# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_11
_audit_block_doi                 10.5517/ccdc.csd.cc2cb4gb
_database_code_depnum_ccdc_archive 'CCDC 2184491'
loop_
_audit_author_name
_audit_author_address
'Zhi-Hong Du'
;Shihezi University
China
;
_audit_update_record             
;
2022-07-06 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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         'C12 H18 N2 O2'
_chemical_formula_sum            'C12 H18 N2 O2'
_chemical_formula_weight         222.28
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.0452(3)
_cell_length_b                   10.0440(5)
_cell_length_c                   9.6566(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.901(2)
_cell_angle_gamma                90
_cell_volume                     586.26(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      74.57
_cell_measurement_theta_min      4.40
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1279 before and 0.0907 after correction. The Ratio of minimum to maximum transmission is 0.7104. 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    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12901
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.807
_diffrn_reflns_theta_min         4.579
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2272
_reflns_number_total             2372
_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         0.219
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.057
_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)+(0.0350P)²+0.1859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0936
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), N1(H1)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.2049(4) 0.5189(2) 0.6213(3) 0.0318(5) Uani 1 1 d . . . . .
C2 C 0.0196(4) 0.5064(3) 0.7041(3) 0.0373(6) Uani 1 1 d . . . . .
H2 H -0.002068 0.566509 0.778643 0.045 Uiso 1 1 calc R . . . .
C3 C -0.1336(5) 0.4063(3) 0.6780(3) 0.0398(6) Uani 1 1 d . . . . .
H3 H -0.262393 0.400205 0.732716 0.048 Uiso 1 1 calc R . . . .
C4 C -0.1002(4) 0.3156(3) 0.5732(3) 0.0373(6) Uani 1 1 d . . . . .
H4 H -0.203031 0.245288 0.558262 0.045 Uiso 1 1 calc R . . . .
C5 C 0.0841(4) 0.3270(3) 0.4892(3) 0.0345(5) Uani 1 1 d . . . . .
H5 H 0.107577 0.264271 0.417292 0.041 Uiso 1 1 calc R . . . .
C6 C 0.2341(4) 0.4305(2) 0.5110(3) 0.0306(5) Uani 1 1 d . . . . .
C7 C 0.4545(4) 0.4125(2) 0.2960(3) 0.0303(5) Uani 1 1 d . . . . .
C8 C 0.6842(4) 0.4436(2) 0.2408(3) 0.0312(5) Uani 1 1 d . . . . .
H8 H 0.779140 0.470027 0.321963 0.037 Uiso 1 1 calc R . . . .
C9 C 0.6844(4) 0.5627(2) 0.1371(3) 0.0319(6) Uani 1 1 d . . . . .
C10 C 0.5604(5) 0.5312(3) 0.0020(3) 0.0416(6) Uani 1 1 d . . . . .
H10A H 0.625951 0.452447 -0.041038 0.062 Uiso 1 1 calc GR . . . .
H10B H 0.571056 0.607182 -0.061103 0.062 Uiso 1 1 calc GR . . . .
H10C H 0.404499 0.513591 0.021633 0.062 Uiso 1 1 calc GR . . . .
C11 C 0.9265(4) 0.5960(3) 0.1042(3) 0.0433(7) Uani 1 1 d . . . . .
H11A H 1.008472 0.613581 0.190616 0.065 Uiso 1 1 calc GR . . . .
H11B H 0.931247 0.674972 0.044767 0.065 Uiso 1 1 calc GR . . . .
H11C H 0.993898 0.520519 0.056264 0.065 Uiso 1 1 calc GR . . . .
C12 C 0.5800(5) 0.6841(3) 0.2063(3) 0.0436(7) Uani 1 1 d . . . . .
H12A H 0.422233 0.667366 0.220411 0.065 Uiso 1 1 calc GR . . . .
H12B H 0.597503 0.762292 0.146768 0.065 Uiso 1 1 calc GR . . . .
H12C H 0.653391 0.700243 0.295897 0.065 Uiso 1 1 calc GR . . . .
N1 N 0.4234(4) 0.4496(2) 0.4293(2) 0.0335(5) Uani 1 1 d . . . . .
H1 H 0.535164 0.490757 0.470088 0.040 Uiso 1 1 calc R . . . .
N2 N 0.7724(4) 0.3169(2) 0.1879(2) 0.0356(5) Uani 1 1 d . . . . .
H2A H 0.711(5) 0.300(4) 0.103(3) 0.043 Uiso 1 1 d R . . . .
H2B H 0.918(6) 0.325(4) 0.174(3) 0.043 Uiso 1 1 d R . . . .
O1 O 0.3640(3) 0.61267(18) 0.6425(2) 0.0377(4) Uani 1 1 d . . . . .
H1A H 0.313693 0.674290 0.691614 0.056 Uiso 1 1 calc GR . . . .
O2 O 0.3132(3) 0.35499(19) 0.22438(18) 0.0377(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
C1 C2 1.392(3) . ?
C1 C6 1.400(3) . ?
C1 O1 1.359(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 N1 1.413(3) . ?
C7 C8 1.528(3) . ?
C7 N1 1.356(3) . ?
C7 O2 1.234(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.560(3) . ?
C8 N2 1.474(3) . ?
C9 C10 1.527(4) . ?
C9 C11 1.539(3) . ?
C9 C12 1.531(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2A 0.91(3) . ?
N2 H2B 0.89(3) . ?
O1 H1A 0.8400 . ?

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 119.5(2) . . ?
O1 C1 C2 123.4(2) . . ?
O1 C1 C6 117.1(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 N1 116.8(2) . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 N1 123.2(2) . . ?
N1 C7 C8 114.5(2) . . ?
O2 C7 C8 121.7(2) . . ?
O2 C7 N1 123.8(2) . . ?
C7 C8 H8 107.1 . . ?
C7 C8 C9 113.0(2) . . ?
C9 C8 H8 107.1 . . ?
N2 C8 C7 106.22(19) . . ?
N2 C8 H8 107.1 . . ?
N2 C8 C9 115.8(2) . . ?
C10 C9 C8 112.6(2) . . ?
C10 C9 C11 108.9(2) . . ?
C10 C9 C12 109.7(2) . . ?
C11 C9 C8 108.0(2) . . ?
C12 C9 C8 109.0(2) . . ?
C12 C9 C11 108.5(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 N1 H1 115.9 . . ?
C7 N1 C6 128.2(2) . . ?
C7 N1 H1 115.9 . . ?
C8 N2 H2A 109(2) . . ?
C8 N2 H2B 109(2) . . ?
H2A N2 H2B 106(3) . . ?
C1 O1 H1A 109.5 . . ?

_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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2184490'
loop_
_audit_author_name
_audit_author_address
'Zhi-Hong Du'
;Shihezi University
China
;
_audit_update_record             
;
2022-07-06 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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         'C14 H14 Cl N O3'
_chemical_formula_sum            'C14 H14 Cl N O3'
_chemical_formula_weight         279.71
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2587(2)
_cell_length_b                   11.3133(3)
_cell_length_c                   15.3314(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1259.01(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.04
_cell_measurement_theta_min      4.86
_shelx_estimated_absorpt_T_max   0.669
_shelx_estimated_absorpt_T_min   0.625
_exptl_absorpt_coefficient_mu    2.730
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1112 before and 0.0721 after correction. The Ratio of minimum to maximum transmission is 0.8554. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30428
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.038
_diffrn_reflns_theta_min         4.858
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2394
_reflns_number_total             2467
_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         0.302
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.086
_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)+(0.0424P)²+0.2938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0769
_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
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), N1(H1)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(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
C1 C 0.6412(3) 0.4350(2) 0.34605(16) 0.0266(5) Uani 1 1 d . . . . .
C2 C 0.7781(4) 0.4661(2) 0.28865(16) 0.0316(5) Uani 1 1 d . . . . .
H2A H 0.896816 0.431026 0.291759 0.038 Uiso 1 1 calc R . . . .
C3 C 0.7370(4) 0.5507(2) 0.22587(16) 0.0346(5) Uani 1 1 d . . . . .
H3 H 0.829329 0.575031 0.185783 0.041 Uiso 1 1 calc R . . . .
C4 C 0.5619(4) 0.5999(2) 0.22130(17) 0.0323(5) Uani 1 1 d . . . . .
H4 H 0.534078 0.656282 0.177331 0.039 Uiso 1 1 calc R . . . .
C5 C 0.4268(3) 0.5665(2) 0.28119(16) 0.0274(5) Uani 1 1 d . . . . .
C6 C 0.4646(3) 0.4855(2) 0.34637(16) 0.0254(5) Uani 1 1 d . . . . .
C7 C 0.3507(3) 0.4270(2) 0.41814(16) 0.0252(5) Uani 1 1 d . . . . .
C8 C 0.4952(3) 0.3387(2) 0.45628(16) 0.0269(5) Uani 1 1 d . . . . .
C9 C 0.2787(3) 0.5009(2) 0.49574(15) 0.0267(5) Uani 1 1 d . . . . .
H9 H 0.227814 0.441906 0.537912 0.032 Uiso 1 1 calc R . . . .
C10 C 0.4309(3) 0.5643(2) 0.54508(17) 0.0291(5) Uani 1 1 d . . . . .
C11 C 0.3715(4) 0.6338(3) 0.62403(18) 0.0396(6) Uani 1 1 d . . . . .
H11A H 0.473622 0.686272 0.642201 0.048 Uiso 1 1 calc R . . . .
H11B H 0.346751 0.578257 0.672554 0.048 Uiso 1 1 calc R . . . .
C12 C 0.1990(5) 0.7088(3) 0.6079(2) 0.0461(7) Uani 1 1 d . . . . .
H12A H 0.152331 0.738811 0.664407 0.055 Uiso 1 1 calc R . . . .
H12B H 0.232365 0.777854 0.571487 0.055 Uiso 1 1 calc R . . . .
C13 C 0.0486(4) 0.6398(3) 0.56308(18) 0.0407(7) Uani 1 1 d . . . . .
H13A H -0.057239 0.692515 0.551124 0.049 Uiso 1 1 calc R . . . .
H13B H 0.005816 0.575460 0.601878 0.049 Uiso 1 1 calc R . . . .
C14 C 0.1188(4) 0.5871(2) 0.47744(19) 0.0355(6) Uani 1 1 d . . . . .
H14A H 0.161668 0.651314 0.438519 0.043 Uiso 1 1 calc R . . . .
H14B H 0.017347 0.544716 0.447709 0.043 Uiso 1 1 calc R . . . .
Cl1 Cl 0.21061(8) 0.63071(6) 0.26794(4) 0.03543(17) Uani 1 1 d . . . . .
N1 N 0.6521(3) 0.34740(18) 0.41083(14) 0.0291(4) Uani 1 1 d . . . . .
H1 H 0.750174 0.303534 0.420361 0.035 Uiso 1 1 calc R . . . .
O1 O 0.4664(2) 0.27027(16) 0.51717(12) 0.0339(4) Uani 1 1 d . . . . .
O2 O 0.2073(2) 0.36193(15) 0.37815(11) 0.0295(4) Uani 1 1 d . . . . .
H2 H 0.151113 0.322474 0.416171 0.044 Uiso 1 1 calc GR . . . .
O3 O 0.5907(3) 0.55582(18) 0.52400(13) 0.0379(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
C1 C2 1.373(4) . ?
C1 C6 1.403(3) . ?
C1 N1 1.406(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.389(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.384(3) . ?
C5 Cl1 1.741(2) . ?
C6 C7 1.527(3) . ?
C7 C8 1.562(3) . ?
C7 C9 1.545(3) . ?
C7 O2 1.415(3) . ?
C8 N1 1.338(3) . ?
C8 O1 1.231(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.519(3) . ?
C9 C14 1.542(3) . ?
C10 C11 1.506(4) . ?
C10 O3 1.208(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.533(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.508(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.529(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 H1 0.8800 . ?
O2 H2 0.8400 . ?

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 124.0(2) . . ?
C2 C1 N1 126.4(2) . . ?
C6 C1 N1 109.6(2) . . ?
C1 C2 H2A 121.1 . . ?
C1 C2 C3 117.7(2) . . ?
C3 C2 H2A 121.1 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 Cl1 116.36(19) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 Cl1 122.66(19) . . ?
C1 C6 C7 108.7(2) . . ?
C5 C6 C1 116.6(2) . . ?
C5 C6 C7 134.4(2) . . ?
C6 C7 C8 100.56(18) . . ?
C6 C7 C9 120.23(19) . . ?
C9 C7 C8 106.55(19) . . ?
O2 C7 C6 108.16(19) . . ?
O2 C7 C8 108.88(18) . . ?
O2 C7 C9 111.49(19) . . ?
N1 C8 C7 109.2(2) . . ?
O1 C8 C7 124.9(2) . . ?
O1 C8 N1 125.8(2) . . ?
C7 C9 H9 105.2 . . ?
C10 C9 C7 113.1(2) . . ?
C10 C9 H9 105.2 . . ?
C10 C9 C14 109.8(2) . . ?
C14 C9 C7 117.2(2) . . ?
C14 C9 H9 105.2 . . ?
C11 C10 C9 116.0(2) . . ?
O3 C10 C9 121.8(2) . . ?
O3 C10 C11 122.1(3) . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C10 C11 C12 113.2(2) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 C11 112.2(2) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 C14 110.6(2) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C9 C14 H14A 109.7 . . ?
C9 C14 H14B 109.7 . . ?
C13 C14 C9 109.9(2) . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C1 N1 H1 124.1 . . ?
C8 N1 C1 111.8(2) . . ?
C8 N1 H1 124.1 . . ?
C7 O2 H2 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
