# 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_exp_793_tp-abc-002a
_database_code_depnum_ccdc_archive 'CCDC 2072747'
loop_
_audit_author_name
_audit_author_address
'Adarash Kumar Shukla'
;bits pilani hyderabad
India
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 N2 O3'
_chemical_formula_sum            'C26 H18 N2 O3'
_chemical_formula_weight         406.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.4393(2)
_cell_length_b                   8.56590(10)
_cell_length_c                   14.2744(4)
_cell_angle_alpha                97.421(2)
_cell_angle_beta                 95.373(2)
_cell_angle_gamma                101.685(2)
_cell_volume                     994.39(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.0150
_cell_measurement_theta_min      5.3750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10645
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.841
_diffrn_reflns_theta_min         5.335
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00   1.00   0.50    1.44    --    0.00  82.00  60.00   66
  2  ω    -20.00  16.00   0.50    1.44    --    0.00 -57.00  30.00   72
  3  ω    -85.00 -49.00   0.50    1.44    --    0.00 -57.00  30.00   72
  4  ω      8.00  75.00   0.50    1.44    --    0.00  82.00  60.00  134
  5  ω    -20.00  29.00   0.50    1.44    --    0.00 -82.00   0.00   98
  6  ω    -84.00 -29.00   0.50    1.44    --    0.00 -82.00   0.00  110
  7  ω     38.00 106.00   0.50    5.75    --  107.20 -61.00 -60.00  136
  8  ω     82.00 159.00   0.50    5.75    --  107.20  15.00   0.00  154
  9  ω     40.00 135.00   0.50    5.75    --  107.20 -82.00-180.00  190
 10  ω     18.00  78.00   0.50    5.75    --  107.20 -77.00 120.00  120
 11  ω     98.00 197.00   0.50    5.75    --  107.20  30.00  30.00  198
 12  ω     62.00 132.00   0.50    5.75    --  107.20 -82.00 -90.00  140
 13  ω    125.00 151.00   0.50    5.75    --  107.20  45.00 -90.00   52
 14  ω    170.00 196.00   0.50    5.75    --  107.20  45.00 -90.00   52
 15  ω     89.00 196.00   0.50    5.75    --  107.20  30.00  60.00  214
 16  ω     85.00 136.00   0.50    5.75    --  107.20 -82.00  60.00  102
 17  ω     35.00  79.00   0.50    5.75    --  107.20 -82.00  60.00   88
 18  ω     37.00  88.00   0.50    5.75    --  107.20 -45.00  30.00  102
 19  ω     19.00 134.00   0.50    5.75    --  107.20 -15.00  60.00  230
 20  ω     84.00 110.00   0.50    5.75    --  107.20 -82.00-150.00   52
 21  ω     23.00 130.00   0.50    5.75    --  107.20 -61.00-180.00  214
 22  ω     79.00 104.00   0.50    5.75    --  107.20 -82.00 -60.00   50
 23  ω     35.00 120.00   0.50    5.75    --  107.20 -82.00 -12.21  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0180244000
_diffrn_orient_matrix_UB_12      -0.0004748000
_diffrn_orient_matrix_UB_13      0.1063733000
_diffrn_orient_matrix_UB_21      -0.1869533000
_diffrn_orient_matrix_UB_22      -0.0435085000
_diffrn_orient_matrix_UB_23      -0.0240404000
_diffrn_orient_matrix_UB_31      0.0030706000
_diffrn_orient_matrix_UB_32      -0.1806454000
_diffrn_orient_matrix_UB_33      -0.0116276000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3766
_reflns_number_total             4180
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+1.2273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1588
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7C(H7C)
2.b Aromatic/amide H refined with riding coordinates:
 C14C(H14C), C20C(H20C), C1C(H1C), C21C(H21C), C11C(H11C), C5C(H5C),
 C24C(H24C), C4C(H4C), C2C(H2C), C22C(H22C), C3C(H3C), C13C(H13C), C12C(H12C),
 C23C(H23C)
2.c Idealised Me refined as rotating group:
 C(HA,HB,HC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1O O -0.3141(2) 0.0039(2) 0.21425(12) 0.0333(4) Uani 1 1 d . . . . .
N2N N 0.2222(2) 0.3797(2) 0.35272(12) 0.0228(4) Uani 1 1 d . . . . .
O2O O 0.1213(2) 0.1781(2) 0.04201(11) 0.0311(4) Uani 1 1 d . . . . .
N1N N 0.1009(2) 0.3156(2) 0.40644(13) 0.0233(4) Uani 1 1 d . . . . .
O3O O 0.3228(2) 0.2964(2) 0.21358(12) 0.0362(4) Uani 1 1 d . . . . .
C19C C 0.3350(3) 0.5251(2) 0.39358(15) 0.0235(4) Uani 1 1 d . . . . .
C18C C 0.0125(3) 0.1845(2) 0.35803(15) 0.0221(4) Uani 1 1 d . . . . .
C16C C -0.0023(3) 0.1743(3) 0.07924(15) 0.0248(4) Uani 1 1 d . . . . .
C C -0.1201(3) 0.0914(3) 0.40387(16) 0.0266(5) Uani 1 1 d . . . . .
HA H -0.116248 0.141924 0.468361 0.040 Uiso 1 1 calc GR . . . .
HB H -0.105366 -0.016902 0.403505 0.040 Uiso 1 1 calc GR . . . .
HC H -0.223816 0.089301 0.369256 0.040 Uiso 1 1 calc GR . . . .
C14C C -0.1699(3) 0.3199(3) -0.02977(16) 0.0325(5) Uani 1 1 d . . . . .
H14C H -0.083391 0.359621 -0.062071 0.039 Uiso 1 1 calc R . . . .
C20C C 0.3399(3) 0.5828(3) 0.48964(16) 0.0263(5) Uani 1 1 d . . . . .
H20C H 0.270441 0.526821 0.526803 0.032 Uiso 1 1 calc R . . . .
C9C C -0.2263(3) 0.0782(3) 0.16510(15) 0.0255(4) Uani 1 1 d . . . . .
C10C C -0.2801(3) 0.1682(3) 0.09020(15) 0.0259(5) Uani 1 1 d . . . . .
C6C C -0.0156(3) -0.1701(2) 0.23359(15) 0.0233(4) Uani 1 1 d . . . . .
C1C C 0.0501(3) -0.2168(3) 0.31568(16) 0.0269(5) Uani 1 1 d . . . . .
H1C H 0.140502 -0.149422 0.352976 0.032 Uiso 1 1 calc R . . . .
C17C C 0.0710(3) 0.1490(2) 0.26418(15) 0.0234(4) Uani 1 1 d . . . . .
C25C C 0.2220(3) 0.2817(3) 0.26918(15) 0.0246(4) Uani 1 1 d . . . . .
C8C C -0.0437(3) 0.0959(2) 0.16611(15) 0.0231(4) Uani 1 1 d . . . . .
C21C C 0.4498(3) 0.7250(3) 0.52956(17) 0.0293(5) Uani 1 1 d . . . . .
H21C H 0.453706 0.764004 0.593822 0.035 Uiso 1 1 calc R . . . .
C15C C -0.1500(3) 0.2284(3) 0.04286(15) 0.0262(5) Uani 1 1 d . . . . .
C11C C -0.4354(3) 0.1944(3) 0.06682(17) 0.0305(5) Uani 1 1 d . . . . .
H11C H -0.522617 0.152048 0.097889 0.037 Uiso 1 1 calc R . . . .
C5C C -0.1464(3) -0.2752(3) 0.17657(15) 0.0262(5) Uani 1 1 d . . . . .
H5C H -0.189597 -0.246076 0.120698 0.031 Uiso 1 1 calc R . . . .
C24C C 0.4383(3) 0.6085(3) 0.33777(17) 0.0320(5) Uani 1 1 d . . . . .
H24C H 0.434769 0.569731 0.273491 0.038 Uiso 1 1 calc R . . . .
C4C C -0.2135(3) -0.4236(3) 0.20231(16) 0.0295(5) Uani 1 1 d . . . . .
H4C H -0.300659 -0.493545 0.163618 0.035 Uiso 1 1 calc R . . . .
C2C C -0.0186(3) -0.3636(3) 0.34242(16) 0.0291(5) Uani 1 1 d . . . . .
H2C H 0.023652 -0.392668 0.398538 0.035 Uiso 1 1 calc R . . . .
C22C C 0.5535(3) 0.8092(3) 0.47464(19) 0.0335(5) Uani 1 1 d . . . . .
H22C H 0.626671 0.904303 0.501759 0.040 Uiso 1 1 calc R . . . .
C3C C -0.1500(3) -0.4665(3) 0.28543(16) 0.0285(5) Uani 1 1 d . . . . .
H3C H -0.195553 -0.564856 0.303269 0.034 Uiso 1 1 calc R . . . .
C13C C -0.3235(4) 0.3493(3) -0.05190(18) 0.0392(6) Uani 1 1 d . . . . .
H13C H -0.339738 0.412029 -0.098975 0.047 Uiso 1 1 calc R . . . .
C12C C -0.4544(3) 0.2866(3) -0.00492(18) 0.0375(6) Uani 1 1 d . . . . .
H12C H -0.556420 0.307047 -0.022045 0.045 Uiso 1 1 calc R . . . .
C23C C 0.5472(3) 0.7506(3) 0.37920(19) 0.0372(6) Uani 1 1 d . . . . .
H23C H 0.616674 0.806864 0.342183 0.045 Uiso 1 1 calc R . . . .
C7C C 0.0579(3) -0.0127(2) 0.20372(14) 0.0227(4) Uani 1 1 d . . . . .
H7C H 0.153211 -0.017643 0.170114 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
O1O C9C 1.212(3) . ?
N2N N1N 1.402(2) . ?
N2N C19C 1.423(3) . ?
N2N C25C 1.366(3) . ?
O2O C16C 1.211(3) . ?
N1N C18C 1.288(3) . ?
O3O C25C 1.216(3) . ?
C19C C20C 1.390(3) . ?
C19C C24C 1.389(3) . ?
C18C C 1.492(3) . ?
C18C C17C 1.487(3) . ?
C16C C8C 1.520(3) . ?
C16C C15C 1.488(3) . ?
C14C C15C 1.396(3) . ?
C14C C13C 1.385(4) . ?
C20C C21C 1.390(3) . ?
C9C C10C 1.485(3) . ?
C9C C8C 1.517(3) . ?
C10C C15C 1.388(3) . ?
C10C C11C 1.392(3) . ?
C6C C1C 1.389(3) . ?
C6C C5C 1.390(3) . ?
C6C C7C 1.498(3) . ?
C1C C2C 1.391(3) . ?
C17C C25C 1.516(3) . ?
C17C C8C 1.583(3) . ?
C17C C7C 1.512(3) . ?
C8C C7C 1.501(3) . ?
C21C C22C 1.386(3) . ?
C11C C12C 1.388(4) . ?
C5C C4C 1.393(3) . ?
C24C C23C 1.391(3) . ?
C4C C3C 1.380(3) . ?
C2C C3C 1.385(3) . ?
C22C C23C 1.382(4) . ?
C13C C12C 1.396(4) . ?

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
N1N N2N C19C 118.13(17) . . ?
C25C N2N N1N 112.78(16) . . ?
C25C N2N C19C 128.84(17) . . ?
C18C N1N N2N 108.87(17) . . ?
C20C C19C N2N 119.25(18) . . ?
C24C C19C N2N 120.20(19) . . ?
C24C C19C C20C 120.55(19) . . ?
N1N C18C C 117.93(19) . . ?
N1N C18C C17C 110.86(18) . . ?
C17C C18C C 131.11(18) . . ?
O2O C16C C8C 126.3(2) . . ?
O2O C16C C15C 126.7(2) . . ?
C15C C16C C8C 106.64(18) . . ?
C13C C14C C15C 117.5(2) . . ?
C19C C20C C21C 119.3(2) . . ?
O1O C9C C10C 125.7(2) . . ?
O1O C9C C8C 127.5(2) . . ?
C10C C9C C8C 106.77(17) . . ?
C15C C10C C9C 110.39(19) . . ?
C15C C10C C11C 121.8(2) . . ?
C11C C10C C9C 127.9(2) . . ?
C1C C6C C5C 119.05(19) . . ?
C1C C6C C7C 120.89(19) . . ?
C5C C6C C7C 119.99(19) . . ?
C6C C1C C2C 120.4(2) . . ?
C18C C17C C25C 103.04(17) . . ?
C18C C17C C8C 124.44(18) . . ?
C18C C17C C7C 128.76(18) . . ?
C25C C17C C8C 117.99(17) . . ?
C7C C17C C25C 120.16(18) . . ?
C7C C17C C8C 57.97(13) . . ?
N2N C25C C17C 103.98(17) . . ?
O3O C25C N2N 127.52(19) . . ?
O3O C25C C17C 128.5(2) . . ?
C16C C8C C17C 120.98(17) . . ?
C9C C8C C16C 105.17(18) . . ?
C9C C8C C17C 119.36(17) . . ?
C7C C8C C16C 120.42(18) . . ?
C7C C8C C9C 126.82(18) . . ?
C7C C8C C17C 58.63(13) . . ?
C22C C21C C20C 120.7(2) . . ?
C14C C15C C16C 129.1(2) . . ?
C10C C15C C16C 109.86(19) . . ?
C10C C15C C14C 121.0(2) . . ?
C12C C11C C10C 117.1(2) . . ?
C6C C5C C4C 120.6(2) . . ?
C19C C24C C23C 119.2(2) . . ?
C3C C4C C5C 119.7(2) . . ?
C3C C2C C1C 120.0(2) . . ?
C23C C22C C21C 119.4(2) . . ?
C4C C3C C2C 120.2(2) . . ?
C14C C13C C12C 121.3(2) . . ?
C11C C12C C13C 121.4(2) . . ?
C22C C23C C24C 120.9(2) . . ?
C6C C7C C17C 123.32(18) . . ?
C6C C7C C8C 122.60(18) . . ?
C8C C7C C17C 63.40(14) . . ?

_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 1.910
_oxdiff_exptl_absorpt_empirical_full_min 0.691
####################################################################### 
# 
# 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_exp-880_tp-19b
_database_code_depnum_ccdc_archive 'CCDC 2101428'
loop_
_audit_author_name
_audit_author_address
'Adarash kumar Shukla'
;bits pilani, hyderabad
India
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.44(C26 H17 Cl N2 O3)'
_chemical_formula_sum            'C11.56 H7.56 Cl0.44 N0.89 O1.33'
_chemical_formula_weight         195.94
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   12.8370(2)
_cell_length_b                   10.83450(10)
_cell_length_c                   16.2470(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.647(2)
_cell_angle_gamma                90
_cell_volume                     2085.44(5)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    7441
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.1860
_cell_measurement_theta_min      5.0200
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    1.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13423
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.974
_diffrn_reflns_theta_min         5.036
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00   1.00   0.50    1.55    --    0.00 -37.00-180.00   90
  2  ω    -30.00  59.00   0.50    1.55    --    0.00  77.00 -60.00  178
  3  ω    -80.00   7.00   0.50    1.55    --    0.00 -37.00 -90.00  174
  4  ω     21.00 138.00   0.50    6.20    --  107.20 -82.00 -30.00  234
  5  ω    101.00 127.00   0.50    6.20    --  107.20 -82.00 150.00   52
  6  ω     37.00 113.00   0.50    6.20    --  107.20 -82.00-180.00  152
  7  ω     54.00 124.00   0.50    6.20    --  107.20 -82.00-120.00  140
  8  ω     22.00  55.00   0.50    6.20    --  107.20 -30.00 -60.00   66
  9  ω     89.00 195.00   0.50    6.20    --  107.20  30.00 -90.00  212
 10  ω     30.00  82.00   0.50    6.20    --  107.20 -82.00 150.00  104
 11  ω     18.00 129.00   0.50    6.20    --  107.20 -61.00  30.00  222
 12  ω    108.00 194.00   0.50    6.20    --  107.20  45.00 150.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0613255000
_diffrn_orient_matrix_UB_12      -0.0279544000
_diffrn_orient_matrix_UB_13      -0.0628692000
_diffrn_orient_matrix_UB_21      0.0066435000
_diffrn_orient_matrix_UB_22      -0.1375127000
_diffrn_orient_matrix_UB_23      0.0256494000
_diffrn_orient_matrix_UB_31      -0.1144523000
_diffrn_orient_matrix_UB_32      -0.0230480000
_diffrn_orient_matrix_UB_33      -0.0770943000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4054
_reflns_number_total             4437
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.077
_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)+(0.0523P)²+0.9611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10C(H10C)
2.b Aromatic/amide H refined with riding coordinates:
 C3C(H3C), C4C(H4C), C5C(H5C), C6C(H6C), C14C(H14C), C15C(H15C), C17C(H17C),
 C18C(H18C), C22C(H22C), C23C(H23C), C24C(H24C), C25C(H25C), C26C(H26C)
2.c Idealised Me refined as rotating group:
 C20C(H20A,H20B,H20C)
;
_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
Cl1C Cl 0.55775(4) -0.14754(4) 0.74194(3) 0.03959(14) Uani 1 1 d . . . . .
O1C O 0.97213(8) 0.40478(10) 0.56215(7) 0.0245(2) Uani 1 1 d . . . . .
O2C O 0.67409(9) 0.66869(10) 0.39360(7) 0.0269(2) Uani 1 1 d . . . . .
O3C O 0.81797(9) 0.20906(10) 0.53184(7) 0.0261(2) Uani 1 1 d . . . . .
N1N N 0.63931(10) 0.25471(12) 0.52762(8) 0.0242(3) Uani 1 1 d . . . . .
N2N N 0.54770(10) 0.32845(13) 0.47509(8) 0.0250(3) Uani 1 1 d . . . . .
C1C C 0.90174(11) 0.48571(13) 0.54375(9) 0.0195(3) Uani 1 1 d . . . . .
C2C C 0.91137(12) 0.60626(14) 0.58901(9) 0.0208(3) Uani 1 1 d . . . . .
C3C C 0.99436(13) 0.64687(15) 0.66858(10) 0.0257(3) Uani 1 1 d . . . . .
H3C H 1.050424 0.593764 0.704371 0.031 Uiso 1 1 calc R . . . .
C4C C 0.99068(13) 0.76919(17) 0.69274(11) 0.0309(4) Uani 1 1 d . . . . .
H4C H 1.044546 0.798306 0.745955 0.037 Uiso 1 1 calc R . . . .
C5C C 0.90757(14) 0.84886(16) 0.63849(11) 0.0317(4) Uani 1 1 d . . . . .
H5C H 0.908464 0.931056 0.655248 0.038 Uiso 1 1 calc R . . . .
C6C C 0.82354(13) 0.80853(15) 0.56010(10) 0.0267(3) Uani 1 1 d . . . . .
H6C H 0.767136 0.861572 0.524669 0.032 Uiso 1 1 calc R . . . .
C7C C 0.82677(12) 0.68570(14) 0.53642(9) 0.0211(3) Uani 1 1 d . . . . .
C8C C 0.75104(12) 0.62170(13) 0.45494(9) 0.0201(3) Uani 1 1 d . . . . .
C9C C 0.79072(11) 0.48906(13) 0.46277(9) 0.0184(3) Uani 1 1 d . . . . .
C10C C 0.76830(11) 0.40192(13) 0.38640(9) 0.0181(3) Uani 1 1 d . . . . .
H10C H 0.829162 0.341481 0.398273 0.022 Uiso 1 1 calc R . . . .
C11C C 0.70216(12) 0.38094(13) 0.44435(9) 0.0193(3) Uani 1 1 d . . . . .
C12C C 0.73288(12) 0.27195(13) 0.50717(9) 0.0206(3) Uani 1 1 d . . . . .
C13C C 0.61979(13) 0.15919(14) 0.57966(10) 0.0233(3) Uani 1 1 d . . . . .
C14C C 0.51038(14) 0.13176(17) 0.57044(12) 0.0319(4) Uani 1 1 d . . . . .
H14C H 0.450193 0.176547 0.530724 0.038 Uiso 1 1 calc R . . . .
C15C C 0.49066(14) 0.03776(18) 0.62028(12) 0.0350(4) Uani 1 1 d . . . . .
H15C H 0.417396 0.019809 0.614708 0.042 Uiso 1 1 calc R . . . .
C16C C 0.58039(14) -0.02921(15) 0.67835(11) 0.0286(3) Uani 1 1 d . . . . .
C17C C 0.68948(15) -0.00145(17) 0.68893(12) 0.0359(4) Uani 1 1 d . . . . .
H17C H 0.749379 -0.046412 0.728830 0.043 Uiso 1 1 calc R . . . .
C18C C 0.70991(14) 0.09360(17) 0.64004(12) 0.0356(4) Uani 1 1 d . . . . .
H18C H 0.783529 0.113396 0.647589 0.043 Uiso 1 1 calc R . . . .
C19C C 0.58039(12) 0.40087(14) 0.42683(9) 0.0215(3) Uani 1 1 d . . . . .
C20C C 0.49547(13) 0.48346(16) 0.36175(10) 0.0276(3) Uani 1 1 d . . . . .
H20A H 0.420943 0.457561 0.354563 0.041 Uiso 1 1 calc GR . . . .
H20B H 0.503097 0.479227 0.305309 0.041 Uiso 1 1 calc GR . . . .
H20C H 0.507639 0.566809 0.383425 0.041 Uiso 1 1 calc GR . . . .
C21C C 0.71808(11) 0.43915(13) 0.28997(9) 0.0183(3) Uani 1 1 d . . . . .
C22C C 0.76089(12) 0.54032(13) 0.26030(9) 0.0210(3) Uani 1 1 d . . . . .
H22C H 0.815475 0.590259 0.301058 0.025 Uiso 1 1 calc R . . . .
C23C C 0.72179(12) 0.56654(14) 0.16947(9) 0.0233(3) Uani 1 1 d . . . . .
H23C H 0.750964 0.633685 0.149730 0.028 Uiso 1 1 calc R . . . .
C24C C 0.63958(12) 0.49317(15) 0.10818(9) 0.0249(3) Uani 1 1 d . . . . .
H24C H 0.613099 0.511975 0.047719 0.030 Uiso 1 1 calc R . . . .
C25C C 0.59697(13) 0.39188(15) 0.13711(10) 0.0256(3) Uani 1 1 d . . . . .
H25C H 0.542374 0.342116 0.096204 0.031 Uiso 1 1 calc R . . . .
C26C C 0.63656(12) 0.36524(14) 0.22789(10) 0.0225(3) Uani 1 1 d . . . . .
H26C H 0.608192 0.297171 0.247333 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
Cl1C C16C 1.7398(16) . ?
O1C C1C 1.2109(18) . ?
O2C C8C 1.2124(17) . ?
O3C C12C 1.2169(18) . ?
N1N N2N 1.4060(17) . ?
N1N C12C 1.3768(19) . ?
N1N C13C 1.4183(19) . ?
N2N C19C 1.288(2) . ?
C1C C2C 1.481(2) . ?
C1C C9C 1.5230(18) . ?
C2C C3C 1.393(2) . ?
C2C C7C 1.391(2) . ?
C3C H3C 0.9300 . ?
C3C C4C 1.388(2) . ?
C4C H4C 0.9300 . ?
C4C C5C 1.391(2) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.385(2) . ?
C6C H6C 0.9300 . ?
C6C C7C 1.390(2) . ?
C7C C8C 1.4790(19) . ?
C8C C9C 1.5135(19) . ?
C9C C10C 1.4963(19) . ?
C9C C11C 1.5786(19) . ?
C10C H10C 0.9800 . ?
C10C C11C 1.5081(19) . ?
C10C C21C 1.5017(18) . ?
C11C C12C 1.5106(19) . ?
C11C C19C 1.4928(19) . ?
C13C C14C 1.386(2) . ?
C13C C18C 1.390(2) . ?
C14C H14C 0.9300 . ?
C14C C15C 1.384(2) . ?
C15C H15C 0.9300 . ?
C15C C16C 1.381(2) . ?
C16C C17C 1.377(2) . ?
C17C H17C 0.9300 . ?
C17C C18C 1.386(2) . ?
C18C H18C 0.9300 . ?
C19C C20C 1.490(2) . ?
C20C H20A 0.9600 . ?
C20C H20B 0.9600 . ?
C20C H20C 0.9600 . ?
C21C C22C 1.393(2) . ?
C21C C26C 1.3931(19) . ?
C22C H22C 0.9300 . ?
C22C C23C 1.3928(19) . ?
C23C H23C 0.9300 . ?
C23C C24C 1.388(2) . ?
C24C H24C 0.9300 . ?
C24C C25C 1.386(2) . ?
C25C H25C 0.9300 . ?
C25C C26C 1.393(2) . ?
C26C H26C 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
N2N N1N C13C 118.56(12) . . ?
C12C N1N N2N 112.33(12) . . ?
C12C N1N C13C 127.85(13) . . ?
C19C N2N N1N 108.86(12) . . ?
O1C C1C C2C 127.19(13) . . ?
O1C C1C C9C 126.27(13) . . ?
C2C C1C C9C 106.22(11) . . ?
C3C C2C C1C 128.87(14) . . ?
C7C C2C C1C 110.16(12) . . ?
C7C C2C C3C 120.79(14) . . ?
C2C C3C H3C 121.1 . . ?
C4C C3C C2C 117.84(14) . . ?
C4C C3C H3C 121.1 . . ?
C3C C4C H4C 119.5 . . ?
C3C C4C C5C 120.96(14) . . ?
C5C C4C H4C 119.5 . . ?
C4C C5C H5C 119.3 . . ?
C6C C5C C4C 121.49(15) . . ?
C6C C5C H5C 119.3 . . ?
C5C C6C H6C 121.3 . . ?
C5C C6C C7C 117.43(15) . . ?
C7C C6C H6C 121.3 . . ?
C2C C7C C8C 110.38(13) . . ?
C6C C7C C2C 121.44(13) . . ?
C6C C7C C8C 128.11(13) . . ?
O2C C8C C7C 125.84(14) . . ?
O2C C8C C9C 127.52(13) . . ?
C7C C8C C9C 106.62(11) . . ?
C1C C9C C11C 120.81(11) . . ?
C8C C9C C1C 105.54(11) . . ?
C8C C9C C11C 119.62(12) . . ?
C10C C9C C1C 121.23(12) . . ?
C10C C9C C8C 125.33(12) . . ?
C10C C9C C11C 58.67(9) . . ?
C9C C10C H10C 112.0 . . ?
C9C C10C C11C 63.39(9) . . ?
C9C C10C C21C 124.33(12) . . ?
C11C C10C H10C 112.0 . . ?
C21C C10C H10C 112.0 . . ?
C21C C10C C11C 124.96(12) . . ?
C10C C11C C9C 57.94(9) . . ?
C10C C11C C12C 118.45(12) . . ?
C12C C11C C9C 118.06(11) . . ?
C19C C11C C9C 123.61(12) . . ?
C19C C11C C10C 131.23(12) . . ?
C19C C11C C12C 102.93(12) . . ?
O3C C12C N1N 126.90(14) . . ?
O3C C12C C11C 128.90(13) . . ?
N1N C12C C11C 104.13(12) . . ?
C14C C13C N1N 119.75(14) . . ?
C14C C13C C18C 120.00(15) . . ?
C18C C13C N1N 120.25(14) . . ?
C13C C14C H14C 120.0 . . ?
C15C C14C C13C 120.05(15) . . ?
C15C C14C H14C 120.0 . . ?
C14C C15C H15C 120.2 . . ?
C16C C15C C14C 119.61(15) . . ?
C16C C15C H15C 120.2 . . ?
C15C C16C Cl1C 120.45(13) . . ?
C17C C16C Cl1C 118.77(13) . . ?
C17C C16C C15C 120.75(15) . . ?
C16C C17C H17C 120.0 . . ?
C16C C17C C18C 119.90(16) . . ?
C18C C17C H17C 120.0 . . ?
C13C C18C H18C 120.2 . . ?
C17C C18C C13C 119.65(15) . . ?
C17C C18C H18C 120.2 . . ?
N2N C19C C11C 111.00(13) . . ?
N2N C19C C20C 118.49(13) . . ?
C20C C19C C11C 130.43(13) . . ?
C19C C20C H20A 109.5 . . ?
C19C C20C H20B 109.5 . . ?
C19C C20C H20C 109.5 . . ?
H20A C20C H20B 109.5 . . ?
H20A C20C H20C 109.5 . . ?
H20B C20C H20C 109.5 . . ?
C22C C21C C10C 120.29(12) . . ?
C22C C21C C26C 119.23(13) . . ?
C26C C21C C10C 120.13(13) . . ?
C21C C22C H22C 120.1 . . ?
C21C C22C C23C 119.86(13) . . ?
C23C C22C H22C 120.1 . . ?
C22C C23C H23C 119.8 . . ?
C24C C23C C22C 120.49(14) . . ?
C24C C23C H23C 119.8 . . ?
C23C C24C H24C 120.0 . . ?
C25C C24C C23C 120.01(13) . . ?
C25C C24C H24C 120.0 . . ?
C24C C25C H25C 120.3 . . ?
C24C C25C C26C 119.49(14) . . ?
C26C C25C H25C 120.3 . . ?
C21C C26C H26C 119.5 . . ?
C25C C26C C21C 120.90(14) . . ?
C25C C26C H26C 119.5 . . ?

_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 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.746
