# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2009774'
loop_
_audit_author_name
_audit_author_address
'Marcin Moskwa'
;Faculty of Chemistry, University of Wroclaw 
Poland
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-09-09 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         'C12 H13 N2, C6 H Br2 O4'
_chemical_formula_sum            'C18 H14 Br2 N2 O4'
_chemical_formula_weight         482.13

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'
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'
Br Br -0.2901 2.4595 '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                   15.252(4)
_cell_length_b                   11.926(2)
_cell_length_c                   10.272(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.83(3)
_cell_angle_gamma                90
_cell_volume                     1768(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8943
_cell_measurement_theta_min      3.3870
_cell_measurement_theta_max      36.1540

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    4.611
_shelx_estimated_absorpt_T_min   0.248
_shelx_estimated_absorpt_T_max   0.475
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.363
_exptl_absorpt_correction_T_max  0.565
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            16895
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.299
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.495
_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             3297
_reflns_number_gt                2826
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_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)+(0.0716P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3297
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.09540(2) 0.27135(3) 0.65888(4) 0.02337(15) Uani 1 1 d . . . . .
Br2 Br 0.41193(2) 0.29420(3) 0.33946(4) 0.02057(15) Uani 1 1 d . . . . .
C1 C 0.1852(2) 0.2776(3) 0.5684(4) 0.0175(7) Uani 1 1 d . . . . .
C2 C 0.2076(2) 0.3753(3) 0.5214(4) 0.0182(7) Uani 1 1 d . . . . .
O2 O 0.16582(18) 0.4706(2) 0.5332(3) 0.0260(6) Uani 1 1 d . . . . .
H2 H 0.182(3) 0.533(4) 0.483(4) 0.039 Uiso 1 1 d . U . . .
C3 C 0.2834(2) 0.3827(3) 0.4556(3) 0.0176(7) Uani 1 1 d . . . . .
O3 O 0.30582(18) 0.48059(19) 0.4314(3) 0.0250(6) Uani 1 1 d . . . . .
C4 C 0.3222(2) 0.2835(3) 0.4298(4) 0.0163(7) Uani 1 1 d . . . . .
C5 C 0.3015(2) 0.1771(3) 0.4732(4) 0.0205(7) Uani 1 1 d . . . . .
O5 O 0.33810(18) 0.0877(2) 0.4596(3) 0.0312(6) Uani 1 1 d . . . . .
C6 C 0.2264(2) 0.1721(3) 0.5457(4) 0.0196(7) Uani 1 1 d . . . . .
O6 O 0.20468(18) 0.0816(2) 0.5790(3) 0.0310(6) Uani 1 1 d . . . . .
N11 N 0.33307(19) 0.6461(2) 0.6165(3) 0.0188(6) Uani 1 1 d . . . . .
H11 H 0.314(2) 0.584(3) 0.542(4) 0.023 Uiso 1 1 d . U . . .
C12 C 0.2905(2) 0.7470(3) 0.5874(4) 0.0216(8) Uani 1 1 d . . . . .
C13 C 0.3183(2) 0.8328(3) 0.6835(4) 0.0254(8) Uani 1 1 d . . . . .
H13 H 0.2899 0.9046 0.6653 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3881(3) 0.8118(4) 0.8064(4) 0.0299(9) Uani 1 1 d . . . . .
H14 H 0.4077 0.8695 0.8732 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4294(3) 0.7068(3) 0.8325(4) 0.0268(8) Uani 1 1 d . . . . .
H15 H 0.4771 0.6924 0.9170 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4006(2) 0.6236(3) 0.7345(4) 0.0225(8) Uani 1 1 d . . . . .
C17 C 0.4426(3) 0.5085(3) 0.7539(4) 0.0274(8) Uani 1 1 d . . . . .
H17A H 0.4027 0.4570 0.7836 0.041 Uiso 1 1 calc R U . . .
H17B H 0.5040 0.5112 0.8241 0.041 Uiso 1 1 calc R U . . .
H17C H 0.4486 0.4821 0.6668 0.041 Uiso 1 1 calc R U . . .
N21 N 0.17047(19) 0.6635(2) 0.3982(3) 0.0200(6) Uani 1 1 d . . . . .
C22 C 0.2166(2) 0.7581(3) 0.4535(4) 0.0200(7) Uani 1 1 d . . . . .
C23 C 0.1991(3) 0.8610(3) 0.3870(4) 0.0286(9) Uani 1 1 d . . . . .
H23 H 0.2325 0.9262 0.4281 0.034 Uiso 1 1 calc R U . . .
C24 C 0.1320(3) 0.8662(3) 0.2598(4) 0.0334(9) Uani 1 1 d . . . . .
H24 H 0.1173 0.9358 0.2127 0.040 Uiso 1 1 calc R U . . .
C25 C 0.0859(3) 0.7695(4) 0.2009(5) 0.0327(9) Uani 1 1 d . . . . .
H25 H 0.0406 0.7718 0.1121 0.039 Uiso 1 1 calc R U . . .
C26 C 0.1064(2) 0.6689(3) 0.2728(4) 0.0239(8) Uani 1 1 d . . . . .
C27 C 0.0589(3) 0.5602(4) 0.2143(4) 0.0364(10) Uani 1 1 d . . . . .
H27A H 0.1021 0.5125 0.1865 0.055 Uiso 1 1 calc R U . . .
H27B H 0.0046 0.5762 0.1342 0.055 Uiso 1 1 calc R U . . .
H27C H 0.0393 0.5214 0.2844 0.055 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
Br1 C1 1.888(4) . ?
Br2 C4 1.890(3) . ?
C1 C2 1.348(5) . ?
C1 C6 1.459(5) . ?
C2 O2 1.327(4) . ?
C2 C3 1.518(5) . ?
O2 H2 0.99(4) . ?
C3 O3 1.264(4) . ?
C3 C4 1.387(5) . ?
C4 C5 1.414(5) . ?
C5 O5 1.232(4) . ?
C5 C6 1.555(5) . ?
C6 O6 1.211(4) . ?
N11 C16 1.340(5) . ?
N11 C12 1.354(4) . ?
N11 H11 1.04(4) . ?
C12 C13 1.390(5) . ?
C12 C22 1.476(6) . ?
C13 C14 1.387(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.501(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N21 C26 1.344(5) . ?
N21 C22 1.354(5) . ?
C22 C23 1.388(5) . ?
C23 C24 1.377(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.512(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.1(3) . . ?
C2 C1 Br1 121.3(3) . . ?
C6 C1 Br1 117.6(2) . . ?
O2 C2 C1 121.5(3) . . ?
O2 C2 C3 116.6(3) . . ?
C1 C2 C3 121.9(3) . . ?
C2 O2 H2 113(2) . . ?
O3 C3 C4 126.3(3) . . ?
O3 C3 C2 115.8(3) . . ?
C4 C3 C2 118.0(3) . . ?
C3 C4 C5 123.6(3) . . ?
C3 C4 Br2 117.2(2) . . ?
C5 C4 Br2 119.1(2) . . ?
O5 C5 C4 125.7(3) . . ?
O5 C5 C6 116.9(3) . . ?
C4 C5 C6 117.3(3) . . ?
O6 C6 C1 123.6(3) . . ?
O6 C6 C5 118.7(3) . . ?
C1 C6 C5 117.8(3) . . ?
C16 N11 C12 123.4(3) . . ?
C16 N11 H11 118(2) . . ?
C12 N11 H11 118(2) . . ?
N11 C12 C13 118.9(3) . . ?
N11 C12 C22 116.9(3) . . ?
C13 C12 C22 124.1(3) . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N11 C16 C15 119.1(3) . . ?
N11 C16 C17 118.3(3) . . ?
C15 C16 C17 122.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 N21 C22 118.7(3) . . ?
N21 C22 C23 122.6(4) . . ?
N21 C22 C12 116.9(3) . . ?
C23 C22 C12 120.4(3) . . ?
C24 C23 C22 118.2(4) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C23 C24 C25 119.7(4) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 119.4(4) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
N21 C26 C25 121.3(3) . . ?
N21 C26 C27 116.5(3) . . ?
C25 C26 C27 122.1(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N21 0.99(4) 1.76(4) 2.698(4) 157(4) .
N11 H11 O3 1.04(4) 1.65(4) 2.678(4) 169(3) .
C13 H13 O6 0.95 2.49 3.428(4) 170.8 1_565
C15 H15 Br2 0.95 2.80 3.609(4) 143.1 2_656
C17 H17A O5 0.98 2.38 3.239(5) 145.8 4_566
C23 H23 O5 0.95 2.46 3.367(4) 158.7 1_565
C23 H23 O6 0.95 2.54 3.272(5) 134.2 1_565
C25 H25 Br1 0.95 2.89 3.835(5) 178.1 2
C27 H27A O6 0.98 2.46 3.425(5) 168.8 4_565

_refine_diff_density_max         0.904
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.150

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2009776'
loop_
_audit_author_name
_audit_author_address
'Marcin Moskwa'
;Faculty of Chemistry, University of Wroclaw 
Poland
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-09-09 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         'C12 H13 N2, 0.5(C6 I2 O4), 0.5(C6 H2 I2 O4)'
_chemical_formula_sum            'C18 H14 I2 N2 O4'
_chemical_formula_weight         576.11

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'
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'
I I -0.4742 1.8119 '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                   10.026(2)
_cell_length_b                   10.281(2)
_cell_length_c                   10.526(2)
_cell_angle_alpha                110.26(2)
_cell_angle_beta                 92.56(2)
_cell_angle_gamma                113.13(2)
_cell_volume                     915(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12873
_cell_measurement_theta_min      3.3840
_cell_measurement_theta_max      36.8300

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.462
_shelx_estimated_absorpt_T_min   0.466
_shelx_estimated_absorpt_T_max   0.625
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_T_max  0.711
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            10778
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.399
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.499
_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             3402
_reflns_number_gt                3239
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0327P)²+0.6412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3402
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
I1A I 0.38166(2) 0.15099(2) 0.54957(2) 0.01384(7) Uani 1 1 d . . . . .
C1A C 0.4501(3) 0.3576(3) 0.5213(3) 0.0126(5) Uani 1 1 d . . . . .
O2A O 0.6561(2) 0.4912(2) 0.70995(19) 0.0160(4) Uani 1 1 d . . . . .
C2A C 0.5758(3) 0.4860(3) 0.6131(3) 0.0118(5) Uani 1 1 d . . . . .
O3A O 0.27530(19) 0.2437(2) 0.31186(19) 0.0153(4) Uani 1 1 d . . . . .
C3A C 0.3767(3) 0.3577(3) 0.4047(3) 0.0113(5) Uani 1 1 d . . . . .
I1B I 0.76243(2) 0.51676(2) 1.23857(2) 0.01386(7) Uani 1 1 d . . . . .
C1B C 0.8979(3) 0.5025(3) 1.0949(3) 0.0126(5) Uani 1 1 d . . . . .
O2B O 1.1161(2) 0.6254(2) 1.26917(19) 0.0179(4) Uani 1 1 d . . . . .
C2B C 1.0572(3) 0.5638(3) 1.1471(3) 0.0128(5) Uani 1 1 d . . . . .
O3B O 0.7010(2) 0.3954(2) 0.90505(19) 0.0155(4) Uani 1 1 d . . . . .
H3B H 0.6863 0.3845 0.8163 0.023 Uiso 1 1 d R U . . .
C3B C 0.8436(3) 0.4477(3) 0.9581(3) 0.0123(5) Uani 1 1 d . . . . .
N11 N 0.1235(2) 0.2234(2) 0.0717(2) 0.0118(4) Uani 1 1 d . . . . .
H11 H 0.1807 0.2607 0.1560 0.014 Uiso 1 1 d R U . . .
C12 C -0.0264(3) 0.1766(3) 0.0523(3) 0.0117(5) Uani 1 1 d . . . . .
C13 C -0.1067(3) 0.1099(3) -0.0827(3) 0.0136(5) Uani 1 1 d . . . . .
H13 H -0.2109 0.0772 -0.0996 0.016 Uiso 1 1 calc R U . . .
C14 C -0.0357(3) 0.0909(3) -0.1919(3) 0.0154(5) Uani 1 1 d . . . . .
H14 H -0.0914 0.0440 -0.2841 0.018 Uiso 1 1 calc R U . . .
C15 C 0.1167(3) 0.1399(3) -0.1682(3) 0.0132(5) Uani 1 1 d . . . . .
H15 H 0.1657 0.1261 -0.2436 0.016 Uiso 1 1 calc R U . . .
C16 C 0.1968(3) 0.2094(3) -0.0325(3) 0.0123(5) Uani 1 1 d . . . . .
C17 C 0.3616(3) 0.2686(3) 0.0043(3) 0.0175(6) Uani 1 1 d . . . . .
H17A H 0.4065 0.3797 0.0604 0.026 Uiso 1 1 calc R U . . .
H17B H 0.4006 0.2489 -0.0806 0.026 Uiso 1 1 calc R U . . .
H17C H 0.3857 0.2160 0.0573 0.026 Uiso 1 1 calc R U . . .
N21 N -0.2466(2) 0.1143(2) 0.1403(2) 0.0132(4) Uani 1 1 d . . . . .
C22 C -0.0968(3) 0.1962(3) 0.1737(3) 0.0123(5) Uani 1 1 d . . . . .
C23 C -0.0180(3) 0.2892(3) 0.3089(3) 0.0151(5) Uani 1 1 d . . . . .
H23 H 0.0862 0.3495 0.3284 0.018 Uiso 1 1 calc R U . . .
C24 C -0.0958(3) 0.2916(3) 0.4146(3) 0.0175(6) Uani 1 1 d . . . . .
H24 H -0.0449 0.3513 0.5085 0.021 Uiso 1 1 calc R U . . .
C25 C -0.2476(3) 0.2066(3) 0.3822(3) 0.0159(6) Uani 1 1 d . . . . .
H25 H -0.3024 0.2061 0.4535 0.019 Uiso 1 1 calc R U . . .
C26 C -0.3203(3) 0.1210(3) 0.2428(3) 0.0132(5) Uani 1 1 d . . . . .
C27 C -0.4867(3) 0.0333(3) 0.2017(3) 0.0177(6) Uani 1 1 d . . . . .
H27A H -0.5161 -0.0283 0.1017 0.027 Uiso 1 1 calc R U . . .
H27B H -0.5310 0.1061 0.2255 0.027 Uiso 1 1 calc R U . . .
H27C H -0.5212 -0.0348 0.2512 0.027 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
I1A C1A 2.093(3) . ?
C1A C2A 1.402(4) . ?
C1A C3A 1.403(4) . ?
O2A C2A 1.243(3) . ?
C2A C3A 1.569(3) 2_666 ?
O3A C3A 1.242(3) . ?
C3A C2A 1.569(3) 2_666 ?
I1B C1B 2.083(3) . ?
C1B C3B 1.347(4) . ?
C1B C2B 1.463(4) . ?
O2B C2B 1.215(3) . ?
C2B C3B 1.525(4) 2_767 ?
O3B C3B 1.327(3) . ?
O3B H3B 0.9000 . ?
C3B C2B 1.525(4) 2_767 ?
N11 C16 1.345(3) . ?
N11 C12 1.366(3) . ?
N11 H11 0.9000 . ?
C12 C13 1.388(4) . ?
C12 C22 1.478(4) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.498(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N21 C26 1.332(3) . ?
N21 C22 1.357(3) . ?
C22 C23 1.388(4) . ?
C23 C24 1.385(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.402(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.505(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A C1A C3A 122.9(2) . . ?
C2A C1A I1A 118.20(18) . . ?
C3A C1A I1A 118.61(18) . . ?
O2A C2A C1A 127.1(2) . . ?
O2A C2A C3A 114.8(2) . 2_666 ?
C1A C2A C3A 118.1(2) . 2_666 ?
O3A C3A C1A 125.9(2) . . ?
O3A C3A C2A 115.7(2) . 2_666 ?
C1A C3A C2A 118.4(2) . 2_666 ?
C3B C1B C2B 120.1(2) . . ?
C3B C1B I1B 121.68(19) . . ?
C2B C1B I1B 118.09(19) . . ?
O2B C2B C1B 124.1(2) . . ?
O2B C2B C3B 117.8(2) . 2_767 ?
C1B C2B C3B 118.1(2) . 2_767 ?
C3B O3B H3B 111.6 . . ?
O3B C3B C1B 122.9(2) . . ?
O3B C3B C2B 115.5(2) . 2_767 ?
C1B C3B C2B 121.6(2) . 2_767 ?
C16 N11 C12 123.6(2) . . ?
C16 N11 H11 114.2 . . ?
C12 N11 H11 122.1 . . ?
N11 C12 C13 117.8(2) . . ?
N11 C12 C22 119.5(2) . . ?
C13 C12 C22 122.7(2) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 119.0(2) . . ?
N11 C16 C17 117.7(2) . . ?
C15 C16 C17 123.3(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 N21 C22 118.1(2) . . ?
N21 C22 C23 123.0(2) . . ?
N21 C22 C12 113.4(2) . . ?
C23 C22 C12 123.5(2) . . ?
C24 C23 C22 118.1(2) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C25 C24 C23 119.3(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 119.2(3) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
N21 C26 C25 122.0(2) . . ?
N21 C26 C27 116.7(2) . . ?
C25 C26 C27 121.3(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 I1A 0.95 3.14 4.074(3) 167.6 1_554
C23 H23 O3A 0.95 2.52 3.155(3) 124.7 .
N11 H11 O3A 0.90 1.95 2.791(3) 154.5 .
N11 H11 O2A 0.90 2.28 2.925(3) 128.4 2_666
O3B H3B O2A 0.90 1.90 2.657(3) 139.8 .
O3B H3B O2B 0.90 2.24 2.666(3) 108.8 2_767

_refine_diff_density_max         0.834
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2009775'
loop_
_audit_author_name
_audit_author_address
'Marcin Moskwa'
;Faculty of Chemistry, University of Wroclaw 
Poland
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-09-09 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         'C12 H13 N2, 0.5(C6 Br2 O4)'
_chemical_formula_sum            'C15 H13 Br N2 O2'
_chemical_formula_weight         333.18

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'
Br Br -0.2901 2.4595 '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                   7.792(4)
_cell_length_b                   9.705(3)
_cell_length_c                   9.938(5)
_cell_angle_alpha                94.41(4)
_cell_angle_beta                 106.41(5)
_cell_angle_gamma                110.28(3)
_cell_volume                     663(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2787
_cell_measurement_theta_min      3.4340
_cell_measurement_theta_max      28.5940

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    3.101
_shelx_estimated_absorpt_T_min   0.511
_shelx_estimated_absorpt_T_max   0.689
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            3927
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.831
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.496
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2436
_reflns_number_gt                2252
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_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)+(0.0148P)²+0.4655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2436
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0556
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.82164(3) 0.35340(3) 1.11080(2) 0.01404(8) Uani 1 1 d . . . . .
C1 C 0.6417(3) 0.1509(3) 1.0454(2) 0.0116(5) Uani 1 1 d . . . . .
C2 C 0.6617(3) 0.0473(3) 1.1348(2) 0.0112(5) Uani 1 1 d . . . . .
O2 O 0.7912(2) 0.07444(18) 1.25107(17) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.4915(3) 0.1161(3) 0.9155(2) 0.0114(5) Uani 1 1 d . . . . .
O3 O 0.4678(2) 0.20526(18) 0.83468(17) 0.0151(4) Uani 1 1 d . . . . .
N21 N 0.2587(3) 0.3479(2) 0.39984(19) 0.0125(4) Uani 1 1 d . . . . .
C22 C 0.2225(3) 0.2426(3) 0.4794(2) 0.0122(5) Uani 1 1 d . . . . .
C23 C 0.2858(3) 0.1249(3) 0.4782(2) 0.0135(5) Uani 1 1 d . . . . .
H23 H 0.2588 0.0534 0.5373 0.016 Uiso 1 1 calc R U . . .
C24 C 0.3895(3) 0.1162(3) 0.3878(2) 0.0159(5) Uani 1 1 d . . . . .
H24 H 0.4349 0.0374 0.3834 0.019 Uiso 1 1 calc R U . . .
C25 C 0.4264(3) 0.2229(3) 0.3039(3) 0.0159(5) Uani 1 1 d . . . . .
H25 H 0.4966 0.2177 0.2409 0.019 Uiso 1 1 calc R U . . .
C26 C 0.3598(3) 0.3382(3) 0.3128(2) 0.0138(5) Uani 1 1 d . . . . .
C27 C 0.3968(4) 0.4581(3) 0.2249(3) 0.0185(5) Uani 1 1 d . . . . .
H27A H 0.2737 0.4490 0.1557 0.028 Uiso 1 1 calc R U . . .
H27B H 0.4833 0.4465 0.1739 0.028 Uiso 1 1 calc R U . . .
H27C H 0.4576 0.5568 0.2880 0.028 Uiso 1 1 calc R U . . .
N11 N 0.1245(3) 0.2090(2) 0.6916(2) 0.0116(4) Uani 1 1 d . . . . .
H11 H 0.221(4) 0.181(3) 0.724(3) 0.014 Uiso 1 1 d . U . . .
C12 C 0.1022(3) 0.2585(2) 0.5669(2) 0.0117(5) Uani 1 1 d . . . . .
C13 C -0.0358(3) 0.3200(3) 0.5232(2) 0.0127(5) Uani 1 1 d . . . . .
H13 H -0.0555 0.3542 0.4352 0.015 Uiso 1 1 calc R U . . .
C14 C -0.1444(3) 0.3310(3) 0.6088(2) 0.0142(5) Uani 1 1 d . . . . .
H14 H -0.2360 0.3762 0.5812 0.017 Uiso 1 1 calc R U . . .
C15 C -0.1206(3) 0.2765(3) 0.7348(2) 0.0144(5) Uani 1 1 d . . . . .
H15 H -0.1975 0.2818 0.7925 0.017 Uiso 1 1 calc R U . . .
C16 C 0.0174(3) 0.2139(3) 0.7757(2) 0.0139(5) Uani 1 1 d . . . . .
C17 C 0.0528(4) 0.1489(3) 0.9078(3) 0.0213(6) Uani 1 1 d . . . . .
H17A H 0.0152 0.0407 0.8808 0.032 Uiso 1 1 calc R U . . .
H17B H -0.0242 0.1682 0.9641 0.032 Uiso 1 1 calc R U . . .
H17C H 0.1907 0.1954 0.9649 0.032 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
Br1 C1 1.905(3) . ?
C1 C3 1.398(3) . ?
C1 C2 1.411(3) . ?
C2 O2 1.238(3) . ?
C2 C3 1.555(3) 2_657 ?
C3 O3 1.250(3) . ?
C3 C2 1.555(3) 2_657 ?
N21 C22 1.341(3) . ?
N21 C26 1.342(3) . ?
C22 C23 1.393(3) . ?
C22 C12 1.483(3) . ?
C23 C24 1.383(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.505(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N11 C16 1.346(3) . ?
N11 C12 1.351(3) . ?
N11 H11 0.87(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.497(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 124.0(2) . . ?
C3 C1 Br1 117.86(18) . . ?
C2 C1 Br1 117.99(17) . . ?
O2 C2 C1 125.9(2) . . ?
O2 C2 C3 116.3(2) . 2_657 ?
C1 C2 C3 117.9(2) . 2_657 ?
O3 C3 C1 125.8(2) . . ?
O3 C3 C2 116.1(2) . 2_657 ?
C1 C3 C2 118.1(2) . 2_657 ?
C22 N21 C26 118.1(2) . . ?
N21 C22 C23 123.8(2) . . ?
N21 C22 C12 114.2(2) . . ?
C23 C22 C12 121.9(2) . . ?
C24 C23 C22 117.5(2) . . ?
C24 C23 H23 121.3 . . ?
C22 C23 H23 121.3 . . ?
C23 C24 C25 119.5(2) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 119.4(2) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
N21 C26 C25 121.7(2) . . ?
N21 C26 C27 116.5(2) . . ?
C25 C26 C27 121.7(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C16 N11 C12 123.5(2) . . ?
C16 N11 H11 117.9(17) . . ?
C12 N11 H11 118.4(17) . . ?
N11 C12 C13 118.8(2) . . ?
N11 C12 C22 119.3(2) . . ?
C13 C12 C22 121.9(2) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N11 C16 C15 118.8(2) . . ?
N11 C16 C17 117.4(2) . . ?
C15 C16 C17 123.8(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O2 0.87(3) 2.48(3) 3.099(3) 129(2) 2_657
N11 H11 O3 0.87(3) 1.85(3) 2.665(3) 155(2) .
C17 H17B Br1 0.98 2.98 3.895(3) 155.8 1_455
C23 H23 O2 0.95 2.58 3.500(3) 163.9 2_657
C25 H25 Br1 0.95 3.10 3.973(3) 153.2 1_554
C27 H27C O3 0.98 2.66 3.225(3) 117.2 2_666
C13 H13 Br1 0.95 3.09 4.002(3) 161.1 1_454
C15 H15 Br1 0.95 3.14 3.934(3) 142.7 1_455
C15 H15 O3 0.95 2.62 3.481(3) 151.4 1_455

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.070

