# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_M_a
_database_code_depnum_ccdc_archive 'CCDC 1909226'
loop_
_audit_author_name
_audit_author_address
'Yogesh Jaiswal'
;IIT Patna
India
;
_audit_update_record             
;
2019-04-10 deposited with the CCDC.	2019-06-18 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         'C9 H8 Br N O3'
_chemical_formula_sum            'C9 H8 Br N O3'
_chemical_formula_weight         258.07

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'
Br Br -0.2901 2.4595 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.507(4)
_cell_length_b                   4.8430(18)
_cell_length_c                   17.180(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.591(9)
_cell_angle_gamma                90
_cell_volume                     941.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2673
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      22.42

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    4.346
_shelx_estimated_absorpt_T_min   0.356
_shelx_estimated_absorpt_T_max   0.356
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            9914
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.732
_diffrn_reflns_theta_max         24.839
_diffrn_reflns_theta_full        24.839
_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             1617
_reflns_number_gt                1029
_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 (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)+(0.0272P)²+1.3371P] 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_number_reflns         1617
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Br01 Br 0.08894(5) 0.30897(13) 0.32121(3) 0.0582(3) Uani 1 1 d . . . . .
O1 O 0.4107(3) 0.4890(7) 0.3264(2) 0.0454(10) Uani 1 1 d . . . . .
O2 O 0.3260(3) 0.7997(8) 0.6268(2) 0.0527(10) Uani 1 1 d . . . . .
O3 O 0.1373(3) 0.9473(8) 0.5739(2) 0.0564(11) Uani 1 1 d . . . . .
N005 N 0.4013(3) 0.0501(8) 0.2834(2) 0.0420(11) Uani 1 1 d . . . . .
H00A H 0.4282 0.0909 0.2413 0.050 Uiso 1 1 calc R U . . .
H00B H 0.3835 -0.1181 0.2922 0.050 Uiso 1 1 calc R U . . .
C006 C 0.3875(4) 0.2454(10) 0.3344(3) 0.0302(12) Uani 1 1 d . . . . .
C007 C 0.2839(4) 0.3584(9) 0.4489(3) 0.0304(12) Uani 1 1 d . . . . .
C008 C 0.2854(4) 0.6613(11) 0.5570(3) 0.0352(12) Uani 1 1 d . . . . .
C009 C 0.1727(4) 0.7479(10) 0.5257(3) 0.0377(14) Uani 1 1 d . . . . .
C00A C 0.1717(4) 0.4521(11) 0.4186(3) 0.0371(13) Uani 1 1 d . . . . .
C00B C 0.3432(4) 0.4678(10) 0.5215(3) 0.0337(12) Uani 1 1 d . . . . .
H00C H 0.4189 0.4096 0.5442 0.040 Uiso 1 1 calc R U . . .
C00C C 0.3443(4) 0.1432(10) 0.4077(3) 0.0370(13) Uani 1 1 d . . . . .
H00D H 0.2897 -0.0085 0.3927 0.044 Uiso 1 1 calc R U . . .
H00E H 0.4113 0.0716 0.4449 0.044 Uiso 1 1 calc R U . . .
C00D C 0.1131(4) 0.6496(11) 0.4557(3) 0.0401(14) Uani 1 1 d . . . . .
H00F H 0.0375 0.7106 0.4338 0.048 Uiso 1 1 calc R U . . .
C00E C 0.2259(5) 0.9459(13) 0.6432(3) 0.0605(17) Uani 1 1 d . . . . .
H00G H 0.1962 0.8571 0.6862 0.073 Uiso 1 1 calc R U . . .
H00H H 0.2481 1.1338 0.6589 0.073 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
Br01 C00A 1.898(5) . ?
O1 C006 1.223(5) . ?
O2 C008 1.377(6) . ?
O2 C00E 1.423(6) . ?
O3 C009 1.381(6) . ?
O3 C00E 1.418(6) . ?
N005 C006 1.320(5) . ?
N005 H00A 0.8600 . ?
N005 H00B 0.8600 . ?
C006 C00C 1.520(6) . ?
C007 C00A 1.377(6) . ?
C007 C00B 1.410(6) . ?
C007 C00C 1.500(6) . ?
C008 C00B 1.357(6) . ?
C008 C009 1.375(6) . ?
C009 C00D 1.357(7) . ?
C00A C00D 1.391(7) . ?
C00B H00C 0.9300 . ?
C00C H00D 0.9700 . ?
C00C H00E 0.9700 . ?
C00D H00F 0.9300 . ?
C00E H00G 0.9700 . ?
C00E H00H 0.9700 . ?

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
C008 O2 C00E 104.9(4) . . ?
C009 O3 C00E 104.7(4) . . ?
C006 N005 H00A 120.0 . . ?
C006 N005 H00B 120.0 . . ?
H00A N005 H00B 120.0 . . ?
O1 C006 N005 124.1(4) . . ?
O1 C006 C00C 121.3(4) . . ?
N005 C006 C00C 114.6(4) . . ?
C00A C007 C00B 118.6(5) . . ?
C00A C007 C00C 122.3(4) . . ?
C00B C007 C00C 119.2(4) . . ?
C00B C008 C009 122.7(5) . . ?
C00B C008 O2 127.7(4) . . ?
C009 C008 O2 109.7(5) . . ?
C00D C009 C008 121.8(5) . . ?
C00D C009 O3 128.3(5) . . ?
C008 C009 O3 109.9(5) . . ?
C007 C00A C00D 123.6(5) . . ?
C007 C00A Br01 119.8(4) . . ?
C00D C00A Br01 116.6(4) . . ?
C008 C00B C007 117.4(4) . . ?
C008 C00B H00C 121.3 . . ?
C007 C00B H00C 121.3 . . ?
C007 C00C C006 114.5(4) . . ?
C007 C00C H00D 108.6 . . ?
C006 C00C H00D 108.6 . . ?
C007 C00C H00E 108.6 . . ?
C006 C00C H00E 108.6 . . ?
H00D C00C H00E 107.6 . . ?
C009 C00D C00A 116.0(5) . . ?
C009 C00D H00F 122.0 . . ?
C00A C00D H00F 122.0 . . ?
O3 C00E O2 108.6(4) . . ?
O3 C00E H00G 110.0 . . ?
O2 C00E H00G 110.0 . . ?
O3 C00E H00H 110.0 . . ?
O2 C00E H00H 110.0 . . ?
H00G C00E H00H 108.3 . . ?

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
C00E O2 C008 C00B -171.5(5) . . . . ?
C00E O2 C008 C009 8.5(5) . . . . ?
C00B C008 C009 C00D -1.8(8) . . . . ?
O2 C008 C009 C00D 178.1(4) . . . . ?
C00B C008 C009 O3 -179.3(4) . . . . ?
O2 C008 C009 O3 0.6(5) . . . . ?
C00E O3 C009 C00D 173.2(5) . . . . ?
C00E O3 C009 C008 -9.5(5) . . . . ?
C00B C007 C00A C00D 0.0(7) . . . . ?
C00C C007 C00A C00D 179.4(4) . . . . ?
C00B C007 C00A Br01 -179.8(3) . . . . ?
C00C C007 C00A Br01 -0.4(6) . . . . ?
C009 C008 C00B C007 1.2(7) . . . . ?
O2 C008 C00B C007 -178.7(4) . . . . ?
C00A C007 C00B C008 -0.3(7) . . . . ?
C00C C007 C00B C008 -179.8(4) . . . . ?
C00A C007 C00C C006 73.8(6) . . . . ?
C00B C007 C00C C006 -106.8(5) . . . . ?
O1 C006 C00C C007 25.3(7) . . . . ?
N005 C006 C00C C007 -157.1(4) . . . . ?
C008 C009 C00D C00A 1.4(7) . . . . ?
O3 C009 C00D C00A 178.4(4) . . . . ?
C007 C00A C00D C009 -0.5(7) . . . . ?
Br01 C00A C00D C009 179.3(4) . . . . ?
C009 O3 C00E O2 14.8(6) . . . . ?
C008 O2 C00E O3 -14.5(6) . . . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_M_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1909424'
loop_
_audit_author_name
_audit_author_address
'Yogesh Jaiswal'
;IIT Patna
India
;
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-06-18 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         ?
_chemical_formula_sum            'C12 H10 I N O'
_chemical_formula_weight         311.11

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.336(7)
_cell_length_b                   4.975(2)
_cell_length_c                   16.193(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.346(13)
_cell_angle_gamma                90
_cell_volume                     1108.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5550
_cell_measurement_theta_min      2.961
_cell_measurement_theta_max      24.555

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.861
_shelx_estimated_absorpt_T_min   0.481
_shelx_estimated_absorpt_T_max   0.598
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            15699
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.961
_diffrn_reflns_theta_max         24.555
_diffrn_reflns_theta_full        24.555
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1844
_reflns_number_gt                1121
_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 (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)+(0.0499P)²+3.3221P] 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_number_reflns         1844
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1006
_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
I1 I 0.84374(5) 0.84697(13) 0.48350(4) 0.0725(3) Uani 1 1 d . . . . .
O1 O 0.5670(4) 0.8323(10) 0.4289(4) 0.0550(15) Uani 1 1 d . . . . .
N1 N 0.5740(4) 1.2620(12) 0.4685(4) 0.0445(17) Uani 1 1 d . . . . .
H2 H 0.5405 1.2336 0.5041 0.053 Uiso 1 1 calc R U . . .
H3 H 0.5945 1.4213 0.4626 0.053 Uiso 1 1 calc R U . . .
C5 C 0.8075(5) 0.5828(14) 0.3063(5) 0.0352(18) Uani 1 1 d . . . . .
C4 C 0.7697(6) 0.7808(15) 0.3526(5) 0.040(2) Uani 1 1 d . . . . .
C3 C 0.6878(6) 0.9230(14) 0.3160(5) 0.044(2) Uani 1 1 d . . . . .
C1 C 0.5940(5) 1.0620(15) 0.4232(5) 0.0385(19) Uani 1 1 d . . . . .
C10 C 0.7544(5) 0.5329(16) 0.2217(5) 0.0403(19) Uani 1 1 d . . . . .
C6 C 0.8929(6) 0.4346(15) 0.3405(5) 0.047(2) Uani 1 1 d . . . . .
H6 H 0.9292 0.4643 0.3971 0.056 Uiso 1 1 calc R U . . .
C9 C 0.7895(7) 0.3294(18) 0.1735(5) 0.052(2) Uani 1 1 d . . . . .
H9 H 0.7542 0.2924 0.1170 0.062 Uiso 1 1 calc R U . . .
C12 C 0.6251(7) 0.8886(16) 0.2262(5) 0.058(3) Uani 1 1 d . . . . .
H12 H 0.5684 0.9836 0.2010 0.070 Uiso 1 1 calc R U . . .
C11 C 0.6673(6) 0.6823(18) 0.1847(5) 0.057(2) Uani 1 1 d . . . . .
H10 H 0.6341 0.6426 0.1279 0.068 Uiso 1 1 calc R U . . .
C8 C 0.8702(7) 0.1967(17) 0.2080(6) 0.055(2) Uani 1 1 d . . . . .
H8 H 0.8916 0.0676 0.1761 0.066 Uiso 1 1 calc R U . . .
C2 C 0.6509(6) 1.1504(15) 0.3622(5) 0.056(2) Uani 1 1 d . . . . .
H5 H 0.7063 1.2551 0.3944 0.067 Uiso 1 1 calc R U . . .
H4 H 0.6100 1.2678 0.3192 0.067 Uiso 1 1 calc R U . . .
C7 C 0.9237(6) 0.2491(18) 0.2927(6) 0.055(2) Uani 1 1 d . . . . .
H7 H 0.9812 0.1559 0.3166 0.066 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
I1 C4 2.112(7) . ?
O1 C1 1.218(8) . ?
N1 C1 1.315(9) . ?
N1 H2 0.8600 . ?
N1 H3 0.8600 . ?
C5 C10 1.390(10) . ?
C5 C6 1.403(10) . ?
C5 C4 1.434(10) . ?
C4 C3 1.357(10) . ?
C3 C12 1.488(11) . ?
C3 C2 1.530(10) . ?
C1 C2 1.513(10) . ?
C10 C11 1.432(11) . ?
C10 C9 1.452(11) . ?
C6 C7 1.356(11) . ?
C6 H6 0.9300 . ?
C9 C8 1.313(11) . ?
C9 H9 0.9300 . ?
C12 C11 1.449(12) . ?
C12 H12 0.9300 . ?
C11 H10 0.9300 . ?
C8 C7 1.394(12) . ?
C8 H8 0.9300 . ?
C2 H5 0.9700 . ?
C2 H4 0.9700 . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H2 120.0 . . ?
C1 N1 H3 120.0 . . ?
H2 N1 H3 120.0 . . ?
C10 C5 C6 118.0(7) . . ?
C10 C5 C4 117.2(7) . . ?
C6 C5 C4 124.8(7) . . ?
C3 C4 C5 122.5(7) . . ?
C3 C4 I1 119.1(6) . . ?
C5 C4 I1 118.4(6) . . ?
C4 C3 C12 125.3(7) . . ?
C4 C3 C2 123.2(7) . . ?
C12 C3 C2 111.5(7) . . ?
O1 C1 N1 123.0(6) . . ?
O1 C1 C2 124.3(7) . . ?
N1 C1 C2 112.7(6) . . ?
C5 C10 C11 119.3(7) . . ?
C5 C10 C9 118.6(7) . . ?
C11 C10 C9 122.1(7) . . ?
C7 C6 C5 121.4(7) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C9 C10 121.2(8) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C12 C3 108.6(8) . . ?
C11 C12 H12 125.7 . . ?
C3 C12 H12 125.7 . . ?
C10 C11 C12 127.1(7) . . ?
C10 C11 H10 116.5 . . ?
C12 C11 H10 116.5 . . ?
C9 C8 C7 120.0(8) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C1 C2 C3 115.3(6) . . ?
C1 C2 H5 108.4 . . ?
C3 C2 H5 108.4 . . ?
C1 C2 H4 108.4 . . ?
C3 C2 H4 108.4 . . ?
H5 C2 H4 107.5 . . ?
C6 C7 C8 120.7(8) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C5 C4 C3 -2.3(10) . . . . ?
C6 C5 C4 C3 178.5(7) . . . . ?
C10 C5 C4 I1 176.6(5) . . . . ?
C6 C5 C4 I1 -2.6(9) . . . . ?
C5 C4 C3 C12 2.2(11) . . . . ?
I1 C4 C3 C12 -176.6(5) . . . . ?
C5 C4 C3 C2 -175.0(6) . . . . ?
I1 C4 C3 C2 6.2(9) . . . . ?
C6 C5 C10 C11 -179.5(7) . . . . ?
C4 C5 C10 C11 1.2(10) . . . . ?
C6 C5 C10 C9 0.5(10) . . . . ?
C4 C5 C10 C9 -178.7(6) . . . . ?
C10 C5 C6 C7 0.4(11) . . . . ?
C4 C5 C6 C7 179.6(7) . . . . ?
C5 C10 C9 C8 -0.9(11) . . . . ?
C11 C10 C9 C8 179.2(8) . . . . ?
C4 C3 C12 C11 -0.9(10) . . . . ?
C2 C3 C12 C11 176.5(6) . . . . ?
C5 C10 C11 C12 -0.1(11) . . . . ?
C9 C10 C11 C12 179.9(7) . . . . ?
C3 C12 C11 C10 -0.1(10) . . . . ?
C10 C9 C8 C7 0.3(12) . . . . ?
O1 C1 C2 C3 -9.3(12) . . . . ?
N1 C1 C2 C3 172.5(7) . . . . ?
C4 C3 C2 C1 -81.5(9) . . . . ?
C12 C3 C2 C1 101.0(8) . . . . ?
C5 C6 C7 C8 -1.1(12) . . . . ?
C9 C8 C7 C6 0.7(12) . . . . ?

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.109

