# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_91571
_database_code_depnum_ccdc_archive 'CCDC 1579087'
_audit_update_record             
;
2017-10-10 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 Cl N O2'
_chemical_formula_sum            'C14 H16 Cl N O2'
_chemical_formula_weight         265.73

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                   11.325(4)
_cell_length_b                   12.043(3)
_cell_length_c                   12.775(4)
_cell_angle_alpha                61.937(13)
_cell_angle_beta                 82.653(16)
_cell_angle_gamma                64.028(12)
_cell_volume                     1375.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6208
_cell_measurement_theta_min      0.907
_cell_measurement_theta_max      0.947

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             560.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15409
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.322
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6308
_reflns_number_gt                4013
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.2600P)²] 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         6208
_refine_ls_number_parameters     331
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.1005
_refine_ls_wR_factor_ref         0.3467
_refine_ls_wR_factor_gt          0.3158
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.83163(11) 0.53045(12) 0.24539(9) 0.0825(4) Uani 1 1 d . U . . .
O1 O 0.9637(3) 0.6909(3) -0.0720(2) 0.0649(6) Uani 1 1 d . . . . .
N1 N 0.8823(2) 0.3248(2) 0.5067(2) 0.0495(6) Uani 1 1 d . . . . .
C1 C 1.0732(3) 0.1196(3) 0.5620(3) 0.0546(7) Uani 1 1 d . . . . .
Cl2 Cl 1.37157(11) 0.49257(14) 0.18786(13) 0.0933(4) Uani 1 1 d . U . . .
O2 O 1.0793(2) 0.3455(3) 0.4608(3) 0.0679(7) Uani 1 1 d . . . . .
N2 N 1.0571(2) 0.6502(2) 0.1015(2) 0.0473(6) Uani 1 1 d . . . . .
C3 C 1.2224(5) -0.1205(4) 0.6408(4) 0.0791(12) Uani 1 1 d . . . . .
H3 H 1.3077 -0.1907 0.6552 0.095 Uiso 1 1 calc R U . . .
O3 O 1.0840(3) 0.6750(3) 0.2644(2) 0.0689(7) Uani 1 1 d . . . . .
C4 C 1.1212(5) -0.1557(4) 0.6802(4) 0.0823(13) Uani 1 1 d . . . . .
H4 H 1.1387 -0.2496 0.7188 0.099 Uiso 1 1 calc R U . . .
O4 O 0.7371(3) 0.2278(3) 0.6003(3) 0.0762(7) Uani 1 1 d . . . . .
C5 C 0.9887(5) -0.0541(4) 0.6645(3) 0.0706(10) Uani 1 1 d . . . . .
H5 H 0.9193 -0.0785 0.6933 0.085 Uiso 1 1 calc R U . . .
C6 C 0.9697(3) 0.0843(3) 0.6034(3) 0.0559(7) Uani 1 1 d . . . . .
C7 C 1.0196(3) 0.2743(3) 0.5029(3) 0.0524(7) Uani 1 1 d . . . . .
C8 C 0.8466(3) 0.2147(3) 0.5741(3) 0.0555(7) Uani 1 1 d . . . . .
C9 C 0.7994(3) 0.4696(3) 0.4775(3) 0.0550(7) Uani 1 1 d . . . . .
H9A H 0.8548 0.5094 0.4836 0.066 Uiso 1 1 calc R U . . .
H9B H 0.7372 0.4722 0.5370 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7205(3) 0.5639(3) 0.3526(3) 0.0558(6) Uani 1 1 d . U . . .
C11 C 0.6720(4) 0.7171(4) 0.3229(5) 0.0815(13) Uani 1 1 d . . . . .
H11 H 0.7508 0.7317 0.3220 0.098 Uiso 1 1 calc R U . . .
C12 C 0.5972(6) 0.8177(5) 0.1954(6) 0.113(2) Uani 1 1 d . . . . .
H12A H 0.5707 0.9125 0.1782 0.169 Uiso 1 1 calc R U . . .
H12B H 0.5206 0.8044 0.1916 0.169 Uiso 1 1 calc R U . . .
H12C H 0.6545 0.7981 0.1380 0.169 Uiso 1 1 calc R U . . .
C13 C 0.5918(6) 0.7512(6) 0.4165(7) 0.115(2) Uani 1 1 d . . . . .
H13A H 0.5957 0.8304 0.4140 0.173 Uiso 1 1 calc R U . . .
H13B H 0.6271 0.6726 0.4939 0.173 Uiso 1 1 calc R U . . .
H13C H 0.5017 0.7722 0.4012 0.173 Uiso 1 1 calc R U . . .
C14 C 0.9298(3) 0.8661(3) 0.0910(3) 0.0488(6) Uani 1 1 d . . . . .
C15 C 0.8739(3) 0.9836(4) 0.1098(3) 0.0594(8) Uani 1 1 d . . . . .
H15 H 0.8978 0.9803 0.1786 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7820(3) 1.1043(4) 0.0218(4) 0.0664(9) Uani 1 1 d . . . . .
H16 H 0.7441 1.1846 0.0311 0.080 Uiso 1 1 calc R U . . .
C17 C 0.7445(3) 1.1098(4) -0.0789(4) 0.0689(9) Uani 1 1 d . . . . .
H17 H 0.6811 1.1931 -0.1356 0.083 Uiso 1 1 calc R U . . .
C18 C 0.7999(3) 0.9919(3) -0.0985(3) 0.0615(8) Uani 1 1 d . . . . .
H18 H 0.7755 0.9950 -0.1670 0.074 Uiso 1 1 calc R U . . .
C19 C 0.8927(3) 0.8713(3) -0.0101(3) 0.0496(7) Uani 1 1 d . . . . .
C20 C 1.0321(3) 0.7229(3) 0.1671(3) 0.0508(7) Uani 1 1 d . . . . .
C21 C 0.9703(3) 0.7318(3) -0.0043(3) 0.0496(6) Uani 1 1 d . . . . .
C22 C 1.1362(3) 0.4998(3) 0.1506(3) 0.0513(7) Uani 1 1 d . . . . .
H22A H 1.0924 0.4631 0.1235 0.062 Uiso 1 1 calc R U . . .
H22B H 1.1379 0.4582 0.2367 0.062 Uiso 1 1 calc R U . . .
C23 C 1.2781(3) 0.4533(3) 0.1185(3) 0.0544(6) Uani 1 1 d . U . . .
C24 C 1.3382(4) 0.2965(4) 0.1529(5) 0.0804(12) Uani 1 1 d . . . . .
H24 H 1.2840 0.2862 0.1072 0.096 Uiso 1 1 calc R U . . .
C25 C 1.3311(7) 0.2072(5) 0.2842(7) 0.131(3) Uani 1 1 d . . . . .
H25A H 1.2451 0.2504 0.3062 0.196 Uiso 1 1 calc R U . . .
H25B H 1.3967 0.1988 0.3317 0.196 Uiso 1 1 calc R U . . .
H25C H 1.3471 0.1163 0.2974 0.196 Uiso 1 1 calc R U . . .
C26 C 1.4774(5) 0.2410(6) 0.1205(6) 0.1068(18) Uani 1 1 d . . . . .
H26A H 1.4836 0.3057 0.0415 0.160 Uiso 1 1 calc R U . . .
H26B H 1.5002 0.1528 0.1234 0.160 Uiso 1 1 calc R U . . .
H26C H 1.5371 0.2290 0.1760 0.160 Uiso 1 1 calc R U . . .
C27 C 1.2864(2) 0.5507(3) -0.0284(2) 0.0441(6) Uani 1 1 d . U . . .
H27A H 1.3766 0.5332 -0.0426 0.066 Uiso 1 1 calc R U . . .
H27B H 1.2351 0.6478 -0.0505 0.066 Uiso 1 1 calc R U . . .
H27C H 1.2521 0.5261 -0.0752 0.066 Uiso 1 1 calc R U . . .
C28 C 0.6084(3) 0.5189(3) 0.3382(3) 0.0526(7) Uani 1 1 d . . . . .
H28A H 0.5813 0.5596 0.2551 0.079 Uiso 1 1 calc R U . . .
H28B H 0.5334 0.5515 0.3781 0.079 Uiso 1 1 calc R U . . .
H28C H 0.6448 0.4191 0.3728 0.079 Uiso 1 1 calc R U . . .
C2 C 1.2020(4) 0.0196(4) 0.5785(4) 0.0706(9) Uani 1 1 d . . . . .
H2 H 1.2714 0.0440 0.5499 0.085 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 C10 1.804(4) . ?
O1 C21 1.202(4) . ?
N1 C8 1.404(4) . ?
N1 C7 1.404(4) . ?
N1 C9 1.451(4) . ?
C1 C6 1.379(5) . ?
C1 C2 1.387(5) . ?
C1 C7 1.488(4) . ?
Cl2 C23 1.790(4) . ?
O2 C7 1.209(4) . ?
N2 C20 1.400(4) . ?
N2 C21 1.416(4) . ?
N2 C22 1.459(3) . ?
C3 C4 1.350(7) . ?
C3 C2 1.406(6) . ?
O3 C20 1.200(4) . ?
C4 C5 1.425(7) . ?
O4 C8 1.202(4) . ?
C5 C6 1.392(5) . ?
C6 C8 1.488(5) . ?
C9 C10 1.551(4) . ?
C10 C11 1.535(4) . ?
C10 C28 1.642(4) . ?
C11 C13 1.510(9) . ?
C11 C12 1.561(7) . ?
C14 C19 1.375(4) . ?
C14 C15 1.399(4) . ?
C14 C20 1.490(4) . ?
C15 C16 1.378(5) . ?
C16 C17 1.370(6) . ?
C17 C18 1.409(5) . ?
C18 C19 1.383(4) . ?
C19 C21 1.485(4) . ?
C22 C23 1.525(4) . ?
C23 C24 1.546(5) . ?
C23 C27 1.699(4) . ?
C24 C26 1.508(6) . ?
C24 C25 1.523(9) . ?

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
C8 N1 C7 110.9(2) . . ?
C8 N1 C9 124.8(3) . . ?
C7 N1 C9 121.6(2) . . ?
C6 C1 C2 122.1(3) . . ?
C6 C1 C7 108.1(3) . . ?
C2 C1 C7 129.8(3) . . ?
C20 N2 C21 111.3(2) . . ?
C20 N2 C22 123.5(2) . . ?
C21 N2 C22 123.3(2) . . ?
C4 C3 C2 121.6(4) . . ?
C3 C4 C5 122.3(4) . . ?
C6 C5 C4 115.6(4) . . ?
C1 C6 C5 121.8(3) . . ?
C1 C6 C8 108.5(3) . . ?
C5 C6 C8 129.7(4) . . ?
O2 C7 N1 125.4(3) . . ?
O2 C7 C1 128.4(3) . . ?
N1 C7 C1 106.2(3) . . ?
O4 C8 N1 125.2(3) . . ?
O4 C8 C6 128.8(3) . . ?
N1 C8 C6 106.0(3) . . ?
N1 C9 C10 116.2(2) . . ?
C11 C10 C9 108.7(3) . . ?
C11 C10 C28 116.3(2) . . ?
C9 C10 C28 112.7(3) . . ?
C11 C10 Cl1 108.6(3) . . ?
C9 C10 Cl1 107.8(2) . . ?
C28 C10 Cl1 102.2(2) . . ?
C13 C11 C10 112.7(4) . . ?
C13 C11 C12 112.2(4) . . ?
C10 C11 C12 111.2(4) . . ?
C19 C14 C15 121.1(3) . . ?
C19 C14 C20 109.0(2) . . ?
C15 C14 C20 129.8(3) . . ?
C16 C15 C14 117.0(3) . . ?
C17 C16 C15 122.0(3) . . ?
C16 C17 C18 121.4(3) . . ?
C19 C18 C17 116.2(3) . . ?
C14 C19 C18 122.2(3) . . ?
C14 C19 C21 108.2(3) . . ?
C18 C19 C21 129.6(3) . . ?
O3 C20 N2 125.2(3) . . ?
O3 C20 C14 129.3(3) . . ?
N2 C20 C14 105.5(2) . . ?
O1 C21 N2 124.9(3) . . ?
O1 C21 C19 129.3(3) . . ?
N2 C21 C19 105.8(2) . . ?
N2 C22 C23 115.8(2) . . ?
C22 C23 C24 109.3(3) . . ?
C22 C23 C27 111.4(2) . . ?
C24 C23 C27 111.3(3) . . ?
C22 C23 Cl2 110.3(2) . . ?
C24 C23 Cl2 112.7(3) . . ?
C27 C23 Cl2 101.73(19) . . ?
C26 C24 C25 110.3(5) . . ?
C26 C24 C23 113.6(4) . . ?
C25 C24 C23 112.2(4) . . ?
C1 C2 C3 116.6(4) . . ?

_refine_diff_density_max         1.453
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.102



####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1579241'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Cl N2 O3'
_chemical_formula_weight         292.71

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'
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   P21/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                   16.319(3)
_cell_length_b                   6.1182(12)
_cell_length_c                   14.399(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.57(3)
_cell_angle_gamma                90.00
_cell_volume                     1362.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3896
_cell_measurement_theta_min      3.3290
_cell_measurement_theta_max      27.5398

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.8000
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10900
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3117
_reflns_number_gt                1969
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0904P)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         3117
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1581
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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 0.44151(4) 0.76801(13) 0.00916(6) 0.0827(3) Uani 1 1 d . . .
N1 N 0.19627(11) 0.5995(3) -0.02676(12) 0.0459(4) Uani 1 1 d . . .
O1 O 0.14324(10) 0.9215(3) 0.01755(12) 0.0631(5) Uani 1 1 d . . .
C1 C -0.03585(15) 0.7135(4) -0.10149(17) 0.0549(6) Uani 1 1 d . . .
H1 H -0.0484 0.8482 -0.0793 0.066 Uiso 1 1 calc R . .
C3 C -0.08215(15) 0.3730(5) -0.18742(17) 0.0635(7) Uani 1 1 d . . .
H3 H -0.1274 0.2830 -0.2223 0.076 Uiso 1 1 calc R . .
O3 O 0.30280(14) 0.7248(4) 0.22181(12) 0.0871(7) Uani 1 1 d . . .
C6 C 0.04865(13) 0.6421(3) -0.08214(14) 0.0470(5) Uani 1 1 d . . .
C5 C 0.06718(13) 0.4417(3) -0.11602(13) 0.0456(5) Uani 1 1 d . . .
O2 O 0.20544(10) 0.2700(3) -0.10381(12) 0.0615(5) Uani 1 1 d . . .
N2 N 0.32522(11) 0.4976(3) 0.10585(12) 0.0500(5) Uani 1 1 d . . .
C2 C -0.10058(15) 0.5752(4) -0.15525(17) 0.0629(6) Uani 1 1 d . . .
H2 H -0.1579 0.6188 -0.1702 0.075 Uiso 1 1 calc R . .
C4 C 0.00203(14) 0.3025(4) -0.16870(15) 0.0542(6) Uani 1 1 d . . .
H4 H 0.0144 0.1673 -0.1906 0.065 Uiso 1 1 calc R . .
C8 C 0.16254(14) 0.4149(3) -0.08472(14) 0.0469(5) Uani 1 1 d . . .
C9 C 0.28789(13) 0.6451(3) 0.02536(15) 0.0472(5) Uani 1 1 d . . .
H9 H 0.2904 0.7916 0.0537 0.057 Uiso 1 1 calc R . .
C11 C 0.3581(2) 0.2776(4) 0.0979(2) 0.0802(8) Uani 1 1 d . . .
H11A H 0.3969 0.2785 0.0590 0.096 Uiso 1 1 calc R . .
H11B H 0.3111 0.1762 0.0690 0.096 Uiso 1 1 calc R . .
C12 C 0.4057(3) 0.2195(5) 0.2039(3) 0.1086(13) Uani 1 1 d . . .
H12A H 0.3964 0.0672 0.2163 0.130 Uiso 1 1 calc R . .
H12B H 0.4673 0.2441 0.2189 0.130 Uiso 1 1 calc R . .
C13 C 0.36948(19) 0.3657(6) 0.2650(2) 0.0906(10) Uani 1 1 d . . .
H13A H 0.4150 0.4173 0.3223 0.109 Uiso 1 1 calc R . .
H13B H 0.3266 0.2889 0.2863 0.109 Uiso 1 1 calc R . .
C14 C 0.32891(15) 0.5536(4) 0.19853(17) 0.0608(6) Uani 1 1 d . . .
C10 C 0.33764(15) 0.6558(5) -0.04755(18) 0.0683(7) Uani 1 1 d . . .
H10A H 0.3063 0.7455 -0.1030 0.082 Uiso 1 1 calc R . .
H10B H 0.3432 0.5101 -0.0715 0.082 Uiso 1 1 calc R . .
C7 C 0.13093(14) 0.7470(3) -0.02451(15) 0.0479(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
Cl1 C10 1.769(2) . ?
N1 C7 1.405(3) . ?
N1 C8 1.408(3) . ?
N1 C9 1.470(3) . ?
O1 C7 1.212(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.388(3) . ?
C1 H1 0.9300 . ?
C3 C4 1.382(3) . ?
C3 C2 1.387(4) . ?
C3 H3 0.9300 . ?
O3 C14 1.217(3) . ?
C6 C5 1.388(3) . ?
C6 C7 1.481(3) . ?
C5 C4 1.385(3) . ?
C5 C8 1.485(3) . ?
O2 C8 1.214(3) . ?
N2 C14 1.360(3) . ?
N2 C9 1.442(3) . ?
N2 C11 1.467(3) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C9 C10 1.519(3) . ?
C9 H9 0.9800 . ?
C11 C12 1.519(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.502(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.507(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 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 C8 111.87(17) . . ?
C7 N1 C9 121.49(17) . . ?
C8 N1 C9 126.63(17) . . ?
C2 C1 C6 117.0(2) . . ?
C2 C1 H1 121.5 . . ?
C6 C1 H1 121.5 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C1 C6 C5 121.4(2) . . ?
C1 C6 C7 129.9(2) . . ?
C5 C6 C7 108.64(18) . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 C8 130.2(2) . . ?
C6 C5 C8 108.38(18) . . ?
C14 N2 C9 120.42(19) . . ?
C14 N2 C11 113.88(19) . . ?
C9 N2 C11 125.64(19) . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C3 C4 C5 117.2(2) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
O2 C8 N1 125.1(2) . . ?
O2 C8 C5 129.50(19) . . ?
N1 C8 C5 105.39(17) . . ?
N2 C9 N1 113.10(16) . . ?
N2 C9 C10 113.61(19) . . ?
N1 C9 C10 109.62(17) . . ?
N2 C9 H9 106.7 . . ?
N1 C9 H9 106.7 . . ?
C10 C9 H9 106.7 . . ?
N2 C11 C12 102.6(2) . . ?
N2 C11 H11A 111.2 . . ?
C12 C11 H11A 111.2 . . ?
N2 C11 H11B 111.2 . . ?
C12 C11 H11B 111.2 . . ?
H11A C11 H11B 109.2 . . ?
C13 C12 C11 106.2(3) . . ?
C13 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C12 C13 C14 104.9(2) . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
C14 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
O3 C14 N2 125.2(2) . . ?
O3 C14 C13 127.1(2) . . ?
N2 C14 C13 107.7(2) . . ?
C9 C10 Cl1 110.00(16) . . ?
C9 C10 H10A 109.7 . . ?
Cl1 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
Cl1 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C7 N1 124.8(2) . . ?
O1 C7 C6 129.6(2) . . ?
N1 C7 C6 105.56(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C1 C6 C7 -177.6(2) . . . . ?
C1 C6 C5 C4 -1.5(3) . . . . ?
C7 C6 C5 C4 177.07(18) . . . . ?
C1 C6 C5 C8 179.14(17) . . . . ?
C7 C6 C5 C8 -2.3(2) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C4 C3 C2 C1 -1.3(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C6 C5 C4 C3 1.0(3) . . . . ?
C8 C5 C4 C3 -179.8(2) . . . . ?
C7 N1 C8 O2 175.1(2) . . . . ?
C9 N1 C8 O2 -3.7(3) . . . . ?
C7 N1 C8 C5 -4.1(2) . . . . ?
C9 N1 C8 C5 177.06(17) . . . . ?
C4 C5 C8 O2 5.4(4) . . . . ?
C6 C5 C8 O2 -175.2(2) . . . . ?
C4 C5 C8 N1 -175.4(2) . . . . ?
C6 C5 C8 N1 3.9(2) . . . . ?
C14 N2 C9 N1 -95.1(2) . . . . ?
C11 N2 C9 N1 81.9(3) . . . . ?
C14 N2 C9 C10 139.2(2) . . . . ?
C11 N2 C9 C10 -43.9(3) . . . . ?
C7 N1 C9 N2 113.1(2) . . . . ?
C8 N1 C9 N2 -68.2(3) . . . . ?
C7 N1 C9 C10 -119.0(2) . . . . ?
C8 N1 C9 C10 59.7(3) . . . . ?
C14 N2 C11 C12 -14.3(3) . . . . ?
C9 N2 C11 C12 168.5(2) . . . . ?
N2 C11 C12 C13 20.9(4) . . . . ?
C11 C12 C13 C14 -20.5(4) . . . . ?
C9 N2 C14 O3 -0.3(4) . . . . ?
C11 N2 C14 O3 -177.6(3) . . . . ?
C9 N2 C14 C13 179.0(2) . . . . ?
C11 N2 C14 C13 1.7(3) . . . . ?
C12 C13 C14 O3 -168.8(3) . . . . ?
C12 C13 C14 N2 12.0(3) . . . . ?
N2 C9 C10 Cl1 -65.1(2) . . . . ?
N1 C9 C10 Cl1 167.29(16) . . . . ?
C8 N1 C7 O1 -177.5(2) . . . . ?
C9 N1 C7 O1 1.4(3) . . . . ?
C8 N1 C7 C6 2.7(2) . . . . ?
C9 N1 C7 C6 -178.36(17) . . . . ?
C1 C6 C7 O1 -1.5(4) . . . . ?
C5 C6 C7 O1 -179.8(2) . . . . ?
C1 C6 C7 N1 178.2(2) . . . . ?
C5 C6 C7 N1 -0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1579238'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl N O2'
_chemical_formula_weight         277.74

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

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

_cell_length_a                   16.501(3)
_cell_length_b                   7.2983(15)
_cell_length_c                   22.711(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2735.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6995
_cell_measurement_theta_min      2.4665
_cell_measurement_theta_max      27.5204

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.7000
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.1500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19947
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3124
_reflns_number_gt                2971
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.8972P] 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         3124
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.97865(4) 0.10617(9) 0.43528(2) 0.0736(2) Uani 1 1 d . . .
O1 O 0.72752(9) 0.0940(2) 0.30772(6) 0.0601(4) Uani 1 1 d . . .
N1 N 0.85976(9) 0.1616(2) 0.28200(6) 0.0415(3) Uani 1 1 d . . .
C2 C 0.76957(15) 0.3684(3) 0.10205(9) 0.0620(6) Uani 1 1 d . . .
H2 H 0.7713 0.4131 0.0637 0.074 Uiso 1 1 calc R . .
O2 O 0.97303(8) 0.2407(2) 0.22732(6) 0.0608(4) Uani 1 1 d . . .
C3 C 0.69541(15) 0.3326(3) 0.12733(10) 0.0631(6) Uani 1 1 d . . .
H3 H 0.6483 0.3547 0.1060 0.076 Uiso 1 1 calc R . .
C4 C 0.68977(13) 0.2639(3) 0.18427(9) 0.0541(5) Uani 1 1 d . . .
H4 H 0.6399 0.2396 0.2016 0.065 Uiso 1 1 calc R . .
C5 C 0.76159(11) 0.2336(2) 0.21388(7) 0.0427(4) Uani 1 1 d . . .
C6 C 0.83602(11) 0.2728(2) 0.18878(7) 0.0423(4) Uani 1 1 d . . .
C7 C 0.90029(11) 0.2272(3) 0.23201(7) 0.0436(4) Uani 1 1 d . . .
C8 C 0.77604(11) 0.1560(2) 0.27336(8) 0.0427(4) Uani 1 1 d . . .
C9 C 0.90186(13) 0.0875(3) 0.33312(8) 0.0492(4) Uani 1 1 d . . .
H9A H 0.9549 0.0444 0.3210 0.059 Uiso 1 1 calc R . .
H9B H 0.8718 -0.0171 0.3479 0.059 Uiso 1 1 calc R . .
C10 C 0.91240(10) 0.2268(3) 0.38322(7) 0.0416(4) Uani 1 1 d . . .
C11 C 0.83402(11) 0.2706(3) 0.41487(8) 0.0487(4) Uani 1 1 d . . .
H11A H 0.8117 0.1583 0.4309 0.058 Uiso 1 1 calc R . .
H11B H 0.7954 0.3186 0.3866 0.058 Uiso 1 1 calc R . .
C12 C 0.84430(13) 0.4089(3) 0.46455(9) 0.0593(5) Uani 1 1 d . . .
H12A H 0.7916 0.4389 0.4808 0.071 Uiso 1 1 calc R . .
H12B H 0.8767 0.3549 0.4957 0.071 Uiso 1 1 calc R . .
C13 C 0.88476(14) 0.5817(3) 0.44304(9) 0.0623(6) Uani 1 1 d . . .
H13A H 0.8939 0.6633 0.4761 0.075 Uiso 1 1 calc R . .
H13B H 0.8493 0.6435 0.4154 0.075 Uiso 1 1 calc R . .
C14 C 0.96490(13) 0.5406(3) 0.41334(9) 0.0601(5) Uani 1 1 d . . .
H14A H 1.0028 0.4933 0.4423 0.072 Uiso 1 1 calc R . .
H14B H 0.9873 0.6530 0.3974 0.072 Uiso 1 1 calc R . .
C15 C 0.95490(11) 0.4014(3) 0.36401(8) 0.0475(4) Uani 1 1 d . . .
H15A H 0.9241 0.4571 0.3323 0.057 Uiso 1 1 calc R . .
H15B H 1.0080 0.3703 0.3487 0.057 Uiso 1 1 calc R . .
C1 C 0.84183(13) 0.3401(3) 0.13192(8) 0.0530(5) Uani 1 1 d . . .
H1 H 0.8917 0.3650 0.1146 0.064 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 C10 1.8350(17) . ?
O1 C8 1.206(2) . ?
N1 C8 1.396(2) . ?
N1 C7 1.402(2) . ?
N1 C9 1.457(2) . ?
C2 C3 1.377(3) . ?
C2 C1 1.387(3) . ?
O2 C7 1.209(2) . ?
C3 C4 1.390(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.384(3) . ?
C5 C8 1.484(2) . ?
C6 C1 1.385(2) . ?
C6 C7 1.483(3) . ?
C9 C10 1.536(3) . ?
C10 C11 1.514(2) . ?
C10 C15 1.519(3) . ?
C11 C12 1.523(3) . ?
C12 C13 1.508(3) . ?
C13 C14 1.515(3) . ?
C14 C15 1.521(3) . ?

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
C8 N1 C7 111.61(14) . . ?
C8 N1 C9 124.95(15) . . ?
C7 N1 C9 123.01(15) . . ?
C3 C2 C1 122.11(19) . . ?
C2 C3 C4 121.1(2) . . ?
C5 C4 C3 117.0(2) . . ?
C4 C5 C6 121.88(17) . . ?
C4 C5 C8 129.97(18) . . ?
C6 C5 C8 108.14(15) . . ?
C5 C6 C1 121.25(18) . . ?
C5 C6 C7 108.40(15) . . ?
C1 C6 C7 130.34(18) . . ?
O2 C7 N1 124.93(17) . . ?
O2 C7 C6 129.31(17) . . ?
N1 C7 C6 105.76(15) . . ?
O1 C8 N1 125.25(17) . . ?
O1 C8 C5 128.71(17) . . ?
N1 C8 C5 106.00(15) . . ?
N1 C9 C10 113.50(15) . . ?
C11 C10 C15 110.69(16) . . ?
C11 C10 C9 113.26(15) . . ?
C15 C10 C9 113.27(15) . . ?
C11 C10 Cl1 107.73(12) . . ?
C15 C10 Cl1 108.22(12) . . ?
C9 C10 Cl1 103.14(12) . . ?
C10 C11 C12 113.36(16) . . ?
C13 C12 C11 111.30(16) . . ?
C12 C13 C14 111.41(19) . . ?
C13 C14 C15 111.44(16) . . ?
C10 C15 C14 113.50(16) . . ?
C6 C1 C2 116.7(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
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C3 C4 C5 C8 -177.48(18) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C8 C5 C6 C1 177.24(16) . . . . ?
C4 C5 C6 C7 179.23(17) . . . . ?
C8 C5 C6 C7 -1.8(2) . . . . ?
C8 N1 C7 O2 -177.78(18) . . . . ?
C9 N1 C7 O2 -5.0(3) . . . . ?
C8 N1 C7 C6 2.02(19) . . . . ?
C9 N1 C7 C6 174.78(15) . . . . ?
C5 C6 C7 O2 179.7(2) . . . . ?
C1 C6 C7 O2 0.8(3) . . . . ?
C5 C6 C7 N1 -0.05(19) . . . . ?
C1 C6 C7 N1 -178.95(18) . . . . ?
C7 N1 C8 O1 174.84(18) . . . . ?
C9 N1 C8 O1 2.2(3) . . . . ?
C7 N1 C8 C5 -3.07(19) . . . . ?
C9 N1 C8 C5 -175.67(15) . . . . ?
C4 C5 C8 O1 4.0(3) . . . . ?
C6 C5 C8 O1 -174.86(19) . . . . ?
C4 C5 C8 N1 -178.16(19) . . . . ?
C6 C5 C8 N1 2.96(19) . . . . ?
C8 N1 C9 C10 -90.6(2) . . . . ?
C7 N1 C9 C10 97.66(19) . . . . ?
N1 C9 C10 C11 71.7(2) . . . . ?
N1 C9 C10 C15 -55.4(2) . . . . ?
N1 C9 C10 Cl1 -172.18(13) . . . . ?
C15 C10 C11 C12 -51.5(2) . . . . ?
C9 C10 C11 C12 -179.94(17) . . . . ?
Cl1 C10 C11 C12 66.65(19) . . . . ?
C10 C11 C12 C13 54.3(2) . . . . ?
C11 C12 C13 C14 -55.1(2) . . . . ?
C12 C13 C14 C15 54.7(2) . . . . ?
C11 C10 C15 C14 51.1(2) . . . . ?
C9 C10 C15 C14 179.53(16) . . . . ?
Cl1 C10 C15 C14 -66.76(18) . . . . ?
C13 C14 C15 C10 -53.3(2) . . . . ?
C5 C6 C1 C2 0.9(3) . . . . ?
C7 C6 C1 C2 179.72(18) . . . . ?
C3 C2 C1 C6 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1579242'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl N O3'
_chemical_formula_weight         251.66

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   '

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

_cell_length_a                   7.3183(15)
_cell_length_b                   8.0932(16)
_cell_length_c                   10.816(2)
_cell_angle_alpha                108.07(3)
_cell_angle_beta                 97.49(3)
_cell_angle_gamma                104.80(3)
_cell_volume                     573.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1460
_cell_measurement_theta_min      2.7978
_cell_measurement_theta_max      27.4584

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6029
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2592
_reflns_number_gt                2085
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0829P)²+0.2286P] 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         2592
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1828
_refine_ls_wR_factor_gt          0.1713
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.098
_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 0.47520(12) 0.23181(14) 0.90057(9) 0.0865(3) Uani 1 1 d . . .
C1 C 0.7165(4) 0.3043(4) 0.3492(3) 0.0672(7) Uani 1 1 d . . .
H1 H 0.7029 0.1851 0.2958 0.081 Uiso 1 1 calc R . .
N1 N 0.7823(3) 0.3743(3) 0.70547(19) 0.0526(5) Uani 1 1 d U . .
O1 O 0.7489(4) 0.0936(2) 0.5484(2) 0.0770(6) Uani 1 1 d . . .
O2 O 0.8265(4) 0.6823(3) 0.8039(2) 0.0814(7) Uani 1 1 d . . .
C6 C 0.7426(3) 0.3563(3) 0.4858(2) 0.0510(6) Uani 1 1 d . . .
C3 C 0.7336(4) 0.6144(5) 0.3730(3) 0.0740(8) Uani 1 1 d . . .
H3 H 0.7307 0.7009 0.3334 0.089 Uiso 1 1 calc R . .
O3 O 0.9970(3) 0.3062(3) 0.8513(2) 0.0747(6) Uani 1 1 d . . .
C4 C 0.7605(4) 0.6658(4) 0.5101(3) 0.0629(7) Uani 1 1 d . . .
H4 H 0.7756 0.7853 0.5638 0.076 Uiso 1 1 calc R . .
C5 C 0.7640(3) 0.5329(3) 0.5638(2) 0.0500(5) Uani 1 1 d . . .
C7 C 0.7569(4) 0.2510(3) 0.5771(3) 0.0551(6) Uani 1 1 d U . .
C8 C 0.7946(4) 0.5488(3) 0.7059(3) 0.0548(6) Uani 1 1 d . . .
C10 C 0.6624(4) 0.1715(4) 0.8292(3) 0.0654(7) Uani 1 1 d . . .
H10 H 0.6076 0.0847 0.7373 0.079 Uiso 1 1 calc R . .
C9 C 0.8171(4) 0.3396(4) 0.8291(3) 0.0586(6) Uani 1 1 d . . .
H9 H 0.8193 0.4471 0.9035 0.070 Uiso 1 1 calc R . .
C12 C 0.9691(4) 0.1334(4) 0.8659(3) 0.0696(7) Uani 1 1 d . . .
H12A H 1.0735 0.1395 0.9341 0.083 Uiso 1 1 calc R . .
H12B H 0.9643 0.0403 0.7824 0.083 Uiso 1 1 calc R . .
C11 C 0.7792(5) 0.0920(5) 0.9060(4) 0.0784(9) Uani 1 1 d . . .
H11A H 0.7955 0.1504 1.0015 0.094 Uiso 1 1 calc R . .
H11B H 0.7187 -0.0389 0.8806 0.094 Uiso 1 1 calc R . .
C2 C 0.7114(4) 0.4387(5) 0.2949(3) 0.0768(9) Uani 1 1 d . . .
H2 H 0.6923 0.4078 0.2028 0.092 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 C10 1.759(3) . ?
C1 C6 1.377(4) . ?
C1 C2 1.393(4) . ?
N1 C8 1.390(3) . ?
N1 C7 1.392(3) . ?
N1 C9 1.453(3) . ?
O1 C7 1.198(3) . ?
O2 C8 1.200(3) . ?
C6 C5 1.372(3) . ?
C6 C7 1.501(3) . ?
C3 C2 1.365(5) . ?
C3 C4 1.382(4) . ?
O3 C9 1.415(3) . ?
O3 C12 1.422(3) . ?
C4 C5 1.376(3) . ?
C5 C8 1.484(3) . ?
C10 C11 1.504(4) . ?
C10 C9 1.532(4) . ?
C12 C11 1.497(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 116.9(3) . . ?
C8 N1 C7 111.8(2) . . ?
C8 N1 C9 121.4(2) . . ?
C7 N1 C9 126.4(2) . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 C7 107.5(2) . . ?
C1 C6 C7 131.5(2) . . ?
C2 C3 C4 121.0(3) . . ?
C9 O3 C12 110.4(2) . . ?
C5 C4 C3 117.2(3) . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 C8 108.8(2) . . ?
C4 C5 C8 129.1(2) . . ?
O1 C7 N1 125.8(2) . . ?
O1 C7 C6 128.3(2) . . ?
N1 C7 C6 105.90(19) . . ?
O2 C8 N1 125.3(2) . . ?
O2 C8 C5 128.8(2) . . ?
N1 C8 C5 105.9(2) . . ?
C11 C10 C9 102.4(2) . . ?
C11 C10 Cl1 114.2(2) . . ?
C9 C10 Cl1 111.6(2) . . ?
O3 C9 N1 111.1(2) . . ?
O3 C9 C10 106.2(2) . . ?
N1 C9 C10 112.8(2) . . ?
O3 C12 C11 105.0(2) . . ?
C12 C11 C10 102.6(2) . . ?
C3 C2 C1 121.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C7 C6 C5 C4 179.1(2) . . . . ?
C1 C6 C5 C8 -178.5(2) . . . . ?
C7 C6 C5 C8 0.6(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C8 178.4(2) . . . . ?
C8 N1 C7 O1 177.1(3) . . . . ?
C9 N1 C7 O1 4.5(4) . . . . ?
C8 N1 C7 C6 -2.8(3) . . . . ?
C9 N1 C7 C6 -175.4(2) . . . . ?
C5 C6 C7 O1 -178.7(3) . . . . ?
C1 C6 C7 O1 0.3(5) . . . . ?
C5 C6 C7 N1 1.2(3) . . . . ?
C1 C6 C7 N1 -179.8(3) . . . . ?
C7 N1 C8 O2 -175.9(3) . . . . ?
C9 N1 C8 O2 -2.9(4) . . . . ?
C7 N1 C8 C5 3.1(3) . . . . ?
C9 N1 C8 C5 176.1(2) . . . . ?
C6 C5 C8 O2 176.7(3) . . . . ?
C4 C5 C8 O2 -1.6(5) . . . . ?
C6 C5 C8 N1 -2.3(3) . . . . ?
C4 C5 C8 N1 179.4(2) . . . . ?
C12 O3 C9 N1 -123.3(2) . . . . ?
C12 O3 C9 C10 -0.3(3) . . . . ?
C8 N1 C9 O3 -107.4(3) . . . . ?
C7 N1 C9 O3 64.5(3) . . . . ?
C8 N1 C9 C10 133.4(2) . . . . ?
C7 N1 C9 C10 -54.7(3) . . . . ?
C11 C10 C9 O3 22.1(3) . . . . ?
Cl1 C10 C9 O3 144.7(2) . . . . ?
C11 C10 C9 N1 144.1(2) . . . . ?
Cl1 C10 C9 N1 -93.4(2) . . . . ?
C9 O3 C12 C11 -22.1(3) . . . . ?
O3 C12 C11 C10 35.3(3) . . . . ?
C9 C10 C11 C12 -34.4(3) . . . . ?
Cl1 C10 C11 C12 -155.1(2) . . . . ?
C4 C3 C2 C1 -0.6(5) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.044
