# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1486543'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Ethyl 3-(4-bromophenyl)-1-((2R,3S)-3-(methoxycarbonyl)-2-propylaziridin-2-yl)-1H-pyrazole-5-carboxylate'
_chemical_name_common            'arylpyrazole substituted aziridine'
_chemical_melting_point          130.6
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Br1 N3 O4'
_chemical_formula_weight         872.61

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           1
_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'

_cell_length_a                   6.9252(14)
_cell_length_b                   8.5633(17)
_cell_length_c                   16.850(3)
_cell_angle_alpha                84.11(3)
_cell_angle_beta                 89.29(3)
_cell_angle_gamma                89.79(3)
_cell_volume                     993.9(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7145
_cell_measurement_theta_min      6.34
_cell_measurement_theta_max      54.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.097
_shelx_estimated_absorpt_T_min   0.818
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   sadabs
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7869
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.169
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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 0.839
_diffrn_reflns_point_group_measured_fraction_full 0.839
_reflns_number_total             5864
_reflns_number_gt                4662
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_max     0.681
_reflns_Friedel_fraction_full    0.681

_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)+(0.0504P)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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5864
_refine_ls_number_parameters     493
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.027
_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
Br1 Br 1.55707(9) 0.69436(8) 0.10834(5) 0.0725(3) Uani 1 1 d . . . . .
O1 O 0.2990(8) 0.7024(7) 0.4815(4) 0.0745(16) Uani 1 1 d . . . . .
O2 O 0.3434(6) 0.8993(6) 0.3838(3) 0.0595(13) Uani 1 1 d . . . . .
O3 O 0.4741(9) 0.1044(7) 0.5643(4) 0.0738(17) Uani 1 1 d . . . . .
O4 O 0.7404(9) 0.0513(6) 0.4968(3) 0.0694(15) Uani 1 1 d . . . . .
N1 N 0.8034(8) 0.5251(6) 0.3726(3) 0.0499(14) Uani 1 1 d . . . . .
N2 N 0.6410(9) 0.5527(7) 0.4139(4) 0.0517(15) Uani 1 1 d . . . . .
N3 N 0.3876(8) 0.3665(7) 0.4541(4) 0.0614(16) Uani 1 1 d . . . . .
H3 H 0.2646 0.3763 0.4493 0.074 Uiso 1 1 calc R U . . .
C1 C 1.3385(11) 0.6878(9) 0.1754(5) 0.0505(19) Uani 1 1 d . . . . .
C2 C 1.1884(10) 0.7953(8) 0.1609(4) 0.0546(18) Uani 1 1 d . . . . .
H2 H 1.1971 0.8736 0.1185 0.066 Uiso 1 1 calc R U . . .
C3 C 1.0268(10) 0.7846(8) 0.2099(4) 0.0528(17) Uani 1 1 d . . . . .
H3A H 0.9261 0.8557 0.1996 0.063 Uiso 1 1 calc R U . . .
C4 C 1.0115(10) 0.6698(8) 0.2741(5) 0.0446(18) Uani 1 1 d . . . . .
C5 C 1.1644(9) 0.5653(7) 0.2891(4) 0.0482(16) Uani 1 1 d . . . . .
H5 H 1.1573 0.4883 0.3321 0.058 Uiso 1 1 calc R U . . .
C6 C 1.3273(9) 0.5754(8) 0.2400(4) 0.0533(17) Uani 1 1 d . . . . .
H6 H 1.4295 0.5060 0.2508 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8385(10) 0.6567(8) 0.3261(5) 0.0448(18) Uani 1 1 d . . . . .
C8 C 0.6928(9) 0.7687(8) 0.3356(4) 0.0491(16) Uani 1 1 d . . . . .
H8 H 0.6825 0.8689 0.3089 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5713(10) 0.6994(8) 0.3918(4) 0.0462(17) Uani 1 1 d . . . . .
C10 C 0.3897(10) 0.7628(9) 0.4267(5) 0.0538(17) Uani 1 1 d . . . . .
C11 C 0.1628(9) 0.9693(9) 0.4063(5) 0.061(2) Uani 1 1 d . . . . .
H11A H 0.1731 1.0058 0.4587 0.074 Uiso 1 1 calc R U . . .
H11B H 0.0596 0.8928 0.4080 0.074 Uiso 1 1 calc R U . . .
C12 C 0.1214(13) 1.1046(10) 0.3450(6) 0.075(3) Uani 1 1 d . . . . .
H12A H 0.1119 1.0672 0.2934 0.112 Uiso 1 1 calc R U . . .
H12B H 0.2239 1.1799 0.3442 0.112 Uiso 1 1 calc R U . . .
H12C H 0.0017 1.1534 0.3581 0.112 Uiso 1 1 calc R U . . .
C13 C 0.5702(9) 0.4331(7) 0.4740(4) 0.0476(16) Uani 1 1 d . . . . .
C14 C 0.6190(11) 0.4631(9) 0.5580(4) 0.060(2) Uani 1 1 d . . . . .
H14A H 0.5634 0.3813 0.5953 0.073 Uiso 1 1 calc R U . . .
H14B H 0.5641 0.5628 0.5695 0.073 Uiso 1 1 calc R U . . .
C15 C 0.8468(16) 0.4663(15) 0.5688(7) 0.112(4) Uani 1 1 d . U . . .
H15A H 0.8978 0.3672 0.5545 0.134 Uiso 1 1 calc R U . . .
H15B H 0.8982 0.5479 0.5301 0.134 Uiso 1 1 calc R U . . .
C16 C 0.921(2) 0.490(2) 0.6423(9) 0.162(6) Uani 1 1 d . U . . .
H16A H 1.0380 0.5496 0.6350 0.243 Uiso 1 1 calc R U . . .
H16B H 0.9467 0.3909 0.6719 0.243 Uiso 1 1 calc R U . . .
H16C H 0.8282 0.5474 0.6711 0.243 Uiso 1 1 calc R U . . .
C17 C 0.5615(10) 0.2706(8) 0.4480(4) 0.0516(17) Uani 1 1 d . . . . .
H17 H 0.6095 0.2577 0.3941 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5863(13) 0.1343(9) 0.5097(5) 0.056(2) Uani 1 1 d . . . . .
C19 C 0.7754(15) -0.0807(10) 0.5557(6) 0.086(3) Uani 1 1 d . . . . .
H19A H 0.7098 -0.1716 0.5407 0.129 Uiso 1 1 calc R U . . .
H19B H 0.7280 -0.0566 0.6069 0.129 Uiso 1 1 calc R U . . .
H19C H 0.9116 -0.1015 0.5587 0.129 Uiso 1 1 calc R U . . .
Br2 Br -0.44117(8) 1.17141(8) 0.20988(5) 0.0702(3) Uani 1 1 d . . . . .
O5 O 0.8224(8) 1.3325(7) -0.1594(4) 0.0728(15) Uani 1 1 d . . . . .
O6 O 0.7720(6) 1.4933(5) -0.0638(3) 0.0560(12) Uani 1 1 d . . . . .
O7 O 0.6451(10) 0.7815(8) -0.2511(4) 0.0767(18) Uani 1 1 d . . . . .
O8 O 0.3837(9) 0.6914(7) -0.1804(4) 0.0749(16) Uani 1 1 d . . . . .
N4 N 0.3122(7) 1.1157(6) -0.0557(3) 0.0459(13) Uani 1 1 d . . . . .
N5 N 0.4778(8) 1.1580(7) -0.0947(4) 0.0475(14) Uani 1 1 d . . . . .
N6 N 0.7291(8) 0.9883(8) -0.1358(4) 0.0626(17) Uani 1 1 d . . . . .
H6A H 0.8521 0.9937 -0.1302 0.075 Uiso 1 1 calc R U . . .
C20 C -0.2192(10) 1.1944(9) 0.1413(5) 0.0457(18) Uani 1 1 d . . . . .
C21 C -0.0735(9) 1.2955(8) 0.1583(4) 0.0519(17) Uani 1 1 d . . . . .
H21 H -0.0834 1.3546 0.2015 0.062 Uiso 1 1 calc R U . . .
C22 C 0.0879(10) 1.3051(8) 0.1086(4) 0.0520(17) Uani 1 1 d . . . . .
H22 H 0.1875 1.3727 0.1186 0.062 Uiso 1 1 calc R U . . .
C23 C 0.1047(10) 1.2171(8) 0.0446(4) 0.0401(17) Uani 1 1 d . . . . .
C24 C -0.0465(9) 1.1193(7) 0.0294(4) 0.0484(16) Uani 1 1 d . . . . .
H24 H -0.0376 1.0600 -0.0138 0.058 Uiso 1 1 calc R U . . .
C25 C -0.2094(9) 1.1084(8) 0.0770(4) 0.0506(17) Uani 1 1 d . . . . .
H25 H -0.3111 1.0438 0.0659 0.061 Uiso 1 1 calc R U . . .
C26 C 0.2767(10) 1.2267(8) -0.0074(5) 0.0429(17) Uani 1 1 d . . . . .
C27 C 0.4230(9) 1.3430(7) -0.0162(4) 0.0458(16) Uani 1 1 d . . . . .
H27 H 0.4319 1.4320 0.0109 0.055 Uiso 1 1 calc R U . . .
C28 C 0.5467(10) 1.2976(8) -0.0722(4) 0.0436(16) Uani 1 1 d . . . . .
C29 C 0.7281(10) 1.3717(8) -0.1048(4) 0.0492(16) Uani 1 1 d . . . . .
C30 C 0.9523(10) 1.5729(9) -0.0881(5) 0.0604(19) Uani 1 1 d . . . . .
H30A H 0.9399 1.6301 -0.1406 0.072 Uiso 1 1 calc R U . . .
H30B H 1.0568 1.4975 -0.0900 0.072 Uiso 1 1 calc R U . . .
C31 C 0.9918(12) 1.6847(11) -0.0263(6) 0.071(2) Uani 1 1 d . . . . .
H31A H 1.1137 1.7354 -0.0379 0.107 Uiso 1 1 calc R U . . .
H31B H 0.9954 1.6272 0.0256 0.107 Uiso 1 1 calc R U . . .
H31C H 0.8912 1.7623 -0.0275 0.107 Uiso 1 1 calc R U . . .
C32 C 0.5475(9) 1.0669(8) -0.1556(4) 0.0453(15) Uani 1 1 d . . . . .
C33 C 0.5078(10) 1.1374(9) -0.2403(4) 0.0530(16) Uani 1 1 d . . . . .
H33A H 0.5539 1.0652 -0.2771 0.064 Uiso 1 1 calc R U . . .
H33B H 0.5808 1.2339 -0.2508 0.064 Uiso 1 1 calc R U . . .
C34 C 0.2951(11) 1.1729(9) -0.2565(5) 0.062(2) Uani 1 1 d . . . . .
H34A H 0.2436 1.2301 -0.2142 0.075 Uiso 1 1 calc R U . . .
H34B H 0.2856 1.2409 -0.3060 0.075 Uiso 1 1 calc R U . . .
C35 C 0.1724(12) 1.0308(12) -0.2623(6) 0.085(3) Uani 1 1 d . . . . .
H35A H 0.2296 0.9672 -0.3001 0.127 Uiso 1 1 calc R U . . .
H35B H 0.0455 1.0630 -0.2796 0.127 Uiso 1 1 calc R U . . .
H35C H 0.1636 0.9710 -0.2110 0.127 Uiso 1 1 calc R U . . .
C36 C 0.5542(10) 0.8935(8) -0.1323(5) 0.0535(18) Uani 1 1 d . . . . .
H36 H 0.5040 0.8560 -0.0792 0.064 Uiso 1 1 calc R U . . .
C37 C 0.5377(13) 0.7857(10) -0.1950(6) 0.059(2) Uani 1 1 d . . . . .
C38 C 0.3480(16) 0.5870(11) -0.2419(7) 0.100(3) Uani 1 1 d . . . . .
H38A H 0.3312 0.6482 -0.2923 0.150 Uiso 1 1 calc R U . . .
H38B H 0.2334 0.5269 -0.2283 0.150 Uiso 1 1 calc R U . . .
H38C H 0.4559 0.5173 -0.2453 0.150 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 1.875(9) . ?
O1 C10 1.185(9) . ?
O2 C10 1.350(9) . ?
O2 C11 1.448(8) . ?
O3 C18 1.205(11) . ?
O4 C18 1.308(10) . ?
O4 C19 1.447(9) . ?
N1 C7 1.326(9) . ?
N1 N2 1.348(9) . ?
N2 C9 1.362(9) . ?
N2 C13 1.447(9) . ?
N3 C13 1.446(8) . ?
N3 C17 1.464(9) . ?
N3 H3 0.8600 . ?
C1 C6 1.379(11) . ?
C1 C2 1.393(10) . ?
C2 C3 1.381(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.393(9) . ?
C4 C7 1.473(11) . ?
C5 C6 1.388(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.408(10) . ?
C8 C9 1.351(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.505(10) . ?
C11 C12 1.501(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C17 1.503(9) . ?
C13 C14 1.506(9) . ?
C14 C15 1.591(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.381(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.492(10) . ?
C17 H17 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Br2 C20 1.910(8) . ?
O5 C29 1.197(9) . ?
O6 C29 1.345(8) . ?
O6 C30 1.459(8) . ?
O7 C37 1.199(11) . ?
O8 C37 1.345(11) . ?
O8 C38 1.459(10) . ?
N4 C26 1.332(9) . ?
N4 N5 1.347(8) . ?
N5 C28 1.379(9) . ?
N5 C32 1.430(9) . ?
N6 C32 1.451(8) . ?
N6 C36 1.458(10) . ?
N6 H6A 0.8600 . ?
C20 C25 1.371(10) . ?
C20 C21 1.384(10) . ?
C21 C22 1.386(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(9) . ?
C23 C26 1.468(11) . ?
C24 C25 1.374(10) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.419(10) . ?
C27 C28 1.352(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.483(10) . ?
C30 C31 1.513(11) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C36 1.497(10) . ?
C32 C33 1.518(9) . ?
C33 C34 1.526(10) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.499(11) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.478(11) . ?
C36 H36 0.9800 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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
C10 O2 C11 115.2(6) . . ?
C18 O4 C19 115.3(7) . . ?
C7 N1 N2 105.6(5) . . ?
N1 N2 C9 111.0(6) . . ?
N1 N2 C13 119.2(5) . . ?
C9 N2 C13 129.8(6) . . ?
C13 N3 C17 62.2(4) . . ?
C13 N3 H3 148.9 . . ?
C17 N3 H3 148.9 . . ?
C6 C1 C2 119.8(8) . . ?
C6 C1 Br1 119.4(6) . . ?
C2 C1 Br1 120.8(6) . . ?
C3 C2 C1 119.5(7) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.3(7) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C5 118.6(7) . . ?
C3 C4 C7 121.6(6) . . ?
C5 C4 C7 119.8(7) . . ?
C6 C5 C4 120.3(7) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 120.4(6) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C8 110.6(7) . . ?
N1 C7 C4 120.3(6) . . ?
C8 C7 C4 129.1(7) . . ?
C9 C8 C7 105.3(6) . . ?
C9 C8 H8 127.4 . . ?
C7 C8 H8 127.4 . . ?
C8 C9 N2 107.5(6) . . ?
C8 C9 C10 129.4(6) . . ?
N2 C9 C10 123.1(7) . . ?
O1 C10 O2 125.2(7) . . ?
O1 C10 C9 126.2(7) . . ?
O2 C10 C9 108.6(6) . . ?
O2 C11 C12 107.4(7) . . ?
O2 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O2 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 N2 113.4(5) . . ?
N3 C13 C17 59.5(4) . . ?
N2 C13 C17 114.9(6) . . ?
N3 C13 C14 122.4(7) . . ?
N2 C13 C14 113.7(5) . . ?
C17 C13 C14 122.5(6) . . ?
C13 C14 C15 110.4(7) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 119.2(12) . . ?
C16 C15 H15A 107.5 . . ?
C14 C15 H15A 107.5 . . ?
C16 C15 H15B 107.5 . . ?
C14 C15 H15B 107.5 . . ?
H15A C15 H15B 107.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 117.1(7) . . ?
N3 C17 C13 58.3(4) . . ?
C18 C17 C13 118.2(6) . . ?
N3 C17 H17 116.8 . . ?
C18 C17 H17 116.8 . . ?
C13 C17 H17 116.8 . . ?
O3 C18 O4 124.5(8) . . ?
O3 C18 C17 123.0(8) . . ?
O4 C18 C17 112.5(8) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C29 O6 C30 114.9(6) . . ?
C37 O8 C38 114.4(7) . . ?
C26 N4 N5 105.8(5) . . ?
N4 N5 C28 111.2(6) . . ?
N4 N5 C32 119.2(5) . . ?
C28 N5 C32 129.4(6) . . ?
C32 N6 C36 61.9(4) . . ?
C32 N6 H6A 149.0 . . ?
C36 N6 H6A 149.0 . . ?
C25 C20 C21 122.3(7) . . ?
C25 C20 Br2 118.5(6) . . ?
C21 C20 Br2 119.2(6) . . ?
C20 C21 C22 117.4(7) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 H21 121.3 . . ?
C23 C22 C21 121.8(7) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 118.5(7) . . ?
C22 C23 C26 121.5(6) . . ?
C24 C23 C26 119.9(7) . . ?
C25 C24 C23 121.1(7) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C20 C25 C24 118.8(6) . . ?
C20 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
N4 C26 C27 110.4(7) . . ?
N4 C26 C23 120.3(6) . . ?
C27 C26 C23 129.3(7) . . ?
C28 C27 C26 105.6(6) . . ?
C28 C27 H27 127.2 . . ?
C26 C27 H27 127.2 . . ?
C27 C28 N5 107.0(6) . . ?
C27 C28 C29 130.0(6) . . ?
N5 C28 C29 123.0(6) . . ?
O5 C29 O6 124.2(7) . . ?
O5 C29 C28 126.4(6) . . ?
O6 C29 C28 109.4(6) . . ?
O6 C30 C31 106.3(6) . . ?
O6 C30 H30A 110.5 . . ?
C31 C30 H30A 110.5 . . ?
O6 C30 H30B 110.5 . . ?
C31 C30 H30B 110.5 . . ?
H30A C30 H30B 108.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 N6 113.1(5) . . ?
N5 C32 C36 114.9(6) . . ?
N6 C32 C36 59.3(4) . . ?
N5 C32 C33 114.7(6) . . ?
N6 C32 C33 120.8(6) . . ?
C36 C32 C33 122.7(6) . . ?
C32 C33 C34 114.0(6) . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
C34 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C35 C34 C33 114.5(6) . . ?
C35 C34 H34A 108.6 . . ?
C33 C34 H34A 108.6 . . ?
C35 C34 H34B 108.6 . . ?
C33 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N6 C36 C37 115.5(7) . . ?
N6 C36 C32 58.8(4) . . ?
C37 C36 C32 119.0(7) . . ?
N6 C36 H36 116.9 . . ?
C37 C36 H36 116.9 . . ?
C32 C36 H36 116.9 . . ?
O7 C37 O8 124.2(8) . . ?
O7 C37 C36 125.5(9) . . ?
O8 C37 C36 110.3(8) . . ?
O8 C38 H38A 109.5 . . ?
O8 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O8 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C9 1.7(8) . . . . ?
C7 N1 N2 C13 -176.4(6) . . . . ?
C6 C1 C2 C3 -2.2(10) . . . . ?
Br1 C1 C2 C3 178.1(5) . . . . ?
C1 C2 C3 C4 0.8(11) . . . . ?
C2 C3 C4 C5 0.6(10) . . . . ?
C2 C3 C4 C7 -179.3(7) . . . . ?
C3 C4 C5 C6 -0.6(10) . . . . ?
C7 C4 C5 C6 179.3(6) . . . . ?
C2 C1 C6 C5 2.3(10) . . . . ?
Br1 C1 C6 C5 -178.0(5) . . . . ?
C4 C5 C6 C1 -0.8(10) . . . . ?
N2 N1 C7 C8 -2.1(8) . . . . ?
N2 N1 C7 C4 177.9(6) . . . . ?
C3 C4 C7 N1 161.9(7) . . . . ?
C5 C4 C7 N1 -18.0(10) . . . . ?
C3 C4 C7 C8 -18.1(11) . . . . ?
C5 C4 C7 C8 161.9(7) . . . . ?
N1 C7 C8 C9 1.7(8) . . . . ?
C4 C7 C8 C9 -178.3(7) . . . . ?
C7 C8 C9 N2 -0.6(8) . . . . ?
C7 C8 C9 C10 179.7(7) . . . . ?
N1 N2 C9 C8 -0.7(8) . . . . ?
C13 N2 C9 C8 177.2(6) . . . . ?
N1 N2 C9 C10 179.0(6) . . . . ?
C13 N2 C9 C10 -3.1(11) . . . . ?
C11 O2 C10 O1 -3.0(11) . . . . ?
C11 O2 C10 C9 175.5(6) . . . . ?
C8 C9 C10 O1 -172.1(8) . . . . ?
N2 C9 C10 O1 8.3(12) . . . . ?
C8 C9 C10 O2 9.5(11) . . . . ?
N2 C9 C10 O2 -170.2(6) . . . . ?
C10 O2 C11 C12 -171.5(6) . . . . ?
C17 N3 C13 N2 106.1(7) . . . . ?
C17 N3 C13 C14 -111.4(7) . . . . ?
N1 N2 C13 N3 -113.5(7) . . . . ?
C9 N2 C13 N3 68.8(9) . . . . ?
N1 N2 C13 C17 -47.7(8) . . . . ?
C9 N2 C13 C17 134.7(7) . . . . ?
N1 N2 C13 C14 100.7(8) . . . . ?
C9 N2 C13 C14 -77.0(9) . . . . ?
N3 C13 C14 C15 156.2(7) . . . . ?
N2 C13 C14 C15 -61.5(8) . . . . ?
C17 C13 C14 C15 84.2(9) . . . . ?
C13 C14 C15 C16 -179.2(11) . . . . ?
C13 N3 C17 C18 108.0(7) . . . . ?
N2 C13 C17 N3 -103.6(6) . . . . ?
C14 C13 C17 N3 111.2(8) . . . . ?
N3 C13 C17 C18 -106.0(8) . . . . ?
N2 C13 C17 C18 150.5(7) . . . . ?
C14 C13 C17 C18 5.2(11) . . . . ?
C19 O4 C18 O3 -2.4(12) . . . . ?
C19 O4 C18 C17 178.6(7) . . . . ?
N3 C17 C18 O3 -2.4(11) . . . . ?
C13 C17 C18 O3 64.3(10) . . . . ?
N3 C17 C18 O4 176.7(6) . . . . ?
C13 C17 C18 O4 -116.6(7) . . . . ?
C26 N4 N5 C28 -0.9(8) . . . . ?
C26 N4 N5 C32 -175.6(5) . . . . ?
C25 C20 C21 C22 -1.3(10) . . . . ?
Br2 C20 C21 C22 178.0(5) . . . . ?
C20 C21 C22 C23 -0.4(10) . . . . ?
C21 C22 C23 C24 1.3(10) . . . . ?
C21 C22 C23 C26 -179.4(7) . . . . ?
C22 C23 C24 C25 -0.6(10) . . . . ?
C26 C23 C24 C25 -179.8(6) . . . . ?
C21 C20 C25 C24 2.0(10) . . . . ?
Br2 C20 C25 C24 -177.3(5) . . . . ?
C23 C24 C25 C20 -1.1(10) . . . . ?
N5 N4 C26 C27 0.3(7) . . . . ?
N5 N4 C26 C23 -179.9(6) . . . . ?
C22 C23 C26 N4 163.4(6) . . . . ?
C24 C23 C26 N4 -17.3(10) . . . . ?
C22 C23 C26 C27 -16.8(11) . . . . ?
C24 C23 C26 C27 162.4(7) . . . . ?
N4 C26 C27 C28 0.5(7) . . . . ?
C23 C26 C27 C28 -179.3(7) . . . . ?
C26 C27 C28 N5 -1.0(7) . . . . ?
C26 C27 C28 C29 -178.9(7) . . . . ?
N4 N5 C28 C27 1.2(8) . . . . ?
C32 N5 C28 C27 175.2(6) . . . . ?
N4 N5 C28 C29 179.3(6) . . . . ?
C32 N5 C28 C29 -6.7(11) . . . . ?
C30 O6 C29 O5 -2.9(10) . . . . ?
C30 O6 C29 C28 177.7(5) . . . . ?
C27 C28 C29 O5 -173.0(7) . . . . ?
N5 C28 C29 O5 9.4(11) . . . . ?
C27 C28 C29 O6 6.3(10) . . . . ?
N5 C28 C29 O6 -171.3(6) . . . . ?
C29 O6 C30 C31 -170.3(6) . . . . ?
N4 N5 C32 N6 -114.7(6) . . . . ?
C28 N5 C32 N6 71.7(9) . . . . ?
N4 N5 C32 C36 -49.2(8) . . . . ?
C28 N5 C32 C36 137.2(7) . . . . ?
N4 N5 C32 C33 101.1(7) . . . . ?
C28 N5 C32 C33 -72.4(8) . . . . ?
C36 N6 C32 N5 106.2(7) . . . . ?
C36 N6 C32 C33 -112.1(7) . . . . ?
N5 C32 C33 C34 -55.5(8) . . . . ?
N6 C32 C33 C34 163.4(6) . . . . ?
C36 C32 C33 C34 92.3(8) . . . . ?
C32 C33 C34 C35 -72.8(9) . . . . ?
C32 N6 C36 C37 109.9(7) . . . . ?
N5 C32 C36 N6 -103.2(6) . . . . ?
C33 C32 C36 N6 109.1(7) . . . . ?
N5 C32 C36 C37 153.0(7) . . . . ?
N6 C32 C36 C37 -103.9(8) . . . . ?
C33 C32 C36 C37 5.2(10) . . . . ?
C38 O8 C37 O7 -3.7(12) . . . . ?
C38 O8 C37 C36 176.3(7) . . . . ?
N6 C36 C37 O7 -7.4(12) . . . . ?
C32 C36 C37 O7 59.5(11) . . . . ?
N6 C36 C37 O8 172.6(6) . . . . ?
C32 C36 C37 O8 -120.5(7) . . . . ?

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.053



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Ethanol
_chemical_properties_physical    ', Heat-sensitive'
