# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_exp_1397-am-r-299-f2
_database_code_depnum_ccdc_archive 'CCDC 2289881'
loop_
_audit_author_name
_audit_author_address
'Rohan A.'
;Bits Pilani Hyderabad campus
India
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H21 Cl2 N O3'
_chemical_formula_sum            'C27 H21 Cl2 N O3'
_chemical_formula_weight         478.35
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.9426(3)
_cell_length_b                   18.2781(4)
_cell_length_c                   14.4279(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.619(2)
_cell_angle_gamma                90
_cell_volume                     2358.16(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2695
_cell_measurement_temperature    140
_cell_measurement_theta_max      73.4540
_cell_measurement_theta_min      3.9060
_shelx_estimated_absorpt_T_max   0.773
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    2.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58360
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.2
_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  0.0458
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14146
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.779
_diffrn_reflns_theta_min         3.903
_diffrn_ambient_temperature      140
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  88.00   0.50    0.50    --    0.00  57.00 -30.00   98
  2  ω    -45.00  17.00   0.50    0.50    --    0.00 -37.00  90.00  124
  3  ω     49.00  85.00   0.50    0.50    --    0.00  37.00  30.00   72
  4  ω     -2.00  24.00   0.50    0.50    --    0.00  37.00  30.00   52
  5  ω    -23.00  33.00   0.50    0.50    --    0.00  57.00 -30.00  112
  6  ω     24.00 132.00   0.50    1.00    --  107.20 -61.00 -90.00  216
  7  ω     31.00 133.00   0.50    1.00    --  107.20 -15.00-120.00  204
  8  ω     71.00 118.00   0.50    1.00    --  107.20 -30.00 -90.00   94
  9  ω    162.00 188.00   0.50    1.00    --  107.20  15.00 -90.00   52
 10  ω    119.00 161.00   0.50    1.00    --  107.20  15.00 -90.00   84
 11  ω    134.00 161.00   0.50    1.00    --  107.20  30.00 150.00   54
 12  ω     90.00 115.00   0.50    1.00    --  107.20  15.00 -90.00   50
 13  ω     18.00 128.00   0.50    1.00    --  107.20 -45.00  30.00  220
 14  ω     18.00 139.00   0.50    1.00    --  107.20 -82.00 -90.00  242
;
_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      0.1370987000
_diffrn_orient_matrix_UB_12      -0.0072859000
_diffrn_orient_matrix_UB_13      0.0649413000
_diffrn_orient_matrix_UB_21      -0.0930385000
_diffrn_orient_matrix_UB_22      0.0291583000
_diffrn_orient_matrix_UB_23      0.0812370000
_diffrn_orient_matrix_UB_31      -0.0472746000
_diffrn_orient_matrix_UB_32      -0.0787546000
_diffrn_orient_matrix_UB_33      0.0241014000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3264
_reflns_number_total             5016
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00080(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.058
_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)+(0.0615P)²+0.4022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1627
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C26(H26), C21(H21), C33(H33), C27(H27), C22(H22),
 C14(H14), C29(H29), C16(H16), C20(H20), C31(H31), C10(H10), C13(H13), C19(H19),
  C11(H11), C12(H12), C18(H18), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.16372(11) 0.66914(6) 0.14513(8) 0.1163(4) Uani 1 1 d . . . . .
Cl2 Cl -0.03908(13) 0.71428(5) 0.49068(8) 0.1123(4) Uani 1 1 d . . . . .
O3 O 0.6990(2) 0.15770(10) 0.60502(12) 0.0643(5) Uani 1 1 d . . . . .
O5 O 0.7808(3) 0.07074(12) 0.82064(13) 0.0692(6) Uani 1 1 d . . . . .
N6 N 0.5579(2) 0.27395(11) 0.56509(14) 0.0542(5) Uani 1 1 d . . . . .
O4 O 0.6251(2) 0.17570(11) 0.74957(14) 0.0796(6) Uani 1 1 d . . . . .
C9 C 0.7317(3) 0.00426(13) 0.68228(16) 0.0519(5) Uani 1 1 d . . . . .
C8 C 0.7911(3) 0.07587(13) 0.72170(15) 0.0503(5) Uani 1 1 d . . . . .
C23 C 0.3936(3) 0.39655(12) 0.51439(16) 0.0507(5) Uani 1 1 d . . . . .
C7 C 0.6953(3) 0.14206(13) 0.69094(17) 0.0544(6) Uani 1 1 d . . . . .
C24 C 0.4746(3) 0.35719(13) 0.44973(17) 0.0531(5) Uani 1 1 d . . . . .
H24 H 0.473970 0.371812 0.386547 0.064 Uiso 1 1 calc R U . . .
C15 C 0.9528(3) 0.09106(13) 0.69478(18) 0.0546(6) Uani 1 1 d . . . . .
C25 C 0.5554(3) 0.29732(13) 0.47721(17) 0.0534(5) Uani 1 1 d . . . . .
H25 H 0.611590 0.271438 0.432360 0.064 Uiso 1 1 calc R U . . .
C26 C 0.3050(3) 0.46167(14) 0.49093(18) 0.0577(6) Uani 1 1 d . . . . .
H26 H 0.253071 0.485237 0.539647 0.069 Uiso 1 1 calc R U . . .
C21 C 0.4815(3) 0.31126(15) 0.62790(18) 0.0636(7) Uani 1 1 d . . . . .
H21 H 0.482995 0.294939 0.690415 0.076 Uiso 1 1 calc R U . . .
C28 C 0.2111(3) 0.55591(14) 0.3799(2) 0.0632(7) Uani 1 1 d . . . . .
C33 C 0.1284(3) 0.59752(14) 0.4425(2) 0.0666(7) Uani 1 1 d . . . . .
H33 H 0.118424 0.581868 0.504884 0.080 Uiso 1 1 calc R U . . .
C27 C 0.2925(3) 0.48978(14) 0.40721(19) 0.0621(6) Uani 1 1 d . . . . .
H27 H 0.341811 0.464216 0.359054 0.075 Uiso 1 1 calc R U . . .
C22 C 0.4006(3) 0.37256(15) 0.60528(18) 0.0634(7) Uani 1 1 d . . . . .
H22 H 0.349316 0.398651 0.652173 0.076 Uiso 1 1 calc R U . . .
C14 C 0.8130(3) -0.05909(14) 0.6964(2) 0.0649(7) Uani 1 1 d . . . . .
H14 H 0.907981 -0.056181 0.726385 0.078 Uiso 1 1 calc R U . . .
C29 C 0.2208(3) 0.57870(16) 0.2882(2) 0.0717(8) Uani 1 1 d . . . . .
H29 H 0.273900 0.550015 0.244640 0.086 Uiso 1 1 calc R U . . .
C16 C 1.0043(3) 0.07488(16) 0.6071(2) 0.0711(7) Uani 1 1 d . . . . .
H16 H 0.939214 0.051630 0.563722 0.085 Uiso 1 1 calc R U . . .
C20 C 1.0492(3) 0.12576(16) 0.7569(2) 0.0746(8) Uani 1 1 d . . . . .
H20 H 1.017510 0.136924 0.817905 0.090 Uiso 1 1 calc R U . . .
C32 C 0.0609(3) 0.66184(14) 0.4127(2) 0.0743(9) Uani 1 1 d . . . . .
C31 C 0.0743(4) 0.68595(16) 0.3219(3) 0.0823(10) Uani 1 1 d . . . . .
H31 H 0.030416 0.730793 0.302452 0.099 Uiso 1 1 calc R U . . .
C10 C 0.5944(3) -0.00217(17) 0.6386(2) 0.0754(8) Uani 1 1 d . . . . .
H10 H 0.535093 0.040259 0.628459 0.090 Uiso 1 1 calc R U . . .
C30 C 0.1532(4) 0.64295(18) 0.2607(2) 0.0792(9) Uani 1 1 d . . . . .
C13 C 0.7604(4) -0.12596(17) 0.6684(2) 0.0819(9) Uani 1 1 d . . . . .
H13 H 0.818524 -0.168690 0.679179 0.098 Uiso 1 1 calc R U . . .
C19 C 1.1944(4) 0.14414(19) 0.7283(3) 0.0981(13) Uani 1 1 d . . . . .
H19 H 1.260399 0.168561 0.770055 0.118 Uiso 1 1 calc R U . . .
C11 C 0.5417(4) -0.0700(2) 0.6092(3) 0.0906(10) Uani 1 1 d . . . . .
H11 H 0.447782 -0.073586 0.578134 0.109 Uiso 1 1 calc R U . . .
C12 C 0.6248(4) -0.13124(19) 0.6250(2) 0.0861(10) Uani 1 1 d . . . . .
H12 H 0.588238 -0.177669 0.605687 0.103 Uiso 1 1 calc R U . . .
C18 C 1.2417(4) 0.1272(2) 0.6409(4) 0.1025(13) Uani 1 1 d . . . . .
H18 H 1.339565 0.140094 0.621922 0.123 Uiso 1 1 calc R U . . .
C17 C 1.1475(4) 0.0917(2) 0.5815(3) 0.0951(11) Uani 1 1 d . . . . .
H17 H 1.181221 0.078500 0.521567 0.114 Uiso 1 1 calc R U . . .
H3 H 0.630(4) 0.212(2) 0.592(3) 0.125(13) Uiso 1 1 d . . . . .
H5 H 0.732(5) 0.100(2) 0.835(3) 0.109(16) 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 C30 1.739(3) . ?
Cl2 C32 1.734(4) . ?
O3 C7 1.273(3) . ?
O3 H3 1.18(4) . ?
O5 C8 1.434(3) . ?
O5 H5 0.73(4) . ?
N6 C25 1.338(3) . ?
N6 C21 1.329(3) . ?
N6 H3 1.36(4) . ?
O4 C7 1.224(3) . ?
C9 C8 1.521(3) . ?
C9 C14 1.382(3) . ?
C9 C10 1.379(3) . ?
C8 C7 1.545(3) . ?
C8 C15 1.527(3) . ?
C23 C24 1.388(3) . ?
C23 C26 1.467(3) . ?
C23 C22 1.384(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.367(3) . ?
C15 C16 1.383(4) . ?
C15 C20 1.390(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.316(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.371(3) . ?
C28 C33 1.398(4) . ?
C28 C27 1.462(3) . ?
C28 C29 1.391(4) . ?
C33 H33 0.9500 . ?
C33 C32 1.387(4) . ?
C27 H27 0.9500 . ?
C22 H22 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.369(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.377(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.372(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.407(5) . ?
C32 C31 1.388(5) . ?
C31 H31 0.9500 . ?
C31 C30 1.382(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.362(5) . ?
C19 H19 0.9500 . ?
C19 C18 1.370(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.361(5) . ?
C12 H12 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.359(6) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 H3 109.2(19) . . ?
C8 O5 H5 106(3) . . ?
C25 N6 H3 122.4(17) . . ?
C21 N6 C25 118.6(2) . . ?
C21 N6 H3 118.9(17) . . ?
C14 C9 C8 119.0(2) . . ?
C10 C9 C8 123.4(2) . . ?
C10 C9 C14 117.5(2) . . ?
O5 C8 C9 106.87(19) . . ?
O5 C8 C7 107.2(2) . . ?
O5 C8 C15 109.6(2) . . ?
C9 C8 C7 112.09(19) . . ?
C9 C8 C15 112.9(2) . . ?
C15 C8 C7 107.96(19) . . ?
C24 C23 C26 123.3(2) . . ?
C22 C23 C24 117.0(2) . . ?
C22 C23 C26 119.7(2) . . ?
O3 C7 C8 115.8(2) . . ?
O4 C7 O3 125.4(2) . . ?
O4 C7 C8 118.8(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C16 C15 C8 121.3(2) . . ?
C16 C15 C20 118.5(3) . . ?
C20 C15 C8 120.1(3) . . ?
N6 C25 C24 122.3(2) . . ?
N6 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
C23 C26 H26 117.7 . . ?
C27 C26 C23 124.7(2) . . ?
C27 C26 H26 117.7 . . ?
N6 C21 H21 119.0 . . ?
N6 C21 C22 122.1(2) . . ?
C22 C21 H21 119.0 . . ?
C33 C28 C27 122.8(2) . . ?
C29 C28 C33 119.3(3) . . ?
C29 C28 C27 117.9(3) . . ?
C28 C33 H33 120.2 . . ?
C32 C33 C28 119.5(3) . . ?
C32 C33 H33 120.2 . . ?
C26 C27 C28 127.4(3) . . ?
C26 C27 H27 116.3 . . ?
C28 C27 H27 116.3 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.7(3) . . ?
C13 C14 H14 119.1 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C20 H20 120.4 . . ?
C15 C20 C19 119.2(3) . . ?
C19 C20 H20 120.4 . . ?
C33 C32 Cl2 119.6(3) . . ?
C33 C32 C31 121.3(3) . . ?
C31 C32 Cl2 119.1(2) . . ?
C32 C31 H31 120.9 . . ?
C30 C31 C32 118.2(3) . . ?
C30 C31 H31 120.9 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C29 C30 Cl1 118.9(3) . . ?
C29 C30 C31 121.8(3) . . ?
C31 C30 Cl1 119.3(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 C20 120.7(3) . . ?
C18 C19 H19 119.7 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C19 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl2 C32 C31 C30 -179.3(2) . . . . ?
O5 C8 C7 O3 175.7(2) . . . . ?
O5 C8 C7 O4 -3.0(3) . . . . ?
O5 C8 C15 C16 158.2(2) . . . . ?
O5 C8 C15 C20 -25.7(3) . . . . ?
N6 C21 C22 C23 1.6(5) . . . . ?
C9 C8 C7 O3 -67.3(3) . . . . ?
C9 C8 C7 O4 114.0(3) . . . . ?
C9 C8 C15 C16 39.2(3) . . . . ?
C9 C8 C15 C20 -144.7(2) . . . . ?
C9 C14 C13 C12 0.3(5) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C8 C9 C14 C13 175.3(3) . . . . ?
C8 C9 C10 C11 -175.8(3) . . . . ?
C8 C15 C16 C17 176.8(3) . . . . ?
C8 C15 C20 C19 -175.3(2) . . . . ?
C23 C24 C25 N6 1.0(4) . . . . ?
C23 C26 C27 C28 -177.4(2) . . . . ?
C7 C8 C15 C16 -85.3(3) . . . . ?
C7 C8 C15 C20 90.8(3) . . . . ?
C24 C23 C26 C27 0.0(4) . . . . ?
C24 C23 C22 C21 -1.8(4) . . . . ?
C15 C8 C7 O3 57.7(3) . . . . ?
C15 C8 C7 O4 -121.1(3) . . . . ?
C15 C16 C17 C18 -2.2(5) . . . . ?
C15 C20 C19 C18 -1.0(5) . . . . ?
C25 N6 C21 C22 0.1(4) . . . . ?
C26 C23 C24 C25 179.5(2) . . . . ?
C26 C23 C22 C21 179.2(3) . . . . ?
C21 N6 C25 C24 -1.4(4) . . . . ?
C28 C33 C32 Cl2 -178.9(2) . . . . ?
C28 C33 C32 C31 -0.2(4) . . . . ?
C28 C29 C30 Cl1 -178.7(2) . . . . ?
C28 C29 C30 C31 -0.3(4) . . . . ?
C33 C28 C27 C26 -2.6(4) . . . . ?
C33 C28 C29 C30 2.1(4) . . . . ?
C33 C32 C31 C30 1.9(4) . . . . ?
C27 C28 C33 C32 176.4(2) . . . . ?
C27 C28 C29 C30 -176.2(3) . . . . ?
C22 C23 C24 C25 0.6(4) . . . . ?
C22 C23 C26 C27 178.9(3) . . . . ?
C14 C9 C8 O5 -68.8(3) . . . . ?
C14 C9 C8 C7 174.1(2) . . . . ?
C14 C9 C8 C15 51.9(3) . . . . ?
C14 C9 C10 C11 -0.7(4) . . . . ?
C14 C13 C12 C11 0.2(5) . . . . ?
C29 C28 C33 C32 -1.8(4) . . . . ?
C29 C28 C27 C26 175.7(3) . . . . ?
C16 C15 C20 C19 0.9(4) . . . . ?
C20 C15 C16 C17 0.6(4) . . . . ?
C20 C19 C18 C17 -0.5(5) . . . . ?
C32 C31 C30 Cl1 176.7(2) . . . . ?
C32 C31 C30 C29 -1.7(4) . . . . ?
C10 C9 C8 O5 106.2(3) . . . . ?
C10 C9 C8 C7 -10.9(3) . . . . ?
C10 C9 C8 C15 -133.1(3) . . . . ?
C10 C9 C14 C13 0.0(4) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C19 C18 C17 C16 2.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.590
_oxdiff_exptl_absorpt_empirical_full_min 0.760
####################################################################### 
# 
# 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_dcl_4
_database_code_depnum_ccdc_archive 'CCDC 2290412'
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
p20210012@hyderabad.bits-pilani.ac.in
arijit.mukherjee@hyderabad.bits-pilani.ac.in
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Cl2 N'
_chemical_formula_sum            'C13 H9 Cl2 N'
_chemical_formula_weight         250.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24HN2Cl2
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.87140(10)
_cell_length_b                   11.4217(3)
_cell_length_c                   26.3704(6)
_cell_angle_alpha                90
_cell_angle_beta                 89.998(2)
_cell_angle_gamma                90
_cell_volume                     1166.05(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4694
_cell_measurement_temperature    295
_cell_measurement_theta_max      78.2020
_cell_measurement_theta_min      4.2300
_shelx_estimated_absorpt_T_max   0.648
_shelx_estimated_absorpt_T_min   0.451
_exptl_absorpt_coefficient_mu    4.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 -2 0.0180
0 7 -2 0.0180
0 7 2 0.0180
0 -7 2 0.0180
0 -7 -2 0.0180
0 7 -2 0.0180
0 7 -2 0.0180
0 -7 -2 0.0180
0 7 2 0.0180
0 -7 2 0.0180
0 -7 2 0.0180
0 7 2 0.0180
0 0 1 0.0000

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.4434 -7.2387 -2.0914 0.7430 -0.6692 -0.0004
0.4465 7.2395 -2.0854 -0.8123 0.4545 -0.3656
-0.4434 7.2387 2.0914 -0.7430 0.6692 0.0004
-0.4465 -7.2395 2.0854 0.8123 -0.4545 0.3656
0.4434 -7.2387 -2.0914 0.7430 -0.6692 -0.0004
-0.4440 7.2388 -2.0836 -0.8825 0.4701 -0.0187
0.4465 7.2395 -2.0854 -0.8123 0.4545 -0.3656
-0.4470 -7.2394 -2.0895 0.6728 -0.6537 0.3465
-0.4434 7.2387 2.0914 -0.7430 0.6692 0.0004
0.4440 -7.2388 2.0836 0.8825 -0.4701 0.0187
-0.4465 -7.2395 2.0854 0.8123 -0.4545 0.3656
0.4470 7.2394 2.0895 -0.6728 0.6537 -0.3465
0.0001 -0.0000 0.9997 0.0334 0.0477 0.0046

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10123
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.367
_diffrn_reflns_theta_min         3.870
_diffrn_ambient_temperature      295
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  21.00   0.50    2.00    --    0.00  57.00 150.00   64
  2  ω      9.00  36.00   0.50    2.00    --    0.00  77.00-150.00   54
  3  ω    -23.00  88.00   0.50    2.00    --    0.00  57.00 -60.00  222
  4  ω    -88.00  -9.00   0.50    2.00    --    0.00 -19.00-180.00  158
  5  ω    -18.00  34.00   0.50    2.00    --    0.00  82.00 150.00  104
  6  ω     24.00  50.00   0.50   24.00    --  107.20 -82.00-120.00   52
  7  ω     51.00 128.00   0.50   24.00    --  107.20 -82.00 -60.00  154
  8  ω     89.00 194.00   0.50   24.00    --  107.20  15.00 120.00  210
  9  ω     26.00 136.00   0.50   24.00    --  107.20 -82.00-180.00  220
 10  ω     95.00 174.00   0.50   24.00    --  107.20  15.00  30.00  158
 11  ω     20.00 129.00   0.50   24.00    --  107.20 -61.00  30.00  218
 12  ω     18.00  83.00   0.50   24.00    --  107.20 -30.00-150.00  130
 13  ω    170.00 197.00   0.50   24.00    --  107.20  15.00 -60.00   54
 14  ω     96.00 122.00   0.50   24.00    --  107.20  77.00  90.00   52
 15  ω    147.00 197.00   0.50   24.00    --  107.20  77.00  90.00  100
 16  ω     73.00  98.00   0.50   24.00    --  107.20 -82.00-120.00   50
 17  ω     64.00 108.00   0.50   24.00    --  107.20 -30.00 -60.00   88
 18  ω     22.00 102.00   0.50   24.00    --  107.20 -61.00-180.00  160
 19  ω     75.00 123.00   0.50   24.00    --  107.20 -82.00  30.00   96
 20  ω     44.00  70.00   0.50   24.00    --  107.20 -82.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): 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      0.0790075000
_diffrn_orient_matrix_UB_12      -0.1074527000
_diffrn_orient_matrix_UB_13      0.0333984000
_diffrn_orient_matrix_UB_21      -0.0173810000
_diffrn_orient_matrix_UB_22      0.0776020000
_diffrn_orient_matrix_UB_23      0.0477125000
_diffrn_orient_matrix_UB_31      -0.3895190000
_diffrn_orient_matrix_UB_32      -0.0251403000
_diffrn_orient_matrix_UB_33      0.0046222000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2141
_reflns_number_total             2483
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0725P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1394
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.529(2)
 0.471(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C9(H9), C7(H7), C11(H11), C5(H5), C2(H2), C3(H3), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2360(11) 1.2877(3) 0.71211(15) 0.0909(10) Uani 1 1 d . . . . .
H1 H 0.201153 1.367457 0.707126 0.109 Uiso 1 1 calc R U . . .
Cl1 Cl -0.4269(3) 0.82371(8) 0.46124(3) 0.0914(3) Uani 1 1 d . . . . .
Cl2 Cl -0.1825(5) 0.47287(7) 0.59060(5) 0.1366(6) Uani 1 1 d . . . . .
C6 C 0.0459(8) 1.0133(2) 0.64132(10) 0.0664(6) Uani 1 1 d . . . . .
H6 H -0.062724 1.046712 0.613387 0.080 Uiso 1 1 calc R U . . .
C8 C -0.0527(8) 0.8188(2) 0.60248(9) 0.0622(6) Uani 1 1 d . . . . .
C9 C -0.0543(9) 0.6994(2) 0.61283(11) 0.0713(7) Uani 1 1 d . . . . .
H9 H 0.025438 0.671994 0.643911 0.086 Uiso 1 1 calc R U . . .
C7 C 0.0758(8) 0.8980(2) 0.64185(9) 0.0656(6) Uani 1 1 d . . . . .
H7 H 0.187552 0.864461 0.669487 0.079 Uiso 1 1 calc R U . . .
N1 N 0.3872(8) 1.2545(3) 0.75507(11) 0.0902(8) Uani 1 1 d . . . . .
C11 C -0.2908(9) 0.6578(2) 0.53020(11) 0.0739(7) Uani 1 1 d . . . . .
H11 H -0.369786 0.604536 0.506184 0.089 Uiso 1 1 calc R U . . .
C5 C 0.1271(9) 1.2125(2) 0.67442(12) 0.0764(8) Uani 1 1 d . . . . .
H5 H 0.026638 1.241600 0.644968 0.092 Uiso 1 1 calc R U . . .
C10 C -0.1749(10) 0.6214(2) 0.57673(12) 0.0778(9) Uani 1 1 d . . . . .
C2 C 0.4220(10) 1.1390(3) 0.76082(12) 0.0858(9) Uani 1 1 d . . . . .
H2 H 0.520260 1.112249 0.790841 0.103 Uiso 1 1 calc R U . . .
C3 C 0.3243(8) 1.0575(3) 0.72598(10) 0.0724(7) Uani 1 1 d . . . . .
H3 H 0.361207 0.978338 0.732242 0.087 Uiso 1 1 calc R U . . .
C13 C -0.1687(8) 0.8562(2) 0.55490(10) 0.0662(6) Uani 1 1 d . . . . .
H13 H -0.166167 0.935458 0.546762 0.079 Uiso 1 1 calc R U . . .
C4 C 0.1693(7) 1.0931(2) 0.68103(9) 0.0641(6) Uani 1 1 d . . . . .
C12 C -0.2858(8) 0.7760(2) 0.52037(10) 0.0659(6) Uani 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 H1 0.9300 . ?
C1 N1 1.330(5) . ?
C1 C5 1.380(4) . ?
Cl1 C12 1.740(3) . ?
Cl2 C10 1.736(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.322(4) . ?
C6 C4 1.469(3) . ?
C8 C9 1.391(3) . ?
C8 C7 1.464(3) . ?
C8 C13 1.399(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C7 H7 0.9300 . ?
N1 C2 1.334(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.371(4) . ?
C11 C12 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.384(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.369(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
N1 C1 H1 117.6 . . ?
N1 C1 C5 124.8(3) . . ?
C5 C1 H1 117.6 . . ?
C7 C6 H6 117.2 . . ?
C7 C6 C4 125.6(2) . . ?
C4 C6 H6 117.2 . . ?
C9 C8 C7 117.9(2) . . ?
C9 C8 C13 118.3(2) . . ?
C13 C8 C7 123.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C6 C7 C8 125.3(2) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C1 N1 C2 115.0(3) . . ?
C10 C11 H11 121.3 . . ?
C10 C11 C12 117.5(2) . . ?
C12 C11 H11 121.3 . . ?
C1 C5 H5 120.4 . . ?
C1 C5 C4 119.1(3) . . ?
C4 C5 H5 120.4 . . ?
C9 C10 Cl2 119.3(2) . . ?
C11 C10 Cl2 118.6(2) . . ?
C11 C10 C9 122.1(3) . . ?
N1 C2 H2 117.6 . . ?
N1 C2 C3 124.8(3) . . ?
C3 C2 H2 117.6 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 120.1 . . ?
C5 C4 C6 118.9(2) . . ?
C5 C4 C3 116.6(2) . . ?
C3 C4 C6 124.5(2) . . ?
C11 C12 Cl1 118.17(19) . . ?
C13 C12 Cl1 119.4(2) . . ?
C13 C12 C11 122.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C2 C3 1.9(6) . . . . ?
C1 C5 C4 C6 178.6(3) . . . . ?
C1 C5 C4 C3 -0.5(5) . . . . ?
C8 C9 C10 Cl2 -178.9(3) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C8 C13 C12 Cl1 -179.6(2) . . . . ?
C8 C13 C12 C11 -0.9(5) . . . . ?
C9 C8 C7 C6 -169.0(3) . . . . ?
C9 C8 C13 C12 1.2(5) . . . . ?
C7 C6 C4 C5 178.3(3) . . . . ?
C7 C6 C4 C3 -2.6(5) . . . . ?
C7 C8 C9 C10 179.8(3) . . . . ?
C7 C8 C13 C12 -179.8(3) . . . . ?
N1 C1 C5 C4 1.2(6) . . . . ?
N1 C2 C3 C4 -1.4(6) . . . . ?
C5 C1 N1 C2 -1.8(6) . . . . ?
C10 C11 C12 Cl1 179.2(3) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C2 C3 C4 C6 -178.4(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C13 C8 C9 C10 -1.2(6) . . . . ?
C13 C8 C7 C6 12.0(5) . . . . ?
C4 C6 C7 C8 179.0(3) . . . . ?
C12 C11 C10 Cl2 179.3(3) . . . . ?
C12 C11 C10 C9 -0.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.825
_oxdiff_exptl_absorpt_empirical_full_min 0.428
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.529(2)
2 0.471(2)

####################################################################### 
# 
# 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_1357-am-l-284-etoh
_database_code_depnum_ccdc_archive 'CCDC 2289890'
loop_
_audit_author_name
_audit_author_address
'Rohan A.'
;Bits Pilani Hyderabad campus
India
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 O3, C13 H10 N'
_chemical_formula_sum            'C27 H21 N O3'
_chemical_formula_weight         407.45
_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                   6.7453(2)
_cell_length_b                   16.8984(3)
_cell_length_c                   18.0463(4)
_cell_angle_alpha                93.589(2)
_cell_angle_beta                 94.776(2)
_cell_angle_gamma                99.891(2)
_cell_volume                     2013.19(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6754
_cell_measurement_temperature    140
_cell_measurement_theta_max      79.1540
_cell_measurement_theta_min      4.9510
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50413
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23775
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.662
_diffrn_reflns_theta_min         4.934
_diffrn_ambient_temperature      140.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -15.00   0.50    0.50    --    0.00 -57.00-150.00  148
  2  ω     17.00  43.00   0.50    0.50    --    0.00  37.00-180.00   52
  3  ω    -89.00 -33.00   0.50    0.50    --    0.00 -37.00 -30.00  112
  4  ω     22.00  89.00   0.50    0.50    --    0.00  37.00  90.00  134
  5  ω    -11.00  15.00   0.50    0.50    --    0.00 -57.00-150.00   52
  6  ω    -29.00  47.00   0.50    0.50    --    0.00  82.00 -90.00  152
  7  ω     56.00  87.00   0.50    0.50    --    0.00  82.00 -90.00   62
  8  ω     25.00 126.00   0.50    0.60    --  107.20 -61.00 150.00  202
  9  ω     80.00 192.00   0.50    0.60    --  107.20  15.00 -90.00  224
 10  ω     61.00  87.00   0.50    0.60    --  107.20 -45.00 -30.00   52
 11  ω     88.00 114.00   0.50    0.60    --  107.20 -82.00 -60.00   52
 12  ω     27.00  53.00   0.50    0.60    --  107.20 -82.00  90.00   52
 13  ω     77.00 140.00   0.50    0.60    --  107.20 -82.00  90.00  126
 14  ω     20.00  62.00   0.50    0.60    --  107.20 -30.00-120.00   84
 15  ω     41.00  75.00   0.50    0.60    --  107.20 -82.00 -60.00   68
 16  ω     89.00 197.00   0.50    0.60    --  107.20  30.00-150.00  216
 17  ω     33.00  98.00   0.50    0.60    --  107.20 -15.00-120.00  130
 18  ω     61.00 132.00   0.50    0.60    --  107.20 -61.00   0.00  142
 19  ω     88.00 140.00   0.50    0.60    --  107.20 -82.00-150.00  104
 20  ω     87.00 196.00   0.50    0.60    --  107.20  45.00 150.00  218
 21  ω     28.00  54.00   0.50    0.60    --  107.20 -61.00   0.00   52
 22  ω     43.00 139.00   0.50    0.60    --  107.20 -82.00   0.00  192
 23  ω     61.00 110.00   0.50    0.60    --  107.20 -30.00 120.00   98
 24  ω     86.00 114.00   0.50    0.60    --  107.20 -82.00  30.00   56
 25  ω     79.00 110.00   0.50    0.60    --  107.20 -82.00-120.00   62
 26  ω     74.00 121.00   0.50    0.60    --  107.20 -30.00-120.00   94
 27  ω     21.00 138.00   0.50    0.60    --  107.20 -82.00 150.00  234
;
_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      -0.1006914000
_diffrn_orient_matrix_UB_12      -0.0621899000
_diffrn_orient_matrix_UB_13      -0.0640397000
_diffrn_orient_matrix_UB_21      -0.1885775000
_diffrn_orient_matrix_UB_22      -0.0195834000
_diffrn_orient_matrix_UB_23      0.0427466000
_diffrn_orient_matrix_UB_31      -0.0924370000
_diffrn_orient_matrix_UB_32      0.0660736000
_diffrn_orient_matrix_UB_33      -0.0381498000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                6467
_reflns_number_total             8483
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     576
_refine_ls_number_reflns         8483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.1399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1477
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C57(H57), C39(H39), C49(H49), C62(H62), C61(H61), C52(H52), C60(H60),
 C17(H17), C59(H59), C44(H44), C48(H48), C40(H40), C31(H31), C19(H19), C33(H33),
  C37(H37), C46(H46), C16(H16), C42(H42), C13(H13), C27(H27), C53(H53),
 C55(H55), C47(H47), C41(H41), C54(H54), C29(H29), C14(H14), C30(H30), C23(H23),
  C15(H15), C20(H20), C28(H28), C34(H34), C22(H22), C21(H21), C36(H36), C35(H35)
;
_atom_sites_solution_hydrogens   mixed
_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
O6 O 1.01791(19) 0.55839(7) 0.35677(7) 0.0346(3) Uani 1 1 d . . . . .
O1 O 0.7602(2) -0.00046(7) 0.30587(7) 0.0369(3) Uani 1 1 d . . . . .
O4 O 0.6936(2) 0.47760(7) 0.19348(7) 0.0370(3) Uani 1 1 d . . . . .
O3 O 0.4549(2) 0.02555(9) 0.14190(8) 0.0421(3) Uani 1 1 d . . . . .
O5 O 1.0195(2) 0.48079(8) 0.23119(8) 0.0423(3) Uani 1 1 d . . . . .
N7 N 0.7604(2) 0.03004(8) 0.44712(8) 0.0255(3) Uani 1 1 d . . . . .
N8 N 0.7289(2) 0.45743(8) 0.05265(8) 0.0268(3) Uani 1 1 d . . . . .
O2 O 0.4406(2) -0.05231(8) 0.26095(8) 0.0464(4) Uani 1 1 d . . . . .
C63 C 0.7601(2) 0.52715(9) 0.01897(9) 0.0250(3) Uani 1 1 d . . . . .
C58 C 0.7573(2) 0.52593(10) -0.06030(9) 0.0267(3) Uani 1 1 d . . . . .
C26 C 0.6805(3) 0.48183(9) 0.35990(9) 0.0272(3) Uani 1 1 d . . . . .
C50 C 0.8152(2) 0.10868(9) 0.47156(9) 0.0252(3) Uani 1 1 d . . . . .
C38 C 0.7306(2) -0.02937(10) 0.49441(9) 0.0255(3) Uani 1 1 d . . . . .
C51 C 0.6938(2) 0.38445(10) 0.01352(9) 0.0265(3) Uani 1 1 d . . . . .
C57 C 0.7195(3) 0.45107(10) -0.10147(10) 0.0299(4) Uani 1 1 d . . . . .
H57 H 0.716473 0.448897 -0.154292 0.036 Uiso 1 1 calc R U . . .
C39 C 0.6704(2) -0.11060(10) 0.46485(10) 0.0299(4) Uani 1 1 d . . . . .
H39 H 0.651347 -0.123535 0.412453 0.036 Uiso 1 1 calc R U . . .
C49 C 0.8398(3) 0.16830(10) 0.41937(10) 0.0303(4) Uani 1 1 d . . . . .
H49 H 0.821333 0.153324 0.367296 0.036 Uiso 1 1 calc R U . . .
C32 C 0.7499(3) 0.61718(9) 0.30262(9) 0.0291(4) Uani 1 1 d . . . . .
C45 C 0.8476(2) 0.13118(10) 0.54969(10) 0.0286(3) Uani 1 1 d . . . . .
C56 C 0.6864(2) 0.37978(10) -0.06617(10) 0.0287(3) Uani 1 1 d . . . . .
C25 C 0.8225(3) 0.53813(9) 0.31658(9) 0.0271(3) Uani 1 1 d . . . . .
C24 C 0.8488(3) 0.49446(9) 0.24028(9) 0.0293(4) Uani 1 1 d . . . . .
C62 C 0.7928(3) 0.60154(10) 0.06266(10) 0.0302(4) Uani 1 1 d . . . . .
H62 H 0.791648 0.602522 0.115311 0.036 Uiso 1 1 calc R U . . .
C61 C 0.8258(3) 0.67180(10) 0.02866(10) 0.0322(4) Uani 1 1 d . . . . .
H61 H 0.849437 0.721740 0.058051 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7703(3) -0.02257(9) 0.13516(9) 0.0296(4) Uani 1 1 d . . . . .
C43 C 0.7616(2) -0.01007(10) 0.57294(9) 0.0287(3) Uani 1 1 d . . . . .
C52 C 0.6607(3) 0.31346(10) 0.05180(11) 0.0331(4) Uani 1 1 d . . . . .
H52 H 0.668663 0.316617 0.104739 0.040 Uiso 1 1 calc R U . . .
C60 C 0.8255(3) 0.67140(10) -0.04978(11) 0.0340(4) Uani 1 1 d . . . . .
H60 H 0.848561 0.721037 -0.072368 0.041 Uiso 1 1 calc R U . . .
C17 C 0.9249(3) -0.05841(10) 0.16602(10) 0.0332(4) Uani 1 1 d . . . . .
H17 H 0.960050 -0.052002 0.218398 0.040 Uiso 1 1 calc R U . . .
C59 C 0.7925(3) 0.60084(10) -0.09321(10) 0.0324(4) Uani 1 1 d . . . . .
H59 H 0.792938 0.601537 -0.145794 0.039 Uiso 1 1 calc R U . . .
C44 C 0.8195(3) 0.07076(11) 0.59891(9) 0.0311(4) Uani 1 1 d . . . . .
H44 H 0.840131 0.084917 0.651115 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6108(3) -0.01239(10) 0.25642(10) 0.0326(4) Uani 1 1 d . . . . .
C18 C 0.7478(3) 0.11498(10) 0.19928(10) 0.0329(4) Uani 1 1 d . . . . .
C48 C 0.8905(3) 0.24773(10) 0.44533(11) 0.0340(4) Uani 1 1 d . . . . .
H48 H 0.903447 0.287988 0.410715 0.041 Uiso 1 1 calc R U . . .
C40 C 0.6403(3) -0.16983(11) 0.51290(11) 0.0340(4) Uani 1 1 d . . . . .
H40 H 0.597882 -0.224251 0.493519 0.041 Uiso 1 1 calc R U . . .
C31 C 0.7471(3) 0.46172(11) 0.42976(10) 0.0345(4) Uani 1 1 d . . . . .
H31 H 0.883326 0.480759 0.449269 0.041 Uiso 1 1 calc R U . . .
C19 C 0.9545(3) 0.14131(11) 0.19936(11) 0.0373(4) Uani 1 1 d . . . . .
H19 H 1.038908 0.104196 0.185926 0.045 Uiso 1 1 calc R U . . .
C33 C 0.8609(3) 0.66985(10) 0.25838(10) 0.0371(4) Uani 1 1 d . . . . .
H33 H 0.974440 0.654901 0.236996 0.044 Uiso 1 1 calc R U . . .
C37 C 0.5865(3) 0.64119(11) 0.33389(10) 0.0384(4) Uani 1 1 d . . . . .
H37 H 0.508689 0.606441 0.364221 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6477(3) 0.02682(10) 0.18165(10) 0.0313(4) Uani 1 1 d . . . . .
C46 C 0.9040(3) 0.21490(11) 0.57365(11) 0.0348(4) Uani 1 1 d . . . . .
H46 H 0.927504 0.231309 0.625410 0.042 Uiso 1 1 calc R U . . .
C16 C 1.0287(3) -0.10346(10) 0.12119(11) 0.0367(4) Uani 1 1 d . . . . .
H16 H 1.133878 -0.127750 0.143189 0.044 Uiso 1 1 calc R U . . .
C42 C 0.7298(3) -0.07411(11) 0.62071(10) 0.0352(4) Uani 1 1 d . . . . .
H42 H 0.749672 -0.062734 0.673292 0.042 Uiso 1 1 calc R U . . .
C13 C 0.7242(3) -0.03307(12) 0.05803(10) 0.0398(4) Uani 1 1 d . . . . .
H13 H 0.619265 -0.008953 0.035607 0.048 Uiso 1 1 calc R U . . .
C27 C 0.4813(3) 0.45185(11) 0.33231(10) 0.0378(4) Uani 1 1 d . . . . .
H27 H 0.433318 0.463902 0.284048 0.045 Uiso 1 1 calc R U . . .
C53 C 0.6174(3) 0.24046(11) 0.01168(12) 0.0383(4) Uani 1 1 d . . . . .
H53 H 0.594621 0.192689 0.037178 0.046 Uiso 1 1 calc R U . . .
C55 C 0.6421(3) 0.30212(11) -0.10533(11) 0.0364(4) Uani 1 1 d . . . . .
H55 H 0.637856 0.297286 -0.158197 0.044 Uiso 1 1 calc R U . . .
C47 C 0.9242(3) 0.27114(10) 0.52290(11) 0.0371(4) Uani 1 1 d . . . . .
H47 H 0.961122 0.326610 0.539474 0.045 Uiso 1 1 calc R U . . .
C41 C 0.6711(3) -0.15160(11) 0.59123(11) 0.0373(4) Uani 1 1 d . . . . .
H41 H 0.650549 -0.193946 0.623525 0.045 Uiso 1 1 calc R U . . .
C54 C 0.6056(3) 0.23449(11) -0.06736(12) 0.0392(4) Uani 1 1 d . . . . .
H54 H 0.572102 0.183022 -0.094125 0.047 Uiso 1 1 calc R U . . .
C29 C 0.4194(3) 0.38583(11) 0.44476(12) 0.0449(5) Uani 1 1 d . . . . .
H29 H 0.330340 0.354014 0.473864 0.054 Uiso 1 1 calc R U . . .
C14 C 0.8282(3) -0.07794(12) 0.01356(11) 0.0455(5) Uani 1 1 d . . . . .
H14 H 0.794031 -0.084265 -0.038875 0.055 Uiso 1 1 calc R U . . .
C30 C 0.6169(3) 0.41390(12) 0.47189(11) 0.0437(5) Uani 1 1 d . . . . .
H30 H 0.665214 0.400665 0.519681 0.052 Uiso 1 1 calc R U . . .
C23 C 0.6275(3) 0.17047(11) 0.21957(11) 0.0420(5) Uani 1 1 d . . . . .
H23 H 0.486017 0.153234 0.220095 0.050 Uiso 1 1 calc R U . . .
C15 C 0.9804(3) -0.11339(11) 0.04447(11) 0.0413(5) Uani 1 1 d . . . . .
H15 H 1.051588 -0.144277 0.013863 0.050 Uiso 1 1 calc R U . . .
C20 C 1.0391(4) 0.22202(11) 0.21909(12) 0.0459(5) Uani 1 1 d . . . . .
H20 H 1.180712 0.239523 0.219075 0.055 Uiso 1 1 calc R U . . .
C28 C 0.3512(3) 0.40442(12) 0.37445(12) 0.0452(5) Uani 1 1 d . . . . .
H28 H 0.215215 0.384703 0.354972 0.054 Uiso 1 1 calc R U . . .
C34 C 0.8072(4) 0.74396(11) 0.24528(11) 0.0489(6) Uani 1 1 d . . . . .
H34 H 0.882787 0.778573 0.214215 0.059 Uiso 1 1 calc R U . . .
C22 C 0.7124(4) 0.25101(12) 0.23911(12) 0.0495(5) Uani 1 1 d . . . . .
H22 H 0.628472 0.288236 0.252758 0.059 Uiso 1 1 calc R U . . .
C21 C 0.9172(4) 0.27680(11) 0.23872(11) 0.0478(5) Uani 1 1 d . . . . .
H21 H 0.974810 0.331754 0.251801 0.057 Uiso 1 1 calc R U . . .
C36 C 0.5360(4) 0.71638(12) 0.32091(12) 0.0507(6) Uani 1 1 d . . . . .
H36 H 0.424394 0.732375 0.342817 0.061 Uiso 1 1 calc R U . . .
C35 C 0.6465(4) 0.76763(11) 0.27663(12) 0.0544(6) Uani 1 1 d . . . . .
H35 H 0.611619 0.818627 0.268037 0.065 Uiso 1 1 calc R U . . .
H8 H 0.726(4) 0.4602(16) 0.1114(16) 0.076(8) Uiso 1 1 d . . . . .
H7 H 0.743(4) 0.0125(15) 0.3902(15) 0.069(8) Uiso 1 1 d . . . . .
H6 H 1.099(4) 0.5298(16) 0.3271(16) 0.075(9) Uiso 1 1 d . . . . .
H3 H 0.370(4) -0.0092(18) 0.1651(17) 0.078(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
O6 C25 1.427(2) . ?
O6 H6 0.96(3) . ?
O1 C9 1.269(2) . ?
O4 C24 1.269(2) . ?
O3 C11 1.428(2) . ?
O3 H3 0.90(3) . ?
O5 C24 1.235(2) . ?
N7 C50 1.3518(19) . ?
N7 C38 1.358(2) . ?
N7 H7 1.04(3) . ?
N8 C63 1.352(2) . ?
N8 C51 1.356(2) . ?
N8 H8 1.06(3) . ?
O2 C9 1.240(2) . ?
C63 C58 1.428(2) . ?
C63 C62 1.415(2) . ?
C58 C57 1.399(2) . ?
C58 C59 1.423(2) . ?
C26 C25 1.529(2) . ?
C26 C31 1.385(2) . ?
C26 C27 1.391(2) . ?
C50 C49 1.420(2) . ?
C50 C45 1.426(2) . ?
C38 C39 1.419(2) . ?
C38 C43 1.424(2) . ?
C51 C56 1.432(2) . ?
C51 C52 1.416(2) . ?
C57 H57 0.9500 . ?
C57 C56 1.391(2) . ?
C39 H39 0.9500 . ?
C39 C40 1.365(2) . ?
C49 H49 0.9500 . ?
C49 C48 1.369(2) . ?
C32 C25 1.528(2) . ?
C32 C33 1.396(2) . ?
C32 C37 1.388(2) . ?
C45 C44 1.394(2) . ?
C45 C46 1.430(2) . ?
C56 C55 1.423(2) . ?
C25 C24 1.559(2) . ?
C62 H62 0.9500 . ?
C62 C61 1.363(2) . ?
C61 H61 0.9500 . ?
C61 C60 1.415(3) . ?
C12 C17 1.388(3) . ?
C12 C11 1.533(2) . ?
C12 C13 1.394(2) . ?
C43 C44 1.394(2) . ?
C43 C42 1.424(2) . ?
C52 H52 0.9500 . ?
C52 C53 1.364(2) . ?
C60 H60 0.9500 . ?
C60 C59 1.360(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.387(2) . ?
C59 H59 0.9500 . ?
C44 H44 0.9500 . ?
C9 C11 1.560(2) . ?
C18 C19 1.389(3) . ?
C18 C11 1.528(2) . ?
C18 C23 1.392(3) . ?
C48 H48 0.9500 . ?
C48 C47 1.419(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.418(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(3) . ?
C37 H37 0.9500 . ?
C37 C36 1.399(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.359(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.389(3) . ?
C42 H42 0.9500 . ?
C42 C41 1.362(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.418(3) . ?
C55 H55 0.9500 . ?
C55 C54 1.366(3) . ?
C47 H47 0.9500 . ?
C41 H41 0.9500 . ?
C54 H54 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.373(3) . ?
C29 C28 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(3) . ?
C30 H30 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.394(3) . ?
C15 H15 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C28 H28 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.370(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.376(3) . ?
C21 H21 0.9500 . ?
C36 H36 0.9500 . ?
C36 C35 1.381(3) . ?
C35 H35 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O6 H6 102.8(17) . . ?
C11 O3 H3 104.1(19) . . ?
C50 N7 C38 122.44(14) . . ?
C50 N7 H7 120.5(14) . . ?
C38 N7 H7 117.0(14) . . ?
C63 N8 C51 122.16(14) . . ?
C63 N8 H8 118.7(14) . . ?
C51 N8 H8 119.1(14) . . ?
N8 C63 C58 120.32(14) . . ?
N8 C63 C62 119.61(15) . . ?
C62 C63 C58 120.06(15) . . ?
C57 C58 C63 118.17(15) . . ?
C57 C58 C59 123.52(16) . . ?
C59 C58 C63 118.31(15) . . ?
C31 C26 C25 120.01(16) . . ?
C31 C26 C27 118.18(16) . . ?
C27 C26 C25 121.77(15) . . ?
N7 C50 C49 119.88(15) . . ?
N7 C50 C45 119.68(15) . . ?
C49 C50 C45 120.44(15) . . ?
N7 C38 C39 119.43(15) . . ?
N7 C38 C43 120.04(15) . . ?
C39 C38 C43 120.53(15) . . ?
N8 C51 C56 119.82(15) . . ?
N8 C51 C52 119.65(15) . . ?
C52 C51 C56 120.52(15) . . ?
C58 C57 H57 119.5 . . ?
C56 C57 C58 120.94(15) . . ?
C56 C57 H57 119.5 . . ?
C38 C39 H39 120.5 . . ?
C40 C39 C38 118.94(16) . . ?
C40 C39 H39 120.5 . . ?
C50 C49 H49 120.5 . . ?
C48 C49 C50 118.92(16) . . ?
C48 C49 H49 120.5 . . ?
C33 C32 C25 117.68(16) . . ?
C37 C32 C25 123.99(15) . . ?
C37 C32 C33 118.26(16) . . ?
C50 C45 C46 118.25(16) . . ?
C44 C45 C50 118.52(15) . . ?
C44 C45 C46 123.22(16) . . ?
C57 C56 C51 118.58(15) . . ?
C57 C56 C55 123.31(16) . . ?
C55 C56 C51 118.10(16) . . ?
O6 C25 C26 110.13(13) . . ?
O6 C25 C32 107.14(13) . . ?
O6 C25 C24 107.18(13) . . ?
C26 C25 C24 109.71(13) . . ?
C32 C25 C26 113.40(14) . . ?
C32 C25 C24 109.06(13) . . ?
O4 C24 C25 116.80(15) . . ?
O5 C24 O4 126.63(16) . . ?
O5 C24 C25 116.56(16) . . ?
C63 C62 H62 120.2 . . ?
C61 C62 C63 119.54(16) . . ?
C61 C62 H62 120.2 . . ?
C62 C61 H61 119.5 . . ?
C62 C61 C60 120.94(16) . . ?
C60 C61 H61 119.5 . . ?
C17 C12 C11 123.29(15) . . ?
C17 C12 C13 117.85(17) . . ?
C13 C12 C11 118.86(16) . . ?
C44 C43 C38 118.11(15) . . ?
C44 C43 C42 123.52(16) . . ?
C42 C43 C38 118.37(16) . . ?
C51 C52 H52 120.4 . . ?
C53 C52 C51 119.13(17) . . ?
C53 C52 H52 120.4 . . ?
C61 C60 H60 119.6 . . ?
C59 C60 C61 120.80(16) . . ?
C59 C60 H60 119.6 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.72(17) . . ?
C16 C17 H17 119.6 . . ?
C58 C59 H59 119.8 . . ?
C60 C59 C58 120.33(16) . . ?
C60 C59 H59 119.8 . . ?
C45 C44 C43 121.20(15) . . ?
C45 C44 H44 119.4 . . ?
C43 C44 H44 119.4 . . ?
O1 C9 C11 116.01(15) . . ?
O2 C9 O1 127.09(17) . . ?
O2 C9 C11 116.90(17) . . ?
C19 C18 C11 122.80(16) . . ?
C19 C18 C23 118.69(17) . . ?
C23 C18 C11 118.43(17) . . ?
C49 C48 H48 119.3 . . ?
C49 C48 C47 121.34(17) . . ?
C47 C48 H48 119.3 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.19(17) . . ?
C41 C40 H40 119.4 . . ?
C26 C31 H31 119.5 . . ?
C26 C31 C30 120.93(18) . . ?
C30 C31 H31 119.5 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.39(19) . . ?
C20 C19 H19 119.8 . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.8(2) . . ?
C34 C33 H33 119.6 . . ?
C32 C37 H37 119.9 . . ?
C32 C37 C36 120.27(19) . . ?
C36 C37 H37 119.9 . . ?
O3 C11 C12 109.18(14) . . ?
O3 C11 C9 107.65(14) . . ?
O3 C11 C18 107.62(14) . . ?
C12 C11 C9 109.58(13) . . ?
C18 C11 C12 113.85(14) . . ?
C18 C11 C9 108.77(14) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 C45 120.46(17) . . ?
C47 C46 H46 119.8 . . ?
C17 C16 H16 119.7 . . ?
C17 C16 C15 120.61(18) . . ?
C15 C16 H16 119.7 . . ?
C43 C42 H42 119.9 . . ?
C41 C42 C43 120.19(17) . . ?
C41 C42 H42 119.9 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.23(19) . . ?
C14 C13 H13 119.4 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.87(18) . . ?
C28 C27 H27 119.6 . . ?
C52 C53 H53 119.4 . . ?
C52 C53 C54 121.27(18) . . ?
C54 C53 H53 119.4 . . ?
C56 C55 H55 119.8 . . ?
C54 C55 C56 120.38(18) . . ?
C54 C55 H55 119.8 . . ?
C48 C47 H47 119.7 . . ?
C46 C47 C48 120.57(16) . . ?
C46 C47 H47 119.7 . . ?
C40 C41 H41 119.6 . . ?
C42 C41 C40 120.78(16) . . ?
C42 C41 H41 119.6 . . ?
C53 C54 H54 119.7 . . ?
C55 C54 C53 120.56(17) . . ?
C55 C54 H54 119.7 . . ?
C30 C29 H29 120.3 . . ?
C30 C29 C28 119.31(18) . . ?
C28 C29 H29 120.3 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.59(18) . . ?
C15 C14 H14 119.7 . . ?
C31 C30 H30 119.8 . . ?
C29 C30 C31 120.46(18) . . ?
C29 C30 H30 119.8 . . ?
C18 C23 H23 119.6 . . ?
C18 C23 C22 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 C16 119.00(18) . . ?
C14 C15 H15 120.5 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.9 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 H28 119.9 . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.78(19) . . ?
C35 C34 H34 119.6 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.61(18) . . ?
C22 C21 H21 120.2 . . ?
C37 C36 H36 119.6 . . ?
C35 C36 C37 120.8(2) . . ?
C35 C36 H36 119.6 . . ?
C34 C35 C36 119.13(18) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C25 C24 O4 -174.12(13) . . . . ?
O6 C25 C24 O5 4.92(19) . . . . ?
O1 C9 C11 O3 -164.87(14) . . . . ?
O1 C9 C11 C12 76.50(18) . . . . ?
O1 C9 C11 C18 -48.5(2) . . . . ?
N7 C50 C49 C48 178.42(15) . . . . ?
N7 C50 C45 C44 -0.6(2) . . . . ?
N7 C50 C45 C46 -179.55(15) . . . . ?
N7 C38 C39 C40 -179.80(15) . . . . ?
N7 C38 C43 C44 1.0(2) . . . . ?
N7 C38 C43 C42 -179.69(14) . . . . ?
N8 C63 C58 C57 0.6(2) . . . . ?
N8 C63 C58 C59 -179.51(15) . . . . ?
N8 C63 C62 C61 179.48(15) . . . . ?
N8 C51 C56 C57 1.1(2) . . . . ?
N8 C51 C56 C55 -177.83(15) . . . . ?
N8 C51 C52 C53 177.36(15) . . . . ?
O2 C9 C11 O3 15.9(2) . . . . ?
O2 C9 C11 C12 -102.76(18) . . . . ?
O2 C9 C11 C18 132.20(17) . . . . ?
C63 N8 C51 C56 -0.8(2) . . . . ?
C63 N8 C51 C52 -179.57(15) . . . . ?
C63 C58 C57 C56 -0.2(2) . . . . ?
C63 C58 C59 C60 -0.8(2) . . . . ?
C63 C62 C61 C60 0.8(3) . . . . ?
C58 C63 C62 C61 -1.4(2) . . . . ?
C58 C57 C56 C51 -0.6(2) . . . . ?
C58 C57 C56 C55 178.28(16) . . . . ?
C26 C25 C24 O4 66.31(18) . . . . ?
C26 C25 C24 O5 -114.64(16) . . . . ?
C26 C31 C30 C29 -0.1(3) . . . . ?
C26 C27 C28 C29 -0.5(3) . . . . ?
C50 N7 C38 C39 179.11(14) . . . . ?
C50 N7 C38 C43 -1.5(2) . . . . ?
C50 C49 C48 C47 1.8(3) . . . . ?
C50 C45 C44 C43 0.2(2) . . . . ?
C50 C45 C46 C47 0.5(3) . . . . ?
C38 N7 C50 C49 -178.61(15) . . . . ?
C38 N7 C50 C45 1.3(2) . . . . ?
C38 C39 C40 C41 -1.0(3) . . . . ?
C38 C43 C44 C45 -0.4(2) . . . . ?
C38 C43 C42 C41 0.0(3) . . . . ?
C51 N8 C63 C58 -0.1(2) . . . . ?
C51 N8 C63 C62 178.95(15) . . . . ?
C51 C56 C55 C54 0.7(3) . . . . ?
C51 C52 C53 C54 0.2(3) . . . . ?
C57 C58 C59 C60 179.10(16) . . . . ?
C57 C56 C55 C54 -178.19(17) . . . . ?
C39 C38 C43 C44 -179.60(15) . . . . ?
C39 C38 C43 C42 -0.3(2) . . . . ?
C39 C40 C41 C42 0.7(3) . . . . ?
C49 C50 C45 C44 179.27(15) . . . . ?
C49 C50 C45 C46 0.3(2) . . . . ?
C49 C48 C47 C46 -0.9(3) . . . . ?
C32 C25 C24 O4 -58.45(19) . . . . ?
C32 C25 C24 O5 120.60(16) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C32 C37 C36 C35 0.4(3) . . . . ?
C45 C50 C49 C48 -1.5(2) . . . . ?
C45 C46 C47 C48 -0.3(3) . . . . ?
C56 C51 C52 C53 -1.4(2) . . . . ?
C56 C55 C54 C53 -1.9(3) . . . . ?
C25 C26 C31 C30 176.60(16) . . . . ?
C25 C26 C27 C28 -176.31(17) . . . . ?
C25 C32 C33 C34 -177.99(16) . . . . ?
C25 C32 C37 C36 176.99(17) . . . . ?
C62 C63 C58 C57 -178.44(15) . . . . ?
C62 C63 C58 C59 1.4(2) . . . . ?
C62 C61 C60 C59 -0.1(3) . . . . ?
C61 C60 C59 C58 0.1(3) . . . . ?
C12 C17 C16 C15 0.2(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C43 C38 C39 C40 0.8(2) . . . . ?
C43 C42 C41 C40 -0.1(3) . . . . ?
C52 C51 C56 C57 179.92(15) . . . . ?
C52 C51 C56 C55 1.0(2) . . . . ?
C52 C53 C54 C55 1.5(3) . . . . ?
C17 C12 C11 O3 -155.19(16) . . . . ?
C17 C12 C11 C9 -37.5(2) . . . . ?
C17 C12 C11 C18 84.5(2) . . . . ?
C17 C12 C13 C14 0.2(3) . . . . ?
C17 C16 C15 C14 0.0(3) . . . . ?
C59 C58 C57 C56 179.92(16) . . . . ?
C44 C45 C46 C47 -178.34(17) . . . . ?
C44 C43 C42 C41 179.23(16) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C18 C23 C22 C21 -0.1(3) . . . . ?
C31 C26 C25 O6 3.5(2) . . . . ?
C31 C26 C25 C32 -116.59(17) . . . . ?
C31 C26 C25 C24 121.20(17) . . . . ?
C31 C26 C27 C28 1.4(3) . . . . ?
C19 C18 C11 O3 -144.34(17) . . . . ?
C19 C18 C11 C12 -23.2(2) . . . . ?
C19 C18 C11 C9 99.30(19) . . . . ?
C19 C18 C23 C22 0.4(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C33 C32 C25 O6 63.25(18) . . . . ?
C33 C32 C25 C26 -175.02(15) . . . . ?
C33 C32 C25 C24 -52.4(2) . . . . ?
C33 C32 C37 C36 0.0(3) . . . . ?
C33 C34 C35 C36 -0.8(3) . . . . ?
C37 C32 C25 O6 -113.72(18) . . . . ?
C37 C32 C25 C26 8.0(2) . . . . ?
C37 C32 C25 C24 130.58(17) . . . . ?
C37 C32 C33 C34 -0.8(3) . . . . ?
C37 C36 C35 C34 0.0(3) . . . . ?
C11 C12 C17 C16 179.03(15) . . . . ?
C11 C12 C13 C14 -179.15(17) . . . . ?
C11 C18 C19 C20 -177.18(17) . . . . ?
C11 C18 C23 C22 177.42(17) . . . . ?
C46 C45 C44 C43 179.08(16) . . . . ?
C42 C43 C44 C45 -179.66(16) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C13 C12 C11 O3 24.2(2) . . . . ?
C13 C12 C11 C9 141.84(16) . . . . ?
C13 C12 C11 C18 -96.11(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C27 C26 C25 O6 -178.88(15) . . . . ?
C27 C26 C25 C32 61.1(2) . . . . ?
C27 C26 C25 C24 -61.1(2) . . . . ?
C27 C26 C31 C30 -1.1(3) . . . . ?
C30 C29 C28 C27 -0.8(3) . . . . ?
C23 C18 C19 C20 -0.3(3) . . . . ?
C23 C18 C11 O3 38.8(2) . . . . ?
C23 C18 C11 C12 159.96(16) . . . . ?
C23 C18 C11 C9 -77.5(2) . . . . ?
C23 C22 C21 C20 -0.3(3) . . . . ?
C28 C29 C30 C31 1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.078
_oxdiff_exptl_absorpt_empirical_full_min 0.570
####################################################################### 
# 
# 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_1333-am-r-276-dcm
_database_code_depnum_ccdc_archive 'CCDC 2289889'
loop_
_audit_author_name
_audit_author_address
'Rohan A.'
;Bits Pilani Hyderabad campus
India
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 O3, C13 H11 Br N'
_chemical_formula_sum            'C27 H22 Br N O3'
_chemical_formula_weight         488.36
_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'
Br Br -0.6763 1.2805 '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                   8.79940(10)
_cell_length_b                   10.29960(10)
_cell_length_c                   13.0538(2)
_cell_angle_alpha                89.3630(10)
_cell_angle_beta                 74.7030(10)
_cell_angle_gamma                82.8310(10)
_cell_volume                     1131.94(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9140
_cell_measurement_temperature    143
_cell_measurement_theta_max      79.1760
_cell_measurement_theta_min      4.2990
_shelx_estimated_absorpt_T_max   0.773
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    2.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84605
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.2
_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  0.0302
_diffrn_reflns_av_unetI/netI     0.0356
_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       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12529
_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         79.457
_diffrn_reflns_theta_min         5.253
_diffrn_ambient_temperature      143.00
_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     38.00  88.00   0.50    0.50    --    0.00  57.00 -30.00  100
  2  ω    -83.00  17.00   0.50    0.50    --    0.00 -37.00   0.00  200
  3  ω     -6.00  35.00   0.50    0.50    --    0.00  57.00-180.00   82
  4  ω    -19.00  34.00   0.50    0.50    --    0.00  57.00 -30.00  106
  5  ω     27.00  89.00   0.50    0.50    --    0.00  37.00  90.00  124
  6  ω     20.00 140.00   0.50    2.01    --  107.20 -82.00-150.00  240
  7  ω     29.00  79.00   0.50    2.01    --  107.20 -82.00  90.00  100
  8  ω     42.00  79.00   0.50    2.01    --  107.20 -82.00  30.00   74
  9  ω    142.00 182.00   0.50    2.01    --  107.20  30.00-150.00   80
 10  ω     56.00 137.00   0.50    2.01    --  107.20 -82.00   0.00  162
 11  ω     77.00 102.00   0.50    2.01    --  107.20 -82.00 150.00   50
 12  ω     88.00 138.00   0.50    2.01    --  107.20 -82.00  90.00  100
 13  ω     23.00  95.00   0.50    2.01    --  107.20 -15.00-150.00  144
 14  ω     90.00 196.00   0.50    2.01    --  107.20  15.00 120.00  212
 15  ω     74.00 137.00   0.50    2.01    --  107.20 -82.00 -90.00  126
 16  ω     25.00  62.00   0.50    2.01    --  107.20 -82.00 -90.00   74
 17  ω     91.00 127.00   0.50    2.01    --  107.20 -30.00  30.00   72
 18  ω     49.00 124.00   0.50    2.01    --  107.20 -30.00 -90.00  150
 19  ω    105.00 134.00   0.50    2.01    --  107.20 -82.00  30.00   58
 20  ω     92.00 118.00   0.50    2.01    --  107.20  30.00 150.00   52
 21  ω    153.00 185.00   0.50    2.01    --  107.20  30.00 150.00   64
 22  ω     42.00 140.00   0.50    2.01    --  107.20 -82.00  60.00  196
 23  ω     18.00 127.00   0.50    2.01    --  107.20 -61.00-150.00  218
 24  ω     89.00 193.00   0.50    2.01    --  107.20  45.00-180.00  208
;
_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      0.0345863000
_diffrn_orient_matrix_UB_12      -0.0260703000
_diffrn_orient_matrix_UB_13      -0.1204469000
_diffrn_orient_matrix_UB_21      0.1796596000
_diffrn_orient_matrix_UB_22      -0.0125397000
_diffrn_orient_matrix_UB_23      -0.0100209000
_diffrn_orient_matrix_UB_31      0.0022399000
_diffrn_orient_matrix_UB_32      -0.1479911000
_diffrn_orient_matrix_UB_33      0.0192255000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                4386
_reflns_number_total             4746
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.315
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.106
_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)+(0.0637P)²+0.7866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1177
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C22(H22), C2(H2), C9(H9), C5(H5), C8(H8), C26(H26), C25(H25),
 C13(H13), C24(H24), C6(H6), C31(H31), C23(H23), C27(H27), C30(H30), C29(H29),
 C12(H12), C11(H11), C28(H28)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br15 Br 0.89997(3) 0.50081(2) 0.31861(2) 0.03675(11) Uani 1 1 d . . . . .
O16 O 0.3293(2) 0.55771(15) 0.24393(12) 0.0299(4) Uani 1 1 d . . . . .
O18 O 0.4797(2) 0.84530(16) 0.30334(14) 0.0271(3) Uani 1 1 d . . . . .
O17 O 0.3641(3) 0.64530(18) 0.39106(13) 0.0416(5) Uani 1 1 d . . . . .
N1 N 0.7147(2) -0.34803(18) 0.65217(15) 0.0269(4) Uani 1 1 d . . . . .
C7 C 0.7609(3) 0.0024(2) 0.47994(18) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.819310 0.063868 0.501281 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7450(3) -0.1203(2) 0.53797(17) 0.0236(4) Uani 1 1 d . . . . .
C33 C 0.4353(3) 0.76379(19) 0.23089(16) 0.0214(4) Uani 1 1 d . . . . .
C32 C 0.3085(3) 0.8468(2) 0.18943(16) 0.0224(4) Uani 1 1 d . . . . .
C21 C 0.3703(3) 0.6448(2) 0.29499(18) 0.0268(4) Uani 1 1 d . . . . .
C3 C 0.7900(3) -0.1346(2) 0.63297(18) 0.0267(4) Uani 1 1 d . . . . .
H3 H 0.832179 -0.065546 0.659461 0.032 Uiso 1 1 calc R U . . .
C22 C 0.7328(3) 0.7298(2) 0.14585(18) 0.0257(4) Uani 1 1 d . . . . .
H22 H 0.747441 0.772372 0.206101 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7945(3) 0.3603(2) 0.28907(19) 0.0277(4) Uani 1 1 d . . . . .
C2 C 0.7730(3) -0.2493(2) 0.68809(18) 0.0286(5) Uani 1 1 d . . . . .
H2 H 0.803230 -0.258201 0.752751 0.034 Uiso 1 1 calc R U . . .
C19 C 0.5799(3) 0.71510(19) 0.14067(16) 0.0215(4) Uani 1 1 d . . . . .
C9 C 0.7834(3) 0.2553(2) 0.35663(18) 0.0264(4) Uani 1 1 d . . . . .
H9 H 0.824203 0.254956 0.417154 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6861(3) -0.2261(2) 0.50219(18) 0.0276(4) Uani 1 1 d . . . . .
H5 H 0.656067 -0.220859 0.437356 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6977(3) 0.0325(2) 0.39874(18) 0.0267(4) Uani 1 1 d . . . . .
H8 H 0.637054 -0.029523 0.380850 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7111(3) 0.1501(2) 0.33403(17) 0.0261(4) Uani 1 1 d . . . . .
C26 C 0.5613(3) 0.6521(2) 0.05125(17) 0.0247(4) Uani 1 1 d . . . . .
H26 H 0.457705 0.641941 0.046045 0.030 Uiso 1 1 calc R U . . .
C25 C 0.6926(3) 0.6043(2) -0.02997(18) 0.0296(5) Uani 1 1 d . . . . .
H25 H 0.678578 0.560517 -0.089893 0.036 Uiso 1 1 calc R U . . .
C13 C 0.7354(3) 0.3660(2) 0.2011(2) 0.0329(5) Uani 1 1 d . . . . .
H13 H 0.744005 0.439749 0.156534 0.039 Uiso 1 1 calc R U . . .
C24 C 0.8447(3) 0.6202(2) -0.02390(19) 0.0313(5) Uani 1 1 d . . . . .
H24 H 0.934546 0.588112 -0.079828 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6716(3) -0.3384(2) 0.56127(18) 0.0280(4) Uani 1 1 d . . . . .
H6 H 0.630406 -0.409667 0.536927 0.034 Uiso 1 1 calc R U . . .
C31 C 0.3557(3) 0.9483(2) 0.12150(18) 0.0284(5) Uani 1 1 d . . . . .
H31 H 0.465374 0.957902 0.097390 0.034 Uiso 1 1 calc R U . . .
C23 C 0.8647(3) 0.6830(2) 0.0639(2) 0.0308(5) Uani 1 1 d . . . . .
H23 H 0.968354 0.694215 0.068325 0.037 Uiso 1 1 calc R U . . .
C27 C 0.1480(3) 0.8337(2) 0.2233(2) 0.0311(5) Uani 1 1 d . . . . .
H27 H 0.113263 0.764847 0.269120 0.037 Uiso 1 1 calc R U . . .
C30 C 0.2455(3) 1.0357(2) 0.0884(2) 0.0346(5) Uani 1 1 d . . . . .
H30 H 0.279750 1.104509 0.042414 0.042 Uiso 1 1 calc R U . . .
C29 C 0.0851(3) 1.0219(3) 0.1227(2) 0.0370(6) Uani 1 1 d . . . . .
H29 H 0.009122 1.080883 0.100044 0.044 Uiso 1 1 calc R U . . .
C12 C 0.6631(3) 0.2614(3) 0.1792(2) 0.0382(6) Uani 1 1 d . . . . .
H12 H 0.621590 0.263071 0.118935 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6511(3) 0.1540(2) 0.2450(2) 0.0320(5) Uani 1 1 d . . . . .
H11 H 0.601514 0.082701 0.229300 0.038 Uiso 1 1 calc R U . . .
C28 C 0.0370(3) 0.9221(3) 0.1900(2) 0.0375(6) Uani 1 1 d . . . . .
H28 H -0.072835 0.913096 0.214041 0.045 Uiso 1 1 calc R U . . .
H18 H 0.452(4) 0.818(3) 0.347(3) 0.033(10) Uiso 1 1 d . . . . .
H1 H 0.708(7) -0.432(6) 0.696(5) 0.12(2) 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
Br15 C14 1.908(2) . ?
O16 C21 1.265(3) . ?
O18 C33 1.431(2) . ?
O18 H18 0.63(4) . ?
O17 C21 1.241(3) . ?
N1 C2 1.336(3) . ?
N1 C6 1.337(3) . ?
N1 H1 1.03(6) . ?
C7 H7 0.9500 . ?
C7 C4 1.470(3) . ?
C7 C8 1.338(3) . ?
C4 C3 1.399(3) . ?
C4 C5 1.397(3) . ?
C33 C32 1.530(3) . ?
C33 C21 1.558(3) . ?
C33 C19 1.523(3) . ?
C32 C31 1.394(3) . ?
C32 C27 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.380(3) . ?
C22 H22 0.9500 . ?
C22 C19 1.392(3) . ?
C22 C23 1.393(3) . ?
C14 C9 1.384(3) . ?
C14 C13 1.378(4) . ?
C2 H2 0.9500 . ?
C19 C26 1.398(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C10 1.467(3) . ?
C10 C11 1.395(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.387(3) . ?
C25 H25 0.9500 . ?
C25 C24 1.392(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.386(4) . ?
C24 H24 0.9500 . ?
C24 C23 1.384(4) . ?
C6 H6 0.9500 . ?
C31 H31 0.9500 . ?
C31 C30 1.390(3) . ?
C23 H23 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.402(4) . ?
C30 H30 0.9500 . ?
C30 C29 1.388(4) . ?
C29 H29 0.9500 . ?
C29 C28 1.378(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.390(3) . ?
C11 H11 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C33 O18 H18 101(3) . . ?
C2 N1 C6 120.73(19) . . ?
C2 N1 H1 117(3) . . ?
C6 N1 H1 122(3) . . ?
C4 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C8 C7 C4 123.6(2) . . ?
C3 C4 C7 119.9(2) . . ?
C5 C4 C7 122.7(2) . . ?
C5 C4 C3 117.45(19) . . ?
O18 C33 C32 106.88(16) . . ?
O18 C33 C21 106.74(17) . . ?
O18 C33 C19 110.10(18) . . ?
C32 C33 C21 112.26(18) . . ?
C19 C33 C32 111.35(16) . . ?
C19 C33 C21 109.38(17) . . ?
C31 C32 C33 117.83(19) . . ?
C27 C32 C33 123.3(2) . . ?
C27 C32 C31 118.6(2) . . ?
O16 C21 C33 116.80(18) . . ?
O17 C21 O16 126.7(2) . . ?
O17 C21 C33 116.5(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C19 C22 H22 119.5 . . ?
C19 C22 C23 120.9(2) . . ?
C23 C22 H22 119.5 . . ?
C9 C14 Br15 118.07(18) . . ?
C13 C14 Br15 119.12(17) . . ?
C13 C14 C9 122.8(2) . . ?
N1 C2 C3 121.2(2) . . ?
N1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C22 C19 C33 121.20(19) . . ?
C22 C19 C26 118.5(2) . . ?
C26 C19 C33 120.26(19) . . ?
C14 C9 H9 120.7 . . ?
C14 C9 C10 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C7 C8 H8 116.2 . . ?
C7 C8 C10 127.7(2) . . ?
C10 C8 H8 116.2 . . ?
C9 C10 C8 122.9(2) . . ?
C9 C10 C11 119.3(2) . . ?
C11 C10 C8 117.8(2) . . ?
C19 C26 H26 119.7 . . ?
C25 C26 C19 120.6(2) . . ?
C25 C26 H26 119.7 . . ?
C26 C25 H25 119.9 . . ?
C26 C25 C24 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C14 C13 H13 120.8 . . ?
C14 C13 C12 118.3(2) . . ?
C12 C13 H13 120.8 . . ?
C25 C24 H24 120.1 . . ?
C23 C24 C25 119.7(2) . . ?
C23 C24 H24 120.1 . . ?
N1 C6 C5 120.8(2) . . ?
N1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C32 C31 H31 119.4 . . ?
C30 C31 C32 121.3(2) . . ?
C30 C31 H31 119.4 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C32 C27 H27 120.0 . . ?
C32 C27 C28 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C31 C30 H30 120.1 . . ?
C29 C30 C31 119.8(2) . . ?
C29 C30 H30 120.1 . . ?
C30 C29 H29 120.3 . . ?
C28 C29 C30 119.5(2) . . ?
C28 C29 H29 120.3 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O18 H18 O17 0.63(4) 2.04(4) 2.539(3) 136(4) . yes
N1 H1 O16 1.03(6) 1.54(6) 2.553(2) 170(5) 2_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br15 C14 C9 C10 -178.00(16) . . . . ?
Br15 C14 C13 C12 178.23(19) . . . . ?
O18 C33 C32 C31 69.9(2) . . . . ?
O18 C33 C32 C27 -104.2(2) . . . . ?
O18 C33 C21 O16 -177.6(2) . . . . ?
O18 C33 C21 O17 2.4(3) . . . . ?
O18 C33 C19 C22 11.9(3) . . . . ?
O18 C33 C19 C26 -169.28(18) . . . . ?
C7 C4 C3 C2 179.1(2) . . . . ?
C7 C4 C5 C6 -179.0(2) . . . . ?
C7 C8 C10 C9 -6.1(4) . . . . ?
C7 C8 C10 C11 172.5(2) . . . . ?
C4 C7 C8 C10 -178.0(2) . . . . ?
C4 C3 C2 N1 0.3(4) . . . . ?
C4 C5 C6 N1 -0.7(4) . . . . ?
C33 C32 C31 C30 -173.9(2) . . . . ?
C33 C32 C27 C28 173.5(2) . . . . ?
C33 C19 C26 C25 -178.23(19) . . . . ?
C32 C33 C21 O16 65.6(3) . . . . ?
C32 C33 C21 O17 -114.4(2) . . . . ?
C32 C33 C19 C22 130.3(2) . . . . ?
C32 C33 C19 C26 -50.9(2) . . . . ?
C32 C31 C30 C29 -0.4(4) . . . . ?
C32 C27 C28 C29 0.6(4) . . . . ?
C21 C33 C32 C31 -173.43(19) . . . . ?
C21 C33 C32 C27 12.5(3) . . . . ?
C21 C33 C19 C22 -105.1(2) . . . . ?
C21 C33 C19 C26 73.7(2) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C22 C19 C26 C25 0.6(3) . . . . ?
C14 C9 C10 C8 178.1(2) . . . . ?
C14 C9 C10 C11 -0.6(3) . . . . ?
C14 C13 C12 C11 0.1(4) . . . . ?
C2 N1 C6 C5 0.0(4) . . . . ?
C19 C33 C32 C31 -50.4(2) . . . . ?
C19 C33 C32 C27 135.5(2) . . . . ?
C19 C33 C21 O16 -58.5(3) . . . . ?
C19 C33 C21 O17 121.5(2) . . . . ?
C19 C22 C23 C24 -0.4(3) . . . . ?
C19 C26 C25 C24 -0.9(3) . . . . ?
C9 C14 C13 C12 -0.6(4) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C5 C4 C3 C2 -1.0(3) . . . . ?
C8 C7 C4 C3 -168.8(2) . . . . ?
C8 C7 C4 C5 11.3(4) . . . . ?
C8 C10 C11 C12 -178.6(2) . . . . ?
C26 C25 C24 C23 0.5(3) . . . . ?
C25 C24 C23 C22 0.1(3) . . . . ?
C13 C14 C9 C10 0.8(3) . . . . ?
C13 C12 C11 C10 0.2(4) . . . . ?
C6 N1 C2 C3 0.2(4) . . . . ?
C31 C32 C27 C28 -0.5(3) . . . . ?
C31 C30 C29 C28 0.4(4) . . . . ?
C23 C22 C19 C33 178.85(19) . . . . ?
C23 C22 C19 C26 0.0(3) . . . . ?
C27 C32 C31 C30 0.4(3) . . . . ?
C30 C29 C28 C27 -0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.988
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# 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_1320_am-r-135-acn
_database_code_depnum_ccdc_archive 'CCDC 2289888'
loop_
_audit_author_name
_audit_author_address
'Rohan A.'
;Bits Pilani Hyderabad campus
India
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-07-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 O3, C13 H11 Cl N'
_chemical_formula_sum            'C27 H22 Cl N O3'
_chemical_formula_weight         443.90
_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      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                   8.5593(2)
_cell_length_b                   10.3705(2)
_cell_length_c                   13.0745(2)
_cell_angle_alpha                88.6790(10)
_cell_angle_beta                 74.542(2)
_cell_angle_gamma                82.8740(10)
_cell_volume                     1109.87(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7780
_cell_measurement_temperature    140
_cell_measurement_theta_max      79.4190
_cell_measurement_theta_min      4.2790
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.720
_exptl_absorpt_coefficient_mu    1.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78110
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12330
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.754
_diffrn_reflns_theta_min         4.297
_diffrn_ambient_temperature      140
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_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  89.00   0.50    0.61    --    0.00  37.00 -60.00  134
  2  ω    -28.00  15.00   0.50    0.61    --    0.00 -57.00-150.00   86
  3  ω    -88.00 -46.00   0.50    0.61    --    0.00 -57.00  60.00   84
  4  ω    -35.00  22.00   0.50    0.61    --    0.00 -57.00  60.00  114
  5  ω    -26.00  19.00   0.50    0.61    --    0.00 -37.00 -30.00   90
  6  ω    -87.00 -38.00   0.50    0.61    --    0.00 -57.00-150.00   98
  7  ω     77.00 139.00   0.50    3.00    --  107.20 -82.00 -60.00  124
  8  ω     84.00 195.00   0.50    3.00    --  107.20  15.00  90.00  222
  9  ω     20.00 138.00   0.50    3.00    --  107.20 -82.00-120.00  236
 10  ω     24.00  74.00   0.50    3.00    --  107.20 -82.00 -30.00  100
 11  ω     18.00  87.00   0.50    3.00    --  107.20 -61.00-180.00  138
 12  ω     25.00  73.00   0.50    3.00    --  107.20 -82.00 -60.00   96
 13  ω     26.00  88.00   0.50    3.00    --  107.20 -45.00  90.00  124
 14  ω     18.00 123.00   0.50    3.00    --  107.20 -82.00 150.00  210
 15  ω     81.00 107.00   0.50    3.00    --  107.20 -82.00  30.00   52
 16  ω    143.00 191.00   0.50    3.00    --  107.20  30.00  30.00   96
 17  ω     97.00 138.00   0.50    3.00    --  107.20  30.00  30.00   82
 18  ω    105.00 191.00   0.50    3.00    --  107.20  45.00 -30.00  172
 19  ω     19.00  90.00   0.50    3.00    --  107.20 -61.00  90.00  142
 20  ω     80.00 108.00   0.50    3.00    --  107.20 -82.00  90.00   56
 21  ω     21.00 120.00   0.50    3.00    --  107.20 -30.00 -30.00  198
 22  ω     80.00 137.00   0.50    3.00    --  107.20 -82.00 -30.00  114
 23  ω     19.00 110.00   0.50    3.00    --  107.20 -30.00-120.00  182
;
_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      0.0071742000
_diffrn_orient_matrix_UB_12      -0.0692923000
_diffrn_orient_matrix_UB_13      -0.1044121000
_diffrn_orient_matrix_UB_21      0.1666577000
_diffrn_orient_matrix_UB_22      -0.0749164000
_diffrn_orient_matrix_UB_23      0.0010210000
_diffrn_orient_matrix_UB_31      -0.0870439000
_diffrn_orient_matrix_UB_32      -0.1095493000
_diffrn_orient_matrix_UB_33      0.0635944000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                4256
_reflns_number_total             4648
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.106
_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)+(0.0474P)²+0.3568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C25(H25), C23(H23), C28(H28), C24(H24), C9(H9), C21(H21), C13(H13),
 C15(H15), C20(H20), C26(H26), C16(H16), C18(H18), C17(H17), C12(H12), C30(H30),
  C32(H32), C11(H11), C10(H10), C31(H31)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.87598(5) 1.49252(3) 0.31627(3) 0.03778(13) Uani 1 1 d . . . . .
O4 O 0.52262(13) 0.16038(10) 0.69531(8) 0.0288(2) Uani 1 1 d . . . . .
O2 O 0.69192(14) 0.43788(9) 0.75415(8) 0.0295(2) Uani 1 1 d . . . . .
O3 O 0.65277(18) 0.35515(11) 0.60756(9) 0.0433(3) Uani 1 1 d . . . . .
N5 N 0.73692(15) 0.64724(11) 0.64928(9) 0.0269(3) Uani 1 1 d . . . . .
C8 C 0.69895(17) 0.14997(12) 0.80996(10) 0.0229(3) Uani 1 1 d . . . . .
C19 C 0.26768(18) 0.27784(13) 0.85390(12) 0.0268(3) Uani 1 1 d . . . . .
H19 H 0.250022 0.239004 0.793483 0.032 Uiso 1 1 calc R U . . .
C14 C 0.42615(17) 0.28743(12) 0.85829(10) 0.0223(3) Uani 1 1 d . . . . .
C22 C 0.75650(17) 0.87760(13) 0.53728(11) 0.0240(3) Uani 1 1 d . . . . .
C25 C 0.76587(17) 1.00157(13) 0.48065(11) 0.0258(3) Uani 1 1 d . . . . .
H25 H 0.823876 1.064075 0.501624 0.031 Uiso 1 1 calc R U . . .
C23 C 0.80215(18) 0.86362(13) 0.63250(11) 0.0262(3) Uani 1 1 d . . . . .
H23 H 0.840879 0.933757 0.659909 0.031 Uiso 1 1 calc R U . . .
C7 C 0.57306(17) 0.23681(12) 0.76768(10) 0.0229(3) Uani 1 1 d . . . . .
C27 C 0.70445(17) 1.14899(13) 0.33695(11) 0.0256(3) Uani 1 1 d . . . . .
C28 C 0.77473(17) 1.25648(13) 0.35867(11) 0.0265(3) Uani 1 1 d . . . . .
H28 H 0.816792 1.257492 0.418912 0.032 Uiso 1 1 calc R U . . .
C6 C 0.64600(18) 0.35379(13) 0.70347(11) 0.0267(3) Uani 1 1 d . . . . .
C24 C 0.79077(18) 0.74793(14) 0.68637(11) 0.0278(3) Uani 1 1 d . . . . .
H24 H 0.821664 0.739289 0.751038 0.033 Uiso 1 1 calc R U . . .
C9 C 0.86502(18) 0.16067(14) 0.78049(12) 0.0304(3) Uani 1 1 d . . . . .
H9 H 0.904614 0.229815 0.736069 0.036 Uiso 1 1 calc R U . . .
C21 C 0.70297(19) 0.76968(14) 0.50014(11) 0.0286(3) Uani 1 1 d . . . . .
H21 H 0.673123 0.774340 0.435061 0.034 Uiso 1 1 calc R U . . .
C13 C 0.64448(18) 0.04717(14) 0.87578(11) 0.0272(3) Uani 1 1 d . . . . .
H13 H 0.531199 0.038442 0.896900 0.033 Uiso 1 1 calc R U . . .
C15 C 0.44962(18) 0.34567(13) 0.94777(11) 0.0247(3) Uani 1 1 d . . . . .
H15 H 0.557286 0.352528 0.952186 0.030 Uiso 1 1 calc R U . . .
C20 C 0.69375(19) 0.65705(14) 0.55809(11) 0.0295(3) Uani 1 1 d . . . . .
H20 H 0.655986 0.584870 0.532807 0.035 Uiso 1 1 calc R U . . .
C29 C 0.78188(18) 1.36142(14) 0.29077(12) 0.0285(3) Uani 1 1 d . . . . .
C26 C 0.69703(18) 1.03112(13) 0.40109(11) 0.0272(3) Uani 1 1 d . . . . .
H26 H 0.636000 0.968063 0.384171 0.033 Uiso 1 1 calc R U . . .
C16 C 0.31675(19) 0.39351(13) 1.03015(11) 0.0290(3) Uani 1 1 d . . . . .
H16 H 0.333765 0.433737 1.090190 0.035 Uiso 1 1 calc R U . . .
C18 C 0.13466(19) 0.32423(14) 0.93658(13) 0.0314(3) Uani 1 1 d . . . . .
H18 H 0.027035 0.316041 0.932757 0.038 Uiso 1 1 calc R U . . .
C17 C 0.15856(19) 0.38246(14) 1.02468(12) 0.0320(3) Uani 1 1 d . . . . .
H17 H 0.067543 0.414685 1.081055 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7530(2) -0.04196(14) 0.91057(12) 0.0317(3) Uani 1 1 d . . . . .
H12 H 0.713904 -0.111241 0.955007 0.038 Uiso 1 1 calc R U . . .
C30 C 0.72047(19) 1.36451(15) 0.20278(13) 0.0326(3) Uani 1 1 d . . . . .
H30 H 0.726673 1.437758 0.157520 0.039 Uiso 1 1 calc R U . . .
C32 C 0.64124(19) 1.15144(15) 0.24869(12) 0.0311(3) Uani 1 1 d . . . . .
H32 H 0.591963 1.079318 0.233981 0.037 Uiso 1 1 calc R U . . .
C11 C 0.9190(2) -0.03032(15) 0.88066(13) 0.0343(3) Uani 1 1 d . . . . .
H11 H 0.993787 -0.091052 0.904620 0.041 Uiso 1 1 calc R U . . .
C10 C 0.97408(19) 0.07098(15) 0.81545(14) 0.0364(4) Uani 1 1 d . . . . .
H10 H 1.087468 0.079311 0.794375 0.044 Uiso 1 1 calc R U . . .
C31 C 0.6497(2) 1.25815(16) 0.18236(13) 0.0355(3) Uani 1 1 d . . . . .
H31 H 0.606740 1.258304 0.122447 0.043 Uiso 1 1 calc R U . . .
H2 H 0.727(3) 0.555(3) 0.692(2) 0.079(8) Uiso 1 1 d . . . . .
H4 H 0.560(3) 0.200(2) 0.6360(19) 0.047(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
Cl1 C29 1.7448(16) . ?
O4 C7 1.4308(15) . ?
O4 H4 0.87(2) . ?
O2 C6 1.2667(17) . ?
O2 H2 1.46(3) . ?
O3 C6 1.2396(18) . ?
N5 C24 1.3416(19) . ?
N5 C20 1.3373(19) . ?
N5 H2 1.10(3) . ?
C8 C7 1.5269(19) . ?
C8 C9 1.388(2) . ?
C8 C13 1.4006(19) . ?
C19 H19 0.9500 . ?
C19 C14 1.389(2) . ?
C19 C18 1.389(2) . ?
C14 C7 1.5268(19) . ?
C14 C15 1.4007(19) . ?
C22 C25 1.4688(18) . ?
C22 C23 1.400(2) . ?
C22 C21 1.4033(19) . ?
C25 H25 0.9500 . ?
C25 C26 1.338(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.3779(19) . ?
C7 C6 1.5582(18) . ?
C27 C28 1.399(2) . ?
C27 C26 1.4646(18) . ?
C27 C32 1.397(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.3854(19) . ?
C24 H24 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.392(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.3765(19) . ?
C13 H13 0.9500 . ?
C13 C12 1.385(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C20 H20 0.9500 . ?
C29 C30 1.385(2) . ?
C26 H26 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.394(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.389(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.386(2) . ?
C32 H32 0.9500 . ?
C32 C31 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(2) . ?
C10 H10 0.9500 . ?
C31 H31 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O4 H4 100.9(15) . . ?
C6 O2 H2 112.3(11) . . ?
C24 N5 H2 121.6(15) . . ?
C20 N5 C24 120.33(12) . . ?
C20 N5 H2 118.1(15) . . ?
C9 C8 C7 123.93(12) . . ?
C9 C8 C13 118.29(13) . . ?
C13 C8 C7 117.58(12) . . ?
C14 C19 H19 119.5 . . ?
C14 C19 C18 120.93(14) . . ?
C18 C19 H19 119.5 . . ?
C19 C14 C7 121.26(12) . . ?
C19 C14 C15 118.68(13) . . ?
C15 C14 C7 120.06(12) . . ?
C23 C22 C25 119.96(12) . . ?
C23 C22 C21 117.27(12) . . ?
C21 C22 C25 122.77(13) . . ?
C22 C25 H25 118.3 . . ?
C26 C25 C22 123.47(13) . . ?
C26 C25 H25 118.3 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.86(13) . . ?
C24 C23 H23 120.1 . . ?
O4 C7 C8 107.53(10) . . ?
O4 C7 C14 110.10(11) . . ?
O4 C7 C6 106.55(10) . . ?
C8 C7 C6 112.43(11) . . ?
C14 C7 C8 110.73(11) . . ?
C14 C7 C6 109.39(10) . . ?
C28 C27 C26 123.11(13) . . ?
C32 C27 C28 119.18(13) . . ?
C32 C27 C26 117.69(13) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 C27 118.81(13) . . ?
C29 C28 H28 120.6 . . ?
O2 C6 C7 117.06(12) . . ?
O3 C6 O2 126.54(13) . . ?
O3 C6 C7 116.40(12) . . ?
N5 C24 C23 121.28(13) . . ?
N5 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.59(14) . . ?
C10 C9 H9 119.7 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 119.94(13) . . ?
C20 C21 H21 120.0 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.09(14) . . ?
C12 C13 H13 119.5 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.57(13) . . ?
C16 C15 H15 119.7 . . ?
N5 C20 C21 121.30(13) . . ?
N5 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C28 C29 Cl1 118.34(12) . . ?
C30 C29 Cl1 119.19(11) . . ?
C30 C29 C28 122.46(14) . . ?
C25 C26 C27 127.81(13) . . ?
C25 C26 H26 116.1 . . ?
C27 C26 H26 116.1 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.99(14) . . ?
C17 C16 H16 120.0 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.15(14) . . ?
C17 C18 H18 119.9 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.68(14) . . ?
C18 C17 H17 120.2 . . ?
C13 C12 H12 119.9 . . ?
C13 C12 C11 120.15(14) . . ?
C11 C12 H12 119.9 . . ?
C29 C30 H30 120.8 . . ?
C29 C30 C31 118.37(13) . . ?
C31 C30 H30 120.8 . . ?
C27 C32 H32 119.7 . . ?
C31 C32 C27 120.65(14) . . ?
C31 C32 H32 119.7 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.18(14) . . ?
C10 C11 H11 120.4 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.70(14) . . ?
C11 C10 H10 119.7 . . ?
C30 C31 C32 120.52(14) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H2 O2 1.10(3) 1.46(3) 2.5555(14) 173(2) . yes
O4 H4 O3 0.87(2) 1.87(2) 2.5312(15) 131(2) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C29 C30 C31 178.44(12) . . . . ?
O4 C7 C6 O2 176.87(12) . . . . ?
O4 C7 C6 O3 -2.96(18) . . . . ?
C8 C7 C6 O2 -65.58(16) . . . . ?
C8 C7 C6 O3 114.60(15) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C8 C13 C12 C11 0.2(2) . . . . ?
C19 C14 C7 O4 -11.34(17) . . . . ?
C19 C14 C7 C8 -130.13(13) . . . . ?
C19 C14 C7 C6 105.42(14) . . . . ?
C19 C14 C15 C16 -0.36(19) . . . . ?
C19 C18 C17 C16 -0.4(2) . . . . ?
C14 C19 C18 C17 0.7(2) . . . . ?
C14 C7 C6 O2 57.87(17) . . . . ?
C14 C7 C6 O3 -121.95(15) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C22 C25 C26 C27 -177.37(13) . . . . ?
C22 C23 C24 N5 0.2(2) . . . . ?
C22 C21 C20 N5 -0.8(2) . . . . ?
C25 C22 C23 C24 178.96(13) . . . . ?
C25 C22 C21 C20 -178.64(13) . . . . ?
C23 C22 C25 C26 -167.09(14) . . . . ?
C23 C22 C21 C20 1.4(2) . . . . ?
C7 C8 C9 C10 -174.52(13) . . . . ?
C7 C8 C13 C12 174.89(13) . . . . ?
C7 C14 C15 C16 179.22(12) . . . . ?
C27 C28 C29 Cl1 -177.88(10) . . . . ?
C27 C28 C29 C30 0.7(2) . . . . ?
C27 C32 C31 C30 -0.3(2) . . . . ?
C28 C27 C26 C25 -6.8(2) . . . . ?
C28 C27 C32 C31 0.9(2) . . . . ?
C28 C29 C30 C31 -0.1(2) . . . . ?
C24 N5 C20 C21 -0.1(2) . . . . ?
C9 C8 C7 O4 106.96(14) . . . . ?
C9 C8 C7 C14 -132.71(14) . . . . ?
C9 C8 C7 C6 -10.01(18) . . . . ?
C9 C8 C13 C12 -0.2(2) . . . . ?
C21 C22 C25 C26 12.9(2) . . . . ?
C21 C22 C23 C24 -1.1(2) . . . . ?
C13 C8 C7 O4 -67.78(15) . . . . ?
C13 C8 C7 C14 52.55(15) . . . . ?
C13 C8 C7 C6 175.25(12) . . . . ?
C13 C8 C9 C10 0.2(2) . . . . ?
C13 C12 C11 C10 -0.3(2) . . . . ?
C15 C14 C7 O4 169.09(11) . . . . ?
C15 C14 C7 C8 50.30(15) . . . . ?
C15 C14 C7 C6 -74.15(15) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C20 N5 C24 C23 0.4(2) . . . . ?
C29 C30 C31 C32 -0.1(2) . . . . ?
C26 C27 C28 C29 177.37(13) . . . . ?
C26 C27 C32 C31 -177.64(14) . . . . ?
C18 C19 C14 C7 -179.93(12) . . . . ?
C18 C19 C14 C15 -0.36(19) . . . . ?
C12 C11 C10 C9 0.3(2) . . . . ?
C32 C27 C28 C29 -1.1(2) . . . . ?
C32 C27 C26 C25 171.66(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.460
_oxdiff_exptl_absorpt_empirical_full_min 0.719
####################################################################### 
# 
# 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_3-cl-stp-hex-crysalis
_database_code_depnum_ccdc_archive 'CCDC 2291018'
loop_
_audit_author_name
_audit_author_address
'Rohan A.'
;Bits Pilani Hyderabad campus
India
;
_audit_update_record             
;
2023-08-27 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Cl N'
_chemical_formula_sum            'C13 H10 Cl N'
_chemical_formula_weight         215.67
_chemical_absolute_configuration ?
_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'

_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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   3.9947(2)
_cell_length_b                   13.9322(5)
_cell_length_c                   9.8346(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.133(4)
_cell_angle_gamma                90
_cell_volume                     538.81(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2764
_cell_measurement_temperature    300
_cell_measurement_theta_max      78.3150
_cell_measurement_theta_min      5.5520
_shelx_estimated_absorpt_T_max   0.766
_shelx_estimated_absorpt_T_min   0.603
_exptl_absorpt_coefficient_mu    2.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.2
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4574
_diffrn_reflns_point_group_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.718
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.682
_diffrn_reflns_theta_min         5.565
_diffrn_ambient_temperature      300
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -45.00   0.50    1.30    --    0.00 -57.00   0.00   76
  2  ω    -15.00  17.00   0.50    1.30    --    0.00  37.00 -90.00   64
  3  ω    -42.00  22.00   0.50    1.30    --    0.00 -57.00   0.00  128
  4  ω    -68.00 -16.00   0.50    1.30    --    0.00 -37.00 -90.00  104
  5  ω    -19.00  18.00   0.50    1.30    --    0.00  37.00-120.00   74
  6  ω     18.00 136.00   0.50    3.50    --  107.20 -82.00 -60.00  236
  7  ω    131.00 195.00   0.50    3.50    --  107.20  77.00  30.00  128
  8  ω    163.00 191.00   0.50    3.50    --  107.20  30.00 150.00   56
  9  ω     57.00 129.00   0.50    3.50    --  107.20 -61.00  90.00  144
 10  ω     81.00 106.00   0.50    3.50    --  107.20  77.00  30.00   50
 11  ω     23.00 132.00   0.50    3.50    --  107.20 -61.00 -60.00  218
 12  ω     94.00 194.00   0.50    3.50    --  107.20  30.00-150.00  200
 13  ω     18.00  52.00   0.50    3.50    --  107.20 -61.00  90.00   68
 14  ω    172.00 197.00   0.50    3.50    --  107.20  15.00 120.00   50
 15  ω    103.00 136.00   0.50    3.50    --  107.20  15.00 120.00   66
 16  ω     88.00 158.00   0.50    3.50    --  107.20  45.00-120.00  140
 17  ω    102.00 128.00   0.50    3.50    --  107.20 -82.00  30.00   52
 18  ω     44.00 136.00   0.50    3.50    --  107.20 -82.00  90.00  184
 19  ω    101.00 126.00   0.50    3.50    --  107.20  30.00  30.00   50
 20  ω     79.00 105.00   0.50    3.50    --  107.20 -82.00-150.00   52
 21  ω     94.00 156.00   0.50    3.50    --  107.20  30.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): 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      0.1679926000
_diffrn_orient_matrix_UB_12      -0.0455480000
_diffrn_orient_matrix_UB_13      0.1379199000
_diffrn_orient_matrix_UB_21      0.1360061000
_diffrn_orient_matrix_UB_22      0.0991803000
_diffrn_orient_matrix_UB_23      0.0526116000
_diffrn_orient_matrix_UB_31      -0.3266581000
_diffrn_orient_matrix_UB_32      0.0178322000
_diffrn_orient_matrix_UB_33      0.0594122000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.454
_reflns_Friedel_fraction_full    0.497
_reflns_Friedel_fraction_max     0.452
_reflns_number_gt                1576
_reflns_number_total             1684
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.40(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1684
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0574P)²+0.0532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.60(3)
 0.40(3)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.6450(3) 0.43287(5) 0.74083(15) 0.0823(3) Uani 1 1 d . . . . .
C5 C 0.5499(7) 0.8429(2) 0.3303(3) 0.0520(6) Uani 1 1 d . . . . .
C11 C 0.5184(8) 0.6134(2) 0.6485(3) 0.0548(7) Uani 1 1 d . . . . .
C9 C 0.4226(8) 0.7812(2) 0.5528(3) 0.0552(7) Uani 1 1 d . . . . .
C13 C 0.4291(10) 0.5802(3) 0.8801(4) 0.0651(8) Uani 1 1 d . . . . .
C8 C 0.5532(8) 0.7697(2) 0.4395(3) 0.0552(7) Uani 1 1 d . . . . .
C12 C 0.5197(8) 0.5517(2) 0.7581(3) 0.0574(7) Uani 1 1 d . . . . .
C10 C 0.4247(7) 0.7095(2) 0.6616(3) 0.0530(6) Uani 1 1 d . . . . .
N2 N 0.5593(9) 0.9756(3) 0.1153(3) 0.0738(8) Uani 1 1 d . . . . .
C15 C 0.3296(9) 0.7376(2) 0.7855(4) 0.0631(8) Uani 1 1 d . . . . .
C6 C 0.4315(9) 0.9357(2) 0.3384(4) 0.0607(8) Uani 1 1 d . . . . .
C4 C 0.6718(10) 0.8189(3) 0.2120(4) 0.0631(8) Uani 1 1 d . . . . .
C14 C 0.3316(11) 0.6742(3) 0.8929(4) 0.0710(9) Uani 1 1 d . . . . .
C7 C 0.4383(10) 0.9977(3) 0.2299(4) 0.0680(9) Uani 1 1 d . . . . .
C3 C 0.6739(10) 0.8864(3) 0.1087(4) 0.0714(9) Uani 1 1 d . . . . .
H9 H 0.295(9) 0.839(3) 0.564(4) 0.053(9) Uiso 1 1 d . . . . .
H8 H 0.662(13) 0.708(4) 0.425(5) 0.084(13) Uiso 1 1 d . . . . .
H15 H 0.263(10) 0.805(3) 0.791(4) 0.070(11) Uiso 1 1 d . . . . .
H6 H 0.326(11) 0.960(3) 0.429(4) 0.068(11) Uiso 1 1 d . . . . .
H11 H 0.569(10) 0.596(3) 0.571(5) 0.063(10) Uiso 1 1 d . . . . .
H3 H 0.762(11) 0.868(3) 0.027(5) 0.070(11) Uiso 1 1 d . . . . .
H4 H 0.759(11) 0.759(3) 0.199(4) 0.071(12) Uiso 1 1 d . . . . .
H14 H 0.251(13) 0.697(3) 0.979(5) 0.091(14) Uiso 1 1 d . . . . .
H13 H 0.460(12) 0.539(4) 0.962(6) 0.087(13) Uiso 1 1 d . . . . .
H7 H 0.357(12) 1.060(3) 0.236(5) 0.077(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 C12 1.747(3) . ?
C5 C8 1.479(4) . ?
C5 C6 1.385(4) . ?
C5 C4 1.379(5) . ?
C11 C12 1.378(4) . ?
C11 C10 1.402(5) . ?
C11 H11 0.86(4) . ?
C9 C8 1.321(5) . ?
C9 C10 1.462(4) . ?
C9 H9 0.97(4) . ?
C13 C12 1.372(5) . ?
C13 C14 1.378(6) . ?
C13 H13 0.98(5) . ?
C8 H8 0.98(5) . ?
C10 C15 1.395(5) . ?
N2 C7 1.339(6) . ?
N2 C3 1.330(6) . ?
C15 C14 1.375(5) . ?
C15 H15 0.98(4) . ?
C6 C7 1.377(5) . ?
C6 H6 1.11(4) . ?
C4 C3 1.385(5) . ?
C4 H4 0.92(5) . ?
C14 H14 1.01(6) . ?
C7 H7 0.94(4) . ?
C3 H3 0.97(5) . ?

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
C6 C5 C8 124.2(3) . . ?
C4 C5 C8 119.1(3) . . ?
C4 C5 C6 116.7(3) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 123(3) . . ?
C10 C11 H11 118(3) . . ?
C8 C9 C10 125.6(3) . . ?
C8 C9 H9 119(2) . . ?
C10 C9 H9 115(2) . . ?
C12 C13 C14 118.4(3) . . ?
C12 C13 H13 123(3) . . ?
C14 C13 H13 119(3) . . ?
C5 C8 H8 116(3) . . ?
C9 C8 C5 125.1(3) . . ?
C9 C8 H8 119(3) . . ?
C11 C12 Cl1 118.5(3) . . ?
C13 C12 Cl1 118.9(3) . . ?
C13 C12 C11 122.6(3) . . ?
C11 C10 C9 123.5(3) . . ?
C15 C10 C11 117.8(3) . . ?
C15 C10 C9 118.7(3) . . ?
C3 N2 C7 115.7(3) . . ?
C10 C15 H15 116(2) . . ?
C14 C15 C10 121.7(3) . . ?
C14 C15 H15 122(2) . . ?
C5 C6 H6 121(2) . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6 120(2) . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 122(3) . . ?
C3 C4 H4 118(3) . . ?
C13 C14 H14 121(3) . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119(3) . . ?
N2 C7 C6 124.6(4) . . ?
N2 C7 H7 117(3) . . ?
C6 C7 H7 119(3) . . ?
N2 C3 C4 123.5(4) . . ?
N2 C3 H3 117(2) . . ?
C4 C3 H3 119(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C6 C7 N2 -1.4(6) . . . . ?
C5 C4 C3 N2 -0.8(6) . . . . ?
C11 C10 C15 C14 1.0(5) . . . . ?
C9 C10 C15 C14 -178.9(3) . . . . ?
C8 C5 C6 C7 -179.5(3) . . . . ?
C8 C5 C4 C3 -179.5(3) . . . . ?
C8 C9 C10 C11 -10.7(5) . . . . ?
C8 C9 C10 C15 169.2(3) . . . . ?
C12 C11 C10 C9 178.5(3) . . . . ?
C12 C11 C10 C15 -1.3(4) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C10 C11 C12 Cl1 -178.8(2) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C10 C9 C8 C5 -179.9(3) . . . . ?
C10 C15 C14 C13 0.0(6) . . . . ?
C6 C5 C8 C9 5.1(5) . . . . ?
C6 C5 C4 C3 0.4(5) . . . . ?
C4 C5 C8 C9 -175.0(3) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C14 C13 C12 Cl1 179.8(3) . . . . ?
C14 C13 C12 C11 0.3(5) . . . . ?
C7 N2 C3 C4 0.0(6) . . . . ?
C3 N2 C7 C6 1.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.694
_oxdiff_exptl_absorpt_empirical_full_min 0.511
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.60(3)
2 0.40(3)

####################################################################### 
# 
# 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_1412-am-r-3brstp
_database_code_depnum_ccdc_archive 'CCDC 2291142'
loop_
_audit_author_name
_audit_author_address
'Rohan A.'
;Bits Pilani Hyderabad campus
India
;
_audit_update_record             
;
2023-08-28 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Br N'
_chemical_formula_sum            'C13 H10 Br N'
_chemical_formula_weight         260.13
_chemical_absolute_configuration ?
_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'
Br Br -0.6763 1.2805 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3605(4)
_cell_length_b                   12.2746(4)
_cell_length_c                   12.3726(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1117.83(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1466
_cell_measurement_temperature    295
_cell_measurement_theta_max      74.9330
_cell_measurement_theta_min      5.0400
_shelx_estimated_absorpt_T_max   0.453
_shelx_estimated_absorpt_T_min   0.333
_exptl_absorpt_coefficient_mu    4.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52328
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3788
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.905
_diffrn_reflns_theta_min         5.076
_diffrn_ambient_temperature      295
_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    -19.00  12.00   0.50    0.50    --    0.00  37.00  30.00   62
  2  ω     41.00  86.00   0.50    0.50    --    0.00  37.00  30.00   90
  3  ω     59.00  86.00   0.50    0.50    --    0.00  57.00 150.00   54
  4  ω     19.00  47.00   0.50    3.00    --  107.20 -30.00  30.00   56
  5  ω    111.00 197.00   0.50    3.00    --  107.20  77.00  60.00  172
  6  ω     77.00 102.00   0.50    3.00    --  107.20  77.00  60.00   50
  7  ω     90.00 115.00   0.50    3.00    --  107.20  30.00 -60.00   50
  8  ω     63.00 124.00   0.50    3.00    --  107.20 -30.00  30.00  122
  9  ω    120.00 191.00   0.50    3.00    --  107.20  30.00 -60.00  142
 10  ω     58.00 127.00   0.50    3.00    --  107.20 -30.00 -90.00  138
;
_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      0.0487695000
_diffrn_orient_matrix_UB_12      -0.0964427000
_diffrn_orient_matrix_UB_13      -0.0742277000
_diffrn_orient_matrix_UB_21      -0.1198348000
_diffrn_orient_matrix_UB_22      0.0486040000
_diffrn_orient_matrix_UB_23      -0.0899888000
_diffrn_orient_matrix_UB_31      0.1644674000
_diffrn_orient_matrix_UB_32      0.0640276000
_diffrn_orient_matrix_UB_33      -0.0434979000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.564
_reflns_Friedel_fraction_full    0.848
_reflns_Friedel_fraction_max     0.759
_reflns_number_gt                1510
_reflns_number_total             2153
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1030P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1832
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C15(H15), C8(H8), C11(H11), C9(H9), C7(H7), C12(H12),
 C4(H4), C3(H3)
;
_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
Br1 Br 0.6463(2) 0.17848(9) 0.06899(6) 0.1199(5) Uani 1 1 d . . . . .
N2 N 0.6307(11) 0.5184(6) 0.8175(6) 0.0964(19) Uani 1 1 d . . . . .
C10 C 0.6272(9) 0.1779(5) 0.4035(5) 0.0693(13) Uani 1 1 d . . . . .
C13 C 0.6120(11) 0.0224(6) 0.2371(6) 0.0825(19) Uani 1 1 d . . . . .
H13 H 0.607291 -0.029113 0.182031 0.099 Uiso 1 1 calc R U . . .
C5 C 0.6260(10) 0.3489(5) 0.6639(6) 0.0733(16) Uani 1 1 d . . . . .
C6 C 0.6034(11) 0.4569(6) 0.6354(7) 0.086(2) Uani 1 1 d . . . . .
H6 H 0.586250 0.475523 0.563256 0.103 Uiso 1 1 calc R U . . .
C15 C 0.6399(11) 0.2086(5) 0.2957(5) 0.0740(15) Uani 1 1 d . . . . .
H15 H 0.652919 0.281723 0.277633 0.089 Uiso 1 1 calc R U . . .
C14 C 0.6331(11) 0.1310(6) 0.2157(6) 0.0788(16) Uani 1 1 d . . . . .
C8 C 0.6187(11) 0.2570(5) 0.5890(5) 0.0753(17) Uani 1 1 d . . . . .
H8 H 0.600602 0.187558 0.617124 0.090 Uiso 1 1 calc R U . . .
C11 C 0.6079(10) 0.0698(6) 0.4271(6) 0.0809(18) Uani 1 1 d . . . . .
H11 H 0.601352 0.047532 0.498863 0.097 Uiso 1 1 calc R U . . .
C9 C 0.6364(10) 0.2677(6) 0.4846(5) 0.0734(15) Uani 1 1 d . . . . .
H9 H 0.656562 0.337630 0.458354 0.088 Uiso 1 1 calc R U . . .
C7 C 0.6060(13) 0.5362(7) 0.7125(8) 0.096(2) Uani 1 1 d . . . . .
H7 H 0.589363 0.607825 0.690051 0.115 Uiso 1 1 calc R U . . .
C12 C 0.5980(12) -0.0071(6) 0.3450(8) 0.093(2) Uani 1 1 d . . . . .
H12 H 0.581639 -0.080097 0.362812 0.112 Uiso 1 1 calc R U . . .
C4 C 0.6471(12) 0.3297(7) 0.7758(6) 0.0870(18) Uani 1 1 d . . . . .
H4 H 0.660488 0.258953 0.801517 0.104 Uiso 1 1 calc R U . . .
C3 C 0.6478(14) 0.4150(7) 0.8455(7) 0.095(2) Uani 1 1 d . . . . .
H3 H 0.661284 0.399473 0.918628 0.114 Uiso 1 1 calc R U . . .


_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
Br1 C14 1.909(8) . ?
N2 C7 1.330(12) . ?
N2 C3 1.322(12) . ?
C10 C15 1.389(9) . ?
C10 C11 1.366(11) . ?
C10 C9 1.491(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(11) . ?
C13 C12 1.388(11) . ?
C5 C6 1.381(11) . ?
C5 C8 1.461(9) . ?
C5 C4 1.413(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.363(11) . ?
C15 H15 0.9300 . ?
C15 C14 1.374(10) . ?
C8 H8 0.9300 . ?
C8 C9 1.305(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(11) . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.356(11) . ?
C3 H3 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
C3 N2 C7 115.2(7) . . ?
C15 C10 C9 116.3(6) . . ?
C11 C10 C15 118.4(6) . . ?
C11 C10 C9 125.3(6) . . ?
C14 C13 H13 121.7 . . ?
C14 C13 C12 116.7(7) . . ?
C12 C13 H13 121.7 . . ?
C6 C5 C8 125.1(7) . . ?
C6 C5 C4 115.1(7) . . ?
C4 C5 C8 119.7(6) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(8) . . ?
C7 C6 H6 119.8 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.1(7) . . ?
C14 C15 H15 119.9 . . ?
C13 C14 Br1 119.2(5) . . ?
C13 C14 C15 122.7(7) . . ?
C15 C14 Br1 118.1(6) . . ?
C5 C8 H8 118.4 . . ?
C9 C8 C5 123.1(7) . . ?
C9 C8 H8 118.4 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(7) . . ?
C12 C11 H11 119.7 . . ?
C10 C9 H9 117.0 . . ?
C8 C9 C10 126.0(6) . . ?
C8 C9 H9 117.0 . . ?
N2 C7 C6 124.6(8) . . ?
N2 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
C13 C12 C11 121.5(7) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.6(8) . . ?
C3 C4 H4 120.2 . . ?
N2 C3 C4 125.1(9) . . ?
N2 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C15 C14 Br1 178.8(6) . . . . ?
C10 C15 C14 C13 0.7(13) . . . . ?
C10 C11 C12 C13 1.7(13) . . . . ?
C5 C6 C7 N2 0.5(15) . . . . ?
C5 C8 C9 C10 -178.9(7) . . . . ?
C5 C4 C3 N2 -0.3(15) . . . . ?
C6 C5 C8 C9 18.2(13) . . . . ?
C6 C5 C4 C3 -1.3(12) . . . . ?
C15 C10 C11 C12 -1.1(11) . . . . ?
C15 C10 C9 C8 176.6(8) . . . . ?
C14 C13 C12 C11 -1.0(13) . . . . ?
C8 C5 C6 C7 177.5(8) . . . . ?
C8 C5 C4 C3 -177.8(8) . . . . ?
C11 C10 C15 C14 -0.1(11) . . . . ?
C11 C10 C9 C8 -3.5(12) . . . . ?
C9 C10 C15 C14 179.8(7) . . . . ?
C9 C10 C11 C12 179.0(7) . . . . ?
C7 N2 C3 C4 2.0(15) . . . . ?
C12 C13 C14 Br1 -178.2(7) . . . . ?
C12 C13 C14 C15 -0.2(13) . . . . ?
C4 C5 C6 C7 1.3(12) . . . . ?
C4 C5 C8 C9 -165.7(8) . . . . ?
C3 N2 C7 C6 -2.1(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.430
_oxdiff_exptl_absorpt_empirical_full_min 0.397
####################################################################### 
# 
# 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_260-nme-crysalis
_database_code_depnum_ccdc_archive 'CCDC 2289891'
loop_
_audit_author_name
_audit_author_address
'Rohan A.'
;Bits Pilani Hyderabad campus
India
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 O3, C5 H4 I N'
_chemical_formula_sum            'C19 H16 I N O3'
_chemical_formula_weight         433.23
_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'
I I -0.3257 6.8362 '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                   6.45360(10)
_cell_length_b                   8.3751(2)
_cell_length_c                   16.1607(5)
_cell_angle_alpha                83.149(2)
_cell_angle_beta                 86.845(2)
_cell_angle_gamma                83.349(2)
_cell_volume                     860.65(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6639
_cell_measurement_temperature    140
_cell_measurement_theta_max      79.3380
_cell_measurement_theta_min      5.3650
_shelx_estimated_absorpt_T_max   0.320
_shelx_estimated_absorpt_T_min   0.156
_exptl_absorpt_coefficient_mu    14.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.2
_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  0.0437
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8384
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.796
_diffrn_reflns_theta_min         5.352
_diffrn_ambient_temperature      140.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  32.00   0.50    0.50    --    0.00 -82.00  30.00  242
  2  ω    -89.00 -32.00   0.50    0.50    --    0.00   0.00  90.00  114
  3  ω    -15.00  50.00   0.50    0.50    --    0.00  37.00-150.00  130
  4  ω      5.00  30.00   0.50    0.50    --    0.00   0.00  90.00   50
  5  ω     18.00 134.00   0.50    1.00    --  107.20 -15.00 -60.00  232
  6  ω     25.00  51.00   0.50    1.00    --  107.20 -30.00-150.00   52
  7  ω     56.00 137.00   0.50    1.00    --  107.20 -82.00-150.00  162
  8  ω     91.00 116.00   0.50    1.00    --  107.20 -82.00  60.00   50
  9  ω     80.00 196.00   0.50    1.00    --  107.20  15.00 -30.00  232
 10  ω     19.00  71.00   0.50    1.00    --  107.20 -82.00-120.00  104
 11  ω     86.00 138.00   0.50    1.00    --  107.20 -82.00-120.00  104
 12  ω     40.00 136.00   0.50    1.00    --  107.20 -82.00   0.00  192
 13  ω     21.00  85.00   0.50    1.00    --  107.20 -61.00 150.00  128
 14  ω     80.00 149.00   0.50    1.00    --  107.20  15.00 -90.00  138
 15  ω     72.00  98.00   0.50    1.00    --  107.20 -82.00 -30.00   52
 16  ω     22.00 136.00   0.50    1.00    --  107.20 -82.00 150.00  228
 17  ω    171.00 197.00   0.50    1.00    --  107.20  15.00 -90.00   52
 18  ω     43.00  76.00   0.50    1.00    --  107.20 -82.00  60.00   66
 19  ω     57.00 120.00   0.50    1.00    --  107.20 -30.00-150.00  126
 20  ω    152.00 177.00   0.50    1.00    --  107.20  30.00-180.00   50
 21  ω     96.00 128.00   0.50    1.00    --  107.20 -45.00   0.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): 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      -0.0367045000
_diffrn_orient_matrix_UB_12      0.0706228000
_diffrn_orient_matrix_UB_13      0.0840188000
_diffrn_orient_matrix_UB_21      0.2247831000
_diffrn_orient_matrix_UB_22      -0.0653925000
_diffrn_orient_matrix_UB_23      0.0233234000
_diffrn_orient_matrix_UB_31      0.0773656000
_diffrn_orient_matrix_UB_32      0.1596331000
_diffrn_orient_matrix_UB_33      -0.0403927000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3506
_reflns_number_total             3605
_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 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.569
_refine_diff_density_min         -1.524
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.074
_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)+(0.0572P)²+2.3242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1121
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C20(H20), C24(H24), C13(H13), C21(H21), C9(H9), C19(H19), C15(H15),
 C10(H10), C18(H18), C11(H11), C16(H16), C17(H17), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.25210(4) -0.36426(3) 0.50054(2) 0.03158(12) Uani 1 1 d . . . . .
O2 O 0.5708(5) 0.2651(4) 0.25244(19) 0.0259(6) Uani 1 1 d . . . . .
O4 O 0.0707(5) 0.4883(4) 0.28265(19) 0.0281(6) Uani 1 1 d . . . . .
O3 O 0.3325(5) 0.2669(4) 0.35799(19) 0.0323(7) Uani 1 1 d . . . . .
N5 N 0.8004(6) 0.0490(4) 0.3413(2) 0.0238(7) Uani 1 1 d . . . . .
C14 C 0.3678(6) 0.6067(5) 0.2166(2) 0.0211(7) Uani 1 1 d . . . . .
C7 C 0.2597(6) 0.4520(5) 0.2353(2) 0.0190(7) Uani 1 1 d . . . . .
C8 C 0.2127(6) 0.3876(5) 0.1540(2) 0.0204(7) Uani 1 1 d . . . . .
C22 C 1.0539(6) -0.1890(5) 0.4312(2) 0.0225(7) Uani 1 1 d . . . . .
C6 C 0.3950(6) 0.3168(5) 0.2882(2) 0.0194(7) Uani 1 1 d . . . . .
C23 C 1.1345(6) -0.1045(5) 0.3596(3) 0.0240(8) Uani 1 1 d . . . . .
H23 H 1.275702 -0.127663 0.340950 0.029 Uiso 1 1 calc R U . . .
C20 C 0.7264(7) -0.0345(5) 0.4096(3) 0.0262(8) Uani 1 1 d . . . . .
H20 H 0.583881 -0.010574 0.426431 0.031 Uiso 1 1 calc R U . . .
C24 C 1.0009(7) 0.0152(5) 0.3164(3) 0.0248(8) Uani 1 1 d . . . . .
H24 H 1.053331 0.074932 0.267560 0.030 Uiso 1 1 calc R U . . .
C13 C 0.0171(6) 0.3425(5) 0.1421(3) 0.0250(8) Uani 1 1 d . . . . .
H13 H -0.091664 0.355960 0.183605 0.030 Uiso 1 1 calc R U . . .
C21 C 0.8470(7) -0.1542(5) 0.4570(3) 0.0268(8) Uani 1 1 d . . . . .
H21 H 0.790159 -0.210977 0.505868 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3688(7) 0.3709(5) 0.0909(3) 0.0252(8) Uani 1 1 d . . . . .
H9 H 0.502403 0.403620 0.097762 0.030 Uiso 1 1 calc R U . . .
C19 C 0.5616(7) 0.6253(5) 0.2454(3) 0.0256(8) Uani 1 1 d . . . . .
H19 H 0.636235 0.538057 0.278361 0.031 Uiso 1 1 calc R U . . .
C15 C 0.2600(7) 0.7379(5) 0.1696(3) 0.0284(9) Uani 1 1 d . . . . .
H15 H 0.126676 0.727716 0.149968 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3306(8) 0.3074(6) 0.0189(3) 0.0311(9) Uani 1 1 d . . . . .
H10 H 0.437571 0.297005 -0.023514 0.037 Uiso 1 1 calc R U . . .
C18 C 0.6471(8) 0.7713(6) 0.2262(3) 0.0340(10) Uani 1 1 d . . . . .
H18 H 0.780684 0.782196 0.245363 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1352(8) 0.2585(6) 0.0083(3) 0.0336(10) Uani 1 1 d . . . . .
H11 H 0.109520 0.212485 -0.040580 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3461(9) 0.8833(5) 0.1513(3) 0.0369(11) Uani 1 1 d . . . . .
H16 H 0.271476 0.971684 0.119205 0.044 Uiso 1 1 calc R U . . .
C17 C 0.5402(9) 0.8999(6) 0.1797(3) 0.0386(11) Uani 1 1 d . . . . .
H17 H 0.598998 0.999231 0.167151 0.046 Uiso 1 1 calc R U . . .
C12 C -0.0205(7) 0.2776(6) 0.0695(3) 0.0334(10) Uani 1 1 d . . . . .
H12 H -0.154467 0.246210 0.062168 0.040 Uiso 1 1 calc R U . . .
H4 H 0.092(10) 0.432(8) 0.333(4) 0.044(17) Uiso 1 1 d . . . . .
H2 H 0.645(12) 0.180(10) 0.296(5) 0.06(2) 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
I1 C22 2.092(4) . ?
O2 C6 1.297(5) . ?
O2 H2 1.03(8) . ?
O4 C7 1.426(4) . ?
O4 H4 0.90(7) . ?
O3 C6 1.218(5) . ?
N5 C20 1.331(6) . ?
N5 C24 1.342(5) . ?
C14 C7 1.532(5) . ?
C14 C19 1.390(6) . ?
C14 C15 1.396(6) . ?
C7 C8 1.536(5) . ?
C7 C6 1.549(5) . ?
C8 C13 1.389(5) . ?
C8 C9 1.401(5) . ?
C22 C23 1.390(6) . ?
C22 C21 1.386(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(6) . ?
C24 H24 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.394(6) . ?
C21 H21 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.382(6) . ?
C19 H19 0.9500 . ?
C19 C18 1.394(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(7) . ?
C18 H18 0.9500 . ?
C18 C17 1.375(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(8) . ?
C17 H17 0.9500 . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 H2 106(4) . . ?
C7 O4 H4 104(4) . . ?
C20 N5 C24 119.1(4) . . ?
C19 C14 C7 124.2(4) . . ?
C19 C14 C15 118.6(4) . . ?
C15 C14 C7 117.2(4) . . ?
O4 C7 C14 108.4(3) . . ?
O4 C7 C8 110.2(3) . . ?
O4 C7 C6 107.3(3) . . ?
C14 C7 C8 110.7(3) . . ?
C14 C7 C6 111.9(3) . . ?
C8 C7 C6 108.3(3) . . ?
C13 C8 C7 121.0(3) . . ?
C13 C8 C9 118.8(4) . . ?
C9 C8 C7 120.2(3) . . ?
C23 C22 I1 118.9(3) . . ?
C21 C22 I1 120.8(3) . . ?
C21 C22 C23 120.3(4) . . ?
O2 C6 C7 115.1(3) . . ?
O3 C6 O2 125.2(4) . . ?
O3 C6 C7 119.7(3) . . ?
C22 C23 H23 121.2 . . ?
C22 C23 C24 117.6(4) . . ?
C24 C23 H23 121.2 . . ?
N5 C20 H20 118.5 . . ?
N5 C20 C21 123.0(4) . . ?
C21 C20 H20 118.5 . . ?
N5 C24 C23 122.2(4) . . ?
N5 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C8 C13 H13 119.9 . . ?
C8 C13 C12 120.3(4) . . ?
C12 C13 H13 119.9 . . ?
C22 C21 H21 121.1 . . ?
C20 C21 C22 117.8(4) . . ?
C20 C21 H21 121.1 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.7 . . ?
C14 C19 H19 119.9 . . ?
C14 C19 C18 120.3(4) . . ?
C18 C19 H19 119.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18 119.6 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C22 C23 C24 -177.8(3) . . . . ?
I1 C22 C21 C20 178.4(3) . . . . ?
O4 C7 C8 C13 -12.3(5) . . . . ?
O4 C7 C8 C9 168.7(3) . . . . ?
O4 C7 C6 O2 177.5(3) . . . . ?
O4 C7 C6 O3 -2.3(5) . . . . ?
N5 C20 C21 C22 -0.7(7) . . . . ?
C14 C7 C8 C13 -132.2(4) . . . . ?
C14 C7 C8 C9 48.8(5) . . . . ?
C14 C7 C6 O2 -63.7(4) . . . . ?
C14 C7 C6 O3 116.5(4) . . . . ?
C14 C19 C18 C17 1.0(7) . . . . ?
C14 C15 C16 C17 -0.1(7) . . . . ?
C7 C14 C19 C18 -179.2(4) . . . . ?
C7 C14 C15 C16 178.9(4) . . . . ?
C7 C8 C13 C12 -177.2(4) . . . . ?
C7 C8 C9 C10 177.5(4) . . . . ?
C8 C7 C6 O2 58.6(4) . . . . ?
C8 C7 C6 O3 -121.2(4) . . . . ?
C8 C13 C12 C11 -0.5(7) . . . . ?
C8 C9 C10 C11 -0.2(7) . . . . ?
C22 C23 C24 N5 -0.5(6) . . . . ?
C6 C7 C8 C13 104.7(4) . . . . ?
C6 C7 C8 C9 -74.2(4) . . . . ?
C23 C22 C21 C20 0.1(6) . . . . ?
C20 N5 C24 C23 0.0(6) . . . . ?
C24 N5 C20 C21 0.7(6) . . . . ?
C13 C8 C9 C10 -1.4(6) . . . . ?
C21 C22 C23 C24 0.5(6) . . . . ?
C9 C8 C13 C12 1.8(6) . . . . ?
C9 C10 C11 C12 1.5(7) . . . . ?
C19 C14 C7 O4 116.6(4) . . . . ?
C19 C14 C7 C8 -122.4(4) . . . . ?
C19 C14 C7 C6 -1.5(5) . . . . ?
C19 C14 C15 C16 0.7(6) . . . . ?
C19 C18 C17 C16 -0.4(7) . . . . ?
C15 C14 C7 O4 -61.5(4) . . . . ?
C15 C14 C7 C8 59.5(4) . . . . ?
C15 C14 C7 C6 -179.6(3) . . . . ?
C15 C14 C19 C18 -1.1(6) . . . . ?
C15 C16 C17 C18 0.0(7) . . . . ?
C10 C11 C12 C13 -1.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.302
_oxdiff_exptl_absorpt_empirical_full_min 0.590
