# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lyq-01
_database_code_depnum_ccdc_archive 'CCDC 1052930'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl N O3'
_chemical_formula_sum            'C18 H12 Cl N O3'
_chemical_formula_weight         325.74
_chemical_absolute_configuration ad


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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   9.3195(4)
_cell_length_b                   10.8944(5)
_cell_length_c                   14.3609(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1458.07(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7975
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.4

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8787
_exptl_absorpt_correction_T_max  0.9441
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10481
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3252
_reflns_number_gt                2375
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0339P)²+0.5410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881, Friedel pairs  1245'
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5056(2) 0.52072(19) 0.77968(14) 0.0306(5) Uani 1 1 d . . .
C2 C 0.6477(2) 0.4479(2) 0.77992(16) 0.0357(5) Uani 1 1 d . . .
C3 C 0.6247(3) 0.5383(2) 0.92356(16) 0.0371(5) Uani 1 1 d . . .
C4 C 0.6520(3) 0.5736(3) 1.01442(17) 0.0468(7) Uani 1 1 d . . .
H4 H 0.7342 0.5482 1.0456 0.056 Uiso 1 1 calc R . .
C5 C 0.5512(3) 0.6483(2) 1.05673(17) 0.0485(7) Uani 1 1 d . . .
H5 H 0.5660 0.6733 1.1179 0.058 Uiso 1 1 calc R . .
C6 C 0.4291(3) 0.6870(2) 1.01036(16) 0.0446(6) Uani 1 1 d . . .
H6 H 0.3636 0.7378 1.0404 0.053 Uiso 1 1 calc R . .
C7 C 0.4037(3) 0.6502(2) 0.91889(16) 0.0390(6) Uani 1 1 d . . .
H7 H 0.3221 0.6761 0.8872 0.047 Uiso 1 1 calc R . .
C8 C 0.5023(2) 0.5745(2) 0.87655(14) 0.0310(5) Uani 1 1 d . . .
C9 C 0.3566(2) 0.3848(2) 0.68731(16) 0.0330(5) Uani 1 1 d . . .
C10 C 0.4038(3) 0.4517(2) 0.60435(15) 0.0344(5) Uani 1 1 d . . .
H10 H 0.3913 0.4153 0.5464 0.041 Uiso 1 1 calc R . .
C11 C 0.4642(2) 0.5630(2) 0.60833(14) 0.0305(5) Uani 1 1 d . . .
C12 C 0.4979(3) 0.6162(2) 0.70231(14) 0.0367(5) Uani 1 1 d . . .
H12A H 0.4250 0.6762 0.7180 0.044 Uiso 1 1 calc R . .
H12B H 0.5892 0.6588 0.6989 0.044 Uiso 1 1 calc R . .
C13 C 0.4909(2) 0.63965(19) 0.52421(15) 0.0310(5) Uani 1 1 d . . .
C14 C 0.5697(3) 0.7480(2) 0.53006(16) 0.0413(6) Uani 1 1 d . . .
H14 H 0.6103 0.7705 0.5867 0.050 Uiso 1 1 calc R . .
C15 C 0.5886(3) 0.8228(2) 0.45294(17) 0.0462(6) Uani 1 1 d . . .
H15 H 0.6409 0.8952 0.4579 0.055 Uiso 1 1 calc R . .
C16 C 0.5294(3) 0.7891(2) 0.36902(16) 0.0388(6) Uani 1 1 d . . .
C17 C 0.4526(3) 0.6827(2) 0.36041(16) 0.0437(6) Uani 1 1 d . . .
H17 H 0.4137 0.6603 0.3032 0.052 Uiso 1 1 calc R . .
C18 C 0.4334(3) 0.6086(2) 0.43790(16) 0.0407(6) Uani 1 1 d . . .
H18 H 0.3808 0.5365 0.4321 0.049 Uiso 1 1 calc R . .
Cl1 Cl 0.55258(10) 0.88440(7) 0.27272(5) 0.0639(2) Uani 1 1 d . . .
N1 N 0.7091(2) 0.4642(2) 0.86502(14) 0.0451(5) Uani 1 1 d . . .
H1 H 0.7901 0.4328 0.8811 0.054 Uiso 1 1 calc R . .
O1 O 0.6947(2) 0.38488(18) 0.71746(12) 0.0513(5) Uani 1 1 d . . .
O2 O 0.39071(16) 0.43132(14) 0.77274(10) 0.0349(4) Uani 1 1 d . . .
O3 O 0.28401(19) 0.29327(15) 0.68588(12) 0.0419(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.451(3) . ?
C1 C8 1.510(3) . ?
C1 C12 1.523(3) . ?
C1 C2 1.544(3) . ?
C2 O1 1.212(3) . ?
C2 N1 1.361(3) . ?
C3 C4 1.384(3) . ?
C3 C8 1.383(3) . ?
C3 N1 1.406(3) . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(3) . ?
C7 H7 0.9300 . ?
C9 O3 1.205(3) . ?
C9 O2 1.365(3) . ?
C9 C10 1.465(3) . ?
C10 C11 1.338(3) . ?
C10 H10 0.9300 . ?
C11 C13 1.490(3) . ?
C11 C12 1.502(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.392(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(3) . ?
C16 Cl1 1.742(2) . ?
C17 C18 1.386(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 H1 0.8600 . ?

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
O2 C1 C8 108.00(16) . . ?
O2 C1 C12 111.94(17) . . ?
C8 C1 C12 113.98(17) . . ?
O2 C1 C2 106.76(16) . . ?
C8 C1 C2 102.39(17) . . ?
C12 C1 C2 113.09(18) . . ?
O1 C2 N1 125.9(2) . . ?
O1 C2 C1 126.9(2) . . ?
N1 C2 C1 107.24(19) . . ?
C4 C3 C8 122.2(2) . . ?
C4 C3 N1 128.4(2) . . ?
C8 C3 N1 109.5(2) . . ?
C5 C4 C3 117.0(2) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 118.4(2) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 C3 120.4(2) . . ?
C7 C8 C1 130.8(2) . . ?
C3 C8 C1 108.81(19) . . ?
O3 C9 O2 117.0(2) . . ?
O3 C9 C10 124.5(2) . . ?
O2 C9 C10 118.4(2) . . ?
C11 C10 C9 122.9(2) . . ?
C11 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C10 C11 C13 122.93(18) . . ?
C10 C11 C12 118.41(19) . . ?
C13 C11 C12 118.54(18) . . ?
C11 C12 C1 113.71(18) . . ?
C11 C12 H12A 108.8 . . ?
C1 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C1 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 117.6(2) . . ?
C18 C13 C11 121.45(19) . . ?
C14 C13 C11 120.94(19) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.5(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 Cl1 119.86(19) . . ?
C15 C16 Cl1 119.16(19) . . ?
C16 C17 C18 119.2(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C13 121.6(2) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
C2 N1 C3 112.1(2) . . ?
C2 N1 H1 124.0 . . ?
C3 N1 H1 124.0 . . ?
C9 O2 C1 118.89(16) . . ?

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
O2 C1 C2 O1 63.8(3) . . . . ?
C8 C1 C2 O1 177.2(2) . . . . ?
C12 C1 C2 O1 -59.7(3) . . . . ?
O2 C1 C2 N1 -114.1(2) . . . . ?
C8 C1 C2 N1 -0.8(2) . . . . ?
C12 C1 C2 N1 122.3(2) . . . . ?
C8 C3 C4 C5 -0.5(4) . . . . ?
N1 C3 C4 C5 179.5(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 C3 -1.3(3) . . . . ?
C6 C7 C8 C1 -179.5(2) . . . . ?
C4 C3 C8 C7 1.4(4) . . . . ?
N1 C3 C8 C7 -178.6(2) . . . . ?
C4 C3 C8 C1 180.0(2) . . . . ?
N1 C3 C8 C1 -0.1(3) . . . . ?
O2 C1 C8 C7 -68.7(3) . . . . ?
C12 C1 C8 C7 56.4(3) . . . . ?
C2 C1 C8 C7 178.9(2) . . . . ?
O2 C1 C8 C3 113.0(2) . . . . ?
C12 C1 C8 C3 -122.0(2) . . . . ?
C2 C1 C8 C3 0.5(2) . . . . ?
O3 C9 C10 C11 168.9(2) . . . . ?
O2 C9 C10 C11 -7.9(3) . . . . ?
C9 C10 C11 C13 -169.9(2) . . . . ?
C9 C10 C11 C12 6.1(4) . . . . ?
C10 C11 C12 C1 19.5(3) . . . . ?
C13 C11 C12 C1 -164.30(19) . . . . ?
O2 C1 C12 C11 -42.6(3) . . . . ?
C8 C1 C12 C11 -165.5(2) . . . . ?
C2 C1 C12 C11 78.1(2) . . . . ?
C10 C11 C13 C18 10.7(4) . . . . ?
C12 C11 C13 C18 -165.3(2) . . . . ?
C10 C11 C13 C14 -172.0(2) . . . . ?
C12 C11 C13 C14 12.0(3) . . . . ?
C18 C13 C14 C15 0.7(4) . . . . ?
C11 C13 C14 C15 -176.7(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C14 C15 C16 Cl1 179.5(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
Cl1 C16 C17 C18 -179.1(2) . . . . ?
C16 C17 C18 C13 -0.3(4) . . . . ?
C14 C13 C18 C17 -0.4(4) . . . . ?
C11 C13 C18 C17 177.0(2) . . . . ?
O1 C2 N1 C3 -177.2(2) . . . . ?
C1 C2 N1 C3 0.8(3) . . . . ?
C4 C3 N1 C2 179.5(3) . . . . ?
C8 C3 N1 C2 -0.5(3) . . . . ?
O3 C9 O2 C1 164.46(19) . . . . ?
C10 C9 O2 C1 -18.5(3) . . . . ?
C8 C1 O2 C9 169.32(18) . . . . ?
C12 C1 O2 C9 43.1(2) . . . . ?
C2 C1 O2 C9 -81.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.055
