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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_13marb_0m
_database_code_depnum_ccdc_archive 'CCDC 1004592'
_audit_update_record             
;
2014-05-22 deposited with the CCDC.
2015-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N4 O Se'
_chemical_formula_sum            'C20 H14 N4 O Se'
_chemical_formula_weight         405.31

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   7.9301(5)
_cell_length_b                   18.6114(12)
_cell_length_c                   11.7983(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.431(2)
_cell_angle_gamma                90.00
_cell_volume                     1730.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    2.187
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_T_max  0.6689
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9788
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3230
_reflns_number_gt                2728
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0398P)²+0.3773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3230
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8231(3) 0.80903(12) 0.7421(2) 0.0112(5) Uani 1 1 d . . .
C2 C 0.9511(3) 0.83424(13) 0.8213(2) 0.0158(6) Uani 1 1 d . . .
H2 H 1.0403 0.8608 0.7978 0.019 Uiso 1 1 calc R . .
C3 C 0.9456(3) 0.81962(14) 0.9364(2) 0.0192(6) Uani 1 1 d . . .
H3 H 1.0324 0.8359 0.9897 0.023 Uiso 1 1 calc R . .
C4 C 0.8128(3) 0.78124(14) 0.9721(2) 0.0183(6) Uani 1 1 d . . .
H4 H 0.8090 0.7719 1.0492 0.022 Uiso 1 1 calc R . .
C5 C 0.6843(3) 0.75662(14) 0.8915(2) 0.0176(6) Uani 1 1 d . . .
H5 H 0.5937 0.7311 0.9152 0.021 Uiso 1 1 calc R . .
C6 C 0.6895(3) 0.76951(13) 0.7770(2) 0.0139(6) Uani 1 1 d . . .
H6 H 0.6043 0.7519 0.7235 0.017 Uiso 1 1 calc R . .
C7 C 0.6362(3) 0.86175(12) 0.5268(2) 0.0098(5) Uani 1 1 d . . .
C8 C 0.6010(3) 0.86967(13) 0.4084(2) 0.0105(5) Uani 1 1 d . . .
C9 C 0.4503(3) 0.90447(12) 0.3644(2) 0.0103(5) Uani 1 1 d . . .
C10 C 0.3410(3) 0.92549(13) 0.4430(2) 0.0101(5) Uani 1 1 d . . .
C11 C 0.3854(3) 0.91315(12) 0.5613(2) 0.0103(5) Uani 1 1 d . . .
C12 C 0.7202(3) 0.84232(13) 0.3358(2) 0.0140(6) Uani 1 1 d . . .
C13 C 0.1781(3) 0.95604(14) 0.4077(2) 0.0134(6) Uani 1 1 d . . .
C14 C 0.4077(3) 0.92017(13) 0.2418(2) 0.0103(5) Uani 1 1 d . . .
C15 C 0.4209(3) 0.86887(13) 0.1573(2) 0.0119(5) Uani 1 1 d . . .
H15 H 0.4625 0.8234 0.1776 0.014 Uiso 1 1 calc R . .
C16 C 0.3733(3) 0.88450(13) 0.0440(2) 0.0134(5) Uani 1 1 d . . .
H16 H 0.3825 0.8497 -0.0115 0.016 Uiso 1 1 calc R . .
C17 C 0.3114(3) 0.95237(13) 0.0128(2) 0.0109(5) Uani 1 1 d . . .
C18 C 0.3019(3) 1.00460(13) 0.0950(2) 0.0114(5) Uani 1 1 d . . .
H18 H 0.2636 1.0505 0.0741 0.014 Uiso 1 1 calc R . .
C19 C 0.3493(3) 0.98852(13) 0.2082(2) 0.0115(5) Uani 1 1 d . . .
H19 H 0.3423 1.0239 0.2632 0.014 Uiso 1 1 calc R . .
C20 C 0.1823(3) 1.03045(13) -0.1308(2) 0.0187(6) Uani 1 1 d . . .
H20A H 0.1517 1.0324 -0.2118 0.028 Uiso 1 1 calc R . .
H20B H 0.2602 1.0686 -0.1081 0.028 Uiso 1 1 calc R . .
H20C H 0.0823 1.0357 -0.0927 0.028 Uiso 1 1 calc R . .
N1 N 0.5336(2) 0.88269(10) 0.60175(16) 0.0103(4) Uani 1 1 d . . .
N2 N 0.8156(3) 0.81829(12) 0.28035(19) 0.0214(5) Uani 1 1 d . . .
N3 N 0.0458(3) 0.98060(12) 0.38633(18) 0.0203(5) Uani 1 1 d . . .
N4 N 0.2822(3) 0.93180(12) 0.6391(2) 0.0150(5) Uani 1 1 d D . .
O1 O 0.2611(2) 0.96260(9) -0.10072(14) 0.0142(4) Uani 1 1 d . . .
Se1 Se 0.85018(3) 0.821398(13) 0.58419(2) 0.01340(10) Uani 1 1 d . . .
H1N4 H 0.192(3) 0.9519(13) 0.617(2) 0.019(8) Uiso 1 1 d D . .
H2N4 H 0.317(4) 0.9251(15) 0.708(3) 0.026(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(4) . ?
C1 C6 1.390(3) . ?
C1 Se1 1.913(2) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.325(3) . ?
C7 C8 1.402(3) . ?
C7 Se1 1.909(2) . ?
C8 C9 1.406(3) . ?
C8 C12 1.438(3) . ?
C9 C10 1.395(3) . ?
C9 C14 1.477(3) . ?
C10 C11 1.420(3) . ?
C10 C13 1.430(3) . ?
C11 N4 1.341(3) . ?
C11 N1 1.344(3) . ?
C12 N2 1.145(3) . ?
C13 N3 1.147(3) . ?
C14 C15 1.393(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9300 . ?
C17 O1 1.367(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O1 1.436(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N4 H1N4 0.827(17) . ?
N4 H2N4 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.4(2) . . ?
C2 C1 Se1 117.62(19) . . ?
C6 C1 Se1 121.63(19) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 124.4(2) . . ?
N1 C7 Se1 117.82(18) . . ?
C8 C7 Se1 117.68(17) . . ?
C7 C8 C9 118.8(2) . . ?
C7 C8 C12 119.1(2) . . ?
C9 C8 C12 122.1(2) . . ?
C10 C9 C8 116.7(2) . . ?
C10 C9 C14 120.3(2) . . ?
C8 C9 C14 123.0(2) . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 C13 121.8(2) . . ?
C11 C10 C13 117.9(2) . . ?
N4 C11 N1 116.3(2) . . ?
N4 C11 C10 121.8(2) . . ?
N1 C11 C10 121.9(2) . . ?
N2 C12 C8 177.5(3) . . ?
N3 C13 C10 175.8(3) . . ?
C15 C14 C19 118.1(2) . . ?
C15 C14 C9 122.5(2) . . ?
C19 C14 C9 119.4(2) . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
O1 C17 C18 123.9(2) . . ?
O1 C17 C16 116.2(2) . . ?
C18 C17 C16 119.9(2) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N1 C11 117.7(2) . . ?
C11 N4 H1N4 118(2) . . ?
C11 N4 H2N4 118(2) . . ?
H1N4 N4 H2N4 124(3) . . ?
C17 O1 C20 115.84(19) . . ?
C7 Se1 C1 101.56(10) . . ?

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 C1 C2 C3 0.2(4) . . . . ?
Se1 C1 C2 C3 -173.14(19) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
Se1 C1 C6 C5 174.04(19) . . . . ?
N1 C7 C8 C9 2.5(4) . . . . ?
Se1 C7 C8 C9 -174.96(17) . . . . ?
N1 C7 C8 C12 -177.8(2) . . . . ?
Se1 C7 C8 C12 4.7(3) . . . . ?
C7 C8 C9 C10 -3.3(3) . . . . ?
C12 C8 C9 C10 177.0(2) . . . . ?
C7 C8 C9 C14 175.4(2) . . . . ?
C12 C8 C9 C14 -4.3(4) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C14 C9 C10 C11 -177.3(2) . . . . ?
C8 C9 C10 C13 -174.9(2) . . . . ?
C14 C9 C10 C13 6.3(4) . . . . ?
C9 C10 C11 N4 -179.1(2) . . . . ?
C13 C10 C11 N4 -2.6(4) . . . . ?
C9 C10 C11 N1 1.5(4) . . . . ?
C13 C10 C11 N1 178.0(2) . . . . ?
C7 C8 C12 N2 45(7) . . . . ?
C9 C8 C12 N2 -135(7) . . . . ?
C9 C10 C13 N3 176(100) . . . . ?
C11 C10 C13 N3 0(4) . . . . ?
C10 C9 C14 C15 -133.3(3) . . . . ?
C8 C9 C14 C15 48.0(3) . . . . ?
C10 C9 C14 C19 45.7(3) . . . . ?
C8 C9 C14 C19 -133.0(3) . . . . ?
C19 C14 C15 C16 -1.8(4) . . . . ?
C9 C14 C15 C16 177.2(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 O1 -177.7(2) . . . . ?
C15 C16 C17 C18 1.7(4) . . . . ?
O1 C17 C18 C19 177.4(2) . . . . ?
C16 C17 C18 C19 -1.9(4) . . . . ?
C17 C18 C19 C14 0.2(4) . . . . ?
C15 C14 C19 C18 1.6(4) . . . . ?
C9 C14 C19 C18 -177.4(2) . . . . ?
C8 C7 N1 C11 0.5(3) . . . . ?
Se1 C7 N1 C11 177.95(17) . . . . ?
N4 C11 N1 C7 178.1(2) . . . . ?
C10 C11 N1 C7 -2.5(3) . . . . ?
C18 C17 O1 C20 -5.1(3) . . . . ?
C16 C17 O1 C20 174.2(2) . . . . ?
N1 C7 Se1 C1 10.5(2) . . . . ?
C8 C7 Se1 C1 -171.89(18) . . . . ?
C2 C1 Se1 C7 -130.99(19) . . . . ?
C6 C1 Se1 C7 55.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.111
