# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_20180022-yc-33_0m
_database_code_depnum_ccdc_archive 'CCDC 1846590'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_audit_creation_date             2018-07-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H6 N6 O6'
_chemical_formula_sum            'C4 H6 N6 O6'
_chemical_formula_weight         234.15
_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                   8.8210(19)
_cell_length_b                   9.509(2)
_cell_length_c                   19.681(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1650.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    635
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0712 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.8981.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8062
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         3.101
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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                1145
_reflns_number_total             1897
_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         0.578
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1897
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.018
_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)+(0.0872P)²+0.7082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1835
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3 O 0.8732(3) 0.6502(2) 0.65153(12) 0.0375(6) Uani 1 1 d . . . . .
O4 O 1.0352(3) 0.5539(3) 0.58384(13) 0.0455(7) Uani 1 1 d . . . . .
O5 O 0.9711(3) 0.2994(3) 0.55330(14) 0.0466(7) Uani 1 1 d . . . . .
O6 O 0.7459(3) 0.2872(3) 0.51196(13) 0.0460(7) Uani 1 1 d . . . . .
N4 N 0.5259(3) 0.4113(3) 0.57584(13) 0.0267(6) Uani 1 1 d . . . . .
H4 H 0.5472 0.3691 0.5372 0.032 Uiso 1 1 calc R . . . .
N5 N 0.9082(3) 0.5574(3) 0.60891(13) 0.0300(6) Uani 1 1 d . . . . .
N3 N 0.6017(3) 0.5609(3) 0.65942(13) 0.0304(7) Uani 1 1 d . . . . .
H3 H 0.6743 0.6022 0.6827 0.036 Uiso 1 1 calc R . . . .
N2 N 0.3601(3) 0.4546(3) 0.67007(13) 0.0295(7) Uani 1 1 d . . . . .
N6 N 0.8417(3) 0.3455(3) 0.54911(14) 0.0317(7) Uani 1 1 d . . . . .
O2 O 0.3270(3) 0.2422(3) 0.71402(16) 0.0570(9) Uani 1 1 d . . . . .
N1 N 0.3802(4) 0.3556(3) 0.72128(16) 0.0445(8) Uani 1 1 d . . . . .
C3 C 0.6372(3) 0.4796(3) 0.60714(14) 0.0222(7) Uani 1 1 d . . . . .
C4 C 0.7947(3) 0.4627(3) 0.58742(15) 0.0244(7) Uani 1 1 d . . . . .
O1 O 0.4499(5) 0.3913(3) 0.77203(14) 0.0746(11) Uani 1 1 d . . . . .
C2 C 0.4442(4) 0.5831(4) 0.67896(18) 0.0348(8) Uani 1 1 d . . . . .
H2A H 0.4391 0.6132 0.7271 0.042 Uiso 1 1 calc R . . . .
H2B H 0.3993 0.6583 0.6506 0.042 Uiso 1 1 calc R . . . .
C1 C 0.3698(4) 0.4016(4) 0.60128(16) 0.0363(8) Uani 1 1 d . . . . .
H1A H 0.3016 0.4568 0.5715 0.044 Uiso 1 1 calc R . . . .
H1B H 0.3361 0.3023 0.6002 0.044 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
O3 N5 1.256(3) . ?
O4 N5 1.225(3) . ?
O5 N6 1.226(4) . ?
O6 N6 1.247(3) . ?
N4 H4 0.8800 . ?
N4 C3 1.328(4) . ?
N4 C1 1.468(4) . ?
N5 C4 1.411(4) . ?
N3 H3 0.8800 . ?
N3 C3 1.325(4) . ?
N3 C2 1.457(4) . ?
N2 N1 1.391(4) . ?
N2 C2 1.440(4) . ?
N2 C1 1.447(4) . ?
N6 C4 1.408(4) . ?
O2 N1 1.184(4) . ?
N1 O1 1.221(4) . ?
C3 C4 1.451(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 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
C3 N4 H4 117.8 . . ?
C3 N4 C1 124.5(3) . . ?
C1 N4 H4 117.8 . . ?
O3 N5 C4 118.3(3) . . ?
O4 N5 O3 120.9(3) . . ?
O4 N5 C4 120.8(3) . . ?
C3 N3 H3 119.5 . . ?
C3 N3 C2 121.0(3) . . ?
C2 N3 H3 119.5 . . ?
N1 N2 C2 114.9(3) . . ?
N1 N2 C1 115.8(3) . . ?
C2 N2 C1 112.3(3) . . ?
O5 N6 O6 120.8(3) . . ?
O5 N6 C4 121.4(3) . . ?
O6 N6 C4 117.8(3) . . ?
O2 N1 N2 118.6(3) . . ?
O2 N1 O1 123.5(3) . . ?
O1 N1 N2 117.9(3) . . ?
N4 C3 C4 122.0(3) . . ?
N3 C3 N4 118.1(3) . . ?
N3 C3 C4 119.9(3) . . ?
N5 C4 C3 121.9(3) . . ?
N6 C4 N5 117.1(3) . . ?
N6 C4 C3 120.8(3) . . ?
N3 C2 H2A 109.7 . . ?
N3 C2 H2B 109.7 . . ?
N2 C2 N3 109.6(3) . . ?
N2 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N4 C1 H1A 109.5 . . ?
N4 C1 H1B 109.5 . . ?
N2 C1 N4 110.6(3) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?

_vrf_PLAT430_z                   
;
PROBLEM: Short Inter D...A Contact O1     ..N5  ..  2.85 Ang.
RESPONSE: Prossibly because of the disorder of O1 atom.
;
# end Validation Reply Form

_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_20180043-yc-27_0m
_database_code_depnum_ccdc_archive 'CCDC 1846307'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_audit_creation_date             2018-07-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 Cl N6 O6'
_chemical_formula_sum            'C4 H5 Cl N6 O6'
_chemical_formula_weight         268.59
_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                   8.582(5)
_cell_length_b                   11.470(7)
_cell_length_c                   10.482(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.736(11)
_cell_angle_gamma                90
_cell_volume                     965.0(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1464
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0756 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.8118.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5264
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.672
_diffrn_reflns_theta_min         2.538
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.975
_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                1791
_reflns_number_total             2198
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.035
_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)+(0.0481P)²+0.0562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.38042(5) 0.91532(4) 0.23174(5) 0.01761(16) Uani 1 1 d . . . . .
O5 O 0.49832(17) 0.81796(12) 0.58774(13) 0.0214(3) Uani 1 1 d . . . . .
O6 O 0.32795(16) 0.95830(12) 0.48839(14) 0.0203(3) Uani 1 1 d . . . . .
O3 O 0.48139(17) 0.62098(12) 0.38201(15) 0.0230(3) Uani 1 1 d . . . . .
O4 O 0.65008(15) 0.76354(14) 0.38477(14) 0.0243(4) Uani 1 1 d . . . . .
N3 N 0.15317(18) 0.72485(14) 0.40698(15) 0.0137(3) Uani 1 1 d . . . . .
N4 N 0.13863(18) 0.71420(14) 0.17786(16) 0.0162(4) Uani 1 1 d . . . . .
H4 H 0.1863 0.7324 0.1188 0.019 Uiso 1 1 calc R . . . .
N6 N 0.40375(19) 0.86868(14) 0.48854(16) 0.0148(3) Uani 1 1 d . . . . .
N2 N -0.01832(19) 0.57764(14) 0.25143(17) 0.0169(4) Uani 1 1 d . . . . .
N5 N 0.51581(19) 0.72302(15) 0.37394(16) 0.0161(4) Uani 1 1 d . . . . .
O2 O 0.1149(2) 0.43828(15) 0.18070(18) 0.0389(4) Uani 1 1 d . . . . .
O1 O 0.1261(2) 0.43511(16) 0.3887(2) 0.0425(5) Uani 1 1 d . . . . .
N1 N 0.0825(2) 0.47825(15) 0.27588(18) 0.0243(4) Uani 1 1 d . . . . .
C3 C 0.2063(2) 0.74698(15) 0.30926(18) 0.0106(4) Uani 1 1 d . . . . .
C4 C 0.3710(2) 0.81158(16) 0.34845(18) 0.0123(4) Uani 1 1 d . . . . .
C2 C 0.0054(2) 0.65000(19) 0.3715(2) 0.0193(4) Uani 1 1 d . . . . .
H2A H 0.0153 0.5988 0.4501 0.023 Uiso 1 1 calc R . . . .
H2B H -0.0943 0.6996 0.3546 0.023 Uiso 1 1 calc R . . . .
C1 C -0.0164(2) 0.64749(19) 0.1362(2) 0.0200(4) Uani 1 1 d . . . . .
H1A H -0.1130 0.7011 0.1072 0.024 Uiso 1 1 calc R . . . .
H1B H -0.0236 0.5962 0.0583 0.024 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
Cl1 C4 1.729(2) . ?
O5 N6 1.217(2) . ?
O6 N6 1.216(2) . ?
O3 N5 1.217(2) . ?
O4 N5 1.210(2) . ?
N3 C3 1.285(2) . ?
N3 C2 1.466(2) . ?
N4 H4 0.8800 . ?
N4 C3 1.345(2) . ?
N4 C1 1.461(2) . ?
N6 C4 1.540(2) . ?
N2 N1 1.399(2) . ?
N2 C2 1.461(3) . ?
N2 C1 1.454(3) . ?
N5 C4 1.553(2) . ?
O2 N1 1.216(2) . ?
O1 N1 1.212(2) . ?
C3 C4 1.518(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 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
C3 N3 C2 115.63(15) . . ?
C3 N4 H4 121.0 . . ?
C3 N4 C1 118.01(15) . . ?
C1 N4 H4 121.0 . . ?
O5 N6 C4 116.93(15) . . ?
O6 N6 O5 126.85(17) . . ?
O6 N6 C4 116.18(15) . . ?
N1 N2 C2 114.63(15) . . ?
N1 N2 C1 114.38(16) . . ?
C1 N2 C2 111.33(16) . . ?
O3 N5 C4 116.20(15) . . ?
O4 N5 O3 127.53(17) . . ?
O4 N5 C4 116.26(16) . . ?
O2 N1 N2 117.59(18) . . ?
O1 N1 N2 117.94(18) . . ?
O1 N1 O2 124.4(2) . . ?
N3 C3 N4 127.93(16) . . ?
N3 C3 C4 116.08(15) . . ?
N4 C3 C4 115.88(15) . . ?
N6 C4 Cl1 110.09(13) . . ?
N6 C4 N5 104.42(13) . . ?
N5 C4 Cl1 109.67(12) . . ?
C3 C4 Cl1 114.64(12) . . ?
C3 C4 N6 107.69(13) . . ?
C3 C4 N5 109.82(14) . . ?
N3 C2 H2A 108.9 . . ?
N3 C2 H2B 108.9 . . ?
N2 C2 N3 113.27(15) . . ?
N2 C2 H2A 108.9 . . ?
N2 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N4 C1 H1A 110.0 . . ?
N4 C1 H1B 110.0 . . ?
N2 C1 N4 108.49(15) . . ?
N2 C1 H1A 110.0 . . ?
N2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?

_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_twin4
_database_code_depnum_ccdc_archive 'CCDC 1846421'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_audit_creation_date             2018-07-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 N7 O8'
_chemical_formula_sum            'C4 H5 N7 O8'
_chemical_formula_weight         279.15
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.886(3)
_cell_length_b                   8.134(4)
_cell_length_c                   20.460(9)
_cell_angle_alpha                99.275(11)
_cell_angle_beta                 90.656(10)
_cell_angle_gamma                93.353(10)
_cell_volume                     964.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2039
_cell_measurement_temperature    173
_cell_measurement_theta_max      24.02
_cell_measurement_theta_min      2.88
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0737 before and 0.0570 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0719 before and 0.0534 after correction.
 The Ratio of minimum to maximum transmission is 0.81.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 14021 reflections, Rint = 0.0850
 (5667 with I > 3sig(I), Rint = 0.0719)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.1013
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            4369
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         1.009
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.980
_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                2965
_reflns_number_total             4369
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      8.674
_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)+(0.0806P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1517
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O4-O13
 -4 with sigma of 0.02
3. Others
 Fixed 1: DFIX(-4)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C5(H5A,H5B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O4 O 0.4861(3) 0.4625(2) 0.73917(9) 0.0166(4) Uani 1 1 d D . . . .
O7 O 0.4629(3) 0.7564(2) 0.64045(9) 0.0155(4) Uani 1 1 d . . . . .
O12 O 0.9835(3) 1.0762(2) 0.76013(9) 0.0161(4) Uani 1 1 d . . . . .
O6 O -0.0259(3) 0.7570(2) 0.61212(9) 0.0173(4) Uani 1 1 d . . . . .
O8 O 0.2999(3) 0.8050(2) 0.73606(9) 0.0164(4) Uani 1 1 d . . . . .
O15 O 0.4677(3) 0.7428(3) 0.88333(9) 0.0195(4) Uani 1 1 d . . . . .
O13 O 0.7954(3) 0.7330(2) 0.75610(9) 0.0171(4) Uani 1 1 d D . . . .
O1 O 0.8239(3) 0.1901(3) 0.51257(10) 0.0211(5) Uani 1 1 d . . . . .
O14 O 0.9485(3) 0.7580(2) 0.85469(9) 0.0169(4) Uani 1 1 d . . . . .
O10 O 1.4155(3) 1.3044(3) 0.98263(9) 0.0212(5) Uani 1 1 d . . . . .
O3 O 0.4985(3) 0.1942(2) 0.73728(9) 0.0195(4) Uani 1 1 d . . . . .
O5 O -0.1797(3) 0.5069(3) 0.61152(9) 0.0203(5) Uani 1 1 d . . . . .
O9 O 1.3593(3) 1.3760(3) 0.88637(10) 0.0215(5) Uani 1 1 d . . . . .
O11 O 1.0032(3) 1.3474(3) 0.76817(9) 0.0191(4) Uani 1 1 d . . . . .
O16 O 0.3429(3) 0.9906(3) 0.89019(10) 0.0218(5) Uani 1 1 d . . . . .
O2 O 0.7880(3) 0.1127(3) 0.60839(11) 0.0283(5) Uani 1 1 d . . . . .
N10 N 0.8685(3) 1.2323(3) 0.85205(10) 0.0095(4) Uani 1 1 d . . . . .
N9 N 1.0620(3) 1.3501(3) 0.95253(10) 0.0124(5) Uani 1 1 d . . . . .
N11 N 0.8378(3) 1.0822(3) 0.94036(10) 0.0114(5) Uani 1 1 d . . . . .
N14 N 0.8220(3) 0.7993(3) 0.81356(10) 0.0116(5) Uani 1 1 d . . . . .
N3 N 0.2931(3) 0.4225(3) 0.56066(10) 0.0115(5) Uani 1 1 d . . . . .
N5 N 0.4495(3) 0.3165(3) 0.71353(10) 0.0119(5) Uani 1 1 d . . . . .
N12 N 0.9601(3) 1.2174(3) 0.78904(10) 0.0129(5) Uani 1 1 d . . . . .
N2 N 0.4746(3) 0.1553(3) 0.55183(10) 0.0127(5) Uani 1 1 d . . . . .
N4 N 0.3310(3) 0.2880(3) 0.65326(10) 0.0112(5) Uani 1 1 d . . . . .
N13 N 0.4799(3) 0.8855(3) 0.87386(10) 0.0148(5) Uani 1 1 d . . . . .
N7 N 0.3272(3) 0.7227(3) 0.68154(10) 0.0116(5) Uani 1 1 d . . . . .
N8 N 1.2948(3) 1.3399(3) 0.93881(11) 0.0146(5) Uani 1 1 d . . . . .
N6 N -0.0284(3) 0.6164(3) 0.62478(10) 0.0125(5) Uani 1 1 d . . . . .
N1 N 0.7126(3) 0.1561(3) 0.55877(11) 0.0156(5) Uani 1 1 d . . . . .
C6 C 0.9222(4) 1.3867(3) 0.89868(12) 0.0126(5) Uani 1 1 d . . . . .
H6A H 1.0047 1.4697 0.8758 0.015 Uiso 1 1 calc R . . . .
H6B H 0.7799 1.4342 0.9162 0.015 Uiso 1 1 calc R . . . .
C3 C 0.2810(4) 0.4241(3) 0.62225(12) 0.0088(5) Uani 1 1 d . . . . .
C2 C 0.3466(4) 0.1287(3) 0.60994(12) 0.0137(6) Uani 1 1 d . . . . .
H2A H 0.4239 0.0502 0.6337 0.016 Uiso 1 1 calc R . . . .
H2B H 0.1921 0.0795 0.5964 0.016 Uiso 1 1 calc R . . . .
C5 C 0.9584(4) 1.2172(3) 0.98506(12) 0.0125(5) Uani 1 1 d . . . . .
H5A H 1.0794 1.1699 1.0090 0.015 Uiso 1 1 calc R . . . .
H5B H 0.8507 1.2668 1.0183 0.015 Uiso 1 1 calc R . . . .
C7 C 0.8111(4) 1.0882(3) 0.87952(12) 0.0098(5) Uani 1 1 d . . . . .
C4 C 0.1704(4) 0.5675(3) 0.66443(12) 0.0086(5) Uani 1 1 d . . . . .
H4 H 0.1133 0.5312 0.7060 0.010 Uiso 1 1 calc R . . . .
C1 C 0.3865(4) 0.2841(3) 0.51738(12) 0.0142(6) Uani 1 1 d . . . . .
H1A H 0.5112 0.3288 0.4920 0.017 Uiso 1 1 calc R . . . .
H1B H 0.2663 0.2314 0.4852 0.017 Uiso 1 1 calc R . . . .
C8 C 0.6800(4) 0.9470(3) 0.83560(12) 0.0103(5) Uani 1 1 d . . . . .
H8 H 0.6207 0.9885 0.7957 0.012 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
O4 N5 1.225(3) . ?
O7 N7 1.218(3) . ?
O12 N12 1.220(3) . ?
O6 N6 1.211(3) . ?
O8 N7 1.223(3) . ?
O15 N13 1.205(3) . ?
O13 N14 1.216(3) . ?
O1 N1 1.215(3) . ?
O14 N14 1.217(3) . ?
O10 N8 1.219(3) . ?
O3 N5 1.223(3) . ?
O5 N6 1.218(3) . ?
O9 N8 1.216(3) . ?
O11 N12 1.217(3) . ?
O16 N13 1.220(3) . ?
O2 N1 1.215(3) . ?
N10 N12 1.393(3) . ?
N10 C6 1.465(3) . ?
N10 C7 1.405(3) . ?
N9 N8 1.406(3) . ?
N9 C6 1.447(3) . ?
N9 C5 1.465(3) . ?
N11 C5 1.455(3) . ?
N11 C7 1.262(3) . ?
N14 C8 1.515(3) . ?
N3 C3 1.261(3) . ?
N3 C1 1.454(3) . ?
N5 N4 1.389(3) . ?
N2 N1 1.406(3) . ?
N2 C2 1.453(3) . ?
N2 C1 1.469(3) . ?
N4 C3 1.405(3) . ?
N4 C2 1.456(3) . ?
N13 C8 1.526(3) . ?
N7 C4 1.510(3) . ?
N6 C4 1.524(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 C4 1.519(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.506(4) . ?
C4 H4 1.0000 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C8 H8 1.0000 . ?

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
N12 N10 C6 118.4(2) . . ?
N12 N10 C7 119.7(2) . . ?
C7 N10 C6 116.8(2) . . ?
N8 N9 C6 114.9(2) . . ?
N8 N9 C5 116.0(2) . . ?
C6 N9 C5 112.8(2) . . ?
C7 N11 C5 121.7(2) . . ?
O13 N14 O14 126.6(2) . . ?
O13 N14 C8 115.9(2) . . ?
O14 N14 C8 117.4(2) . . ?
C3 N3 C1 121.3(2) . . ?
O4 N5 N4 116.5(2) . . ?
O3 N5 O4 126.2(2) . . ?
O3 N5 N4 117.3(2) . . ?
O12 N12 N10 116.9(2) . . ?
O11 N12 O12 127.0(2) . . ?
O11 N12 N10 116.1(2) . . ?
N1 N2 C2 115.6(2) . . ?
N1 N2 C1 116.4(2) . . ?
C2 N2 C1 113.72(19) . . ?
N5 N4 C3 119.4(2) . . ?
N5 N4 C2 119.0(2) . . ?
C3 N4 C2 116.2(2) . . ?
O15 N13 O16 126.9(2) . . ?
O15 N13 C8 119.3(2) . . ?
O16 N13 C8 113.7(2) . . ?
O7 N7 O8 126.3(2) . . ?
O7 N7 C4 118.5(2) . . ?
O8 N7 C4 115.2(2) . . ?
O10 N8 N9 116.3(2) . . ?
O9 N8 O10 126.0(2) . . ?
O9 N8 N9 117.6(2) . . ?
O6 N6 O5 127.1(2) . . ?
O6 N6 C4 118.8(2) . . ?
O5 N6 C4 114.0(2) . . ?
O1 N1 N2 116.8(2) . . ?
O2 N1 O1 125.7(2) . . ?
O2 N1 N2 117.3(2) . . ?
N10 C6 H6A 109.9 . . ?
N10 C6 H6B 109.9 . . ?
N9 C6 N10 109.1(2) . . ?
N9 C6 H6A 109.9 . . ?
N9 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N3 C3 N4 123.5(2) . . ?
N3 C3 C4 118.9(2) . . ?
N4 C3 C4 116.8(2) . . ?
N2 C2 N4 109.0(2) . . ?
N2 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
N4 C2 H2A 109.9 . . ?
N4 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N9 C5 H5A 108.6 . . ?
N9 C5 H5B 108.6 . . ?
N11 C5 N9 114.5(2) . . ?
N11 C5 H5A 108.6 . . ?
N11 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
N10 C7 C8 117.0(2) . . ?
N11 C7 N10 122.6(2) . . ?
N11 C7 C8 119.6(2) . . ?
N7 C4 N6 106.16(19) . . ?
N7 C4 C3 113.37(19) . . ?
N7 C4 H4 109.7 . . ?
N6 C4 H4 109.7 . . ?
C3 C4 N6 108.21(19) . . ?
C3 C4 H4 109.7 . . ?
N3 C1 N2 114.5(2) . . ?
N3 C1 H1A 108.6 . . ?
N3 C1 H1B 108.6 . . ?
N2 C1 H1A 108.6 . . ?
N2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
N14 C8 N13 107.5(2) . . ?
N14 C8 H8 109.2 . . ?
N13 C8 H8 109.2 . . ?
C7 C8 N14 112.91(19) . . ?
C7 C8 N13 108.92(19) . . ?
C7 C8 H8 109.2 . . ?

_vrf_PLAT430_z                   
;
PROBLEM: Short Inter D...A Contact O4     ..O13  ..  2.75 Ang.
RESPONSE: Prossibly because of the existence of disordered proton 
which could interact with O4 and O13 through hydrogen bond
have not been added.
;
# end Validation Reply Form



_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_20180016-yc-30_0m
_database_code_depnum_ccdc_archive 'CCDC 1846317'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_audit_creation_date             2018-01-07
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H6 N6 O6'
_chemical_formula_sum            'C4 H6 N6 O6'
_chemical_formula_weight         234.15
_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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   7.1223(15)
_cell_length_b                   10.448(2)
_cell_length_c                   11.389(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     847.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    749
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.09
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0844 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.8204.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5543
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.645
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_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                685
_reflns_number_total             1013
_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         0.379
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1013
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.122
_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)+(0.1120P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1956
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
2. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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 0.2295(3) 0.3588(2) 0.47802(19) 0.0307(6) Uani 1 1 d . . . . .
N3 N 0.4648(4) 0.2500 0.3675(3) 0.0317(8) Uani 1 2 d S T P . .
O1 O 0.0379(3) 0.4678(2) 0.63852(17) 0.0583(8) Uani 1 1 d . . . . .
O3 O 0.6802(3) 0.35267(19) 0.4778(2) 0.0662(8) Uani 1 1 d . . . . .
N4 N 0.6182(4) 0.2500 0.4486(3) 0.0366(8) Uani 1 2 d S T P . .
N1 N 0.0082(3) 0.3649(3) 0.6868(2) 0.0426(7) Uani 1 1 d . . . . .
C2 C 0.1744(4) 0.2500 0.5265(3) 0.0227(7) Uani 1 2 d S T P . .
C1 C 0.0601(4) 0.2500 0.6320(3) 0.0300(8) Uani 1 2 d S T P A .
C3 C 0.3482(4) 0.3639(2) 0.3747(2) 0.0344(7) Uani 1 1 d . . . . .
O2 O -0.026(2) 0.3446(10) 0.7992(7) 0.054(3) Uani 0.49(3) 1 d . U . A 1
H2 H 0.177(4) 0.425(3) 0.518(2) 0.047(8) Uiso 1 1 d . . . . .
O2A O -0.1074(15) 0.3842(10) 0.7623(12) 0.056(3) Uani 0.51(3) 1 d . U . A 2
H3A H 0.263(4) 0.359(3) 0.302(2) 0.043(8) Uiso 1 1 d . . . . .
H3B H 0.415(4) 0.437(4) 0.379(3) 0.060(9) 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
N2 C2 1.323(3) . ?
N2 C3 1.450(3) . ?
N2 H2 0.91(3) . ?
N3 N4 1.431(4) . ?
N3 C3 1.453(3) 7_565 ?
N3 C3 1.453(3) . ?
O1 N1 1.226(3) . ?
O3 N4 1.207(2) . ?
N4 O3 1.207(2) 7_565 ?
N1 C1 1.403(3) . ?
N1 O2 1.320(7) . ?
N1 O2A 1.207(5) . ?
C2 N2 1.323(3) 7_565 ?
C2 C1 1.451(4) . ?
C1 N1 1.403(3) 7_565 ?
C3 H3A 1.03(3) . ?
C3 H3B 0.90(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
C2 N2 C3 122.9(2) . . ?
C2 N2 H2 109.1(19) . . ?
C3 N2 H2 127.9(19) . . ?
N4 N3 C3 113.57(18) . 7_565 ?
N4 N3 C3 113.57(18) . . ?
C3 N3 C3 109.9(3) 7_565 . ?
O3 N4 N3 117.22(17) 7_565 . ?
O3 N4 N3 117.22(17) . . ?
O3 N4 O3 125.5(3) 7_565 . ?
O1 N1 C1 120.3(2) . . ?
O1 N1 O2 127.5(4) . . ?
O2 N1 C1 110.0(6) . . ?
O2A N1 O1 106.9(7) . . ?
O2A N1 C1 129.7(5) . . ?
N2 C2 N2 118.4(3) . 7_565 ?
N2 C2 C1 120.78(15) . . ?
N2 C2 C1 120.78(15) 7_565 . ?
N1 C1 N1 117.7(3) 7_565 . ?
N1 C1 C2 121.08(15) 7_565 . ?
N1 C1 C2 121.08(15) . . ?
N2 C3 N3 110.4(2) . . ?
N2 C3 H3A 107.8(16) . . ?
N2 C3 H3B 108(2) . . ?
N3 C3 H3A 104.4(16) . . ?
N3 C3 H3B 113.2(19) . . ?
H3A C3 H3B 113(3) . . ?

_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_a
_database_code_depnum_ccdc_archive 'CCDC 1846310'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_audit_creation_date             2017-12-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 Cl N7 O7'
_chemical_formula_sum            'C4 H4 Cl N7 O7'
_chemical_formula_weight         297.59
_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                   8.1381(17)
_cell_length_b                   11.242(2)
_cell_length_c                   11.677(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.132(5)
_cell_angle_gamma                90
_cell_volume                     1026.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1913
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.533
_cell_measurement_theta_min      2.565
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0621 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.9148.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.443
_diffrn_reflns_theta_min         2.565
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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                1899
_reflns_number_total             2341
_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         0.683
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.055
_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)+(0.0589P)²+0.8221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1262
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.01931(8) 0.49336(6) 0.66309(6) 0.0344(2) Uani 1 1 d . . . . .
O4 O 0.1930(2) 0.18195(15) 0.69171(17) 0.0309(4) Uani 1 1 d . . . . .
O2 O 0.0610(2) 0.26545(17) 0.89188(16) 0.0347(5) Uani 1 1 d . . . . .
O6 O 0.6156(3) 0.17877(18) 0.70289(19) 0.0412(5) Uani 1 1 d . . . . .
N3 N 0.3991(2) 0.39952(18) 0.67680(17) 0.0200(4) Uani 1 1 d . . . . .
O3 O -0.0698(2) 0.24502(19) 0.62639(18) 0.0407(5) Uani 1 1 d . . . . .
O5 O 0.3655(3) 0.39366(19) 0.48682(17) 0.0392(5) Uani 1 1 d . . . . .
N2 N 0.4137(2) 0.39080(17) 0.88185(17) 0.0204(4) Uani 1 1 d . . . . .
O1 O 0.0801(3) 0.45668(19) 0.91354(18) 0.0401(5) Uani 1 1 d . . . . .
O7 O 0.6668(3) 0.16585(18) 0.8943(2) 0.0422(5) Uani 1 1 d . . . . .
N1 N 0.0873(2) 0.36478(19) 0.86166(18) 0.0233(4) Uani 1 1 d . . . . .
N7 N 0.0802(2) 0.25633(18) 0.67930(18) 0.0240(4) Uani 1 1 d . . . . .
N5 N 0.6642(2) 0.34749(17) 0.81257(18) 0.0213(4) Uani 1 1 d . . . . .
N6 N 0.6445(2) 0.22131(19) 0.8021(2) 0.0259(5) Uani 1 1 d . . . . .
N4 N 0.2932(3) 0.38559(19) 0.56437(18) 0.0267(5) Uani 1 1 d . . . . .
C2 C 0.3297(3) 0.38996(19) 0.7729(2) 0.0170(4) Uani 1 1 d . . . . .
C1 C 0.1355(3) 0.3762(2) 0.7424(2) 0.0185(5) Uani 1 1 d . . . . .
C3 C 0.5861(3) 0.4086(2) 0.7009(2) 0.0246(5) Uani 1 1 d . . . . .
H3A H 0.6231 0.3714 0.6353 0.030 Uiso 1 1 calc R . . . .
H3B H 0.6213 0.4932 0.7069 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6010(3) 0.3947(2) 0.9095(2) 0.0260(5) Uani 1 1 d . . . . .
H5A H 0.6398 0.4781 0.9255 0.031 Uiso 1 1 calc R . . . .
H5B H 0.6511 0.3480 0.9828 0.031 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
Cl1 C1 1.732(2) . ?
O4 N7 1.220(3) . ?
O2 N1 1.208(3) . ?
O6 N6 1.214(3) . ?
N3 N4 1.365(3) . ?
N3 C2 1.393(3) . ?
N3 C3 1.472(3) . ?
O3 N7 1.212(3) . ?
O5 N4 1.213(3) . ?
N2 C2 1.266(3) . ?
N2 C5 1.469(3) . ?
O1 N1 1.207(3) . ?
O7 N6 1.214(3) . ?
N1 C1 1.554(3) . ?
N7 C1 1.542(3) . ?
N5 N6 1.429(3) . ?
N5 C3 1.455(3) . ?
N5 C5 1.466(3) . ?
C2 C1 1.528(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 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
N4 N3 C2 118.49(18) . . ?
N4 N3 C3 122.32(19) . . ?
C2 N3 C3 118.70(18) . . ?
C2 N2 C5 117.3(2) . . ?
O2 N1 C1 116.58(19) . . ?
O1 N1 O2 127.4(2) . . ?
O1 N1 C1 116.0(2) . . ?
O4 N7 C1 115.60(18) . . ?
O3 N7 O4 127.3(2) . . ?
O3 N7 C1 117.0(2) . . ?
N6 N5 C3 112.40(19) . . ?
N6 N5 C5 111.73(19) . . ?
C3 N5 C5 111.17(19) . . ?
O6 N6 N5 117.4(2) . . ?
O7 N6 O6 125.9(2) . . ?
O7 N6 N5 116.6(2) . . ?
O5 N4 N3 113.7(2) . . ?
N3 C2 C1 116.39(18) . . ?
N2 C2 N3 125.6(2) . . ?
N2 C2 C1 118.0(2) . . ?
N1 C1 Cl1 107.80(14) . . ?
N7 C1 Cl1 111.46(15) . . ?
N7 C1 N1 104.07(17) . . ?
C2 C1 Cl1 115.03(16) . . ?
C2 C1 N1 107.57(17) . . ?
C2 C1 N7 110.22(17) . . ?
N3 C3 H3A 110.1 . . ?
N3 C3 H3B 110.1 . . ?
N5 C3 N3 108.06(18) . . ?
N5 C3 H3A 110.1 . . ?
N5 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N2 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
N5 C5 N2 112.64(18) . . ?
N5 C5 H5A 109.1 . . ?
N5 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?

_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_20180289-yc-40_0m
_database_code_depnum_ccdc_archive 'CCDC 1846311'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_audit_creation_date             2018-04-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 N7 O8'
_chemical_formula_sum            'C4 H5 N7 O8'
_chemical_formula_weight         279.15
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.913(11)
_cell_length_b                   5.827(3)
_cell_length_c                   18.914(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.724(13)
_cell_angle_gamma                90
_cell_volume                     2033.3(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    286
_cell_measurement_temperature    173
_cell_measurement_theta_max      16.69
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0898 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.8452.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13792
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.328
_diffrn_reflns_theta_min         1.724
_diffrn_ambient_temperature      173
_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_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                2520
_reflns_number_total             4094
_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         0.375
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      0.979
_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)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O12 O 0.52521(11) 0.4328(4) 0.19127(13) 0.0369(6) Uani 1 1 d . . . . .
O7 O 0.84745(13) 0.2793(4) 0.33469(12) 0.0390(6) Uani 1 1 d . . . . .
O11 O 0.45988(13) 0.4344(4) 0.08153(13) 0.0427(6) Uani 1 1 d . . . . .
O16 O 0.33107(12) 0.8899(4) 0.34870(14) 0.0419(6) Uani 1 1 d . . . . .
O8 O 0.89304(14) 0.3474(4) 0.44851(12) 0.0437(7) Uani 1 1 d . . . . .
N12 N 0.33045(13) 0.3632(4) 0.24712(13) 0.0218(6) Uani 1 1 d . . . . .
O6 O 0.60039(12) 0.6520(4) 0.32949(13) 0.0421(6) Uani 1 1 d . . . . .
N6 N 0.87042(13) 0.6442(4) 0.37093(13) 0.0220(6) Uani 1 1 d . . . . .
N4 N 0.74680(13) 0.7897(4) 0.32866(13) 0.0226(6) Uani 1 1 d . . . . .
N13 N 0.37311(12) 0.5320(4) 0.36794(13) 0.0220(6) Uani 1 1 d . . . . .
N5 N 0.80503(13) 0.8072(4) 0.45243(13) 0.0265(6) Uani 1 1 d . . . . .
H5 H 0.7999 0.8115 0.4975 0.032 Uiso 1 1 calc R . . . .
O15 O 0.44627(13) 0.8362(4) 0.38888(15) 0.0465(7) Uani 1 1 d . . . . .
N11 N 0.45538(12) 0.3700(4) 0.30249(13) 0.0227(6) Uani 1 1 d . . . . .
H11 H 0.5002 0.3706 0.2965 0.027 Uiso 1 1 calc R . . . .
N14 N 0.38442(14) 0.7677(4) 0.36734(14) 0.0282(6) Uani 1 1 d . . . . .
N2 N 0.65187(14) 0.7708(4) 0.47422(13) 0.0255(6) Uani 1 1 d . . . . .
N9 N 0.47013(14) 0.3922(4) 0.14565(15) 0.0273(6) Uani 1 1 d . . . . .
O1 O 0.71564(14) 1.2659(4) 0.40511(15) 0.0498(7) Uani 1 1 d . . . . .
O5 O 0.58844(12) 1.0205(4) 0.31053(14) 0.0490(7) Uani 1 1 d . . . . .
O10 O 0.47029(14) -0.0475(4) 0.13449(15) 0.0492(7) Uani 1 1 d . . . . .
O3 O 0.58951(12) 0.7214(5) 0.46807(13) 0.0486(7) Uani 1 1 d . . . . .
N7 N 0.86878(14) 0.4076(4) 0.38593(14) 0.0290(6) Uani 1 1 d . . . . .
O4 O 0.69955(14) 0.7429(5) 0.52764(13) 0.0559(8) Uani 1 1 d . . . . .
O14 O 0.32252(14) 0.4866(5) 0.10082(13) 0.0567(8) Uani 1 1 d . . . . .
N3 N 0.61486(14) 0.8514(5) 0.34348(14) 0.0311(6) Uani 1 1 d . . . . .
O9 O 0.40966(15) -0.1068(4) 0.21757(14) 0.0522(7) Uani 1 1 d . . . . .
N8 N 0.43303(15) 0.0119(4) 0.17577(16) 0.0336(7) Uani 1 1 d . . . . .
N10 N 0.34179(15) 0.2904(6) 0.11476(15) 0.0382(7) Uani 1 1 d . . . . .
N1 N 0.67499(16) 1.1478(4) 0.42978(16) 0.0368(7) Uani 1 1 d . . . . .
C2 C 0.74728(15) 0.8172(4) 0.39523(15) 0.0209(6) Uani 1 1 d . . . . .
C6 C 0.39713(15) 0.3476(4) 0.24598(15) 0.0192(6) Uani 1 1 d . . . . .
O13 O 0.31256(14) 0.1163(5) 0.08864(14) 0.0606(8) Uani 1 1 d . . . . .
C7 C 0.43816(15) 0.3928(5) 0.37334(16) 0.0236(7) Uani 1 1 d . . . . .
H7A H 0.4793 0.4658 0.4074 0.028 Uiso 1 1 calc R . . . .
H7B H 0.4303 0.2390 0.3924 0.028 Uiso 1 1 calc R . . . .
C3 C 0.81434(15) 0.7236(5) 0.30959(15) 0.0228(7) Uani 1 1 d . . . . .
H3A H 0.8333 0.8567 0.2871 0.027 Uiso 1 1 calc R . . . .
H3B H 0.8041 0.5998 0.2729 0.027 Uiso 1 1 calc R . . . .
O2 O 0.63410(18) 1.2103(4) 0.46646(19) 0.0749(10) Uani 1 1 d . . . . .
C4 C 0.87604(16) 0.7889(5) 0.43446(17) 0.0256(7) Uani 1 1 d . . . . .
H4A H 0.8935 0.9433 0.4246 0.031 Uiso 1 1 calc R . . . .
H4B H 0.9113 0.7219 0.4758 0.031 Uiso 1 1 calc R . . . .
C1 C 0.67487(15) 0.8896(5) 0.41083(15) 0.0229(7) Uani 1 1 d . . . . .
C5 C 0.41089(15) 0.2676(5) 0.17358(16) 0.0233(7) Uani 1 1 d . . . . .
C8 C 0.31170(15) 0.4422(5) 0.31389(16) 0.0245(7) Uani 1 1 d . . . . .
H8A H 0.2900 0.3128 0.3356 0.029 Uiso 1 1 calc R . . . .
H8B H 0.2745 0.5638 0.3017 0.029 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
O12 N9 1.221(3) . ?
O7 N7 1.220(3) . ?
O11 N9 1.210(3) . ?
O16 N14 1.222(3) . ?
O8 N7 1.223(3) . ?
N12 C6 1.269(4) . ?
N12 C8 1.459(4) . ?
O6 N3 1.210(3) . ?
N6 N7 1.409(3) . ?
N6 C3 1.464(3) . ?
N6 C4 1.453(4) . ?
N4 C2 1.267(4) . ?
N4 C3 1.454(4) . ?
N13 N14 1.390(3) . ?
N13 C7 1.458(4) . ?
N13 C8 1.465(4) . ?
N5 H5 0.8800 . ?
N5 C2 1.359(3) . ?
N5 C4 1.460(4) . ?
O15 N14 1.218(3) . ?
N11 H11 0.8800 . ?
N11 C6 1.362(3) . ?
N11 C7 1.453(4) . ?
N2 O3 1.195(3) . ?
N2 O4 1.208(3) . ?
N2 C1 1.528(4) . ?
N9 C5 1.524(4) . ?
O1 N1 1.200(4) . ?
O5 N3 1.213(3) . ?
O10 N8 1.212(3) . ?
O14 N10 1.211(4) . ?
N3 C1 1.524(4) . ?
O9 N8 1.205(4) . ?
N8 C5 1.546(4) . ?
N10 O13 1.208(4) . ?
N10 C5 1.524(4) . ?
N1 O2 1.203(4) . ?
N1 C1 1.547(4) . ?
C2 C1 1.523(4) . ?
C6 C5 1.522(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 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
C6 N12 C8 118.0(2) . . ?
N7 N6 C3 115.1(2) . . ?
N7 N6 C4 113.7(2) . . ?
C4 N6 C3 112.4(2) . . ?
C2 N4 C3 117.7(2) . . ?
N14 N13 C7 114.9(2) . . ?
N14 N13 C8 116.6(2) . . ?
C7 N13 C8 112.2(2) . . ?
C2 N5 H5 122.0 . . ?
C2 N5 C4 115.9(2) . . ?
C4 N5 H5 122.0 . . ?
C6 N11 H11 122.4 . . ?
C6 N11 C7 115.2(2) . . ?
C7 N11 H11 122.4 . . ?
O16 N14 N13 117.4(2) . . ?
O15 N14 O16 125.2(2) . . ?
O15 N14 N13 117.3(2) . . ?
O3 N2 O4 126.0(3) . . ?
O3 N2 C1 118.6(2) . . ?
O4 N2 C1 115.4(2) . . ?
O12 N9 C5 115.2(2) . . ?
O11 N9 O12 126.3(3) . . ?
O11 N9 C5 118.4(2) . . ?
O7 N7 O8 125.5(2) . . ?
O7 N7 N6 117.2(2) . . ?
O8 N7 N6 117.1(2) . . ?
O6 N3 O5 128.3(3) . . ?
O6 N3 C1 114.5(2) . . ?
O5 N3 C1 117.2(3) . . ?
O10 N8 C5 116.8(3) . . ?
O9 N8 O10 127.5(3) . . ?
O9 N8 C5 115.7(3) . . ?
O14 N10 C5 114.2(3) . . ?
O13 N10 O14 128.0(3) . . ?
O13 N10 C5 117.9(3) . . ?
O1 N1 O2 126.8(3) . . ?
O1 N1 C1 115.8(3) . . ?
O2 N1 C1 117.4(3) . . ?
N4 C2 N5 127.9(3) . . ?
N4 C2 C1 114.7(2) . . ?
N5 C2 C1 117.2(3) . . ?
N12 C6 N11 128.0(3) . . ?
N12 C6 C5 113.9(2) . . ?
N11 C6 C5 117.8(2) . . ?
N13 C7 H7A 109.6 . . ?
N13 C7 H7B 109.6 . . ?
N11 C7 N13 110.1(2) . . ?
N11 C7 H7A 109.6 . . ?
N11 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
N6 C3 H3A 108.7 . . ?
N6 C3 H3B 108.7 . . ?
N4 C3 N6 114.2(2) . . ?
N4 C3 H3A 108.7 . . ?
N4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N6 C4 N5 109.4(2) . . ?
N6 C4 H4A 109.8 . . ?
N6 C4 H4B 109.8 . . ?
N5 C4 H4A 109.8 . . ?
N5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N2 C1 N1 104.2(2) . . ?
N3 C1 N2 107.5(2) . . ?
N3 C1 N1 107.4(2) . . ?
C2 C1 N2 116.8(2) . . ?
C2 C1 N3 109.5(2) . . ?
C2 C1 N1 111.0(2) . . ?
N9 C5 N8 104.7(2) . . ?
N9 C5 N10 106.5(2) . . ?
N10 C5 N8 106.7(2) . . ?
C6 C5 N9 116.8(2) . . ?
C6 C5 N8 111.7(2) . . ?
C6 C5 N10 109.9(2) . . ?
N12 C8 N13 114.2(2) . . ?
N12 C8 H8A 108.7 . . ?
N12 C8 H8B 108.7 . . ?
N13 C8 H8A 108.7 . . ?
N13 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?

_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_20171156-yc-28_0m
_database_code_depnum_ccdc_archive 'CCDC 1846305'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_audit_creation_date             2018-07-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 Cl N7 O8'
_chemical_formula_sum            'C4 H4 Cl N7 O8'
_chemical_formula_weight         313.59
_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      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                   11.4945(17)
_cell_length_b                   11.5752(18)
_cell_length_c                   16.011(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2130.3(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5294
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0675 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.9053.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14748
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_min         2.544
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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                2112
_reflns_number_total             2430
_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         0.270
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.037
_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)+(0.0418P)²+0.7371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0784
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O7) \\sim Ueq, Uanis(O7A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Others
 Sof(O7A)=1-FVAR(1)
 Sof(O7)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl01 Cl 0.58975(3) 0.88279(3) 0.74674(2) 0.02284(11) Uani 1 1 d . . . . .
O5 O 0.55701(10) 0.62421(9) 0.73097(7) 0.0295(3) Uani 1 1 d . . . . .
O4 O 0.51585(12) 1.01445(9) 0.59970(7) 0.0382(3) Uani 1 1 d . . . . .
O8 O 0.56120(11) 0.49128(9) 0.42157(7) 0.0351(3) Uani 1 1 d . . . . .
O7 O 0.679(2) 0.454(2) 0.5091(19) 0.027(2) Uani 0.35(10) 1 d . U P A 1
O3 O 0.33919(10) 0.96376(10) 0.63098(8) 0.0402(3) Uani 1 1 d . . . . .
O2 O 0.32554(10) 0.72427(11) 0.66038(8) 0.0380(3) Uani 1 1 d . . . . .
N4 N 0.64964(10) 0.70032(9) 0.62150(7) 0.0192(2) Uani 1 1 d . . . . .
O1 O 0.36961(10) 0.78982(12) 0.78390(8) 0.0404(3) Uani 1 1 d . . . . .
O6 O 0.72414(12) 0.55246(11) 0.69318(8) 0.0465(3) Uani 1 1 d . . . . .
N5 N 0.51248(11) 0.77996(10) 0.52808(7) 0.0220(3) Uani 1 1 d . . . . .
N2 N 0.44372(11) 0.94993(10) 0.62890(8) 0.0251(3) Uani 1 1 d . . . . .
N6 N 0.65748(11) 0.63884(10) 0.47925(8) 0.0250(3) Uani 1 1 d . . . . .
N7 N 0.63318(12) 0.52113(10) 0.47356(8) 0.0264(3) Uani 1 1 d . . . . .
N3 N 0.64300(11) 0.61832(10) 0.68601(8) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.38598(10) 0.77742(11) 0.70959(8) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.54886(11) 0.76494(10) 0.60148(8) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.49357(11) 0.83804(11) 0.67072(8) 0.0176(3) Uani 1 1 d . . . . .
C3 C 0.72624(12) 0.67590(12) 0.55026(10) 0.0262(3) Uani 1 1 d . . . . .
H3A H 0.7707 0.7462 0.5355 0.031 Uiso 1 1 calc R . . . .
H3B H 0.7824 0.6146 0.5655 0.031 Uiso 1 1 calc R . . . .
C4 C 0.56409(15) 0.71977(12) 0.45721(9) 0.0284(3) Uani 1 1 d . . . . .
H4A H 0.5956 0.7779 0.4179 0.034 Uiso 1 1 calc R . . . .
H4B H 0.5021 0.6767 0.4277 0.034 Uiso 1 1 calc R . . . .
O7A O 0.697(2) 0.4573(11) 0.5229(15) 0.033(2) Uani 0.65(10) 1 d . U P A 2


_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
Cl01 C1 1.7240(13) . ?
O5 N3 1.2247(17) . ?
O4 N2 1.2099(18) . ?
O8 N7 1.2236(18) . ?
O7 N7 1.09(3) . ?
O3 N2 1.2126(17) . ?
O2 N1 1.2174(17) . ?
N4 N3 1.4049(16) . ?
N4 C2 1.4157(16) . ?
N4 C3 1.4684(18) . ?
O1 N1 1.2132(18) . ?
O6 N3 1.2100(16) . ?
N5 C2 1.2596(18) . ?
N5 C4 1.4577(18) . ?
N2 C1 1.5666(16) . ?
N6 N7 1.3938(17) . ?
N6 C3 1.450(2) . ?
N6 C4 1.4678(19) . ?
N7 O7A 1.30(2) . ?
N1 C1 1.5521(17) . ?
C2 C1 1.5325(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 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
N3 N4 C2 118.62(11) . . ?
N3 N4 C3 118.27(11) . . ?
C2 N4 C3 114.61(11) . . ?
C2 N5 C4 121.69(12) . . ?
O4 N2 O3 127.46(13) . . ?
O4 N2 C1 115.14(12) . . ?
O3 N2 C1 117.38(13) . . ?
N7 N6 C3 116.73(12) . . ?
N7 N6 C4 117.49(13) . . ?
C3 N6 C4 113.48(11) . . ?
O8 N7 N6 117.13(13) . . ?
O8 N7 O7A 129.1(10) . . ?
O7 N7 O8 118.6(15) . . ?
O7 N7 N6 124.1(15) . . ?
O7A N7 N6 113.7(10) . . ?
O5 N3 N4 116.00(11) . . ?
O6 N3 O5 126.97(13) . . ?
O6 N3 N4 116.97(13) . . ?
O2 N1 C1 115.07(12) . . ?
O1 N1 O2 127.30(13) . . ?
O1 N1 C1 117.61(12) . . ?
N4 C2 C1 117.86(11) . . ?
N5 C2 N4 123.77(12) . . ?
N5 C2 C1 117.46(11) . . ?
N2 C1 Cl01 106.73(9) . . ?
N1 C1 Cl01 111.32(9) . . ?
N1 C1 N2 104.69(10) . . ?
C2 C1 Cl01 114.25(9) . . ?
C2 C1 N2 107.40(10) . . ?
C2 C1 N1 111.77(10) . . ?
N4 C3 H3A 109.7 . . ?
N4 C3 H3B 109.7 . . ?
N6 C3 N4 109.83(11) . . ?
N6 C3 H3A 109.7 . . ?
N6 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N5 C4 N6 114.55(12) . . ?
N5 C4 H4A 108.6 . . ?
N5 C4 H4B 108.6 . . ?
N6 C4 H4A 108.6 . . ?
N6 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?

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