# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_518mgl14
_database_code_depnum_ccdc_archive 'CCDC 1042677'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2016-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'2-(2,6-dimethylphenyl)-9-methyl-2H-pyrazino[1,2-b]isoquinoline-1,4(3H,6H)-dione '
_chemical_name_common            ?
_chemical_melting_point          133-136
_chemical_formula_moiety         'C21 H20 N2 O2'
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.7074(4)
_cell_length_b                   16.5340(5)
_cell_length_c                   7.8722(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.803(2)
_cell_angle_gamma                90
_cell_volume                     1732.62(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4326
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.27

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            12483
_diffrn_reflns_av_unetI/netI     0.1121
_diffrn_reflns_av_R_equivalents  0.1534
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.964
_diffrn_reflns_theta_max         25.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3139
_reflns_number_gt                1611
_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       'APEX2 V2012 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_structure_solution    'SHELXTL  (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2013)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2013)'

_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)+(0.0523P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0103(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3139
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_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 0.16938(14) 0.00969(12) 1.0447(3) 0.0835(7) Uani 1 1 d . . . . .
O2 O 0.31415(12) 0.25870(10) 0.7513(2) 0.0561(5) Uani 1 1 d . . . . .
N1 N 0.14297(14) 0.13237(12) 0.9157(3) 0.0459(5) Uani 1 1 d . . . . .
N2 N 0.34328(14) 0.13985(11) 0.8977(2) 0.0426(5) Uani 1 1 d . . . . .
C1 C 0.20193(19) 0.07092(17) 0.9918(3) 0.0523(7) Uani 1 1 d . . . . .
C2 C 0.31371(17) 0.08112(16) 1.0130(3) 0.0527(7) Uani 1 1 d . . . . .
H2A H 0.3433 0.0968 1.1330 0.063 Uiso 1 1 calc R U . . .
H2B H 0.3419 0.0291 0.9938 0.063 Uiso 1 1 calc R U . . .
C3 C 0.28514(18) 0.20387(15) 0.8327(3) 0.0423(6) Uani 1 1 d . . . . .
C4 C 0.18149(17) 0.20432(15) 0.8595(3) 0.0419(6) Uani 1 1 d . . . . .
C5 C 0.12595(18) 0.27079(15) 0.8305(3) 0.0469(7) Uani 1 1 d . . . . .
H5 H 0.1514 0.3164 0.7871 0.056 Uiso 1 1 calc R U . . .
C6 C 0.02629(18) 0.27437(16) 0.8648(3) 0.0478(7) Uani 1 1 d . . . . .
C7 C -0.02302(19) 0.34713(17) 0.8709(3) 0.0579(8) Uani 1 1 d . . . . .
H7 H 0.0071 0.3951 0.8490 0.069 Uiso 1 1 calc R U . . .
C8 C -0.1175(2) 0.34938(19) 0.9096(4) 0.0634(8) Uani 1 1 d . . . . .
C9 C -0.1600(2) 0.2765(2) 0.9398(4) 0.0698(9) Uani 1 1 d . . . . .
H9 H -0.2230 0.2766 0.9648 0.084 Uiso 1 1 calc R U . . .
C10 C -0.1116(2) 0.20383(19) 0.9339(4) 0.0627(8) Uani 1 1 d . . . . .
H10 H -0.1421 0.1558 0.9549 0.075 Uiso 1 1 calc R U . . .
C11 C -0.01829(18) 0.20208(16) 0.8969(3) 0.0492(7) Uani 1 1 d . . . . .
C12 C 0.03282(18) 0.12356(16) 0.8795(4) 0.0599(8) Uani 1 1 d . . . . .
H12A H 0.0162 0.0845 0.9602 0.072 Uiso 1 1 calc R U . . .
H12B H 0.0080 0.1028 0.7618 0.072 Uiso 1 1 calc R U . . .
C13 C 0.44124(18) 0.12989(14) 0.8580(3) 0.0418(6) Uani 1 1 d . . . . .
C14 C 0.44284(19) 0.10477(14) 0.6896(3) 0.0472(7) Uani 1 1 d . . . . .
C15 C 0.5367(2) 0.09542(16) 0.6524(4) 0.0609(8) Uani 1 1 d . . . . .
H15 H 0.5404 0.0790 0.5412 0.073 Uiso 1 1 calc R U . . .
C16 C 0.6235(2) 0.11004(17) 0.7767(4) 0.0634(8) Uani 1 1 d . . . . .
H16 H 0.6853 0.1033 0.7492 0.076 Uiso 1 1 calc R U . . .
C17 C 0.61975(19) 0.13452(15) 0.9409(4) 0.0560(7) Uani 1 1 d . . . . .
H17 H 0.6793 0.1440 1.0242 0.067 Uiso 1 1 calc R U . . .
C18 C 0.52801(18) 0.14550(14) 0.9857(3) 0.0456(6) Uani 1 1 d . . . . .
C19 C 0.5269(2) 0.17298(19) 1.1666(4) 0.0677(9) Uani 1 1 d . . . . .
H18A H 0.4706 0.2082 1.1614 0.102 Uiso 1 1 calc R U . . .
H18B H 0.5881 0.2015 1.2167 0.102 Uiso 1 1 calc R U . . .
H18C H 0.5214 0.1268 1.2378 0.102 Uiso 1 1 calc R U . . .
C20 C 0.3483(2) 0.08882(17) 0.5517(3) 0.0650(8) Uani 1 1 d . . . . .
H20A H 0.3244 0.1385 0.4932 0.097 Uiso 1 1 calc R U . . .
H20B H 0.2981 0.0670 0.6054 0.097 Uiso 1 1 calc R U . . .
H20C H 0.3621 0.0507 0.4683 0.097 Uiso 1 1 calc R U . . .
C21 C -0.1696(2) 0.4290(2) 0.9177(5) 0.0953(11) Uani 1 1 d . . . . .
H21A H -0.2330 0.4292 0.8330 0.143 Uiso 1 1 calc R U . . .
H21B H -0.1284 0.4722 0.8926 0.143 Uiso 1 1 calc R U . . .
H21C H -0.1807 0.4363 1.0326 0.143 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 1.219(3) . ?
O2 C3 1.230(3) . ?
N1 C1 1.347(3) . ?
N1 C4 1.415(3) . ?
N1 C12 1.475(3) . ?
N2 C3 1.350(3) . ?
N2 C2 1.452(3) . ?
N2 C13 1.459(3) . ?
C1 C2 1.510(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.485(3) . ?
C4 C5 1.325(3) . ?
C5 C6 1.456(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(3) . ?
C6 C11 1.393(3) . ?
C7 C8 1.400(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(4) . ?
C8 C21 1.506(4) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.497(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.386(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.394(3) . ?
C14 C20 1.502(3) . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.396(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.498(3) . ?
C19 H18A 0.9600 . ?
C19 H18B 0.9600 . ?
C19 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 123.0(2) . . ?
C1 N1 C12 119.3(2) . . ?
C4 N1 C12 117.6(2) . . ?
C3 N2 C2 122.26(19) . . ?
C3 N2 C13 119.85(19) . . ?
C2 N2 C13 117.84(18) . . ?
O1 C1 N1 123.3(2) . . ?
O1 C1 C2 119.9(2) . . ?
N1 C1 C2 116.8(2) . . ?
N2 C2 C1 115.6(2) . . ?
N2 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
N2 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
O2 C3 N2 122.7(2) . . ?
O2 C3 C4 120.6(2) . . ?
N2 C3 C4 116.6(2) . . ?
C5 C4 N1 120.6(2) . . ?
C5 C4 C3 120.6(2) . . ?
N1 C4 C3 118.8(2) . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C11 120.0(2) . . ?
C7 C6 C5 121.9(2) . . ?
C11 C6 C5 118.1(2) . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 117.6(3) . . ?
C9 C8 C21 122.0(3) . . ?
C7 C8 C21 120.3(3) . . ?
C10 C9 C8 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 119.3(2) . . ?
C10 C11 C12 121.0(2) . . ?
C6 C11 C12 119.5(2) . . ?
N1 C12 C11 112.1(2) . . ?
N1 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
N1 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C18 C13 C14 122.7(2) . . ?
C18 C13 N2 119.9(2) . . ?
C14 C13 N2 117.5(2) . . ?
C15 C14 C13 117.2(2) . . ?
C15 C14 C20 120.6(2) . . ?
C13 C14 C20 122.2(2) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C17 117.5(2) . . ?
C13 C18 C19 123.0(2) . . ?
C17 C18 C19 119.5(2) . . ?
C18 C19 H18A 109.5 . . ?
C18 C19 H18B 109.5 . . ?
H18A C19 H18B 109.5 . . ?
C18 C19 H18C 109.5 . . ?
H18A C19 H18C 109.5 . . ?
H18B C19 H18C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C21 H21A 109.5 . . ?
C8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/Hexane'
####################################################################### 
# 
# 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_093mgl15
_database_code_depnum_ccdc_archive 'CCDC 1051289'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2016-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
2-benzyl--2H-pyrazino[1,2-b]isoquinoline-1,4(3H,6H)-dione
_chemical_name_common            ?
_chemical_melting_point          123-125
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34

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      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                   6.0126(2)
_cell_length_b                   8.6199(2)
_cell_length_c                   14.4875(4)
_cell_angle_alpha                87.1650(10)
_cell_angle_beta                 79.5970(10)
_cell_angle_gamma                86.9100(10)
_cell_volume                     736.84(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5570
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.35

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            10958
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         25.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2713
_reflns_number_gt                1910
_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       'APEX2 V2012 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_structure_solution    'SHELXTL  (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2013)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2013)'

_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)+(0.0614P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2713
_refine_ls_number_parameters     264
_refine_ls_number_restraints     243
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.036
_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 1.27587(16) 0.50186(12) 0.61746(7) 0.0521(3) Uani 1 1 d . . . . .
O2 O 0.51426(16) 0.84670(12) 0.61238(7) 0.0569(3) Uani 1 1 d . . . . .
C1 C 1.0991(2) 0.58040(16) 0.61794(9) 0.0380(3) Uani 1 1 d . . . . .
N2 N 0.93383(19) 0.58584(13) 0.69382(8) 0.0431(3) Uani 1 1 d . . . . .
C3 C 0.7133(2) 0.66143(18) 0.69350(10) 0.0462(4) Uani 1 1 d . . . . .
H3A H 0.6737 0.7213 0.7496 0.055 Uiso 1 1 calc R U . . .
H3B H 0.6040 0.5814 0.6981 0.055 Uiso 1 1 calc R U . . .
C4 C 0.6882(2) 0.76681(16) 0.61076(10) 0.0413(4) Uani 1 1 d . . . . .
N5 N 0.85931(17) 0.76737(12) 0.53574(7) 0.0373(3) Uani 1 1 d . . . . .
C6 C 0.8167(2) 0.86794(18) 0.45469(10) 0.0461(4) Uani 1 1 d . . . . .
H6A H 0.7814 0.9732 0.4753 0.055 Uiso 1 1 calc R U . . .
H6B H 0.6849 0.8327 0.4332 0.055 Uiso 1 1 calc R U . . .
C7 C 1.0109(2) 0.87066(16) 0.37342(10) 0.0390(3) Uani 1 1 d . . . . .
C8 C 0.9928(3) 0.96678(17) 0.29511(10) 0.0466(4) Uani 1 1 d . . . . .
H8 H 0.8604 1.0268 0.2931 0.056 Uiso 1 1 calc R U . . .
C9 C 1.1704(3) 0.97362(18) 0.22040(11) 0.0557(4) Uani 1 1 d . . . . .
H9 H 1.1565 1.0377 0.1680 0.067 Uiso 1 1 calc R U . . .
C10 C 1.3683(3) 0.88635(18) 0.22258(11) 0.0530(4) Uani 1 1 d . . . . .
H10 H 1.4881 0.8931 0.1722 0.064 Uiso 1 1 calc R U . . .
C11 C 1.3890(2) 0.78894(17) 0.29933(10) 0.0456(4) Uani 1 1 d . . . . .
H11 H 1.5221 0.7292 0.3003 0.055 Uiso 1 1 calc R U . . .
C12 C 1.2105(2) 0.77985(15) 0.37550(9) 0.0378(3) Uani 1 1 d . . . . .
C13 C 1.2274(2) 0.68176(16) 0.45826(9) 0.0388(4) Uani 1 1 d . . . . .
H13 H 1.3581 0.6193 0.4591 0.047 Uiso 1 1 calc R U . . .
C14 C 1.0624(2) 0.67770(15) 0.53339(9) 0.0339(3) Uani 1 1 d . . . . .
C15 C 0.9589(3) 0.49569(18) 0.78041(10) 0.0505(4) Uani 1 1 d D U . . .
H15A H 1.1012 0.4351 0.7698 0.061 Uiso 1 1 calc R U . A 1
H15B H 0.8378 0.4237 0.7954 0.061 Uiso 1 1 calc R U . A 1
C16 C 0.9536(19) 0.5970(18) 0.8631(7) 0.0394(10) Uani 0.651(13) 1 d D U P B 1
C17 C 1.1329(11) 0.6853(8) 0.8714(4) 0.0545(12) Uani 0.651(13) 1 d D U P B 1
H17 H 1.2617 0.6833 0.8250 0.065 Uiso 0.651(13) 1 calc R U P B 1
C18 C 1.1239(10) 0.7779(6) 0.9488(5) 0.0592(12) Uani 0.651(13) 1 d D U P B 1
H18 H 1.2449 0.8383 0.9532 0.071 Uiso 0.651(13) 1 calc R U P B 1
C19 C 0.9370(13) 0.7790(5) 1.0175(3) 0.0536(12) Uani 0.651(13) 1 d D U P B 1
H19 H 0.9312 0.8385 1.0697 0.064 Uiso 0.651(13) 1 calc R U P B 1
C20 C 0.7562(12) 0.6921(6) 1.0097(3) 0.0591(11) Uani 0.651(13) 1 d D U P B 1
H20 H 0.6283 0.6933 1.0567 0.071 Uiso 0.651(13) 1 calc R U P B 1
C21 C 0.7642(11) 0.6035(10) 0.9328(4) 0.0497(11) Uani 0.651(13) 1 d D U P B 1
H21 H 0.6398 0.5470 0.9276 0.060 Uiso 0.651(13) 1 calc R U P B 1
C16A C 0.973(3) 0.603(4) 0.8568(14) 0.0420(17) Uani 0.349(13) 1 d D U P B 2
C17A C 1.1595(18) 0.6951(15) 0.8467(7) 0.0502(16) Uani 0.349(13) 1 d D U P B 2
H17A H 1.2639 0.6956 0.7908 0.060 Uiso 0.349(13) 1 calc R U P B 2
C18A C 1.1909(17) 0.7847(11) 0.9182(8) 0.0587(16) Uani 0.349(13) 1 d D U P B 2
H18A H 1.3193 0.8425 0.9120 0.070 Uiso 0.349(13) 1 calc R U P B 2
C19A C 1.032(2) 0.7890(10) 0.9992(6) 0.0559(18) Uani 0.349(13) 1 d D U P B 2
H19A H 1.0566 0.8473 1.0485 0.067 Uiso 0.349(13) 1 calc R U P B 2
C20A C 0.8398(19) 0.7093(12) 1.0084(5) 0.0568(17) Uani 0.349(13) 1 d D U P B 2
H20A H 0.7269 0.7197 1.0612 0.068 Uiso 0.349(13) 1 calc R U P B 2
C21A C 0.8147(19) 0.6116(19) 0.9373(8) 0.0501(18) Uani 0.349(13) 1 d D U P B 2
H21A H 0.6886 0.5512 0.9447 0.060 Uiso 0.349(13) 1 calc R U P B 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
O1 C1 1.2283(14) . ?
O2 C4 1.2182(15) . ?
C1 N2 1.3429(17) . ?
C1 C14 1.4927(18) . ?
N2 C3 1.4460(16) . ?
N2 C15 1.4696(17) . ?
C3 C4 1.4925(19) . ?
C4 N5 1.3549(16) . ?
N5 C14 1.4056(16) . ?
N5 C6 1.4765(17) . ?
C6 C7 1.501(2) . ?
C7 C8 1.3883(19) . ?
C7 C12 1.4012(18) . ?
C8 C9 1.378(2) . ?
C9 C10 1.378(2) . ?
C10 C11 1.3796(19) . ?
C11 C12 1.3958(18) . ?
C12 C13 1.4482(18) . ?
C13 C14 1.3342(18) . ?
C15 C16A 1.496(5) . ?
C15 C16 1.512(3) . ?
C16 C17 1.379(4) . ?
C16 C21 1.379(4) . ?
C17 C18 1.400(4) . ?
C18 C19 1.360(4) . ?
C19 C20 1.377(4) . ?
C20 C21 1.374(4) . ?
C16A C21A 1.367(6) . ?
C16A C17A 1.389(6) . ?
C17A C18A 1.368(6) . ?
C18A C19A 1.372(6) . ?
C19A C20A 1.360(7) . ?
C20A C21A 1.397(6) . ?

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
O1 C1 N2 122.29(13) . . ?
O1 C1 C14 120.54(12) . . ?
N2 C1 C14 117.16(11) . . ?
C1 N2 C3 123.70(11) . . ?
C1 N2 C15 120.46(11) . . ?
C3 N2 C15 115.38(11) . . ?
N2 C3 C4 116.87(11) . . ?
O2 C4 N5 122.53(13) . . ?
O2 C4 C3 119.11(12) . . ?
N5 C4 C3 118.35(11) . . ?
C4 N5 C14 123.18(11) . . ?
C4 N5 C6 115.15(11) . . ?
C14 N5 C6 121.66(11) . . ?
N5 C6 C7 114.32(11) . . ?
C8 C7 C12 119.45(13) . . ?
C8 C7 C6 119.12(12) . . ?
C12 C7 C6 121.42(12) . . ?
C9 C8 C7 120.23(14) . . ?
C10 C9 C8 120.60(14) . . ?
C9 C10 C11 120.10(14) . . ?
C10 C11 C12 120.13(13) . . ?
C11 C12 C7 119.48(13) . . ?
C11 C12 C13 121.82(12) . . ?
C7 C12 C13 118.67(12) . . ?
C14 C13 C12 122.43(12) . . ?
C13 C14 N5 121.43(12) . . ?
C13 C14 C1 118.98(12) . . ?
N5 C14 C1 119.55(11) . . ?
N2 C15 C16A 109.9(15) . . ?
N2 C15 C16 112.8(8) . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 C15 122.1(3) . . ?
C21 C16 C15 119.8(3) . . ?
C16 C17 C18 121.0(3) . . ?
C19 C18 C17 119.5(3) . . ?
C18 C19 C20 120.1(3) . . ?
C21 C20 C19 120.2(3) . . ?
C20 C21 C16 121.1(3) . . ?
C21A C16A C17A 118.7(5) . . ?
C21A C16A C15 123.0(6) . . ?
C17A C16A C15 118.2(5) . . ?
C18A C17A C16A 120.5(5) . . ?
C17A C18A C19A 119.8(5) . . ?
C20A C19A C18A 121.0(5) . . ?
C19A C20A C21A 118.8(5) . . ?
C16A C21A C20A 120.9(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
O1 C1 N2 C3 -172.20(13) . . . . ?
C14 C1 N2 C3 9.3(2) . . . . ?
O1 C1 N2 C15 -0.3(2) . . . . ?
C14 C1 N2 C15 -178.86(11) . . . . ?
C1 N2 C3 C4 -13.7(2) . . . . ?
C15 N2 C3 C4 174.05(12) . . . . ?
N2 C3 C4 O2 -171.54(12) . . . . ?
N2 C3 C4 N5 9.7(2) . . . . ?
O2 C4 N5 C14 178.98(12) . . . . ?
C3 C4 N5 C14 -2.3(2) . . . . ?
O2 C4 N5 C6 -2.0(2) . . . . ?
C3 C4 N5 C6 176.72(12) . . . . ?
C4 N5 C6 C7 178.25(12) . . . . ?
C14 N5 C6 C7 -2.68(19) . . . . ?
N5 C6 C7 C8 -177.18(12) . . . . ?
N5 C6 C7 C12 2.0(2) . . . . ?
C12 C7 C8 C9 -0.5(2) . . . . ?
C6 C7 C8 C9 178.74(13) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C10 C11 C12 C13 -178.57(13) . . . . ?
C8 C7 C12 C11 0.8(2) . . . . ?
C6 C7 C12 C11 -178.41(13) . . . . ?
C8 C7 C12 C13 179.23(12) . . . . ?
C6 C7 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 176.66(13) . . . . ?
C7 C12 C13 C14 -1.7(2) . . . . ?
C12 C13 C14 N5 1.1(2) . . . . ?
C12 C13 C14 C1 -176.43(11) . . . . ?
C4 N5 C14 C13 -179.78(12) . . . . ?
C6 N5 C14 C13 1.2(2) . . . . ?
C4 N5 C14 C1 -2.24(19) . . . . ?
C6 N5 C14 C1 178.76(12) . . . . ?
O1 C1 C14 C13 -2.0(2) . . . . ?
N2 C1 C14 C13 176.56(12) . . . . ?
O1 C1 C14 N5 -179.61(12) . . . . ?
N2 C1 C14 N5 -1.03(19) . . . . ?
C1 N2 C15 C16A 113.6(7) . . . . ?
C3 N2 C15 C16A -73.9(7) . . . . ?
C1 N2 C15 C16 118.6(4) . . . . ?
C3 N2 C15 C16 -68.8(4) . . . . ?
N2 C15 C16 C17 -73.7(16) . . . . ?
C16A C15 C16 C17 -15(23) . . . . ?
N2 C15 C16 C21 105.8(14) . . . . ?
C16A C15 C16 C21 164(26) . . . . ?
C21 C16 C17 C18 0.6(19) . . . . ?
C15 C16 C17 C18 -179.9(11) . . . . ?
C16 C17 C18 C19 1.0(12) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C18 C19 C20 C21 0.2(8) . . . . ?
C19 C20 C21 C16 1.4(14) . . . . ?
C17 C16 C21 C20 -2(2) . . . . ?
C15 C16 C21 C20 178.7(11) . . . . ?
N2 C15 C16A C21A 117(3) . . . . ?
C16 C15 C16A C21A -7(21) . . . . ?
N2 C15 C16A C17A -66(3) . . . . ?
C16 C15 C16A C17A 171(27) . . . . ?
C21A C16A C17A C18A 4(4) . . . . ?
C15 C16A C17A C18A -174(2) . . . . ?
C16A C17A C18A C19A -3(2) . . . . ?
C17A C18A C19A C20A -2.1(16) . . . . ?
C18A C19A C20A C21A 5.6(17) . . . . ?
C17A C16A C21A C20A 0(4) . . . . ?
C15 C16A C21A C20A 177(2) . . . . ?
C19A C20A C21A C16A -4(3) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
