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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_18pure_R_210516_0m
_database_code_depnum_ccdc_archive 'CCDC 1487677'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2017-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl N O3'
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.020(4)
_cell_length_b                   10.237(4)
_cell_length_c                   9.318(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.399(6)
_cell_angle_gamma                90
_cell_volume                     764.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1020
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.51

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8947
_exptl_absorpt_correction_T_max  0.9490
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9508
_diffrn_reflns_av_unetI/netI     0.1317
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.462
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             2640
_reflns_number_gt                2245
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.946

_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'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)] 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_abs_structure_details 
;
 Flack x determined using 816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.15(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2640
_refine_ls_number_parameters     209
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.121
_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 -0.04974(17) 0.74994(12) 0.94998(18) 0.0225(4) Uani 1 1 d . . . . .
O1 O 0.4388(4) 0.2022(3) 0.8373(5) 0.0157(8) Uani 1 1 d . . . . .
O2 O 0.4891(4) 0.3904(3) 1.0898(4) 0.0143(8) Uani 1 1 d . . . . .
O3 O 0.7573(5) 0.3830(4) 1.2717(5) 0.0212(9) Uani 1 1 d . . . . .
N1 N 0.1802(6) 0.2992(4) 0.7146(6) 0.0125(10) Uani 1 1 d . . . . .
C1 C 0.3901(6) 0.4195(5) 0.9196(6) 0.0102(11) Uani 1 1 d . U . . .
C2 C 0.3435(7) 0.2920(4) 0.8220(7) 0.0107(11) Uani 1 1 d . U . . .
C3 C 0.1027(7) 0.4087(5) 0.7474(7) 0.0129(11) Uani 1 1 d . . . . .
C4 C 0.2224(6) 0.4786(5) 0.8760(6) 0.0114(11) Uani 1 1 d . U . . .
C5 C 0.1798(7) 0.5861(5) 0.9371(7) 0.0139(11) Uani 1 1 d . U . . .
H5 H 0.2621 0.6358 1.0229 0.017 Uiso 1 1 calc R U . . .
C6 C 0.0126(7) 0.6192(5) 0.8692(7) 0.0148(12) Uani 1 1 d . U . . .
C7 C -0.1072(7) 0.5518(5) 0.7391(7) 0.0144(12) Uani 1 1 d . . . . .
H7 H -0.2207 0.5786 0.6930 0.017 Uiso 1 1 calc R U . . .
C8 C -0.0626(7) 0.4442(5) 0.6749(7) 0.0132(11) Uani 1 1 d . . . . .
H8 H -0.1434 0.3976 0.5847 0.016 Uiso 1 1 calc R U . . .
C9 C 0.6543(7) 0.4099(5) 1.1365(7) 0.0145(12) Uani 1 1 d . . . . .
C10 C 0.6787(7) 0.4624(5) 0.9983(7) 0.0168(12) Uani 1 1 d . . . . .
H10A H 0.7217 0.3936 0.9525 0.020 Uiso 1 1 calc R U . . .
H10B H 0.7580 0.5366 1.0339 0.020 Uiso 1 1 calc R U . . .
C11 C 0.5055(6) 0.5069(5) 0.8746(7) 0.0103(11) Uani 1 1 d . . . . .
H9 H 0.4913 0.5994 0.9003 0.012 Uiso 1 1 calc R U . . .
C12 C 0.4575(6) 0.5003(5) 0.6965(7) 0.0105(11) Uani 1 1 d . . . . .
C13 C 0.3513(7) 0.5933(5) 0.5937(7) 0.0164(12) Uani 1 1 d . . . . .
H13 H 0.3126 0.6618 0.6366 0.020 Uiso 1 1 calc R U . . .
C14 C 0.2996(7) 0.5887(6) 0.4274(7) 0.0218(13) Uani 1 1 d . . . . .
H14 H 0.2257 0.6532 0.3580 0.026 Uiso 1 1 calc R U . . .
C15 C 0.3566(8) 0.4895(6) 0.3645(8) 0.0232(14) Uani 1 1 d . . . . .
H15 H 0.3218 0.4857 0.2516 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4638(7) 0.3966(6) 0.4657(7) 0.0211(13) Uani 1 1 d . . . . .
H16 H 0.5033 0.3290 0.4223 0.025 Uiso 1 1 calc R U . . .
C17 C 0.5145(7) 0.4007(5) 0.6298(7) 0.0169(12) Uani 1 1 d . . . . .
H17 H 0.5884 0.3357 0.6984 0.020 Uiso 1 1 calc R U . . .
C18 C 0.0955(8) 0.2057(6) 0.5847(8) 0.0232(13) Uani 1 1 d . . . . .
H18A H 0.1782 0.1580 0.5644 0.035 Uiso 1 1 calc R U . . .
H18B H 0.0189 0.2522 0.4863 0.035 Uiso 1 1 calc R U . . .
H18C H 0.0322 0.1440 0.6157 0.035 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 C6 1.750(5) . ?
O1 C2 1.222(6) . ?
O2 C9 1.361(6) . ?
O2 C1 1.449(6) . ?
O3 C9 1.204(7) . ?
N1 C2 1.349(7) . ?
N1 C3 1.426(6) . ?
N1 C18 1.454(7) . ?
C1 C4 1.501(7) . ?
C1 C2 1.534(7) . ?
C1 C11 1.569(6) . ?
C3 C8 1.373(8) . ?
C3 C4 1.387(8) . ?
C4 C5 1.373(7) . ?
C5 C6 1.383(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(8) . ?
C7 C8 1.398(7) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.502(8) . ?
C10 C11 1.523(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.511(7) . ?
C11 H9 1.0000 . ?
C12 C13 1.377(8) . ?
C12 C17 1.409(7) . ?
C13 C14 1.399(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(8) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 O2 C1 110.7(4) . . ?
C2 N1 C3 111.1(4) . . ?
C2 N1 C18 123.9(4) . . ?
C3 N1 C18 125.0(5) . . ?
O2 C1 C4 114.6(4) . . ?
O2 C1 C2 109.7(4) . . ?
C4 C1 C2 102.4(4) . . ?
O2 C1 C11 105.0(4) . . ?
C4 C1 C11 114.1(4) . . ?
C2 C1 C11 111.2(4) . . ?
O1 C2 N1 126.7(5) . . ?
O1 C2 C1 125.8(5) . . ?
N1 C2 C1 107.5(4) . . ?
C8 C3 C4 121.7(5) . . ?
C8 C3 N1 129.2(5) . . ?
C4 C3 N1 109.1(4) . . ?
C5 C4 C3 121.1(5) . . ?
C5 C4 C1 130.6(5) . . ?
C3 C4 C1 108.2(4) . . ?
C4 C5 C6 117.4(5) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C7 C6 C5 121.8(5) . . ?
C7 C6 Cl1 118.9(4) . . ?
C5 C6 Cl1 119.3(4) . . ?
C6 C7 C8 120.4(5) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 117.4(5) . . ?
C3 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
O3 C9 O2 120.3(5) . . ?
O3 C9 C10 129.2(5) . . ?
O2 C9 C10 110.4(5) . . ?
C9 C10 C11 104.6(4) . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 C1 112.2(4) . . ?
C10 C11 C1 101.7(4) . . ?
C12 C11 H9 107.6 . . ?
C10 C11 H9 107.6 . . ?
C1 C11 H9 107.6 . . ?
C13 C12 C17 118.1(5) . . ?
C13 C12 C11 119.3(4) . . ?
C17 C12 C11 122.6(5) . . ?
C12 C13 C14 121.2(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 119.9(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O2 C1 C4 -145.3(4) . . . . ?
C9 O2 C1 C2 100.2(4) . . . . ?
C9 O2 C1 C11 -19.3(5) . . . . ?
C3 N1 C2 O1 171.3(4) . . . . ?
C18 N1 C2 O1 -7.8(8) . . . . ?
C3 N1 C2 C1 -10.3(5) . . . . ?
C18 N1 C2 C1 170.6(5) . . . . ?
O2 C1 C2 O1 -46.5(6) . . . . ?
C4 C1 C2 O1 -168.6(5) . . . . ?
C11 C1 C2 O1 69.1(6) . . . . ?
O2 C1 C2 N1 135.0(4) . . . . ?
C4 C1 C2 N1 12.9(5) . . . . ?
C11 C1 C2 N1 -109.3(5) . . . . ?
C2 N1 C3 C8 -174.5(5) . . . . ?
C18 N1 C3 C8 4.6(8) . . . . ?
C2 N1 C3 C4 3.1(5) . . . . ?
C18 N1 C3 C4 -177.9(5) . . . . ?
C8 C3 C4 C5 0.6(7) . . . . ?
N1 C3 C4 C5 -177.2(4) . . . . ?
C8 C3 C4 C1 -176.5(4) . . . . ?
N1 C3 C4 C1 5.7(5) . . . . ?
O2 C1 C4 C5 53.5(7) . . . . ?
C2 C1 C4 C5 172.2(5) . . . . ?
C11 C1 C4 C5 -67.6(7) . . . . ?
O2 C1 C4 C3 -129.8(4) . . . . ?
C2 C1 C4 C3 -11.1(5) . . . . ?
C11 C1 C4 C3 109.1(5) . . . . ?
C3 C4 C5 C6 2.1(7) . . . . ?
C1 C4 C5 C6 178.4(5) . . . . ?
C4 C5 C6 C7 -3.4(7) . . . . ?
C4 C5 C6 Cl1 176.5(4) . . . . ?
C5 C6 C7 C8 2.0(7) . . . . ?
Cl1 C6 C7 C8 -177.9(4) . . . . ?
C4 C3 C8 C7 -2.0(7) . . . . ?
N1 C3 C8 C7 175.3(4) . . . . ?
C6 C7 C8 C3 0.8(7) . . . . ?
C1 O2 C9 O3 -175.3(4) . . . . ?
C1 O2 C9 C10 3.2(5) . . . . ?
O3 C9 C10 C11 -166.9(5) . . . . ?
O2 C9 C10 C11 14.8(5) . . . . ?
C9 C10 C11 C12 -148.8(4) . . . . ?
C9 C10 C11 C1 -24.6(5) . . . . ?
O2 C1 C11 C12 155.8(4) . . . . ?
C4 C1 C11 C12 -77.9(5) . . . . ?
C2 C1 C11 C12 37.3(6) . . . . ?
O2 C1 C11 C10 26.8(5) . . . . ?
C4 C1 C11 C10 153.1(4) . . . . ?
C2 C1 C11 C10 -91.7(5) . . . . ?
C10 C11 C12 C13 -146.7(5) . . . . ?
C1 C11 C12 C13 94.3(5) . . . . ?
C10 C11 C12 C17 34.5(7) . . . . ?
C1 C11 C12 C17 -84.4(5) . . . . ?
C17 C12 C13 C14 0.7(7) . . . . ?
C11 C12 C13 C14 -178.0(5) . . . . ?
C12 C13 C14 C15 -0.5(8) . . . . ?
C13 C14 C15 C16 -0.1(8) . . . . ?
C14 C15 C16 C17 0.4(8) . . . . ?
C15 C16 C17 C12 -0.1(8) . . . . ?
C13 C12 C17 C16 -0.5(7) . . . . ?
C11 C12 C17 C16 178.3(5) . . . . ?

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.128

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Dichloromethane-Petroleum ether'
