# 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_24
_database_code_depnum_ccdc_archive 'CCDC 2110971'
loop_
_audit_author_name
_audit_author_address
'Sureshbabu Popuri'
;Department of Chemistry, IIT Madras
India
;
_audit_update_record             
;
2021-09-21 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0248(3)
_cell_length_b                   9.5325(5)
_cell_length_c                   10.9187(5)
_cell_angle_alpha                82.054(2)
_cell_angle_beta                 77.986(2)
_cell_angle_gamma                69.701(2)
_cell_volume                     764.22(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4285
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.43

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9743
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2672
_reflns_number_gt                2106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_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'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.1214P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2672
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.16007(18) 0.91533(15) 0.65114(13) 0.0447(3) Uani 1 1 d . . . . .
H1 H 0.1808 0.9618 0.5715 0.054 Uiso 1 1 calc R U . . .
C2 C 0.2046(2) 0.95997(17) 0.75148(15) 0.0557(4) Uani 1 1 d . . . . .
H2 H 0.2541 1.0368 0.7393 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1757(2) 0.89095(19) 0.86951(15) 0.0631(5) Uani 1 1 d . . . . .
H3 H 0.2066 0.9207 0.9369 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1013(2) 0.77802(19) 0.88776(14) 0.0619(4) Uani 1 1 d . . . . .
H4 H 0.0822 0.7314 0.9676 0.074 Uiso 1 1 calc R U . . .
C5 C 0.0549(2) 0.73354(17) 0.78808(13) 0.0504(4) Uani 1 1 d . . . . .
H5 H 0.0034 0.6578 0.8012 0.061 Uiso 1 1 calc R U . . .
C6 C 0.08470(17) 0.80166(14) 0.66807(12) 0.0381(3) Uani 1 1 d . . . . .
C7 C 0.03887(17) 0.75374(13) 0.56058(12) 0.0367(3) Uani 1 1 d . . . . .
C8 C -0.11837(17) 0.71645(14) 0.55495(12) 0.0399(3) Uani 1 1 d . . . . .
C9 C -0.27475(19) 0.71449(16) 0.63924(15) 0.0510(4) Uani 1 1 d . . . . .
H9 H -0.2922 0.7378 0.7219 0.061 Uiso 1 1 calc R U . . .
C10 C -0.4017(2) 0.67715(17) 0.59643(18) 0.0613(4) Uani 1 1 d . . . . .
H10 H -0.5061 0.6741 0.6514 0.074 Uiso 1 1 calc R U . . .
C11 C -0.3778(2) 0.64367(17) 0.47254(18) 0.0619(5) Uani 1 1 d . . . . .
H11 H -0.4678 0.6206 0.4465 0.074 Uiso 1 1 calc R U . . .
C12 C -0.2254(2) 0.64368(16) 0.38764(15) 0.0524(4) Uani 1 1 d . . . . .
H12 H -0.2094 0.6203 0.3051 0.063 Uiso 1 1 calc R U . . .
C13 C -0.09611(17) 0.68063(14) 0.43170(13) 0.0406(3) Uani 1 1 d . . . . .
C14 C 0.1559(2) 0.66347(15) 0.24939(12) 0.0447(3) Uani 1 1 d . . . . .
C15 C 0.31712(18) 0.71015(15) 0.19870(12) 0.0427(3) Uani 1 1 d . . . . .
C16 C 0.4646(2) 0.61056(17) 0.12954(13) 0.0563(4) Uani 1 1 d . . . . .
H16 H 0.4637 0.5150 0.1214 0.068 Uiso 1 1 calc R U . . .
C17 C 0.6126(2) 0.6519(2) 0.07269(15) 0.0649(5) Uani 1 1 d . . . . .
H17 H 0.7120 0.5839 0.0276 0.078 Uiso 1 1 calc R U . . .
C18 C 0.6127(2) 0.7938(2) 0.08281(15) 0.0614(4) Uani 1 1 d . . . . .
H18 H 0.7117 0.8224 0.0436 0.074 Uiso 1 1 calc R U . . .
C19 C 0.4670(2) 0.89352(18) 0.15073(14) 0.0561(4) Uani 1 1 d . . . . .
H19 H 0.4677 0.9896 0.1570 0.067 Uiso 1 1 calc R U . . .
C20 C 0.31984(19) 0.85255(16) 0.20966(13) 0.0475(4) Uani 1 1 d . . . . .
H20 H 0.2225 0.9202 0.2567 0.057 Uiso 1 1 calc R U . . .
N1 N 0.14803(14) 0.74307(12) 0.45198(10) 0.0393(3) Uani 1 1 d . . . . .
N2 N 0.06782(14) 0.69729(12) 0.37055(10) 0.0409(3) Uani 1 1 d . . . . .
O1 O 0.09861(16) 0.59889(13) 0.18785(9) 0.0631(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(2) . ?
C1 C6 1.3882(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3922(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4717(18) . ?
C7 N1 1.3126(16) . ?
C7 C8 1.4394(18) . ?
C8 C13 1.3943(19) . ?
C8 C9 1.3974(19) . ?
C9 C10 1.371(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3932(19) . ?
C12 H12 0.9300 . ?
C13 N2 1.3970(16) . ?
C14 O1 1.2173(16) . ?
C14 N2 1.3871(17) . ?
C14 C15 1.487(2) . ?
C15 C16 1.385(2) . ?
C15 C20 1.3872(19) . ?
C16 C17 1.379(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 N2 1.3913(14) . ?

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
C2 C1 C6 120.60(13) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.10(15) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.99(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.32(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.23(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.77(12) . . ?
C1 C6 C7 120.35(12) . . ?
C5 C6 C7 120.88(12) . . ?
N1 C7 C8 111.76(11) . . ?
N1 C7 C6 119.74(11) . . ?
C8 C7 C6 128.49(12) . . ?
C13 C8 C9 119.62(13) . . ?
C13 C8 C7 105.21(11) . . ?
C9 C8 C7 135.13(13) . . ?
C10 C9 C8 118.00(15) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 121.42(15) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 122.04(15) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 116.38(15) . . ?
C11 C12 H12 121.8 . . ?
C13 C12 H12 121.8 . . ?
C12 C13 C8 122.53(13) . . ?
C12 C13 N2 131.26(13) . . ?
C8 C13 N2 106.15(11) . . ?
O1 C14 N2 119.56(13) . . ?
O1 C14 C15 122.27(12) . . ?
N2 C14 C15 118.17(11) . . ?
C16 C15 C20 119.11(13) . . ?
C16 C15 C14 118.08(13) . . ?
C20 C15 C14 122.62(12) . . ?
C17 C16 C15 120.56(14) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.80(15) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.08(15) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.60(15) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 119.84(13) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C7 N1 N2 106.08(10) . . ?
C14 N2 N1 120.95(11) . . ?
C14 N2 C13 128.04(11) . . ?
N1 N2 C13 110.80(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(2) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C6 C7 -179.51(12) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 178.92(13) . . . . ?
C1 C6 C7 N1 40.02(17) . . . . ?
C5 C6 C7 N1 -139.48(13) . . . . ?
C1 C6 C7 C8 -138.89(14) . . . . ?
C5 C6 C7 C8 41.61(19) . . . . ?
N1 C7 C8 C13 0.26(14) . . . . ?
C6 C7 C8 C13 179.24(12) . . . . ?
N1 C7 C8 C9 -177.35(14) . . . . ?
C6 C7 C8 C9 1.6(2) . . . . ?
C13 C8 C9 C10 -0.1(2) . . . . ?
C7 C8 C9 C10 177.22(14) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 1.1(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C11 C12 C13 N2 -176.97(13) . . . . ?
C9 C8 C13 C12 0.61(19) . . . . ?
C7 C8 C13 C12 -177.45(12) . . . . ?
C9 C8 C13 N2 178.07(11) . . . . ?
C7 C8 C13 N2 0.00(13) . . . . ?
O1 C14 C15 C16 -42.4(2) . . . . ?
N2 C14 C15 C16 138.54(14) . . . . ?
O1 C14 C15 C20 132.49(15) . . . . ?
N2 C14 C15 C20 -46.61(19) . . . . ?
C20 C15 C16 C17 0.3(2) . . . . ?
C14 C15 C16 C17 175.32(14) . . . . ?
C15 C16 C17 C18 -1.1(2) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C15 -1.1(2) . . . . ?
C16 C15 C20 C19 0.8(2) . . . . ?
C14 C15 C20 C19 -173.96(13) . . . . ?
C8 C7 N1 N2 -0.41(14) . . . . ?
C6 C7 N1 N2 -179.49(10) . . . . ?
O1 C14 N2 N1 167.01(12) . . . . ?
C15 C14 N2 N1 -13.86(18) . . . . ?
O1 C14 N2 C13 -7.3(2) . . . . ?
C15 C14 N2 C13 171.82(12) . . . . ?
C7 N1 N2 C14 -174.80(11) . . . . ?
C7 N1 N2 C13 0.41(13) . . . . ?
C12 C13 N2 C14 -8.3(2) . . . . ?
C8 C13 N2 C14 174.54(12) . . . . ?
C12 C13 N2 N1 176.90(13) . . . . ?
C8 C13 N2 N1 -0.25(14) . . . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.026



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2110972'
loop_
_audit_author_name
_audit_author_address
'Sureshbabu Popuri'
;Department of Chemistry, IIT Madras
India
;
_audit_update_record             
;
2021-09-21 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 I N2 O'
_chemical_formula_sum            'C14 H9 I N2 O'
_chemical_formula_weight         348.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

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'

_cell_length_a                   4.3661(4)
_cell_length_b                   23.242(2)
_cell_length_c                   12.7698(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.256(3)
_cell_angle_gamma                90
_cell_volume                     1290.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    9073
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      30.49
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.470
_shelx_estimated_absorpt_T_min   0.524
_shelx_estimated_absorpt_T_max   0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4959
_exptl_absorpt_correction_T_max  0.5964
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 venture PHOTON II diffractometer'
_diffrn_measurement_method       'ω and φ scan'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20496
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.506
_diffrn_reflns_theta_max         30.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3837
_reflns_number_gt                3684
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_max     0.955
_reflns_Friedel_fraction_full    0.991

_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.
;

_computing_data_collection       'Bruker Apex3'
_computing_cell_refinement       'Bruker Apex3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP, L.J.Farrugia, (2012)J. Appl. Cryst. 45, 849-854'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0206P)²+0.3812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0179
_refine_ls_wR_factor_ref         0.0459
_refine_ls_wR_factor_gt          0.0455
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.2297(7) 0.27900(13) -0.0424(2) 0.0466(6) Uani 1 1 d . . . . .
C2 C 0.1088(8) 0.28468(13) -0.1463(3) 0.0535(6) Uani 1 1 d . . . . .
H2 H -0.032819 0.258068 -0.175897 0.064 Uiso 1 1 calc R U . . .
C3 C 0.2012(7) 0.33036(14) -0.2053(2) 0.0499(6) Uani 1 1 d . . . . .
H3 H 0.124845 0.333881 -0.275408 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4073(6) 0.37111(12) -0.1607(2) 0.0432(5) Uani 1 1 d . . . . .
C5 C 0.5265(7) 0.36522(12) -0.0560(2) 0.0472(5) Uani 1 1 d . . . . .
H5 H 0.663492 0.392360 -0.025459 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4389(7) 0.31853(12) 0.0024(2) 0.0467(5) Uani 1 1 d . . . . .
H6 H 0.521159 0.313876 0.071619 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5172(7) 0.41607(13) -0.2312(2) 0.0467(6) Uani 1 1 d . . . . .
C8 C 0.7542(7) 0.51359(13) -0.2352(2) 0.0474(5) Uani 1 1 d . . . . .
C9 C 0.9100(8) 0.51486(16) -0.3264(2) 0.0556(7) Uani 1 1 d . . . . .
H9 H 0.919604 0.482944 -0.369884 0.067 Uiso 1 1 calc R U . . .
C10 C 1.0497(9) 0.56702(19) -0.3478(3) 0.0672(9) Uani 1 1 d . . . . .
H10 H 1.156759 0.569725 -0.407291 0.081 Uiso 1 1 calc R U . . .
C11 C 1.0355(10) 0.61446(19) -0.2845(4) 0.0761(11) Uani 1 1 d . . . . .
H11 H 1.129044 0.648495 -0.302843 0.091 Uiso 1 1 calc R U . . .
C12 C 0.8849(10) 0.61258(17) -0.1941(4) 0.0712(9) Uani 1 1 d . . . . .
H12 H 0.878070 0.644739 -0.151060 0.085 Uiso 1 1 calc R U . . .
C13 C 0.7427(9) 0.56104(15) -0.1689(3) 0.0557(7) Uani 1 1 d . . . . .
C14 C 0.5724(9) 0.54187(14) -0.0853(3) 0.0602(7) Uani 1 1 d . . . . .
H14 H 0.529204 0.565051 -0.029100 0.072 Uiso 1 1 calc R U . . .
I1 I 0.09774(3) 0.20971(2) 0.04866(2) 0.05809(7) Uani 1 1 d . . . . .
N1 N 0.5982(6) 0.46947(10) -0.18884(18) 0.0476(5) Uani 1 1 d . . . . .
N2 N 0.4834(8) 0.48814(11) -0.0959(2) 0.0562(6) Uani 1 1 d . . . . .
O1 O 0.5466(7) 0.40671(10) -0.32352(16) 0.0625(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.382(4) . ?
C1 C2 1.388(4) . ?
C1 I1 2.098(3) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(4) . ?
C4 C7 1.487(4) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.217(4) . ?
C7 N1 1.387(4) . ?
C8 N1 1.393(4) . ?
C8 C13 1.394(5) . ?
C8 C9 1.401(4) . ?
C9 C10 1.395(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.400(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.428(5) . ?
C14 N2 1.311(4) . ?
C14 H14 0.9300 . ?
N1 N2 1.399(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
C6 C1 C2 120.7(3) . . ?
C6 C1 I1 119.1(2) . . ?
C2 C1 I1 120.2(2) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 C7 117.6(3) . . ?
C5 C4 C7 122.4(3) . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 120.1(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 N1 119.5(3) . . ?
O1 C7 C4 122.0(3) . . ?
N1 C7 C4 118.5(2) . . ?
N1 C8 C13 106.1(3) . . ?
N1 C8 C9 131.5(3) . . ?
C13 C8 C9 122.4(3) . . ?
C10 C9 C8 115.8(3) . . ?
C10 C9 H9 122.1 . . ?
C8 C9 H9 122.1 . . ?
C11 C10 C9 122.6(4) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 118.3(4) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C8 C13 C12 119.7(3) . . ?
C8 C13 C14 104.9(3) . . ?
C12 C13 C14 135.3(4) . . ?
N2 C14 C13 112.9(3) . . ?
N2 C14 H14 123.5 . . ?
C13 C14 H14 123.5 . . ?
C7 N1 C8 127.6(2) . . ?
C7 N1 N2 120.7(3) . . ?
C8 N1 N2 111.1(2) . . ?
C14 N2 N1 104.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(5) . . . . ?
I1 C1 C2 C3 -179.4(2) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 C7 174.8(3) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C7 C4 C5 C6 -172.9(3) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
I1 C1 C6 C5 -179.1(2) . . . . ?
C4 C5 C6 C1 -1.5(4) . . . . ?
C3 C4 C7 O1 -31.5(4) . . . . ?
C5 C4 C7 O1 141.8(3) . . . . ?
C3 C4 C7 N1 150.8(3) . . . . ?
C5 C4 C7 N1 -35.9(4) . . . . ?
N1 C8 C9 C10 -178.2(3) . . . . ?
C13 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 1.3(6) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
N1 C8 C13 C12 179.2(3) . . . . ?
C9 C8 C13 C12 1.4(5) . . . . ?
N1 C8 C13 C14 -0.6(4) . . . . ?
C9 C8 C13 C14 -178.5(3) . . . . ?
C11 C12 C13 C8 -0.5(6) . . . . ?
C11 C12 C13 C14 179.3(4) . . . . ?
C8 C13 C14 N2 0.0(4) . . . . ?
C12 C13 C14 N2 -179.8(4) . . . . ?
O1 C7 N1 C8 -9.8(5) . . . . ?
C4 C7 N1 C8 167.9(3) . . . . ?
O1 C7 N1 N2 160.1(3) . . . . ?
C4 C7 N1 N2 -22.1(4) . . . . ?
C13 C8 N1 C7 171.8(3) . . . . ?
C9 C8 N1 C7 -10.6(5) . . . . ?
C13 C8 N1 N2 1.1(3) . . . . ?
C9 C8 N1 N2 178.6(3) . . . . ?
C13 C14 N2 N1 0.6(4) . . . . ?
C7 N1 N2 C14 -172.5(3) . . . . ?
C8 N1 N2 C14 -1.1(4) . . . . ?

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
C9 H9 O1 0.93 2.51 2.974(5) 110.8 . yes

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.067



