# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_iw1203
_database_code_depnum_ccdc_archive 'CCDC 1944984'
loop_
_audit_author_name
_audit_author_address
'Ikuhide Fujisawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Cl2 N O'
_chemical_melting_point          ?


_exptl_crystal_description       Block

_exptl_crystal_colour            brown
_diffrn_ambient_temperature      120
_chemical_formula_weight         306.17

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_chemical_absolute_configuration ad

loop_
_space_group_symop_operation_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'

_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.
;

_cell_length_a                   5.7489(4)
_cell_length_b                   10.8111(7)
_cell_length_c                   22.1649(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1377.59(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120

_cell_measurement_reflns_used    6506

_cell_measurement_theta_min      2.6

_cell_measurement_theta_max      25.0

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.10

_exptl_absorpt_coefficient_mu    0.465
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   Numerical

_exptl_absorpt_correction_T_min  0.819

_exptl_absorpt_correction_T_max  0.915

_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
Rigaku CrystalClear-SM Expert 2.0 r16
;

_diffrn_measurement_method       
;
Oscillation method with Fine-Slice process
profile data from φ-scans
;
_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            17718
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.632
_diffrn_reflns_theta_max         30.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4377
_reflns_number_gt                3996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution    'SIR2014 (Burla, Caliandro et al., 2015)'

_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0451P)²+0.2020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(2)

_refine_ls_number_reflns         4377
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
C2 C -0.2799(4) 0.2729(2) 0.43756(9) 0.0181(4) Uani 1 1 d . . . . .
C4 C -0.1451(4) 0.1297(2) 0.35712(10) 0.0196(4) Uani 1 1 d . . . . .
C6 C 0.2201(4) 0.1314(2) 0.29748(9) 0.0193(4) Uani 1 1 d . . . . .
C1 C -0.1328(4) 0.4541(2) 0.39114(10) 0.0199(4) Uani 1 1 d . . . . .
C3 C -0.0722(4) 0.22966(19) 0.40032(9) 0.0173(4) Uani 1 1 d . . . . .
C5 C -0.0077(4) 0.0845(2) 0.31315(10) 0.0202(4) Uani 1 1 d . . . . .
C7 C 0.3045(4) 0.2474(2) 0.30237(10) 0.0214(4) Uani 1 1 d . . . . .
C8 C 0.1768(4) 0.3515(2) 0.32708(10) 0.0215(4) Uani 1 1 d . . . . .
C9 C 0.0058(4) 0.34505(19) 0.36805(9) 0.0175(4) Uani 1 1 d . . . . .
C10 C -0.5009(4) 0.4658(2) 0.45507(10) 0.0196(4) Uani 1 1 d . . . . .
C11 C -0.4398(3) 0.54854(19) 0.50804(10) 0.0176(4) Uani 1 1 d . . . . .
C12 C -0.2319(4) 0.5369(2) 0.53983(9) 0.0192(4) Uani 1 1 d . . . . .
H1 H 0.049(5) 0.202(3) 0.4278(12) 0.026(7) Uiso 1 1 d . . . . .
H2 H -0.301(5) 0.094(2) 0.3620(10) 0.014(6) Uiso 1 1 d . . . . .
H4 H 0.455(5) 0.257(3) 0.2870(12) 0.025(7) Uiso 1 1 d . . . . .
H6 H -0.210(5) 0.504(3) 0.3597(13) 0.031(8) Uiso 1 1 d . . . . .
H7 H -0.023(5) 0.515(3) 0.4138(12) 0.020(6) Uiso 1 1 d . . . . .
H3 H -0.061(5) 0.012(3) 0.2900(12) 0.023(7) Uiso 1 1 d . . . . .
H8 H -0.611(5) 0.408(2) 0.4660(11) 0.014(6) Uiso 1 1 d . . . . .
H5 H 0.223(5) 0.435(3) 0.3117(12) 0.023(7) Uiso 1 1 d . . . . .
H9 H -0.572(5) 0.516(3) 0.4272(12) 0.023(7) Uiso 1 1 d . . . . .
H11 H -0.051(5) 0.603(2) 0.6126(12) 0.017(6) Uiso 1 1 d . . . . .
H12 H -0.668(5) 0.765(3) 0.5925(13) 0.027(7) Uiso 1 1 d . . . . .
N1 N -0.3069(3) 0.39665(17) 0.43016(8) 0.0185(3) Uani 1 1 d . . . . .
O1 O -0.4067(3) 0.20616(15) 0.46780(7) 0.0221(3) Uani 1 1 d . . . . .
Cl1 Cl 0.39631(9) 0.02085(5) 0.26105(2) 0.02446(13) Uani 1 1 d . . . . .
Cl2 Cl -0.30098(13) 0.78687(6) 0.67207(3) 0.03320(16) Uani 1 1 d . . . . .
C13 C -0.1882(4) 0.6118(2) 0.59016(10) 0.0208(4) Uani 1 1 d . . . . .
H10 H -0.127(6) 0.475(3) 0.5254(14) 0.039(9) Uiso 1 1 d . . . . .
H13 H -0.755(4) 0.642(3) 0.5062(12) 0.019(7) Uiso 1 1 d . . . . .
C14 C -0.3550(4) 0.6958(2) 0.60869(10) 0.0220(4) Uani 1 1 d . . . . .
C15 C -0.5634(4) 0.7084(2) 0.57791(10) 0.0223(4) Uani 1 1 d . . . . .
C16 C -0.6040(4) 0.6350(2) 0.52721(10) 0.0205(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
C2 O1 1.226(3) . ?
C2 N1 1.356(3) . ?
C2 C3 1.525(3) . ?
C4 C5 1.346(3) . ?
C4 C3 1.503(3) . ?
C4 H2 0.98(3) . ?
C6 C7 1.349(3) . ?
C6 C5 1.447(3) . ?
C6 Cl1 1.763(2) . ?
C1 N1 1.461(3) . ?
C1 C9 1.512(3) . ?
C1 H6 0.99(3) . ?
C1 H7 1.04(3) . ?
C3 C9 1.506(3) . ?
C3 H1 0.97(3) . ?
C5 H3 0.99(3) . ?
C7 C8 1.450(3) . ?
C7 H4 0.94(3) . ?
C8 C9 1.340(3) . ?
C8 H5 1.00(3) . ?
C10 N1 1.452(3) . ?
C10 C11 1.517(3) . ?
C10 H8 0.92(3) . ?
C10 H9 0.92(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.401(3) . ?
C12 H10 0.95(3) . ?
Cl2 C14 1.743(2) . ?
C13 C14 1.383(3) . ?
C13 H11 0.94(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.395(3) . ?
C15 H12 0.91(3) . ?
C16 H13 0.99(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
O1 C2 N1 125.4(2) . . ?
O1 C2 C3 125.5(2) . . ?
N1 C2 C3 109.07(18) . . ?
C5 C4 C3 124.0(2) . . ?
C5 C4 H2 118.1(14) . . ?
C3 C4 H2 117.9(14) . . ?
C7 C6 C5 129.2(2) . . ?
C7 C6 Cl1 117.44(17) . . ?
C5 C6 Cl1 113.11(16) . . ?
N1 C1 C9 103.29(17) . . ?
N1 C1 H6 110.2(17) . . ?
C9 C1 H6 115.2(17) . . ?
N1 C1 H7 113.5(15) . . ?
C9 C1 H7 109.6(15) . . ?
H6 C1 H7 105(2) . . ?
C4 C3 C9 112.07(17) . . ?
C4 C3 C2 110.30(17) . . ?
C9 C3 C2 103.65(17) . . ?
C4 C3 H1 112.3(17) . . ?
C9 C3 H1 109.8(17) . . ?
C2 C3 H1 108.3(16) . . ?
C4 C5 C6 125.3(2) . . ?
C4 C5 H3 118.9(16) . . ?
C6 C5 H3 115.8(16) . . ?
C6 C7 C8 124.7(2) . . ?
C6 C7 H4 113.8(19) . . ?
C8 C7 H4 121.5(19) . . ?
C9 C8 C7 125.9(2) . . ?
C9 C8 H5 118.2(16) . . ?
C7 C8 H5 115.8(16) . . ?
C8 C9 C3 125.65(19) . . ?
C8 C9 C1 125.1(2) . . ?
C3 C9 C1 109.16(17) . . ?
N1 C10 C11 114.83(17) . . ?
N1 C10 H8 106.2(16) . . ?
C11 C10 H8 110.7(16) . . ?
N1 C10 H9 113.1(17) . . ?
C11 C10 H9 105.9(17) . . ?
H8 C10 H9 106(2) . . ?
C12 C11 C16 119.1(2) . . ?
C12 C11 C10 122.46(19) . . ?
C16 C11 C10 118.31(19) . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H10 115.8(19) . . ?
C13 C12 H10 124(2) . . ?
C2 N1 C10 123.36(18) . . ?
C2 N1 C1 114.33(17) . . ?
C10 N1 C1 122.17(18) . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H11 119.5(16) . . ?
C12 C13 H11 120.9(16) . . ?
C13 C14 C15 121.2(2) . . ?
C13 C14 Cl2 119.12(18) . . ?
C15 C14 Cl2 119.69(18) . . ?
C14 C15 C16 119.0(2) . . ?
C14 C15 H12 117.4(18) . . ?
C16 C15 H12 123.6(18) . . ?
C11 C16 C15 120.9(2) . . ?
C11 C16 H13 120.0(16) . . ?
C15 C16 H13 119.0(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C4 C3 C9 56.2(3) . . . . ?
C5 C4 C3 C2 171.1(2) . . . . ?
O1 C2 C3 C4 54.6(3) . . . . ?
N1 C2 C3 C4 -123.27(19) . . . . ?
O1 C2 C3 C9 174.7(2) . . . . ?
N1 C2 C3 C9 -3.1(2) . . . . ?
C3 C4 C5 C6 -5.6(4) . . . . ?
C7 C6 C5 C4 -29.6(4) . . . . ?
Cl1 C6 C5 C4 156.5(2) . . . . ?
C5 C6 C7 C8 1.8(4) . . . . ?
Cl1 C6 C7 C8 175.46(18) . . . . ?
C6 C7 C8 C9 27.3(4) . . . . ?
C7 C8 C9 C3 5.8(4) . . . . ?
C7 C8 C9 C1 -177.0(2) . . . . ?
C4 C3 C9 C8 -57.1(3) . . . . ?
C2 C3 C9 C8 -176.0(2) . . . . ?
C4 C3 C9 C1 125.28(19) . . . . ?
C2 C3 C9 C1 6.4(2) . . . . ?
N1 C1 C9 C8 175.3(2) . . . . ?
N1 C1 C9 C3 -7.1(2) . . . . ?
N1 C10 C11 C12 -15.3(3) . . . . ?
N1 C10 C11 C16 168.06(19) . . . . ?
C16 C11 C12 C13 -0.4(3) . . . . ?
C10 C11 C12 C13 -177.1(2) . . . . ?
O1 C2 N1 C10 -3.5(3) . . . . ?
C3 C2 N1 C10 174.36(18) . . . . ?
O1 C2 N1 C1 -179.3(2) . . . . ?
C3 C2 N1 C1 -1.4(2) . . . . ?
C11 C10 N1 C2 107.7(2) . . . . ?
C11 C10 N1 C1 -76.9(2) . . . . ?
C9 C1 N1 C2 5.3(2) . . . . ?
C9 C1 N1 C10 -170.53(18) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C12 C13 C14 Cl2 178.98(17) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
Cl2 C14 C15 C16 179.91(18) . . . . ?
C12 C11 C16 C15 -0.7(3) . . . . ?
C10 C11 C16 C15 176.1(2) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H1 O1 0.97(3) 2.53(3) 3.151(3) 122(2) 3_556 yes
C1 H6 Cl1 0.99(3) 2.89(3) 3.768(2) 149(2) 4 yes
C10 H8 O1 0.92(3) 2.56(3) 3.438(3) 159(2) 3_456 yes

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.058

_diffrn_radiation_monochromator  'Graphite Monochromator'

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
