# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mk-1
_database_code_depnum_ccdc_archive 'CCDC 1520950'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;
_audit_creation_date             2016-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        
'8-Methyl-2-nitro-7,8-dihydro-5H-benzo[i]pyrido[3,2-b][1,4,7]oxadiazecin-9(6H)-one '
_chemical_formula_moiety         '1.14(C15 H13 N4 O4)'
_chemical_formula_sum            'C15 H14 N4 O4'
_chemical_formula_weight         314.30
_chemical_melting_point          ?
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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   15.0497(7)
_cell_length_b                   11.1392(5)
_cell_length_c                   16.514(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2768.5(8)
_cell_formula_units_Z            7
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11083
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.59
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2614
_reflns_number_total             3167
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0401P)²+1.6886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1032
_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. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.11954(7) 0.15134(9) 0.20032(6) 0.0159(2) Uani 1 d . . .
O2 O 0.11592(8) -0.02650(11) -0.07854(8) 0.0258(3) Uani 1 d . . .
N3 N 0.18744(8) 0.47155(11) 0.11321(8) 0.0135(3) Uani 1 d . . .
O4 O 0.03350(8) 0.09658(11) -0.14740(7) 0.0252(3) Uani 1 d . . .
C5 C 0.03422(10) 0.49767(13) 0.16718(10) 0.0163(3) Uani 1 d . . .
H5A H 0.0001 0.5394 0.2083 0.020 Uiso 1 calc . . .
H5B H 0.0109 0.5200 0.1145 0.020 Uiso 1 calc . . .
C6 C 0.06154(10) 0.14113(14) -0.01325(9) 0.0146(3) Uani 1 d . . .
N7 N 0.07148(9) 0.06558(12) -0.08423(8) 0.0175(3) Uani 1 d . . .
N9 N 0.02583(8) 0.36782(11) 0.17861(8) 0.0149(3) Uani 1 d . . .
N10 N 0.00677(9) 0.32470(12) 0.04146(8) 0.0162(3) Uani 1 d . . .
C11 C 0.19281(10) 0.18361(13) 0.32270(9) 0.0144(3) Uani 1 d . . .
H11 H 0.1587 0.1206 0.3426 0.017 Uiso 1 calc . . .
C12 C 0.30520(10) 0.33328(14) 0.34269(9) 0.0154(3) Uani 1 d . . .
H12 H 0.3472 0.3703 0.3755 0.019 Uiso 1 calc . . .
C13 C 0.03978(9) 0.29272(13) 0.11435(9) 0.0133(3) Uani 1 d . . .
C14 C 0.08740(10) 0.18381(13) 0.12477(9) 0.0133(3) Uani 1 d . . .
C15 C 0.18233(10) 0.51845(14) 0.03007(9) 0.0162(3) Uani 1 d . . .
H15A H 0.1250 0.5005 0.0076 0.024 Uiso 1 calc . . .
H15B H 0.2276 0.4816 -0.0025 0.024 Uiso 1 calc . . .
H15C H 0.1910 0.6038 0.0308 0.024 Uiso 1 calc . . .
C16 C 0.29322(10) 0.37141(13) 0.26346(9) 0.0147(3) Uani 1 d . . .
H16 H 0.3277 0.4343 0.2438 0.018 Uiso 1 calc . . .
C17 C 0.18187(9) 0.22102(13) 0.24266(9) 0.0126(3) Uani 1 d . . .
C18 C 0.09833(10) 0.10683(13) 0.06086(9) 0.0137(3) Uani 1 d . . .
H18 H 0.1289 0.0348 0.0666 0.016 Uiso 1 calc . . .
C19 C 0.25407(10) 0.23946(14) 0.37275(9) 0.0153(3) Uani 1 d . . .
H19 H 0.2609 0.2143 0.4261 0.018 Uiso 1 calc . . .
C20 C 0.23056(9) 0.31779(13) 0.21223(9) 0.0120(3) Uani 1 d . . .
C21 C 0.01691(10) 0.24940(14) -0.02027(9) 0.0167(3) Uani 1 d . . .
H21 H -0.0070 0.2703 -0.0703 0.020 Uiso 1 calc . . .
C22 C 0.13264(10) 0.53443(13) 0.17314(10) 0.0153(3) Uani 1 d . . .
H22A H 0.1378 0.6203 0.1648 0.018 Uiso 1 calc . . .
H22B H 0.1545 0.5164 0.2270 0.018 Uiso 1 calc . . .
O8 O 0.26611(7) 0.30807(10) 0.07216(6) 0.0171(2) Uani 1 d . . .
C1A C 0.22766(9) 0.36411(13) 0.12608(9) 0.0119(3) Uani 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
O1 C14 1.3862(18) . ?
O1 C17 1.4040(17) . ?
O2 N7 1.2281(18) . ?
N3 C15 1.4709(19) . ?
N3 C22 1.4664(19) . ?
N3 C1A 1.3579(19) . ?
O4 N7 1.2387(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 N9 1.4641(19) . ?
C5 C22 1.540(2) . ?
C6 N7 1.451(2) . ?
C6 C18 1.397(2) . ?
C6 C21 1.385(2) . ?
N9 C13 1.368(2) . ?
N10 C13 1.350(2) . ?
N10 C21 1.329(2) . ?
C11 H11 0.9300 . ?
C11 C17 1.396(2) . ?
C11 C19 1.386(2) . ?
C12 H12 0.9300 . ?
C12 C16 1.387(2) . ?
C12 C19 1.389(2) . ?
C13 C14 1.419(2) . ?
C14 C18 1.370(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C20 1.401(2) . ?
C17 C20 1.397(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C1A 1.514(2) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
O8 C1A 1.2319(18) . ?

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
C14 O1 C17 122.50(11) . . ?
C22 N3 C15 115.52(12) . . ?
C1A N3 C15 118.85(12) . . ?
C1A N3 C22 124.47(13) . . ?
H5A C5 H5B 108.2 . . ?
N9 C5 H5A 109.7 . . ?
N9 C5 H5B 109.7 . . ?
N9 C5 C22 109.72(12) . . ?
C22 C5 H5A 109.7 . . ?
C22 C5 H5B 109.7 . . ?
C18 C6 N7 120.56(14) . . ?
C21 C6 N7 119.17(14) . . ?
C21 C6 C18 120.25(14) . . ?
O2 N7 O4 123.26(14) . . ?
O2 N7 C6 118.61(13) . . ?
O4 N7 C6 118.12(13) . . ?
C13 N9 C5 119.41(13) . . ?
C21 N10 C13 118.37(13) . . ?
C17 C11 H11 119.7 . . ?
C19 C11 H11 119.7 . . ?
C19 C11 C17 120.62(14) . . ?
C16 C12 H12 120.2 . . ?
C16 C12 C19 119.69(14) . . ?
C19 C12 H12 120.2 . . ?
N9 C13 C14 120.42(14) . . ?
N10 C13 N9 118.29(13) . . ?
N10 C13 C14 121.29(14) . . ?
O1 C14 C13 120.55(13) . . ?
C18 C14 O1 119.23(13) . . ?
C18 C14 C13 120.15(14) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16 119.1 . . ?
C12 C16 C20 121.77(14) . . ?
C20 C16 H16 119.1 . . ?
C11 C17 O1 112.68(13) . . ?
C20 C17 O1 126.72(13) . . ?
C20 C17 C11 120.61(13) . . ?
C6 C18 H18 121.4 . . ?
C14 C18 C6 117.15(14) . . ?
C14 C18 H18 121.4 . . ?
C11 C19 C12 119.54(14) . . ?
C11 C19 H19 120.2 . . ?
C12 C19 H19 120.2 . . ?
C16 C20 C1A 116.21(13) . . ?
C17 C20 C16 117.71(14) . . ?
C17 C20 C1A 125.86(13) . . ?
C6 C21 H21 118.6 . . ?
N10 C21 C6 122.75(14) . . ?
N10 C21 H21 118.6 . . ?
N3 C22 C5 111.77(12) . . ?
N3 C22 H22A 109.3 . . ?
N3 C22 H22B 109.3 . . ?
C5 C22 H22A 109.3 . . ?
C5 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
N3 C1A C20 117.40(13) . . ?
O8 C1A N3 122.88(14) . . ?
O8 C1A C20 119.55(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: propanol-2'
