# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_sam12_p21byc
_database_code_depnum_ccdc_archive 'CCDC 1408468'
_audit_update_record             
;
2015-06-24 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_audit_creation_date             2015-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N7 O10, C H Cl3'
_chemical_formula_sum            'C19 H18 Cl3 N7 O10'
_chemical_formula_weight         610.75
_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'
Cl Cl 0.1484 0.1585 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6131(5)
_cell_length_b                   26.0490(10)
_cell_length_c                   8.1912(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.884(2)
_cell_angle_gamma                90
_cell_volume                     2546.43(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4890
_cell_measurement_temperature    156(2)
_cell_measurement_theta_max      23.892
_cell_measurement_theta_min      3.058
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2007/4 (Bruker,2007/4) was used for absorption correction.
wR2(int) was 0.0516 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.8938.
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    1.593
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17884
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.563
_diffrn_ambient_temperature      155.86
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3699
_reflns_number_total             4460
_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 v7.46A (Bruker, 2008)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.442
_refine_diff_density_min         -1.246
_refine_diff_density_rms         0.292
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.511
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4460
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.2858
_refine_ls_R_factor_gt           0.2697
_refine_ls_restrained_S_all      3.507
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6670
_refine_ls_wR_factor_ref         0.6748
_refine_special_details          
'The structure could be solved only in monoclinic space group P2(1)/c, although there are other transformations possible (for example, C-centered monoclinic). The refinement converges to a very high R value 0.027, the source of this is not very obvious to us. Because of this high R value, there are other parameters that are not within the normal range and the alerts at level A and B arise due to this fact. Although, the molecular structure is unambiguously established, the crystal structure (the symmetry or the placement of the molecule in the unit cell) is to be ascertained.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Shared sites
{C2X, C2X'}
{C19, C19'}
3. Uiso/Uaniso restraints and constraints
Uanis(C2X) = Uanis(C2X')
Uanis(C19) = Uanis(C19')
4. Rigid body (RIGU) restrains
 O10, C3X
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O0AA, C1AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N7, C0AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C19(0.5) C18(0.5) O10(0.5) C3X(0.5) H3XA(0.5) H3XB(0.5) C2X(0.5)
 H2XA(0.5) H2XB(0.5) C0AA(0.5) O0AA(0.5) C1AA(0.5) H1AA(0.5) H1AB(0.5)
 C19'(0.5) C2X'(0.5)
6.a Ternary CH refined with riding coordinates:
 C1CL(H1CL)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C12(H12A,H12B), C10(H10A,H10B), C3X(H3XA,H3XB),
 C2X(H2XA,H2XB), C1AA(H1AA,H1AB)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C1(H1), C15(H15), C14(H14)
6.d Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_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
C3 C -0.2757(11) 0.1740(5) 0.1550(18) 0.040(3) Uani 1 1 d . . . . .
H3 H -0.3163 0.1447 0.1702 0.047 Uiso 1 1 calc R . . . .
C6 C -0.1572(10) 0.2606(5) 0.0946(16) 0.034(3) Uani 1 1 d . . . . .
H6 H -0.1198 0.2895 0.0686 0.041 Uiso 1 1 calc R . . . .
C4 C -0.1767(11) 0.1698(5) 0.1044(16) 0.039(3) Uani 1 1 d . . . . .
C5 C -0.1199(11) 0.2107(6) 0.0802(17) 0.043(3) Uani 1 1 d . . . . .
C1 C -0.2514(10) 0.2667(5) 0.1485(15) 0.032(3) Uani 1 1 d . . . . .
H1 H -0.2776 0.3000 0.1642 0.038 Uiso 1 1 calc R . . . .
C2 C -0.3069(10) 0.2216(6) 0.1792(15) 0.036(3) Uani 1 1 d . . . . .
N1 N -0.4038(11) 0.2287(6) 0.2380(16) 0.052(3) Uani 1 1 d . . . . .
N2 N -0.1437(11) 0.1149(4) 0.0896(16) 0.043(3) Uani 1 1 d . . . . .
O4 O -0.0480(9) 0.1064(4) 0.0991(14) 0.049(3) Uani 1 1 d . . . . .
O3 O -0.2098(11) 0.0817(5) 0.078(2) 0.075(4) Uani 1 1 d . . . . .
O1 O -0.4434(9) 0.2724(5) 0.2447(17) 0.059(3) Uani 1 1 d . . . . .
O2 O -0.4470(15) 0.1882(6) 0.266(2) 0.091(5) Uani 1 1 d . . . . .
O5 O -0.0249(9) 0.2028(4) 0.0274(14) 0.047(3) Uani 1 1 d . . . . .
N3 N 0.0237(9) 0.2503(5) 0.0107(17) 0.041(3) Uani 1 1 d . . . . .
N4 N 0.1065(10) 0.2375(5) -0.0376(15) 0.045(3) Uani 1 1 d . . . . .
O6 O 0.1424(10) 0.1950(4) -0.0567(17) 0.056(3) Uani 1 1 d . . . . .
H6A H 0.1644 0.1953 -0.1431 0.084 Uiso 1 1 calc GR . . . .
N5 N 0.1669(11) 0.2812(4) -0.0779(15) 0.042(3) Uani 1 1 d . . . . .
C11 C 0.1887(13) 0.3737(6) -0.086(2) 0.050(4) Uani 1 1 d . . . . .
H11A H 0.1564 0.3756 -0.2131 0.060 Uiso 1 1 calc R . . . .
H11B H 0.1742 0.4068 -0.0377 0.060 Uiso 1 1 calc R . . . .
C9 C 0.2861(14) 0.2735(6) -0.014(2) 0.056(4) Uani 1 1 d . . . . .
H9A H 0.3051 0.2391 -0.0479 0.067 Uiso 1 1 calc R . . . .
H9B H 0.3138 0.2760 0.1131 0.067 Uiso 1 1 calc R . . . .
C12 C 0.1325(12) 0.3302(6) -0.0186(19) 0.047(4) Uani 1 1 d . . . . .
H12A H 0.1563 0.3310 0.1090 0.056 Uiso 1 1 calc R . . . .
H12B H 0.0500 0.3339 -0.0640 0.056 Uiso 1 1 calc R . . . .
C10 C 0.3398(15) 0.3144(6) -0.091(3) 0.060(5) Uani 1 1 d . . . . .
H10A H 0.4223 0.3105 -0.0489 0.073 Uiso 1 1 calc R . . . .
H10B H 0.3135 0.3115 -0.2187 0.073 Uiso 1 1 calc R . . . .
N6 N 0.3070(10) 0.3652(4) -0.0376(15) 0.042(3) Uani 1 1 d . . . . .
C13 C 0.3805(16) 0.4034(7) 0.041(3) 0.059(4) Uani 1 1 d . . . . .
C16 C 0.6898(13) 0.4231(7) 0.129(2) 0.060(5) Uani 1 1 d . . . . .
C15 C 0.5700(14) 0.4348(8) 0.077(3) 0.077(7) Uani 1 1 d . . . . .
H15 H 0.5424 0.4690 0.0584 0.093 Uiso 1 1 calc R . . . .
C14 C 0.497(2) 0.3912(8) 0.056(3) 0.082(6) Uani 1 1 d . . . . .
H14 H 0.5222 0.3570 0.0514 0.098 Uiso 1 1 calc R . . . .
O7 O 0.3447(10) 0.4424(5) 0.0718(15) 0.057(3) Uani 1 1 d . . . . .
O8 O 0.7364(12) 0.3857(5) 0.2091(19) 0.083(5) Uani 1 1 d . . . . .
C19 C 0.9210(10) 0.4200(6) 0.0655(15) 0.035(3) Uani 0.5 1 d . U P A 2
N7 N 0.7499(13) 0.4617(7) 0.090(2) 0.071(5) Uani 1 1 d . U . . .
C18 C 0.861(3) 0.4694(12) 0.098(4) 0.043(7) Uani 0.5 1 d . U P A 2
O9 O 0.8827(10) 0.3894(5) -0.0500(15) 0.065(3) Uani 1 1 d . . . . .
O10 O 1.0453(15) 0.4374(9) 0.124(3) 0.043(5) Uani 0.5 1 d . U P A 1
Cl1 Cl 0.5376(4) 0.4379(2) 0.5926(11) 0.099(3) Uani 1 1 d . . . . .
Cl2 Cl 0.3370(8) 0.3739(3) 0.4424(10) 0.124(3) Uani 1 1 d . . . . .
Cl3 Cl 0.3278(5) 0.4643(3) 0.6295(7) 0.093(2) Uani 1 1 d . . . . .
C1CL C 0.3946(15) 0.4349(7) 0.493(2) 0.068(5) Uani 1 1 d . . . . .
H1CL H 0.3756 0.4552 0.3834 0.082 Uiso 1 1 calc R . . . .
C3X C 1.060(3) 0.4863(18) 0.256(5) 0.055(9) Uani 0.5 1 d . U P A 1
H3XA H 1.1220 0.4810 0.3652 0.066 Uiso 0.5 1 calc R . P A 1
H3XB H 1.0711 0.5189 0.2021 0.066 Uiso 0.5 1 calc R . P A 1
C2X C 0.9405(19) 0.4841(12) 0.284(3) 0.091(8) Uani 0.5 1 d . . P A 2
H2XA H 0.9451 0.5217 0.3021 0.109 Uiso 0.5 1 calc R . P A 2
H2XB H 0.9168 0.4675 0.3756 0.109 Uiso 0.5 1 calc R . P A 2
C0AA C 0.877(2) 0.4510(13) 0.184(4) 0.040(6) Uani 0.5 1 d . U P A 1
O0AA O 1.022(3) 0.4084(10) 0.182(3) 0.068(7) Uani 0.5 1 d . U P A 2
C1AA C 1.045(4) 0.4629(18) 0.276(7) 0.09(2) Uani 0.5 1 d . U P A 2
H1AA H 1.0992 0.4589 0.3936 0.105 Uiso 0.5 1 calc R . P A 2
H1AB H 1.0786 0.4864 0.2107 0.105 Uiso 0.5 1 calc R . P A 2
C19' C 0.9210(10) 0.4200(6) 0.0655(15) 0.035(3) Uani 0.5 1 d . . P A 1
C2X' C 0.9405(19) 0.4841(12) 0.284(3) 0.091(8) Uani 0.5 1 d . . P A 1


_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
C3 H3 0.9500 . ?
C3 C4 1.44(2) . ?
C3 C2 1.34(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.40(2) . ?
C6 C1 1.404(19) . ?
C4 C5 1.33(2) . ?
C4 N2 1.506(17) . ?
C5 O5 1.414(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.431(19) . ?
C2 N1 1.464(19) . ?
N1 O1 1.252(18) . ?
N1 O2 1.242(19) . ?
N2 O4 1.205(16) . ?
N2 O3 1.183(17) . ?
O5 N3 1.409(16) . ?
N3 N4 1.276(17) . ?
N4 O6 1.225(16) . ?
N4 N5 1.466(17) . ?
O6 H6A 0.8400 . ?
N5 C9 1.44(2) . ?
N5 C12 1.479(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.53(2) . ?
C11 N6 1.431(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.50(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N6 1.496(19) . ?
N6 C13 1.37(2) . ?
C13 C14 1.47(3) . ?
C13 O7 1.17(2) . ?
C16 C15 1.46(2) . ?
C16 O8 1.21(2) . ?
C16 N7 1.36(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.44(3) . ?
C14 H14 0.9500 . ?
C19 C18 1.56(3) . ?
C19 O9 1.211(17) . ?
C19 O0AA 1.35(3) . ?
N7 C18 1.39(3) . ?
N7 C0AA 1.57(4) . ?
C18 C2X 1.58(4) . ?
O9 C19' 1.211(17) . ?
O10 C3X 1.64(5) . ?
O10 C19' 1.55(2) . ?
Cl1 C1CL 1.725(18) . ?
Cl2 C1CL 1.741(19) . ?
Cl3 C1CL 1.78(2) . ?
C1CL H1CL 1.0000 . ?
C3X H3XA 0.9900 . ?
C3X H3XB 0.9900 . ?
C3X C2X' 1.60(5) . ?
C2X H2XA 0.9900 . ?
C2X H2XB 0.9900 . ?
C2X C1AA 1.46(5) . ?
C0AA C19' 1.50(3) . ?
C0AA C2X' 1.27(3) . ?
O0AA C1AA 1.59(4) . ?
C1AA H1AA 0.9900 . ?
C1AA H1AB 0.9900 . ?

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
C4 C3 H3 122.0 . . ?
C2 C3 H3 122.0 . . ?
C2 C3 C4 115.9(12) . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C1 118.3(12) . . ?
C1 C6 H6 120.8 . . ?
C3 C4 N2 112.5(12) . . ?
C5 C4 C3 122.6(12) . . ?
C5 C4 N2 124.8(13) . . ?
C6 C5 O5 120.2(13) . . ?
C4 C5 C6 121.1(12) . . ?
C4 C5 O5 118.5(13) . . ?
C6 C1 H1 120.9 . . ?
C6 C1 C2 118.2(12) . . ?
C2 C1 H1 120.9 . . ?
C3 C2 C1 123.6(12) . . ?
C3 C2 N1 118.9(13) . . ?
C1 C2 N1 117.6(13) . . ?
O1 N1 C2 121.1(13) . . ?
O2 N1 C2 114.7(14) . . ?
O2 N1 O1 123.9(14) . . ?
O4 N2 C4 117.8(12) . . ?
O3 N2 C4 119.6(13) . . ?
O3 N2 O4 122.5(12) . . ?
N3 O5 C5 109.8(10) . . ?
N4 N3 O5 103.0(11) . . ?
N3 N4 N5 113.8(12) . . ?
O6 N4 N3 130.6(13) . . ?
O6 N4 N5 115.6(12) . . ?
N4 O6 H6A 109.5 . . ?
N4 N5 C12 111.5(12) . . ?
C9 N5 N4 111.7(11) . . ?
C9 N5 C12 112.6(12) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
N6 C11 H11A 109.6 . . ?
N6 C11 H11B 109.6 . . ?
N6 C11 C12 110.4(12) . . ?
N5 C9 H9A 110.1 . . ?
N5 C9 H9B 110.1 . . ?
N5 C9 C10 108.1(14) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
N5 C12 C11 107.6(11) . . ?
N5 C12 H12A 110.2 . . ?
N5 C12 H12B 110.2 . . ?
C11 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
N6 C10 C9 107.4(11) . . ?
N6 C10 H10A 110.2 . . ?
N6 C10 H10B 110.2 . . ?
C11 N6 C10 114.7(13) . . ?
C13 N6 C11 120.3(13) . . ?
C13 N6 C10 124.9(13) . . ?
N6 C13 C14 112.8(16) . . ?
O7 C13 N6 118.7(17) . . ?
O7 C13 C14 128.0(18) . . ?
O8 C16 C15 127(2) . . ?
O8 C16 N7 120.7(16) . . ?
N7 C16 C15 112.3(16) . . ?
C16 C15 H15 122.2 . . ?
C14 C15 C16 115.5(17) . . ?
C14 C15 H15 122.2 . . ?
C13 C14 H14 122.5 . . ?
C15 C14 C13 115.0(16) . . ?
C15 C14 H14 122.5 . . ?
O9 C19 C18 125.7(18) . . ?
O9 C19 O0AA 116.8(15) . . ?
O0AA C19 C18 117.4(19) . . ?
C16 N7 C18 136(2) . . ?
C16 N7 C0AA 108(2) . . ?
C19 C18 C2X 100(2) . . ?
N7 C18 C19 114(2) . . ?
N7 C18 C2X 113(2) . . ?
C19' O10 C3X 108.5(19) . . ?
Cl1 C1CL Cl2 116.5(12) . . ?
Cl1 C1CL Cl3 108.5(11) . . ?
Cl1 C1CL H1CL 108.1 . . ?
Cl2 C1CL Cl3 107.2(11) . . ?
Cl2 C1CL H1CL 108.1 . . ?
Cl3 C1CL H1CL 108.1 . . ?
O10 C3X H3XA 112.0 . . ?
O10 C3X H3XB 112.0 . . ?
H3XA C3X H3XB 109.6 . . ?
C2X' C3X O10 99(3) . . ?
C2X' C3X H3XA 112.0 . . ?
C2X' C3X H3XB 112.0 . . ?
C18 C2X H2XA 111.8 . . ?
C18 C2X H2XB 111.9 . . ?
H2XA C2X H2XB 109.6 . . ?
C1AA C2X C18 100(2) . . ?
C1AA C2X H2XA 111.8 . . ?
C1AA C2X H2XB 111.9 . . ?
C19' C0AA N7 108.0(19) . . ?
C2X' C0AA N7 122(3) . . ?
C2X' C0AA C19' 120(2) . . ?
C19 O0AA C1AA 97(2) . . ?
C2X C1AA O0AA 109(3) . . ?
C2X C1AA H1AA 109.8 . . ?
C2X C1AA H1AB 109.9 . . ?
O0AA C1AA H1AA 109.8 . . ?
O0AA C1AA H1AB 109.8 . . ?
H1AA C1AA H1AB 108.3 . . ?
O9 C19' O10 122.8(13) . . ?
O9 C19' C0AA 136.4(15) . . ?
C0AA C19' O10 100.8(15) . . ?
C0AA C2X' C3X 111(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
C3 C4 C5 C6 -3(2) . . . . ?
C3 C4 C5 O5 -178.8(12) . . . . ?
C3 C4 N2 O4 -158.4(12) . . . . ?
C3 C4 N2 O3 17.7(18) . . . . ?
C3 C2 N1 O1 -172.3(13) . . . . ?
C3 C2 N1 O2 2.4(19) . . . . ?
C6 C5 O5 N3 4.9(17) . . . . ?
C6 C1 C2 C3 -1.9(18) . . . . ?
C6 C1 C2 N1 179.1(11) . . . . ?
C4 C3 C2 C1 3.5(19) . . . . ?
C4 C3 C2 N1 -177.4(11) . . . . ?
C4 C5 O5 N3 -179.5(11) . . . . ?
C5 C6 C1 C2 -2.4(17) . . . . ?
C5 C4 N2 O4 19(2) . . . . ?
C5 C4 N2 O3 -164.6(15) . . . . ?
C5 O5 N3 N4 -179.7(10) . . . . ?
C1 C6 C5 C4 4.9(19) . . . . ?
C1 C6 C5 O5 -179.6(11) . . . . ?
C1 C2 N1 O1 6.9(18) . . . . ?
C1 C2 N1 O2 -178.5(13) . . . . ?
C2 C3 C4 C5 -1.0(19) . . . . ?
C2 C3 C4 N2 176.8(11) . . . . ?
N2 C4 C5 C6 179.3(11) . . . . ?
N2 C4 C5 O5 3.7(19) . . . . ?
O5 N3 N4 O6 -4.0(19) . . . . ?
O5 N3 N4 N5 175.4(10) . . . . ?
N3 N4 N5 C9 138.9(13) . . . . ?
N3 N4 N5 C12 11.9(16) . . . . ?
N4 N5 C9 C10 168.7(13) . . . . ?
N4 N5 C12 C11 -173.1(10) . . . . ?
O6 N4 N5 C9 -41.6(16) . . . . ?
O6 N4 N5 C12 -168.6(12) . . . . ?
N5 C9 C10 N6 59.1(19) . . . . ?
C11 N6 C13 C14 -170.6(16) . . . . ?
C11 N6 C13 O7 2(2) . . . . ?
C9 N5 C12 C11 60.4(15) . . . . ?
C9 C10 N6 C11 -57.2(19) . . . . ?
C9 C10 N6 C13 127.2(17) . . . . ?
C12 N5 C9 C10 -64.9(17) . . . . ?
C12 C11 N6 C10 54.7(16) . . . . ?
C12 C11 N6 C13 -129.5(15) . . . . ?
C10 N6 C13 C14 5(2) . . . . ?
C10 N6 C13 O7 177.4(15) . . . . ?
N6 C11 C12 N5 -53.0(15) . . . . ?
N6 C13 C14 C15 158.4(19) . . . . ?
C16 C15 C14 C13 167(2) . . . . ?
C16 N7 C18 C19 33(4) . . . . ?
C16 N7 C18 C2X -80(3) . . . . ?
C16 N7 C0AA C19' 90(2) . . . . ?
C16 N7 C0AA C2X' -125(3) . . . . ?
C15 C16 N7 C18 -174(3) . . . . ?
C15 C16 N7 C0AA 168.2(18) . . . . ?
O7 C13 C14 C15 -13(3) . . . . ?
O8 C16 C15 C14 -26(3) . . . . ?
O8 C16 N7 C18 10(4) . . . . ?
O8 C16 N7 C0AA -7(2) . . . . ?
C19 C18 C2X C1AA 29(3) . . . . ?
C19 O0AA C1AA C2X 36(5) . . . . ?
N7 C16 C15 C14 159(2) . . . . ?
N7 C18 C2X C1AA 151(3) . . . . ?
N7 C0AA C19' O9 -28(4) . . . . ?
N7 C0AA C19' O10 151(2) . . . . ?
N7 C0AA C2X' C3X -139(3) . . . . ?
C18 C19 O0AA C1AA -15(4) . . . . ?
C18 C2X C1AA O0AA -42(5) . . . . ?
O9 C19 C18 N7 46(3) . . . . ?
O9 C19 C18 C2X 167.7(17) . . . . ?
O9 C19 O0AA C1AA 169(3) . . . . ?
O10 C3X C2X' C0AA -7(4) . . . . ?
C3X O10 C19' O9 170(2) . . . . ?
C3X O10 C19' C0AA -10(3) . . . . ?
O0AA C19 C18 N7 -129(3) . . . . ?
O0AA C19 C18 C2X -8(3) . . . . ?
C19' O10 C3X C2X' 10(3) . . . . ?
C19' C0AA C2X' C3X 1(5) . . . . ?
C2X' C0AA C19' O9 -173(3) . . . . ?
C2X' C0AA C19' O10 6(4) . . . . ?

_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_inp21byn
_database_code_depnum_ccdc_archive 'CCDC 1408469'
_audit_update_record             
;
2015-06-24 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 N2 O6'
_chemical_formula_weight         204.14

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.0324(6)
_cell_length_b                   5.2469(2)
_cell_length_c                   16.1420(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.826(3)
_cell_angle_gamma                90.00
_cell_volume                     831.66(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    152(2)
_cell_measurement_reflns_used    3664
_cell_measurement_theta_min      2.578
_cell_measurement_theta_max      30.235

_exptl_crystal_description       Plates
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9335
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      152(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 kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6746
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1812
_reflns_number_gt                1552
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'APEX2 (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'

_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)+(0.0443P)²+0.3228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1812
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19963(10) -0.24964(17) -0.01049(6) 0.0235(2) Uani 1 1 d . . .
O2 O 0.02500(9) -0.25327(16) 0.05549(6) 0.0211(2) Uani 1 1 d . . .
O3 O 0.14619(10) 0.08327(18) 0.25801(6) 0.0241(2) Uani 1 1 d . . .
O4 O -0.04401(9) 0.39222(17) 0.29615(6) 0.0225(2) Uani 1 1 d . . .
O5 O -0.15690(10) 0.0602(2) 0.22818(7) 0.0325(3) Uani 1 1 d . . .
O6 O -0.13746(13) 0.1088(2) 0.36369(7) 0.0414(3) Uani 1 1 d . . .
N1 N 0.12370(10) 0.23599(19) 0.12441(7) 0.0164(2) Uani 1 1 d . . .
H1 H 0.0867 0.3546 0.0884 0.020 Uiso 1 1 calc R . .
N2 N -0.11918(12) 0.1661(2) 0.29488(8) 0.0262(3) Uani 1 1 d . . .
C2 C 0.13245(13) -0.1642(2) 0.04736(8) 0.0171(3) Uani 1 1 d . . .
C3 C 0.21193(12) 0.0494(2) 0.09843(8) 0.0170(3) Uani 1 1 d . . .
H3 H 0.2705 -0.0259 0.1503 0.020 Uiso 1 1 calc R . .
C4 C 0.30354(14) 0.1413(3) 0.04013(9) 0.0230(3) Uani 1 1 d . . .
H4B H 0.3905 0.2102 0.0726 0.028 Uiso 1 1 calc R . .
H4A H 0.2579 0.2727 0.0001 0.028 Uiso 1 1 calc R . .
C5 C 0.32546(14) -0.1042(3) -0.00558(9) 0.0259(3) Uani 1 1 d . . .
H5B H 0.3414 -0.0672 -0.0629 0.031 Uiso 1 1 calc R . .
H5A H 0.4045 -0.1996 0.0265 0.031 Uiso 1 1 calc R . .
C6 C 0.09683(12) 0.2327(2) 0.20213(8) 0.0170(3) Uani 1 1 d . . .
C7 C -0.00257(13) 0.4390(2) 0.21721(8) 0.0206(3) Uani 1 1 d . . .
H7B H 0.0415 0.6082 0.2189 0.025 Uiso 1 1 calc R . .
H7A H -0.0834 0.4389 0.1703 0.025 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
O1 C2 1.3362(15) . ?
O1 C5 1.4634(17) . ?
O2 C2 1.2065(16) . ?
O3 C6 1.2210(15) . ?
O4 N2 1.4037(15) . ?
O4 C7 1.4400(15) . ?
O5 N2 1.2017(16) . ?
O6 N2 1.2005(15) . ?
N1 C6 1.3363(16) . ?
N1 C3 1.4388(15) . ?
N1 H1 0.8800 . ?
C2 C3 1.5171(17) . ?
C3 C4 1.5223(17) . ?
C3 H3 1.0000 . ?
C4 C5 1.5226(19) . ?
C4 H4B 0.9900 . ?
C4 H4A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C7 1.5244(17) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?

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 O1 C5 109.89(10) . . ?
N2 O4 C7 112.50(9) . . ?
C6 N1 C3 121.31(10) . . ?
C6 N1 H1 119.3 . . ?
C3 N1 H1 119.3 . . ?
O6 N2 O5 129.31(13) . . ?
O6 N2 O4 112.44(11) . . ?
O5 N2 O4 118.25(11) . . ?
O2 C2 O1 122.41(12) . . ?
O2 C2 C3 127.51(11) . . ?
O1 C2 C3 110.08(10) . . ?
N1 C3 C2 112.01(10) . . ?
N1 C3 C4 116.74(10) . . ?
C2 C3 C4 102.41(10) . . ?
N1 C3 H3 108.4 . . ?
C2 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C3 C4 C5 101.36(10) . . ?
C3 C4 H4B 111.5 . . ?
C5 C4 H4B 111.5 . . ?
C3 C4 H4A 111.5 . . ?
C5 C4 H4A 111.5 . . ?
H4B C4 H4A 109.3 . . ?
O1 C5 C4 105.00(10) . . ?
O1 C5 H5B 110.7 . . ?
C4 C5 H5B 110.7 . . ?
O1 C5 H5A 110.7 . . ?
C4 C5 H5A 110.7 . . ?
H5B C5 H5A 108.8 . . ?
O3 C6 N1 124.92(11) . . ?
O3 C6 C7 121.16(11) . . ?
N1 C6 C7 113.91(10) . . ?
O4 C7 C6 109.72(10) . . ?
O4 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
O4 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
H7B C7 H7A 108.2 . . ?

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
C7 O4 N2 O6 170.32(11) . . . . ?
C7 O4 N2 O5 -10.48(16) . . . . ?
C5 O1 C2 O2 179.63(11) . . . . ?
C5 O1 C2 C3 -1.07(13) . . . . ?
C6 N1 C3 C2 98.81(13) . . . . ?
C6 N1 C3 C4 -143.60(12) . . . . ?
O2 C2 C3 N1 -33.54(17) . . . . ?
O1 C2 C3 N1 147.21(10) . . . . ?
O2 C2 C3 C4 -159.40(12) . . . . ?
O1 C2 C3 C4 21.34(13) . . . . ?
N1 C3 C4 C5 -153.99(11) . . . . ?
C2 C3 C4 C5 -31.27(12) . . . . ?
C2 O1 C5 C4 -19.87(14) . . . . ?
C3 C4 C5 O1 31.65(13) . . . . ?
C3 N1 C6 O3 2.77(19) . . . . ?
C3 N1 C6 C7 -177.92(10) . . . . ?
N2 O4 C7 C6 -65.25(13) . . . . ?
O3 C6 C7 O4 -11.01(16) . . . . ?
N1 C6 C7 O4 169.65(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.046
