# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_dir_05062020_khaja2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2009554'
_audit_update_record             
;
2020-08-05 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 N12 O16'
_chemical_formula_weight         496.18

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.6672(6)
_cell_length_b                   9.6302(5)
_cell_length_c                   9.0564(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.776(2)
_cell_angle_gamma                90.00
_cell_volume                     825.38(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6055
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.19

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6232
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10 
_exptl_special_details 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16741
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         28.29
_reflns_number_total             2027
_reflns_number_gt                1719
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0494P)²+0.2825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2027
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48309(12) 0.59610(14) 0.12512(12) 0.0511(3) Uani 1 1 d . . .
N1 N 0.67180(12) 0.49345(12) 0.59303(12) 0.0311(3) Uani 1 1 d . . .
N2 N 0.71011(12) 0.51843(12) 0.45882(13) 0.0324(3) Uani 1 1 d . . .
O7 O 0.66252(14) 0.65841(13) 0.82196(15) 0.0559(3) Uani 1 1 d . . .
O5 O 0.70044(16) 0.24819(12) 0.71506(16) 0.0598(4) Uani 1 1 d . . .
N5 N 0.59650(13) 0.56395(13) 0.20423(13) 0.0357(3) Uani 1 1 d . . .
O2 O 0.70825(13) 0.56067(16) 0.16561(13) 0.0567(4) Uani 1 1 d . . .
O8 O 0.87453(14) 0.60634(16) 0.93861(14) 0.0612(4) Uani 1 1 d . . .
O6 O 0.82170(15) 0.32365(15) 0.92854(15) 0.0626(4) Uani 1 1 d . . .
O10 O 0.96455(14) 0.59983(15) 0.66385(16) 0.0610(4) Uani 1 1 d . . .
N7 N 0.76531(13) 0.33465(13) 0.79835(15) 0.0400(3) Uani 1 1 d . . .
O9 O 0.97934(14) 0.37404(16) 0.67107(17) 0.0624(4) Uani 1 1 d . . .
N9 N 0.77149(13) 0.59274(13) 0.84066(14) 0.0379(3) Uani 1 1 d . . .
N8 N 0.92388(13) 0.48453(15) 0.68279(15) 0.0415(3) Uani 1 1 d . . .
C1 C 0.59194(14) 0.52962(13) 0.35890(14) 0.0304(3) Uani 1 1 d . . .
C3 C 0.52679(14) 0.48827(13) 0.57489(14) 0.0296(3) Uani 1 1 d . . .
C5 C 0.77726(14) 0.47772(14) 0.72411(15) 0.0309(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0447(6) 0.0786(9) 0.0286(5) 0.0100(5) 0.0045(5) 0.0063(6)
N1 0.0279(5) 0.0418(6) 0.0233(5) 0.0029(4) 0.0046(4) -0.0026(4)
N2 0.0329(6) 0.0388(6) 0.0267(6) 0.0021(4) 0.0086(4) -0.0022(4)
O7 0.0617(8) 0.0459(6) 0.0567(8) -0.0109(5) 0.0041(6) 0.0115(5)
O5 0.0780(9) 0.0356(6) 0.0648(8) -0.0005(5) 0.0122(7) -0.0069(6)
N5 0.0388(6) 0.0435(6) 0.0261(5) 0.0015(5) 0.0098(5) -0.0027(5)
O2 0.0442(7) 0.0921(10) 0.0386(6) 0.0101(6) 0.0196(5) -0.0009(6)
O8 0.0483(7) 0.0904(10) 0.0401(6) -0.0175(6) -0.0024(5) -0.0141(7)
O6 0.0647(8) 0.0727(9) 0.0452(7) 0.0262(6) -0.0012(6) 0.0033(6)
O10 0.0510(7) 0.0705(9) 0.0639(8) 0.0035(6) 0.0171(6) -0.0223(6)
N7 0.0393(6) 0.0406(6) 0.0405(7) 0.0100(5) 0.0089(5) 0.0047(5)
O9 0.0440(7) 0.0743(9) 0.0715(9) 0.0015(7) 0.0182(6) 0.0162(6)
N9 0.0398(7) 0.0408(6) 0.0320(6) -0.0025(5) 0.0050(5) -0.0061(5)
N8 0.0306(6) 0.0597(8) 0.0335(6) 0.0023(5) 0.0046(5) -0.0042(6)
C1 0.0325(6) 0.0346(6) 0.0246(6) 0.0018(5) 0.0072(5) -0.0014(5)
C3 0.0290(6) 0.0357(6) 0.0237(6) 0.0018(5) 0.0044(5) -0.0019(5)
C5 0.0285(6) 0.0363(6) 0.0268(6) 0.0025(5) 0.0027(5) -0.0013(5)

_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 N5 1.2209(16) . ?
N1 N2 1.3623(16) . ?
N1 C3 1.3787(17) . ?
N1 C5 1.4063(16) . ?
N2 C1 1.3091(17) . ?
O7 N9 1.2106(17) . ?
O5 N7 1.2093(18) . ?
N5 O2 1.2020(17) . ?
N5 C1 1.4486(17) . ?
O8 N9 1.1982(16) . ?
O6 N7 1.1984(18) . ?
O10 N8 1.2019(19) . ?
N7 C5 1.5477(17) . ?
O9 N8 1.2058(19) . ?
N9 C5 1.5388(18) . ?
N8 C5 1.5395(18) . ?
C1 C3 1.4098(18) 3_666 ?
C3 C3 1.368(2) 3_666 ?
C3 C1 1.4099(18) 3_666 ?

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
N2 N1 C3 110.80(11) . . ?
N2 N1 C5 119.33(11) . . ?
C3 N1 C5 129.87(11) . . ?
C1 N2 N1 105.87(11) . . ?
O2 N5 O1 126.06(12) . . ?
O2 N5 C1 118.81(12) . . ?
O1 N5 C1 115.11(11) . . ?
O6 N7 O5 128.80(14) . . ?
O6 N7 C5 116.54(13) . . ?
O5 N7 C5 114.66(12) . . ?
O8 N9 O7 127.92(14) . . ?
O8 N9 C5 116.46(13) . . ?
O7 N9 C5 115.62(11) . . ?
O10 N8 O9 129.67(15) . . ?
O10 N8 C5 114.73(13) . . ?
O9 N8 C5 115.58(13) . . ?
N2 C1 C3 111.54(11) . 3_666 ?
N2 C1 N5 119.52(12) . . ?
C3 C1 N5 128.85(12) 3_666 . ?
C3 C3 N1 106.38(14) 3_666 . ?
C3 C3 C1 105.40(14) 3_666 3_666 ?
N1 C3 C1 148.21(12) . 3_666 ?
N1 C5 N9 112.33(11) . . ?
N1 C5 N8 109.57(11) . . ?
N9 C5 N8 107.46(10) . . ?
N1 C5 N7 110.92(11) . . ?
N9 C5 N7 109.05(11) . . ?
N8 C5 N7 107.31(10) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.048
