# Electronic Supplementary Material (ESI) for ChemComm.
# 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_VCINA
_database_code_depnum_ccdc_archive 'CCDC 1505517'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            VCINA
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 N2 O7'
_chemical_formula_weight         298.25

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   5.8274(2)
_cell_length_b                   9.9168(3)
_cell_length_c                   23.1227(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1336.24(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3556
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      22.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9893
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20426
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.49
_reflns_number_total             2735
_reflns_number_gt                2265
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.0264P)²+0.2511P] 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     SHELXL
_refine_ls_extinction_coef       0.0078(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(12)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2735
_refine_ls_number_parameters     211
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.176
_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
O3 O -0.1871(3) 0.75045(17) 0.77380(6) 0.0275(4) Uani 1 1 d . . .
H3 H -0.1866 0.7858 0.7417 0.041 Uiso 1 1 calc R . .
O6 O 0.7525(3) 0.44413(17) 0.87066(7) 0.0247(4) Uani 1 1 d . . .
H6 H 0.7443 0.4290 0.9055 0.037 Uiso 1 1 calc R . .
O1 O 0.1051(3) 0.61076(16) 0.68709(6) 0.0291(4) Uani 1 1 d . . .
O2 O 0.3454(3) 0.57085(15) 0.76082(6) 0.0222(3) Uani 1 1 d . . .
O5 O 0.1665(3) 0.36896(15) 0.83077(7) 0.0231(4) Uani 1 1 d . . .
H5 H 0.0418 0.3968 0.8420 0.035 Uiso 1 1 calc R . .
O4 O 0.0771(3) 0.70763(16) 0.88738(6) 0.0244(4) Uani 1 1 d . . .
H4 H -0.0409 0.7527 0.8874 0.037 Uiso 1 1 calc R . .
O7 O 0.6498(3) 0.35696(16) -0.02238(6) 0.0278(4) Uani 1 1 d . . .
C2 C 0.0181(4) 0.6891(2) 0.78321(9) 0.0196(5) Uani 1 1 d . . .
C10 C 1.0568(4) 0.5821(2) 0.12824(10) 0.0261(5) Uani 1 1 d . . .
H10 H 1.0843 0.5924 0.1676 0.031 Uiso 1 1 calc RD . .
C11 C 0.8811(4) 0.4978(2) 0.11120(10) 0.0240(5) Uani 1 1 d D . .
H11 H 0.7914 0.4543 0.1387 0.029 Uiso 1 1 calc RD . .
C12 C 0.6543(4) 0.3875(2) 0.02986(9) 0.0211(5) Uani 1 1 d . . .
N2 N 0.4981(4) 0.3418(2) 0.06602(8) 0.0310(5) Uani 1 1 d . . .
H2A H 0.3904 0.2899 0.0537 0.037 Uiso 1 1 calc R . .
H2B H 0.5038 0.3639 0.1020 0.037 Uiso 1 1 calc R . .
N1 N 1.1900(3) 0.64970(19) 0.09099(8) 0.0281(5) Uani 1 1 d . . .
C3 C 0.1280(4) 0.6711(2) 0.83307(9) 0.0190(5) Uani 1 1 d . . .
C4 C 0.3418(4) 0.5909(2) 0.82317(8) 0.0185(5) Uani 1 1 d . . .
C5 C 0.3438(4) 0.4535(2) 0.85242(9) 0.0180(5) Uani 1 1 d . . .
C6 C 0.5673(4) 0.3790(3) 0.84180(10) 0.0225(5) Uani 1 1 d . . .
C1 C 0.1481(4) 0.6224(2) 0.73816(9) 0.0202(5) Uani 1 1 d . . .
C7 C 0.8392(4) 0.4785(2) 0.05286(9) 0.0223(5) Uani 1 1 d . . .
C9 C 1.1482(5) 0.6309(3) 0.03468(10) 0.0351(6) Uani 1 1 d . . .
H9 H 1.2392 0.6766 0.0081 0.042 Uiso 1 1 calc R . .
C8 C 0.9781(4) 0.5477(2) 0.01382(10) 0.0311(6) Uani 1 1 d . . .
H8 H 0.9562 0.5378 -0.0258 0.037 Uiso 1 1 calc R . .
H5A H 0.328(4) 0.4685(19) 0.8940(9) 0.010(5) Uiso 1 1 d . . .
H6B H 0.554(4) 0.284(2) 0.8544(9) 0.022(6) Uiso 1 1 d . . .
H6A H 0.602(4) 0.376(2) 0.7980(10) 0.023(6) Uiso 1 1 d . . .
H4A H 0.481(4) 0.641(2) 0.8325(9) 0.019(6) 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
O3 C2 1.359(3) . ?
O3 H3 0.8200 . ?
O6 C6 1.424(3) . ?
O6 H6 0.8200 . ?
O1 C1 1.213(2) . ?
O2 C1 1.363(3) . ?
O2 C4 1.456(2) . ?
O5 C5 1.422(3) . ?
O5 H5 0.8200 . ?
O4 C3 1.340(3) . ?
O4 H4 0.8200 . ?
O7 C12 1.245(2) . ?
C2 C3 1.331(3) . ?
C2 C1 1.448(3) . ?
C10 N1 1.339(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 C7 1.384(3) . ?
C11 H11 0.9300 . ?
C12 N2 1.316(3) . ?
C12 C7 1.503(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N1 C9 1.338(3) . ?
C3 C4 1.496(3) . ?
C4 C5 1.521(3) . ?
C4 H4A 0.97(2) . ?
C5 C6 1.517(3) . ?
C5 H5A 0.98(2) . ?
C6 H6B 0.99(2) . ?
C6 H6A 1.03(2) . ?
C7 C8 1.392(3) . ?
C9 C8 1.377(4) . ?
C9 H9 0.9300 . ?
C8 H8 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 O3 H3 109.5 . . ?
C6 O6 H6 109.5 . . ?
C1 O2 C4 108.49(16) . . ?
C5 O5 H5 109.5 . . ?
C3 O4 H4 109.5 . . ?
C3 C2 O3 128.5(2) . . ?
C3 C2 C1 108.07(19) . . ?
O3 C2 C1 123.34(19) . . ?
N1 C10 C11 123.3(2) . . ?
N1 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C10 C11 C7 119.5(2) . . ?
C10 C11 H11 120.2 . . ?
C7 C11 H11 120.2 . . ?
O7 C12 N2 121.2(2) . . ?
O7 C12 C7 120.3(2) . . ?
N2 C12 C7 118.53(19) . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C9 N1 C10 116.8(2) . . ?
C2 C3 O4 132.0(2) . . ?
C2 C3 C4 109.86(18) . . ?
O4 C3 C4 118.10(18) . . ?
O2 C4 C3 103.68(17) . . ?
O2 C4 C5 108.51(16) . . ?
C3 C4 C5 114.52(18) . . ?
O2 C4 H4A 106.0(13) . . ?
C3 C4 H4A 112.8(13) . . ?
C5 C4 H4A 110.6(13) . . ?
O5 C5 C6 106.22(16) . . ?
O5 C5 C4 111.48(18) . . ?
C6 C5 C4 111.80(19) . . ?
O5 C5 H5A 111.5(13) . . ?
C6 C5 H5A 108.3(12) . . ?
C4 C5 H5A 107.5(11) . . ?
O6 C6 C5 110.71(18) . . ?
O6 C6 H6B 110.7(13) . . ?
C5 C6 H6B 110.6(13) . . ?
O6 C6 H6A 109.0(13) . . ?
C5 C6 H6A 109.7(13) . . ?
H6B C6 H6A 106.1(17) . . ?
O1 C1 O2 120.8(2) . . ?
O1 C1 C2 129.5(2) . . ?
O2 C1 C2 109.64(18) . . ?
C11 C7 C8 117.5(2) . . ?
C11 C7 C12 123.6(2) . . ?
C8 C7 C12 118.9(2) . . ?
N1 C9 C8 123.7(2) . . ?
N1 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?

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
N1 C10 C11 C7 1.2(3) . . . . ?
C11 C10 N1 C9 -1.0(3) . . . . ?
O3 C2 C3 O4 -1.2(4) . . . . ?
C1 C2 C3 O4 -177.3(2) . . . . ?
O3 C2 C3 C4 176.6(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 O2 C4 C3 -4.8(2) . . . . ?
C1 O2 C4 C5 117.33(19) . . . . ?
C2 C3 C4 O2 2.6(2) . . . . ?
O4 C3 C4 O2 -179.29(17) . . . . ?
C2 C3 C4 C5 -115.5(2) . . . . ?
O4 C3 C4 C5 62.7(3) . . . . ?
O2 C4 C5 O5 -52.7(2) . . . . ?
C3 C4 C5 O5 62.6(2) . . . . ?
O2 C4 C5 C6 66.0(2) . . . . ?
C3 C4 C5 C6 -178.69(17) . . . . ?
O5 C5 C6 O6 -170.05(17) . . . . ?
C4 C5 C6 O6 68.1(2) . . . . ?
C4 O2 C1 O1 -175.7(2) . . . . ?
C4 O2 C1 C2 5.3(2) . . . . ?
C3 C2 C1 O1 177.5(2) . . . . ?
O3 C2 C1 O1 1.2(4) . . . . ?
C3 C2 C1 O2 -3.7(2) . . . . ?
O3 C2 C1 O2 180.00(18) . . . . ?
C10 C11 C7 C8 -0.6(3) . . . . ?
C10 C11 C7 C12 179.1(2) . . . . ?
O7 C12 C7 C11 -168.0(2) . . . . ?
N2 C12 C7 C11 12.3(3) . . . . ?
O7 C12 C7 C8 11.8(3) . . . . ?
N2 C12 C7 C8 -167.9(2) . . . . ?
C10 N1 C9 C8 0.3(4) . . . . ?
N1 C9 C8 C7 0.2(4) . . . . ?
C11 C7 C8 C9 0.0(4) . . . . ?
C12 C7 C8 C9 -179.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_VCINA2
_database_code_depnum_ccdc_archive 'CCDC 1505518'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            VCINA2
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 N4 O8'
_chemical_formula_weight         420.38

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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'

_cell_length_a                   8.9340(9)
_cell_length_b                   5.1587(5)
_cell_length_c                   43.225(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.000(7)
_cell_angle_gamma                90.00
_cell_volume                     1989.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2362
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9893
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15625
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6509
_reflns_number_gt                4764
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.0275P)²+0.1710P] 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     SHELXL
_refine_ls_extinction_coef       0.0046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(11)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6509
_refine_ls_number_parameters     554
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3827(2) 0.5046(5) 0.04939(5) 0.0262(6) Uani 1 1 d U . .
O2 O 0.5306(2) 0.8423(5) 0.03902(5) 0.0212(5) Uani 1 1 d . . .
O3 O 0.5102(3) 0.5599(5) 0.11478(5) 0.0311(7) Uani 1 1 d . . .
H3 H 0.4423 0.4579 0.1102 0.047 Uiso 1 1 calc R . .
O4 O 0.7212(3) 1.0185(5) 0.11076(5) 0.0244(6) Uani 1 1 d . . .
H4 H 0.6935 0.9744 0.1278 0.037 Uiso 1 1 calc R . .
O5 O 0.8522(3) 0.7566(4) 0.04204(5) 0.0247(6) Uani 1 1 d . . .
H5 H 0.8089 0.6622 0.0292 0.037 Uiso 1 1 calc R . .
O6 O 0.7130(3) 1.3670(5) 0.00940(5) 0.0327(7) Uani 1 1 d . . .
H6 H 0.6728 1.4059 -0.0075 0.049 Uiso 1 1 calc R . .
C6 C 0.7683(4) 1.1055(7) 0.00825(7) 0.0227(9) Uani 1 1 d . . .
H6A H 0.8645 1.1021 -0.0012 0.027 Uiso 1 1 calc R . .
H6B H 0.6988 0.9977 -0.0040 0.027 Uiso 1 1 calc R . .
C5 C 0.7843(4) 1.0065(7) 0.04110(7) 0.0183(8) Uani 1 1 d . . .
H5A H 0.8520 1.1248 0.0528 0.022 Uiso 1 1 calc R . .
C4 C 0.6357(3) 1.0091(8) 0.05652(7) 0.0200(8) Uani 1 1 d . . .
H4A H 0.5964 1.1865 0.0562 0.024 Uiso 1 1 calc R . .
C1 C 0.4754(4) 0.6648(7) 0.05887(8) 0.0206(8) Uani 1 1 d U . .
C2 C 0.5411(3) 0.7037(7) 0.08959(7) 0.0190(8) Uani 1 1 d . . .
C3 C 0.6348(3) 0.9067(7) 0.08862(7) 0.0178(9) Uani 1 1 d . . .
O7 O -0.1562(2) 0.8560(5) 0.45089(5) 0.0274(6) Uani 1 1 d . . .
O8 O -0.0023(2) 0.5195(5) 0.46091(5) 0.0222(6) Uani 1 1 d . . .
O9 O -0.0760(3) 0.7844(5) 0.38489(5) 0.0331(7) Uani 1 1 d . . .
H9 H -0.1371 0.8930 0.3899 0.050 Uiso 1 1 calc R . .
O10 O 0.1370(3) 0.3291(5) 0.38826(5) 0.0268(6) Uani 1 1 d . . .
H10 H 0.1132 0.3978 0.3716 0.040 Uiso 1 1 calc R . .
O11 O 0.3156(3) 0.6066(5) 0.45411(6) 0.0248(7) Uani 1 1 d . . .
O12 O 0.2072(3) -0.0037(5) 0.48952(6) 0.0352(7) Uani 1 1 d . . .
H12 H 0.1869 -0.0446 0.5072 0.053 Uiso 1 1 calc R . .
C12 C 0.2621(4) 0.2589(7) 0.48954(8) 0.0267(9) Uani 1 1 d . . .
H12A H 0.3656 0.2642 0.4975 0.032 Uiso 1 1 calc R . .
H12B H 0.2028 0.3670 0.5026 0.032 Uiso 1 1 calc R . .
C11 C 0.2501(4) 0.3567(7) 0.45639(7) 0.0210(8) Uani 1 1 d . . .
H11A H 0.3086 0.2384 0.4440 0.025 Uiso 1 1 calc R . .
C10 C 0.0902(3) 0.3487(7) 0.44303(7) 0.0193(8) Uani 1 1 d . . .
H10A H 0.0521 0.1710 0.4441 0.023 Uiso 1 1 calc R . .
C9 C 0.0670(4) 0.4467(6) 0.41074(8) 0.0196(9) Uani 1 1 d . . .
C8 C -0.0270(4) 0.6475(7) 0.41019(7) 0.0197(8) Uani 1 1 d . . .
C7 C -0.0713(4) 0.6943(7) 0.44126(8) 0.0217(8) Uani 1 1 d . . .
O15 O 0.3953(3) 0.8718(5) 0.34141(5) 0.0313(6) Uani 1 1 d . . .
N5 N 0.7258(3) 0.1638(6) 0.38566(7) 0.0277(8) Uani 1 1 d . . .
N6 N 0.3312(3) 0.8632(6) 0.39099(6) 0.0249(7) Uani 1 1 d . . .
H6C H 0.2663 0.9848 0.3880 0.030 Uiso 1 1 calc R . .
H6D H 0.3450 0.7947 0.4090 0.030 Uiso 1 1 calc R . .
C29 C 0.5675(3) 0.4939(7) 0.40490(7) 0.0216(8) Uani 1 1 d . . .
H29 H 0.5314 0.5805 0.4218 0.026 Uiso 1 1 calc R . .
C25 C 0.5205(4) 0.5648(7) 0.37496(8) 0.0224(9) Uani 1 1 d . . .
C30 C 0.4097(4) 0.7816(7) 0.36787(8) 0.0218(9) Uani 1 1 d . . .
C26 C 0.5801(4) 0.4339(7) 0.35051(8) 0.0275(10) Uani 1 1 d . . .
H26 H 0.5526 0.4778 0.3301 0.033 Uiso 1 1 calc R . .
C27 C 0.6811(4) 0.2368(8) 0.35704(8) 0.0338(10) Uani 1 1 d . . .
H27 H 0.7205 0.1495 0.3405 0.041 Uiso 1 1 calc R . .
C28 C 0.6687(4) 0.2922(7) 0.40914(8) 0.0270(9) Uani 1 1 d . . .
H28 H 0.6984 0.2440 0.4293 0.032 Uiso 1 1 calc R . .
O14 O 0.5490(3) 1.2859(5) 0.27292(6) 0.0404(7) Uani 1 1 d . . .
N4 N 0.5140(3) 0.8574(6) 0.27984(7) 0.0378(9) Uani 1 1 d . . .
H4B H 0.4881 0.8771 0.2986 0.045 Uiso 1 1 calc R . .
H4C H 0.5166 0.7048 0.2719 0.045 Uiso 1 1 calc R . .
N3 N 0.6608(3) 0.9515(6) 0.16878(7) 0.0293(8) Uani 1 1 d . . .
C20 C 0.5274(5) 0.8182(9) 0.21224(8) 0.0450(12) Uani 1 1 d . . .
H20 H 0.4598 0.7035 0.2205 0.054 Uiso 1 1 calc R . .
C19 C 0.5908(4) 1.0102(8) 0.23030(8) 0.0253(9) Uani 1 1 d . . .
C24 C 0.5500(4) 1.0631(8) 0.26316(8) 0.0275(9) Uani 1 1 d . . .
C23 C 0.6920(4) 1.1711(8) 0.21683(9) 0.0410(11) Uani 1 1 d . . .
H23 H 0.7386 1.3035 0.2283 0.049 Uiso 1 1 calc R . .
C22 C 0.7240(5) 1.1356(9) 0.18642(9) 0.0432(12) Uani 1 1 d . . .
H22 H 0.7931 1.2455 0.1778 0.052 Uiso 1 1 calc R . .
C21 C 0.5634(5) 0.7945(9) 0.18184(9) 0.0451(12) Uani 1 1 d . . .
H21 H 0.5181 0.6637 0.1699 0.054 Uiso 1 1 calc R . .
O16 O 0.0755(3) 0.8730(6) 0.22542(6) 0.0466(8) Uani 1 1 d . . .
N7 N 0.0954(3) 0.4807(7) 0.33154(7) 0.0340(8) Uani 1 1 d . . .
N8 N 0.0902(4) 0.4456(6) 0.21514(7) 0.0360(9) Uani 1 1 d . . .
H8A H 0.0868 0.4704 0.1954 0.043 Uiso 1 1 calc R . .
H8B H 0.0970 0.2908 0.2225 0.043 Uiso 1 1 calc R . .
C33 C 0.1746(4) 0.3424(8) 0.31256(8) 0.0356(10) Uani 1 1 d . . .
H33 H 0.2338 0.2090 0.3209 0.043 Uiso 1 1 calc R . .
C32 C 0.1744(4) 0.3848(8) 0.28095(8) 0.0366(11) Uani 1 1 d . . .
H32 H 0.2308 0.2791 0.2686 0.044 Uiso 1 1 calc R . .
C31 C 0.0913(4) 0.5824(7) 0.26804(8) 0.0243(9) Uani 1 1 d . . .
C36 C 0.0851(4) 0.6462(8) 0.23424(8) 0.0282(9) Uani 1 1 d . . .
C35 C 0.0107(5) 0.7335(9) 0.28768(9) 0.0515(13) Uani 1 1 d . . .
H35 H -0.0455 0.8732 0.2800 0.062 Uiso 1 1 calc R . .
C34 C 0.0145(6) 0.6750(10) 0.31874(10) 0.0601(15) Uani 1 1 d . . .
H34 H -0.0423 0.7760 0.3316 0.072 Uiso 1 1 calc R . .
O13 O -0.0246(3) 0.4962(5) 0.15363(5) 0.0330(6) Uani 1 1 d . . .
N1 N 0.2968(3) 1.1991(6) 0.11306(7) 0.0264(7) Uani 1 1 d . . .
N2 N -0.0957(3) 0.4918(6) 0.10291(6) 0.0245(7) Uani 1 1 d . . .
H2A H -0.1578 0.3666 0.1051 0.029 Uiso 1 1 calc R . .
H2B H -0.0856 0.5583 0.0849 0.029 Uiso 1 1 calc R . .
C15 C 0.2348(4) 1.0699(7) 0.08924(8) 0.0276(9) Uani 1 1 d . . .
H15 H 0.2603 1.1171 0.0694 0.033 Uiso 1 1 calc R . .
C13 C 0.0932(3) 0.8004(7) 0.12157(7) 0.0189(8) Uani 1 1 d . . .
C18 C -0.0152(4) 0.5828(7) 0.12737(8) 0.0202(8) Uani 1 1 d . . .
C17 C 0.1560(4) 0.9352(7) 0.14650(8) 0.0279(10) Uani 1 1 d . . .
H17 H 0.1306 0.8953 0.1665 0.034 Uiso 1 1 calc R . .
C16 C 0.2572(4) 1.1308(8) 0.14126(9) 0.0338(10) Uani 1 1 d . . .
H16 H 0.3000 1.2194 0.1583 0.041 Uiso 1 1 calc R . .
C14 C 0.1343(4) 0.8688(7) 0.09212(8) 0.0227(9) Uani 1 1 d . . .
H14 H 0.0951 0.7811 0.0747 0.027 Uiso 1 1 calc R . .
H11 H 0.280(4) 0.709(7) 0.4651(8) 0.026(13) 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
O1 C1 1.225(4) . ?
O2 C1 1.364(4) . ?
O2 C4 1.456(4) . ?
O3 C2 1.358(4) . ?
O3 H3 0.8200 . ?
O4 C3 1.329(4) . ?
O4 H4 0.8200 . ?
O5 C5 1.424(4) . ?
O5 H5 0.8200 . ?
O6 C6 1.438(4) . ?
O6 H6 0.8200 . ?
C6 C5 1.509(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 C4 1.517(4) . ?
C5 H5A 0.9800 . ?
C4 C3 1.485(4) . ?
C4 H4A 0.9800 . ?
C1 C2 1.438(4) . ?
C2 C3 1.343(4) . ?
O7 C7 1.216(4) . ?
O8 C7 1.364(4) . ?
O8 C10 1.457(4) . ?
O9 C8 1.355(4) . ?
O9 H9 0.8200 . ?
O10 C9 1.329(4) . ?
O10 H10 0.8200 . ?
O11 C11 1.421(4) . ?
O11 H11 0.79(4) . ?
O12 C12 1.441(4) . ?
O12 H12 0.8200 . ?
C12 C11 1.518(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.513(4) . ?
C11 H11A 0.9800 . ?
C10 C9 1.489(4) . ?
C10 H10A 0.9800 . ?
C9 C8 1.333(4) . ?
C8 C7 1.440(4) . ?
O15 C30 1.235(4) . ?
N5 C27 1.334(4) . ?
N5 C28 1.335(4) . ?
N6 C30 1.319(4) . ?
N6 H6C 0.8600 . ?
N6 H6D 0.8600 . ?
C29 C28 1.384(5) . ?
C29 C25 1.389(4) . ?
C29 H29 0.9300 . ?
C25 C26 1.384(5) . ?
C25 C30 1.514(5) . ?
C26 C27 1.379(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
O14 C24 1.225(4) . ?
N4 C24 1.332(5) . ?
N4 H4B 0.8600 . ?
N4 H4C 0.8600 . ?
N3 C22 1.325(4) . ?
N3 C21 1.336(5) . ?
C20 C19 1.366(5) . ?
C20 C21 1.374(5) . ?
C20 H20 0.9300 . ?
C19 C23 1.379(5) . ?
C19 C24 1.510(5) . ?
C23 C22 1.372(5) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
O16 C36 1.232(4) . ?
N7 C33 1.320(4) . ?
N7 C34 1.338(5) . ?
N8 C36 1.326(4) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
C33 C32 1.384(5) . ?
C33 H33 0.9300 . ?
C32 C31 1.363(5) . ?
C32 H32 0.9300 . ?
C31 C35 1.383(5) . ?
C31 C36 1.496(5) . ?
C35 C34 1.375(5) . ?
C35 H35 0.9300 . ?
C34 H34 0.9300 . ?
O13 C18 1.227(4) . ?
N1 C15 1.324(4) . ?
N1 C16 1.334(4) . ?
N2 C18 1.333(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C15 C14 1.382(5) . ?
C15 H15 0.9300 . ?
C13 C17 1.377(4) . ?
C13 C14 1.388(4) . ?
C13 C18 1.512(5) . ?
C17 C16 1.382(5) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C14 H14 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
C1 O2 C4 108.3(2) . . ?
C2 O3 H3 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 O5 H5 109.5 . . ?
C6 O6 H6 109.5 . . ?
O6 C6 C5 107.5(3) . . ?
O6 C6 H6A 110.2 . . ?
C5 C6 H6A 110.2 . . ?
O6 C6 H6B 110.2 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
O5 C5 C4 112.1(3) . . ?
O5 C5 C6 110.6(3) . . ?
C4 C5 C6 111.6(3) . . ?
O5 C5 H5A 107.4 . . ?
C4 C5 H5A 107.4 . . ?
C6 C5 H5A 107.4 . . ?
O2 C4 C3 103.9(3) . . ?
O2 C4 C5 108.8(3) . . ?
C3 C4 C5 117.1(3) . . ?
O2 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
O1 C1 O2 120.2(3) . . ?
O1 C1 C2 129.7(3) . . ?
O2 C1 C2 110.1(3) . . ?
C3 C2 O3 127.2(3) . . ?
C3 C2 C1 107.8(3) . . ?
O3 C2 C1 125.1(3) . . ?
O4 C3 C2 131.0(3) . . ?
O4 C3 C4 119.1(3) . . ?
C2 C3 C4 109.9(3) . . ?
C7 O8 C10 108.6(2) . . ?
C8 O9 H9 109.5 . . ?
C9 O10 H10 109.5 . . ?
C11 O11 H11 113(3) . . ?
C12 O12 H12 109.5 . . ?
O12 C12 C11 107.8(3) . . ?
O12 C12 H12A 110.2 . . ?
C11 C12 H12A 110.2 . . ?
O12 C12 H12B 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
O11 C11 C10 112.5(3) . . ?
O11 C11 C12 111.0(3) . . ?
C10 C11 C12 111.7(3) . . ?
O11 C11 H11A 107.1 . . ?
C10 C11 H11A 107.1 . . ?
C12 C11 H11A 107.1 . . ?
O8 C10 C9 103.7(3) . . ?
O8 C10 C11 109.3(3) . . ?
C9 C10 C11 115.5(3) . . ?
O8 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
O10 C9 C8 131.4(3) . . ?
O10 C9 C10 118.8(3) . . ?
C8 C9 C10 109.7(3) . . ?
C9 C8 O9 126.6(3) . . ?
C9 C8 C7 108.5(3) . . ?
O9 C8 C7 124.9(3) . . ?
O7 C7 O8 120.7(3) . . ?
O7 C7 C8 129.9(3) . . ?
O8 C7 C8 109.4(3) . . ?
C27 N5 C28 117.2(3) . . ?
C30 N6 H6C 120.0 . . ?
C30 N6 H6D 120.0 . . ?
H6C N6 H6D 120.0 . . ?
C28 C29 C25 119.0(3) . . ?
C28 C29 H29 120.5 . . ?
C25 C29 H29 120.5 . . ?
C26 C25 C29 118.3(3) . . ?
C26 C25 C30 118.7(3) . . ?
C29 C25 C30 123.1(3) . . ?
O15 C30 N6 123.2(3) . . ?
O15 C30 C25 120.1(3) . . ?
N6 C30 C25 116.8(3) . . ?
C27 C26 C25 118.5(3) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
N5 C27 C26 124.0(4) . . ?
N5 C27 H27 118.0 . . ?
C26 C27 H27 118.0 . . ?
N5 C28 C29 123.0(3) . . ?
N5 C28 H28 118.5 . . ?
C29 C28 H28 118.5 . . ?
C24 N4 H4B 120.0 . . ?
C24 N4 H4C 120.0 . . ?
H4B N4 H4C 120.0 . . ?
C22 N3 C21 117.3(3) . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C19 C23 117.2(3) . . ?
C20 C19 C24 123.8(3) . . ?
C23 C19 C24 119.0(3) . . ?
O14 C24 N4 123.7(3) . . ?
O14 C24 C19 120.0(3) . . ?
N4 C24 C19 116.3(3) . . ?
C22 C23 C19 119.9(4) . . ?
C22 C23 H23 120.1 . . ?
C19 C23 H23 120.1 . . ?
N3 C22 C23 122.9(4) . . ?
N3 C22 H22 118.6 . . ?
C23 C22 H22 118.5 . . ?
N3 C21 C20 122.7(4) . . ?
N3 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
C33 N7 C34 116.3(3) . . ?
C36 N8 H8A 120.0 . . ?
C36 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
N7 C33 C32 123.7(4) . . ?
N7 C33 H33 118.1 . . ?
C32 C33 H33 118.1 . . ?
C31 C32 C33 119.6(3) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C32 C31 C35 117.4(3) . . ?
C32 C31 C36 123.8(3) . . ?
C35 C31 C36 118.8(3) . . ?
O16 C36 N8 123.5(3) . . ?
O16 C36 C31 120.6(4) . . ?
N8 C36 C31 115.8(3) . . ?
C34 C35 C31 119.3(4) . . ?
C34 C35 H35 120.4 . . ?
C31 C35 H35 120.4 . . ?
N7 C34 C35 123.6(4) . . ?
N7 C34 H34 118.2 . . ?
C35 C34 H34 118.2 . . ?
C15 N1 C16 117.2(3) . . ?
C18 N2 H2A 120.0 . . ?
C18 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C15 C14 123.7(3) . . ?
N1 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
C17 C13 C14 118.2(3) . . ?
C17 C13 C18 118.9(3) . . ?
C14 C13 C18 122.9(3) . . ?
O13 C18 N2 123.1(3) . . ?
O13 C18 C13 119.9(3) . . ?
N2 C18 C13 117.0(3) . . ?
C13 C17 C16 118.9(3) . . ?
C13 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
N1 C16 C17 123.4(3) . . ?
N1 C16 H16 118.3 . . ?
C17 C16 H16 118.3 . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?

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
O6 C6 C5 O5 -174.5(2) . . . . ?
O6 C6 C5 C4 59.9(4) . . . . ?
C1 O2 C4 C3 0.2(3) . . . . ?
C1 O2 C4 C5 125.6(3) . . . . ?
O5 C5 C4 O2 -64.4(3) . . . . ?
C6 C5 C4 O2 60.4(4) . . . . ?
O5 C5 C4 C3 52.9(4) . . . . ?
C6 C5 C4 C3 177.7(3) . . . . ?
C4 O2 C1 O1 179.1(3) . . . . ?
C4 O2 C1 C2 -0.6(3) . . . . ?
O1 C1 C2 C3 -178.8(3) . . . . ?
O2 C1 C2 C3 0.8(4) . . . . ?
O1 C1 C2 O3 0.4(6) . . . . ?
O2 C1 C2 O3 180.0(3) . . . . ?
O3 C2 C3 O4 0.7(6) . . . . ?
C1 C2 C3 O4 179.9(3) . . . . ?
O3 C2 C3 C4 -179.8(3) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
O2 C4 C3 O4 179.8(3) . . . . ?
C5 C4 C3 O4 59.9(4) . . . . ?
O2 C4 C3 C2 0.3(4) . . . . ?
C5 C4 C3 C2 -119.6(3) . . . . ?
O12 C12 C11 O11 -174.4(3) . . . . ?
O12 C12 C11 C10 59.2(4) . . . . ?
C7 O8 C10 C9 0.3(3) . . . . ?
C7 O8 C10 C11 124.0(3) . . . . ?
O11 C11 C10 O8 -63.3(3) . . . . ?
C12 C11 C10 O8 62.2(4) . . . . ?
O11 C11 C10 C9 53.1(4) . . . . ?
C12 C11 C10 C9 178.7(3) . . . . ?
O8 C10 C9 O10 -179.7(3) . . . . ?
C11 C10 C9 O10 60.7(4) . . . . ?
O8 C10 C9 C8 -0.1(4) . . . . ?
C11 C10 C9 C8 -119.7(3) . . . . ?
O10 C9 C8 O9 0.5(6) . . . . ?
C10 C9 C8 O9 -179.1(3) . . . . ?
O10 C9 C8 C7 179.4(4) . . . . ?
C10 C9 C8 C7 -0.1(4) . . . . ?
C10 O8 C7 O7 179.2(3) . . . . ?
C10 O8 C7 C8 -0.4(4) . . . . ?
C9 C8 C7 O7 -179.2(4) . . . . ?
O9 C8 C7 O7 -0.2(6) . . . . ?
C9 C8 C7 O8 0.3(4) . . . . ?
O9 C8 C7 O8 179.3(3) . . . . ?
C28 C29 C25 C26 -1.5(5) . . . . ?
C28 C29 C25 C30 179.7(3) . . . . ?
C26 C25 C30 O15 -13.7(5) . . . . ?
C29 C25 C30 O15 165.0(3) . . . . ?
C26 C25 C30 N6 165.6(3) . . . . ?
C29 C25 C30 N6 -15.6(5) . . . . ?
C29 C25 C26 C27 1.1(5) . . . . ?
C30 C25 C26 C27 179.9(3) . . . . ?
C28 N5 C27 C26 -0.4(6) . . . . ?
C25 C26 C27 N5 -0.1(6) . . . . ?
C27 N5 C28 C29 -0.1(5) . . . . ?
C25 C29 C28 N5 1.0(5) . . . . ?
C21 C20 C19 C23 -1.1(6) . . . . ?
C21 C20 C19 C24 175.5(4) . . . . ?
C20 C19 C24 O14 -144.9(4) . . . . ?
C23 C19 C24 O14 31.6(5) . . . . ?
C20 C19 C24 N4 33.9(5) . . . . ?
C23 C19 C24 N4 -149.6(4) . . . . ?
C20 C19 C23 C22 0.6(6) . . . . ?
C24 C19 C23 C22 -176.2(4) . . . . ?
C21 N3 C22 C23 -0.8(6) . . . . ?
C19 C23 C22 N3 0.4(7) . . . . ?
C22 N3 C21 C20 0.2(6) . . . . ?
C19 C20 C21 N3 0.8(7) . . . . ?
C34 N7 C33 C32 -1.6(6) . . . . ?
N7 C33 C32 C31 1.4(6) . . . . ?
C33 C32 C31 C35 0.4(6) . . . . ?
C33 C32 C31 C36 179.2(4) . . . . ?
C32 C31 C36 O16 -144.3(4) . . . . ?
C35 C31 C36 O16 34.5(6) . . . . ?
C32 C31 C36 N8 35.9(5) . . . . ?
C35 C31 C36 N8 -145.3(4) . . . . ?
C32 C31 C35 C34 -1.7(7) . . . . ?
C36 C31 C35 C34 179.4(4) . . . . ?
C33 N7 C34 C35 0.1(7) . . . . ?
C31 C35 C34 N7 1.5(8) . . . . ?
C16 N1 C15 C14 -0.9(5) . . . . ?
C17 C13 C18 O13 -13.8(5) . . . . ?
C14 C13 C18 O13 165.3(3) . . . . ?
C17 C13 C18 N2 167.0(3) . . . . ?
C14 C13 C18 N2 -13.9(5) . . . . ?
C14 C13 C17 C16 -0.4(5) . . . . ?
C18 C13 C17 C16 178.8(3) . . . . ?
C15 N1 C16 C17 -0.2(5) . . . . ?
C13 C17 C16 N1 0.8(5) . . . . ?
N1 C15 C14 C13 1.3(5) . . . . ?
C17 C13 C14 C15 -0.6(5) . . . . ?
C18 C13 C14 C15 -179.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_VCNA
_database_code_depnum_ccdc_archive 'CCDC 1505519'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            VCNA
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N4 O14'
_chemical_formula_weight         596.49

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.0886(2)
_cell_length_b                   7.2518(3)
_cell_length_c                   17.1681(7)
_cell_angle_alpha                93.324(3)
_cell_angle_beta                 93.952(3)
_cell_angle_gamma                97.338(3)
_cell_volume                     625.42(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3674
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      25.96

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             310
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9893
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8089
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4194
_reflns_number_gt                3709
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.1209P)²+1.4273P] 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_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4194
_refine_ls_number_parameters     343
_refine_ls_number_restraints     256
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2003
_refine_ls_wR_factor_gt          0.1927
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.501
_refine_ls_shift/su_max          0.059
_refine_ls_shift/su_mean         0.003

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
O7 O -0.0393(4) 0.3014(3) -0.12871(12) 0.0179(4) Uani 1 1 d U . .
O14 O 1.3541(4) 0.8056(3) 0.91082(12) 0.0164(4) Uani 1 1 d U . .
O10 O 0.7629(4) 0.1376(3) 0.73223(11) 0.0146(4) Uani 1 1 d U . .
H10 H 0.8711 0.1962 0.7652 0.022 Uiso 1 1 calc R . .
O13 O 0.6722(4) 0.4356(3) 0.34205(12) 0.0202(4) Uani 1 1 d U . .
H13 H 0.5709 0.3438 0.3239 0.030 Uiso 1 1 calc R . .
O9 O 1.0703(4) 0.3225(3) 0.56595(11) 0.0141(4) Uani 1 1 d U . .
O12 O 0.5823(4) 0.4597(3) 0.51144(12) 0.0152(4) Uani 1 1 d U . .
H12 H 0.4375 0.4236 0.5274 0.023 Uiso 1 1 calc R . .
O11 O 0.4800(4) 0.0001(3) 0.57343(11) 0.0147(4) Uani 1 1 d U . .
H11 H 0.4197 -0.0349 0.6140 0.022 Uiso 1 1 calc R . .
O8 O 1.2420(4) 0.3821(3) 0.69030(11) 0.01280(15) Uani 1 1 d U . .
O6 O 0.1758(4) 0.8862(3) 0.43664(12) 0.0177(4) Uani 1 1 d U . .
H6 H 0.3020 0.9373 0.4657 0.027 Uiso 1 1 calc R . .
O2 O 0.2646(4) 0.7188(3) 0.20821(11) 0.0132(4) Uani 1 1 d U . .
O1 O 0.0682(4) 0.7120(3) 0.08641(12) 0.0159(4) Uani 1 1 d U . .
O5 O 0.3334(4) 1.0815(3) 0.30493(11) 0.0136(4) Uani 1 1 d U . .
H5 H 0.1804 1.0520 0.2859 0.020 Uiso 1 1 calc R . .
O3 O 0.5558(4) 0.9639(3) 0.05251(11) 0.0138(4) Uani 1 1 d U . .
H3 H 0.4392 0.9240 0.0181 0.021 Uiso 1 1 calc RD . .
O4 O 0.8648(4) 1.0326(3) 0.20752(12) 0.0146(4) Uani 1 1 d U . .
H4 H 0.9107 1.0871 0.1691 0.022 Uiso 1 1 calc RD . .
N2 N 0.3967(5) 0.3228(3) -0.14778(15) 0.0158(4) Uani 1 1 d U . .
H2A H 0.3648 0.3195 -0.1977 0.019 Uiso 1 1 calc R . .
H2B H 0.5578 0.3316 -0.1277 0.019 Uiso 1 1 calc R . .
N1 N 0.1255(5) 0.2244(4) 0.10807(14) 0.0143(4) Uani 1 1 d U . .
N3 N 1.1979(5) 0.8501(3) 0.67249(14) 0.01280(15) Uani 1 1 d U . .
N4 N 0.9176(5) 0.7817(3) 0.92879(15) 0.0162(4) Uani 1 1 d U . .
H4A H 0.9492 0.7908 0.9788 0.019 Uiso 1 1 calc R . .
H4B H 0.7564 0.7690 0.9085 0.019 Uiso 1 1 calc R . .
C12 C 0.1981(6) 0.3143(4) -0.10179(17) 0.01280(15) Uani 1 1 d U . .
C7 C 0.2642(6) 0.3218(4) -0.01563(16) 0.0126(4) Uani 1 1 d U . .
C11 C 0.4994(6) 0.4134(4) 0.02133(16) 0.0141(4) Uani 1 1 d U . .
H11A H 0.6272 0.4743 -0.0078 0.017 Uiso 1 1 calc R . .
C10 C 0.5433(6) 0.4138(4) 0.10181(17) 0.0152(4) Uani 1 1 d U . .
H10A H 0.6977 0.4781 0.1276 0.018 Uiso 1 1 calc R . .
C9 C 0.3527(6) 0.3165(4) 0.14330(17) 0.0149(4) Uani 1 1 d U . .
H9 H 0.3831 0.3150 0.1973 0.018 Uiso 1 1 calc R . .
C8 C 0.0810(6) 0.2279(4) 0.02986(16) 0.0154(4) Uani 1 1 d U . .
H8 H -0.0770 0.1656 0.0055 0.019 Uiso 1 1 calc R . .
C24 C 1.1159(6) 0.7872(4) 0.88318(16) 0.0128(4) Uani 1 1 d U . .
C19 C 1.0546(6) 0.7722(4) 0.79732(17) 0.01280(15) Uani 1 1 d U . .
C20 C 1.2395(6) 0.8600(4) 0.74970(16) 0.0117(4) Uani 1 1 d U . .
H20 H 1.3958 0.9271 0.7731 0.014 Uiso 1 1 calc R . .
C21 C 0.9734(6) 0.7536(4) 0.63700(17) 0.0132(4) Uani 1 1 d U . .
H21 H 0.9472 0.7469 0.5827 0.016 Uiso 1 1 calc R . .
C22 C 0.7801(6) 0.6638(4) 0.68030(16) 0.01280(15) Uani 1 1 d U . .
H22 H 0.6264 0.5971 0.6552 0.015 Uiso 1 1 calc R . .
C23 C 0.8189(6) 0.6747(4) 0.76103(16) 0.01280(15) Uani 1 1 d U . .
H23 H 0.6898 0.6179 0.7908 0.015 Uiso 1 1 calc R . .
C14 C 0.8261(6) 0.1840(4) 0.65961(16) 0.0124(4) Uani 1 1 d U . .
C15 C 0.6980(6) 0.1196(4) 0.59069(16) 0.0112(4) Uani 1 1 d U . .
C16 C 0.8447(6) 0.2017(4) 0.52566(16) 0.0118(4) Uani 1 1 d U . .
H16 H 0.9109 0.1016 0.4950 0.014 Uiso 1 1 calc R . .
C17 C 0.6790(6) 0.3080(4) 0.47093(16) 0.0122(4) Uani 1 1 d U . .
H17 H 0.5261 0.2218 0.4476 0.015 Uiso 1 1 calc R . .
C18 C 0.8385(6) 0.3848(4) 0.40476(17) 0.0161(4) Uani 1 1 d U . .
H18A H 0.9610 0.4930 0.4252 0.019 Uiso 1 1 calc R . .
H18B H 0.9424 0.2911 0.3854 0.019 Uiso 1 1 calc R . .
C13 C 1.0650(6) 0.3040(4) 0.64481(16) 0.01280(15) Uani 1 1 d U . .
C6 C 0.2717(6) 0.7906(4) 0.37189(16) 0.0137(4) Uani 1 1 d U . .
H6A H 0.1213 0.7278 0.3385 0.016 Uiso 1 1 calc R . .
H6B H 0.3736 0.6961 0.3911 0.016 Uiso 1 1 calc R . .
C5 C 0.4459(6) 0.9194(4) 0.32316(17) 0.0136(4) Uani 1 1 d U . .
H5A H 0.6135 0.9599 0.3547 0.016 Uiso 1 1 calc R . .
C4 C 0.5123(6) 0.8088(4) 0.24995(16) 0.0118(4) Uani 1 1 d U . .
H4D H 0.6238 0.7142 0.2651 0.014 Uiso 1 1 calc R . .
C1 C 0.2576(6) 0.7689(4) 0.13273(17) 0.0150(4) Uani 1 1 d U . .
C2 C 0.4967(6) 0.8896(4) 0.12042(16) 0.0125(4) Uani 1 1 d U . .
C3 C 0.6405(6) 0.9230(4) 0.18894(16) 0.0121(4) Uani 1 1 d 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
O7 C12 1.253(4) . ?
O14 C24 1.258(4) . ?
O10 C14 1.359(3) . ?
O10 H10 0.8200 . ?
O13 C18 1.418(4) . ?
O13 H13 0.8200 . ?
O9 C13 1.370(3) . ?
O9 C16 1.458(3) . ?
O12 C17 1.426(4) . ?
O12 H12 0.8200 . ?
O11 C15 1.323(3) . ?
O11 H11 0.8200 . ?
O8 C13 1.210(3) . ?
O6 C6 1.423(4) . ?
O6 H6 0.8200 . ?
O2 C1 1.365(4) . ?
O2 C4 1.463(3) . ?
O1 C1 1.219(3) . ?
O5 C5 1.414(4) . ?
O5 H5 0.8200 . ?
O3 C2 1.349(3) . ?
O3 H3 0.8200 . ?
O4 C3 1.313(3) . ?
O4 H4 0.8200 . ?
N2 C12 1.322(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N1 C9 1.345(4) . ?
N1 C8 1.349(4) . ?
N3 C20 1.324(4) . ?
N3 C21 1.348(4) . ?
N4 C24 1.318(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C12 C7 1.490(4) . ?
C7 C11 1.386(4) . ?
C7 C8 1.394(4) . ?
C11 C10 1.384(4) . ?
C11 H11A 0.9300 . ?
C10 C9 1.387(4) . ?
C10 H10A 0.9300 . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C24 C19 1.480(4) . ?
C19 C23 1.399(4) . ?
C19 C20 1.404(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C14 C15 1.340(4) . ?
C14 C13 1.448(4) . ?
C15 C16 1.496(4) . ?
C16 C17 1.526(4) . ?
C16 H16 0.9800 . ?
C17 C18 1.531(4) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C6 C5 1.530(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 C4 1.532(4) . ?
C5 H5A 0.9800 . ?
C4 C3 1.505(4) . ?
C4 H4D 0.9800 . ?
C1 C2 1.441(4) . ?
C2 C3 1.335(4) . ?

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 O10 H10 109.5 . . ?
C18 O13 H13 109.5 . . ?
C13 O9 C16 108.7(2) . . ?
C17 O12 H12 109.5 . . ?
C15 O11 H11 109.5 . . ?
C6 O6 H6 109.5 . . ?
C1 O2 C4 108.8(2) . . ?
C5 O5 H5 109.5 . . ?
C2 O3 H3 109.5 . . ?
C3 O4 H4 109.5 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C9 N1 C8 118.8(3) . . ?
C20 N3 C21 120.3(3) . . ?
C24 N4 H4A 120.0 . . ?
C24 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O7 C12 N2 121.9(3) . . ?
O7 C12 C7 120.2(3) . . ?
N2 C12 C7 117.9(3) . . ?
C11 C7 C8 118.4(3) . . ?
C11 C7 C12 123.7(3) . . ?
C8 C7 C12 117.9(2) . . ?
C10 C11 C7 119.7(3) . . ?
C10 C11 H11A 120.2 . . ?
C7 C11 H11A 120.2 . . ?
C11 C10 C9 118.8(3) . . ?
C11 C10 H10A 120.6 . . ?
C9 C10 H10A 120.6 . . ?
N1 C9 C10 122.2(3) . . ?
N1 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
N1 C8 C7 122.1(3) . . ?
N1 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
O14 C24 N4 121.7(3) . . ?
O14 C24 C19 119.7(3) . . ?
N4 C24 C19 118.6(3) . . ?
C23 C19 C20 118.1(3) . . ?
C23 C19 C24 122.9(3) . . ?
C20 C19 C24 119.0(2) . . ?
N3 C20 C19 122.0(3) . . ?
N3 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
N3 C21 C22 121.1(3) . . ?
N3 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C19 119.2(3) . . ?
C22 C23 H23 120.4 . . ?
C19 C23 H23 120.4 . . ?
C15 C14 O10 127.8(3) . . ?
C15 C14 C13 108.4(3) . . ?
O10 C14 C13 123.6(2) . . ?
O11 C15 C14 131.3(3) . . ?
O11 C15 C16 119.1(2) . . ?
C14 C15 C16 109.6(2) . . ?
O9 C16 C15 103.8(2) . . ?
O9 C16 C17 111.9(2) . . ?
C15 C16 C17 114.2(2) . . ?
O9 C16 H16 108.9 . . ?
C15 C16 H16 108.9 . . ?
C17 C16 H16 108.9 . . ?
O12 C17 C16 112.0(2) . . ?
O12 C17 C18 108.2(2) . . ?
C16 C17 C18 111.6(2) . . ?
O12 C17 H17 108.3 . . ?
C16 C17 H17 108.3 . . ?
C18 C17 H17 108.3 . . ?
O13 C18 C17 112.1(2) . . ?
O13 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
O13 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
O8 C13 O9 121.0(3) . . ?
O8 C13 C14 129.8(3) . . ?
O9 C13 C14 109.2(2) . . ?
O6 C6 C5 113.2(2) . . ?
O6 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
O6 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
O5 C5 C6 113.1(2) . . ?
O5 C5 C4 112.4(2) . . ?
C6 C5 C4 109.4(2) . . ?
O5 C5 H5A 107.2 . . ?
C6 C5 H5A 107.2 . . ?
C4 C5 H5A 107.2 . . ?
O2 C4 C3 102.8(2) . . ?
O2 C4 C5 108.8(2) . . ?
C3 C4 C5 115.6(2) . . ?
O2 C4 H4D 109.8 . . ?
C3 C4 H4D 109.8 . . ?
C5 C4 H4D 109.8 . . ?
O1 C1 O2 120.9(3) . . ?
O1 C1 C2 129.0(3) . . ?
O2 C1 C2 110.0(2) . . ?
C3 C2 O3 126.3(3) . . ?
C3 C2 C1 107.9(3) . . ?
O3 C2 C1 125.7(2) . . ?
O4 C3 C2 130.0(3) . . ?
O4 C3 C4 119.8(2) . . ?
C2 C3 C4 110.2(2) . . ?

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
O7 C12 C7 C11 -150.6(3) . . . . ?
N2 C12 C7 C11 29.0(4) . . . . ?
O7 C12 C7 C8 30.8(4) . . . . ?
N2 C12 C7 C8 -149.6(3) . . . . ?
C8 C7 C11 C10 -1.7(4) . . . . ?
C12 C7 C11 C10 179.7(3) . . . . ?
C7 C11 C10 C9 2.1(5) . . . . ?
C8 N1 C9 C10 -0.4(5) . . . . ?
C11 C10 C9 N1 -1.0(5) . . . . ?
C9 N1 C8 C7 0.8(5) . . . . ?
C11 C7 C8 N1 0.3(5) . . . . ?
C12 C7 C8 N1 178.9(3) . . . . ?
O14 C24 C19 C23 151.2(3) . . . . ?
N4 C24 C19 C23 -29.2(4) . . . . ?
O14 C24 C19 C20 -29.1(4) . . . . ?
N4 C24 C19 C20 150.6(3) . . . . ?
C21 N3 C20 C19 -0.1(4) . . . . ?
C23 C19 C20 N3 -1.1(4) . . . . ?
C24 C19 C20 N3 179.2(3) . . . . ?
C20 N3 C21 C22 0.5(4) . . . . ?
N3 C21 C22 C23 0.3(5) . . . . ?
C21 C22 C23 C19 -1.5(4) . . . . ?
C20 C19 C23 C22 1.8(4) . . . . ?
C24 C19 C23 C22 -178.4(3) . . . . ?
O10 C14 C15 O11 1.3(6) . . . . ?
C13 C14 C15 O11 176.4(3) . . . . ?
O10 C14 C15 C16 -177.3(3) . . . . ?
C13 C14 C15 C16 -2.1(3) . . . . ?
C13 O9 C16 C15 3.4(3) . . . . ?
C13 O9 C16 C17 127.0(3) . . . . ?
O11 C15 C16 O9 -179.4(2) . . . . ?
C14 C15 C16 O9 -0.7(3) . . . . ?
O11 C15 C16 C17 58.5(3) . . . . ?
C14 C15 C16 C17 -122.8(3) . . . . ?
O9 C16 C17 O12 -57.8(3) . . . . ?
C15 C16 C17 O12 59.7(3) . . . . ?
O9 C16 C17 C18 63.7(3) . . . . ?
C15 C16 C17 C18 -178.8(2) . . . . ?
O12 C17 C18 O13 -73.3(3) . . . . ?
C16 C17 C18 O13 163.1(2) . . . . ?
C16 O9 C13 O8 175.4(3) . . . . ?
C16 O9 C13 C14 -4.8(3) . . . . ?
C15 C14 C13 O8 -175.8(3) . . . . ?
O10 C14 C13 O8 -0.5(5) . . . . ?
C15 C14 C13 O9 4.4(3) . . . . ?
O10 C14 C13 O9 179.8(3) . . . . ?
O6 C6 C5 O5 -47.4(3) . . . . ?
O6 C6 C5 C4 -173.4(2) . . . . ?
C1 O2 C4 C3 2.1(3) . . . . ?
C1 O2 C4 C5 125.2(2) . . . . ?
O5 C5 C4 O2 -72.1(3) . . . . ?
C6 C5 C4 O2 54.3(3) . . . . ?
O5 C5 C4 C3 42.9(3) . . . . ?
C6 C5 C4 C3 169.4(2) . . . . ?
C4 O2 C1 O1 -179.4(3) . . . . ?
C4 O2 C1 C2 0.9(3) . . . . ?
O1 C1 C2 C3 176.3(3) . . . . ?
O2 C1 C2 C3 -4.0(3) . . . . ?
O1 C1 C2 O3 -0.2(5) . . . . ?
O2 C1 C2 O3 179.5(3) . . . . ?
O3 C2 C3 O4 0.7(5) . . . . ?
C1 C2 C3 O4 -175.8(3) . . . . ?
O3 C2 C3 C4 -178.2(3) . . . . ?
C1 C2 C3 C4 5.3(3) . . . . ?
O2 C4 C3 O4 176.3(2) . . . . ?
C5 C4 C3 O4 57.8(4) . . . . ?
O2 C4 C3 C2 -4.7(3) . . . . ?
C5 C4 C3 C2 -123.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.109
####################################################################### 
# 
# 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_2016234_0m
_database_code_depnum_ccdc_archive 'CCDC 1505520'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2016-07-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '3(C6 H6 N2 O), C6 H8 O6'
_chemical_formula_sum            'C24 H26 N6 O9'
_chemical_formula_weight         542.51
_chemical_absolute_configuration .
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.074(2)
_cell_length_b                   29.696(14)
_cell_length_c                   8.498(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.16(3)
_cell_angle_gamma                90
_cell_volume                     1246.9(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    679
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.57
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0967 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.7845.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1143
_diffrn_reflns_av_unetI/netI     0.1677
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9170
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                1926
_reflns_number_total             4135
_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.
;
_reflns_threshold_expression     'I > 2σ(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1890
_refine_ls_R_factor_gt           0.0825
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1299P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2024
_refine_ls_wR_factor_ref         0.2638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 O5, C5
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
C5 \\sim O5: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(O6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C4(H4A), C5(H5A)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C16(H16),
 C21(H21), C22(H22), C23(H23), C20(H20)
4.d Fitted hexagon refined as free rotating group:
 N5(C21,C22,C23,C19,C20)
4.e Tetrahedral OH refined with riding coordinates:
 O4(H4), O3(H3), O5(H5), O6(H6)
4.f X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4B,H4C), N6(H6C,H6D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N2 N 1.1043(11) 0.4889(2) 0.5760(8) 0.076(2) Uani 1 1 d . . . . .
H2A H 1.0853 0.5127 0.6302 0.091 Uiso 1 1 calc R . . . .
H2B H 1.2589 0.4757 0.5920 0.091 Uiso 1 1 calc R . . . .
O7 O 0.6665(9) 0.49011(16) 0.4390(7) 0.0690(18) Uani 1 1 d . . . . .
O8 O 1.0088(9) 0.57890(18) 0.7017(7) 0.0700(18) Uani 1 1 d . . . . .
O1 O 0.6192(9) 0.42902(16) 0.7710(6) 0.0562(15) Uani 1 1 d . . . . .
O4 O 1.3888(8) 0.33831(16) 0.9621(6) 0.0510(14) Uani 1 1 d . . . . .
H4 H 1.4660 0.3554 1.0338 0.077 Uiso 1 1 calc R . . . .
O3 O 1.1405(9) 0.42640(16) 1.0257(5) 0.0508(14) Uani 1 1 d . . . . .
H3 H 1.0390 0.4482 1.0141 0.076 Uiso 1 1 calc R . . . .
O5 O 0.7718(8) 0.28265(16) 0.9023(5) 0.0469(13) Uani 1 1 d . U . . .
H5 H 0.7443 0.3082 0.9319 0.070 Uiso 1 1 calc R . . . .
O6 O 0.8983(12) 0.2612(2) 0.5113(7) 0.096(2) Uani 1 1 d . U . . .
H6 H 0.8120 0.2493 0.4285 0.143 Uiso 1 1 calc R . . . .
O9 O 1.0171(8) 0.51110(16) 0.0341(7) 0.0619(17) Uani 1 1 d . . . . .
N1 N 0.7315(9) 0.37409(19) 0.1936(6) 0.0430(16) Uani 1 1 d . . . . .
N3 N 0.4772(14) 0.71148(19) 0.7085(9) 0.080(3) Uani 1 1 d . . . . .
N4 N 0.5773(11) 0.5769(2) 0.5725(8) 0.073(2) Uani 1 1 d . . . . .
H4B H 0.6002 0.5504 0.5369 0.088 Uiso 1 1 calc R . . . .
H4C H 0.4208 0.5895 0.5470 0.088 Uiso 1 1 calc R . . . .
O2 O 0.7524(8) 0.36175(14) 0.6901(5) 0.0467(13) Uani 1 1 d . . . . .
N6 N 0.5600(11) 0.5083(2) -0.0370(8) 0.067(2) Uani 1 1 d . U . . .
H6C H 0.5651 0.4842 -0.0926 0.081 Uiso 1 1 calc R . . . .
H6D H 0.4067 0.5198 -0.0317 0.081 Uiso 1 1 calc R . . . .
C12 C 0.8907(14) 0.4723(3) 0.4656(9) 0.055(2) Uani 1 1 d . . . . .
C7 C 0.9310(12) 0.4286(2) 0.3905(8) 0.046(2) Uani 1 1 d . . . . .
C8 C 0.7206(12) 0.4134(2) 0.2658(8) 0.044(2) Uani 1 1 d . . . . .
H8 H 0.5682 0.4314 0.2324 0.052 Uiso 1 1 calc R . . . .
C9 C 0.9505(12) 0.3484(2) 0.2393(8) 0.043(2) Uani 1 1 d . . . . .
H9 H 0.9582 0.3213 0.1856 0.052 Uiso 1 1 calc R . . . .
C10 C 1.1630(12) 0.3600(2) 0.3608(7) 0.0417(19) Uani 1 1 d . . . . .
H10 H 1.3080 0.3405 0.3955 0.050 Uiso 1 1 calc R . . . .
C11 C 1.1563(12) 0.4013(2) 0.4302(8) 0.047(2) Uani 1 1 d . . . . .
H11 H 1.3072 0.4112 0.5061 0.057 Uiso 1 1 calc R . . . .
C18 C 0.7773(13) 0.5977(2) 0.6641(8) 0.045(2) Uani 1 1 d . . . . .
C13 C 0.7454(13) 0.6435(2) 0.7161(8) 0.046(2) Uani 1 1 d . . . . .
C14 C 0.5102(15) 0.6694(3) 0.6578(9) 0.067(3) Uani 1 1 d . . . . .
H14 H 0.3708 0.6567 0.5803 0.080 Uiso 1 1 calc R . . . .
C15 C 0.6764(15) 0.7278(3) 0.8254(9) 0.065(3) Uani 1 1 d . . . . .
H15 H 0.6530 0.7560 0.8677 0.077 Uiso 1 1 calc R . . . .
C17 C 0.9476(15) 0.6627(3) 0.8336(9) 0.065(3) Uani 1 1 d . . . . .
H17 H 1.1059 0.6469 0.8764 0.078 Uiso 1 1 calc R . . . .
C16 C 0.9122(19) 0.7053(3) 0.8862(12) 0.095(3) Uani 1 1 d . . . . .
H16 H 1.0485 0.7189 0.9633 0.114 Uiso 1 1 calc R . . . .
C1 C 0.7894(13) 0.3989(2) 0.7945(8) 0.043(2) Uani 1 1 d . . . . .
C4 C 0.9917(12) 0.3325(2) 0.7388(8) 0.0394(19) Uani 1 1 d . . . . .
H4A H 1.0896 0.3318 0.6518 0.047 Uiso 1 1 calc R . . . .
C5 C 0.9088(13) 0.2852(2) 0.7710(8) 0.049(2) Uani 1 1 d . U . . .
H5A H 1.0751 0.2674 0.8030 0.059 Uiso 1 1 calc R . . . .
C6 C 0.7396(13) 0.2634(3) 0.6246(8) 0.053(2) Uani 1 1 d . . . . .
H6A H 0.6861 0.2334 0.6503 0.063 Uiso 1 1 calc R . . . .
H6B H 0.5777 0.2810 0.5830 0.063 Uiso 1 1 calc R . . . .
C3 C 1.1632(12) 0.3568(2) 0.8840(7) 0.0404(19) Uani 1 1 d . . . . .
C2 C 1.0495(13) 0.3964(2) 0.9062(8) 0.0433(19) Uani 1 1 d . . . . .
C24 C 0.7950(12) 0.5282(2) 0.0427(9) 0.052(2) Uani 1 1 d . . . . .
N5 N 1.0213(6) 0.62182(12) 0.3284(4) 0.076(2) Uani 1 1 d . . . . .
C21 C 0.8087(7) 0.65234(13) 0.2892(5) 0.080(3) Uani 1 1 d G . . . .
H21 H 0.8168 0.6794 0.3450 0.096 Uiso 1 1 calc R . . . .
C22 C 0.5840(7) 0.64236(18) 0.1666(6) 0.074(3) Uani 1 1 d G . . . .
H22 H 0.4418 0.6628 0.1404 0.089 Uiso 1 1 calc R . . . .
C23 C 0.5718(8) 0.6019(2) 0.0832(5) 0.066(3) Uani 1 1 d G . . . .
H23 H 0.4215 0.5952 0.0012 0.079 Uiso 1 1 calc R . . . .
C19 C 0.7844(9) 0.57135(16) 0.1224(5) 0.046(2) Uani 1 1 d G . . . .
C20 C 1.0091(8) 0.58132(12) 0.2450(5) 0.068(3) Uani 1 1 d G . . . .
H20 H 1.1514 0.5609 0.2712 0.082 Uiso 1 1 calc R . . . .


_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
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C12 1.355(8) . ?
O7 C12 1.228(8) . ?
O8 C18 1.274(8) . ?
O1 C1 1.228(8) . ?
O4 H4 0.8200 . ?
O4 C3 1.306(7) . ?
O3 H3 0.8200 . ?
O3 C2 1.351(8) . ?
O5 H5 0.8200 . ?
O5 C5 1.445(9) . ?
O6 H6 0.8200 . ?
O6 C6 1.390(9) . ?
O9 C24 1.253(8) . ?
N1 C8 1.326(9) . ?
N1 C9 1.331(8) . ?
N3 C14 1.345(10) . ?
N3 C15 1.336(9) . ?
N4 H4B 0.8600 . ?
N4 H4C 0.8600 . ?
N4 C18 1.287(8) . ?
O2 C1 1.400(8) . ?
O2 C4 1.474(7) . ?
N6 H6C 0.8600 . ?
N6 H6D 0.8600 . ?
N6 C24 1.365(8) . ?
C12 C7 1.481(10) . ?
C7 C8 1.397(8) . ?
C7 C11 1.379(9) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.356(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.364(9) . ?
C11 H11 0.9300 . ?
C18 C13 1.450(10) . ?
C13 C14 1.411(10) . ?
C13 C17 1.382(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.365(11) . ?
C17 H17 0.9300 . ?
C17 C16 1.366(11) . ?
C16 H16 0.9300 . ?
C1 C2 1.441(8) . ?
C4 H4A 0.9800 . ?
C4 C5 1.508(9) . ?
C4 C3 1.521(8) . ?
C5 H5A 0.9800 . ?
C5 C6 1.490(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 C2 1.342(9) . ?
C24 C19 1.457(8) . ?
N5 C21 1.3900 . ?
N5 C20 1.3900 . ?
C21 H21 0.9300 . ?
C21 C22 1.3900 . ?
C22 H22 0.9300 . ?
C22 C23 1.3900 . ?
C23 H23 0.9300 . ?
C23 C19 1.3900 . ?
C19 C20 1.3900 . ?
C20 H20 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
H2A N2 H2B 120.0 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
C3 O4 H4 109.5 . . ?
C2 O3 H3 109.5 . . ?
C5 O5 H5 109.5 . . ?
C6 O6 H6 109.5 . . ?
C8 N1 C9 119.3(5) . . ?
C15 N3 C14 116.5(7) . . ?
H4B N4 H4C 120.0 . . ?
C18 N4 H4B 120.0 . . ?
C18 N4 H4C 120.0 . . ?
C1 O2 C4 107.7(4) . . ?
H6C N6 H6D 120.0 . . ?
C24 N6 H6C 120.0 . . ?
C24 N6 H6D 120.0 . . ?
N2 C12 C7 116.7(6) . . ?
O7 C12 N2 122.2(7) . . ?
O7 C12 C7 120.8(6) . . ?
C8 C7 C12 117.0(6) . . ?
C11 C7 C12 126.8(6) . . ?
C11 C7 C8 116.3(6) . . ?
N1 C8 C7 122.0(6) . . ?
N1 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
N1 C9 H9 118.6 . . ?
N1 C9 C10 122.9(6) . . ?
C10 C9 H9 118.6 . . ?
C9 C10 H10 121.2 . . ?
C9 C10 C11 117.6(6) . . ?
C11 C10 H10 121.2 . . ?
C7 C11 H11 119.2 . . ?
C10 C11 C7 121.6(6) . . ?
C10 C11 H11 119.2 . . ?
O8 C18 N4 119.8(7) . . ?
O8 C18 C13 119.7(6) . . ?
N4 C18 C13 120.4(6) . . ?
C14 C13 C18 123.3(6) . . ?
C17 C13 C18 119.5(6) . . ?
C17 C13 C14 117.2(7) . . ?
N3 C14 C13 123.5(7) . . ?
N3 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N3 C15 H15 118.2 . . ?
N3 C15 C16 123.7(8) . . ?
C16 C15 H15 118.2 . . ?
C13 C17 H17 120.4 . . ?
C16 C17 C13 119.2(7) . . ?
C16 C17 H17 120.4 . . ?
C15 C16 C17 119.9(8) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
O1 C1 O2 118.9(5) . . ?
O1 C1 C2 130.4(6) . . ?
O2 C1 C2 110.3(5) . . ?
O2 C4 H4A 109.1 . . ?
O2 C4 C5 110.7(5) . . ?
O2 C4 C3 103.3(5) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 C3 115.2(5) . . ?
C3 C4 H4A 109.1 . . ?
O5 C5 C4 113.1(6) . . ?
O5 C5 H5A 107.1 . . ?
O5 C5 C6 109.6(5) . . ?
C4 C5 H5A 107.1 . . ?
C6 C5 C4 112.6(6) . . ?
C6 C5 H5A 107.1 . . ?
O6 C6 C5 106.5(6) . . ?
O6 C6 H6A 110.4 . . ?
O6 C6 H6B 110.4 . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
O4 C3 C4 119.1(6) . . ?
O4 C3 C2 130.7(6) . . ?
C2 C3 C4 110.2(5) . . ?
O3 C2 C1 124.5(6) . . ?
C3 C2 O3 126.8(5) . . ?
C3 C2 C1 108.1(5) . . ?
O9 C24 N6 119.5(7) . . ?
O9 C24 C19 120.8(5) . . ?
N6 C24 C19 119.4(6) . . ?
C21 N5 C20 120.0 . . ?
N5 C21 H21 120.0 . . ?
C22 C21 N5 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C19 C23 C22 120.0 . . ?
C19 C23 H23 120.0 . . ?
C23 C19 C24 124.8(4) . . ?
C23 C19 C20 120.0 . . ?
C20 C19 C24 115.2(4) . . ?
N5 C20 H20 120.0 . . ?
C19 C20 N5 120.0 . . ?
C19 C20 H20 120.0 . . ?

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
N2 C12 C7 C8 -174.1(7) . . . . ?
N2 C12 C7 C11 5.5(12) . . . . ?
O7 C12 C7 C8 12.4(11) . . . . ?
O7 C12 C7 C11 -168.1(8) . . . . ?
O8 C18 C13 C14 168.9(7) . . . . ?
O8 C18 C13 C17 -14.0(11) . . . . ?
O1 C1 C2 O3 9.6(12) . . . . ?
O1 C1 C2 C3 -178.8(8) . . . . ?
O4 C3 C2 O3 -4.1(12) . . . . ?
O4 C3 C2 C1 -175.5(7) . . . . ?
O5 C5 C6 O6 -171.6(5) . . . . ?
O9 C24 C19 C23 151.0(5) . . . . ?
O9 C24 C19 C20 -28.5(8) . . . . ?
N1 C9 C10 C11 -4.6(10) . . . . ?
N3 C15 C16 C17 -3.7(15) . . . . ?
N4 C18 C13 C14 -7.0(11) . . . . ?
N4 C18 C13 C17 170.1(7) . . . . ?
O2 C1 C2 O3 -177.5(6) . . . . ?
O2 C1 C2 C3 -5.8(8) . . . . ?
O2 C4 C5 O5 -62.1(6) . . . . ?
O2 C4 C5 C6 62.8(7) . . . . ?
O2 C4 C3 O4 176.9(5) . . . . ?
O2 C4 C3 C2 -4.9(7) . . . . ?
N6 C24 C19 C23 -22.6(9) . . . . ?
N6 C24 C19 C20 157.9(5) . . . . ?
C12 C7 C8 N1 -177.8(7) . . . . ?
C12 C7 C11 C10 175.0(7) . . . . ?
C8 N1 C9 C10 1.9(10) . . . . ?
C8 C7 C11 C10 -5.4(11) . . . . ?
C9 N1 C8 C7 -0.9(10) . . . . ?
C9 C10 C11 C7 6.4(11) . . . . ?
C11 C7 C8 N1 2.6(10) . . . . ?
C18 C13 C14 N3 178.4(8) . . . . ?
C18 C13 C17 C16 -177.7(8) . . . . ?
C13 C17 C16 C15 1.6(14) . . . . ?
C14 N3 C15 C16 4.3(13) . . . . ?
C14 C13 C17 C16 -0.5(12) . . . . ?
C15 N3 C14 C13 -3.1(13) . . . . ?
C17 C13 C14 N3 1.3(12) . . . . ?
C1 O2 C4 C5 125.1(6) . . . . ?
C1 O2 C4 C3 1.2(6) . . . . ?
C4 O2 C1 O1 176.4(6) . . . . ?
C4 O2 C1 C2 2.6(7) . . . . ?
C4 C5 C6 O6 61.6(8) . . . . ?
C4 C3 C2 O3 178.0(6) . . . . ?
C4 C3 C2 C1 6.5(8) . . . . ?
C5 C4 C3 O4 56.0(8) . . . . ?
C5 C4 C3 C2 -125.8(6) . . . . ?
C3 C4 C5 O5 54.6(7) . . . . ?
C3 C4 C5 C6 179.5(6) . . . . ?
C24 C19 C20 N5 179.5(5) . . . . ?
N5 C21 C22 C23 0.0 . . . . ?
C21 N5 C20 C19 0.0 . . . . ?
C21 C22 C23 C19 0.0 . . . . ?
C22 C23 C19 C24 -179.5(5) . . . . ?
C22 C23 C19 C20 0.0 . . . . ?
C23 C19 C20 N5 0.0 . . . . ?
C20 N5 C21 C22 0.0 . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2015514_0m
_database_code_depnum_ccdc_archive 'CCDC 1505521'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2016-07-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H8 O6, C6 H6 N2 O, C H4 O'
_chemical_formula_sum            'C13 H18 N2 O8'
_chemical_formula_weight         330.29
_chemical_absolute_configuration .
_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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.0892(3)
_cell_length_b                   7.5329(5)
_cell_length_c                   19.7851(12)
_cell_angle_alpha                84.757(4)
_cell_angle_beta                 85.752(4)
_cell_angle_gamma                81.727(4)
_cell_volume                     746.03(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5368
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.441
_cell_measurement_theta_min      2.741
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1019 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.8354.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9818
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.035
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4579
_reflns_number_total             4853
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.177
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       0.121(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.1080
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1573P)²+5.7268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3047
_refine_ls_wR_factor_ref         0.3099
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(2) 0(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 O1S-H1S
 0.95 with sigma of 0.001
 C1S-H1S
 1.9 with sigma of 0.02
 C1S-H1S
 1.9 with sigma of 0.001
 C1S-O1S
 1.54 with sigma of 0.02
 C1S-O1S
 1.45 with sigma of 0.001
4. Rigid bond restraints
 O2, C1, C2, O3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C20) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C4) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
6.a Ternary CH refined with riding coordinates:
 C4(H4A), C5(H5A), C16(H16), C17(H17)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C18(H18A,H18B)
6.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10A), C11(H11A), C8(H8), C21(H21), C22(H22), C23(H23), C20(H20)
6.d Tetrahedral OH refined with riding coordinates:
 O3(H3), O4(H4), O5(H5), O6(H6), O10(H10), O11(H11), O12(H12), O13(H13)
6.e X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4B,H4C)
6.f Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C1S(H1SA,H1SB,H1SC)
6.g Idealised tetrahedral OH refined as rotating group:
 O2S(H2S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.4593(8) 0.9818(6) 0.9783(2) 0.0255(11) Uani 1 1 d . . . . .
O3 O 0.9340(8) 0.7150(6) 1.0116(2) 0.0287(12) Uani 1 1 d . U . . .
H3 H 0.8151 0.7458 1.0402 0.043 Uiso 1 1 calc R . . . .
O4 O 1.2615(8) 0.7050(7) 0.8774(2) 0.0300(12) Uani 1 1 d . . . . .
H4 H 1.3078 0.6411 0.9114 0.045 Uiso 1 1 calc R . . . .
O5 O 0.7195(8) 0.6938(6) 0.7920(2) 0.0262(11) Uani 1 1 d . . . . .
H5 H 0.5813 0.7201 0.8151 0.039 Uiso 1 1 calc R . . . .
O6 O 0.8191(10) 1.1334(6) 0.7041(3) 0.0364(13) Uani 1 1 d . . . . .
H6 H 0.9630 1.0997 0.6846 0.055 Uiso 1 1 calc R . . . .
O2 O 0.6556(8) 1.0100(6) 0.8738(2) 0.0239(11) Uani 1 1 d . U . . .
C1 C 0.6441(12) 0.9367(8) 0.9400(3) 0.0264(15) Uani 1 1 d . U . . .
C2 C 0.8884(11) 0.8139(8) 0.9519(3) 0.0204(14) Uani 1 1 d . U . . .
C3 C 1.0360(11) 0.8073(7) 0.8919(3) 0.0156(13) Uani 1 1 d . . . . .
C4 C 0.9037(11) 0.9330(8) 0.8387(3) 0.0185(13) Uani 1 1 d . U . . .
H4A H 1.0130 1.0288 0.8251 0.022 Uiso 1 1 calc R . . . .
C5 C 0.8505(11) 0.8483(8) 0.7774(3) 0.0204(14) Uani 1 1 d . . . . .
H5A H 1.0230 0.8094 0.7540 0.025 Uiso 1 1 calc R . . . .
C6 C 0.6895(13) 0.9802(8) 0.7275(3) 0.0280(16) Uani 1 1 d . . . . .
H6A H 0.6591 0.9178 0.6886 0.034 Uiso 1 1 calc R . . . .
H6B H 0.5175 1.0213 0.7494 0.034 Uiso 1 1 calc R . . . .
O8 O 0.6676(9) 0.1634(6) 0.3191(2) 0.0297(12) Uani 1 1 d . . . . .
O10 O 0.1633(8) 0.4113(6) 0.2877(2) 0.0250(11) Uani 1 1 d . . . . .
H10 H 0.2667 0.3706 0.2573 0.037 Uiso 1 1 calc R . . . .
O11 O -0.0888(9) 0.4842(6) 0.4293(2) 0.0308(12) Uani 1 1 d . . . . .
H11 H -0.1633 0.5315 0.3956 0.046 Uiso 1 1 calc R . . . .
O12 O 0.0382(8) 0.0332(6) 0.4810(2) 0.0220(10) Uani 1 1 d . . . . .
H12 H -0.0398 -0.0316 0.5088 0.033 Uiso 1 1 calc R . . . .
O13 O 0.2087(9) -0.0417(6) 0.6188(2) 0.0295(12) Uani 1 1 d . . . . .
H13 H 0.1819 -0.1389 0.6071 0.044 Uiso 1 1 calc R . . . .
O9 O 0.5201(7) 0.1830(6) 0.4284(2) 0.0235(11) Uani 1 1 d . . . . .
C13 C 0.4941(11) 0.2263(8) 0.3610(3) 0.0189(12) Uani 1 1 d . U . . .
C14 C 0.2544(11) 0.3446(7) 0.3492(3) 0.0190(12) Uani 1 1 d . U . . .
C15 C 0.1288(12) 0.3841(8) 0.4106(3) 0.0248(16) Uani 1 1 d . . . . .
C16 C 0.2930(11) 0.2846(8) 0.4657(3) 0.0199(14) Uani 1 1 d . . . . .
H16 H 0.3594 0.3718 0.4916 0.024 Uiso 1 1 calc R . . . .
C17 C 0.1468(11) 0.1572(8) 0.5148(3) 0.0219(15) Uani 1 1 d . . . . .
H17 H 0.0040 0.2282 0.5407 0.026 Uiso 1 1 calc R . . . .
C18 C 0.3447(12) 0.0507(9) 0.5648(3) 0.0295(17) Uani 1 1 d . . . . .
H18A H 0.4688 -0.0352 0.5406 0.035 Uiso 1 1 calc R . . . .
H18B H 0.4457 0.1332 0.5831 0.035 Uiso 1 1 calc R . . . .
O7 O 0.7515(8) 0.8245(7) 0.1331(2) 0.0329(13) Uani 1 1 d . . . . .
N1 N 0.6113(10) 0.6805(7) 0.3402(3) 0.0265(13) Uani 1 1 d . . . . .
N2 N 0.3162(10) 0.8559(8) 0.1176(3) 0.0272(14) Uani 1 1 d . . . . .
H2A H 0.3423 0.8761 0.0743 0.033 Uiso 1 1 calc R . . . .
H2B H 0.1571 0.8557 0.1356 0.033 Uiso 1 1 calc R . . . .
C9 C 0.3854(13) 0.7667(8) 0.3700(3) 0.0257(16) Uani 1 1 d . . . . .
H9 H 0.3606 0.7534 0.4171 0.031 Uiso 1 1 calc R . . . .
C10 C 0.1982(12) 0.8693(7) 0.3352(3) 0.0253(15) Uani 1 1 d . . . . .
H10A H 0.0480 0.9265 0.3581 0.030 Uiso 1 1 calc R . . . .
C11 C 0.2266(12) 0.8915(9) 0.2640(4) 0.0290(17) Uani 1 1 d . . . . .
H11A H 0.0935 0.9583 0.2389 0.035 Uiso 1 1 calc R . . . .
C7 C 0.4619(12) 0.8096(7) 0.2318(3) 0.0212(14) Uani 1 1 d . . . . .
C8 C 0.6474(11) 0.7019(7) 0.2723(3) 0.0191(14) Uani 1 1 d . . . . .
H8 H 0.8010 0.6433 0.2513 0.023 Uiso 1 1 calc R . . . .
C12 C 0.5196(11) 0.8255(8) 0.1563(3) 0.0229(15) Uani 1 1 d . . . . .
O14 O 0.3751(8) 0.3126(6) 0.1640(2) 0.0271(11) Uani 1 1 d . . . . .
N3 N 0.5226(9) 0.4787(6) -0.0395(3) 0.0226(13) Uani 1 1 d . . . . .
N4 N 0.8139(10) 0.2804(8) 0.1796(3) 0.0301(15) Uani 1 1 d . . . . .
H4B H 0.7875 0.2648 0.2231 0.036 Uiso 1 1 calc R . . . .
H4C H 0.9733 0.2781 0.1616 0.036 Uiso 1 1 calc R . . . .
C21 C 0.7434(11) 0.4006(8) -0.0710(3) 0.0201(14) Uani 1 1 d . . . . .
H21 H 0.7661 0.4227 -0.1179 0.024 Uiso 1 1 calc R . . . .
C22 C 0.9424(11) 0.2876(7) -0.0375(3) 0.0198(14) Uani 1 1 d . . . . .
H22 H 1.0964 0.2367 -0.0607 0.024 Uiso 1 1 calc R . . . .
C23 C 0.8987(11) 0.2546(8) 0.0329(3) 0.0201(6) Uani 1 1 d . U . . .
H23 H 1.0255 0.1793 0.0574 0.024 Uiso 1 1 calc R . . . .
C19 C 0.6663(11) 0.3337(8) 0.0665(3) 0.0227(15) Uani 1 1 d . . . . .
C20 C 0.4841(12) 0.4434(8) 0.0274(3) 0.0261(6) Uani 1 1 d . U . . .
H20 H 0.3267 0.4952 0.0488 0.031 Uiso 1 1 calc R . . . .
C24 C 0.6097(12) 0.3079(8) 0.1406(3) 0.0211(6) Uani 1 1 d . U . . .
O2S O 1.1507(13) 0.6209(8) 0.5922(4) 0.065(2) Uani 1 1 d . . . . .
H2S H 1.2287 0.5361 0.6151 0.097 Uiso 1 1 calc GR . . . .
C2S C 0.874(2) 0.6071(13) 0.5959(6) 0.079(3) Uani 1 1 d . . . . .
H2SA H 0.8143 0.5782 0.6423 0.119 Uiso 1 1 calc GR . . . .
H2SB H 0.8426 0.5140 0.5686 0.119 Uiso 1 1 calc GR . . . .
H2SC H 0.7770 0.7197 0.5793 0.119 Uiso 1 1 calc GR . . . .
C1S C 0.27873(4) 0.40135(4) 0.75486(3) 0.052(2) Uani 1 1 d D . . . .
H1SA H 0.3470 0.5080 0.7646 0.078 Uiso 1 1 calc GR . . . .
H1SB H 0.3480 0.3020 0.7853 0.078 Uiso 1 1 calc GR . . . .
H1SC H 0.0881 0.4200 0.7606 0.078 Uiso 1 1 calc GR . . . .
O1S O 0.35901(10) 0.36222(12) 0.68532(4) 0.0549(18) Uani 1 1 d D . . . .
H1S H 0.53836(13) 0.3854(3) 0.68074(5) 0.082 Uiso 1 1 d DR . . . .


_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 C1 1.193(7) . ?
O3 H3 0.8200 . ?
O3 C2 1.355(7) . ?
O4 H4 0.8200 . ?
O4 C3 1.316(7) . ?
O5 H5 0.8200 . ?
O5 C5 1.420(7) . ?
O6 H6 0.8200 . ?
O6 C6 1.434(8) . ?
O2 C1 1.375(8) . ?
O2 C4 1.465(6) . ?
C1 C2 1.459(8) . ?
C2 C3 1.358(8) . ?
C3 C4 1.482(7) . ?
C4 H4A 0.9800 . ?
C4 C5 1.481(9) . ?
C5 H5A 0.9800 . ?
C5 C6 1.530(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O8 C13 1.239(7) . ?
O10 H10 0.8200 . ?
O10 C14 1.361(7) . ?
O11 H11 0.8200 . ?
O11 C15 1.297(7) . ?
O12 H12 0.8200 . ?
O12 C17 1.393(8) . ?
O13 H13 0.8200 . ?
O13 C18 1.413(7) . ?
O9 C13 1.355(7) . ?
O9 C16 1.479(7) . ?
C13 C14 1.424(7) . ?
C14 C15 1.368(9) . ?
C15 C16 1.500(8) . ?
C16 H16 0.9800 . ?
C16 C17 1.533(8) . ?
C17 H17 0.9800 . ?
C17 C18 1.551(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O7 C12 1.233(7) . ?
N1 C9 1.359(8) . ?
N1 C8 1.342(8) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C12 1.315(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.330(9) . ?
C10 H10A 0.9300 . ?
C10 C11 1.402(10) . ?
C11 H11A 0.9300 . ?
C11 C7 1.402(8) . ?
C7 C8 1.401(8) . ?
C7 C12 1.498(9) . ?
C8 H8 0.9300 . ?
O14 C24 1.245(7) . ?
N3 C21 1.330(7) . ?
N3 C20 1.332(8) . ?
N4 H4B 0.8600 . ?
N4 H4C 0.8600 . ?
N4 C24 1.322(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.398(8) . ?
C23 H23 0.9300 . ?
C23 C19 1.397(8) . ?
C19 C20 1.383(8) . ?
C19 C24 1.473(9) . ?
C20 H20 0.9300 . ?
O2S H2S 0.8200 . ?
O2S C2S 1.426(13) . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 0.9600 . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C1S O1S 1.4502(8) . ?
O1S H1S 0.9500(10) . ?

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 O3 H3 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 O5 H5 109.5 . . ?
C6 O6 H6 109.5 . . ?
C1 O2 C4 109.4(4) . . ?
O1 C1 O2 120.8(5) . . ?
O1 C1 C2 130.2(6) . . ?
O2 C1 C2 108.9(5) . . ?
O3 C2 C1 123.4(5) . . ?
O3 C2 C3 128.8(5) . . ?
C3 C2 C1 107.5(5) . . ?
O4 C3 C2 128.8(5) . . ?
O4 C3 C4 120.7(5) . . ?
C2 C3 C4 110.5(5) . . ?
O2 C4 C3 103.5(4) . . ?
O2 C4 H4A 109.1 . . ?
O2 C4 C5 111.2(5) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 C3 114.7(5) . . ?
C5 C4 H4A 109.1 . . ?
O5 C5 C4 113.7(5) . . ?
O5 C5 H5A 107.3 . . ?
O5 C5 C6 108.6(5) . . ?
C4 C5 H5A 107.3 . . ?
C4 C5 C6 112.4(5) . . ?
C6 C5 H5A 107.3 . . ?
O6 C6 C5 112.9(5) . . ?
O6 C6 H6A 109.0 . . ?
O6 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C14 O10 H10 109.5 . . ?
C15 O11 H11 109.5 . . ?
C17 O12 H12 109.5 . . ?
C18 O13 H13 109.5 . . ?
C13 O9 C16 107.8(4) . . ?
O8 C13 O9 120.0(5) . . ?
O8 C13 C14 128.9(5) . . ?
O9 C13 C14 111.2(5) . . ?
O10 C14 C13 126.7(5) . . ?
O10 C14 C15 124.7(5) . . ?
C15 C14 C13 108.6(5) . . ?
O11 C15 C14 134.4(6) . . ?
O11 C15 C16 117.4(5) . . ?
C14 C15 C16 108.2(5) . . ?
O9 C16 C15 104.1(4) . . ?
O9 C16 H16 109.1 . . ?
O9 C16 C17 110.7(4) . . ?
C15 C16 H16 109.1 . . ?
C15 C16 C17 114.7(5) . . ?
C17 C16 H16 109.1 . . ?
O12 C17 C16 112.2(5) . . ?
O12 C17 H17 109.1 . . ?
O12 C17 C18 108.0(5) . . ?
C16 C17 H17 109.1 . . ?
C16 C17 C18 109.4(5) . . ?
C18 C17 H17 109.1 . . ?
O13 C18 C17 111.0(5) . . ?
O13 C18 H18A 109.4 . . ?
O13 C18 H18B 109.4 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C8 N1 C9 118.0(5) . . ?
H2A N2 H2B 120.0 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
N1 C9 H9 118.3 . . ?
C10 C9 N1 123.3(6) . . ?
C10 C9 H9 118.3 . . ?
C9 C10 H10A 119.9 . . ?
C9 C10 C11 120.1(6) . . ?
C11 C10 H10A 119.9 . . ?
C10 C11 H11A 121.0 . . ?
C7 C11 C10 117.9(6) . . ?
C7 C11 H11A 121.0 . . ?
C11 C7 C12 123.4(5) . . ?
C8 C7 C11 118.1(6) . . ?
C8 C7 C12 118.5(5) . . ?
N1 C8 C7 122.3(5) . . ?
N1 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
O7 C12 N2 122.6(6) . . ?
O7 C12 C7 119.4(5) . . ?
N2 C12 C7 117.8(5) . . ?
C21 N3 C20 118.7(5) . . ?
H4B N4 H4C 120.0 . . ?
C24 N4 H4B 120.0 . . ?
C24 N4 H4C 120.0 . . ?
N3 C21 H21 118.2 . . ?
N3 C21 C22 123.6(6) . . ?
C22 C21 H21 118.2 . . ?
C21 C22 H22 121.7 . . ?
C21 C22 C23 116.5(5) . . ?
C23 C22 H22 121.7 . . ?
C22 C23 H23 119.7 . . ?
C19 C23 C22 120.5(5) . . ?
C19 C23 H23 119.7 . . ?
C23 C19 C24 123.5(5) . . ?
C20 C19 C23 117.2(6) . . ?
C20 C19 C24 119.3(5) . . ?
N3 C20 C19 123.4(5) . . ?
N3 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
O14 C24 N4 122.7(6) . . ?
O14 C24 C19 119.5(5) . . ?
N4 C24 C19 117.8(5) . . ?
C2S O2S H2S 109.5 . . ?
O2S C2S H2SA 109.5 . . ?
O2S C2S H2SB 109.5 . . ?
O2S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
C1S O1S H1S 102.68(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
O1 C1 C2 O3 5.8(11) . . . . ?
O1 C1 C2 C3 179.9(7) . . . . ?
O3 C2 C3 O4 -1.1(11) . . . . ?
O3 C2 C3 C4 176.8(6) . . . . ?
O4 C3 C4 O2 176.2(5) . . . . ?
O4 C3 C4 C5 54.9(7) . . . . ?
O5 C5 C6 O6 -174.1(5) . . . . ?
O2 C1 C2 O3 -177.4(5) . . . . ?
O2 C1 C2 C3 -3.4(7) . . . . ?
O2 C4 C5 O5 -66.6(6) . . . . ?
O2 C4 C5 C6 57.3(6) . . . . ?
C1 O2 C4 C3 -0.2(6) . . . . ?
C1 O2 C4 C5 123.4(5) . . . . ?
C1 C2 C3 O4 -174.7(6) . . . . ?
C1 C2 C3 C4 3.2(7) . . . . ?
C2 C3 C4 O2 -1.9(6) . . . . ?
C2 C3 C4 C5 -123.2(6) . . . . ?
C3 C4 C5 O5 50.4(6) . . . . ?
C3 C4 C5 C6 174.3(5) . . . . ?
C4 O2 C1 O1 179.3(6) . . . . ?
C4 O2 C1 C2 2.2(7) . . . . ?
C4 C5 C6 O6 59.2(7) . . . . ?
O8 C13 C14 O10 1.4(11) . . . . ?
O8 C13 C14 C15 -177.7(6) . . . . ?
O10 C14 C15 O11 -0.2(12) . . . . ?
O10 C14 C15 C16 -179.9(5) . . . . ?
O11 C15 C16 O9 179.2(5) . . . . ?
O11 C15 C16 C17 58.1(7) . . . . ?
O12 C17 C18 O13 -69.0(6) . . . . ?
O9 C13 C14 O10 -178.4(5) . . . . ?
O9 C13 C14 C15 2.5(7) . . . . ?
O9 C16 C17 O12 -62.3(6) . . . . ?
O9 C16 C17 C18 57.5(6) . . . . ?
C13 O9 C16 C15 2.5(6) . . . . ?
C13 O9 C16 C17 126.2(5) . . . . ?
C13 C14 C15 O11 179.0(7) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
C14 C15 C16 O9 -1.1(6) . . . . ?
C14 C15 C16 C17 -122.2(6) . . . . ?
C15 C16 C17 O12 55.2(6) . . . . ?
C15 C16 C17 C18 174.9(5) . . . . ?
C16 O9 C13 O8 177.0(5) . . . . ?
C16 O9 C13 C14 -3.1(6) . . . . ?
C16 C17 C18 O13 168.6(5) . . . . ?
N1 C9 C10 C11 0.7(10) . . . . ?
C9 N1 C8 C7 0.2(9) . . . . ?
C9 C10 C11 C7 -2.9(10) . . . . ?
C10 C11 C7 C8 3.7(9) . . . . ?
C10 C11 C7 C12 -178.8(6) . . . . ?
C11 C7 C8 N1 -2.5(9) . . . . ?
C11 C7 C12 O7 148.0(6) . . . . ?
C11 C7 C12 N2 -26.1(9) . . . . ?
C8 N1 C9 C10 0.8(9) . . . . ?
C8 C7 C12 O7 -34.5(9) . . . . ?
C8 C7 C12 N2 151.3(6) . . . . ?
C12 C7 C8 N1 180.0(6) . . . . ?
N3 C21 C22 C23 1.3(9) . . . . ?
C21 N3 C20 C19 2.1(10) . . . . ?
C21 C22 C23 C19 -0.4(9) . . . . ?
C22 C23 C19 C20 0.4(9) . . . . ?
C22 C23 C19 C24 -178.7(6) . . . . ?
C23 C19 C20 N3 -1.3(10) . . . . ?
C23 C19 C24 O14 -149.6(6) . . . . ?
C23 C19 C24 N4 30.4(9) . . . . ?
C20 N3 C21 C22 -2.1(9) . . . . ?
C20 C19 C24 O14 31.3(9) . . . . ?
C20 C19 C24 N4 -148.7(6) . . . . ?
C24 C19 C20 N3 177.9(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(2)
2 0(2)

####################################################################### 
# 
# 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_2016507_0m
_database_code_depnum_ccdc_archive 'CCDC 1505522'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2016-09-14
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C O2, C6 H7 N2 O'
_chemical_formula_sum            'C7 H7 N2 O3'
_chemical_formula_weight         167.15
_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'

_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.
;
_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_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                   7.2149(4)
_cell_length_b                   12.4451(7)
_cell_length_c                   15.6775(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1407.69(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    701
_cell_measurement_temperature    170
_cell_measurement_theta_max      22.198
_cell_measurement_theta_min      3.274
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0831 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.8712.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9098
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.068
_diffrn_reflns_theta_max         25.068
_diffrn_reflns_theta_min         2.598
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                883
_reflns_number_total             1256
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.9232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2-H2
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C3(H3), C5(H5)
3.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.035
;
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
O2 O 0.5157(3) 0.64013(14) 0.51364(10) 0.0276(5) Uani 1 1 d . . . . .
O1 O 0.5697(3) 0.48974(14) 0.88571(10) 0.0302(5) Uani 1 1 d . . . . .
O3 O 0.4282(3) 0.54498(14) 0.40041(10) 0.0301(5) Uani 1 1 d . . . . .
N2 N 0.6135(3) 0.67392(16) 0.66842(12) 0.0205(5) Uani 1 1 d D . . . .
N1 N 0.5169(3) 0.63752(17) 0.96592(11) 0.0245(5) Uani 1 1 d . . . . .
H1A H 0.4878 0.5998 1.0115 0.029 Uiso 1 1 calc R . . . .
H1B H 0.5151 0.7082 0.9680 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5777(3) 0.61581(18) 0.73842(13) 0.0181(5) Uani 1 1 d . . . . .
H1 H 0.5309 0.5448 0.7329 0.022 Uiso 1 1 calc R . . . .
C2 C 0.6085(3) 0.65848(19) 0.81917(13) 0.0179(5) Uani 1 1 d . . . . .
C6 C 0.5634(3) 0.58806(19) 0.89442(14) 0.0197(6) Uani 1 1 d . . . . .
C4 C 0.7172(3) 0.81982(19) 0.75215(14) 0.0221(6) Uani 1 1 d . . . . .
H4 H 0.7666 0.8904 0.7558 0.026 Uiso 1 1 calc R . . . .
C7 C 0.4832(3) 0.55206(19) 0.47431(14) 0.0206(6) Uani 1 1 d . . . . .
C3 C 0.6785(3) 0.7623(2) 0.82512(14) 0.0200(6) Uani 1 1 d . . . . .
H3 H 0.6997 0.7937 0.8795 0.024 Uiso 1 1 calc R . . . .
C5 C 0.6833(3) 0.7737(2) 0.67369(14) 0.0210(6) Uani 1 1 d . . . . .
H5 H 0.7096 0.8128 0.6231 0.025 Uiso 1 1 calc R . . . .
H2 H 0.586(4) 0.642(3) 0.6165(14) 0.065(11) Uiso 1 1 d 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
O2 C7 1.279(3) . ?
O1 C6 1.232(3) . ?
O3 C7 1.228(3) . ?
N2 C1 1.339(3) . ?
N2 C5 1.342(3) . ?
N2 H2 0.924(17) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C6 1.322(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(3) . ?
C2 C6 1.505(3) . ?
C2 C3 1.391(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.378(3) . ?
C4 C5 1.379(3) . ?
C7 C7 1.545(5) 5_666 ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?

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
C1 N2 C5 121.4(2) . . ?
C1 N2 H2 117(2) . . ?
C5 N2 H2 122(2) . . ?
H1A N1 H1B 120.0 . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
N2 C1 H1 119.7 . . ?
N2 C1 C2 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C6 117.2(2) . . ?
C1 C2 C3 118.3(2) . . ?
C3 C2 C6 124.5(2) . . ?
O1 C6 N1 124.5(2) . . ?
O1 C6 C2 118.9(2) . . ?
N1 C6 C2 116.6(2) . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
O2 C7 C7 116.0(2) . 5_666 ?
O3 C7 O2 125.1(2) . . ?
O3 C7 C7 118.9(3) . 5_666 ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
N2 C5 C4 120.4(2) . . ?
N2 C5 H5 119.8 . . ?
C4 C5 H5 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
N2 C1 C2 C6 179.6(2) . . . . ?
N2 C1 C2 C3 -0.5(3) . . . . ?
C1 N2 C5 C4 -1.1(4) . . . . ?
C1 C2 C6 O1 26.9(3) . . . . ?
C1 C2 C6 N1 -152.3(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C6 C2 C3 C4 179.3(2) . . . . ?
C3 C2 C6 O1 -153.1(2) . . . . ?
C3 C2 C6 N1 27.7(4) . . . . ?
C3 C4 C5 N2 0.0(4) . . . . ?
C5 N2 C1 C2 1.4(4) . . . . ?
C5 C4 C3 C2 0.9(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
