# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ab021
_database_code_depnum_ccdc_archive 'CCDC 1420522'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Br N3 O2'
_chemical_formula_weight         344.17

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                   5.2396(12)
_cell_length_b                   10.766(2)
_cell_length_c                   12.305(2)
_cell_angle_alpha                97.556(10)
_cell_angle_beta                 93.106(12)
_cell_angle_gamma                95.573(10)
_cell_volume                     683.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3366
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      28.14

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.016
_shelx_estimated_absorpt_T_min   0.418
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5426
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with four batch runs at phi = 0.00 deg 
 (600 frames), at phi = 90.00 deg (600 frames), at phi = 180.00 deg 
 (600 frames), and at phi = 270.00 deg (600 frames). 
 A fifth batch run is collected at phi = 0.00 deg (50 frames) to monitor 
 crystal and diffractometer stability. Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(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            5941
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         28.224
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3252
_reflns_number_gt                2734
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_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)+(0.0498P)²+0.2395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     186
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.032
_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 -0.00975(6) -0.32821(2) 0.54624(2) 0.05491(12) Uani 1 1 d . . . . .
O1 O -0.3792(3) -0.07672(14) 0.10725(11) 0.0342(3) Uani 1 1 d . . . . .
O2 O 0.3610(3) 0.13220(13) 0.27907(14) 0.0387(4) Uani 1 1 d . . . . .
N1 N -0.0233(3) 0.03240(15) 0.20435(13) 0.0257(3) Uani 1 1 d . . . . .
N2 N -0.2124(3) 0.10709(16) 0.05492(14) 0.0319(4) Uani 1 1 d . . . . .
H2A H -0.3235 0.0946 -0.0027 0.038 Uiso 1 1 calc R U . . .
N3 N -0.0526(3) 0.21610(16) 0.06890(14) 0.0296(3) Uani 1 1 d . . . . .
C3 C -0.2174(3) 0.01547(18) 0.12130(15) 0.0268(4) Uani 1 1 d . . . . .
C4 C 0.1329(3) 0.23144(17) 0.14531(15) 0.0261(4) Uani 1 1 d . . . . .
C5 C 0.1759(3) 0.13218(17) 0.21567(15) 0.0260(4) Uani 1 1 d . . . . .
C6 C -0.0245(3) -0.05694(17) 0.28271(15) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.1523(4) -0.1445(2) 0.2793(2) 0.0359(4) Uani 1 1 d . . . . .
H7A H 0.2714 -0.1488 0.2237 0.043 Uiso 1 1 calc R U . . .
C8 C 0.1546(4) -0.2264(2) 0.3578(2) 0.0397(5) Uani 1 1 d . . . . .
H8A H 0.2754 -0.2868 0.3565 0.048 Uiso 1 1 calc R U . . .
C9 C -0.0201(4) -0.21886(18) 0.43731(16) 0.0307(4) Uani 1 1 d . . . . .
C10 C -0.2005(4) -0.13262(19) 0.44059(16) 0.0329(4) Uani 1 1 d . . . . .
H10A H -0.3212 -0.1293 0.4955 0.040 Uiso 1 1 calc R U . . .
C11 C -0.2012(4) -0.05068(19) 0.36154(16) 0.0306(4) Uani 1 1 d . . . . .
H11A H -0.3232 0.0091 0.3622 0.037 Uiso 1 1 calc R U . . .
C12 C 0.2925(4) 0.35565(18) 0.16130(16) 0.0275(4) Uani 1 1 d D . . . .
C13 C 0.2635(9) 0.4400(4) 0.0829(4) 0.0350(9) Uiso 0.5 1 d D . P A 1
H13A H 0.1468 0.4151 0.0203 0.042 Uiso 0.5 1 calc R U P A 1
C14 C 0.4022(9) 0.5578(4) 0.0961(4) 0.0369(9) Uiso 0.5 1 d D . P A 1
H14A H 0.3797 0.6129 0.0429 0.044 Uiso 0.5 1 calc R U P A 1
C16' C 0.6144(9) 0.5124(4) 0.2596(4) 0.0351(10) Uiso 0.5 1 d D . P A 1
H16A H 0.7394 0.5371 0.3193 0.042 Uiso 0.5 1 calc R U P A 1
C17' C 0.4779(9) 0.3938(4) 0.2482(4) 0.0310(10) Uiso 0.5 1 d D . P A 1
H17A H 0.5109 0.3382 0.2999 0.037 Uiso 0.5 1 calc R U P A 1
C13' C 0.1824(8) 0.4575(4) 0.1223(4) 0.0303(8) Uiso 0.5 1 d D . P A 2
H13B H 0.0136 0.4452 0.0877 0.036 Uiso 0.5 1 calc R U P A 2
C14' C 0.3203(9) 0.5749(4) 0.1344(4) 0.0342(9) Uiso 0.5 1 d D . P A 2
H14B H 0.2455 0.6431 0.1080 0.041 Uiso 0.5 1 calc R U P A 2
C16 C 0.6710(9) 0.4965(4) 0.2289(4) 0.0329(10) Uiso 0.5 1 d D . P A 2
H16B H 0.8362 0.5100 0.2669 0.039 Uiso 0.5 1 calc R U P A 2
C17 C 0.5334(8) 0.3773(4) 0.2178(4) 0.0276(9) Uiso 0.5 1 d D . P A 2
H17B H 0.6042 0.3109 0.2488 0.033 Uiso 0.5 1 calc R U P A 2
C15 C 0.5718(4) 0.5950(2) 0.18569(19) 0.0392(5) Uani 1 1 d D . . . .
H15A H 0.6598 0.6775 0.1968 0.047 Uiso 0.5 1 calc R U P A 1
H15B H 0.6703 0.6746 0.1903 0.047 Uiso 0.5 1 calc R U P A 2


_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 C9 1.8987(19) . ?
O1 C3 1.228(2) . ?
O2 C5 1.211(2) . ?
N1 C3 1.384(2) . ?
N1 C5 1.411(2) . ?
N1 C6 1.448(2) . ?
N2 N3 1.360(2) . ?
N2 C3 1.360(2) . ?
N3 C4 1.298(2) . ?
C4 C5 1.487(3) . ?
C4 C12 1.491(3) . ?
C6 C11 1.377(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.397(3) . ?
C12 C17 1.391(4) . ?
C12 C17' 1.396(4) . ?
C12 C13' 1.414(4) . ?
C12 C13 1.421(5) . ?
C13 C14 1.385(6) . ?
C14 C15 1.368(5) . ?
C16' C15 1.376(5) . ?
C16' C17' 1.388(6) . ?
C13' C14' 1.379(5) . ?
C14' C15 1.414(5) . ?
C16 C15 1.379(5) . ?
C16 C17 1.396(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
C3 N1 C5 122.96(16) . . ?
C3 N1 C6 118.38(15) . . ?
C5 N1 C6 118.66(14) . . ?
N3 N2 C3 126.36(15) . . ?
C4 N3 N2 118.60(16) . . ?
O1 C3 N2 122.51(16) . . ?
O1 C3 N1 122.47(17) . . ?
N2 C3 N1 115.01(16) . . ?
N3 C4 C5 121.55(16) . . ?
N3 C4 C12 116.27(16) . . ?
C5 C4 C12 122.13(15) . . ?
O2 C5 N1 120.15(17) . . ?
O2 C5 C4 125.62(16) . . ?
N1 C5 C4 114.23(15) . . ?
C11 C6 C7 121.08(18) . . ?
C11 C6 N1 118.53(17) . . ?
C7 C6 N1 120.37(18) . . ?
C6 C7 C8 119.5(2) . . ?
C9 C8 C7 119.2(2) . . ?
C8 C9 C10 121.71(19) . . ?
C8 C9 Br1 118.89(16) . . ?
C10 C9 Br1 119.39(16) . . ?
C9 C10 C11 118.7(2) . . ?
C6 C11 C10 119.75(19) . . ?
C17 C12 C13' 119.2(3) . . ?
C17' C12 C13 117.0(3) . . ?
C17 C12 C4 123.6(2) . . ?
C17' C12 C4 123.7(2) . . ?
C13' C12 C4 117.1(2) . . ?
C13 C12 C4 119.2(2) . . ?
C14 C13 C12 121.2(4) . . ?
C15 C14 C13 120.1(4) . . ?
C15 C16' C17' 121.1(4) . . ?
C16' C17' C12 120.5(4) . . ?
C14' C13' C12 119.9(3) . . ?
C13' C14' C15 120.8(4) . . ?
C15 C16 C17 121.2(4) . . ?
C12 C17 C16 120.0(3) . . ?
C14 C15 C16' 119.8(3) . . ?
C16 C15 C14' 118.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 N3 C4 7.8(3) . . . . ?
N3 N2 C3 O1 175.06(19) . . . . ?
N3 N2 C3 N1 -6.3(3) . . . . ?
C5 N1 C3 O1 174.50(18) . . . . ?
C6 N1 C3 O1 -5.1(3) . . . . ?
C5 N1 C3 N2 -4.1(3) . . . . ?
C6 N1 C3 N2 176.24(17) . . . . ?
N2 N3 C4 C5 1.1(3) . . . . ?
N2 N3 C4 C12 -176.52(17) . . . . ?
C3 N1 C5 O2 -168.89(19) . . . . ?
C6 N1 C5 O2 10.7(3) . . . . ?
C3 N1 C5 C4 11.5(3) . . . . ?
C6 N1 C5 C4 -168.88(16) . . . . ?
N3 C4 C5 O2 170.4(2) . . . . ?
C12 C4 C5 O2 -12.1(3) . . . . ?
N3 C4 C5 N1 -10.0(3) . . . . ?
C12 C4 C5 N1 167.49(17) . . . . ?
C3 N1 C6 C11 -74.4(2) . . . . ?
C5 N1 C6 C11 105.9(2) . . . . ?
C3 N1 C6 C7 106.9(2) . . . . ?
C5 N1 C6 C7 -72.7(2) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
N1 C6 C7 C8 177.57(18) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C9 Br1 -178.45(17) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
Br1 C9 C10 C11 178.37(14) . . . . ?
C7 C6 C11 C10 1.0(3) . . . . ?
N1 C6 C11 C10 -177.67(16) . . . . ?
C9 C10 C11 C6 0.0(3) . . . . ?
N3 C4 C12 C17 -162.9(3) . . . . ?
C5 C4 C12 C17 19.5(4) . . . . ?
N3 C4 C12 C17' 171.7(3) . . . . ?
C5 C4 C12 C17' -5.9(4) . . . . ?
N3 C4 C12 C13' 21.2(3) . . . . ?
C5 C4 C12 C13' -156.4(3) . . . . ?
N3 C4 C12 C13 -10.4(3) . . . . ?
C5 C4 C12 C13 172.1(3) . . . . ?
C17 C12 C13 C14 -26.4(6) . . . . ?
C17' C12 C13 C14 -3.8(6) . . . . ?
C13' C12 C13 C14 84.8(6) . . . . ?
C4 C12 C13 C14 178.1(4) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C15 C16' C17' C12 -0.3(8) . . . . ?
C17 C12 C17' C16' 85.0(8) . . . . ?
C13' C12 C17' C16' -26.7(6) . . . . ?
C13 C12 C17' C16' 3.8(6) . . . . ?
C4 C12 C17' C16' -178.2(4) . . . . ?
C17 C12 C13' C14' 4.0(6) . . . . ?
C17' C12 C13' C14' 26.5(5) . . . . ?
C13 C12 C13' C14' -78.0(6) . . . . ?
C4 C12 C13' C14' -179.9(4) . . . . ?
C12 C13' C14' C15 0.0(7) . . . . ?
C17' C12 C17 C16 -82.7(8) . . . . ?
C13' C12 C17 C16 -4.3(6) . . . . ?
C13 C12 C17 C16 25.6(6) . . . . ?
C4 C12 C17 C16 179.8(4) . . . . ?
C15 C16 C17 C12 0.7(7) . . . . ?
C13 C14 C15 C16' 3.5(7) . . . . ?
C13 C14 C15 C16 26.8(6) . . . . ?
C13 C14 C15 C14' -79.7(7) . . . . ?
C17' C16' C15 C14 -3.5(7) . . . . ?
C17' C16' C15 C16 -83.0(9) . . . . ?
C17' C16' C15 C14' 26.9(6) . . . . ?
C17 C16 C15 C14 -27.6(6) . . . . ?
C17 C16 C15 C16' 83.6(9) . . . . ?
C17 C16 C15 C14' 3.3(7) . . . . ?
C13' C14' C15 C14 83.9(7) . . . . ?
C13' C14' C15 C16' -26.7(6) . . . . ?
C13' C14' C15 C16 -3.6(6) . . . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_ab023a
_database_code_depnum_ccdc_archive 'CCDC 1420523'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N4 O'
_chemical_formula_weight         200.20

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   19.8268(18)
_cell_length_b                   5.0233(5)
_cell_length_c                   8.7396(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     870.43(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5112
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.21

_exptl_crystal_description       plate
_exptl_crystal_colour            gold
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6108
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(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            9035
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.054
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.924
_reflns_number_total             1885
_reflns_number_gt                1418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.839
_reflns_Friedel_fraction_full    0.916

_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_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)+(0.0550P)²+0.0538P] 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 540 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1885
_refine_ls_number_parameters     137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.013
_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 0.63503(13) 0.7791(5) 0.3596(3) 0.0366(7) Uani 1 1 d . . . . .
N1 N 0.67156(13) 0.4444(6) 0.5170(3) 0.0255(7) Uani 1 1 d . . . . .
N2 N 0.70248(13) 0.1086(5) 0.6721(3) 0.0254(7) Uani 1 1 d . . . . .
N3 N 0.74758(15) 0.6935(5) 0.3814(4) 0.0292(7) Uani 1 1 d . . . . .
H3A H 0.7564 0.8197 0.3145 0.035 Uiso 1 1 calc R U . . .
N4 N 0.80245(14) 0.5610(6) 0.4409(4) 0.0285(7) Uani 1 1 d . . . . .
C1 C 0.68107(18) 0.6519(7) 0.4143(4) 0.0277(9) Uani 1 1 d . . . . .
C2 C 0.79164(17) 0.3669(6) 0.5353(4) 0.0250(8) Uani 1 1 d . . . . .
C3 C 0.72390(16) 0.2953(6) 0.5789(4) 0.0238(7) Uani 1 1 d . . . . .
C4 C 0.85003(17) 0.2188(7) 0.5982(4) 0.0316(8) Uani 1 1 d . . . . .
H4A H 0.8916 0.2825 0.5499 0.047 Uiso 1 1 calc R U . . .
H4B H 0.8445 0.0284 0.5774 0.047 Uiso 1 1 calc R U . . .
H4C H 0.8526 0.2476 0.7090 0.047 Uiso 1 1 calc R U . . .
C5 C 0.61163(17) 0.3403(6) 0.5758(4) 0.0250(8) Uani 1 1 d . . . . .
C6 C 0.63193(16) 0.1335(6) 0.6711(4) 0.0243(7) Uani 1 1 d . . . . .
C7 C 0.58407(17) -0.0152(7) 0.7508(4) 0.0292(8) Uani 1 1 d . . . . .
H7A H 0.5969 -0.1576 0.8161 0.035 Uiso 1 1 calc R U . . .
C8 C 0.51739(18) 0.0530(7) 0.7307(5) 0.0336(9) Uani 1 1 d . . . . .
H8A H 0.4837 -0.0436 0.7845 0.040 Uiso 1 1 calc R U . . .
C9 C 0.49775(18) 0.2602(7) 0.6335(5) 0.0335(9) Uani 1 1 d . . . . .
H9A H 0.4512 0.3003 0.6229 0.040 Uiso 1 1 calc R U . . .
C10 C 0.54427(17) 0.4077(7) 0.5527(4) 0.0317(9) Uani 1 1 d . . . . .
H10A H 0.5312 0.5470 0.4854 0.038 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 1.212(4) . ?
N1 C1 1.389(4) . ?
N1 C3 1.389(4) . ?
N1 C5 1.396(4) . ?
N2 C3 1.313(5) . ?
N2 C6 1.404(4) . ?
N3 C1 1.366(5) . ?
N3 N4 1.377(4) . ?
N4 C2 1.295(5) . ?
C2 C3 1.442(5) . ?
C2 C4 1.482(5) . ?
C5 C6 1.391(5) . ?
C5 C10 1.392(5) . ?
C6 C7 1.394(4) . ?
C7 C8 1.377(5) . ?
C8 C9 1.399(5) . ?
C9 C10 1.377(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 C3 123.7(3) . . ?
C1 N1 C5 129.4(3) . . ?
C3 N1 C5 106.9(3) . . ?
C3 N2 C6 104.8(3) . . ?
C1 N3 N4 127.6(3) . . ?
C2 N4 N3 118.3(3) . . ?
O1 C1 N3 124.3(3) . . ?
O1 C1 N1 123.3(3) . . ?
N3 C1 N1 112.4(3) . . ?
N4 C2 C3 120.7(3) . . ?
N4 C2 C4 119.0(3) . . ?
C3 C2 C4 120.3(3) . . ?
N2 C3 N1 112.7(3) . . ?
N2 C3 C2 130.1(3) . . ?
N1 C3 C2 117.3(3) . . ?
C6 C5 C10 123.1(3) . . ?
C6 C5 N1 104.7(3) . . ?
C10 C5 N1 132.2(3) . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 N2 111.0(3) . . ?
C7 C6 N2 128.8(3) . . ?
C8 C7 C6 117.2(3) . . ?
C7 C8 C9 122.0(3) . . ?
C10 C9 C8 121.7(3) . . ?
C9 C10 C5 115.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N3 N4 C2 2.6(5) . . . . ?
N4 N3 C1 O1 178.7(3) . . . . ?
N4 N3 C1 N1 -1.9(5) . . . . ?
C3 N1 C1 O1 179.2(3) . . . . ?
C5 N1 C1 O1 0.6(6) . . . . ?
C3 N1 C1 N3 -0.2(4) . . . . ?
C5 N1 C1 N3 -178.9(3) . . . . ?
N3 N4 C2 C3 -1.1(5) . . . . ?
N3 N4 C2 C4 178.9(3) . . . . ?
C6 N2 C3 N1 0.5(4) . . . . ?
C6 N2 C3 C2 179.5(3) . . . . ?
C1 N1 C3 N2 -179.4(3) . . . . ?
C5 N1 C3 N2 -0.5(4) . . . . ?
C1 N1 C3 C2 1.4(4) . . . . ?
C5 N1 C3 C2 -179.6(3) . . . . ?
N4 C2 C3 N2 -179.7(4) . . . . ?
C4 C2 C3 N2 0.3(6) . . . . ?
N4 C2 C3 N1 -0.7(5) . . . . ?
C4 C2 C3 N1 179.3(3) . . . . ?
C1 N1 C5 C6 179.1(3) . . . . ?
C3 N1 C5 C6 0.3(3) . . . . ?
C1 N1 C5 C10 -0.4(6) . . . . ?
C3 N1 C5 C10 -179.2(4) . . . . ?
C10 C5 C6 C7 -0.9(5) . . . . ?
N1 C5 C6 C7 179.5(3) . . . . ?
C10 C5 C6 N2 179.6(3) . . . . ?
N1 C5 C6 N2 0.0(4) . . . . ?
C3 N2 C6 C5 -0.3(4) . . . . ?
C3 N2 C6 C7 -179.8(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
N2 C6 C7 C8 179.2(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 C5 -0.9(5) . . . . ?
C6 C5 C10 C9 1.5(5) . . . . ?
N1 C5 C10 C9 -179.1(4) . . . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4

