# 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_376MGL14
_database_code_depnum_ccdc_archive 'CCDC 1496194'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
N-(2,6-dimethylphenyl)-2-(N-(prop-2-yn-1-yl)acetamido)pentanamide
_chemical_name_common            ?
_chemical_melting_point          149-152
_chemical_formula_moiety         'C18 H24 N2 O2'
_chemical_formula_sum            'C18 H24 N2 O2'
_chemical_formula_weight         300.39

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.344(3)
_cell_length_b                   22.993(7)
_cell_length_c                   16.649(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3576.9(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3648
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.54

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   '(Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            22418
_diffrn_reflns_av_unetI/netI     0.1164
_diffrn_reflns_av_R_equivalents  0.1461
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4111
_reflns_number_gt                1886
_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 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (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)+(0.0957P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0077(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4111
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1588
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2355
_refine_ls_wR_factor_gt          0.1767
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.8234(2) 0.48898(12) 0.22349(13) 0.0858(8) Uani 1 1 d . . . . .
O2 O 0.60764(17) 0.34820(9) 0.27661(12) 0.0578(6) Uani 1 1 d . . . . .
N1 N 0.7344(2) 0.44706(9) 0.33346(12) 0.0425(6) Uani 1 1 d . . . . .
N2 N 0.8176(2) 0.30793(10) 0.24077(13) 0.0463(6) Uani 1 1 d . . . . .
H2 H 0.901(3) 0.3158(13) 0.2392(16) 0.056 Uiso 1 1 d . U . . .
C1 C 0.8236(2) 0.39579(11) 0.32056(15) 0.0416(6) Uani 1 1 d . . . . .
H1 H 0.9022 0.4074 0.2851 0.050 Uiso 1 1 calc R U . . .
C2 C 0.8902(3) 0.37325(13) 0.39777(17) 0.0542(8) Uani 1 1 d . . . . .
H2A H 0.8148 0.3665 0.4367 0.065 Uiso 1 1 calc R U . . .
H2B H 0.9358 0.3362 0.3869 0.065 Uiso 1 1 calc R U . . .
C3 C 0.9995(3) 0.41408(15) 0.43409(18) 0.0658(9) Uani 1 1 d . . . . .
H3A H 0.9602 0.4531 0.4359 0.079 Uiso 1 1 calc R U . . .
H3B H 1.0841 0.4149 0.4004 0.079 Uiso 1 1 calc R U . . .
C4 C 1.0415(4) 0.39532(18) 0.5187(2) 0.0981(13) Uani 1 1 d . . . . .
H4A H 1.1182 0.4194 0.5377 0.147 Uiso 1 1 calc R U . . .
H4B H 1.0721 0.3555 0.5178 0.147 Uiso 1 1 calc R U . . .
H4C H 0.9605 0.3992 0.5538 0.147 Uiso 1 1 calc R U . . .
C5 C 0.7387(2) 0.34873(11) 0.27697(14) 0.0410(6) Uani 1 1 d . . . . .
C6 C 0.6551(4) 0.54488(15) 0.2970(3) 0.0867(12) Uani 1 1 d . . . . .
H6A H 0.6658 0.5563 0.3522 0.130 Uiso 1 1 calc R U . . .
H6B H 0.5563 0.5366 0.2862 0.130 Uiso 1 1 calc R U . . .
H6C H 0.6870 0.5758 0.2627 0.130 Uiso 1 1 calc R U . . .
C7 C 0.7432(3) 0.49146(13) 0.28139(18) 0.0547(8) Uani 1 1 d . . . . .
C8 C 0.6222(3) 0.44444(14) 0.39549(16) 0.0541(8) Uani 1 1 d . . . . .
H8A H 0.5403 0.4666 0.3771 0.065 Uiso 1 1 calc R U . . .
H8B H 0.5919 0.4043 0.4015 0.065 Uiso 1 1 calc R U . . .
C9 C 0.6653(3) 0.46637(15) 0.47373(19) 0.0623(9) Uani 1 1 d . . . . .
C10 C 0.6952(3) 0.48180(17) 0.5386(2) 0.0794(11) Uani 1 1 d . . . . .
H10 H 0.7189 0.4941 0.5901 0.095 Uiso 1 1 calc R U . . .
C11 C 0.7557(3) 0.26181(12) 0.19512(18) 0.0504(7) Uani 1 1 d . . . . .
C12 C 0.7667(3) 0.26355(14) 0.11249(18) 0.0609(8) Uani 1 1 d . . . . .
C13 C 0.7011(4) 0.21992(19) 0.0685(2) 0.0914(12) Uani 1 1 d . . . . .
H13 H 0.7061 0.2207 0.0127 0.110 Uiso 1 1 calc R U . . .
C14 C 0.6294(5) 0.1758(2) 0.1059(3) 0.1028(14) Uani 1 1 d . . . . .
H14 H 0.5862 0.1468 0.0755 0.123 Uiso 1 1 calc R U . . .
C15 C 0.6212(4) 0.17435(15) 0.1871(3) 0.0891(12) Uani 1 1 d . . . . .
H15 H 0.5719 0.1441 0.2117 0.107 Uiso 1 1 calc R U . . .
C16 C 0.6848(3) 0.21715(14) 0.23490(19) 0.0631(9) Uani 1 1 d . . . . .
C17 C 0.6795(4) 0.21404(16) 0.3248(2) 0.0879(12) Uani 1 1 d . . . . .
H17A H 0.6571 0.1750 0.3410 0.132 Uiso 1 1 calc R U . . .
H17B H 0.6073 0.2401 0.3444 0.132 Uiso 1 1 calc R U . . .
H17C H 0.7709 0.2250 0.3465 0.132 Uiso 1 1 calc R U . . .
C18 C 0.8460(4) 0.31160(18) 0.0704(2) 0.0856(11) Uani 1 1 d . . . . .
H18A H 0.8364 0.3070 0.0134 0.128 Uiso 1 1 calc R U . . .
H18B H 0.9454 0.3100 0.0848 0.128 Uiso 1 1 calc R U . . .
H18C H 0.8069 0.3485 0.0863 0.128 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 C7 1.222(3) . ?
O2 C5 1.225(3) . ?
N1 C7 1.342(3) . ?
N1 C1 1.459(3) . ?
N1 C8 1.473(3) . ?
N2 C5 1.337(3) . ?
N2 C11 1.427(3) . ?
N2 H2 0.80(3) . ?
C1 C2 1.519(4) . ?
C1 C5 1.525(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.513(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.524(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C7 1.501(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C9 1.454(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.171(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C11 C16 1.390(4) . ?
C12 C13 1.385(5) . ?
C12 C18 1.503(5) . ?
C13 C14 1.365(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.399(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.499(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C7 N1 C1 119.0(2) . . ?
C7 N1 C8 121.9(2) . . ?
C1 N1 C8 118.4(2) . . ?
C5 N2 C11 122.6(2) . . ?
C5 N2 H2 113(2) . . ?
C11 N2 H2 123(2) . . ?
N1 C1 C2 112.6(2) . . ?
N1 C1 C5 110.28(18) . . ?
C2 C1 C5 111.9(2) . . ?
N1 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
C5 C1 H1 107.2 . . ?
C3 C2 C1 113.8(2) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 111.6(3) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 N2 122.8(2) . . ?
O2 C5 C1 121.9(2) . . ?
N2 C5 C1 115.2(2) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 N1 120.8(3) . . ?
O1 C7 C6 120.7(3) . . ?
N1 C7 C6 118.5(3) . . ?
C9 C8 N1 114.6(2) . . ?
C9 C8 H8A 108.6 . . ?
N1 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
N1 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 176.3(4) . . ?
C9 C10 H10 180.0 . . ?
C12 C11 C16 122.1(3) . . ?
C12 C11 N2 118.6(3) . . ?
C16 C11 N2 119.2(3) . . ?
C11 C12 C13 118.2(3) . . ?
C11 C12 C18 121.5(3) . . ?
C13 C12 C18 120.3(3) . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 121.8(4) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C15 116.8(3) . . ?
C11 C16 C17 121.8(3) . . ?
C15 C16 C17 121.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C1 C2 137.4(2) . . . . ?
C8 N1 C1 C2 -52.1(3) . . . . ?
C7 N1 C1 C5 -96.7(3) . . . . ?
C8 N1 C1 C5 73.8(3) . . . . ?
N1 C1 C2 C3 -67.0(3) . . . . ?
C5 C1 C2 C3 168.0(2) . . . . ?
C1 C2 C3 C4 169.0(3) . . . . ?
C11 N2 C5 O2 3.2(4) . . . . ?
C11 N2 C5 C1 -177.9(2) . . . . ?
N1 C1 C5 O2 -20.6(3) . . . . ?
C2 C1 C5 O2 105.7(3) . . . . ?
N1 C1 C5 N2 160.6(2) . . . . ?
C2 C1 C5 N2 -73.2(3) . . . . ?
C1 N1 C7 O1 0.8(4) . . . . ?
C8 N1 C7 O1 -169.4(3) . . . . ?
C1 N1 C7 C6 -177.7(2) . . . . ?
C8 N1 C7 C6 12.1(4) . . . . ?
C7 N1 C8 C9 -95.8(3) . . . . ?
C1 N1 C8 C9 94.0(3) . . . . ?
C5 N2 C11 C12 106.7(3) . . . . ?
C5 N2 C11 C16 -72.4(3) . . . . ?
C16 C11 C12 C13 1.7(4) . . . . ?
N2 C11 C12 C13 -177.3(3) . . . . ?
C16 C11 C12 C18 -178.9(3) . . . . ?
N2 C11 C12 C18 2.0(4) . . . . ?
C11 C12 C13 C14 -1.0(5) . . . . ?
C18 C12 C13 C14 179.6(3) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C12 C11 C16 C15 -1.6(4) . . . . ?
N2 C11 C16 C15 177.5(3) . . . . ?
C12 C11 C16 C17 177.0(3) . . . . ?
N2 C11 C16 C17 -4.0(4) . . . . ?
C14 C15 C16 C11 0.7(5) . . . . ?
C14 C15 C16 C17 -177.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.80(3) 2.08(3) 2.878(3) 170(3) 6_656

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone-Hexanes'
####################################################################### 
# 
# 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_361MGL14
_database_code_depnum_ccdc_archive 'CCDC 1496196'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'4-Acetyl-1-(2,6-dimethylphenyl)-6-methyl-3-propyl-3,4-dihydropyrazin-2(1H)-one '
_chemical_name_common            ?
_chemical_melting_point          136-137
_chemical_formula_moiety         'C18 H24 N2 O2'
_chemical_formula_sum            'C18 H24 N2 O2'
_chemical_formula_weight         300.39

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.2997(3)
_cell_length_b                   8.7192(3)
_cell_length_c                   27.1071(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.6360(10)
_cell_angle_gamma                90
_cell_volume                     1710.00(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5857
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.279
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_process_details   '(Sheldrick, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            16910
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.456
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3930
_reflns_number_gt                2836
_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 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (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)+(0.0586P)²+0.3143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3930
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 -0.22229(14) -0.10403(13) 0.38723(5) 0.0546(3) Uani 1 1 d . . . . .
O2 O 0.25666(17) -0.43706(12) 0.44885(4) 0.0519(3) Uani 1 1 d . . . . .
N1 N 0.02913(14) 0.04767(13) 0.38552(4) 0.0326(3) Uani 1 1 d . . . . .
C2 C 0.22559(18) 0.05876(16) 0.38893(5) 0.0339(3) Uani 1 1 d . . . . .
C3 C 0.32978(19) -0.06226(16) 0.40303(6) 0.0365(3) Uani 1 1 d . . . . .
H3 H 0.4579 -0.0535 0.4068 0.044 Uiso 1 1 calc R U . . .
N4 N 0.24808(15) -0.20398(13) 0.41233(5) 0.0344(3) Uani 1 1 d . . . . .
C5 C 0.06583(18) -0.23132(16) 0.38424(5) 0.0341(3) Uani 1 1 d . . . . .
H5 H 0.0089 -0.3178 0.3996 0.041 Uiso 1 1 calc R U . . .
C6 C -0.05627(18) -0.09165(16) 0.38691(5) 0.0348(3) Uani 1 1 d . . . . .
C7 C -0.08201(18) 0.18555(15) 0.38191(6) 0.0350(3) Uani 1 1 d . . . . .
C8 C -0.0962(2) 0.26938(17) 0.42494(6) 0.0400(4) Uani 1 1 d . . . . .
C9 C -0.1998(2) 0.40365(18) 0.42049(7) 0.0515(4) Uani 1 1 d . . . . .
H9 H -0.2110 0.4618 0.4487 0.062 Uiso 1 1 calc R U . . .
C10 C -0.2856(2) 0.45137(19) 0.37498(8) 0.0569(5) Uani 1 1 d . . . . .
H10 H -0.3540 0.5417 0.3726 0.068 Uiso 1 1 calc R U . . .
C11 C -0.2712(2) 0.3666(2) 0.33299(8) 0.0562(5) Uani 1 1 d . . . . .
H11 H -0.3307 0.4000 0.3024 0.067 Uiso 1 1 calc R U . . .
C12 C -0.1691(2) 0.23130(19) 0.33548(6) 0.0450(4) Uani 1 1 d . . . . .
C13 C -0.0024(3) 0.2175(2) 0.47459(6) 0.0591(5) Uani 1 1 d . . . . .
H13A H 0.0055 0.3017 0.4976 0.089 Uiso 1 1 calc R U . . .
H13B H 0.1197 0.1817 0.4713 0.089 Uiso 1 1 calc R U . . .
H13C H -0.0723 0.1357 0.4868 0.089 Uiso 1 1 calc R U . . .
C14 C -0.1532(3) 0.1377(3) 0.28967(7) 0.0726(6) Uani 1 1 d . . . . .
H14A H -0.2013 0.1953 0.2606 0.109 Uiso 1 1 calc R U . . .
H14B H -0.2225 0.0445 0.2908 0.109 Uiso 1 1 calc R U . . .
H14C H -0.0257 0.1135 0.2883 0.109 Uiso 1 1 calc R U . . .
C15 C 0.3054(2) 0.20858(17) 0.37595(7) 0.0484(4) Uani 1 1 d . . . . .
H15A H 0.4376 0.2006 0.3793 0.073 Uiso 1 1 calc R U . . .
H15B H 0.2714 0.2867 0.3980 0.073 Uiso 1 1 calc R U . . .
H15C H 0.2585 0.2350 0.3423 0.073 Uiso 1 1 calc R U . . .
C16 C 0.3295(2) -0.31285(17) 0.44472(6) 0.0386(3) Uani 1 1 d . . . . .
C17 C 0.5089(2) -0.2693(2) 0.47474(7) 0.0560(5) Uani 1 1 d . . . . .
H17A H 0.4917 -0.1789 0.4938 0.084 Uiso 1 1 calc R U . . .
H17B H 0.5993 -0.2494 0.4528 0.084 Uiso 1 1 calc R U . . .
H17C H 0.5509 -0.3518 0.4968 0.084 Uiso 1 1 calc R U . . .
C18 C 0.0750(2) -0.27068(18) 0.32970(6) 0.0442(4) Uani 1 1 d . . . . .
H18A H -0.0499 -0.2830 0.3128 0.053 Uiso 1 1 calc R U . . .
H18B H 0.1308 -0.1854 0.3142 0.053 Uiso 1 1 calc R U . . .
C19 C 0.1829(3) -0.4138(2) 0.32237(7) 0.0630(5) Uani 1 1 d . . . . .
H19A H 0.3095 -0.3991 0.3377 0.076 Uiso 1 1 calc R U . . .
H19B H 0.1314 -0.4978 0.3395 0.076 Uiso 1 1 calc R U . . .
C20 C 0.1842(4) -0.4584(3) 0.26894(9) 0.0909(8) Uani 1 1 d . . . . .
H20A H 0.2579 -0.5490 0.2673 0.136 Uiso 1 1 calc R U . . .
H20B H 0.2355 -0.3763 0.2516 0.136 Uiso 1 1 calc R U . . .
H20C H 0.0600 -0.4785 0.2538 0.136 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 C6 1.2179(16) . ?
O2 C16 1.2183(18) . ?
N1 C6 1.3682(17) . ?
N1 C2 1.4281(16) . ?
N1 C7 1.4463(16) . ?
C2 C3 1.3269(19) . ?
C2 C15 1.4911(19) . ?
C3 N4 1.4093(17) . ?
C3 H3 0.9300 . ?
N4 C16 1.3737(18) . ?
N4 C5 1.4620(18) . ?
C5 C6 1.5166(19) . ?
C5 C18 1.528(2) . ?
C5 H5 0.9800 . ?
C7 C12 1.391(2) . ?
C7 C8 1.392(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.497(2) . ?
C9 C10 1.372(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9300 . ?
C12 C14 1.503(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.496(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.503(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.501(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C6 N1 C2 121.04(11) . . ?
C6 N1 C7 119.10(11) . . ?
C2 N1 C7 119.84(11) . . ?
C3 C2 N1 119.80(12) . . ?
C3 C2 C15 122.53(13) . . ?
N1 C2 C15 117.66(12) . . ?
C2 C3 N4 120.59(12) . . ?
C2 C3 H3 119.7 . . ?
N4 C3 H3 119.7 . . ?
C16 N4 C3 124.25(12) . . ?
C16 N4 C5 120.45(12) . . ?
C3 N4 C5 115.29(11) . . ?
N4 C5 C6 110.13(11) . . ?
N4 C5 C18 112.75(12) . . ?
C6 C5 C18 109.16(12) . . ?
N4 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
C18 C5 H5 108.2 . . ?
O1 C6 N1 122.43(13) . . ?
O1 C6 C5 121.39(13) . . ?
N1 C6 C5 116.03(11) . . ?
C12 C7 C8 122.12(13) . . ?
C12 C7 N1 118.97(13) . . ?
C8 C7 N1 118.90(13) . . ?
C9 C8 C7 118.01(15) . . ?
C9 C8 C13 120.74(16) . . ?
C7 C8 C13 121.25(14) . . ?
C10 C9 C8 120.76(17) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.41(15) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 121.03(16) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 117.66(16) . . ?
C7 C12 C14 121.05(15) . . ?
C11 C12 C14 121.29(16) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 N4 121.06(14) . . ?
O2 C16 C17 122.46(14) . . ?
N4 C16 C17 116.47(13) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C5 113.92(14) . . ?
C19 C18 H18A 108.8 . . ?
C5 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C5 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 114.40(17) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 N1 C2 C3 -13.0(2) . . . . ?
C7 N1 C2 C3 165.30(14) . . . . ?
C6 N1 C2 C15 166.70(14) . . . . ?
C7 N1 C2 C15 -15.0(2) . . . . ?
N1 C2 C3 N4 3.1(2) . . . . ?
C15 C2 C3 N4 -176.53(14) . . . . ?
C2 C3 N4 C16 -152.31(15) . . . . ?
C2 C3 N4 C5 28.4(2) . . . . ?
C16 N4 C5 C6 133.50(13) . . . . ?
C3 N4 C5 C6 -47.16(16) . . . . ?
C16 N4 C5 C18 -104.31(15) . . . . ?
C3 N4 C5 C18 75.03(15) . . . . ?
C2 N1 C6 O1 175.28(14) . . . . ?
C7 N1 C6 O1 -3.0(2) . . . . ?
C2 N1 C6 C5 -9.01(19) . . . . ?
C7 N1 C6 C5 172.69(12) . . . . ?
N4 C5 C6 O1 -146.59(14) . . . . ?
C18 C5 C6 O1 89.12(17) . . . . ?
N4 C5 C6 N1 37.66(17) . . . . ?
C18 C5 C6 N1 -86.63(15) . . . . ?
C6 N1 C7 C12 -81.63(17) . . . . ?
C2 N1 C7 C12 100.05(16) . . . . ?
C6 N1 C7 C8 99.27(16) . . . . ?
C2 N1 C7 C8 -79.06(17) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
N1 C7 C8 C9 178.38(12) . . . . ?
C12 C7 C8 C13 179.56(15) . . . . ?
N1 C7 C8 C13 -1.4(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C13 C8 C9 C10 179.93(16) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
N1 C7 C12 C11 -178.39(13) . . . . ?
C8 C7 C12 C14 -179.32(16) . . . . ?
N1 C7 C12 C14 1.6(2) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C10 C11 C12 C14 179.84(17) . . . . ?
C3 N4 C16 O2 -175.44(14) . . . . ?
C5 N4 C16 O2 3.8(2) . . . . ?
C3 N4 C16 C17 5.5(2) . . . . ?
C5 N4 C16 C17 -175.25(13) . . . . ?
N4 C5 C18 C19 60.95(18) . . . . ?
C6 C5 C18 C19 -176.32(14) . . . . ?
C5 C18 C19 C20 176.81(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O1 0.93 2.50 3.3733(17) 156.2 1_655
C17 H17C O2 0.96 2.64 3.582(2) 166.4 3_646

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone-Hexanes'
####################################################################### 
# 
# 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_364mgl15
_database_code_depnum_ccdc_archive 'CCDC 1496197'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-(2,6-Dimethylphenyl)-1,4-dimethylpyrazino[2,1-a]isoindole-3,6(2H,4H)-dione
_chemical_name_common            ?
_chemical_melting_point          200-203
_chemical_formula_moiety         ?
_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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.2348(7)
_cell_length_b                   26.914(2)
_cell_length_c                   8.2642(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.859(2)
_cell_angle_gamma                90
_cell_volume                     1733.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      25.28

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_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          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_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            19869
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.712
_diffrn_reflns_theta_max         25.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3138
_reflns_number_gt                2384
_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    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0924P)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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3138
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1508
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.11643(18) 0.16164(4) -0.12434(16) 0.0613(4) Uani 1 1 d . . . . .
O2 O 0.21100(17) -0.02738(4) -0.07469(15) 0.0560(4) Uani 1 1 d . . . . .
N1 N 0.16505(17) 0.14123(5) 0.15337(16) 0.0407(4) Uani 1 1 d . . . . .
C2 C 0.1579(2) 0.13052(6) -0.0114(2) 0.0417(4) Uani 1 1 d . . . . .
C3 C 0.2163(2) 0.07967(6) -0.0466(2) 0.0390(4) Uani 1 1 d . . . . .
H3 H 0.1433 0.0692 -0.1605 0.047 Uiso 1 1 calc R U . . .
N4 N 0.19826(17) 0.04356(5) 0.07575(15) 0.0391(4) Uani 1 1 d . . . . .
C5 C 0.2130(2) -0.00678(6) 0.0579(2) 0.0405(4) Uani 1 1 d . . . . .
C5A C 0.2333(2) -0.02788(6) 0.2269(2) 0.0415(4) Uani 1 1 d . . . . .
C6 C 0.2482(3) -0.07716(6) 0.2769(2) 0.0536(5) Uani 1 1 d . . . . .
H6 H 0.2481 -0.1023 0.1997 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2632(3) -0.08803(7) 0.4438(3) 0.0668(6) Uani 1 1 d . . . . .
H7 H 0.2747 -0.1209 0.4806 0.080 Uiso 1 1 calc R U . . .
C8 C 0.2611(3) -0.05058(7) 0.5567(3) 0.0686(6) Uani 1 1 d . . . . .
H8 H 0.2702 -0.0587 0.6686 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2460(3) -0.00126(7) 0.5078(2) 0.0585(6) Uani 1 1 d . . . . .
H9 H 0.2434 0.0236 0.5852 0.070 Uiso 1 1 calc R U . . .
C9A C 0.2348(2) 0.01055(6) 0.3407(2) 0.0419(4) Uani 1 1 d . . . . .
C9B C 0.2148(2) 0.05712(6) 0.24536(19) 0.0381(4) Uani 1 1 d . . . . .
C10 C 0.2031(2) 0.10471(6) 0.2861(2) 0.0405(4) Uani 1 1 d . . . . .
C11 C 0.4000(2) 0.08263(7) -0.0483(3) 0.0607(5) Uani 1 1 d . . . . .
H11A H 0.4743 0.0921 0.0631 0.091 Uiso 1 1 calc R U . . .
H11B H 0.4073 0.1069 -0.1308 0.091 Uiso 1 1 calc R U . . .
H11C H 0.4345 0.0508 -0.0780 0.091 Uiso 1 1 calc R U . . .
C12 C 0.2282(3) 0.12269(7) 0.4629(2) 0.0651(6) Uani 1 1 d . . . . .
H12A H 0.1185 0.1271 0.4785 0.098 Uiso 1 1 calc R U . . .
H12B H 0.2883 0.1538 0.4804 0.098 Uiso 1 1 calc R U . . .
H12C H 0.2941 0.0987 0.5437 0.098 Uiso 1 1 calc R U . . .
C13 C 0.1222(2) 0.19147(5) 0.1882(2) 0.0404(4) Uani 1 1 d . . . . .
C14 C 0.2482(2) 0.22816(6) 0.2157(2) 0.0482(5) Uani 1 1 d . . . . .
C15 C 0.2037(3) 0.27619(6) 0.2451(3) 0.0593(5) Uani 1 1 d . . . . .
H15 H 0.2841 0.3016 0.2620 0.071 Uiso 1 1 calc R U . . .
C16 C 0.0418(3) 0.28662(7) 0.2492(3) 0.0661(6) Uani 1 1 d . . . . .
H16 H 0.0139 0.3190 0.2696 0.079 Uiso 1 1 calc R U . . .
C17 C -0.0788(3) 0.25000(7) 0.2239(3) 0.0598(5) Uani 1 1 d . . . . .
H17 H -0.1874 0.2578 0.2281 0.072 Uiso 1 1 calc R U . . .
C18 C -0.0421(2) 0.20120(6) 0.1920(2) 0.0456(4) Uani 1 1 d . . . . .
C19 C 0.4261(3) 0.21685(8) 0.2146(3) 0.0739(7) Uani 1 1 d . . . . .
H19A H 0.4246 0.2126 0.0988 0.111 Uiso 1 1 calc R U . . .
H19B H 0.4664 0.1869 0.2778 0.111 Uiso 1 1 calc R U . . .
H19C H 0.5011 0.2438 0.2663 0.111 Uiso 1 1 calc R U . . .
C20 C -0.1743(3) 0.16106(7) 0.1664(3) 0.0627(6) Uani 1 1 d . . . . .
H20A H -0.1736 0.1487 0.2757 0.094 Uiso 1 1 calc R U . . .
H20B H -0.1483 0.1344 0.1015 0.094 Uiso 1 1 calc R U . . .
H20C H -0.2856 0.1743 0.1058 0.094 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 C2 1.2178(19) . ?
O2 C5 1.2232(19) . ?
N1 C2 1.374(2) . ?
N1 C10 1.430(2) . ?
N1 C13 1.4495(19) . ?
C2 C3 1.510(2) . ?
C3 N4 1.4446(19) . ?
C3 C11 1.519(2) . ?
C3 H3 0.9800 . ?
N4 C5 1.373(2) . ?
N4 C9B 1.4118(19) . ?
C5 C5A 1.466(2) . ?
C5A C6 1.383(2) . ?
C5A C9A 1.395(2) . ?
C6 C7 1.376(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9300 . ?
C9 C9A 1.391(2) . ?
C9 H9 0.9300 . ?
C9A C9B 1.461(2) . ?
C9B C10 1.336(2) . ?
C10 C12 1.489(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.388(2) . ?
C13 C14 1.396(2) . ?
C14 C15 1.386(2) . ?
C14 C19 1.499(3) . ?
C15 C16 1.374(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(2) . ?
C17 H17 0.9300 . ?
C18 C20 1.499(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C2 N1 C10 122.99(13) . . ?
C2 N1 C13 117.19(13) . . ?
C10 N1 C13 119.73(13) . . ?
O1 C2 N1 121.79(15) . . ?
O1 C2 C3 120.22(15) . . ?
N1 C2 C3 117.83(13) . . ?
N4 C3 C2 111.30(12) . . ?
N4 C3 C11 111.70(13) . . ?
C2 C3 C11 109.55(14) . . ?
N4 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C11 C3 H3 108.1 . . ?
C5 N4 C9B 112.24(13) . . ?
C5 N4 C3 123.78(12) . . ?
C9B N4 C3 121.51(13) . . ?
O2 C5 N4 124.59(15) . . ?
O2 C5 C5A 129.93(15) . . ?
N4 C5 C5A 105.47(12) . . ?
C6 C5A C9A 121.94(15) . . ?
C6 C5A C5 128.89(15) . . ?
C9A C5A C5 109.17(14) . . ?
C7 C6 C5A 118.29(16) . . ?
C7 C6 H6 120.9 . . ?
C5A C6 H6 120.9 . . ?
C6 C7 C8 120.44(17) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 121.67(18) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C9A 118.73(17) . . ?
C8 C9 H9 120.6 . . ?
C9A C9 H9 120.6 . . ?
C9 C9A C5A 118.90(15) . . ?
C9 C9A C9B 133.72(15) . . ?
C5A C9A C9B 107.31(14) . . ?
C10 C9B N4 120.41(14) . . ?
C10 C9B C9A 133.76(15) . . ?
N4 C9B C9A 105.76(13) . . ?
C9B C10 N1 118.79(14) . . ?
C9B C10 C12 124.08(15) . . ?
N1 C10 C12 117.12(14) . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.74(14) . . ?
C18 C13 N1 118.81(14) . . ?
C14 C13 N1 118.45(15) . . ?
C15 C14 C13 117.63(16) . . ?
C15 C14 C19 120.28(17) . . ?
C13 C14 C19 122.09(15) . . ?
C16 C15 C14 120.54(17) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.80(17) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 121.18(18) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 117.09(16) . . ?
C13 C18 C20 121.96(15) . . ?
C17 C18 C20 120.93(17) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 N1 C2 O1 176.08(16) . . . . ?
C13 N1 C2 O1 -0.4(2) . . . . ?
C10 N1 C2 C3 -8.5(2) . . . . ?
C13 N1 C2 C3 174.98(14) . . . . ?
O1 C2 C3 N4 -158.61(15) . . . . ?
N1 C2 C3 N4 25.9(2) . . . . ?
O1 C2 C3 C11 77.4(2) . . . . ?
N1 C2 C3 C11 -98.10(17) . . . . ?
C2 C3 N4 C5 168.25(14) . . . . ?
C11 C3 N4 C5 -68.9(2) . . . . ?
C2 C3 N4 C9B -30.96(19) . . . . ?
C11 C3 N4 C9B 91.84(17) . . . . ?
C9B N4 C5 O2 -176.54(15) . . . . ?
C3 N4 C5 O2 -14.2(2) . . . . ?
C9B N4 C5 C5A 2.52(17) . . . . ?
C3 N4 C5 C5A 164.87(14) . . . . ?
O2 C5 C5A C6 -3.1(3) . . . . ?
N4 C5 C5A C6 177.93(17) . . . . ?
O2 C5 C5A C9A 177.36(17) . . . . ?
N4 C5 C5A C9A -1.63(18) . . . . ?
C9A C5A C6 C7 0.7(3) . . . . ?
C5 C5A C6 C7 -178.86(17) . . . . ?
C5A C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C9A -0.8(3) . . . . ?
C8 C9 C9A C5A 2.2(3) . . . . ?
C8 C9 C9A C9B 178.55(19) . . . . ?
C6 C5A C9A C9 -2.1(3) . . . . ?
C5 C5A C9A C9 177.46(15) . . . . ?
C6 C5A C9A C9B -179.40(16) . . . . ?
C5 C5A C9A C9B 0.20(19) . . . . ?
C5 N4 C9B C10 -179.70(15) . . . . ?
C3 N4 C9B C10 17.5(2) . . . . ?
C5 N4 C9B C9A -2.42(17) . . . . ?
C3 N4 C9B C9A -165.23(13) . . . . ?
C9 C9A C9B C10 1.3(4) . . . . ?
C5A C9A C9B C10 178.02(18) . . . . ?
C9 C9A C9B N4 -175.41(18) . . . . ?
C5A C9A C9B N4 1.27(18) . . . . ?
N4 C9B C10 N1 3.1(2) . . . . ?
C9A C9B C10 N1 -173.26(16) . . . . ?
N4 C9B C10 C12 -176.53(15) . . . . ?
C9A C9B C10 C12 7.1(3) . . . . ?
C2 N1 C10 C9B -7.1(2) . . . . ?
C13 N1 C10 C9B 169.25(15) . . . . ?
C2 N1 C10 C12 172.51(15) . . . . ?
C13 N1 C10 C12 -11.1(2) . . . . ?
C2 N1 C13 C18 98.22(17) . . . . ?
C10 N1 C13 C18 -78.38(19) . . . . ?
C2 N1 C13 C14 -81.48(19) . . . . ?
C10 N1 C13 C14 101.92(18) . . . . ?
C18 C13 C14 C15 -1.1(3) . . . . ?
N1 C13 C14 C15 178.60(15) . . . . ?
C18 C13 C14 C19 178.80(17) . . . . ?
N1 C13 C14 C19 -1.5(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C19 C14 C15 C16 -178.86(19) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C14 C13 C18 C17 0.4(2) . . . . ?
N1 C13 C18 C17 -179.32(15) . . . . ?
C14 C13 C18 C20 -178.42(16) . . . . ?
N1 C13 C18 C20 1.9(2) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C16 C17 C18 C20 179.24(18) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.059


_exptl_crystal_recrystallization_method 
'Liquid-Liquid Difussion: Dichlormethane-Acetone'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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_399MGL15
_database_code_depnum_ccdc_archive 'CCDC 1496198'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2-Benzyl-4-isopropyl-1-methylpyrazino[2,1-a]isoindole-3,6(2H,4H)-dione '
_chemical_name_common            ?
_chemical_melting_point          201-204
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O2'
_chemical_formula_weight         346.41

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.0741(5)
_cell_length_b                   8.4735(3)
_cell_length_c                   16.5267(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.0190(10)
_cell_angle_gamma                90
_cell_volume                     1785.99(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.39

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            13978
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.497
_diffrn_reflns_theta_max         25.390
_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             3275
_reflns_number_gt                2711
_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 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_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)+(0.0511P)²+0.3679P] 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         3275
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.16268(9) 0.26249(14) -0.11421(7) 0.0644(3) Uani 1 1 d . . . . .
O2 O 0.35756(8) -0.27080(12) -0.07016(6) 0.0509(3) Uani 1 1 d . . . . .
N1 N 0.30339(9) 0.27252(14) 0.02001(7) 0.0445(3) Uani 1 1 d . . . . .
C2 C 0.23541(11) 0.19459(18) -0.05522(9) 0.0455(3) Uani 1 1 d . . . . .
C3 C 0.24860(10) 0.01875(17) -0.06397(8) 0.0409(3) Uani 1 1 d . . . . .
H3 H 0.2421 -0.0006 -0.1246 0.049 Uiso 1 1 calc R U . . .
N4 N 0.35212(8) -0.03456(13) -0.00213(6) 0.0385(3) Uani 1 1 d . . . . .
C5 C 0.39504(10) -0.17743(16) -0.00798(8) 0.0383(3) Uani 1 1 d . . . . .
C5A C 0.49145(9) -0.19089(16) 0.07511(8) 0.0384(3) Uani 1 1 d . . . . .
C6 C 0.56212(10) -0.31486(18) 0.10317(9) 0.0466(3) Uani 1 1 d . . . . .
H6 H 0.5535 -0.4033 0.0674 0.056 Uiso 1 1 calc R U . . .
C7 C 0.64558(11) -0.3029(2) 0.18566(10) 0.0552(4) Uani 1 1 d . . . . .
H7 H 0.6939 -0.3848 0.2065 0.066 Uiso 1 1 calc R U . . .
C8 C 0.65809(11) -0.1702(2) 0.23775(10) 0.0583(4) Uani 1 1 d . . . . .
H8 H 0.7151 -0.1646 0.2932 0.070 Uiso 1 1 calc R U . . .
C9 C 0.58849(11) -0.04576(19) 0.20989(9) 0.0505(4) Uani 1 1 d . . . . .
H9 H 0.5983 0.0427 0.2458 0.061 Uiso 1 1 calc R U . . .
C9A C 0.50304(10) -0.05540(16) 0.12664(8) 0.0387(3) Uani 1 1 d . . . . .
C9B C 0.41530(9) 0.04950(16) 0.07590(8) 0.0372(3) Uani 1 1 d . . . . .
C10 C 0.39311(10) 0.19969(16) 0.08704(8) 0.0401(3) Uani 1 1 d . . . . .
C11 C 0.28496(14) 0.44325(18) 0.02551(11) 0.0575(4) Uani 1 1 d . . . . .
H11A H 0.2413 0.4820 -0.0340 0.069 Uiso 1 1 calc R U . . .
H11B H 0.3516 0.4980 0.0464 0.069 Uiso 1 1 calc R U . . .
C12 C 0.16205(11) -0.07802(19) -0.05237(10) 0.0513(4) Uani 1 1 d . . . . .
H12 H 0.1796 -0.1897 -0.0535 0.062 Uiso 1 1 calc R U . . .
C13 C 0.15980(15) -0.0480(2) 0.03742(12) 0.0716(5) Uani 1 1 d . . . . .
H13A H 0.1380 0.0587 0.0396 0.107 Uiso 1 1 calc R U . . .
H13B H 0.2286 -0.0642 0.0843 0.107 Uiso 1 1 calc R U . . .
H13C H 0.1113 -0.1195 0.0451 0.107 Uiso 1 1 calc R U . . .
C14 C 0.05421(12) -0.0523(2) -0.12950(13) 0.0751(5) Uani 1 1 d . . . . .
H14A H 0.0044 -0.1229 -0.1232 0.113 Uiso 1 1 calc R U . . .
H14B H 0.0582 -0.0726 -0.1851 0.113 Uiso 1 1 calc R U . . .
H14C H 0.0323 0.0548 -0.1286 0.113 Uiso 1 1 calc R U . . .
C15 C 0.46120(13) 0.29734(18) 0.16477(10) 0.0561(4) Uani 1 1 d . . . . .
H15A H 0.5135 0.2315 0.2083 0.084 Uiso 1 1 calc R U . . .
H15B H 0.4192 0.3458 0.1910 0.084 Uiso 1 1 calc R U . . .
H15C H 0.4948 0.3777 0.1452 0.084 Uiso 1 1 calc R U . . .
C16 C 0.23332(13) 0.48352(19) 0.08623(11) 0.0573(4) Uani 1 1 d . . . . .
C17 C 0.28037(18) 0.5857(2) 0.15677(13) 0.0821(6) Uani 1 1 d . . . . .
H17 H 0.3452 0.6297 0.1675 0.098 Uiso 1 1 calc R U . . .
C18 C 0.2319(3) 0.6237(3) 0.21212(16) 0.1096(9) Uani 1 1 d . . . . .
H18 H 0.2641 0.6931 0.2595 0.132 Uiso 1 1 calc R U . . .
C19 C 0.1375(3) 0.5595(4) 0.1968(2) 0.1160(10) Uani 1 1 d . . . . .
H19 H 0.1058 0.5834 0.2346 0.139 Uiso 1 1 calc R U . . .
C20 C 0.0889(2) 0.4603(3) 0.1266(2) 0.1069(8) Uani 1 1 d . . . . .
H20 H 0.0237 0.4181 0.1159 0.128 Uiso 1 1 calc R U . . .
C21 C 0.13628(16) 0.4219(2) 0.07096(15) 0.0795(6) Uani 1 1 d . . . . .
H21 H 0.1026 0.3542 0.0230 0.095 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 C2 1.2187(16) . ?
O2 C5 1.2255(15) . ?
N1 C2 1.3751(18) . ?
N1 C10 1.4211(17) . ?
N1 C11 1.4793(19) . ?
C2 C3 1.516(2) . ?
C3 N4 1.4532(16) . ?
C3 C12 1.5462(19) . ?
C3 H3 0.9800 . ?
N4 C5 1.3744(17) . ?
N4 C9B 1.4110(16) . ?
C5 C5A 1.4710(17) . ?
C5A C6 1.3847(19) . ?
C5A C9A 1.3974(19) . ?
C6 C7 1.376(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(2) . ?
C8 H8 0.9300 . ?
C9 C9A 1.3951(18) . ?
C9 H9 0.9300 . ?
C9A C9B 1.4637(18) . ?
C9B C10 1.3415(19) . ?
C10 C15 1.4872(19) . ?
C11 C16 1.506(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.519(2) . ?
C12 C14 1.530(2) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.376(2) . ?
C16 C21 1.382(3) . ?
C17 C18 1.391(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.357(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.360(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C10 123.05(12) . . ?
C2 N1 C11 116.88(12) . . ?
C10 N1 C11 119.86(12) . . ?
O1 C2 N1 121.63(14) . . ?
O1 C2 C3 118.88(13) . . ?
N1 C2 C3 119.46(12) . . ?
N4 C3 C2 111.42(11) . . ?
N4 C3 C12 110.86(11) . . ?
C2 C3 C12 112.01(12) . . ?
N4 C3 H3 107.4 . . ?
C2 C3 H3 107.4 . . ?
C12 C3 H3 107.4 . . ?
C5 N4 C9B 112.53(10) . . ?
C5 N4 C3 124.33(11) . . ?
C9B N4 C3 122.86(11) . . ?
O2 C5 N4 125.56(12) . . ?
O2 C5 C5A 129.25(13) . . ?
N4 C5 C5A 105.19(11) . . ?
C6 C5A C9A 122.47(12) . . ?
C6 C5A C5 128.30(13) . . ?
C9A C5A C5 109.21(11) . . ?
C7 C6 C5A 117.86(14) . . ?
C7 C6 H6 121.1 . . ?
C5A C6 H6 121.1 . . ?
C6 C7 C8 120.50(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.94(13) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C9A 118.61(14) . . ?
C8 C9 H9 120.7 . . ?
C9A C9 H9 120.7 . . ?
C9 C9A C5A 118.62(13) . . ?
C9 C9A C9B 134.11(13) . . ?
C5A C9A C9B 107.28(11) . . ?
C10 C9B N4 120.73(12) . . ?
C10 C9B C9A 133.34(12) . . ?
N4 C9B C9A 105.66(11) . . ?
C9B C10 N1 119.12(12) . . ?
C9B C10 C15 122.96(13) . . ?
N1 C10 C15 117.86(12) . . ?
N1 C11 C16 114.15(12) . . ?
N1 C11 H11A 108.7 . . ?
C16 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
C16 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C14 111.53(14) . . ?
C13 C12 C3 112.04(13) . . ?
C14 C12 C3 112.15(13) . . ?
C13 C12 H12 106.9 . . ?
C14 C12 H12 106.9 . . ?
C3 C12 H12 106.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.46(18) . . ?
C17 C16 C11 120.80(17) . . ?
C21 C16 C11 120.71(16) . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.3(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 120.4(2) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?

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
C10 N1 C2 O1 -175.48(13) . . . . ?
C11 N1 C2 O1 -0.8(2) . . . . ?
C10 N1 C2 C3 6.63(19) . . . . ?
C11 N1 C2 C3 -178.65(12) . . . . ?
O1 C2 C3 N4 164.64(12) . . . . ?
N1 C2 C3 N4 -17.40(17) . . . . ?
O1 C2 C3 C12 -70.53(16) . . . . ?
N1 C2 C3 C12 107.42(14) . . . . ?
C2 C3 N4 C5 -164.74(11) . . . . ?
C12 C3 N4 C5 69.79(16) . . . . ?
C2 C3 N4 C9B 21.75(17) . . . . ?
C12 C3 N4 C9B -103.71(14) . . . . ?
C9B N4 C5 O2 -177.77(12) . . . . ?
C3 N4 C5 O2 8.1(2) . . . . ?
C9B N4 C5 C5A 2.91(14) . . . . ?
C3 N4 C5 C5A -171.19(11) . . . . ?
O2 C5 C5A C6 -1.1(2) . . . . ?
N4 C5 C5A C6 178.17(13) . . . . ?
O2 C5 C5A C9A 180.00(13) . . . . ?
N4 C5 C5A C9A -0.71(13) . . . . ?
C9A C5A C6 C7 0.9(2) . . . . ?
C5 C5A C6 C7 -177.81(12) . . . . ?
C5A C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C9A 0.2(2) . . . . ?
C8 C9 C9A C5A 0.1(2) . . . . ?
C8 C9 C9A C9B 179.94(14) . . . . ?
C6 C5A C9A C9 -0.71(19) . . . . ?
C5 C5A C9A C9 178.25(12) . . . . ?
C6 C5A C9A C9B 179.44(12) . . . . ?
C5 C5A C9A C9B -1.59(14) . . . . ?
C5 N4 C9B C10 170.98(12) . . . . ?
C3 N4 C9B C10 -14.82(19) . . . . ?
C5 N4 C9B C9A -3.89(14) . . . . ?
C3 N4 C9B C9A 170.31(11) . . . . ?
C9 C9A C9B C10 9.5(3) . . . . ?
C5A C9A C9B C10 -170.70(14) . . . . ?
C9 C9A C9B N4 -176.58(14) . . . . ?
C5A C9A C9B N4 3.24(13) . . . . ?
N4 C9B C10 N1 1.48(19) . . . . ?
C9A C9B C10 N1 174.68(13) . . . . ?
N4 C9B C10 C15 -175.48(12) . . . . ?
C9A C9B C10 C15 -2.3(2) . . . . ?
C2 N1 C10 C9B 2.20(19) . . . . ?
C11 N1 C10 C9B -172.37(12) . . . . ?
C2 N1 C10 C15 179.31(12) . . . . ?
C11 N1 C10 C15 4.74(18) . . . . ?
C2 N1 C11 C16 102.70(16) . . . . ?
C10 N1 C11 C16 -82.40(17) . . . . ?
N4 C3 C12 C13 66.91(16) . . . . ?
C2 C3 C12 C13 -58.22(16) . . . . ?
N4 C3 C12 C14 -166.76(13) . . . . ?
C2 C3 C12 C14 68.10(17) . . . . ?
N1 C11 C16 C17 122.71(17) . . . . ?
N1 C11 C16 C21 -59.0(2) . . . . ?
C21 C16 C17 C18 1.0(3) . . . . ?
C11 C16 C17 C18 179.35(18) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 -1.3(4) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C17 C16 C21 C20 -1.2(3) . . . . ?
C11 C16 C21 C20 -179.52(18) . . . . ?
C19 C20 C21 C16 0.2(4) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 
'Liquid-Liquid diffusion: Dichloromethane-Acetone'
