# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1437990'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.13 H3.02 Br0.26 N0.55 O0.04'
_chemical_formula_weight         57.43

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.520(3)
_cell_length_b                   11.8717(9)
_cell_length_c                   16.0987(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.855(2)
_cell_angle_gamma                90.00
_cell_volume                     6162.5(8)
_cell_formula_units_Z            94
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3054
_cell_measurement_theta_min      5.053
_cell_measurement_theta_max      46.494

_exptl_crystal_description       cube
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2720
_exptl_absorpt_coefficient_mu    3.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21936
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         28.33
_reflns_number_total             7678
_reflns_number_gt                4118
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0807P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3054
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1730
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.072
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.062161(16) 0.01644(5) 0.40201(4) 0.05562(19) Uani 1 1 d . . .
Br2 Br 0.249384(17) 0.25007(6) 0.34703(3) 0.0650(2) Uani 1 1 d . . .
Br3 Br 0.06556(2) 0.66799(5) 0.39196(5) 0.0762(2) Uani 1 1 d . . .
C1 C 0.19449(13) 0.6499(4) 0.5451(3) 0.0365(11) Uani 1 1 d . . .
C2 C 0.19001(12) 0.7680(4) 0.5426(3) 0.0365(11) Uani 1 1 d . . .
C3 C 0.18786(13) 0.8277(4) 0.4666(3) 0.0369(11) Uani 1 1 d . . .
C4 C 0.19091(12) 0.7694(4) 0.3930(3) 0.0356(10) Uani 1 1 d . . .
C5 C 0.19535(13) 0.6526(4) 0.3944(3) 0.0371(11) Uani 1 1 d . . .
C6 C 0.19839(12) 0.5927(4) 0.4715(3) 0.0337(10) Uani 1 1 d . . .
C7 C 0.19408(16) 0.5853(5) 0.6260(3) 0.0553(14) Uani 1 1 d . . .
H7A H 0.1687 0.6005 0.6407 0.083 Uiso 1 1 calc R . .
H7B H 0.2172 0.6083 0.6727 0.083 Uiso 1 1 calc R . .
H7C H 0.1961 0.5060 0.6159 0.083 Uiso 1 1 calc R . .
C8 C 0.18877(15) 0.8299(4) 0.6236(3) 0.0473(12) Uani 1 1 d . . .
H8A H 0.2080 0.7944 0.6728 0.057 Uiso 1 1 calc R . .
H8B H 0.1980 0.9068 0.6201 0.057 Uiso 1 1 calc R . .
C9 C 0.18164(16) 0.9545(4) 0.4640(4) 0.0517(13) Uani 1 1 d . . .
H9A H 0.1624 0.9741 0.4962 0.078 Uiso 1 1 calc R . .
H9B H 0.1709 0.9785 0.4051 0.078 Uiso 1 1 calc R . .
H9C H 0.2077 0.9910 0.4889 0.078 Uiso 1 1 calc R . .
C10 C 0.19540(16) 0.5890(5) 0.3126(3) 0.0573(14) Uani 1 1 d . . .
H10A H 0.1930 0.5097 0.3217 0.086 Uiso 1 1 calc R . .
H10B H 0.2208 0.6036 0.2980 0.086 Uiso 1 1 calc R . .
H10C H 0.1724 0.6135 0.2662 0.086 Uiso 1 1 calc R . .
C11 C 0.19070(15) 0.8323(4) 0.3116(3) 0.0469(12) Uani 1 1 d . . .
H11A H 0.2008 0.9082 0.3268 0.056 Uiso 1 1 calc R . .
H11B H 0.2097 0.7956 0.2844 0.056 Uiso 1 1 calc R . .
C12 C 0.20704(13) 0.4686(4) 0.4761(3) 0.0440(12) Uani 1 1 d . . .
H12A H 0.2234 0.4501 0.4368 0.053 Uiso 1 1 calc R . .
H12B H 0.2233 0.4496 0.5341 0.053 Uiso 1 1 calc R . .
C13 C 0.13021(15) 0.4370(5) 0.4318(4) 0.0585(15) Uani 1 1 d . . .
H13 H 0.1220 0.5121 0.4270 0.070 Uiso 1 1 calc R . .
C14 C 0.12763(18) 0.2521(4) 0.4310(4) 0.0527(13) Uani 1 1 d . . .
H14 H 0.1177 0.1785 0.4258 0.063 Uiso 1 1 calc R . .
C15 C 0.16824(16) 0.2847(4) 0.4543(3) 0.0478(12) Uani 1 1 d . . .
H15 H 0.1912 0.2373 0.4678 0.057 Uiso 1 1 calc R . .
C16 C 0.11125(16) 0.8263(5) 0.5779(4) 0.0541(14) Uani 1 1 d . . .
H16 H 0.1079 0.8173 0.5190 0.065 Uiso 1 1 calc R . .
C17 C 0.1395(2) 0.8457(5) 0.7175(4) 0.0656(17) Uani 1 1 d . . .
H17 H 0.1594 0.8515 0.7705 0.079 Uiso 1 1 calc R . .
C19 C 0.1428(2) 0.8521(5) 0.1618(4) 0.0624(15) Uani 1 1 d . . .
H19 H 0.1631 0.8545 0.1324 0.075 Uiso 1 1 calc R . .
C20 C 0.11310(15) 0.8392(4) 0.2663(3) 0.0488(13) Uani 1 1 d . . .
H20 H 0.1088 0.8312 0.3207 0.059 Uiso 1 1 calc R . .
C27 C 0.05958(18) 0.3492(5) 0.3918(6) 0.099(3) Uani 1 1 d . . .
H27A H 0.0494 0.3311 0.3316 0.149 Uiso 1 1 calc R . .
H27B H 0.0503 0.4232 0.4019 0.149 Uiso 1 1 calc R . .
H27C H 0.0493 0.2952 0.4253 0.149 Uiso 1 1 calc R . .
C28 C 0.0987(2) 0.8493(5) 0.7040(4) 0.077(2) Uani 1 1 d . . .
H28 H 0.0846 0.8589 0.7459 0.093 Uiso 1 1 calc R . .
C29 C 0.1023(2) 0.8612(5) 0.1265(4) 0.0666(17) Uani 1 1 d . . .
H29 H 0.0890 0.8710 0.0682 0.080 Uiso 1 1 calc R . .
C30 C 0.03867(17) 0.8555(6) 0.1862(4) 0.082(2) Uani 1 1 d . . .
H30A H 0.0253 0.7920 0.1532 0.123 Uiso 1 1 calc R . .
H30B H 0.0267 0.9239 0.1584 0.123 Uiso 1 1 calc R . .
H30C H 0.0349 0.8522 0.2432 0.123 Uiso 1 1 calc R . .
C31 C 0.03576(19) 0.8320(7) 0.5694(5) 0.097(3) Uani 1 1 d . . .
H31A H 0.0321 0.7953 0.5147 0.146 Uiso 1 1 calc R . .
H31B H 0.0250 0.9074 0.5603 0.146 Uiso 1 1 calc R . .
H31C H 0.0212 0.7909 0.6033 0.146 Uiso 1 1 calc R . .
N1 N 0.16897(11) 0.4001(3) 0.4542(2) 0.0385(9) Uani 1 1 d . . .
N2 N 0.10471(13) 0.3467(4) 0.4170(3) 0.0584(12) Uani 1 1 d . . .
N3 N 0.14691(13) 0.8318(3) 0.6379(3) 0.0477(10) Uani 1 1 d . . .
N5 N 0.14957(12) 0.8387(3) 0.2491(3) 0.0445(10) Uani 1 1 d . . .
N6 N 0.08349(14) 0.8532(4) 0.1923(3) 0.0539(11) Uani 1 1 d . . .
N4 N 0.08075(15) 0.8359(4) 0.6159(3) 0.0635(13) Uani 1 1 d . . .
O1 O 1.0000 0.1629(6) 0.2500 0.102(2) Uani 1 2 d S . .
H1D H 0.9775 0.1851 0.2595 0.122 Uiso 0.50 1 d PR . .
H1C H 1.0051 0.0965 0.2697 0.153 Uiso 0.50 1 d PR . .
C32 C 0.0279(5) 0.3933(13) 0.5824(10) 0.094(4) Uiso 0.50 1 d P . .
N7 N 0.0831(6) 0.4922(16) 0.6444(18) 0.202(11) Uani 0.50 1 d P . .
C33 C 0.0466(7) 0.4860(17) 0.6384(14) 0.128(6) Uiso 0.50 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.403(6) . ?
C1 C2 1.409(6) . ?
C1 C7 1.515(6) . ?
C2 C3 1.399(6) . ?
C2 C8 1.508(6) . ?
C3 C4 1.399(6) . ?
C3 C9 1.519(6) . ?
C4 C5 1.394(6) . ?
C4 C11 1.507(6) . ?
C5 C6 1.410(6) . ?
C5 C10 1.519(7) . ?
C6 C12 1.499(6) . ?
C8 N3 1.483(6) . ?
C11 N5 1.470(6) . ?
C12 N1 1.472(5) . ?
C13 N1 1.324(6) . ?
C13 N2 1.351(6) . ?
C14 N2 1.345(6) . ?
C14 C15 1.365(7) . ?
C15 N1 1.370(6) . ?
C16 N3 1.317(6) . ?
C16 N4 1.332(7) . ?
C17 C28 1.327(9) . ?
C17 N3 1.379(7) . ?
C19 C29 1.326(8) . ?
C19 N5 1.371(7) . ?
C20 N5 1.325(6) . ?
C20 N6 1.336(6) . ?
C27 N2 1.455(7) . ?
C28 N4 1.391(8) . ?
C29 N6 1.375(7) . ?
C30 N6 1.479(7) . ?
C31 N4 1.490(8) . ?
C32 C33 1.45(2) . ?
N7 C33 1.20(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.4(4) . . ?
C6 C1 C7 120.3(4) . . ?
C2 C1 C7 120.2(4) . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 C8 120.2(4) . . ?
C1 C2 C8 119.2(4) . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 C9 120.6(4) . . ?
C2 C3 C9 120.0(4) . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 C11 118.8(4) . . ?
C3 C4 C11 120.4(4) . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 C10 120.4(4) . . ?
C6 C5 C10 119.7(4) . . ?
C1 C6 C5 119.9(4) . . ?
C1 C6 C12 119.7(4) . . ?
C5 C6 C12 120.4(4) . . ?
N3 C8 C2 113.1(4) . . ?
N5 C11 C4 113.7(4) . . ?
N1 C12 C6 112.8(4) . . ?
N1 C13 N2 108.2(5) . . ?
N2 C14 C15 106.9(4) . . ?
C14 C15 N1 107.4(5) . . ?
N3 C16 N4 108.4(5) . . ?
C28 C17 N3 106.9(5) . . ?
C29 C19 N5 108.1(5) . . ?
N5 C20 N6 108.5(4) . . ?
C17 C28 N4 107.6(5) . . ?
C19 C29 N6 107.2(5) . . ?
C13 N1 C15 108.3(4) . . ?
C13 N1 C12 127.2(4) . . ?
C15 N1 C12 124.5(4) . . ?
C14 N2 C13 109.2(4) . . ?
C14 N2 C27 124.5(4) . . ?
C13 N2 C27 126.3(5) . . ?
C16 N3 C17 109.3(5) . . ?
C16 N3 C8 126.4(4) . . ?
C17 N3 C8 124.3(4) . . ?
C20 N5 C19 108.1(4) . . ?
C20 N5 C11 127.1(4) . . ?
C19 N5 C11 124.7(4) . . ?
C20 N6 C29 108.1(5) . . ?
C20 N6 C30 123.7(5) . . ?
C29 N6 C30 128.2(5) . . ?
C16 N4 C28 107.8(5) . . ?
C16 N4 C31 124.5(5) . . ?
C28 N4 C31 127.7(5) . . ?
N7 C33 C32 111(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.866
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.118
