# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2249461'
loop_
_audit_author_name
_audit_author_address
'Noimur Rahman'
;UM DAE Centre for Excellence in Basic Sciences
India
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         339.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   9.58700(10)
_cell_length_b                   16.55580(10)
_cell_length_c                   10.71170(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.0720(10)
_cell_angle_gamma                90
_cell_volume                     1586.47(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    14977
_cell_measurement_theta_min      5.1630
_cell_measurement_theta_max      76.9060

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.848
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_T_min  0.71164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.626
_oxdiff_exptl_absorpt_empirical_full_max 1.758
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      298(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            19468
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.169
_diffrn_reflns_theta_max         76.864
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1089668000
_diffrn_orient_matrix_UB_12      -0.0662708000
_diffrn_orient_matrix_UB_13      -0.0085806000
_diffrn_orient_matrix_UB_21      0.0609756000
_diffrn_orient_matrix_UB_22      0.0572546000
_diffrn_orient_matrix_UB_23      -0.0816165000
_diffrn_orient_matrix_UB_31      0.1185975000
_diffrn_orient_matrix_UB_32      0.0315220000
_diffrn_orient_matrix_UB_33      0.1304548000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  25.00   0.50    0.39    --  -48.29  19.00 -90.00   94
  2  ω    -20.00   6.00   0.50    0.39    --  -48.29  77.00-180.00   52
  3  ω    -42.00 -17.00   0.50    1.55    --  -86.25  37.00-120.00   50
  4  ω    -68.00 -42.00   0.50    0.39    --  -48.29  77.00-180.00   52
  5  ω    -77.00  21.00   0.50    0.39    --  -48.29  97.00  13.00  196
  6  ω    -49.00 -23.00   0.50    1.55    --  -86.25  97.00  13.00   52
  7  ω    -64.00 -15.00   0.50    1.55    --  -86.25  57.00  30.00   98
  8  ω    -42.00 -14.00   0.50    1.55    --  -86.25  37.00  90.00   56
  9  ω    -41.00 -13.00   0.50    1.55    --  -86.25  37.00 150.00   56
 10  ω   -114.00 -37.00   0.50    0.39    --  -48.29 -77.00 -60.00  154
 11  ω    -95.00 -63.00   0.50    1.55    --  -86.25 -77.00 -60.00   64
 12  ω   -120.00 -86.00   0.50    1.55    --  -86.25 -97.00 -94.00   68
 13  ω   -116.00 -73.00   0.50    0.39    --  -48.29-125.00  30.00   86
 14  ω   -149.00-115.00   0.50    1.55    --  -86.25 -77.00 -60.00   68
 15  ω     -6.00  81.00   0.50    0.39    --   48.29 -97.00 -94.00  174
 16  ω     53.00 105.00   0.50    1.55    --  107.39 -97.00 -94.00  104
 17  ω     76.00 111.00   0.50    1.55    --  107.39-125.00 -90.00   70
 18  ω     67.00 107.00   0.50    1.55    --  107.39-103.00-129.28   80
 19  ω     38.00  63.00   0.50    1.55    --  107.39 -57.00 -90.00   50
 20  ω     35.00  66.00   0.50    1.55    --  107.39 -57.00 -30.00   62
 21  ω     44.00  94.00   0.50    1.55    --  107.39 -99.00   0.00  100
 22  ω     67.00 106.00   0.50    1.55    --  107.39-125.00   0.00   78
 23  ω     76.00 106.00   0.50    1.55    --  107.39-110.00  50.80   60
 24  ω     62.00  88.00   0.50    1.55    --  107.39 -77.00  60.00   52
 25  ω     35.00 101.00   0.50    1.55    --  107.39 -99.00  60.00  132
 26  ω     81.00 106.00   0.50    1.55    --  107.39 -77.00 150.00   50
 27  ω     38.00 106.00   0.50    1.55    --  107.39-125.00 150.00  136
 28  ω     41.00  66.00   0.50    1.55    --  107.39 -57.00  30.00   50
 29  ω     36.00  62.00   0.50    1.55    --  107.39 -57.00  60.00   52
 30  ω     41.00  72.00   0.50    1.55    --  107.39-110.00  50.80   62
 31  ω     35.00  71.00   0.50    1.55    --  107.39 -77.00 150.00   72
 32  ω     96.00 140.00   0.50    1.55    --  107.39  19.00   0.00   88
 33  ω    145.00 178.00   0.50    1.55    --  107.39  19.00   0.00   66
 34  ω    134.00 173.00   0.50    1.55    --  107.39  37.00 -60.00   78
 35  ω    136.00 161.00   0.50    1.55    --  107.39  57.00-120.00   50
 36  ω    108.00 141.00   0.50    1.55    --  107.39  97.00  13.00   66
 37  ω     99.00 170.00   0.50    1.55    --  107.39 125.00 -60.00  142
 38  ω     95.00 178.00   0.50    1.55    --  107.39  37.00 -90.00  166
 39  ω     96.00 127.00   0.50    1.55    --  107.39  37.00 -60.00   62
 40  ω    105.00 145.00   0.50    1.55    --  107.39  77.00 150.00   80
 41  ω     37.00  68.00   0.50    1.55    --  107.39-125.00 -90.00   62
 42  ω     35.00  61.00   0.50    1.55    --  107.39-103.00-129.28   52
 43  ω     35.00 111.00   0.50    1.55    --  107.39-125.00-180.00  152
 44  ω    -13.00  19.00   0.50    0.39    --   48.29 -19.00   0.00   64
;
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_digest_frames     
;
0166060621cf7fc910d4b265b53b555192000301e69
;
_diffrn_oxdiff_digest_hkl        
;
01059d1c3a7da1a21fda59d3043dd7d5b02af6
;
_reflns_number_total             3288
_reflns_number_gt                2904
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep 3 for windows'
_computing_publication_material  'WinGX 2021.3'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.4415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0053(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3288
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.05883(16) 0.41444(9) 0.38092(14) 0.0368(3) Uani 1 1 d . . . . .
C2 C -0.10960(17) 0.39163(10) 0.48031(16) 0.0430(4) Uani 1 1 d . . . . .
H2 H -0.206200 0.404241 0.474711 0.052 Uiso 1 1 calc R U . . .
C3 C -0.01375(16) 0.34938(10) 0.58922(15) 0.0406(3) Uani 1 1 d . . . . .
H3 H -0.046533 0.334453 0.657766 0.049 Uiso 1 1 calc R U . . .
C4 C 0.13005(15) 0.32883(8) 0.59830(13) 0.0329(3) Uani 1 1 d . . . . .
C5 C 0.17685(17) 0.35284(11) 0.49435(15) 0.0431(4) Uani 1 1 d . . . . .
H5 H 0.272690 0.339690 0.498378 0.052 Uiso 1 1 calc R U . . .
C6 C 0.08306(17) 0.39584(10) 0.38553(15) 0.0437(4) Uani 1 1 d . . . . .
H6 H 0.115174 0.411805 0.317062 0.052 Uiso 1 1 calc R U . . .
C7 C 0.23440(15) 0.28022(8) 0.71788(13) 0.0323(3) Uani 1 1 d . . . . .
H7 H 0.234914 0.224208 0.688450 0.039 Uiso 1 1 calc R U . . .
C8 C 0.39327(14) 0.31093(8) 0.76460(13) 0.0314(3) Uani 1 1 d . . . . .
C9 C 0.49681(15) 0.28309(8) 0.70098(14) 0.0346(3) Uani 1 1 d . . . . .
C10 C 0.65193(17) 0.31868(9) 0.74860(17) 0.0424(4) Uani 1 1 d . . . . .
H10A H 0.686791 0.319906 0.674088 0.051 Uiso 1 1 calc R U . . .
H10B H 0.718260 0.283416 0.816439 0.051 Uiso 1 1 calc R U . . .
C11 C 0.66322(15) 0.40399(9) 0.80660(15) 0.0371(3) Uani 1 1 d . . . . .
C12 C 0.59434(16) 0.40175(10) 0.91576(15) 0.0392(3) Uani 1 1 d . . . . .
H12A H 0.662629 0.374379 0.993934 0.047 Uiso 1 1 calc R U . . .
H12B H 0.581626 0.456618 0.941591 0.047 Uiso 1 1 calc R U . . .
C13 C 0.44736(14) 0.35983(8) 0.87113(13) 0.0317(3) Uani 1 1 d . . . . .
C14 C 0.24901(15) 0.32894(8) 0.94387(13) 0.0319(3) Uani 1 1 d . . . . .
C15 C 0.18532(15) 0.27955(8) 0.83753(14) 0.0331(3) Uani 1 1 d . . . . .
C16 C 0.07063(16) 0.22586(9) 0.83959(15) 0.0379(3) Uani 1 1 d . . . . .
C17 C 0.5813(2) 0.46354(11) 0.69585(19) 0.0523(4) Uani 1 1 d . . . . .
H17A H 0.478366 0.447775 0.655453 0.079 Uiso 1 1 calc R U . . .
H17B H 0.626781 0.463598 0.629338 0.079 Uiso 1 1 calc R U . . .
H17C H 0.587064 0.516737 0.733060 0.079 Uiso 1 1 calc R U . . .
C18 C 0.82790(18) 0.42849(11) 0.87020(19) 0.0513(4) Uani 1 1 d . . . . .
H18A H 0.872278 0.429198 0.802884 0.077 Uiso 1 1 calc R U . . .
H18B H 0.879785 0.390309 0.938591 0.077 Uiso 1 1 calc R U . . .
H18C H 0.834827 0.481303 0.908964 0.077 Uiso 1 1 calc R U . . .
N1 N -0.15928(15) 0.46032(9) 0.26621(13) 0.0459(3) Uani 1 1 d . . . . .
N2 N -0.02329(17) 0.18220(9) 0.83808(16) 0.0540(4) Uani 1 1 d . . . . .
N3 N 0.20972(15) 0.33975(9) 1.05070(13) 0.0410(3) Uani 1 1 d . . . . .
O1 O -0.10913(16) 0.48887(11) 0.18717(14) 0.0723(5) Uani 1 1 d . . . . .
O2 O -0.28942(16) 0.46662(13) 0.25380(17) 0.0885(6) Uani 1 1 d . . . . .
O3 O 0.36979(11) 0.37636(6) 0.95377(10) 0.0357(3) Uani 1 1 d . . . . .
O4 O 0.45999(12) 0.22957(7) 0.61591(11) 0.0457(3) Uani 1 1 d . . . . .
H1N H 0.131(2) 0.3139(12) 1.055(2) 0.056(6) Uiso 1 1 d . . . . .
H2N H 0.278(2) 0.3567(13) 1.125(2) 0.057(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(2) . ?
C1 C6 1.378(2) . ?
C1 N1 1.4708(19) . ?
C2 C3 1.387(2) . ?
C3 C4 1.389(2) . ?
C4 C5 1.399(2) . ?
C4 C7 1.5388(19) . ?
C5 C6 1.386(2) . ?
C7 C8 1.5101(18) . ?
C7 C15 1.5159(19) . ?
C8 C13 1.3421(19) . ?
C8 C9 1.4658(18) . ?
C9 O4 1.2284(18) . ?
C9 C10 1.508(2) . ?
C10 C11 1.531(2) . ?
C11 C17 1.525(2) . ?
C11 C18 1.532(2) . ?
C11 C12 1.5362(19) . ?
C12 C13 1.4870(19) . ?
C13 O3 1.3729(16) . ?
C14 N3 1.3392(18) . ?
C14 C15 1.356(2) . ?
C14 O3 1.3712(16) . ?
C15 C16 1.4202(19) . ?
C16 N2 1.150(2) . ?
N1 O1 1.2100(19) . ?
N1 O2 1.211(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.09(14) . . ?
C2 C1 N1 118.79(13) . . ?
C6 C1 N1 119.12(13) . . ?
C1 C2 C3 118.59(14) . . ?
C2 C3 C4 121.54(14) . . ?
C3 C4 C5 117.96(13) . . ?
C3 C4 C7 121.21(12) . . ?
C5 C4 C7 120.82(12) . . ?
C6 C5 C4 121.23(14) . . ?
C1 C6 C5 118.59(14) . . ?
C8 C7 C15 107.76(11) . . ?
C8 C7 C4 112.09(11) . . ?
C15 C7 C4 113.65(11) . . ?
C13 C8 C9 117.76(12) . . ?
C13 C8 C7 121.35(12) . . ?
C9 C8 C7 120.73(12) . . ?
O4 C9 C8 120.64(13) . . ?
O4 C9 C10 121.22(12) . . ?
C8 C9 C10 118.06(12) . . ?
C9 C10 C11 114.52(12) . . ?
C17 C11 C10 109.83(13) . . ?
C17 C11 C18 109.57(13) . . ?
C10 C11 C18 109.62(12) . . ?
C17 C11 C12 111.43(13) . . ?
C10 C11 C12 107.43(12) . . ?
C18 C11 C12 108.92(13) . . ?
C13 C12 C11 112.55(12) . . ?
C8 C13 O3 122.36(12) . . ?
C8 C13 C12 125.92(12) . . ?
O3 C13 C12 111.72(11) . . ?
N3 C14 C15 128.19(13) . . ?
N3 C14 O3 110.28(12) . . ?
C15 C14 O3 121.53(12) . . ?
C14 C15 C16 118.80(13) . . ?
C14 C15 C7 121.52(12) . . ?
C16 C15 C7 119.68(12) . . ?
N2 C16 C15 178.41(16) . . ?
O1 N1 O2 122.86(15) . . ?
O1 N1 C1 118.74(14) . . ?
O2 N1 C1 118.39(14) . . ?
C14 O3 C13 118.30(11) . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2249462'
loop_
_audit_author_name
_audit_author_address
'Noimur Rahman'
;UM DAE Centre for Excellence in Basic Sciences
India
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Cl N2 O2'
_chemical_formula_weight         328.79

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   9.41130(10)
_cell_length_b                   16.82570(10)
_cell_length_c                   10.91390(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.1240(10)
_cell_angle_gamma                90
_cell_volume                     1600.99(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    42907
_cell_measurement_theta_min      2.6200
_cell_measurement_theta_max      77.1160

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.204
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_T_min  0.68317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.596
_oxdiff_exptl_absorpt_empirical_full_max 2.526
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      298(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            56280
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.104
_diffrn_reflns_theta_max         77.336
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0497419000
_diffrn_orient_matrix_UB_12      -0.0803104000
_diffrn_orient_matrix_UB_13      0.0387930000
_diffrn_orient_matrix_UB_21      0.0952264000
_diffrn_orient_matrix_UB_22      -0.0439613000
_diffrn_orient_matrix_UB_23      -0.0667708000
_diffrn_orient_matrix_UB_31      0.1402940000
_diffrn_orient_matrix_UB_32      0.0013488000
_diffrn_orient_matrix_UB_33      0.1313434000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  56.50   0.50    0.20    --   54.00  79.00 -56.08   51
  2  ω     36.00  71.50   0.50    0.20    --   48.29  37.00-120.00   71
  3  ω     76.00 110.00   0.50    0.20    --   48.29  37.00-120.00   68
  4  ω     94.00 119.50   0.50    0.20    --   54.00  79.00 -56.08   51
  5  ω    100.80 126.30   0.50    0.20    --   54.00  80.00 -27.29   51
  6  ω     85.00 111.00   0.50    0.20    --   54.00  78.00   7.50   52
  7  ω    116.00 142.00   0.50    0.80    --  107.75 133.00  63.00   52
  8  ω    124.00 150.00   0.50    0.80    --  107.75  77.00  90.00   52
  9  ω    143.00 171.00   0.50    0.80    --  107.75  77.00 120.00   56
 10  ω    126.00 168.00   0.50    0.80    --  107.75  77.00 150.00   84
 11  ω     85.00 137.00   0.50    0.80    --  107.75  77.00  30.00  104
 12  ω    144.00 175.50   0.50    0.80    --  107.75  77.00   0.00   63
 13  ω    132.00 174.00   0.50    0.80    --  107.75  77.00 -60.00   84
 14  ω    142.00 176.00   0.50    0.80    --  107.75  77.00-120.00   68
 15  ω    132.00 170.00   0.50    0.80    --  107.75  45.00-150.00   76
 16  ω    120.00 146.00   0.50    0.80    --  107.75  77.00-180.00   52
 17  ω    119.00 176.50   0.50    0.80    --  107.75  77.00-150.00  115
 18  ω    149.00 175.00   0.50    0.80    --  107.75 125.00-150.00   52
 19  ω    129.00 175.00   0.50    0.80    --  107.75 125.00 -90.00   92
 20  ω    129.00 177.00   0.50    0.80    --  107.75  77.00 -30.00   96
 21  ω    125.00 172.50   0.50    0.80    --  107.75  45.00   0.00   95
 22  ω    109.00 134.50   0.50    0.80    --  107.75 136.00-119.00   51
 23  ω    105.00 131.00   0.50    0.80    --  107.75 125.00-150.00   52
 24  ω     94.00 176.00   0.50    0.80    --  107.75  77.00 -90.00  164
 25  ω     93.00 149.00   0.50    0.80    --  107.75  61.00 -30.00  112
 26  ω     92.00 145.50   0.50    0.80    --  107.75  61.00 -90.00  107
 27  ω     91.00 165.00   0.50    0.80    --  107.75  61.00-180.00  148
 28  ω     86.00 125.50   0.50    0.80    --  107.75  77.00 -60.00   79
 29  ω     85.00 124.50   0.50    0.80    --  107.75  77.00 -30.00   79
 30  ω     94.00 163.50   0.50    0.80    --  107.75  61.00  30.00  139
 31  ω     93.00 118.50   0.50    0.80    --  107.75  77.00  90.00   51
 32  ω     93.00 173.00   0.50    0.80    --  107.75  61.00 150.00  160
 33  ω     93.00 167.00   0.50    0.80    --  107.75  61.00 120.00  148
 34  ω     85.00 136.50   0.50    0.80    --  107.75  77.00 120.00  103
 35  ω     96.00 172.00   0.50    0.80    --  107.75  61.00  90.00  152
 36  ω     91.00 155.00   0.50    0.80    --  107.75  61.00 -60.00  128
 37  ω     86.00 116.00   0.50    0.80    --  107.75  77.00-180.00   60
 38  ω     86.00 114.00   0.50    0.80    --  107.75  77.00-150.00   56
 39  ω     85.00 127.00   0.50    0.80    --  107.75  77.00-120.00   84
 40  ω     93.00 133.00   0.50    0.80    --  107.75  61.00-150.00   80
 41  ω     79.00 155.00   0.50    0.80    --  102.00  79.00-138.57  152
 42  ω     91.00 126.50   0.50    0.80    --  107.75  61.00   0.00   71
 43  ω     91.00 175.00   0.50    0.80    --  107.75  61.00  60.00  168
 44  ω     86.00 115.50   0.50    0.80    --  107.75  77.00 150.00   59
 45  ω     72.00 129.50   0.50    0.20    --   58.00  80.00 135.85  115
 46  ω     85.00 143.00   0.50    0.80    --  107.75  77.00  60.00  116
 47  ω     85.00 132.50   0.50    0.80    --  107.75  77.00   0.00   95
 48  ω     64.00  90.00   0.50    0.20    --   54.00  80.00-121.53   52
 49  ω     37.00  72.50   0.50    0.20    --   58.00  74.00 -77.91   71
 50  ω     41.00  68.50   0.50    0.20    --   62.00  72.00-105.59   55
 51  ω     30.00  55.50   0.50    0.20    --   54.00  80.00-121.53   51
 52  ω     39.00  64.50   0.50    0.20    --   62.00  79.00-174.36   51
 53  ω     41.00  66.50   0.50    0.20    --   62.00  74.00-177.90   51
 54  ω     10.00  35.50   0.50    0.20    --   38.00  88.00 -91.78   51
 55  ω     30.00  55.50   0.50    0.20    --   54.00  80.00 -27.29   51
 56  ω     39.00  69.00   0.50    0.20    --   58.00  72.00 -13.71   60
 57  ω     41.00  67.00   0.50    0.20    --   62.00  73.00   9.53   52
 58  ω     30.00  68.00   0.50    0.20    --   54.00  80.00  30.00   76
 59  ω     42.00  67.50   0.50    0.20    --   62.00  72.00  90.89   51
 60  ω     39.00  64.50   0.50    0.20    --   62.00  78.00 106.72   51
 61  ω     34.00  59.50   0.50    0.20    --   58.00  80.00 135.85   51
 62  ω     39.00 122.50   0.50    0.20    --   48.29  19.00 120.00  167
 63  ω     40.00  66.00   0.50    0.80    --  107.75 -94.00   0.00   52
 64  ω     75.00 101.00   0.50    0.80    --  107.75 -94.00   0.00   52
 65  ω     80.00 117.50   0.50    0.80    --  107.75-133.00  -5.00   75
 66  ω     79.00 108.50   0.50    0.80    --  107.75-125.00 -60.00   59
 67  ω     82.00 111.50   0.50    0.80    --  107.75-125.00 -30.00   59
 68  ω     70.00 111.50   0.50    0.80    --  107.75-125.00 -90.00   83
 69  ω     48.00 109.50   0.50    0.80    --  107.75-125.00  30.00  123
 70  ω     84.00 110.00   0.50    0.80    --  107.75-125.00  90.00   52
 71  ω     71.00 119.00   0.50    0.80    --  107.75-136.00 176.00   96
 72  ω     59.00  99.00   0.50    0.80    --  107.75 -94.00 150.00   80
 73  ω     54.00 111.50   0.50    0.80    --  107.75-125.00 150.00  115
 74  ω     41.00  98.50   0.50    0.20    --   48.29-136.00 176.00  115
 75  ω     35.00  96.50   0.50    0.80    --  107.75 -94.00  90.00  123
 76  ω     42.00 107.50   0.50    0.80    --  107.75-125.00   0.00  131
 77  ω     40.00  99.50   0.50    0.20    --   48.29-133.00  -5.00  119
 78  ω     39.00  69.00   0.50    0.80    --  107.75 -77.00 -90.00   60
 79  ω     42.00  67.50   0.50    0.80    --  107.75 -61.00-150.00   51
 80  ω     37.00  91.00   0.50    0.80    --  107.75 -77.00-150.00  108
 81  ω     35.00  60.50   0.50    0.80    --  107.75 -61.00-120.00   51
 82  ω     39.00  83.00   0.50    0.80    --  107.75 -77.00-180.00   88
 83  ω     35.00  60.50   0.50    0.80    --  107.75-125.00 -90.00   51
 84  ω     38.00  63.50   0.50    0.80    --  107.75-125.00 -60.00   51
 85  ω     35.00  88.50   0.50    0.80    --  107.75 -77.00  30.00  107
 86  ω     38.00  64.00   0.50    0.80    --  107.75 -61.00  30.00   52
 87  ω     37.00 105.00   0.50    0.80    --  107.75 -94.00  30.00  136
 88  ω     35.00  68.50   0.50    0.80    --  107.75 -61.00 -90.00   67
 89  ω     45.00  70.50   0.50    0.80    --  107.75 -61.00 -30.00   51
 90  ω     43.00 103.00   0.50    0.80    --  107.75 -94.00-180.00  120
 91  ω     12.00  38.00   0.50    0.20    --   38.00  91.00  35.42   52
 92  ω     32.00  57.50   0.50    0.20    --   54.00  78.00   7.50   51
 93  ω      7.00  32.50   0.50    0.20    --   38.00  94.00   6.10   51
 94  ω    -11.00  23.00   0.50    0.20    --   18.00  95.00  -6.41   68
 95  ω     12.00  37.50   0.50    0.20    --   38.00  84.00 148.18   51
 96  ω    -15.00  17.00   0.50    0.20    --   18.00  98.00 166.02   64
 97  ω    -62.00 -37.50   0.50    0.20    --  -48.29 133.00  63.00   49
 98  ω    -78.00 -53.50   0.50    0.80    --  -86.25 133.00  63.00   49
 99  ω    -80.00 -55.50   0.50    0.20    --  -48.29 136.00-119.00   49
100  ω    -73.00 -47.50   0.50    0.20    --  -66.00 -67.00-126.04   51
101  ω    -58.00 -32.00   0.50    0.20    --  -54.00 -76.00-141.60   52
102  ω    -70.00 -44.00   0.50    0.20    --  -66.00 -79.00-172.51   52
103  ω    -78.00 -52.50   0.50    0.80    --  -70.00 -64.00 -95.39   51
104  ω    -76.00 -50.50   0.50    0.80    --  -74.00 -79.00-136.70   51
105  ω    -85.00 -59.50   0.50    0.80    --  -82.00 -77.00-102.75   51
106  ω    -86.00 -60.00   0.50    0.80    --  -82.00 -78.00 -67.35   52
107  ω    -81.00 -55.50   0.50    0.80    --  -78.00 -76.00 -36.64   51
108  ω    -63.00 -37.50   0.50    0.20    --  -58.00 -73.00   9.68   51
109  ω    -71.00 -27.00   0.50    0.20    --  -48.29 -77.00  60.00   88
110  ω    -78.00 -52.50   0.50    0.80    --  -70.00 -68.00  67.07   51
111  ω    -76.20 -50.70   0.50    0.80    --  -70.00 -68.00 114.58   51
112  ω    -77.00 -51.50   0.50    0.80    --  -70.00 -67.00  44.50   51
113  ω    -81.00 -55.50   0.50    0.80    --  -74.00 -65.00  -2.13   51
114  ω    -85.00 -59.50   0.50    0.80    --  -82.00 -77.00   9.29   51
115  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  30.00   51
116  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  90.00   51
117  ω    -86.00 -60.50   0.50    0.80    --  -78.00 -71.00 144.02   51
118  ω    -81.00 -55.50   0.50    0.80    --  -74.00 -66.00 163.42   51
119  ω    -91.00 -65.50   0.50    0.80    --  -86.25 -72.00 127.98   51
120  ω    -92.00 -64.50   0.50    0.80    --  -86.25 -74.00 160.54   55
121  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00 120.00   51
122  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  60.00   51
123  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00   0.00   51
124  ω    -89.00 -63.00   0.50    0.80    --  -86.25 -80.00 -32.19   52
125  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00 -90.00   51
126  ω    -95.00 -69.50   0.50    0.80    --  -86.25 -62.00 -99.98   51
127  ω    -90.00 -64.00   0.50    0.80    --  -86.25 -77.00-150.00   52
128  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00-180.00   51
129  ω    -97.00 -67.00   0.50    0.80    --  -86.25 -75.00-115.04   60
130  ω    -90.00 -64.50   0.50    0.80    --  -86.25 -75.00 -48.11   51
131  ω    -87.00 -62.50   0.50    0.80    --  -86.25 -80.00-133.45   49
132  ω   -108.00 -68.50   0.50    0.20    --  -48.29-133.00  -5.00   79
133  ω   -118.00 -92.50   0.50    0.20    --  -48.29-136.00 176.00   51
134  ω   -136.00-111.50   0.50    0.80    --  -86.25-136.00 176.00   49
135  ω   -146.00 -60.50   0.50    0.80    --  -78.00 -64.00  14.83  171
136  ω   -137.00-112.50   0.50    0.80    --  -86.25-133.00  -5.00   49
137  ω   -133.00 -67.50   0.50    0.80    --  -86.25 -67.00 -29.04  131
138  ω   -135.00-109.00   0.50    0.20    --  -66.00 -79.00-172.51   52
139  ω   -159.00-133.00   0.50    0.80    --  -86.25 -77.00-150.00   52
;
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_digest_frames     
;
0182ab7078d715560ade0a0830909ca45c0003686e3
;
_diffrn_oxdiff_digest_hkl        
;
01b80112dee8ee39c9738f5fea6c80a777c7c6
;
_reflns_number_total             3363
_reflns_number_gt                2879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep 3 for windows'
_computing_publication_material  'WinGX 2021.3'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+1.2500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3363
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.2959
_refine_ls_wR_factor_gt          0.1908
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.19708(12) 0.47008(6) 0.23003(9) 0.0703(4) Uani 1 1 d . . . . .
O1 O 0.3735(2) 0.37284(12) 0.92772(19) 0.0395(5) Uani 1 1 d . . . . .
O2 O 0.4714(3) 0.24235(14) 0.5875(2) 0.0527(6) Uani 1 1 d . . . . .
N2 N 0.2122(3) 0.33091(18) 1.0192(3) 0.0453(6) Uani 1 1 d . . . . .
C8 C 0.3999(3) 0.31468(16) 0.7387(3) 0.0352(6) Uani 1 1 d . . . . .
C4 C 0.1278(3) 0.32815(16) 0.5740(3) 0.0367(6) Uani 1 1 d . . . . .
C14 C 0.2534(3) 0.32256(16) 0.9152(3) 0.0352(6) Uani 1 1 d . . . . .
C13 C 0.4530(3) 0.36039(16) 0.8468(3) 0.0347(6) Uani 1 1 d . . . . .
C7 C 0.2395(3) 0.27992(16) 0.6899(3) 0.0353(6) Uani 1 1 d . . . . .
H7 H 0.244119 0.225703 0.658840 0.042 Uiso 1 1 calc R U . . .
C15 C 0.1919(3) 0.27530(17) 0.8081(3) 0.0372(6) Uani 1 1 d . . . . .
C9 C 0.5066(3) 0.29275(17) 0.6746(3) 0.0405(6) Uani 1 1 d . . . . .
N1 N -0.0235(4) 0.17880(19) 0.7986(3) 0.0610(8) Uani 1 1 d . . . . .
C16 C 0.0739(3) 0.22132(18) 0.8043(3) 0.0431(7) Uani 1 1 d . . . . .
C11 C 0.6708(3) 0.41211(18) 0.7893(3) 0.0434(7) Uani 1 1 d . . . . .
C12 C 0.6017(3) 0.40362(19) 0.8959(3) 0.0438(7) Uani 1 1 d . . . . .
H12A H 0.673629 0.375357 0.971236 0.053 Uiso 1 1 calc R U . . .
H12B H 0.586360 0.456076 0.925704 0.053 Uiso 1 1 calc R U . . .
C1 C -0.0732(4) 0.41515(18) 0.3617(3) 0.0465(7) Uani 1 1 d . . . . .
C10 C 0.6636(4) 0.33014(19) 0.7259(4) 0.0495(8) Uani 1 1 d . . . . .
H10A H 0.698589 0.335157 0.653236 0.059 Uiso 1 1 calc R U . . .
H10B H 0.734011 0.294805 0.790845 0.059 Uiso 1 1 calc R U . . .
C3 C -0.0064(3) 0.3600(2) 0.5774(3) 0.0466(7) Uani 1 1 d . . . . .
H3 H -0.029618 0.352180 0.652130 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1597(4) 0.3416(2) 0.4602(3) 0.0489(7) Uani 1 1 d . . . . .
H5 H 0.249227 0.321030 0.455539 0.059 Uiso 1 1 calc R U . . .
C6 C 0.0605(5) 0.3848(2) 0.3547(3) 0.0544(8) Uani 1 1 d . . . . .
H6 H 0.083370 0.393295 0.279941 0.065 Uiso 1 1 calc R U . . .
C2 C -0.1071(4) 0.4032(2) 0.4724(4) 0.0540(8) Uani 1 1 d . . . . .
H2 H -0.196711 0.423838 0.476816 0.065 Uiso 1 1 calc R U . . .
C18 C 0.8383(4) 0.4399(3) 0.8562(4) 0.0622(10) Uani 1 1 d . . . . .
H18A H 0.883944 0.443740 0.791193 0.093 Uiso 1 1 calc R U . . .
H18B H 0.894542 0.402258 0.922975 0.093 Uiso 1 1 calc R U . . .
H18C H 0.840858 0.490971 0.896137 0.093 Uiso 1 1 calc R U . . .
C17 C 0.5811(5) 0.4720(2) 0.6834(4) 0.0617(10) Uani 1 1 d . . . . .
H17A H 0.581360 0.522669 0.723890 0.093 Uiso 1 1 calc R U . . .
H17B H 0.477297 0.453907 0.640253 0.093 Uiso 1 1 calc R U . . .
H17C H 0.628071 0.477019 0.619531 0.093 Uiso 1 1 calc R U . . .
H1N H 0.138(5) 0.301(2) 1.027(4) 0.050(10) Uiso 1 1 d . . . . .
H2N H 0.282(6) 0.347(3) 1.088(5) 0.065(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.737(3) . ?
O1 C13 1.372(3) . ?
O1 C14 1.377(3) . ?
O2 C9 1.223(4) . ?
N2 C14 1.338(4) . ?
N2 H1N 0.89(4) . ?
N2 H2N 0.83(5) . ?
C8 C13 1.337(4) . ?
C8 C9 1.471(4) . ?
C8 C7 1.516(4) . ?
C4 C3 1.386(4) . ?
C4 C5 1.401(4) . ?
C4 C7 1.537(4) . ?
C14 C15 1.350(4) . ?
C13 C12 1.486(4) . ?
C7 C15 1.518(4) . ?
C7 H7 0.9800 . ?
C15 C16 1.423(4) . ?
C9 C10 1.506(4) . ?
N1 C16 1.146(4) . ?
C11 C17 1.526(5) . ?
C11 C10 1.533(4) . ?
C11 C18 1.539(4) . ?
C11 C12 1.539(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C1 C2 1.377(5) . ?
C1 C6 1.387(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 C2 1.385(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C13 O1 C14 117.9(2) . . ?
C14 N2 H1N 121(3) . . ?
C14 N2 H2N 114(3) . . ?
H1N N2 H2N 119(4) . . ?
C13 C8 C9 117.9(2) . . ?
C13 C8 C7 121.6(2) . . ?
C9 C8 C7 120.3(2) . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 C7 122.0(2) . . ?
C5 C4 C7 120.4(3) . . ?
N2 C14 C15 129.0(3) . . ?
N2 C14 O1 109.9(2) . . ?
C15 C14 O1 121.1(2) . . ?
C8 C13 O1 122.8(2) . . ?
C8 C13 C12 126.0(2) . . ?
O1 C13 C12 111.1(2) . . ?
C8 C7 C15 107.1(2) . . ?
C8 C7 C4 111.5(2) . . ?
C15 C7 C4 113.4(2) . . ?
C8 C7 H7 108.2 . . ?
C15 C7 H7 108.2 . . ?
C4 C7 H7 108.2 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 C7 122.5(2) . . ?
C16 C15 C7 119.0(3) . . ?
O2 C9 C8 120.7(3) . . ?
O2 C9 C10 121.3(3) . . ?
C8 C9 C10 117.9(3) . . ?
N1 C16 C15 178.3(4) . . ?
C17 C11 C10 109.5(3) . . ?
C17 C11 C18 109.6(3) . . ?
C10 C11 C18 110.5(3) . . ?
C17 C11 C12 111.3(3) . . ?
C10 C11 C12 107.4(2) . . ?
C18 C11 C12 108.6(3) . . ?
C13 C12 C11 112.4(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 Cl1 119.9(3) . . ?
C6 C1 Cl1 119.4(3) . . ?
C9 C10 C11 114.4(2) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.538
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.132

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2249463'
loop_
_audit_author_name
_audit_author_address
'Noimur Rahman'
;UM DAE Centre for Excellence in Basic Sciences
India
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   15.84440(10)
_cell_length_b                   6.53500(10)
_cell_length_c                   16.25570(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.6360(10)
_cell_angle_gamma                90
_cell_volume                     1664.08(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    36083
_cell_measurement_theta_min      2.7730
_cell_measurement_theta_max      76.9090

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.643
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_T_min  0.52016
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.578
_oxdiff_exptl_absorpt_empirical_full_max 1.807
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      298(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            45459
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.632
_diffrn_reflns_theta_max         77.073
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0386305000
_diffrn_orient_matrix_UB_12      0.1937927000
_diffrn_orient_matrix_UB_13      0.0447434000
_diffrn_orient_matrix_UB_21      -0.0409468000
_diffrn_orient_matrix_UB_22      -0.0568257000
_diffrn_orient_matrix_UB_23      0.0770793000
_diffrn_orient_matrix_UB_31      0.0806342000
_diffrn_orient_matrix_UB_32      -0.1216543000
_diffrn_orient_matrix_UB_33      0.0352876000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  53.00   0.50    0.19    --   48.17  77.00   0.00   52
  2  ω     34.00  60.00   0.50    0.19    --   58.00  79.00   9.12   52
  3  ω     42.00  86.00   0.50    0.19    --   62.00  74.00 -22.08   88
  4  ω     42.00  68.00   0.50    0.19    --   66.00  79.00 -94.80   52
  5  ω     38.00  69.00   0.50    0.19    --   58.00  70.00 -34.12   62
  6  ω     51.00  77.00   0.50    0.19    --   74.00  78.00 -33.36   52
  7  ω    105.00 156.00   0.50    0.78    --  107.39  94.00 -64.00  102
  8  ω    147.00 178.00   0.50    0.78    --  107.39  77.00   0.00   62
  9  ω    143.00 177.00   0.50    0.78    --  107.39  37.00  60.00   68
 10  ω    108.00 178.00   0.50    0.78    --  107.39  19.00   0.00  140
 11  ω    104.00 135.00   0.50    0.19    --   62.00  80.00 117.49   62
 12  ω    102.00 135.00   0.50    0.78    --  107.39  37.00  60.00   66
 13  ω    105.00 176.00   0.50    0.78    --  107.39  57.00 120.00  142
 14  ω     96.00 176.00   0.50    0.78    --  107.39  37.00  90.00  160
 15  ω     95.00 153.00   0.50    0.78    --  107.39  57.00 -60.00  116
 16  ω    107.00 133.00   0.50    0.19    --   70.00  77.00-140.14   52
 17  ω     91.00 126.00   0.50    0.19    --   54.00  76.00-174.23   70
 18  ω     94.00 178.00   0.50    0.78    --  107.39  57.00 -90.00  168
 19  ω    100.00 176.00   0.50    0.78    --  107.39  37.00-120.00  152
 20  ω     87.00 129.00   0.50    0.78    --  107.39  77.00   0.00   84
 21  ω     50.00  77.00   0.50    0.19    --   70.00  77.00-140.14   54
 22  ω     39.00  81.00   0.50    0.19    --   58.00  73.00-149.34   84
 23  ω     38.00  64.00   0.50    0.19    --   62.00  79.00-107.23   52
 24  ω     45.00  70.00   0.50    0.19    --   66.00  73.00-141.86   50
 25  ω     30.00  55.00   0.50    0.19    --   54.00  79.00-100.79   50
 26  ω     28.00  54.00   0.50    0.19    --   48.17  77.00-120.00   52
 27  ω     32.00  77.00   0.50    0.19    --   54.00  75.00 -58.80   90
 28  ω     27.00  69.00   0.50    0.19    --   50.00  78.00  26.97   84
 29  ω     38.00  64.00   0.50    0.19    --   62.00  80.00  39.97   52
 30  ω     34.00  61.00   0.50    0.19    --   58.00  79.00  80.11   54
 31  ω     43.00  69.00   0.50    0.19    --   66.00  77.00  57.26   52
 32  ω     38.00  63.00   0.50    0.19    --   62.00  80.00 117.49   50
 33  ω     73.00 165.00   0.50    0.78    --   94.00  74.00 165.82  184
 34  ω     36.00  65.00   0.50    0.78    --  107.39 -57.00 120.00   58
 35  ω     36.00 106.00   0.50    0.78    --  107.39 -99.00  60.00  140
 36  ω     71.00 105.00   0.50    0.78    --  107.39-125.00 120.00   68
 37  ω     38.00  63.00   0.50    0.78    --  107.39 -57.00   0.00   50
 38  ω     36.00 103.00   0.50    0.78    --  107.39 -99.00 -30.00  134
 39  ω     76.00 106.00   0.50    0.78    --  107.39 -99.00 -90.00   60
 40  ω     58.00 109.00   0.50    0.78    --  107.39-125.00 -90.00  102
 41  ω     59.00 100.00   0.50    0.78    --  107.39 -99.00-180.00   82
 42  ω     45.00  71.00   0.50    0.78    --  107.39 -94.00-175.00   52
 43  ω     41.00  66.00   0.50    0.78    --  107.39 -57.00-120.00   50
 44  ω     35.00  65.00   0.50    0.78    --  107.39 -57.00 -60.00   60
 45  ω     39.00  64.00   0.50    0.78    --  107.39 -57.00 -30.00   50
 46  ω     36.00  61.00   0.50    0.78    --  107.39 -57.00  30.00   50
 47  ω     53.00 103.00   0.50    0.78    --  107.39 -99.00   0.00  100
 48  ω     37.00  64.00   0.50    0.78    --  107.39-125.00 120.00   54
 49  ω     36.00 107.00   0.50    0.78    --  107.39-106.00 140.96  142
 50  ω     41.00  66.00   0.50    0.78    --  107.39 -57.00  60.00   50
 51  ω     35.00  66.00   0.50    0.78    --  107.39 -57.00 150.00   62
 52  ω      0.00  25.00   0.50    0.19    --   22.00  88.00  76.16   50
 53  ω     13.00  38.00   0.50    0.19    --   42.00  91.00  84.18   50
 54  ω    -18.00  13.00   0.50    0.19    --   14.00 102.00  64.14   62
 55  ω    -62.00  -5.00   0.50    0.19    --  -48.17  94.00 -64.00  114
 56  ω      4.00  41.00   0.50    0.19    --   48.17 -37.00-120.00   74
 57  ω    -11.00  78.00   0.50    0.19    --   48.17 -94.00-175.00  178
 58  ω     39.00  72.00   0.50    0.78    --  107.39 -99.00 -90.00   66
 59  ω     32.00  63.00   0.50    0.19    --   54.00  76.00-174.23   62
 60  ω      8.00  40.00   0.50    0.19    --   38.00  92.00-174.72   64
 61  ω    -42.00 -16.00   0.50    0.19    --    6.00 130.00-109.41   52
 62  ω    -26.00  21.00   0.50    0.19    --  -48.17  19.00-150.00   94
 63  ω    -39.00 -13.00   0.50    0.78    --  -86.25  37.00-120.00   52
 64  ω    -62.00 -32.00   0.50    0.78    --  -86.25  57.00 -30.00   60
 65  ω    -71.00 -46.00   0.50    0.78    --  -86.25  94.00 -64.00   50
 66  ω    -94.00 -54.00   0.50    0.19    --  -48.17 -19.00-180.00   80
 67  ω    -76.00 -51.00   0.50    0.78    --  -74.00 -77.00-111.08   50
 68  ω    -91.00 -44.00   0.50    0.19    --  -48.17 -37.00 -60.00   94
 69  ω    -80.00 -55.00   0.50    0.78    --  -74.00 -68.00 -17.44   50
 70  ω    -82.00 -57.00   0.50    0.78    --  -78.00 -75.00 -81.03   50
 71  ω    -87.00 -62.00   0.50    0.78    --  -86.25 -79.00 -43.66   50
 72  ω    -92.00 -63.00   0.50    0.78    --  -86.25 -77.00 -30.00   58
 73  ω    -92.00 -66.00   0.50    0.78    --  -86.25 -72.00 -20.20   52
 74  ω    -97.00 -63.00   0.50    0.78    --  -86.25 -77.00 -60.00   68
 75  ω   -101.00 -66.00   0.50    0.78    --  -86.25 -77.00 -90.00   70
 76  ω    -96.00 -65.00   0.50    0.78    --  -86.25 -74.00-120.53   62
 77  ω    -89.00 -64.00   0.50    0.78    --  -86.25 -76.00-165.13   50
 78  ω   -108.00 -65.00   0.50    0.78    --  -86.25 -72.00-177.66   86
 79  ω   -112.00 -70.00   0.50    0.78    --  -86.25 -71.00-132.68   84
 80  ω   -137.00-107.00   0.50    0.78    --  -78.00 -75.00 -81.03   60
 81  ω   -134.00 -65.00   0.50    0.78    --  -86.25 -73.00-144.16  138
 82  ω   -133.00-108.00   0.50    0.78    --  -86.25 -76.00-165.13   50
 83  ω   -145.00-120.00   0.50    0.78    --  -86.25 -94.00-175.00   50
 84  ω   -156.00-121.00   0.50    0.78    --  -86.25 -71.00-132.68   70
 85  ω   -145.00-119.00   0.50    0.78    --  -86.25 -77.00 -90.00   52
 86  ω   -141.00-115.00   0.50    0.78    --  -86.25 -77.00 -60.00   52
 87  ω    -94.00 -63.00   0.50    0.78    --  -86.25 -77.00   0.00   62
 88  ω    -93.00 -64.00   0.50    0.78    --  -86.25 -76.00  61.26   58
 89  ω    -77.00 -52.00   0.50    0.78    --  -74.00 -75.00  76.77   50
 90  ω    -50.00 -25.00   0.50    0.19    --  -48.17 -77.00 120.00   50
 91  ω    -76.00 -51.00   0.50    0.78    --  -74.00 -76.00 112.00   50
 92  ω    -87.00 -62.00   0.50    0.19    --  -48.17 -77.00 120.00   50
 93  ω    -83.00 -58.00   0.50    0.78    --  -78.00 -74.00 153.18   50
 94  ω    -85.00 -60.00   0.50    0.78    --  -82.00 -74.00 169.82   50
 95  ω    -91.00 -65.00   0.50    0.78    --  -86.25 -77.00 150.00   52
 96  ω    -92.00 -66.00   0.50    0.78    --  -86.25 -70.00 100.65   52
 97  ω    -85.00 -60.00   0.50    0.78    --  -82.00 -77.00  81.45   50
 98  ω    -99.00 -70.00   0.50    0.78    --  -86.25 -73.00  76.53   58
 99  ω    -93.00 -64.00   0.50    0.78    --  -86.25 -76.00 120.83   58
100  ω    -93.00 -65.00   0.50    0.78    --  -86.25 -74.00 168.24   56
101  ω    -89.00 -64.00   0.50    0.78    --  -86.25 -75.00  96.02   50
102  ω   -102.00 -65.00   0.50    0.78    --  -86.25 -76.00  48.35   74
103  ω   -109.00 -63.00   0.50    0.78    --  -86.25 -77.00  30.00   92
104  ω   -115.00 -67.00   0.50    0.78    --  -86.25 -73.00 132.37   96
105  ω   -130.00-104.00   0.50    0.78    --  -86.25 -75.00  96.02   52
106  ω   -159.00-133.00   0.50    0.78    --  -86.25 -77.00   0.00   52
107  ω   -156.00-131.00   0.50    0.78    --  -86.25 -76.00  48.35   50
108  ω   -155.00-115.00   0.50    0.78    --  -86.25 -73.00  76.53   80
109  ω   -155.00-129.00   0.50    0.78    --  -86.25 -77.00 150.00   52
110  ω   -152.00-113.00   0.50    0.78    --  -86.25 -70.00 100.65   78
111  ω   -154.00-128.00   0.50    0.78    --  -86.25 -76.00  61.26   52
112  ω   -154.00-129.00   0.50    0.78    --  -86.25 -77.00  30.00   50
113  ω   -156.00-131.00   0.50    0.78    --  -86.25 -79.00 -43.66   50
;
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_digest_frames     
;
0186c931aec372f5da699b8684d38a3415000374315
;
_diffrn_oxdiff_digest_hkl        
;
0174032e5e99c36a0b4b8ce20f6f75eae46bbf
;
_reflns_number_total             3468
_reflns_number_gt                3067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep 3 for windows'
_computing_publication_material  'WinGX 2021.3'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1875P)²+0.4091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0056(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3468
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2688
_refine_ls_wR_factor_gt          0.2053
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58510(10) 0.1127(2) 0.78338(9) 0.0451(4) Uani 1 1 d . . . . .
O2 O 0.56402(10) 0.6094(2) 0.57040(9) 0.0473(4) Uani 1 1 d . . . . .
N2 N 0.56818(13) 0.1589(3) 0.91562(11) 0.0455(5) Uani 1 1 d . . . . .
C4 C 0.43104(11) 0.5556(3) 0.69818(10) 0.0341(4) Uani 1 1 d . . . . .
C8 C 0.56723(11) 0.3714(3) 0.67827(11) 0.0328(4) Uani 1 1 d . . . . .
C7 C 0.52537(11) 0.5200(3) 0.73063(10) 0.0322(4) Uani 1 1 d . . . . .
H006 H 0.555029 0.651565 0.730360 0.039 Uiso 1 1 calc R U . . .
N1 N 0.50508(16) 0.6909(3) 0.93192(11) 0.0590(6) Uani 1 1 d . . . . .
C14 C 0.56131(11) 0.2468(3) 0.84058(10) 0.0345(4) Uani 1 1 d . . . . .
C15 C 0.53732(11) 0.4413(3) 0.81939(11) 0.0329(4) Uani 1 1 d . . . . .
C16 C 0.51866(13) 0.5756(3) 0.88222(11) 0.0389(5) Uani 1 1 d . . . . .
C13 C 0.59490(12) 0.1864(3) 0.70581(11) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.58048(11) 0.4349(3) 0.59408(11) 0.0354(4) Uani 1 1 d . . . . .
C11 C 0.68034(12) 0.1353(3) 0.58895(12) 0.0412(5) Uani 1 1 d . . . . .
C3 C 0.39549(13) 0.7467(3) 0.70655(13) 0.0448(5) Uani 1 1 d . . . . .
H3 H 0.430063 0.854390 0.728581 0.054 Uiso 1 1 calc R U . . .
C5 C 0.37775(13) 0.3989(3) 0.66360(13) 0.0439(5) Uani 1 1 d . . . . .
H5 H 0.400430 0.269815 0.656797 0.053 Uiso 1 1 calc R U . . .
C12 C 0.63967(16) 0.0356(3) 0.65852(13) 0.0480(5) Uani 1 1 d . . . . .
H12B H 0.599126 -0.067287 0.634631 0.058 Uiso 1 1 calc R U . . .
H12A H 0.683696 -0.032736 0.696669 0.058 Uiso 1 1 calc R U . . .
C10 C 0.61367(14) 0.2751(3) 0.53980(12) 0.0441(5) Uani 1 1 d . . . . .
H10B H 0.638815 0.342948 0.496251 0.053 Uiso 1 1 calc R U . . .
H10A H 0.566284 0.192733 0.513423 0.053 Uiso 1 1 calc R U . . .
C1 C 0.25512(13) 0.6239(4) 0.64841(13) 0.0507(6) Uani 1 1 d . . . . .
C6 C 0.29126(14) 0.4327(4) 0.63914(14) 0.0514(6) Uani 1 1 d . . . . .
H6 H 0.256780 0.325835 0.616146 0.062 Uiso 1 1 calc R U . . .
C2 C 0.30851(14) 0.7789(4) 0.68229(14) 0.0532(6) Uani 1 1 d . . . . .
H2 H 0.285805 0.907948 0.689064 0.064 Uiso 1 1 calc R U . . .
C17 C 0.70725(18) -0.0329(4) 0.53221(15) 0.0584(7) Uani 1 1 d . . . . .
H17B H 0.746034 -0.125269 0.564573 0.088 Uiso 1 1 calc R U . . .
H17A H 0.734862 0.028190 0.489599 0.088 Uiso 1 1 calc R U . . .
H17C H 0.657672 -0.106798 0.506979 0.088 Uiso 1 1 calc R U . . .
C18 C 0.75848(15) 0.2623(5) 0.6243(2) 0.0718(8) Uani 1 1 d . . . . .
H18C H 0.741335 0.371149 0.657826 0.108 Uiso 1 1 calc R U . . .
H18B H 0.783951 0.319039 0.579358 0.108 Uiso 1 1 calc R U . . .
H18A H 0.799199 0.176576 0.657776 0.108 Uiso 1 1 calc R U . . .
C19 C 0.16068(16) 0.6571(6) 0.62264(19) 0.0740(9) Uani 1 1 d . . . . .
H19B H 0.151727 0.774716 0.586998 0.111 Uiso 1 1 calc R U . . .
H19A H 0.134059 0.679086 0.671203 0.111 Uiso 1 1 calc R U . . .
H19C H 0.136118 0.538731 0.593320 0.111 Uiso 1 1 calc R U . . .
H1N H 0.5435(18) 0.214(4) 0.9549(18) 0.053(7) Uiso 1 1 d . . . . .
H2N H 0.575(2) 0.033(6) 0.920(2) 0.073(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.371(2) . ?
O1 C13 1.380(2) . ?
O2 C9 1.219(2) . ?
N2 C14 1.338(2) . ?
C4 C3 1.385(3) . ?
C4 C5 1.391(3) . ?
C4 C7 1.526(2) . ?
C8 C13 1.340(2) . ?
C8 C9 1.475(2) . ?
C8 C7 1.509(2) . ?
C7 C15 1.517(2) . ?
N1 C16 1.148(3) . ?
C14 C15 1.356(3) . ?
C15 C16 1.411(2) . ?
C13 C12 1.493(2) . ?
C9 C10 1.512(3) . ?
C11 C18 1.529(3) . ?
C11 C10 1.528(3) . ?
C11 C12 1.529(3) . ?
C11 C17 1.536(3) . ?
C3 C2 1.391(3) . ?
C5 C6 1.386(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.392(3) . ?
C1 C19 1.508(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
C14 O1 C13 118.48(14) . . ?
C3 C4 C5 118.18(18) . . ?
C3 C4 C7 119.65(17) . . ?
C5 C4 C7 122.09(16) . . ?
C13 C8 C9 118.62(16) . . ?
C13 C8 C7 122.81(16) . . ?
C9 C8 C7 118.55(15) . . ?
C8 C7 C15 108.39(14) . . ?
C8 C7 C4 113.17(14) . . ?
C15 C7 C4 110.88(14) . . ?
N2 C14 C15 127.98(17) . . ?
N2 C14 O1 110.53(16) . . ?
C15 C14 O1 121.46(16) . . ?
C14 C15 C16 118.71(16) . . ?
C14 C15 C7 123.35(15) . . ?
C16 C15 C7 117.88(15) . . ?
N1 C16 C15 177.3(2) . . ?
C8 C13 O1 122.95(16) . . ?
C8 C13 C12 125.48(16) . . ?
O1 C13 C12 111.56(15) . . ?
O2 C9 C8 120.18(17) . . ?
O2 C9 C10 122.58(16) . . ?
C8 C9 C10 117.23(16) . . ?
C18 C11 C10 109.2(2) . . ?
C18 C11 C12 111.2(2) . . ?
C10 C11 C12 107.85(16) . . ?
C18 C11 C17 109.38(19) . . ?
C10 C11 C17 110.26(17) . . ?
C12 C11 C17 108.99(17) . . ?
C4 C3 C2 120.6(2) . . ?
C6 C5 C4 120.8(2) . . ?
C13 C12 C11 112.67(16) . . ?
C9 C10 C11 112.44(15) . . ?
C2 C1 C6 117.67(19) . . ?
C2 C1 C19 121.9(2) . . ?
C6 C1 C19 120.4(3) . . ?
C5 C6 C1 121.1(2) . . ?
C1 C2 C3 121.6(2) . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.094

