# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_wj_b1_0013
_database_code_depnum_ccdc_archive 'CCDC 1844137'
_audit_update_record             
;
2018-05-18 deposited with the CCDC.
2018-07-03 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2014/7

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Mariana Pastore'
_cambridge_user_crsid            mp797
_cambridge_supervisor_name       'William Jones'
_cambridge_supervisor_crsid      wj10
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             MP118
_cambridge_data_id               WJ_B1_0013

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H8 N4 O2), 3(C4 H7 N O)'
_chemical_formula_sum            'C26 H37 N11 O7'
_chemical_formula_weight         615.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.5056(3)
_cell_length_b                   25.0862(9)
_cell_length_c                   15.2376(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.195(2)
_cell_angle_gamma                90
_cell_volume                     2864.58(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      66.79

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.893
_shelx_estimated_absorpt_T_min   0.808
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49605
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.397
_diffrn_reflns_theta_max         66.798
_diffrn_reflns_theta_full        66.798
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5085
_reflns_number_gt                4616
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
_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.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
Refined as a 2-component twin (HKLF-5).
Refined BASF = 0.1066(8).

#-------------------------------------------------------------------------------
CELLNOW
#-------------------------------------------------------------------------------
 Domain 2 rotated from domain 1 by 179.9 degrees about
 reciprocal axis  1.000  0.004 -0.111  and real axis  1.000  0.000  0.000

 Twin law to convert hkl from first to      1.000   0.000  -0.001
 this domain (SHELXL TWIN matrix):          0.007  -1.000   0.002
                                           -0.222  -0.001  -1.000

#-------------------------------------------------------------------------------
TWINABS
#-------------------------------------------------------------------------------
 Statistics for singles of twin component  1
 -------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1    0.0  0.0389   0.807 - 0.906   0.967 - 1.072   1.281    1176     910
    2  103.4  0.0349   0.882 - 1.068   0.966 - 1.026   1.485     652     531
    3  103.4  0.0290   0.908 - 1.186   0.990 - 1.070   1.295    1146     928
    4  103.4  0.0322   0.886 - 1.064   0.967 - 1.026   1.229    1257    1025
    5   88.4  0.0263   0.775 - 0.966   0.966 - 1.072   1.287    3306    2844
    6   -4.6  0.0293   0.904 - 0.960   0.979 - 1.072   1.554     755     682
    7  103.4  0.0269   0.822 - 0.978   0.967 - 1.065   1.297     968     828
    8    5.4  0.0284   0.752 - 0.849   0.966 - 1.057   1.529    1865    1675
    9  103.4  0.0374   0.979 - 1.124   0.968 - 1.032   1.607     496     349
   10  103.4  0.0356   0.924 - 1.203   0.986 - 1.061   1.322    1227     954
   11  103.4  0.0270   0.802 - 0.919   0.966 - 1.055   1.201    2265    1923
   12  103.4  0.0281   0.837 - 0.927   0.967 - 1.072   1.325    2603    2136

   All scans  0.0315   0.752 - 1.203   0.966 - 1.072   1.368   17716   14785


 Statistics for singles of twin component  2
 -------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1    0.0  0.1181   0.551 - 0.791   0.942 - 1.095   1.281    1197     586
    2  103.4  0.0921   0.540 - 0.591   0.962 - 1.102   1.485     621     337
    3  103.4  0.0982   0.622 - 0.927   0.941 - 1.102   1.295    1103     564
    4  103.4  0.1224   0.610 - 0.900   0.962 - 1.103   1.229    1259     624
    5   88.4  0.0765   0.590 - 1.151   0.941 - 1.098   1.287    3287    1976
    6   -4.6  0.0608   0.584 - 0.810   0.965 - 1.102   1.554     762     567
    7  103.4  0.1260   0.695 - 0.814   0.962 - 1.103   1.297     961     490
    8    5.4  0.0609   0.766 - 1.141   0.941 - 1.083   1.529    1881    1307
    9  103.4  0.1481   0.545 - 0.667   0.964 - 1.102   1.607     488     210
   10  103.4  0.1490   0.874 - 1.298   0.941 - 1.097   1.322    1212     478
   11  103.4  0.0998   0.577 - 0.859   0.962 - 1.103   1.201    2284    1291
   12  103.4  0.1775   0.636 - 1.173   0.941 - 1.097   1.325    2526    1037

   All scans  0.0938   0.540 - 1.298   0.941 - 1.103   1.368   17581    9467


 Statistics for all composite reflections
 ----------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1    0.0  0.0650   0.699 - 0.845   0.972 - 1.069   1.281     208     166
    2  103.4  0.0612   0.579 - 1.041   0.966 - 1.093   1.485    1124     942
    3  103.4  0.0476   0.691 - 1.167   0.990 - 1.070   1.295     884     740
    4  103.4  0.0499   0.695 - 1.049   0.964 - 1.077   1.229     778     653
    5   88.4  0.0438   0.628 - 1.103   0.961 - 1.089   1.287    3192    2830
    6   -4.6  0.0504   0.634 - 0.954   0.966 - 1.070   1.554     427     368
    7  103.4  0.0420   0.734 - 0.963   0.975 - 1.078   1.297    1290    1076
    8    5.4  0.0765   0.776 - 1.077   0.965 - 1.039   1.529     547     493
    9  103.4  0.0697   0.573 - 1.096   0.967 - 1.079   1.607    1286    1038
   10  103.4  0.0490   0.900 - 1.242   0.958 - 1.064   1.322     775     655
   11  103.4  0.0412   0.618 - 0.879   0.966 - 1.082   1.201    1686    1480
   12  103.4  0.0494   0.680 - 1.119   0.966 - 1.081   1.325    2181    1841

   All scans  0.0526   0.573 - 1.242   0.958 - 1.093   1.368   14378   12282


 Statistics for all single and composite reflections
 ---------------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1    0.0  0.0497   0.551 - 0.906   0.942 - 1.095   1.281    2581    1662
    2  103.4  0.0516   0.540 - 1.068   0.962 - 1.102   1.485    2397    1810
    3  103.4  0.0417   0.622 - 1.186   0.941 - 1.102   1.295    3133    2232
    4  103.4  0.0443   0.610 - 1.064   0.962 - 1.103   1.229    3294    2302
    5   88.4  0.0371   0.590 - 1.151   0.941 - 1.098   1.287    9785    7650
    6   -4.6  0.0394   0.584 - 0.960   0.965 - 1.102   1.554    1944    1617
    7  103.4  0.0386   0.695 - 0.978   0.962 - 1.103   1.297    3219    2394
    8    5.4  0.0427   0.752 - 1.141   0.941 - 1.083   1.529    4293    3475
    9  103.4  0.0623   0.545 - 1.124   0.964 - 1.102   1.607    2270    1597
   10  103.4  0.0499   0.874 - 1.298   0.941 - 1.097   1.322    3214    2087
   11  103.4  0.0371   0.577 - 0.919   0.962 - 1.103   1.201    6235    4694
   12  103.4  0.0452   0.636 - 1.173   0.941 - 1.097   1.325    7310    5014

   All scans  0.0436   0.540 - 1.298   0.941 - 1.103   1.368   49675   36534

 su = K * Sqrt[ sigma^2(I) + (g)^2 ]  where sigma(I) is estimated by SAINT

 The above statistics are based on all non-rejected data, ignoring
 reflections without equivalents when estimating R(int) and K.

#-------------------------------------------------------------------------------
 HKLF 5 dataset constructed from all observations involving domain 1
    8591 Corrected reflections written to file wj_b1_0013_0m_5.hkl
 Reflections merged according to point-group 2/m   
 Single reflections that also occur in composites omitted
 Minimum and maximum apparent transmission:  0.637790  0.752819
 Additional spherical absorption correction applied with mu*r =  0.2000
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+1.4703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_extinction_coef       0.00119(12)
_refine_ls_number_reflns         5085
_refine_ls_number_parameters     423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.052

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1961(2) 0.37992(5) 0.50875(9) 0.0372(4) Uani 1 1 d . . . . .
O2 O 0.13965(18) 0.21599(5) 0.63709(8) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.1744(2) 0.29756(6) 0.57351(9) 0.0237(3) Uani 1 1 d . . . . .
N2 N 0.2704(2) 0.21835(6) 0.50641(9) 0.0212(3) Uani 1 1 d . . . . .
N3 N 0.3697(2) 0.32021(6) 0.36004(10) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.376(3) 0.3547(9) 0.3404(14) 0.029(5) Uiso 1 1 d . . . . .
N4 N 0.4049(2) 0.23158(6) 0.36563(10) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.2229(2) 0.33177(7) 0.50553(12) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.1923(2) 0.24213(7) 0.57594(11) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.3256(2) 0.24917(7) 0.43848(11) 0.0201(4) Uani 1 1 d . . . . .
C4 C 0.3026(2) 0.30324(7) 0.43769(11) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.4278(3) 0.27632(7) 0.32038(12) 0.0260(4) Uani 1 1 d . . . . .
H5A H 0.4805 0.2770 0.2651 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0906(3) 0.32259(9) 0.64780(13) 0.0354(5) Uani 1 1 d . . . . .
H6A H 0.1059 0.2996 0.6996 0.053 Uiso 1 1 calc R U . . .
H6B H -0.0370 0.3277 0.6329 0.053 Uiso 1 1 calc R U . . .
H6C H 0.1468 0.3572 0.6605 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3025(3) 0.16089(7) 0.50903(13) 0.0284(4) Uani 1 1 d . . . . .
H7A H 0.1912 0.1423 0.5202 0.043 Uiso 1 1 calc R U . . .
H7B H 0.3926 0.1527 0.5561 0.043 Uiso 1 1 calc R U . . .
H7C H 0.3453 0.1492 0.4526 0.043 Uiso 1 1 calc R U . . .
O3 O 0.5427(2) 0.62094(5) 0.15642(9) 0.0350(3) Uani 1 1 d . . . . .
O4 O 0.68140(19) 0.78975(5) 0.06653(9) 0.0326(3) Uani 1 1 d . . . . .
N5 N 0.6168(2) 0.70584(6) 0.11346(9) 0.0236(3) Uani 1 1 d . . . . .
N6 N 0.5613(2) 0.78221(6) 0.19930(10) 0.0239(3) Uani 1 1 d . . . . .
N7 N 0.4081(2) 0.67462(6) 0.32080(10) 0.0265(3) Uani 1 1 d . . . . .
H7 H 0.390(4) 0.6392(12) 0.3345(18) 0.059(8) Uiso 1 1 d . . . . .
N8 N 0.4231(2) 0.76339(6) 0.33735(10) 0.0265(3) Uani 1 1 d . . . . .
C8 C 0.5463(2) 0.66901(7) 0.17241(12) 0.0241(4) Uani 1 1 d . . . . .
C9 C 0.6228(2) 0.76126(7) 0.12345(11) 0.0237(4) Uani 1 1 d . . . . .
C10 C 0.4917(2) 0.74863(7) 0.26043(11) 0.0219(4) Uani 1 1 d . . . . .
C11 C 0.4848(2) 0.69482(7) 0.24774(11) 0.0225(4) Uani 1 1 d . . . . .
C12 C 0.3751(3) 0.71695(8) 0.37131(12) 0.0281(4) Uani 1 1 d . . . . .
H12A H 0.3223 0.7141 0.4263 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6926(3) 0.68502(8) 0.03361(12) 0.0311(4) Uani 1 1 d . . . . .
H13A H 0.8141 0.6987 0.0295 0.047 Uiso 1 1 calc R U . . .
H13B H 0.6187 0.6964 -0.0180 0.047 Uiso 1 1 calc R U . . .
H13C H 0.6956 0.6460 0.0361 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5736(3) 0.83957(7) 0.21450(13) 0.0320(4) Uani 1 1 d . . . . .
H14A H 0.6990 0.8506 0.2159 0.048 Uiso 1 1 calc R U . . .
H14B H 0.5236 0.8482 0.2708 0.048 Uiso 1 1 calc R U . . .
H14C H 0.5065 0.8584 0.1670 0.048 Uiso 1 1 calc R U . . .
O1A O 0.3513(2) 0.42579(5) 0.30924(9) 0.0361(4) Uani 1 1 d . . . . .
N1A N 0.4039(2) 0.49136(6) 0.21018(10) 0.0292(4) Uani 1 1 d . . . . .
H1A H 0.396(3) 0.5186(10) 0.2504(16) 0.042(7) Uiso 1 1 d . . . . .
C1A C 0.3819(3) 0.44110(7) 0.23356(12) 0.0269(4) Uani 1 1 d . . . . .
C2A C 0.3979(3) 0.40575(8) 0.15495(13) 0.0390(5) Uani 1 1 d . . . . .
H2AA H 0.4973 0.3801 0.1649 0.047 Uiso 1 1 calc R U . . .
H2AB H 0.2860 0.3856 0.1421 0.047 Uiso 1 1 calc R U . . .
C3A C 0.4336(5) 0.44280(9) 0.08109(15) 0.0561(8) Uani 1 1 d . . . . .
H3AA H 0.3382 0.4397 0.0338 0.067 Uiso 1 1 calc R U . . .
H3AB H 0.5491 0.4340 0.0563 0.067 Uiso 1 1 calc R U . . .
C4A C 0.4386(3) 0.49895(8) 0.11804(12) 0.0313(4) Uani 1 1 d . . . . .
H4AA H 0.5568 0.5156 0.1117 0.038 Uiso 1 1 calc R U . . .
H4AB H 0.3456 0.5216 0.0882 0.038 Uiso 1 1 calc R U . . .
O1B O 0.3455(2) 0.56734(5) 0.34868(8) 0.0332(3) Uani 1 1 d . . . . .
N1B N 0.2710(2) 0.50387(6) 0.44799(10) 0.0273(4) Uani 1 1 d . . . . .
H1B H 0.283(3) 0.4767(9) 0.4129(14) 0.029(6) Uiso 1 1 d . . . . .
C1B C 0.3082(2) 0.55326(7) 0.42371(12) 0.0246(4) Uani 1 1 d . . . . .
C2B C 0.3034(3) 0.58940(8) 0.50186(12) 0.0349(5) Uani 1 1 d . . . . .
H2BA H 0.2292 0.6212 0.4879 0.042 Uiso 1 1 calc R U . . .
H2BB H 0.4252 0.6011 0.5213 0.042 Uiso 1 1 calc R U . . .
C3B C 0.2220(3) 0.55578(8) 0.57217(13) 0.0351(5) Uani 1 1 d . . . . .
H3BA H 0.0954 0.5655 0.5780 0.042 Uiso 1 1 calc R U . . .
H3BB H 0.2877 0.5608 0.6297 0.042 Uiso 1 1 calc R U . . .
C4B C 0.2381(3) 0.49794(7) 0.54078(12) 0.0281(4) Uani 1 1 d . . . . .
H4BA H 0.3385 0.4794 0.5728 0.034 Uiso 1 1 calc R U . . .
H4BB H 0.1266 0.4779 0.5487 0.034 Uiso 1 1 calc R U . . .
O1C O 0.4309(3) 0.04980(6) 0.57691(11) 0.0562(5) Uani 1 1 d . . . . .
N1C N 0.4794(2) -0.03888(7) 0.60241(11) 0.0320(4) Uani 1 1 d . . . . .
H1C H 0.515(3) -0.0462(9) 0.5497(17) 0.041(6) Uiso 1 1 d . . . . .
C1C C 0.4414(3) 0.01089(8) 0.62585(13) 0.0340(5) Uani 1 1 d . . . . .
C2C C 0.4117(3) 0.01178(8) 0.72293(13) 0.0347(5) Uani 1 1 d . . . . .
H2CA H 0.2987 0.0302 0.7345 0.042 Uiso 1 1 calc R U . . .
H2CB H 0.5113 0.0300 0.7559 0.042 Uiso 1 1 calc R U . . .
C3C C 0.4035(3) -0.04700(9) 0.74868(13) 0.0373(5) Uani 1 1 d . . . . .
H3CA H 0.2782 -0.0589 0.7516 0.045 Uiso 1 1 calc R U . . .
H3CB H 0.4671 -0.0532 0.8064 0.045 Uiso 1 1 calc R U . . .
C4C C 0.4956(3) -0.07631(8) 0.67549(13) 0.0352(5) Uani 1 1 d . . . . .
H4CA H 0.6223 -0.0836 0.6928 0.042 Uiso 1 1 calc R U . . .
H4CB H 0.4345 -0.1103 0.6604 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.226(2) . ?
O2 C2 1.223(2) . ?
N1 C2 1.397(2) . ?
N1 C1 1.409(2) . ?
N1 C6 1.467(2) . ?
N2 C3 1.374(2) . ?
N2 C2 1.375(2) . ?
N2 C7 1.462(2) . ?
N3 C5 1.341(2) . ?
N3 C4 1.379(2) . ?
N3 H3 0.92(2) . ?
N4 C5 1.333(2) . ?
N4 C3 1.362(2) . ?
C1 C4 1.417(2) . ?
C3 C4 1.367(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O3 C8 1.230(2) . ?
O4 C9 1.224(2) . ?
N5 C9 1.399(2) . ?
N5 C8 1.412(2) . ?
N5 C13 1.468(2) . ?
N6 C9 1.373(2) . ?
N6 C10 1.380(2) . ?
N6 C14 1.460(2) . ?
N7 C12 1.343(2) . ?
N7 C11 1.378(2) . ?
N7 H7 0.92(3) . ?
N8 C12 1.332(2) . ?
N8 C10 1.358(2) . ?
C8 C11 1.417(3) . ?
C10 C11 1.364(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1A C1A 1.249(2) . ?
N1A C1A 1.323(2) . ?
N1A C4A 1.455(2) . ?
N1A H1A 0.92(2) . ?
C1A C2A 1.501(3) . ?
C2A C3A 1.495(3) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.517(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
O1B C1B 1.243(2) . ?
N1B C1B 1.327(2) . ?
N1B C4B 1.456(2) . ?
N1B H1B 0.87(2) . ?
C1B C2B 1.499(2) . ?
C2B C3B 1.518(3) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.535(3) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
O1C C1C 1.228(3) . ?
N1C C1C 1.334(3) . ?
N1C C4C 1.456(3) . ?
N1C H1C 0.88(2) . ?
C1C C2C 1.508(3) . ?
C2C C3C 1.528(3) . ?
C2C H2CA 0.9900 . ?
C2C H2CB 0.9900 . ?
C3C C4C 1.532(3) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C4C H4CA 0.9900 . ?
C4C H4CB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 126.69(14) . . ?
C2 N1 C6 116.77(15) . . ?
C1 N1 C6 116.50(15) . . ?
C3 N2 C2 119.71(15) . . ?
C3 N2 C7 121.29(14) . . ?
C2 N2 C7 118.90(14) . . ?
C5 N3 C4 106.07(15) . . ?
C5 N3 H3 127.1(13) . . ?
C4 N3 H3 126.8(13) . . ?
C5 N4 C3 102.92(15) . . ?
O1 C1 N1 121.42(16) . . ?
O1 C1 C4 127.14(17) . . ?
N1 C1 C4 111.44(15) . . ?
O2 C2 N2 121.62(16) . . ?
O2 C2 N1 121.27(16) . . ?
N2 C2 N1 117.11(15) . . ?
N4 C3 C4 112.02(15) . . ?
N4 C3 N2 126.54(15) . . ?
C4 C3 N2 121.44(15) . . ?
C3 C4 N3 105.19(15) . . ?
C3 C4 C1 123.56(16) . . ?
N3 C4 C1 131.24(17) . . ?
N4 C5 N3 113.80(16) . . ?
N4 C5 H5A 123.1 . . ?
N3 C5 H5A 123.1 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 N5 C8 126.30(15) . . ?
C9 N5 C13 115.62(15) . . ?
C8 N5 C13 118.08(15) . . ?
C9 N6 C10 119.49(15) . . ?
C9 N6 C14 119.31(15) . . ?
C10 N6 C14 121.19(15) . . ?
C12 N7 C11 105.71(15) . . ?
C12 N7 H7 126.7(17) . . ?
C11 N7 H7 127.4(17) . . ?
C12 N8 C10 102.74(15) . . ?
O3 C8 N5 121.35(16) . . ?
O3 C8 C11 127.14(17) . . ?
N5 C8 C11 111.52(15) . . ?
O4 C9 N6 121.60(17) . . ?
O4 C9 N5 120.90(16) . . ?
N6 C9 N5 117.50(15) . . ?
N8 C10 C11 112.27(15) . . ?
N8 C10 N6 126.32(16) . . ?
C11 C10 N6 121.41(16) . . ?
C10 C11 N7 105.30(15) . . ?
C10 C11 C8 123.73(16) . . ?
N7 C11 C8 130.97(16) . . ?
N8 C12 N7 113.99(16) . . ?
N8 C12 H12A 123.0 . . ?
N7 C12 H12A 123.0 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N6 C14 H14A 109.5 . . ?
N6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1A N1A C4A 114.62(16) . . ?
C1A N1A H1A 120.9(15) . . ?
C4A N1A H1A 124.5(15) . . ?
O1A C1A N1A 125.03(17) . . ?
O1A C1A C2A 125.61(17) . . ?
N1A C1A C2A 109.36(16) . . ?
C3A C2A C1A 105.02(16) . . ?
C3A C2A H2AA 110.7 . . ?
C1A C2A H2AA 110.7 . . ?
C3A C2A H2AB 110.7 . . ?
C1A C2A H2AB 110.7 . . ?
H2AA C2A H2AB 108.8 . . ?
C2A C3A C4A 107.44(17) . . ?
C2A C3A H3AA 110.2 . . ?
C4A C3A H3AA 110.2 . . ?
C2A C3A H3AB 110.2 . . ?
C4A C3A H3AB 110.2 . . ?
H3AA C3A H3AB 108.5 . . ?
N1A C4A C3A 103.57(15) . . ?
N1A C4A H4AA 111.0 . . ?
C3A C4A H4AA 111.0 . . ?
N1A C4A H4AB 111.0 . . ?
C3A C4A H4AB 111.0 . . ?
H4AA C4A H4AB 109.0 . . ?
C1B N1B C4B 114.56(15) . . ?
C1B N1B H1B 121.8(14) . . ?
C4B N1B H1B 122.9(14) . . ?
O1B C1B N1B 125.67(17) . . ?
O1B C1B C2B 125.12(16) . . ?
N1B C1B C2B 109.18(16) . . ?
C1B C2B C3B 104.65(15) . . ?
C1B C2B H2BA 110.8 . . ?
C3B C2B H2BA 110.8 . . ?
C1B C2B H2BB 110.8 . . ?
C3B C2B H2BB 110.8 . . ?
H2BA C2B H2BB 108.9 . . ?
C2B C3B C4B 105.27(15) . . ?
C2B C3B H3BA 110.7 . . ?
C4B C3B H3BA 110.7 . . ?
C2B C3B H3BB 110.7 . . ?
C4B C3B H3BB 110.7 . . ?
H3BA C3B H3BB 108.8 . . ?
N1B C4B C3B 103.10(14) . . ?
N1B C4B H4BA 111.1 . . ?
C3B C4B H4BA 111.1 . . ?
N1B C4B H4BB 111.1 . . ?
C3B C4B H4BB 111.1 . . ?
H4BA C4B H4BB 109.1 . . ?
C1C N1C C4C 114.12(17) . . ?
C1C N1C H1C 121.3(15) . . ?
C4C N1C H1C 123.2(15) . . ?
O1C C1C N1C 126.06(19) . . ?
O1C C1C C2C 125.15(19) . . ?
N1C C1C C2C 108.78(17) . . ?
C1C C2C C3C 104.35(16) . . ?
C1C C2C H2CA 110.9 . . ?
C3C C2C H2CA 110.9 . . ?
C1C C2C H2CB 110.9 . . ?
C3C C2C H2CB 110.9 . . ?
H2CA C2C H2CB 108.9 . . ?
C2C C3C C4C 104.46(16) . . ?
C2C C3C H3CA 110.9 . . ?
C4C C3C H3CA 110.9 . . ?
C2C C3C H3CB 110.9 . . ?
C4C C3C H3CB 110.9 . . ?
H3CA C3C H3CB 108.9 . . ?
N1C C4C C3C 103.03(16) . . ?
N1C C4C H4CA 111.2 . . ?
C3C C4C H4CA 111.2 . . ?
N1C C4C H4CB 111.2 . . ?
C3C C4C H4CB 111.2 . . ?
H4CA C4C H4CB 109.1 . . ?

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
C2 N1 C1 O1 177.62(18) . . . . ?
C6 N1 C1 O1 0.1(3) . . . . ?
C2 N1 C1 C4 -2.5(3) . . . . ?
C6 N1 C1 C4 179.90(17) . . . . ?
C3 N2 C2 O2 179.13(17) . . . . ?
C7 N2 C2 O2 -4.5(3) . . . . ?
C3 N2 C2 N1 -0.4(2) . . . . ?
C7 N2 C2 N1 175.99(16) . . . . ?
C1 N1 C2 O2 -177.27(17) . . . . ?
C6 N1 C2 O2 0.3(3) . . . . ?
C1 N1 C2 N2 2.3(3) . . . . ?
C6 N1 C2 N2 179.85(16) . . . . ?
C5 N4 C3 C4 -0.6(2) . . . . ?
C5 N4 C3 N2 178.80(18) . . . . ?
C2 N2 C3 N4 179.87(17) . . . . ?
C7 N2 C3 N4 3.5(3) . . . . ?
C2 N2 C3 C4 -0.8(3) . . . . ?
C7 N2 C3 C4 -177.16(17) . . . . ?
N4 C3 C4 N3 0.5(2) . . . . ?
N2 C3 C4 N3 -178.88(16) . . . . ?
N4 C3 C4 C1 179.84(17) . . . . ?
N2 C3 C4 C1 0.4(3) . . . . ?
C5 N3 C4 C3 -0.3(2) . . . . ?
C5 N3 C4 C1 -179.5(2) . . . . ?
O1 C1 C4 C3 -179.06(19) . . . . ?
N1 C1 C4 C3 1.1(3) . . . . ?
O1 C1 C4 N3 0.1(4) . . . . ?
N1 C1 C4 N3 -179.76(18) . . . . ?
C3 N4 C5 N3 0.4(2) . . . . ?
C4 N3 C5 N4 -0.1(2) . . . . ?
C9 N5 C8 O3 177.93(18) . . . . ?
C13 N5 C8 O3 -2.3(3) . . . . ?
C9 N5 C8 C11 -2.1(3) . . . . ?
C13 N5 C8 C11 177.65(16) . . . . ?
C10 N6 C9 O4 178.15(17) . . . . ?
C14 N6 C9 O4 -2.9(3) . . . . ?
C10 N6 C9 N5 -2.1(3) . . . . ?
C14 N6 C9 N5 176.83(16) . . . . ?
C8 N5 C9 O4 -177.38(17) . . . . ?
C13 N5 C9 O4 2.9(3) . . . . ?
C8 N5 C9 N6 2.9(3) . . . . ?
C13 N5 C9 N6 -176.86(16) . . . . ?
C12 N8 C10 C11 0.3(2) . . . . ?
C12 N8 C10 N6 180.00(18) . . . . ?
C9 N6 C10 N8 -178.73(17) . . . . ?
C14 N6 C10 N8 2.4(3) . . . . ?
C9 N6 C10 C11 0.9(3) . . . . ?
C14 N6 C10 C11 -178.00(17) . . . . ?
N8 C10 C11 N7 -0.2(2) . . . . ?
N6 C10 C11 N7 -179.88(16) . . . . ?
N8 C10 C11 C8 179.49(17) . . . . ?
N6 C10 C11 C8 -0.2(3) . . . . ?
C12 N7 C11 C10 0.0(2) . . . . ?
C12 N7 C11 C8 -179.68(19) . . . . ?
O3 C8 C11 C10 -179.32(19) . . . . ?
N5 C8 C11 C10 0.7(3) . . . . ?
O3 C8 C11 N7 0.3(3) . . . . ?
N5 C8 C11 N7 -179.73(18) . . . . ?
C10 N8 C12 N7 -0.4(2) . . . . ?
C11 N7 C12 N8 0.3(2) . . . . ?
C4A N1A C1A O1A 179.8(2) . . . . ?
C4A N1A C1A C2A -0.6(3) . . . . ?
O1A C1A C2A C3A 179.7(2) . . . . ?
N1A C1A C2A C3A 0.2(3) . . . . ?
C1A C2A C3A C4A 0.3(3) . . . . ?
C1A N1A C4A C3A 0.7(3) . . . . ?
C2A C3A C4A N1A -0.6(3) . . . . ?
C4B N1B C1B O1B 177.87(19) . . . . ?
C4B N1B C1B C2B -0.5(2) . . . . ?
O1B C1B C2B C3B 170.8(2) . . . . ?
N1B C1B C2B C3B -10.8(2) . . . . ?
C1B C2B C3B C4B 17.1(2) . . . . ?
C1B N1B C4B C3B 11.4(2) . . . . ?
C2B C3B C4B N1B -17.1(2) . . . . ?
C4C N1C C1C O1C 175.8(2) . . . . ?
C4C N1C C1C C2C -4.6(3) . . . . ?
O1C C1C C2C C3C 169.1(2) . . . . ?
N1C C1C C2C C3C -10.5(2) . . . . ?
C1C C2C C3C C4C 20.3(2) . . . . ?
C1C N1C C4C C3C 17.5(2) . . . . ?
C2C C3C C4C N1C -22.5(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_wj_b2_0021
_database_code_depnum_ccdc_archive 'CCDC 1844138'
_audit_update_record             
;
2018-05-18 deposited with the CCDC.
2018-07-03 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2014/7

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Mariana Pastore'
_cambridge_user_crsid            mp797
_cambridge_supervisor_name       'William Jones'
_cambridge_supervisor_crsid      wj10
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             MP119
_cambridge_data_id               WJ_B2_0021

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N4 O2, C4 H7 N O'
_chemical_formula_sum            'C11 H15 N5 O3'
_chemical_formula_weight         265.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6482(3)
_cell_length_b                   8.7311(4)
_cell_length_c                   10.9852(5)
_cell_angle_alpha                82.631(2)
_cell_angle_beta                 84.273(2)
_cell_angle_gamma                83.701(3)
_cell_volume                     626.18(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7785
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      66.59

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.887
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14518
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.073
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_full        66.595
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2206
_reflns_number_gt                1872
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.2451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2206
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.036

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22474(18) 0.57427(12) 0.78316(9) 0.0343(3) Uani 1 1 d . . . . .
O2 O 0.24935(18) 0.91440(12) 0.42992(10) 0.0328(3) Uani 1 1 d . . . . .
N1 N 0.23053(18) 0.74306(13) 0.60488(11) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.25740(18) 0.65914(13) 0.40713(10) 0.0231(3) Uani 1 1 d . . . . .
N3 N 0.24169(19) 0.31840(14) 0.61284(12) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.237(3) 0.261(2) 0.6919(18) 0.037(5) Uiso 1 1 d . . . . .
N4 N 0.26281(19) 0.37965(14) 0.40750(11) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.2317(2) 0.59433(16) 0.66961(13) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.2460(2) 0.77986(17) 0.47698(13) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.2540(2) 0.50969(16) 0.46410(13) 0.0208(3) Uani 1 1 d . . . . .
C4 C 0.2408(2) 0.47764(16) 0.58990(13) 0.0213(3) Uani 1 1 d . . . . .
C5 C 0.2547(2) 0.26694(17) 0.50160(13) 0.0252(3) Uani 1 1 d . . . . .
H5A H 0.2577 0.1604 0.4911 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2193(3) 0.87612(18) 0.67529(14) 0.0316(4) Uani 1 1 d . . . . .
H6A H 0.2055 0.8399 0.7636 0.047 Uiso 1 1 calc R U . . .
H6B H 0.1015 0.9488 0.6540 0.047 Uiso 1 1 calc R U . . .
H6C H 0.3435 0.9286 0.6552 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2759(3) 0.69275(19) 0.27265(14) 0.0336(4) Uani 1 1 d . . . . .
H7A H 0.3901 0.7549 0.2466 0.050 Uiso 1 1 calc R U . . .
H7B H 0.1502 0.7507 0.2455 0.050 Uiso 1 1 calc R U . . .
H7C H 0.2996 0.5952 0.2358 0.050 Uiso 1 1 calc R U . . .
O1A O 0.20761(19) 0.13989(13) 0.83878(10) 0.0356(3) Uani 1 1 d . . . . .
N1A N 0.2723(2) 0.31187(17) 0.96681(12) 0.0341(3) Uani 1 1 d . . . . .
H1A H 0.264(3) 0.393(3) 0.9121(19) 0.046(6) Uiso 1 1 d . . . . .
C1A C 0.2351(2) 0.17372(18) 0.94179(13) 0.0277(3) Uani 1 1 d . . . . .
C2A C 0.2301(3) 0.0644(2) 1.05985(14) 0.0363(4) Uani 1 1 d . . . . .
H2AA H 0.3111 -0.0355 1.0481 0.044 Uiso 1 1 calc R U . . .
H2AB H 0.0890 0.0442 1.0899 0.044 Uiso 1 1 calc R U . . .
C3A C 0.3232(3) 0.1502(2) 1.14942(15) 0.0419(4) Uani 1 1 d . . . . .
H3AA H 0.2544 0.1321 1.2334 0.050 Uiso 1 1 calc R U . . .
H3AB H 0.4699 0.1164 1.1524 0.050 Uiso 1 1 calc R U . . .
C4A C 0.2895(3) 0.3207(2) 1.09743(15) 0.0392(4) Uani 1 1 d . . . . .
H4AA H 0.1636 0.3719 1.1365 0.047 Uiso 1 1 calc R U . . .
H4AB H 0.4058 0.3775 1.1089 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2341(18) . ?
O2 C2 1.2228(18) . ?
N1 C2 1.3965(19) . ?
N1 C1 1.3979(19) . ?
N1 C6 1.4675(19) . ?
N2 C2 1.3726(19) . ?
N2 C3 1.3744(18) . ?
N2 C7 1.4642(18) . ?
N3 C5 1.3467(19) . ?
N3 C4 1.3803(19) . ?
N3 H3 0.94(2) . ?
N4 C5 1.3340(19) . ?
N4 C3 1.3559(19) . ?
C1 C4 1.419(2) . ?
C3 C4 1.370(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1A C1A 1.2409(18) . ?
N1A C1A 1.325(2) . ?
N1A C4A 1.463(2) . ?
N1A H1A 0.87(2) . ?
C1A C2A 1.508(2) . ?
C2A C3A 1.525(2) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.525(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 126.47(12) . . ?
C2 N1 C6 115.11(12) . . ?
C1 N1 C6 118.39(12) . . ?
C2 N2 C3 119.72(12) . . ?
C2 N2 C7 118.93(12) . . ?
C3 N2 C7 121.34(12) . . ?
C5 N3 C4 105.88(12) . . ?
C5 N3 H3 129.2(11) . . ?
C4 N3 H3 124.9(11) . . ?
C5 N4 C3 103.07(12) . . ?
O1 C1 N1 121.23(13) . . ?
O1 C1 C4 126.62(13) . . ?
N1 C1 C4 112.15(12) . . ?
O2 C2 N2 121.78(13) . . ?
O2 C2 N1 120.97(13) . . ?
N2 C2 N1 117.26(12) . . ?
N4 C3 C4 112.23(12) . . ?
N4 C3 N2 126.31(12) . . ?
C4 C3 N2 121.46(13) . . ?
C3 C4 N3 105.11(12) . . ?
C3 C4 C1 122.88(13) . . ?
N3 C4 C1 132.00(13) . . ?
N4 C5 N3 113.70(13) . . ?
N4 C5 H5A 123.1 . . ?
N3 C5 H5A 123.1 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1A N1A C4A 114.23(14) . . ?
C1A N1A H1A 121.6(13) . . ?
C4A N1A H1A 123.1(13) . . ?
O1A C1A N1A 125.85(14) . . ?
O1A C1A C2A 125.62(14) . . ?
N1A C1A C2A 108.52(13) . . ?
C1A C2A C3A 103.94(13) . . ?
C1A C2A H2AA 111.0 . . ?
C3A C2A H2AA 111.0 . . ?
C1A C2A H2AB 111.0 . . ?
C3A C2A H2AB 111.0 . . ?
H2AA C2A H2AB 109.0 . . ?
C4A C3A C2A 104.26(13) . . ?
C4A C3A H3AA 110.9 . . ?
C2A C3A H3AA 110.9 . . ?
C4A C3A H3AB 110.9 . . ?
C2A C3A H3AB 110.9 . . ?
H3AA C3A H3AB 108.9 . . ?
N1A C4A C3A 102.54(13) . . ?
N1A C4A H4AA 111.3 . . ?
C3A C4A H4AA 111.3 . . ?
N1A C4A H4AB 111.3 . . ?
C3A C4A H4AB 111.3 . . ?
H4AA C4A H4AB 109.2 . . ?

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
C2 N1 C1 O1 177.23(13) . . . . ?
C6 N1 C1 O1 -0.4(2) . . . . ?
C2 N1 C1 C4 -2.9(2) . . . . ?
C6 N1 C1 C4 179.40(13) . . . . ?
C3 N2 C2 O2 179.70(14) . . . . ?
C7 N2 C2 O2 0.6(2) . . . . ?
C3 N2 C2 N1 -0.25(19) . . . . ?
C7 N2 C2 N1 -179.38(13) . . . . ?
C1 N1 C2 O2 -177.83(14) . . . . ?
C6 N1 C2 O2 -0.1(2) . . . . ?
C1 N1 C2 N2 2.1(2) . . . . ?
C6 N1 C2 N2 179.85(13) . . . . ?
C5 N4 C3 C4 0.00(16) . . . . ?
C5 N4 C3 N2 179.99(14) . . . . ?
C2 N2 C3 N4 179.58(13) . . . . ?
C7 N2 C3 N4 -1.3(2) . . . . ?
C2 N2 C3 C4 -0.4(2) . . . . ?
C7 N2 C3 C4 178.69(13) . . . . ?
N4 C3 C4 N3 0.08(16) . . . . ?
N2 C3 C4 N3 -179.91(12) . . . . ?
N4 C3 C4 C1 179.39(13) . . . . ?
N2 C3 C4 C1 -0.6(2) . . . . ?
C5 N3 C4 C3 -0.12(15) . . . . ?
C5 N3 C4 C1 -179.35(15) . . . . ?
O1 C1 C4 C3 -178.07(14) . . . . ?
N1 C1 C4 C3 2.1(2) . . . . ?
O1 C1 C4 N3 1.0(3) . . . . ?
N1 C1 C4 N3 -178.79(14) . . . . ?
C3 N4 C5 N3 -0.09(16) . . . . ?
C4 N3 C5 N4 0.14(17) . . . . ?
C4A N1A C1A O1A 177.38(16) . . . . ?
C4A N1A C1A C2A -2.2(2) . . . . ?
O1A C1A C2A C3A 166.44(16) . . . . ?
N1A C1A C2A C3A -13.99(19) . . . . ?
C1A C2A C3A C4A 23.67(18) . . . . ?
C1A N1A C4A C3A 17.3(2) . . . . ?
C2A C3A C4A N1A -24.46(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1A 0.94(2) 1.82(2) 2.7593(17) 173.7(17) .
N1A H1A O1 0.87(2) 2.00(2) 2.8639(18) 175.6(19) .

