# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1801
_database_code_depnum_ccdc_archive 'CCDC 1944275'
loop_
_audit_author_name
_audit_author_address
'Abhi Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H10 I N3 O'
_chemical_formula_sum            'C11 H10 I N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         327.12

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   26.035(8)
_cell_length_b                   4.7746(16)
_cell_length_c                   9.927(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.80(2)
_cell_angle_gamma                90
_cell_volume                     1216.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4834
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      19.97
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    2.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.81

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            26370
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_theta_min         0.79
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2204
_reflns_number_gt                1378
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1792
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_number_reflns         2204
_refine_ls_number_parameters     153
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0947P)²+0.9002P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.505
_refine_diff_density_min         -1.043
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
N N1 0.1930(2) 0.6544(11) 0.4859(5) 0.0562(12) Uani d . . . 1 . .
N N2 0.1928(2) 0.5231(13) 0.6060(5) 0.0761(16) Uani d . . . 1 . .
C C3 0.1490(3) 0.3781(18) 0.5870(7) 0.081(2) Uani d . . . 1 . .
H H3 0.1383 0.2645 0.6531 0.098 Uiso calc U . R 1 . .
C C4 0.1207(2) 0.4154(13) 0.4566(6) 0.0607(15) Uani d . . . 1 . .
C C5 0.1506(2) 0.5921(13) 0.3961(6) 0.0606(15) Uani d . . . 1 . .
H H5 0.1427 0.6585 0.3069 0.073 Uiso calc U . R 1 . .
I I6 0.05031(2) 0.23651(11) 0.37163(6) 0.0938(4) Uani d . . . 1 . .
C C7 0.2363(3) 0.8305(13) 0.4676(7) 0.0621(16) Uani d . . . 1 . .
H H7A 0.2406 0.9749 0.5374 0.075 Uiso calc U . R 1 . .
H H7B 0.2282 0.9223 0.3794 0.075 Uiso calc U . R 1 . .
C C8 0.2870(2) 0.6738(11) 0.4752(6) 0.0499(14) Uani d . . . 1 . .
C C9 0.2922(2) 0.4631(12) 0.3819(5) 0.0537(14) Uani d . . . 1 . .
H H9 0.2636 0.4147 0.3163 0.064 Uiso calc U . R 1 . .
C C10 0.3385(2) 0.3249(12) 0.3847(6) 0.0542(15) Uani d . . . 1 . .
H H10 0.3413 0.188 0.3197 0.065 Uiso calc U . R 1 . .
C C11 0.3818(2) 0.3889(11) 0.4850(5) 0.0451(12) Uani d . . . 1 . .
C C12 0.3763(2) 0.5935(12) 0.5790(5) 0.0560(14) Uani d . . . 1 . .
H H12 0.4043 0.6377 0.647 0.067 Uiso calc U . R 1 . .
C C13 0.3298(3) 0.7338(11) 0.5736(7) 0.0575(16) Uani d . . . 1 . .
H H13 0.3271 0.8725 0.6379 0.069 Uiso calc U . R 1 . .
C C14 0.4313(3) 0.2327(11) 0.4879(6) 0.0500(14) Uani d . . . 1 . .
O O15 0.44288(17) 0.1336(12) 0.3815(4) 0.0668(12) Uani d . . . 1 . .
H H16A 0.490(2) 0.090(10) 0.613(5) 0.034(13) Uiso d . . . 1 . .
H H16B 0.452(3) 0.241(11) 0.680(6) 0.07(2) Uiso d . . D 1 . .
N N16 0.4626(3) 0.2037(13) 0.6076(5) 0.0628(15) 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
N1 C5 . 1.329(7) ?
N1 N2 . 1.347(6) ?
N1 C7 . 1.442(8) ?
N2 C3 . 1.322(8) ?
C3 C4 . 1.388(9) ?
C3 H3 . 0.93 ?
C4 C5 . 1.355(8) ?
C4 I6 . 2.066(6) ?
C5 H5 . 0.93 ?
I6 I6 2_545 4.0298(14) ?
C7 C8 . 1.508(9) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C13 . 1.381(9) ?
C8 C9 . 1.390(8) ?
C9 C10 . 1.372(8) ?
C9 H9 . 0.93 ?
C10 C11 . 1.404(8) ?
C10 H10 . 0.93 ?
C11 C12 . 1.376(7) ?
C11 C14 . 1.484(8) ?
C12 C13 . 1.376(9) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 O15 . 1.241(7) ?
C14 N16 . 1.329(9) ?
N16 H16A . 0.89(5) ?
N16 H16B . 0.83(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
C5 N1 N2 . . 111.2(5) ?
C5 N1 C7 . . 128.6(5) ?
N2 N1 C7 . . 120.1(5) ?
C3 N2 N1 . . 104.5(5) ?
N2 C3 C4 . . 112.0(6) ?
N2 C3 H3 . . 124.0 ?
C4 C3 H3 . . 124.0 ?
C5 C4 C3 . . 103.8(6) ?
C5 C4 I6 . . 127.8(5) ?
C3 C4 I6 . . 128.4(5) ?
N1 C5 C4 . . 108.5(6) ?
N1 C5 H5 . . 125.8 ?
C4 C5 H5 . . 125.8 ?
C4 I6 I6 . 2_545 158.44(16) ?
N1 C7 C8 . . 113.6(5) ?
N1 C7 H7A . . 108.8 ?
C8 C7 H7A . . 108.8 ?
N1 C7 H7B . . 108.8 ?
C8 C7 H7B . . 108.8 ?
H7A C7 H7B . . 107.7 ?
C13 C8 C9 . . 117.6(6) ?
C13 C8 C7 . . 121.8(5) ?
C9 C8 C7 . . 120.6(6) ?
C10 C9 C8 . . 121.3(5) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 120.5(5) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C12 C11 C10 . . 118.1(5) ?
C12 C11 C14 . . 122.3(5) ?
C10 C11 C14 . . 119.6(5) ?
C11 C12 C13 . . 120.9(6) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C8 . . 121.6(5) ?
C12 C13 H13 . . 119.2 ?
C8 C13 H13 . . 119.2 ?
O15 C14 N16 . . 121.3(6) ?
O15 C14 C11 . . 120.7(5) ?
N16 C14 C11 . . 117.9(5) ?
C14 N16 H16A . . 119.(3) ?
C14 N16 H16B . . 120.(6) ?
H16A N16 H16B . . 118.(6) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 C3 . . . . 0.0(7) ?
C7 N1 N2 C3 . . . . -178.7(6) ?
N1 N2 C3 C4 . . . . -0.4(8) ?
N2 C3 C4 C5 . . . . 0.5(8) ?
N2 C3 C4 I6 . . . . 179.1(5) ?
N2 N1 C5 C4 . . . . 0.3(7) ?
C7 N1 C5 C4 . . . . 178.9(6) ?
C3 C4 C5 N1 . . . . -0.5(7) ?
I6 C4 C5 N1 . . . . -179.1(4) ?
C5 N1 C7 C8 . . . . -114.1(7) ?
N2 N1 C7 C8 . . . . 64.4(7) ?
N1 C7 C8 C13 . . . . -118.8(6) ?
N1 C7 C8 C9 . . . . 61.5(7) ?
C13 C8 C9 C10 . . . . -1.9(8) ?
C7 C8 C9 C10 . . . . 177.8(5) ?
C8 C9 C10 C11 . . . . 1.7(8) ?
C9 C10 C11 C12 . . . . -0.3(8) ?
C9 C10 C11 C14 . . . . 178.7(5) ?
C10 C11 C12 C13 . . . . -0.8(8) ?
C14 C11 C12 C13 . . . . -179.8(5) ?
C11 C12 C13 C8 . . . . 0.6(9) ?
C9 C8 C13 C12 . . . . 0.8(8) ?
C7 C8 C13 C12 . . . . -178.9(5) ?
C12 C11 C14 O15 . . . . -152.5(6) ?
C10 C11 C14 O15 . . . . 28.6(8) ?
C12 C11 C14 N16 . . . . 27.3(8) ?
C10 C11 C14 N16 . . . . -151.6(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
N16 H16A O15 3_656 0.89(5) 2.04(5) 2.928(8) 174.(4) ?
N16 H16B O15 4_566 0.83(4) 2.14(5) 2.955(7) 166.(7) ?

#data_global
_audit_creation_method           'APEX2 v2014.11-0'
####################################################################### 
# 
# 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_1802
_database_code_depnum_ccdc_archive 'CCDC 1944277'
loop_
_audit_author_name
_audit_author_address
'Abhi Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2018-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N3, 0.5(C2 H2 O4)'
_chemical_formula_sum            'C14 H14 N3 O2'
_chemical_formula_weight         256.28
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.478(3)
_cell_length_b                   10.115(3)
_cell_length_c                   13.052(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.830(12)
_cell_angle_gamma                90
_cell_volume                     1324.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.92
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0926 before and 0.0591 after correction. The Ratio of minimum to maximum transmission is 0.8924. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.138
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.468
_diffrn_reflns_theta_min         2.031
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1429
_reflns_number_total             2426
_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 APEX2'
_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         0.148
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.012(2)
_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   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.017
_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)+(0.0628P)²+0.1984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1422
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O19-H19
 0.84 with sigma of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C13(H13), C14(H14)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
N1 N 0.72884(19) 0.78680(19) 0.18533(14) 0.0514(5) Uani 1 1 d . . . . .
N2 N 0.7335(2) 0.90805(19) 0.22576(15) 0.0540(5) Uani 1 1 d . . . . .
C3 C 0.6170(3) 0.9597(3) 0.1824(2) 0.0637(7) Uani 1 1 d . . . . .
C4 C 0.5387(3) 0.8716(3) 0.1147(2) 0.0750(8) Uani 1 1 d . . . . .
H4 H 0.4508 0.8847 0.0739 0.090 Uiso 1 1 calc R . . . .
C5 C 0.6109(3) 0.7627(3) 0.1175(2) 0.0629(7) Uani 1 1 d . . . . .
C6 C 0.5885(3) 1.0951(3) 0.2086(3) 0.0980(10) Uani 1 1 d . . . . .
H6A H 0.6169 1.1066 0.2849 0.147 Uiso 1 1 calc GR . . . .
H6B H 0.4944 1.1113 0.1820 0.147 Uiso 1 1 calc GR . . . .
H6C H 0.6354 1.1561 0.1763 0.147 Uiso 1 1 calc GR . . . .
C7 C 0.5797(3) 0.6370(3) 0.0609(3) 0.0975(11) Uani 1 1 d . . . . .
H7A H 0.6336 0.6271 0.0131 0.146 Uiso 1 1 calc GR . . . .
H7B H 0.4872 0.6355 0.0206 0.146 Uiso 1 1 calc GR . . . .
H7C H 0.5979 0.5658 0.1117 0.146 Uiso 1 1 calc GR . . . .
C8 C 0.8419(2) 0.7019(2) 0.21796(19) 0.0563(6) Uani 1 1 d . . . . .
H8A H 0.9206 0.7554 0.2484 0.068 Uiso 1 1 calc R . . . .
H8B H 0.8535 0.6580 0.1552 0.068 Uiso 1 1 calc R . . . .
C9 C 0.8328(2) 0.6005(2) 0.29699(17) 0.0482(6) Uani 1 1 d . . . . .
C10 C 0.8627(3) 0.4736(2) 0.2826(2) 0.0665(7) Uani 1 1 d . . . . .
H10 H 0.8826 0.4493 0.2201 0.080 Uiso 1 1 calc R . . . .
C11 C 0.8644(3) 0.3817(3) 0.3571(2) 0.0743(8) Uani 1 1 d . . . . .
H11 H 0.8868 0.2948 0.3468 0.089 Uiso 1 1 calc R . . . .
C12 C 0.8335(2) 0.4157(3) 0.4468(2) 0.0583(7) Uani 1 1 d . . . . .
C13 C 0.7996(3) 0.5418(3) 0.4607(2) 0.0622(7) Uani 1 1 d . . . . .
H13 H 0.7770 0.5655 0.5221 0.075 Uiso 1 1 calc R . . . .
C14 C 0.7986(3) 0.6328(2) 0.38592(19) 0.0581(7) Uani 1 1 d . . . . .
H14 H 0.7741 0.7192 0.3954 0.070 Uiso 1 1 calc R . . . .
C15 C 0.8358(3) 0.3207(3) 0.5259(3) 0.0829(9) Uani 1 1 d . . . . .
N16 N 0.8363(3) 0.2460(3) 0.5889(3) 0.1245(12) Uani 1 1 d . . . . .
C17 C 0.9377(3) 0.9771(2) 0.46094(18) 0.0543(6) Uani 1 1 d . . . . .
O18 O 0.8577(2) 0.9148(2) 0.48657(14) 0.0925(7) Uani 1 1 d . . . . .
O19 O 0.92922(18) 1.01208(17) 0.36588(13) 0.0615(5) Uani 1 1 d D . . . .
H19 H 0.854(3) 0.975(3) 0.315(2) 0.118(12) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.330(2) . ?
N1 C5 1.318(3) . ?
N1 C8 1.425(3) . ?
N2 C3 1.297(3) . ?
C3 C4 1.352(4) . ?
C3 C6 1.464(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.330(4) . ?
C5 C7 1.460(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.477(3) . ?
C9 C10 1.348(3) . ?
C9 C14 1.350(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.342(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.346(3) . ?
C12 C13 1.351(3) . ?
C12 C15 1.405(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.339(3) . ?
C14 H14 0.9300 . ?
C15 N16 1.116(3) . ?
C17 C17 1.479(5) 3_776 ?
C17 O18 1.173(3) . ?
C17 O19 1.268(3) . ?
O19 H19 0.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 120.35(19) . . ?
C5 N1 N2 110.8(2) . . ?
C5 N1 C8 128.8(2) . . ?
C3 N2 N1 106.0(2) . . ?
N2 C3 C4 109.7(2) . . ?
N2 C3 C6 120.3(3) . . ?
C4 C3 C6 130.0(3) . . ?
C3 C4 H4 126.4 . . ?
C5 C4 C3 107.1(2) . . ?
C5 C4 H4 126.4 . . ?
N1 C5 C4 106.3(2) . . ?
N1 C5 C7 122.0(3) . . ?
C4 C5 C7 131.7(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
N1 C8 C9 114.25(19) . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 C14 118.7(2) . . ?
C14 C9 C8 121.3(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 C15 120.5(3) . . ?
C13 C12 C15 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
N16 C15 C12 179.2(3) . . ?
O18 C17 C17 122.2(3) . 3_776 ?
O18 C17 O19 125.2(2) . . ?
O19 C17 C17 112.6(3) . 3_776 ?
C17 O19 H19 112.6(19) . . ?

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
O19 H19 N2 0.95(3) 1.60(3) 2.547(3) 177(3) .

_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_1704
_database_code_depnum_ccdc_archive 'CCDC 1944276'
loop_
_audit_author_name
_audit_author_address
'Abhi Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H8 I N3'
_chemical_formula_sum            'C11 H8 I N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         309.10
_chemical_absolute_configuration ?

_chemical_melting_point          ?

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

_cell_length_a                   4.4460(14)
_cell_length_b                   13.030(4)
_cell_length_c                   19.520(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1130.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1358
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      15.42
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Needles
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.078
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592

_exptl_absorpt_coefficient_mu    2.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.81

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            11996
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.91
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             2154
_reflns_number_gt                1183
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1061
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_number_reflns         2154
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.407
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0029(8)
_refine_ls_abs_structure_details 
;
Flack x determined using 328 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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 0.610(3) 0.7034(9) 0.6249(7) 0.059(3) Uani d . . . 1 . .
C C2 0.454(3) 0.6987(9) 0.6853(7) 0.067(4) Uani d . . . 1 . .
H H2 0.4613 0.6388 0.7112 0.081 Uiso calc U . R 1 . .
C C3 0.286(3) 0.7800(10) 0.7088(6) 0.072(3) Uani d . . . 1 . .
H H3 0.1823 0.7756 0.7501 0.086 Uiso calc U . R 1 . .
C C4 0.276(3) 0.8674(8) 0.6705(7) 0.058(3) Uani d . . . 1 . .
C C5 0.427(3) 0.8742(10) 0.6110(8) 0.074(4) Uani d . . . 1 . .
H H5 0.417 0.9343 0.5854 0.088 Uiso calc U . R 1 . .
C C6 0.598(3) 0.7929(10) 0.5874(6) 0.069(4) Uani d . . . 1 . .
H H6 0.7048 0.7986 0.5466 0.083 Uiso calc U . R 1 . .
C C7 0.098(4) 0.9557(12) 0.6946(8) 0.089(5) Uani d . . . 1 . .
N N8 -0.028(4) 1.0205(10) 0.7157(8) 0.120(6) Uani d . . . 1 . .
C C9 0.790(3) 0.6135(9) 0.6003(7) 0.081(4) Uani d . . . 1 . .
H H9A 0.9024 0.6338 0.56 0.098 Uiso calc U . R 1 . .
H H9B 0.9339 0.5948 0.6355 0.098 Uiso calc U . R 1 . .
N N10 0.610(2) 0.5246(8) 0.5837(6) 0.063(3) Uani d . . . 1 . .
N N11 0.450(3) 0.5238(9) 0.5239(6) 0.074(3) Uani d . . . 1 . .
C C12 0.309(3) 0.4342(11) 0.5260(7) 0.076(4) Uani d . . . 1 . .
H H12 0.1775 0.4122 0.4919 0.091 Uiso calc U . R 1 . .
C C13 0.375(2) 0.3762(9) 0.5838(7) 0.054(3) Uani d . . . 1 . .
C C14 0.570(2) 0.4376(10) 0.6193(7) 0.065(3) Uani d . . . 1 . .
H H14 0.66 0.4217 0.661 0.078 Uiso calc U . R 1 . .
I I15 0.22088(19) 0.23444(6) 0.61193(5) 0.0834(5) 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 C2 . 1.370(16) ?
C1 C6 . 1.377(17) ?
C1 C9 . 1.498(16) ?
C2 C3 . 1.374(16) ?
C2 H2 . 0.93 ?
C3 C4 . 1.363(14) ?
C3 H3 . 0.93 ?
C4 C5 . 1.346(16) ?
C4 C7 . 1.472(19) ?
C5 C6 . 1.382(16) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 N8 . 1.095(17) ?
C9 N10 . 1.443(13) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
N10 C14 . 1.342(14) ?
N10 N11 . 1.369(13) ?
N11 C12 . 1.327(15) ?
C12 C13 . 1.390(15) ?
C12 H12 . 0.93 ?
C13 C14 . 1.368(15) ?
C13 I15 . 2.046(11) ?
C14 H14 . 0.93 ?

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
C2 C1 C6 . . 118.4(12) ?
C2 C1 C9 . . 120.8(12) ?
C6 C1 C9 . . 120.8(12) ?
C1 C2 C3 . . 121.9(12) ?
C1 C2 H2 . . 119.1 ?
C3 C2 H2 . . 119.1 ?
C4 C3 C2 . . 118.6(12) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C5 C4 C3 . . 120.8(13) ?
C5 C4 C7 . . 119.5(12) ?
C3 C4 C7 . . 119.7(14) ?
C4 C5 C6 . . 120.8(13) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 119.5(12) ?
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
N8 C7 C4 . . 176.(2) ?
N10 C9 C1 . . 113.8(11) ?
N10 C9 H9A . . 108.8 ?
C1 C9 H9A . . 108.8 ?
N10 C9 H9B . . 108.8 ?
C1 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
C14 N10 N11 . . 111.5(10) ?
C14 N10 C9 . . 129.5(11) ?
N11 N10 C9 . . 119.0(11) ?
C12 N11 N10 . . 103.1(11) ?
N11 C12 C13 . . 113.7(12) ?
N11 C12 H12 . . 123.1 ?
C13 C12 H12 . . 123.1 ?
C14 C13 C12 . . 103.2(11) ?
C14 C13 I15 . . 127.2(11) ?
C12 C13 I15 . . 129.6(10) ?
N10 C14 C13 . . 108.4(12) ?
N10 C14 H14 . . 125.8 ?
C13 C14 H14 . . 125.8 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.5(18) ?
C9 C1 C2 C3 . . . . -179.8(11) ?
C1 C2 C3 C4 . . . . 0.2(19) ?
C2 C3 C4 C5 . . . . -0.4(19) ?
C2 C3 C4 C7 . . . . -179.9(13) ?
C3 C4 C5 C6 . . . . -0.2(19) ?
C7 C4 C5 C6 . . . . 179.3(12) ?
C2 C1 C6 C5 . . . . -1.1(16) ?
C9 C1 C6 C5 . . . . 179.2(12) ?
C4 C5 C6 C1 . . . . 1.0(18) ?
C2 C1 C9 N10 . . . . 65.2(15) ?
C6 C1 C9 N10 . . . . -115.1(12) ?
C1 C9 N10 C14 . . . . -103.7(14) ?
C1 C9 N10 N11 . . . . 75.9(14) ?
C14 N10 N11 C12 . . . . 1.3(13) ?
C9 N10 N11 C12 . . . . -178.4(11) ?
N10 N11 C12 C13 . . . . -1.2(15) ?
N11 C12 C13 C14 . . . . 0.7(15) ?
N11 C12 C13 I15 . . . . -180.0(8) ?
N11 N10 C14 C13 . . . . -0.9(13) ?
C9 N10 C14 C13 . . . . 178.7(12) ?
C12 C13 C14 N10 . . . . 0.1(13) ?
I15 C13 C14 N10 . . . . -179.2(7) ?

