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

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

data_I-Me_BA
_database_code_depnum_ccdc_archive 'CCDC 2092007'
loop_
_audit_author_name
_audit_author_address
'Abhijeet S. Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
APEX2 v2014.11-0
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C7 H7 I N2 O, C7 H6 O2'
_chemical_formula_sum            'C14 H13 I N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         384.16

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   4.1768(8)
_cell_length_b                   11.513(2)
_cell_length_c                   15.476(3)
_cell_angle_alpha                78.42(3)
_cell_angle_beta                 86.37(3)
_cell_angle_gamma                86.54(3)
_cell_volume                     726.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9529
_cell_measurement_theta_min      3.923
_cell_measurement_theta_max      69.666
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.413
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.064
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

_exptl_absorpt_coefficient_mu    17.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1400 before and 0.0850 after correction.
The Ratio of minimum to maximum transmission is 0.0587.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_correction_T_min  0.05
_exptl_absorpt_correction_T_max  0.40

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            11978
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         70.27
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2543
_reflns_number_gt                2443
_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)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1257
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         2543
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0887P)²+0.8219P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.616
_refine_diff_density_min         -1.123
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.0134(11) 0.4679(4) 0.1725(3) 0.0328(9) Uani d . . . 1 . .
N N2 0.8083(11) 0.5200(4) 0.2248(3) 0.0372(9) Uani d . . . 1 . .
C C3 0.7303(12) 0.6349(4) 0.2005(3) 0.0371(10) Uani d . . . 1 . .
H H3 0.5821 0.6711 0.2374 0.044 Uiso calc U . R 1 . .
C C4 0.8542(11) 0.7036(4) 0.1245(3) 0.0352(9) Uani d . . . 1 . .
C C5 1.0693(12) 0.6510(4) 0.0701(3) 0.0378(10) Uani d . . . 1 . .
H H5 1.1587 0.6967 0.017 0.045 Uiso calc U . R 1 . .
C C6 1.1511(13) 0.5324(5) 0.0941(3) 0.0388(10) Uani d . . . 1 . .
H H6 1.2989 0.4946 0.0581 0.047 Uiso calc U . R 1 . .
I I7 0.70926(7) 0.88290(2) 0.09023(2) 0.04707(18) Uani d . . . 1 . .
H H8 0.956(13) 0.313(5) 0.250(3) 0.032(13) Uiso d . . D 1 . .
N N8 1.0643(10) 0.3466(4) 0.2032(3) 0.0356(8) Uani d . . D 1 . .
C C9 1.2606(12) 0.2679(5) 0.1656(4) 0.0403(11) Uani d . . . 1 . .
O O10 1.4416(11) 0.2984(4) 0.1018(3) 0.0589(11) Uani d . . . 1 . .
C C11 1.2290(16) 0.1406(5) 0.2113(5) 0.0543(14) Uani d . . . 1 . .
H H11A 1.2998 0.0884 0.1703 0.081 Uiso calc U . R 1 . .
H H11B 1.0041 0.1273 0.2308 0.081 Uiso calc U . R 1 . .
H H11C 1.3626 0.1231 0.2626 0.081 Uiso calc U . R 1 . .
C C12 1.3211(12) 0.2652(4) 0.4814(3) 0.0336(9) Uani d . . . 1 . .
C C13 1.1778(13) 0.3409(4) 0.5348(3) 0.0391(10) Uani d . . . 1 . .
H H13 1.199 0.4242 0.5183 0.047 Uiso calc U . R 1 . .
C C14 1.0061(14) 0.2936(5) 0.6114(4) 0.0482(13) Uani d . . . 1 . .
H H14 0.9065 0.345 0.6473 0.058 Uiso calc U . R 1 . .
C C15 0.9769(17) 0.1723(6) 0.6368(4) 0.0551(14) Uani d . . . 1 . .
H H15 0.86 0.1404 0.6901 0.066 Uiso calc U . R 1 . .
C C16 1.1201(17) 0.0971(5) 0.5837(4) 0.0549(14) Uani d . . . 1 . .
H H16 1.1022 0.0137 0.6008 0.066 Uiso calc U . R 1 . .
C C17 1.2869(15) 0.1440(5) 0.5065(3) 0.0458(12) Uani d . . . 1 . .
H H17 1.3802 0.0927 0.4698 0.055 Uiso calc U . R 1 . .
C C18 1.5061(13) 0.3123(4) 0.3986(3) 0.0359(10) Uani d . . . 1 . .
O O19 1.6505(10) 0.2486(3) 0.3535(2) 0.0452(9) Uani d . . . 1 . .
H H20 1.619(15) 0.453(6) 0.336(3) 0.06(2) Uiso d . . D 1 . .
O O20 1.5010(11) 0.4293(3) 0.3773(2) 0.0496(10) Uani d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.340(6) ?
C1 N8 . 1.390(6) ?
C1 C6 . 1.398(7) ?
N2 C3 . 1.327(6) ?
C3 C4 . 1.369(7) ?
C3 H3 . 0.95 ?
C4 C5 . 1.387(7) ?
C4 I7 . 2.088(5) ?
C5 C6 . 1.370(7) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
I7 I7 2_675 3.8924(15) ?
N8 C9 . 1.376(6) ?
N8 H8 . 0.86(4) ?
C9 O10 . 1.211(7) ?
C9 C11 . 1.504(9) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C17 . 1.385(7) ?
C12 C13 . 1.401(6) ?
C12 C18 . 1.477(7) ?
C13 C14 . 1.377(8) ?
C13 H13 . 0.95 ?
C14 C15 . 1.384(9) ?
C14 H14 . 0.95 ?
C15 C16 . 1.395(8) ?
C15 H15 . 0.95 ?
C16 C17 . 1.373(8) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 O19 . 1.219(6) ?
C18 O20 . 1.320(6) ?
O20 H20 . 0.80(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N8 . . 113.4(4) ?
N2 C1 C6 . . 121.5(4) ?
N8 C1 C6 . . 125.1(4) ?
C3 N2 C1 . . 118.9(4) ?
N2 C3 C4 . . 122.9(4) ?
N2 C3 H3 . . 118.6 ?
C4 C3 H3 . . 118.6 ?
C3 C4 C5 . . 118.8(4) ?
C3 C4 I7 . . 120.1(3) ?
C5 C4 I7 . . 121.1(4) ?
C6 C5 C4 . . 119.1(4) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C1 . . 118.9(4) ?
C5 C6 H6 . . 120.6 ?
C1 C6 H6 . . 120.6 ?
C4 I7 I7 . 2_675 143.23(13) ?
C9 N8 C1 . . 127.9(4) ?
C9 N8 H8 . . 113.(4) ?
C1 N8 H8 . . 119.(4) ?
O10 C9 N8 . . 123.2(5) ?
O10 C9 C11 . . 123.3(4) ?
N8 C9 C11 . . 113.5(5) ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C17 C12 C13 . . 119.4(5) ?
C17 C12 C18 . . 119.3(4) ?
C13 C12 C18 . . 121.3(4) ?
C14 C13 C12 . . 119.6(5) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C13 C14 C15 . . 120.8(5) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C14 C15 C16 . . 119.5(5) ?
C14 C15 H15 . . 120.2 ?
C16 C15 H15 . . 120.2 ?
C17 C16 C15 . . 119.8(5) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C16 C17 C12 . . 120.9(5) ?
C16 C17 H17 . . 119.6 ?
C12 C17 H17 . . 119.6 ?
O19 C18 O20 . . 122.8(5) ?
O19 C18 C12 . . 122.9(4) ?
O20 C18 C12 . . 114.2(4) ?
C18 O20 H20 . . 113.(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N8 H8 O19 1_455 0.86(4) 2.04(4) 2.889(6) 173.(6) ?
O20 H20 N2 1_655 0.80(3) 1.88(3) 2.664(6) 167.(8) ?



####################################################################### 
# 
# 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_I-Me_4Cl-BA
_database_code_depnum_ccdc_archive 'CCDC 2092010'
loop_
_audit_author_name
_audit_author_address
'Boris B Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_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         'C7 H7 I N2 O, C7 H5 Cl O2'
_chemical_formula_sum            'C14 H12 Cl I N2 O3'
_chemical_formula_weight         418.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H12N2O3Cl1I1
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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.35000(10)
_cell_length_b                   11.5717(2)
_cell_length_c                   15.4381(3)
_cell_angle_alpha                78.041(2)
_cell_angle_beta                 88.920(2)
_cell_angle_gamma                87.755(2)
_cell_volume                     759.61(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12376
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.6050
_cell_measurement_theta_min      2.8840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.289
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.111a (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    1.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method 'crystallized from ethyl acetate'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.016
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15874
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.860
_diffrn_reflns_theta_min         2.926
_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 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -16.00   0.50    1.20    --  -43.30  96.00 -90.00   94
  2  ω     -8.00  26.00   0.50    1.20    --  -43.30  96.00 -90.00   68
  3  ω      4.00  50.00   0.50    1.20    --   43.30 -96.00 160.00   92
  4  ω    -72.00 -47.00   0.50    4.00    --  -90.25  96.00 -90.00   50
  5  ω     73.00 104.00   0.50    4.00    --  111.75 -96.00 160.00   62
  6  ω    142.00 167.00   0.50    4.00    --  111.75  96.00 -90.00   50
  7  ω    -70.00 -28.00   0.50    1.20    --  -43.30  77.00   0.00   84
  8  ω    -23.00  28.00   0.50    1.20    --  -43.30  77.00   0.00  102
  9  ω    -43.00  34.00   0.50    1.20    --  -43.30  38.00 -60.00  154
 10  ω   -116.00 -19.00   0.50    1.20    --  -43.30 -77.00-180.00  194
 11  ω     65.00  97.00   0.50    1.20    --   43.30-125.00-180.00   64
 12  ω   -134.00-108.00   0.50    4.00    --  -90.25 -96.00 160.00   52
 13  ω   -156.00 -83.00   0.50    4.00    --  -90.25 -94.00 -90.00  146
 14  ω    106.00 153.00   0.50    4.00    --  111.75  45.00-120.00   94
 15  ω     38.00  63.00   0.50    4.00    --  111.75 -61.00  60.00   50
 16  ω     89.00 169.00   0.50    4.00    --  111.75  30.00   0.00  160
 17  ω     73.00  98.00   0.50    4.00    --  111.75 -94.00  60.00   50
 18  ω     89.00 147.00   0.50    4.00    --  111.75  30.00 150.00  116
 19  ω     86.00 112.00   0.50    4.00    --  111.75-125.00-120.00   52
 20  ω     73.00 101.00   0.50    4.00    --  111.75  15.00  90.00   56
 21  ω     42.00  68.00   0.50    4.00    --  111.75 -94.00  60.00   52
 22  ω     84.00 111.00   0.50    4.00    --  111.75-125.00   0.00   54
 23  ω     77.00 106.00   0.50    4.00    --  111.75 -94.00   0.00   58
 24  ω     38.00  64.00   0.50    4.00    --  111.75-125.00   0.00   52
 25  ω     59.00  84.00   0.50    4.00    --  111.75-125.00-150.00   50
 26  ω     67.00  97.00   0.50    4.00    --  111.75 -94.00-120.00   60
 27  ω     38.00  64.00   0.50    4.00    --  111.75 -94.00  90.00   52
 28  ω     81.00 106.00   0.50    4.00    --  111.75 -94.00  90.00   50
 29  ω     40.00  91.00   0.50    4.00    --  111.75 -77.00   0.00  102
 30  ω     91.00 158.00   0.50    4.00    --  111.75  45.00-180.00  134
 31  ω     50.00 100.00   0.50    4.00    --  111.75 -94.00  30.00  100
 32  ω     47.00  72.00   0.50    4.00    --  111.75-125.00-120.00   50
 33  ω     80.00 105.00   0.50    4.00    --  111.75 -77.00  90.00   50
 34  ω     89.00 119.00   0.50    4.00    --  111.75  61.00 -90.00   60
 35  ω    140.00 166.00   0.50    4.00    --  111.75  61.00 -90.00   52
 36  ω    147.00 176.00   0.50    4.00    --  111.75  15.00-150.00   58
 37  ω     43.00  93.00   0.50    4.00    --  111.75 -94.00 -90.00  100
 38  ω     83.00 144.00   0.50    4.00    --  111.75  15.00 -90.00  122
 39  ω     39.00  65.00   0.50    4.00    --  111.75 -61.00  30.00   52
 40  ω     49.00  75.00   0.50    4.00    --  111.75 -77.00  90.00   52
 41  ω     38.00  80.00   0.50    4.00    --  111.75 -68.00  84.83   84
 42  ω    144.00 170.00   0.50    4.00    --  111.75  77.00 120.00   52
 43  ω     42.00  67.00   0.50    4.00    --  111.75 -77.00 -60.00   50
 44  ω     70.00 109.00   0.50    4.00    --  111.75-118.00 -49.22   78
 45  ω     52.00  93.00   0.50    4.00    --  111.75 -94.00 -30.00   82
 46  ω     87.00 112.00   0.50    4.00    --  111.75-125.00-150.00   50
 47  ω     80.00 112.00   0.50    4.00    --  111.75-125.00  30.00   64
 48  ω     57.00 106.00   0.50    4.00    --  111.75-125.00 120.00   98
 49  ω     91.00 151.00   0.50    4.00    --  111.75  45.00 150.00  120
 50  ω    127.00 153.00   0.50    4.00    --  111.75  77.00 150.00   52
 51  ω     54.00 104.00   0.50    4.00    --  111.75 -77.00-180.00  100
 52  ω     45.00  77.00   0.50    4.00    --  111.75 -77.00-150.00   64
 53  ω    109.00 176.00   0.50    4.00    --  111.75  15.00  90.00  134
 54  ω     38.00  74.00   0.50    4.00    --  111.75-125.00 -30.00   72
 55  ω     45.00  70.00   0.50    4.00    --  111.75 -61.00 150.00   50
 56  ω     91.00 117.00   0.50    4.00    --  111.75  58.00 135.98   52
 57  ω     91.00 116.00   0.50    4.00    --  111.75  61.00-180.00   50
 58  ω    116.00 141.00   0.50    4.00    --  111.75  77.00  30.00   50
 59  ω    115.00 141.00   0.50    4.00    --  111.75 -80.00-102.39   52
 60  ω     43.00  68.00   0.50    4.00    --  111.75 -94.00   0.00   50
 61  ω    118.00 143.00   0.50    4.00    --  111.75  96.00 -90.00   50
 62  ω     80.00 108.00   0.50    4.00    --  111.75-125.00  90.00   56
 63  ω     84.00 119.00   0.50    4.00    --  111.75  77.00  60.00   70
 64  ω    125.00 151.00   0.50    4.00    --  111.75  77.00  60.00   52
 65  ω     38.00  63.00   0.50    4.00    --  111.75 -61.00 -30.00   50
 66  ω     96.00 122.00   0.50    4.00    --  111.75  67.00-164.73   52
 67  ω    150.00 176.00   0.50    4.00    --  111.75  67.00-164.73   52
 68  ω     49.00  75.00   0.50    4.00    --  111.75 -77.00  30.00   52
 69  ω     62.00  88.00   0.50    4.00    --  111.75 -94.00-180.00   52
 70  ω     81.00 106.00   0.50    4.00    --  111.75 -94.00 120.00   50
 71  ω    143.00 169.00   0.50    4.00    --  111.75  45.00-180.00   52
 72  ω    143.00 169.00   0.50    4.00    --  111.75  45.00-150.00   52
 73  ω    117.00 143.00   0.50    4.00    --  111.75 -83.00 107.03   52
 74  ω     47.00  73.00   0.50    4.00    --  111.75-125.00  90.00   52
 75  ω   -116.00 -14.00   0.50    1.20    --  -43.30 -77.00   0.00  204
 76  ω   -116.00 -20.00   0.50    1.20    --  -43.30 -57.00 -90.00  192
 77  ω   -116.00 -20.00   0.50    1.20    --  -43.30 -57.00  90.00  192
 78  ω   -116.00 -14.00   0.50    1.20    --  -43.30 -77.00  60.00  204
 79  ω   -116.00 -14.00   0.50    1.20    --  -43.30 -77.00 -90.00  204
 80  ω   -120.00 -20.00   0.50    1.20    --  -43.30 -38.00-180.00  200
 81  ω    -34.00  43.00   0.50    1.20    --   43.30 -38.00 150.00  154
 82  ω     14.00 117.00   0.50    1.20    --   43.30  77.00-180.00  206
 83  ω     12.00 123.00   0.50    1.20    --   43.30  19.00  30.00  222
 84  ω     14.00 117.00   0.50    1.20    --   43.30  77.00 -60.00  206
 85  ω     83.00 133.00   0.50    4.00    --  111.75  77.00-120.00  100
;
_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      0.0837231000
_diffrn_orient_matrix_UB_12      -0.1016123000
_diffrn_orient_matrix_UB_13      0.0783973000
_diffrn_orient_matrix_UB_21      0.0919216000
_diffrn_orient_matrix_UB_22      0.0905336000
_diffrn_orient_matrix_UB_23      0.0544153000
_diffrn_orient_matrix_UB_31      -0.3319252000
_diffrn_orient_matrix_UB_32      0.0046853000
_diffrn_orient_matrix_UB_33      0.0360399000
_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                3028
_reflns_number_total             3214
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (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    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0228
_refine_ls_restrained_S_all      1.102
_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)+(0.0307P)²+0.2288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C16(H16), C17(H17), C14(H14), C13(H13), C6(H6), C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_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
I7 I 0.80093(4) 0.10114(2) 0.20037(2) 0.04752(7) Uani 1 1 d . . . . .
Cl19 Cl -0.34675(14) 0.84890(5) 0.58830(4) 0.04592(14) Uani 1 1 d . . . . .
O20 O 0.5984(4) 0.73609(17) 0.26388(12) 0.0461(4) Uani 1 1 d . . . . .
O21 O 0.5272(5) 0.55495(16) 0.34477(12) 0.0503(5) Uani 1 1 d . . . . .
H21 H 0.643293 0.535093 0.305854 0.075 Uiso 1 1 calc R U . . .
O10 O 1.4157(5) 0.67883(19) 0.04415(14) 0.0562(5) Uani 1 1 d . . . . .
N8 N 1.0463(5) 0.63508(19) 0.15097(14) 0.0416(4) Uani 1 1 d . . . . .
H8 H 0.933208 0.666808 0.188435 0.050 Uiso 1 1 calc R U . . .
N2 N 0.8397(5) 0.46367(19) 0.22504(13) 0.0408(4) Uani 1 1 d . . . . .
C1 C 1.0244(5) 0.5139(2) 0.15851(15) 0.0369(5) Uani 1 1 d . . . . .
C15 C -0.1094(5) 0.7965(2) 0.51193(16) 0.0365(5) Uani 1 1 d . . . . .
C12 C 0.2776(5) 0.7142(2) 0.39267(15) 0.0347(4) Uani 1 1 d . . . . .
C16 C -0.0121(6) 0.6787(2) 0.52982(16) 0.0389(5) Uani 1 1 d . . . . .
H16 H -0.076886 0.626800 0.582427 0.047 Uiso 1 1 calc R U . . .
C4 C 0.9151(6) 0.2785(2) 0.18153(16) 0.0381(5) Uani 1 1 d . . . . .
C18 C 0.4839(6) 0.6705(2) 0.32750(16) 0.0386(5) Uani 1 1 d . . . . .
C17 C 0.1808(6) 0.6383(2) 0.46978(16) 0.0383(5) Uani 1 1 d . . . . .
H17 H 0.248514 0.557546 0.481126 0.046 Uiso 1 1 calc R U . . .
C14 C -0.0187(6) 0.8739(2) 0.43572(16) 0.0391(5) Uani 1 1 d . . . . .
H14 H -0.089708 0.954204 0.424266 0.047 Uiso 1 1 calc R U . . .
C13 C 0.1777(6) 0.8322(2) 0.37633(16) 0.0395(5) Uani 1 1 d . . . . .
H13 H 0.244318 0.884617 0.324188 0.047 Uiso 1 1 calc R U . . .
C6 C 1.1707(6) 0.4478(2) 0.10236(16) 0.0425(5) Uani 1 1 d . . . . .
H6 H 1.307336 0.484071 0.056956 0.051 Uiso 1 1 calc R U . . .
C9 C 1.2223(6) 0.7112(2) 0.09238(16) 0.0425(5) Uani 1 1 d . . . . .
C3 C 0.7856(6) 0.3479(2) 0.23623(16) 0.0417(5) Uani 1 1 d . . . . .
H3 H 0.653807 0.312724 0.283325 0.050 Uiso 1 1 calc R U . . .
C5 C 1.1131(6) 0.3291(2) 0.11406(16) 0.0412(5) Uani 1 1 d . . . . .
H5 H 1.208061 0.282630 0.076335 0.049 Uiso 1 1 calc R U . . .
C11 C 1.1535(8) 0.8395(3) 0.0931(2) 0.0549(7) Uani 1 1 d . . . . .
H11A H 1.340574 0.884124 0.077680 0.082 Uiso 1 1 calc R U . . .
H11B H 1.081959 0.847101 0.152316 0.082 Uiso 1 1 calc R U . . .
H11C H 0.993303 0.870713 0.049856 0.082 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
I7 C4 2.090(2) . ?
Cl19 C15 1.739(2) . ?
O20 C18 1.221(3) . ?
O21 C18 1.315(3) . ?
O10 C9 1.213(3) . ?
N8 C1 1.390(3) . ?
N8 C9 1.370(3) . ?
N2 C1 1.340(3) . ?
N2 C3 1.345(3) . ?
C1 C6 1.399(3) . ?
C15 C16 1.384(3) . ?
C15 C14 1.384(3) . ?
C12 C18 1.488(3) . ?
C12 C17 1.394(3) . ?
C12 C13 1.390(3) . ?
C16 C17 1.379(4) . ?
C4 C3 1.380(3) . ?
C4 C5 1.387(3) . ?
C14 C13 1.387(4) . ?
C6 C5 1.380(4) . ?
C9 C11 1.505(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N8 C1 128.0(2) . . ?
C1 N2 C3 119.2(2) . . ?
N8 C1 C6 125.0(2) . . ?
N2 C1 N8 113.5(2) . . ?
N2 C1 C6 121.5(2) . . ?
C16 C15 Cl19 119.00(18) . . ?
C16 C15 C14 121.8(2) . . ?
C14 C15 Cl19 119.24(19) . . ?
C17 C12 C18 121.0(2) . . ?
C13 C12 C18 119.7(2) . . ?
C13 C12 C17 119.3(2) . . ?
C17 C16 C15 118.7(2) . . ?
C3 C4 I7 119.37(18) . . ?
C3 C4 C5 119.0(2) . . ?
C5 C4 I7 121.65(18) . . ?
O20 C18 O21 123.7(2) . . ?
O20 C18 C12 122.9(2) . . ?
O21 C18 C12 113.4(2) . . ?
C16 C17 C12 120.9(2) . . ?
C15 C14 C13 118.9(2) . . ?
C14 C13 C12 120.4(2) . . ?
C5 C6 C1 118.9(2) . . ?
O10 C9 N8 123.4(3) . . ?
O10 C9 C11 122.8(2) . . ?
N8 C9 C11 113.8(2) . . ?
N2 C3 C4 122.1(2) . . ?
C6 C5 C4 119.2(2) . . ?

_olex2_date_sample_data_collection 2021-06-15
_olex2_date_sample_submission    2021-06-15
_olex2_exptl_crystal_mounting_method 'mounted on a MITeGen loop'
_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 1.893
_oxdiff_exptl_absorpt_empirical_full_min 0.569
####################################################################### 
# 
# 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_I-Pr_BA
_database_code_depnum_ccdc_archive 'CCDC 2092013'
loop_
_audit_author_name
_audit_author_address
'Abhijeet S. Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2020-01-31
_audit_creation_method           
;
APEX2 v2014.11-0
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H11 I N2 O, C7 H6 O2'
_chemical_formula_sum            'C16 H17 I N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         412.21

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   15.6069(6)
_cell_length_b                   4.7766(2)
_cell_length_c                   22.7736(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.088(3)
_cell_angle_gamma                90
_cell_volume                     1696.60(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3433
_cell_measurement_theta_min      5.67
_cell_measurement_theta_max      63.58
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

_exptl_absorpt_coefficient_mu    14.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1453 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.4548.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_correction_T_min  0.29
_exptl_absorpt_correction_T_max  0.59

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13110
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         70.46
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_refine_special_details          
;
;

_reflns_number_total             3111
_reflns_number_gt                2171
_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)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1550
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.109
_refine_ls_number_reflns         3111
_refine_ls_number_parameters     208
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+1.2079P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.908
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4091(4) 1.0314(11) 0.5795(2) 0.0618(13) Uani d . . . 1 . .
N N2 0.3461(3) 0.8617(11) 0.5981(2) 0.0667(12) Uani d . . . 1 . .
C C3 0.2684(4) 0.8722(14) 0.5709(2) 0.0700(15) Uani d . . . 1 . .
H H3 0.2253 0.755 0.5837 0.084 Uiso calc U . R 1 . .
C C4 0.2507(4) 1.0486(14) 0.5253(3) 0.0723(16) Uani d . . . 1 . .
C C5 0.3137(4) 1.2241(14) 0.5060(2) 0.0737(15) Uani d . . . 1 . .
H H5 0.3023 1.3466 0.475 0.088 Uiso calc U . R 1 . .
C C6 0.3925(4) 1.2162(14) 0.5328(2) 0.0703(15) Uani d . . . 1 . .
H H6 0.4357 1.3335 0.5201 0.084 Uiso calc U . R 1 . .
I I7 0.12704(3) 1.04247(13) 0.48459(2) 0.1001(3) Uani d . . . 1 . .
H H8 0.484(4) 0.869(12) 0.635(3) 0.09(2) Uiso d . . D 1 . .
N N8 0.4858(3) 1.0011(11) 0.6097(2) 0.0669(12) Uani d . . D 1 . .
C C9 0.5591(4) 1.1539(13) 0.6044(2) 0.0654(14) Uani d . . . 1 . .
O O10 0.5664(3) 1.3503(11) 0.5711(2) 0.0841(13) Uani d . . . 1 . .
C C11 0.6316(4) 1.0551(14) 0.6454(3) 0.0776(17) Uani d . . . 1 . .
H H11A 0.6101 1.0407 0.6847 0.093 Uiso calc U . R 1 . .
H H11B 0.6482 0.8684 0.6334 0.093 Uiso calc U . R 1 . .
C C12 0.7089(4) 1.2328(19) 0.6479(4) 0.097(2) Uani d . . . 1 . .
H H12A 0.6944 1.4132 0.6644 0.116 Uiso calc U . R 1 . .
H H12B 0.7274 1.2643 0.6082 0.116 Uiso calc U . R 1 . .
C C13 0.7815(4) 1.110(2) 0.6836(4) 0.107(3) Uani d . . . 1 . .
H H13A 0.7978 0.9343 0.6668 0.161 Uiso calc U . R 1 . .
H H13B 0.764 1.0802 0.7231 0.161 Uiso calc U . R 1 . .
H H13C 0.8294 1.2359 0.6839 0.161 Uiso calc U . R 1 . .
C C14 0.4289(3) 1.2515(11) 0.7643(2) 0.0538(11) Uani d . . . 1 . .
C C15 0.5031(3) 1.2203(14) 0.7986(3) 0.0717(15) Uani d . . . 1 . .
H H15 0.5517 1.3236 0.7903 0.086 Uiso calc U . R 1 . .
C C16 0.5051(5) 1.0376(16) 0.8449(3) 0.086(2) Uani d . . . 1 . .
H H16 0.5552 1.0168 0.8678 0.103 Uiso calc U . R 1 . .
C C17 0.4336(5) 0.8842(16) 0.8577(3) 0.0827(19) Uani d . . . 1 . .
H H17 0.4354 0.7596 0.8891 0.099 Uiso calc U . R 1 . .
C C18 0.3609(4) 0.9151(15) 0.8247(3) 0.0750(16) Uani d . . . 1 . .
H H18 0.3127 0.8113 0.8338 0.09 Uiso calc U . R 1 . .
C C19 0.3563(3) 1.0987(13) 0.7774(2) 0.0632(13) Uani d . . . 1 . .
H H19 0.3057 1.119 0.755 0.076 Uiso calc U . R 1 . .
C C20 0.4278(3) 1.4530(12) 0.7146(2) 0.0573(12) Uani d . . . 1 . .
O O21 0.4912(2) 1.5829(9) 0.7013(2) 0.0757(11) Uani d . . . 1 . .
H H22 0.357(4) 1.614(11) 0.666(3) 0.08(2) Uiso d . . D 1 . .
O O22 0.3529(2) 1.4812(9) 0.68671(19) 0.0690(11) Uani d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.354(7) ?
C1 N8 . 1.366(8) ?
C1 C6 . 1.400(8) ?
N2 C3 . 1.342(7) ?
C3 C4 . 1.358(9) ?
C3 H3 . 0.93 ?
C4 C5 . 1.376(9) ?
C4 I7 . 2.111(6) ?
C5 C6 . 1.353(8) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
I7 I7 3_576 4.0724(10) ?
N8 C9 . 1.366(8) ?
N8 H8 . 0.85(4) ?
C9 O10 . 1.215(7) ?
C9 C11 . 1.515(8) ?
C11 C12 . 1.475(9) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 C13 . 1.490(9) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
C14 C15 . 1.382(7) ?
C14 C19 . 1.389(7) ?
C14 C20 . 1.486(7) ?
C15 C16 . 1.367(9) ?
C15 H15 . 0.93 ?
C16 C17 . 1.376(10) ?
C16 H16 . 0.93 ?
C17 C18 . 1.346(9) ?
C17 H17 . 0.93 ?
C18 C19 . 1.389(8) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?
C20 O21 . 1.217(7) ?
C20 O22 . 1.316(6) ?
O22 H22 . 0.80(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N8 . . 114.4(5) ?
N2 C1 C6 . . 119.9(6) ?
N8 C1 C6 . . 125.7(6) ?
C3 N2 C1 . . 119.2(5) ?
N2 C3 C4 . . 122.1(6) ?
N2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C3 C4 C5 . . 119.6(6) ?
C3 C4 I7 . . 119.0(5) ?
C5 C4 I7 . . 121.4(5) ?
C6 C5 C4 . . 119.2(6) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C1 . . 120.0(6) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
C4 I7 I7 . 3_576 143.72(17) ?
C9 N8 C1 . . 128.4(5) ?
C9 N8 H8 . . 120.(5) ?
C1 N8 H8 . . 112.(5) ?
O10 C9 N8 . . 124.4(6) ?
O10 C9 C11 . . 122.7(6) ?
N8 C9 C11 . . 112.9(5) ?
C12 C11 C9 . . 115.9(6) ?
C12 C11 H11A . . 108.3 ?
C9 C11 H11A . . 108.3 ?
C12 C11 H11B . . 108.3 ?
C9 C11 H11B . . 108.3 ?
H11A C11 H11B . . 107.4 ?
C11 C12 C13 . . 113.5(6) ?
C11 C12 H12A . . 108.9 ?
C13 C12 H12A . . 108.9 ?
C11 C12 H12B . . 108.9 ?
C13 C12 H12B . . 108.9 ?
H12A C12 H12B . . 107.7 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C15 C14 C19 . . 119.6(5) ?
C15 C14 C20 . . 119.2(5) ?
C19 C14 C20 . . 121.2(5) ?
C16 C15 C14 . . 120.0(6) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 120.5(6) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C18 C17 C16 . . 119.8(6) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C19 . . 121.4(6) ?
C17 C18 H18 . . 119.3 ?
C19 C18 H18 . . 119.3 ?
C14 C19 C18 . . 118.7(5) ?
C14 C19 H19 . . 120.7 ?
C18 C19 H19 . . 120.7 ?
O21 C20 O22 . . 123.0(5) ?
O21 C20 C14 . . 122.2(5) ?
O22 C20 C14 . . 114.8(5) ?
C20 O22 H22 . . 106.(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N8 H8 O21 1_545 0.85(4) 2.04(4) 2.886(6) 173.(7) ?
O22 H22 N2 1_565 0.80(4) 1.95(4) 2.715(6) 162.(8) ?



####################################################################### 
# 
# 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_I-Et_BA
_database_code_depnum_ccdc_archive 'CCDC 2092012'
loop_
_audit_author_name
_audit_author_address
'Abhijeet S. Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2019-09-12
_audit_creation_method           
;
APEX2 v2014.11-0
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H9 I N2 O, C7 H6 O2'
_chemical_formula_sum            'C15 H15 I N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         398.19

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   14.2075(8)
_cell_length_b                   4.9292(3)
_cell_length_c                   22.1266(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.025(2)
_cell_angle_gamma                90
_cell_volume                     1549.56(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6383
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      68.15
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784

_exptl_absorpt_coefficient_mu    16.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1250 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.5071.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_correction_T_min  0.14
_exptl_absorpt_correction_T_max  0.42

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            10580
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         68.40
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             2742
_reflns_number_gt                2488
_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)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1075
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         2742
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.8861P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.796
_refine_diff_density_min         -1.147
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4329(3) -0.0224(7) 0.58792(18) 0.0319(8) Uani d . . . 1 . .
N N2 0.3672(2) 0.1584(6) 0.60415(14) 0.0342(7) Uani d . . . 1 . .
C C3 0.2862(3) 0.1676(8) 0.57358(17) 0.0353(8) Uani d . . . 1 . .
H H3 0.2399 0.2965 0.5852 0.042 Uiso calc U . R 1 . .
C C4 0.2676(3) -0.0027(7) 0.52598(19) 0.0337(8) Uani d . . . 1 . .
C C5 0.3346(3) -0.1913(8) 0.50902(17) 0.0381(8) Uani d . . . 1 . .
H H5 0.3232 -0.3113 0.4762 0.046 Uiso calc U . R 1 . .
C C6 0.4176(3) -0.2022(8) 0.54014(16) 0.0364(8) Uani d . . . 1 . .
H H6 0.4645 -0.3309 0.5294 0.044 Uiso calc U . R 1 . .
I I7 0.13927(2) 0.03010(6) 0.47969(2) 0.04749(15) Uani d . . . 1 . .
H H8 0.517(3) 0.108(10) 0.648(2) 0.041(12) Uiso d . . . 1 . .
N N8 0.5137(3) -0.0104(6) 0.62229(17) 0.0340(7) Uani d . . . 1 . .
C C9 0.5919(2) -0.1769(7) 0.61962(16) 0.0335(8) Uani d . . . 1 . .
O O10 0.5981(2) -0.3681(6) 0.58556(13) 0.0452(7) Uani d . . . 1 . .
C C11 0.6692(3) -0.0926(8) 0.66240(19) 0.0394(9) Uani d . . . 1 . .
H H11A 0.7046 0.06 0.6443 0.047 Uiso calc U . R 1 . .
H H11B 0.6406 -0.027 0.7005 0.047 Uiso calc U . R 1 . .
C C12 0.7367(3) -0.3193(9) 0.6767(2) 0.0465(10) Uani d . . . 1 . .
H H12A 0.7614 -0.3955 0.639 0.07 Uiso calc U . R 1 . .
H H12B 0.7038 -0.4612 0.6994 0.07 Uiso calc U . R 1 . .
H H12C 0.7889 -0.2485 0.701 0.07 Uiso calc U . R 1 . .
C C13 0.4412(2) -0.2488(7) 0.77424(15) 0.0273(7) Uani d . . . 1 . .
C C14 0.5171(2) -0.2232(8) 0.81312(17) 0.0361(8) Uani d . . . 1 . .
H H14 0.5708 -0.3357 0.8081 0.043 Uiso calc U . R 1 . .
C C15 0.5149(3) -0.0349(8) 0.8591(2) 0.0426(10) Uani d . . . 1 . .
H H15 0.5672 -0.0176 0.8857 0.051 Uiso calc U . R 1 . .
C C16 0.4364(3) 0.1299(9) 0.86687(18) 0.0407(9) Uani d . . . 1 . .
H H16 0.4347 0.2582 0.8989 0.049 Uiso calc U . R 1 . .
C C17 0.3610(3) 0.1066(8) 0.82792(18) 0.0367(8) Uani d . . . 1 . .
H H17 0.3078 0.2211 0.8328 0.044 Uiso calc U . R 1 . .
C C18 0.3626(2) -0.0834(7) 0.78165(17) 0.0310(7) Uani d . . . 1 . .
H H18 0.3103 -0.1006 0.7551 0.037 Uiso calc U . R 1 . .
C C19 0.4453(3) -0.4536(7) 0.72502(18) 0.0295(8) Uani d . . . 1 . .
O O20 0.51521(18) -0.5940(6) 0.71571(13) 0.0377(6) Uani d . . . 1 . .
H H21 0.368(3) -0.601(10) 0.666(2) 0.051(14) Uiso d . . . 1 . .
O O21 0.3679(2) -0.4704(5) 0.69251(14) 0.0375(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.340(5) ?
C1 N8 . 1.378(6) ?
C1 C6 . 1.396(5) ?
N2 C3 . 1.336(5) ?
C3 C4 . 1.373(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.383(5) ?
C4 I7 . 2.097(4) ?
C5 C6 . 1.366(5) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
I7 I7 3_556 4.0693(6) ?
N8 C9 . 1.383(5) ?
N8 H8 . 0.82(5) ?
C9 O10 . 1.210(5) ?
C9 C11 . 1.508(5) ?
C11 C12 . 1.506(6) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.384(5) ?
C13 C18 . 1.392(5) ?
C13 C19 . 1.487(5) ?
C14 C15 . 1.378(6) ?
C14 H14 . 0.95 ?
C15 C16 . 1.390(6) ?
C15 H15 . 0.95 ?
C16 C17 . 1.379(6) ?
C16 H16 . 0.95 ?
C17 C18 . 1.388(6) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 O20 . 1.228(5) ?
C19 O21 . 1.317(5) ?
O21 H21 . 0.88(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N8 . . 113.8(3) ?
N2 C1 C6 . . 121.1(4) ?
N8 C1 C6 . . 125.1(3) ?
C3 N2 C1 . . 119.2(3) ?
N2 C3 C4 . . 122.2(3) ?
N2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C3 C4 C5 . . 119.1(4) ?
C3 C4 I7 . . 119.6(3) ?
C5 C4 I7 . . 121.2(3) ?
C6 C5 C4 . . 119.0(3) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C1 . . 119.4(3) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
C4 I7 I7 . 3_556 137.04(11) ?
C1 N8 C9 . . 128.3(3) ?
C1 N8 H8 . . 118.(3) ?
C9 N8 H8 . . 114.(3) ?
O10 C9 N8 . . 123.2(4) ?
O10 C9 C11 . . 123.6(3) ?
N8 C9 C11 . . 113.2(3) ?
C12 C11 C9 . . 113.0(3) ?
C12 C11 H11A . . 109.0 ?
C9 C11 H11A . . 109.0 ?
C12 C11 H11B . . 109.0 ?
C9 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C18 . . 119.9(3) ?
C14 C13 C19 . . 119.1(3) ?
C18 C13 C19 . . 121.0(3) ?
C15 C14 C13 . . 120.2(4) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.2(4) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C17 C16 C15 . . 119.8(4) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C16 C17 C18 . . 120.3(4) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C17 C18 C13 . . 119.7(3) ?
C17 C18 H18 . . 120.2 ?
C13 C18 H18 . . 120.2 ?
O20 C19 O21 . . 123.3(3) ?
O20 C19 C13 . . 122.5(4) ?
O21 C19 C13 . . 114.2(3) ?
C19 O21 H21 . . 115.(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N8 H8 O20 1_565 0.82(5) 2.09(5) 2.913(4) 176.(4) ?
O21 H21 N2 1_545 0.88(5) 1.81(5) 2.678(4) 174.(5) ?



####################################################################### 
# 
# 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_I-Et_4Cl-BA
_database_code_depnum_ccdc_archive 'CCDC 2092014'
loop_
_audit_author_name
_audit_author_address
'Abhijeet S. Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2019-09-10
_audit_creation_method           
;
APEX2 v2014.11-0
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H9 I N2 O, C7 H5 Cl O2'
_chemical_formula_sum            'C15 H14 Cl I N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         432.63

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   34.113(3)
_cell_length_b                   4.0412(3)
_cell_length_c                   28.573(2)
_cell_angle_alpha                90
_cell_angle_beta                 124.614(3)
_cell_angle_gamma                90
_cell_volume                     3241.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7108
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      68.12
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.042
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696

_exptl_absorpt_coefficient_mu    17.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.3236.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_correction_T_min  0.21
_exptl_absorpt_correction_T_max  0.53

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            12254
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       34

_refine_special_details          
;
;

_reflns_number_total             2888
_reflns_number_gt                2636
_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)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1737
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_refine_ls_number_reflns         2888
_refine_ls_number_parameters     208
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+78.6144P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.943
_refine_diff_density_min         -0.876
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3275(3) 0.135(3) 0.4893(4) 0.042(2) Uani d . . . 1 . .
N N2 0.3694(3) 0.289(2) 0.5150(3) 0.0437(19) Uani d . . . 1 . .
C C3 0.3917(3) 0.373(3) 0.5695(4) 0.045(2) Uani d . . . 1 . .
H H3 0.4216 0.4829 0.5875 0.054 Uiso calc U . R 1 . .
C C4 0.3736(3) 0.309(3) 0.6009(4) 0.041(2) Uani d . . . 1 . .
C C5 0.3307(4) 0.142(3) 0.5752(4) 0.052(3) Uani d . . . 1 . .
H H5 0.3178 0.0896 0.5962 0.062 Uiso calc U . R 1 . .
C C6 0.3071(3) 0.053(3) 0.5191(4) 0.050(3) Uani d . . . 1 . .
H H6 0.2777 -0.0622 0.5006 0.06 Uiso calc U . R 1 . .
I I7 0.41136(2) 0.45935(17) 0.68601(3) 0.0497(3) Uani d . . . 1 . .
H H8 0.322(3) 0.18(2) 0.421(4) 0.04(3) Uiso d . . D 1 . .
N N8 0.3069(3) 0.066(2) 0.4324(3) 0.046(2) Uani d . . D 1 . .
C C9 0.2656(3) -0.101(3) 0.3948(4) 0.049(2) Uani d . . . 1 . .
O O10 0.2411(3) -0.224(3) 0.4085(4) 0.075(3) Uani d . . . 1 . .
C C11 0.2543(3) -0.119(3) 0.3356(4) 0.052(3) Uani d . . . 1 . .
H H11A 0.2774 -0.2682 0.3357 0.063 Uiso calc U . R 1 . .
H H11B 0.2578 0.1038 0.324 0.063 Uiso calc U . R 1 . .
C C12 0.2037(4) -0.246(4) 0.2923(5) 0.068(3) Uani d . . . 1 . .
H H12A 0.1973 -0.2467 0.2543 0.102 Uiso calc U . R 1 . .
H H12B 0.1808 -0.1005 0.2925 0.102 Uiso calc U . R 1 . .
H H12C 0.2006 -0.471 0.3026 0.102 Uiso calc U . R 1 . .
C C13 0.4181(3) -0.302(3) 0.3967(4) 0.037(2) Uani d . . . 1 . .
C C14 0.3938(3) -0.239(3) 0.3392(4) 0.042(2) Uani d . . . 1 . .
H H14 0.3611 -0.296 0.3146 0.051 Uiso calc U . R 1 . .
C C15 0.4165(3) -0.094(3) 0.3172(4) 0.044(2) Uani d . . . 1 . .
H H15 0.3999 -0.0544 0.2775 0.053 Uiso calc U . R 1 . .
C C16 0.4642(3) -0.005(2) 0.3538(4) 0.039(2) Uani d . . . 1 . .
C C17 0.4889(3) -0.070(3) 0.4112(4) 0.046(2) Uani d . . . 1 . .
H H17 0.5217 -0.0148 0.4358 0.055 Uiso calc U . R 1 . .
C C18 0.4659(3) -0.214(3) 0.4326(4) 0.043(2) Uani d . . . 1 . .
H H18 0.4826 -0.2538 0.4723 0.052 Uiso calc U . R 1 . .
C C19 0.3921(3) -0.464(3) 0.4185(4) 0.041(2) Uani d . . . 1 . .
O O20 0.3528(2) -0.587(2) 0.3872(3) 0.0489(17) Uani d . . . 1 . .
H H21 0.398(4) -0.54(3) 0.482(5) 0.07(4) Uiso d . . D 1 . .
O O21 0.4164(2) -0.474(2) 0.4740(3) 0.058(2) Uani d . . D 1 . .
Cl Cl22 0.49379(8) 0.1660(7) 0.32658(10) 0.0514(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.336(12) ?
C1 N8 . 1.385(12) ?
C1 C6 . 1.408(13) ?
N2 C3 . 1.331(12) ?
C3 C4 . 1.373(12) ?
C3 H3 . 0.95 ?
C4 C5 . 1.382(14) ?
C4 I7 . 2.093(9) ?
C5 C6 . 1.373(15) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
I7 Cl22 6_566 3.674(3) ?
N8 C9 . 1.371(12) ?
N8 H8 . 0.87(5) ?
C9 O10 . 1.214(12) ?
C9 C11 . 1.508(15) ?
C11 C12 . 1.532(13) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.378(12) ?
C13 C18 . 1.392(12) ?
C13 C19 . 1.493(12) ?
C14 C15 . 1.377(13) ?
C14 H14 . 0.95 ?
C15 C16 . 1.392(13) ?
C15 H15 . 0.95 ?
C16 C17 . 1.378(13) ?
C16 Cl22 . 1.729(9) ?
C17 C18 . 1.370(13) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 O20 . 1.217(11) ?
C19 O21 . 1.308(11) ?
O21 H21 . 0.82(5) ?
Cl22 I7 5_666 3.770(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N8 . . 114.2(8) ?
N2 C1 C6 . . 121.3(9) ?
N8 C1 C6 . . 124.6(8) ?
C3 N2 C1 . . 119.0(8) ?
N2 C3 C4 . . 123.1(9) ?
N2 C3 H3 . . 118.4 ?
C4 C3 H3 . . 118.4 ?
C3 C4 C5 . . 118.5(9) ?
C3 C4 I7 . . 119.7(7) ?
C5 C4 I7 . . 121.8(7) ?
C6 C5 C4 . . 119.4(9) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 118.7(9) ?
C5 C6 H6 . . 120.6 ?
C1 C6 H6 . . 120.6 ?
C4 I7 Cl22 . 6_566 166.7(3) ?
C9 N8 C1 . . 129.0(8) ?
C9 N8 H8 . . 122.(6) ?
C1 N8 H8 . . 108.(7) ?
O10 C9 N8 . . 122.6(10) ?
O10 C9 C11 . . 124.0(9) ?
N8 C9 C11 . . 113.4(9) ?
C9 C11 C12 . . 111.9(9) ?
C9 C11 H11A . . 109.2 ?
C12 C11 H11A . . 109.2 ?
C9 C11 H11B . . 109.2 ?
C12 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C18 . . 119.4(8) ?
C14 C13 C19 . . 118.8(8) ?
C18 C13 C19 . . 121.9(8) ?
C15 C14 C13 . . 120.7(8) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 119.1(8) ?
C14 C15 H15 . . 120.4 ?
C16 C15 H15 . . 120.4 ?
C17 C16 C15 . . 120.5(8) ?
C17 C16 Cl22 . . 119.7(7) ?
C15 C16 Cl22 . . 119.7(7) ?
C18 C17 C16 . . 119.8(8) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C13 . . 120.4(8) ?
C17 C18 H18 . . 119.8 ?
C13 C18 H18 . . 119.8 ?
O20 C19 O21 . . 123.5(8) ?
O20 C19 C13 . . 122.7(8) ?
O21 C19 C13 . . 113.8(8) ?
C19 O21 H21 . . 106.(9) ?
C16 Cl22 I7 . 5_666 162.7(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N8 H8 O20 1_565 0.87(5) 2.03(5) 2.894(10) 173.(9) ?
O21 H21 N2 1_545 0.82(5) 1.84(6) 2.643(10) 166.(13) ?



####################################################################### 
# 
# 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_I-Et_35M-BA
_database_code_depnum_ccdc_archive 'CCDC 2092016'
loop_
_audit_author_name
_audit_author_address
'Christer B. Aakeroy'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_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         'C8 H9 I N2 O, C9 H10 O2'
_chemical_formula_sum            'C17 H19 I N2 O3'
_chemical_formula_weight         426.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H19IN2O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.5288(2)
_cell_length_b                   12.8682(4)
_cell_length_c                   15.2840(4)
_cell_angle_alpha                97.439(2)
_cell_angle_beta                 94.401(3)
_cell_angle_gamma                93.065(3)
_cell_volume                     878.80(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15005
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.7210
_cell_measurement_theta_min      2.9380
_shelx_estimated_absorpt_T_max   0.483
_shelx_estimated_absorpt_T_min   0.213
_exptl_absorpt_coefficient_mu    14.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.111a (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    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method 'crystallized from ethylacetate'
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.059
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24138
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.029
_diffrn_reflns_theta_min         2.926
_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 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  -5.00   0.50    1.80    --  -43.05 112.00  19.00  148
  2  ω     25.00  86.00   0.50    1.80    --   43.05-112.00 -72.00  122
  3  ω   -128.00-100.00   0.50    7.40    --  -90.25-112.00 -72.00   56
  4  ω    -70.00 -43.00   0.50    7.40    --  -90.25 112.00  19.00   54
  5  ω     82.00 107.00   0.50    7.40    --  111.75-112.00 -72.00   50
  6  ω    108.00 164.00   0.50    7.40    --  111.75 112.00  19.00  112
  7  ω    -63.00  28.00   0.50    1.80    --  -43.05  57.00 -60.00  182
  8  ω    -52.00 -14.00   0.50    1.80    --  -43.05 -77.00-150.00   76
  9  ω    -51.00 -20.00   0.50    1.80    --  -43.05 -38.00-150.00   62
 10  ω    -62.00 -14.00   0.50    1.80    --  -43.05 -77.00  90.00   96
 11  ω   -120.00 -73.00   0.50    1.80    --  -43.05 -38.00   0.00   94
 12  ω    -68.00 -20.00   0.50    1.80    --  -43.05 -38.00   0.00   96
 13  ω    -66.00 -20.00   0.50    1.80    --  -43.05 -57.00 -90.00   92
 14  ω     83.00 114.00   0.50    1.80    --   43.05  57.00-120.00   62
 15  ω     38.00  95.00   0.50    1.80    --   43.05-125.00  30.00  114
 16  ω     25.00  62.00   0.50    1.80    --   43.05  38.00  60.00   74
 17  ω     29.00  59.00   0.50    1.80    --   43.05  57.00-120.00   60
 18  ω     82.00 110.00   0.50    1.80    --   43.05  57.00  90.00   56
 19  ω     23.00  49.00   0.50    1.80    --   43.05  57.00  90.00   52
 20  ω     15.00  43.00   0.50    1.80    --   46.00  87.00 -53.97   56
 21  ω     14.00  39.00   0.50    1.80    --   46.00  85.00-102.22   50
 22  ω     17.00  42.00   0.50    1.80    --   50.00  87.00  39.44   50
 23  ω     16.00  43.00   0.50    1.80    --   50.00  90.00 129.80   54
 24  ω     17.00  42.00   0.50    1.80    --   50.00  87.00  82.02   50
 25  ω     17.00  42.00   0.50    1.80    --   50.00  86.00-140.93   50
 26  ω   -120.00 -93.00   0.50    1.80    --  -54.00 -76.00  57.11   54
 27  ω    -66.00 -25.00   0.50    1.80    --  -54.00 -76.00  57.11   82
 28  ω    -90.00 -34.00   0.50    1.80    --  -58.00 -67.00-155.28  112
 29  ω     32.00  86.00   0.50    1.80    --   58.00  76.00  -6.61  108
 30  ω    -67.00 -39.00   0.50    1.80    --  -62.00 -63.00-141.26   56
 31  ω     34.00  61.00   0.50    1.80    --   62.00  75.00 148.80   54
 32  ω    100.00 125.00   0.50    1.80    --   62.00  75.00 148.80   50
 33  ω    -65.00 -37.00   0.50    1.80    --  -66.00 -76.00 -74.21   56
 34  ω    -95.00 -46.00   0.50    1.80    --  -66.00 -55.00 122.55   98
 35  ω    -75.00 -45.00   0.50    1.80    --  -66.00 -60.00 145.26   60
 36  ω    -74.00 -46.00   0.50    1.80    --  -66.00 -59.00-126.80   56
 37  ω   -111.00 -83.00   0.50    1.80    --  -66.00 -65.00-177.16   56
 38  ω    -78.00 -43.00   0.50    1.80    --  -66.00 -65.00-177.16   70
 39  ω    -73.00 -45.00   0.50    7.40    --  -70.00 -67.00  86.78   56
 40  ω    -67.00 -42.00   0.50    7.40    --  -70.00 -75.00-138.16   50
 41  ω    -74.00 -47.00   0.50    7.40    --  -70.00 -63.00 162.05   54
 42  ω   -138.00-110.00   0.50    7.40    --  -70.00 -67.00  86.78   56
 43  ω    -94.00 -62.00   0.50    7.40    --  -74.00 -54.00  58.54   64
 44  ω    -74.00 -46.00   0.50    7.40    --  -74.00 -74.00 -75.85   56
 45  ω    -79.00 -51.00   0.50    7.40    --  -74.00 -62.00 -62.50   56
 46  ω    -78.00 -50.00   0.50    7.40    --  -74.00 -61.00-141.34   56
 47  ω    -72.00 -47.00   0.50    7.40    --  -74.00 -73.00 113.57   50
 48  ω   -112.00 -84.00   0.50    7.40    --  -74.00 -58.00 -52.85   56
 49  ω    -81.00 -53.00   0.50    7.40    --  -74.00 -58.00 -52.85   56
 50  ω    -78.00 -51.00   0.50    7.40    --  -78.00 -72.00-158.59   54
 51  ω    -79.00 -54.00   0.50    7.40    --  -82.00 -74.00  43.24   50
 52  ω   -148.00-119.00   0.50    7.40    --  -82.00 -74.00  43.24   58
 53  ω    -82.00 -54.00   0.50    7.40    --  -82.00 -74.00 -75.68   56
 54  ω    -82.00 -54.00   0.50    7.40    --  -82.00 -75.00 131.65   56
 55  ω    -81.00 -53.00   0.50    7.40    --  -82.00 -76.00   5.80   56
 56  ω    -80.00 -55.00   0.50    7.40    --  -82.00 -71.00  21.41   50
 57  ω   -160.00-133.00   0.50    7.40    --  -86.00 -73.00   3.05   54
 58  ω    -87.00 -60.00   0.50    7.40    --  -86.00 -73.00   3.05   54
 59  ω    -90.00 -63.00   0.50    7.40    --  -90.00 -71.00 161.19   54
 60  ω    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00 -30.00   56
 61  ω    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00-180.00   56
 62  ω   -159.00-131.00   0.50    7.40    --  -90.25 -77.00 -30.00   56
 63  ω    -90.00 -65.00   0.50    7.40    --  -90.25 -68.00 -54.36   50
 64  ω    -87.00 -62.00   0.50    7.40    --  -90.25 -75.00  66.30   50
 65  ω    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00  30.00   56
 66  ω   -114.00 -63.00   0.50    7.40    --  -90.25 -77.00 120.00  102
 67  ω    -90.00 -63.00   0.50    7.40    --  -90.25 -73.00-174.33   54
 68  ω    -88.00 -61.00   0.50    7.40    --  -90.25 -77.00 -60.00   54
 69  ω    -89.00 -62.00   0.50    7.40    --  -90.25 -74.00 127.72   54
 70  ω    -88.00 -61.00   0.50    7.40    --  -90.25 -77.00-120.00   54
 71  ω    -91.00 -64.00   0.50    7.40    --  -90.25 -71.00  42.63   54
 72  ω    -86.00 -61.00   0.50    7.40    --  -90.25 -77.00   0.00   50
 73  ω    -91.00 -63.00   0.50    7.40    --  -90.25 -72.00  -0.09   56
 74  ω    -87.00 -62.00   0.50    7.40    --  -90.25 -76.00 -85.25   50
 75  ω   -147.00-121.00   0.50    7.40    --  -90.25 -72.00  -0.09   52
 76  ω    -90.00 -63.00   0.50    7.40    --  -90.25 -73.00-143.56   54
 77  ω     35.00 108.00   0.50    7.40    --  110.00-112.00  28.88  146
 78  ω    139.00 178.00   0.50    7.40    --  111.75  77.00 -60.00   78
 79  ω     84.00 125.00   0.50    7.40    --  111.75  77.00 -60.00   82
 80  ω    115.00 159.00   0.50    7.40    --  111.75 125.00  90.00   88
 81  ω    120.00 159.00   0.50    7.40    --  111.75 125.00 -60.00   78
 82  ω     41.00  84.00   0.50    7.40    --  111.75-125.00 -30.00   86
 83  ω     83.00 115.00   0.50    7.40    --  111.75  77.00-150.00   64
 84  ω     85.00 175.00   0.50    7.40    --  111.75  77.00   0.00  180
 85  ω     73.00 100.00   0.50    7.40    --  111.75 -94.00-150.00   54
 86  ω     88.00 173.00   0.50    7.40    --  111.75  61.00 120.00  170
 87  ω     41.00  68.00   0.50    7.40    --  111.75 -94.00-150.00   54
 88  ω     42.00  71.00   0.50    7.40    --  111.75 -61.00  30.00   58
 89  ω     88.00 173.00   0.50    7.40    --  111.75  61.00-120.00  170
 90  ω     89.00 147.00   0.50    7.40    --  111.75  61.00 -90.00  116
 91  ω     78.00 105.00   0.50    7.40    --  111.75 -77.00 150.00   54
 92  ω     93.00 125.00   0.50    7.40    --  111.75  45.00  60.00   64
 93  ω     42.00 105.00   0.50    7.40    --  111.75-125.00   0.00  126
 94  ω     71.00 104.00   0.50    7.40    --  111.75 -77.00-120.00   66
 95  ω     90.00 167.00   0.50    7.40    --  111.75  61.00 -60.00  154
 96  ω     44.00  78.00   0.50    7.40    --  111.75-114.00  41.78   68
 97  ω    121.00 174.00   0.50    7.40    --  111.75  77.00  30.00  106
 98  ω     88.00 116.00   0.50    7.40    --  111.75  77.00  30.00   56
 99  ω     55.00 106.00   0.50    7.40    --  111.75 -94.00  60.00  102
100  ω    130.00 178.00   0.50    7.40    --  111.75  77.00 -90.00   96
101  ω     85.00 115.00   0.50    7.40    --  111.75  77.00 -90.00   60
102  ω     80.00 106.00   0.50    7.40    --  111.75 -94.00 -60.00   52
103  ω    130.00 162.00   0.50    7.40    --  111.75  61.00 -30.00   64
104  ω     43.00  69.00   0.50    7.40    --  111.75 -61.00 -90.00   52
105  ω    131.00 158.00   0.50    7.40    --  111.75  15.00   0.00   54
106  ω     40.00  67.00   0.50    7.40    --  111.75 -94.00 -60.00   54
107  ω     38.00  63.00   0.50    7.40    --  111.75 -61.00 -30.00   50
108  ω     44.00  69.00   0.50    7.40    --  111.75 -61.00   0.00   50
109  ω     87.00 112.00   0.50    7.40    --  111.75  15.00   0.00   50
110  ω     89.00 175.00   0.50    7.40    --  111.75  61.00-150.00  172
111  ω     39.00  99.00   0.50    7.40    --  111.75 -77.00  90.00  120
112  ω     38.00  75.00   0.50    7.40    --  111.75 -77.00 150.00   74
113  ω    129.00 157.00   0.50    7.40    --  111.75  15.00-180.00   56
114  ω     85.00 135.00   0.50    7.40    --  111.75  77.00-120.00  100
115  ω     90.00 123.00   0.50    7.40    --  111.75  61.00 -30.00   66
116  ω     62.00 108.00   0.50    7.40    --  111.75  15.00-180.00   92
117  ω    121.00 148.00   0.50    7.40    --  111.75-177.00 178.98   54
118  ω     66.00 105.00   0.50    7.40    --  111.75-177.00 178.98   78
119  ω    153.00 178.00   0.50    7.40    --  111.75  61.00-180.00   50
120  ω     91.00 139.00   0.50    7.40    --  111.75  61.00 150.00   96
121  ω     65.00 106.00   0.50    7.40    --  111.75 -94.00  90.00   82
122  ω     43.00  68.00   0.50    7.40    --  111.75 -61.00-120.00   50
123  ω     83.00 157.00   0.50    7.40    --  111.75  77.00  60.00  148
124  ω     92.00 133.00   0.50    7.40    --  111.75  61.00-180.00   82
125  ω     85.00 174.00   0.50    7.40    --  111.75  71.00  81.25  178
126  ω    140.00 177.00   0.50    7.40    --  111.75  77.00 -30.00   74
127  ω     85.00 112.00   0.50    7.40    --  111.75  77.00 -30.00   54
128  ω    124.00 170.00   0.50    7.40    --  111.75  45.00-180.00   92
129  ω     92.00 136.00   0.50    7.40    --  111.75  45.00   0.00   88
130  ω     41.00 100.00   0.50    7.40    --  111.75 -94.00-120.00  118
131  ω    117.00 175.00   0.50    7.40    --  111.75  77.00 150.00  116
132  ω    139.00 166.00   0.50    7.40    --  111.75  77.00-180.00   54
133  ω     88.00 134.00   0.50    7.40    --  111.75  77.00-180.00   92
134  ω     83.00 113.00   0.50    7.40    --  111.75  77.00 150.00   60
135  ω    129.00 156.00   0.50    7.40    --  111.75  77.00  90.00   54
136  ω     98.00 126.00   0.50    7.40    --  111.75  45.00 150.00   56
137  ω     86.00 113.00   0.50    7.40    --  111.75  77.00  90.00   54
138  ω     89.00 155.00   0.50    7.40    --  111.75  61.00  60.00  132
139  ω     82.00 112.00   0.50    7.40    --  111.75-125.00 -90.00   60
140  ω    118.00 148.00   0.50    7.40    --  111.75 125.00-120.00   60
141  ω     79.00 111.00   0.50    7.40    --  111.75-125.00-150.00   64
142  ω    142.00 168.00   0.50    7.40    --  111.75  61.00  30.00   52
143  ω     61.00 102.00   0.50    7.40    --  111.75 -94.00 120.00   82
144  ω     72.00  97.00   0.50    7.40    --  111.75 -77.00 -60.00   50
145  ω     96.00 160.00   0.50    7.40    --  111.75  61.00   0.00  128
146  ω     88.00 115.00   0.50    7.40    --  111.75  61.00  30.00   54
147  ω     41.00  66.00   0.50    7.40    --  111.75-125.00 -90.00   50
148  ω     42.00  95.00   0.50    7.40    --  111.75 -77.00  30.00  106
149  ω     38.00  63.00   0.50    7.40    --  111.75 -61.00 120.00   50
150  ω    126.00 172.00   0.50    7.40    --  111.75  77.00-150.00   92
;
_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      0.0920977000
_diffrn_orient_matrix_UB_12      0.0278304000
_diffrn_orient_matrix_UB_13      -0.0895335000
_diffrn_orient_matrix_UB_21      0.1146551000
_diffrn_orient_matrix_UB_22      0.1104642000
_diffrn_orient_matrix_UB_23      0.0447875000
_diffrn_orient_matrix_UB_31      0.3086289000
_diffrn_orient_matrix_UB_32      -0.0407468000
_diffrn_orient_matrix_UB_33      0.0196271000
_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                3224
_reflns_number_total             3664
_reflns_odcompleteness_completeness 92.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     83.67
_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 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (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         0.954
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.076
_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)+(0.0555P)²+1.3675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C14(H14), C3(H3), C5(H5), C18(H18), C6(H6), C16(H16)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_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
I7 I -0.42527(7) 0.05471(2) 0.37867(2) 0.05303(14) Uani 1 1 d . . . . .
O21 O 0.4839(7) 0.2011(2) 0.7056(2) 0.0504(7) Uani 1 1 d . . . . .
H21 H 0.352984 0.225797 0.673746 0.076 Uiso 1 1 calc R U . . .
O20 O 0.5592(7) 0.3689(2) 0.7664(2) 0.0543(8) Uani 1 1 d . . . . .
O10 O -0.2238(8) 0.5642(3) 0.6346(2) 0.0586(8) Uani 1 1 d . . . . .
N2 N 0.0648(8) 0.2600(3) 0.5911(2) 0.0424(7) Uani 1 1 d . . . . .
N8 N 0.0897(8) 0.4333(3) 0.6495(2) 0.0441(8) Uani 1 1 d . . . . .
H8 H 0.255296 0.419178 0.678335 0.053 Uiso 1 1 calc R U . . .
C1 C -0.0399(9) 0.3547(3) 0.5853(3) 0.0410(8) Uani 1 1 d . . . . .
C9 C -0.0125(10) 0.5313(3) 0.6732(3) 0.0452(9) Uani 1 1 d . . . . .
C4 C -0.2634(9) 0.1875(3) 0.4664(3) 0.0435(9) Uani 1 1 d . . . . .
C14 C 0.9805(10) 0.3145(3) 0.8958(3) 0.0458(9) Uani 1 1 d . . . . .
H14 H 0.939178 0.386403 0.897990 0.055 Uiso 1 1 calc R U . . .
C13 C 0.8359(9) 0.2410(3) 0.8293(3) 0.0415(9) Uani 1 1 d . . . . .
C17 C 1.1027(10) 0.1037(4) 0.8881(3) 0.0486(10) Uani 1 1 d . . . . .
C19 C 0.6130(10) 0.2766(3) 0.7644(3) 0.0450(9) Uani 1 1 d . . . . .
C3 C -0.0454(10) 0.1786(3) 0.5325(3) 0.0439(9) Uani 1 1 d . . . . .
H3 H 0.029696 0.111711 0.536583 0.053 Uiso 1 1 calc R U . . .
C5 C -0.3726(10) 0.2861(4) 0.4605(3) 0.0475(10) Uani 1 1 d . . . . .
H5 H -0.523364 0.294520 0.415659 0.057 Uiso 1 1 calc R U . . .
C18 C 0.8985(10) 0.1356(4) 0.8257(3) 0.0478(10) Uani 1 1 d . . . . .
H18 H 0.800979 0.085137 0.780366 0.057 Uiso 1 1 calc R U . . .
C15 C 1.1833(10) 0.2846(4) 0.9587(3) 0.0492(10) Uani 1 1 d . . . . .
C6 C -0.2608(10) 0.3698(3) 0.5194(3) 0.0476(10) Uani 1 1 d . . . . .
H6 H -0.331238 0.437490 0.516065 0.057 Uiso 1 1 calc R U . . .
C16 C 1.2409(10) 0.1785(4) 0.9537(3) 0.0509(10) Uani 1 1 d . . . . .
H16 H 1.379290 0.157099 0.996656 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1568(12) 0.5907(4) 0.7542(4) 0.0580(12) Uani 1 1 d . . . . .
H11A H 0.371965 0.586949 0.747793 0.070 Uiso 1 1 calc R U . . .
H11B H 0.111023 0.556351 0.806379 0.070 Uiso 1 1 calc R U . . .
C23 C 1.1718(14) -0.0105(4) 0.8830(4) 0.0678(14) Uani 1 1 d . . . . .
H23A H 1.127573 -0.036709 0.938299 0.102 Uiso 1 1 calc R U . . .
H23B H 1.382300 -0.017175 0.874168 0.102 Uiso 1 1 calc R U . . .
H23C H 1.050190 -0.051569 0.833316 0.102 Uiso 1 1 calc R U . . .
C22 C 1.3418(13) 0.3640(5) 1.0302(4) 0.0665(13) Uani 1 1 d . . . . .
H22A H 1.553309 0.370218 1.020780 0.100 Uiso 1 1 calc R U . . .
H22B H 1.317861 0.341198 1.088119 0.100 Uiso 1 1 calc R U . . .
H22C H 1.257451 0.432312 1.028232 0.100 Uiso 1 1 calc R U . . .
C12 C 0.0858(15) 0.7054(4) 0.7709(4) 0.0667(14) Uani 1 1 d . . . . .
H12A H 0.143065 0.741228 0.721337 0.100 Uiso 1 1 calc R U . . .
H12B H 0.196078 0.739121 0.825809 0.100 Uiso 1 1 calc R U . . .
H12C H -0.127587 0.709913 0.776224 0.100 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
I7 C4 2.092(4) . ?
O21 C19 1.313(5) . ?
O20 C19 1.222(5) . ?
O10 C9 1.211(5) . ?
N2 C1 1.342(5) . ?
N2 C3 1.334(5) . ?
N8 C1 1.387(6) . ?
N8 C9 1.380(5) . ?
C1 C6 1.403(6) . ?
C9 C11 1.501(7) . ?
C4 C3 1.377(6) . ?
C4 C5 1.397(6) . ?
C14 C13 1.393(6) . ?
C14 C15 1.384(6) . ?
C13 C19 1.493(6) . ?
C13 C18 1.396(6) . ?
C17 C18 1.392(6) . ?
C17 C16 1.383(7) . ?
C17 C23 1.512(7) . ?
C5 C6 1.360(7) . ?
C15 C16 1.396(7) . ?
C15 C22 1.506(7) . ?
C11 C12 1.522(7) . ?

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 118.8(4) . . ?
C9 N8 C1 127.1(4) . . ?
N2 C1 N8 113.8(4) . . ?
N2 C1 C6 121.6(4) . . ?
N8 C1 C6 124.6(4) . . ?
O10 C9 N8 123.5(4) . . ?
O10 C9 C11 123.5(4) . . ?
N8 C9 C11 113.0(4) . . ?
C3 C4 I7 119.9(3) . . ?
C3 C4 C5 118.4(4) . . ?
C5 C4 I7 121.7(3) . . ?
C15 C14 C13 121.0(4) . . ?
C14 C13 C19 119.1(4) . . ?
C14 C13 C18 119.4(4) . . ?
C18 C13 C19 121.5(4) . . ?
C18 C17 C23 120.1(5) . . ?
C16 C17 C18 118.7(4) . . ?
C16 C17 C23 121.2(4) . . ?
O21 C19 C13 114.5(4) . . ?
O20 C19 O21 123.6(4) . . ?
O20 C19 C13 121.9(4) . . ?
N2 C3 C4 122.8(4) . . ?
C6 C5 C4 119.3(4) . . ?
C17 C18 C13 120.5(4) . . ?
C14 C15 C16 118.3(4) . . ?
C14 C15 C22 121.2(4) . . ?
C16 C15 C22 120.5(4) . . ?
C5 C6 C1 119.0(4) . . ?
C17 C16 C15 122.0(4) . . ?
C9 C11 C12 113.3(4) . . ?

_olex2_date_sample_data_collection 2021-06-22
_olex2_date_sample_submission    2021-06-22
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_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 3.314
_oxdiff_exptl_absorpt_empirical_full_min 0.628
####################################################################### 
# 
# 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_Br-Et_35M-BA
_database_code_depnum_ccdc_archive 'CCDC 2092017'
loop_
_audit_author_name
_audit_author_address
'Christer B. Aakeroy'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-21
_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         'C8 H9 Br N2 O, C9 H10 O2'
_chemical_formula_sum            'C17 H19 Br N2 O3'
_chemical_formula_weight         379.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H19 Br1 N2 O3'
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                   4.7003(3)
_cell_length_b                   12.7927(5)
_cell_length_c                   14.1635(6)
_cell_angle_alpha                97.664(3)
_cell_angle_beta                 93.157(5)
_cell_angle_gamma                91.561(4)
_cell_volume                     842.24(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4204
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.9120
_cell_measurement_theta_min      3.1430
_shelx_estimated_absorpt_T_max   0.774
_shelx_estimated_absorpt_T_min   0.161
_exptl_absorpt_coefficient_mu    3.467
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72908
_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    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_preparation       'grown from 1:1 mixture'
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9084
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.194
_diffrn_reflns_theta_min         3.154
_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 0.992
_diffrn_measured_fraction_theta_max 0.945
_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  70.00   0.50    0.05    --   47.70  63.00 129.00   68
  2  ω     88.00 117.00   0.50    0.05    --   47.70  63.00 129.00   58
  3  ω    102.00 139.00   0.50    0.14    --  107.74 125.00 -60.00   74
  4  ω     42.00 118.00   0.50    0.05    --   47.70  57.00 -60.00  152
  5  ω     39.00  65.00   0.50    0.05    --   47.70 -63.00  -7.00   52
  6  ω     -7.00  32.00   0.50    0.05    --   47.70 -63.00  -7.00   78
  7  ω     40.00  74.00   0.50    0.14    --  107.74 -99.00 120.00   68
  8  ω     84.00 111.00   0.50    0.14    --  107.74-125.00 150.00   54
  9  ω     35.00  61.00   0.50    0.14    --  107.74-125.00 150.00   52
 10  ω     64.00 103.00   0.50    0.14    --  107.74-125.00  90.00   78
 11  ω     81.00 106.00   0.50    0.14    --  107.74 -99.00 120.00   50
 12  ω     81.00 106.00   0.50    0.14    --  107.74 -99.00  60.00   50
 13  ω     65.00 111.00   0.50    0.14    --  107.74-125.00   0.00   92
 14  ω     38.00 104.00   0.50    0.14    --  107.74 -99.00 -30.00  132
 15  ω     35.00  99.00   0.50    0.14    --  107.74 -99.00-150.00  128
 16  ω     36.00  82.00   0.50    0.14    --  107.74 -99.00-180.00   92
 17  ω     39.00 100.00   0.50    0.14    --  107.74 -77.00-150.00  122
 18  ω     78.00 103.00   0.50    0.14    --  107.74 -77.00-120.00   50
 19  ω     49.00  75.00   0.50    0.14    --  107.74 -77.00-120.00   52
 20  ω     38.00  64.00   0.50    0.14    --  107.74 -57.00-120.00   52
 21  ω     79.00 104.00   0.50    0.14    --  107.74 -77.00 -30.00   50
 22  ω     35.00  63.00   0.50    0.14    --  107.74 -57.00 -30.00   56
 23  ω     35.00  60.00   0.50    0.14    --  107.74 -63.00  -7.00   50
 24  ω     37.00  62.00   0.50    0.14    --  107.74 -57.00 150.00   50
 25  ω    113.00 178.00   0.50    0.14    --  107.74  38.00  30.00  130
 26  ω     93.00 165.00   0.50    0.14    --  107.74  57.00  60.00  144
 27  ω     92.00 176.00   0.50    0.14    --  107.74  63.00 129.00  168
 28  ω    111.00 162.00   0.50    0.14    --  107.74  38.00 -60.00  102
 29  ω    -26.00  25.00   0.50    0.05    --  -47.70  19.00 120.00  102
 30  ω    -16.00  25.00   0.50    0.05    --  -47.70  63.00 129.00   82
 31  ω    -62.00 -30.00   0.50    0.05    --  -47.70  63.00 129.00   64
 32  ω    -68.00 -43.00   0.50    0.14    --  -86.25  63.00 129.00   50
 33  ω    -62.00 -16.00   0.50    0.14    --  -86.25  57.00 120.00   92
 34  ω    -43.00 -18.00   0.50    0.14    --  -86.25  38.00  60.00   50
 35  ω    -66.00 -22.00   0.50    0.14    --  -86.25  57.00 -60.00   88
 36  ω    -43.00 -18.00   0.50    0.14    --  -86.25  38.00-120.00   50
 37  ω    -39.00 -14.00   0.50    0.14    --  -86.25  38.00-150.00   50
 38  ω    -67.00 -30.00   0.50    0.05    --  -47.70 -63.00  -7.00   74
 39  ω   -122.00 -80.00   0.50    0.14    --  -86.25 -63.00  -7.00   84
 40  ω   -113.00 -83.00   0.50    0.05    --  -47.70 -63.00  -7.00   60
 41  ω   -140.00 -94.00   0.50    0.14    --  -86.25 -99.00  90.00   92
;
_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      -0.0325501000
_diffrn_orient_matrix_UB_12      0.1057571000
_diffrn_orient_matrix_UB_13      -0.0396366000
_diffrn_orient_matrix_UB_21      -0.2423556000
_diffrn_orient_matrix_UB_22      -0.0499786000
_diffrn_orient_matrix_UB_23      -0.0707108000
_diffrn_orient_matrix_UB_31      -0.2192885000
_diffrn_orient_matrix_UB_32      0.0331743000
_diffrn_orient_matrix_UB_33      0.0742735000
_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                3072
_reflns_number_total             3358
_reflns_odcompleteness_completeness 99.44
_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         1.135
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1064P)²+0.1332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C18(H18), C5(H5), C6(H6), C3(H3), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_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
Br7 Br 0.58059(7) 0.05209(2) 0.38155(2) 0.03285(18) Uani 1 1 d . . . . .
O21 O 0.4758(5) 0.19546(18) 0.70192(16) 0.0292(5) Uani 1 1 d . . . . .
H21 H 0.350265 0.220099 0.667419 0.044 Uiso 1 1 calc R U . . .
O10 O 0.7712(5) 0.56144(18) 0.62925(17) 0.0324(5) Uani 1 1 d . . . . .
O20 O 0.5430(5) 0.36547(17) 0.76386(16) 0.0299(5) Uani 1 1 d . . . . .
N2 N 1.0551(6) 0.2518(2) 0.58648(19) 0.0266(5) Uani 1 1 d . . . . .
N8 N 1.0763(5) 0.4269(2) 0.64414(19) 0.0258(5) Uani 1 1 d . . . . .
H8 H 1.239586 0.412443 0.672141 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7234(7) 0.1748(3) 0.4621(2) 0.0266(6) Uani 1 1 d . . . . .
C18 C 0.8947(7) 0.1309(3) 0.8232(2) 0.0274(6) Uani 1 1 d . . . . .
H18 H 0.794850 0.079257 0.777997 0.033 Uiso 1 1 calc R U . . .
C5 C 0.6064(7) 0.2736(3) 0.4551(2) 0.0276(6) Uani 1 1 d . . . . .
H5 H 0.452932 0.280340 0.410037 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7178(7) 0.3599(3) 0.5145(2) 0.0278(6) Uani 1 1 d . . . . .
H6 H 0.642977 0.427634 0.511123 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9789(7) 0.5276(2) 0.6688(2) 0.0261(6) Uani 1 1 d . . . . .
C3 C 0.9438(7) 0.1674(2) 0.5277(2) 0.0274(6) Uani 1 1 d . . . . .
H3 H 1.021363 0.100277 0.532000 0.033 Uiso 1 1 calc R U . . .
C14 C 0.9775(6) 0.3133(3) 0.8921(2) 0.0271(6) Uani 1 1 d . . . . .
H14 H 0.934308 0.385585 0.893257 0.033 Uiso 1 1 calc R U . . .
C17 C 1.1062(7) 0.1006(2) 0.8864(2) 0.0285(6) Uani 1 1 d . . . . .
C13 C 0.8305(6) 0.2378(2) 0.8267(2) 0.0243(6) Uani 1 1 d . . . . .
C1 C 0.9449(6) 0.3470(2) 0.5805(2) 0.0242(6) Uani 1 1 d . . . . .
C15 C 1.1877(6) 0.2847(2) 0.9561(2) 0.0272(6) Uani 1 1 d . . . . .
C11 C 1.1557(7) 0.5906(3) 0.7500(2) 0.0315(7) Uani 1 1 d . . . . .
H11A H 1.358182 0.590457 0.734189 0.038 Uiso 1 1 calc R U . . .
H11B H 1.140094 0.555809 0.808035 0.038 Uiso 1 1 calc R U . . .
C16 C 1.2460(7) 0.1768(3) 0.9517(2) 0.0290(6) Uani 1 1 d . . . . .
H16 H 1.386911 0.155786 0.995444 0.035 Uiso 1 1 calc R U . . .
C19 C 0.6024(6) 0.2727(3) 0.7615(2) 0.0266(6) Uani 1 1 d . . . . .
C23 C 1.1807(8) -0.0137(3) 0.8820(3) 0.0369(8) Uani 1 1 d . . . . .
H23A H 1.045754 -0.057164 0.836878 0.055 Uiso 1 1 calc R U . . .
H23B H 1.170169 -0.035617 0.945433 0.055 Uiso 1 1 calc R U . . .
H23C H 1.374452 -0.022686 0.860694 0.055 Uiso 1 1 calc R U . . .
C12 C 1.0651(8) 0.7044(3) 0.7715(3) 0.0358(7) Uani 1 1 d . . . . .
H12A H 1.088035 0.740338 0.715270 0.054 Uiso 1 1 calc R U . . .
H12B H 1.184264 0.740924 0.825501 0.054 Uiso 1 1 calc R U . . .
H12C H 0.864860 0.705233 0.787417 0.054 Uiso 1 1 calc R U . . .
C22 C 1.3500(8) 0.3660(3) 1.0254(2) 0.0358(7) Uani 1 1 d . . . . .
H22A H 1.485156 0.404772 0.991463 0.054 Uiso 1 1 calc R U . . .
H22B H 1.454346 0.331449 1.073726 0.054 Uiso 1 1 calc R U . . .
H22C H 1.216924 0.415326 1.056527 0.054 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
Br7 C4 1.896(3) . ?
O21 H21 0.8400 . ?
O21 C19 1.316(4) . ?
O10 C9 1.217(4) . ?
O20 C19 1.223(4) . ?
N2 C3 1.347(4) . ?
N2 C1 1.348(4) . ?
N8 H8 0.8800 . ?
N8 C9 1.386(4) . ?
N8 C1 1.377(4) . ?
C4 C5 1.406(4) . ?
C4 C3 1.367(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.399(5) . ?
C18 C13 1.404(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(5) . ?
C6 H6 0.9500 . ?
C6 C1 1.408(4) . ?
C9 C11 1.508(5) . ?
C3 H3 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.387(5) . ?
C14 C15 1.394(5) . ?
C17 C16 1.377(5) . ?
C17 C23 1.506(4) . ?
C13 C19 1.493(4) . ?
C15 C16 1.409(4) . ?
C15 C22 1.493(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.525(5) . ?
C16 H16 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O21 H21 109.5 . . ?
C3 N2 C1 118.8(3) . . ?
C9 N8 H8 116.5 . . ?
C1 N8 H8 116.5 . . ?
C1 N8 C9 127.0(3) . . ?
C5 C4 Br7 120.9(2) . . ?
C3 C4 Br7 119.7(2) . . ?
C3 C4 C5 119.4(3) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C13 119.7(3) . . ?
C13 C18 H18 120.1 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C1 119.2(3) . . ?
C1 C6 H6 120.4 . . ?
O10 C9 N8 123.4(3) . . ?
O10 C9 C11 123.5(3) . . ?
N8 C9 C11 113.0(3) . . ?
N2 C3 C4 122.4(3) . . ?
N2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 120.9(3) . . ?
C15 C14 H14 119.5 . . ?
C18 C17 C23 120.2(3) . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 C23 120.8(3) . . ?
C18 C13 C19 121.2(3) . . ?
C14 C13 C18 120.2(3) . . ?
C14 C13 C19 118.6(3) . . ?
N2 C1 N8 113.4(3) . . ?
N2 C1 C6 121.5(3) . . ?
N8 C1 C6 125.1(3) . . ?
C14 C15 C16 117.7(3) . . ?
C14 C15 C22 121.0(3) . . ?
C16 C15 C22 121.2(3) . . ?
C9 C11 H11A 109.0 . . ?
C9 C11 H11B 109.0 . . ?
C9 C11 C12 113.1(3) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C17 C16 C15 122.4(3) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
O21 C19 C13 114.1(3) . . ?
O20 C19 O21 123.9(3) . . ?
O20 C19 C13 122.0(3) . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
O21 H21 N2 0.84 1.84 2.672(3) 170.8 1_455 yes
N8 H8 O20 0.88 2.03 2.889(3) 163.8 1_655 yes
C5 H5 O10 0.95 2.42 3.110(4) 129.1 2_666 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
Br7 C4 C5 C6 -179.6(2) . . . . ?
Br7 C4 C3 N2 179.6(2) . . . . ?
O10 C9 C11 C12 -5.5(5) . . . . ?
N8 C9 C11 C12 174.9(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C18 C17 C16 C15 -1.2(5) . . . . ?
C18 C13 C19 O21 -0.8(4) . . . . ?
C18 C13 C19 O20 179.7(3) . . . . ?
C5 C4 C3 N2 -0.1(5) . . . . ?
C5 C6 C1 N2 0.1(4) . . . . ?
C5 C6 C1 N8 180.0(3) . . . . ?
C9 N8 C1 N2 -166.2(3) . . . . ?
C9 N8 C1 C6 13.9(5) . . . . ?
C3 N2 C1 N8 180.0(3) . . . . ?
C3 N2 C1 C6 -0.1(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C14 C13 C19 O21 179.9(3) . . . . ?
C14 C13 C19 O20 0.3(4) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C17 C18 C13 C14 0.5(4) . . . . ?
C17 C18 C13 C19 -178.9(3) . . . . ?
C13 C18 C17 C16 0.6(4) . . . . ?
C13 C18 C17 C23 -178.8(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C13 C14 C15 C22 178.9(3) . . . . ?
C1 N2 C3 C4 0.1(5) . . . . ?
C1 N8 C9 O10 -7.2(5) . . . . ?
C1 N8 C9 C11 172.5(3) . . . . ?
C15 C14 C13 C18 -0.9(4) . . . . ?
C15 C14 C13 C19 178.5(3) . . . . ?
C23 C17 C16 C15 178.2(3) . . . . ?
C22 C15 C16 C17 -177.8(3) . . . . ?

_olex2_date_sample_completion    2020-12-13
_olex2_date_sample_data_collection 2020-12-12
_olex2_date_sample_submission    2020-12-10
_olex2_exptl_crystal_mounting_method 'mounted on a glass fibre'
_olex2_submission_original_sample_id AA-Br-propyl-3,5-dimethyl-BA
_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 2.045
_oxdiff_exptl_absorpt_empirical_full_min 0.524
####################################################################### 
# 
# 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_I-Me_35M-BA
_database_code_depnum_ccdc_archive 'CCDC 2092009'
loop_
_audit_author_name
_audit_author_address
'Abhijeet S. Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2019-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 I N2 O, C9 H10 O2'
_chemical_formula_sum            'C16 H17 I N2 O3'
_chemical_formula_weight         412.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4358(2)
_cell_length_b                   10.5039(2)
_cell_length_c                   11.7955(3)
_cell_angle_alpha                69.3730(10)
_cell_angle_beta                 82.684(2)
_cell_angle_gamma                73.631(2)
_cell_volume                     826.87(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5245
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.47
_cell_measurement_theta_min      4.01
_shelx_estimated_absorpt_T_max   0.436
_shelx_estimated_absorpt_T_min   0.283
_exptl_absorpt_coefficient_mu    15.337
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1182 before and 0.0683 after correction. The Ratio of minimum to maximum transmission is 0.6948. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11691
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         70.173
_diffrn_reflns_theta_min         4.006
_diffrn_ambient_temperature      199.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2697
_reflns_number_total             2904
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker MicroStar'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.266
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       0.0063(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.050
_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)+(0.0599P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N8-H8
 0.88 with sigma of 0.04
 O20-H20
 0.82 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C13(H13), C15(H15), C17(H17)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6450(5) 0.2261(4) 0.7628(3) 0.0177(6) Uani 1 1 d . . . . .
N2 N 0.7263(4) 0.2231(3) 0.6549(3) 0.0213(6) Uani 1 1 d . . . . .
C3 C 0.7878(5) 0.0996(4) 0.6358(3) 0.0232(7) Uani 1 1 d . . . . .
H3 H 0.8459 0.0979 0.5596 0.028 Uiso 1 1 calc R . . . .
C4 C 0.7701(5) -0.0260(4) 0.7230(3) 0.0205(7) Uani 1 1 d . . . . .
C5 C 0.6911(5) -0.0238(4) 0.8359(3) 0.0219(7) Uani 1 1 d . . . . .
H5 H 0.6801 -0.1086 0.8979 0.026 Uiso 1 1 calc R . . . .
C6 C 0.6288(5) 0.1031(4) 0.8567(3) 0.0211(7) Uani 1 1 d . . . . .
H6 H 0.5760 0.1068 0.9336 0.025 Uiso 1 1 calc R . . . .
I7 I 0.85946(4) -0.21165(2) 0.68039(2) 0.03361(16) Uani 1 1 d . . . . .
H8 H 0.579(7) 0.428(4) 0.705(3) 0.026(11) Uiso 1 1 d D . . . .
N8 N 0.5822(4) 0.3609(3) 0.7697(3) 0.0206(6) Uani 1 1 d D . . . .
C9 C 0.4759(5) 0.4019(4) 0.8612(3) 0.0220(7) Uani 1 1 d . . . . .
O10 O 0.4374(4) 0.3194(3) 0.9574(2) 0.0322(6) Uani 1 1 d . . . . .
C11 C 0.4139(7) 0.5594(4) 0.8320(4) 0.0336(9) Uani 1 1 d . . . . .
H11A H 0.2767 0.5896 0.8366 0.050 Uiso 1 1 calc GR . . . .
H11B H 0.4588 0.6056 0.7500 0.050 Uiso 1 1 calc GR . . . .
H11C H 0.4660 0.5855 0.8904 0.050 Uiso 1 1 calc GR . . . .
C12 C 0.2029(5) 0.3319(4) 0.6407(3) 0.0210(7) Uani 1 1 d . . . . .
C13 C 0.1054(5) 0.3646(4) 0.7396(3) 0.0235(7) Uani 1 1 d . . . . .
H13 H 0.0662 0.4598 0.7371 0.028 Uiso 1 1 calc R . . . .
C14 C 0.0649(5) 0.2593(4) 0.8420(3) 0.0251(7) Uani 1 1 d . . . . .
C15 C 0.1239(5) 0.1215(4) 0.8423(3) 0.0279(8) Uani 1 1 d . . . . .
H15 H 0.0961 0.0488 0.9119 0.033 Uiso 1 1 calc R . . . .
C16 C 0.2228(5) 0.0853(4) 0.7441(4) 0.0253(7) Uani 1 1 d . . . . .
C17 C 0.2626(5) 0.1925(4) 0.6429(3) 0.0228(7) Uani 1 1 d . . . . .
H17 H 0.3303 0.1710 0.5753 0.027 Uiso 1 1 calc R . . . .
C18 C 0.2496(5) 0.4441(4) 0.5308(3) 0.0232(7) Uani 1 1 d . . . . .
O19 O 0.3374(5) 0.4198(3) 0.4432(3) 0.0387(7) Uani 1 1 d . . . . .
H20 H 0.218(9) 0.629(6) 0.478(4) 0.050(17) Uiso 1 1 d D . . . .
O20 O 0.1880(5) 0.5715(3) 0.5383(3) 0.0352(7) Uani 1 1 d D . . . .
C21 C -0.0388(7) 0.2959(5) 0.9492(4) 0.0372(9) Uani 1 1 d . . . . .
H21A H 0.0479 0.3120 0.9956 0.056 Uiso 1 1 calc GR . . . .
H21B H -0.0913 0.2182 1.0011 0.056 Uiso 1 1 calc GR . . . .
H21C H -0.1405 0.3814 0.9207 0.056 Uiso 1 1 calc GR . . . .
C22 C 0.2857(6) -0.0655(4) 0.7477(5) 0.0374(9) Uani 1 1 d . . . . .
H22A H 0.1757 -0.1009 0.7516 0.056 Uiso 1 1 calc GR . . . .
H22B H 0.3608 -0.1226 0.8194 0.056 Uiso 1 1 calc GR . . . .
H22C H 0.3616 -0.0710 0.6745 0.056 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.344(5) . ?
C1 C6 1.399(5) . ?
C1 N8 1.388(4) . ?
N2 C3 1.337(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(5) . ?
C4 C5 1.391(5) . ?
C4 I7 2.090(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(5) . ?
C6 H6 0.9500 . ?
N8 H8 0.83(3) . ?
N8 C9 1.376(5) . ?
C9 O10 1.219(5) . ?
C9 C11 1.509(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.389(5) . ?
C12 C17 1.397(5) . ?
C12 C18 1.493(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(5) . ?
C14 C15 1.388(6) . ?
C14 C21 1.506(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.402(6) . ?
C16 C17 1.389(5) . ?
C16 C22 1.507(5) . ?
C17 H17 0.9500 . ?
C18 O19 1.216(5) . ?
C18 O20 1.317(5) . ?
O20 H20 0.81(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C6 121.7(3) . . ?
N2 C1 N8 113.3(3) . . ?
N8 C1 C6 124.9(3) . . ?
C3 N2 C1 119.0(3) . . ?
N2 C3 H3 118.8 . . ?
N2 C3 C4 122.5(3) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 I7 119.3(2) . . ?
C5 C4 I7 122.1(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(3) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C1 N8 H8 117(3) . . ?
C9 N8 C1 127.9(3) . . ?
C9 N8 H8 112(3) . . ?
N8 C9 C11 113.5(3) . . ?
O10 C9 N8 123.5(3) . . ?
O10 C9 C11 122.9(3) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.6(3) . . ?
C13 C12 C18 121.0(3) . . ?
C17 C12 C18 118.4(3) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C21 120.0(4) . . ?
C15 C14 C13 118.2(3) . . ?
C15 C14 C21 121.8(3) . . ?
C14 C15 H15 118.7 . . ?
C14 C15 C16 122.6(3) . . ?
C16 C15 H15 118.7 . . ?
C15 C16 C22 121.2(4) . . ?
C17 C16 C15 118.2(3) . . ?
C17 C16 C22 120.6(4) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
O19 C18 C12 123.1(3) . . ?
O19 C18 O20 123.3(3) . . ?
O20 C18 C12 113.6(3) . . ?
C18 O20 H20 111(5) . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
N8 H8 O19 0.83(3) 2.08(4) 2.879(4) 161(5) 2_666
O20 H20 N2 0.81(4) 1.87(4) 2.683(4) 174(7) 2_666


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Br-Et_BA
_database_code_depnum_ccdc_archive 'CCDC 2103264'
loop_
_audit_author_name
_audit_author_address
'Christer B. Aakeroy'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-25
_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         'C8 H9 Br N2 O, C7 H6 O2'
_chemical_formula_sum            'C15 H15 Br N2 O3'
_chemical_formula_weight         351.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   14.0457(6)
_cell_length_b                   4.9964(3)
_cell_length_c                   21.3687(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.928(3)
_cell_angle_gamma                90
_cell_volume                     1499.41(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4526
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.3290
_cell_measurement_theta_min      3.7220
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.681
_exptl_absorpt_coefficient_mu    3.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.111a (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    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crystallized from ethyl acetate'
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.353
_diffrn_reflns_theta_min         3.738
_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 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -61.00   0.50   17.73    --  -43.05-147.00 103.00   94
  2  ω    -83.00 -14.00   0.50   17.73    --  -43.05 124.00 -12.00  138
  3  ω     41.00  66.00   0.50   17.73    --   43.05-124.00 -90.00   50
  4  ω     78.00 103.00   0.50   17.73    --   43.05-147.00 103.00   50
  5  ω   -134.00 -76.00   0.50   70.93    --  -90.25-124.00 -90.00  116
  6  ω    -87.00 -62.00   0.50   70.93    --  -90.25 147.00 153.00   50
  7  ω    100.00 126.00   0.50   70.93    --  111.75 147.00 153.00   52
  8  ω     98.00 124.00   0.50   70.93    --  111.75 124.00 -12.00   52
  9  ω     78.00 111.00   0.50   70.93    --  111.75-124.00 -90.00   66
 10  ω     73.00 126.00   0.50   70.93    --  111.75-147.00 103.00  106
 11  ω   -118.00 -85.00   0.50   17.73    --  -43.05-178.00-180.00   66
 12  ω    -38.00  33.00   0.50   17.73    --  -43.05  38.00 120.00  142
 13  ω    -17.00  26.00   0.50   17.73    --   43.05 -19.00 150.00   86
 14  ω    -36.00  25.00   0.50   17.73    --   43.05 -19.00 -90.00  122
 15  ω     84.00 112.00   0.50   70.93    --  111.75-125.00 -60.00   56
 16  ω     92.00 118.00   0.50   70.93    --  111.75  77.00 -30.00   52
 17  ω    126.00 178.00   0.50   70.93    --  111.75  77.00  60.00  104
 18  ω     80.00 105.00   0.50   70.93    --  111.75 -94.00 -60.00   50
 19  ω     99.00 124.00   0.50   70.93    --  111.75 125.00-120.00   50
 20  ω     47.00  83.00   0.50   70.93    --  111.75 -77.00 -60.00   72
 21  ω    103.00 128.00   0.50   70.93    --  111.75  45.00-120.00   50
 22  ω     70.00 103.00   0.50   70.93    --  111.75 -77.00  30.00   66
 23  ω     39.00  65.00   0.50   70.93    --  111.75 -59.00 -15.46   52
 24  ω     82.00 108.00   0.50   70.93    --  111.75-110.00 -56.09   52
 25  ω     73.00  99.00   0.50   70.93    --  111.75 -94.00-150.00   52
 26  ω     73.00 100.00   0.50   70.93    --  111.75 -77.00 -30.00   54
 27  ω     78.00 104.00   0.50   70.93    --  111.75 -94.00 -30.00   52
 28  ω     70.00 102.00   0.50   70.93    --  111.75  15.00   0.00   64
 29  ω    118.00 178.00   0.50   70.93    --  111.75  15.00   0.00  120
 30  ω     42.00  70.00   0.50   70.93    --  111.75 -61.00-180.00   56
 31  ω     45.00  70.00   0.50   70.93    --  111.75 -61.00 150.00   50
 32  ω    122.00 155.00   0.50   70.93    --  111.75  45.00-150.00   66
 33  ω    153.00 178.00   0.50   70.93    --  111.75  77.00 -30.00   50
 34  ω    130.00 173.00   0.50   70.93    --  111.75  45.00-120.00   86
 35  ω     41.00  99.00   0.50   70.93    --  111.75 -94.00 -83.65  116
 36  ω     70.00 104.00   0.50   70.93    --  111.75 -77.00  90.00   68
 37  ω     42.00  67.00   0.50   70.93    --  111.75 -96.00 -62.29   50
 38  ω     46.00  86.00   0.50   70.93    --  111.75-125.00  60.00   80
 39  ω     97.00 122.00   0.50   70.93    --  111.75  77.00  60.00   50
 40  ω    108.00 140.00   0.50   70.93    --  111.75  61.00  30.00   64
 41  ω    111.00 137.00   0.50   70.93    --  111.75  61.00  60.00   52
 42  ω    139.00 165.00   0.50   70.93    --  111.75 136.00  74.49   52
 43  ω     97.00 123.00   0.50   70.93    --  111.75  74.00-104.15   52
 44  ω    148.00 177.00   0.50   70.93    --  111.75  74.00-104.15   58
 45  ω    131.00 158.00   0.50   70.93    --  111.75 124.00 -12.00   54
;
_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      -0.0775407000
_diffrn_orient_matrix_UB_12      -0.1887418000
_diffrn_orient_matrix_UB_13      -0.0263798000
_diffrn_orient_matrix_UB_21      -0.0647415000
_diffrn_orient_matrix_UB_22      0.2425319000
_diffrn_orient_matrix_UB_23      -0.0138196000
_diffrn_orient_matrix_UB_31      0.0428466000
_diffrn_orient_matrix_UB_32      0.0249692000
_diffrn_orient_matrix_UB_33      -0.0656438000
_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                2338
_reflns_number_total             3137
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (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  (Sheldrick, 2015)'
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.022
_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)+(0.0665P)²+0.7429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1300
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C3(H3), C18(H18), C14(H14), C6(H6), C17(H17), C5(H5), C16(H16),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_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
Br7 Br 0.13950(3) 0.02579(10) 0.47917(2) 0.06556(18) Uani 1 1 d . . . . .
O20 O 0.51574(15) 0.4117(5) 0.71762(11) 0.0527(5) Uani 1 1 d . . . . .
O21 O 0.36738(16) 0.5356(5) 0.69247(10) 0.0523(5) Uani 1 1 d . . . . .
H21 H 0.372538 0.413050 0.665820 0.078 Uiso 1 1 calc R U . . .
O10 O 0.59424(18) -0.3595(6) 0.58272(11) 0.0608(6) Uani 1 1 d . . . . .
N8 N 0.5106(2) -0.0062(5) 0.62128(12) 0.0497(6) Uani 1 1 d . . . . .
H8 H 0.513616 0.122369 0.649399 0.060 Uiso 1 1 calc R U . . .
N2 N 0.36194(19) 0.1630(6) 0.60223(12) 0.0501(6) Uani 1 1 d . . . . .
C13 C 0.4428(2) 0.7546(7) 0.77699(13) 0.0441(6) Uani 1 1 d . . . . .
C19 C 0.4463(2) 0.5503(7) 0.72645(14) 0.0450(7) Uani 1 1 d . . . . .
C1 C 0.4275(2) -0.0177(6) 0.58570(14) 0.0463(7) Uani 1 1 d . . . . .
C4 C 0.2582(2) -0.0026(7) 0.52239(14) 0.0496(7) Uani 1 1 d . . . . .
C3 C 0.2790(2) 0.1697(8) 0.57069(14) 0.0527(7) Uani 1 1 d . . . . .
H3 H 0.232675 0.298576 0.582154 0.063 Uiso 1 1 calc R U . . .
C9 C 0.5889(2) -0.1694(7) 0.61833(14) 0.0494(7) Uani 1 1 d . . . . .
C18 C 0.3648(2) 0.9247(7) 0.78281(14) 0.0479(7) Uani 1 1 d . . . . .
H18 H 0.312450 0.911842 0.754249 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5189(2) 0.7739(7) 0.81939(15) 0.0521(7) Uani 1 1 d . . . . .
H14 H 0.572082 0.657915 0.815661 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4102(3) -0.2027(7) 0.53750(14) 0.0532(8) Uani 1 1 d . . . . .
H6 H 0.456628 -0.332957 0.527167 0.064 Uiso 1 1 calc R U . . .
C17 C 0.3640(2) 1.1130(8) 0.83060(15) 0.0519(7) Uani 1 1 d . . . . .
H17 H 0.311186 1.230238 0.834586 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3247(3) -0.1915(8) 0.50558(14) 0.0535(8) Uani 1 1 d . . . . .
H5 H 0.311454 -0.312498 0.472267 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6686(2) -0.0887(8) 0.66251(16) 0.0566(8) Uani 1 1 d . . . . .
H11A H 0.701984 0.067779 0.644809 0.068 Uiso 1 1 calc R U . . .
H11B H 0.641021 -0.032895 0.702807 0.068 Uiso 1 1 calc R U . . .
C16 C 0.4403(3) 1.1300(8) 0.87255(15) 0.0560(8) Uani 1 1 d . . . . .
H16 H 0.439470 1.258518 0.905312 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5170(3) 0.9614(8) 0.86680(16) 0.0585(9) Uani 1 1 d . . . . .
H15 H 0.569047 0.973945 0.895615 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7399(3) -0.3082(9) 0.67469(19) 0.0649(9) Uani 1 1 d . . . . .
H12A H 0.764572 -0.372903 0.634802 0.097 Uiso 1 1 calc R U . . .
H12B H 0.709033 -0.456046 0.696649 0.097 Uiso 1 1 calc R U . . .
H12C H 0.792595 -0.238657 0.700555 0.097 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
Br7 C4 1.899(3) . ?
O20 C19 1.213(4) . ?
O21 C19 1.317(4) . ?
O10 C9 1.220(4) . ?
N8 C1 1.385(4) . ?
N8 C9 1.372(4) . ?
N2 C1 1.341(4) . ?
N2 C3 1.337(4) . ?
C13 C19 1.487(4) . ?
C13 C18 1.394(5) . ?
C13 C14 1.393(4) . ?
C1 C6 1.402(5) . ?
C4 C3 1.372(5) . ?
C4 C5 1.379(5) . ?
C9 C11 1.507(5) . ?
C18 C17 1.389(5) . ?
C14 C15 1.380(5) . ?
C6 C5 1.372(5) . ?
C17 C16 1.389(5) . ?
C11 C12 1.505(5) . ?
C16 C15 1.375(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N8 C1 128.3(3) . . ?
C3 N2 C1 118.7(3) . . ?
C18 C13 C19 121.2(3) . . ?
C14 C13 C19 119.0(3) . . ?
C14 C13 C18 119.7(3) . . ?
O20 C19 O21 123.6(3) . . ?
O20 C19 C13 122.7(3) . . ?
O21 C19 C13 113.6(3) . . ?
N8 C1 C6 124.4(3) . . ?
N2 C1 N8 113.8(3) . . ?
N2 C1 C6 121.7(3) . . ?
C3 C4 Br7 119.5(3) . . ?
C3 C4 C5 119.3(3) . . ?
C5 C4 Br7 121.2(2) . . ?
N2 C3 C4 122.4(3) . . ?
O10 C9 N8 123.3(3) . . ?
O10 C9 C11 123.1(3) . . ?
N8 C9 C11 113.6(3) . . ?
C17 C18 C13 119.6(3) . . ?
C15 C14 C13 120.1(3) . . ?
C5 C6 C1 118.5(3) . . ?
C16 C17 C18 120.1(3) . . ?
C6 C5 C4 119.3(3) . . ?
C12 C11 C9 113.5(3) . . ?
C15 C16 C17 120.2(3) . . ?
C16 C15 C14 120.4(3) . . ?


_olex2_date_sample_data_collection 2021-06-23
_olex2_date_sample_submission    2021-06-23
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_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 2.357
_oxdiff_exptl_absorpt_empirical_full_min 0.574
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H-Et_4Cl-BA
_database_code_depnum_ccdc_archive 'CCDC 2092015'
loop_
_audit_author_name
_audit_author_address
'Boris B Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_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         'C7 H5 Cl O2, C8 H10 N2 O'
_chemical_formula_sum            'C15 H15 Cl N2 O3'
_chemical_formula_weight         306.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H15 N2 O3 Cl'
_chemical_oxdiff_usercomment     'redo experiment 42 at 200K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.3651(2)
_cell_length_b                   4.47304(5)
_cell_length_c                   21.7942(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.2128(14)
_cell_angle_gamma                90
_cell_volume                     1438.32(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9567
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      77.2250
_cell_measurement_theta_min      3.1160
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.485
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67801
_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    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crystallized from ethylacetate'
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13927
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.583
_diffrn_reflns_theta_min         3.146
_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 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  36.00   0.50    5.00    --   47.95 -54.00  11.00   66
  2  ω     36.00  62.00   0.50   25.00    --  107.75 -54.00  11.00   52
  3  ω     69.00  99.00   0.50   25.00    --  107.75 -77.00   0.00   60
  4  ω     72.00 103.00   0.50   25.00    --  107.75 -77.00  60.00   62
  5  ω     65.00 104.00   0.50   25.00    --  107.75 -94.00   0.00   78
  6  ω     69.00  95.00   0.50   25.00    --  107.75 -94.00 -30.00   52
  7  ω     61.00  87.00   0.50   25.00    --  107.75 -77.00 -90.00   52
  8  ω     66.00  92.00   0.50   25.00    --  107.75 -77.00-150.00   52
  9  ω     44.00  70.00   0.50   25.00    --  107.75 -61.00 -90.00   52
 10  ω     40.00  90.00   0.50   25.00    --  107.75 -77.00 -30.00  100
 11  ω     41.00  70.00   0.50   25.00    --  107.75 -61.00  60.00   58
 12  ω     42.00  71.00   0.50   25.00    --  107.75 -61.00  90.00   58
 13  ω     41.00  67.00   0.50   25.00    --  107.75 -77.00  60.00   52
 14  ω     41.00  66.00   0.50   25.00    --  107.75 -77.00  90.00   50
 15  ω     42.00  91.00   0.50   25.00    --  107.75 -77.00 150.00   98
 16  ω     47.00  72.00   0.50   25.00    --  107.75-125.00 120.00   50
 17  ω     35.00  66.00   0.50   25.00    --  107.75 -94.00 120.00   62
 18  ω     35.00  65.00   0.50   25.00    --  107.75 -77.00   0.00   60
 19  ω     40.00  65.00   0.50   25.00    --  107.75 -94.00 -30.00   50
 20  ω     35.00  60.00   0.50   25.00    --  107.75 -61.00   0.00   50
 21  ω    102.00 133.00   0.50   25.00    --  107.75  30.00 -60.00   62
 22  ω    137.00 163.00   0.50   25.00    --  107.75  30.00 -60.00   52
 23  ω    133.00 159.00   0.50   25.00    --  107.75  61.00 -90.00   52
 24  ω    113.00 152.00   0.50   25.00    --  107.75  45.00-120.00   78
 25  ω     91.00 118.00   0.50   25.00    --  107.75  61.00 -90.00   54
 26  ω    113.00 139.00   0.50   25.00    --  107.75  45.00  60.00   52
 27  ω    141.00 175.00   0.50   25.00    --  107.75  45.00  60.00   68
 28  ω    147.00 175.00   0.50   25.00    --  107.75  77.00  60.00   56
 29  ω    142.00 176.00   0.50   25.00    --  107.75  61.00 120.00   68
 30  ω    127.00 177.00   0.50   25.00    --  107.75  54.00 155.00  100
 31  ω    127.00 153.00   0.50   25.00    --  107.75  45.00 120.00   52
 32  ω    113.00 147.00   0.50   25.00    --  107.75  15.00 120.00   68
 33  ω    105.00 168.00   0.50   25.00    --  107.75  45.00 150.00  126
 34  ω    111.00 136.00   0.50   25.00    --  107.75  61.00 120.00   50
 35  ω     86.00 121.00   0.50   25.00    --  107.75  77.00  60.00   70
 36  ω     76.00 101.00   0.50    5.00    --   47.95  54.00 155.00   50
 37  ω    -18.00  26.00   0.50    5.00    --  -47.95  19.00 -90.00   88
 38  ω    -61.00  25.00   0.50    5.00    --  -47.95  54.00 155.00  172
 39  ω     35.00  60.00   0.50   25.00    --  107.75 -61.00-120.00   50
 40  ω     36.00  62.00   0.50   25.00    --  107.75 -77.00-180.00   52
 41  ω     38.00  64.00   0.50   25.00    --  107.75 -77.00-150.00   52
 42  ω     39.00  69.00   0.50   25.00    --  107.75 -61.00-150.00   60
 43  ω   -111.00 -73.00   0.50    5.00    --  -47.95-125.00 150.00   76
 44  ω   -119.00 -58.00   0.50    5.00    --  -47.95 -54.00  11.00  122
 45  ω   -140.00-115.00   0.50   25.00    --  -86.25 -54.00  11.00   50
 46  ω    -62.00 -37.00   0.50   25.00    --  -86.25  54.00 155.00   50
;
_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      -0.0812127000
_diffrn_orient_matrix_UB_12      0.0245937000
_diffrn_orient_matrix_UB_13      -0.0601497000
_diffrn_orient_matrix_UB_21      0.0536005000
_diffrn_orient_matrix_UB_22      0.2224710000
_diffrn_orient_matrix_UB_23      -0.0293963000
_diffrn_orient_matrix_UB_31      0.0379036000
_diffrn_orient_matrix_UB_32      -0.2616546000
_diffrn_orient_matrix_UB_33      -0.0306402000
_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                2862
_reflns_number_total             3062
_reflns_odcompleteness_completeness 96.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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         0.224
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.085
_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)+(0.0559P)²+0.2951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N7(H7), C17(H17), C16(H16), C13(H13), C6(H6), C14(H14), C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O20(H20)
;
_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
Cl7 Cl 0.67442(2) 1.34329(8) 0.69834(2) 0.05040(13) Uani 1 1 d . . . . .
O20 O 0.35038(7) 0.4724(3) 0.51811(5) 0.0523(3) Uani 1 1 d . . . . .
H20 H 0.304823 0.361423 0.505218 0.078 Uiso 1 1 calc R U . . .
O19 O 0.31310(7) 0.4436(3) 0.60990(5) 0.0531(3) Uani 1 1 d . . . . .
O9 O 0.08695(8) -0.3518(2) 0.58341(5) 0.0541(3) Uani 1 1 d . . . . .
N7 N 0.17452(8) 0.0083(3) 0.55597(5) 0.0453(3) Uani 1 1 d . . . . .
H7 H 0.212900 0.152497 0.572457 0.054 Uiso 1 1 calc R U . . .
N2 N 0.20983(8) 0.1280(3) 0.46369(6) 0.0439(3) Uani 1 1 d . . . . .
C1 C 0.15565(9) -0.0313(3) 0.49031(6) 0.0405(3) Uani 1 1 d . . . . .
C17 C 0.50027(9) 0.8263(3) 0.57298(6) 0.0432(3) Uani 1 1 d . . . . .
H17 H 0.491841 0.757889 0.530454 0.052 Uiso 1 1 calc R U . . .
C12 C 0.44050(9) 0.7357(3) 0.60704(6) 0.0400(3) Uani 1 1 d . . . . .
C8 C 0.14093(9) -0.1486(3) 0.59818(6) 0.0433(3) Uani 1 1 d . . . . .
C16 C 0.57186(9) 1.0152(3) 0.60056(6) 0.0447(3) Uani 1 1 d . . . . .
H16 H 0.612088 1.079067 0.577068 0.054 Uiso 1 1 calc R U . . .
C15 C 0.58396(9) 1.1094(3) 0.66260(6) 0.0411(3) Uani 1 1 d . . . . .
C18 C 0.36215(9) 0.5364(3) 0.57863(6) 0.0425(3) Uani 1 1 d . . . . .
C13 C 0.45465(10) 0.8350(3) 0.66970(7) 0.0473(3) Uani 1 1 d . . . . .
H13 H 0.414389 0.773651 0.693373 0.057 Uiso 1 1 calc R U . . .
C6 C 0.08678(9) -0.2146(3) 0.45428(7) 0.0460(3) Uani 1 1 d . . . . .
H6 H 0.048762 -0.323369 0.473989 0.055 Uiso 1 1 calc R U . . .
C14 C 0.52601(10) 1.0204(3) 0.69770(7) 0.0470(3) Uani 1 1 d . . . . .
H14 H 0.535429 1.086516 0.740489 0.056 Uiso 1 1 calc R U . . .
C3 C 0.19617(10) 0.1072(4) 0.40012(7) 0.0499(3) Uani 1 1 d . . . . .
H3 H 0.233834 0.221380 0.381071 0.060 Uiso 1 1 calc R U . . .
C5 C 0.07524(10) -0.2340(4) 0.38946(7) 0.0508(3) Uani 1 1 d . . . . .
H5 H 0.029337 -0.359356 0.363916 0.061 Uiso 1 1 calc R U . . .
C4 C 0.13082(10) -0.0700(4) 0.36143(7) 0.0532(3) Uani 1 1 d . . . . .
H4 H 0.123671 -0.080564 0.316761 0.064 Uiso 1 1 calc R U . . .
C10 C 0.18016(11) -0.0469(4) 0.66660(7) 0.0541(4) Uani 1 1 d . . . . .
H10A H 0.244791 -0.105753 0.681170 0.065 Uiso 1 1 calc R U . . .
H10B H 0.177306 0.173983 0.668142 0.065 Uiso 1 1 calc R U . . .
C11 C 0.13169(11) -0.1753(4) 0.71185(7) 0.0553(4) Uani 1 1 d . . . . .
H11A H 0.068161 -0.111414 0.698796 0.083 Uiso 1 1 calc R U . . .
H11B H 0.160718 -0.104073 0.755271 0.083 Uiso 1 1 calc R U . . .
H11C H 0.134638 -0.394079 0.710927 0.083 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
Cl7 C15 1.7403(14) . ?
O20 H20 0.8400 . ?
O20 C18 1.3119(16) . ?
O19 C18 1.2213(16) . ?
O9 C8 1.2120(17) . ?
N7 H7 0.8800 . ?
N7 C1 1.3897(17) . ?
N7 C8 1.3676(17) . ?
N2 C1 1.3442(17) . ?
N2 C3 1.3454(19) . ?
C1 C6 1.394(2) . ?
C17 H17 0.9500 . ?
C17 C12 1.3927(18) . ?
C17 C16 1.384(2) . ?
C12 C18 1.4869(19) . ?
C12 C13 1.3941(19) . ?
C8 C10 1.5140(19) . ?
C16 H16 0.9500 . ?
C16 C15 1.3783(19) . ?
C15 C14 1.3844(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.377(2) . ?
C14 H14 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.369(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(2) . ?
C4 H4 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.506(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O20 H20 109.5 . . ?
C1 N7 H7 115.9 . . ?
C8 N7 H7 115.9 . . ?
C8 N7 C1 128.15(12) . . ?
C1 N2 C3 118.07(12) . . ?
N7 C1 C6 124.20(12) . . ?
N2 C1 N7 113.61(12) . . ?
N2 C1 C6 122.18(12) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C12 120.57(12) . . ?
C17 C12 C18 122.03(12) . . ?
C17 C12 C13 118.92(13) . . ?
C13 C12 C18 119.06(12) . . ?
O9 C8 N7 124.41(13) . . ?
O9 C8 C10 122.80(13) . . ?
N7 C8 C10 112.78(12) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 C17 119.06(12) . . ?
C15 C16 H16 120.5 . . ?
C16 C15 Cl7 119.66(10) . . ?
C16 C15 C14 121.52(13) . . ?
C14 C15 Cl7 118.82(11) . . ?
O20 C18 C12 114.69(11) . . ?
O19 C18 O20 123.61(13) . . ?
O19 C18 C12 121.70(12) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.95(13) . . ?
C14 C13 H13 119.5 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.36(13) . . ?
C5 C6 H6 120.8 . . ?
C15 C14 H14 120.5 . . ?
C13 C14 C15 118.98(13) . . ?
C13 C14 H14 120.5 . . ?
N2 C3 H3 118.3 . . ?
N2 C3 C4 123.43(13) . . ?
C4 C3 H3 118.3 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 119.92(14) . . ?
C4 C5 H5 120.0 . . ?
C3 C4 C5 118.02(13) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C8 C10 H10A 108.9 . . ?
C8 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C8 113.37(13) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
O20 H20 N2 0.84 1.82 2.6484(16) 170.0 . yes
N7 H7 O19 0.88 2.01 2.8825(16) 172.6 . 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
Cl7 C15 C14 C13 -179.81(11) . . . . ?
O9 C8 C10 C11 -12.2(2) . . . . ?
N7 C1 C6 C5 179.98(13) . . . . ?
N7 C8 C10 C11 169.17(14) . . . . ?
N2 C1 C6 C5 0.8(2) . . . . ?
N2 C3 C4 C5 0.7(2) . . . . ?
C1 N7 C8 O9 -0.7(2) . . . . ?
C1 N7 C8 C10 177.90(13) . . . . ?
C1 N2 C3 C4 -0.8(2) . . . . ?
C1 C6 C5 C4 -0.8(2) . . . . ?
C17 C12 C18 O20 -4.80(18) . . . . ?
C17 C12 C18 O19 175.65(13) . . . . ?
C17 C12 C13 C14 0.3(2) . . . . ?
C17 C16 C15 Cl7 179.22(10) . . . . ?
C17 C16 C15 C14 -0.3(2) . . . . ?
C12 C17 C16 C15 0.9(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C8 N7 C1 N2 -170.37(13) . . . . ?
C8 N7 C1 C6 10.4(2) . . . . ?
C16 C17 C12 C18 179.13(12) . . . . ?
C16 C17 C12 C13 -0.9(2) . . . . ?
C16 C15 C14 C13 -0.3(2) . . . . ?
C18 C12 C13 C14 -179.73(13) . . . . ?
C13 C12 C18 O20 175.20(12) . . . . ?
C13 C12 C18 O19 -4.4(2) . . . . ?
C6 C5 C4 C3 0.1(2) . . . . ?
C3 N2 C1 N7 -179.26(12) . . . . ?
C3 N2 C1 C6 0.02(19) . . . . ?


_olex2_date_sample_submission    2020-12-16
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_olex2_submission_original_sample_id AA-propyl-H:4ClBA
_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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.714
