# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Zhang, Wei'
_publ_contact_author_email       zhangwei6275@lzu.edu.cn

_publ_section_title              
;
One-pot synthesis of benzo[f]quinolin-3-ones and
benzo[a]phenanthridein-5-ones by the photoinduced
inter- and intramolecular reactions of
6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones
with phenylacetylene
;
_publ_author_name                'Wei Zhang'

data_pna21
_database_code_depnum_ccdc_archive 'CCDC 800642'
#TrackingRef 'Pna21.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2'
_chemical_formula_weight         225.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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                   7.168(3)
_cell_length_b                   15.046(7)
_cell_length_c                   9.688(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1044.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1209
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9670
_exptl_absorpt_correction_T_max  0.9725
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5818
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.98
_reflns_number_total             2025
_reflns_number_gt                1542
_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 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^)+(0.0469P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(17)
_refine_ls_number_reflns         2025
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.974
_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 0.1106(4) 0.14372(17) 1.0232(3) 0.0467(7) Uani 1 1 d . . .
H1A H -0.0235 0.1366 1.0309 0.056 Uiso 1 1 calc R . .
H1B H 0.1545 0.1729 1.1064 0.056 Uiso 1 1 calc R . .
C2 C 0.1997(4) 0.05386(16) 1.0122(3) 0.0507(7) Uani 1 1 d . . .
H2A H 0.1571 0.0166 1.0876 0.061 Uiso 1 1 calc R . .
H2B H 0.3341 0.0599 1.0196 0.061 Uiso 1 1 calc R . .
C3 C 0.1508(4) 0.01017(17) 0.8754(3) 0.0504(7) Uani 1 1 d . . .
H3A H 0.2148 -0.0464 0.8677 0.061 Uiso 1 1 calc R . .
H3B H 0.0176 -0.0008 0.8711 0.061 Uiso 1 1 calc R . .
C4 C 0.2082(3) 0.07009(15) 0.7586(3) 0.0365(6) Uani 1 1 d . . .
C5 C 0.2681(4) 0.03472(17) 0.6352(2) 0.0421(6) Uani 1 1 d . . .
H5 H 0.2755 -0.0265 0.6227 0.051 Uiso 1 1 calc R . .
C6 C 0.3170(3) 0.09255(17) 0.5305(3) 0.0401(6) Uani 1 1 d . . .
C7 C 0.3097(3) 0.18319(16) 0.5415(2) 0.0362(6) Uani 1 1 d . . .
C8 C 0.2513(4) 0.22134(15) 0.6669(2) 0.0336(5) Uani 1 1 d . . .
C9 C 0.2045(3) 0.16369(16) 0.7764(2) 0.0322(5) Uani 1 1 d . . .
C10 C 0.4158(4) 0.1465(2) 0.3338(3) 0.0535(8) Uani 1 1 d . . .
H10 H 0.4616 0.1503 0.2442 0.064 Uiso 1 1 calc R . .
C11 C 0.3748(4) 0.21726(18) 0.4123(3) 0.0484(7) Uani 1 1 d . . .
H11 H 0.3864 0.2767 0.3877 0.058 Uiso 1 1 calc R . .
C12 C 0.2391(3) 0.31454(15) 0.6884(3) 0.0398(6) Uani 1 1 d . . .
H12 H 0.2696 0.3530 0.6168 0.048 Uiso 1 1 calc R . .
C13 C 0.1848(3) 0.34782(18) 0.8094(3) 0.0436(7) Uani 1 1 d . . .
H13 H 0.1751 0.4091 0.8196 0.052 Uiso 1 1 calc R . .
C14 C 0.1409(3) 0.29153(17) 0.9241(3) 0.0413(6) Uani 1 1 d . . .
N1 N 0.1530(3) 0.20063(13) 0.90239(18) 0.0362(5) Uani 1 1 d . . .
O1 O 0.3823(3) 0.06785(12) 0.40155(18) 0.0538(5) Uani 1 1 d . . .
O2 O 0.0941(3) 0.32032(13) 1.03908(19) 0.0595(6) 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
C1 0.0498(15) 0.0558(17) 0.0345(14) 0.0067(14) 0.0054(13) 0.0025(13)
C2 0.0549(16) 0.0499(17) 0.0471(17) 0.0141(15) 0.0052(13) -0.0036(14)
C3 0.0515(17) 0.0397(17) 0.0601(18) 0.0078(13) 0.0041(13) -0.0047(13)
C4 0.0343(13) 0.0328(14) 0.0425(14) -0.0012(11) 0.0005(11) -0.0001(11)
C5 0.0457(15) 0.0324(13) 0.0483(16) -0.0059(12) -0.0002(12) -0.0016(12)
C6 0.0417(14) 0.0420(15) 0.0364(14) -0.0128(13) -0.0010(11) 0.0017(12)
C7 0.0341(12) 0.0442(15) 0.0303(13) -0.0001(13) -0.0045(10) -0.0001(12)
C8 0.0301(12) 0.0354(13) 0.0353(14) -0.0023(12) -0.0035(9) 0.0018(11)
C9 0.0296(12) 0.0343(13) 0.0329(14) -0.0010(11) -0.0020(10) -0.0001(11)
C10 0.0569(19) 0.070(2) 0.0334(14) 0.0009(14) 0.0044(13) 0.0004(15)
C11 0.0494(18) 0.0541(17) 0.0418(15) 0.0038(15) -0.0010(13) 0.0034(14)
C12 0.0403(14) 0.0361(14) 0.0429(16) 0.0019(13) -0.0054(13) -0.0022(11)
C13 0.0440(17) 0.0331(16) 0.0538(18) -0.0063(12) -0.0040(13) 0.0019(12)
C14 0.0370(14) 0.0443(16) 0.0428(16) -0.0085(13) -0.0011(12) 0.0061(12)
N1 0.0381(11) 0.0386(12) 0.0318(12) -0.0022(10) 0.0003(9) 0.0039(9)
O1 0.0621(12) 0.0582(13) 0.0410(11) -0.0148(10) 0.0049(10) 0.0026(10)
O2 0.0713(13) 0.0593(12) 0.0481(12) -0.0176(10) 0.0089(10) 0.0110(10)

_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 N1 1.481(3) . ?
C1 C2 1.499(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.520(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.505(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.377(3) . ?
C4 C9 1.419(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(3) . ?
C6 O1 1.384(3) . ?
C7 C8 1.408(3) . ?
C7 C11 1.431(4) . ?
C8 C9 1.411(3) . ?
C8 C12 1.420(3) . ?
C9 N1 1.391(3) . ?
C10 C11 1.340(4) . ?
C10 O1 1.375(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.333(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.432(4) . ?
C13 H13 0.9300 . ?
C14 O2 1.241(3) . ?
C14 N1 1.387(3) . ?

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
N1 C1 C2 112.2(2) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 C3 110.7(2) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 109.5(2) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C9 119.7(2) . . ?
C5 C4 C3 120.4(2) . . ?
C9 C4 C3 119.9(2) . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 O1 110.5(2) . . ?
C7 C6 C5 124.1(2) . . ?
O1 C6 C5 125.4(2) . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 C11 106.0(2) . . ?
C8 C7 C11 134.9(2) . . ?
C9 C8 C7 118.0(2) . . ?
C9 C8 C12 118.8(2) . . ?
C7 C8 C12 123.2(2) . . ?
N1 C9 C8 118.5(2) . . ?
N1 C9 C4 120.6(2) . . ?
C8 C9 C4 120.9(2) . . ?
C11 C10 O1 112.0(2) . . ?
C11 C10 H10 124.0 . . ?
O1 C10 H10 124.0 . . ?
C10 C11 C7 106.4(3) . . ?
C10 C11 H11 126.8 . . ?
C7 C11 H11 126.8 . . ?
C13 C12 C8 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C8 C12 H12 119.4 . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
O2 C14 N1 119.8(2) . . ?
O2 C14 C13 123.3(2) . . ?
N1 C14 C13 116.8(2) . . ?
C14 N1 C9 122.97(19) . . ?
C14 N1 C1 115.93(19) . . ?
C9 N1 C1 121.1(2) . . ?
C10 O1 C6 104.98(19) . . ?

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
N1 C1 C2 C3 -52.7(3) . . . . ?
C1 C2 C3 C4 56.4(3) . . . . ?
C2 C3 C4 C5 147.1(2) . . . . ?
C2 C3 C4 C9 -31.5(3) . . . . ?
C9 C4 C5 C6 -2.2(4) . . . . ?
C3 C4 C5 C6 179.2(2) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C4 C5 C6 O1 179.0(2) . . . . ?
O1 C6 C7 C8 -178.3(2) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
O1 C6 C7 C11 -0.3(3) . . . . ?
C5 C6 C7 C11 178.9(2) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C11 C7 C8 C9 -176.8(2) . . . . ?
C6 C7 C8 C12 180.0(2) . . . . ?
C11 C7 C8 C12 2.6(4) . . . . ?
C7 C8 C9 N1 177.7(2) . . . . ?
C12 C8 C9 N1 -1.7(3) . . . . ?
C7 C8 C9 C4 -2.8(4) . . . . ?
C12 C8 C9 C4 177.8(2) . . . . ?
C5 C4 C9 N1 -176.9(2) . . . . ?
C3 C4 C9 N1 1.8(4) . . . . ?
C5 C4 C9 C8 3.6(4) . . . . ?
C3 C4 C9 C8 -177.7(2) . . . . ?
O1 C10 C11 C7 0.1(3) . . . . ?
C6 C7 C11 C10 0.1(3) . . . . ?
C8 C7 C11 C10 177.7(3) . . . . ?
C9 C8 C12 C13 0.0(3) . . . . ?
C7 C8 C12 C13 -179.4(2) . . . . ?
C8 C12 C13 C14 1.7(4) . . . . ?
C12 C13 C14 O2 178.3(3) . . . . ?
C12 C13 C14 N1 -1.6(3) . . . . ?
O2 C14 N1 C9 180.0(2) . . . . ?
C13 C14 N1 C9 -0.2(3) . . . . ?
O2 C14 N1 C1 -1.0(3) . . . . ?
C13 C14 N1 C1 178.9(2) . . . . ?
C8 C9 N1 C14 1.8(3) . . . . ?
C4 C9 N1 C14 -177.8(2) . . . . ?
C8 C9 N1 C1 -177.2(2) . . . . ?
C4 C9 N1 C1 3.3(3) . . . . ?
C2 C1 N1 C14 -156.2(2) . . . . ?
C2 C1 N1 C9 22.8(3) . . . . ?
C11 C10 O1 C6 -0.3(3) . . . . ?
C7 C6 O1 C10 0.3(3) . . . . ?
C5 C6 O1 C10 -178.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037


# Attachment '- P212121.cif'

data_p212121
_database_code_depnum_ccdc_archive 'CCDC 806191'
#TrackingRef '- P212121.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Cl N O'
_chemical_formula_weight         319.77

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.272(4)
_cell_length_b                   11.909(6)
_cell_length_c                   17.041(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1475.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    869
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      18.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9301
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7084
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.40
_reflns_number_total             2705
_reflns_number_gt                1551
_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 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^)+(0.0895P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(16)
_refine_ls_number_reflns         2705
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1772
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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 0.4261(6) 0.4874(4) -0.0317(3) 0.0517(12) Uani 1 1 d . . .
H1 H 0.4689 0.5348 -0.0710 0.062 Uiso 1 1 calc R . .
C2 C 0.4451(7) 0.3725(4) -0.0402(4) 0.0672(16) Uani 1 1 d . . .
H2 H 0.5021 0.3435 -0.0846 0.081 Uiso 1 1 calc R . .
C3 C 0.3795(10) 0.3000(4) 0.0173(4) 0.084(2) Uani 1 1 d . . .
H3 H 0.3858 0.2227 0.0101 0.101 Uiso 1 1 calc R . .
C4 C 0.3070(8) 0.3427(4) 0.0833(4) 0.0704(17) Uani 1 1 d . . .
H4 H 0.2662 0.2940 0.1222 0.085 Uiso 1 1 calc R . .
C5 C 0.2912(7) 0.4583(4) 0.0951(3) 0.0573(13) Uani 1 1 d . . .
C6 C 0.2348(7) 0.4964(5) 0.1711(3) 0.0700(15) Uani 1 1 d . . .
C7 C 0.2191(11) 0.6491(6) 0.2661(3) 0.094(2) Uani 1 1 d . . .
H7A H 0.0917 0.6729 0.2686 0.113 Uiso 1 1 calc R . .
H7B H 0.2359 0.5884 0.3033 0.113 Uiso 1 1 calc R . .
C8 C 0.3360(13) 0.7410(7) 0.2870(4) 0.118(3) Uani 1 1 d . . .
H8A H 0.4630 0.7161 0.2859 0.141 Uiso 1 1 calc R . .
H8B H 0.3079 0.7644 0.3402 0.141 Uiso 1 1 calc R . .
C9 C 0.3145(10) 0.8405(5) 0.2325(4) 0.091(2) Uani 1 1 d . . .
H9A H 0.4129 0.8937 0.2422 0.110 Uiso 1 1 calc R . .
H9B H 0.1988 0.8778 0.2435 0.110 Uiso 1 1 calc R . .
C10 C 0.3187(7) 0.8047(4) 0.1466(3) 0.0621(14) Uani 1 1 d . . .
C11 C 0.2976(6) 0.6891(4) 0.1262(3) 0.0526(12) Uani 1 1 d . . .
C12 C 0.3245(6) 0.6530(4) 0.0489(3) 0.0461(11) Uani 1 1 d . . .
C13 C 0.3437(6) 0.5333(3) 0.0351(3) 0.0454(11) Uani 1 1 d . . .
C14 C 0.3225(6) 0.7364(3) -0.0126(3) 0.0453(11) Uani 1 1 d . . .
C15 C 0.2914(7) 0.7100(4) -0.0933(3) 0.0498(12) Uani 1 1 d . . .
H15 H 0.2721 0.6357 -0.1080 0.060 Uiso 1 1 calc R . .
C16 C 0.2895(7) 0.7908(5) -0.1484(3) 0.0632(14) Uani 1 1 d . . .
H16 H 0.2686 0.7711 -0.2005 0.076 Uiso 1 1 calc R . .
C17 C 0.3174(8) 0.9009(5) -0.1301(4) 0.0713(16) Uani 1 1 d . . .
H17 H 0.3210 0.9543 -0.1699 0.086 Uiso 1 1 calc R . .
C18 C 0.3400(7) 0.9333(4) -0.0546(4) 0.0644(15) Uani 1 1 d . . .
H18 H 0.3545 1.0089 -0.0423 0.077 Uiso 1 1 calc R . .
C19 C 0.3413(7) 0.8514(4) 0.0058(3) 0.0529(13) Uani 1 1 d . . .
C20 C 0.3475(7) 0.8788(4) 0.0876(3) 0.0631(15) Uani 1 1 d . . .
Cl1 Cl 0.3887(3) 1.01631(12) 0.11301(12) 0.1023(7) Uani 1 1 d . . .
N1 N 0.2613(6) 0.6080(4) 0.1852(2) 0.0655(13) Uani 1 1 d . . .
O1 O 0.1738(6) 0.4359(3) 0.2281(2) 0.0879(13) 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
C1 0.053(3) 0.047(2) 0.055(3) -0.004(2) -0.006(2) 0.004(2)
C2 0.069(4) 0.056(3) 0.076(4) -0.014(3) -0.016(3) 0.014(3)
C3 0.103(5) 0.044(3) 0.106(5) 0.009(4) -0.036(5) 0.002(4)
C4 0.066(4) 0.056(3) 0.089(4) 0.025(3) -0.015(4) -0.008(3)
C5 0.046(3) 0.061(3) 0.065(3) 0.013(3) -0.006(3) 0.002(2)
C6 0.064(4) 0.074(4) 0.072(4) 0.008(4) -0.003(3) 0.012(3)
C7 0.107(5) 0.126(6) 0.049(4) 0.003(4) 0.006(4) 0.007(5)
C8 0.114(7) 0.174(8) 0.066(4) -0.031(5) 0.001(5) -0.019(6)
C9 0.100(5) 0.098(5) 0.076(4) -0.032(4) -0.009(4) 0.010(4)
C10 0.050(3) 0.065(3) 0.071(4) -0.016(3) -0.010(3) 0.015(3)
C11 0.038(3) 0.062(3) 0.058(3) -0.003(3) -0.009(3) 0.009(2)
C12 0.036(3) 0.050(3) 0.052(3) -0.001(2) 0.000(3) -0.002(2)
C13 0.034(2) 0.041(2) 0.061(3) 0.001(2) -0.011(2) -0.002(2)
C14 0.034(3) 0.042(2) 0.059(3) 0.004(2) -0.002(3) 0.000(2)
C15 0.044(3) 0.053(3) 0.053(3) 0.001(3) -0.003(2) 0.000(2)
C16 0.062(4) 0.069(3) 0.059(3) 0.015(3) -0.003(3) -0.002(3)
C17 0.058(3) 0.069(4) 0.088(4) 0.034(3) 0.010(3) 0.011(3)
C18 0.051(3) 0.042(3) 0.100(5) 0.013(3) 0.004(3) 0.006(2)
C19 0.038(3) 0.044(2) 0.077(4) -0.003(3) 0.000(3) 0.005(2)
C20 0.050(3) 0.048(3) 0.091(4) -0.017(3) -0.016(3) 0.010(2)
Cl1 0.1050(13) 0.0533(8) 0.1486(16) -0.0205(9) -0.0386(12) 0.0017(8)
N1 0.062(3) 0.098(3) 0.037(2) 0.012(2) 0.004(2) 0.013(3)
O1 0.086(3) 0.084(2) 0.093(3) 0.059(2) 0.023(3) -0.001(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
C1 C2 1.383(6) . ?
C1 C13 1.397(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.341(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(7) . ?
C4 H4 0.9300 . ?
C5 C13 1.410(6) . ?
C5 C6 1.432(7) . ?
C6 O1 1.289(6) . ?
C6 N1 1.365(7) . ?
C7 C8 1.431(9) . ?
C7 N1 1.495(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.513(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.525(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C20 1.354(7) . ?
C10 C11 1.429(7) . ?
C11 C12 1.399(7) . ?
C11 N1 1.419(6) . ?
C12 C14 1.445(6) . ?
C12 C13 1.451(6) . ?
C14 C19 1.412(6) . ?
C14 C15 1.429(6) . ?
C15 C16 1.344(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.354(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.418(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.433(7) . ?
C20 Cl1 1.721(5) . ?

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 C13 121.0(5) . . ?
C2 C1 H1 119.5 . . ?
C13 C1 H1 119.5 . . ?
C1 C2 C3 120.4(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.8(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C13 119.8(5) . . ?
C4 C5 C6 117.8(5) . . ?
C13 C5 C6 122.2(5) . . ?
O1 C6 N1 117.4(5) . . ?
O1 C6 C5 127.1(5) . . ?
N1 C6 C5 115.3(5) . . ?
C8 C7 N1 111.0(6) . . ?
C8 C7 H7A 109.4 . . ?
N1 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
N1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 112.6(6) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 111.6(5) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C20 C10 C11 117.6(5) . . ?
C20 C10 C9 122.3(5) . . ?
C11 C10 C9 120.1(5) . . ?
C12 C11 N1 118.9(4) . . ?
C12 C11 C10 120.7(5) . . ?
N1 C11 C10 120.2(5) . . ?
C11 C12 C14 118.1(4) . . ?
C11 C12 C13 117.9(4) . . ?
C14 C12 C13 123.9(4) . . ?
C1 C13 C5 117.3(4) . . ?
C1 C13 C12 123.9(4) . . ?
C5 C13 C12 118.5(4) . . ?
C19 C14 C15 116.3(4) . . ?
C19 C14 C12 120.3(4) . . ?
C15 C14 C12 123.3(4) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.8(5) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 120.6(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.7(5) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 120.4(5) . . ?
C14 C19 C20 116.1(4) . . ?
C18 C19 C20 123.4(4) . . ?
C10 C20 C19 124.7(4) . . ?
C10 C20 Cl1 117.4(4) . . ?
C19 C20 Cl1 117.8(4) . . ?
C6 N1 C11 124.3(4) . . ?
C6 N1 C7 116.9(5) . . ?
C11 N1 C7 118.0(5) . . ?

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
C13 C1 C2 C3 1.0(8) . . . . ?
C1 C2 C3 C4 -3.8(9) . . . . ?
C2 C3 C4 C5 1.6(9) . . . . ?
C3 C4 C5 C13 3.3(9) . . . . ?
C3 C4 C5 C6 -172.0(5) . . . . ?
C4 C5 C6 O1 -9.5(8) . . . . ?
C13 C5 C6 O1 175.4(5) . . . . ?
C4 C5 C6 N1 165.8(5) . . . . ?
C13 C5 C6 N1 -9.3(7) . . . . ?
N1 C7 C8 C9 60.4(8) . . . . ?
C7 C8 C9 C10 -47.3(9) . . . . ?
C8 C9 C10 C20 -163.3(6) . . . . ?
C8 C9 C10 C11 14.7(8) . . . . ?
C20 C10 C11 C12 6.3(7) . . . . ?
C9 C10 C11 C12 -171.8(5) . . . . ?
C20 C10 C11 N1 -178.0(5) . . . . ?
C9 C10 C11 N1 3.9(7) . . . . ?
N1 C11 C12 C14 167.1(4) . . . . ?
C10 C11 C12 C14 -17.1(7) . . . . ?
N1 C11 C12 C13 -9.9(6) . . . . ?
C10 C11 C12 C13 165.9(4) . . . . ?
C2 C1 C13 C5 3.8(7) . . . . ?
C2 C1 C13 C12 178.0(5) . . . . ?
C4 C5 C13 C1 -5.8(7) . . . . ?
C6 C5 C13 C1 169.2(4) . . . . ?
C4 C5 C13 C12 179.6(4) . . . . ?
C6 C5 C13 C12 -5.4(7) . . . . ?
C11 C12 C13 C1 -159.1(4) . . . . ?
C14 C12 C13 C1 24.0(7) . . . . ?
C11 C12 C13 C5 15.0(6) . . . . ?
C14 C12 C13 C5 -161.8(4) . . . . ?
C11 C12 C14 C19 16.2(7) . . . . ?
C13 C12 C14 C19 -166.9(4) . . . . ?
C11 C12 C14 C15 -160.0(4) . . . . ?
C13 C12 C14 C15 16.8(7) . . . . ?
C19 C14 C15 C16 3.1(7) . . . . ?
C12 C14 C15 C16 179.5(5) . . . . ?
C14 C15 C16 C17 0.1(8) . . . . ?
C15 C16 C17 C18 -3.0(9) . . . . ?
C16 C17 C18 C19 2.3(8) . . . . ?
C15 C14 C19 C18 -3.7(7) . . . . ?
C12 C14 C19 C18 179.8(4) . . . . ?
C15 C14 C19 C20 171.8(4) . . . . ?
C12 C14 C19 C20 -4.7(7) . . . . ?
C17 C18 C19 C14 1.1(7) . . . . ?
C17 C18 C19 C20 -174.1(5) . . . . ?
C11 C10 C20 C19 6.1(8) . . . . ?
C9 C10 C20 C19 -175.8(5) . . . . ?
C11 C10 C20 Cl1 -175.6(4) . . . . ?
C9 C10 C20 Cl1 2.4(7) . . . . ?
C14 C19 C20 C10 -6.8(8) . . . . ?
C18 C19 C20 C10 168.6(5) . . . . ?
C14 C19 C20 Cl1 174.9(3) . . . . ?
C18 C19 C20 Cl1 -9.7(7) . . . . ?
O1 C6 N1 C11 -169.0(4) . . . . ?
C5 C6 N1 C11 15.3(7) . . . . ?
O1 C6 N1 C7 0.8(8) . . . . ?
C5 C6 N1 C7 -175.0(5) . . . . ?
C12 C11 N1 C6 -5.8(7) . . . . ?
C10 C11 N1 C6 178.4(5) . . . . ?
C12 C11 N1 C7 -175.5(5) . . . . ?
C10 C11 N1 C7 8.7(7) . . . . ?
C8 C7 N1 C6 148.6(6) . . . . ?
C8 C7 N1 C11 -40.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045