# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_mo_2017143_0m
_database_code_depnum_ccdc_archive 'CCDC 1558514'
_audit_update_record             
;
2017-09-03 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_audit_creation_date             2017-03-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H N4 O5, H4 N O'
_chemical_formula_sum            'C3 H5 N5 O6'
_chemical_formula_weight         207.12
_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                   6.7360(7)
_cell_length_b                   8.1254(9)
_cell_length_c                   8.4748(9)
_cell_angle_alpha                62.402(2)
_cell_angle_beta                 83.171(2)
_cell_angle_gamma                65.905(2)
_cell_volume                     373.84(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2555
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.04
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0472 before and 0.0358 after correction. The Ratio of minimum to maximum transmission is 0.9037. The λ/2 correction factor is 0.0015.'
_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    1.840
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.24
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4266
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.722
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1529
_reflns_number_total             1699
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.071
_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)+(0.0612P)²+0.0749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0995
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups, All O(H) groups
2.a Rotating group:
 O6(H6), N5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
O5 O 0.80369(15) 0.68264(14) 0.35839(12) 0.0270(2) Uani 1 1 d . . . . .
O3 O 0.85782(14) 0.22899(14) 0.85109(13) 0.0269(2) Uani 1 1 d . . . . .
O1 O 0.24444(16) 0.79432(13) 0.65419(13) 0.0302(2) Uani 1 1 d . . . . .
O2 O 0.22528(15) 0.53872(14) 0.89478(13) 0.0277(2) Uani 1 1 d . . . . .
O4 O 0.57608(15) 0.20220(14) 0.99592(13) 0.0295(2) Uani 1 1 d . . . . .
O6 O 0.70682(18) 0.99007(14) 0.73988(13) 0.0340(3) Uani 1 1 d . . . . .
H6 H 0.7038 0.9301 0.6794 0.041 Uiso 1 1 d GR . . . .
N2 N 0.65879(16) 0.30670(15) 0.87304(13) 0.0200(2) Uani 1 1 d . . . . .
N1 N 0.33073(16) 0.61501(15) 0.77051(13) 0.0202(2) Uani 1 1 d . . . . .
N5 N 0.81717(17) 0.84588(16) 0.90841(14) 0.0243(2) Uani 1 1 d . . . . .
H5A H 0.7360 0.7851 0.9727 0.029 Uiso 1 1 d GR . . . .
H5B H 0.9372 0.7585 0.8975 0.029 Uiso 1 1 d GR . . . .
N3 N 0.69084(17) 0.56391(17) 0.47065(14) 0.0247(2) Uani 1 1 d . . . . .
N4 N 0.73231(19) 0.74702(16) 0.58831(15) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.54590(18) 0.50756(17) 0.75604(15) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.65409(18) 0.60787(17) 0.60359(15) 0.0195(3) Uani 1 1 d . . . . .
C3 C 0.8206(2) 0.7837(2) 0.43797(19) 0.0283(3) Uani 1 1 d . . . . .
H3 H 0.8911 0.8749 0.3893 0.034 Uiso 1 1 calc R . . . .
H5C H 0.847(3) 0.918(3) 0.956(3) 0.044(5) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O5 0.0294(5) 0.0302(5) 0.0251(5) -0.0144(4) 0.0096(4) -0.0153(4)
O3 0.0172(4) 0.0254(5) 0.0316(5) -0.0120(4) 0.0007(3) -0.0036(3)
O1 0.0286(5) 0.0172(4) 0.0310(5) -0.0061(4) 0.0025(4) -0.0024(4)
O2 0.0246(4) 0.0242(5) 0.0299(5) -0.0120(4) 0.0107(4) -0.0085(4)
O4 0.0277(5) 0.0218(4) 0.0284(5) -0.0046(4) 0.0056(4) -0.0091(4)
O6 0.0467(6) 0.0236(5) 0.0259(5) -0.0111(4) -0.0070(4) -0.0064(4)
N2 0.0199(5) 0.0193(5) 0.0211(5) -0.0100(4) 0.0009(4) -0.0069(4)
N1 0.0217(5) 0.0184(5) 0.0213(5) -0.0106(4) 0.0024(4) -0.0071(4)
N5 0.0232(5) 0.0192(5) 0.0267(5) -0.0091(4) 0.0005(4) -0.0063(4)
N3 0.0256(5) 0.0300(6) 0.0245(5) -0.0147(5) 0.0079(4) -0.0156(4)
N4 0.0328(6) 0.0238(5) 0.0300(6) -0.0157(5) 0.0092(4) -0.0157(5)
C1 0.0203(5) 0.0184(5) 0.0189(5) -0.0090(5) 0.0021(4) -0.0072(4)
C2 0.0182(5) 0.0178(5) 0.0211(5) -0.0091(4) 0.0005(4) -0.0055(4)
C3 0.0329(7) 0.0234(6) 0.0327(7) -0.0147(5) 0.0103(5) -0.0146(5)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 N3 1.4108(14) . ?
O5 C3 1.3227(17) . ?
O3 N2 1.2606(13) . ?
O1 N1 1.2435(14) . ?
O2 N1 1.2549(14) . ?
O4 N2 1.2429(13) . ?
O6 H6 0.8613 . ?
O6 N5 1.3986(14) . ?
N2 C1 1.3754(15) . ?
N1 C1 1.3790(15) . ?
N5 H5A 0.8606 . ?
N5 H5B 0.8606 . ?
N5 H5C 0.94(2) . ?
N3 C2 1.3010(15) . ?
N4 C2 1.3811(16) . ?
N4 C3 1.2956(17) . ?
C1 C2 1.4663(16) . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O5 N3 106.32(9) . . ?
N5 O6 H6 109.7 . . ?
O3 N2 C1 116.30(10) . . ?
O4 N2 O3 119.81(10) . . ?
O4 N2 C1 123.90(10) . . ?
O1 N1 O2 120.82(10) . . ?
O1 N1 C1 116.67(10) . . ?
O2 N1 C1 122.51(10) . . ?
O6 N5 H5A 109.2 . . ?
O6 N5 H5B 109.8 . . ?
O6 N5 H5C 105.8(12) . . ?
H5A N5 H5B 109.4 . . ?
H5A N5 H5C 112.4 . . ?
H5B N5 H5C 110.2 . . ?
C2 N3 O5 103.42(10) . . ?
C3 N4 C2 102.25(11) . . ?
N2 C1 N1 122.54(11) . . ?
N2 C1 C2 118.73(10) . . ?
N1 C1 C2 118.62(10) . . ?
N3 C2 N4 114.09(11) . . ?
N3 C2 C1 120.69(11) . . ?
N4 C2 C1 125.18(11) . . ?
O5 C3 H3 123.0 . . ?
N4 C3 O5 113.92(12) . . ?
N4 C3 H3 123.0 . . ?

_iucr_refine_instructions_details 
;

    mo_2017143_0m.res created by SHELXL-2014/7

TITL mo_2017143_0m_a.res in P-1
REM Old TITL mo_2017143_0m in P-1
REM SHELXT solution in P-1
REM R1 0.122, Rweak 0.007, Alpha 0.030, Orientation as input
REM Formula found by SHELXT: C9 N3 O2
CELL 0.71073 6.736 8.1254 8.4748 62.402 83.171 65.905
ZERR 2 0.0007 0.0009 0.0009 0.002 0.002 0.002
LATT 1
SFAC C H N O
UNIT 6 10 10 12
 
L.S. 10
PLAN  20
TEMP -103.15
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\mo_2017143_0m.hkl">
REM </olex2.extras>
 
WGHT    0.061200    0.074900
FVAR       1.30211
O5    4    0.803694    0.682644    0.358393    11.00000    0.02945    0.03019 =
         0.02514   -0.01437    0.00964   -0.01534
O3    4    0.857819    0.228985    0.851087    11.00000    0.01724    0.02541 =
         0.03164   -0.01205    0.00073   -0.00361
O1    4    0.244444    0.794321    0.654194    11.00000    0.02865    0.01715 =
         0.03097   -0.00614    0.00250   -0.00241
O2    4    0.225278    0.538724    0.894780    11.00000    0.02458    0.02421 =
         0.02993   -0.01201    0.01066   -0.00852
O4    4    0.576077    0.202202    0.995916    11.00000    0.02771    0.02177 =
         0.02836   -0.00460    0.00556   -0.00914
O6    4    0.706818    0.990067    0.739876    11.00000    0.04669    0.02357 =
         0.02590   -0.01108   -0.00698   -0.00637
AFIX   7
H6    2    0.703834    0.930099    0.679443    11.00000   -1.20000
AFIX   0
 
N2    3    0.658793    0.306698    0.873042    11.00000    0.01986    0.01933 =
         0.02106   -0.00996    0.00094   -0.00692
N1    3    0.330729    0.615011    0.770507    11.00000    0.02172    0.01843 =
         0.02127   -0.01061    0.00238   -0.00706
N5    3    0.817168    0.845880    0.908407    11.00000    0.02316    0.01920 =
         0.02674   -0.00908    0.00055   -0.00626
AFIX   7
H5A   2    0.735964    0.785082    0.972743    11.00000   -1.20000
H5B   2    0.937172    0.758467    0.897502    11.00000   -1.20000
AFIX   0
 
N3    3    0.690837    0.563906    0.470649    11.00000    0.02557    0.03002 =
         0.02455   -0.01468    0.00795   -0.01557
N4    3    0.732309    0.747024    0.588310    11.00000    0.03283    0.02376 =
         0.03004   -0.01567    0.00924   -0.01571
C1    1    0.545897    0.507556    0.756036    11.00000    0.02031    0.01844 =
         0.01893   -0.00905    0.00209   -0.00720
C2    1    0.654094    0.607868    0.603590    11.00000    0.01822    0.01784 =
         0.02114   -0.00913    0.00047   -0.00552
C3    1    0.820612    0.783677    0.437973    11.00000    0.03286    0.02335 =
         0.03269   -0.01473    0.01025   -0.01455
AFIX  43
H3    2    0.891133    0.874873    0.389300    11.00000   -1.20000
AFIX   0
 
H5C   2    0.846846    0.918399    0.956206    11.00000    0.04383
HKLF 4
 
REM  mo_2017143_0m_a.res in P-1
REM R1 =  0.0333 for    1529 Fo > 4sig(Fo)  and  0.0367 for all    1699 data
REM    133 parameters refined using      0 restraints
 
END  
     
WGHT      0.0614      0.0754 

REM Highest difference peak  0.301,  deepest hole -0.266,  1-sigma level  0.056
Q1    1   0.5932  0.5646  0.6857  11.00000  0.05    0.30
Q2    1   0.4560  0.5478  0.7590  11.00000  0.05    0.24
Q3    1   0.5848  0.4111  0.7911  11.00000  0.05    0.24
Q4    1   0.6161  0.6208  0.5305  11.00000  0.05    0.21
Q5    1   0.7540  0.7819  0.6563  11.00000  0.05    0.19
Q6    1   0.8628  0.8985  0.3049  11.00000  0.05    0.17
Q7    1   0.6876  0.6822  0.6086  11.00000  0.05    0.16
Q8    1   0.7211  0.8141  0.4732  11.00000  0.05    0.15
Q9    1   0.6441  0.7233  0.5611  11.00000  0.05    0.15
Q10   1   0.5770  0.6016  0.3984  11.00000  0.05    0.15
Q11   1   0.5083  0.2490  1.0403  11.00000  0.05    0.15
Q12   1   0.4456  0.2375  0.9660  11.00000  0.05    0.15
Q13   1   0.2766  0.3962  0.9741  11.00000  0.05    0.14
Q14   1   0.5208  0.5151  0.9388  11.00000  0.05    0.13
Q15   1   0.9240  0.1378  0.9005  11.00000  0.05    0.13
Q16   1   0.1083  0.5829  0.7977  11.00000  0.05    0.12
Q17   1   0.9185  0.5450  0.6751  11.00000  0.05    0.12
Q18   1   0.7543  0.8869  0.9888  11.00000  0.05    0.12
Q19   1   0.5170  1.0760  0.6812  11.00000  0.05    0.12
Q20   1   0.8382  0.7190  0.4159  11.00000  0.05    0.12

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0333 for 1529 Fo > 4sig(Fo) and 0.0367 for all 4266 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.30, deepest hole -0.27
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0367
  REM R1_gt = 0.0333
  REM wR_ref = 0.0995
  REM GOOF = 1.071
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 4266
  REM Reflections_gt = 1529
  REM Parameters = n/a
  REM Hole = -0.27
  REM Peak = 0.30
  REM Flack = n/a

  
;
_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 1558516'
_audit_update_record             
;
2017-09-03 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_audit_creation_date             2017-03-14
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H K N4 O5'
_chemical_formula_sum            'C3 H K N4 O5'
_chemical_formula_weight         212.18
_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'
K K 0.2009 0.2494 '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                   6.8618(10)
_cell_length_b                   7.1833(10)
_cell_length_c                   7.7371(11)
_cell_angle_alpha                84.776(3)
_cell_angle_beta                 82.401(3)
_cell_angle_gamma                64.520(2)
_cell_volume                     341.00(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0691 before and 0.0315 after correction.
 The Ratio of minimum to maximum transmission is 0.75.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0789 before and 0.0473 after correction.
 The Ratio of minimum to maximum transmission is 0.75.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 5733 reflections, Rint = 0.0640
 (4661 with I > 3sig(I), Rint = 0.0637)
;
_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    2.066
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   0.856
_exptl_transmission_factor_min   0.830
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.962
_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            1511
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         2.658
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1438
_reflns_number_total             1511
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.154
_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)+(0.0602P)²+0.2884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1056
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.037
;
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
K1 K 0.18853(7) 0.16397(6) 0.93814(5) 0.01425(17) Uani 1 1 d . . . . .
O4 O 0.1996(3) 0.8253(2) 0.7799(2) 0.0191(3) Uani 1 1 d . . . . .
O3 O 0.1990(3) 0.5402(2) 0.9001(2) 0.0199(3) Uani 1 1 d . . . . .
O1 O 0.5727(3) 0.2182(2) 0.8792(2) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.8376(3) 0.2704(2) 0.7290(2) 0.0222(4) Uani 1 1 d . . . . .
O5 O 0.7292(3) 0.8136(3) 0.4428(2) 0.0228(4) Uani 1 1 d . . . . .
N1 N 0.6425(3) 0.3353(3) 0.7915(2) 0.0135(4) Uani 1 1 d . . . . .
N2 N 0.2976(3) 0.6344(3) 0.8150(2) 0.0126(3) Uani 1 1 d . . . . .
C2 C 0.6138(3) 0.6664(3) 0.6564(3) 0.0124(4) Uani 1 1 d . . . . .
N4 N 0.7072(3) 0.7724(3) 0.7290(2) 0.0214(4) Uani 1 1 d . . . . .
N3 N 0.6213(4) 0.6837(3) 0.4878(2) 0.0223(4) Uani 1 1 d . . . . .
C1 C 0.5138(3) 0.5409(3) 0.7569(2) 0.0121(4) Uani 1 1 d . . . . .
C3 C 0.7724(4) 0.8565(4) 0.5930(3) 0.0215(5) Uani 1 1 d . . . . .
H3 H 0.843(5) 0.952(4) 0.593(4) 0.021(7) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
K1 0.0153(3) 0.0133(2) 0.0152(2) -0.00109(15) -0.00253(16) -0.00666(18)
O4 0.0164(8) 0.0084(6) 0.0296(8) 0.0002(6) -0.0047(6) -0.0020(6)
O3 0.0172(8) 0.0171(7) 0.0249(8) -0.0007(6) 0.0057(6) -0.0092(6)
O1 0.0212(8) 0.0130(7) 0.0203(7) 0.0040(5) -0.0035(6) -0.0071(6)
O2 0.0101(7) 0.0202(7) 0.0313(9) -0.0045(6) 0.0009(6) -0.0019(6)
O5 0.0303(9) 0.0304(8) 0.0160(7) 0.0005(6) 0.0009(6) -0.0219(8)
N1 0.0147(9) 0.0132(8) 0.0127(8) -0.0013(6) -0.0035(6) -0.0053(7)
N2 0.0136(8) 0.0108(7) 0.0136(8) -0.0019(6) -0.0015(6) -0.0051(6)
C2 0.0118(9) 0.0126(8) 0.0137(9) -0.0008(7) -0.0016(7) -0.0057(7)
N4 0.0308(11) 0.0289(10) 0.0160(8) 0.0011(7) -0.0050(7) -0.0233(9)
N3 0.0312(11) 0.0302(10) 0.0163(9) 0.0002(7) -0.0017(8) -0.0236(9)
C1 0.0127(10) 0.0115(8) 0.0133(9) 0.0000(7) -0.0022(7) -0.0060(7)
C3 0.0256(12) 0.0261(11) 0.0201(10) 0.0015(8) -0.0030(9) -0.0181(10)

_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
K1 K1 4.1638(9) 2_557 ?
K1 K1 4.0921(10) 2_657 ?
K1 O4 3.1896(17) 2_567 ?
K1 O4 2.7896(16) 1_545 ?
K1 O3 2.7227(16) . ?
K1 O3 2.8098(16) 2_567 ?
K1 O1 2.8006(17) . ?
K1 O1 2.8728(15) 2_657 ?
K1 O2 2.8675(18) 1_455 ?
K1 O5 2.9294(17) 2_666 ?
K1 N2 3.3965(18) 2_567 ?
K1 N4 2.8873(19) 2_667 ?
O4 K1 3.1897(17) 2_567 ?
O4 K1 2.7896(16) 1_565 ?
O4 N2 1.262(2) . ?
O3 K1 2.8098(16) 2_567 ?
O3 N2 1.243(2) . ?
O1 K1 2.8728(15) 2_657 ?
O1 N1 1.247(2) . ?
O2 K1 2.8676(18) 1_655 ?
O2 N1 1.256(2) . ?
O5 K1 2.9294(17) 2_666 ?
O5 N3 1.416(2) . ?
O5 C3 1.330(3) . ?
N1 C1 1.379(2) . ?
N2 K1 3.3965(18) 2_567 ?
N2 C1 1.369(3) . ?
C2 N4 1.378(3) . ?
C2 N3 1.295(3) . ?
C2 C1 1.467(3) . ?
N4 K1 2.8873(19) 2_667 ?
N4 C3 1.290(3) . ?
C3 H3 0.99(3) . ?

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
K1 K1 K1 112.43(2) 2_657 2_557 ?
O4 K1 K1 118.37(3) 2_567 2_657 ?
O4 K1 K1 49.96(4) 1_545 2_557 ?
O4 K1 K1 91.50(4) 1_545 2_657 ?
O4 K1 K1 42.03(3) 2_567 2_557 ?
O4 K1 O4 91.99(5) 1_545 2_567 ?
O4 K1 O3 121.73(5) 1_545 2_567 ?
O4 K1 O1 115.06(5) 1_545 . ?
O4 K1 O1 67.93(5) 1_545 2_657 ?
O4 K1 O2 66.97(5) 1_545 1_455 ?
O4 K1 O5 67.05(5) 1_545 2_666 ?
O4 K1 N2 105.94(5) 1_545 2_567 ?
O4 K1 N2 21.80(4) 2_567 2_567 ?
O4 K1 N4 134.59(5) 1_545 2_667 ?
O3 K1 K1 77.39(4) 2_567 2_557 ?
O3 K1 K1 146.99(4) . 2_557 ?
O3 K1 K1 136.09(4) 2_567 2_657 ?
O3 K1 K1 96.71(4) . 2_657 ?
O3 K1 O4 148.09(5) . 1_545 ?
O3 K1 O4 41.85(4) 2_567 2_567 ?
O3 K1 O4 110.63(4) . 2_567 ?
O3 K1 O3 70.73(5) . 2_567 ?
O3 K1 O1 56.36(5) . . ?
O3 K1 O1 134.95(5) . 2_657 ?
O3 K1 O1 120.10(5) 2_567 2_657 ?
O3 K1 O2 95.49(5) . 1_455 ?
O3 K1 O2 69.13(5) 2_567 1_455 ?
O3 K1 O5 81.16(5) . 2_666 ?
O3 K1 O5 118.58(5) 2_567 2_666 ?
O3 K1 N2 90.88(4) . 2_567 ?
O3 K1 N2 20.43(4) 2_567 2_567 ?
O3 K1 N4 74.37(6) 2_567 2_667 ?
O3 K1 N4 75.32(5) . 2_667 ?
O1 K1 K1 156.07(3) . 2_557 ?
O1 K1 K1 44.54(3) . 2_657 ?
O1 K1 K1 43.14(3) 2_657 2_657 ?
O1 K1 K1 69.66(3) 2_657 2_557 ?
O1 K1 O4 145.36(5) . 2_567 ?
O1 K1 O4 82.81(4) 2_657 2_567 ?
O1 K1 O3 122.57(5) . 2_567 ?
O1 K1 O1 87.69(4) . 2_657 ?
O1 K1 O2 131.84(5) . 1_455 ?
O1 K1 O5 75.89(5) . 2_666 ?
O1 K1 O5 118.47(5) 2_657 2_666 ?
O1 K1 N2 138.68(5) . 2_567 ?
O1 K1 N2 103.52(4) 2_657 2_567 ?
O1 K1 N4 72.32(5) . 2_667 ?
O1 K1 N4 67.74(5) 2_657 2_667 ?
O2 K1 K1 64.55(4) 1_455 2_557 ?
O2 K1 K1 154.63(4) 1_455 2_657 ?
O2 K1 O4 77.36(5) 1_455 2_567 ?
O2 K1 O1 129.55(5) 1_455 2_657 ?
O2 K1 O5 60.46(5) 1_455 2_666 ?
O2 K1 N2 69.09(5) 1_455 2_567 ?
O2 K1 N4 143.33(6) 1_455 2_667 ?
O5 K1 K1 107.59(3) 2_666 2_557 ?
O5 K1 K1 99.66(4) 2_666 2_657 ?
O5 K1 O4 137.35(5) 2_666 2_567 ?
O5 K1 N2 127.64(5) 2_666 2_567 ?
N2 K1 K1 132.69(3) 2_567 2_657 ?
N2 K1 K1 58.18(3) 2_567 2_557 ?
N4 K1 K1 104.45(4) 2_667 2_557 ?
N4 K1 K1 61.73(4) 2_667 2_657 ?
N4 K1 O4 73.24(5) 2_667 2_567 ?
N4 K1 O5 147.37(5) 2_667 2_666 ?
N4 K1 N2 75.55(5) 2_667 2_567 ?
K1 O4 K1 88.01(5) 1_565 2_567 ?
N2 O4 K1 130.63(13) . 1_565 ?
N2 O4 K1 88.36(11) . 2_567 ?
K1 O3 K1 109.27(5) . 2_567 ?
N2 O3 K1 107.47(12) . 2_567 ?
N2 O3 K1 141.99(13) . . ?
K1 O1 K1 92.31(4) . 2_657 ?
N1 O1 K1 128.66(12) . 2_657 ?
N1 O1 K1 138.34(12) . . ?
N1 O2 K1 123.22(13) . 1_655 ?
N3 O5 K1 108.31(11) . 2_666 ?
C3 O5 K1 145.42(13) . 2_666 ?
C3 O5 N3 105.64(16) . . ?
O1 N1 O2 121.00(17) . . ?
O1 N1 C1 123.01(17) . . ?
O2 N1 C1 115.99(17) . . ?
O4 N2 K1 69.84(11) . 2_567 ?
O4 N2 C1 116.88(17) . . ?
O3 N2 K1 52.10(10) . 2_567 ?
O3 N2 O4 120.23(17) . . ?
O3 N2 C1 122.89(17) . . ?
C1 N2 K1 165.09(13) . 2_567 ?
N4 C2 C1 124.31(18) . . ?
N3 C2 N4 114.64(18) . . ?
N3 C2 C1 121.05(18) . . ?
C2 N4 K1 140.88(14) . 2_667 ?
C3 N4 K1 116.95(14) . 2_667 ?
C3 N4 C2 102.04(18) . . ?
C2 N3 O5 103.39(17) . . ?
N1 C1 C2 118.54(17) . . ?
N2 C1 N1 123.04(17) . . ?
N2 C1 C2 118.41(17) . . ?
O5 C3 H3 119.3(16) . . ?
N4 C3 O5 114.29(19) . . ?
N4 C3 H3 126.3(16) . . ?

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
K1 O4 N2 K1 85.97(13) 1_565 . . 2_567 ?
K1 O4 N2 O3 99.7(2) 1_565 . . . ?
K1 O4 N2 O3 13.75(18) 2_567 . . . ?
K1 O4 N2 C1 -165.47(15) 2_567 . . . ?
K1 O4 N2 C1 -79.5(2) 1_565 . . . ?
K1 O3 N2 K1 164.7(2) . . . 2_567 ?
K1 O3 N2 O4 148.22(16) . . . . ?
K1 O3 N2 O4 -16.4(2) 2_567 . . . ?
K1 O3 N2 C1 162.74(15) 2_567 . . . ?
K1 O3 N2 C1 -32.6(3) . . . . ?
K1 O1 N1 O2 21.5(3) 2_657 . . . ?
K1 O1 N1 O2 -146.17(16) . . . . ?
K1 O1 N1 C1 33.9(3) . . . . ?
K1 O1 N1 C1 -158.48(14) 2_657 . . . ?
K1 O2 N1 O1 -71.2(2) 1_655 . . . ?
K1 O2 N1 C1 108.76(16) 1_655 . . . ?
K1 O5 N3 C2 173.37(14) 2_666 . . . ?
K1 O5 C3 N4 -168.77(18) 2_666 . . . ?
K1 N2 C1 N1 63.8(5) 2_567 . . . ?
K1 N2 C1 C2 -114.9(5) 2_567 . . . ?
K1 N4 C3 O5 176.82(15) 2_667 . . . ?
O4 N2 C1 N1 177.50(18) . . . . ?
O4 N2 C1 C2 -1.2(3) . . . . ?
O3 N2 C1 N1 -1.7(3) . . . . ?
O3 N2 C1 C2 179.56(18) . . . . ?
O1 N1 C1 N2 -0.4(3) . . . . ?
O1 N1 C1 C2 178.29(17) . . . . ?
O2 N1 C1 N2 179.62(18) . . . . ?
O2 N1 C1 C2 -1.6(3) . . . . ?
C2 N4 C3 O5 0.0(3) . . . . ?
N4 C2 N3 O5 -0.1(3) . . . . ?
N4 C2 C1 N1 -89.3(3) . . . . ?
N4 C2 C1 N2 89.5(3) . . . . ?
N3 O5 C3 N4 0.0(3) . . . . ?
N3 C2 N4 K1 -175.47(18) . . . 2_667 ?
N3 C2 N4 C3 0.1(3) . . . . ?
N3 C2 C1 N1 90.2(3) . . . . ?
N3 C2 C1 N2 -91.0(3) . . . . ?
C1 C2 N4 K1 4.1(4) . . . 2_667 ?
C1 C2 N4 C3 179.6(2) . . . . ?
C1 C2 N3 O5 -179.67(17) . . . . ?
C3 O5 N3 C2 0.1(2) . . . . ?

_iucr_refine_instructions_details 
;

    twin4.res created by SHELXL-2014/7

TITL twin4_a.res in P-1
REM Old TITL twin4 in P-1 #2
REM SHELXT solution in P-1
REM R1 0.098, Rweak 0.009, Alpha 0.046, Orientation as input
REM Formula found by SHELXT: C7 N2 O3 Cl
CELL 0.71073 6.8618 7.1833 7.7371 84.776 82.401 64.52
ZERR 2 0.001 0.001 0.0011 0.003 0.003 0.002
LATT 1
SFAC C H K N O
UNIT 6 2 2 8 10
 
L.S. 10
PLAN  -20 0 0
TEMP -103.15
BOND $H
LIST 6
MORE -1
CONF
fmap 2
acta
OMIT 3 2 4
OMIT -4 -2 3
OMIT 1 0 3
OMIT -2 -1 2
OMIT 1 2 2
REM <olex2.extras>
REM <HklSrc "%.\\twin4.hkl">
REM </olex2.extras>
 
WGHT    0.060200    0.288400
FVAR       0.45579
K1    3    0.188527    0.163967    0.938138    11.00000    0.01531    0.01327 =
         0.01521   -0.00109   -0.00253   -0.00666
O4    5    0.199604    0.825263    0.779940    11.00000    0.01644    0.00840 =
         0.02961    0.00016   -0.00468   -0.00202
O3    5    0.198993    0.540219    0.900105    11.00000    0.01724    0.01710 =
         0.02493   -0.00066    0.00573   -0.00923
O1    5    0.572746    0.218168    0.879201    11.00000    0.02125    0.01298 =
         0.02032    0.00396   -0.00348   -0.00709
O2    5    0.837620    0.270383    0.728968    11.00000    0.01008    0.02018 =
         0.03133   -0.00452    0.00085   -0.00193
O5    5    0.729221    0.813589    0.442758    11.00000    0.03031    0.03038 =
         0.01598    0.00047    0.00088   -0.02191
N1    4    0.642469    0.335283    0.791451    11.00000    0.01472    0.01323 =
         0.01269   -0.00130   -0.00353   -0.00530
N2    4    0.297630    0.634434    0.814970    11.00000    0.01355    0.01084 =
         0.01358   -0.00186   -0.00151   -0.00505
C2    1    0.613839    0.666353    0.656364    11.00000    0.01179    0.01258 =
         0.01370   -0.00077   -0.00159   -0.00573
N4    4    0.707189    0.772426    0.729000    11.00000    0.03084    0.02889 =
         0.01603    0.00108   -0.00498   -0.02328
N3    4    0.621331    0.683742    0.487805    11.00000    0.03119    0.03021 =
         0.01630    0.00018   -0.00172   -0.02365
C1    1    0.513776    0.540860    0.756947    11.00000    0.01274    0.01151 =
         0.01325   -0.00003   -0.00221   -0.00598
C3    1    0.772377    0.856545    0.593043    11.00000    0.02556    0.02608 =
         0.02014    0.00148   -0.00299   -0.01811
H3    2    0.842693    0.951688    0.592509    11.00000    0.02054
HKLF 4
 
REM  twin4_a.res in P-1
REM R1 =  0.0330 for    1438 Fo > 4sig(Fo)  and  0.0343 for all    1511 data
REM    122 parameters refined using      0 restraints
 
END  
     
WGHT      0.0598      0.2883 

REM Highest difference peak  0.371,  deepest hole -0.500,  1-sigma level  0.119
Q1    1   0.4180  0.5364  0.7291  11.00000  0.05    0.37
Q2    1   0.5861  1.0210  0.4428  11.00000  0.05    0.32
Q3    1   0.5781  0.6023  0.7063  11.00000  0.05    0.31
Q4    1   0.6945  0.6784  0.6937  11.00000  0.05    0.31
Q5    1   0.3181  0.4224  1.0830  11.00000  0.05    0.31
Q6    1   0.9117  1.0377  0.6456  11.00000  0.05    0.30
Q7    1   0.5749  0.4707  0.8090  11.00000  0.05    0.28
Q8    1   0.6163  0.5824  0.4198  11.00000  0.05    0.28
Q9    1   0.5218 -0.0027  0.6898  11.00000  0.05    0.28
Q10   1   0.4120 -0.0012  1.0993  11.00000  0.05    0.28
Q11   1   0.4689  0.5042  0.6052  11.00000  0.05    0.27
Q12   1   0.4575  0.0255  0.9384  11.00000  0.05    0.26
Q13   1   0.5319  0.4434  0.7247  11.00000  0.05    0.26
Q14   1   0.1170  0.5438  0.8763  11.00000  0.05    0.25
Q15   1   0.7466  1.0388  0.5636  11.00000  0.05    0.25
Q16   1   0.5000  0.0000  1.0000  10.50000  0.05    0.25
Q17   1   0.2519  0.4210  0.6346  11.00000  0.05    0.25
Q18   1   0.0504 -0.0518  1.1344  11.00000  0.05    0.25
Q19   1   0.2211  0.1322  0.6418  11.00000  0.05    0.24
Q20   1   1.0139  0.9088  0.6431  11.00000  0.05    0.23

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0330 for 1438 Fo > 4sig(Fo) and 0.0343 for all 1516 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.37, deepest hole -0.50
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0343
  REM R1_gt = 0.0330
  REM wR_ref = 0.1056
  REM GOOF = 1.154
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1516
  REM Reflections_gt = 1438
  REM Parameters = n/a
  REM Hole = -0.50
  REM Peak = 0.37
  REM Flack = n/a

  
;
_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_2017369-yc-17_0m
_database_code_depnum_ccdc_archive 'CCDC 1558529'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H N6 O2, H4 N'
_chemical_formula_sum            'C3 H5 N7 O2'
_chemical_formula_weight         171.14
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   3.7059(9)
_cell_length_b                   25.344(6)
_cell_length_c                   7.2132(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.824(4)
_cell_angle_gamma                90
_cell_volume                     663.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    956
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      3.22
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_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    1.714
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2873
_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         27.428
_diffrn_reflns_theta_min         3.215
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1276
_reflns_number_total             1420
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1420
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.032
_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)+(0.0339P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(2)
 0(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H,H) groups
3. Restrained distances
 N7-H7B
 0.82 with sigma of 0.01
 N7-H7A
 0.82 with sigma of 0.01
 H7B-H7A
 1.296731 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.029
;
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
N5 N 0.1449(7) 0.21626(8) 1.0208(4) 0.0238(6) Uani 1 1 d . . . . .
O1 O 0.2113(6) 0.04338(7) 1.0221(3) 0.0267(5) Uani 1 1 d . . . . .
O2 O 0.3058(6) 0.19329(8) 0.7539(3) 0.0298(5) Uani 1 1 d . . . . .
N7 N 0.5970(7) 0.04836(10) 0.7014(3) 0.0198(5) Uani 1 1 d D . . . .
H7A H 0.771(7) 0.0390(12) 0.785(4) 0.030 Uiso 1 1 d DR . . . .
H7B H 0.676(8) 0.0643(12) 0.619(3) 0.030 Uiso 1 1 d DR . . . .
N2 N 0.0088(6) 0.05622(9) 1.3013(3) 0.0250(6) Uani 1 1 d . . . . .
N3 N -0.0882(7) 0.09743(9) 1.3910(3) 0.0266(6) Uani 1 1 d . . . . .
N4 N -0.0544(7) 0.14204(9) 1.2967(4) 0.0214(5) Uani 1 1 d . . . . .
N6 N 0.2427(8) 0.14581(9) 0.8443(4) 0.0261(6) Uani 1 1 d . . . . .
C3 C 0.2424(8) 0.23186(11) 0.8675(4) 0.0278(7) Uani 1 1 d . . . . .
H3 H 0.2667 0.2681 0.8385 0.033 Uiso 1 1 calc R . . . .
C2 C 0.1498(7) 0.16225(10) 0.9998(4) 0.0182(6) Uani 1 1 d . . . . .
C1 C 0.0648(7) 0.12722(10) 1.1436(4) 0.0176(6) Uani 1 1 d . . . . .
N1 N 0.1027(6) 0.07481(8) 1.1458(3) 0.0197(5) Uani 1 1 d . . . . .
H7C H 0.459(11) 0.0661(15) 0.759(6) 0.037(10) Uiso 1 1 d . . . . .
H7D H 0.460(9) 0.0209(14) 0.649(5) 0.026(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N5 0.0329(14) 0.0157(11) 0.0236(14) 0.0041(11) 0.0079(11) -0.0002(10)
O1 0.0382(13) 0.0185(10) 0.0220(11) -0.0040(9) 0.0028(9) 0.0076(8)
O2 0.0413(14) 0.0247(11) 0.0256(13) 0.0063(9) 0.0123(10) -0.0016(9)
N7 0.0223(12) 0.0203(13) 0.0177(13) -0.0001(10) 0.0062(10) 0.0009(10)
N2 0.0324(14) 0.0216(12) 0.0190(13) 0.0038(11) 0.0005(11) -0.0051(10)
N3 0.0317(14) 0.0274(13) 0.0212(15) 0.0033(10) 0.0061(11) -0.0060(11)
N4 0.0262(13) 0.0208(11) 0.0181(13) -0.0001(10) 0.0064(10) -0.0012(9)
N6 0.0374(15) 0.0200(13) 0.0237(13) 0.0042(11) 0.0126(12) 0.0009(10)
C3 0.0312(17) 0.0189(14) 0.033(2) 0.0045(13) 0.0062(14) -0.0001(11)
C2 0.0180(13) 0.0166(12) 0.0191(15) 0.0021(11) 0.0015(11) 0.0016(11)
C1 0.0188(13) 0.0155(12) 0.0180(14) -0.0002(11) 0.0023(12) 0.0002(10)
N1 0.0229(12) 0.0175(11) 0.0170(11) -0.0005(10) 0.0003(10) -0.0001(9)

_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
N5 C3 1.293(4) . ?
N5 C2 1.378(3) . ?
O1 N1 1.319(3) . ?
O2 N6 1.411(3) . ?
O2 C3 1.327(4) . ?
N7 H7A 0.823(14) . ?
N7 H7B 0.821(14) . ?
N7 H7C 0.85(4) . ?
N7 H7D 0.90(4) . ?
N2 N3 1.317(3) . ?
N2 N1 1.328(3) . ?
N3 N4 1.338(3) . ?
N4 C1 1.325(4) . ?
N6 C2 1.307(4) . ?
C3 H3 0.9500 . ?
C2 C1 1.448(3) . ?
C1 N1 1.336(3) . ?

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 N5 C2 101.4(2) . . ?
C3 O2 N6 106.0(2) . . ?
H7A N7 H7B 109(3) . . ?
H7A N7 H7C 104(3) . . ?
H7A N7 H7D 112(3) . . ?
H7B N7 H7C 116(3) . . ?
H7B N7 H7D 109(3) . . ?
H7C N7 H7D 106(3) . . ?
N3 N2 N1 106.2(2) . . ?
N2 N3 N4 110.9(2) . . ?
C1 N4 N3 105.4(2) . . ?
C2 N6 O2 102.9(2) . . ?
N5 C3 O2 114.7(2) . . ?
N5 C3 H3 122.6 . . ?
O2 C3 H3 122.6 . . ?
N5 C2 C1 121.4(2) . . ?
N6 C2 N5 115.0(2) . . ?
N6 C2 C1 123.6(2) . . ?
N4 C1 C2 125.6(2) . . ?
N4 C1 N1 108.9(2) . . ?
N1 C1 C2 125.5(2) . . ?
O1 N1 N2 121.8(2) . . ?
O1 N1 C1 129.7(2) . . ?
N2 N1 C1 108.5(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
N5 C2 C1 N4 6.2(4) . . . . ?
N5 C2 C1 N1 -172.0(2) . . . . ?
O2 N6 C2 N5 0.1(3) . . . . ?
O2 N6 C2 C1 -178.6(2) . . . . ?
N2 N3 N4 C1 0.5(3) . . . . ?
N3 N2 N1 O1 -179.3(2) . . . . ?
N3 N2 N1 C1 0.6(3) . . . . ?
N3 N4 C1 C2 -178.6(3) . . . . ?
N3 N4 C1 N1 -0.1(3) . . . . ?
N4 C1 N1 O1 179.6(3) . . . . ?
N4 C1 N1 N2 -0.3(3) . . . . ?
N6 O2 C3 N5 -0.2(4) . . . . ?
N6 C2 C1 N4 -175.1(3) . . . . ?
N6 C2 C1 N1 6.6(4) . . . . ?
C3 N5 C2 N6 -0.2(4) . . . . ?
C3 N5 C2 C1 178.5(2) . . . . ?
C3 O2 N6 C2 0.0(3) . . . . ?
C2 N5 C3 O2 0.2(4) . . . . ?
C2 C1 N1 O1 -2.0(5) . . . . ?
C2 C1 N1 N2 178.2(2) . . . . ?
N1 N2 N3 N4 -0.7(3) . . . . ?

_iucr_refine_instructions_details 
;

    mo_2017369-yc-17_0m.res created by SHELXL-2014/7

TITL mo_2017369-YC-17_0m in Cc
CELL 0.71073 3.7059 25.344 7.2132 90 101.824 90
ZERR 4 0.0009 0.0057 0.0017 0 0.004 0
LATT -7
SYMM +X,-Y,0.5+Z
SFAC C H N O
UNIT 12 20 28 8
DFIX 0.82 0.01 N7 H7b
DFIX 0.82 0.01 N7 H7a
DANG 1.296731 0.02 H7b H7a
 
L.S. 10
PLAN  -20 0 0
TEMP -100.15
HTAB
BOND $H
CONF
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
OMIT 0 14 -4
OMIT -1 13 -3
OMIT 3 7 -6
OMIT 0 2 0
REM <olex2.extras>
REM <HklSrc "%.\\mo_2017369-YC-17_0m.hkl">
REM </olex2.extras>
 
WGHT    0.033900
BASF  -0.34899
FVAR       0.24183
N5    3    0.144888    0.216257    1.020766    11.00000    0.03295    0.01574 =
         0.02356    0.00406    0.00792   -0.00017
O1    4    0.211318    0.043380    1.022081    11.00000    0.03822    0.01847 =
         0.02199   -0.00397    0.00279    0.00756
O2    4    0.305841    0.193290    0.753886    11.00000    0.04127    0.02472 =
         0.02565    0.00630    0.01228   -0.00160
N7    3    0.596987    0.048361    0.701421    11.00000    0.02226    0.02026 =
         0.01767   -0.00013    0.00618    0.00088
H7A   2    0.770913    0.039037    0.785214    11.00000   -1.50000
H7B   2    0.675560    0.064311    0.618780    11.00000   -1.50000
N2    3    0.008815    0.056217    1.301342    11.00000    0.03235    0.02165 =
         0.01899    0.00380    0.00050   -0.00515
N3    3   -0.088241    0.097435    1.390993    11.00000    0.03166    0.02742 =
         0.02117    0.00331    0.00614   -0.00603
N4    3   -0.054379    0.142040    1.296712    11.00000    0.02624    0.02078 =
         0.01809   -0.00014    0.00638   -0.00125
N6    3    0.242713    0.145812    0.844267    11.00000    0.03743    0.01997 =
         0.02369    0.00421    0.01256    0.00093
C3    1    0.242391    0.231857    0.867510    11.00000    0.03123    0.01891 =
         0.03320    0.00451    0.00617   -0.00006
AFIX  43
H3    2    0.266691    0.268085    0.838538    11.00000   -1.20000
AFIX   0
C2    1    0.149773    0.162251    0.999811    11.00000    0.01801    0.01660 =
         0.01912    0.00207    0.00154    0.00159
C1    1    0.064827    0.127223    1.143590    11.00000    0.01875    0.01551 =
         0.01798   -0.00016    0.00229    0.00017
N1    3    0.102739    0.074808    1.145761    11.00000    0.02288    0.01749 =
         0.01704   -0.00049    0.00031   -0.00010
 
H7C   2    0.459232    0.066088    0.759184    11.00000    0.03652
H7D   2    0.459920    0.020906    0.649263    11.00000    0.02648
HKLF 4
 
REM  mo_2017369-YC-17_0m in Cc
REM R1 =  0.0354 for    1276 Fo > 4sig(Fo)  and  0.0409 for all    1420 data
REM    124 parameters refined using      5 restraints
 
END  
     
WGHT      0.0339      0.0000 

REM Instructions for potential hydrogen bonds
EQIV $1 x+1, y, z
HTAB N7 O1_$1
EQIV $2 x+1, -y, z-1/2
HTAB N7 N2_$2
EQIV $3 x+1, y, z-1
HTAB N7 N3_$3
EQIV $4 x+1/2, -y+1/2, z-1/2
HTAB C3 N4_$4
HTAB N7 O1
HTAB N7 N6
EQIV $5 x, -y, z-1/2
HTAB N7 O1_$5

REM Highest difference peak  0.157,  deepest hole -0.190,  1-sigma level  0.043
Q1    1   0.0633  0.1447  1.0637  11.00000  0.05    0.16
Q2    1   0.5008  0.1810  0.5423  11.00000  0.05    0.15
Q3    1   0.0541  0.2354  1.0954  11.00000  0.05    0.14
Q4    1  -0.1562  0.1688  1.2841  11.00000  0.05    0.14
Q5    1   0.0121  0.1010  1.0998  11.00000  0.05    0.13
Q6    1  -0.2232  0.1009  1.5882  11.00000  0.05    0.12
Q7    1  -0.3507  0.0090  1.3919  11.00000  0.05    0.12
Q8    1  -0.1892  0.0882  1.4976  11.00000  0.05    0.12
Q9    1   0.1409  0.1892  1.0440  11.00000  0.05    0.12
Q10   1   0.4300  0.1488  0.5288  11.00000  0.05    0.12
Q11   1  -0.2734  0.1400  0.9215  11.00000  0.05    0.11
Q12   1   0.1742  0.0030  1.0662  11.00000  0.05    0.11
Q13   1   0.0530  0.1327  0.7426  11.00000  0.05    0.11
Q14   1  -0.0610  0.0274  1.4388  11.00000  0.05    0.11
Q15   1   0.1334 -0.0316  1.0630  11.00000  0.05    0.11
Q16   1  -0.0043  0.1058  1.6265  11.00000  0.05    0.11
Q17   1   0.7856  0.1758  0.5263  11.00000  0.05    0.11
Q18   1   1.0763  0.1965  0.5363  11.00000  0.05    0.11
Q19   1   0.0947  0.0694  1.5311  11.00000  0.05    0.11
Q20   1   0.1836  0.2590  1.2122  11.00000  0.05    0.11

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0354 for 1276 Fo > 4sig(Fo) and 0.0409 for all 2919 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.16, deepest hole -0.19
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0409
  REM R1_gt = 0.0354
  REM wR_ref = 0.0776
  REM GOOF = 1.032
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 2919
  REM Reflections_gt = 1276
  REM Parameters = n/a
  REM Hole = -0.19
  REM Peak = 0.16
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(2)
2 0(2)

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

data_mo_2017343-yc-16_0m
_database_code_depnum_ccdc_archive 'CCDC 1558528'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H2 N6 O2'
_chemical_formula_sum            'C3 H2 N6 O2'
_chemical_formula_weight         154.11
_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                   9.0167(19)
_cell_length_b                   10.224(2)
_cell_length_c                   13.146(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1211.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3104
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1037 before and 0.0492 after correction. The Ratio of minimum to maximum transmission is 0.9003. The λ/2 correction factor is 0.0015.'
_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    1.689
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8094
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.099
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1184
_reflns_number_total             1385
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.120
_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)+(0.0509P)²+0.1664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
;
_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
O2 O 0.58428(9) 0.65320(8) 0.53351(7) 0.0293(2) Uani 1 1 d . . . . .
O1 O 0.47190(11) 0.36213(9) 0.76004(7) 0.0376(3) Uani 1 1 d . . . . .
N6 N 0.68952(11) 0.56324(9) 0.51142(7) 0.0236(2) Uani 1 1 d . . . . .
N3 N 0.81328(12) 0.38552(10) 0.50408(7) 0.0272(3) Uani 1 1 d . . . . .
N1 N 0.64225(13) 0.26236(9) 0.66742(8) 0.0343(3) Uani 1 1 d . . . . .
N2 N 0.52567(13) 0.45649(10) 0.69159(8) 0.0323(3) Uani 1 1 d . . . . .
N4 N 0.85908(13) 0.46670(10) 0.42912(8) 0.0338(3) Uani 1 1 d . . . . .
N5 N 0.78309(12) 0.57588(10) 0.43237(8) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.70788(13) 0.44717(10) 0.55537(8) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.62438(13) 0.39142(10) 0.64003(8) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.54665(17) 0.25248(13) 0.73989(11) 0.0382(3) Uani 1 1 d . . . . .
H2 H 0.631(2) 0.745(2) 0.5213(15) 0.078(6) Uiso 1 1 d . . . . .
H1 H 0.5234(18) 0.1810(18) 0.7817(14) 0.054(5) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0275(5) 0.0181(4) 0.0424(5) 0.0009(3) 0.0005(4) 0.0020(3)
O1 0.0443(6) 0.0352(5) 0.0335(5) 0.0019(4) 0.0132(4) -0.0065(4)
N6 0.0254(5) 0.0170(5) 0.0283(5) 0.0015(3) -0.0006(4) -0.0021(4)
N3 0.0304(6) 0.0207(5) 0.0307(5) 0.0026(4) 0.0042(4) -0.0013(4)
N1 0.0435(7) 0.0214(5) 0.0379(6) 0.0064(4) 0.0075(5) -0.0017(5)
N2 0.0399(6) 0.0264(5) 0.0306(5) 0.0005(4) 0.0077(4) -0.0024(4)
N4 0.0382(6) 0.0263(5) 0.0369(6) 0.0067(4) 0.0095(5) 0.0006(5)
N5 0.0354(6) 0.0266(5) 0.0344(6) 0.0072(4) 0.0060(4) -0.0010(4)
C3 0.0252(6) 0.0165(5) 0.0258(5) -0.0003(4) -0.0019(4) -0.0028(4)
C2 0.0264(6) 0.0187(5) 0.0258(5) -0.0009(4) -0.0014(4) -0.0035(4)
C1 0.0492(9) 0.0278(7) 0.0378(7) 0.0060(5) 0.0087(6) -0.0082(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N6 1.3531(13) . ?
O2 H2 1.04(2) . ?
O1 N2 1.4055(14) . ?
O1 C1 1.3347(17) . ?
N6 N5 1.3448(14) . ?
N6 C3 1.3303(14) . ?
N3 N4 1.3530(14) . ?
N3 C3 1.3248(15) . ?
N1 C2 1.3773(14) . ?
N1 C1 1.2888(18) . ?
N2 C2 1.3016(16) . ?
N4 N5 1.3104(15) . ?
C3 C2 1.4596(15) . ?
C1 H1 0.938(19) . ?

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
N6 O2 H2 107.0(11) . . ?
C1 O1 N2 105.98(10) . . ?
N5 N6 O2 122.72(9) . . ?
C3 N6 O2 126.91(10) . . ?
C3 N6 N5 110.07(10) . . ?
C3 N3 N4 107.32(10) . . ?
C1 N1 C2 100.96(11) . . ?
C2 N2 O1 102.62(10) . . ?
N5 N4 N3 109.83(10) . . ?
N4 N5 N6 105.75(9) . . ?
N6 C3 C2 127.98(10) . . ?
N3 C3 N6 107.02(10) . . ?
N3 C3 C2 124.91(10) . . ?
N1 C2 C3 120.87(10) . . ?
N2 C2 N1 115.70(10) . . ?
N2 C2 C3 123.38(10) . . ?
O1 C1 H1 115.2(11) . . ?
N1 C1 O1 114.74(11) . . ?
N1 C1 H1 130.0(11) . . ?

_iucr_refine_instructions_details 
;

    mo_2017343-yc-16_0m.res created by SHELXL-2014/7

TITL mo_2017343-yc-16_0m_a.res in Pbca
REM Old TITL mo_2017343-YC-16_0m in Pbca
REM SHELXT solution in Pbca
REM R1 0.131, Rweak 0.002, Alpha 0.011, Orientation as input
REM Formula found by SHELXT: C9 N O
CELL 0.71073 9.0167 10.2244 13.1461 90 90 90
ZERR 8 0.0019 0.0022 0.0028 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 24 16 48 16
 
L.S. 20
PLAN  20 0 0
TEMP -100.15
BOND $H
list 4
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\mo_2017343-YC-16_0m.hkl">
REM </olex2.extras>
 
WGHT    0.050900    0.166400
FVAR       0.63753
O2    4    0.584276    0.653202    0.533512    11.00000    0.02754    0.01809 =
         0.04237    0.00093    0.00048    0.00201
O1    4    0.471902    0.362134    0.760036    11.00000    0.04426    0.03515 =
         0.03350    0.00194    0.01320   -0.00646
N6    3    0.689516    0.563245    0.511422    11.00000    0.02543    0.01702 =
         0.02825    0.00151   -0.00062   -0.00208
N3    3    0.813278    0.385520    0.504080    11.00000    0.03036    0.02071 =
         0.03067    0.00257    0.00425   -0.00126
N1    3    0.642252    0.262358    0.667417    11.00000    0.04351    0.02145 =
         0.03790    0.00641    0.00749   -0.00169
N2    3    0.525675    0.456490    0.691587    11.00000    0.03994    0.02642 =
         0.03059    0.00051    0.00775   -0.00241
N4    3    0.859077    0.466697    0.429119    11.00000    0.03823    0.02630 =
         0.03689    0.00672    0.00951    0.00058
N5    3    0.783094    0.575875    0.432370    11.00000    0.03536    0.02656 =
         0.03443    0.00721    0.00596   -0.00102
C3    1    0.707878    0.447167    0.555366    11.00000    0.02520    0.01649 =
         0.02575   -0.00029   -0.00195   -0.00277
C2    1    0.624381    0.391418    0.640028    11.00000    0.02640    0.01867 =
         0.02575   -0.00091   -0.00137   -0.00352
C1    1    0.546652    0.252478    0.739894    11.00000    0.04918    0.02775 =
         0.03780    0.00600    0.00868   -0.00816
H2    2    0.631484    0.744895    0.521335    11.00000    0.07843
H1    2    0.523422    0.180955    0.781704    11.00000    0.05425
HKLF 4
 
REM  mo_2017343-yc-16_0m_a.res in Pbca
REM R1 =  0.0368 for    1184 Fo > 4sig(Fo)  and  0.0422 for all    1385 data
REM    108 parameters refined using      0 restraints
 
END  
     
WGHT      0.0509      0.1664 

REM Highest difference peak  0.220,  deepest hole -0.372,  1-sigma level  0.090
Q1    1   0.6513  0.3295  0.6545  11.00000  0.05    0.22
Q2    1   0.6703  0.4261  0.5974  11.00000  0.05    0.21
Q3    1   0.7124  0.5800  0.7374  11.00000  0.05    0.20
Q4    1   0.7486  0.5441  0.7458  11.00000  0.05    0.19
Q5    1   1.0000  0.3666  0.5233  11.00000  0.05    0.17
Q6    1   0.7645  0.3229  0.7590  11.00000  0.05    0.17
Q7    1   0.4704  0.7644  0.5150  11.00000  0.05    0.16
Q8    1   0.5296  0.7012  0.4739  11.00000  0.05    0.16
Q9    1   0.7571  0.2686  0.7182  11.00000  0.05    0.16
Q10   1   0.9296  0.4198  0.3765  11.00000  0.05    0.15
Q11   1   0.7042  0.2147  0.6506  11.00000  0.05    0.15
Q12   1   0.4893  0.6167  0.5262  11.00000  0.05    0.15
Q13   1   0.2888  0.4218  0.7498  11.00000  0.05    0.15
Q14   1   0.8471  0.4281  0.3621  11.00000  0.05    0.14
Q15   1   0.4920  0.8136  0.4557  11.00000  0.05    0.14
Q16   1   0.4516  0.7020  0.5172  11.00000  0.05    0.14
Q17   1   0.7655  0.1823  0.7689  11.00000  0.05    0.14
Q18   1   0.7209  0.1714  0.6927  11.00000  0.05    0.14
Q19   1   0.9655  0.4685  0.4240  11.00000  0.05    0.14
Q20   1   1.0522  0.4370  0.4641  11.00000  0.05    0.14

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0368 for 1184 Fo > 4sig(Fo) and 0.0422 for all 8902 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.22, deepest hole -0.37
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0422
  REM R1_gt = 0.0368
  REM wR_ref = 0.0933
  REM GOOF = 1.120
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 8902
  REM Reflections_gt = 1184
  REM Parameters = n/a
  REM Hole = -0.37
  REM Peak = 0.22
  REM Flack = n/a

  
;
_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_yc-9_0m
_database_code_depnum_ccdc_archive 'CCDC 1558515'
_audit_update_record             
;
2017-09-03 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_audit_creation_date             2017-03-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H N4 O5, H4 N'
_chemical_formula_sum            'C3 H5 N5 O5'
_chemical_formula_weight         191.12
_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                   7.0339(14)
_cell_length_b                   7.2398(14)
_cell_length_c                   7.9636(15)
_cell_angle_alpha                84.593(3)
_cell_angle_beta                 83.386(4)
_cell_angle_gamma                64.874(3)
_cell_volume                     364.26(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1323
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      3.11
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0600 before and 0.0411 after correction. The Ratio of minimum to maximum transmission is 0.8853. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_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  0.0263
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3072
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.051
_diffrn_reflns_theta_min         2.578
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1319
_reflns_number_total             1544
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.056
_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)+(0.0887P)²+0.2136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1530
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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 0.4269(2) 0.7707(2) 0.1206(2) 0.0308(4) Uani 1 1 d . . . . .
O4 O 0.1669(2) 0.7331(3) 0.2735(2) 0.0356(4) Uani 1 1 d . . . . .
O1 O 0.7821(2) 0.4506(2) 0.1097(2) 0.0315(4) Uani 1 1 d . . . . .
O2 O 0.7787(3) 0.1775(2) 0.2470(2) 0.0321(4) Uani 1 1 d . . . . .
N1 N 0.6857(3) 0.3628(3) 0.2003(2) 0.0208(4) Uani 1 1 d . . . . .
O5 O 0.2618(3) 0.1960(3) 0.5601(2) 0.0418(5) Uani 1 1 d . . . . .
N2 N 0.3553(3) 0.6626(3) 0.2126(2) 0.0215(4) Uani 1 1 d . . . . .
N5 N -0.1819(3) 0.8321(3) 0.0509(2) 0.0230(4) Uani 1 1 d . . . . .
N4 N 0.2805(4) 0.2372(4) 0.2847(3) 0.0430(6) Uani 1 1 d . . . . .
C1 C 0.4749(3) 0.4607(3) 0.2537(2) 0.0196(4) Uani 1 1 d . . . . .
C2 C 0.3741(3) 0.3409(3) 0.3539(2) 0.0216(4) Uani 1 1 d . . . . .
N3 N 0.3701(4) 0.3212(4) 0.5165(2) 0.0388(6) Uani 1 1 d . . . . .
C3 C 0.2168(5) 0.1558(5) 0.4159(3) 0.0424(7) Uani 1 1 d . . . . .
H3 H 0.1447 0.0750 0.4096 0.051 Uiso 1 1 calc R . . . .
H5A H -0.257(5) 0.753(5) 0.100(4) 0.034(7) Uiso 1 1 d . . . . .
H5B H -0.235(7) 0.945(7) -0.006(5) 0.068(12) Uiso 1 1 d . . . . .
H5C H -0.053(7) 0.772(7) -0.006(5) 0.076(13) Uiso 1 1 d . . . . .
H5D H -0.150(7) 0.880(7) 0.133(6) 0.073(12) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0294(8) 0.0225(8) 0.0371(9) 0.0090(6) -0.0077(7) -0.0085(7)
O4 0.0170(7) 0.0352(10) 0.0470(10) -0.0050(7) -0.0018(7) -0.0034(7)
O1 0.0253(8) 0.0245(8) 0.0415(9) -0.0024(7) 0.0104(7) -0.0104(7)
O2 0.0303(8) 0.0168(8) 0.0446(10) 0.0005(6) -0.0051(7) -0.0055(6)
N1 0.0217(8) 0.0172(8) 0.0226(8) -0.0040(6) -0.0014(6) -0.0066(7)
O5 0.0589(12) 0.0632(13) 0.0227(8) 0.0006(8) 0.0023(8) -0.0461(11)
N2 0.0192(8) 0.0214(9) 0.0225(8) -0.0028(6) -0.0057(6) -0.0058(7)
N5 0.0240(9) 0.0214(9) 0.0228(9) -0.0022(7) -0.0042(7) -0.0078(8)
N4 0.0672(15) 0.0674(16) 0.0230(10) 0.0018(9) -0.0089(9) -0.0552(14)
C1 0.0191(9) 0.0187(10) 0.0207(9) -0.0008(7) -0.0039(7) -0.0072(8)
C2 0.0222(9) 0.0256(10) 0.0195(9) -0.0020(7) -0.0030(7) -0.0119(8)
N3 0.0609(14) 0.0555(14) 0.0211(10) -0.0005(9) -0.0029(9) -0.0449(12)
C3 0.0557(16) 0.0617(18) 0.0325(13) -0.0016(11) -0.0021(11) -0.0468(15)

_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 N2 1.243(2) . ?
O4 N2 1.255(2) . ?
O1 N1 1.245(2) . ?
O2 N1 1.258(2) . ?
N1 C1 1.379(3) . ?
O5 N3 1.410(2) . ?
O5 C3 1.316(3) . ?
N2 C1 1.371(3) . ?
N5 H5A 0.96(3) . ?
N5 H5B 0.85(4) . ?
N5 H5C 0.91(5) . ?
N5 H5D 0.86(5) . ?
N4 C2 1.372(3) . ?
N4 C3 1.281(3) . ?
C1 C2 1.468(3) . ?
C2 N3 1.287(3) . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 120.68(17) . . ?
O1 N1 C1 122.58(17) . . ?
O2 N1 C1 116.74(17) . . ?
C3 O5 N3 105.61(16) . . ?
O3 N2 O4 121.43(18) . . ?
O3 N2 C1 122.66(17) . . ?
O4 N2 C1 115.92(17) . . ?
H5A N5 H5B 126(3) . . ?
H5A N5 H5C 121(3) . . ?
H5A N5 H5D 107(3) . . ?
H5B N5 H5C 101(4) . . ?
H5B N5 H5D 96(4) . . ?
H5C N5 H5D 100(4) . . ?
C3 N4 C2 102.34(19) . . ?
N1 C1 C2 118.25(17) . . ?
N2 C1 N1 122.72(17) . . ?
N2 C1 C2 119.00(17) . . ?
N4 C2 C1 123.76(18) . . ?
N3 C2 N4 114.06(19) . . ?
N3 C2 C1 122.16(18) . . ?
C2 N3 O5 103.62(17) . . ?
O5 C3 H3 122.8 . . ?
N4 C3 O5 114.4(2) . . ?
N4 C3 H3 122.8 . . ?

_iucr_refine_instructions_details 
;

    mo_yc-9_0m.res created by SHELXL-2014/7

TITL mo_yc-9_0m_a.res in P-1
REM Old TITL mo_yc-9_0m in P-1
REM SHELXT solution in P-1
REM R1 0.157, Rweak 0.017, Alpha 0.055, Orientation as input
REM Formula found by SHELXT: C6 O4 N3
CELL 0.71073 7.0339 7.2398 7.9636 84.593 83.386 64.874
ZERR 2 0.0014 0.0014 0.0015 0.003 0.004 0.003
LATT 1
SFAC C H N O
UNIT 6 10 10 10
 
L.S. 4
PLAN  20
TEMP 23
BOND $H
list 4
fmap 2
acta
OMIT -3 -2 2
OMIT -2 1 0
REM <olex2.extras>
REM <HklSrc "%.\\mo_yc-9_0m.hkl">
REM </olex2.extras>
 
WGHT    0.088700    0.213600
FVAR       1.39976
O3    4    0.426903    0.770662    0.120620    11.00000    0.02944    0.02248 =
         0.03714    0.00902   -0.00768   -0.00846
O4    4    0.166918    0.733132    0.273474    11.00000    0.01703    0.03518 =
         0.04699   -0.00498   -0.00176   -0.00338
O1    4    0.782088    0.450602    0.109684    11.00000    0.02529    0.02448 =
         0.04153   -0.00244    0.01038   -0.01040
O2    4    0.778683    0.177546    0.246996    11.00000    0.03032    0.01677 =
         0.04460    0.00050   -0.00507   -0.00548
N1    3    0.685744    0.362845    0.200259    11.00000    0.02170    0.01716 =
         0.02258   -0.00402   -0.00136   -0.00661
O5    4    0.261847    0.196046    0.560130    11.00000    0.05891    0.06321 =
         0.02270    0.00062    0.00225   -0.04614
N2    3    0.355320    0.662586    0.212649    11.00000    0.01921    0.02141 =
         0.02250   -0.00278   -0.00565   -0.00575
N5    3   -0.181938    0.832085    0.050862    11.00000    0.02402    0.02136 =
         0.02277   -0.00220   -0.00419   -0.00778
N4    3    0.280544    0.237224    0.284698    11.00000    0.06720    0.06745 =
         0.02301    0.00178   -0.00894   -0.05516
C1    1    0.474940    0.460666    0.253665    11.00000    0.01912    0.01866 =
         0.02066   -0.00084   -0.00393   -0.00716
C2    1    0.374067    0.340928    0.353935    11.00000    0.02224    0.02564 =
         0.01954   -0.00203   -0.00302   -0.01193
N3    3    0.370140    0.321159    0.516505    11.00000    0.06089    0.05552 =
         0.02107   -0.00047   -0.00289   -0.04490
C3    1    0.216784    0.155801    0.415850    11.00000    0.05568    0.06171 =
         0.03247   -0.00162   -0.00210   -0.04677
AFIX  43
H3    2    0.144685    0.075012    0.409627    11.00000   -1.20000
AFIX   0
H5A   2   -0.257054    0.752898    0.099835    11.00000    0.03449
H5B   2   -0.234859    0.944947   -0.005777    11.00000    0.06785
H5C   2   -0.053459    0.771871   -0.005977    11.00000    0.07604
H5D   2   -0.150312    0.880258    0.132597    11.00000    0.07307
HKLF 4
 
REM  mo_yc-9_0m_a.res in P-1
REM R1 =  0.0516 for    1319 Fo > 4sig(Fo)  and  0.0585 for all    1544 data
REM    134 parameters refined using      0 restraints
 
END  
     
WGHT      0.0889      0.2135 

REM Highest difference peak  0.351,  deepest hole -0.425,  1-sigma level  0.107
Q1    1   0.0000  1.0000  0.0000  10.50000  0.05    0.35
Q2    1   0.0350  0.1385  0.4602  11.00000  0.05    0.29
Q3    1   0.4096  0.4106  0.2965  11.00000  0.05    0.29
Q4    1  -0.0353  0.1742  0.3810  11.00000  0.05    0.27
Q5    1   0.6226  0.3633  0.4945  11.00000  0.05    0.26
Q6    1   0.5087  0.5480  0.4085  11.00000  0.05    0.26
Q7    1   0.4474  0.4054  0.1168  11.00000  0.05    0.25
Q8    1   0.4652  0.5127  0.0308  11.00000  0.05    0.25
Q9    1   0.9748  0.3414  0.2130  11.00000  0.05    0.25
Q10   1   0.1181  0.3341  0.5887  11.00000  0.05    0.24
Q11   1   0.8282  0.4986  0.2009  11.00000  0.05    0.24
Q12   1   0.5759  0.5534  0.3446  11.00000  0.05    0.24
Q13   1  -0.0991  0.5868  0.1847  11.00000  0.05    0.24
Q14   1   0.5864  0.2283  0.5516  11.00000  0.05    0.23
Q15   1   0.8426  0.5566  0.2215  11.00000  0.05    0.23
Q16   1   0.4385 -0.0689  0.5971  11.00000  0.05    0.22
Q17   1   0.0522  0.8559  0.1347  11.00000  0.05    0.22
Q18   1   0.4743  0.6231 -0.0130  11.00000  0.05    0.22
Q19   1   0.9490  0.4819  0.2447  11.00000  0.05    0.21
Q20   1   0.1652  0.6097  0.1441  11.00000  0.05    0.20

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0516 for 1319 Fo > 4sig(Fo) and 0.0585 for all 3075 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.35, deepest hole -0.43
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0585
  REM R1_gt = 0.0516
  REM wR_ref = 0.1530
  REM GOOF = 1.056
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 3075
  REM Reflections_gt = 1319
  REM Parameters = n/a
  REM Hole = -0.43
  REM Peak = 0.35
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
