# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mo_dm15225_0m
_database_code_depnum_ccdc_archive 'CCDC 1058933'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_audit_creation_date             2015-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H13 N S, C H Cl3'
_chemical_formula_sum            'C18 H14 Cl3 N S'
_chemical_formula_weight         382.71
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7687(6)
_cell_length_b                   9.4304(7)
_cell_length_c                   12.8027(10)
_cell_angle_alpha                101.3420(10)
_cell_angle_beta                 104.7500(10)
_cell_angle_gamma                102.5070(10)
_cell_volume                     853.44(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4893
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0315 before and 0.0237 after correction.
The Ratio of minimum to maximum transmission is 0.9109.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0110
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8613
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.558
_diffrn_reflns_theta_min         1.707
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4419
_reflns_number_total             5173
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         5173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.178
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1503
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.24140(6) 0.19647(4) 0.04041(3) 0.03012(12) Uani 1 1 d . . . . .
N1 N 0.37173(16) 0.01035(13) 0.14952(10) 0.0208(2) Uani 1 1 d . . . . .
C1 C 0.40036(19) -0.12806(15) 0.15058(11) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.49581(19) -0.15206(18) 0.25477(11) 0.0235(3) Uani 1 1 d . . . . .
H2 H 0.5340 -0.0724 0.3214 0.028 Uiso 1 1 calc R . . . .
C3 C 0.5325(2) -0.28241(19) 0.26094(13) 0.0288(3) Uani 1 1 d . . . . .
H3 H 0.6005 -0.2934 0.3305 0.035 Uiso 1 1 calc R . . . .
C4 C 0.4704(2) -0.40304(17) 0.16448(13) 0.0262(3) Uani 1 1 d . . . . .
H4 H 0.4939 -0.4966 0.1695 0.031 Uiso 1 1 calc R . . . .
C5 C 0.3760(2) -0.38830(15) 0.06263(12) 0.0222(3) Uani 1 1 d . . . . .
H5 H 0.3353 -0.4717 -0.0017 0.027 Uiso 1 1 calc R . . . .
C6 C 0.33840(18) -0.25019(15) 0.05229(11) 0.0190(2) Uani 1 1 d . . . . .
C7 C 0.24654(18) -0.22644(15) -0.05257(11) 0.0187(2) Uani 1 1 d . . . . .
C8 C 0.22653(18) -0.08525(15) -0.05293(11) 0.0192(2) Uani 1 1 d . . . . .
C9 C 0.28967(18) 0.02689(15) 0.05117(11) 0.0197(2) Uani 1 1 d . . . . .
C10 C 0.1312(2) -0.03625(16) -0.15074(13) 0.0271(3) Uani 1 1 d . . . . .
H10A H 0.0013 -0.1001 -0.1844 0.033 Uiso 1 1 calc R . . . .
H10B H 0.1949 -0.0476 -0.2084 0.033 Uiso 1 1 calc R . . . .
C11 C 0.1347(2) 0.12899(19) -0.11126(15) 0.0325(3) Uani 1 1 d . . . . .
H11A H 0.0066 0.1383 -0.1318 0.039 Uiso 1 1 calc R . . . .
H11B H 0.2062 0.1909 -0.1484 0.039 Uiso 1 1 calc R . . . .
C12 C 0.17317(18) -0.35181(14) -0.15735(11) 0.0197(2) Uani 1 1 d . . . . .
C13 C 0.2437(2) -0.34450(16) -0.24655(11) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.3383 -0.2580 -0.2410 0.027 Uiso 1 1 calc R . . . .
C14 C 0.1765(2) -0.46309(18) -0.34370(12) 0.0274(3) Uani 1 1 d . . . . .
H14 H 0.2267 -0.4579 -0.4037 0.033 Uiso 1 1 calc R . . . .
C15 C 0.0362(2) -0.58887(17) -0.35295(13) 0.0298(3) Uani 1 1 d . . . . .
H15 H -0.0098 -0.6698 -0.4192 0.036 Uiso 1 1 calc R . . . .
C16 C -0.0368(2) -0.59613(17) -0.26501(14) 0.0297(3) Uani 1 1 d . . . . .
H16 H -0.1338 -0.6816 -0.2716 0.036 Uiso 1 1 calc R . . . .
C17 C 0.0318(2) -0.47844(16) -0.16737(13) 0.0256(3) Uani 1 1 d . . . . .
H17 H -0.0178 -0.4843 -0.1072 0.031 Uiso 1 1 calc R . . . .
Cl1 Cl 0.44198(6) -0.21510(5) -0.47736(3) 0.03636(13) Uani 1 1 d . . . . .
Cl2 Cl 0.82926(7) -0.05872(7) -0.42510(4) 0.04883(15) Uani 1 1 d . . . . .
Cl3 Cl 0.72317(8) -0.34758(5) -0.37800(4) 0.04633(15) Uani 1 1 d . . . . .
C18 C 0.6661(2) -0.17908(18) -0.38424(12) 0.0269(3) Uani 1 1 d . . . . .
H18 H 0.6680 -0.1270 -0.3078 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.7428(13) . ?
S1 C11 1.8244(19) . ?
N1 C1 1.3728(17) . ?
N1 C9 1.3144(18) . ?
C1 C2 1.4381(18) . ?
C1 C6 1.4224(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.333(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3732(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.4184(18) . ?
C6 C7 1.4357(18) . ?
C7 C8 1.3743(18) . ?
C7 C12 1.4891(18) . ?
C8 C9 1.4225(18) . ?
C8 C10 1.4946(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.533(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3935(19) . ?
C12 C17 1.3958(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(2) . ?
C17 H17 0.9500 . ?
Cl1 C18 1.7594(16) . ?
Cl2 C18 1.7655(17) . ?
Cl3 C18 1.7507(16) . ?
C18 H18 1.0000 . ?

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
C9 S1 C11 93.16(7) . . ?
C9 N1 C1 116.33(11) . . ?
N1 C1 C2 119.22(12) . . ?
N1 C1 C6 122.59(12) . . ?
C6 C1 C2 118.19(12) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.17(13) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.67(14) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.05(14) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.87(13) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 118.63(12) . . ?
C5 C6 C1 118.00(12) . . ?
C5 C6 C7 123.34(12) . . ?
C6 C7 C12 120.85(11) . . ?
C8 C7 C6 118.00(12) . . ?
C8 C7 C12 121.14(12) . . ?
C7 C8 C9 118.25(12) . . ?
C7 C8 C10 127.25(12) . . ?
C9 C8 C10 114.33(12) . . ?
N1 C9 S1 120.23(10) . . ?
N1 C9 C8 126.11(12) . . ?
C8 C9 S1 113.63(10) . . ?
C8 C10 H10A 109.8 . . ?
C8 C10 H10B 109.8 . . ?
C8 C10 C11 109.27(13) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
S1 C11 H11A 109.8 . . ?
S1 C11 H11B 109.8 . . ?
C10 C11 S1 109.50(11) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C7 120.75(12) . . ?
C13 C12 C17 119.14(12) . . ?
C17 C12 C7 120.11(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.50(14) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.02(14) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.85(14) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.15(14) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.32(14) . . ?
C16 C17 H17 119.8 . . ?
Cl1 C18 Cl2 110.02(8) . . ?
Cl1 C18 H18 108.4 . . ?
Cl2 C18 H18 108.4 . . ?
Cl3 C18 Cl1 110.75(8) . . ?
Cl3 C18 Cl2 110.93(9) . . ?
Cl3 C18 H18 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -178.11(14) . . . . ?
N1 C1 C6 C5 179.72(12) . . . . ?
N1 C1 C6 C7 1.6(2) . . . . ?
C1 N1 C9 S1 178.47(10) . . . . ?
C1 N1 C9 C8 0.8(2) . . . . ?
C1 C2 C3 C4 -2.7(2) . . . . ?
C1 C6 C7 C8 1.33(19) . . . . ?
C1 C6 C7 C12 -177.90(12) . . . . ?
C2 C1 C6 C5 -0.58(19) . . . . ?
C2 C1 C6 C7 -178.66(12) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 177.59(13) . . . . ?
C5 C6 C7 C8 -176.64(12) . . . . ?
C5 C6 C7 C12 4.1(2) . . . . ?
C6 C1 C2 C3 2.2(2) . . . . ?
C6 C7 C8 C9 -3.02(19) . . . . ?
C6 C7 C8 C10 -177.93(13) . . . . ?
C6 C7 C12 C13 -116.79(14) . . . . ?
C6 C7 C12 C17 63.38(18) . . . . ?
C7 C8 C9 S1 -175.70(10) . . . . ?
C7 C8 C9 N1 2.1(2) . . . . ?
C7 C8 C10 C11 177.37(14) . . . . ?
C7 C12 C13 C14 179.02(13) . . . . ?
C7 C12 C17 C16 -179.80(13) . . . . ?
C8 C7 C12 C13 64.02(18) . . . . ?
C8 C7 C12 C17 -115.81(15) . . . . ?
C8 C10 C11 S1 -3.33(16) . . . . ?
C9 S1 C11 C10 2.87(12) . . . . ?
C9 N1 C1 C2 177.64(12) . . . . ?
C9 N1 C1 C6 -2.67(19) . . . . ?
C9 C8 C10 C11 2.29(18) . . . . ?
C10 C8 C9 S1 -0.14(15) . . . . ?
C10 C8 C9 N1 177.64(13) . . . . ?
C11 S1 C9 N1 -179.56(12) . . . . ?
C11 S1 C9 C8 -1.64(11) . . . . ?
C12 C7 C8 C9 176.20(12) . . . . ?
C12 C7 C8 C10 1.3(2) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C13 C12 C17 C16 0.4(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C15 C16 C17 C12 0.6(2) . . . . ?
C17 C12 C13 C14 -1.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cd15160
_database_code_depnum_ccdc_archive 'CCDC 1430157'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2770(12)
_cell_length_b                   8.8610(13)
_cell_length_c                   20.949(3)
_cell_angle_alpha                78.278(3)
_cell_angle_beta                 83.751(3)
_cell_angle_gamma                64.580(3)
_cell_volume                     1358.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2240
_cell_measurement_theta_min      5.451
_cell_measurement_theta_max      51.012

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.275
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6481
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8191
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.986
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5322
_reflns_number_gt                3796
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.2393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5322
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.24150(9) 0.47487(9) 0.28863(3) 0.0810(2) Uani 1 1 d . . . . .
Cl2 Cl 0.10978(11) 1.04481(10) 0.76336(4) 0.1005(3) Uani 1 1 d . . . . .
N1 N 0.2839(2) 0.1046(2) -0.07681(8) 0.0566(4) Uani 1 1 d . . . . .
N2 N 0.3702(2) 0.2926(2) 0.50518(8) 0.0603(5) Uani 1 1 d . . . . .
O1 O 0.2222(2) -0.10506(19) -0.01076(8) 0.0720(4) Uani 1 1 d . . . . .
O2 O 0.1696(2) 0.5098(2) 0.43563(7) 0.0819(5) Uani 1 1 d . . . . .
C1 C 0.2402(2) 0.0936(2) 0.04018(9) 0.0486(5) Uani 1 1 d . . . . .
C2 C 0.1903(3) -0.0199(3) 0.09323(12) 0.0675(6) Uani 1 1 d . . . . .
H2A H 0.0703 0.0394 0.1103 0.081 Uiso 1 1 calc R U . . .
H2B H 0.2738 -0.0654 0.1286 0.081 Uiso 1 1 calc R U . . .
C3 C 0.2011(3) -0.1593(3) 0.05851(13) 0.0713(6) Uani 1 1 d . . . . .
H3A H 0.3022 -0.2646 0.0738 0.086 Uiso 1 1 calc R U . . .
H3B H 0.0929 -0.1777 0.0672 0.086 Uiso 1 1 calc R U . . .
C4 C 0.2521(3) 0.0362(3) -0.01916(11) 0.0529(5) Uani 1 1 d . . . . .
C5 C 0.2644(2) 0.2356(2) 0.03910(9) 0.0434(4) Uani 1 1 d . . . . .
C6 C 0.2991(2) 0.3205(2) -0.02345(9) 0.0454(4) Uani 1 1 d . . . . .
C7 C 0.3093(2) 0.2493(3) -0.07933(9) 0.0503(5) Uani 1 1 d . . . . .
C8 C 0.3468(3) 0.3298(3) -0.14037(10) 0.0631(6) Uani 1 1 d . . . . .
H8 H 0.3574 0.2822 -0.1771 0.076 Uiso 1 1 calc R U . . .
C9 C 0.3679(3) 0.4757(3) -0.14659(11) 0.0708(7) Uani 1 1 d . . . . .
H9 H 0.3922 0.5273 -0.1875 0.085 Uiso 1 1 calc R U . . .
C10 C 0.3533(3) 0.5488(3) -0.09215(11) 0.0688(6) Uani 1 1 d . . . . .
H10 H 0.3653 0.6502 -0.0969 0.083 Uiso 1 1 calc R U . . .
C11 C 0.3214(3) 0.4720(3) -0.03201(10) 0.0560(5) Uani 1 1 d . . . . .
H11 H 0.3143 0.5208 0.0041 0.067 Uiso 1 1 calc R U . . .
C12 C 0.2566(2) 0.2980(2) 0.10083(8) 0.0428(4) Uani 1 1 d . . . . .
C13 C 0.3830(3) 0.2002(3) 0.14789(9) 0.0512(5) Uani 1 1 d . . . . .
H13 H 0.4725 0.0965 0.1406 0.061 Uiso 1 1 calc R U . . .
C14 C 0.3775(3) 0.2551(3) 0.20540(9) 0.0557(5) Uani 1 1 d . . . . .
H14 H 0.4625 0.1885 0.2369 0.067 Uiso 1 1 calc R U . . .
C15 C 0.2461(3) 0.4082(3) 0.21599(9) 0.0516(5) Uani 1 1 d . . . . .
C16 C 0.1192(3) 0.5062(3) 0.17070(10) 0.0555(5) Uani 1 1 d . . . . .
H16 H 0.0298 0.6095 0.1785 0.067 Uiso 1 1 calc R U . . .
C17 C 0.1242(3) 0.4511(3) 0.11303(10) 0.0523(5) Uani 1 1 d . . . . .
H17 H 0.0375 0.5178 0.0821 0.063 Uiso 1 1 calc R U . . .
C18 C 0.2164(3) 0.5767(3) 0.53017(10) 0.0541(5) Uani 1 1 d . . . . .
C19 C 0.0777(3) 0.7390(3) 0.49521(11) 0.0733(7) Uani 1 1 d . . . . .
H19A H 0.1162 0.8303 0.4884 0.088 Uiso 1 1 calc R U . . .
H19B H -0.0360 0.7728 0.5190 0.088 Uiso 1 1 calc R U . . .
C20 C 0.0653(4) 0.6906(3) 0.43080(11) 0.0767(7) Uani 1 1 d . . . . .
H20A H -0.0585 0.7199 0.4223 0.092 Uiso 1 1 calc R U . . .
H20B H 0.1116 0.7512 0.3953 0.092 Uiso 1 1 calc R U . . .
C21 C 0.2606(3) 0.4507(3) 0.49167(10) 0.0579(5) Uani 1 1 d . . . . .
C22 C 0.4530(3) 0.2462(3) 0.56410(10) 0.0532(5) Uani 1 1 d . . . . .
C23 C 0.4184(3) 0.3609(3) 0.60733(10) 0.0518(5) Uani 1 1 d . . . . .
C24 C 0.2923(3) 0.5337(3) 0.58901(9) 0.0503(5) Uani 1 1 d . . . . .
C25 C 0.5109(3) 0.2997(3) 0.66628(11) 0.0646(6) Uani 1 1 d . . . . .
H25 H 0.4901 0.3732 0.6953 0.078 Uiso 1 1 calc R U . . .
C26 C 0.6307(3) 0.1344(3) 0.68151(13) 0.0782(7) Uani 1 1 d . . . . .
H26 H 0.6903 0.0961 0.7207 0.094 Uiso 1 1 calc R U . . .
C27 C 0.6640(3) 0.0226(3) 0.63827(14) 0.0758(7) Uani 1 1 d . . . . .
H27 H 0.7463 -0.0897 0.6488 0.091 Uiso 1 1 calc R U . . .
C28 C 0.5776(3) 0.0765(3) 0.58111(12) 0.0668(6) Uani 1 1 d . . . . .
H28 H 0.6009 0.0007 0.5528 0.080 Uiso 1 1 calc R U . . .
C29 C 0.2464(3) 0.6611(3) 0.63246(9) 0.0500(5) Uani 1 1 d . . . . .
C30 C 0.1413(3) 0.6564(3) 0.68809(10) 0.0607(5) Uani 1 1 d . . . . .
H30 H 0.0998 0.5719 0.6987 0.073 Uiso 1 1 calc R U . . .
C31 C 0.0966(3) 0.7754(3) 0.72823(11) 0.0642(6) Uani 1 1 d . . . . .
H31 H 0.0254 0.7715 0.7655 0.077 Uiso 1 1 calc R U . . .
C32 C 0.1583(3) 0.8983(3) 0.71245(10) 0.0579(5) Uani 1 1 d . . . . .
C33 C 0.2624(3) 0.9066(3) 0.65772(11) 0.0645(6) Uani 1 1 d . . . . .
H33 H 0.3038 0.9912 0.6475 0.077 Uiso 1 1 calc R U . . .
C34 C 0.3053(3) 0.7877(3) 0.61788(10) 0.0628(6) Uani 1 1 d . . . . .
H34 H 0.3755 0.7933 0.5804 0.075 Uiso 1 1 calc R U . . .


_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 C15 1.7318(19) . ?
Cl2 C32 1.734(2) . ?
N1 C4 1.290(3) . ?
N1 C7 1.376(3) . ?
N2 C21 1.293(3) . ?
N2 C22 1.378(3) . ?
O1 C4 1.351(2) . ?
O1 C3 1.449(3) . ?
O2 C21 1.350(2) . ?
O2 C20 1.445(3) . ?
C1 C5 1.352(3) . ?
C1 C4 1.415(3) . ?
C1 C2 1.490(3) . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.438(3) . ?
C5 C12 1.491(2) . ?
C6 C11 1.406(3) . ?
C6 C7 1.417(3) . ?
C7 C8 1.405(3) . ?
C8 C9 1.356(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.383(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C24 1.354(3) . ?
C18 C21 1.407(3) . ?
C18 C19 1.504(3) . ?
C19 C20 1.523(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 C28 1.408(3) . ?
C22 C23 1.415(3) . ?
C23 C25 1.408(3) . ?
C23 C24 1.434(3) . ?
C24 C29 1.490(3) . ?
C25 C26 1.365(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.398(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.354(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C34 1.374(3) . ?
C29 C30 1.381(3) . ?
C30 C31 1.384(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.359(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.367(3) . ?
C33 C34 1.380(3) . ?
C33 H33 0.9300 . ?
C34 H34 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
C4 N1 C7 114.83(17) . . ?
C21 N2 C22 114.64(18) . . ?
C4 O1 C3 108.33(16) . . ?
C21 O2 C20 108.55(17) . . ?
C5 C1 C4 118.94(18) . . ?
C5 C1 C2 132.82(18) . . ?
C4 C1 C2 108.13(18) . . ?
C1 C2 C3 102.48(19) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
O1 C3 C2 107.66(18) . . ?
O1 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
O1 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N1 C4 O1 120.15(18) . . ?
N1 C4 C1 127.45(19) . . ?
O1 C4 C1 112.38(19) . . ?
C1 C5 C6 117.11(17) . . ?
C1 C5 C12 120.49(17) . . ?
C6 C5 C12 122.40(17) . . ?
C11 C6 C7 118.27(18) . . ?
C11 C6 C5 123.18(17) . . ?
C7 C6 C5 118.54(18) . . ?
N1 C7 C8 118.11(18) . . ?
N1 C7 C6 123.10(18) . . ?
C8 C7 C6 118.8(2) . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 121.3(2) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C17 C12 C13 118.55(17) . . ?
C17 C12 C5 121.68(16) . . ?
C13 C12 C5 119.76(16) . . ?
C14 C13 C12 120.65(18) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.65(19) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.87(18) . . ?
C16 C15 Cl1 120.21(16) . . ?
C14 C15 Cl1 118.92(16) . . ?
C15 C16 C17 119.56(18) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 120.71(18) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C24 C18 C21 119.00(19) . . ?
C24 C18 C19 132.8(2) . . ?
C21 C18 C19 108.10(19) . . ?
C18 C19 C20 102.17(19) . . ?
C18 C19 H19A 111.3 . . ?
C20 C19 H19A 111.3 . . ?
C18 C19 H19B 111.3 . . ?
C20 C19 H19B 111.3 . . ?
H19A C19 H19B 109.2 . . ?
O2 C20 C19 107.90(18) . . ?
O2 C20 H20A 110.1 . . ?
C19 C20 H20A 110.1 . . ?
O2 C20 H20B 110.1 . . ?
C19 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
N2 C21 O2 119.77(19) . . ?
N2 C21 C18 127.6(2) . . ?
O2 C21 C18 112.60(19) . . ?
N2 C22 C28 117.6(2) . . ?
N2 C22 C23 123.00(19) . . ?
C28 C22 C23 119.4(2) . . ?
C25 C23 C22 118.17(19) . . ?
C25 C23 C24 123.11(19) . . ?
C22 C23 C24 118.72(18) . . ?
C18 C24 C23 117.00(18) . . ?
C18 C24 C29 121.17(18) . . ?
C23 C24 C29 121.83(17) . . ?
C26 C25 C23 121.1(2) . . ?
C26 C25 H25 119.4 . . ?
C23 C25 H25 119.4 . . ?
C25 C26 C27 120.1(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C22 120.6(2) . . ?
C27 C28 H28 119.7 . . ?
C22 C28 H28 119.7 . . ?
C34 C29 C30 118.16(19) . . ?
C34 C29 C24 121.00(17) . . ?
C30 C29 C24 120.83(19) . . ?
C29 C30 C31 121.1(2) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C32 C31 C30 119.1(2) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C31 C32 C33 121.3(2) . . ?
C31 C32 Cl2 119.90(17) . . ?
C33 C32 Cl2 118.79(18) . . ?
C32 C33 C34 119.1(2) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C29 C34 C33 121.28(19) . . ?
C29 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 -176.4(2) . . . . ?
C4 C1 C2 C3 7.5(2) . . . . ?
C4 O1 C3 C2 9.2(2) . . . . ?
C1 C2 C3 O1 -10.0(2) . . . . ?
C7 N1 C4 O1 178.96(16) . . . . ?
C7 N1 C4 C1 0.3(3) . . . . ?
C3 O1 C4 N1 176.67(19) . . . . ?
C3 O1 C4 C1 -4.5(2) . . . . ?
C5 C1 C4 N1 -0.2(3) . . . . ?
C2 C1 C4 N1 176.5(2) . . . . ?
C5 C1 C4 O1 -178.97(17) . . . . ?
C2 C1 C4 O1 -2.3(2) . . . . ?
C4 C1 C5 C6 0.7(3) . . . . ?
C2 C1 C5 C6 -175.1(2) . . . . ?
C4 C1 C5 C12 -178.71(16) . . . . ?
C2 C1 C5 C12 5.5(3) . . . . ?
C1 C5 C6 C11 178.05(18) . . . . ?
C12 C5 C6 C11 -2.6(3) . . . . ?
C1 C5 C6 C7 -1.2(2) . . . . ?
C12 C5 C6 C7 178.14(16) . . . . ?
C4 N1 C7 C8 179.21(18) . . . . ?
C4 N1 C7 C6 -0.9(3) . . . . ?
C11 C6 C7 N1 -177.92(17) . . . . ?
C5 C6 C7 N1 1.4(3) . . . . ?
C11 C6 C7 C8 2.0(3) . . . . ?
C5 C6 C7 C8 -178.70(17) . . . . ?
N1 C7 C8 C9 177.97(19) . . . . ?
C6 C7 C8 C9 -1.9(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 1.4(4) . . . . ?
C9 C10 C11 C6 -1.3(3) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C5 C6 C11 C10 -179.69(19) . . . . ?
C1 C5 C12 C17 -114.9(2) . . . . ?
C6 C5 C12 C17 65.8(2) . . . . ?
C1 C5 C12 C13 64.2(2) . . . . ?
C6 C5 C12 C13 -115.1(2) . . . . ?
C17 C12 C13 C14 -0.4(3) . . . . ?
C5 C12 C13 C14 -179.57(18) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C13 C14 C15 Cl1 180.00(16) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
Cl1 C15 C16 C17 -179.80(16) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C13 C12 C17 C16 0.6(3) . . . . ?
C5 C12 C17 C16 179.75(18) . . . . ?
C24 C18 C19 C20 178.5(2) . . . . ?
C21 C18 C19 C20 -5.1(2) . . . . ?
C21 O2 C20 C19 -8.1(3) . . . . ?
C18 C19 C20 O2 7.9(3) . . . . ?
C22 N2 C21 O2 -178.90(18) . . . . ?
C22 N2 C21 C18 -0.9(3) . . . . ?
C20 O2 C21 N2 -176.8(2) . . . . ?
C20 O2 C21 C18 4.9(3) . . . . ?
C24 C18 C21 N2 -0.7(3) . . . . ?
C19 C18 C21 N2 -177.7(2) . . . . ?
C24 C18 C21 O2 177.40(18) . . . . ?
C19 C18 C21 O2 0.4(3) . . . . ?
C21 N2 C22 C28 -178.42(19) . . . . ?
C21 N2 C22 C23 1.4(3) . . . . ?
N2 C22 C23 C25 -179.91(19) . . . . ?
C28 C22 C23 C25 -0.1(3) . . . . ?
N2 C22 C23 C24 -0.4(3) . . . . ?
C28 C22 C23 C24 179.44(18) . . . . ?
C21 C18 C24 C23 1.8(3) . . . . ?
C19 C18 C24 C23 177.9(2) . . . . ?
C21 C18 C24 C29 -178.36(18) . . . . ?
C19 C18 C24 C29 -2.3(4) . . . . ?
C25 C23 C24 C18 178.28(19) . . . . ?
C22 C23 C24 C18 -1.3(3) . . . . ?
C25 C23 C24 C29 -1.6(3) . . . . ?
C22 C23 C24 C29 178.87(18) . . . . ?
C22 C23 C25 C26 0.0(3) . . . . ?
C24 C23 C25 C26 -179.6(2) . . . . ?
C23 C25 C26 C27 0.2(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C27 C28 C22 0.2(4) . . . . ?
N2 C22 C28 C27 179.9(2) . . . . ?
C23 C22 C28 C27 0.1(3) . . . . ?
C18 C24 C29 C34 -72.0(3) . . . . ?
C23 C24 C29 C34 107.8(2) . . . . ?
C18 C24 C29 C30 107.1(2) . . . . ?
C23 C24 C29 C30 -73.1(3) . . . . ?
C34 C29 C30 C31 -0.2(3) . . . . ?
C24 C29 C30 C31 -179.3(2) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C30 C31 C32 C33 0.3(3) . . . . ?
C30 C31 C32 Cl2 -178.02(18) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
Cl2 C32 C33 C34 178.35(18) . . . . ?
C30 C29 C34 C33 0.5(3) . . . . ?
C24 C29 C34 C33 179.6(2) . . . . ?
C32 C33 C34 C29 -0.4(4) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd15153
_database_code_depnum_ccdc_archive 'CCDC 1430177'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Cl2 N O'
_chemical_formula_weight         318.18

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7899(17)
_cell_length_b                   9.516(2)
_cell_length_c                   11.134(2)
_cell_angle_alpha                99.138(5)
_cell_angle_beta                 97.433(5)
_cell_angle_gamma                109.903(5)
_cell_volume                     751.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    927
_cell_measurement_theta_min      4.664
_cell_measurement_theta_max      47.929

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.429
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5421
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4343
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.890
_diffrn_reflns_theta_max         25.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2804
_reflns_number_gt                1894
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0954P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2804
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1707
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.17222(12) 0.89454(9) 0.46934(10) 0.0701(4) Uani 1 1 d . . . . .
Cl2 Cl 0.49215(12) 0.26032(9) 0.45285(8) 0.0641(3) Uani 1 1 d . . . . .
N1 N 0.2453(3) 0.1066(3) 0.0028(2) 0.0473(7) Uani 1 1 d . . . . .
O1 O 0.0591(3) 0.1418(3) 0.1352(2) 0.0676(7) Uani 1 1 d . . . . .
C1 C 0.5645(4) 0.2702(3) 0.0354(3) 0.0415(7) Uani 1 1 d . . . . .
C2 C 0.7323(5) 0.3080(4) -0.0093(3) 0.0586(9) Uani 1 1 d . . . . .
H2 H 0.8363 0.3910 0.0357 0.070 Uiso 1 1 calc R U . . .
C3 C 0.7445(6) 0.2250(5) -0.1173(4) 0.0726(11) Uani 1 1 d . . . . .
H3 H 0.8561 0.2520 -0.1455 0.087 Uiso 1 1 calc R U . . .
C4 C 0.5898(6) 0.0994(4) -0.1857(3) 0.0653(10) Uani 1 1 d . . . . .
H4 H 0.5990 0.0432 -0.2593 0.078 Uiso 1 1 calc R U . . .
C5 C 0.4268(5) 0.0590(3) -0.1455(3) 0.0529(8) Uani 1 1 d . . . . .
H5 H 0.3247 -0.0254 -0.1909 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4122(4) 0.1441(3) -0.0359(3) 0.0418(7) Uani 1 1 d . . . . .
C7 C 0.2142(4) 0.1822(3) 0.1065(3) 0.0478(8) Uani 1 1 d . . . . .
C8 C 0.3737(4) 0.3139(3) 0.1815(3) 0.0416(7) Uani 1 1 d . . . . .
C9 C 0.5403(4) 0.3545(3) 0.1470(2) 0.0388(7) Uani 1 1 d . . . . .
C10 C 0.7024(4) 0.4888(3) 0.2236(2) 0.0381(7) Uani 1 1 d . . . . .
C11 C 0.8498(4) 0.4699(3) 0.2939(3) 0.0454(7) Uani 1 1 d . . . . .
H11 H 0.8508 0.3719 0.2906 0.054 Uiso 1 1 calc R U . . .
C12 C 0.9947(4) 0.5936(3) 0.3687(3) 0.0463(8) Uani 1 1 d . . . . .
H12 H 1.0927 0.5797 0.4160 0.056 Uiso 1 1 calc R U . . .
C13 C 0.9926(4) 0.7378(3) 0.3722(3) 0.0437(7) Uani 1 1 d . . . . .
C14 C 0.8528(5) 0.7608(3) 0.3025(3) 0.0523(8) Uani 1 1 d . . . . .
H14 H 0.8545 0.8594 0.3047 0.063 Uiso 1 1 calc R U . . .
C15 C 0.7071(5) 0.6355(3) 0.2279(3) 0.0500(8) Uani 1 1 d . . . . .
H15 H 0.6108 0.6508 0.1799 0.060 Uiso 1 1 calc R U . . .
C16 C 0.3324(4) 0.3939(3) 0.2956(3) 0.0512(8) Uani 1 1 d . . . . .
H16A H 0.2247 0.4198 0.2711 0.061 Uiso 1 1 calc R U . . .
H16B H 0.4372 0.4891 0.3308 0.061 Uiso 1 1 calc R U . . .
C17 C 0.2952(4) 0.3029(4) 0.3948(3) 0.0614(10) Uani 1 1 d . . . . .
H17A H 0.1895 0.2081 0.3609 0.074 Uiso 1 1 calc R U . . .
H17B H 0.2635 0.3606 0.4626 0.074 Uiso 1 1 calc R U . . .
H1 H 0.135(5) 0.016(4) -0.048(4) 0.080(12) Uiso 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
Cl1 C13 1.740(3) . ?
Cl2 C17 1.785(4) . ?
N1 C7 1.355(4) . ?
N1 C6 1.372(4) . ?
N1 H1 1.01(4) . ?
O1 C7 1.238(4) . ?
C1 C6 1.401(4) . ?
C1 C2 1.411(5) . ?
C1 C9 1.439(4) . ?
C2 C3 1.363(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.352(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.467(4) . ?
C8 C9 1.348(4) . ?
C8 C16 1.504(4) . ?
C9 C10 1.493(3) . ?
C10 C15 1.377(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.355(5) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.506(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C6 125.1(2) . . ?
C7 N1 H1 116(2) . . ?
C6 N1 H1 119(2) . . ?
C6 C1 C2 117.1(3) . . ?
C6 C1 C9 118.8(3) . . ?
C2 C1 C9 124.1(3) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C6 C5 120.0(3) . . ?
N1 C6 C1 118.7(3) . . ?
C5 C6 C1 121.3(3) . . ?
O1 C7 N1 121.4(3) . . ?
O1 C7 C8 122.3(3) . . ?
N1 C7 C8 116.3(3) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 C16 125.1(2) . . ?
C7 C8 C16 114.3(3) . . ?
C8 C9 C1 120.6(2) . . ?
C8 C9 C10 120.4(3) . . ?
C1 C9 C10 119.0(3) . . ?
C15 C10 C11 118.1(3) . . ?
C15 C10 C9 120.5(3) . . ?
C11 C10 C9 121.4(2) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 Cl1 119.2(2) . . ?
C12 C13 Cl1 119.4(2) . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 121.2(3) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C8 C16 C17 114.8(3) . . ?
C8 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
C8 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 Cl2 111.8(2) . . ?
C16 C17 H17A 109.3 . . ?
Cl2 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
Cl2 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?

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
C6 C1 C2 C3 0.1(5) . . . . ?
C9 C1 C2 C3 -178.6(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C7 N1 C6 C5 -179.0(3) . . . . ?
C7 N1 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 N1 177.7(3) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
C2 C1 C6 N1 -178.2(3) . . . . ?
C9 C1 C6 N1 0.6(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C9 C1 C6 C5 179.3(3) . . . . ?
C6 N1 C7 O1 179.8(3) . . . . ?
C6 N1 C7 C8 0.0(5) . . . . ?
O1 C7 C8 C9 -179.9(3) . . . . ?
N1 C7 C8 C9 -0.1(5) . . . . ?
O1 C7 C8 C16 0.3(5) . . . . ?
N1 C7 C8 C16 -179.9(3) . . . . ?
C7 C8 C9 C1 0.5(5) . . . . ?
C16 C8 C9 C1 -179.7(3) . . . . ?
C7 C8 C9 C10 180.0(3) . . . . ?
C16 C8 C9 C10 -0.2(5) . . . . ?
C6 C1 C9 C8 -0.7(4) . . . . ?
C2 C1 C9 C8 177.9(3) . . . . ?
C6 C1 C9 C10 179.8(3) . . . . ?
C2 C1 C9 C10 -1.6(5) . . . . ?
C8 C9 C10 C15 -70.8(4) . . . . ?
C1 C9 C10 C15 108.7(3) . . . . ?
C8 C9 C10 C11 107.9(3) . . . . ?
C1 C9 C10 C11 -72.6(4) . . . . ?
C15 C10 C11 C12 1.7(4) . . . . ?
C9 C10 C11 C12 -177.1(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C11 C12 C13 Cl1 178.4(2) . . . . ?
C12 C13 C14 C15 1.3(5) . . . . ?
Cl1 C13 C14 C15 -178.2(3) . . . . ?
C11 C10 C15 C14 -1.4(5) . . . . ?
C9 C10 C15 C14 177.3(3) . . . . ?
C13 C14 C15 C10 0.0(5) . . . . ?
C9 C8 C16 C17 -111.2(3) . . . . ?
C7 C8 C16 C17 68.6(4) . . . . ?
C8 C16 C17 Cl2 62.0(3) . . . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.114

_shelxl_version_number           2013-4

