formula_sum            'C17 H11 Cl3 N2 O3'
_chemical_formula_weight         397.63

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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.6511(3)
_cell_length_b                   8.6274(3)
_cell_length_c                   14.5395(7)
_cell_angle_alpha                90.123(2)
_cell_angle_beta                 94.525(3)
_cell_angle_gamma                99.594(3)
_cell_volume                     819.97(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3181
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.48

_exptl_crystal_description       rod
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11250
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3715
_reflns_number_gt                2898
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0492P)^2^+0.1456P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'geom except OH coords freely refined'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0071(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3715
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0851
_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
N1 N 0.14244(19) 0.63569(15) 0.92173(9) 0.0146(3) Uani 1 1 d . . .
C1 C -0.0378(2) 0.66563(18) 0.87709(11) 0.0158(3) Uani 1 1 d . . .
N2 N -0.1702(2) 0.73348(15) 0.91529(9) 0.0166(3) Uani 1 1 d . . .
C2 C -0.1214(2) 0.79209(18) 1.00469(11) 0.0167(3) Uani 1 1 d . . .
C3 C -0.2519(2) 0.88209(19) 1.04353(12) 0.0196(4) Uani 1 1 d . . .
H3 H -0.3755 0.8971 1.0101 0.024 Uiso 1 1 calc R . .
C4 C -0.2003(3) 0.94848(19) 1.13003(12) 0.0222(4) Uani 1 1 d . . .
H4 H -0.2890 1.0090 1.1561 0.027 Uiso 1 1 calc R . .
C5 C -0.0183(3) 0.92780(19) 1.18015(12) 0.0213(4) Uani 1 1 d . . .
H5 H 0.0174 0.9763 1.2392 0.026 Uiso 1 1 calc R . .
C6 C 0.1089(2) 0.83740(19) 1.14387(11) 0.0192(4) Uani 1 1 d . . .
H6 H 0.2311 0.8218 1.1783 0.023 Uiso 1 1 calc R . .
C7 C 0.0580(2) 0.76842(18) 1.05619(11) 0.0158(3) Uani 1 1 d . . .
C8 C 0.1965(2) 0.67843(18) 1.01500(11) 0.0157(3) Uani 1 1 d . . .
O1 O 0.35078(17) 0.64334(14) 1.05530(8) 0.0212(3) Uani 1 1 d . . .
C9 C 0.3060(2) 0.58892(19) 0.86974(11) 0.0159(3) Uani 1 1 d . . .
H9 H 0.3919 0.5290 0.9111 0.019 Uiso 1 1 calc R . .
O2 O 0.42678(17) 0.72966(13) 0.84351(8) 0.0176(3) Uani 1 1 d . . .
H2 H 0.539(3) 0.723(2) 0.8595(14) 0.026 Uiso 1 1 d . . .
C10 C 0.2222(2) 0.49033(18) 0.78584(11) 0.0165(3) Uani 1 1 d . . .
C11 C 0.3409(3) 0.39065(19) 0.74902(11) 0.0197(4) Uani 1 1 d . . .
H11 H 0.4683 0.3786 0.7801 0.024 Uiso 1 1 calc R . .
C12 C 0.2740(3) 0.3093(2) 0.66742(12) 0.0243(4) Uani 1 1 d . . .
H12 H 0.3555 0.2411 0.6430 0.029 Uiso 1 1 calc R . .
C13 C 0.0874(3) 0.3263(2) 0.62048(12) 0.0266(4) Uani 1 1 d . . .
H13 H 0.0426 0.2703 0.5643 0.032 Uiso 1 1 calc R . .
C14 C -0.0312(3) 0.4249(2) 0.65622(12) 0.0238(4) Uani 1 1 d . . .
H14 H -0.1578 0.4374 0.6246 0.029 Uiso 1 1 calc R . .
C15 C 0.0355(2) 0.50622(19) 0.73902(11) 0.0174(3) Uani 1 1 d . . .
C16 C -0.0910(2) 0.61045(19) 0.77812(11) 0.0186(3) Uani 1 1 d . . .
O3 O -0.23696(18) 0.65190(16) 0.73531(8) 0.0282(3) Uani 1 1 d . . .
C17 C 0.4419(3) 0.8143(2) 0.62829(12) 0.0232(4) Uani 1 1 d . . .
H17 H 0.4644 0.7632 0.6891 0.028 Uiso 1 1 calc R . .
Cl1 Cl 0.46117(8) 0.68003(6) 0.53965(3) 0.03290(14) Uani 1 1 d . . .
Cl2 Cl 0.62940(7) 0.98375(6) 0.62257(4) 0.03665(15) Uani 1 1 d . . .
Cl3 Cl 0.19517(7) 0.86669(6) 0.62000(3) 0.03135(14) 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
N1 0.0122(6) 0.0173(7) 0.0146(7) 0.0007(5) 0.0008(5) 0.0033(5)
C1 0.0126(7) 0.0154(8) 0.0185(8) 0.0031(6) 0.0006(6) 0.0005(6)
N2 0.0137(7) 0.0169(7) 0.0195(7) 0.0009(6) 0.0018(5) 0.0030(5)
C2 0.0163(8) 0.0141(8) 0.0190(8) 0.0029(7) 0.0039(6) -0.0008(6)
C3 0.0171(8) 0.0183(8) 0.0242(9) 0.0019(7) 0.0045(7) 0.0032(7)
C4 0.0240(9) 0.0166(8) 0.0270(9) -0.0004(7) 0.0085(7) 0.0036(7)
C5 0.0270(9) 0.0186(8) 0.0178(9) -0.0024(7) 0.0050(7) 0.0009(7)
C6 0.0189(8) 0.0199(8) 0.0180(8) 0.0015(7) 0.0019(7) 0.0008(7)
C7 0.0156(8) 0.0147(8) 0.0167(8) 0.0026(6) 0.0029(6) 0.0009(6)
C8 0.0151(8) 0.0148(8) 0.0160(8) 0.0004(6) 0.0005(6) -0.0007(6)
O1 0.0192(6) 0.0262(6) 0.0189(6) 0.0003(5) -0.0029(5) 0.0077(5)
C9 0.0137(8) 0.0187(8) 0.0165(8) 0.0006(6) 0.0013(6) 0.0059(6)
O2 0.0104(5) 0.0209(6) 0.0213(6) 0.0008(5) 0.0005(5) 0.0027(5)
C10 0.0182(8) 0.0167(8) 0.0146(8) 0.0020(6) 0.0014(6) 0.0026(6)
C11 0.0210(8) 0.0178(8) 0.0210(9) 0.0019(7) 0.0045(7) 0.0039(7)
C12 0.0300(10) 0.0206(9) 0.0230(9) -0.0007(7) 0.0073(7) 0.0041(7)
C13 0.0334(10) 0.0256(9) 0.0194(9) -0.0055(7) 0.0010(8) 0.0012(8)
C14 0.0224(9) 0.0280(9) 0.0198(9) -0.0002(7) -0.0015(7) 0.0023(7)
C15 0.0168(8) 0.0188(8) 0.0161(8) 0.0006(7) 0.0019(6) 0.0012(7)
C16 0.0144(8) 0.0224(8) 0.0180(8) 0.0015(7) 0.0003(6) 0.0006(7)
O3 0.0206(6) 0.0455(8) 0.0205(7) -0.0007(6) -0.0036(5) 0.0141(6)
C17 0.0273(9) 0.0240(9) 0.0188(9) -0.0003(7) 0.0005(7) 0.0060(7)
Cl1 0.0454(3) 0.0329(3) 0.0233(2) -0.00588(19) 0.0007(2) 0.0161(2)
Cl2 0.0317(3) 0.0314(3) 0.0429(3) 0.0042(2) -0.0063(2) -0.0017(2)
Cl3 0.0280(3) 0.0365(3) 0.0319(3) -0.0006(2) 0.00352(19) 0.0120(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3805(19) . ?
N1 C8 1.408(2) . ?
N1 C9 1.481(2) . ?
C1 N2 1.294(2) . ?
C1 C16 1.511(2) . ?
N2 C2 1.388(2) . ?
C2 C7 1.402(2) . ?
C2 C3 1.405(2) . ?
C3 C4 1.375(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.375(2) . ?
C6 C7 1.398(2) . ?
C7 C8 1.461(2) . ?
C8 O1 1.2237(18) . ?
C9 O2 1.4109(19) . ?
C9 C10 1.501(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.396(2) . ?
C11 C12 1.381(2) . ?
C12 C13 1.398(2) . ?
C13 C14 1.379(3) . ?
C14 C15 1.395(2) . ?
C15 C16 1.471(2) . ?
C16 O3 1.2161(19) . ?
C17 Cl1 1.7573(17) . ?
C17 Cl2 1.7629(18) . ?
C17 Cl3 1.7690(17) . ?

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
C1 N1 C8 121.36(13) . . ?
C1 N1 C9 121.27(13) . . ?
C8 N1 C9 116.16(12) . . ?
N2 C1 N1 124.41(15) . . ?
N2 C1 C16 116.85(13) . . ?
N1 C1 C16 118.69(14) . . ?
C1 N2 C2 118.17(13) . . ?
N2 C2 C7 121.82(14) . . ?
N2 C2 C3 119.06(14) . . ?
C7 C2 C3 119.08(15) . . ?
C4 C3 C2 119.91(15) . . ?
C3 C4 C5 120.73(15) . . ?
C6 C5 C4 120.03(16) . . ?
C5 C6 C7 119.91(15) . . ?
C6 C7 C2 120.31(14) . . ?
C6 C7 C8 120.45(14) . . ?
C2 C7 C8 119.15(14) . . ?
O1 C8 N1 120.76(14) . . ?
O1 C8 C7 124.61(15) . . ?
N1 C8 C7 114.61(13) . . ?
O2 C9 N1 106.36(12) . . ?
O2 C9 C10 110.04(13) . . ?
N1 C9 C10 112.35(12) . . ?
C11 C10 C15 118.94(15) . . ?
C11 C10 C9 119.39(14) . . ?
C15 C10 C9 121.42(14) . . ?
C12 C11 C10 120.23(16) . . ?
C11 C12 C13 120.62(16) . . ?
C14 C13 C12 119.65(16) . . ?
C13 C14 C15 119.78(16) . . ?
C14 C15 C10 120.77(15) . . ?
C14 C15 C16 120.15(14) . . ?
C10 C15 C16 119.07(14) . . ?
O3 C16 C15 123.32(15) . . ?
O3 C16 C1 118.83(14) . . ?
C15 C16 C1 117.84(13) . . ?
Cl1 C17 Cl2 110.52(10) . . ?
Cl1 C17 Cl3 110.12(9) . . ?
Cl2 C17 Cl3 110.03(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 N2 -0.1(2) . . . . ?
C9 N1 C1 N2 -166.96(15) . . . . ?
C8 N1 C1 C16 -177.39(13) . . . . ?
C9 N1 C1 C16 15.7(2) . . . . ?
N1 C1 N2 C2 5.6(2) . . . . ?
C16 C1 N2 C2 -177.00(13) . . . . ?
C1 N2 C2 C7 -5.2(2) . . . . ?
C1 N2 C2 C3 172.63(15) . . . . ?
N2 C2 C3 C4 -176.39(15) . . . . ?
C7 C2 C3 C4 1.5(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
C5 C6 C7 C8 177.03(15) . . . . ?
N2 C2 C7 C6 175.98(14) . . . . ?
C3 C2 C7 C6 -1.9(2) . . . . ?
N2 C2 C7 C8 -0.6(2) . . . . ?
C3 C2 C7 C8 -178.38(14) . . . . ?
C1 N1 C8 O1 175.81(15) . . . . ?
C9 N1 C8 O1 -16.6(2) . . . . ?
C1 N1 C8 C7 -5.6(2) . . . . ?
C9 N1 C8 C7 161.98(13) . . . . ?
C6 C7 C8 O1 7.7(3) . . . . ?
C2 C7 C8 O1 -175.76(15) . . . . ?
C6 C7 C8 N1 -170.85(14) . . . . ?
C2 C7 C8 N1 5.7(2) . . . . ?
C1 N1 C9 O2 86.48(16) . . . . ?
C8 N1 C9 O2 -81.07(15) . . . . ?
C1 N1 C9 C10 -34.0(2) . . . . ?
C8 N1 C9 C10 158.48(13) . . . . ?
O2 C9 C10 C11 85.06(17) . . . . ?
N1 C9 C10 C11 -156.63(14) . . . . ?
O2 C9 C10 C15 -89.25(18) . . . . ?
N1 C9 C10 C15 29.1(2) . . . . ?
C15 C10 C11 C12 0.0(2) . . . . ?
C9 C10 C11 C12 -174.41(15) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C13 C14 C15 C16 -179.40(16) . . . . ?
C11 C10 C15 C14 -0.6(2) . . . . ?
C9 C10 C15 C14 173.78(15) . . . . ?
C11 C10 C15 C16 179.52(15) . . . . ?
C9 C10 C15 C16 -6.1(2) . . . . ?
C14 C15 C16 O3 -12.7(3) . . . . ?
C10 C15 C16 O3 167.21(16) . . . . ?
C14 C15 C16 C1 166.13(15) . . . . ?
C10 C15 C16 C1 -13.9(2) . . . . ?
N2 C1 C16 O3 10.8(2) . . . . ?
N1 C1 C16 O3 -171.71(15) . . . . ?
N2 C1 C16 C15 -168.14(14) . . . . ?
N1 C1 C16 C15 9.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.78(2) 2.02(2) 2.7935(17) 171(2) 1_655
O2 H2 O3 0.78(2) 2.57(2) 2.9963(17) 116.7(17) 1_655

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.065

#===END