# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_22019781dzh_0m
_database_code_depnum_ccdc_archive 'CCDC 1959103'
loop_
_audit_author_name
_audit_author_address
'zhenhua ding'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2019-10-14 deposited with the CCDC.	2019-11-15 downloaded from the CCDC.
;
_audit_creation_date             2019-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_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'
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                   10.2125(19)
_cell_length_b                   11.318(2)
_cell_length_c                   11.717(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.447(6)
_cell_angle_gamma                90
_cell_volume                     1332.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3299
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      25.712
_cell_measurement_theta_min      2.522
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0785 before and 0.0509 after correction. The Ratio of minimum to maximum transmission is 0.8869. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13272
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.467
_diffrn_reflns_theta_min         2.522
_diffrn_ambient_temperature      303.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1788
_reflns_number_total             2734
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.051
_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)+(0.0456P)²+0.1836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1182
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C15(H15), C5(H5), C16(H16), C3(H3), C4(H4), C8(H8), C2(H2), C12(H12),
 C13(H13)
;
_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
O1 O 0.42410(12) 0.44588(9) 0.80132(9) 0.0526(3) Uani 1 1 d . . . . .
N1 N 0.62285(16) 0.51101(13) 0.77829(13) 0.0603(4) Uani 1 1 d . . . . .
C6 C 0.60995(17) 0.37812(13) 0.94386(13) 0.0475(4) Uani 1 1 d . . . . .
C7 C 0.55789(17) 0.44782(14) 0.84117(14) 0.0493(4) Uani 1 1 d . . . . .
C14 C 0.11199(18) 0.22790(15) 0.43580(15) 0.0538(4) Uani 1 1 d . . . . .
C11 C 0.21340(17) 0.42235(14) 0.56760(14) 0.0532(4) Uani 1 1 d . . . . .
C1 C 0.52524(19) 0.32044(15) 1.00605(15) 0.0551(5) Uani 1 1 d . . . . .
H1 H 0.433459 0.326834 0.983018 0.066 Uiso 1 1 calc R . . . .
C15 C 0.16846(18) 0.21380(15) 0.55172(15) 0.0561(5) Uani 1 1 d . . . . .
H15 H 0.172824 0.139296 0.585659 0.067 Uiso 1 1 calc R . . . .
C9 C 0.4052(2) 0.51567(14) 0.70298(14) 0.0555(5) Uani 1 1 d . . . . .
C5 C 0.74595(19) 0.36768(16) 0.98007(15) 0.0587(5) Uani 1 1 d . . . . .
H5 H 0.803599 0.406013 0.939313 0.070 Uiso 1 1 calc R . . . .
C16 C 0.21785(18) 0.31028(15) 0.61609(15) 0.0571(5) Uani 1 1 d . . . . .
H16 H 0.255169 0.300410 0.693994 0.069 Uiso 1 1 calc R . . . .
N2 N 0.01397(19) 0.04858(17) 0.31398(17) 0.0880(6) Uani 1 1 d . . . . .
C3 C 0.7130(2) 0.24332(16) 1.13708(16) 0.0640(5) Uani 1 1 d . . . . .
H3 H 0.747579 0.197703 1.201536 0.077 Uiso 1 1 calc R . . . .
C17 C 0.05821(19) 0.12751(18) 0.36790(17) 0.0640(5) Uani 1 1 d . . . . .
C4 C 0.7968(2) 0.30068(17) 1.07639(16) 0.0653(5) Uani 1 1 d . . . . .
H4 H 0.888450 0.294412 1.100269 0.078 Uiso 1 1 calc R . . . .
C10 C 0.2674(2) 0.52923(15) 0.63888(16) 0.0631(5) Uani 1 1 d . . . . .
H10A H 0.264144 0.596819 0.587537 0.076 Uiso 1 1 calc R . . . .
H10B H 0.209638 0.546054 0.694071 0.076 Uiso 1 1 calc R . . . .
C8 C 0.5249(2) 0.55421(16) 0.69051(16) 0.0635(5) Uani 1 1 d . . . . .
H8 H 0.540710 0.603468 0.630962 0.076 Uiso 1 1 calc R . . . .
C2 C 0.5777(2) 0.25373(15) 1.10198(16) 0.0616(5) Uani 1 1 d . . . . .
H2 H 0.520789 0.215330 1.143399 0.074 Uiso 1 1 calc R . . . .
C12 C 0.1573(2) 0.43433(17) 0.45178(16) 0.0667(6) Uani 1 1 d . . . . .
H12 H 0.153882 0.508629 0.417483 0.080 Uiso 1 1 calc R . . . .
C13 C 0.1065(2) 0.33879(17) 0.38627(16) 0.0690(6) Uani 1 1 d . . . . .
H13 H 0.068360 0.348792 0.308559 0.083 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
O1 C7 1.362(2) . ?
O1 C9 1.3813(19) . ?
N1 C7 1.293(2) . ?
N1 C8 1.387(2) . ?
C6 C7 1.456(2) . ?
C6 C1 1.391(2) . ?
C6 C5 1.382(2) . ?
C14 C15 1.385(2) . ?
C14 C17 1.438(3) . ?
C14 C13 1.380(2) . ?
C11 C16 1.387(2) . ?
C11 C10 1.516(2) . ?
C11 C12 1.381(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(2) . ?
C9 C10 1.478(3) . ?
C9 C8 1.331(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.380(2) . ?
C16 H16 0.9300 . ?
N2 C17 1.139(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(3) . ?
C3 C2 1.374(3) . ?
C4 H4 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.372(3) . ?
C13 H13 0.9300 . ?

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
C7 O1 C9 104.88(13) . . ?
C7 N1 C8 103.99(16) . . ?
C1 C6 C7 121.24(16) . . ?
C5 C6 C7 119.74(16) . . ?
C5 C6 C1 119.01(16) . . ?
O1 C7 C6 117.90(15) . . ?
N1 C7 O1 113.58(15) . . ?
N1 C7 C6 128.48(16) . . ?
C15 C14 C17 120.06(17) . . ?
C13 C14 C15 119.69(16) . . ?
C13 C14 C17 120.26(17) . . ?
C16 C11 C10 121.49(15) . . ?
C12 C11 C16 117.99(16) . . ?
C12 C11 C10 120.52(16) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.82(18) . . ?
C2 C1 H1 120.1 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.62(16) . . ?
C16 C15 H15 120.2 . . ?
O1 C9 C10 117.36(17) . . ?
C8 C9 O1 106.66(16) . . ?
C8 C9 C10 135.97(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.40(17) . . ?
C4 C5 H5 119.8 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.45(16) . . ?
C15 C16 H16 119.3 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.50(18) . . ?
C2 C3 H3 120.2 . . ?
N2 C17 C14 179.1(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.45(18) . . ?
C3 C4 H4 119.8 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 C11 114.51(14) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N1 C8 H8 124.6 . . ?
C9 C8 N1 110.89(16) . . ?
C9 C8 H8 124.6 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.81(18) . . ?
C3 C2 H2 119.6 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.32(17) . . ?
C13 C12 H12 119.3 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 119.94(17) . . ?
C12 C13 H13 120.0 . . ?


_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_22019736dzh_0m
_database_code_depnum_ccdc_archive 'CCDC 1959105'
loop_
_audit_author_name
_audit_author_address
'kang xu'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2019-10-14 deposited with the CCDC.	2019-11-15 downloaded from the CCDC.
;
_audit_creation_date             2019-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl N O2'
_chemical_formula_sum            'C16 H14 Cl N O2'
_chemical_formula_weight         287.73
_chemical_absolute_configuration rm
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   32.857(4)
_cell_length_b                   5.0957(6)
_cell_length_c                   8.5639(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.850(4)
_cell_angle_gamma                90
_cell_volume                     1403.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1607
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.160
_cell_measurement_theta_min      2.534
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1066 before and 0.0569 after correction. The Ratio of minimum to maximum transmission is 0.9195. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6972
_diffrn_reflns_point_group_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.438
_diffrn_reflns_theta_min         2.534
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.737
_reflns_Friedel_fraction_max     0.692
_reflns_number_gt                1838
_reflns_number_total             2456
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.016
_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)+(0.0508P)²+0.2047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C1(H1A), C4(H4), C14(H14), C11(H11), C3(H3), C13(H13),
 C16(H16), C2(H2)
;
_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 0.71239(5) 0.2005(3) 0.68648(15) 0.0589(5) Uani 1 1 d . . . . .
O1 O 0.42232(10) 0.5473(6) 0.4406(3) 0.0314(8) Uani 1 1 d . . . . .
O2 O 0.50854(11) 0.1820(7) 0.5666(4) 0.0415(9) Uani 1 1 d . . . . .
N1 N 0.42643(11) 0.1148(7) 0.3914(4) 0.0276(9) Uani 1 1 d . . . . .
H1 H 0.417678 -0.044887 0.405742 0.033 Uiso 1 1 calc R . . . .
C6 C 0.36696(14) 0.2757(8) 0.4891(5) 0.0235(10) Uani 1 1 d . . . . .
C7 C 0.40728(14) 0.3218(8) 0.4418(5) 0.0256(10) Uani 1 1 d . . . . .
C5 C 0.34120(14) 0.0672(9) 0.4252(5) 0.0305(11) Uani 1 1 d . . . . .
H5 H 0.350724 -0.058604 0.358992 0.037 Uiso 1 1 calc R . . . .
C1 C 0.35271(14) 0.4569(9) 0.5859(5) 0.0282(10) Uani 1 1 d . . . . .
H1A H 0.369942 0.599950 0.629063 0.034 Uiso 1 1 calc R . . . .
C12 C 0.57880(15) 0.2814(9) 0.4250(5) 0.0300(11) Uani 1 1 d . . . . .
C9 C 0.50225(15) 0.2122(9) 0.4235(5) 0.0271(10) Uani 1 1 d . . . . .
C4 C 0.30193(15) 0.0437(9) 0.4581(6) 0.0332(11) Uani 1 1 d . . . . .
H4 H 0.284526 -0.098107 0.414190 0.040 Uiso 1 1 calc R . . . .
C14 C 0.64463(16) 0.0565(10) 0.4664(6) 0.0382(12) Uani 1 1 d . . . . .
H14 H 0.661437 -0.080768 0.438963 0.046 Uiso 1 1 calc R . . . .
C11 C 0.59628(15) 0.4553(9) 0.5458(6) 0.0343(11) Uani 1 1 d . . . . .
H11 H 0.579740 0.594277 0.572959 0.041 Uiso 1 1 calc R . . . .
C3 C 0.28783(15) 0.2244(9) 0.5541(5) 0.0329(11) Uani 1 1 d . . . . .
H3 H 0.260664 0.208704 0.575251 0.039 Uiso 1 1 calc R . . . .
C13 C 0.60382(16) 0.0819(9) 0.3874(6) 0.0370(12) Uani 1 1 d . . . . .
H13 H 0.592634 -0.039628 0.305728 0.044 Uiso 1 1 calc R . . . .
C16 C 0.63697(16) 0.4313(11) 0.6271(6) 0.0385(12) Uani 1 1 d . . . . .
H16 H 0.648265 0.550101 0.710224 0.046 Uiso 1 1 calc R . . . .
C2 C 0.31367(16) 0.4311(10) 0.6202(5) 0.0331(11) Uani 1 1 d . . . . .
H2 H 0.304357 0.553848 0.688675 0.040 Uiso 1 1 calc R . . . .
C8 C 0.46103(14) 0.1506(9) 0.3142(5) 0.0300(11) Uani 1 1 d . . . . .
H8A H 0.454191 0.294900 0.235853 0.036 Uiso 1 1 calc R . . . .
H8B H 0.464329 -0.011226 0.254074 0.036 Uiso 1 1 calc R . . . .
C15 C 0.66084(16) 0.2316(10) 0.5854(6) 0.0366(12) Uani 1 1 d . . . . .
C10 C 0.53450(15) 0.3112(10) 0.3357(6) 0.0361(12) Uani 1 1 d . . . . .
H10A H 0.529106 0.499275 0.310739 0.043 Uiso 1 1 calc R . . . .
H10B H 0.531223 0.215835 0.233143 0.043 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 1.744(5) . ?
O1 C7 1.252(5) . ?
O2 C9 1.210(5) . ?
N1 H1 0.8800 . ?
N1 C7 1.344(6) . ?
N1 C8 1.439(6) . ?
C6 C7 1.481(6) . ?
C6 C5 1.398(6) . ?
C6 C1 1.385(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.382(6) . ?
C1 H1A 0.9500 . ?
C1 C2 1.379(7) . ?
C12 C11 1.394(7) . ?
C12 C13 1.386(7) . ?
C12 C10 1.507(7) . ?
C9 C8 1.513(6) . ?
C9 C10 1.507(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.376(7) . ?
C14 H14 0.9500 . ?
C14 C13 1.378(7) . ?
C14 C15 1.376(7) . ?
C11 H11 0.9500 . ?
C11 C16 1.380(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.398(7) . ?
C13 H13 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.376(7) . ?
C2 H2 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C7 N1 H1 119.5 . . ?
C7 N1 C8 120.9(4) . . ?
C8 N1 H1 119.5 . . ?
C5 C6 C7 121.1(4) . . ?
C1 C6 C7 119.3(4) . . ?
C1 C6 C5 119.3(4) . . ?
O1 C7 N1 120.4(4) . . ?
O1 C7 C6 121.6(4) . . ?
N1 C7 C6 117.9(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C1 H1A 119.8 . . ?
C2 C1 C6 120.5(4) . . ?
C2 C1 H1A 119.8 . . ?
C11 C12 C10 121.4(5) . . ?
C13 C12 C11 117.7(5) . . ?
C13 C12 C10 120.9(4) . . ?
O2 C9 C8 123.0(4) . . ?
O2 C9 C10 123.8(4) . . ?
C10 C9 C8 113.2(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.8 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.5(5) . . ?
C12 C11 H11 119.1 . . ?
C16 C11 C12 121.8(5) . . ?
C16 C11 H11 119.1 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.7(5) . . ?
C2 C3 H3 120.2 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C11 C16 H16 120.7 . . ?
C15 C16 C11 118.6(5) . . ?
C15 C16 H16 120.7 . . ?
C1 C2 C3 120.0(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N1 C8 C9 115.7(4) . . ?
N1 C8 H8A 108.3 . . ?
N1 C8 H8B 108.3 . . ?
C9 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C14 C15 Cl1 119.8(4) . . ?
C16 C15 Cl1 119.0(4) . . ?
C16 C15 C14 121.1(5) . . ?
C12 C10 H10A 108.6 . . ?
C12 C10 H10B 108.6 . . ?
C9 C10 C12 114.7(4) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
