# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_BzMeBnO_a
_database_code_depnum_ccdc_archive 'CCDC 1520599'
_audit_update_record             
;
2016-12-03 deposited with the CCDC.
2018-04-03 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            'C15 H14 N2 O'
_chemical_formula_weight         238.28

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      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                   10.5352(5)
_cell_length_b                   5.6590(3)
_cell_length_c                   20.7179(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.495(2)
_cell_angle_gamma                90
_cell_volume                     1229.50(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    8924
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.80

_exptl_crystal_description       Cubic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             550
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Photon area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42477
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2492
_reflns_number_gt                1766
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0702P)²+0.2715P] 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       0.050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2492
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
O1 O 0.13595(13) 0.1514(2) 0.69857(6) 0.0690(4) Uani 1 1 d . . . . .
N2 N 0.25374(13) 0.2273(2) 0.61168(6) 0.0495(4) Uani 1 1 d . . . . .
N1 N 0.09385(12) 0.4653(3) 0.62720(6) 0.0507(4) Uani 1 1 d . . . . .
C10 C 0.47432(14) 0.0893(3) 0.64767(7) 0.0436(4) Uani 1 1 d . . . . .
C3 C 0.14509(14) 0.5431(3) 0.57196(7) 0.0453(4) Uani 1 1 d . . . . .
C8 C 0.24692(14) 0.3947(3) 0.56230(7) 0.0451(4) Uani 1 1 d . . . . .
C1 C 0.15835(15) 0.2680(3) 0.65149(8) 0.0506(4) Uani 1 1 d . . . . .
C11 C 0.50453(16) 0.2951(3) 0.68146(8) 0.0503(4) Uani 1 1 d . . . . .
H11 H 0.4420 0.4087 0.6855 0.060 Uiso 1 1 calc R U . . .
C9 C 0.34082(16) 0.0300(3) 0.61926(8) 0.0533(4) Uani 1 1 d . . . . .
H9A H 0.3458 -0.0421 0.5771 0.064 Uiso 1 1 calc R U . . .
H9B H 0.3056 -0.0867 0.6468 0.064 Uiso 1 1 calc R U . . .
C7 C 0.31915(16) 0.4275(3) 0.51108(8) 0.0566(5) Uani 1 1 d . . . . .
H7 H 0.3877 0.3293 0.5049 0.068 Uiso 1 1 calc R U . . .
C15 C 0.56914(17) -0.0761(3) 0.64247(9) 0.0577(5) Uani 1 1 d . . . . .
H15 H 0.5509 -0.2141 0.6190 0.069 Uiso 1 1 calc R U . . .
C4 C 0.11139(17) 0.7254(3) 0.52969(8) 0.0573(5) Uani 1 1 d . . . . .
H4 H 0.0426 0.8232 0.5356 0.069 Uiso 1 1 calc R U . . .
C12 C 0.62720(18) 0.3330(4) 0.70927(8) 0.0607(5) Uani 1 1 d . . . . .
H12 H 0.6469 0.4736 0.7312 0.073 Uiso 1 1 calc R U . . .
C6 C 0.28546(19) 0.6131(4) 0.46909(8) 0.0654(5) Uani 1 1 d . . . . .
H6 H 0.3327 0.6404 0.4341 0.078 Uiso 1 1 calc R U . . .
C5 C 0.18355(19) 0.7574(4) 0.47817(8) 0.0652(5) Uani 1 1 d . . . . .
H5 H 0.1628 0.8792 0.4489 0.078 Uiso 1 1 calc R U . . .
C13 C 0.71963(18) 0.1673(4) 0.70502(10) 0.0702(6) Uani 1 1 d . . . . .
H13 H 0.8017 0.1931 0.7245 0.084 Uiso 1 1 calc R U . . .
C2 C -0.00987(16) 0.5759(4) 0.65736(9) 0.0675(6) Uani 1 1 d . . . . .
H2A H -0.0209 0.4977 0.6976 0.101 Uiso 1 1 calc R U . . .
H2B H -0.0871 0.5636 0.6289 0.101 Uiso 1 1 calc R U . . .
H2C H 0.0098 0.7395 0.6655 0.101 Uiso 1 1 calc R U . . .
C14 C 0.69066(19) -0.0382(4) 0.67172(11) 0.0734(6) Uani 1 1 d . . . . .
H14 H 0.7532 -0.1526 0.6688 0.088 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
O1 C1 1.2192(19) . ?
N2 C1 1.379(2) . ?
N2 C8 1.391(2) . ?
N2 C9 1.444(2) . ?
N1 C1 1.377(2) . ?
N1 C3 1.3835(19) . ?
N1 C2 1.452(2) . ?
C10 C11 1.380(2) . ?
C10 C15 1.381(2) . ?
C10 C9 1.510(2) . ?
C3 C4 1.377(2) . ?
C3 C8 1.392(2) . ?
C8 C7 1.376(2) . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C6 1.388(3) . ?
C7 H7 0.9300 . ?
C15 C14 1.380(3) . ?
C15 H15 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C12 C13 1.361(3) . ?
C12 H12 0.9300 . ?
C6 C5 1.376(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C8 109.67(13) . . ?
C1 N2 C9 123.77(14) . . ?
C8 N2 C9 126.45(14) . . ?
C1 N1 C3 110.03(13) . . ?
C1 N1 C2 123.91(14) . . ?
C3 N1 C2 126.04(15) . . ?
C11 C10 C15 118.57(15) . . ?
C11 C10 C9 123.12(14) . . ?
C15 C10 C9 118.22(15) . . ?
C4 C3 N1 131.85(15) . . ?
C4 C3 C8 121.05(15) . . ?
N1 C3 C8 107.10(14) . . ?
C7 C8 C3 121.35(16) . . ?
C7 C8 N2 131.71(15) . . ?
C3 C8 N2 106.95(13) . . ?
O1 C1 N2 126.58(17) . . ?
O1 C1 N1 127.20(16) . . ?
N2 C1 N1 106.22(13) . . ?
C10 C11 C12 120.27(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
N2 C9 C10 115.40(14) . . ?
N2 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
N2 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C8 C7 C6 117.27(17) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C14 C15 C10 120.55(18) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C3 C4 C5 117.53(17) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C13 C12 C11 120.86(19) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C5 C6 C7 121.28(17) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C5 C4 121.50(17) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C12 C13 C14 119.39(18) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C13 C14 C15 120.34(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_INT1_a
_database_code_depnum_ccdc_archive 'CCDC 1520603'
_audit_update_record             
;
2016-12-03 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        C11H12I2N2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 I2 N2'
_chemical_formula_weight         426.03

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'

_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                   10.1088(11)
_cell_length_b                   10.1122(11)
_cell_length_c                   15.6369(16)
_cell_angle_alpha                106.118(4)
_cell_angle_beta                 90.862(4)
_cell_angle_gamma                117.901(4)
_cell_volume                     1337.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8623
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      24.68

_exptl_crystal_description       Cube
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.116
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    4.676
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Photon area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26112
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5073
_reflns_number_gt                3344
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0532P)²+77.6773P] 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       0.0000(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5073
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0958
_refine_ls_wR_factor_ref         0.2484
_refine_ls_wR_factor_gt          0.2280
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.090
_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 0.37639(17) 0.40065(17) 0.86408(10) 0.0496(4) Uani 1 1 d . . . . .
I3 I 0.01741(17) 0.49131(19) 0.63410(10) 0.0517(4) Uani 1 1 d . . . . .
I5 I 0.65198(18) 0.3180(2) 0.62322(12) 0.0649(5) Uani 1 1 d . . . . .
I2 I 0.2037(2) 0.04179(19) 0.87376(12) 0.0642(5) Uani 1 1 d . . . . .
N4 N 0.328(2) 0.501(2) 0.6231(13) 0.051(5) Uani 1 1 d . . . . .
N2 N 0.404(2) 0.722(2) 0.8750(12) 0.052(5) Uani 1 1 d . . . . .
C16 C 0.260(3) 0.332(3) 0.6090(16) 0.062(7) Uani 1 1 d . . . . .
H16A H 0.1743 0.3016 0.6411 0.074 Uiso 1 1 calc R U . . .
H16B H 0.3339 0.3141 0.6366 0.074 Uiso 1 1 calc R U . . .
C8 C 0.292(3) 0.722(2) 1.1325(19) 0.066(7) Uani 1 1 d . . . . .
H8 H 0.3613 0.7326 1.1772 0.079 Uiso 1 1 calc R U . . .
C1 C 0.475(3) 0.633(3) 0.8674(15) 0.056(6) Uani 1 1 d . . . . .
N1 N 0.617(3) 0.730(2) 0.8660(13) 0.080(8) Uani 1 1 d . . . . .
N3 N 0.349(2) 0.722(2) 0.6330(13) 0.063(6) Uani 1 1 d . . . . .
C17 C 0.206(2) 0.225(3) 0.5142(17) 0.055(6) Uani 1 1 d . . . . .
C12 C 0.249(3) 0.583(3) 0.6312(15) 0.067(8) Uani 1 1 d . . . . .
C7 C 0.315(3) 0.703(2) 1.0492(17) 0.051(6) Uani 1 1 d . . . . .
H7 H 0.3999 0.6935 1.0350 0.062 Uiso 1 1 calc R U . . .
C22 C 0.154(3) 0.266(3) 0.4487(16) 0.059(6) Uani 1 1 d . . . . .
H22 H 0.1608 0.3643 0.4616 0.070 Uiso 1 1 calc R U . . .
C6 C 0.222(3) 0.698(3) 0.9799(18) 0.063(6) Uani 1 1 d . . . . .
C18 C 0.201(3) 0.083(3) 0.494(2) 0.068(7) Uani 1 1 d . . . . .
H18 H 0.2335 0.0537 0.5384 0.081 Uiso 1 1 calc R U . . .
C21 C 0.092(3) 0.153(3) 0.3615(19) 0.077(8) Uani 1 1 d . . . . .
H21 H 0.0494 0.1751 0.3179 0.092 Uiso 1 1 calc R U . . .
C9 C 0.155(4) 0.725(3) 1.153(2) 0.087(9) Uani 1 1 d . . . . .
H9 H 0.1327 0.7352 1.2112 0.105 Uiso 1 1 calc R U . . .
C4 C 0.514(3) 0.877(3) 0.8783(16) 0.071(8) Uani 1 1 d . . . . .
H4 H 0.4927 0.9580 0.8825 0.085 Uiso 1 1 calc R U . . .
C5 C 0.247(4) 0.671(4) 0.8835(16) 0.087(10) Uani 1 1 d . . . . .
H5A H 0.1866 0.5591 0.8499 0.104 Uiso 1 1 calc R U . . .
H5B H 0.2124 0.7273 0.8568 0.104 Uiso 1 1 calc R U . . .
C11 C 0.091(3) 0.701(3) 0.999(2) 0.075(8) Uani 1 1 d . . . . .
H11 H 0.0267 0.6963 0.9536 0.090 Uiso 1 1 calc R U . . .
C19 C 0.147(3) -0.015(3) 0.407(3) 0.087(10) Uani 1 1 d . . . . .
H19 H 0.1467 -0.1110 0.3918 0.104 Uiso 1 1 calc R U . . .
C20 C 0.094(4) 0.021(3) 0.341(2) 0.079(8) Uani 1 1 d . . . . .
H20 H 0.0597 -0.0481 0.2817 0.095 Uiso 1 1 calc R U . . .
C14 C 0.505(4) 0.753(4) 0.6257(19) 0.092(7) Uani 1 1 d . . . . .
H14 H 0.5925 0.8410 0.6233 0.110 Uiso 1 1 calc R U . . .
C10 C 0.055(3) 0.713(3) 1.084(3) 0.087(10) Uani 1 1 d . . . . .
H10 H -0.0355 0.7128 1.0955 0.104 Uiso 1 1 calc R U . . .
C13 C 0.321(4) 0.856(3) 0.636(2) 0.092(10) Uani 1 1 d . . . . .
H13A H 0.2139 0.8204 0.6311 0.138 Uiso 1 1 calc R U . . .
H13B H 0.3581 0.8951 0.5871 0.138 Uiso 1 1 calc R U . . .
H13C H 0.3729 0.9399 0.6924 0.138 Uiso 1 1 calc R U . . .
C3 C 0.664(4) 0.893(4) 0.8746(19) 0.092(7) Uani 1 1 d . . . . .
H3 H 0.7582 0.9791 0.8769 0.110 Uiso 1 1 calc R U . . .
C15 C 0.472(3) 0.598(5) 0.6238(17) 0.087(11) Uani 1 1 d . . . . .
H15 H 0.5458 0.5685 0.6231 0.104 Uiso 1 1 calc R U . . .
C2 C 0.747(3) 0.687(3) 0.863(2) 0.088(9) Uani 1 1 d . . . . .
H2A H 0.7695 0.6782 0.9206 0.131 Uiso 1 1 calc R U . . .
H2B H 0.8357 0.7682 0.8512 0.131 Uiso 1 1 calc R U . . .
H2C H 0.7142 0.5881 0.8167 0.131 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 C1 2.06(2) . ?
I1 I2 3.259(2) . ?
I3 C12 2.09(2) . ?
N4 C15 1.32(3) . ?
N4 C12 1.38(3) . ?
N4 C16 1.46(3) . ?
N2 C1 1.38(3) . ?
N2 C4 1.42(3) . ?
N2 C5 1.44(4) . ?
C16 C17 1.48(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C8 C7 1.31(3) . ?
C8 C9 1.44(4) . ?
C8 H8 0.9300 . ?
C1 N1 1.31(3) . ?
N1 C3 1.45(4) . ?
N1 C2 1.56(4) . ?
N3 C12 1.28(3) . ?
N3 C14 1.47(4) . ?
N3 C13 1.50(3) . ?
C17 C18 1.36(3) . ?
C17 C22 1.38(3) . ?
C7 C6 1.40(3) . ?
C7 H7 0.9300 . ?
C22 C21 1.41(3) . ?
C22 H22 0.9300 . ?
C6 C11 1.37(4) . ?
C6 C5 1.50(4) . ?
C18 C19 1.37(4) . ?
C18 H18 0.9300 . ?
C21 C20 1.29(4) . ?
C21 H21 0.9300 . ?
C9 C10 1.41(4) . ?
C9 H9 0.9300 . ?
C4 C3 1.45(4) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C11 C10 1.37(4) . ?
C11 H11 0.9300 . ?
C19 C20 1.37(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C14 C15 1.43(5) . ?
C14 H14 0.9300 . ?
C10 H10 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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 I1 I2 174.7(7) . . ?
C15 N4 C12 108(2) . . ?
C15 N4 C16 126(2) . . ?
C12 N4 C16 125(2) . . ?
C1 N2 C4 108(2) . . ?
C1 N2 C5 126(2) . . ?
C4 N2 C5 126(2) . . ?
N4 C16 C17 117(2) . . ?
N4 C16 H16A 108.1 . . ?
C17 C16 H16A 108.1 . . ?
N4 C16 H16B 108.1 . . ?
C17 C16 H16B 108.1 . . ?
H16A C16 H16B 107.3 . . ?
C7 C8 C9 118(3) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
N1 C1 N2 104(2) . . ?
N1 C1 I1 129(2) . . ?
N2 C1 I1 126.2(19) . . ?
C1 N1 C3 120(3) . . ?
C1 N1 C2 124(2) . . ?
C3 N1 C2 116(2) . . ?
C12 N3 C14 118(3) . . ?
C12 N3 C13 126(2) . . ?
C14 N3 C13 115(2) . . ?
C18 C17 C22 121(2) . . ?
C18 C17 C16 118(2) . . ?
C22 C17 C16 121(2) . . ?
N3 C12 N4 105(2) . . ?
N3 C12 I3 129(2) . . ?
N4 C12 I3 126(2) . . ?
C8 C7 C6 124(3) . . ?
C8 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
C17 C22 C21 118(2) . . ?
C17 C22 H22 121.1 . . ?
C21 C22 H22 121.1 . . ?
C11 C6 C7 118(3) . . ?
C11 C6 C5 118(2) . . ?
C7 C6 C5 124(2) . . ?
C17 C18 C19 117(3) . . ?
C17 C18 H18 121.4 . . ?
C19 C18 H18 121.4 . . ?
C20 C21 C22 122(3) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C10 C9 C8 119(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N2 C4 C3 112(3) . . ?
N2 C4 H4 123.9 . . ?
C3 C4 H4 123.9 . . ?
N2 C5 C6 113(2) . . ?
N2 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C10 C11 C6 121(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C18 C19 C20 123(3) . . ?
C18 C19 H19 118.4 . . ?
C20 C19 H19 118.4 . . ?
C21 C20 C19 119(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C15 C14 N3 94(2) . . ?
C15 C14 H14 133.1 . . ?
N3 C14 H14 133.1 . . ?
C11 C10 C9 119(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C3 N1 95(2) . . ?
C4 C3 H3 132.3 . . ?
N1 C3 H3 132.3 . . ?
N4 C15 C14 115(3) . . ?
N4 C15 H15 122.6 . . ?
C14 C15 H15 122.6 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

_refine_diff_density_max         2.659
_refine_diff_density_min         -1.425
_refine_diff_density_rms         0.266

####################################################################### 
# 
# 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_BnImI_b
_database_code_depnum_ccdc_archive 'CCDC 1520602'
_audit_update_record             
;
2016-12-03 deposited with the CCDC.
2018-04-03 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            'C10 H9 I N2'
_chemical_formula_weight         285.10

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.7463(3)
_cell_length_b                   9.1092(3)
_cell_length_c                   13.1444(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1047.24(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.34

_exptl_crystal_description       Cubic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.184
_exptl_absorpt_coefficient_mu    3.014
_shelx_estimated_absorpt_T_min   0.492
_shelx_estimated_absorpt_T_max   0.607
_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      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Photon area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22060
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.797
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2146
_reflns_number_gt                2101
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0144P)²+0.1759P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0290(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 864 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2146
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0132
_refine_ls_R_factor_gt           0.0126
_refine_ls_wR_factor_ref         0.0296
_refine_ls_wR_factor_gt          0.0294
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_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 0.26362(2) 0.71820(2) 0.46940(2) 0.04565(8) Uani 1 1 d . . . . .
N1 N 0.5672(3) 0.6858(3) 0.36253(19) 0.0487(6) Uani 1 1 d . . . . .
C1 C 0.4215(3) 0.6520(3) 0.3601(2) 0.0406(6) Uani 1 1 d . . . . .
C10 C 0.1800(4) 0.7610(4) 0.1645(2) 0.0533(8) Uani 1 1 d . . . . .
C4 C 0.2353(5) 0.5145(3) 0.2471(3) 0.0543(8) Uani 1 1 d . . . . .
C5 C 0.1439(3) 0.6161(3) 0.1800(2) 0.0444(6) Uani 1 1 d . . . . .
C2 C 0.6273(4) 0.6220(4) 0.2759(3) 0.0565(8) Uani 1 1 d . . . . .
N2 N 0.3848(3) 0.5705(3) 0.27722(19) 0.0454(6) Uani 1 1 d . . . . .
C8 C -0.0346(4) 0.7887(6) 0.0537(3) 0.0717(11) Uani 1 1 d . . . . .
C3 C 0.5190(4) 0.5533(4) 0.2239(3) 0.0571(8) Uani 1 1 d . . . . .
C9 C 0.0900(5) 0.8468(5) 0.1012(3) 0.0645(9) Uani 1 1 d . . . . .
C6 C 0.0164(4) 0.5584(5) 0.1323(3) 0.0593(8) Uani 1 1 d . . . . .
C7 C -0.0721(5) 0.6429(6) 0.0696(3) 0.0749(11) Uani 1 1 d . . . . .
H3 H 0.257(5) 0.418(4) 0.213(3) 0.077(10) Uiso 1 1 d . . . . .
H9 H 0.255(4) 0.799(4) 0.195(3) 0.064(10) Uiso 1 1 d . . . . .
H1 H 0.731(5) 0.627(4) 0.262(3) 0.070(10) Uiso 1 1 d . . . . .
H5 H -0.006(4) 0.469(5) 0.146(3) 0.070(13) Uiso 1 1 d . . . . .
H2 H 0.523(5) 0.507(5) 0.166(4) 0.096(17) Uiso 1 1 d . . . . .
H7 H -0.094(6) 0.832(5) 0.014(3) 0.092(15) Uiso 1 1 d . . . . .
H6 H -0.164(6) 0.607(6) 0.038(4) 0.115(16) Uiso 1 1 d . . . . .
H4 H 0.182(4) 0.500(4) 0.304(3) 0.058(11) Uiso 1 1 d . . . . .
H8 H 0.120(5) 0.931(6) 0.093(3) 0.089(15) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.082(3) . ?
N1 C1 1.312(4) . ?
N1 C2 1.382(4) . ?
C1 N2 1.357(4) . ?
C10 C5 1.373(5) . ?
C10 C9 1.386(5) . ?
C10 H9 0.84(4) . ?
C4 N2 1.459(4) . ?
C4 C5 1.507(4) . ?
C4 H3 1.00(4) . ?
C4 H4 0.89(3) . ?
C5 C6 1.383(4) . ?
C2 C3 1.325(5) . ?
C2 H1 0.92(4) . ?
N2 C3 1.376(4) . ?
C8 C9 1.364(6) . ?
C8 C7 1.384(7) . ?
C8 H7 0.83(5) . ?
C3 H2 0.87(5) . ?
C9 H8 0.82(5) . ?
C6 C7 1.368(6) . ?
C6 H5 0.86(4) . ?
C7 H6 0.96(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
C1 N1 C2 104.5(3) . . ?
N1 C1 N2 112.2(3) . . ?
N1 C1 I1 124.0(2) . . ?
N2 C1 I1 123.8(2) . . ?
C5 C10 C9 120.0(3) . . ?
C5 C10 H9 120(2) . . ?
C9 C10 H9 120(2) . . ?
N2 C4 C5 114.8(3) . . ?
N2 C4 H3 105(3) . . ?
C5 C4 H3 112(2) . . ?
N2 C4 H4 107(2) . . ?
C5 C4 H4 108(2) . . ?
H3 C4 H4 110(3) . . ?
C10 C5 C6 118.9(3) . . ?
C10 C5 C4 123.7(3) . . ?
C6 C5 C4 117.4(3) . . ?
C3 C2 N1 110.6(3) . . ?
C3 C2 H1 128(2) . . ?
N1 C2 H1 121(2) . . ?
C1 N2 C3 105.6(3) . . ?
C1 N2 C4 128.4(3) . . ?
C3 N2 C4 125.9(3) . . ?
C9 C8 C7 119.5(4) . . ?
C9 C8 H7 127(3) . . ?
C7 C8 H7 113(3) . . ?
C2 C3 N2 107.1(3) . . ?
C2 C3 H2 131(3) . . ?
N2 C3 H2 122(3) . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H8 124(3) . . ?
C10 C9 H8 115(3) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H5 122(3) . . ?
C5 C6 H5 117(3) . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H6 123(3) . . ?
C8 C7 H6 117(3) . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_MeBzOCOOEt_a
_database_code_depnum_ccdc_archive 'CCDC 1520600'
_audit_update_record             
;
2016-12-03 deposited with the CCDC.
2018-04-03 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            'C11 H12 N2 O3'
_chemical_formula_weight         220.23

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      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                   4.6419(3)
_cell_length_b                   24.9757(17)
_cell_length_c                   9.3367(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.371(2)
_cell_angle_gamma                90
_cell_volume                     1073.50(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3883
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.06

_exptl_crystal_description       cubic
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Photon area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19635
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2121
_reflns_number_gt                1201
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0438P)²+0.4417P] 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       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2121
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
O2 O 0.3545(4) 0.60376(6) 0.59324(19) 0.0561(5) Uani 1 1 d . . . . .
O1 O 0.6152(4) 0.53863(7) 0.7145(2) 0.0657(6) Uani 1 1 d . . . . .
O3 O 0.4965(4) 0.70489(7) 0.6628(2) 0.0739(7) Uani 1 1 d . . . . .
N1 N 0.7191(4) 0.62616(7) 0.7653(2) 0.0476(6) Uani 1 1 d . . . . .
N2 N 0.8803(5) 0.70555(8) 0.8450(2) 0.0534(6) Uani 1 1 d . . . . .
C6 C 1.0510(5) 0.66714(10) 0.9236(3) 0.0478(6) Uani 1 1 d . . . . .
C7 C 0.9533(5) 0.61715(9) 0.8754(3) 0.0447(6) Uani 1 1 d . . . . .
C9 C 0.5613(6) 0.58487(11) 0.6913(3) 0.0497(7) Uani 1 1 d . . . . .
C2 C 1.0819(6) 0.57137(10) 0.9340(3) 0.0553(7) Uani 1 1 d . . . . .
H2 H 1.0176 0.5377 0.9018 0.066 Uiso 1 1 calc R U . . .
C1 C 0.6754(6) 0.68226(10) 0.7471(3) 0.0534(7) Uani 1 1 d . . . . .
C5 C 1.2804(6) 0.67331(11) 1.0312(3) 0.0592(8) Uani 1 1 d . . . . .
H5 H 1.3458 0.7070 1.0630 0.071 Uiso 1 1 calc R U . . .
C10 C 0.1876(6) 0.56255(11) 0.5089(3) 0.0624(8) Uani 1 1 d . . . . .
H10A H 0.0848 0.5404 0.5711 0.075 Uiso 1 1 calc R U . . .
H10B H 0.3155 0.5398 0.4613 0.075 Uiso 1 1 calc R U . . .
C3 C 1.3125(6) 0.57740(12) 1.0435(3) 0.0638(8) Uani 1 1 d . . . . .
H3 H 1.4030 0.5471 1.0863 0.077 Uiso 1 1 calc R U . . .
C4 C 1.4087(6) 0.62708(12) 1.0896(3) 0.0651(8) Uani 1 1 d . . . . .
H4 H 1.5649 0.6297 1.1624 0.078 Uiso 1 1 calc R U . . .
C11 C -0.0229(6) 0.59056(12) 0.3996(3) 0.0716(9) Uani 1 1 d . . . . .
H11A H -0.1428 0.6141 0.4479 0.107 Uiso 1 1 calc R U . . .
H11B H -0.1428 0.5646 0.3445 0.107 Uiso 1 1 calc R U . . .
H11C H 0.0816 0.6110 0.3361 0.107 Uiso 1 1 calc R U . . .
C8 C 0.9108(7) 0.76339(10) 0.8603(3) 0.0769(10) Uani 1 1 d . . . . .
H8A H 1.0286 0.7767 0.7908 0.115 Uiso 1 1 calc R U . . .
H8B H 1.0013 0.7718 0.9559 0.115 Uiso 1 1 calc R U . . .
H8C H 0.7224 0.7798 0.8442 0.115 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
O2 C9 1.325(3) . ?
O2 C10 1.457(3) . ?
O1 C9 1.196(3) . ?
O3 C1 1.208(3) . ?
N1 C9 1.395(3) . ?
N1 C7 1.416(3) . ?
N1 C1 1.423(3) . ?
N2 C1 1.362(3) . ?
N2 C6 1.392(3) . ?
N2 C8 1.457(3) . ?
C6 C5 1.376(3) . ?
C6 C7 1.383(3) . ?
C7 C2 1.371(3) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9300 . ?
C5 C4 1.379(4) . ?
C5 H5 0.9300 . ?
C10 C11 1.493(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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 O2 C10 114.2(2) . . ?
C9 N1 C7 123.2(2) . . ?
C9 N1 C1 127.6(2) . . ?
C7 N1 C1 109.13(19) . . ?
C1 N2 C6 111.2(2) . . ?
C1 N2 C8 122.7(2) . . ?
C6 N2 C8 126.2(2) . . ?
C5 C6 C7 122.0(2) . . ?
C5 C6 N2 130.0(2) . . ?
C7 C6 N2 108.0(2) . . ?
C2 C7 C6 121.0(2) . . ?
C2 C7 N1 132.6(2) . . ?
C6 C7 N1 106.4(2) . . ?
O1 C9 O2 125.8(2) . . ?
O1 C9 N1 122.7(2) . . ?
O2 C9 N1 111.5(2) . . ?
C7 C2 C3 117.2(2) . . ?
C7 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
O3 C1 N2 126.8(2) . . ?
O3 C1 N1 127.9(2) . . ?
N2 C1 N1 105.3(2) . . ?
C6 C5 C4 116.7(3) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
O2 C10 C11 107.1(2) . . ?
O2 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1520601'
_audit_update_record             
;
2016-12-03 deposited with the CCDC.
2018-04-03 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            'C10 H13 Br N2 O'
_chemical_formula_weight         257.13

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'
Br Br -0.2901 2.4595 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.9971(5)
_cell_length_b                   8.2161(5)
_cell_length_c                   14.9390(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.864(2)
_cell_angle_gamma                90
_cell_volume                     1102.93(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    5394
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      24.13

_exptl_crystal_description       Cubic
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.697
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Photon Area Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20511
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2260
_reflns_number_gt                1616
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0239P)²+0.8398P] 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       0.0083(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2260
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Br1 Br 0.47196(4) 0.03492(4) 0.75795(2) 0.06075(15) Uani 1 1 d . . . . .
N1 N 0.5150(3) 0.4507(3) 0.66575(15) 0.0476(6) Uani 1 1 d . . . . .
N2 N 0.3464(3) 0.3149(3) 0.58696(17) 0.0527(6) Uani 1 1 d . . . . .
O2 O 0.5099(3) 0.3852(4) 0.85807(17) 0.0888(8) Uani 1 1 d . . . . .
H13 H 0.4984 0.2921 0.8392 0.133 Uiso 1 1 calc R U . . .
C1 C 0.5871(3) 0.3752(3) 0.59682(18) 0.0449(7) Uani 1 1 d . . . . .
C6 C 0.4803(3) 0.2892(3) 0.54636(19) 0.0453(7) Uani 1 1 d . . . . .
C2 C 0.7353(3) 0.3785(4) 0.5748(2) 0.0564(8) Uani 1 1 d . . . . .
H1 H 0.8076 0.4347 0.6091 0.068 Uiso 1 1 calc R U . . .
C5 C 0.5149(4) 0.2043(4) 0.4703(2) 0.0560(8) Uani 1 1 d . . . . .
H4 H 0.4431 0.1468 0.4364 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3722(4) 0.4103(4) 0.6573(2) 0.0559(8) Uani 1 1 d . . . . .
H8 H 0.3001 0.4445 0.6956 0.067 Uiso 1 1 calc R U . . .
C9 C 0.5831(4) 0.5529(4) 0.7366(2) 0.0598(8) Uani 1 1 d . . . . .
H9 H 0.5128 0.6362 0.7526 0.072 Uiso 1 1 calc R U . . .
H10 H 0.6697 0.6069 0.7143 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6603(4) 0.2092(4) 0.4477(2) 0.0651(9) Uani 1 1 d . . . . .
H3 H 0.6877 0.1545 0.3966 0.078 Uiso 1 1 calc R U . . .
C3 C 0.7685(4) 0.2937(4) 0.4991(2) 0.0650(9) Uani 1 1 d . . . . .
H2 H 0.8662 0.2926 0.4815 0.078 Uiso 1 1 calc R U . . .
C10 C 0.6286(4) 0.4565(4) 0.8179(2) 0.0668(9) Uani 1 1 d . . . . .
H11 H 0.6974 0.3720 0.8014 0.080 Uiso 1 1 calc R U . . .
H12 H 0.6806 0.5273 0.8610 0.080 Uiso 1 1 calc R U . . .
C7 C 0.2018(4) 0.2441(5) 0.5593(3) 0.0794(11) Uani 1 1 d . . . . .
H6 H 0.2027 0.1297 0.5723 0.119 Uiso 1 1 calc R U . . .
H5 H 0.1829 0.2604 0.4961 0.119 Uiso 1 1 calc R U . . .
H7 H 0.1251 0.2961 0.5914 0.119 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
N1 C8 1.326(4) . ?
N1 C1 1.390(4) . ?
N1 C9 1.461(4) . ?
N2 C8 1.322(4) . ?
N2 C6 1.392(4) . ?
N2 C7 1.465(4) . ?
O2 C10 1.381(4) . ?
O2 H13 0.8200 . ?
C1 C6 1.385(4) . ?
C1 C2 1.390(4) . ?
C6 C5 1.382(4) . ?
C2 C3 1.374(4) . ?
C2 H1 0.9300 . ?
C5 C4 1.368(5) . ?
C5 H4 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.491(5) . ?
C9 H9 0.9700 . ?
C9 H10 0.9700 . ?
C4 C3 1.394(5) . ?
C4 H3 0.9300 . ?
C3 H2 0.9300 . ?
C10 H11 0.9700 . ?
C10 H12 0.9700 . ?
C7 H6 0.9600 . ?
C7 H5 0.9600 . ?
C7 H7 0.9600 . ?

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
C8 N1 C1 107.7(3) . . ?
C8 N1 C9 125.6(3) . . ?
C1 N1 C9 126.7(3) . . ?
C8 N2 C6 108.3(3) . . ?
C8 N2 C7 125.2(3) . . ?
C6 N2 C7 126.4(3) . . ?
C10 O2 H13 109.5 . . ?
C6 C1 C2 121.9(3) . . ?
C6 C1 N1 107.1(3) . . ?
C2 C1 N1 131.0(3) . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 N2 132.1(3) . . ?
C1 C6 N2 106.1(3) . . ?
C3 C2 C1 115.8(3) . . ?
C3 C2 H1 122.1 . . ?
C1 C2 H1 122.1 . . ?
C4 C5 C6 116.4(3) . . ?
C4 C5 H4 121.8 . . ?
C6 C5 H4 121.8 . . ?
N2 C8 N1 110.8(3) . . ?
N2 C8 H8 124.6 . . ?
N1 C8 H8 124.6 . . ?
N1 C9 C10 111.9(3) . . ?
N1 C9 H9 109.2 . . ?
C10 C9 H9 109.2 . . ?
N1 C9 H10 109.2 . . ?
C10 C9 H10 109.2 . . ?
H9 C9 H10 107.9 . . ?
C5 C4 C3 122.0(3) . . ?
C5 C4 H3 119.0 . . ?
C3 C4 H3 119.0 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H2 119.0 . . ?
C4 C3 H2 119.0 . . ?
O2 C10 C9 113.1(3) . . ?
O2 C10 H11 109.0 . . ?
C9 C10 H11 109.0 . . ?
O2 C10 H12 109.0 . . ?
C9 C10 H12 109.0 . . ?
H11 C10 H12 107.8 . . ?
N2 C7 H6 109.5 . . ?
N2 C7 H5 109.5 . . ?
H6 C7 H5 109.5 . . ?
N2 C7 H7 109.5 . . ?
H6 C7 H7 109.5 . . ?
H5 C7 H7 109.5 . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_7_a
_database_code_depnum_ccdc_archive 'CCDC 1587815'
_audit_update_record             
;
2017-11-27 deposited with the CCDC.
2018-04-03 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            'C21 H14 Cl N3 O'
_chemical_formula_weight         359.8141

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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.070(4)
_cell_length_b                   20.668(16)
_cell_length_c                   16.000(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.39(2)
_cell_angle_gamma                90
_cell_volume                     1674(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3544
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.67

_exptl_crystal_description       Needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             858
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.958
_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      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-Ray
_diffrn_measurement_device_type  'Photon area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14899
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         25.663
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3144
_reflns_number_gt                1213
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] 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       0.009(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3144
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2245
_refine_ls_R_factor_gt           0.1177
_refine_ls_wR_factor_ref         0.3965
_refine_ls_wR_factor_gt          0.3100
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
Cl1 Cl 1.3402(5) 0.05599(11) 0.34460(15) 0.1249(11) Uani 1 1 d . . . . .
O1 O 0.6171(10) 0.1726(2) 0.6535(3) 0.0949(16) Uani 1 1 d . . . . .
N2 N 0.4801(11) 0.2347(3) 0.5410(3) 0.0799(17) Uani 1 1 d . . . . .
N3 N 0.6414(12) 0.2246(3) 0.4031(4) 0.0855(17) Uani 1 1 d . . . . .
N1 N 0.3051(12) 0.2976(3) 0.4399(4) 0.0846(17) Uani 1 1 d . . . . .
C7 C 0.6379(14) 0.1860(3) 0.5792(4) 0.0774(19) Uani 1 1 d . . . . .
C8 C 0.2901(13) 0.2733(3) 0.5782(4) 0.0784(19) Uani 1 1 d . . . . .
C5 C 0.8060(14) 0.1755(3) 0.4359(4) 0.0794(19) Uani 1 1 d . . . . .
C6 C 0.8121(13) 0.1558(3) 0.5201(4) 0.0758(19) Uani 1 1 d . . . . .
C00A C 0.4893(15) 0.2512(3) 0.4559(4) 0.0777(19) Uani 1 1 d . . . . .
C13 C 0.1764(14) 0.3121(3) 0.5127(5) 0.0789(19) Uani 1 1 d . . . . .
C15 C 0.4317(15) 0.3852(3) 0.3431(4) 0.083(2) Uani 1 1 d . . . . .
C4 C 0.9757(14) 0.1452(4) 0.3825(5) 0.086(2) Uani 1 1 d . . . . .
H4 H 0.9780 0.1582 0.3269 0.104 Uiso 1 1 calc R U . . .
C1 C 0.9780(15) 0.1050(3) 0.5483(5) 0.089(2) Uani 1 1 d . . . . .
H1 H 0.9742 0.0913 0.6035 0.107 Uiso 1 1 calc R U . . .
C16 C 0.6048(16) 0.3837(4) 0.2793(4) 0.093(2) Uani 1 1 d . . . . .
H16 H 0.6136 0.3476 0.2449 0.112 Uiso 1 1 calc R U . . .
C20 C 0.4213(16) 0.4392(4) 0.3932(5) 0.096(2) Uani 1 1 d . . . . .
H20 H 0.3041 0.4407 0.4357 0.115 Uiso 1 1 calc R U . . .
C9 C 0.2084(16) 0.2776(4) 0.6584(5) 0.092(2) Uani 1 1 d . . . . .
H9 H 0.2870 0.2528 0.7015 0.110 Uiso 1 1 calc R U . . .
C2 C 1.1455(16) 0.0751(3) 0.4964(5) 0.094(2) Uani 1 1 d . . . . .
H2 H 1.2587 0.0422 0.5156 0.113 Uiso 1 1 calc R U . . .
C12 C -0.0229(16) 0.3549(4) 0.5287(5) 0.094(2) Uani 1 1 d . . . . .
H12 H -0.0985 0.3812 0.4866 0.113 Uiso 1 1 calc R U . . .
C14 C 0.2566(16) 0.3270(4) 0.3568(4) 0.099(2) Uani 1 1 d . . . . .
H14A H 0.0731 0.3403 0.3500 0.119 Uiso 1 1 calc R U . . .
H14B H 0.2865 0.2948 0.3143 0.119 Uiso 1 1 calc R U . . .
C3 C 1.1389(16) 0.0964(4) 0.4119(5) 0.096(2) Uani 1 1 d . . . . .
C19 C 0.5869(19) 0.4915(4) 0.3800(5) 0.103(3) Uani 1 1 d . . . . .
H19 H 0.5802 0.5276 0.4143 0.124 Uiso 1 1 calc R U . . .
C10 C 0.0050(18) 0.3201(4) 0.6726(5) 0.105(2) Uani 1 1 d . . . . .
H10 H -0.0576 0.3235 0.7259 0.126 Uiso 1 1 calc R U . . .
C11 C -0.1060(16) 0.3577(4) 0.6079(6) 0.101(2) Uani 1 1 d . . . . .
H11 H -0.2424 0.3859 0.6191 0.121 Uiso 1 1 calc R U . . .
C17 C 0.7676(18) 0.4380(4) 0.2674(5) 0.103(3) Uani 1 1 d . . . . .
H17 H 0.8833 0.4377 0.2244 0.124 Uiso 1 1 calc R U . . .
C18 C 0.7571(18) 0.4906(4) 0.3180(6) 0.107(3) Uani 1 1 d . . . . .
H18 H 0.8667 0.5259 0.3101 0.128 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
Cl1 C3 1.741(8) . ?
O1 C7 1.231(7) . ?
N2 C7 1.402(8) . ?
N2 C00A 1.407(8) . ?
N2 C8 1.409(8) . ?
N3 C00A 1.298(8) . ?
N3 C5 1.396(9) . ?
N1 C00A 1.352(8) . ?
N1 C13 1.401(9) . ?
N1 C14 1.470(8) . ?
C7 C6 1.470(9) . ?
C8 C9 1.375(9) . ?
C8 C13 1.415(9) . ?
C5 C4 1.396(9) . ?
C5 C6 1.406(8) . ?
C6 C1 1.404(9) . ?
C13 C12 1.379(10) . ?
C15 C20 1.377(10) . ?
C15 C16 1.385(9) . ?
C15 C14 1.517(10) . ?
C4 C3 1.371(10) . ?
C4 H4 0.9300 . ?
C1 C2 1.370(9) . ?
C1 H1 0.9300 . ?
C16 C17 1.412(10) . ?
C16 H16 0.9300 . ?
C20 C19 1.393(11) . ?
C20 H20 0.9300 . ?
C9 C10 1.384(10) . ?
C9 H9 0.9300 . ?
C2 C3 1.420(10) . ?
C2 H2 0.9300 . ?
C12 C11 1.360(10) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C19 C18 1.353(10) . ?
C19 H19 0.9300 . ?
C10 C11 1.388(11) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C17 C18 1.359(10) . ?
C17 H17 0.9300 . ?
C18 H18 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
C7 N2 C00A 123.0(6) . . ?
C7 N2 C8 127.5(6) . . ?
C00A N2 C8 109.5(6) . . ?
C00A N3 C5 115.4(6) . . ?
C00A N1 C13 110.2(6) . . ?
C00A N1 C14 122.8(6) . . ?
C13 N1 C14 127.1(6) . . ?
O1 C7 N2 120.2(6) . . ?
O1 C7 C6 127.9(6) . . ?
N2 C7 C6 111.9(6) . . ?
C9 C8 N2 133.0(7) . . ?
C9 C8 C13 121.5(7) . . ?
N2 C8 C13 105.5(6) . . ?
C4 C5 N3 118.2(7) . . ?
C4 C5 C6 118.5(7) . . ?
N3 C5 C6 123.3(7) . . ?
C1 C6 C5 120.2(7) . . ?
C1 C6 C7 118.9(6) . . ?
C5 C6 C7 120.9(6) . . ?
N3 C00A N1 127.4(6) . . ?
N3 C00A N2 125.5(7) . . ?
N1 C00A N2 107.1(6) . . ?
C12 C13 N1 132.4(7) . . ?
C12 C13 C8 119.8(7) . . ?
N1 C13 C8 107.8(6) . . ?
C20 C15 C16 119.6(7) . . ?
C20 C15 C14 121.0(7) . . ?
C16 C15 C14 119.4(7) . . ?
C3 C4 C5 120.1(7) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C2 C1 C6 121.6(7) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C15 C16 C17 118.9(7) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C15 C20 C19 119.8(8) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C8 C9 C10 117.6(7) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C1 C2 C3 117.1(7) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C11 C12 C13 118.1(7) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
N1 C14 C15 112.9(6) . . ?
N1 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N1 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C4 C3 C2 122.4(7) . . ?
C4 C3 Cl1 120.3(7) . . ?
C2 C3 Cl1 117.3(7) . . ?
C18 C19 C20 121.2(8) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C9 C10 C11 120.4(8) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 122.5(8) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C18 C17 C16 120.7(8) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 119.8(8) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?

_refine_diff_density_max         0.752
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.095

