# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_17228-e
_database_code_depnum_ccdc_archive 'CCDC 2079841'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;University of Kentucky
United States of America
;
_audit_update_record             
;
2021-04-25 deposited with the CCDC.	2021-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H11 Cl N2 O2, C4 H9 N O'
_chemical_formula_sum            'C17 H20 Cl N3 O3'
_chemical_formula_weight         349.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 Cl1'
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      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                   15.4376(4)
_cell_length_b                   5.92226(13)
_cell_length_c                   19.0732(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.548(3)
_cell_angle_gamma                90
_cell_volume                     1714.31(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4210
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9240
_cell_measurement_theta_min      4.6980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             736
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9510
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.856
_diffrn_reflns_theta_min         4.717
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4674
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 103.00   1.00    1.00    --   42.20  38.00 -60.00   77
  2  ω     26.00 114.00   1.00    1.00    --   42.20  38.00-150.00   88
  3  ω     16.00  64.00   1.00    2.99    --   92.50 -77.00 150.00   48
  4  ω     81.00 107.00   1.00    2.99    --   92.50 -61.00 -60.00   26
  5  ω     93.00 165.00   1.00    2.99    --   92.50  45.00  90.00   72
  6  ω     12.00  48.00   1.00    2.99    --   92.50 -95.00  30.00   36
  7  ω     19.00  96.00   1.00    2.99    --   92.50 -45.00 150.00   77
  8  ω    121.00 157.00   1.00    2.99    --   92.50  15.00 -30.00   36
  9  ω     10.00  53.00   1.00    2.99    --   92.50 -95.00   0.00   43
 10  ω     59.00  84.00   1.00    2.99    --   92.50 -95.00   0.00   25
 11  ω     93.00 127.00   1.00    2.99    --   92.50  61.00  30.00   34
 12  ω     46.00  72.00   1.00    2.99    --   92.50 -61.00 -60.00   26
 13  ω     18.00  44.00   1.00    2.99    --   92.50 -30.00-180.00   26
 14  ω     41.00 103.00   1.00    2.99    --   92.50  15.00 -30.00   62
 15  ω     89.00 115.00   1.00    2.99    --   92.50 -90.00 123.15   26
 16  ω     81.00 107.00   1.00    2.99    --   92.50 125.00   0.00   26
 17  ω    130.00 156.00   1.00    2.99    --   92.50 125.00   0.00   26
 18  ω     73.00  99.00   1.00    2.99    --   92.50  45.00-150.00   26
 19  ω     39.00  72.00   1.00    2.99    --   92.50 -95.00 150.00   33
 20  ω     24.00  49.00   1.00    2.99    --   92.50-125.00-180.00   25
 21  ω     40.00  75.00   1.00    2.99    --   92.50 -90.00 123.15   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0904347000
_diffrn_orient_matrix_UB_12      -0.0916939000
_diffrn_orient_matrix_UB_13      0.0097124000
_diffrn_orient_matrix_UB_21      0.0347221000
_diffrn_orient_matrix_UB_22      -0.0278531000
_diffrn_orient_matrix_UB_23      0.0805398000
_diffrn_orient_matrix_UB_31      -0.0303038000
_diffrn_orient_matrix_UB_32      0.2418509000
_diffrn_orient_matrix_UB_33      0.0129925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2517
_reflns_number_total             3017
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_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         0.282
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.035
_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)+(0.0610P)²+0.4319P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(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:
 N7(H7), C4(H4), C12(H12), C11(H11), C2(H2), C13(H13), C3(H3)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
2.c Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_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
Cl17 Cl 0.12763(4) 1.33253(10) 0.49578(3) 0.0736(2) Uani 1 1 d . . . . .
N21 N 0.93382(10) 0.3509(3) 0.66318(9) 0.0538(4) Uani 1 1 d . . . . .
O16 O 0.29890(10) 0.1582(3) 0.74643(9) 0.0760(5) Uani 1 1 d . . . . .
H16 H 0.2502 0.1427 0.7571 0.114 Uiso 1 1 calc GR . . . .
N7 N 0.32255(9) 0.6781(3) 0.60322(8) 0.0496(4) Uani 1 1 d . . . . .
H7 H 0.2771 0.6539 0.6223 0.060 Uiso 1 1 calc R . . . .
C1 C 0.31353(11) 0.8622(3) 0.55667(9) 0.0439(4) Uani 1 1 d . . . . .
C14 C 0.29658(12) 0.3249(3) 0.70100(10) 0.0493(4) Uani 1 1 d . . . . .
O19 O 0.84997(9) 0.5861(3) 0.71250(8) 0.0691(4) Uani 1 1 d . . . . .
C10 C 0.37875(11) 0.3527(3) 0.67239(9) 0.0437(4) Uani 1 1 d . . . . .
O15 O 0.23155(9) 0.4430(3) 0.68448(8) 0.0635(4) Uani 1 1 d . . . . .
C4 C 0.28713(14) 1.2385(4) 0.46752(11) 0.0629(5) Uani 1 1 d . . . . .
H4 H 0.2782 1.3646 0.4380 0.075 Uiso 1 1 calc R . . . .
C5 C 0.22407(13) 1.1704(3) 0.50565(10) 0.0529(5) Uani 1 1 d . . . . .
N8 N 0.46512(10) 0.5534(3) 0.59905(9) 0.0540(4) Uani 1 1 d . . . . .
C12 C 0.52389(13) 0.2254(4) 0.66435(12) 0.0614(5) Uani 1 1 d . . . . .
H12 H 0.5704 0.1244 0.6763 0.074 Uiso 1 1 calc R . . . .
C24 C 0.78370(14) 0.2378(4) 0.66501(13) 0.0650(5) Uani 1 1 d . . . . .
H24A H 0.7682 0.2186 0.6143 0.097 Uiso 1 1 calc GR . . . .
H24B H 0.7337 0.2943 0.6830 0.097 Uiso 1 1 calc GR . . . .
H24C H 0.8014 0.0951 0.6869 0.097 Uiso 1 1 calc GR . . . .
C18 C 0.16230(13) 0.9145(4) 0.59008(12) 0.0629(5) Uani 1 1 d . . . . .
H18A H 0.1487 0.7577 0.5812 0.094 Uiso 1 1 calc GR . . . .
H18B H 0.1105 1.0036 0.5742 0.094 Uiso 1 1 calc GR . . . .
H18C H 0.1823 0.9375 0.6403 0.094 Uiso 1 1 calc GR . . . .
C11 C 0.44746(12) 0.2022(3) 0.69135(10) 0.0529(4) Uani 1 1 d . . . . .
H11 H 0.4421 0.0844 0.7225 0.063 Uiso 1 1 calc R . . . .
C20 C 0.85835(12) 0.4025(3) 0.68185(10) 0.0515(4) Uani 1 1 d . . . . .
C22 C 0.94682(18) 0.1450(4) 0.62440(16) 0.0842(8) Uani 1 1 d . . . . .
H22A H 0.8987 0.0433 0.6256 0.126 Uiso 1 1 calc GR . . . .
H22B H 1.0010 0.0744 0.6463 0.126 Uiso 1 1 calc GR . . . .
H22C H 0.9493 0.1819 0.5758 0.126 Uiso 1 1 calc GR . . . .
C9 C 0.38996(11) 0.5291(3) 0.62426(9) 0.0426(4) Uani 1 1 d . . . . .
C6 C 0.23341(11) 0.9843(3) 0.55034(9) 0.0463(4) Uani 1 1 d . . . . .
C2 C 0.37687(12) 0.9287(4) 0.51781(10) 0.0535(5) Uani 1 1 d . . . . .
H2 H 0.4288 0.8465 0.5213 0.064 Uiso 1 1 calc R . . . .
C23 C 1.00799(12) 0.5074(4) 0.67696(12) 0.0656(6) Uani 1 1 d . . . . .
H23A H 1.0208 0.5611 0.6325 0.098 Uiso 1 1 calc GR . . . .
H23B H 1.0587 0.4311 0.7030 0.098 Uiso 1 1 calc GR . . . .
H23C H 0.9933 0.6328 0.7044 0.098 Uiso 1 1 calc GR . . . .
C13 C 0.52886(13) 0.4029(4) 0.61922(12) 0.0615(5) Uani 1 1 d . . . . .
H13 H 0.5806 0.4196 0.6013 0.074 Uiso 1 1 calc R . . . .
C3 C 0.36330(14) 1.1158(4) 0.47411(12) 0.0641(6) Uani 1 1 d . . . . .
H3 H 0.4066 1.1592 0.4487 0.077 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
Cl17 C5 1.7524(19) . ?
N21 C20 1.315(2) . ?
N21 C22 1.459(3) . ?
N21 C23 1.459(3) . ?
O16 C14 1.310(2) . ?
N7 C1 1.397(2) . ?
N7 C9 1.368(2) . ?
C1 C6 1.419(2) . ?
C1 C2 1.388(2) . ?
C14 C10 1.479(2) . ?
C14 O15 1.217(2) . ?
O19 C20 1.252(2) . ?
C10 C11 1.382(3) . ?
C10 C9 1.422(2) . ?
C4 C5 1.378(3) . ?
C4 C3 1.368(3) . ?
C5 C6 1.385(3) . ?
N8 C9 1.342(2) . ?
N8 C13 1.331(3) . ?
C12 C11 1.378(3) . ?
C12 C13 1.370(3) . ?
C24 C20 1.499(3) . ?
C18 C6 1.502(3) . ?
C2 C3 1.379(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
C20 N21 C22 122.85(19) . . ?
C20 N21 C23 120.57(17) . . ?
C23 N21 C22 116.48(18) . . ?
C9 N7 C1 132.24(15) . . ?
N7 C1 C6 115.85(15) . . ?
C2 C1 N7 124.26(16) . . ?
C2 C1 C6 119.89(17) . . ?
O16 C14 C10 113.99(16) . . ?
O15 C14 O16 121.73(16) . . ?
O15 C14 C10 124.29(16) . . ?
C11 C10 C14 120.04(16) . . ?
C11 C10 C9 117.67(16) . . ?
C9 C10 C14 122.28(15) . . ?
C3 C4 C5 118.32(19) . . ?
C4 C5 Cl17 116.85(15) . . ?
C4 C5 C6 123.62(18) . . ?
C6 C5 Cl17 119.53(15) . . ?
C13 N8 C9 117.80(16) . . ?
C13 C12 C11 117.50(18) . . ?
C12 C11 C10 120.43(18) . . ?
N21 C20 C24 118.38(18) . . ?
O19 C20 N21 120.02(18) . . ?
O19 C20 C24 121.60(17) . . ?
N7 C9 C10 119.18(15) . . ?
N8 C9 N7 119.14(15) . . ?
N8 C9 C10 121.69(16) . . ?
C1 C6 C18 121.53(16) . . ?
C5 C6 C1 116.69(17) . . ?
C5 C6 C18 121.78(17) . . ?
C3 C2 C1 120.45(18) . . ?
N8 C13 C12 124.89(18) . . ?
C4 C3 C2 121.01(19) . . ?

_olex2_date_sample_data_collection 2017-03-08
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.812
