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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_crl37621
_database_code_depnum_ccdc_archive 'CCDC 2034164'
loop_
_audit_author_name
_audit_author_address
'Somaraju Yugandar'
;Tokyo Institute of Technology 
Japan
;
_audit_update_record             
;
2020-09-28 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
_audit_creation_date             2019-09-12
_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         'C18 H14 Cl N O3'
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/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'
'-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                   29.8793(17)
_cell_length_b                   7.7831(4)
_cell_length_c                   12.7135(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.634(5)
_cell_angle_gamma                90
_cell_volume                     2950.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      75.8360
_cell_measurement_theta_min      3.5290
_shelx_estimated_absorpt_T_max   0.793
_shelx_estimated_absorpt_T_min   0.444
_exptl_absorpt_coefficient_mu    2.427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8475
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.193
_diffrn_reflns_theta_min         5.876
_diffrn_ambient_temperature      93.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   5.00   0.50    0.05    --  -45.95  10.00 100.00   50
  2  ω    -69.00 -43.00   0.50    0.20    -- -102.00  61.00 120.00   52
  3  ω   -111.00 -29.00   0.50    0.20    -- -102.00 125.00  90.00  164
  4  ω    -68.00 -32.00   0.50    0.20    -- -102.00  61.00 -60.00   72
  5  ω    -21.00  21.00   0.50    0.05    --  -45.95  19.00-150.00   84
  6  ω    -14.00  26.00   0.50    0.05    --   45.95 -10.00 -73.00   80
  7  ω     46.00  90.00   0.50    0.20    --  104.61 -94.00-150.00   88
  8  ω     34.00 110.00   0.50    0.20    --  104.61-125.00-150.00  152
  9  ω     33.00  73.00   0.50    0.20    --  104.61 -61.00 -30.00   80
 10  ω     33.00 118.00   0.50    0.05    --   45.95  10.00 100.00  170
 11  ω     89.00 173.00   0.50    0.20    --  104.61  10.00 100.00  168
 12  ω     99.00 154.00   0.50    0.20    --  104.61  45.00 -30.00  110
 13  ω     27.00  86.00   0.50    0.05    --   45.95-125.00 120.00  118
 14  ω    -67.00 -35.00   0.50    0.20    -- -102.00  77.00-150.00   64
 15  ω    -97.00 -71.00   0.50    0.05    --  -45.95 -10.00 -73.00   52
 16  ω   -113.00 -88.00   0.50    0.20    -- -102.00 -10.00 -73.00   50
 17  ω   -116.00 -85.00   0.50    0.20    -- -102.00 -61.00-120.00   62
 18  ω   -104.00 -74.00   0.50    0.05    --  -45.95-125.00-150.00   60
 19  ω   -140.00-107.00   0.50    0.20    -- -102.00 -30.00-150.00   66
 20  ω   -173.00-130.00   0.50    0.20    -- -102.00 -61.00-120.00   86
 21  ω   -101.00 -74.00   0.50    0.20    -- -102.00  77.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2639
_reflns_number_total             2914
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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         0.371
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.106
_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)+(0.0811P)²+1.5765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1253
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C14(H14), C17(H17), C13(H13), C2(H2), C6(H6), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.03669(2) 0.53269(5) 0.65803(3) 0.02832(16) Uani 1 1 d . . . . .
O1 O 0.21196(4) 0.79735(14) 0.23150(9) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.46271(4) 0.63055(16) -0.03167(9) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.26112(4) 0.58000(16) 0.09466(9) 0.0243(3) Uani 1 1 d . . . . .
N1 N 0.17121(4) 0.78073(18) 0.28005(10) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.18052(5) 0.6868(2) 0.36492(12) 0.0188(3) Uani 1 1 d . . . . .
C8 C 0.22666(5) 0.6393(2) 0.37455(12) 0.0196(3) Uani 1 1 d . . . . .
H8 H 0.241617 0.571923 0.428290 0.024 Uiso 1 1 calc R . . . .
C9 C 0.24429(5) 0.71158(19) 0.28998(12) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.14482(5) 0.6457(2) 0.43595(12) 0.0188(3) Uani 1 1 d . . . . .
C11 C 0.29402(5) 0.6421(2) 0.14208(12) 0.0193(3) Uani 1 1 d . . . . .
C15 C 0.42087(5) 0.6348(2) 0.00477(12) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.33840(5) 0.64702(19) 0.09666(12) 0.0189(3) Uani 1 1 d . . . . .
C16 C 0.41851(5) 0.6967(2) 0.10749(13) 0.0222(3) Uani 1 1 d . . . . .
H16 H 0.444912 0.734809 0.146137 0.027 Uiso 1 1 calc R . . . .
C14 C 0.38205(5) 0.5834(2) -0.05316(12) 0.0219(3) Uani 1 1 d . . . . .
H14 H 0.383474 0.544304 -0.123652 0.026 Uiso 1 1 calc R . . . .
C17 C 0.37765(5) 0.7022(2) 0.15270(12) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.376175 0.743945 0.222620 0.025 Uiso 1 1 calc R . . . .
C10 C 0.29027(5) 0.7189(2) 0.25201(12) 0.0197(3) Uani 1 1 d . . . . .
H10A H 0.310948 0.656510 0.302548 0.024 Uiso 1 1 calc R . . . .
H10B H 0.300100 0.840347 0.250984 0.024 Uiso 1 1 calc R . . . .
C13 C 0.34138(5) 0.5899(2) -0.00695(12) 0.0213(3) Uani 1 1 d . . . . .
H13 H 0.314911 0.554798 -0.046477 0.026 Uiso 1 1 calc R . . . .
C2 C 0.06734(6) 0.6661(2) 0.48003(13) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.037444 0.703790 0.463969 0.029 Uiso 1 1 calc R . . . .
C6 C 0.12146(6) 0.5153(2) 0.59619(12) 0.0218(3) Uani 1 1 d . . . . .
H6 H 0.128145 0.451161 0.658785 0.026 Uiso 1 1 calc R . . . .
C1 C 0.07845(6) 0.5746(2) 0.57138(13) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.10074(6) 0.7015(2) 0.41272(13) 0.0229(4) Uani 1 1 d . . . . .
H3 H 0.093683 0.764551 0.349865 0.028 Uiso 1 1 calc R . . . .
C5 C 0.15483(5) 0.5515(2) 0.52765(13) 0.0205(3) Uani 1 1 d . . . . .
H5 H 0.184557 0.511805 0.543549 0.025 Uiso 1 1 calc R . . . .
C18 C 0.46702(6) 0.5602(3) -0.13453(13) 0.0269(4) Uani 1 1 d . . . . .
H18A H 0.450411 0.631789 -0.187012 0.040 Uiso 1 1 calc GR . . . .
H18B H 0.454854 0.443213 -0.137270 0.040 Uiso 1 1 calc GR . . . .
H18C H 0.498762 0.557301 -0.149729 0.040 Uiso 1 1 calc GR . . . .


_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 1.7467(17) . ?
O1 N1 1.4055(17) . ?
O1 C9 1.3566(19) . ?
O3 C15 1.3608(19) . ?
O3 C18 1.431(2) . ?
O2 C11 1.220(2) . ?
N1 C7 1.318(2) . ?
C7 C8 1.425(2) . ?
C7 C4 1.476(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.350(2) . ?
C9 C10 1.486(2) . ?
C4 C3 1.401(2) . ?
C4 C5 1.393(2) . ?
C11 C12 1.480(2) . ?
C11 C10 1.531(2) . ?
C15 C16 1.398(2) . ?
C15 C14 1.393(2) . ?
C12 C17 1.400(2) . ?
C12 C13 1.398(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.384(2) . ?
C17 H17 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 H13 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.385(2) . ?
C2 C3 1.383(2) . ?
C6 H6 0.9500 . ?
C6 C1 1.383(2) . ?
C6 C5 1.394(2) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C9 O1 N1 108.69(11) . . ?
C15 O3 C18 117.29(13) . . ?
C7 N1 O1 105.48(12) . . ?
N1 C7 C8 111.53(14) . . ?
N1 C7 C4 119.86(14) . . ?
C8 C7 C4 128.61(14) . . ?
C7 C8 H8 127.8 . . ?
C9 C8 C7 104.33(14) . . ?
C9 C8 H8 127.8 . . ?
O1 C9 C10 116.35(13) . . ?
C8 C9 O1 109.97(14) . . ?
C8 C9 C10 133.65(15) . . ?
C3 C4 C7 120.68(14) . . ?
C5 C4 C7 120.06(14) . . ?
C5 C4 C3 119.26(15) . . ?
O2 C11 C12 122.10(14) . . ?
O2 C11 C10 120.18(14) . . ?
C12 C11 C10 117.72(13) . . ?
O3 C15 C16 115.36(14) . . ?
O3 C15 C14 124.41(14) . . ?
C14 C15 C16 120.23(15) . . ?
C17 C12 C11 123.48(14) . . ?
C13 C12 C11 118.13(14) . . ?
C13 C12 C17 118.38(15) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.81(15) . . ?
C17 C16 H16 120.1 . . ?
C15 C14 H14 120.4 . . ?
C13 C14 C15 119.29(14) . . ?
C13 C14 H14 120.4 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.79(14) . . ?
C16 C17 H17 119.6 . . ?
C9 C10 C11 113.84(13) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.45(15) . . ?
C14 C13 H13 119.3 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C3 C2 C1 118.52(15) . . ?
C1 C6 H6 120.6 . . ?
C1 C6 C5 118.77(15) . . ?
C5 C6 H6 120.6 . . ?
C2 C1 Cl1 118.83(13) . . ?
C6 C1 Cl1 118.98(13) . . ?
C6 C1 C2 122.19(15) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 120.90(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C5 C6 120.34(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
O1 N1 C7 C8 -0.15(17) . . . . ?
O1 N1 C7 C4 179.29(12) . . . . ?
O1 C9 C10 C11 -61.04(18) . . . . ?
O3 C15 C16 C17 -178.43(14) . . . . ?
O3 C15 C14 C13 178.56(15) . . . . ?
O2 C11 C12 C17 -173.69(15) . . . . ?
O2 C11 C12 C13 4.8(2) . . . . ?
O2 C11 C10 C9 -1.0(2) . . . . ?
N1 O1 C9 C8 0.09(16) . . . . ?
N1 O1 C9 C10 -178.41(12) . . . . ?
N1 C7 C8 C9 0.21(18) . . . . ?
N1 C7 C4 C3 1.7(2) . . . . ?
N1 C7 C4 C5 -177.75(14) . . . . ?
C7 C8 C9 O1 -0.17(17) . . . . ?
C7 C8 C9 C10 177.96(16) . . . . ?
C7 C4 C3 C2 -178.75(14) . . . . ?
C7 C4 C5 C6 178.65(14) . . . . ?
C8 C7 C4 C3 -178.92(15) . . . . ?
C8 C7 C4 C5 1.6(2) . . . . ?
C8 C9 C10 C11 120.91(19) . . . . ?
C9 O1 N1 C7 0.04(15) . . . . ?
C4 C7 C8 C9 -179.18(15) . . . . ?
C11 C12 C17 C16 177.08(15) . . . . ?
C11 C12 C13 C14 -177.05(15) . . . . ?
C15 C16 C17 C12 -0.2(2) . . . . ?
C15 C14 C13 C12 0.0(2) . . . . ?
C12 C11 C10 C9 178.71(13) . . . . ?
C16 C15 C14 C13 -1.7(2) . . . . ?
C14 C15 C16 C17 1.8(2) . . . . ?
C17 C12 C13 C14 1.6(2) . . . . ?
C10 C11 C12 C17 6.6(2) . . . . ?
C10 C11 C12 C13 -174.91(14) . . . . ?
C13 C12 C17 C16 -1.4(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C6 C5 C4 0.0(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C3 C2 C1 Cl1 178.86(12) . . . . ?
C3 C2 C1 C6 -1.2(2) . . . . ?
C5 C4 C3 C2 0.7(2) . . . . ?
C5 C6 C1 Cl1 -178.96(12) . . . . ?
C5 C6 C1 C2 1.0(2) . . . . ?
C18 O3 C15 C16 176.97(15) . . . . ?
C18 O3 C15 C14 -3.3(2) . . . . ?

_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
;
