# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Bz-act-Cl
_database_code_depnum_ccdc_archive 'CCDC 2089318'
loop_
_audit_author_name
_audit_author_address
'Pierre Le Magueres'
;Rigaku Americas Corporation 
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Cl N2 O'
_chemical_formula_sum            'C14 H9 Cl N2 O'
_chemical_formula_weight         256.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H9 N2 O Cl'
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                   5.10890(10)
_cell_length_b                   22.0087(4)
_cell_length_c                   10.5605(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.571(2)
_cell_angle_gamma                90
_cell_volume                     1170.90(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6026
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1920
_cell_measurement_theta_min      4.6920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.76a (Rigaku Oxford Diffraction, 2020)
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    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -1 0.0325
0 -3 1 0.0413
1 5 -1 0.0501
0 -2 -1 0.0167
0 5 1 0.0302
-1 -2 0 0.0334
-1 -5 1 0.0293
1 2 -2 0.0417
2 1 -3 0.0558
-1 3 1 0.0300
-1 0 3 0.0255
1 -3 -1 0.0551
0 -3 -1 0.0131
-1 10 4 0.0186
1 -11 -4 0.0076

_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.028
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
-0.0063 2.9933 -1.0003 0.0485 0.0276 -0.2507
0.0063 -2.9933 1.0003 -0.0485 -0.0276 0.2507
0.9918 4.9765 -1.0104 0.3797 0.0754 -0.2658
-0.0049 -2.0062 -0.9944 -0.0537 -0.1963 -0.0018
0.0040 5.0059 0.9908 0.1150 0.3306 -0.1476
-0.9981 -1.9831 0.0102 -0.3312 -0.0479 0.0152
-0.9918 -4.9765 1.0104 -0.3797 -0.0754 0.2658
0.9872 1.9704 -2.0037 0.3055 -0.1656 -0.2178
1.9807 0.9475 -3.0070 0.5625 -0.3588 -0.1850
-0.9941 3.0227 1.0010 -0.2162 0.2827 -0.1324
-0.9824 0.0358 2.9980 -0.2518 0.3619 0.2196
0.9941 -3.0227 -1.0010 0.2162 -0.2827 0.1324
-0.0046 -3.0061 -0.9932 -0.0742 -0.2410 0.0480
-0.9798 10.0411 3.9830 -0.0346 0.9163 -0.1768
0.9801 -11.0410 -3.9818 0.0141 -0.9611 0.2266

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8652
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.387
_diffrn_reflns_theta_min         4.017
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  69.00   0.50    1.60    --  101.80 -61.00  30.00   80
  2  ω     29.00  69.00   0.50    1.60    --  101.80 -61.00  60.00   80
  3  ω     29.00  69.00   0.50    1.60    --  101.80 -61.00 120.00   80
  4  ω     29.00  69.00   0.50    1.60    --  101.80 -61.00 -90.00   80
  5  ω     29.00  69.00   0.50    1.60    --  101.80 -61.00-120.00   80
  6  ω    122.00 174.00   0.50    1.60    --  101.80  45.00-150.00  104
  7  ω     30.00 118.00   0.50    0.40    --   45.89  60.00 135.00  176
  8  ω    -28.00  30.00   0.50    0.40    --  -45.89  19.00 120.00  116
  9  ω    -44.00  27.00   0.50    0.40    --  -45.89  37.00  90.00  142
 10  ω    -53.00 -20.00   0.50    1.60    --  -91.75  45.00  60.00   66
 11  ω    -53.00 -20.00   0.50    1.60    --  -91.75  45.00  30.00   66
 12  ω    -68.00   0.00   0.50    0.40    --  -45.89  77.00-150.00  136
 13  ω    -53.00 -20.00   0.50    1.60    --  -91.75  45.00-150.00   66
 14  ω    -53.00 -20.00   0.50    1.60    --  -91.75  45.00-120.00   66
 15  ω   -163.00-122.00   0.50    1.60    --  -91.75 -45.00 -60.00   82
 16  ω   -163.00-127.00   0.50    1.60    --  -91.75 -61.00 -90.00   72
 17  ω   -163.00-126.00   0.50    1.60    --  -91.75 -77.00 -30.00   74
 18  ω   -163.00-127.00   0.50    1.60    --  -91.75 -61.00-120.00   72
 19  ω   -163.00-127.00   0.50    1.60    --  -91.75 -61.00 -30.00   72
 20  ω    -82.00 -29.00   0.50    0.40    --  -45.89 125.00 120.00  106
 21  ω   -163.00-127.00   0.50    1.60    --  -91.75 -61.00  90.00   72
 22  ω   -163.00-126.00   0.50    1.60    --  -91.75 -77.00  60.00   74
 23  ω   -163.00-122.00   0.50    1.60    --  -91.75 -45.00   0.00   82
 24  ω   -163.00-121.00   0.50    1.60    --  -91.75 -94.00 120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2911374000
_diffrn_orient_matrix_UB_12      0.0205352000
_diffrn_orient_matrix_UB_13      0.0111693000
_diffrn_orient_matrix_UB_21      -0.0401649000
_diffrn_orient_matrix_UB_22      0.0448920000
_diffrn_orient_matrix_UB_23      0.1070078000
_diffrn_orient_matrix_UB_31      0.0844749000
_diffrn_orient_matrix_UB_32      -0.0496389000
_diffrn_orient_matrix_UB_33      0.1015227000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2101
_reflns_number_total             2241
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.4354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0683
_refine_special_details          ?
_olex2_refinement_description    
;
;
_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
Cl12 Cl -0.27524(6) 0.65769(2) 0.06889(3) 0.02803(11) Uani 1 1 d . . . . .
O9 O 1.01737(18) 0.35816(4) 0.20977(8) 0.0240(2) Uani 1 1 d . . . . .
N7 N 0.9821(2) 0.42670(5) 0.36935(10) 0.0186(2) Uani 1 1 d . . . . .
N6 N 0.6939(2) 0.50506(5) 0.38572(9) 0.0196(2) Uani 1 1 d . . . . .
C4 C 0.3311(2) 0.53098(5) 0.21747(11) 0.0194(2) Uani 1 1 d . . . . .
C1 C 0.7623(2) 0.46034(5) 0.31101(11) 0.0178(2) Uani 1 1 d . . . . .
C18 C 1.4929(2) 0.31309(5) 0.35616(12) 0.0209(3) Uani 1 1 d . . . . .
C10 C 0.1186(3) 0.57197(6) 0.17105(12) 0.0220(3) Uani 1 1 d . . . . .
C8 C 1.0872(2) 0.37634(5) 0.31945(11) 0.0185(2) Uani 1 1 d . . . . .
C2 C 0.6200(3) 0.44793(6) 0.18845(12) 0.0218(3) Uani 1 1 d . . . . .
C13 C 1.2952(2) 0.34259(5) 0.40939(12) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.4812(2) 0.53851(5) 0.33948(11) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.4035(3) 0.48363(6) 0.14276(11) 0.0223(3) Uani 1 1 d . . . . .
C11 C -0.0482(3) 0.60787(6) 0.12834(12) 0.0232(3) Uani 1 1 d . . . . .
C17 C 1.6797(3) 0.27738(6) 0.43281(13) 0.0236(3) Uani 1 1 d . . . . .
C14 C 1.2842(3) 0.33548(5) 0.53953(12) 0.0212(3) Uani 1 1 d . . . . .
C16 C 1.6684(3) 0.27019(6) 0.56256(13) 0.0253(3) Uani 1 1 d . . . . .
C15 C 1.4713(3) 0.29913(6) 0.61555(12) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.433(3) 0.5704(7) 0.3951(14) 0.019(3) Uiso 1 1 d . . . . .
H2 H 0.676(3) 0.4166(7) 0.1411(15) 0.027(4) Uiso 1 1 d . . . . .
H18 H 1.499(3) 0.3179(7) 0.2666(15) 0.023(4) Uiso 1 1 d . . . . .
H14 H 1.146(3) 0.3557(7) 0.5764(14) 0.023(4) Uiso 1 1 d . . . . .
H17 H 1.814(3) 0.2577(7) 0.3966(15) 0.027(4) Uiso 1 1 d . . . . .
H16 H 1.795(3) 0.2445(7) 0.6151(16) 0.029(4) Uiso 1 1 d . . . . .
H3 H 0.301(3) 0.4765(7) 0.0591(15) 0.029(4) Uiso 1 1 d . . . . .
H7 H 1.057(3) 0.4411(7) 0.4418(16) 0.026(4) Uiso 1 1 d . . . . .
H15 H 1.460(3) 0.2944(8) 0.7061(17) 0.035(4) 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
Cl12 C11 1.6431(13) . ?
O9 C8 1.2213(14) . ?
N7 C1 1.3995(16) . ?
N7 C8 1.3742(16) . ?
N7 H7 0.858(16) . ?
N6 C1 1.3435(16) . ?
N6 C5 1.3359(16) . ?
C4 C10 1.4340(17) . ?
C4 C5 1.3955(16) . ?
C4 C3 1.3934(18) . ?
C1 C2 1.4020(16) . ?
C18 C13 1.3955(18) . ?
C18 C17 1.3880(18) . ?
C18 H18 0.958(15) . ?
C10 C11 1.1941(18) . ?
C8 C13 1.4991(16) . ?
C2 C3 1.3770(18) . ?
C2 H2 0.926(16) . ?
C13 C14 1.3936(17) . ?
C5 H5 0.972(15) . ?
C3 H3 0.962(16) . ?
C17 C16 1.3900(19) . ?
C17 H17 0.946(17) . ?
C14 C15 1.3941(18) . ?
C14 H14 0.969(16) . ?
C16 C15 1.386(2) . ?
C16 H16 0.962(16) . ?
C15 H15 0.973(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N7 H7 113.9(10) . . ?
C8 N7 C1 126.44(10) . . ?
C8 N7 H7 119.7(11) . . ?
C5 N6 C1 117.66(10) . . ?
C5 C4 C10 120.63(11) . . ?
C3 C4 C10 122.28(11) . . ?
C3 C4 C5 117.06(11) . . ?
N7 C1 C2 123.94(11) . . ?
N6 C1 N7 113.39(10) . . ?
N6 C1 C2 122.63(11) . . ?
C13 C18 H18 119.4(9) . . ?
C17 C18 C13 120.14(12) . . ?
C17 C18 H18 120.5(9) . . ?
C11 C10 C4 176.04(14) . . ?
O9 C8 N7 123.83(11) . . ?
O9 C8 C13 120.20(11) . . ?
N7 C8 C13 115.95(10) . . ?
C1 C2 H2 118.9(10) . . ?
C3 C2 C1 118.39(11) . . ?
C3 C2 H2 122.7(10) . . ?
C18 C13 C8 117.37(11) . . ?
C14 C13 C18 119.71(11) . . ?
C14 C13 C8 122.68(11) . . ?
N6 C5 C4 124.10(11) . . ?
N6 C5 H5 116.7(8) . . ?
C4 C5 H5 119.2(8) . . ?
C4 C3 H3 119.2(9) . . ?
C2 C3 C4 120.10(11) . . ?
C2 C3 H3 120.7(9) . . ?
C10 C11 Cl12 179.37(13) . . ?
C18 C17 C16 120.14(12) . . ?
C18 C17 H17 119.9(9) . . ?
C16 C17 H17 119.9(10) . . ?
C13 C14 C15 119.75(12) . . ?
C13 C14 H14 119.7(9) . . ?
C15 C14 H14 120.5(9) . . ?
C17 C16 H16 120.1(10) . . ?
C15 C16 C17 119.86(12) . . ?
C15 C16 H16 120.0(10) . . ?
C14 C15 H15 118.8(10) . . ?
C16 C15 C14 120.40(12) . . ?
C16 C15 H15 120.8(10) . . ?

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
O9 C8 C13 C18 32.29(16) . . . . ?
O9 C8 C13 C14 -142.04(12) . . . . ?
N7 C1 C2 C3 178.62(11) . . . . ?
N7 C8 C13 C18 -148.92(11) . . . . ?
N7 C8 C13 C14 36.75(16) . . . . ?
N6 C1 C2 C3 0.79(19) . . . . ?
C1 N7 C8 O9 8.25(19) . . . . ?
C1 N7 C8 C13 -170.49(11) . . . . ?
C1 N6 C5 C4 -1.91(18) . . . . ?
C1 C2 C3 C4 0.33(19) . . . . ?
C18 C13 C14 C15 0.20(18) . . . . ?
C18 C17 C16 C15 -0.47(19) . . . . ?
C10 C4 C5 N6 -174.88(11) . . . . ?
C10 C4 C3 C2 175.75(12) . . . . ?
C8 N7 C1 N6 176.01(11) . . . . ?
C8 N7 C1 C2 -1.99(19) . . . . ?
C8 C13 C14 C15 174.41(11) . . . . ?
C13 C18 C17 C16 0.87(18) . . . . ?
C13 C14 C15 C16 0.19(19) . . . . ?
C5 N6 C1 N7 -178.07(10) . . . . ?
C5 N6 C1 C2 -0.04(17) . . . . ?
C5 C4 C3 C2 -2.06(18) . . . . ?
C3 C4 C5 N6 2.96(18) . . . . ?
C17 C18 C13 C8 -175.24(11) . . . . ?
C17 C18 C13 C14 -0.73(18) . . . . ?
C17 C16 C15 C14 -0.05(19) . . . . ?


_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 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.844
####################################################################### 
# 
# 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_2act-Br
_database_code_depnum_ccdc_archive 'CCDC 2089323'
loop_
_audit_author_name
_audit_author_address
'Christer B. Aakeroy'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Br N3 O'
_chemical_formula_sum            'C13 H8 Br N3 O'
_chemical_formula_weight         302.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 Br1 N3 O1'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   3.8797(2)
_cell_length_b                   21.3190(14)
_cell_length_c                   14.8922(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.148(5)
_cell_angle_gamma                90
_cell_volume                     1226.79(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4602
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      75.0960
_cell_measurement_theta_min      3.5950
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.566
_exptl_absorpt_coefficient_mu    4.499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.96a (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    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method 'crystallized from acetone'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.032
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7916
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.529
_diffrn_reflns_theta_min         3.630
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  30.00   0.50    3.95    --  -43.30  59.00  44.00  182
  2  ω    -68.00 -21.00   0.50    3.95    --  -43.30 -59.00 -95.00   94
  3  ω   -111.00 -86.00   0.50    3.95    --  -43.30 -59.00 -95.00   50
  4  ω   -163.00-134.00   0.50   15.82    --  -90.25 -59.00 -95.00   58
  5  ω    -66.00 -41.00   0.50   15.82    --  -90.25  59.00  44.00   50
  6  ω     38.00  63.00   0.50   15.82    --  111.75 -59.00 -95.00   50
  7  ω    114.00 178.00   0.50   15.82    --  111.75  59.00  44.00  128
  8  ω    -84.00 -48.00   0.50    3.95    --  -43.30 125.00 150.00   72
  9  ω    -45.00 -14.00   0.50    3.95    --  -43.30 125.00 150.00   62
 10  ω     67.00 107.00   0.50    3.95    --   43.30  59.00  44.00   80
 11  ω    -51.00 -26.00   0.50   15.82    --  -90.25  45.00-180.00   50
 12  ω    -50.00 -24.00   0.50   15.82    --  -90.25  45.00-150.00   52
 13  ω     38.00  64.00   0.50   15.82    --  111.75 -61.00 -30.00   52
 14  ω     42.00  71.00   0.50   15.82    --  111.75 -61.00 120.00   58
 15  ω     92.00 133.00   0.50   15.82    --  111.75  45.00 -30.00   82
 16  ω     42.00  70.00   0.50   15.82    --  111.75 -94.00 -90.00   56
 17  ω     39.00  93.00   0.50   15.82    --  111.75-125.00 120.00  108
 18  ω     74.00  99.00   0.50   15.82    --  111.75 -94.00 -90.00   50
 19  ω     48.00 104.00   0.50   15.82    --  111.75 -77.00   0.00  112
 20  ω     43.00  71.00   0.50   15.82    --  111.75 -61.00 150.00   56
 21  ω     45.00  70.00   0.50   15.82    --  111.75 -61.00 -60.00   50
 22  ω     39.00  71.00   0.50   15.82    --  111.75 -61.00-150.00   64
 23  ω     96.00 137.00   0.50   15.82    --  111.75 125.00-120.00   82
 24  ω     45.00  70.00   0.50   15.82    --  111.75 -61.00-180.00   50
 25  ω     97.00 166.00   0.50   15.82    --  111.75  77.00 120.00  138
 26  ω    117.00 158.00   0.50   15.82    --  111.75  30.00 120.00   82
 27  ω     80.00 105.00   0.50   15.82    --  111.75 -77.00 -90.00   50
 28  ω     45.00  70.00   0.50   15.82    --  111.75 -61.00  30.00   50
 29  ω    142.00 168.00   0.50   15.82    --  111.75  45.00 -30.00   52
 30  ω     48.00  78.00   0.50   15.82    --  111.75-125.00-150.00   60
 31  ω     41.00 107.00   0.50   15.82    --  111.75-125.00-120.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2856562000
_diffrn_orient_matrix_UB_12      -0.0457678000
_diffrn_orient_matrix_UB_13      0.0368812000
_diffrn_orient_matrix_UB_21      0.2287520000
_diffrn_orient_matrix_UB_22      0.0215190000
_diffrn_orient_matrix_UB_23      -0.0736032000
_diffrn_orient_matrix_UB_31      0.1576763000
_diffrn_orient_matrix_UB_32      0.0516262000
_diffrn_orient_matrix_UB_33      0.0633743000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2208
_reflns_number_total             2542
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.938
_refine_diff_density_min         -1.707
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.099
_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)+(0.0615P)²+4.2645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1540
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C3(H3), C6(H6), C5(H5), C18(H18), C15(H15), C16(H16), C17(H17)
;
_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
Br9 Br 0.06063(14) 0.20185(3) 0.65898(3) 0.0428(2) Uani 1 1 d . . . . .
O12 O 0.9191(11) 0.54863(19) 0.3567(3) 0.0546(10) Uani 1 1 d . . . . .
N2 N 0.3699(11) 0.37891(18) 0.3067(2) 0.0345(8) Uani 1 1 d . . . . .
N10 N 0.6306(11) 0.47129(18) 0.2727(3) 0.0362(9) Uani 1 1 d . . . . .
H10 H 0.563336 0.460626 0.216795 0.043 Uiso 1 1 calc R U . . .
N14 N 0.7346(12) 0.5328(2) 0.1200(3) 0.0450(10) Uani 1 1 d . . . . .
C4 C 0.3597(12) 0.3404(2) 0.4577(3) 0.0341(10) Uani 1 1 d . . . . .
C3 C 0.2768(13) 0.3361(2) 0.3651(3) 0.0349(10) Uani 1 1 d . . . . .
H3 H 0.147080 0.300894 0.342304 0.042 Uiso 1 1 calc R U . . .
C1 C 0.5488(13) 0.4293(2) 0.3396(3) 0.0335(9) Uani 1 1 d . . . . .
C11 C 0.8032(14) 0.5271(2) 0.2842(3) 0.0394(11) Uani 1 1 d . . . . .
C6 C 0.6390(13) 0.4380(2) 0.4313(3) 0.0391(10) Uani 1 1 d . . . . .
H6 H 0.763246 0.474188 0.452575 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5446(13) 0.3931(2) 0.4901(3) 0.0374(10) Uani 1 1 d . . . . .
H5 H 0.605081 0.397795 0.552996 0.045 Uiso 1 1 calc R U . . .
C7 C 0.2560(13) 0.2934(2) 0.5190(3) 0.0357(10) Uani 1 1 d . . . . .
C13 C 0.8466(13) 0.5609(2) 0.1983(3) 0.0395(11) Uani 1 1 d . . . . .
C8 C 0.1759(13) 0.2564(3) 0.5738(3) 0.0428(11) Uani 1 1 d . . . . .
C18 C 0.9977(16) 0.6203(3) 0.2021(5) 0.0547(14) Uani 1 1 d . . . . .
H18 H 1.070666 0.639316 0.258356 0.066 Uiso 1 1 calc R U . . .
C15 C 0.7760(16) 0.5637(3) 0.0436(4) 0.0549(14) Uani 1 1 d . . . . .
H15 H 0.697525 0.544454 -0.012073 0.066 Uiso 1 1 calc R U . . .
C16 C 0.9284(16) 0.6224(3) 0.0419(5) 0.0628(17) Uani 1 1 d . . . . .
H16 H 0.955824 0.642568 -0.013920 0.075 Uiso 1 1 calc R U . . .
C17 C 1.0383(19) 0.6510(3) 0.1213(5) 0.0655(18) Uani 1 1 d . . . . .
H17 H 1.141569 0.691401 0.121354 0.079 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
Br9 C8 1.807(5) . ?
O12 C11 1.222(6) . ?
N2 C3 1.332(6) . ?
N2 C1 1.348(6) . ?
N10 C1 1.397(6) . ?
N10 C11 1.369(6) . ?
N14 C13 1.347(7) . ?
N14 C15 1.335(7) . ?
C4 C3 1.391(6) . ?
C4 C5 1.395(7) . ?
C4 C7 1.438(6) . ?
C1 C6 1.390(6) . ?
C11 C13 1.490(7) . ?
C6 C5 1.369(7) . ?
C7 C8 1.195(7) . ?
C13 C18 1.395(7) . ?
C18 C17 1.392(9) . ?
C15 C16 1.387(8) . ?
C16 C17 1.363(10) . ?

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 C1 118.0(4) . . ?
C11 N10 C1 127.5(4) . . ?
C15 N14 C13 117.7(5) . . ?
C3 C4 C5 117.5(4) . . ?
C3 C4 C7 122.1(5) . . ?
C5 C4 C7 120.4(4) . . ?
N2 C3 C4 123.4(4) . . ?
N2 C1 N10 113.2(4) . . ?
N2 C1 C6 122.6(4) . . ?
C6 C1 N10 124.2(4) . . ?
O12 C11 N10 125.0(5) . . ?
O12 C11 C13 121.1(5) . . ?
N10 C11 C13 113.9(4) . . ?
C5 C6 C1 118.5(5) . . ?
C6 C5 C4 120.0(4) . . ?
C8 C7 C4 176.4(6) . . ?
N14 C13 C11 118.4(4) . . ?
N14 C13 C18 122.7(5) . . ?
C18 C13 C11 118.9(5) . . ?
C7 C8 Br9 178.5(5) . . ?
C17 C18 C13 118.1(6) . . ?
N14 C15 C16 123.0(6) . . ?
C17 C16 C15 119.2(6) . . ?
C16 C17 C18 119.3(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
C6 H6 O12 0.95 2.25 2.863(6) 121.2 . yes

_olex2_date_sample_data_collection 2021-02-19
_olex2_date_sample_submission    2021-02-17
_olex2_exptl_crystal_mounting_method 'mounted on  a MiTegen loop'
_olex2_submission_original_sample_id 2act-Br
_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 2.695
_oxdiff_exptl_absorpt_empirical_full_min 0.548
####################################################################### 
# 
# 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_4act-I
_database_code_depnum_ccdc_archive 'CCDC 2089330'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 I N3 O'
_chemical_formula_sum            'C13 H8 I N3 O'
_chemical_formula_weight         349.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 I1 N3 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.2100(2)
_cell_length_b                   13.0373(2)
_cell_length_c                   18.7180(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.054(2)
_cell_angle_gamma                90
_cell_volume                     2427.18(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13528
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      33.5470
_cell_measurement_theta_min      2.2070
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    2.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method '?crystallized from acetone/THF'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15079
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.419
_diffrn_reflns_theta_min         2.234
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  19.00   0.50    4.50    --   12.33 -45.00  33.00  156
  2  ω     47.00  86.00   0.50    4.50    --   12.33-178.00  30.00   78
  3  ω     53.00  84.00   0.50    4.50    --   12.33-178.00 -30.00   62
  4  ω     38.00  63.00   0.50    4.50    --   12.33-178.00-120.00   50
  5  ω     22.00  84.00   0.50    4.50    --   12.33  45.00-175.00  124
  6  ω    -63.00  -4.00   0.50    4.50    --   12.33 -19.00 -90.00  118
  7  ω    -80.00 -20.00   0.50    4.50    --  -12.49 -19.00  30.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0652652000
_diffrn_orient_matrix_UB_12      0.0100293000
_diffrn_orient_matrix_UB_13      0.0055851000
_diffrn_orient_matrix_UB_21      0.0154848000
_diffrn_orient_matrix_UB_22      -0.0286943000
_diffrn_orient_matrix_UB_23      0.0330318000
_diffrn_orient_matrix_UB_31      0.0243011000
_diffrn_orient_matrix_UB_32      0.0450989000
_diffrn_orient_matrix_UB_33      0.0197672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3962
_reflns_number_total             4104
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.842
_refine_diff_density_min         -2.296
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       0.00048(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+6.9695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C3(H3), C5(H5), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18)
;
_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
I9 I -0.20134(2) 0.60045(2) 0.36415(2) 0.01513(7) Uani 1 1 d . . . . .
O12 O 0.70399(19) 0.36189(15) 0.47465(11) 0.0197(4) Uani 1 1 d . . . . .
N2 N 0.3696(2) 0.37190(16) 0.29644(12) 0.0140(3) Uani 1 1 d . . . . .
N10 N 0.58604(19) 0.33413(16) 0.35631(12) 0.0140(4) Uani 1 1 d . . . . .
H10 H 0.593794 0.310148 0.313517 0.017 Uiso 1 1 calc R U . . .
N16 N 1.0527(2) 0.18447(17) 0.37471(14) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.2471(3) 0.41054(17) 0.29465(16) 0.0158(4) Uani 1 1 d . . . . .
H3 H 0.182388 0.409438 0.249345 0.019 Uiso 1 1 calc R U . . .
C4 C 0.2095(2) 0.45231(18) 0.35578(15) 0.0156(4) Uani 1 1 d . . . . .
C5 C 0.3043(2) 0.4501(2) 0.42236(15) 0.0183(4) Uani 1 1 d . . . . .
H5 H 0.281833 0.476102 0.465470 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4311(3) 0.41000(19) 0.42566(16) 0.0170(4) Uani 1 1 d . . . . .
H6 H 0.496295 0.407373 0.470730 0.020 Uiso 1 1 calc R U . . .
C1 C 0.4604(2) 0.37349(17) 0.36076(14) 0.0136(4) Uani 1 1 d . . . . .
C11 C 0.6981(2) 0.32969(17) 0.41283(14) 0.0133(4) Uani 1 1 d . . . . .
C13 C 0.8191(2) 0.28023(17) 0.39454(14) 0.0141(4) Uani 1 1 d . . . . .
C14 C 0.8129(3) 0.20647(19) 0.34045(15) 0.0172(4) Uani 1 1 d . . . . .
H14 H 0.729345 0.187905 0.309241 0.021 Uiso 1 1 calc R U . . .
C15 C 0.9323(3) 0.1602(2) 0.33299(16) 0.0193(5) Uani 1 1 d . . . . .
H15 H 0.927849 0.108944 0.296451 0.023 Uiso 1 1 calc R U . . .
C17 C 1.0573(2) 0.2563(2) 0.42600(16) 0.0193(5) Uani 1 1 d . . . . .
H17 H 1.142529 0.274721 0.455479 0.023 Uiso 1 1 calc R U . . .
C18 C 0.9442(2) 0.3055(2) 0.43852(16) 0.0181(4) Uani 1 1 d . . . . .
H18 H 0.951863 0.355310 0.476263 0.022 Uiso 1 1 calc R U . . .
C7 C 0.0804(2) 0.49820(19) 0.35227(16) 0.0184(4) Uani 1 1 d . . . . .
C8 C -0.0232(2) 0.53931(19) 0.35668(16) 0.0184(4) 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
I9 C8 2.019(2) . ?
O12 C11 1.220(3) . ?
N2 C3 1.342(3) . ?
N2 C1 1.344(3) . ?
N10 C1 1.401(3) . ?
N10 C11 1.373(3) . ?
N16 C15 1.337(3) . ?
N16 C17 1.335(4) . ?
C3 C4 1.397(4) . ?
C4 C5 1.395(4) . ?
C4 C7 1.435(3) . ?
C5 C6 1.384(3) . ?
C6 C1 1.399(4) . ?
C11 C13 1.500(3) . ?
C13 C14 1.387(4) . ?
C13 C18 1.394(3) . ?
C14 C15 1.395(3) . ?
C17 C18 1.386(3) . ?
C7 C8 1.206(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 C1 117.9(2) . . ?
C11 N10 C1 125.7(2) . . ?
C17 N16 C15 117.7(2) . . ?
N2 C3 C4 123.6(2) . . ?
C3 C4 C7 123.0(2) . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C7 119.6(2) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C6 C1 118.1(3) . . ?
N2 C1 N10 113.4(2) . . ?
N2 C1 C6 122.9(2) . . ?
C6 C1 N10 123.7(2) . . ?
O12 C11 N10 124.8(2) . . ?
O12 C11 C13 119.8(2) . . ?
N10 C11 C13 115.3(2) . . ?
C14 C13 C11 124.1(2) . . ?
C14 C13 C18 118.6(2) . . ?
C18 C13 C11 117.1(2) . . ?
C13 C14 C15 118.4(2) . . ?
N16 C15 C14 123.3(2) . . ?
N16 C17 C18 123.5(2) . . ?
C17 C18 C13 118.6(2) . . ?
C8 C7 C4 173.4(3) . . ?
C7 C8 I9 176.9(2) . . ?

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
C6 H6 O12 0.95 2.19 2.801(3) 121.3 . yes

_olex2_exptl_crystal_mounting_method 'mounted on a glass fibre'
_olex2_submission_original_sample_id 4act-I
_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 1.849
_oxdiff_exptl_absorpt_empirical_full_min 0.639
####################################################################### 
# 
# 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_4act-Cl
_database_code_depnum_ccdc_archive 'CCDC 2089327'
loop_
_audit_author_name
_audit_author_address
'Pierre Le Magueres'
;Rigaku Americas Corporation 
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-03-03
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Cl N3 O'
_chemical_formula_sum            'C13 H8 Cl N3 O'
_chemical_formula_weight         257.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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                   3.77350(10)
_cell_length_b                   10.1396(2)
_cell_length_c                   29.0994(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.876(2)
_cell_angle_gamma                90
_cell_volume                     1113.26(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4423
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2880
_cell_measurement_theta_min      3.0390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.80a (Rigaku Oxford Diffraction, 2020)
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    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.031
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            3178
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.514
_diffrn_reflns_theta_min         3.038
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    116.00 160.00   0.50    2.40    --  104.42 101.00 -40.00   88
  2  ω     42.00  68.00   0.50    2.40    --  104.42 -61.00 -90.00   52
  3  ω     37.00  65.00   0.50    2.40    --  104.42 -77.00-150.00   56
  4  ω     71.00  97.00   0.50    2.40    --  104.42 -77.00-150.00   52
  5  ω     -2.00  23.00   0.50    0.60    --  -46.02  19.00-120.00   50
  6  ω    -49.00 -20.00   0.50    2.40    --  -91.75  45.00 -90.00   58
  7  ω    -10.00  15.00   0.50    0.60    --  -46.02  19.00 -30.00   50
  8  ω    -49.00 -20.00   0.50    2.40    --  -91.75  45.00  90.00   58
  9  ω    -81.00 -19.00   0.50    2.40    --  -91.75 112.00  47.00  124
 10  ω   -166.00 -79.00   0.50    2.40    --  -91.75 -27.00  40.00  174
 11  ω   -110.00 -44.00   0.50    0.60    --  -46.02 -27.00  40.00  132
 12  ω    -71.00 -40.00   0.50    2.40    --  -91.75 101.00 -40.00   62
 13  ω    -68.00 -35.00   0.50    0.60    --  -46.02 125.00   0.00   66
 14  ω     59.00  85.00   0.50    0.60    --   46.02-125.00 120.00   52
 15  ω   -146.00-106.00   0.50    2.40    --  -91.75-101.00-144.00   80
 16  ω    -53.00 -28.00   0.50    2.40    --  -91.75  45.00 -60.00   50
 17  ω    109.00 136.00   0.50    2.40    --  101.80 125.00  60.00   54
 18  ω     29.00  54.00   0.50    2.40    --  101.80 -61.00-150.00   50
 19  ω     82.00 108.00   0.50    2.40    --  101.80-125.00-120.00   52
 20  ω    136.00 162.00   0.50    2.40    --  101.80  61.00-150.00   52
 21  ω    142.00 168.00   0.50    2.40    --  101.80 125.00  60.00   52
 22  ω     33.00  63.00   0.50    2.40    --  101.80 -61.00   0.00   60
 23  ω     33.00 107.00   0.50    0.60    --   46.02  19.00 -60.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0773164000
_diffrn_orient_matrix_UB_12      -0.0058335000
_diffrn_orient_matrix_UB_13      -0.0521027000
_diffrn_orient_matrix_UB_21      0.1229322000
_diffrn_orient_matrix_UB_22      -0.1448497000
_diffrn_orient_matrix_UB_23      -0.0008797000
_diffrn_orient_matrix_UB_31      -0.3815970000
_diffrn_orient_matrix_UB_32      -0.0454399000
_diffrn_orient_matrix_UB_33      0.0094145000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2965
_reflns_number_total             3178
_reflns_special_details          
;
 _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 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.064
_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)+(0.0392P)²+0.6193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0910
_refine_special_details          
;
 Refined as a 3-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.66(4)
 0.130(7) 0.21(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C14(H14), C15(H15), C3(H3), C6(H6), C5(H5), C18(H18), C17(H17)
;
_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
Cl9 Cl 0.81514(14) 0.86432(5) 0.48472(2) 0.02728(15) Uani 1 1 d . . . . .
O12 O 0.3556(4) -0.00363(15) 0.39613(5) 0.0292(4) Uani 1 1 d . . . . .
N10 N 0.3012(4) 0.16666(16) 0.34458(6) 0.0181(4) Uani 1 1 d . . . . .
H10 H 0.240647 0.184576 0.315928 0.022 Uiso 1 1 calc R U . . .
N2 N 0.3061(4) 0.39037(17) 0.35423(6) 0.0185(4) Uani 1 1 d . . . . .
N16 N 0.0132(4) -0.24163(17) 0.25110(6) 0.0193(4) Uani 1 1 d . . . . .
C4 C 0.5747(5) 0.4979(2) 0.41993(7) 0.0184(4) Uani 1 1 d . . . . .
C14 C 0.2784(5) -0.03578(19) 0.27383(7) 0.0179(4) Uani 1 1 d . . . . .
H14 H 0.400731 0.042063 0.265199 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2909(5) 0.0364(2) 0.35760(7) 0.0188(4) Uani 1 1 d . . . . .
C7 C 0.6611(5) 0.6196(2) 0.44236(7) 0.0213(4) Uani 1 1 d . . . . .
C15 C 0.1843(5) -0.12898(19) 0.24115(7) 0.0189(4) Uani 1 1 d . . . . .
H15 H 0.243534 -0.112611 0.210053 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3943(5) 0.4981(2) 0.37785(7) 0.0191(4) Uani 1 1 d . . . . .
H3 H 0.329551 0.581114 0.365095 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1918(5) -0.05750(19) 0.31948(7) 0.0168(4) Uani 1 1 d . . . . .
C6 C 0.5821(5) 0.2607(2) 0.41442(7) 0.0186(4) Uani 1 1 d . . . . .
H6 H 0.644965 0.176314 0.426193 0.022 Uiso 1 1 calc R U . . .
C5 C 0.6685(5) 0.3746(2) 0.43812(7) 0.0195(4) Uani 1 1 d . . . . .
H5 H 0.791584 0.369347 0.466780 0.023 Uiso 1 1 calc R U . . .
C1 C 0.3990(5) 0.2737(2) 0.37250(7) 0.0175(4) Uani 1 1 d . . . . .
C18 C 0.0210(5) -0.1752(2) 0.33055(7) 0.0187(4) Uani 1 1 d . . . . .
H18 H -0.037451 -0.194710 0.361454 0.022 Uiso 1 1 calc R U . . .
C8 C 0.7286(5) 0.7236(2) 0.45934(7) 0.0216(4) Uani 1 1 d . . . . .
C17 C -0.0610(5) -0.2626(2) 0.29554(7) 0.0202(4) Uani 1 1 d . . . . .
H17 H -0.176994 -0.342496 0.303359 0.024 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
Cl9 C8 1.637(2) . ?
O12 C11 1.214(2) . ?
N10 H10 0.8800 . ?
N10 C11 1.375(3) . ?
N10 C1 1.402(3) . ?
N2 C3 1.331(3) . ?
N2 C1 1.341(3) . ?
N16 C15 1.346(3) . ?
N16 C17 1.344(3) . ?
C4 C7 1.431(3) . ?
C4 C3 1.392(3) . ?
C4 C5 1.401(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C14 C13 1.390(3) . ?
C11 C13 1.505(3) . ?
C7 C8 1.190(3) . ?
C15 H15 0.9500 . ?
C3 H3 0.9500 . ?
C13 C18 1.396(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.382(3) . ?
C6 C1 1.399(3) . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.382(3) . ?
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
C11 N10 H10 116.8 . . ?
C11 N10 C1 126.33(17) . . ?
C1 N10 H10 116.8 . . ?
C3 N2 C1 117.25(17) . . ?
C17 N16 C15 116.68(18) . . ?
C3 C4 C7 120.31(19) . . ?
C3 C4 C5 116.81(18) . . ?
C5 C4 C7 122.87(18) . . ?
C15 C14 H14 120.4 . . ?
C15 C14 C13 119.14(19) . . ?
C13 C14 H14 120.4 . . ?
O12 C11 N10 124.75(19) . . ?
O12 C11 C13 120.88(19) . . ?
N10 C11 C13 114.36(17) . . ?
C8 C7 C4 177.2(2) . . ?
N16 C15 C14 123.43(19) . . ?
N16 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
N2 C3 C4 124.63(19) . . ?
N2 C3 H3 117.7 . . ?
C4 C3 H3 117.7 . . ?
C14 C13 C11 122.99(18) . . ?
C14 C13 C18 118.17(18) . . ?
C18 C13 C11 118.76(18) . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C1 117.74(19) . . ?
C1 C6 H6 121.1 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.09(18) . . ?
C6 C5 H5 120.0 . . ?
N2 C1 N10 112.86(17) . . ?
N2 C1 C6 123.47(18) . . ?
C6 C1 N10 123.65(18) . . ?
C13 C18 H18 120.8 . . ?
C17 C18 C13 118.49(19) . . ?
C17 C18 H18 120.8 . . ?
C7 C8 Cl9 177.6(2) . . ?
N16 C17 C18 124.1(2) . . ?
N16 C17 H17 118.0 . . ?
C18 C17 H17 118.0 . . ?

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
O12 C11 C13 C14 -147.8(2) . . . . ?
O12 C11 C13 C18 28.8(3) . . . . ?
N10 C11 C13 C14 31.9(3) . . . . ?
N10 C11 C13 C18 -151.45(18) . . . . ?
C14 C13 C18 C17 -1.6(3) . . . . ?
C11 N10 C1 N2 -165.31(18) . . . . ?
C11 N10 C1 C6 16.3(3) . . . . ?
C11 C13 C18 C17 -178.33(18) . . . . ?
C7 C4 C3 N2 179.23(19) . . . . ?
C7 C4 C5 C6 -178.98(19) . . . . ?
C15 N16 C17 C18 1.4(3) . . . . ?
C15 C14 C13 C11 178.43(17) . . . . ?
C15 C14 C13 C18 1.8(3) . . . . ?
C3 N2 C1 N10 -178.68(17) . . . . ?
C3 N2 C1 C6 -0.2(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C13 C14 C15 N16 -0.5(3) . . . . ?
C13 C18 C17 N16 -0.1(3) . . . . ?
C5 C4 C3 N2 0.1(3) . . . . ?
C5 C6 C1 N10 178.72(18) . . . . ?
C5 C6 C1 N2 0.5(3) . . . . ?
C1 N10 C11 O12 2.4(3) . . . . ?
C1 N10 C11 C13 -177.27(17) . . . . ?
C1 N2 C3 C4 -0.1(3) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C17 N16 C15 C14 -1.1(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.202
_oxdiff_exptl_absorpt_empirical_full_min 0.798
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.66(4)
2 0.130(7)
3 0.21(4)

_twin_special_details            
;
Component 2 rotated by -179.9769° 
around [-0.00 0.00 1.00] (reciprocal) or [0.12 -0.00 0.99] (direct)
;
####################################################################### 
# 
# 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_3act-I
_database_code_depnum_ccdc_archive 'CCDC 2089326'
loop_
_audit_author_name
_audit_author_address
'Pierre Le Magueres'
;Rigaku Americas Corporation 
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 I N3 O'
_chemical_formula_sum            'C13 H8 I N3 O'
_chemical_formula_weight         349.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 I N3 O'
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      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                   12.7284(3)
_cell_length_b                   6.7266(2)
_cell_length_c                   14.4741(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.558(3)
_cell_angle_gamma                90
_cell_volume                     1199.47(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7750
_cell_measurement_theta_min      3.1550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.908
_exptl_absorpt_correction_T_max  0.46137
_exptl_absorpt_correction_T_min  0.41004
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.83a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
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    1.933
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -2 0.0192
1 0 1 0.0309
-1 0 -1 0.0309
-2 -1 2 0.0148
-1 -2 -1 0.0190
-2 -2 1 0.0175
1 2 -2 0.0177
3 0 1 0.0399
-1 1 3 0.0369
2 0 -3 0.0453
-3 2 2 0.0309
3 -1 3 0.0344
-5 1 0 0.0215
-1 -1 2 0.0145

_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.041
_exptl_crystal_size_rad          0.030
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
0.0081 0.9979 -2.0093 0.0235 -0.2215 -0.2264
0.9969 0.0011 1.0042 -0.0393 0.1776 -0.0403
-0.9969 -0.0011 -1.0042 0.0393 -0.1776 0.0403
-2.0073 -0.9989 2.0034 -0.0953 0.0197 0.3555
-1.0020 -1.9995 -0.9907 0.2930 -0.0412 0.3959
-2.0071 -1.9987 1.0089 0.1067 0.0112 0.5090
1.0102 1.9976 -2.0132 -0.0674 -0.1888 -0.4687
2.9961 0.0021 1.0102 0.0326 0.3794 -0.1693
-1.0052 1.0006 2.9941 -0.3883 0.0609 -0.0404
2.0074 -0.0010 -2.9979 0.2974 -0.0282 -0.2019
-2.9991 1.9983 1.9801 -0.5118 -0.2858 -0.1134
2.9880 -0.9959 3.0195 0.0091 0.6009 0.0571
-4.9954 0.9968 -0.0216 -0.3064 -0.5728 0.1449
-1.0077 -0.9984 2.0064 -0.0594 0.1206 0.2909

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8148
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.057
_diffrn_reflns_theta_max         67.057
_diffrn_reflns_theta_min         3.588
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  62.00   0.50    0.50    --   62.80   0.00-150.00   52
  2  ω     47.00  92.00   0.50    0.50    --   62.80  15.00-180.00   90
  3  ω     58.00  93.00   0.50    0.50    --   62.80  15.00 -30.00   70
  4  ω     43.00  85.00   0.50    0.50    --   62.80   0.00 -30.00   84
  5  ω     68.00  97.00   0.50    0.50    --   68.75  20.00  70.06   58
  6  ω     41.00  93.00   0.50    0.50    --   62.80  15.00 120.00  104
  7  ω     43.00  86.00   0.50    0.50    --   62.80   0.00  90.00   86
  8  ω    -71.00 -44.00   0.50    0.50    --  -35.00 -22.00 129.64   54
  9  ω    -60.00 -33.00   0.50    0.50    --  -33.58 -15.00   0.00   54
 10  ω    -65.00 -31.00   0.50    0.50    --  -35.00 -20.00 150.37   68
 11  ω    -72.00 -47.00   0.50    0.50    --  -35.00 -22.00 -67.14   50
 12  ω    -47.00 -22.00   0.50    0.50    --  -35.00 114.00  -7.76   50
 13  ω    -50.00 -25.00   0.50    0.50    --  -35.00 116.00  18.43   50
 14  ω    -52.00 -27.00   0.50    0.50    --  -35.00 121.00-158.39   50
 15  ω    -28.00  -2.00   0.50    0.50    --  -33.58  15.00-150.00   52
 16  ω    -26.00   2.00   0.50    0.50    --  -33.58  15.00-180.00   56
 17  ω    -39.00 -14.00   0.50    0.50    --  -33.58   0.00-180.00   50
 18  ω     32.00  67.00   0.50    0.50    --   62.80-125.00-180.00   70
 19  ω     40.00  66.00   0.50    0.50    --   62.80-125.00-150.00   52
 20  ω     51.00  78.00   0.50    0.50    --   62.80-125.00 -60.00   54
 21  ω     42.00  81.00   0.50    0.50    --   62.80-125.00-120.00   78
 22  ω     32.00  81.00   0.50    0.50    --   62.80-125.00 -90.00   98
 23  ω     32.00  68.00   0.50    0.50    --   62.80-125.00  30.00   72
 24  ω     53.00  89.00   0.50    0.50    --   68.75-126.00  57.99   72
 25  ω     38.00  64.00   0.50    0.50    --   62.80-125.00  90.00   52
 26  ω     35.00  69.00   0.50    0.50    --   68.75-133.00 142.78   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0362131000
_diffrn_orient_matrix_UB_12      -0.1275673000
_diffrn_orient_matrix_UB_13      -0.0749070000
_diffrn_orient_matrix_UB_21      0.1007565000
_diffrn_orient_matrix_UB_22      -0.0679851000
_diffrn_orient_matrix_UB_23      0.0768823000
_diffrn_orient_matrix_UB_31      -0.0645498000
_diffrn_orient_matrix_UB_32      -0.1776215000
_diffrn_orient_matrix_UB_33      0.0241877000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode 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                1957
_reflns_number_total             2136
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.181
_refine_diff_density_min         -1.580
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.091
_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)+(0.0683P)²+0.7768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C14(H14), C6(H6), C16(H16), C3(H3), C18(H18), C5(H5), C17(H17)
;
_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
I9 I -0.08866(2) -0.10567(4) 0.32887(2) 0.02876(16) Uani 1 1 d . . . . .
O12 O 0.3771(2) 0.9864(5) 0.6393(2) 0.0361(8) Uani 1 1 d . . . . .
N15 N 0.7531(3) 0.8869(5) 0.7491(3) 0.0303(9) Uani 1 1 d . . . . .
N10 N 0.4431(3) 0.7099(5) 0.5809(2) 0.0275(8) Uani 1 1 d . . . . .
H10 H 0.502288 0.657810 0.573770 0.033 Uiso 1 1 calc R U . . .
N2 N 0.3673(3) 0.4233(5) 0.5101(3) 0.0291(8) Uani 1 1 d . . . . .
C13 C 0.5683(4) 0.9569(8) 0.6675(3) 0.0257(9) Uani 1 1 d . . . . .
C8 C 0.0229(4) 0.1019(6) 0.3888(4) 0.0303(11) Uani 1 1 d . . . . .
C14 C 0.6504(4) 0.8288(7) 0.7157(3) 0.0284(9) Uani 1 1 d . . . . .
H14 H 0.632613 0.697459 0.724841 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2444(4) 0.6748(8) 0.5356(3) 0.0324(10) Uani 1 1 d . . . . .
H6 H 0.234162 0.801840 0.557123 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7770(4) 1.0776(7) 0.7352(3) 0.0324(11) Uani 1 1 d . . . . .
H16 H 0.848589 1.119546 0.756932 0.039 Uiso 1 1 calc R U . . .
C4 C 0.1749(4) 0.3618(7) 0.4655(4) 0.0299(11) Uani 1 1 d . . . . .
C3 C 0.2815(3) 0.3067(7) 0.4755(3) 0.0301(10) Uani 1 1 d . . . . .
H3 H 0.294677 0.178772 0.456790 0.036 Uiso 1 1 calc R U . . .
C18 C 0.5938(4) 1.1552(8) 0.6566(3) 0.0311(10) Uani 1 1 d . . . . .
H18 H 0.540601 1.245720 0.627366 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4530(4) 0.8882(6) 0.6290(4) 0.0285(11) Uani 1 1 d . . . . .
C7 C 0.0888(3) 0.2246(7) 0.4239(3) 0.0304(10) Uani 1 1 d . . . . .
C1 C 0.3471(4) 0.6031(6) 0.5421(3) 0.0274(11) Uani 1 1 d . . . . .
C5 C 0.1570(4) 0.5544(7) 0.4963(3) 0.0315(10) Uani 1 1 d . . . . .
H5 H 0.086660 0.600127 0.490147 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7003(4) 1.2132(7) 0.6904(3) 0.0318(10) Uani 1 1 d . . . . .
H17 H 0.720265 1.344053 0.682944 0.038 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
I9 C8 2.024(5) . ?
O12 C11 1.210(6) . ?
N15 C14 1.334(6) . ?
N15 C16 1.345(6) . ?
N10 H10 0.8600 . ?
N10 C11 1.377(6) . ?
N10 C1 1.407(6) . ?
N2 C3 1.335(6) . ?
N2 C1 1.343(6) . ?
C13 C14 1.397(7) . ?
C13 C18 1.391(7) . ?
C13 C11 1.505(7) . ?
C8 C7 1.195(6) . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
C6 C1 1.373(7) . ?
C6 C5 1.379(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(7) . ?
C4 C3 1.379(7) . ?
C4 C7 1.443(6) . ?
C4 C5 1.406(7) . ?
C3 H3 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.377(6) . ?
C5 H5 0.9300 . ?
C17 H17 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
C14 N15 C16 117.6(4) . . ?
C11 N10 H10 116.3 . . ?
C11 N10 C1 127.3(4) . . ?
C1 N10 H10 116.3 . . ?
C3 N2 C1 116.7(4) . . ?
C14 C13 C11 122.2(4) . . ?
C18 C13 C14 118.7(4) . . ?
C18 C13 C11 119.1(4) . . ?
C7 C8 I9 179.8(5) . . ?
N15 C14 C13 122.8(4) . . ?
N15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C1 C6 H6 120.8 . . ?
C1 C6 C5 118.5(5) . . ?
C5 C6 H6 120.8 . . ?
N15 C16 H16 118.5 . . ?
N15 C16 C17 122.9(5) . . ?
C17 C16 H16 118.5 . . ?
C3 C4 C7 119.7(4) . . ?
C3 C4 C5 116.6(4) . . ?
C5 C4 C7 123.7(4) . . ?
N2 C3 C4 124.9(4) . . ?
N2 C3 H3 117.6 . . ?
C4 C3 H3 117.6 . . ?
C13 C18 H18 121.0 . . ?
C17 C18 C13 117.9(5) . . ?
C17 C18 H18 121.0 . . ?
O12 C11 N10 124.3(5) . . ?
O12 C11 C13 121.4(4) . . ?
N10 C11 C13 114.3(4) . . ?
C8 C7 C4 175.5(5) . . ?
N2 C1 N10 112.0(4) . . ?
N2 C1 C6 123.6(4) . . ?
C6 C1 N10 124.3(4) . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C16 C17 C18 119.9(5) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?

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
N15 C16 C17 C18 -0.7(7) . . . . ?
C13 C18 C17 C16 -1.4(7) . . . . ?
C14 N15 C16 C17 1.3(7) . . . . ?
C14 C13 C18 C17 2.8(6) . . . . ?
C14 C13 C11 O12 135.8(5) . . . . ?
C14 C13 C11 N10 -45.3(6) . . . . ?
C16 N15 C14 C13 0.1(7) . . . . ?
C3 N2 C1 N10 177.3(4) . . . . ?
C3 N2 C1 C6 -4.1(7) . . . . ?
C3 C4 C5 C6 -1.1(7) . . . . ?
C18 C13 C14 N15 -2.2(7) . . . . ?
C18 C13 C11 O12 -43.0(7) . . . . ?
C18 C13 C11 N10 135.9(4) . . . . ?
C11 N10 C1 N2 -172.4(4) . . . . ?
C11 N10 C1 C6 8.9(7) . . . . ?
C11 C13 C14 N15 179.0(4) . . . . ?
C11 C13 C18 C17 -178.4(4) . . . . ?
C7 C4 C3 N2 177.8(4) . . . . ?
C7 C4 C5 C6 179.7(4) . . . . ?
C1 N10 C11 O12 -5.1(7) . . . . ?
C1 N10 C11 C13 176.0(4) . . . . ?
C1 N2 C3 C4 3.9(7) . . . . ?
C1 C6 C5 C4 0.9(7) . . . . ?
C5 C6 C1 N10 -179.8(4) . . . . ?
C5 C6 C1 N2 1.8(7) . . . . ?
C5 C4 C3 N2 -1.4(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.777
_oxdiff_exptl_absorpt_empirical_full_min 0.678
####################################################################### 
# 
# 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_3act-Cl
_database_code_depnum_ccdc_archive 'CCDC 2089325'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
averkiev@ksu.edu
_chemical_name_common            ?
_chemical_name_systematic        3act-Cl
_chemical_formula_moiety         'C13 H8 Cl N3 O'
_chemical_formula_sum            'C13 H8 Cl N3 O'
_chemical_formula_weight         257.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H18 N3 O Cl'
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                   3.84600(10)
_cell_length_b                   9.8013(2)
_cell_length_c                   29.8606(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.485(2)
_cell_angle_gamma                90
_cell_volume                     1123.54(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10206
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.8990
_cell_measurement_theta_min      2.9640
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    2.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'recrystallized from touluene, ACN, and ethylacetate'
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            11353
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.222
_diffrn_reflns_theta_min         2.965
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 -39.00   0.50    5.43    --  -47.95 -38.00 -90.00   50
  2  ω   -108.00 -76.00   0.50    5.43    --  -47.95 -38.00 -90.00   64
  3  ω   -117.00 -76.00   0.50    5.43    --  -47.95-125.00   0.00   82
  4  ω   -103.00 -76.00   0.50    5.43    --  -47.95-124.00  76.00   54
  5  ω    -51.00 -14.00   0.50   21.73    --  -86.25  45.00-150.00   74
  6  ω    -89.00 -63.00   0.50   21.73    --  -86.25 148.00 -39.00   52
  7  ω   -100.00 -65.00   0.50    5.43    --  -47.95 148.00 -39.00   70
  8  ω    -50.00 -17.00   0.50   21.73    --  -86.25  45.00  90.00   66
  9  ω    -63.00 -38.00   0.50    5.43    --  -47.95 124.00 155.00   50
 10  ω    -62.00 -36.00   0.50   21.73    --  -86.25 124.00 155.00   52
 11  ω   -147.00 -73.00   0.50   21.73    --  -86.25 -45.00 120.00  148
 12  ω   -119.00 -89.00   0.50   21.73    --  -86.25-124.00  76.00   60
 13  ω    -98.00 -73.00   0.50    5.43    --  -47.95-125.00  90.00   50
 14  ω   -102.00 -62.00   0.50    5.43    --  -47.95-148.00 -87.00   80
 15  ω   -127.00-102.00   0.50   21.73    --  -86.25-148.00 -87.00   50
 16  ω     36.00  95.00   0.50    5.43    --   47.95-124.00  76.00  118
 17  ω     49.00  74.00   0.50   21.73    --  107.75-124.00  76.00   50
 18  ω     73.00  99.00   0.50   21.73    --  107.75 -94.00 120.00   52
 19  ω     44.00  70.00   0.50   21.73    --  107.75 -61.00  90.00   52
 20  ω     36.00  61.00   0.50   21.73    --  107.75 -61.00  30.00   50
 21  ω     46.00 102.00   0.50   21.73    --  107.75 -77.00   0.00  112
 22  ω     80.00 105.00   0.50   21.73    --  107.75 -77.00 -60.00   50
 23  ω     77.00 107.00   0.50   21.73    --  107.75-106.00 -74.59   60
 24  ω     63.00  88.00   0.50   21.73    --  107.75-148.00 -87.00   50
 25  ω     57.00  84.00   0.50   21.73    --  107.75-125.00 -90.00   54
 26  ω     67.00 112.00   0.50   21.73    --  107.75-125.00-150.00   90
 27  ω     54.00  80.00   0.50    5.43    --   47.95-148.00 -87.00   52
 28  ω     36.00  69.00   0.50   21.73    --  107.75 -61.00-120.00   66
 29  ω     52.00  93.00   0.50   21.73    --  107.75 -77.00-150.00   82
 30  ω     47.00 106.00   0.50   21.73    --  107.75 -94.00 -90.00  118
 31  ω     87.00 112.00   0.50   21.73    --  107.75-125.00   0.00   50
 32  ω     42.00  69.00   0.50   21.73    --  107.75 -77.00 -60.00   54
 33  ω     41.00  67.00   0.50   21.73    --  107.75 -61.00 -60.00   52
 34  ω     35.00  60.00   0.50   21.73    --  107.75 -61.00 -30.00   50
 35  ω     35.00  69.00   0.50   21.73    --  107.75 -61.00 -90.00   68
 36  ω     94.00 167.00   0.50   21.73    --  107.75  15.00 -90.00  146
 37  ω    110.00 178.00   0.50   21.73    --  107.75  15.00 -30.00  136
 38  ω    103.00 156.00   0.50   21.73    --  107.75  30.00 120.00  106
 39  ω    144.00 178.00   0.50   21.73    --  107.75  61.00 150.00   68
 40  ω    122.00 147.00   0.50   21.73    --  107.75 124.00 155.00   50
 41  ω    100.00 139.00   0.50   21.73    --  107.75  61.00 150.00   78
 42  ω     80.00 117.50   0.50   21.73    --  107.75 148.00 -39.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1510452000
_diffrn_orient_matrix_UB_12      -0.1301535000
_diffrn_orient_matrix_UB_13      -0.0226384000
_diffrn_orient_matrix_UB_21      -0.0811971000
_diffrn_orient_matrix_UB_22      -0.0572895000
_diffrn_orient_matrix_UB_23      0.0462612000
_diffrn_orient_matrix_UB_31      -0.3627840000
_diffrn_orient_matrix_UB_32      0.0669608000
_diffrn_orient_matrix_UB_33      -0.0044030000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2235
_reflns_number_total             2305
_reflns_odcompleteness_completeness 98.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.046
_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)+(0.0622P)²+1.2212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1174
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C18(H18), C17(H17), C14(H14), C16(H16), C3(H3), C6(H6), C5(H5)
;
_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
Cl9 Cl 0.06243(14) 0.15043(5) 0.58637(2) 0.03146(18) Uani 1 1 d . . . . .
O12 O 0.5805(4) 0.64663(13) 0.33272(4) 0.0224(3) Uani 1 1 d . . . . .
N10 N 0.6434(4) 0.41342(15) 0.33393(5) 0.0162(3) Uani 1 1 d . . . . .
H10 H 0.707186 0.343663 0.317788 0.019 Uiso 1 1 calc R U . . .
N15 N 1.0063(4) 0.67546(15) 0.20964(5) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.6104(4) 0.25540(15) 0.38984(5) 0.0173(3) Uani 1 1 d . . . . .
C7 C 0.2632(4) 0.24943(19) 0.50487(7) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.5453(4) 0.38468(18) 0.37741(6) 0.0154(3) Uani 1 1 d . . . . .
C18 C 0.6442(4) 0.44210(17) 0.23466(6) 0.0152(3) Uani 1 1 d . . . . .
H18 H 0.522849 0.362633 0.243120 0.018 Uiso 1 1 calc R U . . .
C13 C 0.7457(4) 0.54079(17) 0.26636(6) 0.0146(3) Uani 1 1 d . . . . .
C17 C 0.7242(5) 0.46235(17) 0.19043(6) 0.0168(4) Uani 1 1 d . . . . .
H17 H 0.656725 0.397217 0.167994 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6497(4) 0.53916(17) 0.31416(6) 0.0158(4) Uani 1 1 d . . . . .
C14 C 0.9248(4) 0.65494(17) 0.25206(6) 0.0158(4) Uani 1 1 d . . . . .
H14 H 0.993006 0.722246 0.273744 0.019 Uiso 1 1 calc R U . . .
C16 C 0.9044(5) 0.57935(18) 0.17951(6) 0.0164(4) Uani 1 1 d . . . . .
H16 H 0.958397 0.592140 0.149170 0.020 Uiso 1 1 calc R U . . .
C3 C 0.5202(5) 0.21662(19) 0.43031(6) 0.0191(4) Uani 1 1 d . . . . .
H3 H 0.566272 0.125004 0.439204 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3622(5) 0.30208(19) 0.46044(6) 0.0181(4) Uani 1 1 d . . . . .
C6 C 0.3899(5) 0.47981(18) 0.40499(6) 0.0185(4) Uani 1 1 d . . . . .
H6 H 0.348242 0.570932 0.395238 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2991(5) 0.43706(19) 0.44672(6) 0.0199(4) Uani 1 1 d . . . . .
H5 H 0.193662 0.499216 0.466200 0.024 Uiso 1 1 calc R U . . .
C8 C 0.1813(5) 0.2097(2) 0.53721(7) 0.0259(4) 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
Cl9 C8 1.668(2) . ?
O12 C11 1.227(2) . ?
N10 H10 0.8800 . ?
N10 C1 1.402(2) . ?
N10 C11 1.367(2) . ?
N15 C14 1.339(2) . ?
N15 C16 1.344(2) . ?
N2 C1 1.340(2) . ?
N2 C3 1.333(2) . ?
C7 C4 1.494(3) . ?
C7 C8 1.105(3) . ?
C1 C6 1.402(2) . ?
C18 H18 0.9500 . ?
C18 C13 1.393(2) . ?
C18 C17 1.389(2) . ?
C13 C11 1.496(2) . ?
C13 C14 1.394(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.389(2) . ?
C14 H14 0.9500 . ?
C16 H16 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 C5 1.402(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.380(2) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N10 H10 116.8 . . ?
C11 N10 H10 116.8 . . ?
C11 N10 C1 126.42(15) . . ?
C14 N15 C16 116.91(15) . . ?
C3 N2 C1 117.80(15) . . ?
C8 C7 C4 178.1(2) . . ?
N2 C1 N10 112.96(15) . . ?
N2 C1 C6 123.07(16) . . ?
C6 C1 N10 123.96(16) . . ?
C13 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C13 118.56(16) . . ?
C18 C13 C11 124.45(16) . . ?
C18 C13 C14 118.21(16) . . ?
C14 C13 C11 117.12(15) . . ?
C18 C17 H17 120.5 . . ?
C18 C17 C16 118.94(16) . . ?
C16 C17 H17 120.5 . . ?
O12 C11 N10 124.64(16) . . ?
O12 C11 C13 119.66(15) . . ?
N10 C11 C13 115.70(14) . . ?
N15 C14 C13 123.97(16) . . ?
N15 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
N15 C16 C17 123.41(16) . . ?
N15 C16 H16 118.3 . . ?
C17 C16 H16 118.3 . . ?
N2 C3 H3 117.9 . . ?
N2 C3 C4 124.13(17) . . ?
C4 C3 H3 117.9 . . ?
C3 C4 C7 120.64(16) . . ?
C3 C4 C5 116.91(16) . . ?
C5 C4 C7 122.45(16) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 C1 117.97(17) . . ?
C5 C6 H6 121.0 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.12(16) . . ?
C6 C5 H5 119.9 . . ?
C7 C8 Cl9 179.3(2) . . ?

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
C6 H6 O12 0.95 2.24 2.839(2) 119.8 . 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
N10 C1 C6 C5 178.55(17) . . . . ?
N2 C1 C6 C5 -0.3(3) . . . . ?
N2 C3 C4 C7 178.79(17) . . . . ?
N2 C3 C4 C5 -0.5(3) . . . . ?
C7 C4 C5 C6 -178.78(17) . . . . ?
C1 N10 C11 O12 2.7(3) . . . . ?
C1 N10 C11 C13 -176.66(15) . . . . ?
C1 N2 C3 C4 0.1(3) . . . . ?
C1 C6 C5 C4 -0.1(3) . . . . ?
C18 C13 C11 O12 -141.91(18) . . . . ?
C18 C13 C11 N10 37.5(2) . . . . ?
C18 C13 C14 N15 -0.2(3) . . . . ?
C18 C17 C16 N15 -0.2(3) . . . . ?
C13 C18 C17 C16 0.5(2) . . . . ?
C17 C18 C13 C11 174.14(15) . . . . ?
C17 C18 C13 C14 -0.3(2) . . . . ?
C11 N10 C1 N2 -171.37(16) . . . . ?
C11 N10 C1 C6 9.7(3) . . . . ?
C11 C13 C14 N15 -175.09(16) . . . . ?
C14 N15 C16 C17 -0.4(2) . . . . ?
C14 C13 C11 O12 32.6(2) . . . . ?
C14 C13 C11 N10 -147.96(16) . . . . ?
C16 N15 C14 C13 0.5(3) . . . . ?
C3 N2 C1 N10 -178.64(15) . . . . ?
C3 N2 C1 C6 0.3(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?

_olex2_date_sample_data_collection 2020-12-15
_olex2_date_sample_submission    2020-12-14
_olex2_exptl_crystal_mounting_method 'mounted on a glass fibre'
_olex2_submission_original_sample_id 3-act-Cl
_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.510
####################################################################### 
# 
# 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_2act-Cl
_database_code_depnum_ccdc_archive 'CCDC 2089322'
loop_
_audit_author_name
_audit_author_address
'Christer B. Aakeroy'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Cl N3 O'
_chemical_formula_sum            'C13 H8 Cl N3 O'
_chemical_formula_weight         257.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 Cl1 N3 O1'
_chemical_oxdiff_usercomment     'Sample from exp_40 but different cell'
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                   3.79810(10)
_cell_length_b                   11.5441(2)
_cell_length_c                   25.4972(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.106(2)
_cell_angle_gamma                90
_cell_volume                     1117.73(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6074
_cell_measurement_temperature    100.00(18)
_cell_measurement_theta_max      76.2800
_cell_measurement_theta_min      3.4430
_shelx_estimated_absorpt_T_max   0.660
_shelx_estimated_absorpt_T_min   0.310
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method 'recrystallized from acetone'
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.154
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8420
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.261
_diffrn_reflns_theta_min         3.467
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00 -28.00   0.50    2.91    --  -47.95 103.00 -73.00  106
  2  ω    -23.00   4.00   0.50    2.91    --  -47.95 103.00 -73.00   54
  3  ω    -47.00 -22.00   0.50   11.64    --  -86.25 103.00 -73.00   50
  4  ω    -21.00  28.00   0.50    2.91    --  -47.95  19.00-150.00   98
  5  ω     25.00  50.00   0.50    2.91    --   47.95-103.00-174.00   50
  6  ω     80.00 106.00   0.50   11.64    --  107.75-103.00-174.00   52
  7  ω     67.00  98.00   0.50   11.64    --  107.75 -77.00 -90.00   62
  8  ω     76.00 108.00   0.50   11.64    --  107.75-125.00 -60.00   64
  9  ω     40.00  70.00   0.50   11.64    --  107.75 -61.00  60.00   60
 10  ω     43.00  69.00   0.50   11.64    --  107.75 -61.00  30.00   52
 11  ω     41.00  70.00   0.50   11.64    --  107.75 -61.00 -30.00   58
 12  ω     36.00  69.00   0.50   11.64    --  107.75 -61.00 -90.00   66
 13  ω     35.00  60.00   0.50   11.64    --  107.75 -61.00 -60.00   50
 14  ω     35.00  66.00   0.50   11.64    --  107.75 -77.00-120.00   62
 15  ω     36.00 103.00   0.50   11.64    --  107.75 -94.00-150.00  134
 16  ω     72.00  98.00   0.50   11.64    --  107.75 -94.00-180.00   52
 17  ω     37.00  62.00   0.50   11.64    --  107.75-125.00 -60.00   50
 18  ω     42.00  68.00   0.50   11.64    --  107.75-125.00   0.00   52
 19  ω     38.00  71.00   0.50   11.64    --  107.75 -61.00   0.00   66
 20  ω     94.00 149.00   0.50   11.64    --  107.75  15.00  30.00  110
 21  ω    107.00 156.00   0.50   11.64    --  107.75 103.00 -73.00   98
 22  ω    144.00 177.00   0.50   11.64    --  107.75  61.00-150.00   66
 23  ω    147.00 172.00   0.50   11.64    --  107.75 125.00-150.00   50
 24  ω    111.00 141.00   0.50   11.64    --  107.75  61.00-150.00   60
 25  ω    102.00 128.00   0.50   11.64    --  107.75 125.00-150.00   52
 26  ω    131.00 156.00   0.50   11.64    --  107.75 125.00  60.00   50
 27  ω     43.00  69.00   0.50   11.64    --  107.75 -61.00 120.00   52
 28  ω     35.00  61.00   0.50   11.64    --  107.75 -77.00 -90.00   52
 29  ω     35.00  61.00   0.50   11.64    --  107.75 -77.00-180.00   52
 30  ω   -118.00 -73.00   0.50    2.91    --  -47.95-125.00   0.00   90
 31  ω   -111.00 -75.00   0.50    2.91    --  -47.95-125.00  60.00   72
 32  ω   -112.00 -79.00   0.50    2.91    --  -47.95-125.00-120.00   66
 33  ω   -104.00 -77.00   0.50   11.64    --  -86.25 -45.00-150.00   54
 34  ω   -129.00-104.00   0.50   11.64    --  -86.25-103.00-174.00   50
 35  ω   -157.00-131.00   0.50   11.64    --  -86.25 -45.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2585123000
_diffrn_orient_matrix_UB_12      -0.0717099000
_diffrn_orient_matrix_UB_13      -0.0326273000
_diffrn_orient_matrix_UB_21      -0.0685948000
_diffrn_orient_matrix_UB_22      -0.1063516000
_diffrn_orient_matrix_UB_23      0.0348326000
_diffrn_orient_matrix_UB_31      -0.3051028000
_diffrn_orient_matrix_UB_32      -0.0368238000
_diffrn_orient_matrix_UB_33      -0.0370603000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2199
_reflns_number_total             2342
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0385
_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)+(0.0585P)²+0.6051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C3(H3), C6(H6), C18(H18), C5(H5), C17(H17), C16(H16), C15(H15)
;
_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
Cl9 Cl 0.15600(11) 1.02644(4) 0.64871(2) 0.02973(15) Uani 1 1 d . . . . .
O12 O 0.4855(4) 0.64600(11) 0.33010(5) 0.0334(3) Uani 1 1 d . . . . .
N10 N 0.6948(4) 0.56855(12) 0.40751(5) 0.0238(3) Uani 1 1 d . . . . .
H10 H 0.808881 0.508190 0.420302 0.029 Uiso 1 1 calc R U . . .
N2 N 0.6983(4) 0.62667(12) 0.49323(5) 0.0240(3) Uani 1 1 d . . . . .
N14 N 0.9309(4) 0.38089(12) 0.35551(5) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.5976(4) 0.65313(14) 0.44395(6) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.6163(4) 0.70121(15) 0.53077(6) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.684861 0.682862 0.565824 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4351(4) 0.80509(14) 0.52181(6) 0.0232(3) Uani 1 1 d . . . . .
C6 C 0.4150(4) 0.75406(15) 0.43045(6) 0.0240(3) Uani 1 1 d . . . . .
H6 H 0.347854 0.769574 0.395056 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6712(4) 0.44727(15) 0.27394(6) 0.0250(3) Uani 1 1 d . . . . .
H18 H 0.553453 0.507045 0.254945 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3349(4) 0.83070(15) 0.47003(6) 0.0247(3) Uani 1 1 d . . . . .
H5 H 0.212266 0.900474 0.462134 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7561(4) 0.46070(14) 0.32705(6) 0.0232(3) Uani 1 1 d . . . . .
C11 C 0.6336(4) 0.56859(15) 0.35456(6) 0.0245(3) Uani 1 1 d . . . . .
C17 C 0.7630(4) 0.34453(15) 0.24953(6) 0.0266(3) Uani 1 1 d . . . . .
H17 H 0.702720 0.331617 0.213666 0.032 Uiso 1 1 calc R U . . .
C16 C 0.9436(4) 0.26116(15) 0.27826(7) 0.0268(3) Uani 1 1 d . . . . .
H16 H 1.010519 0.190090 0.262529 0.032 Uiso 1 1 calc R U . . .
C15 C 1.0253(4) 0.28377(15) 0.33081(7) 0.0256(3) Uani 1 1 d . . . . .
H15 H 1.155029 0.227192 0.350123 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3498(4) 0.88050(15) 0.56426(6) 0.0254(3) Uani 1 1 d . . . . .
C8 C 0.2729(4) 0.94339(15) 0.59968(7) 0.0268(4) 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
Cl9 C8 1.6434(18) . ?
O12 C11 1.221(2) . ?
N10 C1 1.402(2) . ?
N10 C11 1.365(2) . ?
N2 C1 1.341(2) . ?
N2 C3 1.329(2) . ?
N14 C13 1.341(2) . ?
N14 C15 1.338(2) . ?
C1 C6 1.396(2) . ?
C3 C4 1.399(2) . ?
C4 C5 1.399(2) . ?
C4 C7 1.431(2) . ?
C6 C5 1.380(2) . ?
C18 C13 1.394(2) . ?
C18 C17 1.387(3) . ?
C13 C11 1.508(2) . ?
C17 C16 1.384(2) . ?
C16 C15 1.394(2) . ?
C7 C8 1.199(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N10 C1 127.81(14) . . ?
C3 N2 C1 117.44(14) . . ?
C15 N14 C13 117.09(14) . . ?
N2 C1 N10 112.84(14) . . ?
N2 C1 C6 123.53(15) . . ?
C6 C1 N10 123.62(14) . . ?
N2 C3 C4 123.97(15) . . ?
C3 C4 C7 121.04(15) . . ?
C5 C4 C3 117.34(15) . . ?
C5 C4 C7 121.60(15) . . ?
C5 C6 C1 118.05(14) . . ?
C17 C18 C13 118.39(16) . . ?
C6 C5 C4 119.66(15) . . ?
N14 C13 C18 123.50(16) . . ?
N14 C13 C11 118.02(14) . . ?
C18 C13 C11 118.44(15) . . ?
O12 C11 N10 124.99(16) . . ?
O12 C11 C13 120.67(15) . . ?
N10 C11 C13 114.32(14) . . ?
C16 C17 C18 118.91(15) . . ?
C17 C16 C15 118.53(16) . . ?
N14 C15 C16 123.53(16) . . ?
C8 C7 C4 178.97(18) . . ?
C7 C8 Cl9 177.97(17) . . ?

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
C6 H6 O12 0.95 2.26 2.864(2) 121.1 . yes

_olex2_date_sample_data_collection 2021-01-13
_olex2_date_sample_submission    2021-01-12
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_olex2_submission_original_sample_id 2act-Cl
_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.520
####################################################################### 
# 
# 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_Bz-act-I-Form-1
_database_code_depnum_ccdc_archive 'CCDC 2089320'
loop_
_audit_author_name
_audit_author_address
'Pierre Le Magueres'
;Rigaku Americas Corporation 
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 I N2 O'
_chemical_formula_sum            'C14 H9 I N2 O'
_chemical_formula_weight         348.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H9 I N2 O'
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      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                   4.08450(10)
_cell_length_b                   16.1979(4)
_cell_length_c                   19.1245(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.784(2)
_cell_angle_gamma                90
_cell_volume                     1258.84(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.8110
_cell_measurement_theta_min      3.5680
_shelx_estimated_absorpt_T_max   0.669
_shelx_estimated_absorpt_T_min   0.482
_exptl_absorpt_coefficient_mu    19.896
_exptl_absorpt_correction_T_max  0.838
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.83a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.837
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 -1 0.0228
-1 -2 1 0.0084
0 -1 2 0.0064
0 -2 -3 0.0149
0 2 3 0.0069
0 1 -2 0.0175
1 -2 -2 0.0194
1 9 -3 0.0171
0 0 1 0.0072
-1 -1 3 0.0042
0 -1 0 0.0114
-1 5 -1 0.0153

_exptl_crystal_size_max          0.043
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.022
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
0.9986 2.0040 -0.9935 0.4228 0.0302 0.0154
-0.9986 -2.0040 1.4937 -0.4281 -0.0336 0.0246
0.0005 -0.9996 2.4987 -0.0622 -0.1039 0.1878
0.0008 -1.9995 -2.5052 -0.0456 -0.1577 -0.2244
-0.0008 1.9995 2.5052 0.0456 0.1577 0.2244
-0.0005 0.9996 -2.4987 0.0622 0.1039 -0.1878
1.0004 -1.9948 -1.5024 0.2844 -0.3152 -0.0733
1.1689 9.2873 -2.5484 0.7602 0.6496 -0.0091
0.0000 0.0000 0.5002 -0.0053 -0.0033 0.0400
-0.9990 -1.0042 2.9964 -0.4079 0.0436 0.1568
0.0005 -0.9997 -0.0022 -0.0359 -0.0872 -0.0122
-1.0019 4.9938 -0.9919 -0.1503 0.5934 -0.0901

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8164
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.202
_diffrn_reflns_theta_min         3.584
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  -3.00   0.50    5.00    --  -35.00  15.00-150.00   50
  2  ω     39.00  79.00   0.50    5.00    --   61.20-125.00 -90.00   80
  3  ω     45.00  71.00   0.50    5.00    --   61.20-125.00-150.00   52
  4  ω     44.00  70.00   0.50    5.00    --   61.20  15.00 150.00   52
  5  ω     36.00  64.00   0.50    5.00    --   61.20-125.00 -30.00   56
  6  ω     78.00 103.00   0.50    5.00    --   61.20  15.00 150.00   50
  7  ω     55.00  93.00   0.50    5.00    --   70.01-125.00 -90.00   76
  8  ω     79.00 113.00   0.50    5.00    --   70.01  15.00 -90.00   68
  9  ω     67.00  95.00   0.50    5.00    --   74.10-119.00-154.00   56
 10  ω     73.00 107.00   0.50    5.00    --   74.10   0.00-180.00   68
 11  ω     41.00  66.00   0.50    5.00    --   74.10   0.00-180.00   50
 12  ω     89.00 115.00   0.50    5.00    --   74.10  15.00-120.00   52
 13  ω     32.00  76.00   0.50    5.00    --   74.10-125.00   0.00   88
 14  ω     39.00 100.00   0.50    5.00    --   74.10-125.00 -60.00  122
 15  ω    -18.00   8.00   0.50    5.00    --  -34.26  15.00 -60.00   52
 16  ω    -28.00  -3.00   0.50    5.00    --  -35.00  15.00 -90.00   50
 17  ω     34.00  66.00   0.50    5.00    --   61.20  15.00-120.00   64
 18  ω     69.00 104.00   0.50    5.00    --   61.20  15.00-120.00   70
 19  ω     57.00  91.00   0.50    5.00    --   74.10  15.00-120.00   68
 20  ω     38.00  68.00   0.50    5.00    --   74.10-125.00-120.00   60
 21  ω     74.00 100.00   0.50    5.00    --   74.10-125.00-120.00   52
 22  ω     34.00  60.00   0.50    5.00    --   74.10-125.00 -30.00   52
 23  ω    -69.00 -28.00   0.50    5.00    --  -35.00 -15.00 -90.00   82
 24  ω     57.00  83.00   0.50    5.00    --   61.20-125.00  30.00   52
 25  ω     73.00  99.00   0.50    5.00    --   74.10-125.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.3404394000
_diffrn_orient_matrix_UB_12      0.0361184000
_diffrn_orient_matrix_UB_13      -0.0105246000
_diffrn_orient_matrix_UB_21      -0.1512551000
_diffrn_orient_matrix_UB_22      0.0871529000
_diffrn_orient_matrix_UB_23      -0.0066730000
_diffrn_orient_matrix_UB_31      0.0708302000
_diffrn_orient_matrix_UB_32      0.0120492000
_diffrn_orient_matrix_UB_33      0.0799816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode 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                2183
_reflns_number_total             2361
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.110
_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)+(0.0250P)²+5.8103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0828
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C6(H6), C3(H3), C5(H5), C14(H14), C18(H18), C17(H17), C16(H16),
 C15(H15)
;
_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
I9 I 1.19403(8) 0.66171(2) 0.81365(2) 0.03048(12) Uani 1 1 d . . . . .
O12 O -0.0486(12) 0.3639(2) 0.4485(2) 0.0524(12) Uani 1 1 d . . . . .
N2 N 0.5915(11) 0.3197(2) 0.6292(2) 0.0304(9) Uani 1 1 d . . . . .
N10 N 0.2378(11) 0.2874(2) 0.5329(2) 0.0302(9) Uani 1 1 d . . . . .
H10 H 0.285280 0.237390 0.545233 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3441(14) 0.4344(3) 0.5642(3) 0.0341(12) Uani 1 1 d . . . . .
H6 H 0.208868 0.453666 0.525626 0.041 Uiso 1 1 calc R U . . .
C1 C 0.3917(13) 0.3489(3) 0.5753(3) 0.0283(11) Uani 1 1 d . . . . .
C13 C -0.1304(13) 0.2197(3) 0.4416(3) 0.0325(11) Uani 1 1 d . . . . .
C3 C 0.7421(13) 0.3737(3) 0.6747(3) 0.0330(11) Uani 1 1 d . . . . .
H3 H 0.877698 0.353173 0.712742 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7065(13) 0.4586(3) 0.6682(3) 0.0302(11) Uani 1 1 d . . . . .
C8 C 0.9978(14) 0.5672(3) 0.7569(3) 0.0341(12) Uani 1 1 d . . . . .
C5 C 0.4993(14) 0.4879(3) 0.6109(3) 0.0350(12) Uani 1 1 d . . . . .
H5 H 0.467892 0.544397 0.604752 0.042 Uiso 1 1 calc R U . . .
C14 C -0.1089(14) 0.1419(3) 0.4723(3) 0.0369(12) Uani 1 1 d . . . . .
H14 H 0.010723 0.134981 0.515936 0.044 Uiso 1 1 calc R U . . .
C11 C 0.0193(13) 0.2967(3) 0.4738(3) 0.0324(11) Uani 1 1 d . . . . .
C18 C -0.3150(14) 0.2291(4) 0.3762(3) 0.0389(13) Uani 1 1 d . . . . .
H18 H -0.334145 0.280855 0.355170 0.047 Uiso 1 1 calc R U . . .
C7 C 0.8707(13) 0.5149(3) 0.7187(3) 0.0342(12) Uani 1 1 d . . . . .
C17 C -0.4676(15) 0.1620(4) 0.3432(3) 0.0471(15) Uani 1 1 d . . . . .
H17 H -0.588891 0.168793 0.299746 0.057 Uiso 1 1 calc R U . . .
C16 C -0.4435(15) 0.0850(4) 0.3734(3) 0.0468(15) Uani 1 1 d . . . . .
H16 H -0.546679 0.039949 0.350459 0.056 Uiso 1 1 calc R U . . .
C15 C -0.2634(15) 0.0746(4) 0.4388(3) 0.0438(14) Uani 1 1 d . . . . .
H15 H -0.247203 0.022799 0.459765 0.053 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
I9 C8 1.997(5) . ?
O12 C11 1.212(6) . ?
N2 C1 1.335(6) . ?
N2 C3 1.339(6) . ?
N10 H10 0.8600 . ?
N10 C1 1.394(6) . ?
N10 C11 1.376(6) . ?
C6 H6 0.9300 . ?
C6 C1 1.411(7) . ?
C6 C5 1.354(7) . ?
C13 C14 1.388(8) . ?
C13 C11 1.494(7) . ?
C13 C18 1.402(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(7) . ?
C4 C5 1.399(7) . ?
C4 C7 1.443(7) . ?
C8 C7 1.202(7) . ?
C5 H5 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.384(8) . ?
C18 H18 0.9300 . ?
C18 C17 1.375(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.375(9) . ?
C16 H16 0.9300 . ?
C16 C15 1.395(8) . ?
C15 H15 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
C1 N2 C3 118.4(4) . . ?
C1 N10 H10 116.0 . . ?
C11 N10 H10 116.0 . . ?
C11 N10 C1 128.1(4) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C1 118.7(5) . . ?
N2 C1 N10 113.6(4) . . ?
N2 C1 C6 121.9(5) . . ?
N10 C1 C6 124.6(4) . . ?
C14 C13 C11 125.3(4) . . ?
C14 C13 C18 118.8(5) . . ?
C18 C13 C11 115.9(5) . . ?
N2 C3 H3 118.2 . . ?
N2 C3 C4 123.5(5) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 C5 117.1(5) . . ?
C3 C4 C7 121.9(5) . . ?
C5 C4 C7 120.9(4) . . ?
C7 C8 I9 174.7(5) . . ?
C6 C5 C4 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
O12 C11 N10 121.9(5) . . ?
O12 C11 C13 121.2(4) . . ?
N10 C11 C13 116.8(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.1(6) . . ?
C17 C18 H18 119.9 . . ?
C8 C7 C4 174.3(5) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 120.9(5) . . ?
C16 C17 H17 119.5 . . ?
C17 C16 H16 120.2 . . ?
C17 C16 C15 119.6(5) . . ?
C15 C16 H16 120.2 . . ?
C14 C15 C16 119.7(6) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?

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
N2 C3 C4 C5 0.5(9) . . . . ?
N2 C3 C4 C7 179.5(5) . . . . ?
C1 N2 C3 C4 -1.3(8) . . . . ?
C1 N10 C11 O12 5.2(9) . . . . ?
C1 N10 C11 C13 -175.0(5) . . . . ?
C1 C6 C5 C4 1.0(8) . . . . ?
C13 C14 C15 C16 -0.1(9) . . . . ?
C13 C18 C17 C16 0.2(9) . . . . ?
C3 N2 C1 N10 -177.5(5) . . . . ?
C3 N2 C1 C6 1.9(8) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C5 C6 C1 N2 -1.8(8) . . . . ?
C5 C6 C1 N10 177.5(5) . . . . ?
C14 C13 C11 O12 -169.4(6) . . . . ?
C14 C13 C11 N10 10.9(8) . . . . ?
C14 C13 C18 C17 -0.8(9) . . . . ?
C11 N10 C1 N2 180.0(5) . . . . ?
C11 N10 C1 C6 0.5(9) . . . . ?
C11 C13 C14 C15 178.5(5) . . . . ?
C11 C13 C18 C17 -178.7(5) . . . . ?
C18 C13 C14 C15 0.7(9) . . . . ?
C18 C13 C11 O12 8.4(8) . . . . ?
C18 C13 C11 N10 -171.3(5) . . . . ?
C18 C17 C16 C15 0.4(10) . . . . ?
C7 C4 C5 C6 -179.4(5) . . . . ?
C17 C16 C15 C14 -0.4(9) . . . . ?

_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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.832
####################################################################### 
# 
# 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_Bz-act-I-Form-2
_database_code_depnum_ccdc_archive 'CCDC 2089321'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
averkiev@ksu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 I N2 O'
_chemical_formula_sum            'C14 H9 I N2 O'
_chemical_formula_weight         348.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H10N4O4I1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.25520(10)
_cell_length_b                   15.3923(3)
_cell_length_c                   16.4781(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.244(2)
_cell_angle_gamma                90
_cell_volume                     1319.13(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16617
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      33.5650
_cell_measurement_theta_min      2.4790
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.554
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.573
_diffrn_reflns_theta_min         2.498
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  84.00   0.50   60.00    --   12.42  57.00 -60.00  100
  2  ω     -2.00  60.00   0.50   60.00    --   12.42  57.00 -90.00  124
  3  ω     -3.00  26.00   0.50   60.00    --   12.42  77.00  60.00   58
  4  ω     -2.00  79.00   0.50   60.00    --   12.42  57.00 150.00  162
  5  ω     15.00  52.00   0.50   60.00    --   12.42-112.00 123.00   74
  6  ω    -57.00  -7.00   0.50   60.00    --   12.42 -19.00 -30.00  100
  7  ω    -62.00   5.00   0.50   60.00    --   12.42 -19.00-150.00  134
  8  ω    -84.00   1.00   0.50   60.00    --  -12.58 -57.00 -60.00  170
  9  ω     50.00  75.00   0.50   60.00    --   12.42-178.00  30.00   50
 10  ω     40.00  83.00   0.50   60.00    --   12.42-178.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062624000
_diffrn_orient_matrix_UB_12      0.0112230000
_diffrn_orient_matrix_UB_13      -0.0419856000
_diffrn_orient_matrix_UB_21      0.1268740000
_diffrn_orient_matrix_UB_22      0.0168026000
_diffrn_orient_matrix_UB_23      0.0078779000
_diffrn_orient_matrix_UB_31      0.0496875000
_diffrn_orient_matrix_UB_32      -0.0414094000
_diffrn_orient_matrix_UB_33      -0.0081962000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4037
_reflns_number_total             4674
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_refine_diff_density_max         1.385
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.5979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0732
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C3(H3), C5(H5), C6(H6), C14(H14), C18(H18), C15(H15), C16(H16),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I9 I 0.34356(3) 0.26065(2) 0.81958(2) 0.03943(6) Uani 1 1 d . . . . .
O12 O 0.9591(2) 0.70864(9) 0.47106(8) 0.0341(3) Uani 1 1 d . . . . .
N2 N 0.3918(2) 0.62013(9) 0.60208(8) 0.0260(2) Uani 1 1 d . . . . .
N10 N 0.5526(2) 0.69784(9) 0.50316(8) 0.0269(3) Uani 1 1 d . . . . .
H10 H 0.399075 0.721690 0.493589 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5542(3) 0.48079(10) 0.65078(9) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.5743(3) 0.62417(9) 0.55349(9) 0.0223(2) Uani 1 1 d . . . . .
C3 C 0.3837(3) 0.55020(11) 0.64900(9) 0.0272(3) Uani 1 1 d . . . . .
H3 H 0.253537 0.547433 0.683428 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4631(4) 0.35256(13) 0.74702(12) 0.0383(4) Uani 1 1 d . . . . .
C5 C 0.7486(3) 0.48741(10) 0.60153(10) 0.0272(3) Uani 1 1 d . . . . .
H5 H 0.871774 0.442247 0.601525 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7610(3) 0.55997(10) 0.55278(10) 0.0256(3) Uani 1 1 d . . . . .
H6 H 0.893562 0.565908 0.519590 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7407(3) 0.73722(10) 0.46710(10) 0.0265(3) Uani 1 1 d . . . . .
C7 C 0.5184(3) 0.40818(11) 0.70213(10) 0.0316(3) Uani 1 1 d . . . . .
C13 C 0.6601(3) 0.82032(11) 0.42419(10) 0.0302(3) Uani 1 1 d . . . . .
C14 C 0.4235(4) 0.82998(14) 0.37596(12) 0.0410(4) Uani 1 1 d . . . . .
H14 H 0.304020 0.783311 0.369853 0.049 Uiso 1 1 calc R U . . .
C18 C 0.8325(4) 0.88901(14) 0.43213(15) 0.0468(5) Uani 1 1 d . . . . .
H18 H 0.996598 0.882211 0.464173 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3625(4) 0.90880(19) 0.33649(15) 0.0542(6) Uani 1 1 d . . . . .
H15 H 0.201637 0.915264 0.302511 0.065 Uiso 1 1 calc R U . . .
C16 C 0.5316(5) 0.97743(16) 0.34596(17) 0.0581(6) Uani 1 1 d . . . . .
H16 H 0.485881 1.031303 0.319716 0.070 Uiso 1 1 calc R U . . .
C17 C 0.7666(5) 0.96782(16) 0.39345(18) 0.0596(6) Uani 1 1 d . . . . .
H17 H 0.884348 1.014997 0.399908 0.072 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
I9 C8 2.0103(18) . ?
O12 C11 1.222(2) . ?
N2 C1 1.3363(19) . ?
N2 C3 1.330(2) . ?
N10 H10 0.8800 . ?
N10 C1 1.3997(19) . ?
N10 C11 1.366(2) . ?
C4 C3 1.392(2) . ?
C4 C5 1.397(2) . ?
C4 C7 1.430(2) . ?
C1 C6 1.394(2) . ?
C3 H3 0.9500 . ?
C8 C7 1.194(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C11 C13 1.493(2) . ?
C13 C14 1.384(3) . ?
C13 C18 1.386(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.391(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.372(4) . ?
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
C3 N2 C1 118.15(13) . . ?
C1 N10 H10 116.0 . . ?
C11 N10 H10 116.0 . . ?
C11 N10 C1 127.93(13) . . ?
C3 C4 C5 117.01(14) . . ?
C3 C4 C7 118.25(14) . . ?
C5 C4 C7 124.74(15) . . ?
N2 C1 N10 112.84(13) . . ?
N2 C1 C6 122.59(13) . . ?
C6 C1 N10 124.55(13) . . ?
N2 C3 C4 124.02(14) . . ?
N2 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
C7 C8 I9 175.91(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.72(14) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.44(14) . . ?
C5 C6 H6 120.8 . . ?
O12 C11 N10 123.33(15) . . ?
O12 C11 C13 122.29(15) . . ?
N10 C11 C13 114.36(14) . . ?
C8 C7 C4 172.2(2) . . ?
C14 C13 C11 122.30(17) . . ?
C14 C13 C18 119.56(17) . . ?
C18 C13 C11 118.13(16) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C18 H18 119.8 . . ?
C13 C18 C17 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?

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
O12 C11 C13 C14 139.48(19) . . . . ?
O12 C11 C13 C18 -39.1(3) . . . . ?
N2 C1 C6 C5 3.1(2) . . . . ?
N10 C1 C6 C5 -175.31(15) . . . . ?
N10 C11 C13 C14 -42.3(2) . . . . ?
N10 C11 C13 C18 139.05(18) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C1 N2 C3 C4 0.1(2) . . . . ?
C1 N10 C11 O12 4.3(3) . . . . ?
C1 N10 C11 C13 -173.87(15) . . . . ?
C3 N2 C1 N10 175.94(14) . . . . ?
C3 N2 C1 C6 -2.7(2) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C5 C4 C3 N2 1.9(2) . . . . ?
C11 N10 C1 N2 157.00(16) . . . . ?
C11 N10 C1 C6 -24.4(3) . . . . ?
C11 C13 C14 C15 -178.86(19) . . . . ?
C11 C13 C18 C17 -179.9(2) . . . . ?
C7 C4 C3 N2 -177.93(15) . . . . ?
C7 C4 C5 C6 178.47(15) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C13 C18 C17 C16 -1.1(4) . . . . ?
C14 C13 C18 C17 1.4(3) . . . . ?
C14 C15 C16 C17 1.5(4) . . . . ?
C18 C13 C14 C15 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?

_olex2_date_sample_data_collection 2021-04-22
_olex2_date_sample_submission    2021-01-12
_olex2_exptl_crystal_mounting_method 'mounted on a MiTegen loop'
_olex2_submission_original_sample_id 'Bz-act_1 (Form II)'
_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 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.713
####################################################################### 
# 
# 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_Bz-act-Br
_database_code_depnum_ccdc_archive 'CCDC 2089319'
loop_
_audit_author_name
_audit_author_address
'Pierre Le Magueres'
;Rigaku Americas Corporation 
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-03-03
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Br N2 O'
_chemical_formula_sum            'C14 H9 Br N2 O'
_chemical_formula_weight         301.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H9 Br N2 O'
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      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                   5.19740(10)
_cell_length_b                   21.9187(5)
_cell_length_c                   10.6585(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.577(2)
_cell_angle_gamma                90
_cell_volume                     1193.59(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6530
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.3100
_cell_measurement_theta_min      4.0340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.76a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.037
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8888
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.059
_diffrn_reflns_theta_min         4.034
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  69.00   0.50    0.40    --  101.80 -61.00 -90.00   80
  2  ω     29.00  69.00   0.50    0.40    --  101.80 -61.00-120.00   80
  3  ω     29.00 127.00   0.50    0.40    --  101.80 -82.00-153.00  196
  4  ω     29.00  69.00   0.50    0.40    --  101.80 -61.00-150.00   80
  5  ω    127.00 175.00   0.50    0.40    --  101.80  61.00-150.00   96
  6  ω     29.00  69.00   0.50    0.40    --  101.80 -61.00 120.00   80
  7  ω     33.00  97.00   0.50    0.10    --   45.89  19.00 120.00  128
  8  ω    -44.00  27.00   0.50    0.10    --  -45.89  37.00  90.00  142
  9  ω    -73.00 -19.00   0.50    0.40    --  -91.75  61.00  90.00  108
 10  ω    -53.00 -20.00   0.50    0.40    --  -91.75  45.00  60.00   66
 11  ω    -53.00 -20.00   0.50    0.40    --  -91.75  45.00  30.00   66
 12  ω    -53.00 -20.00   0.50    0.40    --  -91.75  45.00   0.00   66
 13  ω    -61.00  15.00   0.50    0.10    --  -45.89  57.00-150.00  152
 14  ω    -82.00 -29.00   0.50    0.10    --  -45.89 125.00 -30.00  106
 15  ω    -82.00 -29.00   0.50    0.10    --  -45.89 125.00 120.00  106
 16  ω   -163.00-126.00   0.50    0.40    --  -91.75 -77.00  60.00   74
 17  ω   -163.00-127.00   0.50    0.40    --  -91.75 -61.00  90.00   72
 18  ω   -163.00-127.00   0.50    0.40    --  -91.75 -61.00 -60.00   72
 19  ω   -163.00-126.00   0.50    0.40    --  -91.75 -77.00-150.00   74
 20  ω   -163.00-126.00   0.50    0.40    --  -91.75 -77.00-180.00   74
 21  ω   -163.00-127.00   0.50    0.40    --  -91.75 -61.00 -30.00   72
 22  ω   -163.00-122.00   0.50    0.40    --  -91.75 -45.00  30.00   82
 23  ω   -163.00-121.00   0.50    0.40    --  -91.75 -94.00 150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2234294000
_diffrn_orient_matrix_UB_12      -0.0025867000
_diffrn_orient_matrix_UB_13      -0.0768977000
_diffrn_orient_matrix_UB_21      0.0930884000
_diffrn_orient_matrix_UB_22      -0.0610167000
_diffrn_orient_matrix_UB_23      0.0644060000
_diffrn_orient_matrix_UB_31      -0.1797969000
_diffrn_orient_matrix_UB_32      -0.0347871000
_diffrn_orient_matrix_UB_33      -0.1075318000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2181
_reflns_number_total             2304
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0244
_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)+(0.0374P)²+0.7574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0671
_refine_special_details          ?
_olex2_refinement_description    
;
;
_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
Br9 Br 1.28732(4) 0.66096(2) 0.92888(2) 0.02487(10) Uani 1 1 d . . . . .
O12 O -0.0209(3) 0.35732(7) 0.78949(12) 0.0242(3) Uani 1 1 d . . . . .
N10 N 0.0102(3) 0.42613(7) 0.63107(15) 0.0191(3) Uani 1 1 d . . . . .
N2 N 0.3022(3) 0.50258(7) 0.61297(14) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.6628(4) 0.52878(8) 0.78124(18) 0.0203(4) Uani 1 1 d . . . . .
C11 C -0.0947(3) 0.37605(8) 0.68078(17) 0.0188(4) Uani 1 1 d . . . . .
C13 C -0.3076(4) 0.34302(8) 0.59242(19) 0.0191(4) Uani 1 1 d . . . . .
C1 C 0.2307(3) 0.45919(8) 0.68872(17) 0.0182(3) Uani 1 1 d . . . . .
C18 C -0.5000(4) 0.31457(8) 0.64681(18) 0.0209(4) Uani 1 1 d . . . . .
C7 C 0.8757(4) 0.56937(9) 0.82650(17) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.5148(4) 0.53550(8) 0.65880(18) 0.0206(4) Uani 1 1 d . . . . .
C8 C 1.0419(4) 0.60536(9) 0.86729(18) 0.0224(4) Uani 1 1 d . . . . .
C14 C -0.3059(4) 0.33564(8) 0.46254(19) 0.0208(4) Uani 1 1 d . . . . .
C6 C 0.3690(4) 0.44761(9) 0.81166(18) 0.0215(4) Uani 1 1 d . . . . .
C15 C -0.4973(4) 0.29998(9) 0.38851(19) 0.0253(4) Uani 1 1 d . . . . .
C17 C -0.6915(4) 0.27958(9) 0.57195(19) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.5873(4) 0.48276(9) 0.85714(17) 0.0225(4) Uani 1 1 d . . . . .
C16 C -0.6908(4) 0.27191(9) 0.44274(19) 0.0248(4) Uani 1 1 d . . . . .
H14 H -0.180(4) 0.3533(11) 0.4230(19) 0.015(5) Uiso 1 1 d . . . . .
H18 H -0.492(4) 0.3194(10) 0.734(2) 0.016(5) Uiso 1 1 d . . . . .
H15 H -0.498(5) 0.2943(11) 0.299(2) 0.031(6) Uiso 1 1 d . . . . .
H16 H -0.826(6) 0.2480(12) 0.390(3) 0.036(7) Uiso 1 1 d . . . . .
H6 H 0.320(5) 0.4194(12) 0.857(2) 0.034(7) Uiso 1 1 d . . . . .
H3 H 0.560(4) 0.5661(10) 0.601(2) 0.020(5) Uiso 1 1 d . . . . .
H5 H 0.688(5) 0.4758(11) 0.943(2) 0.026(6) Uiso 1 1 d . . . . .
H10 H -0.059(4) 0.4401(10) 0.561(2) 0.017(5) Uiso 1 1 d . . . . .
H17 H -0.812(5) 0.2595(11) 0.609(2) 0.028(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
Br9 C8 1.7987(19) . ?
O12 C11 1.223(2) . ?
N10 C11 1.374(2) . ?
N10 C1 1.399(2) . ?
N10 H10 0.82(2) . ?
N2 C1 1.343(2) . ?
N2 C3 1.335(2) . ?
C4 C7 1.433(3) . ?
C4 C3 1.396(3) . ?
C4 C5 1.394(3) . ?
C11 C13 1.501(2) . ?
C13 C18 1.392(3) . ?
C13 C14 1.395(3) . ?
C1 C6 1.397(3) . ?
C18 C17 1.387(3) . ?
C18 H18 0.93(2) . ?
C7 C8 1.192(3) . ?
C3 H3 0.97(2) . ?
C14 C15 1.391(3) . ?
C14 H14 0.93(2) . ?
C6 C5 1.383(3) . ?
C6 H6 0.85(3) . ?
C15 C16 1.392(3) . ?
C15 H15 0.97(3) . ?
C17 C16 1.388(3) . ?
C17 H17 0.91(3) . ?
C5 H5 0.98(2) . ?
C16 H16 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N10 C1 126.52(16) . . ?
C11 N10 H10 120.5(16) . . ?
C1 N10 H10 113.0(16) . . ?
C3 N2 C1 117.68(15) . . ?
C3 C4 C7 120.55(17) . . ?
C5 C4 C7 122.44(17) . . ?
C5 C4 C3 116.97(17) . . ?
O12 C11 N10 123.78(17) . . ?
O12 C11 C13 119.97(17) . . ?
N10 C11 C13 116.24(15) . . ?
C18 C13 C11 117.26(17) . . ?
C18 C13 C14 119.80(17) . . ?
C14 C13 C11 122.70(18) . . ?
N2 C1 N10 113.41(15) . . ?
N2 C1 C6 122.74(17) . . ?
C6 C1 N10 123.82(17) . . ?
C13 C18 H18 117.5(14) . . ?
C17 C18 C13 120.17(18) . . ?
C17 C18 H18 122.3(14) . . ?
C8 C7 C4 175.9(2) . . ?
N2 C3 C4 124.20(18) . . ?
N2 C3 H3 115.1(13) . . ?
C4 C3 H3 120.7(13) . . ?
C7 C8 Br9 178.72(18) . . ?
C13 C14 H14 122.4(13) . . ?
C15 C14 C13 119.59(19) . . ?
C15 C14 H14 118.0(13) . . ?
C1 C6 H6 120.5(18) . . ?
C5 C6 C1 118.36(18) . . ?
C5 C6 H6 121.1(17) . . ?
C14 C15 C16 120.58(18) . . ?
C14 C15 H15 120.4(15) . . ?
C16 C15 H15 119.0(15) . . ?
C18 C17 C16 120.36(19) . . ?
C18 C17 H17 119.5(16) . . ?
C16 C17 H17 120.1(16) . . ?
C4 C5 H5 119.7(15) . . ?
C6 C5 C4 120.00(17) . . ?
C6 C5 H5 120.3(15) . . ?
C15 C16 H16 120.0(16) . . ?
C17 C16 C15 119.49(18) . . ?
C17 C16 H16 120.5(16) . . ?

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
O12 C11 C13 C18 32.5(3) . . . . ?
O12 C11 C13 C14 -141.86(19) . . . . ?
N10 C11 C13 C18 -148.76(17) . . . . ?
N10 C11 C13 C14 36.9(2) . . . . ?
N10 C1 C6 C5 178.75(17) . . . . ?
N2 C1 C6 C5 0.5(3) . . . . ?
C11 N10 C1 N2 174.24(16) . . . . ?
C11 N10 C1 C6 -4.2(3) . . . . ?
C11 C13 C18 C17 -175.31(17) . . . . ?
C11 C13 C14 C15 174.39(17) . . . . ?
C13 C18 C17 C16 0.9(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C1 N10 C11 O12 7.5(3) . . . . ?
C1 N10 C11 C13 -171.19(16) . . . . ?
C1 N2 C3 C4 -1.8(3) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C18 C17 C16 C15 -0.4(3) . . . . ?
C7 C4 C3 N2 -174.86(18) . . . . ?
C7 C4 C5 C6 175.49(18) . . . . ?
C3 N2 C1 N10 -178.38(16) . . . . ?
C3 N2 C1 C6 0.0(3) . . . . ?
C3 C4 C5 C6 -2.2(3) . . . . ?
C14 C13 C18 C17 -0.8(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C5 C4 C3 N2 2.8(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 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.752
####################################################################### 
# 
# 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_4act-Br
_database_code_depnum_ccdc_archive 'CCDC 2089329'
loop_
_audit_author_name
_audit_author_address
'Pierre Le Magueres'
;Rigaku Americas Corporation 
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Br N3 O'
_chemical_formula_sum            'C13 H8 Br N3 O'
_chemical_formula_weight         302.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 Br N3 O'
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                   6.75090(10)
_cell_length_b                   9.2249(2)
_cell_length_c                   10.2422(2)
_cell_angle_alpha                112.512(2)
_cell_angle_beta                 93.859(2)
_cell_angle_gamma                97.720(2)
_cell_volume                     578.97(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7400
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.3840
_cell_measurement_theta_min      4.7130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.76a (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    1.733
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8710
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.953
_diffrn_reflns_theta_min         4.713
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  15.00   0.50    0.05    --  -45.89  57.00-120.00  152
  2  ω     33.00 118.00   0.50    0.05    --   45.89  46.00 -39.00  170
  3  ω     33.00  64.00   0.50    0.05    --   45.89  31.00  99.80   62
  4  ω    -28.00  30.00   0.50    0.05    --  -45.89  19.00  30.00  116
  5  ω    -28.00  30.00   0.50    0.05    --  -45.89  19.00   0.00  116
  6  ω    -28.00  30.00   0.50    0.05    --  -45.89  19.00 -90.00  116
  7  ω     33.00 121.00   0.50    0.05    --   45.89  19.00  90.00  176
  8  ω    -28.00  30.00   0.50    0.05    --  -45.89  19.00 150.00  116
  9  ω    -64.00 -33.00   0.50    0.05    --  -45.89 -31.00  49.50   62
 10  ω   -118.00 -33.00   0.50    0.05    --  -45.89 -46.00 171.00  170
 11  ω   -108.00 -19.00   0.50    0.20    --  -91.75  77.00   0.00  178
 12  ω    -54.00 -19.00   0.50    0.20    --  -91.75  46.00 -39.00   70
 13  ω    -64.00 -33.00   0.50    0.05    --  -45.89 -31.00-172.18   62
 14  ω     29.00  69.00   0.50    0.20    --  101.80 -61.00-180.00   80
 15  ω     29.00  69.00   0.50    0.20    --  101.80 -61.00  30.00   80
 16  ω     29.00  69.00   0.50    0.20    --  101.80 -61.00  60.00   80
 17  ω     29.00 104.00   0.50    0.20    --  101.80 -77.00 150.00  150
 18  ω     29.00  69.00   0.50    0.20    --  101.80 -61.00 -30.00   80
 19  ω     29.00 104.00   0.50    0.20    --  101.80 -94.00 -60.00  150
 20  ω     36.00 108.00   0.50    0.20    --  101.80-125.00-180.00  144
 21  ω     36.00 108.00   0.50    0.20    --  101.80-125.00 -90.00  144
 22  ω     29.00 104.00   0.50    0.20    --  101.80 -94.00-180.00  150
 23  ω     36.00 108.00   0.50    0.20    --  101.80-125.00 -60.00  144
 24  ω     29.00 104.00   0.50    0.20    --  101.80 -94.00   0.00  150
 25  ω     29.00 104.00   0.50    0.20    --  101.80 -94.00  60.00  150
 26  ω     36.00 108.00   0.50    0.20    --  101.80-125.00 150.00  144
 27  ω   -166.00 -79.00   0.50    0.20    --  -91.75 -29.00-133.85  174
 28  ω   -163.00-126.00   0.50    0.20    --  -91.75 -77.00-120.00   74
 29  ω   -163.00-126.00   0.50    0.20    --  -91.75 -77.00 -90.00   74
 30  ω   -163.00-126.00   0.50    0.20    --  -91.75 -77.00 -30.00   74
 31  ω   -163.00-127.00   0.50    0.20    --  -91.75 -61.00  30.00   72
 32  ω   -166.00 -88.00   0.50    0.20    --  -91.75 -30.00 150.00  156
 33  ω   -163.00-122.00   0.50    0.20    --  -91.75 -45.00   0.00   82
 34  ω   -163.00-122.00   0.50    0.20    --  -91.75 -45.00 -60.00   82
 35  ω   -163.00-122.00   0.50    0.20    --  -91.75 -45.00 -90.00   82
 36  ω   -163.00-121.00   0.50    0.20    --  -91.75 -94.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0694677000
_diffrn_orient_matrix_UB_12      -0.1431762000
_diffrn_orient_matrix_UB_13      0.0382985000
_diffrn_orient_matrix_UB_21      0.2082596000
_diffrn_orient_matrix_UB_22      0.0283165000
_diffrn_orient_matrix_UB_23      0.0855826000
_diffrn_orient_matrix_UB_31      -0.0757834000
_diffrn_orient_matrix_UB_32      0.1113365000
_diffrn_orient_matrix_UB_33      0.1348078000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2241
_reflns_number_total             2274
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.5745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0648
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C5(H5), C18(H18), C6(H6), C17(H17), C14(H14), C15(H15), 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
Br9 Br 1.10451(3) 0.22100(2) 0.99377(2) 0.01994(9) Uani 1 1 d . . . . .
O12 O -0.0952(2) 0.47274(17) 0.62915(15) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.2509(3) 0.1161(2) 0.60909(18) 0.0174(3) Uani 1 1 d . . . . .
N10 N -0.0047(2) 0.22493(19) 0.54686(17) 0.0163(3) Uani 1 1 d . . . . .
H10 H -0.049974 0.128093 0.488995 0.020 Uiso 1 1 calc R U . . .
N16 N -0.5568(3) 0.1852(2) 0.17134(18) 0.0191(4) Uani 1 1 d . . . . .
C13 C -0.2705(3) 0.2755(2) 0.4108(2) 0.0148(4) Uani 1 1 d . . . . .
C5 C 0.4545(3) 0.4090(2) 0.8084(2) 0.0171(4) Uani 1 1 d . . . . .
H5 H 0.522056 0.506772 0.875208 0.021 Uiso 1 1 calc R U . . .
C4 C 0.5410(3) 0.2721(2) 0.7806(2) 0.0171(4) Uani 1 1 d . . . . .
C11 C -0.1163(3) 0.3362(2) 0.5410(2) 0.0149(4) Uani 1 1 d . . . . .
C7 C 0.7298(3) 0.2698(2) 0.8520(2) 0.0192(4) Uani 1 1 d . . . . .
C18 C -0.4626(3) 0.3131(2) 0.4248(2) 0.0172(4) Uani 1 1 d . . . . .
H18 H -0.498475 0.369481 0.514052 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2691(3) 0.3991(2) 0.7367(2) 0.0162(4) Uani 1 1 d . . . . .
H6 H 0.209169 0.488851 0.755043 0.019 Uiso 1 1 calc R U . . .
C1 C 0.1741(3) 0.2499(2) 0.6356(2) 0.0151(4) Uani 1 1 d . . . . .
C17 C -0.5997(3) 0.2649(2) 0.3027(2) 0.0198(4) Uani 1 1 d . . . . .
H17 H -0.728512 0.289334 0.312842 0.024 Uiso 1 1 calc R U . . .
C14 C -0.2246(3) 0.1902(2) 0.2753(2) 0.0161(4) Uani 1 1 d . . . . .
H14 H -0.098265 0.161322 0.262446 0.019 Uiso 1 1 calc R U . . .
C15 C -0.3710(3) 0.1488(2) 0.1592(2) 0.0177(4) Uani 1 1 d . . . . .
H15 H -0.338843 0.093117 0.068609 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4302(3) 0.1286(2) 0.6796(2) 0.0183(4) Uani 1 1 d . . . . .
H3 H 0.485002 0.036404 0.660499 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8819(3) 0.2537(3) 0.9077(2) 0.0205(4) 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
Br9 C8 1.809(2) . ?
O12 C11 1.219(2) . ?
N2 C1 1.341(3) . ?
N2 C3 1.335(3) . ?
N10 H10 0.8600 . ?
N10 C11 1.369(2) . ?
N10 C1 1.398(2) . ?
N16 C17 1.337(3) . ?
N16 C15 1.343(3) . ?
C13 C11 1.504(3) . ?
C13 C18 1.389(3) . ?
C13 C14 1.389(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.401(3) . ?
C5 C6 1.381(3) . ?
C4 C7 1.433(3) . ?
C4 C3 1.401(3) . ?
C7 C8 1.196(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.388(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.400(3) . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
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 C1 117.71(17) . . ?
C11 N10 H10 116.1 . . ?
C11 N10 C1 127.77(17) . . ?
C1 N10 H10 116.1 . . ?
C17 N16 C15 117.24(17) . . ?
C18 C13 C11 119.15(17) . . ?
C14 C13 C11 122.22(17) . . ?
C14 C13 C18 118.52(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.16(18) . . ?
C5 C4 C7 124.16(19) . . ?
C3 C4 C5 116.92(18) . . ?
C3 C4 C7 118.89(19) . . ?
O12 C11 N10 125.11(17) . . ?
O12 C11 C13 121.52(17) . . ?
N10 C11 C13 113.36(16) . . ?
C8 C7 C4 174.2(2) . . ?
C13 C18 H18 120.7 . . ?
C17 C18 C13 118.60(18) . . ?
C17 C18 H18 120.7 . . ?
C5 C6 H6 121.0 . . ?
C5 C6 C1 117.95(18) . . ?
C1 C6 H6 121.0 . . ?
N2 C1 N10 112.67(17) . . ?
N2 C1 C6 123.24(18) . . ?
N10 C1 C6 124.02(18) . . ?
N16 C17 C18 123.61(19) . . ?
N16 C17 H17 118.2 . . ?
C18 C17 H17 118.2 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.71(18) . . ?
C15 C14 H14 120.6 . . ?
N16 C15 C14 123.30(18) . . ?
N16 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
N2 C3 C4 123.99(19) . . ?
N2 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
C7 C8 Br9 177.0(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
C13 C18 C17 N16 -0.8(3) . . . . ?
C13 C14 C15 N16 -0.9(3) . . . . ?
C5 C4 C3 N2 0.6(3) . . . . ?
C5 C6 C1 N2 2.4(3) . . . . ?
C5 C6 C1 N10 -174.25(18) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C11 N10 C1 N2 -176.68(18) . . . . ?
C11 N10 C1 C6 0.3(3) . . . . ?
C11 C13 C18 C17 176.01(18) . . . . ?
C11 C13 C14 C15 -175.10(18) . . . . ?
C7 C4 C3 N2 178.44(19) . . . . ?
C18 C13 C11 O12 -43.5(3) . . . . ?
C18 C13 C11 N10 137.57(19) . . . . ?
C18 C13 C14 C15 1.2(3) . . . . ?
C6 C5 C4 C7 -178.32(18) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C1 N2 C3 C4 0.9(3) . . . . ?
C1 N10 C11 O12 -12.8(3) . . . . ?
C1 N10 C11 C13 166.08(18) . . . . ?
C17 N16 C15 C14 -0.2(3) . . . . ?
C14 C13 C11 O12 132.8(2) . . . . ?
C14 C13 C11 N10 -46.1(3) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
C15 N16 C17 C18 1.1(3) . . . . ?
C3 N2 C1 N10 174.57(17) . . . . ?
C3 N2 C1 C6 -2.5(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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.735
