# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_konglingheng20200324_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1992558'
loop_
_audit_author_name
_audit_author_address
'klh '
;snnu
China
;
_audit_update_record             
;
2020-03-25 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_audit_creation_date             2020-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H9 Cl O3'
_chemical_formula_sum            'C17 H9 Cl O3'
_chemical_formula_weight         296.69
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2844(11)
_cell_length_b                   8.6986(12)
_cell_length_c                   10.7524(15)
_cell_angle_alpha                68.114(4)
_cell_angle_beta                 78.900(4)
_cell_angle_gamma                68.561(4)
_cell_volume                     667.83(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.468
_cell_measurement_theta_min      2.647
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1173 before and 0.0701 after correction.
The Ratio of minimum to maximum transmission is 0.9280.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            41128
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.045
_diffrn_ambient_temperature      153.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2673
_reflns_number_total             3060
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.184
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0674P)²+0.2189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.14153(6) 0.36229(6) 0.40787(4) 0.04304(17) Uani 1 1 d . . . . .
O1 O 0.42922(13) -0.09886(14) 0.75733(11) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.47078(15) 0.12752(16) 0.58314(12) 0.0288(3) Uani 1 1 d . . . . .
O3 O 0.23920(18) -0.01096(17) 0.97214(13) 0.0374(3) Uani 1 1 d . . . . .
C4 C 0.2373(2) -0.1436(2) 0.96019(16) 0.0273(3) Uani 1 1 d . . . . .
C5 C 0.14049(19) -0.05467(19) 0.73397(15) 0.0219(3) Uani 1 1 d . . . . .
C6 C 0.19222(19) 0.07528(19) 0.63256(15) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.4318(2) -0.4064(2) 0.71507(16) 0.0268(3) Uani 1 1 d . . . . .
H7 H 0.4661 -0.3228 0.6385 0.032 Uiso 1 1 calc R . . . .
C8 C 0.4690(2) -0.5765(2) 0.71642(18) 0.0318(4) Uani 1 1 d . . . . .
H8 H 0.5285 -0.6084 0.6404 0.038 Uiso 1 1 calc R . . . .
C9 C 0.34445(19) -0.3590(2) 0.82572(15) 0.0230(3) Uani 1 1 d . . . . .
C10 C 0.2934(2) -0.4819(2) 0.93839(16) 0.0284(3) Uani 1 1 d . . . . .
C11 C 0.4201(2) -0.6996(2) 0.82765(19) 0.0344(4) Uani 1 1 d . . . . .
H11 H 0.4465 -0.8157 0.8282 0.041 Uiso 1 1 calc R . . . .
C12 C 0.37480(19) 0.04697(19) 0.64791(15) 0.0219(3) Uani 1 1 d . . . . .
C13 C -0.0899(2) 0.1964(2) 0.54808(18) 0.0333(4) Uani 1 1 d . . . . .
H13 H -0.1707 0.2826 0.4846 0.040 Uiso 1 1 calc R . . . .
C14 C 0.29134(19) -0.17170(19) 0.82174(15) 0.0223(3) Uani 1 1 d . . . . .
C15 C 0.0773(2) 0.2027(2) 0.53757(16) 0.0271(3) Uani 1 1 d . . . . .
C16 C 0.1768(3) -0.2768(2) 1.06663(17) 0.0351(4) Uani 1 1 d . . . . .
H16 H 0.1173 -0.2529 1.1456 0.042 Uiso 1 1 calc R . . . .
C17 C -0.0258(2) -0.0634(2) 0.74542(17) 0.0282(3) Uani 1 1 d . . . . .
H17 H -0.0602 -0.1537 0.8152 0.034 Uiso 1 1 calc R . . . .
C18 C 0.3325(3) -0.6524(2) 0.93807(18) 0.0343(4) Uani 1 1 d . . . . .
H18 H 0.2987 -0.7368 1.0144 0.041 Uiso 1 1 calc R . . . .
C19 C 0.2035(3) -0.4320(2) 1.05506(17) 0.0368(4) Uani 1 1 d . . . . .
H19 H 0.1615 -0.5148 1.1271 0.044 Uiso 1 1 calc R . . . .
C20 C -0.1399(2) 0.0650(3) 0.65078(19) 0.0335(4) Uani 1 1 d . . . . .
H20 H -0.2549 0.0628 0.6565 0.040 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 C15 1.7226(17) . ?
O1 C12 1.3675(18) . ?
O1 C14 1.4433(17) . ?
O2 C12 1.1993(18) . ?
O3 C4 1.213(2) . ?
C4 C14 1.553(2) . ?
C4 C16 1.455(2) . ?
C5 C6 1.380(2) . ?
C5 C14 1.515(2) . ?
C5 C17 1.387(2) . ?
C6 C12 1.473(2) . ?
C6 C15 1.392(2) . ?
C7 C8 1.392(2) . ?
C7 C9 1.387(2) . ?
C8 C11 1.384(3) . ?
C9 C10 1.399(2) . ?
C9 C14 1.511(2) . ?
C10 C18 1.399(2) . ?
C10 C19 1.458(2) . ?
C11 C18 1.385(3) . ?
C13 C15 1.387(2) . ?
C13 C20 1.388(3) . ?
C16 C19 1.336(3) . ?
C17 C20 1.389(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
C12 O1 C14 111.55(11) . . ?
O3 C4 C14 119.38(15) . . ?
O3 C4 C16 124.01(15) . . ?
C16 C4 C14 116.51(14) . . ?
C6 C5 C14 108.40(12) . . ?
C6 C5 C17 121.83(15) . . ?
C17 C5 C14 129.76(14) . . ?
C5 C6 C12 108.41(13) . . ?
C5 C6 C15 120.42(14) . . ?
C15 C6 C12 131.17(14) . . ?
C9 C7 C8 119.91(15) . . ?
C11 C8 C7 120.55(16) . . ?
C7 C9 C10 120.07(14) . . ?
C7 C9 C14 120.47(14) . . ?
C10 C9 C14 119.29(14) . . ?
C9 C10 C18 119.18(15) . . ?
C9 C10 C19 119.84(15) . . ?
C18 C10 C19 120.97(15) . . ?
C8 C11 C18 119.62(16) . . ?
O1 C12 C6 107.85(12) . . ?
O2 C12 O1 121.08(14) . . ?
O2 C12 C6 131.07(14) . . ?
C15 C13 C20 120.36(16) . . ?
O1 C14 C4 108.57(12) . . ?
O1 C14 C5 103.75(11) . . ?
O1 C14 C9 110.30(12) . . ?
C5 C14 C4 106.60(12) . . ?
C9 C14 C4 115.33(12) . . ?
C9 C14 C5 111.58(12) . . ?
C6 C15 Cl1 120.99(13) . . ?
C13 C15 Cl1 120.53(13) . . ?
C13 C15 C6 118.47(16) . . ?
C19 C16 C4 121.07(15) . . ?
C5 C17 C20 117.30(16) . . ?
C11 C18 C10 120.66(16) . . ?
C16 C19 C10 123.84(16) . . ?
C13 C20 C17 121.60(15) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
