# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_zhaoyl140710_0m
_database_code_depnum_ccdc_archive 'CCDC 1028181'
_audit_update_record             
;
2015-04-08 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Cl N2 O'
_chemical_formula_weight         308.75

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'
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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   3.9823(6)
_cell_length_b                   11.7455(17)
_cell_length_c                   16.580(2)
_cell_angle_alpha                86.931(3)
_cell_angle_beta                 84.919(3)
_cell_angle_gamma                89.788(3)
_cell_volume                     771.36(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4449
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2707
_reflns_number_gt                1850
_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)+(0.0929P)²+0.0979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2707
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1354
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1679(8) 0.2738(2) -0.12569(15) 0.0477(7) Uani 1 1 d . . .
C2 C 1.1053(8) 0.1990(2) -0.18315(17) 0.0514(7) Uani 1 1 d . . .
C3 C 0.9260(7) 0.1019(2) -0.16018(16) 0.0478(7) Uani 1 1 d . . .
C4 C 0.8046(8) 0.0794(3) -0.08062(18) 0.0543(8) Uani 1 1 d . . .
C5 C 0.8659(7) 0.1554(2) -0.02362(17) 0.0470(7) Uani 1 1 d . . .
C6 C 1.0505(6) 0.2543(2) -0.04432(14) 0.0371(6) Uani 1 1 d . . .
C7 C 1.1336(7) 0.3347(2) 0.01459(15) 0.0421(6) Uani 1 1 d . . .
C8 C 1.0462(7) 0.3290(2) 0.09382(15) 0.0441(7) Uani 1 1 d . . .
C9 C 1.1582(7) 0.4166(2) 0.14512(14) 0.0420(6) Uani 1 1 d . . .
C10 C 1.0381(7) 0.4090(2) 0.23395(14) 0.0408(6) Uani 1 1 d . . .
C11 C 1.1603(7) 0.5031(2) 0.27727(15) 0.0475(7) Uani 1 1 d . . .
C12 C 0.7335(6) 0.2997(2) 0.34445(14) 0.0407(6) Uani 1 1 d . . .
C13 C 0.7434(8) 0.3695(3) 0.40961(16) 0.0528(8) Uani 1 1 d . . .
C14 C 0.6116(8) 0.3317(3) 0.48580(17) 0.0589(8) Uani 1 1 d . . .
C15 C 0.4586(7) 0.2258(3) 0.50023(16) 0.0523(7) Uani 1 1 d . . .
C16 C 0.4474(8) 0.1578(3) 0.43498(18) 0.0561(8) Uani 1 1 d . . .
C17 C 0.5753(7) 0.1948(3) 0.35855(16) 0.0507(7) Uani 1 1 d . . .
C18 C 0.3174(13) 0.1869(4) 0.5844(2) 0.0767(11) Uani 1 1 d . . .
Cl1 Cl 0.8486(2) 0.00414(8) -0.23164(5) 0.0814(4) Uani 1 1 d . . .
H1 H 0.634(7) 0.376(2) 0.5306(18) 0.057(8) Uiso 1 1 d . . .
H2 H 0.841(7) 0.440(2) 0.4063(16) 0.055(8) Uiso 1 1 d . . .
H3 H 0.561(6) 0.149(2) 0.3171(15) 0.040(7) Uiso 1 1 d . . .
H4 H 0.316(8) 0.085(3) 0.4426(18) 0.068(9) Uiso 1 1 d . . .
H5 H 0.909(7) 0.270(2) 0.1238(17) 0.055(8) Uiso 1 1 d . . .
H6 H 1.266(7) 0.395(2) -0.0053(15) 0.045(7) Uiso 1 1 d . . .
H7 H 1.300(7) 0.341(2) -0.1365(16) 0.055(8) Uiso 1 1 d . . .
H8 H 1.175(7) 0.214(2) -0.2366(19) 0.064(9) Uiso 1 1 d . . .
H9 H 0.689(7) 0.015(2) -0.0656(16) 0.052(8) Uiso 1 1 d . . .
H10 H 0.781(8) 0.141(2) 0.0287(19) 0.067(9) Uiso 1 1 d . . .
H11 H 0.141(11) 0.233(3) 0.604(3) 0.113(16) Uiso 1 1 d . . .
H12 H 0.185(11) 0.117(4) 0.579(3) 0.117(16) Uiso 1 1 d . . .
H13 H 0.472(13) 0.179(4) 0.620(3) 0.14(2) Uiso 1 1 d . . .
N1 N 1.2622(8) 0.5780(2) 0.30908(16) 0.0739(8) Uani 1 1 d . . .
N2 N 0.8567(5) 0.32432(18) 0.26341(11) 0.0410(5) Uani 1 1 d . . .
O1 O 1.3474(6) 0.49451(17) 0.12047(11) 0.0627(6) 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 C2 1.369(4) . ?
C1 C6 1.395(3) . ?
C1 H7 0.95(3) . ?
C2 C3 1.366(4) . ?
C2 H8 0.91(3) . ?
C3 C4 1.376(4) . ?
C3 Cl1 1.741(2) . ?
C4 C5 1.373(4) . ?
C4 H9 0.90(3) . ?
C5 C6 1.388(3) . ?
C5 H10 0.91(3) . ?
C6 C7 1.453(3) . ?
C7 C8 1.327(4) . ?
C7 H6 0.91(3) . ?
C8 C9 1.465(3) . ?
C8 H5 0.97(3) . ?
C9 O1 1.218(3) . ?
C9 C10 1.506(3) . ?
C10 N2 1.281(3) . ?
C10 C11 1.457(3) . ?
C11 N1 1.143(3) . ?
C12 C17 1.385(4) . ?
C12 C13 1.394(3) . ?
C12 N2 1.404(3) . ?
C13 C14 1.375(4) . ?
C13 H2 0.92(3) . ?
C14 C15 1.387(4) . ?
C14 H1 0.94(3) . ?
C15 C16 1.383(4) . ?
C15 C18 1.505(4) . ?
C16 C17 1.372(4) . ?
C16 H4 1.00(3) . ?
C17 H3 0.90(2) . ?
C18 H11 0.94(4) . ?
C18 H12 0.98(4) . ?
C18 H13 0.89(5) . ?

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
C2 C1 C6 121.8(3) . . ?
C2 C1 H7 124.0(16) . . ?
C6 C1 H7 114.1(16) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H8 119.5(18) . . ?
C1 C2 H8 121.3(19) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 Cl1 120.2(2) . . ?
C4 C3 Cl1 118.9(2) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H9 119.9(17) . . ?
C3 C4 H9 120.6(17) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H10 118.9(19) . . ?
C6 C5 H10 119.7(19) . . ?
C5 C6 C1 117.2(2) . . ?
C5 C6 C7 123.2(2) . . ?
C1 C6 C7 119.6(2) . . ?
C8 C7 C6 127.5(2) . . ?
C8 C7 H6 116.6(16) . . ?
C6 C7 H6 115.8(16) . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H5 126.2(16) . . ?
C9 C8 H5 113.3(16) . . ?
O1 C9 C8 123.9(2) . . ?
O1 C9 C10 117.8(2) . . ?
C8 C9 C10 118.3(2) . . ?
N2 C10 C11 127.6(2) . . ?
N2 C10 C9 119.8(2) . . ?
C11 C10 C9 112.6(2) . . ?
N1 C11 C10 177.9(3) . . ?
C17 C12 C13 117.9(2) . . ?
C17 C12 N2 114.4(2) . . ?
C13 C12 N2 127.6(2) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H2 115.4(17) . . ?
C12 C13 H2 124.4(17) . . ?
C13 C14 C15 121.9(3) . . ?
C13 C14 H1 120.2(17) . . ?
C15 C14 H1 117.9(17) . . ?
C16 C15 C14 117.4(2) . . ?
C16 C15 C18 122.0(3) . . ?
C14 C15 C18 120.6(3) . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H4 119.6(17) . . ?
C15 C16 H4 118.6(17) . . ?
C16 C17 C12 121.2(3) . . ?
C16 C17 H3 119.3(15) . . ?
C12 C17 H3 119.5(15) . . ?
C15 C18 H11 112(3) . . ?
C15 C18 H12 107(3) . . ?
H11 C18 H12 98(3) . . ?
C15 C18 H13 114(3) . . ?
H11 C18 H13 111(4) . . ?
H12 C18 H13 114(4) . . ?
C10 N2 C12 128.3(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
C6 C1 C2 C3 -0.7(5) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C1 C2 C3 Cl1 -178.9(2) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
Cl1 C3 C4 C5 179.6(2) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -177.3(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C6 C7 178.0(3) . . . . ?
C5 C6 C7 C8 -1.4(5) . . . . ?
C1 C6 C7 C8 -179.4(3) . . . . ?
C6 C7 C8 C9 178.7(2) . . . . ?
C7 C8 C9 O1 -4.0(4) . . . . ?
C7 C8 C9 C10 177.1(3) . . . . ?
O1 C9 C10 N2 -175.5(3) . . . . ?
C8 C9 C10 N2 3.4(4) . . . . ?
O1 C9 C10 C11 2.7(4) . . . . ?
C8 C9 C10 C11 -178.4(2) . . . . ?
N2 C10 C11 N1 172(9) . . . . ?
C9 C10 C11 N1 -6(9) . . . . ?
C17 C12 C13 C14 2.8(4) . . . . ?
N2 C12 C13 C14 -179.7(3) . . . . ?
C12 C13 C14 C15 -1.7(5) . . . . ?
C13 C14 C15 C16 1.0(5) . . . . ?
C13 C14 C15 C18 179.9(4) . . . . ?
C14 C15 C16 C17 -1.6(5) . . . . ?
C18 C15 C16 C17 179.6(3) . . . . ?
C15 C16 C17 C12 2.8(5) . . . . ?
C13 C12 C17 C16 -3.4(4) . . . . ?
N2 C12 C17 C16 178.8(3) . . . . ?
C11 C10 N2 C12 -0.9(5) . . . . ?
C9 C10 N2 C12 177.0(2) . . . . ?
C17 C12 N2 C10 -173.2(3) . . . . ?
C13 C12 N2 C10 9.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.059
