# Electronic Supplementary Material (ESI) for Organic .
# 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_ohj248_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26

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   P2(1)2(1)2(1)

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

_cell_length_a                   4.896
_cell_length_b                   11.351
_cell_length_c                   21.440
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1191.5
_cell_formula_units_Z            4
_cell_measurement_temperature    97(2)
_cell_measurement_reflns_used    5329
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.18

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      97(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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14837
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2683
_reflns_number_gt                2401
_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, 1997)'
_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)+(0.0307P)²+0.2906P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(12)
_refine_ls_number_reflns         2683
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 -0.3300(3) 0.86955(11) 0.02533(5) 0.0190(3) Uani 1 1 d . . .
H1 H -0.3535 0.8211 -0.0062 0.023 Uiso 1 1 calc R . .
O1 O 0.0228(2) 0.77289(9) 0.07594(5) 0.0206(2) Uani 1 1 d . . .
O2 O -0.1041(2) 1.14603(10) 0.21027(5) 0.0241(3) Uani 1 1 d . . .
C1 C -0.6885(3) 1.01629(14) -0.00239(7) 0.0207(3) Uani 1 1 d . . .
H1 H -0.7434 0.9766 -0.0393 0.025 Uiso 1 1 calc R . .
C2 C -0.8136(3) 1.12075(14) 0.01649(7) 0.0229(3) Uani 1 1 d . . .
H2 H -0.9576 1.1527 -0.0079 0.028 Uiso 1 1 calc R . .
C3 C -0.7315(3) 1.17901(13) 0.07044(7) 0.0216(3) Uani 1 1 d . . .
H3 H -0.8212 1.2497 0.0823 0.026 Uiso 1 1 calc R . .
C4 C -0.5192(3) 1.13523(13) 0.10741(7) 0.0194(3) Uani 1 1 d . . .
H4 H -0.4624 1.1761 0.1438 0.023 Uiso 1 1 calc R . .
C5 C -0.3926(3) 1.03038(13) 0.08973(6) 0.0168(3) Uani 1 1 d . . .
C6 C -0.4812(3) 0.97307(13) 0.03488(6) 0.0177(3) Uani 1 1 d . . .
C7 C -0.1427(3) 0.85422(13) 0.07129(6) 0.0170(3) Uani 1 1 d . . .
C8 C -0.1724(3) 0.95763(13) 0.11593(6) 0.0169(3) Uani 1 1 d . . .
C9 C -0.0013(3) 0.96066(13) 0.16508(6) 0.0180(3) Uani 1 1 d . . .
H9 H 0.1129 0.8937 0.1702 0.022 Uiso 1 1 calc R . .
C10 C 0.0316(3) 1.05570(13) 0.21246(6) 0.0179(3) Uani 1 1 d . . .
C11 C 0.2493(3) 1.04003(14) 0.26121(6) 0.0196(3) Uani 1 1 d . . .
C12 C 0.3102(3) 1.13689(15) 0.29901(7) 0.0240(3) Uani 1 1 d . . .
H12 H 0.2111 1.2082 0.2939 0.029 Uiso 1 1 calc R . .
C13 C 0.5138(3) 1.12997(16) 0.34386(7) 0.0275(4) Uani 1 1 d . . .
H13 H 0.5538 1.1965 0.3692 0.033 Uiso 1 1 calc R . .
C14 C 0.6586(3) 1.02641(16) 0.35179(7) 0.0280(4) Uani 1 1 d . . .
H14 H 0.7994 1.0221 0.3822 0.034 Uiso 1 1 calc R . .
C15 C 0.5983(3) 0.92872(16) 0.31528(7) 0.0274(4) Uani 1 1 d . . .
H15 H 0.6971 0.8575 0.3209 0.033 Uiso 1 1 calc R . .
C16 C 0.3930(3) 0.93507(15) 0.27034(7) 0.0241(4) Uani 1 1 d . . .
H16 H 0.3506 0.8678 0.2458 0.029 Uiso 1 1 calc R . .


_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 C7 1.3574(18) . ?
N1 C6 1.4039(19) . ?
N1 H1 0.8800 . ?
O1 C7 1.2324(17) . ?
O2 C10 1.2227(18) . ?
C1 C6 1.381(2) . ?
C1 C2 1.395(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(2) . ?
C5 C8 1.470(2) . ?
C7 C8 1.522(2) . ?
C8 C9 1.347(2) . ?
C9 C10 1.491(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.503(2) . ?
C11 C12 1.398(2) . ?
C11 C16 1.397(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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 N1 C6 110.96(12) . . ?
C7 N1 H1 124.5 . . ?
C6 N1 H1 124.5 . . ?
C6 C1 C2 117.17(14) . . ?
C6 C1 H1 121.4 . . ?
C2 C1 H1 121.4 . . ?
C3 C2 C1 121.21(14) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.13(14) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.66(14) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 118.88(13) . . ?
C4 C5 C8 134.57(14) . . ?
C6 C5 C8 106.55(13) . . ?
C1 C6 N1 126.88(14) . . ?
C1 C6 C5 122.94(14) . . ?
N1 C6 C5 110.18(13) . . ?
O1 C7 N1 126.80(13) . . ?
O1 C7 C8 126.15(13) . . ?
N1 C7 C8 107.04(12) . . ?
C9 C8 C5 137.83(14) . . ?
C9 C8 C7 116.90(13) . . ?
C5 C8 C7 105.27(12) . . ?
C8 C9 C10 128.24(13) . . ?
C8 C9 H9 115.9 . . ?
C10 C9 H9 115.9 . . ?
O2 C10 C9 121.47(13) . . ?
O2 C10 C11 120.74(13) . . ?
C9 C10 C11 117.70(13) . . ?
C12 C11 C16 118.81(14) . . ?
C12 C11 C10 117.46(14) . . ?
C16 C11 C10 123.73(13) . . ?
C13 C12 C11 120.70(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.12(15) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.00(14) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.09(16) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.26(15) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?

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
N1 H1 O1 0.88 1.93 2.8013(15) 168.7 3_465

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 981300'
#######################################################################
#
#                 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_ohj247

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   21.180(3)
_cell_length_b                   3.9011(6)
_cell_length_c                   16.838(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.004(9)
_cell_angle_gamma                90.00
_cell_volume                     1387.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    97(2)
_cell_measurement_reflns_used    1437
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.98

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      97(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            11915
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_sigmaI/netI    0.0918
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.59
_reflns_number_total             3181
_reflns_number_gt                2015
_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)+(0.0598P)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         3181
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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
O1 O 0.32106(7) 0.2708(4) 0.36168(8) 0.0319(4) Uani 1 1 d . . .
O2 O 0.11056(7) 0.7029(4) 0.22897(8) 0.0259(4) Uani 1 1 d . . .
O3 O 0.44792(7) -0.2245(4) 0.05416(8) 0.0290(4) Uani 1 1 d . . .
N1 N 0.08156(7) 0.4942(4) 0.34905(9) 0.0200(4) Uani 1 1 d . . .
C1 C 0.42395(10) -0.2588(6) -0.02680(12) 0.0307(5) Uani 1 1 d . . .
H1A H 0.3873 -0.4130 -0.0298 0.046 Uiso 1 1 calc R . .
H1B H 0.4570 -0.3536 -0.0584 0.046 Uiso 1 1 calc R . .
H1C H 0.4111 -0.0333 -0.0479 0.046 Uiso 1 1 calc R . .
C2 C 0.40841(9) -0.1016(5) 0.10735(12) 0.0246(5) Uani 1 1 d . . .
C3 C 0.34634(9) -0.0002(5) 0.08875(12) 0.0229(5) Uani 1 1 d . . .
H3 H 0.3285 -0.0135 0.0355 0.028 Uiso 1 1 calc R . .
C4 C 0.31066(9) 0.1205(5) 0.14851(12) 0.0231(5) Uani 1 1 d . . .
H4 H 0.2682 0.1894 0.1355 0.028 Uiso 1 1 calc R . .
C5 C 0.33518(9) 0.1438(5) 0.22722(11) 0.0200(4) Uani 1 1 d . . .
C6 C 0.29855(9) 0.2685(5) 0.29284(12) 0.0223(5) Uani 1 1 d . . .
C7 C 0.23339(9) 0.3997(5) 0.27335(11) 0.0214(5) Uani 1 1 d . . .
H7 H 0.2253 0.5030 0.2226 0.026 Uiso 1 1 calc R . .
C8 C 0.18509(9) 0.3868(5) 0.32025(11) 0.0196(4) Uani 1 1 d . . .
C9 C 0.17476(9) 0.2422(5) 0.39855(11) 0.0193(4) Uani 1 1 d . . .
C10 C 0.11160(9) 0.3169(5) 0.41384(11) 0.0198(4) Uani 1 1 d . . .
C11 C 0.08588(10) 0.2263(5) 0.48347(11) 0.0230(5) Uani 1 1 d . . .
H11 H 0.0434 0.2827 0.4926 0.028 Uiso 1 1 calc R . .
C12 C 0.12414(10) 0.0489(5) 0.54023(12) 0.0252(5) Uani 1 1 d . . .
H12 H 0.1079 -0.0138 0.5894 0.030 Uiso 1 1 calc R . .
C13 C 0.21159(10) 0.0618(5) 0.45548(11) 0.0225(5) Uani 1 1 d . . .
H13 H 0.2542 0.0059 0.4467 0.027 Uiso 1 1 calc R . .
C14 C 0.18581(10) -0.0369(5) 0.52550(12) 0.0246(5) Uani 1 1 d . . .
H14 H 0.2108 -0.1652 0.5640 0.029 Uiso 1 1 calc R . .
C15 C 0.01744(9) 0.6270(5) 0.34678(11) 0.0227(5) Uani 1 1 d . . .
H15A H 0.0081 0.7530 0.2970 0.034 Uiso 1 1 calc R . .
H15B H 0.0133 0.7814 0.3920 0.034 Uiso 1 1 calc R . .
H15C H -0.0124 0.4362 0.3498 0.034 Uiso 1 1 calc R . .
C16 C 0.12268(9) 0.5479(5) 0.29128(11) 0.0204(4) Uani 1 1 d . . .
C17 C 0.39787(10) 0.0387(6) 0.24426(12) 0.0277(5) Uani 1 1 d . . .
H17 H 0.4157 0.0501 0.2975 0.033 Uiso 1 1 calc R . .
C18 C 0.43396(10) -0.0804(6) 0.18575(12) 0.0286(5) Uani 1 1 d . . .
H18 H 0.4765 -0.1486 0.1986 0.034 Uiso 1 1 calc R . .


_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
O1 C6 1.222(2) . ?
O2 C16 1.223(2) . ?
O3 C2 1.355(2) . ?
O3 C1 1.427(2) . ?
N1 C16 1.366(2) . ?
N1 C10 1.406(2) . ?
N1 C15 1.451(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.388(3) . ?
C2 C18 1.394(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C17 1.400(3) . ?
C5 C6 1.476(3) . ?
C6 C7 1.487(3) . ?
C7 C8 1.336(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.464(3) . ?
C8 C16 1.513(3) . ?
C9 C13 1.385(3) . ?
C9 C10 1.410(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 C14 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C18 1.369(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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 O3 C1 118.00(16) . . ?
C16 N1 C10 110.58(15) . . ?
C16 N1 C15 124.63(16) . . ?
C10 N1 C15 124.61(16) . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 C3 124.79(18) . . ?
O3 C2 C18 115.48(18) . . ?
C3 C2 C18 119.72(19) . . ?
C4 C3 C2 119.35(18) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.92(18) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C17 117.46(18) . . ?
C4 C5 C6 123.62(18) . . ?
C17 C5 C6 118.92(18) . . ?
O1 C6 C5 121.45(18) . . ?
O1 C6 C7 120.09(18) . . ?
C5 C6 C7 118.45(17) . . ?
C8 C7 C6 126.41(18) . . ?
C8 C7 H7 116.8 . . ?
C6 C7 H7 116.8 . . ?
C7 C8 C9 135.67(18) . . ?
C7 C8 C16 118.76(17) . . ?
C9 C8 C16 105.56(16) . . ?
C13 C9 C10 118.30(18) . . ?
C13 C9 C8 134.96(18) . . ?
C10 C9 C8 106.74(16) . . ?
C11 C10 N1 127.17(18) . . ?
C11 C10 C9 122.73(18) . . ?
N1 C10 C9 110.10(16) . . ?
C10 C11 C12 117.86(19) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C14 C12 C11 120.46(19) . . ?
C14 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C9 C13 C14 119.54(19) . . ?
C9 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C12 C14 C13 121.07(19) . . ?
C12 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 N1 125.50(18) . . ?
O2 C16 C8 127.47(18) . . ?
N1 C16 C8 107.01(16) . . ?
C18 C17 C5 121.40(19) . . ?
C18 C17 H17 119.3 . . ?
C5 C17 H17 119.3 . . ?
C17 C18 C2 120.15(19) . . ?
C17 C18 H18 119.9 . . ?
C2 C18 H18 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 981301'
#######################################################################
#
#                 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_ohj252_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 Cl N O2'
_chemical_formula_weight         283.70

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   P2(1)/n

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

_cell_length_a                   14.514(3)
_cell_length_b                   8.7030(19)
_cell_length_c                   21.592(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.575(8)
_cell_angle_gamma                90.00
_cell_volume                     2569.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    97(2)
_cell_measurement_reflns_used    4262
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.01

_exptl_crystal_description       PLATE
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9215
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      97(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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30547
_diffrn_reflns_av_R_equivalents  0.1246
_diffrn_reflns_av_sigmaI/netI    0.1173
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         27.63
_reflns_number_total             5741
_reflns_number_gt                3493
_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, 1997)'
_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)+(0.0950P)²+1.7401P] 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         5741
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2146
_refine_ls_wR_factor_gt          0.1808
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Cl1 Cl 0.41585(7) 0.29617(11) 1.21573(5) 0.0368(3) Uani 1 1 d . . .
N1 N 0.7949(2) 0.4643(3) 0.89124(14) 0.0237(6) Uani 1 1 d . . .
H1 H 0.8444 0.5141 0.8858 0.028 Uiso 1 1 calc R . .
O1 O 0.81168(17) 0.5453(3) 0.99621(12) 0.0290(6) Uani 1 1 d . . .
O2 O 0.49952(19) 0.2118(3) 0.93197(13) 0.0354(7) Uani 1 1 d . . .
C1 C 0.7392(3) 0.3251(4) 0.78459(18) 0.0257(8) Uani 1 1 d . . .
H1A H 0.7887 0.3670 0.7699 0.031 Uiso 1 1 calc R . .
C2 C 0.6707(3) 0.2208(4) 0.74617(18) 0.0270(8) Uani 1 1 d . . .
H2 H 0.6740 0.1897 0.7048 0.032 Uiso 1 1 calc R . .
C3 C 0.5974(3) 0.1618(4) 0.76763(18) 0.0270(8) Uani 1 1 d . . .
H3 H 0.5513 0.0911 0.7407 0.032 Uiso 1 1 calc R . .
C4 C 0.5909(2) 0.2055(4) 0.82827(18) 0.0251(8) Uani 1 1 d . . .
H4 H 0.5406 0.1653 0.8426 0.030 Uiso 1 1 calc R . .
C5 C 0.6590(2) 0.3088(4) 0.86755(17) 0.0237(8) Uani 1 1 d . . .
C6 C 0.7322(2) 0.3647(4) 0.84448(18) 0.0236(8) Uani 1 1 d . . .
C7 C 0.7688(2) 0.4729(4) 0.94548(18) 0.0234(8) Uani 1 1 d . . .
C8 C 0.6775(2) 0.3754(4) 0.93311(18) 0.0235(8) Uani 1 1 d . . .
C9 C 0.6369(3) 0.3704(4) 0.98065(18) 0.0251(8) Uani 1 1 d . . .
H9 H 0.6693 0.4276 1.0193 0.030 Uiso 1 1 calc R . .
C10 C 0.5481(3) 0.2868(4) 0.97993(18) 0.0269(8) Uani 1 1 d . . .
C11 C 0.5176(3) 0.2939(4) 1.03968(18) 0.0275(8) Uani 1 1 d . . .
C12 C 0.4427(3) 0.1952(5) 1.0422(2) 0.0328(9) Uani 1 1 d . . .
H12 H 0.4135 0.1271 1.0067 0.039 Uiso 1 1 calc R . .
C13 C 0.4108(3) 0.1953(5) 1.0956(2) 0.0327(9) Uani 1 1 d . . .
H13 H 0.3602 0.1278 1.0971 0.039 Uiso 1 1 calc R . .
C14 C 0.4541(3) 0.2959(4) 1.14723(19) 0.0301(9) Uani 1 1 d . . .
C15 C 0.5285(3) 0.3946(4) 1.14630(19) 0.0294(8) Uani 1 1 d . . .
H15 H 0.5571 0.4626 1.1820 0.035 Uiso 1 1 calc R . .
C16 C 0.5605(3) 0.3930(4) 1.09309(19) 0.0296(8) Uani 1 1 d . . .
H16 H 0.6121 0.4595 1.0924 0.036 Uiso 1 1 calc R . .
Cl2 Cl 0.81833(8) 0.61536(12) 0.14538(5) 0.0403(3) Uani 1 1 d . . .
N1A N 0.4879(2) 0.8115(3) 0.49487(14) 0.0238(6) Uani 1 1 d . . .
H1A1 H 0.4427 0.8671 0.5030 0.029 Uiso 1 1 calc R . .
O1A O 0.47549(17) 0.9111(3) 0.39333(12) 0.0268(6) Uani 1 1 d . . .
O2A O 0.77135(19) 0.5455(3) 0.44190(14) 0.0373(7) Uani 1 1 d . . .
C1A C 0.5367(3) 0.6489(4) 0.59598(18) 0.0267(8) Uani 1 1 d . . .
H1A2 H 0.4916 0.6945 0.6138 0.032 Uiso 1 1 calc R . .
C2A C 0.5992(3) 0.5301(4) 0.62875(19) 0.0282(8) Uani 1 1 d . . .
H2A H 0.5961 0.4931 0.6694 0.034 Uiso 1 1 calc R . .
C3A C 0.6658(3) 0.4654(4) 0.60270(19) 0.0306(9) Uani 1 1 d . . .
H3A H 0.7074 0.3852 0.6260 0.037 Uiso 1 1 calc R . .
C4A C 0.6729(3) 0.5152(4) 0.54346(19) 0.0291(8) Uani 1 1 d . . .
H4A H 0.7187 0.4699 0.5262 0.035 Uiso 1 1 calc R . .
C5A C 0.6116(2) 0.6329(4) 0.50968(17) 0.0239(8) Uani 1 1 d . . .
C6A C 0.5435(2) 0.6969(4) 0.53682(18) 0.0250(8) Uani 1 1 d . . .
C7A C 0.5132(2) 0.8247(4) 0.44043(18) 0.0239(8) Uani 1 1 d . . .
C8A C 0.5965(2) 0.7131(4) 0.44702(17) 0.0231(7) Uani 1 1 d . . .
C9A C 0.6353(2) 0.7101(4) 0.39871(18) 0.0252(8) Uani 1 1 d . . .
H9A H 0.6051 0.7754 0.3623 0.030 Uiso 1 1 calc R . .
C10A C 0.7189(3) 0.6183(4) 0.39471(19) 0.0276(8) Uani 1 1 d . . .
C11A C 0.7410(3) 0.6213(4) 0.33174(19) 0.0268(8) Uani 1 1 d . . .
C12A C 0.8302(3) 0.5613(4) 0.3317(2) 0.0298(8) Uani 1 1 d . . .
H12A H 0.8746 0.5195 0.3710 0.036 Uiso 1 1 calc R . .
C13A C 0.8549(3) 0.5619(4) 0.2753(2) 0.0323(9) Uani 1 1 d . . .
H13A H 0.9165 0.5229 0.2761 0.039 Uiso 1 1 calc R . .
C14A C 0.7894(3) 0.6198(4) 0.2175(2) 0.0305(9) Uani 1 1 d . . .
C15A C 0.6997(3) 0.6789(4) 0.2158(2) 0.0327(9) Uani 1 1 d . . .
H15A H 0.6551 0.7184 0.1760 0.039 Uiso 1 1 calc R . .
C16A C 0.6762(3) 0.6796(4) 0.27287(19) 0.0289(8) Uani 1 1 d . . .
H16A H 0.6151 0.7202 0.2720 0.035 Uiso 1 1 calc R . .


_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 C14 1.745(4) . ?
N1 C7 1.348(4) . ?
N1 C6 1.408(4) . ?
N1 H1 0.8800 . ?
O1 C7 1.236(4) . ?
O2 C10 1.227(4) . ?
C1 C6 1.375(5) . ?
C1 C2 1.396(5) . ?
C1 H1A 0.9500 . ?
C2 C3 1.393(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(5) . ?
C5 C8 1.469(5) . ?
C7 C8 1.521(5) . ?
C8 C9 1.344(5) . ?
C9 C10 1.476(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.499(5) . ?
C11 C12 1.401(5) . ?
C11 C16 1.407(5) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(5) . ?
C15 C16 1.376(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
Cl2 C14A 1.743(4) . ?
N1A C7A 1.349(5) . ?
N1A C6A 1.406(4) . ?
N1A H1A1 0.8800 . ?
O1A C7A 1.235(4) . ?
O2A C10A 1.225(4) . ?
C1A C6A 1.378(5) . ?
C1A C2A 1.401(5) . ?
C1A H1A2 0.9500 . ?
C2A C3A 1.389(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.387(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.392(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.420(5) . ?
C5A C8A 1.472(5) . ?
C7A C8A 1.520(5) . ?
C8A C9A 1.341(5) . ?
C9A C10A 1.479(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.498(5) . ?
C11A C12A 1.396(5) . ?
C11A C16A 1.399(5) . ?
C12A C13A 1.380(5) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.386(6) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.389(5) . ?
C15A C16A 1.384(5) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?

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 N1 C6 110.8(3) . . ?
C7 N1 H1 124.6 . . ?
C6 N1 H1 124.6 . . ?
C6 C1 C2 117.4(3) . . ?
C6 C1 H1A 121.3 . . ?
C2 C1 H1A 121.3 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 C8 134.8(3) . . ?
C6 C5 C8 106.9(3) . . ?
C1 C6 C5 123.4(3) . . ?
C1 C6 N1 126.5(3) . . ?
C5 C6 N1 110.1(3) . . ?
O1 C7 N1 126.4(3) . . ?
O1 C7 C8 126.2(3) . . ?
N1 C7 C8 107.4(3) . . ?
C9 C8 C5 137.6(3) . . ?
C9 C8 C7 117.6(3) . . ?
C5 C8 C7 104.8(3) . . ?
C8 C9 C10 127.7(3) . . ?
C8 C9 H9 116.1 . . ?
C10 C9 H9 116.1 . . ?
O2 C10 C9 121.6(3) . . ?
O2 C10 C11 119.8(3) . . ?
C9 C10 C11 118.6(3) . . ?
C12 C11 C16 118.7(3) . . ?
C12 C11 C10 117.7(3) . . ?
C16 C11 C10 123.6(3) . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 Cl1 118.8(3) . . ?
C13 C14 Cl1 119.6(3) . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C7A N1A C6A 110.9(3) . . ?
C7A N1A H1A1 124.5 . . ?
C6A N1A H1A1 124.5 . . ?
C6A C1A C2A 117.1(3) . . ?
C6A C1A H1A2 121.4 . . ?
C2A C1A H1A2 121.4 . . ?
C3A C2A C1A 121.0(3) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C4A C3A C2A 121.6(4) . . ?
C4A C3A H3A 119.2 . . ?
C2A C3A H3A 119.2 . . ?
C3A C4A C5A 118.8(3) . . ?
C3A C4A H4A 120.6 . . ?
C5A C4A H4A 120.6 . . ?
C4A C5A C6A 118.9(3) . . ?
C4A C5A C8A 134.6(3) . . ?
C6A C5A C8A 106.5(3) . . ?
C1A C6A N1A 127.5(3) . . ?
C1A C6A C5A 122.6(3) . . ?
N1A C6A C5A 109.9(3) . . ?
O1A C7A N1A 126.5(3) . . ?
O1A C7A C8A 125.8(3) . . ?
N1A C7A C8A 107.7(3) . . ?
C9A C8A C5A 137.2(3) . . ?
C9A C8A C7A 117.9(3) . . ?
C5A C8A C7A 104.9(3) . . ?
C8A C9A C10A 128.5(3) . . ?
C8A C9A H9A 115.8 . . ?
C10A C9A H9A 115.8 . . ?
O2A C10A C9A 121.6(3) . . ?
O2A C10A C11A 120.1(3) . . ?
C9A C10A C11A 118.2(3) . . ?
C12A C11A C16A 118.4(3) . . ?
C12A C11A C10A 118.4(3) . . ?
C16A C11A C10A 123.2(3) . . ?
C13A C12A C11A 121.0(4) . . ?
C13A C12A H12A 119.5 . . ?
C11A C12A H12A 119.5 . . ?
C12A C13A C14A 119.6(3) . . ?
C12A C13A H13A 120.2 . . ?
C14A C13A H13A 120.2 . . ?
C13A C14A C15A 120.8(4) . . ?
C13A C14A Cl2 119.9(3) . . ?
C15A C14A Cl2 119.3(3) . . ?
C16A C15A C14A 119.1(4) . . ?
C16A C15A H15A 120.4 . . ?
C14A C15A H15A 120.4 . . ?
C15A C16A C11A 121.1(3) . . ?
C15A C16A H16A 119.5 . . ?
C11A C16A H16A 119.5 . . ?

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
N1 H1 O1A 0.88 1.96 2.822(4) 164.4 4_676

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 981302'
#######################################################################
#
#                 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_ohj268p-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 Cl N O2'
_chemical_formula_sum            'C16 H10 Cl N O2'
_chemical_formula_weight         283.70

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                   5.3737(8)
_cell_length_b                   10.8985(17)
_cell_length_c                   11.5417(18)
_cell_angle_alpha                98.268(5)
_cell_angle_beta                 99.008(5)
_cell_angle_gamma                100.544(5)
_cell_volume                     645.90(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5071
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.67

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9115
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8230
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         27.86
_reflns_number_total             8230
_reflns_number_gt                7383
_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, 1997)'
_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)+(0.1257P)²+0.8962P] 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         8230
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1984
_refine_ls_wR_factor_gt          0.1913
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cl1 Cl -0.31908(9) 0.88484(4) 0.51572(5) 0.01940(16) Uani 1 1 d . . .
O1 O -0.1053(3) 0.56651(12) 0.14739(13) 0.0232(4) Uani 1 1 d . . .
O2 O 0.3555(3) 0.56086(12) 0.36517(13) 0.0172(3) Uani 1 1 d . . .
N1 N 0.3039(3) 0.59779(14) 0.56113(15) 0.0147(3) Uani 1 1 d . . .
H1N H 0.4051 0.5526 0.5903 0.018 Uiso 1 1 calc R . .
C1 C 0.6554(4) 0.8807(2) 0.0935(2) 0.0294(5) Uani 1 1 d . . .
H1 H 0.7910 0.9278 0.0671 0.035 Uiso 1 1 calc R . .
C2 C 0.5544(4) 0.7564(2) 0.0394(2) 0.0294(5) Uani 1 1 d . . .
H9 H 0.6236 0.7200 -0.0226 0.035 Uiso 1 1 calc R . .
C3 C 0.3494(4) 0.6851(2) 0.07713(19) 0.0227(5) Uani 1 1 d . . .
H3 H 0.2803 0.6016 0.0399 0.027 Uiso 1 1 calc R . .
C4 C 0.2493(4) 0.73963(17) 0.17066(17) 0.0150(4) Uani 1 1 d . . .
C5 C 0.0276(4) 0.66311(16) 0.20931(18) 0.0151(4) Uani 1 1 d . . .
C6 C -0.0428(4) 0.71415(16) 0.32565(18) 0.0153(4) Uani 1 1 d . . .
H4 H -0.1661 0.7640 0.3236 0.018 Uiso 1 1 calc R . .
C7 C 0.0611(3) 0.69198(16) 0.43100(18) 0.0132(4) Uani 1 1 d . . .
C8 C 0.0141(3) 0.72816(16) 0.55201(17) 0.0131(4) Uani 1 1 d . . .
C9 C 0.1654(3) 0.66901(16) 0.62803(18) 0.0143(4) Uani 1 1 d . . .
C10 C 0.1679(4) 0.68124(17) 0.74848(19) 0.0184(4) Uani 1 1 d . . .
H5 H 0.2701 0.6411 0.7967 0.022 Uiso 1 1 calc R . .
C11 C 0.0107(4) 0.75637(18) 0.79541(19) 0.0190(4) Uani 1 1 d . . .
H2 H 0.0067 0.7658 0.8764 0.023 Uiso 1 1 calc R . .
C12 C 0.2578(3) 0.60919(15) 0.44460(17) 0.0132(4) Uani 1 1 d . . .
C13 C -0.1349(3) 0.80421(16) 0.60298(18) 0.0143(4) Uani 1 1 d . . .
C14 C -0.1400(4) 0.81747(18) 0.72360(19) 0.0187(4) Uani 1 1 d . . .
H6 H -0.2438 0.8671 0.7565 0.022 Uiso 1 1 calc R . .
C15 C 0.3528(4) 0.86473(17) 0.2262(2) 0.0196(4) Uani 1 1 d . . .
H7 H 0.2864 0.9008 0.2894 0.023 Uiso 1 1 calc R . .
C16 C 0.5559(4) 0.9360(2) 0.1870(2) 0.0265(5) Uani 1 1 d . . .
H8 H 0.6241 1.0200 0.2232 0.032 Uiso 1 1 calc R . .


_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 C13 1.740(2) . ?
O1 C5 1.215(2) . ?
O2 C12 1.228(2) . ?
N1 C12 1.357(3) . ?
N1 C9 1.404(2) . ?
N1 H1N 0.8600 . ?
C1 C2 1.379(3) . ?
C1 C16 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H9 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C15 1.392(3) . ?
C4 C5 1.491(3) . ?
C5 C6 1.509(3) . ?
C6 C7 1.330(3) . ?
C6 H4 0.9300 . ?
C7 C8 1.469(3) . ?
C7 C12 1.514(3) . ?
C8 C13 1.387(3) . ?
C8 C9 1.406(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.395(3) . ?
C10 H5 0.9300 . ?
C11 C14 1.390(3) . ?
C11 H2 0.9300 . ?
C13 C14 1.384(3) . ?
C14 H6 0.9300 . ?
C15 C16 1.395(3) . ?
C15 H7 0.9300 . ?
C16 H8 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
C12 N1 C9 111.44(16) . . ?
C12 N1 H1N 124.3 . . ?
C9 N1 H1N 124.3 . . ?
C2 C1 C16 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C16 C1 H1 119.8 . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H9 119.8 . . ?
C3 C2 H9 119.8 . . ?
C4 C3 C2 119.46(19) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C15 120.17(18) . . ?
C3 C4 C5 119.07(17) . . ?
C15 C4 C5 120.76(18) . . ?
O1 C5 C4 122.34(19) . . ?
O1 C5 C6 119.65(17) . . ?
C4 C5 C6 117.86(15) . . ?
C7 C6 C5 123.82(17) . . ?
C7 C6 H4 118.1 . . ?
C5 C6 H4 118.1 . . ?
C6 C7 C8 132.31(17) . . ?
C6 C7 C12 122.63(18) . . ?
C8 C7 C12 104.96(16) . . ?
C13 C8 C9 117.53(18) . . ?
C13 C8 C7 135.18(18) . . ?
C9 C8 C7 107.28(16) . . ?
C10 C9 N1 127.45(18) . . ?
C10 C9 C8 123.22(18) . . ?
N1 C9 C8 109.33(17) . . ?
C9 C10 C11 117.25(19) . . ?
C9 C10 H5 121.4 . . ?
C11 C10 H5 121.4 . . ?
C14 C11 C10 121.4(2) . . ?
C14 C11 H2 119.3 . . ?
C10 C11 H2 119.3 . . ?
O2 C12 N1 126.53(17) . . ?
O2 C12 C7 126.54(17) . . ?
N1 C12 C7 106.93(16) . . ?
C14 C13 C8 120.88(19) . . ?
C14 C13 Cl1 118.82(16) . . ?
C8 C13 Cl1 120.30(16) . . ?
C13 C14 C11 119.72(19) . . ?
C13 C14 H6 120.1 . . ?
C11 C14 H6 120.1 . . ?
C4 C15 C16 120.0(2) . . ?
C4 C15 H7 120.0 . . ?
C16 C15 H7 120.0 . . ?
C1 C16 C15 119.45(19) . . ?
C1 C16 H8 120.3 . . ?
C15 C16 H8 120.3 . . ?

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
C16 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C15 0.1(3) . . . . ?
C2 C3 C4 C5 179.19(19) . . . . ?
C3 C4 C5 O1 -16.7(3) . . . . ?
C15 C4 C5 O1 162.39(19) . . . . ?
C3 C4 C5 C6 167.87(17) . . . . ?
C15 C4 C5 C6 -13.1(3) . . . . ?
O1 C5 C6 C7 96.6(2) . . . . ?
C4 C5 C6 C7 -87.8(2) . . . . ?
C5 C6 C7 C8 -177.52(17) . . . . ?
C5 C6 C7 C12 -1.8(3) . . . . ?
C6 C7 C8 C13 -6.0(3) . . . . ?
C12 C7 C8 C13 177.73(19) . . . . ?
C6 C7 C8 C9 175.02(18) . . . . ?
C12 C7 C8 C9 -1.28(18) . . . . ?
C12 N1 C9 C10 -179.01(17) . . . . ?
C12 N1 C9 C8 1.7(2) . . . . ?
C13 C8 C9 C10 1.3(3) . . . . ?
C7 C8 C9 C10 -179.47(16) . . . . ?
C13 C8 C9 N1 -179.32(15) . . . . ?
C7 C8 C9 N1 -0.10(19) . . . . ?
N1 C9 C10 C11 -179.18(17) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C14 -0.7(3) . . . . ?
C9 N1 C12 O2 178.05(16) . . . . ?
C9 N1 C12 C7 -2.43(19) . . . . ?
C6 C7 C12 O2 5.0(3) . . . . ?
C8 C7 C12 O2 -178.22(16) . . . . ?
C6 C7 C12 N1 -174.50(16) . . . . ?
C8 C7 C12 N1 2.25(18) . . . . ?
C9 C8 C13 C14 -2.1(3) . . . . ?
C7 C8 C13 C14 178.94(18) . . . . ?
C9 C8 C13 Cl1 177.86(12) . . . . ?
C7 C8 C13 Cl1 -1.1(3) . . . . ?
C8 C13 C14 C11 1.6(3) . . . . ?
Cl1 C13 C14 C11 -178.41(14) . . . . ?
C10 C11 C14 C13 -0.1(3) . . . . ?
C3 C4 C15 C16 0.7(3) . . . . ?
C5 C4 C15 C16 -178.38(18) . . . . ?
C2 C1 C16 C15 0.1(3) . . . . ?
C4 C15 C16 C1 -0.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.918
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.102
_database_code_depnum_ccdc_archive 'CCDC 981303'
#######################################################################
#
#                 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_ohj266

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 Cl N2 O2'
_chemical_formula_sum            'C16 H11 Cl N2 O2'
_chemical_formula_weight         298.72

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   P12(1)/c1

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                   11.728(4)
_cell_length_b                   16.825(5)
_cell_length_c                   7.205(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.87(2)
_cell_angle_gamma                90.00
_cell_volume                     1374.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(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          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5835
_diffrn_reflns_av_R_equivalents  0.1110
_diffrn_reflns_av_sigmaI/netI    0.1396
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.86
_reflns_number_total             2726
_reflns_number_gt                1387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2726
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1581
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.2125
_refine_ls_wR_factor_gt          0.1796
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.431
_refine_ls_shift/su_mean         0.060

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 0.38310(10) 0.20038(6) 1.0470(2) 0.0380(4) Uani 1 1 d . . .
O1 O 0.3426(3) 0.50000(17) 1.2442(5) 0.0425(9) Uani 1 1 d . . .
O2 O 0.1052(2) 0.48622(16) 0.8784(6) 0.0394(9) Uani 1 1 d . . .
N1 N 0.3523(3) 0.6843(2) 0.8669(7) 0.0380(11) Uani 1 1 d . . .
N2 N 0.0190(3) 0.3634(2) 0.7964(7) 0.0340(10) Uani 1 1 d . . .
C1 C 0.3698(4) 0.6642(3) 0.6953(8) 0.0356(12) Uani 1 1 d . . .
H1 H 0.3754 0.7047 0.6104 0.043 Uiso 1 1 calc R . .
C2 C 0.3444(4) 0.6237(2) 0.9829(8) 0.0341(11) Uani 1 1 d . . .
H11 H 0.3336 0.6358 1.1032 0.041 Uiso 1 1 calc R . .
C3 C 0.3511(3) 0.5437(2) 0.9370(7) 0.0275(11) Uani 1 1 d . . .
C4 C 0.3379(4) 0.4828(2) 1.0794(8) 0.0288(11) Uani 1 1 d . . .
C5 C 0.3237(4) 0.3960(2) 1.0250(7) 0.0292(11) Uani 1 1 d . . .
H5 H 0.3905 0.3639 1.0510 0.035 Uiso 1 1 calc R . .
C6 C 0.2190(4) 0.3634(2) 0.9408(7) 0.0260(10) Uani 1 1 d . . .
C7 C 0.1795(4) 0.2809(2) 0.9001(7) 0.0256(10) Uani 1 1 d . . .
C8 C 0.0574(4) 0.2837(2) 0.8164(8) 0.0307(11) Uani 1 1 d . . .
C9 C -0.0096(4) 0.2158(3) 0.7640(9) 0.0393(13) Uani 1 1 d . . .
H6 H -0.0898 0.2187 0.7048 0.047 Uiso 1 1 calc R . .
C10 C 0.0478(4) 0.1430(3) 0.8034(8) 0.0399(13) Uani 1 1 d . . .
H2 H 0.0046 0.0963 0.7717 0.048 Uiso 1 1 calc R . .
C11 C 0.3681(3) 0.5252(2) 0.7575(8) 0.0324(12) Uani 1 1 d . . .
H4 H 0.3714 0.4727 0.7193 0.039 Uiso 1 1 calc R . .
C12 C 0.3797(4) 0.5867(2) 0.6387(8) 0.0352(12) Uani 1 1 d . . .
H3 H 0.3943 0.5762 0.5202 0.042 Uiso 1 1 calc R . .
C13 C 0.1112(4) 0.4142(2) 0.8701(8) 0.0309(11) Uani 1 1 d . . .
C14 C 0.2331(4) 0.2073(2) 0.9390(7) 0.0311(11) Uani 1 1 d . . .
C15 C 0.1670(4) 0.1382(3) 0.8881(8) 0.0365(12) Uani 1 1 d . . .
H7 H 0.2034 0.0888 0.9114 0.044 Uiso 1 1 calc R . .
C16 C -0.1005(4) 0.3892(3) 0.7159(10) 0.0486(15) Uani 1 1 d . . .
H9 H -0.1102 0.4421 0.7592 0.073 Uiso 1 1 calc R . .
H10 H -0.1538 0.3539 0.7565 0.073 Uiso 1 1 calc R . .
H8 H -0.1172 0.3887 0.5783 0.073 Uiso 1 1 calc R . .


_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 C14 1.735(5) . ?
O1 C4 1.210(6) . ?
O2 C13 1.216(5) . ?
N1 C2 1.337(6) . ?
N1 C1 1.348(7) . ?
N2 C13 1.374(6) . ?
N2 C8 1.409(5) . ?
N2 C16 1.440(6) . ?
C1 C12 1.379(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(6) . ?
C2 H11 0.9300 . ?
C3 C11 1.393(7) . ?
C3 C4 1.486(6) . ?
C4 C5 1.510(6) . ?
C5 C6 1.340(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.468(5) . ?
C6 C13 1.503(6) . ?
C7 C14 1.385(6) . ?
C7 C8 1.405(7) . ?
C8 C9 1.383(6) . ?
C9 C10 1.392(7) . ?
C9 H6 0.9300 . ?
C10 C15 1.376(7) . ?
C10 H2 0.9300 . ?
C11 C12 1.372(6) . ?
C11 H4 0.9300 . ?
C12 H3 0.9300 . ?
C14 C15 1.394(6) . ?
C15 H7 0.9300 . ?
C16 H9 0.9600 . ?
C16 H10 0.9600 . ?
C16 H8 0.9600 . ?

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 N1 C1 115.7(4) . . ?
C13 N2 C8 110.7(4) . . ?
C13 N2 C16 123.8(4) . . ?
C8 N2 C16 125.5(4) . . ?
N1 C1 C12 123.5(4) . . ?
N1 C1 H1 118.2 . . ?
C12 C1 H1 118.2 . . ?
N1 C2 C3 124.9(5) . . ?
N1 C2 H11 117.6 . . ?
C3 C2 H11 117.6 . . ?
C2 C3 C11 117.8(4) . . ?
C2 C3 C4 118.7(4) . . ?
C11 C3 C4 123.5(4) . . ?
O1 C4 C3 121.7(4) . . ?
O1 C4 C5 117.4(4) . . ?
C3 C4 C5 120.8(4) . . ?
C6 C5 C4 122.7(4) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C7 133.1(4) . . ?
C5 C6 C13 120.9(4) . . ?
C7 C6 C13 105.9(4) . . ?
C14 C7 C8 118.5(4) . . ?
C14 C7 C6 134.5(4) . . ?
C8 C7 C6 106.8(3) . . ?
C9 C8 C7 122.3(4) . . ?
C9 C8 N2 127.9(4) . . ?
C7 C8 N2 109.8(3) . . ?
C8 C9 C10 117.4(5) . . ?
C8 C9 H6 121.3 . . ?
C10 C9 H6 121.3 . . ?
C15 C10 C9 121.6(4) . . ?
C15 C10 H2 119.2 . . ?
C9 C10 H2 119.2 . . ?
C12 C11 C3 118.1(4) . . ?
C12 C11 H4 120.9 . . ?
C3 C11 H4 120.9 . . ?
C11 C12 C1 119.9(5) . . ?
C11 C12 H3 120.1 . . ?
C1 C12 H3 120.0 . . ?
O2 C13 N2 126.2(4) . . ?
O2 C13 C6 127.2(4) . . ?
N2 C13 C6 106.7(3) . . ?
C7 C14 C15 120.0(5) . . ?
C7 C14 Cl1 120.4(3) . . ?
C15 C14 Cl1 119.6(3) . . ?
C10 C15 C14 120.1(4) . . ?
C10 C15 H7 120.0 . . ?
C14 C15 H7 120.0 . . ?
N2 C16 H9 109.5 . . ?
N2 C16 H10 109.5 . . ?
H9 C16 H10 109.5 . . ?
N2 C16 H8 109.5 . . ?
H9 C16 H8 109.5 . . ?
H10 C16 H8 109.5 . . ?

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
C2 N1 C1 C12 -0.3(7) . . . . ?
C1 N1 C2 C3 -1.0(7) . . . . ?
N1 C2 C3 C11 0.4(7) . . . . ?
N1 C2 C3 C4 -178.5(4) . . . . ?
C2 C3 C4 O1 -13.4(6) . . . . ?
C11 C3 C4 O1 167.7(4) . . . . ?
C2 C3 C4 C5 169.6(4) . . . . ?
C11 C3 C4 C5 -9.3(6) . . . . ?
O1 C4 C5 C6 97.6(6) . . . . ?
C3 C4 C5 C6 -85.2(6) . . . . ?
C4 C5 C6 C7 -169.6(5) . . . . ?
C4 C5 C6 C13 8.7(7) . . . . ?
C5 C6 C7 C14 2.9(9) . . . . ?
C13 C6 C7 C14 -175.6(5) . . . . ?
C5 C6 C7 C8 177.2(5) . . . . ?
C13 C6 C7 C8 -1.3(5) . . . . ?
C14 C7 C8 C9 -3.0(8) . . . . ?
C6 C7 C8 C9 -178.3(5) . . . . ?
C14 C7 C8 N2 177.4(4) . . . . ?
C6 C7 C8 N2 2.0(5) . . . . ?
C13 N2 C8 C9 178.3(5) . . . . ?
C16 N2 C8 C9 0.2(9) . . . . ?
C13 N2 C8 C7 -2.0(6) . . . . ?
C16 N2 C8 C7 179.9(5) . . . . ?
C7 C8 C9 C10 2.2(8) . . . . ?
N2 C8 C9 C10 -178.2(5) . . . . ?
C8 C9 C10 C15 -1.1(8) . . . . ?
C2 C3 C11 C12 1.4(6) . . . . ?
C4 C3 C11 C12 -179.7(4) . . . . ?
C3 C11 C12 C1 -2.6(6) . . . . ?
N1 C1 C12 C11 2.1(7) . . . . ?
C8 N2 C13 O2 -177.9(5) . . . . ?
C16 N2 C13 O2 0.3(8) . . . . ?
C8 N2 C13 C6 1.1(5) . . . . ?
C16 N2 C13 C6 179.3(5) . . . . ?
C5 C6 C13 O2 0.4(8) . . . . ?
C7 C6 C13 O2 179.1(5) . . . . ?
C5 C6 C13 N2 -178.6(5) . . . . ?
C7 C6 C13 N2 0.1(5) . . . . ?
C8 C7 C14 C15 2.6(7) . . . . ?
C6 C7 C14 C15 176.3(5) . . . . ?
C8 C7 C14 Cl1 -178.6(4) . . . . ?
C6 C7 C14 Cl1 -4.8(8) . . . . ?
C9 C10 C15 C14 0.8(8) . . . . ?
C7 C14 C15 C10 -1.6(8) . . . . ?
Cl1 C14 C15 C10 179.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.834
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.834
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.105
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.086
;
_database_code_depnum_ccdc_archive 'CCDC 981304'
