# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047945'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C7 H5 I O2'
_chemical_formula_sum            'C20 H14 I N O2'
_chemical_formula_weight         427.22

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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 '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                   7.1369(15)
_cell_length_b                   8.7725(17)
_cell_length_c                   14.2906(13)
_cell_angle_alpha                77.820(13)
_cell_angle_beta                 81.659(13)
_cell_angle_gamma                79.743(17)
_cell_volume                     855.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5398
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            light-brown
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    1.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4744
_exptl_absorpt_correction_T_max  0.7248
_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5398
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2992
_reflns_number_gt                2498
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_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)+(0.0398P)²+0.3350P] 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     SHELXL
_refine_ls_extinction_coef       0.0328(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_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 0.6600(6) 1.3301(5) 0.6122(4) 0.0713(12) Uani 1 1 d . . .
H1 H 0.6393 1.4223 0.5665 0.086 Uiso 1 1 calc R . .
C2 C 0.6508(6) 1.3391(6) 0.7055(5) 0.0829(15) Uani 1 1 d . . .
H2 H 0.6245 1.4370 0.7238 0.099 Uiso 1 1 calc R . .
C3 C 0.6808(6) 1.2013(6) 0.7752(4) 0.0791(14) Uani 1 1 d . . .
H3 H 0.6750 1.2094 0.8395 0.095 Uiso 1 1 calc R . .
C4 C 0.7181(5) 1.0563(5) 0.7514(3) 0.0609(10) Uani 1 1 d . . .
H4 H 0.7359 0.9664 0.7990 0.073 Uiso 1 1 calc R . .
C5 C 0.8159(5) 0.7294(4) 0.5154(3) 0.0550(9) Uani 1 1 d . . .
H5 H 0.8345 0.6411 0.5641 0.066 Uiso 1 1 calc R . .
C6 C 0.8250(6) 0.7108(6) 0.4242(4) 0.0726(12) Uani 1 1 d . . .
H6 H 0.8481 0.6098 0.4102 0.087 Uiso 1 1 calc R . .
C7 C 0.7997(6) 0.8436(8) 0.3490(3) 0.0806(14) Uani 1 1 d . . .
H7 H 0.8071 0.8291 0.2859 0.097 Uiso 1 1 calc R . .
C8 C 0.7652(6) 0.9906(6) 0.3677(3) 0.0680(11) Uani 1 1 d . . .
H8 H 0.7499 1.0767 0.3173 0.082 Uiso 1 1 calc R . .
C9 C 0.7142(5) 1.1646(4) 0.4873(3) 0.0550(10) Uani 1 1 d . . .
H9 H 0.6976 1.2539 0.4392 0.066 Uiso 1 1 calc R . .
N10 N 0.7681(4) 0.8976(3) 0.6311(2) 0.0420(6) Uani 1 1 d . . .
C11 C 0.7011(5) 1.1809(4) 0.5819(3) 0.0485(8) Uani 1 1 d . . .
C12 C 0.7299(4) 1.0424(4) 0.6533(2) 0.0440(8) Uani 1 1 d . . .
C13 C 0.7518(4) 1.0158(4) 0.4630(2) 0.0470(8) Uani 1 1 d . . .
C14 C 0.7781(4) 0.8825(4) 0.5389(2) 0.0416(7) Uani 1 1 d . . .
C15 C 1.0072(5) 0.4416(4) 0.8607(3) 0.0472(8) Uani 1 1 d . . .
C16 C 0.8515(5) 0.4166(4) 0.9286(2) 0.0457(8) Uani 1 1 d . . .
H16 H 0.7356 0.4840 0.9231 0.055 Uiso 1 1 calc R . .
C17 C 0.8700(5) 0.2899(4) 1.0050(2) 0.0494(8) Uani 1 1 d . . .
C18 C 1.0397(6) 0.1886(4) 1.0152(3) 0.0620(11) Uani 1 1 d . . .
H18 H 1.0498 0.1029 1.0661 0.074 Uiso 1 1 calc R . .
C19 C 1.1951(7) 0.2176(5) 0.9476(4) 0.0735(12) Uani 1 1 d . . .
H19 H 1.3120 0.1520 0.9540 0.088 Uiso 1 1 calc R . .
C20 C 1.1793(6) 0.3417(5) 0.8711(3) 0.0619(10) Uani 1 1 d . . .
H20 H 1.2850 0.3587 0.8260 0.074 Uiso 1 1 calc R . .
C21 C 0.9912(6) 0.5722(4) 0.7748(3) 0.0533(9) Uani 1 1 d . . .
O22 O 0.8228(4) 0.6618(3) 0.7751(2) 0.0653(7) Uani 1 1 d D . .
H22 H 0.807(7) 0.745(4) 0.718(2) 0.098 Uiso 1 1 d D . .
O23 O 1.1187(4) 0.5894(4) 0.7105(2) 0.0797(8) Uani 1 1 d . . .
I24 I 0.62964(4) 0.25088(4) 1.104731(19) 0.07747(19) Uani 1 1 d . . .


_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 1.344(7) . ?
C1 C11 1.432(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.401(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(6) . ?
C3 H3 0.9300 . ?
C4 C12 1.422(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.338(6) . ?
C5 C14 1.422(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.413(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.344(7) . ?
C7 H7 0.9300 . ?
C8 C13 1.413(5) . ?
C8 H8 0.9300 . ?
C9 C11 1.377(5) . ?
C9 C13 1.391(5) . ?
C9 H9 0.9300 . ?
N10 C14 1.343(4) . ?
N10 C12 1.346(4) . ?
C11 C12 1.416(5) . ?
C13 C14 1.422(5) . ?
C15 C16 1.382(5) . ?
C15 C20 1.383(5) . ?
C15 C21 1.495(5) . ?
C16 C17 1.387(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(5) . ?
C17 I24 2.094(4) . ?
C18 C19 1.384(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O23 1.200(5) . ?
C21 O22 1.313(5) . ?
O22 H22 0.98(2) . ?

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 C11 121.1(4) . . ?
C2 C1 H1 119.5 . . ?
C11 C1 H1 119.5 . . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 121.6(5) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C12 119.7(4) . . ?
C3 C4 H4 120.1 . . ?
C12 C4 H4 120.1 . . ?
C6 C5 C14 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C14 C5 H5 119.5 . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C13 120.7(4) . . ?
C7 C8 H8 119.6 . . ?
C13 C8 H8 119.6 . . ?
C11 C9 C13 120.7(3) . . ?
C11 C9 H9 119.7 . . ?
C13 C9 H9 119.7 . . ?
C14 N10 C12 119.5(3) . . ?
C9 C11 C12 118.2(3) . . ?
C9 C11 C1 123.6(4) . . ?
C12 C11 C1 118.2(4) . . ?
N10 C12 C11 122.0(3) . . ?
N10 C12 C4 118.8(3) . . ?
C11 C12 C4 119.2(3) . . ?
C9 C13 C8 123.6(4) . . ?
C9 C13 C14 117.7(3) . . ?
C8 C13 C14 118.7(4) . . ?
N10 C14 C13 121.9(3) . . ?
N10 C14 C5 119.6(3) . . ?
C13 C14 C5 118.5(3) . . ?
C16 C15 C20 119.5(4) . . ?
C16 C15 C21 121.0(3) . . ?
C20 C15 C21 119.5(4) . . ?
C15 C16 C17 119.2(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 121.7(4) . . ?
C18 C17 I24 119.8(3) . . ?
C16 C17 I24 118.5(3) . . ?
C17 C18 C19 118.2(4) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C20 C19 C18 121.0(4) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C15 120.4(4) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O23 C21 O22 123.7(4) . . ?
O23 C21 C15 122.7(4) . . ?
O22 C21 C15 113.5(3) . . ?
C21 O22 H22 115(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
C11 C1 C2 C3 -0.3(6) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C2 C3 C4 C12 0.8(6) . . . . ?
C14 C5 C6 C7 0.9(6) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C13 -0.5(6) . . . . ?
C13 C9 C11 C12 0.9(5) . . . . ?
C13 C9 C11 C1 -179.1(3) . . . . ?
C2 C1 C11 C9 -179.3(4) . . . . ?
C2 C1 C11 C12 0.7(5) . . . . ?
C14 N10 C12 C11 -0.5(4) . . . . ?
C14 N10 C12 C4 179.4(3) . . . . ?
C9 C11 C12 N10 -0.4(5) . . . . ?
C1 C11 C12 N10 179.6(3) . . . . ?
C9 C11 C12 C4 179.7(3) . . . . ?
C1 C11 C12 C4 -0.3(5) . . . . ?
C3 C4 C12 N10 179.6(3) . . . . ?
C3 C4 C12 C11 -0.4(5) . . . . ?
C11 C9 C13 C8 179.3(3) . . . . ?
C11 C9 C13 C14 -0.6(5) . . . . ?
C7 C8 C13 C9 -179.2(4) . . . . ?
C7 C8 C13 C14 0.8(5) . . . . ?
C12 N10 C14 C13 0.8(4) . . . . ?
C12 N10 C14 C5 -179.1(3) . . . . ?
C9 C13 C14 N10 -0.3(4) . . . . ?
C8 C13 C14 N10 179.8(3) . . . . ?
C9 C13 C14 C5 179.7(3) . . . . ?
C8 C13 C14 C5 -0.3(4) . . . . ?
C6 C5 C14 N10 179.4(3) . . . . ?
C6 C5 C14 C13 -0.6(5) . . . . ?
C20 C15 C16 C17 -1.2(5) . . . . ?
C21 C15 C16 C17 177.1(3) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C15 C16 C17 I24 -178.3(2) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
I24 C17 C18 C19 179.6(3) . . . . ?
C17 C18 C19 C20 -1.5(6) . . . . ?
C18 C19 C20 C15 0.6(6) . . . . ?
C16 C15 C20 C19 0.7(6) . . . . ?
C21 C15 C20 C19 -177.6(4) . . . . ?
C16 C15 C21 O23 -173.7(4) . . . . ?
C20 C15 C21 O23 4.6(6) . . . . ?
C16 C15 C21 O22 3.9(5) . . . . ?
C20 C15 C21 O22 -177.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047946'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C7 H6 O2'
_chemical_formula_sum            'C20 H15 N O2'
_chemical_formula_weight         301.33

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.9451(3)
_cell_length_b                   13.4053(3)
_cell_length_c                   13.4770(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.006(3)
_cell_angle_gamma                90.00
_cell_volume                     1560.93(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    20140
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            light-orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.990

_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20140
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0107
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2738
_reflns_number_gt                2414
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_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)+(0.0405P)²+0.3645P] 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     SHELXL
_refine_ls_extinction_coef       0.0062(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2738
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.22153(19) 0.32629(12) 0.08638(16) 0.0667(5) Uani 1 1 d . . .
H1 H 0.1273 0.3272 0.0368 0.080 Uiso 1 1 calc R . .
C2 C 0.2242(2) 0.30866(13) 0.18528(17) 0.0762(6) Uani 1 1 d . . .
H2 H 0.1320 0.2981 0.2034 0.091 Uiso 1 1 calc R . .
C3 C 0.3652(3) 0.30617(13) 0.26111(15) 0.0747(5) Uani 1 1 d . . .
H3 H 0.3651 0.2942 0.3291 0.090 Uiso 1 1 calc R . .
C4 C 0.5008(2) 0.32082(12) 0.23698(12) 0.0614(4) Uani 1 1 d . . .
H4 H 0.5931 0.3177 0.2882 0.074 Uiso 1 1 calc R . .
C5 C 0.78735(18) 0.39675(11) -0.00661(13) 0.0571(4) Uani 1 1 d . . .
H5 H 0.8781 0.3960 0.0461 0.069 Uiso 1 1 calc R . .
C6 C 0.7935(2) 0.41562(12) -0.10424(14) 0.0678(5) Uani 1 1 d . . .
H6 H 0.8887 0.4271 -0.1180 0.081 Uiso 1 1 calc R . .
C7 C 0.6578(3) 0.41806(13) -0.18498(14) 0.0716(5) Uani 1 1 d . . .
H7 H 0.6643 0.4308 -0.2516 0.086 Uiso 1 1 calc R . .
C8 C 0.5188(2) 0.40214(12) -0.16708(12) 0.0636(4) Uani 1 1 d . . .
H8 H 0.4301 0.4049 -0.2213 0.076 Uiso 1 1 calc R . .
C9 C 0.36588(17) 0.36396(10) -0.04308(12) 0.0524(4) Uani 1 1 d . . .
H9 H 0.2743 0.3661 -0.0950 0.063 Uiso 1 1 calc R . .
N10 N 0.64051(13) 0.35820(8) 0.11301(8) 0.0466(3) Uani 1 1 d . . .
C11 C 0.36122(16) 0.34362(10) 0.05655(12) 0.0495(4) Uani 1 1 d . . .
C12 C 0.50368(16) 0.34096(10) 0.13396(11) 0.0464(3) Uani 1 1 d . . .
C13 C 0.50580(17) 0.38119(10) -0.06644(11) 0.0476(3) Uani 1 1 d . . .
C14 C 0.64339(16) 0.37815(9) 0.01558(10) 0.0440(3) Uani 1 1 d . . .
C15 C 1.07989(16) 0.46761(10) 0.38337(10) 0.0462(3) Uani 1 1 d . . .
C16 C 1.15405(19) 0.55777(12) 0.40821(12) 0.0596(4) Uani 1 1 d . . .
H16 H 1.1203 0.6134 0.3673 0.072 Uiso 1 1 calc R . .
C17 C 1.2773(2) 0.56603(13) 0.49299(13) 0.0727(5) Uani 1 1 d . . .
H17 H 1.3269 0.6271 0.5092 0.087 Uiso 1 1 calc R . .
C18 C 1.3274(2) 0.48477(14) 0.55371(13) 0.0710(5) Uani 1 1 d . . .
H18 H 1.4115 0.4905 0.6108 0.085 Uiso 1 1 calc R . .
C19 C 1.2542(2) 0.39519(13) 0.53062(13) 0.0736(5) Uani 1 1 d . . .
H19 H 1.2878 0.3401 0.5724 0.088 Uiso 1 1 calc R . .
C20 C 1.1306(2) 0.38629(12) 0.44557(12) 0.0622(4) Uani 1 1 d . . .
H20 H 1.0810 0.3251 0.4300 0.075 Uiso 1 1 calc R . .
C21 C 0.94880(17) 0.46067(12) 0.29007(11) 0.0521(4) Uani 1 1 d . . .
O22 O 0.88723(13) 0.37100(8) 0.27383(9) 0.0651(3) Uani 1 1 d D . .
H22 H 0.799(2) 0.3708(15) 0.2125(13) 0.098 Uiso 1 1 d D . .
O23 O 0.90519(15) 0.53006(9) 0.23309(9) 0.0824(4) Uani 1 1 d . . .


_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 1.348(3) . ?
C1 C11 1.427(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.349(2) . ?
C3 H3 0.9300 . ?
C4 C12 1.421(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.355(2) . ?
C5 C14 1.418(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.343(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.419(2) . ?
C8 H8 0.9300 . ?
C9 C11 1.381(2) . ?
C9 C13 1.387(2) . ?
C9 H9 0.9300 . ?
N10 C12 1.3454(18) . ?
N10 C14 1.3467(17) . ?
C11 C12 1.423(2) . ?
C13 C14 1.4261(19) . ?
C15 C16 1.378(2) . ?
C15 C20 1.378(2) . ?
C15 C21 1.484(2) . ?
C16 C17 1.372(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O23 1.2051(18) . ?
C21 O22 1.3167(18) . ?
O22 H22 0.987(15) . ?

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 C11 120.96(17) . . ?
C2 C1 H1 119.5 . . ?
C11 C1 H1 119.5 . . ?
C1 C2 C3 120.47(17) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 121.04(17) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C12 120.53(17) . . ?
C3 C4 H4 119.7 . . ?
C12 C4 H4 119.7 . . ?
C6 C5 C14 120.35(15) . . ?
C6 C5 H5 119.8 . . ?
C14 C5 H5 119.8 . . ?
C5 C6 C7 120.82(16) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.75(15) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C13 120.79(16) . . ?
C7 C8 H8 119.6 . . ?
C13 C8 H8 119.6 . . ?
C11 C9 C13 120.64(13) . . ?
C11 C9 H9 119.7 . . ?
C13 C9 H9 119.7 . . ?
C12 N10 C14 119.13(12) . . ?
C9 C11 C12 118.09(13) . . ?
C9 C11 C1 123.70(15) . . ?
C12 C11 C1 118.20(15) . . ?
N10 C12 C4 119.03(13) . . ?
N10 C12 C11 122.17(13) . . ?
C4 C12 C11 118.79(14) . . ?
C9 C13 C8 123.52(14) . . ?
C9 C13 C14 117.90(13) . . ?
C8 C13 C14 118.59(14) . . ?
N10 C14 C5 119.24(13) . . ?
N10 C14 C13 122.06(13) . . ?
C5 C14 C13 118.70(13) . . ?
C16 C15 C20 118.96(14) . . ?
C16 C15 C21 119.09(13) . . ?
C20 C15 C21 121.95(13) . . ?
C17 C16 C15 120.39(14) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.18(16) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.09(15) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.06(15) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.31(15) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O23 C21 O22 123.12(14) . . ?
O23 C21 C15 123.10(14) . . ?
O22 C21 C15 113.76(12) . . ?
C21 O22 H22 110.7(12) . . ?

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
C11 C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C12 1.1(3) . . . . ?
C14 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C13 -0.8(3) . . . . ?
C13 C9 C11 C12 0.0(2) . . . . ?
C13 C9 C11 C1 179.26(13) . . . . ?
C2 C1 C11 C9 -178.71(15) . . . . ?
C2 C1 C11 C12 0.5(2) . . . . ?
C14 N10 C12 C4 -179.43(12) . . . . ?
C14 N10 C12 C11 -0.35(19) . . . . ?
C3 C4 C12 N10 178.00(14) . . . . ?
C3 C4 C12 C11 -1.1(2) . . . . ?
C9 C11 C12 N10 0.5(2) . . . . ?
C1 C11 C12 N10 -178.79(12) . . . . ?
C9 C11 C12 C4 179.56(13) . . . . ?
C1 C11 C12 C4 0.28(19) . . . . ?
C11 C9 C13 C8 179.77(14) . . . . ?
C11 C9 C13 C14 -0.60(19) . . . . ?
C7 C8 C13 C9 -179.90(15) . . . . ?
C7 C8 C13 C14 0.5(2) . . . . ?
C12 N10 C14 C5 179.74(12) . . . . ?
C12 N10 C14 C13 -0.27(19) . . . . ?
C6 C5 C14 N10 179.08(13) . . . . ?
C6 C5 C14 C13 -0.9(2) . . . . ?
C9 C13 C14 N10 0.75(19) . . . . ?
C8 C13 C14 N10 -179.60(13) . . . . ?
C9 C13 C14 C5 -179.26(12) . . . . ?
C8 C13 C14 C5 0.38(19) . . . . ?
C20 C15 C16 C17 0.6(3) . . . . ?
C21 C15 C16 C17 -178.86(15) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C16 C15 C20 C19 -0.5(3) . . . . ?
C21 C15 C20 C19 178.96(16) . . . . ?
C16 C15 C21 O23 1.5(2) . . . . ?
C20 C15 C21 O23 -177.96(16) . . . . ?
C16 C15 C21 O22 179.81(14) . . . . ?
C20 C15 C21 O22 0.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.023
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047947'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 F O2, C13 H9 N'
_chemical_formula_sum            'C20 H14 F N O2'
_chemical_formula_weight         319.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   6.9901(10)
_cell_length_b                   23.197(4)
_cell_length_c                   9.8827(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.349(14)
_cell_angle_gamma                90.00
_cell_volume                     1585.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10327
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5381
_exptl_absorpt_correction_T_max  0.8158

_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10327
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2783
_reflns_number_gt                2207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_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)+(0.0569P)²+0.4154P] 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     SHELXL
_refine_ls_extinction_coef       0.0110(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2783
_refine_ls_number_parameters     249
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      2.677
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.004

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 0.1983(8) -0.1147(2) 0.3220(7) 0.0626(15) Uani 1 1 d . . .
H1 H 0.2045 -0.1473 0.3772 0.075 Uiso 1 1 calc R . .
C2 C 0.1693(9) -0.1205(3) 0.1851(8) 0.0763(19) Uani 1 1 d . . .
H2 H 0.1539 -0.1571 0.1465 0.092 Uiso 1 1 calc R . .
C3 C 0.1620(9) -0.0718(4) 0.1000(7) 0.078(2) Uani 1 1 d . . .
H3 H 0.1448 -0.0767 0.0057 0.094 Uiso 1 1 calc R . .
C4 C 0.1795(8) -0.0177(3) 0.1527(6) 0.0668(16) Uani 1 1 d . . .
H4 H 0.1732 0.0140 0.0947 0.080 Uiso 1 1 calc R . .
C5 C 0.2644(8) 0.1093(2) 0.5384(7) 0.0637(16) Uani 1 1 d . . .
H5 H 0.2511 0.1406 0.4790 0.076 Uiso 1 1 calc R . .
C6 C 0.2965(9) 0.1181(3) 0.6755(8) 0.0747(19) Uani 1 1 d . . .
H6 H 0.3044 0.1555 0.7094 0.090 Uiso 1 1 calc R . .
C7 C 0.3180(8) 0.0715(3) 0.7668(7) 0.0737(19) Uani 1 1 d . . .
H7 H 0.3414 0.0785 0.8604 0.088 Uiso 1 1 calc R . .
C8 C 0.3052(7) 0.0166(3) 0.7208(6) 0.0597(15) Uani 1 1 d . . .
H8 H 0.3197 -0.0138 0.7829 0.072 Uiso 1 1 calc R . .
C9 C 0.2528(7) -0.0501(2) 0.5234(5) 0.0486(13) Uani 1 1 d . . .
H9 H 0.2640 -0.0817 0.5820 0.058 Uiso 1 1 calc R . .
N10 N 0.2212(5) 0.04430(18) 0.3489(4) 0.0491(11) Uani 1 1 d . . .
C11 C 0.2195(6) -0.0590(2) 0.3832(5) 0.0471(13) Uani 1 1 d . . .
C12 C 0.2074(6) -0.0097(2) 0.2965(5) 0.0470(13) Uani 1 1 d . . .
C13 C 0.2696(6) 0.0049(2) 0.5776(5) 0.0457(12) Uani 1 1 d . . .
C14 C 0.2512(6) 0.0525(2) 0.4856(5) 0.0454(12) Uani 1 1 d . . .
C15 C 0.3405(17) 0.1956(4) 0.0440(9) 0.045(2) Uani 0.926(14) 1 d P A 1
C17 C 0.1788(18) 0.2719(5) -0.0952(12) 0.066(3) Uani 0.926(14) 1 d P A 1
H17 H 0.0675 0.2935 -0.1218 0.079 Uiso 0.926(14) 1 calc PR A 1
C18 C 0.342(3) 0.2833(6) -0.1506(13) 0.068(4) Uani 0.926(14) 1 d P A 1
H18 H 0.3427 0.3119 -0.2166 0.082 Uiso 0.926(14) 1 calc PR A 1
C19 C 0.5052(19) 0.2523(5) -0.1078(14) 0.069(4) Uani 0.926(14) 1 d P A 1
H19 H 0.6185 0.2603 -0.1433 0.082 Uiso 0.926(14) 1 calc PR A 1
C15A C 0.288(18) 0.198(6) 0.048(15) 0.05(4) Uiso 0.074(14) 1 d PD A 2
C19A C 0.124(13) 0.267(5) -0.104(13) 0.03(3) Uiso 0.074(14) 1 d PD A 2
H19A H 0.0126 0.2864 -0.1397 0.037 Uiso 0.074(14) 1 calc PR A 2
C18A C 0.300(18) 0.277(10) -0.15(2) 0.08(8) Uiso 0.074(14) 1 d PD A 2
H18A H 0.3026 0.3033 -0.2203 0.095 Uiso 0.074(14) 1 calc PR A 2
C17A C 0.471(17) 0.252(10) -0.09(2) 0.11(10) Uiso 0.074(14) 1 d PD A 2
H17A H 0.5868 0.2597 -0.1229 0.129 Uiso 0.074(14) 1 calc PR A 2
C16 C 0.1774(9) 0.2286(4) 0.0000(9) 0.0491(17) Uani 0.926(14) 1 d P A 1
C20 C 0.5036(15) 0.2093(4) -0.0131(10) 0.059(2) Uani 0.926(14) 1 d P A 1
H20 H 0.6166 0.1886 0.0138 0.070 Uiso 0.926(14) 1 calc PR A 1
C20A C 0.122(14) 0.225(7) -0.004(17) 0.070 Uiso 0.074(14) 1 d PD A 2
H20A H 0.0074 0.2166 0.0287 0.070 Uiso 0.074(14) 1 calc PR A 2
C16A C 0.463(15) 0.213(7) 0.015(15) 0.08(6) Uiso 0.074(14) 1 d PD A 2
C21 C 0.3498(8) 0.1461(2) 0.1433(6) 0.0546(14) Uani 1 1 d . . .
O22 O 0.1933(7) 0.1340(2) 0.1894(5) 0.0844(15) Uani 1 1 d D A .
H22 H 0.212(11) 0.099(3) 0.247(8) 0.127 Uiso 1 1 d D . .
O23 O 0.4999(7) 0.1205(2) 0.1737(6) 0.1018(19) Uani 1 1 d . A .
F24 F 0.0093(5) 0.21945(17) 0.0513(4) 0.0709(16) Uani 0.926(14) 1 d P A 1
F25 F 0.620(17) 0.179(6) 0.042(17) 0.25(7) Uiso 0.074(14) 1 d PD A 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 1.346(9) . ?
C1 C11 1.424(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.405(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(9) . ?
C3 H3 0.9300 . ?
C4 C12 1.418(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.356(9) . ?
C5 C14 1.415(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.351(9) . ?
C7 H7 0.9300 . ?
C8 C13 1.427(7) . ?
C8 H8 0.9300 . ?
C9 C13 1.383(7) . ?
C9 C11 1.387(7) . ?
C9 H9 0.9300 . ?
N10 C14 1.350(7) . ?
N10 C12 1.353(7) . ?
C11 C12 1.425(7) . ?
C13 C14 1.424(7) . ?
C15 C20 1.381(15) . ?
C15 C16 1.388(11) . ?
C15 C21 1.506(9) . ?
C17 C18 1.364(16) . ?
C17 C16 1.378(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(11) . ?
C19 H19 0.9300 . ?
C15A C16A 1.36(4) . ?
C15A C20A 1.36(4) . ?
C15A C21 1.54(10) . ?
C19A C20A 1.38(4) . ?
C19A C18A 1.39(5) . ?
C19A H19A 0.9300 . ?
C18A C17A 1.38(5) . ?
C18A H18A 0.9300 . ?
C17A C16A 1.38(4) . ?
C17A H17A 0.9300 . ?
C16 F24 1.362(8) . ?
C20 H20 0.9300 . ?
C20A H20A 0.9300 . ?
C16A F25 1.35(5) . ?
C21 O23 1.204(7) . ?
C21 O22 1.276(7) . ?
O22 H22 1.00(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 120.6(6) . . ?
C2 C1 H1 119.7 . . ?
C11 C1 H1 119.7 . . ?
C1 C2 C3 120.5(6) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.4(6) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C12 119.8(6) . . ?
C3 C4 H4 120.1 . . ?
C12 C4 H4 120.1 . . ?
C6 C5 C14 120.1(6) . . ?
C6 C5 H5 120.0 . . ?
C14 C5 H5 120.0 . . ?
C5 C6 C7 120.9(6) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 121.0(6) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C13 120.3(6) . . ?
C7 C8 H8 119.8 . . ?
C13 C8 H8 119.8 . . ?
C13 C9 C11 121.1(5) . . ?
C13 C9 H9 119.4 . . ?
C11 C9 H9 119.4 . . ?
C14 N10 C12 120.4(4) . . ?
C9 C11 C1 123.5(5) . . ?
C9 C11 C12 117.9(5) . . ?
C1 C11 C12 118.7(5) . . ?
N10 C12 C4 119.7(5) . . ?
N10 C12 C11 121.2(5) . . ?
C4 C12 C11 119.0(5) . . ?
C9 C13 C14 118.3(5) . . ?
C9 C13 C8 123.4(5) . . ?
C14 C13 C8 118.3(5) . . ?
N10 C14 C5 119.5(5) . . ?
N10 C14 C13 121.1(4) . . ?
C5 C14 C13 119.4(5) . . ?
C20 C15 C16 115.7(6) . . ?
C20 C15 C21 118.8(8) . . ?
C16 C15 C21 125.4(8) . . ?
C18 C17 C16 120.3(8) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.0(9) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 120.5(13) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C16A C15A C20A 122(5) . . ?
C16A C15A C21 100(9) . . ?
C20A C15A C21 138(9) . . ?
C20A C19A C18A 117(5) . . ?
C20A C19A H19A 121.5 . . ?
C18A C19A H19A 121.3 . . ?
C19A C18A C17A 123(5) . . ?
C19A C18A H18A 118.6 . . ?
C17A C18A H18A 118.5 . . ?
C16A C17A C18A 118(5) . . ?
C16A C17A H17A 121.1 . . ?
C18A C17A H17A 121.3 . . ?
F24 C16 C17 117.3(7) . . ?
F24 C16 C15 120.7(6) . . ?
C17 C16 C15 121.9(7) . . ?
C19 C20 C15 122.5(10) . . ?
C19 C20 H20 118.8 . . ?
C15 C20 H20 118.8 . . ?
C15A C20A C19A 120(4) . . ?
C15A C20A H20A 120.0 . . ?
C19A C20A H20A 119.9 . . ?
F25 C16A C15A 122(10) . . ?
F25 C16A C17A 114(10) . . ?
C15A C16A C17A 119(4) . . ?
O23 C21 O22 124.3(5) . . ?
O23 C21 C15A 133(5) . . ?
O22 C21 C15A 102(5) . . ?
O23 C21 C15 119.4(7) . . ?
O22 C21 C15 116.3(6) . . ?
C21 O22 H22 110(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
C11 C1 C2 C3 0.9(9) . . . . ?
C1 C2 C3 C4 -1.5(9) . . . . ?
C2 C3 C4 C12 0.5(9) . . . . ?
C14 C5 C6 C7 0.3(8) . . . . ?
C5 C6 C7 C8 -0.7(9) . . . . ?
C6 C7 C8 C13 0.1(8) . . . . ?
C13 C9 C11 C1 -179.1(4) . . . . ?
C13 C9 C11 C12 1.4(7) . . . . ?
C2 C1 C11 C9 -178.9(5) . . . . ?
C2 C1 C11 C12 0.6(7) . . . . ?
C14 N10 C12 C4 -178.8(4) . . . . ?
C14 N10 C12 C11 1.5(6) . . . . ?
C3 C4 C12 N10 -178.8(5) . . . . ?
C3 C4 C12 C11 1.0(7) . . . . ?
C9 C11 C12 N10 -2.3(7) . . . . ?
C1 C11 C12 N10 178.2(4) . . . . ?
C9 C11 C12 C4 178.0(4) . . . . ?
C1 C11 C12 C4 -1.5(7) . . . . ?
C11 C9 C13 C14 0.2(7) . . . . ?
C11 C9 C13 C8 -179.5(4) . . . . ?
C7 C8 C13 C9 -179.3(5) . . . . ?
C7 C8 C13 C14 0.9(7) . . . . ?
C12 N10 C14 C5 -179.7(4) . . . . ?
C12 N10 C14 C13 0.2(6) . . . . ?
C6 C5 C14 N10 -179.3(5) . . . . ?
C6 C5 C14 C13 0.7(7) . . . . ?
C9 C13 C14 N10 -1.1(6) . . . . ?
C8 C13 C14 N10 178.7(4) . . . . ?
C9 C13 C14 C5 178.9(4) . . . . ?
C8 C13 C14 C5 -1.3(6) . . . . ?
C16 C17 C18 C19 -2(2) . . . . ?
C17 C18 C19 C20 2(2) . . . . ?
C18 C17 C16 F24 180.0(12) . . . . ?
C18 C17 C16 C15 0.7(18) . . . . ?
C20 C15 C16 F24 -178.9(8) . . . . ?
C21 C15 C16 F24 3.3(14) . . . . ?
C20 C15 C16 C17 0.3(15) . . . . ?
C21 C15 C16 C17 -177.5(9) . . . . ?
C18 C19 C20 C15 -0.5(19) . . . . ?
C16 C15 C20 C19 -0.4(15) . . . . ?
C21 C15 C20 C19 177.5(10) . . . . ?
C21 C15A C20A C19A -171(16) . . . . ?
C20A C15A C16A F25 -166(18) . . . . ?
C21 C15A C16A F25 13(22) . . . . ?
C21 C15A C16A C17A 168(18) . . . . ?
C18A C17A C16A F25 164(23) . . . . ?
C16A C15A C21 O23 -7(18) . . . . ?
C20A C15A C21 O23 172(18) . . . . ?
C16A C15A C21 O22 173(11) . . . . ?
C20A C15A C21 O22 -8(24) . . . . ?
C16A C15A C21 C15 -7(20) . . . . ?
C20 C15 C21 O23 2.1(12) . . . . ?
C16 C15 C21 O23 179.8(9) . . . . ?
C20 C15 C21 O22 -177.7(8) . . . . ?
C16 C15 C21 O22 0.1(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.034
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047948'
_audit_update_record             
;
2015-06-25 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 Cl O2, C13 H9 N'
_chemical_formula_sum            'C20 H14 Cl N O2'
_chemical_formula_weight         335.77

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           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                   7.2762(5)
_cell_length_b                   8.8886(12)
_cell_length_c                   13.2173(14)
_cell_angle_alpha                72.108(11)
_cell_angle_beta                 82.067(7)
_cell_angle_gamma                89.098(8)
_cell_volume                     805.38(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5615
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_T_max  0.8907

_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5615
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2828
_reflns_number_gt                1848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0527P)²+0.1509P] 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     SHELXL
_refine_ls_extinction_coef       0.0070(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2828
_refine_ls_number_parameters     250
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.021
_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 0.6806(3) 0.7275(4) 1.2574(2) 0.0791(7) Uani 1 1 d . . .
H1 H 0.6348 0.7553 1.3183 0.095 Uiso 1 1 calc R . .
C2 C 0.7243(4) 0.5758(4) 1.2672(3) 0.0869(8) Uani 1 1 d . . .
H2 H 0.7092 0.5006 1.3347 0.104 Uiso 1 1 calc R . .
C3 C 0.7917(4) 0.5310(3) 1.1771(3) 0.0856(8) Uani 1 1 d . . .
H3 H 0.8195 0.4258 1.1853 0.103 Uiso 1 1 calc R . .
C4 C 0.8174(3) 0.6375(3) 1.0783(2) 0.0723(7) Uani 1 1 d . . .
H4 H 0.8624 0.6052 1.0192 0.087 Uiso 1 1 calc R . .
C5 C 0.8007(3) 1.1662(3) 0.8467(2) 0.0682(6) Uani 1 1 d . . .
H5 H 0.8519 1.1323 0.7893 0.082 Uiso 1 1 calc R . .
C6 C 0.7603(3) 1.3196(3) 0.8300(2) 0.0811(8) Uani 1 1 d . . .
H6 H 0.7844 1.3904 0.7610 0.097 Uiso 1 1 calc R . .
C7 C 0.6825(3) 1.3743(3) 0.9148(3) 0.0840(8) Uani 1 1 d . . .
H7 H 0.6544 1.4805 0.9014 0.101 Uiso 1 1 calc R . .
C8 C 0.6481(3) 1.2747(3) 1.0154(3) 0.0770(7) Uani 1 1 d . . .
H8 H 0.5970 1.3124 1.0710 0.092 Uiso 1 1 calc R . .
C9 C 0.6602(3) 1.0025(3) 1.1387(2) 0.0650(6) Uani 1 1 d . . .
H9 H 0.6103 1.0351 1.1969 0.078 Uiso 1 1 calc R . .
N10 N 0.8060(2) 0.9038(2) 0.96483(15) 0.0574(5) Uani 1 1 d . . .
C11 C 0.7041(3) 0.8454(3) 1.15490(18) 0.0586(6) Uani 1 1 d . . .
C12 C 0.7763(3) 0.7992(3) 1.06390(19) 0.0570(6) Uani 1 1 d . . .
C13 C 0.6897(3) 1.1113(3) 1.03727(19) 0.0570(6) Uani 1 1 d . . .
C14 C 0.7660(3) 1.0571(2) 0.95028(18) 0.0540(5) Uani 1 1 d . . .
C15 C 0.9761(6) 0.8011(3) 0.6283(2) 0.0549(8) Uani 0.852(3) 1 d P A 1
C15A C 0.895(2) 0.775(2) 0.6337(12) 0.045(6) Uiso 0.148(3) 1 d PD A 2
C16 C 0.9128(4) 0.7331(3) 0.5577(2) 0.0585(7) Uani 0.852(3) 1 d P A 1
C16A C 1.072(3) 0.800(3) 0.5846(16) 0.075(6) Uiso 0.148(3) 1 d PD A 2
C17 C 1.0276(6) 0.7207(5) 0.4682(3) 0.0696(9) Uani 0.852(3) 1 d P A 1
H17 H 0.9840 0.6719 0.4229 0.084 Uiso 0.852(3) 1 calc PR A 1
C17A C 1.101(4) 0.760(3) 0.4864(19) 0.078(8) Uiso 0.148(3) 1 d PD A 2
H17A H 1.2140 0.7881 0.4422 0.093 Uiso 0.148(3) 1 calc PR A 2
C18 C 1.2049(5) 0.7802(4) 0.4469(3) 0.0795(9) Uani 0.852(3) 1 d P A 1
H18 H 1.2818 0.7729 0.3864 0.095 Uiso 0.852(3) 1 calc PR A 1
C18A C 0.969(3) 0.682(3) 0.455(2) 0.086(10) Uiso 0.148(3) 1 d PD A 2
H18A H 0.9973 0.6531 0.3927 0.103 Uiso 0.148(3) 1 calc PR A 2
C19A C 0.801(3) 0.647(3) 0.5111(18) 0.112(7) Uiso 0.148(3) 1 d PD A 2
H19A H 0.7107 0.5925 0.4919 0.135 Uiso 0.148(3) 1 calc PR A 2
C19 C 1.2696(4) 0.8495(4) 0.5125(3) 0.0772(9) Uani 0.852(3) 1 d P A 1
H19 H 1.3901 0.8916 0.4968 0.093 Uiso 0.852(3) 1 calc PR A 1
C20A C 0.770(4) 0.699(3) 0.601(2) 0.124(10) Uiso 0.148(3) 1 d PD A 2
H20A H 0.6524 0.6790 0.6410 0.149 Uiso 0.148(3) 1 calc PR A 2
C20 C 1.1578(6) 0.8578(4) 0.6023(3) 0.0738(9) Uani 0.852(3) 1 d P A 1
H20 H 1.2059 0.9035 0.6480 0.089 Uiso 0.852(3) 1 calc PR A 1
C21 C 0.8552(4) 0.8159(3) 0.7290(2) 0.0738(7) Uani 1 1 d D . .
O22 O 0.9568(3) 0.8234(2) 0.79944(16) 0.0950(6) Uani 1 1 d D A .
H22 H 0.888(4) 0.848(4) 0.863(2) 0.143 Uiso 1 1 d D . .
O23 O 0.6906(3) 0.8287(3) 0.73869(19) 0.1224(8) Uani 1 1 d . A .
Cl24 Cl 0.68929(11) 0.65432(12) 0.57798(8) 0.0890(4) Uani 0.852(3) 1 d P A 1
Cl25 Cl 1.2322(10) 0.8964(9) 0.6176(6) 0.110(3) Uiso 0.148(3) 1 d P A 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 1.351(4) . ?
C1 C11 1.426(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.347(4) . ?
C3 H3 0.9300 . ?
C4 C12 1.423(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.347(3) . ?
C5 C14 1.405(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.344(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.427(3) . ?
C8 H8 0.9300 . ?
C9 C13 1.382(3) . ?
C9 C11 1.385(3) . ?
C9 H9 0.9300 . ?
N10 C12 1.344(3) . ?
N10 C14 1.349(2) . ?
C11 C12 1.419(3) . ?
C13 C14 1.420(3) . ?
C15 C20 1.382(6) . ?
C15 C16 1.387(4) . ?
C15 C21 1.531(4) . ?
C15A C20A 1.337(18) . ?
C15A C16A 1.349(17) . ?
C15A C21 1.406(14) . ?
C16 C17 1.383(4) . ?
C16 Cl24 1.734(3) . ?
C16A C17A 1.435(17) . ?
C16A Cl25 1.64(2) . ?
C17 C18 1.361(6) . ?
C17 H17 0.9300 . ?
C17A C18A 1.375(18) . ?
C17A H17A 0.9300 . ?
C18 C19 1.342(4) . ?
C18 H18 0.9300 . ?
C18A C19A 1.327(18) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.384(18) . ?
C19A H19A 0.9300 . ?
C19 C20 1.364(4) . ?
C19 H19 0.9300 . ?
C20A H20A 0.9300 . ?
C20 H20 0.9300 . ?
C21 O23 1.194(3) . ?
C21 O22 1.284(3) . ?
O22 H22 1.006(18) . ?

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 C11 120.7(3) . . ?
C2 C1 H1 119.6 . . ?
C11 C1 H1 119.6 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C12 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C12 C4 H4 119.8 . . ?
C6 C5 C14 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C14 C5 H5 119.8 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C13 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C13 C8 H8 119.8 . . ?
C13 C9 C11 120.9(2) . . ?
C13 C9 H9 119.5 . . ?
C11 C9 H9 119.5 . . ?
C12 N10 C14 119.75(17) . . ?
C9 C11 C12 117.9(2) . . ?
C9 C11 C1 123.9(2) . . ?
C12 C11 C1 118.1(2) . . ?
N10 C12 C11 121.78(19) . . ?
N10 C12 C4 119.3(2) . . ?
C11 C12 C4 118.9(2) . . ?
C9 C13 C14 118.01(19) . . ?
C9 C13 C8 123.6(2) . . ?
C14 C13 C8 118.4(2) . . ?
N10 C14 C5 119.40(19) . . ?
N10 C14 C13 121.6(2) . . ?
C5 C14 C13 119.0(2) . . ?
C20 C15 C16 116.0(3) . . ?
C20 C15 C21 120.8(3) . . ?
C16 C15 C21 123.3(3) . . ?
C20A C15A C16A 121.6(19) . . ?
C20A C15A C21 121.7(16) . . ?
C16A C15A C21 116.3(15) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 Cl24 116.3(3) . . ?
C15 C16 Cl24 122.4(3) . . ?
C15A C16A C17A 113(2) . . ?
C15A C16A Cl25 124.8(16) . . ?
C17A C16A Cl25 121.0(18) . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C18A C17A C16A 123(3) . . ?
C18A C17A H17A 118.6 . . ?
C16A C17A H17A 118.6 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C19A C18A C17A 121(3) . . ?
C19A C18A H18A 119.3 . . ?
C17A C18A H18A 119.3 . . ?
C18A C19A C20A 115(3) . . ?
C18A C19A H19A 122.5 . . ?
C20A C19A H19A 122.5 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15A C20A C19A 125(3) . . ?
C15A C20A H20A 117.4 . . ?
C19A C20A H20A 117.4 . . ?
C19 C20 C15 122.7(4) . . ?
C19 C20 H20 118.6 . . ?
C15 C20 H20 118.6 . . ?
O23 C21 O22 124.3(3) . . ?
O23 C21 C15A 103.3(7) . . ?
O22 C21 C15A 132.1(7) . . ?
O23 C21 C15 125.1(3) . . ?
O22 C21 C15 110.4(3) . . ?
C21 O22 H22 114(2) . . ?

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
C11 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C12 0.1(4) . . . . ?
C14 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C13 -0.3(4) . . . . ?
C13 C9 C11 C12 -1.4(3) . . . . ?
C13 C9 C11 C1 178.8(2) . . . . ?
C2 C1 C11 C9 179.2(2) . . . . ?
C2 C1 C11 C12 -0.7(3) . . . . ?
C14 N10 C12 C11 -0.3(3) . . . . ?
C14 N10 C12 C4 179.47(18) . . . . ?
C9 C11 C12 N10 1.5(3) . . . . ?
C1 C11 C12 N10 -178.62(19) . . . . ?
C9 C11 C12 C4 -178.27(19) . . . . ?
C1 C11 C12 C4 1.6(3) . . . . ?
C3 C4 C12 N10 178.9(2) . . . . ?
C3 C4 C12 C11 -1.3(3) . . . . ?
C11 C9 C13 C14 0.1(3) . . . . ?
C11 C9 C13 C8 -179.8(2) . . . . ?
C7 C8 C13 C9 179.2(2) . . . . ?
C7 C8 C13 C14 -0.6(3) . . . . ?
C12 N10 C14 C5 178.87(18) . . . . ?
C12 N10 C14 C13 -1.0(3) . . . . ?
C6 C5 C14 N10 179.4(2) . . . . ?
C6 C5 C14 C13 -0.7(3) . . . . ?
C9 C13 C14 N10 1.2(3) . . . . ?
C8 C13 C14 N10 -178.98(19) . . . . ?
C9 C13 C14 C5 -178.74(19) . . . . ?
C8 C13 C14 C5 1.1(3) . . . . ?
C20 C15 C16 C17 1.3(4) . . . . ?
C21 C15 C16 C17 -179.3(3) . . . . ?
C20 C15 C16 Cl24 179.5(2) . . . . ?
C21 C15 C16 Cl24 -1.1(4) . . . . ?
C20A C15A C16A C17A 9(3) . . . . ?
C21 C15A C16A C17A -178.3(16) . . . . ?
C20A C15A C16A Cl25 178.1(19) . . . . ?
C21 C15A C16A Cl25 -10(3) . . . . ?
C15 C16 C17 C18 -1.9(4) . . . . ?
Cl24 C16 C17 C18 179.8(2) . . . . ?
C15A C16A C17A C18A -9(4) . . . . ?
Cl25 C16A C17A C18A -179(2) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C16A C17A C18A C19A 4(5) . . . . ?
C17A C18A C19A C20A 2(4) . . . . ?
C17 C18 C19 C20 1.2(5) . . . . ?
C16A C15A C20A C19A -5(4) . . . . ?
C21 C15A C20A C19A -176(2) . . . . ?
C18A C19A C20A C15A -2(4) . . . . ?
C18 C19 C20 C15 -1.8(5) . . . . ?
C16 C15 C20 C19 0.5(4) . . . . ?
C21 C15 C20 C19 -178.9(3) . . . . ?
C20A C15A C21 O23 -27(2) . . . . ?
C16A C15A C21 O23 160.3(15) . . . . ?
C20A C15A C21 O22 145.5(17) . . . . ?
C16A C15A C21 O22 -27(2) . . . . ?
C20A C15A C21 C15 176(3) . . . . ?
C16A C15A C21 C15 3.4(11) . . . . ?
C20 C15 C21 O23 149.9(3) . . . . ?
C16 C15 C21 O23 -29.5(4) . . . . ?
C20 C15 C21 O22 -25.7(3) . . . . ?
C16 C15 C21 O22 155.0(2) . . . . ?
C20 C15 C21 C15A 178(2) . . . . ?
C16 C15 C21 C15A -1.6(18) . . . . ?


_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.028
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047949'
_audit_update_record             
;
2015-06-25 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 Br O2, C13 H9 N'
_chemical_formula_sum            'C20 H14 Br N O2'
_chemical_formula_weight         380.23

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'
Br Br -0.2901 2.4595 '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                   7.3546(8)
_cell_length_b                   8.9384(10)
_cell_length_c                   13.2163(16)
_cell_angle_alpha                72.725(10)
_cell_angle_beta                 80.733(10)
_cell_angle_gamma                88.490(9)
_cell_volume                     818.59(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5555
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            light-brown
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    2.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5542
_exptl_absorpt_correction_T_max  0.8790
_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5555
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2879
_reflns_number_gt                2199
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_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)+(0.0776P)²+0.0775P] 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         2879
_refine_ls_number_parameters     249
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_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
C1 C 0.6874(6) 0.7258(5) 0.7620(4) 0.0692(11) Uani 1 1 d . . .
H1 H 0.6423 0.7533 0.8237 0.083 Uiso 1 1 calc R . .
C2 C 0.7336(6) 0.5773(5) 0.7694(4) 0.0787(14) Uani 1 1 d . . .
H2 H 0.7216 0.5029 0.8365 0.094 Uiso 1 1 calc R . .
C3 C 0.7997(7) 0.5327(5) 0.6775(5) 0.0790(14) Uani 1 1 d . . .
H3 H 0.8287 0.4286 0.6845 0.095 Uiso 1 1 calc R . .
C4 C 0.8224(6) 0.6380(5) 0.5784(4) 0.0714(12) Uani 1 1 d . . .
H4 H 0.8662 0.6061 0.5182 0.086 Uiso 1 1 calc R . .
C5 C 0.7976(6) 1.1619(5) 0.3518(4) 0.0672(11) Uani 1 1 d . . .
H5 H 0.8492 1.1291 0.2932 0.081 Uiso 1 1 calc R . .
C6 C 0.7542(6) 1.3136(5) 0.3383(4) 0.0770(13) Uani 1 1 d . . .
H6 H 0.7765 1.3846 0.2699 0.092 Uiso 1 1 calc R . .
C7 C 0.6762(7) 1.3666(5) 0.4251(5) 0.0799(14) Uani 1 1 d . . .
H7 H 0.6468 1.4716 0.4131 0.096 Uiso 1 1 calc R . .
C8 C 0.6433(6) 1.2673(5) 0.5259(5) 0.0732(13) Uani 1 1 d . . .
H8 H 0.5917 1.3039 0.5828 0.088 Uiso 1 1 calc R . .
C9 C 0.6610(5) 0.9972(5) 0.6455(4) 0.0600(10) Uani 1 1 d . . .
H9 H 0.6109 1.0288 0.7049 0.072 Uiso 1 1 calc R . .
N10 N 0.8068(4) 0.9023(3) 0.4677(3) 0.0566(8) Uani 1 1 d . . .
C11 C 0.7073(5) 0.8423(4) 0.6592(3) 0.0549(9) Uani 1 1 d . . .
C12 C 0.7787(5) 0.7980(4) 0.5667(3) 0.0532(9) Uani 1 1 d . . .
C13 C 0.6879(5) 1.1057(4) 0.5448(3) 0.0535(9) Uani 1 1 d . . .
C14 C 0.7641(5) 1.0533(4) 0.4559(3) 0.0514(9) Uani 1 1 d . . .
C15 C 0.9774(6) 0.8022(4) 0.1279(3) 0.0504(10) Uani 0.928(2) 1 d P A 1
C15A C 0.862(11) 0.741(12) 0.136(7) 0.152(14) Uiso 0.072(2) 1 d PDU A 2
C16 C 0.9170(5) 0.7325(4) 0.0577(3) 0.0506(9) Uani 0.928(2) 1 d P A 1
C20A C 0.745(8) 0.690(9) 0.079(8) 0.152(14) Uiso 0.072(2) 1 d PDU A 2
H20A H 0.6177 0.6985 0.0942 0.183 Uiso 0.072(2) 1 calc PR A 2
C17 C 1.0299(7) 0.7217(5) -0.0329(4) 0.0617(11) Uani 0.928(2) 1 d P A 1
H17 H 0.9872 0.6713 -0.0771 0.074 Uiso 0.928(2) 1 calc PR A 1
C19A C 0.827(13) 0.627(11) -0.001(8) 0.152(14) Uiso 0.072(2) 1 d PDU A 2
H19A H 0.7632 0.5553 -0.0213 0.183 Uiso 0.072(2) 1 calc PR A 2
C18 C 1.2038(7) 0.7842(5) -0.0589(4) 0.0666(12) Uani 0.928(2) 1 d P A 1
H18 H 1.2787 0.7777 -0.1212 0.080 Uiso 0.928(2) 1 calc PR A 1
C18A C 1.005(14) 0.674(15) -0.048(9) 0.152(14) Uiso 0.072(2) 1 d PDU A 2
H18A H 1.0657 0.6309 -0.1001 0.183 Uiso 0.072(2) 1 calc PR A 2
C19 C 1.2689(6) 0.8566(5) 0.0062(4) 0.0684(12) Uani 0.928(2) 1 d P A 1
H19 H 1.3875 0.9000 -0.0112 0.082 Uiso 0.928(2) 1 calc PR A 1
C17A C 1.092(10) 0.784(12) -0.018(9) 0.152(14) Uiso 0.072(2) 1 d PDU A 2
H17A H 1.1853 0.8485 -0.0653 0.183 Uiso 0.072(2) 1 calc PR A 2
C20 C 1.1558(9) 0.8638(6) 0.0977(4) 0.0696(14) Uani 0.928(2) 1 d PD A 1
H20 H 1.2011 0.9126 0.1419 0.084 Uiso 0.928(2) 1 calc PR A 1
C16A C 1.037(9) 0.796(14) 0.085(10) 0.152(14) Uiso 0.072(2) 1 d PDU A 2
C21 C 0.8630(7) 0.8175(5) 0.2289(4) 0.0662(11) Uani 1 1 d . . .
O22 O 0.9640(5) 0.8251(4) 0.2993(3) 0.0917(11) Uani 1 1 d D A .
H22 H 0.877(7) 0.845(8) 0.357(4) 0.138 Uiso 1 1 d D . .
O23 O 0.6985(6) 0.8313(6) 0.2406(3) 0.1139(14) Uani 1 1 d . A .
Br24 Br 0.67713(6) 0.64397(6) 0.08401(4) 0.0774(3) Uani 0.928(2) 1 d PD A 1
Br25 Br 1.2339(14) 0.8925(11) 0.1135(9) 0.097(4) Uiso 0.072(2) 1 d P A 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 1.341(6) . ?
C1 C11 1.434(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.399(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(7) . ?
C3 H3 0.9300 . ?
C4 C12 1.425(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.351(6) . ?
C5 C14 1.417(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.352(7) . ?
C7 H7 0.9300 . ?
C8 C13 1.429(6) . ?
C8 H8 0.9300 . ?
C9 C13 1.382(6) . ?
C9 C11 1.383(5) . ?
C9 H9 0.9300 . ?
N10 C14 1.346(4) . ?
N10 C12 1.351(5) . ?
C11 C12 1.413(5) . ?
C13 C14 1.419(5) . ?
C15 C20 1.387(8) . ?
C15 C16 1.391(6) . ?
C15 C21 1.499(6) . ?
C15A C16A 1.381(18) . ?
C15A C20A 1.39(2) . ?
C15A C21 1.58(7) . ?
C16 C17 1.371(6) . ?
C16 Br24 1.890(4) . ?
C20A C19A 1.388(19) . ?
C20A H20A 0.9300 . ?
C17 C18 1.359(7) . ?
C17 H17 0.9300 . ?
C19A C18A 1.376(18) . ?
C19A H19A 0.9300 . ?
C18 C19 1.367(7) . ?
C18 H18 0.9300 . ?
C18A C17A 1.37(2) . ?
C18A H18A 0.9300 . ?
C19 C20 1.370(7) . ?
C19 H19 0.9300 . ?
C17A C16A 1.392(19) . ?
C17A H17A 0.9300 . ?
C20 H20 0.9300 . ?
C16A Br25 1.85(2) . ?
C21 O23 1.202(6) . ?
C21 O22 1.299(5) . ?
O22 H22 0.97(2) . ?

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 C11 120.2(4) . . ?
C2 C1 H1 119.9 . . ?
C11 C1 H1 119.9 . . ?
C1 C2 C3 120.9(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C12 119.7(5) . . ?
C3 C4 H4 120.1 . . ?
C12 C4 H4 120.1 . . ?
C6 C5 C14 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C14 C5 H5 120.3 . . ?
C5 C6 C7 121.6(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C13 119.8(5) . . ?
C7 C8 H8 120.1 . . ?
C13 C8 H8 120.1 . . ?
C13 C9 C11 121.0(4) . . ?
C13 C9 H9 119.5 . . ?
C11 C9 H9 119.5 . . ?
C14 N10 C12 119.3(3) . . ?
C9 C11 C12 117.9(4) . . ?
C9 C11 C1 123.4(4) . . ?
C12 C11 C1 118.8(4) . . ?
N10 C12 C11 122.1(3) . . ?
N10 C12 C4 119.0(4) . . ?
C11 C12 C4 119.0(4) . . ?
C9 C13 C14 118.0(3) . . ?
C9 C13 C8 123.4(4) . . ?
C14 C13 C8 118.6(4) . . ?
N10 C14 C5 118.7(4) . . ?
N10 C14 C13 121.8(3) . . ?
C5 C14 C13 119.6(3) . . ?
C20 C15 C16 115.4(4) . . ?
C20 C15 C21 119.7(4) . . ?
C16 C15 C21 124.8(4) . . ?
C16A C15A C20A 119.4(19) . . ?
C16A C15A C21 94(5) . . ?
C20A C15A C21 142(6) . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 Br24 116.6(3) . . ?
C15 C16 Br24 121.8(3) . . ?
C19A C20A C15A 117(2) . . ?
C19A C20A H20A 121.6 . . ?
C15A C20A H20A 121.6 . . ?
C18 C17 C16 120.5(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C18A C19A C20A 117.9(18) . . ?
C18A C19A H19A 121.1 . . ?
C20A C19A H19A 121.1 . . ?
C17 C18 C19 120.2(5) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C17A C18A C19A 119(2) . . ?
C17A C18A H18A 120.3 . . ?
C19A C18A H18A 120.3 . . ?
C18 C19 C20 118.6(5) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C18A C17A C16A 118(2) . . ?
C18A C17A H17A 120.8 . . ?
C16A C17A H17A 120.8 . . ?
C19 C20 C15 123.5(5) . . ?
C19 C20 H20 118.2 . . ?
C15 C20 H20 118.2 . . ?
C15A C16A C17A 117.0(19) . . ?
C15A C16A Br25 138(6) . . ?
C17A C16A Br25 105(6) . . ?
O23 C21 O22 123.9(4) . . ?
O23 C21 C15 124.0(4) . . ?
O22 C21 C15 111.9(4) . . ?
O23 C21 C15A 93(3) . . ?
O22 C21 C15A 140(4) . . ?
C15 C21 C15A 38(3) . . ?
C21 O22 H22 104(4) . . ?

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
C11 C1 C2 C3 -0.8(6) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C2 C3 C4 C12 0.1(7) . . . . ?
C14 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 0.6(7) . . . . ?
C6 C7 C8 C13 -0.1(7) . . . . ?
C13 C9 C11 C12 -1.5(5) . . . . ?
C13 C9 C11 C1 178.1(3) . . . . ?
C2 C1 C11 C9 179.4(4) . . . . ?
C2 C1 C11 C12 -0.9(6) . . . . ?
C14 N10 C12 C11 -0.6(5) . . . . ?
C14 N10 C12 C4 179.3(3) . . . . ?
C9 C11 C12 N10 1.8(5) . . . . ?
C1 C11 C12 N10 -177.9(3) . . . . ?
C9 C11 C12 C4 -178.1(3) . . . . ?
C1 C11 C12 C4 2.2(5) . . . . ?
C3 C4 C12 N10 178.2(4) . . . . ?
C3 C4 C12 C11 -1.8(6) . . . . ?
C11 C9 C13 C14 0.2(5) . . . . ?
C11 C9 C13 C8 -179.8(4) . . . . ?
C7 C8 C13 C9 179.1(4) . . . . ?
C7 C8 C13 C14 -0.8(6) . . . . ?
C12 N10 C14 C5 178.8(3) . . . . ?
C12 N10 C14 C13 -0.8(5) . . . . ?
C6 C5 C14 N10 179.4(4) . . . . ?
C6 C5 C14 C13 -0.9(5) . . . . ?
C9 C13 C14 N10 1.1(5) . . . . ?
C8 C13 C14 N10 -179.0(3) . . . . ?
C9 C13 C14 C5 -178.5(3) . . . . ?
C8 C13 C14 C5 1.4(5) . . . . ?
C20 C15 C16 C17 2.0(6) . . . . ?
C21 C15 C16 C17 -179.6(4) . . . . ?
C20 C15 C16 Br24 -179.3(3) . . . . ?
C21 C15 C16 Br24 -0.9(5) . . . . ?
C16A C15A C20A C19A 30(12) . . . . ?
C21 C15A C20A C19A -180(12) . . . . ?
C15 C16 C17 C18 -2.2(6) . . . . ?
Br24 C16 C17 C18 179.0(3) . . . . ?
C15A C20A C19A C18A -26(12) . . . . ?
C16 C17 C18 C19 1.0(7) . . . . ?
C20A C19A C18A C17A -2(15) . . . . ?
C17 C18 C19 C20 0.3(7) . . . . ?
C19A C18A C17A C16A 27(14) . . . . ?
C18 C19 C20 C15 -0.4(7) . . . . ?
C16 C15 C20 C19 -0.8(6) . . . . ?
C21 C15 C20 C19 -179.3(4) . . . . ?
C20A C15A C16A C17A -6(16) . . . . ?
C21 C15A C16A C17A -168(10) . . . . ?
C20A C15A C16A Br25 172(10) . . . . ?
C21 C15A C16A Br25 10(15) . . . . ?
C18A C17A C16A C15A -22(14) . . . . ?
C18A C17A C16A Br25 158(9) . . . . ?
C20 C15 C21 O23 147.4(5) . . . . ?
C16 C15 C21 O23 -31.0(7) . . . . ?
C20 C15 C21 O22 -28.1(5) . . . . ?
C16 C15 C21 O22 153.6(4) . . . . ?
C20 C15 C21 C15A -175(7) . . . . ?
C16 C15 C21 C15A 7(7) . . . . ?
C16A C15A C21 O23 151(7) . . . . ?
C20A C15A C21 O23 -3(13) . . . . ?
C16A C15A C21 O22 -52(9) . . . . ?
C20A C15A C21 O22 154(9) . . . . ?
C16A C15A C21 C15 1(6) . . . . ?
C20A C15A C21 C15 -152(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.060

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047950'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C7 H5 I O2'
_chemical_formula_sum            'C20 H14 I N O2'
_chemical_formula_weight         427.22

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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 '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                   7.7648(9)
_cell_length_b                   8.6946(9)
_cell_length_c                   13.3033(14)
_cell_angle_alpha                74.823(8)
_cell_angle_beta                 86.113(9)
_cell_angle_gamma                82.446(9)
_cell_volume                     858.76(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5757
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            light-brown
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    1.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_T_max  0.9805

_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5757
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3008
_reflns_number_gt                2593
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_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)+(0.0726P)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         3008
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.1477(7) 0.2567(6) 0.9304(5) 0.0612(14) Uani 1 1 d . . .
H1 H 0.1482 0.1617 0.9827 0.073 Uiso 1 1 calc R . .
C2 C 0.1021(9) 0.2611(8) 0.8326(6) 0.0759(19) Uani 1 1 d . . .
H2 H 0.0724 0.1688 0.8185 0.091 Uiso 1 1 calc R . .
C3 C 0.0993(8) 0.4065(8) 0.7514(5) 0.0701(16) Uani 1 1 d . . .
H3 H 0.0688 0.4083 0.6846 0.084 Uiso 1 1 calc R . .
C4 C 0.1409(7) 0.5411(7) 0.7717(4) 0.0599(13) Uani 1 1 d . . .
H4 H 0.1377 0.6354 0.7186 0.072 Uiso 1 1 calc R . .
C5 C 0.3239(7) 0.8223(6) 1.0019(4) 0.0560(13) Uani 1 1 d . . .
H5 H 0.3185 0.9154 0.9478 0.067 Uiso 1 1 calc R . .
C6 C 0.3728(8) 0.8237(7) 1.0982(5) 0.0651(15) Uani 1 1 d . . .
H6 H 0.3982 0.9192 1.1096 0.078 Uiso 1 1 calc R . .
C7 C 0.3854(8) 0.6838(7) 1.1806(5) 0.0672(15) Uani 1 1 d . . .
H7 H 0.4224 0.6868 1.2450 0.081 Uiso 1 1 calc R . .
C8 C 0.3442(7) 0.5458(7) 1.1665(4) 0.0575(13) Uani 1 1 d . . .
H8 H 0.3502 0.4546 1.2220 0.069 Uiso 1 1 calc R . .
C9 C 0.2470(6) 0.3961(5) 1.0509(4) 0.0485(11) Uani 1 1 d . . .
H9 H 0.2523 0.3026 1.1047 0.058 Uiso 1 1 calc R . .
N10 N 0.2318(5) 0.6775(5) 0.8892(3) 0.0464(9) Uani 1 1 d . . .
C11 C 0.1945(6) 0.3955(5) 0.9530(4) 0.0472(11) Uani 1 1 d . . .
C12 C 0.1892(6) 0.5409(6) 0.8723(4) 0.0460(11) Uani 1 1 d . . .
C13 C 0.2914(6) 0.5368(5) 1.0681(4) 0.0456(10) Uani 1 1 d . . .
C14 C 0.2810(6) 0.6767(5) 0.9848(4) 0.0433(10) Uani 1 1 d . . .
C15 C 0.4726(6) 1.0788(5) 0.6201(3) 0.0406(10) Uani 1 1 d . . .
C16 C 0.6381(6) 1.1220(5) 0.5870(4) 0.0468(11) Uani 1 1 d . . .
C17 C 0.6625(8) 1.2458(7) 0.5013(4) 0.0630(14) Uani 1 1 d . . .
H17 H 0.7740 1.2720 0.4803 0.076 Uiso 1 1 calc R . .
C18 C 0.5223(9) 1.3310(7) 0.4464(4) 0.0675(16) Uani 1 1 d . . .
H18 H 0.5390 1.4155 0.3884 0.081 Uiso 1 1 calc R . .
C19 C 0.3574(9) 1.2925(7) 0.4764(5) 0.0675(15) Uani 1 1 d . . .
H19 H 0.2624 1.3502 0.4391 0.081 Uiso 1 1 calc R . .
C20 C 0.3344(7) 1.1674(6) 0.5623(4) 0.0519(12) Uani 1 1 d . . .
H20 H 0.2225 1.1414 0.5822 0.062 Uiso 1 1 calc R . .
C21 C 0.4352(6) 0.9453(6) 0.7143(4) 0.0465(11) Uani 1 1 d . . .
O22 O 0.2745(5) 0.9199(4) 0.7276(3) 0.0588(9) Uani 1 1 d D . .
H22 H 0.260(8) 0.826(4) 0.786(3) 0.071 Uiso 1 1 d D . .
O23 O 0.5463(6) 0.8744(6) 0.7732(4) 0.0934(16) Uani 1 1 d . . .
I24 I 0.87088(4) 1.00359(5) 0.65946(3) 0.0669(2) Uani 1 1 d . . .


_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 1.361(9) . ?
C1 C11 1.414(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.431(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(8) . ?
C3 H3 0.9300 . ?
C4 C12 1.414(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(8) . ?
C5 C14 1.426(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.344(7) . ?
C7 H7 0.9300 . ?
C8 C13 1.421(7) . ?
C8 H8 0.9300 . ?
C9 C13 1.392(6) . ?
C9 C11 1.392(7) . ?
C9 H9 0.9300 . ?
N10 C14 1.351(6) . ?
N10 C12 1.351(6) . ?
C11 C12 1.425(7) . ?
C13 C14 1.413(7) . ?
C15 C20 1.385(7) . ?
C15 C16 1.397(6) . ?
C15 C21 1.510(6) . ?
C16 C17 1.370(7) . ?
C16 I24 2.117(5) . ?
C17 C18 1.371(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O23 1.199(6) . ?
C21 O22 1.288(6) . ?
O22 H22 0.98(2) . ?

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 C11 120.5(6) . . ?
C2 C1 H1 119.8 . . ?
C11 C1 H1 119.8 . . ?
C1 C2 C3 120.5(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C12 121.0(5) . . ?
C3 C4 H4 119.5 . . ?
C12 C4 H4 119.5 . . ?
C6 C5 C14 119.5(5) . . ?
C6 C5 H5 120.3 . . ?
C14 C5 H5 120.3 . . ?
C5 C6 C7 121.3(5) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C13 121.1(5) . . ?
C7 C8 H8 119.4 . . ?
C13 C8 H8 119.4 . . ?
C13 C9 C11 119.9(4) . . ?
C13 C9 H9 120.1 . . ?
C11 C9 H9 120.1 . . ?
C14 N10 C12 119.3(4) . . ?
C9 C11 C1 122.7(5) . . ?
C9 C11 C12 118.4(4) . . ?
C1 C11 C12 118.9(5) . . ?
N10 C12 C4 119.2(4) . . ?
N10 C12 C11 121.7(4) . . ?
C4 C12 C11 119.1(4) . . ?
C9 C13 C14 118.6(4) . . ?
C9 C13 C8 122.6(4) . . ?
C14 C13 C8 118.8(4) . . ?
N10 C14 C13 122.2(4) . . ?
N10 C14 C5 118.7(4) . . ?
C13 C14 C5 119.1(4) . . ?
C20 C15 C16 116.9(4) . . ?
C20 C15 C21 118.6(4) . . ?
C16 C15 C21 124.6(4) . . ?
C17 C16 C15 121.5(5) . . ?
C17 C16 I24 114.1(4) . . ?
C15 C16 I24 124.4(3) . . ?
C16 C17 C18 119.9(5) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.4(5) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 119.2(6) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C15 122.1(5) . . ?
C19 C20 H20 118.9 . . ?
C15 C20 H20 118.9 . . ?
O23 C21 O22 123.6(5) . . ?
O23 C21 C15 121.9(4) . . ?
O22 C21 C15 114.4(4) . . ?
C21 O22 H22 111(4) . . ?

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
C11 C1 C2 C3 -0.5(9) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C2 C3 C4 C12 0.6(9) . . . . ?
C14 C5 C6 C7 1.4(8) . . . . ?
C5 C6 C7 C8 -2.0(9) . . . . ?
C6 C7 C8 C13 1.6(9) . . . . ?
C13 C9 C11 C1 180.0(4) . . . . ?
C13 C9 C11 C12 0.4(7) . . . . ?
C2 C1 C11 C9 -178.1(5) . . . . ?
C2 C1 C11 C12 1.4(8) . . . . ?
C14 N10 C12 C4 -178.8(5) . . . . ?
C14 N10 C12 C11 0.1(7) . . . . ?
C3 C4 C12 N10 179.2(5) . . . . ?
C3 C4 C12 C11 0.3(8) . . . . ?
C9 C11 C12 N10 -0.7(7) . . . . ?
C1 C11 C12 N10 179.8(4) . . . . ?
C9 C11 C12 C4 178.2(5) . . . . ?
C1 C11 C12 C4 -1.3(7) . . . . ?
C11 C9 C13 C14 0.3(7) . . . . ?
C11 C9 C13 C8 179.3(5) . . . . ?
C7 C8 C13 C9 -179.7(5) . . . . ?
C7 C8 C13 C14 -0.7(8) . . . . ?
C12 N10 C14 C13 0.7(7) . . . . ?
C12 N10 C14 C5 -179.3(4) . . . . ?
C9 C13 C14 N10 -0.9(7) . . . . ?
C8 C13 C14 N10 -179.9(4) . . . . ?
C9 C13 C14 C5 179.1(4) . . . . ?
C8 C13 C14 C5 0.1(7) . . . . ?
C6 C5 C14 N10 179.6(5) . . . . ?
C6 C5 C14 C13 -0.4(7) . . . . ?
C20 C15 C16 C17 -0.2(7) . . . . ?
C21 C15 C16 C17 -179.3(4) . . . . ?
C20 C15 C16 I24 -178.7(3) . . . . ?
C21 C15 C16 I24 2.1(6) . . . . ?
C15 C16 C17 C18 0.4(8) . . . . ?
I24 C16 C17 C18 179.2(4) . . . . ?
C16 C17 C18 C19 -0.4(9) . . . . ?
C17 C18 C19 C20 0.1(9) . . . . ?
C18 C19 C20 C15 0.2(8) . . . . ?
C16 C15 C20 C19 -0.2(7) . . . . ?
C21 C15 C20 C19 179.0(5) . . . . ?
C20 C15 C21 O23 -172.7(6) . . . . ?
C16 C15 C21 O23 6.4(8) . . . . ?
C20 C15 C21 O22 4.5(6) . . . . ?
C16 C15 C21 O22 -176.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.309
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.111
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047951'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C7 H5 F O2'
_chemical_formula_sum            'C20 H14 F N O2'
_chemical_formula_weight         319.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   6.889(2)
_cell_length_b                   8.789(2)
_cell_length_c                   13.861(5)
_cell_angle_alpha                74.83(3)
_cell_angle_beta                 79.38(3)
_cell_angle_gamma                80.60(2)
_cell_volume                     790.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4881
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            light-orange
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9183
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4881
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2766
_reflns_number_gt                1871
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_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)+(0.0670P)²+0.0461P] 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     SHELXL
_refine_ls_extinction_coef       0.0161(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2766
_refine_ls_number_parameters     234
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.1413(3) 1.3109(2) 0.60331(19) 0.0609(6) Uani 1 1 d . . .
H1 H 0.1354 1.4059 0.5541 0.073 Uiso 1 1 calc R . .
C2 C 0.1077(3) 1.3145(3) 0.7022(2) 0.0706(7) Uani 1 1 d . . .
H2 H 0.0793 1.4115 0.7201 0.085 Uiso 1 1 calc R . .
C3 C 0.1155(3) 1.1734(3) 0.77737(18) 0.0691(6) Uani 1 1 d . . .
H3 H 0.0933 1.1773 0.8450 0.083 Uiso 1 1 calc R . .
C4 C 0.1549(3) 1.0318(2) 0.75306(16) 0.0580(5) Uani 1 1 d . . .
H4 H 0.1580 0.9390 0.8041 0.070 Uiso 1 1 calc R . .
C5 C 0.3123(3) 0.7181(2) 0.50897(18) 0.0578(5) Uani 1 1 d . . .
H5 H 0.3165 0.6271 0.5614 0.069 Uiso 1 1 calc R . .
C6 C 0.3470(3) 0.7047(3) 0.4121(2) 0.0667(6) Uani 1 1 d . . .
H6 H 0.3734 0.6043 0.3988 0.080 Uiso 1 1 calc R . .
C7 C 0.3440(3) 0.8396(3) 0.33147(19) 0.0704(7) Uani 1 1 d . . .
H7 H 0.3689 0.8282 0.2653 0.085 Uiso 1 1 calc R . .
C8 C 0.3051(3) 0.9856(3) 0.34936(16) 0.0598(6) Uani 1 1 d . . .
H8 H 0.3040 1.0744 0.2953 0.072 Uiso 1 1 calc R . .
C9 C 0.2240(2) 1.1524(2) 0.47357(15) 0.0493(5) Uani 1 1 d . . .
H9 H 0.2217 1.2441 0.4216 0.059 Uiso 1 1 calc R . .
N10 N 0.2331(2) 0.87892(17) 0.62877(12) 0.0468(4) Uani 1 1 d . . .
C11 C 0.1854(2) 1.1652(2) 0.57326(14) 0.0450(5) Uani 1 1 d . . .
C12 C 0.1920(2) 1.0222(2) 0.65043(14) 0.0440(5) Uani 1 1 d . . .
C13 C 0.2656(2) 1.0060(2) 0.45011(14) 0.0452(5) Uani 1 1 d . . .
C14 C 0.2696(2) 0.8687(2) 0.53118(14) 0.0439(5) Uani 1 1 d . . .
C15 C 0.4334(3) 0.4285(2) 0.88501(15) 0.0554(5) Uani 1 1 d . B .
C16 C 0.6148(3) 0.3466(3) 0.90367(17) 0.0707(6) Uani 1 1 d . . .
H16 H 0.7297 0.3730 0.8593 0.085 Uiso 1 1 calc R A 1
C17 C 0.6244(10) 0.2274(6) 0.9872(4) 0.0765(16) Uani 0.870(6) 1 d PD B 1
C19 C 0.2844(7) 0.2621(6) 1.0357(3) 0.0851(15) Uani 0.870(6) 1 d PD B 1
H19 H 0.1710 0.2329 1.0805 0.102 Uiso 0.870(6) 1 d PR B 1
C19A C 0.640(12) 0.191(3) 0.989(5) 0.14(3) Uiso 0.130(6) 1 d PD B 2
H19A H 0.7545 0.1193 0.9948 0.163 Uiso 0.130(6) 1 calc PR B 2
C17A C 0.292(10) 0.260(10) 1.013(2) 0.20(4) Uiso 0.130(6) 1 d PD B 2
C18 C 0.4638(5) 0.1808(3) 1.0529(2) 0.0896(8) Uani 1 1 d . . .
H18 H 0.4756 0.0953 1.1085 0.107 Uiso 1 1 calc R B 1
C20 C 0.2656(4) 0.3867(3) 0.95112(19) 0.0741(7) Uani 1 1 d . . .
H20 H 0.1412 0.4409 0.9395 0.089 Uiso 1 1 calc R B 1
C21 C 0.4252(3) 0.5611(2) 0.79251(16) 0.0598(6) Uani 1 1 d . . .
O22 O 0.2493(2) 0.63467(17) 0.78228(12) 0.0750(5) Uani 1 1 d D B .
H22 H 0.249(4) 0.725(3) 0.7218(16) 0.113 Uiso 1 1 d D . .
O23 O 0.5724(3) 0.59341(19) 0.73258(13) 0.0917(6) Uani 1 1 d . B .
F24 F 0.8019(3) 0.1454(3) 1.00586(15) 0.1355(12) Uani 0.870(6) 1 d P B 1
F25 F 0.165(3) 0.223(2) 1.0917(18) 0.170(9) Uiso 0.130(6) 1 d PD B 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 1.356(3) . ?
C1 C11 1.418(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.346(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.421(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.352(3) . ?
C5 C14 1.409(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.345(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.425(3) . ?
C8 H8 0.9300 . ?
C9 C13 1.381(3) . ?
C9 C11 1.389(3) . ?
C9 H9 0.9300 . ?
N10 C12 1.344(2) . ?
N10 C14 1.354(2) . ?
C11 C12 1.422(2) . ?
C13 C14 1.418(2) . ?
C15 C16 1.369(3) . ?
C15 C20 1.372(3) . ?
C15 C21 1.492(3) . ?
C16 C17 1.347(5) . ?
C16 C19A 1.56(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.342(7) . ?
C17 F24 1.346(7) . ?
C19 C18 1.351(6) . ?
C19 C20 1.388(6) . ?
C19 H19 0.9300 . ?
C19A C18 1.37(7) . ?
C19A H19A 0.9300 . ?
C17A C20 1.22(8) . ?
C17A F25 1.28(2) . ?
C17A C18 1.40(8) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C21 O23 1.208(2) . ?
C21 O22 1.291(2) . ?
O22 H22 0.991(17) . ?
F25 H19 0.1601 . ?

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 C11 121.4(2) . . ?
C2 C1 H1 119.3 . . ?
C11 C1 H1 119.3 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C12 120.89(19) . . ?
C3 C4 H4 119.6 . . ?
C12 C4 H4 119.6 . . ?
C6 C5 C14 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C14 C5 H5 119.7 . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C13 120.9(2) . . ?
C7 C8 H8 119.6 . . ?
C13 C8 H8 119.6 . . ?
C13 C9 C11 121.26(16) . . ?
C13 C9 H9 119.4 . . ?
C11 C9 H9 119.4 . . ?
C12 N10 C14 119.76(15) . . ?
C9 C11 C1 124.55(18) . . ?
C9 C11 C12 117.65(17) . . ?
C1 C11 C12 117.80(19) . . ?
N10 C12 C4 119.37(17) . . ?
N10 C12 C11 121.78(18) . . ?
C4 C12 C11 118.86(17) . . ?
C9 C13 C14 117.84(18) . . ?
C9 C13 C8 123.72(17) . . ?
C14 C13 C8 118.44(18) . . ?
N10 C14 C5 119.48(17) . . ?
N10 C14 C13 121.72(17) . . ?
C5 C14 C13 118.80(19) . . ?
C16 C15 C20 119.4(2) . . ?
C16 C15 C21 118.5(2) . . ?
C20 C15 C21 122.1(2) . . ?
C17 C16 C15 119.1(3) . . ?
C15 C16 C19A 123(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C19A C16 H16 115.7 . . ?
C18 C17 F24 117.0(3) . . ?
C18 C17 C16 123.4(5) . . ?
F24 C17 C16 119.5(5) . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.2 . . ?
C18 C19A C16 108(3) . . ?
C18 C19A H19A 126.1 . . ?
C16 C19A H19A 126.1 . . ?
C20 C17A F25 121(7) . . ?
C20 C17A C18 131(4) . . ?
F25 C17A C18 98(4) . . ?
C20 C17A H19 117.1 . . ?
C18 C17A H19 102.0 . . ?
C17 C18 C19 117.9(3) . . ?
C19 C18 C19A 127(2) . . ?
C17 C18 C17A 108.8(16) . . ?
C19A C18 C17A 117(3) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C19A C18 H18 110.8 . . ?
C17A C18 H18 129.2 . . ?
C15 C20 C19 119.0(3) . . ?
C17A C20 H20 124.5 . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
O23 C21 O22 123.85(19) . . ?
O23 C21 C15 121.8(2) . . ?
O22 C21 C15 114.4(2) . . ?
C21 O22 H22 112.6(15) . . ?

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
C11 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C12 0.8(3) . . . . ?
C14 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C13 -0.3(3) . . . . ?
C13 C9 C11 C1 -179.94(16) . . . . ?
C13 C9 C11 C12 0.6(2) . . . . ?
C2 C1 C11 C9 -179.10(17) . . . . ?
C2 C1 C11 C12 0.4(3) . . . . ?
C14 N10 C12 C4 -179.66(14) . . . . ?
C14 N10 C12 C11 0.0(2) . . . . ?
C3 C4 C12 N10 179.25(17) . . . . ?
C3 C4 C12 C11 -0.5(3) . . . . ?
C9 C11 C12 N10 -0.3(2) . . . . ?
C1 C11 C12 N10 -179.83(14) . . . . ?
C9 C11 C12 C4 179.41(14) . . . . ?
C1 C11 C12 C4 -0.1(2) . . . . ?
C11 C9 C13 C14 -0.6(2) . . . . ?
C11 C9 C13 C8 179.58(15) . . . . ?
C7 C8 C13 C9 -179.73(17) . . . . ?
C7 C8 C13 C14 0.4(3) . . . . ?
C12 N10 C14 C5 -179.89(15) . . . . ?
C12 N10 C14 C13 0.0(2) . . . . ?
C6 C5 C14 N10 179.26(15) . . . . ?
C6 C5 C14 C13 -0.6(3) . . . . ?
C9 C13 C14 N10 0.3(2) . . . . ?
C8 C13 C14 N10 -179.83(14) . . . . ?
C9 C13 C14 C5 -179.85(14) . . . . ?
C8 C13 C14 C5 0.0(2) . . . . ?
C20 C15 C16 C17 -0.6(4) . . . . ?
C21 C15 C16 C17 179.6(3) . . . . ?
C20 C15 C16 C19A 9(3) . . . . ?
C21 C15 C16 C19A -171(3) . . . . ?
C15 C16 C17 C18 1.8(7) . . . . ?
C19A C16 C17 C18 -118(22) . . . . ?
C15 C16 C17 F24 179.5(4) . . . . ?
C19A C16 C17 F24 60(21) . . . . ?
C17 C16 C19A C18 49(18) . . . . ?
C15 C16 C19A C18 -16(5) . . . . ?
F24 C17 C18 C19 179.8(4) . . . . ?
C16 C17 C18 C19 -2.5(7) . . . . ?
F24 C17 C18 C19A -41(15) . . . . ?
C16 C17 C18 C19A 136(15) . . . . ?
F24 C17 C18 C17A -170(3) . . . . ?
C16 C17 C18 C17A 8(3) . . . . ?
C20 C19 C18 C17 2.0(6) . . . . ?
C20 C19 C18 C19A -9(3) . . . . ?
C20 C19 C18 C17A -46(12) . . . . ?
C16 C19A C18 C17 -31(11) . . . . ?
C16 C19A C18 C19 16(5) . . . . ?
C16 C19A C18 C17A 25(5) . . . . ?
C20 C17A C18 C17 -25(5) . . . . ?
F25 C17A C18 C17 -169(3) . . . . ?
C20 C17A C18 C19 111(16) . . . . ?
F25 C17A C18 C19 -33(9) . . . . ?
C20 C17A C18 C19A -36(6) . . . . ?
F25 C17A C18 C19A 179(3) . . . . ?
F25 C17A C20 C15 164(3) . . . . ?
C18 C17A C20 C15 27(5) . . . . ?
F25 C17A C20 C19 46(11) . . . . ?
C18 C17A C20 C19 -92(13) . . . . ?
C16 C15 C20 C17A -12(2) . . . . ?
C21 C15 C20 C17A 168(2) . . . . ?
C16 C15 C20 C19 0.2(4) . . . . ?
C21 C15 C20 C19 180.0(3) . . . . ?
C18 C19 C20 C17A 66(13) . . . . ?
C18 C19 C20 C15 -0.9(6) . . . . ?
C16 C15 C21 O23 2.7(3) . . . . ?
C20 C15 C21 O23 -177.1(2) . . . . ?
C16 C15 C21 O22 -178.14(19) . . . . ?
C20 C15 C21 O22 2.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.031
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047952'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C7 H5 Cl O2'
_chemical_formula_sum            'C20 H14 Cl N O2'
_chemical_formula_weight         335.77

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'
O O 0.0106 0.0060 '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'
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                   7.0786(7)
_cell_length_b                   8.7908(10)
_cell_length_c                   13.8032(13)
_cell_angle_alpha                76.757(9)
_cell_angle_beta                 83.524(8)
_cell_angle_gamma                78.472(9)
_cell_volume                     817.19(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            light-orange
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8794
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6365
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2842
_reflns_number_gt                2326
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_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)+(0.0540P)²+0.1754P] 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     SHELXL
_refine_ls_extinction_coef       0.0073(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2842
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.1505(3) 1.3276(2) 0.10468(16) 0.0654(5) Uani 1 1 d . . .
H1 H 0.1383 1.4222 0.0571 0.078 Uiso 1 1 calc R . .
C2 C 0.1276(3) 1.3323(3) 0.20257(18) 0.0746(6) Uani 1 1 d . . .
H2 H 0.1003 1.4298 0.2216 0.090 Uiso 1 1 calc R . .
C3 C 0.1448(3) 1.1915(3) 0.27541(16) 0.0694(5) Uani 1 1 d . . .
H3 H 0.1294 1.1963 0.3425 0.083 Uiso 1 1 calc R . .
C4 C 0.1834(2) 1.0492(2) 0.24977(13) 0.0564(4) Uani 1 1 d . . .
H4 H 0.1928 0.9570 0.2994 0.068 Uiso 1 1 calc R . .
C5 C 0.3159(2) 0.7285(2) 0.00489(15) 0.0598(5) Uani 1 1 d . . .
H5 H 0.3279 0.6381 0.0559 0.072 Uiso 1 1 calc R . .
C6 C 0.3378(3) 0.7137(3) -0.09164(17) 0.0724(6) Uani 1 1 d . . .
H6 H 0.3627 0.6131 -0.1062 0.087 Uiso 1 1 calc R . .
C7 C 0.3231(3) 0.8488(3) -0.16995(16) 0.0776(6) Uani 1 1 d . . .
H7 H 0.3390 0.8365 -0.2357 0.093 Uiso 1 1 calc R . .
C8 C 0.2864(3) 0.9953(3) -0.15074(13) 0.0671(5) Uani 1 1 d . . .
H8 H 0.2785 1.0833 -0.2034 0.081 Uiso 1 1 calc R . .
C9 C 0.2198(2) 1.1655(2) -0.02589(12) 0.0534(4) Uani 1 1 d . . .
H9 H 0.2109 1.2567 -0.0763 0.064 Uiso 1 1 calc R . .
N10 N 0.25102(17) 0.89344(15) 0.12470(9) 0.0444(3) Uani 1 1 d . . .
C11 C 0.1933(2) 1.17967(18) 0.07288(12) 0.0468(4) Uani 1 1 d . . .
C12 C 0.2102(2) 1.03769(18) 0.14773(11) 0.0430(4) Uani 1 1 d . . .
C13 C 0.2594(2) 1.0179(2) -0.05077(11) 0.0471(4) Uani 1 1 d . . .
C14 C 0.2750(2) 0.88082(18) 0.02843(11) 0.0432(4) Uani 1 1 d . . .
C15 C 0.4796(2) 0.43440(18) 0.37529(11) 0.0486(4) Uani 1 1 d . . .
C16 C 0.3174(2) 0.40549(19) 0.43668(12) 0.0524(4) Uani 1 1 d . . .
H16 H 0.1985 0.4711 0.4240 0.063 Uiso 1 1 calc R . .
C17 C 0.3332(3) 0.2784(2) 0.51695(13) 0.0600(5) Uani 1 1 d . . .
C18 C 0.5063(3) 0.1806(2) 0.53748(15) 0.0682(5) Uani 1 1 d . . .
H18 H 0.5147 0.0951 0.5918 0.082 Uiso 1 1 calc R . .
C19 C 0.6670(3) 0.2107(2) 0.47681(16) 0.0747(6) Uani 1 1 d . . .
H19 H 0.7858 0.1453 0.4902 0.090 Uiso 1 1 calc R . .
C20 C 0.6550(3) 0.3371(2) 0.39584(14) 0.0655(5) Uani 1 1 d . . .
H20 H 0.7653 0.3565 0.3552 0.079 Uiso 1 1 calc R . .
C21 C 0.4671(3) 0.5686(2) 0.28574(12) 0.0545(4) Uani 1 1 d . . .
O22 O 0.29316(19) 0.65025(14) 0.27391(9) 0.0663(4) Uani 1 1 d D . .
H22 H 0.286(3) 0.742(2) 0.2170(15) 0.099 Uiso 1 1 d D . .
O23 O 0.6059(2) 0.59408(19) 0.22976(11) 0.0886(5) Uani 1 1 d . . .
Cl24 Cl 0.12817(9) 0.24263(9) 0.59382(5) 0.1113(3) Uani 1 1 d . . .


_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 1.352(3) . ?
C1 C11 1.432(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.345(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.424(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.357(3) . ?
C5 C14 1.416(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.343(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.425(2) . ?
C8 H8 0.9300 . ?
C9 C13 1.384(2) . ?
C9 C11 1.386(2) . ?
C9 H9 0.9300 . ?
N10 C12 1.345(2) . ?
N10 C14 1.3477(19) . ?
C11 C12 1.420(2) . ?
C13 C14 1.425(2) . ?
C15 C20 1.377(2) . ?
C15 C16 1.378(2) . ?
C15 C21 1.498(2) . ?
C16 C17 1.378(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(3) . ?
C17 Cl24 1.7360(19) . ?
C18 C19 1.367(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O23 1.204(2) . ?
C21 O22 1.302(2) . ?
O22 H22 0.984(16) . ?

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 C11 121.26(18) . . ?
C2 C1 H1 119.4 . . ?
C11 C1 H1 119.4 . . ?
C1 C2 C3 120.34(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.93(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C12 120.93(18) . . ?
C3 C4 H4 119.5 . . ?
C12 C4 H4 119.5 . . ?
C6 C5 C14 120.38(19) . . ?
C6 C5 H5 119.8 . . ?
C14 C5 H5 119.8 . . ?
C5 C6 C7 120.78(19) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.65(18) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C13 120.97(19) . . ?
C7 C8 H8 119.5 . . ?
C13 C8 H8 119.5 . . ?
C13 C9 C11 121.11(14) . . ?
C13 C9 H9 119.4 . . ?
C11 C9 H9 119.4 . . ?
C12 N10 C14 120.03(13) . . ?
C9 C11 C12 117.77(15) . . ?
C9 C11 C1 124.50(16) . . ?
C12 C11 C1 117.73(15) . . ?
N10 C12 C11 121.79(14) . . ?
N10 C12 C4 119.41(14) . . ?
C11 C12 C4 118.80(15) . . ?
C9 C13 C14 117.91(14) . . ?
C9 C13 C8 123.86(16) . . ?
C14 C13 C8 118.23(17) . . ?
N10 C14 C5 119.64(15) . . ?
N10 C14 C13 121.38(14) . . ?
C5 C14 C13 118.98(15) . . ?
C20 C15 C16 119.50(16) . . ?
C20 C15 C21 119.61(16) . . ?
C16 C15 C21 120.88(15) . . ?
C17 C16 C15 119.36(16) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 121.53(17) . . ?
C18 C17 Cl24 119.39(14) . . ?
C16 C17 Cl24 119.08(14) . . ?
C17 C18 C19 118.85(17) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C20 120.74(18) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 120.02(18) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
O23 C21 O22 124.29(16) . . ?
O23 C21 C15 122.11(17) . . ?
O22 C21 C15 113.58(14) . . ?
C21 O22 H22 113.6(14) . . ?

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
C11 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C12 0.7(3) . . . . ?
C14 C5 C6 C7 1.0(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C13 -0.6(3) . . . . ?
C13 C9 C11 C12 0.7(2) . . . . ?
C13 C9 C11 C1 -179.51(15) . . . . ?
C2 C1 C11 C9 -179.57(17) . . . . ?
C2 C1 C11 C12 0.2(2) . . . . ?
C14 N10 C12 C11 -0.7(2) . . . . ?
C14 N10 C12 C4 179.41(13) . . . . ?
C9 C11 C12 N10 0.2(2) . . . . ?
C1 C11 C12 N10 -179.64(14) . . . . ?
C9 C11 C12 C4 -179.98(14) . . . . ?
C1 C11 C12 C4 0.2(2) . . . . ?
C3 C4 C12 N10 179.16(15) . . . . ?
C3 C4 C12 C11 -0.7(2) . . . . ?
C11 C9 C13 C14 -0.9(2) . . . . ?
C11 C9 C13 C8 179.38(15) . . . . ?
C7 C8 C13 C9 -179.50(16) . . . . ?
C7 C8 C13 C14 0.8(2) . . . . ?
C12 N10 C14 C5 -179.32(13) . . . . ?
C12 N10 C14 C13 0.5(2) . . . . ?
C6 C5 C14 N10 179.06(15) . . . . ?
C6 C5 C14 C13 -0.7(2) . . . . ?
C9 C13 C14 N10 0.4(2) . . . . ?
C8 C13 C14 N10 -179.94(13) . . . . ?
C9 C13 C14 C5 -179.84(14) . . . . ?
C8 C13 C14 C5 -0.1(2) . . . . ?
C20 C15 C16 C17 -0.8(2) . . . . ?
C21 C15 C16 C17 178.30(15) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C17 Cl24 -179.90(13) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
Cl24 C17 C18 C19 -179.54(16) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C16 C15 C20 C19 0.7(3) . . . . ?
C21 C15 C20 C19 -178.40(17) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C20 C15 C21 O23 0.8(3) . . . . ?
C16 C15 C21 O23 -178.30(17) . . . . ?
C20 C15 C21 O22 179.14(15) . . . . ?
C16 C15 C21 O22 0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.028
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1047953'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
#=============================================================
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
?
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C7 H5 Br O2'
_chemical_formula_sum            'C20 H14 Br N O2'
_chemical_formula_weight         380.23

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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                   7.0948(14)
_cell_length_b                   8.7528(19)
_cell_length_c                   13.960(2)
_cell_angle_alpha                77.328(15)
_cell_angle_beta                 83.389(14)
_cell_angle_gamma                79.591(17)
_cell_volume                     829.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5353
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    2.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3521
_exptl_absorpt_correction_T_max  0.8070
_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5353
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0923
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2921
_reflns_number_gt                1587
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_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)+(0.0182P)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     SHELXL
_refine_ls_extinction_coef       0.0081(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2921
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
C1 C 0.6520(6) 1.3281(5) 0.6071(4) 0.0652(13) Uani 1 1 d . . .
H1 H 0.6365 1.4220 0.5602 0.078 Uiso 1 1 calc R . .
C2 C 0.6341(7) 1.3346(7) 0.7024(5) 0.0797(16) Uani 1 1 d . . .
H2 H 0.6069 1.4325 0.7210 0.096 Uiso 1 1 calc R . .
C3 C 0.6563(6) 1.1949(7) 0.7746(4) 0.0712(14) Uani 1 1 d . . .
H3 H 0.6442 1.2015 0.8407 0.085 Uiso 1 1 calc R . .
C4 C 0.6945(6) 1.0519(6) 0.7504(3) 0.0558(12) Uani 1 1 d . . .
H4 H 0.7066 0.9606 0.7996 0.067 Uiso 1 1 calc R . .
C5 C 0.8165(6) 0.7278(5) 0.5107(4) 0.0601(12) Uani 1 1 d . . .
H5 H 0.8293 0.6385 0.5612 0.072 Uiso 1 1 calc R . .
C6 C 0.8356(6) 0.7116(6) 0.4151(4) 0.0737(15) Uani 1 1 d . . .
H6 H 0.8626 0.6105 0.4011 0.088 Uiso 1 1 calc R . .
C7 C 0.8157(6) 0.8435(8) 0.3379(4) 0.0756(15) Uani 1 1 d . . .
H7 H 0.8273 0.8295 0.2732 0.091 Uiso 1 1 calc R . .
C8 C 0.7800(6) 0.9901(7) 0.3566(3) 0.0660(13) Uani 1 1 d . . .
H8 H 0.7704 1.0773 0.3045 0.079 Uiso 1 1 calc R . .
C9 C 0.7166(5) 1.1625(5) 0.4785(3) 0.0543(12) Uani 1 1 d . . .
H9 H 0.7043 1.2526 0.4285 0.065 Uiso 1 1 calc R . .
N10 N 0.7564(4) 0.8943(4) 0.6276(2) 0.0431(8) Uani 1 1 d . . .
C11 C 0.6947(5) 1.1787(5) 0.5753(3) 0.0476(11) Uani 1 1 d . . .
C12 C 0.7166(5) 1.0395(5) 0.6499(3) 0.0424(10) Uani 1 1 d . . .
C13 C 0.7568(5) 1.0141(5) 0.4548(3) 0.0436(10) Uani 1 1 d . . .
C14 C 0.7770(5) 0.8809(5) 0.5325(3) 0.0398(10) Uani 1 1 d . . .
C15 C 0.9908(6) 0.4371(5) 0.8699(3) 0.0467(11) Uani 1 1 d . . .
C16 C 0.8311(6) 0.4091(4) 0.9348(3) 0.0501(11) Uani 1 1 d . A .
H16 H 0.7136 0.4752 0.9251 0.060 Uiso 1 1 calc R . .
C17 C 0.8483(6) 0.2833(5) 1.0132(3) 0.0551(12) Uani 1 1 d . . .
C18 C 1.0180(8) 0.1836(5) 1.0290(3) 0.0696(14) Uani 1 1 d . A .
H18 H 1.0262 0.0971 1.0816 0.083 Uiso 1 1 calc R . .
C19 C 1.1768(7) 0.2129(6) 0.9658(4) 0.0768(15) Uani 1 1 d . . .
H19 H 1.2942 0.1472 0.9766 0.092 Uiso 1 1 calc R A .
C20 C 1.1635(7) 0.3381(6) 0.8872(3) 0.0666(13) Uani 1 1 d . A .
H20 H 1.2720 0.3566 0.8450 0.080 Uiso 1 1 calc R . .
C21 C 0.9766(7) 0.5695(5) 0.7814(3) 0.0568(12) Uani 1 1 d . . .
O22 O 0.8051(5) 0.6554(3) 0.7750(2) 0.0647(8) Uani 1 1 d D . .
H22 H 0.800(6) 0.746(4) 0.719(2) 0.097 Uiso 1 1 d D . .
O23 O 1.1117(5) 0.5925(4) 0.7223(2) 0.0837(11) Uani 1 1 d . . .
Br24 Br 0.62702(8) 0.24723(7) 1.09971(4) 0.0981(3) Uani 1 1 d . A 1


_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 1.335(6) . ?
C1 C11 1.442(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.401(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.340(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.421(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(6) . ?
C5 C14 1.411(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.339(6) . ?
C7 H7 0.9300 . ?
C8 C13 1.419(6) . ?
C8 H8 0.9300 . ?
C9 C11 1.377(5) . ?
C9 C13 1.383(5) . ?
C9 H9 0.9300 . ?
N10 C14 1.348(4) . ?
N10 C12 1.347(4) . ?
C11 C12 1.415(5) . ?
C13 C14 1.406(5) . ?
C15 C20 1.379(6) . ?
C15 C16 1.390(5) . ?
C15 C21 1.497(6) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(6) . ?
C17 Br24 1.897(4) . ?
C18 C19 1.375(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O23 1.206(4) . ?
C21 O22 1.311(5) . ?
O22 H22 0.982(19) . ?

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 C11 121.5(5) . . ?
C2 C1 H1 119.3 . . ?
C11 C1 H1 119.3 . . ?
C1 C2 C3 120.4(5) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C12 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
C12 C4 H4 119.9 . . ?
C6 C5 C14 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C14 C5 H5 120.2 . . ?
C5 C6 C7 121.4(5) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C13 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C13 C8 H8 119.6 . . ?
C11 C9 C13 120.9(4) . . ?
C11 C9 H9 119.6 . . ?
C13 C9 H9 119.6 . . ?
C14 N10 C12 119.5(3) . . ?
C9 C11 C12 118.3(4) . . ?
C9 C11 C1 124.8(4) . . ?
C12 C11 C1 116.9(4) . . ?
N10 C12 C11 121.3(4) . . ?
N10 C12 C4 118.9(4) . . ?
C11 C12 C4 119.8(4) . . ?
C9 C13 C14 117.8(4) . . ?
C9 C13 C8 123.4(4) . . ?
C14 C13 C8 118.8(4) . . ?
N10 C14 C13 122.2(4) . . ?
N10 C14 C5 118.7(4) . . ?
C13 C14 C5 119.2(4) . . ?
C20 C15 C16 118.8(4) . . ?
C20 C15 C21 120.1(4) . . ?
C16 C15 C21 121.1(4) . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 121.7(4) . . ?
C18 C17 Br24 119.9(3) . . ?
C16 C17 Br24 118.3(4) . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 120.5(5) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C15 120.7(4) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
O23 C21 O22 124.2(4) . . ?
O23 C21 C15 122.2(5) . . ?
O22 C21 C15 113.5(4) . . ?
C21 O22 H22 113(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
C11 C1 C2 C3 -0.2(7) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C3 C4 C12 1.0(7) . . . . ?
C14 C5 C6 C7 -0.5(7) . . . . ?
C5 C6 C7 C8 1.1(7) . . . . ?
C6 C7 C8 C13 -1.7(7) . . . . ?
C13 C9 C11 C12 0.7(6) . . . . ?
C13 C9 C11 C1 -179.7(4) . . . . ?
C2 C1 C11 C9 -179.5(4) . . . . ?
C2 C1 C11 C12 0.1(6) . . . . ?
C14 N10 C12 C11 0.4(5) . . . . ?
C14 N10 C12 C4 179.8(3) . . . . ?
C9 C11 C12 N10 -0.5(5) . . . . ?
C1 C11 C12 N10 179.9(3) . . . . ?
C9 C11 C12 C4 -179.9(4) . . . . ?
C1 C11 C12 C4 0.5(5) . . . . ?
C3 C4 C12 N10 179.5(4) . . . . ?
C3 C4 C12 C11 -1.1(6) . . . . ?
C11 C9 C13 C14 -0.9(6) . . . . ?
C11 C9 C13 C8 179.7(4) . . . . ?
C7 C8 C13 C9 -178.9(4) . . . . ?
C7 C8 C13 C14 1.7(6) . . . . ?
C12 N10 C14 C13 -0.5(5) . . . . ?
C12 N10 C14 C5 -179.3(3) . . . . ?
C9 C13 C14 N10 0.8(5) . . . . ?
C8 C13 C14 N10 -179.8(3) . . . . ?
C9 C13 C14 C5 179.5(3) . . . . ?
C8 C13 C14 C5 -1.1(5) . . . . ?
C6 C5 C14 N10 179.3(4) . . . . ?
C6 C5 C14 C13 0.5(6) . . . . ?
C20 C15 C16 C17 -0.9(6) . . . . ?
C21 C15 C16 C17 177.8(4) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C15 C16 C17 Br24 -179.4(3) . . . . ?
C16 C17 C18 C19 1.7(7) . . . . ?
Br24 C17 C18 C19 -179.4(3) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C18 C19 C20 C15 0.0(7) . . . . ?
C16 C15 C20 C19 1.1(6) . . . . ?
C21 C15 C20 C19 -177.5(4) . . . . ?
C20 C15 C21 O23 1.3(6) . . . . ?
C16 C15 C21 O23 -177.3(4) . . . . ?
C20 C15 C21 O22 -179.0(4) . . . . ?
C16 C15 C21 O22 2.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.053
