# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mx7039
_database_code_depnum_ccdc_archive 'CCDC 1888714'
loop_
_audit_author_name
_audit_author_address
Wang
;Ares
China
;
_audit_update_record             
;
2019-08-08 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;
_audit_creation_date             2018-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 Cl N O2'
_chemical_formula_sum            'C10 H6 Cl N O2'
_chemical_formula_weight         207.61
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.082(4)
_cell_length_b                   5.884(2)
_cell_length_c                   19.020(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.210(6)
_cell_angle_gamma                90
_cell_volume                     887.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4815
_cell_measurement_theta_min      2.5693
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.053
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6521
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.569
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1933
_reflns_number_total             2009
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2009
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+0.3748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C7 \\sim C8 \\sim C10 \\sim C8A \\sim C7A: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(C8A) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C7A)=Sof(H7A)=Sof(C10A)=1-FVAR(1)
 Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C10)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C7A(H7A)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C8A(H8AA,H8AB)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.65750(6) 0.83756(8) 0.61215(2) 0.04208(16) Uani 1 1 d . . . . .
N1 N 0.9316(2) -0.1248(3) 0.27844(9) 0.0517(4) Uani 1 1 d . . . . .
O1 O 0.85260(15) 0.16417(19) 0.41561(6) 0.0355(3) Uani 1 1 d . . . . .
C1 C 0.70796(18) 0.5167(3) 0.43172(8) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.56139(17) 0.7015(2) 0.32791(7) 0.0478(3) Uani 1 1 d . . . . .
C2 C 0.66348(19) 0.6753(3) 0.47964(9) 0.0310(3) Uani 1 1 d . . . . .
H2 H 0.600921 0.807133 0.462138 0.037 Uiso 1 1 calc R . . . .
C3 C 0.71084(19) 0.6393(3) 0.55223(8) 0.0315(3) Uani 1 1 d . . . . .
C4 C 0.7997(2) 0.4450(3) 0.57898(9) 0.0372(4) Uani 1 1 d . . . . .
H4 H 0.827865 0.419683 0.629223 0.045 Uiso 1 1 calc R . . . .
C5 C 0.8466(2) 0.2896(3) 0.53232(9) 0.0360(4) Uani 1 1 d . . . . .
H5 H 0.909583 0.158556 0.550232 0.043 Uiso 1 1 calc R . . . .
C6 C 0.80115(19) 0.3260(3) 0.45869(8) 0.0290(3) Uani 1 1 d . . . . .
C7 C 0.7575(5) 0.1628(5) 0.34249(17) 0.0324(10) Uani 0.531(6) 1 d . U P A 1
H7 H 0.643546 0.096756 0.342572 0.039 Uiso 0.531(6) 1 calc R . P A 1
C8 C 0.7343(10) 0.4009(11) 0.3090(5) 0.0318(13) Uani 0.531(6) 1 d . U P A 1
H8A H 0.845380 0.464990 0.305059 0.038 Uiso 0.531(6) 1 calc R . P A 1
H8B H 0.664103 0.391498 0.260236 0.038 Uiso 0.531(6) 1 calc R . P A 1
C9 C 0.6531(2) 0.5468(3) 0.35360(9) 0.0344(4) Uani 1 1 d . . . . .
C10 C 0.8520(9) 0.0034(19) 0.3040(6) 0.0366(15) Uani 0.531(6) 1 d . U P A 1
C8A C 0.7012(11) 0.3410(13) 0.3071(5) 0.0327(15) Uani 0.469(6) 1 d . U P A 2
H8AA H 0.609154 0.227255 0.299541 0.039 Uiso 0.469(6) 1 calc R . P A 2
H8AB H 0.715670 0.397284 0.259630 0.039 Uiso 0.469(6) 1 calc R . P A 2
C7A C 0.8604(5) 0.2333(7) 0.34476(17) 0.0328(11) Uani 0.469(6) 1 d . U P A 2
H7A H 0.954278 0.345480 0.347191 0.039 Uiso 0.469(6) 1 calc R . P A 2
C10A C 0.9026(10) 0.030(2) 0.3082(6) 0.0346(16) Uani 0.469(6) 1 d . . P A 2


_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 C3 1.7426(16) . ?
N1 C10 1.158(11) . ?
N1 C10A 1.122(13) . ?
O1 C6 1.3722(18) . ?
O1 C7 1.452(4) . ?
O1 C7A 1.421(3) . ?
C1 C2 1.400(2) . ?
C1 C6 1.392(2) . ?
C1 C9 1.476(2) . ?
O2 C9 1.215(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(2) . ?
C3 C4 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.536(8) . ?
C7 C10 1.489(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.450(9) . ?
C9 C8A 1.591(9) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C7A 1.487(10) . ?
C7A H7A 1.0000 . ?
C7A C10A 1.456(13) . ?

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
C6 O1 C7 114.23(16) . . ?
C6 O1 C7A 116.26(18) . . ?
C2 C1 C9 120.69(14) . . ?
C6 C1 C2 119.11(14) . . ?
C6 C1 C9 120.18(14) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.62(15) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 Cl1 119.83(13) . . ?
C2 C3 C4 121.09(15) . . ?
C4 C3 Cl1 119.08(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.75(15) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.59(16) . . ?
C6 C5 H5 120.2 . . ?
O1 C6 C1 122.95(14) . . ?
O1 C6 C5 116.26(14) . . ?
C1 C6 C5 120.79(14) . . ?
O1 C7 H7 108.5 . . ?
O1 C7 C8 113.0(4) . . ?
O1 C7 C10 104.4(4) . . ?
C8 C7 H7 108.5 . . ?
C10 C7 H7 108.5 . . ?
C10 C7 C8 113.8(6) . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 C7 109.3(6) . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C1 C9 C8A 114.2(4) . . ?
O2 C9 C1 122.35(15) . . ?
O2 C9 C8 121.2(4) . . ?
O2 C9 C8A 122.9(4) . . ?
C8 C9 C1 115.9(4) . . ?
N1 C10 C7 175.4(10) . . ?
C9 C8A H8AA 109.7 . . ?
C9 C8A H8AB 109.7 . . ?
H8AA C8A H8AB 108.2 . . ?
C7A C8A C9 109.8(6) . . ?
C7A C8A H8AA 109.7 . . ?
C7A C8A H8AB 109.7 . . ?
O1 C7A C8A 112.6(5) . . ?
O1 C7A H7A 108.6 . . ?
O1 C7A C10A 106.0(5) . . ?
C8A C7A H7A 108.6 . . ?
C10A C7A C8A 112.4(5) . . ?
C10A C7A H7A 108.6 . . ?
N1 C10A C7A 178.0(10) . . ?

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
Cl1 C3 C4 C5 -178.31(13) . . . . ?
O1 C7 C8 C9 -56.7(6) . . . . ?
C1 C2 C3 Cl1 179.41(11) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C1 C9 C8A C7A -30.8(6) . . . . ?
O2 C9 C8A C7A 157.9(4) . . . . ?
C2 C1 C6 O1 -178.83(13) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C2 C1 C9 O2 -3.7(2) . . . . ?
C2 C1 C9 C8 167.6(3) . . . . ?
C2 C1 C9 C8A -175.1(3) . . . . ?
C2 C3 C4 C5 2.4(2) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 O1 179.89(15) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C6 O1 C7 C8 47.0(5) . . . . ?
C6 O1 C7 C10 171.1(4) . . . . ?
C6 O1 C7A C8A -51.7(5) . . . . ?
C6 O1 C7A C10A -175.0(3) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C1 C9 O2 174.50(16) . . . . ?
C6 C1 C9 C8 -14.2(3) . . . . ?
C6 C1 C9 C8A 3.1(4) . . . . ?
C7 O1 C6 C1 -20.0(2) . . . . ?
C7 O1 C6 C5 159.7(2) . . . . ?
C7 C8 C9 C1 39.1(5) . . . . ?
C7 C8 C9 O2 -149.5(4) . . . . ?
C9 C1 C2 C3 177.62(14) . . . . ?
C9 C1 C6 O1 2.9(2) . . . . ?
C9 C1 C6 C5 -176.79(14) . . . . ?
C9 C8A C7A O1 54.8(6) . . . . ?
C9 C8A C7A C10A 174.5(5) . . . . ?
C10 C7 C8 C9 -175.5(5) . . . . ?
C7A O1 C6 C1 21.5(3) . . . . ?
C7A O1 C6 C5 -158.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mx7044
_database_code_depnum_ccdc_archive 'CCDC 1888716'
loop_
_audit_author_name
_audit_author_address
wqt
;Institute of Chemistry
China
;
_audit_update_record             
;
2019-01-04 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;
_audit_creation_date             2018-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 Cl N O2'
_chemical_formula_sum            'C11 H8 Cl N O2'
_chemical_formula_weight         221.63
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.406(3)
_cell_length_b                   9.108(2)
_cell_length_c                   10.949(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.637(4)
_cell_angle_gamma                90
_cell_volume                     1004.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3223
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4797
_cell_measurement_theta_min      1.9224
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       palte
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.143
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6493
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.023
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2204
_reflns_number_total             2272
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.3334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0954
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.84382(3) 1.05126(4) 0.53522(3) 0.03848(14) Uani 1 1 d . . . . .
C1 C 0.82175(12) 0.86617(15) 0.49445(12) 0.0290(3) Uani 1 1 d . . . . .
O1 O 0.76921(12) 0.42950(11) 0.39966(11) 0.0412(3) Uani 1 1 d . . . . .
H1 H 0.713909 0.417827 0.329762 0.062 Uiso 1 1 calc GR . . . .
N1 N 0.35886(14) 0.88514(16) -0.15423(12) 0.0431(3) Uani 1 1 d . . . . .
O2 O 0.59451(10) 0.50846(12) 0.19994(9) 0.0367(2) Uani 1 1 d . . . . .
C2 C 0.89245(13) 0.75917(17) 0.57624(12) 0.0328(3) Uani 1 1 d . . . . .
C3 C 0.87025(14) 0.61369(17) 0.54042(13) 0.0357(3) Uani 1 1 d . . . . .
H3 H 0.916588 0.539155 0.594773 0.043 Uiso 1 1 calc R . . . .
C4 C 0.78199(14) 0.57322(15) 0.42703(13) 0.0312(3) Uani 1 1 d . . . . .
C5 C 0.71186(12) 0.68313(15) 0.34507(11) 0.0266(3) Uani 1 1 d . . . . .
C6 C 0.73398(12) 0.83046(15) 0.38107(12) 0.0273(3) Uani 1 1 d . . . . .
H6 H 0.688494 0.905996 0.327352 0.033 Uiso 1 1 calc R . . . .
C7 C 0.98977(15) 0.7983(2) 0.69862(14) 0.0429(4) Uani 1 1 d . . . . .
H7A H 1.061786 0.857543 0.681246 0.064 Uiso 1 1 calc GR . . . .
H7B H 1.026637 0.708325 0.742881 0.064 Uiso 1 1 calc GR . . . .
H7C H 0.944302 0.854704 0.751459 0.064 Uiso 1 1 calc GR . . . .
C8 C 0.61970(13) 0.63951(15) 0.22590(12) 0.0280(3) Uani 1 1 d . . . . .
C9 C 0.55672(14) 0.75283(15) 0.13174(12) 0.0325(3) Uani 1 1 d . . . . .
H9 H 0.580139 0.853325 0.146063 0.039 Uiso 1 1 calc R . . . .
C10 C 0.46827(13) 0.71265(15) 0.02841(12) 0.0314(3) Uani 1 1 d . . . . .
H10 H 0.443624 0.612035 0.019427 0.038 Uiso 1 1 calc R . . . .
C11 C 0.40692(14) 0.81113(16) -0.07122(13) 0.0322(3) 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
Cl1 C1 1.7442(15) . ?
C1 C2 1.400(2) . ?
C1 C6 1.3813(18) . ?
O1 H1 0.8400 . ?
O1 C4 1.3420(17) . ?
N1 C11 1.1405(19) . ?
O2 C8 1.2396(17) . ?
C2 C3 1.385(2) . ?
C2 C7 1.5041(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3944(19) . ?
C4 C5 1.4173(19) . ?
C5 C6 1.4012(19) . ?
C5 C8 1.4654(17) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.4887(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.3171(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.4318(19) . ?

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 Cl1 119.68(10) . . ?
C6 C1 Cl1 118.16(11) . . ?
C6 C1 C2 122.15(13) . . ?
C4 O1 H1 109.5 . . ?
C1 C2 C7 122.10(14) . . ?
C3 C2 C1 117.51(12) . . ?
C3 C2 C7 120.39(14) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.03(13) . . ?
C4 C3 H3 119.0 . . ?
O1 C4 C3 117.55(13) . . ?
O1 C4 C5 122.78(12) . . ?
C3 C4 C5 119.66(13) . . ?
C4 C5 C8 119.25(12) . . ?
C6 C5 C4 118.47(12) . . ?
C6 C5 C8 122.28(12) . . ?
C1 C6 C5 120.17(12) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C5 121.21(12) . . ?
O2 C8 C9 118.57(12) . . ?
C5 C8 C9 120.21(12) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.47(13) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.0 . . ?
C9 C10 C11 124.10(13) . . ?
C11 C10 H10 118.0 . . ?
N1 C11 C10 177.04(15) . . ?

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
O1 H1 O2 0.84 1.83 2.5680(16) 145.5 .

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
Cl1 C1 C2 C3 179.20(10) . . . . ?
Cl1 C1 C2 C7 -1.05(18) . . . . ?
Cl1 C1 C6 C5 -179.24(9) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
O1 C4 C5 C6 -178.77(12) . . . . ?
O1 C4 C5 C8 0.9(2) . . . . ?
O2 C8 C9 C10 5.4(2) . . . . ?
C2 C1 C6 C5 0.80(19) . . . . ?
C2 C3 C4 O1 178.76(13) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.09(19) . . . . ?
C3 C4 C5 C8 179.77(12) . . . . ?
C4 C5 C6 C1 -0.40(18) . . . . ?
C4 C5 C8 O2 5.48(19) . . . . ?
C4 C5 C8 C9 -173.01(12) . . . . ?
C5 C8 C9 C10 -176.07(12) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C6 C1 C2 C7 178.91(12) . . . . ?
C6 C5 C8 O2 -174.85(12) . . . . ?
C6 C5 C8 C9 6.66(18) . . . . ?
C7 C2 C3 C4 -179.24(13) . . . . ?
C8 C5 C6 C1 179.93(11) . . . . ?
C8 C9 C10 C11 -176.56(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
