# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mo_NP0K4_46_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1587528'
loop_
_audit_author_name
_audit_author_address
'Shiva Kumar kota'
;Osmania University
India
;
_audit_update_record             
;
2019-04-10 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N4 O'
_chemical_formula_sum            'C20 H20 N4 O'
_chemical_formula_weight         332.40

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                   9.1911(11)
_cell_length_b                   10.2029(14)
_cell_length_c                   10.5844(14)
_cell_angle_alpha                105.786(4)
_cell_angle_beta                 112.987(4)
_cell_angle_gamma                97.227(4)
_cell_volume                     848.58(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7414
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.70

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28075
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         28.814
_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             4402
_reflns_number_gt                3296
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0383P)²+0.6324P] 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         4402
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_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
C1 C -0.0615(3) 0.2079(2) -0.1073(2) 0.0248(4) Uani 1 1 d . . . . .
H1A H -0.1176 0.2819 -0.0917 0.037 Uiso 1 1 calc R U . . .
H1B H -0.1245 0.1194 -0.1137 0.037 Uiso 1 1 calc R U . . .
H1C H -0.0519 0.1946 -0.1987 0.037 Uiso 1 1 calc R U . . .
C2 C 0.1066(2) 0.2504(2) 0.0188(2) 0.0202(4) Uani 1 1 d . . . . .
C3 C 0.1896(3) 0.1500(2) 0.0522(2) 0.0227(4) Uani 1 1 d . . . . .
H3 H 0.1401 0.0532 -0.0068 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3428(2) 0.1887(2) 0.1698(2) 0.0211(4) Uani 1 1 d . . . . .
H4 H 0.3961 0.1179 0.1907 0.025 Uiso 1 1 calc R U . . .
C5 C 0.4209(2) 0.3305(2) 0.2586(2) 0.0181(4) Uani 1 1 d . . . . .
C6 C 0.3391(2) 0.4316(2) 0.2237(2) 0.0183(4) Uani 1 1 d . . . . .
H6 H 0.3891 0.5288 0.2811 0.022 Uiso 1 1 calc R U . . .
C7 C 0.1859(2) 0.3911(2) 0.1061(2) 0.0198(4) Uani 1 1 d . . . . .
H7 H 0.1327 0.4617 0.0842 0.024 Uiso 1 1 calc R U . . .
C8 C 0.5827(2) 0.3659(2) 0.3843(2) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.7121(2) 0.4872(2) 0.4663(2) 0.0164(4) Uani 1 1 d . . . . .
C10 C 0.7480(2) 0.63284(19) 0.4705(2) 0.0165(4) Uani 1 1 d . . . . .
C11 C 1.0172(2) 0.6701(2) 0.6681(2) 0.0192(4) Uani 1 1 d . . . . .
C12 C 1.1662(2) 0.7656(2) 0.7692(2) 0.0222(4) Uani 1 1 d . . . . .
H12 H 1.1894 0.8593 0.7699 0.027 Uiso 1 1 calc R U . . .
C13 C 1.2808(2) 0.7228(2) 0.8690(2) 0.0228(4) Uani 1 1 d . . . . .
H13 H 1.3832 0.7875 0.9387 0.027 Uiso 1 1 calc R U . . .
C14 C 1.2475(3) 0.5861(2) 0.8684(2) 0.0236(4) Uani 1 1 d . . . . .
H14 H 1.3273 0.5577 0.9370 0.028 Uiso 1 1 calc R U . . .
C15 C 1.0986(2) 0.4911(2) 0.7682(2) 0.0211(4) Uani 1 1 d . . . . .
H15 H 1.0751 0.3976 0.7678 0.025 Uiso 1 1 calc R U . . .
C16 C 0.9843(2) 0.5342(2) 0.6684(2) 0.0178(4) Uani 1 1 d . . . . .
C17 C 0.7302(3) 0.9355(2) 0.5426(2) 0.0229(4) Uani 1 1 d . . . . .
H17A H 0.6521 0.9127 0.5804 0.034 Uiso 1 1 calc R U . . .
H17B H 0.7335 1.0296 0.5359 0.034 Uiso 1 1 calc R U . . .
H17C H 0.8393 0.9340 0.6092 0.034 Uiso 1 1 calc R U . . .
C18 C 0.6765(2) 0.82650(19) 0.3906(2) 0.0180(4) Uani 1 1 d . . . . .
C19 C 0.5113(3) 0.8377(2) 0.2868(2) 0.0271(5) Uani 1 1 d . . . . .
H19A H 0.4740 0.7673 0.1891 0.041 Uiso 1 1 calc R U . . .
H19B H 0.5229 0.9324 0.2810 0.041 Uiso 1 1 calc R U . . .
H19C H 0.4310 0.8206 0.3239 0.041 Uiso 1 1 calc R U . . .
C20 C 0.8027(3) 0.8515(2) 0.3330(2) 0.0269(5) Uani 1 1 d . . . . .
H20A H 0.9069 0.8399 0.3978 0.040 Uiso 1 1 calc R U . . .
H20B H 0.8189 0.9474 0.3307 0.040 Uiso 1 1 calc R U . . .
H20C H 0.7632 0.7832 0.2339 0.040 Uiso 1 1 calc R U . . .
N1 N 0.6293(2) 0.26161(17) 0.43654(18) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.7775(2) 0.31004(17) 0.54441(18) 0.0205(4) Uani 1 1 d . . . . .
N3 N 0.82856(19) 0.44578(16) 0.56245(17) 0.0171(3) Uani 1 1 d . . . . .
N4 N 0.64594(19) 0.68027(16) 0.38978(17) 0.0165(3) Uani 1 1 d . . . . .
O1 O 0.90690(16) 0.71585(14) 0.56922(15) 0.0214(3) Uani 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 1.504(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.391(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 C8 1.473(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.368(2) . ?
C8 C9 1.392(3) . ?
C9 N3 1.363(2) . ?
C9 C10 1.466(3) . ?
C10 N4 1.248(2) . ?
C10 O1 1.399(2) . ?
C11 O1 1.377(2) . ?
C11 C16 1.382(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 N3 1.411(2) . ?
C17 C18 1.529(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N4 1.480(2) . ?
C18 C19 1.528(3) . ?
C18 C20 1.531(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 N2 1.308(2) . ?
N2 N3 1.341(2) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.27(19) . . ?
C7 C2 C1 121.58(18) . . ?
C3 C2 C1 121.15(18) . . ?
C4 C3 C2 121.19(18) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.22(18) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 117.67(18) . . ?
C6 C5 C8 123.28(17) . . ?
C4 C5 C8 119.04(17) . . ?
C7 C6 C5 120.36(18) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 122.26(18) . . ?
C6 C7 H7 118.9 . . ?
C2 C7 H7 118.9 . . ?
N1 C8 C9 107.48(17) . . ?
N1 C8 C5 118.33(17) . . ?
C9 C8 C5 134.15(17) . . ?
N3 C9 C8 103.76(16) . . ?
N3 C9 C10 118.99(17) . . ?
C8 C9 C10 137.24(17) . . ?
N4 C10 O1 121.51(16) . . ?
N4 C10 C9 122.88(17) . . ?
O1 C10 C9 115.60(15) . . ?
O1 C11 C16 122.40(17) . . ?
O1 C11 C12 117.61(17) . . ?
C16 C11 C12 119.99(18) . . ?
C13 C12 C11 119.18(19) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.59(19) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.27(18) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.01(18) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 120.96(18) . . ?
C11 C16 N3 115.63(17) . . ?
C15 C16 N3 123.41(17) . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 C19 105.04(15) . . ?
N4 C18 C17 111.93(15) . . ?
C19 C18 C17 108.38(16) . . ?
N4 C18 C20 110.23(15) . . ?
C19 C18 C20 110.01(16) . . ?
C17 C18 C20 111.05(17) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 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 . . ?
N2 N1 C8 110.13(16) . . ?
N1 N2 N3 106.84(15) . . ?
N2 N3 C9 111.79(16) . . ?
N2 N3 C16 123.76(15) . . ?
C9 N3 C16 124.45(16) . . ?
C10 N4 C18 124.76(16) . . ?
C11 O1 C10 122.57(15) . . ?

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 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 C4 -178.76(18) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C4 C5 C8 178.79(18) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C8 C5 C6 C7 -178.54(17) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
C1 C2 C7 C6 178.96(18) . . . . ?
C6 C5 C8 N1 159.88(17) . . . . ?
C4 C5 C8 N1 -19.3(3) . . . . ?
C6 C5 C8 C9 -22.9(3) . . . . ?
C4 C5 C8 C9 158.0(2) . . . . ?
N1 C8 C9 N3 0.33(19) . . . . ?
C5 C8 C9 N3 -177.15(19) . . . . ?
N1 C8 C9 C10 179.3(2) . . . . ?
C5 C8 C9 C10 1.8(4) . . . . ?
N3 C9 C10 N4 -177.40(17) . . . . ?
C8 C9 C10 N4 3.8(3) . . . . ?
N3 C9 C10 O1 4.1(2) . . . . ?
C8 C9 C10 O1 -174.7(2) . . . . ?
O1 C11 C12 C13 -179.19(17) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
O1 C11 C16 C15 179.22(17) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
O1 C11 C16 N3 -1.3(3) . . . . ?
C12 C11 C16 N3 179.24(17) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C14 C15 C16 N3 -179.55(17) . . . . ?
C9 C8 N1 N2 0.0(2) . . . . ?
C5 C8 N1 N2 177.95(15) . . . . ?
C8 N1 N2 N3 -0.3(2) . . . . ?
N1 N2 N3 C9 0.6(2) . . . . ?
N1 N2 N3 C16 -179.37(16) . . . . ?
C8 C9 N3 N2 -0.56(19) . . . . ?
C10 C9 N3 N2 -179.74(15) . . . . ?
C8 C9 N3 C16 179.39(16) . . . . ?
C10 C9 N3 C16 0.2(3) . . . . ?
C11 C16 N3 N2 178.24(16) . . . . ?
C15 C16 N3 N2 -2.3(3) . . . . ?
C11 C16 N3 C9 -1.7(3) . . . . ?
C15 C16 N3 C9 177.74(17) . . . . ?
O1 C10 N4 C18 -1.8(3) . . . . ?
C9 C10 N4 C18 179.75(16) . . . . ?
C19 C18 N4 C10 -173.81(18) . . . . ?
C17 C18 N4 C10 -56.4(2) . . . . ?
C20 C18 N4 C10 67.7(2) . . . . ?
C16 C11 O1 C10 6.0(3) . . . . ?
C12 C11 O1 C10 -174.52(17) . . . . ?
N4 C10 O1 C11 174.30(17) . . . . ?
C9 C10 O1 C11 -7.2(2) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_mo_NPK2_165_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1864070'
loop_
_audit_author_name
_audit_author_address
'Dr. K. Shiva Kumar'
;Osmania University
India
;
_audit_update_record             
;
2018-08-27 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N4'
_chemical_formula_sum            'C20 H20 N4'
_chemical_formula_weight         316.40

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'

_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                   9.0962(5)
_cell_length_b                   10.1454(6)
_cell_length_c                   18.0969(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.369(2)
_cell_angle_gamma                90
_cell_volume                     1668.64(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9708
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.52

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62594
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5099
_reflns_number_gt                4378
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0703P)²+0.4658P] 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         5099
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25582(13) 0.57376(13) 0.80708(6) 0.0236(2) Uani 1 1 d . . . . .
H1A H 0.1533 0.5763 0.7883 0.035 Uiso 1 1 calc R U . . .
H1B H 0.2749 0.6491 0.8400 0.035 Uiso 1 1 calc R U . . .
H1C H 0.2737 0.4916 0.8345 0.035 Uiso 1 1 calc R U . . .
C2 C 0.35651(12) 0.58036(11) 0.74330(6) 0.0179(2) Uani 1 1 d . . . . .
C3 C 0.41809(12) 0.46720(11) 0.71422(6) 0.0196(2) Uani 1 1 d . . . . .
H3 H 0.3982 0.3843 0.7361 0.024 Uiso 1 1 calc R U . . .
C4 C 0.50794(12) 0.47223(10) 0.65399(6) 0.0178(2) Uani 1 1 d . . . . .
H4 H 0.5480 0.3933 0.6350 0.021 Uiso 1 1 calc R U . . .
C5 C 0.53939(11) 0.59338(10) 0.62134(6) 0.01418(19) Uani 1 1 d . . . . .
C6 C 0.47973(12) 0.70787(10) 0.65097(6) 0.0182(2) Uani 1 1 d . . . . .
H6 H 0.5011 0.7912 0.6300 0.022 Uiso 1 1 calc R U . . .
C7 C 0.38950(13) 0.70073(11) 0.71081(6) 0.0197(2) Uani 1 1 d . . . . .
H7 H 0.3494 0.7795 0.7300 0.024 Uiso 1 1 calc R U . . .
C8 C 0.63229(11) 0.60185(10) 0.55743(6) 0.01378(19) Uani 1 1 d . . . . .
C9 C 0.71306(11) 0.50798(10) 0.52084(5) 0.01307(18) Uani 1 1 d . . . . .
C10 C 0.76109(11) 0.36868(10) 0.51560(6) 0.01342(19) Uani 1 1 d . . . . .
C11 C 0.86398(11) 0.37037(10) 0.45156(6) 0.01461(19) Uani 1 1 d . . . . .
C12 C 0.95100(12) 0.27689(11) 0.41800(6) 0.0185(2) Uani 1 1 d . . . . .
H12 H 0.9513 0.1880 0.4346 0.022 Uiso 1 1 calc R U . . .
C13 C 1.03779(12) 0.31458(12) 0.35982(6) 0.0209(2) Uani 1 1 d . . . . .
H13 H 1.0965 0.2504 0.3368 0.025 Uiso 1 1 calc R U . . .
C14 C 1.04015(12) 0.44431(12) 0.33486(6) 0.0207(2) Uani 1 1 d . . . . .
H14 H 1.1007 0.4676 0.2954 0.025 Uiso 1 1 calc R U . . .
C15 C 0.95439(12) 0.54017(11) 0.36733(6) 0.0183(2) Uani 1 1 d . . . . .
H15 H 0.9543 0.6291 0.3508 0.022 Uiso 1 1 calc R U . . .
C16 C 0.86981(11) 0.50011(10) 0.42447(6) 0.01457(19) Uani 1 1 d . . . . .
C17 C 0.74412(12) 0.14194(10) 0.56371(6) 0.0170(2) Uani 1 1 d . . . . .
C18 C 0.69240(13) 0.07523(11) 0.49139(7) 0.0217(2) Uani 1 1 d . . . . .
H18A H 0.5877 0.0938 0.4815 0.033 Uiso 1 1 calc R U . . .
H18B H 0.7071 -0.0202 0.4957 0.033 Uiso 1 1 calc R U . . .
H18C H 0.7492 0.1093 0.4507 0.033 Uiso 1 1 calc R U . . .
C19 C 0.90628(13) 0.11522(11) 0.58496(7) 0.0232(2) Uani 1 1 d . . . . .
H19A H 0.9688 0.1608 0.5503 0.035 Uiso 1 1 calc R U . . .
H19B H 0.9252 0.0202 0.5830 0.035 Uiso 1 1 calc R U . . .
H19C H 0.9286 0.1476 0.6352 0.035 Uiso 1 1 calc R U . . .
C20 C 0.65052(15) 0.08927(12) 0.62559(7) 0.0269(3) Uani 1 1 d . . . . .
H20A H 0.6775 0.1349 0.6719 0.040 Uiso 1 1 calc R U . . .
H20B H 0.6679 -0.0055 0.6317 0.040 Uiso 1 1 calc R U . . .
H20C H 0.5462 0.1047 0.6128 0.040 Uiso 1 1 calc R U . . .
N1 N 0.71346(10) 0.28428(8) 0.56105(5) 0.01522(18) Uani 1 1 d . . . . .
N2 N 0.77766(10) 0.57771(8) 0.46745(5) 0.01438(18) Uani 1 1 d . . . . .
N3 N 0.65426(10) 0.72096(9) 0.52300(5) 0.01718(19) Uani 1 1 d . . . . .
N4 N 0.74369(10) 0.70608(9) 0.46793(5) 0.01773(19) Uani 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 1.5042(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.3904(15) . ?
C2 C7 1.3934(16) . ?
C3 C4 1.3901(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3985(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3983(14) . ?
C5 C8 1.4628(14) . ?
C6 C7 1.3874(15) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N3 1.3780(13) . ?
C8 C9 1.3876(14) . ?
C9 N2 1.3514(13) . ?
C9 C10 1.4834(14) . ?
C10 N1 1.2756(13) . ?
C10 C11 1.5195(14) . ?
C11 C12 1.3909(14) . ?
C11 C16 1.4063(14) . ?
C12 C13 1.3953(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3919(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3919(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3756(14) . ?
C15 H15 0.9500 . ?
C16 N2 1.4076(13) . ?
C17 N1 1.4712(13) . ?
C17 C18 1.5302(16) . ?
C17 C20 1.5308(16) . ?
C17 C19 1.5330(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 N4 1.3386(12) . ?
N3 N4 1.3208(13) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.82(10) . . ?
C3 C2 C1 121.42(10) . . ?
C7 C2 C1 120.75(10) . . ?
C2 C3 C4 121.71(10) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 120.05(10) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 118.59(10) . . ?
C4 C5 C8 121.37(9) . . ?
C6 C5 C8 120.03(9) . . ?
C7 C6 C5 120.50(10) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 121.31(10) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
N3 C8 C9 107.25(9) . . ?
N3 C8 C5 120.56(9) . . ?
C9 C8 C5 132.18(9) . . ?
N2 C9 C8 103.67(9) . . ?
N2 C9 C10 108.36(9) . . ?
C8 C9 C10 147.95(9) . . ?
N1 C10 C9 119.31(9) . . ?
N1 C10 C11 137.37(9) . . ?
C9 C10 C11 103.32(8) . . ?
C12 C11 C16 117.11(10) . . ?
C12 C11 C10 134.82(10) . . ?
C16 C11 C10 108.04(9) . . ?
C11 C12 C13 119.51(10) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 121.39(10) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 120.48(10) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 116.84(10) . . ?
C16 C15 H15 121.6 . . ?
C14 C15 H15 121.6 . . ?
C15 C16 C11 124.67(10) . . ?
C15 C16 N2 127.91(10) . . ?
C11 C16 N2 107.40(9) . . ?
N1 C17 C18 110.79(9) . . ?
N1 C17 C20 104.85(9) . . ?
C18 C17 C20 108.11(9) . . ?
N1 C17 C19 111.15(9) . . ?
C18 C17 C19 113.26(9) . . ?
C20 C17 C19 108.26(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 N1 C17 127.67(9) . . ?
N4 N2 C9 113.41(9) . . ?
N4 N2 C16 133.68(9) . . ?
C9 N2 C16 112.88(9) . . ?
N4 N3 C8 110.26(8) . . ?
N3 N4 N2 105.41(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
C7 C2 C3 C4 -0.99(16) . . . . ?
C1 C2 C3 C4 178.18(10) . . . . ?
C2 C3 C4 C5 0.45(17) . . . . ?
C3 C4 C5 C6 0.53(16) . . . . ?
C3 C4 C5 C8 -179.36(10) . . . . ?
C4 C5 C6 C7 -0.96(16) . . . . ?
C8 C5 C6 C7 178.93(10) . . . . ?
C5 C6 C7 C2 0.42(17) . . . . ?
C3 C2 C7 C6 0.56(17) . . . . ?
C1 C2 C7 C6 -178.63(10) . . . . ?
C4 C5 C8 N3 175.73(10) . . . . ?
C6 C5 C8 N3 -4.16(15) . . . . ?
C4 C5 C8 C9 -5.58(17) . . . . ?
C6 C5 C8 C9 174.52(11) . . . . ?
N3 C8 C9 N2 0.17(11) . . . . ?
C5 C8 C9 N2 -178.64(10) . . . . ?
N3 C8 C9 C10 178.15(15) . . . . ?
C5 C8 C9 C10 -0.7(2) . . . . ?
N2 C9 C10 N1 179.93(9) . . . . ?
C8 C9 C10 N1 2.0(2) . . . . ?
N2 C9 C10 C11 0.54(10) . . . . ?
C8 C9 C10 C11 -177.38(15) . . . . ?
N1 C10 C11 C12 -1.7(2) . . . . ?
C9 C10 C11 C12 177.52(12) . . . . ?
N1 C10 C11 C16 -179.51(12) . . . . ?
C9 C10 C11 C16 -0.30(10) . . . . ?
C16 C11 C12 C13 -0.43(15) . . . . ?
C10 C11 C12 C13 -178.10(11) . . . . ?
C11 C12 C13 C14 0.49(17) . . . . ?
C12 C13 C14 C15 -0.45(17) . . . . ?
C13 C14 C15 C16 0.34(16) . . . . ?
C14 C15 C16 C11 -0.31(16) . . . . ?
C14 C15 C16 N2 178.06(10) . . . . ?
C12 C11 C16 C15 0.35(16) . . . . ?
C10 C11 C16 C15 178.62(9) . . . . ?
C12 C11 C16 N2 -178.29(9) . . . . ?
C10 C11 C16 N2 -0.03(11) . . . . ?
C9 C10 N1 C17 178.06(9) . . . . ?
C11 C10 N1 C17 -2.83(19) . . . . ?
C18 C17 N1 C10 -59.91(14) . . . . ?
C20 C17 N1 C10 -176.30(10) . . . . ?
C19 C17 N1 C10 66.95(14) . . . . ?
C8 C9 N2 N4 -0.05(11) . . . . ?
C10 C9 N2 N4 -178.91(8) . . . . ?
C8 C9 N2 C16 178.25(8) . . . . ?
C10 C9 N2 C16 -0.61(11) . . . . ?
C15 C16 N2 N4 -0.34(18) . . . . ?
C11 C16 N2 N4 178.25(11) . . . . ?
C15 C16 N2 C9 -178.18(10) . . . . ?
C11 C16 N2 C9 0.41(11) . . . . ?
C9 C8 N3 N4 -0.25(12) . . . . ?
C5 C8 N3 N4 178.72(9) . . . . ?
C8 N3 N4 N2 0.22(11) . . . . ?
C9 N2 N4 N3 -0.11(12) . . . . ?
C16 N2 N4 N3 -177.94(10) . . . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.141

