# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_pm-skb-03-161
_database_code_depnum_ccdc_archive 'CCDC 2100734'
loop_
_audit_author_name
_audit_author_address
'SHYAMAL KANTI BERA'
;NISER
India
;
_audit_update_record             
;
2021-08-01 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2015/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 O2'
_chemical_formula_sum            'C19 H14 O2'
_chemical_formula_weight         274.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C76 H56 O8 '
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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+1/2, y+1/2, -z+1/2'
'-x+, -y+, -z+'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.01478(16)
_cell_length_b                   4.81292(5)
_cell_length_c                   18.38696(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.4467(9)
_cell_angle_gamma                90
_cell_volume                     1412.96(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14940
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9140
_cell_measurement_theta_min      3.7980
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23012
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.285
_diffrn_reflns_theta_min         3.527
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -35.00   0.50    1.21    --  -38.50 -35.00 -67.00  140
  2  ω    -42.00  29.00   0.50    1.21    --  -38.50  35.00  89.00  142
  3  ω    -18.00  52.00   0.50    1.21    --   48.56 -35.00 -67.00  140
  4  ω     45.00 116.00   0.50    1.21    --   48.56  35.00  89.00  142
  5  ω     98.00 168.00   0.50    6.52    --  101.38  35.00  89.00  140
  6  ω     35.00 105.00   0.50    6.52    --  101.38 -35.00 -67.00  140
  7  ω    -50.00  24.00   0.50    1.21    --  -38.50  57.00 -30.00  148
  8  ω    -86.00  -6.00   0.50    1.21    --  -38.50 125.00 150.00  160
  9  ω   -101.00 -27.00   0.50    1.21    --  -38.50 -57.00  90.00  148
 10  ω     45.00 115.00   0.50    1.21    --   48.56  37.00-150.00  140
 11  ω    -21.00  54.00   0.50    1.21    --   48.56 -19.00 -90.00  150
 12  ω     37.00 106.00   0.50    6.52    --  101.38 -45.00 150.00  138
 13  ω     32.00 109.00   0.50    6.52    --  101.38-111.00  90.00  154
 14  ω     33.00 110.00   0.50    6.52    --  101.38 -15.00  90.00  154
 15  ω     33.00 107.00   0.50    6.52    --  101.38 -94.00-150.00  148
 16  ω     37.00 106.00   0.50    6.52    --  101.38 -45.00  60.00  138
 17  ω     33.00 107.00   0.50    6.52    --  101.38 -94.00   0.00  148
 18  ω     61.00 146.00   0.50    6.52    --  101.38 178.00 -30.00  170
 19  ω     33.00 110.00   0.50    6.52    --  101.38 -15.00 -30.00  154
 20  ω     33.00 107.00   0.50    6.52    --  101.38 -94.00  90.00  148
 21  ω     61.00 146.00   0.50    6.52    --  101.38 178.00  30.00  170
 22  ω     93.00 170.00   0.50    6.52    --  101.38  15.00-120.00  154
 23  ω    104.00 171.00   0.50    6.52    --  101.38 111.00 -60.00  134
 24  ω     32.00 109.00   0.50    6.52    --  101.38-111.00   0.00  154
 25  ω     88.00 164.00   0.50    6.52    --  101.38  61.00 -60.00  152
 26  ω    104.00 171.00   0.50    6.52    --  101.38 111.00 150.00  134
 27  ω     32.00 109.00   0.50    6.52    --  101.38-111.00 150.00  154
 28  ω     97.00 166.00   0.50    6.52    --  101.38  45.00 -30.00  138
 29  ω    104.00 171.00   0.50    6.52    --  101.38 111.00  30.00  134
 30  ω     32.00 109.00   0.50    6.52    --  101.38-111.00 -60.00  154
 31  ω     37.00 125.00   0.50    6.52    --  101.38 -77.00  90.00  176
 32  ω     37.00 112.00   0.50    1.21    --   48.56  57.00 -90.00  150
 33  ω     37.00 112.00   0.50    1.21    --   48.56  57.00 150.00  150
 34  ω     37.00 112.00   0.50    1.21    --   48.56  57.00-120.00  150
 35  ω     37.00 112.00   0.50    1.21    --   48.56  57.00   0.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0776470000
_diffrn_orient_matrix_UB_12      -0.1008586000
_diffrn_orient_matrix_UB_13      0.0369160000
_diffrn_orient_matrix_UB_21      -0.0291762000
_diffrn_orient_matrix_UB_22      0.3030610000
_diffrn_orient_matrix_UB_23      0.0071961000
_diffrn_orient_matrix_UB_31      -0.0492724000
_diffrn_orient_matrix_UB_32      -0.0204907000
_diffrn_orient_matrix_UB_33      -0.0751680000
_diffrn_oxdiff_digest_frames     
;
017d4b8658a40255668194ef64d136d02400031859d
;
_diffrn_oxdiff_digest_hkl        
;
014b692e28f32174cbdac1e501455b2d1eb3fe
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2626
_reflns_number_total             2873
_reflns_odcompleteness_completeness 99.93
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (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         0.122
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_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     190
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.035
_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)+(0.0598P)²+0.1721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1105
_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 Ternary CH refined with riding coordinates:
 C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00B(H00D), C00D(H00E), C00E(H00F), C00F(H00G), C00G(H00H),
 C00H(H00I), C00I(H00J), C00J(H00K), C00K(H00L), C00L(H00M)
;
_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
O001 O 0.56745(4) 0.30860(18) 0.59742(4) 0.0579(2) Uani 1 1 d . . . . .
O002 O 0.79517(5) 0.08167(19) 0.69414(5) 0.0653(2) Uani 1 1 d . . . . .
C003 C 0.72727(6) 0.1621(2) 0.66787(6) 0.0506(3) Uani 1 1 d . . . . .
C004 C 0.71831(6) 0.3646(2) 0.60768(5) 0.0501(3) Uani 1 1 d . . . . .
C005 C 0.46477(6) 0.1657(2) 0.76536(6) 0.0525(3) Uani 1 1 d . . . . .
C006 C 0.49291(6) 0.1186(2) 0.69467(6) 0.0506(3) Uani 1 1 d . . . . .
C007 C 0.57373(6) 0.2465(2) 0.67460(5) 0.0477(2) Uani 1 1 d . . . . .
H007 H 0.5831 0.4200 0.7019 0.057 Uiso 1 1 calc R . . . .
C008 C 0.64679(7) 0.0536(2) 0.69312(6) 0.0548(3) Uani 1 1 d . . . . .
H00A H 0.6532 0.0268 0.7455 0.066 Uiso 1 1 calc R . . . .
H00B H 0.6347 -0.1259 0.6707 0.066 Uiso 1 1 calc R . . . .
C009 C 0.63888(7) 0.4217(2) 0.57382(6) 0.0516(3) Uani 1 1 d . . . . .
C00A C 0.78777(8) 0.4939(3) 0.58176(7) 0.0631(3) Uani 1 1 d . . . . .
H00C H 0.8408 0.4581 0.6040 0.076 Uiso 1 1 calc R . . . .
C00B C 0.44956(8) -0.0594(3) 0.64758(7) 0.0635(3) Uani 1 1 d . . . . .
H00D H 0.4684 -0.0911 0.6017 0.076 Uiso 1 1 calc R . . . .
C00C C 0.39102(7) 0.0273(3) 0.78446(7) 0.0613(3) Uani 1 1 d . . . . .
C00D C 0.63019(8) 0.5975(3) 0.51390(6) 0.0677(3) Uani 1 1 d . . . . .
H00E H 0.5776 0.6304 0.4904 0.081 Uiso 1 1 calc R . . . .
C00E C 0.50664(8) 0.3415(3) 0.81823(7) 0.0661(3) Uani 1 1 d . . . . .
H00F H 0.5551 0.4337 0.8071 0.079 Uiso 1 1 calc R . . . .
C00F C 0.34852(8) -0.1526(3) 0.73383(8) 0.0726(4) Uani 1 1 d . . . . .
H00G H 0.3003 -0.2431 0.7463 0.087 Uiso 1 1 calc R . . . .
C00G C 0.77900(9) 0.6736(3) 0.52371(7) 0.0738(4) Uani 1 1 d . . . . .
H00H H 0.8257 0.7620 0.5074 0.089 Uiso 1 1 calc R . . . .
C00H C 0.70020(10) 0.7225(3) 0.48962(7) 0.0762(4) Uani 1 1 d . . . . .
H00I H 0.6945 0.8417 0.4497 0.091 Uiso 1 1 calc R . . . .
C00I C 0.37682(9) -0.1954(3) 0.66738(8) 0.0757(4) Uani 1 1 d . . . . .
H00J H 0.3481 -0.3152 0.6346 0.091 Uiso 1 1 calc R . . . .
C00J C 0.36281(9) 0.0718(4) 0.85447(9) 0.0805(4) Uani 1 1 d . . . . .
H00K H 0.3145 -0.0174 0.8672 0.097 Uiso 1 1 calc R . . . .
C00K C 0.47717(10) 0.3779(4) 0.88516(8) 0.0859(5) Uani 1 1 d . . . . .
H00L H 0.5056 0.4944 0.9190 0.103 Uiso 1 1 calc R . . . .
C00L C 0.40454(11) 0.2416(4) 0.90344(9) 0.0919(5) Uani 1 1 d . . . . .
H00M H 0.3849 0.2677 0.9492 0.110 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
O001 C007 1.4461(12) . ?
O001 C009 1.3675(13) . ?
O002 C003 1.2183(12) . ?
C003 C004 1.4734(16) . ?
C003 C008 1.4973(15) . ?
C004 C009 1.3995(15) . ?
C004 C00A 1.3908(16) . ?
C005 C006 1.4264(16) . ?
C005 C00C 1.4235(16) . ?
C005 C00E 1.4177(17) . ?
C006 C007 1.5049(14) . ?
C006 C00B 1.3682(16) . ?
C007 H007 0.9800 . ?
C007 C008 1.5116(14) . ?
C008 H00A 0.9700 . ?
C008 H00B 0.9700 . ?
C009 C00D 1.3874(17) . ?
C00A H00C 0.9300 . ?
C00A C00G 1.373(2) . ?
C00B H00D 0.9300 . ?
C00B C00I 1.4085(18) . ?
C00C C00F 1.408(2) . ?
C00C C00J 1.413(2) . ?
C00D H00E 0.9300 . ?
C00D C00H 1.3770(19) . ?
C00E H00F 0.9300 . ?
C00E C00K 1.3630(19) . ?
C00F H00G 0.9300 . ?
C00F C00I 1.351(2) . ?
C00G H00H 0.9300 . ?
C00G C00H 1.385(2) . ?
C00H H00I 0.9300 . ?
C00I H00J 0.9300 . ?
C00J H00K 0.9300 . ?
C00J C00L 1.353(2) . ?
C00K H00L 0.9300 . ?
C00K C00L 1.399(2) . ?
C00L H00M 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
C009 O001 C007 113.42(8) . . ?
O002 C003 C004 122.67(10) . . ?
O002 C003 C008 121.98(10) . . ?
C004 C003 C008 115.31(9) . . ?
C009 C004 C003 119.76(10) . . ?
C00A C004 C003 121.30(10) . . ?
C00A C004 C009 118.90(11) . . ?
C00C C005 C006 118.50(11) . . ?
C00E C005 C006 123.63(10) . . ?
C00E C005 C00C 117.87(11) . . ?
C005 C006 C007 119.79(9) . . ?
C00B C006 C005 119.71(10) . . ?
C00B C006 C007 120.31(10) . . ?
O001 C007 C006 109.24(8) . . ?
O001 C007 H007 108.8 . . ?
O001 C007 C008 109.99(9) . . ?
C006 C007 H007 108.8 . . ?
C006 C007 C008 111.03(9) . . ?
C008 C007 H007 108.8 . . ?
C003 C008 C007 112.70(9) . . ?
C003 C008 H00A 109.1 . . ?
C003 C008 H00B 109.1 . . ?
C007 C008 H00A 109.1 . . ?
C007 C008 H00B 109.1 . . ?
H00A C008 H00B 107.8 . . ?
O001 C009 C004 122.31(10) . . ?
O001 C009 C00D 117.38(10) . . ?
C00D C009 C004 120.31(11) . . ?
C004 C00A H00C 119.6 . . ?
C00G C00A C004 120.81(12) . . ?
C00G C00A H00C 119.6 . . ?
C006 C00B H00D 119.5 . . ?
C006 C00B C00I 121.10(12) . . ?
C00I C00B H00D 119.5 . . ?
C00F C00C C005 119.50(12) . . ?
C00F C00C C00J 121.56(12) . . ?
C00J C00C C005 118.93(12) . . ?
C009 C00D H00E 120.3 . . ?
C00H C00D C009 119.34(12) . . ?
C00H C00D H00E 120.3 . . ?
C005 C00E H00F 119.4 . . ?
C00K C00E C005 121.15(13) . . ?
C00K C00E H00F 119.4 . . ?
C00C C00F H00G 119.6 . . ?
C00I C00F C00C 120.85(12) . . ?
C00I C00F H00G 119.6 . . ?
C00A C00G H00H 120.2 . . ?
C00A C00G C00H 119.59(12) . . ?
C00H C00G H00H 120.2 . . ?
C00D C00H C00G 121.01(13) . . ?
C00D C00H H00I 119.5 . . ?
C00G C00H H00I 119.5 . . ?
C00B C00I H00J 119.8 . . ?
C00F C00I C00B 120.33(13) . . ?
C00F C00I H00J 119.8 . . ?
C00C C00J H00K 119.3 . . ?
C00L C00J C00C 121.41(13) . . ?
C00L C00J H00K 119.3 . . ?
C00E C00K H00L 119.7 . . ?
C00E C00K C00L 120.62(15) . . ?
C00L C00K H00L 119.7 . . ?
C00J C00L C00K 120.02(14) . . ?
C00J C00L H00M 120.0 . . ?
C00K C00L H00M 120.0 . . ?

_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 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.684
####################################################################### 
# 
# 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_pm-skb-03-59
_database_code_depnum_ccdc_archive 'CCDC 2100733'
loop_
_audit_author_name
_audit_author_address
'SHYAMAL KANTI BERA'
;NISER
India
;
_audit_update_record             
;
2021-12-29 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_audit_creation_date             2021-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2015/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 N2 O3'
_chemical_formula_sum            'C15 H12 N2 O3'
_chemical_formula_weight         268.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H22 N4 O6 '
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, -y+, -z+'

_cell_length_a                   7.5622(4)
_cell_length_b                   8.5111(5)
_cell_length_c                   10.0206(5)
_cell_angle_alpha                88.894(4)
_cell_angle_beta                 75.135(4)
_cell_angle_gamma                85.294(4)
_cell_volume                     621.27(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.5810
_cell_measurement_theta_min      4.5560
_shelx_estimated_absorpt_T_max   0.867
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (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_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             278
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10647
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.232
_diffrn_reflns_theta_min         4.565
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  19.00   0.50    0.50    --  -38.50  96.00-137.00  184
  2  ω     33.00 106.00   0.50    2.10    --  101.38 -96.00 113.00  146
  3  ω    104.00 170.00   0.50    2.10    --  101.38  96.00-137.00  132
  4  ω    -42.00  28.00   0.50    0.50    --  -38.50  37.00 120.00  140
  5  ω   -101.00 -27.00   0.50    0.50    --  -38.50 -57.00 -30.00  148
  6  ω     37.00 112.00   0.50    0.50    --   48.56  57.00 -30.00  150
  7  ω    -21.00  54.00   0.50    0.50    --   48.56 -19.00-180.00  150
  8  ω      3.00  83.00   0.50    0.50    --   48.56 -96.00 113.00  160
  9  ω    -14.00  60.00   0.50    0.50    --   48.56 -57.00  30.00  148
 10  ω     33.00 110.00   0.50    2.10    --  101.38 -15.00-180.00  154
 11  ω     37.00 125.00   0.50    2.10    --  101.38 -77.00 -90.00  176
 12  ω     33.00 107.00   0.50    2.10    --  101.38 -94.00-120.00  148
 13  ω     32.00 109.00   0.50    2.10    --  101.38-111.00 -30.00  154
 14  ω     97.00 166.00   0.50    2.10    --  101.38  45.00 120.00  138
 15  ω     39.00 115.00   0.50    2.10    --  101.38 -61.00 -60.00  152
 16  ω    104.00 171.00   0.50    2.10    --  101.38 111.00 -30.00  134
 17  ω     37.00 106.00   0.50    2.10    --  101.38 -45.00-150.00  138
 18  ω    103.00 166.00   0.50    2.10    --  101.38  77.00   0.00  126
 19  ω     32.00 109.00   0.50    2.10    --  101.38-111.00-150.00  154
 20  ω     37.00 106.00   0.50    2.10    --  101.38 -45.00 -30.00  138
 21  ω     33.00 105.00   0.50    2.10    --  101.38 -30.00   0.00  144
 22  ω     32.00 109.00   0.50    2.10    --  101.38-111.00  60.00  154
 23  ω     39.00 115.00   0.50    2.10    --  101.38 -61.00  90.00  152
 24  ω    103.00 166.00   0.50    2.10    --  101.38  77.00 120.00  126
 25  ω     98.00 170.00   0.50    2.10    --  101.38  30.00  90.00  144
 26  ω     32.00 109.00   0.50    2.10    --  101.38-111.00 120.00  154
 27  ω     97.00 166.00   0.50    2.10    --  101.38  45.00 150.00  138
 28  ω     37.00 112.00   0.50    0.50    --   48.56  57.00 150.00  150
 29  ω     37.00 112.00   0.50    0.50    --   48.56  57.00  30.00  150
 30  ω     37.00 112.00   0.50    0.50    --   48.56  57.00-120.00  150
 31  ω     37.00 112.00   0.50    0.50    --   48.56  57.00-150.00  150
 32  ω     37.00 112.00   0.50    0.50    --   48.56  57.00 -60.00  150
 33  ω     37.00 112.00   0.50    0.50    --   48.56  57.00  90.00  150
 34  ω     97.00 166.00   0.50    2.10    --  101.38  45.00 -60.00  138
 35  ω     88.00 137.00   0.50    2.10    --  101.38  61.00 -30.00   98
 36  ω     88.00 164.00   0.50    2.10    --  101.38  61.00-150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0265428000
_diffrn_orient_matrix_UB_12      -0.0690119000
_diffrn_orient_matrix_UB_13      -0.1454548000
_diffrn_orient_matrix_UB_21      -0.2077854000
_diffrn_orient_matrix_UB_22      -0.0172506000
_diffrn_orient_matrix_UB_23      0.0306857000
_diffrn_orient_matrix_UB_31      -0.0288214000
_diffrn_orient_matrix_UB_32      0.1671088000
_diffrn_orient_matrix_UB_33      -0.0565884000
_diffrn_oxdiff_digest_frames     
;
0161f5ed6f29671e3f8de91ab2e1a4d1d900037e6df
;
_diffrn_oxdiff_digest_hkl        
;
016f78398687cb8d5b8e8dd9c833e435eba3e2
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2275
_reflns_number_total             2514
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (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         0.992
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      1.089
_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)+(0.0948P)²+0.5304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1872
_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 Ternary CH refined with riding coordinates:
 C00K(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00b,H00f)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J)
;
_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
O001 O 0.8126(2) 0.72035(18) 0.81793(19) 0.0385(4) Uani 1 1 d . . . . .
O002 O 0.7824(3) -0.29001(19) 0.4532(2) 0.0476(5) Uani 1 1 d . . . . .
N003 N 0.4323(2) 0.4317(2) 0.76184(19) 0.0302(4) Uani 1 1 d . . . . .
H003 H 0.3666 0.3523 0.7737 0.036 Uiso 1 1 calc R . . . .
N004 N 0.8217(3) -0.1678(2) 0.3889(2) 0.0349(5) Uani 1 1 d . . . . .
O005 O 0.8986(3) -0.1685(2) 0.2673(2) 0.0616(6) Uani 1 1 d . . . . .
C006 C 0.3733(3) 0.5693(2) 0.8374(2) 0.0264(4) Uani 1 1 d . . . . .
C007 C 0.4995(3) 0.6713(2) 0.8604(2) 0.0268(5) Uani 1 1 d . . . . .
C008 C 0.7722(3) -0.0176(2) 0.4626(2) 0.0268(5) Uani 1 1 d . . . . .
C009 C 0.6984(3) 0.6318(2) 0.8054(2) 0.0292(5) Uani 1 1 d . . . . .
C00A C 0.1855(3) 0.6098(2) 0.8926(2) 0.0299(5) Uani 1 1 d . . . . .
H00A H 0.1002 0.5426 0.8797 0.036 Uiso 1 1 calc R . . . .
C00B C 0.6642(3) 0.2664(3) 0.5965(2) 0.0341(5) Uani 1 1 d . . . . .
C00C C 0.4357(3) 0.8104(3) 0.9361(2) 0.0326(5) Uani 1 1 d . . . . .
H00C H 0.5198 0.8775 0.9510 0.039 Uiso 1 1 calc R . . . .
C00D C 0.1258(3) 0.7480(3) 0.9656(2) 0.0314(5) Uani 1 1 d . . . . .
H00D H 0.0006 0.7739 0.9998 0.038 Uiso 1 1 calc R . . . .
C00E C 0.2510(3) 0.8496(2) 0.9889(2) 0.0333(5) Uani 1 1 d . . . . .
H00E H 0.2101 0.9421 1.0392 0.040 Uiso 1 1 calc R . . . .
C00F C 0.7520(3) 0.4743(3) 0.7339(2) 0.0330(5) Uani 1 1 d . . . . .
H00B H 0.7680 0.3944 0.8011 0.040 Uiso 1 1 calc R . . . .
H00F H 0.8685 0.4790 0.6657 0.040 Uiso 1 1 calc R . . . .
C00G C 0.6640(3) -0.0168(3) 0.5967(2) 0.0325(5) Uani 1 1 d . . . . .
H00G H 0.6284 -0.1104 0.6411 0.039 Uiso 1 1 calc R . . . .
C00H C 0.6096(3) 0.1275(3) 0.6635(2) 0.0353(5) Uani 1 1 d . . . . .
H00H H 0.5363 0.1309 0.7536 0.042 Uiso 1 1 calc R . . . .
C00I C 0.7766(3) 0.2599(3) 0.4624(3) 0.0368(5) Uani 1 1 d . . . . .
H00I H 0.8150 0.3528 0.4179 0.044 Uiso 1 1 calc R . . . .
C00J C 0.8317(3) 0.1183(3) 0.3947(2) 0.0355(5) Uani 1 1 d . . . . .
H00J H 0.9073 0.1143 0.3054 0.043 Uiso 1 1 calc R . . . .
C00K C 0.6076(3) 0.4271(3) 0.6629(2) 0.0347(5) Uani 1 1 d . . . . .
H00K H 0.5998 0.5042 0.5903 0.042 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
O001 C009 1.223(3) . ?
O002 N004 1.230(3) . ?
N003 H003 0.8600 . ?
N003 C006 1.386(2) . ?
N003 C00K 1.435(3) . ?
N004 O005 1.208(3) . ?
N004 C008 1.462(3) . ?
C006 C007 1.405(3) . ?
C006 C00A 1.402(3) . ?
C007 C009 1.476(3) . ?
C007 C00C 1.401(3) . ?
C008 C00G 1.382(3) . ?
C008 C00J 1.379(3) . ?
C009 C00F 1.508(3) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.378(3) . ?
C00B C00H 1.388(3) . ?
C00B C00I 1.393(3) . ?
C00B C00K 1.513(3) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.376(3) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.398(3) . ?
C00E H00E 0.9300 . ?
C00F H00B 0.9700 . ?
C00F H00F 0.9700 . ?
C00F C00K 1.530(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.390(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00J 1.374(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 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
C006 N003 H003 121.4 . . ?
C006 N003 C00K 117.27(17) . . ?
C00K N003 H003 121.4 . . ?
O002 N004 C008 118.54(18) . . ?
O005 N004 O002 122.05(19) . . ?
O005 N004 C008 119.41(19) . . ?
N003 C006 C007 120.96(18) . . ?
N003 C006 C00A 120.47(18) . . ?
C00A C006 C007 118.57(18) . . ?
C006 C007 C009 120.16(18) . . ?
C00C C007 C006 119.68(19) . . ?
C00C C007 C009 120.16(19) . . ?
C00G C008 N004 118.70(18) . . ?
C00J C008 N004 118.76(19) . . ?
C00J C008 C00G 122.52(19) . . ?
O001 C009 C007 122.26(19) . . ?
O001 C009 C00F 122.10(19) . . ?
C007 C009 C00F 115.64(18) . . ?
C006 C00A H00A 119.6 . . ?
C00D C00A C006 120.7(2) . . ?
C00D C00A H00A 119.6 . . ?
C00H C00B C00I 119.4(2) . . ?
C00H C00B C00K 122.9(2) . . ?
C00I C00B C00K 117.7(2) . . ?
C007 C00C H00C 119.4 . . ?
C00E C00C C007 121.3(2) . . ?
C00E C00C H00C 119.4 . . ?
C00A C00D H00D 119.6 . . ?
C00A C00D C00E 120.9(2) . . ?
C00E C00D H00D 119.6 . . ?
C00C C00E C00D 118.84(19) . . ?
C00C C00E H00E 120.6 . . ?
C00D C00E H00E 120.6 . . ?
C009 C00F H00B 109.2 . . ?
C009 C00F H00F 109.2 . . ?
C009 C00F C00K 111.98(18) . . ?
H00B C00F H00F 107.9 . . ?
C00K C00F H00B 109.2 . . ?
C00K C00F H00F 109.2 . . ?
C008 C00G H00G 120.9 . . ?
C008 C00G C00H 118.28(19) . . ?
C00H C00G H00G 120.9 . . ?
C00B C00H C00G 120.4(2) . . ?
C00B C00H H00H 119.8 . . ?
C00G C00H H00H 119.8 . . ?
C00B C00I H00I 119.5 . . ?
C00J C00I C00B 121.0(2) . . ?
C00J C00I H00I 119.5 . . ?
C008 C00J H00J 120.8 . . ?
C00I C00J C008 118.4(2) . . ?
C00I C00J H00J 120.8 . . ?
N003 C00K C00B 112.22(18) . . ?
N003 C00K C00F 109.21(19) . . ?
N003 C00K H00K 108.4 . . ?
C00B C00K C00F 110.12(19) . . ?
C00B C00K H00K 108.4 . . ?
C00F C00K H00K 108.4 . . ?

_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 2.391
_oxdiff_exptl_absorpt_empirical_full_min 0.334
####################################################################### 
# 
# 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_pm-skb-03-129
_database_code_depnum_ccdc_archive 'CCDC 2100735'
loop_
_audit_author_name
_audit_author_address
'SHYAMAL KANTI BERA'
;NISER
India
;
_audit_update_record             
;
2021-08-01 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2015/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Cl N O'
_chemical_formula_sum            'C15 H12 Cl N O'
_chemical_formula_weight         257.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H12ClNO
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'
Cl Cl 0.3639 0.7018 '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                   17.5707(3)
_cell_length_b                   10.71140(10)
_cell_length_c                   13.5943(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.535(2)
_cell_angle_gamma                90
_cell_volume                     2465.07(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15093
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.0760
_cell_measurement_theta_min      3.4090
_shelx_estimated_absorpt_T_max   0.650
_shelx_estimated_absorpt_T_min   0.622
_exptl_absorpt_coefficient_mu    2.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (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_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18437
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.374
_diffrn_reflns_theta_min         4.886
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -20.00   0.50    0.53    --  -38.50 -69.00 -81.00  162
  2  ω    -56.00  25.00   0.50    0.53    --  -38.50  69.00  50.00  162
  3  ω     31.00 112.00   0.50    0.53    --   48.56  69.00  50.00  162
  4  ω     83.00 165.00   0.50    1.80    --  101.38  69.00  50.00  164
  5  ω     38.00 120.00   0.50    1.80    --  101.38 -69.00 -81.00  164
  6  ω    -42.00  28.00   0.50    0.53    --  -38.50  37.00   0.00  140
  7  ω   -101.00 -24.00   0.50    0.53    --  -38.50 -63.00 175.51  154
  8  ω    -62.00  26.00   0.50    0.53    --  -38.50  77.00 -30.00  176
  9  ω   -108.00 -33.00   0.50    0.53    --  -38.50 -19.00  60.00  150
 10  ω    -14.00  67.00   0.50    0.53    --   48.56 -69.00 -81.00  162
 11  ω     32.00 109.00   0.50    1.80    --  101.38-111.00 -60.00  154
 12  ω    103.00 166.00   0.50    1.80    --  101.38  77.00 150.00  126
 13  ω     33.00 107.00   0.50    1.80    --  101.38 -94.00 120.00  148
 14  ω     98.00 170.00   0.50    1.80    --  101.38  30.00 120.00  144
 15  ω     97.00 166.00   0.50    1.80    --  101.38  45.00-120.00  138
 16  ω     33.00 107.00   0.50    1.80    --  101.38 -94.00-180.00  148
 17  ω     32.00 109.00   0.50    1.80    --  101.38-111.00  30.00  154
 18  ω    103.00 166.00   0.50    1.80    --  101.38  77.00 -90.00  126
 19  ω     85.00 164.00   0.50    1.80    --  101.38  66.00 -15.47  158
 20  ω     37.00 106.00   0.50    1.80    --  101.38 -45.00   0.00  138
 21  ω    103.00 166.00   0.50    1.80    --  101.38  77.00  30.00  126
 22  ω     37.00 106.00   0.50    1.80    --  101.38 -45.00-150.00  138
 23  ω     32.00 109.00   0.50    1.80    --  101.38-111.00-180.00  154
 24  ω     32.00 109.00   0.50    1.80    --  101.38-111.00  60.00  154
 25  ω     33.00 107.00   0.50    1.80    --  101.38 -94.00 -60.00  148
 26  ω     39.00 115.00   0.50    1.80    --  101.38 -61.00   0.00  152
 27  ω     37.00 106.00   0.50    1.80    --  101.38 -45.00 120.00  138
 28  ω    103.00 166.00   0.50    1.80    --  101.38  77.00 -30.00  126
 29  ω    104.00 171.00   0.50    1.80    --  101.38 111.00 -30.00  134
 30  ω    103.00 166.00   0.50    1.80    --  101.38  77.00 -60.00  126
 31  ω     37.00  96.00   0.50    0.53    --   48.56  57.00-120.00  118
 32  ω     37.00 112.00   0.50    0.53    --   48.56  57.00 -30.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0687989000
_diffrn_orient_matrix_UB_12      -0.0937079000
_diffrn_orient_matrix_UB_13      0.0296236000
_diffrn_orient_matrix_UB_21      -0.0190501000
_diffrn_orient_matrix_UB_22      -0.0239813000
_diffrn_orient_matrix_UB_23      0.1026536000
_diffrn_orient_matrix_UB_31      -0.0563304000
_diffrn_orient_matrix_UB_32      -0.1065281000
_diffrn_orient_matrix_UB_33      -0.0491777000
_diffrn_oxdiff_digest_frames     
;
01351c9ba5f9534918b17082c835796788000432218
;
_diffrn_oxdiff_digest_hkl        
;
0126fd85d55b25c10a94c04492a50725271c9b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2460
_reflns_number_total             2519
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (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         1.280
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.028
_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)+(0.0597P)²+6.5477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1242
_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 Ternary CH refined with riding coordinates:
 C005(H005)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C008(H008), C00A(H00C), C00C(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I)
;
_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
Cl01 Cl 0.60675(3) -0.10253(5) 0.35119(4) 0.03238(18) Uani 1 1 d . . . . .
O002 O 0.59257(10) 0.46892(15) 0.83776(10) 0.0298(4) Uani 1 1 d . . . . .
N003 N 0.63347(9) 0.46540(15) 0.55544(11) 0.0185(3) Uani 1 1 d . . . . .
H003 H 0.6567 0.4527 0.5082 0.022 Uiso 1 1 calc R . . . .
C004 C 0.58556(11) 0.25267(17) 0.52020(13) 0.0179(4) Uani 1 1 d . . . . .
C005 C 0.57879(11) 0.37263(17) 0.57640(13) 0.0179(4) Uani 1 1 d . . . . .
H005 H 0.5247 0.4045 0.5518 0.022 Uiso 1 1 calc R . . . .
C006 C 0.64719(10) 0.57326(18) 0.61234(14) 0.0171(4) Uani 1 1 d . . . . .
C007 C 0.63145(11) 0.58126(18) 0.70888(14) 0.0189(4) Uani 1 1 d . . . . .
C008 C 0.66591(12) 0.08735(18) 0.47949(15) 0.0219(4) Uani 1 1 d . . . . .
H008 H 0.7151 0.0507 0.4865 0.026 Uiso 1 1 calc R . . . .
C009 C 0.59741(11) 0.35103(18) 0.69152(14) 0.0204(4) Uani 1 1 d . . . . .
H00A H 0.5561 0.2998 0.7057 0.024 Uiso 1 1 calc R . . . .
H00B H 0.6466 0.3051 0.7137 0.024 Uiso 1 1 calc R . . . .
C00A C 0.65907(11) 0.19636(18) 0.53137(14) 0.0207(4) Uani 1 1 d . . . . .
H00C H 0.7040 0.2325 0.5741 0.025 Uiso 1 1 calc R . . . .
C00B C 0.60443(11) 0.46997(19) 0.75272(14) 0.0210(4) Uani 1 1 d . . . . .
C00C C 0.67877(11) 0.67874(19) 0.57546(15) 0.0204(4) Uani 1 1 d . . . . .
H00D H 0.6902 0.6750 0.5125 0.024 Uiso 1 1 calc R . . . .
C00D C 0.59835(12) 0.03391(18) 0.41698(15) 0.0221(4) Uani 1 1 d . . . . .
C00E C 0.51926(12) 0.19720(19) 0.45669(15) 0.0235(4) Uani 1 1 d . . . . .
H00E H 0.4701 0.2342 0.4485 0.028 Uiso 1 1 calc R . . . .
C00F C 0.67590(12) 0.79623(19) 0.72675(15) 0.0234(4) Uani 1 1 d . . . . .
H00F H 0.6851 0.8702 0.7639 0.028 Uiso 1 1 calc R . . . .
C00G C 0.64538(12) 0.69388(19) 0.76377(15) 0.0227(4) Uani 1 1 d . . . . .
H00G H 0.6337 0.6993 0.8264 0.027 Uiso 1 1 calc R . . . .
C00H C 0.69291(11) 0.78709(19) 0.63161(15) 0.0225(4) Uani 1 1 d . . . . .
H00H H 0.7141 0.8556 0.6062 0.027 Uiso 1 1 calc R . . . .
C00I C 0.52491(12) 0.0871(2) 0.40494(16) 0.0258(4) Uani 1 1 d . . . . .
H00I H 0.4800 0.0500 0.3630 0.031 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
Cl01 C00D 1.740(2) . ?
O002 C00B 1.228(2) . ?
N003 H003 0.8600 . ?
N003 C005 1.462(2) . ?
N003 C006 1.375(2) . ?
C004 C005 1.516(3) . ?
C004 C00A 1.397(3) . ?
C004 C00E 1.385(3) . ?
C005 H005 0.9800 . ?
C005 C009 1.528(2) . ?
C006 C007 1.415(2) . ?
C006 C00C 1.409(3) . ?
C007 C00B 1.467(3) . ?
C007 C00G 1.405(3) . ?
C008 H008 0.9300 . ?
C008 C00A 1.386(3) . ?
C008 C00D 1.385(3) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C00B 1.508(3) . ?
C00A H00C 0.9300 . ?
C00C H00D 0.9300 . ?
C00C C00H 1.375(3) . ?
C00D C00I 1.380(3) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.390(3) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.374(3) . ?
C00F C00H 1.407(3) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 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
C005 N003 H003 120.4 . . ?
C006 N003 H003 120.4 . . ?
C006 N003 C005 119.12(14) . . ?
C00A C004 C005 120.44(17) . . ?
C00E C004 C005 120.77(17) . . ?
C00E C004 C00A 118.80(17) . . ?
N003 C005 C004 109.48(14) . . ?
N003 C005 H005 108.9 . . ?
N003 C005 C009 109.31(15) . . ?
C004 C005 H005 108.9 . . ?
C004 C005 C009 111.32(15) . . ?
C009 C005 H005 108.9 . . ?
N003 C006 C007 121.63(17) . . ?
N003 C006 C00C 120.00(16) . . ?
C00C C006 C007 118.36(17) . . ?
C006 C007 C00B 119.51(17) . . ?
C00G C007 C006 119.69(17) . . ?
C00G C007 C00B 120.74(16) . . ?
C00A C008 H008 120.5 . . ?
C00D C008 H008 120.5 . . ?
C00D C008 C00A 118.92(18) . . ?
C005 C009 H00A 108.8 . . ?
C005 C009 H00B 108.8 . . ?
H00A C009 H00B 107.7 . . ?
C00B C009 C005 113.61(16) . . ?
C00B C009 H00A 108.8 . . ?
C00B C009 H00B 108.8 . . ?
C004 C00A H00C 119.6 . . ?
C008 C00A C004 120.82(18) . . ?
C008 C00A H00C 119.6 . . ?
O002 C00B C007 122.99(18) . . ?
O002 C00B C009 120.13(18) . . ?
C007 C00B C009 116.72(15) . . ?
C006 C00C H00D 119.7 . . ?
C00H C00C C006 120.62(17) . . ?
C00H C00C H00D 119.7 . . ?
C008 C00D Cl01 119.06(15) . . ?
C00I C00D Cl01 119.43(16) . . ?
C00I C00D C008 121.51(18) . . ?
C004 C00E H00E 119.4 . . ?
C004 C00E C00I 121.15(18) . . ?
C00I C00E H00E 119.4 . . ?
C00G C00F H00F 120.6 . . ?
C00G C00F C00H 118.77(18) . . ?
C00H C00F H00F 120.6 . . ?
C007 C00G H00G 119.3 . . ?
C00F C00G C007 121.34(18) . . ?
C00F C00G H00G 119.3 . . ?
C00C C00H C00F 121.19(18) . . ?
C00C C00H H00H 119.4 . . ?
C00F C00H H00H 119.4 . . ?
C00D C00I C00E 118.80(19) . . ?
C00D C00I H00I 120.6 . . ?
C00E C00I H00I 120.6 . . ?

_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 1.895
_oxdiff_exptl_absorpt_empirical_full_min 0.574
####################################################################### 
# 
# 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_pm-skb-03-172r
_database_code_depnum_ccdc_archive 'CCDC 2100736'
loop_
_audit_author_name
_audit_author_address
'SHYAMAL KANTI BERA'
;NISER
India
;
_audit_update_record             
;
2021-08-01 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2015/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Cl O2'
_chemical_formula_sum            'C15 H11 Cl O2'
_chemical_formula_weight         258.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H11 Cl O2'
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'
O O 0.0492 0.0322 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+1/2, y+1/2, -z+1/2'
'-x+, -y+, -z+'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.86690(10)
_cell_length_b                   5.12440(10)
_cell_length_c                   19.6290(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.6480(10)
_cell_angle_gamma                90
_cell_volume                     1192.38(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15408
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.0120
_cell_measurement_theta_min      3.7390
_shelx_estimated_absorpt_T_max   0.637
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    2.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (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_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16935
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.297
_diffrn_reflns_theta_min         4.268
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00  -5.00   0.50    1.00    --  -38.50 124.00-120.00  162
  2  ω   -102.00 -17.00   0.50    1.00    --  -38.50 147.00  44.00  170
  3  ω     38.00 114.00   0.50    1.00    --   48.56-147.00  -4.00  152
  4  ω     27.00  99.00   0.50    1.00    --   48.56-124.00 160.00  144
  5  ω     36.00 112.00   0.50    5.00    --  101.38-124.00 160.00  152
  6  ω     85.00 165.00   0.50    5.00    --  101.38 147.00  44.00  160
  7  ω     98.00 167.00   0.50    5.00    --  101.38 124.00-120.00  138
  8  ω     38.00 128.00   0.50    5.00    --  101.38-147.00  -4.00  180
  9  ω   -101.00 -27.00   0.50    1.00    --  -38.50 -57.00 -60.00  148
 10  ω   -101.00 -27.00   0.50    1.00    --  -38.50 -57.00-120.00  148
 11  ω   -101.00 -27.00   0.50    1.00    --  -38.50 -57.00 -30.00  148
 12  ω     37.00 112.00   0.50    1.00    --   48.56  57.00  30.00  150
 13  ω    -18.00  52.00   0.50    1.00    --   48.56 -37.00  90.00  140
 14  ω    -18.00  52.00   0.50    1.00    --   48.56 -37.00 -60.00  140
 15  ω     37.00 106.00   0.50    5.00    --  101.38 -45.00 150.00  138
 16  ω     39.00 115.00   0.50    5.00    --  101.38 -61.00   0.00  152
 17  ω     39.00 115.00   0.50    5.00    --  101.38 -61.00 -60.00  152
 18  ω     32.00 109.00   0.50    5.00    --  101.38-111.00 -30.00  154
 19  ω    103.00 166.00   0.50    5.00    --  101.38  77.00-150.00  126
 20  ω     32.00 109.00   0.50    5.00    --  101.38-111.00 120.00  154
 21  ω     33.00 105.00   0.50    5.00    --  101.38 -30.00-180.00  144
 22  ω     97.00 166.00   0.50    5.00    --  101.38  45.00 120.00  138
 23  ω    103.00 166.00   0.50    5.00    --  101.38  77.00   0.00  126
 24  ω     34.00 106.00   0.50    5.00    --  101.38 -94.00-150.00  144
 25  ω     99.00 145.00   0.50    5.00    --  101.38  45.00 150.00   92
 26  ω     39.00 109.00   0.50    5.00    --  101.38-111.00  30.00  140
 27  ω     33.00  99.00   0.50    5.00    --  101.38-111.00   0.00  132
 28  ω    102.00 144.00   0.50    5.00    --  101.38  45.00 -90.00   84
 29  ω     40.00 106.00   0.50    5.00    --  101.38 -61.00 120.00  132
 30  ω    105.00 166.00   0.50    5.00    --  101.38  77.00 150.00  122
 31  ω    121.00 168.00   0.50    5.00    --  101.38 111.00 -90.00   94
 32  ω     99.00 166.00   0.50    5.00    --  101.38  30.00  60.00  134
 33  ω    110.00 169.00   0.50    5.00    --  101.38  30.00-180.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0229382000
_diffrn_orient_matrix_UB_12      0.0957888000
_diffrn_orient_matrix_UB_13      -0.0737237000
_diffrn_orient_matrix_UB_21      0.0711225000
_diffrn_orient_matrix_UB_22      -0.2268685000
_diffrn_orient_matrix_UB_23      -0.0264433000
_diffrn_orient_matrix_UB_31      -0.1062777000
_diffrn_orient_matrix_UB_32      -0.1725911000
_diffrn_orient_matrix_UB_33      -0.0062116000
_diffrn_oxdiff_digest_frames     
;
0102a22a51b3e79217f80e099ca29394500003399bc
;
_diffrn_oxdiff_digest_hkl        
;
0196b4f02c07a39ea742e1fdee8ac21da1a4ca
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2432
_reflns_number_total             2447
_reflns_odcompleteness_completeness 99.96
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (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         0.304
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.073
_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)+(0.0406P)²+0.6788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0820
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C11(H11), C2(H2), C4(H4), C3(H3), C14(H14), 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
Cl1 Cl 0.87486(3) 0.22877(7) 0.76633(2) 0.02768(12) Uani 1 1 d . . . . .
O1 O 0.80863(7) 0.41539(18) 0.45662(4) 0.0174(2) Uani 1 1 d . . . . .
O2 O 0.46633(7) 0.33639(19) 0.42516(5) 0.0207(2) Uani 1 1 d . . . . .
C1 C 0.75239(10) 0.5595(2) 0.40722(6) 0.0163(2) Uani 1 1 d . . . . .
C6 C 0.63465(10) 0.5519(2) 0.39689(6) 0.0164(2) Uani 1 1 d . . . . .
C9 C 0.73892(10) 0.3508(2) 0.51331(6) 0.0161(2) Uani 1 1 d . . . . .
H9 H 0.7135 0.5163 0.5348 0.019 Uiso 1 1 calc R . . . .
C10 C 0.81028(10) 0.1996(2) 0.56499(6) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.58277(11) 0.7196(3) 0.34837(6) 0.0189(3) Uani 1 1 d . . . . .
H5 H 0.5030 0.7184 0.3416 0.023 Uiso 1 1 calc R . . . .
C15 C 0.87463(10) -0.0136(3) 0.54580(6) 0.0192(3) Uani 1 1 d . . . . .
H15 H 0.8763 -0.0619 0.4991 0.023 Uiso 1 1 calc R . . . .
C11 C 0.80900(11) 0.2717(3) 0.63313(7) 0.0186(3) Uani 1 1 d . . . . .
H11 H 0.7655 0.4169 0.6466 0.022 Uiso 1 1 calc R . . . .
C8 C 0.63570(10) 0.1999(2) 0.48665(6) 0.0177(3) Uani 1 1 d . . . . .
H8A H 0.6598 0.0360 0.4649 0.021 Uiso 1 1 calc R . . . .
H8B H 0.5883 0.1538 0.5251 0.021 Uiso 1 1 calc R . . . .
C7 C 0.56783(10) 0.3628(2) 0.43525(6) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.81726(11) 0.7207(3) 0.36730(7) 0.0196(3) Uani 1 1 d . . . . .
H2 H 0.8972 0.7191 0.3729 0.024 Uiso 1 1 calc R . . . .
C4 C 0.64643(11) 0.8861(3) 0.31047(6) 0.0214(3) Uani 1 1 d . . . . .
H4 H 0.6106 1.0019 0.2785 0.026 Uiso 1 1 calc R . . . .
C12 C 0.87207(10) 0.1288(3) 0.68134(6) 0.0200(3) Uani 1 1 d . . . . .
C3 C 0.76409(11) 0.8832(3) 0.31943(7) 0.0218(3) Uani 1 1 d . . . . .
H3 H 0.8081 0.9941 0.2924 0.026 Uiso 1 1 calc R . . . .
C14 C 0.93635(11) -0.1554(3) 0.59498(7) 0.0221(3) Uani 1 1 d . . . . .
H14 H 0.9799 -0.3009 0.5817 0.026 Uiso 1 1 calc R . . . .
C13 C 0.93497(11) -0.0862(3) 0.66334(7) 0.0223(3) Uani 1 1 d . . . . .
H13 H 0.9763 -0.1844 0.6971 0.027 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 C12 1.7440(13) . ?
O1 C1 1.3681(15) . ?
O1 C9 1.4550(14) . ?
O2 C7 1.2191(15) . ?
C1 C6 1.4031(17) . ?
C1 C2 1.3945(18) . ?
C6 C5 1.4035(18) . ?
C6 C7 1.4799(17) . ?
C9 H9 1.0000 . ?
C9 C10 1.5056(16) . ?
C9 C8 1.5209(17) . ?
C10 C15 1.3950(18) . ?
C10 C11 1.3882(18) . ?
C5 H5 0.9500 . ?
C5 C4 1.3801(19) . ?
C15 H15 0.9500 . ?
C15 C14 1.3896(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3879(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5127(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3855(19) . ?
C4 H4 0.9500 . ?
C4 C3 1.3993(19) . ?
C12 C13 1.386(2) . ?
C3 H3 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.389(2) . ?
C13 H13 0.9500 . ?

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
C1 O1 C9 112.89(9) . . ?
O1 C1 C6 122.50(11) . . ?
O1 C1 C2 117.01(11) . . ?
C2 C1 C6 120.48(11) . . ?
C1 C6 C5 118.93(12) . . ?
C1 C6 C7 119.88(11) . . ?
C5 C6 C7 121.17(11) . . ?
O1 C9 H9 108.8 . . ?
O1 C9 C10 108.08(9) . . ?
O1 C9 C8 109.25(10) . . ?
C10 C9 H9 108.8 . . ?
C10 C9 C8 112.90(10) . . ?
C8 C9 H9 108.8 . . ?
C15 C10 C9 121.26(11) . . ?
C11 C10 C9 118.78(11) . . ?
C11 C10 C15 119.93(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.69(12) . . ?
C4 C5 H5 119.7 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.96(12) . . ?
C14 C15 H15 120.0 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.15(12) . . ?
C12 C11 H11 120.4 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C7 C8 C9 110.15(10) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
O2 C7 C6 122.59(11) . . ?
O2 C7 C8 122.60(11) . . ?
C6 C7 C8 114.80(10) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.42(12) . . ?
C3 C2 H2 120.3 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.58(12) . . ?
C3 C4 H4 120.2 . . ?
C11 C12 Cl1 118.88(11) . . ?
C13 C12 Cl1 119.40(10) . . ?
C13 C12 C11 121.70(12) . . ?
C2 C3 C4 120.80(12) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.57(12) . . ?
C13 C14 H14 119.7 . . ?
C12 C13 C14 118.67(12) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?

_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.785
