# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_151030e
_database_code_depnum_ccdc_archive 'CCDC 1517853'
_audit_update_record             
;
2016-11-17 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 F O2'
_chemical_formula_weight         280.28

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.4990(9)
_cell_length_b                   6.1878(7)
_cell_length_c                   11.9593(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.735(2)
_cell_angle_gamma                90.00
_cell_volume                     682.84(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    807
_cell_measurement_theta_min      3.129
_cell_measurement_theta_max      25.622

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3374
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0825
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2235
_reflns_number_gt                1332
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0432P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.3(18)
_refine_ls_number_reflns         2235
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
F1 F -0.0139(3) 0.0091(6) 0.8973(2) 0.1004(11) Uani 1 1 d . . .
O1 O 0.3209(3) 0.6558(5) 0.6529(2) 0.0618(9) Uani 1 1 d . . .
H1 H 0.3608 0.7083 0.6055 0.093 Uiso 1 1 calc R . .
O2 O 0.3931(2) -0.1534(5) 0.4621(2) 0.0490(8) Uani 1 1 d . . .
C1 C 0.2582(4) 0.4644(7) 0.6123(3) 0.0411(10) Uani 1 1 d . . .
C2 C 0.2645(4) 0.3792(6) 0.5086(3) 0.0415(10) Uani 1 1 d . . .
H2 H 0.3125 0.4548 0.4615 0.050 Uiso 1 1 calc R . .
C3 C 0.2003(4) 0.1801(7) 0.4716(3) 0.0408(10) Uani 1 1 d . . .
C4 C 0.1288(4) 0.0694(7) 0.5401(3) 0.0441(10) Uani 1 1 d . . .
H4 H 0.0835 -0.0609 0.5148 0.053 Uiso 1 1 calc R . .
C5 C 0.1233(4) 0.1510(8) 0.6481(3) 0.0425(10) Uani 1 1 d . . .
C6 C 0.1868(4) 0.3526(7) 0.6863(3) 0.0384(10) Uani 1 1 d . . .
C7 C 0.1799(4) 0.4319(8) 0.7942(3) 0.0550(13) Uani 1 1 d . . .
H7 H 0.2216 0.5649 0.8187 0.066 Uiso 1 1 calc R . .
C8 C 0.1128(5) 0.3170(9) 0.8645(3) 0.0640(14) Uani 1 1 d . . .
H8 H 0.1090 0.3698 0.9365 0.077 Uiso 1 1 calc R . .
C9 C 0.0512(5) 0.1212(10) 0.8260(4) 0.0645(15) Uani 1 1 d . . .
C10 C 0.0542(4) 0.0346(8) 0.7227(4) 0.0560(12) Uani 1 1 d . . .
H10 H 0.0116 -0.0990 0.7007 0.067 Uiso 1 1 calc R . .
C11 C 0.2150(4) 0.0896(7) 0.3586(3) 0.0488(11) Uani 1 1 d . . .
H11A H 0.2383 0.2066 0.3121 0.059 Uiso 1 1 calc R . .
H11B H 0.1222 0.0302 0.3184 0.059 Uiso 1 1 calc R . .
C12 C 0.3284(4) -0.0831(7) 0.3687(3) 0.0415(10) Uani 1 1 d . . .
C13 C 0.3571(4) -0.1774(8) 0.2619(3) 0.0396(9) Uani 1 1 d . . .
C14 C 0.2945(4) -0.0969(8) 0.1536(3) 0.0539(12) Uani 1 1 d . . .
H14 H 0.2323 0.0211 0.1456 0.065 Uiso 1 1 calc R . .
C15 C 0.3248(5) -0.1928(9) 0.0568(3) 0.0677(14) Uani 1 1 d . . .
H15 H 0.2813 -0.1397 -0.0159 0.081 Uiso 1 1 calc R . .
C16 C 0.4165(5) -0.3618(9) 0.0672(4) 0.0708(15) Uani 1 1 d . . .
H16 H 0.4370 -0.4233 0.0019 0.085 Uiso 1 1 calc R . .
C17 C 0.4800(4) -0.4434(8) 0.1748(4) 0.0604(13) Uani 1 1 d . . .
H17 H 0.5421 -0.5615 0.1817 0.072 Uiso 1 1 calc R . .
C18 C 0.4517(4) -0.3506(7) 0.2717(3) 0.0514(11) Uani 1 1 d . . .
H18 H 0.4963 -0.4043 0.3441 0.062 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.356(5) . ?
O1 C1 1.362(5) . ?
O1 H1 0.8200 . ?
O2 C12 1.220(4) . ?
C1 C2 1.362(5) . ?
C1 C6 1.416(5) . ?
C2 C3 1.399(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(5) . ?
C3 C11 1.499(5) . ?
C4 C5 1.400(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(6) . ?
C5 C10 1.423(5) . ?
C6 C7 1.397(5) . ?
C7 C8 1.368(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.353(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.501(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.487(5) . ?
C13 C14 1.383(5) . ?
C13 C18 1.386(6) . ?
C14 C15 1.390(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.347(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C2 C1 O1 123.4(4) . . ?
C2 C1 C6 120.7(4) . . ?
O1 C1 C6 115.8(3) . . ?
C1 C2 C3 121.2(4) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 C11 121.3(4) . . ?
C2 C3 C11 119.1(4) . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 C10 121.3(4) . . ?
C6 C5 C10 118.0(4) . . ?
C7 C6 C5 119.9(4) . . ?
C7 C6 C1 122.7(4) . . ?
C5 C6 C1 117.4(3) . . ?
C8 C7 C6 121.1(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 118.4(4) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 F1 118.9(5) . . ?
C10 C9 C8 123.7(4) . . ?
F1 C9 C8 117.5(5) . . ?
C9 C10 C5 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C5 C10 H10 120.5 . . ?
C3 C11 C12 114.3(3) . . ?
C3 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C3 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
O2 C12 C13 119.4(4) . . ?
O2 C12 C11 121.5(3) . . ?
C13 C12 C11 119.0(3) . . ?
C14 C13 C18 119.0(3) . . ?
C14 C13 C12 122.5(4) . . ?
C18 C13 C12 118.6(3) . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 120.3(4) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.9(3) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C1 C2 C3 C11 -177.8(3) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C11 C3 C4 C5 176.4(4) . . . . ?
C3 C4 C5 C6 2.4(6) . . . . ?
C3 C4 C5 C10 -177.6(4) . . . . ?
C4 C5 C6 C7 179.8(4) . . . . ?
C10 C5 C6 C7 -0.2(5) . . . . ?
C4 C5 C6 C1 -1.4(6) . . . . ?
C10 C5 C6 C1 178.6(3) . . . . ?
C2 C1 C6 C7 178.8(4) . . . . ?
O1 C1 C6 C7 0.2(5) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
O1 C1 C6 C5 -178.6(3) . . . . ?
C5 C6 C7 C8 0.2(6) . . . . ?
C1 C6 C7 C8 -178.5(4) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 C10 0.6(7) . . . . ?
C7 C8 C9 F1 179.6(4) . . . . ?
F1 C9 C10 C5 -179.5(4) . . . . ?
C8 C9 C10 C5 -0.6(7) . . . . ?
C4 C5 C10 C9 -179.6(4) . . . . ?
C6 C5 C10 C9 0.3(6) . . . . ?
C4 C3 C11 C12 -77.4(5) . . . . ?
C2 C3 C11 C12 100.8(4) . . . . ?
C3 C11 C12 O2 5.7(5) . . . . ?
C3 C11 C12 C13 -177.2(4) . . . . ?
O2 C12 C13 C14 -175.9(4) . . . . ?
C11 C12 C13 C14 6.9(6) . . . . ?
O2 C12 C13 C18 3.2(6) . . . . ?
C11 C12 C13 C18 -173.9(4) . . . . ?
C18 C13 C14 C15 1.3(6) . . . . ?
C12 C13 C14 C15 -179.6(4) . . . . ?
C13 C14 C15 C16 -1.0(7) . . . . ?
C14 C15 C16 C17 0.9(8) . . . . ?
C15 C16 C17 C18 -1.0(7) . . . . ?
C16 C17 C18 C13 1.3(6) . . . . ?
C14 C13 C18 C17 -1.4(6) . . . . ?
C12 C13 C18 C17 179.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.170
_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_160418a
_database_code_depnum_ccdc_archive 'CCDC 1554760'
_audit_update_record             
;
2017-06-07 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Cl N O2'
_chemical_formula_weight         297.73

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.3531(7)
_cell_length_b                   10.7592(9)
_cell_length_c                   14.2252(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.868(2)
_cell_angle_gamma                90.00
_cell_volume                     1414.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    945
_cell_measurement_theta_min      2.899
_cell_measurement_theta_max      25.813

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9449
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6514
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_av_sigmaI/netI    0.1544
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2460
_reflns_number_gt                958
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0584P)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       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2460
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1916
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.1814
_refine_ls_wR_factor_gt          0.1557
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Cl1 Cl 1.42929(17) 0.13498(17) 1.05148(13) 0.0803(7) Uani 1 1 d . . .
N1 N 0.7182(5) 0.2233(5) 0.8021(3) 0.0513(13) Uani 1 1 d . . .
O1 O 0.6942(4) 0.1448(4) 0.4692(2) 0.0580(12) Uani 1 1 d . . .
H1 H 0.7281 0.1680 0.4224 0.087 Uiso 1 1 calc R . .
O2 O 0.8992(5) 0.4917(4) 0.8271(3) 0.0720(14) Uani 1 1 d . . .
C1 C 0.6182(7) 0.1387(7) 0.8029(5) 0.068(2) Uani 1 1 d . . .
H1A H 0.5845 0.1252 0.8602 0.081 Uiso 1 1 calc R . .
C2 C 0.5579(7) 0.0672(6) 0.7258(5) 0.069(2) Uani 1 1 d . . .
H2 H 0.4878 0.0077 0.7319 0.083 Uiso 1 1 calc R . .
C3 C 0.6038(6) 0.0865(6) 0.6412(4) 0.0584(18) Uani 1 1 d . . .
H3 H 0.5657 0.0399 0.5882 0.070 Uiso 1 1 calc R . .
C4 C 0.7086(6) 0.1767(5) 0.6342(4) 0.0397(15) Uani 1 1 d . . .
C5 C 0.7690(6) 0.2447(5) 0.7167(4) 0.0415(15) Uani 1 1 d . . .
C6 C 0.8832(6) 0.3277(5) 0.7139(4) 0.0446(16) Uani 1 1 d . . .
C7 C 0.9328(6) 0.3509(5) 0.6293(4) 0.0496(16) Uani 1 1 d . . .
C8 C 0.8676(7) 0.2890(6) 0.5463(4) 0.0509(16) Uani 1 1 d . . .
H8 H 0.8986 0.3075 0.4888 0.061 Uiso 1 1 calc R . .
C9 C 0.7621(7) 0.2042(6) 0.5474(4) 0.0492(16) Uani 1 1 d . . .
C10 C 0.9454(7) 0.3910(6) 0.8032(4) 0.0487(16) Uani 1 1 d . . .
C11 C 1.0729(6) 0.3326(5) 0.8620(4) 0.0425(15) Uani 1 1 d . . .
C12 C 1.1304(6) 0.2245(5) 0.8332(4) 0.0519(16) Uani 1 1 d . . .
H12 H 1.0932 0.1917 0.7740 0.062 Uiso 1 1 calc R . .
C13 C 1.2426(7) 0.1622(6) 0.8896(5) 0.0589(18) Uani 1 1 d . . .
H13 H 1.2805 0.0889 0.8691 0.071 Uiso 1 1 calc R . .
C14 C 1.2962(6) 0.2132(6) 0.9777(5) 0.0503(16) Uani 1 1 d . . .
C15 C 1.2431(6) 0.3236(6) 1.0081(4) 0.0559(17) Uani 1 1 d . . .
H15 H 1.2810 0.3571 1.0669 0.067 Uiso 1 1 calc R . .
C16 C 1.1333(6) 0.3830(6) 0.9498(4) 0.0505(16) Uani 1 1 d . . .
H16 H 1.0984 0.4582 0.9691 0.061 Uiso 1 1 calc R . .
C17 C 1.0612(6) 0.4363(6) 0.6261(4) 0.0625(19) Uani 1 1 d . . .
H17A H 1.0557 0.5056 0.6678 0.094 Uiso 1 1 calc R . .
H17B H 1.0599 0.4658 0.5623 0.094 Uiso 1 1 calc R . .
H17C H 1.1493 0.3913 0.6462 0.094 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.719(6) . ?
N1 C1 1.306(7) . ?
N1 C5 1.389(6) . ?
O1 C9 1.353(6) . ?
O1 H1 0.8200 . ?
O2 C10 1.233(6) . ?
C1 C2 1.386(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.354(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.425(7) . ?
C4 C9 1.433(7) . ?
C5 C6 1.397(7) . ?
C6 C7 1.378(7) . ?
C6 C10 1.480(8) . ?
C7 C8 1.409(7) . ?
C7 C17 1.518(7) . ?
C8 C9 1.347(7) . ?
C8 H8 0.9300 . ?
C10 C11 1.486(8) . ?
C11 C12 1.369(7) . ?
C11 C16 1.398(7) . ?
C12 C13 1.391(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(7) . ?
C15 C16 1.375(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C1 N1 C5 117.7(5) . . ?
C9 O1 H1 109.5 . . ?
N1 C1 C2 125.8(6) . . ?
N1 C1 H1A 117.1 . . ?
C2 C1 H1A 117.1 . . ?
C3 C2 C1 118.1(6) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 C9 123.3(6) . . ?
C5 C4 C9 117.3(5) . . ?
N1 C5 C6 119.8(5) . . ?
N1 C5 C4 119.3(5) . . ?
C6 C5 C4 120.8(5) . . ?
C7 C6 C5 120.2(5) . . ?
C7 C6 C10 121.7(5) . . ?
C5 C6 C10 118.0(5) . . ?
C6 C7 C8 119.0(5) . . ?
C6 C7 C17 120.7(5) . . ?
C8 C7 C17 120.2(5) . . ?
C9 C8 C7 122.3(6) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 O1 124.3(5) . . ?
C8 C9 C4 120.2(6) . . ?
O1 C9 C4 115.4(5) . . ?
O2 C10 C6 122.2(6) . . ?
O2 C10 C11 120.1(6) . . ?
C6 C10 C11 117.6(5) . . ?
C12 C11 C16 118.2(6) . . ?
C12 C11 C10 120.6(5) . . ?
C16 C11 C10 121.1(5) . . ?
C11 C12 C13 122.2(6) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 117.7(6) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C15 C14 C13 121.6(6) . . ?
C15 C14 Cl1 119.4(5) . . ?
C13 C14 Cl1 118.9(5) . . ?
C16 C15 C14 118.8(6) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C11 121.3(6) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.3(10) . . . . ?
N1 C1 C2 C3 -0.9(11) . . . . ?
C1 C2 C3 C4 -0.2(9) . . . . ?
C2 C3 C4 C5 1.8(9) . . . . ?
C2 C3 C4 C9 -179.3(6) . . . . ?
C1 N1 C5 C6 -175.3(5) . . . . ?
C1 N1 C5 C4 1.4(8) . . . . ?
C3 C4 C5 N1 -2.5(8) . . . . ?
C9 C4 C5 N1 178.5(5) . . . . ?
C3 C4 C5 C6 174.2(5) . . . . ?
C9 C4 C5 C6 -4.7(8) . . . . ?
N1 C5 C6 C7 -179.0(5) . . . . ?
C4 C5 C6 C7 4.3(8) . . . . ?
N1 C5 C6 C10 -0.5(8) . . . . ?
C4 C5 C6 C10 -177.2(5) . . . . ?
C5 C6 C7 C8 -0.6(8) . . . . ?
C10 C6 C7 C8 -179.0(5) . . . . ?
C5 C6 C7 C17 -177.2(5) . . . . ?
C10 C6 C7 C17 4.3(8) . . . . ?
C6 C7 C8 C9 -2.6(9) . . . . ?
C17 C7 C8 C9 174.0(5) . . . . ?
C7 C8 C9 O1 178.4(5) . . . . ?
C7 C8 C9 C4 2.1(9) . . . . ?
C3 C4 C9 C8 -177.3(5) . . . . ?
C5 C4 C9 C8 1.6(8) . . . . ?
C3 C4 C9 O1 6.0(8) . . . . ?
C5 C4 C9 O1 -175.0(5) . . . . ?
C7 C6 C10 O2 88.4(7) . . . . ?
C5 C6 C10 O2 -90.1(7) . . . . ?
C7 C6 C10 C11 -88.1(7) . . . . ?
C5 C6 C10 C11 93.4(6) . . . . ?
O2 C10 C11 C12 -176.1(5) . . . . ?
C6 C10 C11 C12 0.5(8) . . . . ?
O2 C10 C11 C16 6.8(8) . . . . ?
C6 C10 C11 C16 -176.6(5) . . . . ?
C16 C11 C12 C13 2.1(8) . . . . ?
C10 C11 C12 C13 -175.1(5) . . . . ?
C11 C12 C13 C14 0.0(9) . . . . ?
C12 C13 C14 C15 -1.5(9) . . . . ?
C12 C13 C14 Cl1 177.1(4) . . . . ?
C13 C14 C15 C16 0.8(9) . . . . ?
Cl1 C14 C15 C16 -177.8(4) . . . . ?
C14 C15 C16 C11 1.4(8) . . . . ?
C12 C11 C16 C15 -2.8(8) . . . . ?
C10 C11 C16 C15 174.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.065
