# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1013398'
_audit_update_record             
;
2014-07-11 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 Cl N O'
_chemical_formula_sum            'C17 H12 Cl N O'
_chemical_formula_weight         281.73

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                   7.1491(6)
_cell_length_b                   9.2336(9)
_cell_length_c                   10.4719(9)
_cell_angle_alpha                91.207(4)
_cell_angle_beta                 97.280(3)
_cell_angle_gamma                90.918(3)
_cell_volume                     685.42(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3754
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      25.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7017
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'


_exptl_special_details           
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9560
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.87
_reflns_number_total             2614
_reflns_number_gt                2013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.1274P] 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         2614
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.2902(2) 0.68985(18) 0.36687(16) 0.0393(4) Uani 1 1 d . . .
C2 C 0.2861(3) 0.6210(2) 0.24701(17) 0.0471(5) Uani 1 1 d . . .
H2 H 0.3935 0.6231 0.2054 0.057 Uiso 1 1 calc R . .
C3 C 0.1258(3) 0.5497(2) 0.18886(18) 0.0514(5) Uani 1 1 d . . .
H3 H 0.1247 0.5043 0.1086 0.062 Uiso 1 1 calc R . .
C4 C -0.0328(3) 0.54660(19) 0.25112(18) 0.0454(4) Uani 1 1 d . . .
C5 C -0.0334(3) 0.6128(2) 0.36994(18) 0.0484(5) Uani 1 1 d . . .
H5 H -0.1414 0.6100 0.4110 0.058 Uiso 1 1 calc R . .
C6 C 0.1286(3) 0.6835(2) 0.42751(18) 0.0468(4) Uani 1 1 d . . .
H6 H 0.1292 0.7276 0.5082 0.056 Uiso 1 1 calc R . .
C7 C 0.5099(3) 0.76116(19) 0.56456(16) 0.0424(4) Uani 1 1 d . . .
H7 H 0.4333 0.7085 0.6130 0.051 Uiso 1 1 calc R . .
C8 C 0.4623(2) 0.76716(18) 0.42950(16) 0.0387(4) Uani 1 1 d . . .
C9 C 0.5761(3) 0.84514(19) 0.36032(16) 0.0413(4) Uani 1 1 d . . .
H9 H 0.5440 0.8508 0.2717 0.050 Uiso 1 1 calc R . .
C10 C 0.7426(3) 0.91821(19) 0.41949(16) 0.0407(4) Uani 1 1 d . . .
C11 C 0.6665(3) 0.83163(18) 0.62433(15) 0.0379(4) Uani 1 1 d . . .
C12 C 0.7190(3) 0.83309(18) 0.76572(15) 0.0412(4) Uani 1 1 d . . .
C13 C 0.9049(3) 0.8315(2) 0.82172(17) 0.0477(5) Uani 1 1 d . . .
H13 H 1.0020 0.8321 0.7704 0.057 Uiso 1 1 calc R . .
C14 C 0.9460(3) 0.8290(2) 0.95451(18) 0.0571(5) Uani 1 1 d . . .
H14 H 1.0711 0.8269 0.9918 0.069 Uiso 1 1 calc R . .
C15 C 0.8050(4) 0.8296(2) 1.03163(19) 0.0645(6) Uani 1 1 d . . .
H15 H 0.8341 0.8278 1.1207 0.077 Uiso 1 1 calc R . .
C16 C 0.6199(4) 0.8328(2) 0.97643(19) 0.0655(6) Uani 1 1 d . . .
H16 H 0.5238 0.8337 1.0286 0.079 Uiso 1 1 calc R . .
C17 C 0.5758(3) 0.8346(2) 0.84436(17) 0.0543(5) Uani 1 1 d . . .
H17 H 0.4504 0.8367 0.8078 0.065 Uiso 1 1 calc R . .
N1 N 0.7798(2) 0.90537(15) 0.55089(13) 0.0388(4) Uani 1 1 d D . .
H1 H 0.880(2) 0.946(2) 0.5874(17) 0.047 Uiso 1 1 d D . .
O1 O 0.85187(18) 0.99115(15) 0.36061(11) 0.0525(4) Uani 1 1 d . . .
Cl1 Cl -0.23781(7) 0.45999(6) 0.17798(5) 0.0662(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 C6 1.388(3) . ?
C1 C2 1.392(2) . ?
C1 C8 1.484(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 Cl1 1.7396(18) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.360(2) . ?
C7 C8 1.415(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(2) . ?
C9 C10 1.423(2) . ?
C9 H9 0.9300 . ?
C10 O1 1.252(2) . ?
C10 N1 1.376(2) . ?
C11 N1 1.369(2) . ?
C11 C12 1.480(2) . ?
C12 C13 1.384(3) . ?
C12 C17 1.393(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N1 H1 0.847(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
C6 C1 C2 118.17(17) . . ?
C6 C1 C8 120.47(16) . . ?
C2 C1 C8 121.35(16) . . ?
C3 C2 C1 121.23(18) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 119.12(17) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 121.21(17) . . ?
C5 C4 Cl1 118.98(15) . . ?
C3 C4 Cl1 119.81(15) . . ?
C4 C5 C6 119.11(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 121.14(17) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C11 C7 C8 120.66(16) . . ?
C11 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 118.77(15) . . ?
C9 C8 C1 121.70(15) . . ?
C7 C8 C1 119.53(15) . . ?
C8 C9 C10 122.03(15) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
O1 C10 N1 119.90(15) . . ?
O1 C10 C9 124.63(15) . . ?
N1 C10 C9 115.47(15) . . ?
C7 C11 N1 118.71(15) . . ?
C7 C11 C12 122.82(15) . . ?
N1 C11 C12 118.47(15) . . ?
C13 C12 C17 119.22(16) . . ?
C13 C12 C11 122.15(16) . . ?
C17 C12 C11 118.62(17) . . ?
C12 C13 C14 119.78(19) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.55(19) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C11 N1 C10 124.33(15) . . ?
C11 N1 H1 119.0(13) . . ?
C10 N1 H1 116.7(13) . . ?

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
C6 C1 C2 C3 0.8(3) . . . . ?
C8 C1 C2 C3 -179.76(17) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 Cl1 178.84(15) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
Cl1 C4 C5 C6 -179.08(14) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C8 C1 C6 C5 179.52(16) . . . . ?
C11 C7 C8 C9 -0.1(3) . . . . ?
C11 C7 C8 C1 -179.70(17) . . . . ?
C6 C1 C8 C9 -142.86(19) . . . . ?
C2 C1 C8 C9 37.7(3) . . . . ?
C6 C1 C8 C7 36.7(2) . . . . ?
C2 C1 C8 C7 -142.76(18) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C1 C8 C9 C10 -179.27(16) . . . . ?
C8 C9 C10 O1 180.00(18) . . . . ?
C8 C9 C10 N1 -0.4(3) . . . . ?
C8 C7 C11 N1 -1.7(3) . . . . ?
C8 C7 C11 C12 177.80(16) . . . . ?
C7 C11 C12 C13 144.69(19) . . . . ?
N1 C11 C12 C13 -35.8(2) . . . . ?
C7 C11 C12 C17 -34.6(3) . . . . ?
N1 C11 C12 C17 144.86(17) . . . . ?
C17 C12 C13 C14 1.1(3) . . . . ?
C11 C12 C13 C14 -178.24(16) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C11 C12 C17 C16 178.59(18) . . . . ?
C7 C11 N1 C10 2.6(3) . . . . ?
C12 C11 N1 C10 -176.90(16) . . . . ?
O1 C10 N1 C11 178.09(17) . . . . ?
C9 C10 N1 C11 -1.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.87
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1013399'
_audit_update_record             
;
2014-07-11 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl N O2'
_chemical_formula_sum            'C18 H14 Cl N O2'
_chemical_formula_weight         311.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   15.8518(10)
_cell_length_b                   7.2952(5)
_cell_length_c                   13.5752(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.043(3)
_cell_angle_gamma                90.00
_cell_volume                     1508.73(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3204
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.06

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6520
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11515
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         26.56
_reflns_number_total             3082
_reflns_number_gt                2142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0779P)²+0.6163P] 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         3082
_refine_ls_number_parameters     203
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1642
_refine_ls_wR_factor_gt          0.1443
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.71611(15) 0.2699(3) 0.66069(16) 0.0457(5) Uani 1 1 d . . .
C2 C 0.6407(2) 0.2395(6) 0.5849(2) 0.0942(12) Uani 1 1 d . . .
H2 H 0.6431 0.2393 0.5172 0.113 Uiso 1 1 calc R . .
C3 C 0.5619(2) 0.2093(6) 0.6039(2) 0.1023(14) Uani 1 1 d . . .
H3 H 0.5124 0.1883 0.5495 0.123 Uiso 1 1 calc R . .
C4 C 0.55442(17) 0.2094(4) 0.7003(2) 0.0625(7) Uani 1 1 d . . .
C5 C 0.6269(2) 0.2393(7) 0.7772(2) 0.1089(15) Uani 1 1 d . . .
H5 H 0.6234 0.2411 0.8445 0.131 Uiso 1 1 calc R . .
C6 C 0.70693(19) 0.2675(7) 0.7573(2) 0.1076(15) Uani 1 1 d . . .
H6 H 0.7564 0.2856 0.8122 0.129 Uiso 1 1 calc R . .
C7 C 0.88023(15) 0.3026(3) 0.72084(16) 0.0426(5) Uani 1 1 d . . .
H7 H 0.8787 0.2661 0.7860 0.051 Uiso 1 1 calc R . .
C8 C 0.80129(15) 0.3087(3) 0.64009(16) 0.0419(5) Uani 1 1 d . . .
C9 C 0.80664(15) 0.3556(3) 0.54436(16) 0.0466(6) Uani 1 1 d . . .
H9 H 0.7555 0.3579 0.4905 0.056 Uiso 1 1 calc R . .
C10 C 0.88737(15) 0.4007(3) 0.52446(15) 0.0436(5) Uani 1 1 d . . .
C11 C 0.95777(14) 0.3495(3) 0.70405(15) 0.0397(5) Uani 1 1 d . . .
C12 C 1.04223(14) 0.3469(3) 0.78499(16) 0.0416(5) Uani 1 1 d . . .
C13 C 1.12080(16) 0.3074(3) 0.76376(18) 0.0509(6) Uani 1 1 d . . .
H13 H 1.1212 0.2852 0.6964 0.061 Uiso 1 1 calc R . .
C14 C 1.19831(17) 0.3004(4) 0.8405(2) 0.0604(7) Uani 1 1 d . . .
H14 H 1.2506 0.2741 0.8251 0.072 Uiso 1 1 calc R . .
C15 C 1.19803(17) 0.3324(4) 0.93986(19) 0.0577(7) Uani 1 1 d . . .
C16 C 1.12165(19) 0.3749(4) 0.96351(18) 0.0599(7) Uani 1 1 d . . .
H16 H 1.1221 0.3988 1.0309 0.072 Uiso 1 1 calc R . .
C17 C 1.04448(16) 0.3816(3) 0.88650(17) 0.0523(6) Uani 1 1 d . . .
H17 H 0.9926 0.4100 0.9025 0.063 Uiso 1 1 calc R . .
C18 C 0.4618(2) 0.1954(5) 0.8120(3) 0.0935(11) Uani 1 1 d . . .
H18A H 0.4792 0.3155 0.8389 0.140 Uiso 1 1 calc R . .
H18B H 0.4976 0.1051 0.8557 0.140 Uiso 1 1 calc R . .
H18C H 0.4013 0.1754 0.8090 0.140 Uiso 1 1 calc R . .
N1 N 0.95971(12) 0.3981(3) 0.60714(13) 0.0420(4) Uani 1 1 d D . .
H1 H 1.0069(12) 0.441(3) 0.5963(17) 0.050 Uiso 1 1 d D . .
O1 O 0.89465(10) 0.4450(3) 0.43798(10) 0.0557(5) Uani 1 1 d . . .
O2 O 0.47269(13) 0.1812(4) 0.71235(16) 0.0885(8) Uani 1 1 d . . .
Cl1 Cl 1.29534(5) 0.31935(13) 1.03758(6) 0.0911(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 C6 1.359(3) . ?
C1 C2 1.363(4) . ?
C1 C8 1.480(3) . ?
C2 C3 1.362(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.346(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.340(4) . ?
C4 O2 1.365(3) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.355(3) . ?
C7 C8 1.418(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(3) . ?
C9 C10 1.418(3) . ?
C9 H9 0.9300 . ?
C10 O1 1.253(2) . ?
C10 N1 1.365(3) . ?
C11 N1 1.371(3) . ?
C11 C12 1.479(3) . ?
C12 C13 1.384(3) . ?
C12 C17 1.392(3) . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(4) . ?
C15 Cl1 1.737(3) . ?
C16 C17 1.373(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.414(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1 0.860(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
C6 C1 C2 114.9(2) . . ?
C6 C1 C8 122.1(2) . . ?
C2 C1 C8 123.0(2) . . ?
C3 C2 C1 122.8(2) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 O2 124.7(2) . . ?
C3 C4 O2 117.2(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 122.6(3) . . ?
C1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C11 C7 C8 120.66(19) . . ?
C11 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 117.9(2) . . ?
C9 C8 C1 121.8(2) . . ?
C7 C8 C1 120.28(18) . . ?
C8 C9 C10 122.3(2) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
O1 C10 N1 120.0(2) . . ?
O1 C10 C9 124.0(2) . . ?
N1 C10 C9 115.93(18) . . ?
C7 C11 N1 119.3(2) . . ?
C7 C11 C12 123.30(18) . . ?
N1 C11 C12 117.43(18) . . ?
C13 C12 C17 117.8(2) . . ?
C13 C12 C11 122.01(19) . . ?
C17 C12 C11 120.2(2) . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 Cl1 119.9(2) . . ?
C16 C15 Cl1 119.3(2) . . ?
C15 C16 C17 119.2(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 N1 C11 123.80(18) . . ?
C10 N1 H1 115.3(16) . . ?
C11 N1 H1 120.6(16) . . ?
C4 O2 C18 118.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.56
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1013400'
_audit_update_record             
;
2014-07-11 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28

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

_symmetry_cell_setting           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                   6.3743(7)
_cell_length_b                   10.3034(13)
_cell_length_c                   10.5322(12)
_cell_angle_alpha                80.064(4)
_cell_angle_beta                 72.725(5)
_cell_angle_gamma                76.743(4)
_cell_volume                     638.85(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    950
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      23.55

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Pink
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4212
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.64
_reflns_number_total             2645
_reflns_number_gt                1672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1064P)²+0.1174P] 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         2645
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1706
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   0.854
_refine_ls_restrained_S_all      0.854
_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 0.5951(4) 0.33539(19) 0.8413(2) 0.0420(5) Uani 1 1 d . . .
C2 C 0.5565(4) 0.2132(2) 0.9143(3) 0.0542(6) Uani 1 1 d . . .
H2 H 0.4413 0.1761 0.9068 0.065 Uiso 1 1 calc R . .
C3 C 0.6874(5) 0.1461(2) 0.9980(3) 0.0645(7) Uani 1 1 d . . .
H3 H 0.6596 0.0643 1.0461 0.077 Uiso 1 1 calc R . .
C4 C 0.8570(5) 0.1988(3) 1.0105(3) 0.0642(7) Uani 1 1 d . . .
H4 H 0.9464 0.1524 1.0655 0.077 Uiso 1 1 calc R . .
C5 C 0.8951(4) 0.3209(3) 0.9415(3) 0.0626(7) Uani 1 1 d . . .
H5 H 1.0092 0.3577 0.9509 0.075 Uiso 1 1 calc R . .
C6 C 0.7638(4) 0.3895(2) 0.8577(2) 0.0512(6) Uani 1 1 d . . .
H6 H 0.7896 0.4725 0.8122 0.061 Uiso 1 1 calc R . .
C7 C 0.3918(4) 0.54827(18) 0.7403(2) 0.0407(5) Uani 1 1 d . . .
H7 H 0.4474 0.5976 0.7847 0.049 Uiso 1 1 calc R . .
C8 C 0.4572(3) 0.40636(18) 0.7504(2) 0.0396(5) Uani 1 1 d . . .
C9 C 0.3816(4) 0.33701(19) 0.6781(2) 0.0449(5) Uani 1 1 d . . .
H9 H 0.4286 0.2444 0.6813 0.054 Uiso 1 1 calc R . .
C10 C 0.2338(4) 0.40206(18) 0.5985(2) 0.0425(5) Uani 1 1 d . . .
C11 C 0.2487(3) 0.61234(17) 0.6663(2) 0.0364(5) Uani 1 1 d . . .
C12 C 0.1628(4) 0.75892(18) 0.6593(2) 0.0374(5) Uani 1 1 d . . .
C13 C -0.0661(4) 0.8100(2) 0.6867(2) 0.0468(6) Uani 1 1 d . . .
H13 H -0.1663 0.7524 0.7025 0.056 Uiso 1 1 calc R . .
C14 C -0.1446(4) 0.9465(2) 0.6904(2) 0.0526(6) Uani 1 1 d . . .
H14 H -0.2978 0.9798 0.7106 0.063 Uiso 1 1 calc R . .
C15 C 0.0017(4) 1.0334(2) 0.6647(2) 0.0530(6) Uani 1 1 d . . .
H15 H -0.0519 1.1250 0.6675 0.064 Uiso 1 1 calc R . .
C16 C 0.2284(4) 0.9832(2) 0.6347(2) 0.0506(6) Uani 1 1 d . . .
H16 H 0.3279 1.0417 0.6155 0.061 Uiso 1 1 calc R . .
C17 C 0.3096(4) 0.84687(19) 0.6327(2) 0.0429(5) Uani 1 1 d . . .
H17 H 0.4630 0.8141 0.6136 0.052 Uiso 1 1 calc R . .
N1 N 0.1729(3) 0.53911(15) 0.59792(17) 0.0400(4) Uani 1 1 d D . .
H1 H 0.077(3) 0.582(2) 0.551(2) 0.048 Uiso 1 1 d D . .
O1 O 0.1574(3) 0.34268(13) 0.53351(17) 0.0556(5) 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 C6 1.384(3) . ?
C1 C2 1.390(3) . ?
C1 C8 1.479(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.358(3) . ?
C7 C8 1.420(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C9 C10 1.424(3) . ?
C9 H9 0.9300 . ?
C10 O1 1.249(2) . ?
C10 N1 1.375(2) . ?
C11 N1 1.372(2) . ?
C11 C12 1.481(2) . ?
C12 C17 1.386(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N1 H1 0.890(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
C6 C1 C2 118.1(2) . . ?
C6 C1 C8 121.07(19) . . ?
C2 C1 C8 120.8(2) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.6(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C11 C7 C8 120.38(18) . . ?
C11 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 118.38(18) . . ?
C9 C8 C1 121.16(17) . . ?
C7 C8 C1 120.41(18) . . ?
C8 C9 C10 122.22(17) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
O1 C10 N1 120.04(18) . . ?
O1 C10 C9 124.34(17) . . ?
N1 C10 C9 115.60(17) . . ?
C7 C11 N1 119.42(16) . . ?
C7 C11 C12 122.84(17) . . ?
N1 C11 C12 117.70(17) . . ?
C17 C12 C13 119.08(18) . . ?
C17 C12 C11 120.03(19) . . ?
C13 C12 C11 120.78(18) . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.32(19) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C11 N1 C10 123.92(17) . . ?
C11 N1 H1 118.3(15) . . ?
C10 N1 H1 117.8(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
C6 C1 C2 C3 -1.8(3) . . . . ?
C8 C1 C2 C3 179.2(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
C8 C1 C6 C5 -178.8(2) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C11 C7 C8 C9 3.3(3) . . . . ?
C11 C7 C8 C1 -174.0(2) . . . . ?
C6 C1 C8 C9 145.0(2) . . . . ?
C2 C1 C8 C9 -36.0(3) . . . . ?
C6 C1 C8 C7 -37.8(3) . . . . ?
C2 C1 C8 C7 141.3(2) . . . . ?
C7 C8 C9 C10 -2.6(3) . . . . ?
C1 C8 C9 C10 174.7(2) . . . . ?
C8 C9 C10 O1 -178.5(2) . . . . ?
C8 C9 C10 N1 0.4(3) . . . . ?
C8 C7 C11 N1 -2.0(3) . . . . ?
C8 C7 C11 C12 175.83(19) . . . . ?
C7 C11 C12 C17 49.4(3) . . . . ?
N1 C11 C12 C17 -132.8(2) . . . . ?
C7 C11 C12 C13 -126.9(2) . . . . ?
N1 C11 C12 C13 50.9(3) . . . . ?
C17 C12 C13 C14 -1.6(3) . . . . ?
C11 C12 C13 C14 174.71(19) . . . . ?
C12 C13 C14 C15 1.3(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C15 C16 C17 C12 0.9(3) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C11 C12 C17 C16 -175.82(19) . . . . ?
C7 C11 N1 C10 -0.3(3) . . . . ?
C12 C11 N1 C10 -178.21(19) . . . . ?
O1 C10 N1 C11 -180.0(2) . . . . ?
C9 C10 N1 C11 1.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.887
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.887
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1013401'
_audit_update_record             
;
2014-07-11 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 N O3'
_chemical_formula_sum            'C26 H23 N O3'
_chemical_formula_weight         397.45

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   'C c'
_symmetry_space_group_name_Hall  'C -2yc'

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

_cell_length_a                   19.554(3)
_cell_length_b                   14.7990(17)
_cell_length_c                   7.5795(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.157(6)
_cell_angle_gamma                90.00
_cell_volume                     2151.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1421
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      19.69

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
;
 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8914
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         28.59
_reflns_number_total             5151
_reflns_number_gt                2936
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0493P)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    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.9(14)
_refine_ls_number_reflns         5151
_refine_ls_number_parameters     274
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_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 0.19537(14) 0.4933(2) -0.0272(3) 0.0456(6) Uani 1 1 d . . .
C2 C 0.21054(14) 0.4029(2) -0.0553(3) 0.0473(7) Uani 1 1 d . . .
H2 H 0.2563 0.3847 -0.0514 0.057 Uiso 1 1 calc R . .
C3 C 0.15680(15) 0.34044(19) -0.0890(3) 0.0479(7) Uani 1 1 d . . .
C4 C 0.08847(15) 0.36640(19) -0.0879(3) 0.0491(7) Uani 1 1 d . . .
C5 C 0.07392(14) 0.45558(19) -0.0570(4) 0.0492(7) Uani 1 1 d . . .
C6 C 0.12717(14) 0.5196(2) -0.0272(4) 0.0504(7) Uani 1 1 d . . .
H6 H 0.1171 0.5797 -0.0075 0.060 Uiso 1 1 calc R . .
C7 C 0.24069(14) 0.64600(19) -0.0781(3) 0.0469(7) Uani 1 1 d . . .
H7 H 0.1991 0.6578 -0.1576 0.056 Uiso 1 1 calc R . .
C8 C 0.25156(13) 0.56231(19) 0.0048(3) 0.0436(6) Uani 1 1 d . . .
C9 C 0.31492(13) 0.54736(19) 0.1181(3) 0.0448(6) Uani 1 1 d . . .
H9 H 0.3248 0.4914 0.1730 0.054 Uiso 1 1 calc R . .
C10 C 0.36392(12) 0.61712(18) 0.1494(3) 0.0420(6) Uani 1 1 d . . .
C11 C 0.29188(13) 0.71244(18) -0.0424(3) 0.0413(6) Uani 1 1 d . . .
C12 C 0.28230(14) 0.80235(18) -0.1299(3) 0.0471(6) Uani 1 1 d . . .
C13 C 0.33892(14) 0.8507(2) -0.1660(4) 0.0563(8) Uani 1 1 d . . .
H13 H 0.3837 0.8278 -0.1296 0.068 Uiso 1 1 calc R . .
C14 C 0.32930(18) 0.9317(2) -0.2546(4) 0.0661(9) Uani 1 1 d . . .
H14 H 0.3676 0.9627 -0.2798 0.079 Uiso 1 1 calc R . .
C15 C 0.2641(2) 0.9676(2) -0.3065(5) 0.0712(10) Uani 1 1 d . . .
H15 H 0.2582 1.0227 -0.3668 0.085 Uiso 1 1 calc R . .
C16 C 0.20716(19) 0.9220(2) -0.2688(4) 0.0679(9) Uani 1 1 d . . .
H16 H 0.1627 0.9465 -0.3021 0.082 Uiso 1 1 calc R . .
C17 C 0.21630(15) 0.8397(2) -0.1816(4) 0.0580(8) Uani 1 1 d . . .
H17 H 0.1777 0.8089 -0.1571 0.070 Uiso 1 1 calc R . .
C18 C 0.43158(13) 0.60683(18) 0.2779(3) 0.0440(6) Uani 1 1 d . . .
C19 C 0.47053(15) 0.5280(2) 0.2884(4) 0.0553(8) Uani 1 1 d . . .
H19 H 0.4533 0.4781 0.2191 0.066 Uiso 1 1 calc R . .
C20 C 0.53497(17) 0.5234(2) 0.4016(4) 0.0676(9) Uani 1 1 d . . .
H20 H 0.5610 0.4706 0.4064 0.081 Uiso 1 1 calc R . .
C21 C 0.56114(16) 0.5952(2) 0.5064(4) 0.0647(9) Uani 1 1 d . . .
H21 H 0.6047 0.5913 0.5814 0.078 Uiso 1 1 calc R . .
C22 C 0.52301(17) 0.6725(2) 0.5004(4) 0.0662(9) Uani 1 1 d . . .
H22 H 0.5403 0.7212 0.5731 0.079 Uiso 1 1 calc R . .
C23 C 0.45864(16) 0.6789(2) 0.3866(4) 0.0592(8) Uani 1 1 d . . .
H23 H 0.4332 0.7322 0.3830 0.071 Uiso 1 1 calc R . .
C24 C -0.01364(17) 0.5677(2) -0.0510(5) 0.0752(10) Uani 1 1 d . . .
H24A H -0.0634 0.5725 -0.0647 0.113 Uiso 1 1 calc R . .
H24B H 0.0015 0.6003 -0.1461 0.113 Uiso 1 1 calc R . .
H24C H 0.0082 0.5928 0.0629 0.113 Uiso 1 1 calc R . .
C25 C 0.0275(2) 0.2456(2) 0.0113(5) 0.0860(12) Uani 1 1 d . . .
H25A H 0.0225 0.2798 0.1157 0.129 Uiso 1 1 calc R . .
H25B H 0.0682 0.2080 0.0398 0.129 Uiso 1 1 calc R . .
H25C H -0.0129 0.2085 -0.0259 0.129 Uiso 1 1 calc R . .
C26 C 0.23413(19) 0.2213(2) -0.1328(5) 0.0693(9) Uani 1 1 d . . .
H26A H 0.2526 0.2556 -0.2204 0.104 Uiso 1 1 calc R . .
H26B H 0.2327 0.1585 -0.1647 0.104 Uiso 1 1 calc R . .
H26C H 0.2633 0.2293 -0.0165 0.104 Uiso 1 1 calc R . .
O1 O 0.00533(10) 0.47507(15) -0.0583(3) 0.0665(6) Uani 1 1 d . . .
O2 O 0.03478(11) 0.30547(13) -0.1295(3) 0.0635(6) Uani 1 1 d . . .
O3 O 0.16578(11) 0.25178(13) -0.1280(3) 0.0662(6) Uani 1 1 d . . .
N1 N 0.35254(11) 0.69847(15) 0.0709(3) 0.0438(5) 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 C6 1.389(4) . ?
C1 C2 1.396(4) . ?
C1 C8 1.485(4) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 O3 1.364(3) . ?
C3 C4 1.392(4) . ?
C4 O2 1.373(3) . ?
C4 C5 1.380(4) . ?
C5 O1 1.370(3) . ?
C5 C6 1.393(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(4) . ?
C7 C11 1.392(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C9 C10 1.397(3) . ?
C9 H9 0.9300 . ?
C10 N1 1.342(3) . ?
C10 C18 1.491(3) . ?
C11 N1 1.339(3) . ?
C11 C12 1.483(4) . ?
C12 C17 1.389(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.389(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.382(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O1 1.424(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O2 1.415(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O3 1.417(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.0(3) . . ?
C6 C1 C8 119.2(3) . . ?
C2 C1 C8 120.8(2) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
O3 C3 C2 123.8(3) . . ?
O3 C3 C4 115.5(2) . . ?
C2 C3 C4 120.6(3) . . ?
O2 C4 C5 119.6(3) . . ?
O2 C4 C3 120.6(3) . . ?
C5 C4 C3 119.6(2) . . ?
O1 C5 C4 115.7(2) . . ?
O1 C5 C6 123.9(3) . . ?
C4 C5 C6 120.4(2) . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C11 120.1(3) . . ?
C8 C7 H7 119.9 . . ?
C11 C7 H7 119.9 . . ?
C7 C8 C9 117.7(2) . . ?
C7 C8 C1 119.8(2) . . ?
C9 C8 C1 122.5(3) . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N1 C10 C9 122.6(2) . . ?
N1 C10 C18 115.5(2) . . ?
C9 C10 C18 121.9(2) . . ?
N1 C11 C7 122.0(2) . . ?
N1 C11 C12 116.4(2) . . ?
C7 C11 C12 121.6(2) . . ?
C17 C12 C13 118.2(3) . . ?
C17 C12 C11 120.9(3) . . ?
C13 C12 C11 120.9(2) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C23 C18 C19 118.1(3) . . ?
C23 C18 C10 119.8(3) . . ?
C19 C18 C10 122.1(2) . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.9(3) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C5 O1 C24 117.7(2) . . ?
C4 O2 C25 114.9(2) . . ?
C3 O3 C26 118.2(2) . . ?
C11 N1 C10 118.2(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
C6 C1 C2 C3 2.1(4) . . . . ?
C8 C1 C2 C3 -178.5(2) . . . . ?
C1 C2 C3 O3 176.2(2) . . . . ?
C1 C2 C3 C4 -2.6(4) . . . . ?
O3 C3 C4 O2 -1.9(4) . . . . ?
C2 C3 C4 O2 177.0(2) . . . . ?
O3 C3 C4 C5 -177.4(2) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
O2 C4 C5 O1 4.4(4) . . . . ?
C3 C4 C5 O1 180.0(2) . . . . ?
O2 C4 C5 C6 -175.4(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
O1 C5 C6 C1 179.6(3) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C8 C1 C6 C5 -180.0(2) . . . . ?
C11 C7 C8 C9 -1.7(4) . . . . ?
C11 C7 C8 C1 177.1(2) . . . . ?
C6 C1 C8 C7 -42.9(4) . . . . ?
C2 C1 C8 C7 137.7(3) . . . . ?
C6 C1 C8 C9 135.8(3) . . . . ?
C2 C1 C8 C9 -43.6(3) . . . . ?
C7 C8 C9 C10 2.2(4) . . . . ?
C1 C8 C9 C10 -176.5(2) . . . . ?
C8 C9 C10 N1 -1.2(4) . . . . ?
C8 C9 C10 C18 176.6(2) . . . . ?
C8 C7 C11 N1 0.1(4) . . . . ?
C8 C7 C11 C12 179.4(2) . . . . ?
N1 C11 C12 C17 -151.2(2) . . . . ?
C7 C11 C12 C17 29.5(4) . . . . ?
N1 C11 C12 C13 30.2(4) . . . . ?
C7 C11 C12 C13 -149.1(3) . . . . ?
C17 C12 C13 C14 -1.8(4) . . . . ?
C11 C12 C13 C14 176.9(3) . . . . ?
C12 C13 C14 C15 1.3(5) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C12 0.4(5) . . . . ?
C13 C12 C17 C16 1.0(4) . . . . ?
C11 C12 C17 C16 -177.7(3) . . . . ?
N1 C10 C18 C23 36.5(3) . . . . ?
C9 C10 C18 C23 -141.4(3) . . . . ?
N1 C10 C18 C19 -140.9(3) . . . . ?
C9 C10 C18 C19 41.2(3) . . . . ?
C23 C18 C19 C20 -1.5(4) . . . . ?
C10 C18 C19 C20 176.0(3) . . . . ?
C18 C19 C20 C21 0.9(5) . . . . ?
C19 C20 C21 C22 0.4(5) . . . . ?
C20 C21 C22 C23 -1.1(5) . . . . ?
C19 C18 C23 C22 0.8(4) . . . . ?
C10 C18 C23 C22 -176.7(3) . . . . ?
C21 C22 C23 C18 0.5(5) . . . . ?
C4 C5 O1 C24 -171.8(3) . . . . ?
C6 C5 O1 C24 8.0(4) . . . . ?
C5 C4 O2 C25 -105.3(3) . . . . ?
C3 C4 O2 C25 79.2(3) . . . . ?
C2 C3 O3 C26 0.6(4) . . . . ?
C4 C3 O3 C26 179.4(2) . . . . ?
C7 C11 N1 C10 1.0(4) . . . . ?
C12 C11 N1 C10 -178.3(2) . . . . ?
C9 C10 N1 C11 -0.4(4) . . . . ?
C18 C10 N1 C11 -178.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.59
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.131
_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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1013402'
_audit_update_record             
;
2014-07-11 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.347(2)
_cell_length_b                   7.3632(11)
_cell_length_c                   13.382(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.250(7)
_cell_angle_gamma                90.00
_cell_volume                     1412.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    695
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.02

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6057
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3678
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         28.23
_reflns_number_total             2767
_reflns_number_gt                1543
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1060P)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         2767
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1724
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_restrained_S_all      0.825
_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 0.19463(16) 0.2159(3) 0.72643(19) 0.0335(6) Uani 1 1 d . . .
C2 C 0.11489(18) 0.1228(4) 0.7512(2) 0.0497(8) Uani 1 1 d . . .
H2 H 0.1179 0.0389 0.8031 0.060 Uiso 1 1 calc R . .
C3 C 0.03053(19) 0.1529(4) 0.6996(3) 0.0602(10) Uani 1 1 d . . .
H3 H -0.0225 0.0894 0.7169 0.072 Uiso 1 1 calc R . .
C4 C 0.02547(19) 0.2766(4) 0.6230(2) 0.0550(9) Uani 1 1 d . . .
H4 H -0.0310 0.2971 0.5884 0.066 Uiso 1 1 calc R . .
C5 C 0.10344(18) 0.3698(4) 0.5974(2) 0.0497(8) Uani 1 1 d . . .
H5 H 0.0996 0.4544 0.5458 0.060 Uiso 1 1 calc R . .
C6 C 0.18837(17) 0.3392(3) 0.6480(2) 0.0381(7) Uani 1 1 d . . .
H6 H 0.2413 0.4016 0.6293 0.046 Uiso 1 1 calc R . .
C7 C 0.36972(16) 0.1885(3) 0.72834(19) 0.0320(6) Uani 1 1 d . . .
H7 H 0.3680 0.2243 0.6616 0.038 Uiso 1 1 calc R . .
C8 C 0.28635(16) 0.1796(3) 0.78048(19) 0.0309(6) Uani 1 1 d . . .
C9 C 0.28982(17) 0.1323(3) 0.88020(19) 0.0343(6) Uani 1 1 d . . .
H9 H 0.2350 0.1292 0.9151 0.041 Uiso 1 1 calc R . .
C10 C 0.37666(18) 0.0879(3) 0.93087(19) 0.0327(6) Uani 1 1 d . . .
C11 C 0.45324(15) 0.1448(3) 0.77522(18) 0.0291(6) Uani 1 1 d . . .
C12 C 0.54254(15) 0.1475(3) 0.72560(18) 0.0281(6) Uani 1 1 d . . .
C13 C 0.62607(17) 0.1969(3) 0.77595(19) 0.0350(6) Uani 1 1 d . . .
H13 H 0.6256 0.2275 0.8434 0.042 Uiso 1 1 calc R . .
C14 C 0.70871(17) 0.2010(3) 0.7275(2) 0.0382(7) Uani 1 1 d . . .
H14 H 0.7631 0.2369 0.7622 0.046 Uiso 1 1 calc R . .
C15 C 0.71216(17) 0.1525(3) 0.6278(2) 0.0343(6) Uani 1 1 d . . .
C16 C 0.63030(18) 0.1025(3) 0.5762(2) 0.0407(7) Uani 1 1 d . . .
H16 H 0.6313 0.0697 0.5092 0.049 Uiso 1 1 calc R . .
C17 C 0.54775(17) 0.1017(3) 0.6251(2) 0.0378(7) Uani 1 1 d . . .
H17 H 0.4933 0.0694 0.5895 0.045 Uiso 1 1 calc R . .
C18 C 0.8048(2) 0.1054(5) 0.4860(3) 0.0801(13) Uani 1 1 d . . .
H18A H 0.7782 -0.0134 0.4770 0.120 Uiso 1 1 calc R . .
H18B H 0.8693 0.1026 0.4695 0.120 Uiso 1 1 calc R . .
H18C H 0.7718 0.1903 0.4432 0.120 Uiso 1 1 calc R . .
N1 N 0.45397(14) 0.0952(2) 0.87438(15) 0.0306(5) Uani 1 1 d D . .
H1 H 0.5056(14) 0.060(3) 0.9055(19) 0.037 Uiso 1 1 d D . .
O1 O 0.38398(12) 0.0425(2) 1.02150(13) 0.0430(5) Uani 1 1 d . . .
O2 O 0.79765(13) 0.1596(3) 0.58693(17) 0.0541(6) 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 1.385(4) . ?
C1 C6 1.388(3) . ?
C1 C8 1.501(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.369(3) . ?
C7 C8 1.410(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(3) . ?
C9 C10 1.433(3) . ?
C9 H9 0.9300 . ?
C10 O1 1.258(3) . ?
C10 N1 1.368(3) . ?
C11 N1 1.376(3) . ?
C11 C12 1.466(4) . ?
C12 C17 1.391(4) . ?
C12 C13 1.400(3) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C15 O2 1.363(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.415(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1 0.875(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 C6 118.4(2) . . ?
C2 C1 C8 120.9(2) . . ?
C6 C1 C8 120.7(2) . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C11 C7 C8 120.4(2) . . ?
C11 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 C1 120.6(2) . . ?
C7 C8 C1 119.9(2) . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
O1 C10 N1 120.3(2) . . ?
O1 C10 C9 123.7(3) . . ?
N1 C10 C9 116.0(2) . . ?
C7 C11 N1 118.5(2) . . ?
C7 C11 C12 123.7(2) . . ?
N1 C11 C12 117.82(18) . . ?
C17 C12 C13 116.8(2) . . ?
C17 C12 C11 121.03(19) . . ?
C13 C12 C11 122.2(2) . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
O2 C15 C14 116.3(2) . . ?
O2 C15 C16 124.6(3) . . ?
C14 C15 C16 119.1(3) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 122.6(2) . . ?
C16 C17 H17 118.7 . . ?
C12 C17 H17 118.7 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 N1 C11 124.61(19) . . ?
C10 N1 H1 114.5(18) . . ?
C11 N1 H1 120.8(18) . . ?
C15 O2 C18 118.2(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
C6 C1 C2 C3 -0.5(4) . . . . ?
C8 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
C8 C1 C6 C5 179.0(2) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C11 C7 C8 C9 2.2(3) . . . . ?
C11 C7 C8 C1 -175.98(18) . . . . ?
C2 C1 C8 C9 -33.0(3) . . . . ?
C6 C1 C8 C9 149.3(2) . . . . ?
C2 C1 C8 C7 145.1(3) . . . . ?
C6 C1 C8 C7 -32.6(3) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C1 C8 C9 C10 176.60(19) . . . . ?
C8 C9 C10 O1 -179.4(2) . . . . ?
C8 C9 C10 N1 -0.1(3) . . . . ?
C8 C7 C11 N1 -1.1(3) . . . . ?
C8 C7 C11 C12 178.83(18) . . . . ?
C7 C11 C12 C17 -33.8(3) . . . . ?
N1 C11 C12 C17 146.1(2) . . . . ?
C7 C11 C12 C13 145.7(2) . . . . ?
N1 C11 C12 C13 -34.4(3) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
C11 C12 C13 C14 -179.0(2) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C14 C15 O2 -179.4(2) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
O2 C15 C16 C17 -179.5(2) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C12 -0.8(4) . . . . ?
C13 C12 C17 C16 0.6(3) . . . . ?
C11 C12 C17 C16 -179.9(2) . . . . ?
O1 C10 N1 C11 -179.39(19) . . . . ?
C9 C10 N1 C11 1.3(3) . . . . ?
C7 C11 N1 C10 -0.7(3) . . . . ?
C12 C11 N1 C10 179.38(18) . . . . ?
C14 C15 O2 C18 178.0(2) . . . . ?
C16 C15 O2 C18 -2.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.792
_diffrn_reflns_theta_full        28.23
_diffrn_measured_fraction_theta_full 0.792
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1029360'
_audit_update_record             
;
2014-10-15 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Department of ChemistryUniversity of AnywhereSometownSomewhere, UK'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2 O3'
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   15.617(8)
_cell_length_b                   5.565(3)
_cell_length_c                   18.620(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.024(5)
_cell_angle_gamma                90.00
_cell_volume                     1489.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    932
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      18.36

_exptl_crystal_description       Prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11286
_diffrn_reflns_av_R_equivalents  0.1068
_diffrn_reflns_av_sigmaI/netI    0.1274
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         26.38
_reflns_number_total             2972
_reflns_number_gt                1051
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1780P)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         2972
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1994
_refine_ls_R_factor_gt           0.0891
_refine_ls_wR_factor_ref         0.3334
_refine_ls_wR_factor_gt          0.2575
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_restrained_S_all      0.908
_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 0.1107(4) 1.2820(10) 0.4139(4) 0.0640(16) Uani 1 1 d . . .
C2 C 0.0525(6) 1.145(2) 0.3625(6) 0.168(5) Uani 1 1 d . . .
H2 H 0.0739 1.0027 0.3494 0.202 Uiso 1 1 calc R . .
C3 C -0.0396(7) 1.200(3) 0.3262(6) 0.210(8) Uani 1 1 d . . .
H3 H -0.0773 1.0914 0.2894 0.252 Uiso 1 1 calc R . .
C4 C -0.0770(6) 1.383(3) 0.3384(10) 0.205(8) Uani 1 1 d . . .
H4 H -0.1406 1.4122 0.3139 0.246 Uiso 1 1 calc R . .
C5 C -0.0215(9) 1.528(3) 0.3872(16) 0.348(15) Uani 1 1 d . . .
H5 H -0.0444 1.6742 0.3960 0.418 Uiso 1 1 calc R . .
C6 C 0.0758(7) 1.4740(19) 0.4299(11) 0.257(10) Uani 1 1 d . . .
H6 H 0.1131 1.5778 0.4686 0.308 Uiso 1 1 calc R . .
C7 C 0.2365(3) 1.0431(10) 0.5174(3) 0.0621(16) Uani 1 1 d . . .
H7 H 0.1916 0.9979 0.5359 0.075 Uiso 1 1 calc R . .
C8 C 0.2138(4) 1.2407(11) 0.4572(3) 0.0713(18) Uani 1 1 d . . .
H8 H 0.2393 1.3894 0.4858 0.086 Uiso 1 1 calc R . .
C9 C 0.2651(3) 1.1945(10) 0.4077(3) 0.0618(16) Uani 1 1 d . . .
H9 H 0.2342 1.0567 0.3751 0.074 Uiso 1 1 calc R . .
C10 C 0.3655(3) 1.1219(9) 0.4490(3) 0.0520(14) Uani 1 1 d . . .
C11 C 0.3176(3) 0.9320(9) 0.5446(3) 0.0501(13) Uani 1 1 d . . .
C12 C 0.3472(3) 0.7511(9) 0.6075(3) 0.0471(13) Uani 1 1 d . . .
C13 C 0.4064(3) 0.5626(9) 0.6087(3) 0.0561(14) Uani 1 1 d . . .
H13 H 0.4297 0.5499 0.5698 0.067 Uiso 1 1 calc R . .
C14 C 0.4302(4) 0.3952(10) 0.6678(3) 0.0621(15) Uani 1 1 d . . .
H14 H 0.4692 0.2687 0.6678 0.075 Uiso 1 1 calc R . .
C15 C 0.3987(4) 0.4091(11) 0.7259(3) 0.0682(16) Uani 1 1 d . . .
H15 H 0.4153 0.2921 0.7647 0.082 Uiso 1 1 calc R . .
C16 C 0.3423(4) 0.5959(11) 0.7276(3) 0.0677(16) Uani 1 1 d . . .
H16 H 0.3213 0.6080 0.7678 0.081 Uiso 1 1 calc R . .
C17 C 0.3168(3) 0.7671(10) 0.6685(3) 0.0594(15) Uani 1 1 d . . .
H17 H 0.2788 0.8945 0.6698 0.071 Uiso 1 1 calc R . .
O1 O 0.4234(2) 1.1769(7) 0.4222(2) 0.0696(12) Uani 1 1 d . . .
O2 O 0.2792(4) 1.5941(8) 0.3796(3) 0.1002(17) Uani 1 1 d . . .
O3 O 0.2330(3) 1.3447(8) 0.2842(3) 0.0885(14) Uani 1 1 d . . .
N1 N 0.3829(3) 0.9882(8) 0.5120(2) 0.0505(12) Uani 1 1 d D . .
H1A H 0.4365(19) 0.928(8) 0.533(3) 0.061 Uiso 1 1 d D . .
N2 N 0.2579(3) 1.3947(10) 0.3522(3) 0.0616(13) 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 C6 1.286(10) . ?
C1 C2 1.281(10) . ?
C1 C8 1.509(8) . ?
C2 C3 1.363(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.240(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.27(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.445(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.319(6) . ?
C7 C8 1.510(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.462(6) . ?
C8 H8 0.9800 . ?
C9 N2 1.493(6) . ?
C9 C10 1.506(7) . ?
C9 H9 0.9800 . ?
C10 O1 1.231(5) . ?
C10 N1 1.325(6) . ?
C11 N1 1.410(6) . ?
C11 C12 1.475(7) . ?
C12 C13 1.393(7) . ?
C12 C17 1.395(6) . ?
C13 C14 1.378(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
O2 N2 1.212(6) . ?
O3 N2 1.204(5) . ?
N1 H1A 0.84(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
C6 C1 C2 115.2(8) . . ?
C6 C1 C8 117.6(8) . . ?
C2 C1 C8 127.3(7) . . ?
C1 C2 C3 122.8(11) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 125.0(14) . . ?
C4 C3 H3 117.5 . . ?
C2 C3 H3 117.5 . . ?
C3 C4 C5 114.5(11) . . ?
C3 C4 H4 122.8 . . ?
C5 C4 H4 122.8 . . ?
C4 C5 C6 122.7(13) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C1 C6 C5 119.7(12) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C11 C7 C8 122.5(4) . . ?
C11 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C1 115.1(5) . . ?
C9 C8 C7 108.2(4) . . ?
C1 C8 C7 113.5(4) . . ?
C9 C8 H8 106.5 . . ?
C1 C8 H8 106.5 . . ?
C7 C8 H8 106.5 . . ?
C8 C9 N2 113.1(4) . . ?
C8 C9 C10 116.3(4) . . ?
N2 C9 C10 109.6(4) . . ?
C8 C9 H9 105.6 . . ?
N2 C9 H9 105.6 . . ?
C10 C9 H9 105.6 . . ?
O1 C10 N1 124.8(4) . . ?
O1 C10 C9 120.7(4) . . ?
N1 C10 C9 114.5(4) . . ?
C7 C11 N1 118.5(5) . . ?
C7 C11 C12 125.5(4) . . ?
N1 C11 C12 116.0(4) . . ?
C13 C12 C17 118.1(5) . . ?
C13 C12 C11 121.8(4) . . ?
C17 C12 C11 120.2(4) . . ?
C14 C13 C12 119.5(5) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 122.1(5) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 119.9(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.4(5) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C12 121.1(5) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C10 N1 C11 125.0(4) . . ?
C10 N1 H1A 117(3) . . ?
C11 N1 H1A 118(3) . . ?
O3 N2 O2 125.2(5) . . ?
O3 N2 C9 117.5(5) . . ?
O2 N2 C9 117.3(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
C6 C1 C2 C3 1.0(17) . . . . ?
C8 C1 C2 C3 -179.5(9) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 2(3) . . . . ?
C3 C4 C5 C6 -5(3) . . . . ?
C2 C1 C6 C5 -4(2) . . . . ?
C8 C1 C6 C5 176.9(14) . . . . ?
C4 C5 C6 C1 6(3) . . . . ?
C6 C1 C8 C9 -126.9(10) . . . . ?
C2 C1 C8 C9 53.5(10) . . . . ?
C6 C1 C8 C7 107.7(10) . . . . ?
C2 C1 C8 C7 -71.8(9) . . . . ?
C11 C7 C8 C9 30.7(8) . . . . ?
C11 C7 C8 C1 159.7(5) . . . . ?
C1 C8 C9 N2 59.3(7) . . . . ?
C7 C8 C9 N2 -172.6(5) . . . . ?
C1 C8 C9 C10 -172.5(5) . . . . ?
C7 C8 C9 C10 -44.4(7) . . . . ?
C8 C9 C10 O1 -148.5(5) . . . . ?
N2 C9 C10 O1 -18.6(7) . . . . ?
C8 C9 C10 N1 34.7(7) . . . . ?
N2 C9 C10 N1 164.6(5) . . . . ?
C8 C7 C11 N1 -4.7(8) . . . . ?
C8 C7 C11 C12 175.0(5) . . . . ?
C7 C11 C12 C13 147.7(5) . . . . ?
N1 C11 C12 C13 -32.6(7) . . . . ?
C7 C11 C12 C17 -33.1(8) . . . . ?
N1 C11 C12 C17 146.7(5) . . . . ?
C17 C12 C13 C14 2.2(7) . . . . ?
C11 C12 C13 C14 -178.5(4) . . . . ?
C12 C13 C14 C15 -0.8(8) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
C14 C15 C16 C17 1.1(8) . . . . ?
C15 C16 C17 C12 0.4(8) . . . . ?
C13 C12 C17 C16 -2.1(7) . . . . ?
C11 C12 C17 C16 178.7(5) . . . . ?
O1 C10 N1 C11 177.6(5) . . . . ?
C9 C10 N1 C11 -5.8(7) . . . . ?
C7 C11 N1 C10 -9.2(8) . . . . ?
C12 C11 N1 C10 171.0(5) . . . . ?
C8 C9 N2 O3 -127.1(5) . . . . ?
C10 C9 N2 O3 101.3(6) . . . . ?
C8 C9 N2 O2 54.2(7) . . . . ?
C10 C9 N2 O2 -77.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.066
