# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_FINAL
_database_code_depnum_ccdc_archive 'CCDC 1010756'
_audit_update_record             
;
2014-06-27 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'[3-cyano-4-(2-oxo-3aH-indol-3-yl)-4a, 8a-dihydrochromen-2-yl] amine; [3-cyano-4-(2-oxo-dihydro-1$l^{2}-indol-3-yl)-4a,8a-dihydro-1$l^{3}-benzopyran-2-yl]amine'
_chemical_formula_moiety         'C18 H13 N3 O2'
_chemical_formula_sum            'C18 H13 N3 O2'
_chemical_formula_weight         303.31
_chemical_absolute_configuration unk
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'


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


_cell_length_a                   10.5876(4)
_cell_length_b                   12.4088(5)
_cell_length_c                   12.5358(5)
_cell_angle_alpha                68.982(4)
_cell_angle_beta                 84.668(3)
_cell_angle_gamma                88.342(3)
_cell_volume                     1530.70(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8499
_cell_measurement_theta_min      3.7950
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.27
_exptl_special_details           ?

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.991

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9821
_diffrn_orient_matrix_ub_11      0.0013964000
_diffrn_orient_matrix_ub_12      -0.0029925000
_diffrn_orient_matrix_ub_13      -0.0587746000
_diffrn_orient_matrix_ub_21      -0.0129059000
_diffrn_orient_matrix_ub_22      0.0824142000
_diffrn_orient_matrix_ub_23      -0.0149210000
_diffrn_orient_matrix_ub_31      0.0887562000
_diffrn_orient_matrix_ub_32      -0.0016712000
_diffrn_orient_matrix_ub_33      -0.0209034000
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_number            13257
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.1
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             5397
_reflns_number_gt                3869
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
       CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
      CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5356
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.141
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.62906(11) 0.92032(11) 0.38824(11) 0.0480(3) Uani 1 1 d . . .
O1 O -0.14610(12) 0.90979(12) -0.19198(12) 0.0539(4) Uani 1 1 d . . .
C29 C 0.41447(16) 0.64446(14) 0.48248(15) 0.0389(4) Uani 1 1 d . . .
H29 H 0.4456 0.5683 0.5286 0.047 Uiso 1 1 calc R . .
N6 N 0.24165(14) 0.66375(13) 0.37611(13) 0.0452(4) Uani 1 1 d . . .
H6 H 0.1654 0.6692 0.3563 0.054 Uiso 1 1 calc R . .
O2 O 0.06018(14) 0.64730(14) 0.23005(13) 0.0673(5) Uani 1 1 d . . .
C3 C 0.02120(16) 0.79752(15) -0.01613(15) 0.0400(4) Uani 1 1 d . . .
H3 H 0.0909 0.8187 0.0189 0.048 Uiso 1 1 calc R . .
O4 O 0.19481(13) 0.61523(13) 0.56963(12) 0.0605(4) Uani 1 1 d . . .
C4 C -0.09465(16) 0.86466(14) 0.00356(16) 0.0385(4) Uani 1 1 d . . .
C20 C 0.41893(16) 0.85626(14) 0.46285(15) 0.0359(4) Uani 1 1 d . . .
C19 C 0.50278(16) 0.93785(14) 0.39395(15) 0.0370(4) Uani 1 1 d . . .
N4 N 0.47499(16) 1.04377(13) 0.32236(15) 0.0552(5) Uani 1 1 d . . .
H4A H 0.5348 1.0894 0.2811 0.066 Uiso 1 1 calc R . .
H4B H 0.3973 1.066 0.3177 0.066 Uiso 1 1 calc R . .
C10 C 0.18517(18) 0.82011(15) -0.18337(16) 0.0441(5) Uani 1 1 d . . .
C22 C 0.59910(17) 0.73004(15) 0.53667(16) 0.0403(4) Uani 1 1 d . . .
C2 C 0.05837(16) 0.83506(15) -0.14348(16) 0.0410(4) Uani 1 1 d . . .
N3 N -0.10469(15) 0.54432(13) 0.20741(14) 0.0492(4) Uani 1 1 d . . .
H3A H -0.1254 0.5052 0.2786 0.059 Uiso 1 1 calc R . .
C11 C 0.00393(16) 0.66466(15) 0.03878(16) 0.0388(4) Uani 1 1 d . . .
H11 H 0.0797 0.6296 0.0138 0.047 Uiso 1 1 calc R . .
C18 C -0.11010(16) 0.61049(14) 0.01360(16) 0.0377(4) Uani 1 1 d . . .
C27 C 0.67736(17) 0.81926(16) 0.46500(17) 0.0429(5) Uani 1 1 d . . .
C31 C 0.35062(17) 0.68037(14) 0.29875(16) 0.0395(4) Uani 1 1 d . . .
C35 C 0.57624(18) 0.67808(16) 0.29880(19) 0.0486(5) Uani 1 1 d . . .
H35 H 0.6492 0.6692 0.337 0.058 Uiso 1 1 calc R . .
C30 C 0.27031(17) 0.63828(15) 0.48469(16) 0.0419(4) Uani 1 1 d . . .
C13 C -0.16809(17) 0.53722(14) 0.11733(16) 0.0408(4) Uani 1 1 d . . .
C28 C 0.29091(19) 0.88922(16) 0.46867(16) 0.0442(5) Uani 1 1 d . . .
C21 C 0.45750(16) 0.73499(14) 0.53178(15) 0.0374(4) Uani 1 1 d . . .
H21 H 0.4176 0.715 0.6102 0.045 Uiso 1 1 calc R . .
C5 C -0.1264(2) 0.87952(17) 0.10726(18) 0.0530(5) Uani 1 1 d . . .
H5 H -0.0759 0.8468 0.1675 0.064 Uiso 1 1 calc R . .
C1 C -0.02575(17) 0.88286(16) -0.22211(17) 0.0446(5) Uani 1 1 d . . .
C36 C 0.45760(16) 0.66825(14) 0.35828(16) 0.0369(4) Uani 1 1 d . . .
N2 N 0.28857(16) 0.81110(14) -0.21527(17) 0.0630(5) Uani 1 1 d . . .
C9 C -0.17113(17) 0.91643(15) -0.08332(17) 0.0437(5) Uani 1 1 d . . .
N1 N -0.00847(17) 0.90725(17) -0.33498(14) 0.0688(6) Uani 1 1 d . . .
H1A H 0.063 0.8924 -0.3653 0.083 Uiso 1 1 calc R . .
H1B H -0.0688 0.9378 -0.3775 0.083 Uiso 1 1 calc R . .
N5 N 0.18779(18) 0.91876(17) 0.47278(17) 0.0685(5) Uani 1 1 d . . .
C12 C -0.00746(17) 0.61972(16) 0.16945(17) 0.0473(5) Uani 1 1 d . . .
C6 C -0.2323(2) 0.94234(19) 0.1223(2) 0.0625(6) Uani 1 1 d . . .
H6A H -0.2521 0.9517 0.1923 0.075 Uiso 1 1 calc R . .
C17 C -0.1605(2) 0.61775(16) -0.08619(18) 0.0517(5) Uani 1 1 d . . .
H17 H -0.1237 0.6653 -0.1572 0.062 Uiso 1 1 calc R . .
C14 C -0.27246(19) 0.47154(17) 0.1251(2) 0.0552(6) Uani 1 1 d . . .
H14 H -0.3086 0.4225 0.1957 0.066 Uiso 1 1 calc R . .
C32 C 0.3575(2) 0.70252(17) 0.18228(18) 0.0518(5) Uani 1 1 d . . .
H32 H 0.2848 0.7098 0.144 0.062 Uiso 1 1 calc R . .
C23 C 0.6588(2) 0.63335(18) 0.60843(19) 0.0572(6) Uani 1 1 d . . .
H23 H 0.6095 0.5724 0.6592 0.069 Uiso 1 1 calc R . .
C33 C 0.4774(2) 0.71339(18) 0.1249(2) 0.0588(6) Uani 1 1 d . . .
H33 H 0.4853 0.7292 0.0463 0.071 Uiso 1 1 calc R . .
C8 C -0.2778(2) 0.97971(18) -0.0698(2) 0.0599(6) Uani 1 1 d . . .
H8 H -0.3277 1.0139 -0.1303 0.072 Uiso 1 1 calc R . .
C34 C 0.5849(2) 0.70136(18) 0.1816(2) 0.0564(6) Uani 1 1 d . . .
H34 H 0.6642 0.7089 0.141 0.068 Uiso 1 1 calc R . .
C26 C 0.80753(19) 0.8144(2) 0.4627(2) 0.0583(6) Uani 1 1 d . . .
H26 H 0.8571 0.8764 0.4142 0.07 Uiso 1 1 calc R . .
C15 C -0.3223(2) 0.48045(19) 0.0245(2) 0.0640(6) Uani 1 1 d . . .
H15 H -0.3934 0.4372 0.0267 0.077 Uiso 1 1 calc R . .
C7 C -0.3078(2) 0.99064(19) 0.0351(2) 0.0668(7) Uani 1 1 d . . .
H7 H -0.38 1.0311 0.0464 0.08 Uiso 1 1 calc R . .
C25 C 0.8634(2) 0.7162(2) 0.5334(2) 0.0709(7) Uani 1 1 d . . .
H25 H 0.9513 0.7111 0.5319 0.085 Uiso 1 1 calc R . .
C24 C 0.7894(2) 0.6256(2) 0.6063(2) 0.0721(7) Uani 1 1 d . . .
H24 H 0.8271 0.5593 0.6539 0.087 Uiso 1 1 calc R . .
C16 C -0.2675(2) 0.55257(19) -0.0783(2) 0.0668(7) Uani 1 1 d . . .
H16 H -0.303 0.5582 -0.1452 0.08 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C19 1.348(2) . ?
O3 C27 1.396(2) . ?
O1 C1 1.362(2) . ?
O1 C9 1.394(2) . ?
C29 C36 1.505(2) . ?
C29 C30 1.528(2) . ?
C29 C21 1.559(2) . ?
C29 H29 0.98 . ?
N6 C30 1.344(2) . ?
N6 C31 1.406(2) . ?
N6 H6 0.86 . ?
O2 O2 0.000(3) 1 ?
O2 C12 1.228(2) . ?
C3 C2 1.510(2) . ?
C3 C4 1.514(2) . ?
C3 C11 1.551(2) . ?
C3 H3 0.98 . ?
O4 C30 1.221(2) . ?
C4 C9 1.374(3) . ?
C4 C5 1.387(3) . ?
C20 C19 1.357(2) . ?
C20 C28 1.407(2) . ?
C20 C21 1.508(2) . ?
C19 N4 1.342(2) . ?
N4 H4A 0.86 . ?
N4 H4B 0.86 . ?
C10 N2 1.146(2) . ?
C10 C2 1.419(2) . ?
C22 C27 1.386(3) . ?
C22 C23 1.391(3) . ?
C22 C21 1.505(2) . ?
C2 C1 1.353(3) . ?
N3 C12 1.344(2) . ?
N3 C13 1.396(2) . ?
N3 H3A 0.86 . ?
C11 C18 1.510(2) . ?
C11 C12 1.523(3) . ?
C11 H11 0.98 . ?
C18 C17 1.378(3) . ?
C18 C13 1.389(3) . ?
C27 C26 1.376(3) . ?
C31 C32 1.381(3) . ?
C31 C36 1.389(2) . ?
C35 C36 1.385(2) . ?
C35 C34 1.386(3) . ?
C35 H35 0.93 . ?
C13 C14 1.368(3) . ?
C28 N5 1.144(2) . ?
C21 H21 0.98 . ?
C5 C6 1.384(3) . ?
C5 H5 0.93 . ?
C1 N1 1.332(2) . ?
C9 C8 1.389(3) . ?
N1 H1A 0.86 . ?
N1 H1B 0.86 . ?
C12 O2 1.228(2) 1 ?
C6 C7 1.363(3) . ?
C6 H6A 0.93 . ?
C17 C16 1.386(3) . ?
C17 H17 0.93 . ?
C14 C15 1.378(3) . ?
C14 H14 0.93 . ?
C32 C33 1.384(3) . ?
C32 H32 0.93 . ?
C23 C24 1.381(3) . ?
C23 H23 0.93 . ?
C33 C34 1.374(3) . ?
C33 H33 0.93 . ?
C8 C7 1.377(3) . ?
C8 H8 0.93 . ?
C34 H34 0.93 . ?
C26 C25 1.380(3) . ?
C26 H26 0.93 . ?
C15 C16 1.365(3) . ?
C15 H15 0.93 . ?
C7 H7 0.93 . ?
C25 C24 1.376(4) . ?
C25 H25 0.93 . ?
C24 H24 0.93 . ?
C16 H16 0.93 . ?

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
C19 O3 C27 118.90(14) . . ?
C1 O1 C9 117.54(15) . . ?
C36 C29 C30 102.79(14) . . ?
C36 C29 C21 115.36(14) . . ?
C30 C29 C21 112.39(14) . . ?
C36 C29 H29 108.7 . . ?
C30 C29 H29 108.7 . . ?
C21 C29 H29 108.7 . . ?
C30 N6 C31 112.22(15) . . ?
C30 N6 H6 123.9 . . ?
C31 N6 H6 123.9 . . ?
O2 O2 C12 0(10) 1 . ?
C2 C3 C4 108.90(15) . . ?
C2 C3 C11 111.24(14) . . ?
C4 C3 C11 113.82(14) . . ?
C2 C3 H3 107.5 . . ?
C4 C3 H3 107.5 . . ?
C11 C3 H3 107.5 . . ?
C9 C4 C5 117.23(18) . . ?
C9 C4 C3 120.46(16) . . ?
C5 C4 C3 122.29(18) . . ?
C19 C20 C28 117.00(16) . . ?
C19 C20 C21 123.02(15) . . ?
C28 C20 C21 119.98(15) . . ?
N4 C19 O3 110.58(15) . . ?
N4 C19 C20 126.63(16) . . ?
O3 C19 C20 122.79(15) . . ?
C19 N4 H4A 120 . . ?
C19 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
N2 C10 C2 177.93(19) . . ?
C27 C22 C23 116.52(17) . . ?
C27 C22 C21 121.49(16) . . ?
C23 C22 C21 121.89(17) . . ?
C1 C2 C10 118.21(17) . . ?
C1 C2 C3 122.11(16) . . ?
C10 C2 C3 119.68(16) . . ?
C12 N3 C13 111.87(16) . . ?
C12 N3 H3A 124.1 . . ?
C13 N3 H3A 124.1 . . ?
C18 C11 C12 102.22(14) . . ?
C18 C11 C3 118.62(14) . . ?
C12 C11 C3 113.34(15) . . ?
C18 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C3 C11 H11 107.3 . . ?
C17 C18 C13 118.43(17) . . ?
C17 C18 C11 133.57(17) . . ?
C13 C18 C11 107.97(16) . . ?
C26 C27 C22 122.87(18) . . ?
C26 C27 O3 115.13(17) . . ?
C22 C27 O3 122.00(15) . . ?
C32 C31 C36 122.68(17) . . ?
C32 C31 N6 128.19(17) . . ?
C36 C31 N6 109.11(16) . . ?
C36 C35 C34 119.20(19) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
O4 C30 N6 126.24(17) . . ?
O4 C30 C29 126.16(18) . . ?
N6 C30 C29 107.60(15) . . ?
C14 C13 C18 123.12(19) . . ?
C14 C13 N3 127.41(18) . . ?
C18 C13 N3 109.47(16) . . ?
N5 C28 C20 178.3(2) . . ?
C22 C21 C20 109.63(14) . . ?
C22 C21 C29 109.92(14) . . ?
C20 C21 C29 112.56(14) . . ?
C22 C21 H21 108.2 . . ?
C20 C21 H21 108.2 . . ?
C29 C21 H21 108.2 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
N1 C1 C2 127.57(18) . . ?
N1 C1 O1 110.34(17) . . ?
C2 C1 O1 122.06(17) . . ?
C35 C36 C31 118.84(18) . . ?
C35 C36 C29 133.03(17) . . ?
C31 C36 C29 108.13(15) . . ?
C4 C9 C8 122.64(19) . . ?
C4 C9 O1 122.07(16) . . ?
C8 C9 O1 115.28(18) . . ?
C1 N1 H1A 120 . . ?
C1 N1 H1B 120 . . ?
H1A N1 H1B 120 . . ?
O2 C12 O2 0.00(14) 1 . ?
O2 C12 N3 125.68(19) 1 . ?
O2 C12 N3 125.68(19) . . ?
O2 C12 C11 126.16(17) 1 . ?
O2 C12 C11 126.16(17) . . ?
N3 C12 C11 108.16(16) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C18 C17 C16 118.5(2) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C13 C14 C15 117.7(2) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C31 C32 C33 117.13(19) . . ?
C31 C32 H32 121.4 . . ?
C33 C32 H32 121.4 . . ?
C24 C23 C22 121.7(2) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C34 C33 C32 121.4(2) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C7 C8 C9 118.5(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C33 C34 C35 120.68(19) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C27 C26 C25 119.0(2) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C24 C25 C26 120.1(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C15 C16 C17 122.0(2) . . ?
C15 C16 H16 119 . . ?
C17 C16 H16 119 . . ?

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 C3 C4 C9 20.3(2) . . . . ?
C11 C3 C4 C9 -104.48(18) . . . . ?
C2 C3 C4 C5 -157.93(15) . . . . ?
C11 C3 C4 C5 77.3(2) . . . . ?
C27 O3 C19 N4 173.65(15) . . . . ?
C27 O3 C19 C20 -7.2(2) . . . . ?
C28 C20 C19 N4 -6.7(3) . . . . ?
C21 C20 C19 N4 173.55(17) . . . . ?
C28 C20 C19 O3 174.30(15) . . . . ?
C21 C20 C19 O3 -5.5(3) . . . . ?
N2 C10 C2 C1 97(6) . . . . ?
N2 C10 C2 C3 -84(6) . . . . ?
C4 C3 C2 C1 -23.6(2) . . . . ?
C11 C3 C2 C1 102.6(2) . . . . ?
C4 C3 C2 C10 156.48(15) . . . . ?
C11 C3 C2 C10 -77.28(19) . . . . ?
C2 C3 C11 C18 -71.7(2) . . . . ?
C4 C3 C11 C18 51.8(2) . . . . ?
C2 C3 C11 C12 168.47(14) . . . . ?
C4 C3 C11 C12 -68.05(19) . . . . ?
C12 C11 C18 C17 177.1(2) . . . . ?
C3 C11 C18 C17 51.6(3) . . . . ?
C12 C11 C18 C13 -5.00(18) . . . . ?
C3 C11 C18 C13 -130.45(16) . . . . ?
C23 C22 C27 C26 0.4(3) . . . . ?
C21 C22 C27 C26 -176.09(17) . . . . ?
C23 C22 C27 O3 179.35(17) . . . . ?
C21 C22 C27 O3 2.9(3) . . . . ?
C19 O3 C27 C26 -172.52(16) . . . . ?
C19 O3 C27 C22 8.5(2) . . . . ?
C30 N6 C31 C32 176.93(18) . . . . ?
C30 N6 C31 C36 -1.6(2) . . . . ?
C31 N6 C30 O4 -176.94(18) . . . . ?
C31 N6 C30 C29 3.57(19) . . . . ?
C36 C29 C30 O4 176.52(18) . . . . ?
C21 C29 C30 O4 -58.8(2) . . . . ?
C36 C29 C30 N6 -3.99(17) . . . . ?
C21 C29 C30 N6 120.66(16) . . . . ?
C17 C18 C13 C14 0.3(3) . . . . ?
C11 C18 C13 C14 -177.95(17) . . . . ?
C17 C18 C13 N3 -178.69(16) . . . . ?
C11 C18 C13 N3 3.0(2) . . . . ?
C12 N3 C13 C14 -178.36(18) . . . . ?
C12 N3 C13 C18 0.6(2) . . . . ?
C19 C20 C28 N5 -27(7) . . . . ?
C21 C20 C28 N5 152(7) . . . . ?
C27 C22 C21 C20 -13.4(2) . . . . ?
C23 C22 C21 C20 170.30(17) . . . . ?
C27 C22 C21 C29 110.82(18) . . . . ?
C23 C22 C21 C29 -65.5(2) . . . . ?
C19 C20 C21 C22 15.0(2) . . . . ?
C28 C20 C21 C22 -164.80(15) . . . . ?
C19 C20 C21 C29 -107.73(19) . . . . ?
C28 C20 C21 C29 72.5(2) . . . . ?
C36 C29 C21 C22 -67.38(19) . . . . ?
C30 C29 C21 C22 175.22(14) . . . . ?
C36 C29 C21 C20 55.1(2) . . . . ?
C30 C29 C21 C20 -62.27(19) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C6 179.36(16) . . . . ?
C10 C2 C1 N1 8.1(3) . . . . ?
C3 C2 C1 N1 -171.80(18) . . . . ?
C10 C2 C1 O1 -174.03(16) . . . . ?
C3 C2 C1 O1 6.1(3) . . . . ?
C9 O1 C1 N1 -164.74(16) . . . . ?
C9 O1 C1 C2 17.0(2) . . . . ?
C34 C35 C36 C31 1.0(3) . . . . ?
C34 C35 C36 C29 -179.81(18) . . . . ?
C32 C31 C36 C35 -0.4(3) . . . . ?
N6 C31 C36 C35 178.23(14) . . . . ?
C32 C31 C36 C29 -179.79(16) . . . . ?
N6 C31 C36 C29 -1.19(19) . . . . ?
C30 C29 C36 C35 -176.22(17) . . . . ?
C21 C29 C36 C35 61.1(2) . . . . ?
C30 C29 C36 C31 3.08(17) . . . . ?
C21 C29 C36 C31 -119.59(16) . . . . ?
C5 C4 C9 C8 -1.2(3) . . . . ?
C3 C4 C9 C8 -179.45(16) . . . . ?
C5 C4 C9 O1 178.24(15) . . . . ?
C3 C4 C9 O1 0.0(2) . . . . ?
C1 O1 C9 C4 -20.1(2) . . . . ?
C1 O1 C9 C8 159.33(17) . . . . ?
O2 O2 C12 N3 0.00(6) 1 . . . ?
O2 O2 C12 C11 0.00(15) 1 . . . ?
C13 N3 C12 O2 176.05(19) . . . 1 ?
C13 N3 C12 O2 176.05(19) . . . . ?
C13 N3 C12 C11 -3.9(2) . . . . ?
C18 C11 C12 O2 -174.61(19) . . . 1 ?
C3 C11 C12 O2 -45.8(3) . . . 1 ?
C18 C11 C12 O2 -174.61(19) . . . . ?
C3 C11 C12 O2 -45.8(3) . . . . ?
C18 C11 C12 N3 5.38(19) . . . . ?
C3 C11 C12 N3 134.23(16) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C13 C18 C17 C16 0.7(3) . . . . ?
C11 C18 C17 C16 178.41(19) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
N3 C13 C14 C15 178.04(18) . . . . ?
C36 C31 C32 C33 -0.5(3) . . . . ?
N6 C31 C32 C33 -178.77(18) . . . . ?
C27 C22 C23 C24 -1.6(3) . . . . ?
C21 C22 C23 C24 174.92(18) . . . . ?
C31 C32 C33 C34 0.7(3) . . . . ?
C4 C9 C8 C7 -0.1(3) . . . . ?
O1 C9 C8 C7 -179.56(17) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C36 C35 C34 C33 -0.7(3) . . . . ?
C22 C27 C26 C25 0.9(3) . . . . ?
O3 C27 C26 C25 -178.13(18) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C9 C8 C7 C6 1.5(3) . . . . ?
C27 C26 C25 C24 -1.1(3) . . . . ?
C26 C25 C24 C23 -0.1(4) . . . . ?
C22 C23 C24 C25 1.4(3) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C18 C17 C16 C15 -1.2(3) . . . . ?

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
N1 H1A N5 0.86 2.24 2.998(3) 146.7 1_554
N1 H1B N5 0.86 2.19 2.991(3) 154.4 2_575
N3 H3A O4 0.86 2.04 2.879(2) 165.2 2_566
N4 H4A N2 0.86 2.19 3.036(2) 165.7 2_675
C6 H6A O3 0.93 2.56 3.435(3) 157.8 1_455
N6 H6 O2 0.86 2.12 2.834(2) 140.7 1
C32 H32 O2 0.93 2.54 3.197(3) 127.9 1

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_melting_point          273
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_FINAL
_database_code_depnum_ccdc_archive 'CCDC 1010757'
_audit_update_record             
;
2014-06-27 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
(trans-7,7a)-5-amino-2-methyl-1,3-dioxo-7-(p-tolyl)-2,3,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazole-6-carbonitrile
_chemical_formula_moiety         'C18 H14 Cl N3 O3'
_chemical_formula_sum            'C18 H14 Cl N3 O3'
_chemical_formula_weight         354.76
_chemical_absolute_configuration unk
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P-1 '
_symmetry_space_group_name_Hall  '-P 1'


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

_cell_length_a                   8.5442(11)
_cell_length_b                   9.0229(11)
_cell_length_c                   12.0114(11)
_cell_angle_alpha                75.054(9)
_cell_angle_beta                 69.757(10)
_cell_angle_gamma                76.217(11)
_cell_volume                     827.99(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8499
_cell_measurement_theta_min      3.7950
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             366
_exptl_special_details           ?

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.991

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9821
_diffrn_orient_matrix_ub_11      0.0013964000
_diffrn_orient_matrix_ub_12      -0.0029925000
_diffrn_orient_matrix_ub_13      -0.0587746000
_diffrn_orient_matrix_ub_21      -0.0129059000
_diffrn_orient_matrix_ub_22      0.0824142000
_diffrn_orient_matrix_ub_23      -0.0149210000
_diffrn_orient_matrix_ub_31      0.0887562000
_diffrn_orient_matrix_ub_32      -0.0016712000
_diffrn_orient_matrix_ub_33      -0.0209034000
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_number            7502
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.8
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             2927
_reflns_number_gt                2363
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
       CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
      CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.124
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   0.606
_refine_ls_restrained_S_all      0.606
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.047
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H3B H 0.213(5) 0.417(4) 0.472(4) 0.115(13) Uiso 1 1 d . . .
H3A H 0.291(5) 0.424(4) 0.558(3) 0.103(12) Uiso 1 1 d . . .
Cl1 Cl 0.23958(10) 0.53505(7) 0.91019(6) 0.0699(3) Uani 1 1 d . . .
O1 O 0.22565(19) -0.13492(16) 1.07076(13) 0.0422(4) Uani 1 1 d . . .
O2 O 0.29129(17) 0.29640(16) 1.33449(13) 0.0409(4) Uani 1 1 d . . .
C4 C 0.2863(2) 0.0999(2) 1.10179(14) 0.0282(4) Uani 1 1 d . . .
C5 C 0.2913(2) 0.2584(2) 1.05893(16) 0.0362(4) Uani 1 1 d . . .
H5 H 0.3319 0.3121 1.0968 0.043 Uiso 1 1 calc R . .
N3 N 0.01319(19) 0.29715(18) 1.35394(14) 0.0347(4) Uani 1 1 d . . .
H3 H -0.0253 0.3928 1.36 0.042 Uiso 1 1 calc R . .
C3 C 0.3328(2) 0.0139(2) 1.21546(15) 0.0264(4) Uani 1 1 d . . .
H3C H 0.4393 0.0415 1.211 0.032 Uiso 1 1 calc R . .
C18 C 0.0146(2) 0.0458(2) 1.34545(14) 0.0266(4) Uani 1 1 d . . .
C2 C 0.3596(2) -0.1598(2) 1.22068(16) 0.0291(4) Uani 1 1 d . . .
C8 C 0.1793(3) 0.1008(3) 0.93797(18) 0.0421(5) Uani 1 1 d . . .
H8 H 0.1442 0.0465 0.8972 0.051 Uiso 1 1 calc R . .
C9 C 0.2320(2) 0.0236(2) 1.03825(16) 0.0327(4) Uani 1 1 d . . .
C13 C -0.0865(2) 0.1911(2) 1.35743(15) 0.0301(4) Uani 1 1 d . . .
C10 C 0.4409(2) -0.2633(2) 1.30254(17) 0.0341(4) Uani 1 1 d . . .
C11 C 0.1942(2) 0.05925(19) 1.33201(15) 0.0259(4) Uani 1 1 d . . .
H11 H 0.2246 -0.0067 1.4026 0.031 Uiso 1 1 calc R . .
C6 C 0.2363(3) 0.3360(2) 0.96028(17) 0.0426(5) Uani 1 1 d . . .
C17 C -0.0600(2) -0.0776(2) 1.35083(16) 0.0333(4) Uani 1 1 d . . .
H17 H 0.0041 -0.1759 1.3454 0.04 Uiso 1 1 calc R . .
C1 C 0.2981(2) -0.2231(2) 1.15613(17) 0.0356(4) Uani 1 1 d . . .
C14 C -0.2582(2) 0.2194(2) 1.37088(17) 0.0380(5) Uani 1 1 d . . .
H14 H -0.3224 0.3174 1.3777 0.046 Uiso 1 1 calc R . .
N2 N 0.5089(3) -0.3473(2) 1.36803(17) 0.0536(5) Uani 1 1 d . . .
C7 C 0.1795(3) 0.2585(3) 0.89946(18) 0.0461(5) Uani 1 1 d . . .
H7 H 0.1421 0.3123 0.8337 0.055 Uiso 1 1 calc R . .
C12 C 0.1766(2) 0.2304(2) 1.33985(15) 0.0291(4) Uani 1 1 d . . .
C16 C -0.2331(3) -0.0519(3) 1.36460(18) 0.0410(5) Uani 1 1 d . . .
H16 H -0.284 -0.1338 1.3677 0.049 Uiso 1 1 calc R . .
C15 C -0.3304(3) 0.0947(3) 1.37378(18) 0.0421(5) Uani 1 1 d . . .
H15 H -0.445 0.1096 1.3819 0.051 Uiso 1 1 calc R . .
N1 N 0.2953(3) -0.3742(2) 1.16606(19) 0.0583(6) Uani 1 1 d . . .
H1A H 0.2516 -0.4019 1.1215 0.07 Uiso 1 1 calc R . .
H1B H 0.3372 -0.4434 1.217 0.07 Uiso 1 1 calc R . .
O3 O 0.1907(2) 0.4436(2) 0.5485(2) 0.0661(5) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.744(2) . ?
O1 C1 1.361(2) . ?
O1 C9 1.391(2) . ?
O2 C12 1.238(2) . ?
C4 C9 1.393(3) . ?
C4 C5 1.394(3) . ?
C4 C3 1.519(2) . ?
C5 C6 1.385(3) . ?
C5 H5 0.93 . ?
N3 C12 1.352(2) . ?
N3 C13 1.409(2) . ?
N3 H3 0.86 . ?
C3 C2 1.516(2) . ?
C3 C11 1.565(2) . ?
C3 H3C 0.98 . ?
C18 C17 1.386(3) . ?
C18 C13 1.399(3) . ?
C18 C11 1.517(2) . ?
C2 C1 1.363(3) . ?
C2 C10 1.418(3) . ?
C8 C7 1.378(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.93 . ?
C13 C14 1.386(3) . ?
C10 N2 1.153(3) . ?
C11 C12 1.540(2) . ?
C11 H11 0.98 . ?
C6 C7 1.389(3) . ?
C17 C16 1.399(3) . ?
C17 H17 0.93 . ?
C1 N1 1.343(3) . ?
C14 C15 1.395(3) . ?
C14 H14 0.93 . ?
C7 H7 0.93 . ?
C16 C15 1.393(3) . ?
C16 H16 0.93 . ?
C15 H15 0.93 . ?
N1 H1A 0.86 . ?
N1 H1B 0.86 . ?
O3 H3B 0.95(4) . ?
O3 H3A 0.88(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 118.72(14) . . ?
C9 C4 C5 117.43(17) . . ?
C9 C4 C3 120.85(16) . . ?
C5 C4 C3 121.69(16) . . ?
C6 C5 C4 120.32(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C12 N3 C13 111.90(15) . . ?
C12 N3 H3 124 . . ?
C13 N3 H3 124 . . ?
C2 C3 C4 109.14(14) . . ?
C2 C3 C11 110.58(14) . . ?
C4 C3 C11 111.65(13) . . ?
C2 C3 H3C 108.5 . . ?
C4 C3 H3C 108.5 . . ?
C11 C3 H3C 108.5 . . ?
C17 C18 C13 118.98(16) . . ?
C17 C18 C11 132.85(16) . . ?
C13 C18 C11 108.14(15) . . ?
C1 C2 C10 117.54(17) . . ?
C1 C2 C3 122.92(16) . . ?
C10 C2 C3 119.37(15) . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 O1 115.12(17) . . ?
C8 C9 C4 122.31(19) . . ?
O1 C9 C4 122.57(16) . . ?
C14 C13 C18 123.06(18) . . ?
C14 C13 N3 127.46(18) . . ?
C18 C13 N3 109.48(15) . . ?
N2 C10 C2 179.1(2) . . ?
C18 C11 C12 102.33(13) . . ?
C18 C11 C3 116.06(13) . . ?
C12 C11 C3 113.17(14) . . ?
C18 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C3 C11 H11 108.3 . . ?
C5 C6 C7 121.4(2) . . ?
C5 C6 Cl1 119.52(18) . . ?
C7 C6 Cl1 119.11(16) . . ?
C18 C17 C16 118.98(18) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
N1 C1 O1 110.08(17) . . ?
N1 C1 C2 127.47(18) . . ?
O1 C1 C2 122.44(17) . . ?
C13 C14 C15 117.13(18) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C8 C7 C6 119.07(19) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
O2 C12 N3 125.56(17) . . ?
O2 C12 C11 126.31(16) . . ?
N3 C12 C11 108.13(15) . . ?
C15 C16 C17 120.90(19) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C15 C14 120.91(18) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C1 N1 H1A 120 . . ?
C1 N1 H1B 120 . . ?
H1A N1 H1B 120 . . ?
H3B O3 H3A 103(3) . . ?

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
C9 C4 C5 C6 3.0(3) . . . . ?
C3 C4 C5 C6 -175.19(16) . . . . ?
C9 C4 C3 C2 16.5(2) . . . . ?
C5 C4 C3 C2 -165.38(16) . . . . ?
C9 C4 C3 C11 -106.03(18) . . . . ?
C5 C4 C3 C11 72.1(2) . . . . ?
C4 C3 C2 C1 -19.2(2) . . . . ?
C11 C3 C2 C1 103.97(19) . . . . ?
C4 C3 C2 C10 165.65(15) . . . . ?
C11 C3 C2 C10 -71.15(19) . . . . ?
C7 C8 C9 O1 179.37(17) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C1 O1 C9 C8 170.37(17) . . . . ?
C1 O1 C9 C4 -10.0(3) . . . . ?
C5 C4 C9 C8 -1.9(3) . . . . ?
C3 C4 C9 C8 176.23(17) . . . . ?
C5 C4 C9 O1 178.43(16) . . . . ?
C3 C4 C9 O1 -3.4(3) . . . . ?
C17 C18 C13 C14 -2.0(3) . . . . ?
C11 C18 C13 C14 179.67(15) . . . . ?
C17 C18 C13 N3 177.75(15) . . . . ?
C11 C18 C13 N3 -0.55(19) . . . . ?
C12 N3 C13 C14 179.94(17) . . . . ?
C12 N3 C13 C18 0.2(2) . . . . ?
C1 C2 C10 N2 98(15) . . . . ?
C3 C2 C10 N2 -86(15) . . . . ?
C17 C18 C11 C12 -177.30(17) . . . . ?
C13 C18 C11 C12 0.67(17) . . . . ?
C17 C18 C11 C3 59.0(2) . . . . ?
C13 C18 C11 C3 -123.06(15) . . . . ?
C2 C3 C11 C18 -69.32(18) . . . . ?
C4 C3 C11 C18 52.4(2) . . . . ?
C2 C3 C11 C12 172.79(13) . . . . ?
C4 C3 C11 C12 -65.49(18) . . . . ?
C4 C5 C6 C7 -1.9(3) . . . . ?
C4 C5 C6 Cl1 178.68(14) . . . . ?
C13 C18 C17 C16 1.8(2) . . . . ?
C11 C18 C17 C16 179.61(17) . . . . ?
C9 O1 C1 N1 -173.45(17) . . . . ?
C9 O1 C1 C2 7.6(3) . . . . ?
C10 C2 C1 N1 4.7(3) . . . . ?
C3 C2 C1 N1 -170.52(19) . . . . ?
C10 C2 C1 O1 -176.59(17) . . . . ?
C3 C2 C1 O1 8.2(3) . . . . ?
C18 C13 C14 C15 0.8(3) . . . . ?
N3 C13 C14 C15 -178.93(17) . . . . ?
C9 C8 C7 C6 1.5(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
Cl1 C6 C7 C8 179.03(15) . . . . ?
C13 N3 C12 O2 -179.62(16) . . . . ?
C13 N3 C12 C11 0.27(19) . . . . ?
C18 C11 C12 O2 179.32(16) . . . . ?
C3 C11 C12 O2 -55.0(2) . . . . ?
C18 C11 C12 N3 -0.57(17) . . . . ?
C3 C11 C12 N3 125.07(15) . . . . ?
C18 C17 C16 C15 -0.5(3) . . . . ?
C17 C16 C15 C14 -0.7(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?

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
N1 H1A Cl1 0.86 2.78 3.583(2) 156 1_545
N1 H1B O2 0.86 2.45 3.135(2) 136.9 1_545
N3 H3 O3 0.86 2.04 2.818(2) 150.5 2_567
O3 H3A N2 0.88(4) 2.09(4) 2.936(3) 163(3) 2_657

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_FINAL
_database_code_depnum_ccdc_archive 'CCDC 1010767'
_audit_update_record             
;
2014-06-27 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
(4S)-2-amino-4-[(3R)-2-oxo-3,3a,4,5,6,7-hexahydro-2H-indol-3-yl]-6-[(oxoimino)-$l^{1}-oxidanyl]-4a,5,6,7,8,8a-hexahydro-4H-chromene-3-carbonitrile
_chemical_formula_moiety         'C18 H12 N4 O4'
_chemical_formula_sum            'C18 H12 N4 O4'
_chemical_formula_weight         348.32
_chemical_absolute_configuration unk
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P-1 '
_symmetry_space_group_name_Hall  'P 1'


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


_cell_length_a                   8.7120(17)
_cell_length_b                   9.422(2)
_cell_length_c                   12.348(3)
_cell_angle_alpha                68.00(2)
_cell_angle_beta                 70.789(19)
_cell_angle_gamma                71.259(3)
_cell_volume                     864.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      3.7950
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_special_details           ?

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.991

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9821
_diffrn_orient_matrix_ub_11      0.0013964000
_diffrn_orient_matrix_ub_12      -0.0029925000
_diffrn_orient_matrix_ub_13      -0.0587746000
_diffrn_orient_matrix_ub_21      -0.0129059000
_diffrn_orient_matrix_ub_22      0.0824142000
_diffrn_orient_matrix_ub_23      -0.0149210000
_diffrn_orient_matrix_ub_31      0.0887562000
_diffrn_orient_matrix_ub_32      -0.0016712000
_diffrn_orient_matrix_ub_33      -0.0209034000
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_number            6710
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             3028
_reflns_number_gt                1492
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
       CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
      CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.2290
_refine_ls_wR_factor_gt          0.1809
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_restrained_S_all      0.99
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.046
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2896(3) 0.2258(3) 0.1524(2) 0.0672(8) Uani 1 1 d . . .
N1 N 0.3740(4) 0.0218(3) 0.3006(3) 0.0732(11) Uani 1 1 d . . .
H1A H 0.4154 -0.0243 0.3627 0.088 Uiso 1 1 calc R . .
H1B H 0.3436 -0.0319 0.2715 0.088 Uiso 1 1 calc R . .
C9 C 0.2717(4) 0.3825(4) 0.0841(3) 0.0528(9) Uani 1 1 d . . .
C3 C 0.3488(4) 0.4517(4) 0.2348(3) 0.0484(9) Uani 1 1 d . . .
H3 H 0.4475 0.4929 0.2161 0.058 Uiso 1 1 calc R . .
C4 C 0.2984(4) 0.4950(4) 0.1180(3) 0.0494(9) Uani 1 1 d . . .
C10 C 0.4724(5) 0.2127(4) 0.3840(3) 0.0564(10) Uani 1 1 d . . .
C1 C 0.3568(4) 0.1764(4) 0.2494(3) 0.0512(9) Uani 1 1 d . . .
O4 O 0.2959(4) 0.7734(3) 0.2600(3) 0.0818(9) Uani 1 1 d . . .
C5 C 0.2737(5) 0.6467(4) 0.0422(3) 0.0628(10) Uani 1 1 d . . .
H5 H 0.2944 0.7253 0.0602 0.075 Uiso 1 1 calc R . .
C18 C 0.0385(4) 0.5023(4) 0.3491(3) 0.0491(9) Uani 1 1 d . . .
C2 C 0.3983(4) 0.2761(4) 0.2844(3) 0.0475(9) Uani 1 1 d . . .
C11 C 0.2119(4) 0.5251(4) 0.3280(3) 0.0467(9) Uani 1 1 d . . .
H11 H 0.2449 0.4818 0.4047 0.056 Uiso 1 1 calc R . .
C8 C 0.2226(5) 0.4171(5) -0.0211(3) 0.0698(11) Uani 1 1 d . . .
H8 H 0.2092 0.3382 -0.0429 0.084 Uiso 1 1 calc R . .
N2 N 0.5313(5) 0.1667(4) 0.4650(3) 0.0823(11) Uani 1 1 d . . .
C6 C 0.2195(5) 0.6832(5) -0.0585(3) 0.0724(12) Uani 1 1 d . . .
N4 N 0.0248(4) 0.7643(4) 0.2834(3) 0.0699(10) Uani 1 1 d . . .
H4 H -0.0181 0.8635 0.2618 0.084 Uiso 1 1 calc R . .
C12 C 0.1874(6) 0.7028(5) 0.2871(3) 0.0611(10) Uani 1 1 d . . .
N3 N 0.1849(6) 0.8479(6) -0.1338(4) 0.1061(16) Uani 1 1 d . . .
C13 C -0.0659(5) 0.6495(5) 0.3186(3) 0.0603(10) Uani 1 1 d . . .
C17 C -0.0242(5) 0.3703(5) 0.3928(3) 0.0648(11) Uani 1 1 d . . .
H17 H 0.0442 0.2711 0.416 0.078 Uiso 1 1 calc R . .
O3 O 0.1189(6) 0.8793(4) -0.2148(3) 0.1415(17) Uani 1 1 d . . .
C14 C -0.2329(6) 0.6687(7) 0.3265(4) 0.0881(15) Uani 1 1 d . . .
H14 H -0.3017 0.768 0.3044 0.106 Uiso 1 1 calc R . .
C7 C 0.1943(5) 0.5711(6) -0.0922(3) 0.0804(14) Uani 1 1 d . . .
H7 H 0.1587 0.5986 -0.162 0.097 Uiso 1 1 calc R . .
C16 C -0.1932(6) 0.3877(8) 0.4017(4) 0.0873(15) Uani 1 1 d . . .
H16 H -0.2375 0.2992 0.4303 0.105 Uiso 1 1 calc R . .
O2 O 0.2189(6) 0.9461(5) -0.1069(4) 0.1421(18) Uani 1 1 d . . .
C15 C -0.2935(6) 0.5338(10) 0.3687(4) 0.0993(18) Uani 1 1 d . . .
H15 H -0.4053 0.5429 0.3746 0.119 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.365(4) . ?
O1 C9 1.386(4) . ?
N1 C1 1.333(4) . ?
N1 H1A 0.86 . ?
N1 H1B 0.86 . ?
C9 C4 1.382(5) . ?
C9 C8 1.391(5) . ?
C3 C2 1.502(4) . ?
C3 C4 1.516(4) . ?
C3 C11 1.545(5) . ?
C3 H3 0.98 . ?
C4 C5 1.377(5) . ?
C10 N2 1.149(4) . ?
C10 C2 1.418(4) . ?
C1 C2 1.351(4) . ?
O4 C12 1.215(4) . ?
C5 C6 1.360(5) . ?
C5 H5 0.93 . ?
C18 C17 1.369(5) . ?
C18 C13 1.384(5) . ?
C18 C11 1.518(4) . ?
C11 C12 1.520(5) . ?
C11 H11 0.98 . ?
C8 C7 1.376(6) . ?
C8 H8 0.93 . ?
C6 C7 1.369(6) . ?
C6 N3 1.472(6) . ?
N4 C12 1.357(5) . ?
N4 C13 1.398(5) . ?
N4 H4 0.86 . ?
N3 O3 1.211(5) . ?
N3 O2 1.234(6) . ?
C13 C14 1.382(5) . ?
C17 C16 1.400(6) . ?
C17 H17 0.93 . ?
C14 C15 1.386(7) . ?
C14 H14 0.93 . ?
C7 H7 0.93 . ?
C16 C15 1.366(7) . ?
C16 H16 0.93 . ?
C15 H15 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 118.5(3) . . ?
C1 N1 H1A 120 . . ?
C1 N1 H1B 120 . . ?
H1A N1 H1B 120 . . ?
C4 C9 O1 123.0(3) . . ?
C4 C9 C8 122.8(3) . . ?
O1 C9 C8 114.2(3) . . ?
C2 C3 C4 109.6(3) . . ?
C2 C3 C11 111.7(3) . . ?
C4 C3 C11 112.7(3) . . ?
C2 C3 H3 107.5 . . ?
C4 C3 H3 107.5 . . ?
C11 C3 H3 107.5 . . ?
C5 C4 C9 116.8(3) . . ?
C5 C4 C3 122.4(3) . . ?
C9 C4 C3 120.8(3) . . ?
N2 C10 C2 177.5(4) . . ?
N1 C1 C2 126.9(3) . . ?
N1 C1 O1 110.7(3) . . ?
C2 C1 O1 122.4(3) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C17 C18 C13 120.0(4) . . ?
C17 C18 C11 132.1(3) . . ?
C13 C18 C11 107.8(3) . . ?
C1 C2 C10 118.2(3) . . ?
C1 C2 C3 123.3(3) . . ?
C10 C2 C3 118.0(3) . . ?
C18 C11 C12 103.3(3) . . ?
C18 C11 C3 115.2(3) . . ?
C12 C11 C3 111.2(3) . . ?
C18 C11 H11 109 . . ?
C12 C11 H11 109 . . ?
C3 C11 H11 109 . . ?
C7 C8 C9 118.3(4) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C5 C6 C7 122.0(4) . . ?
C5 C6 N3 119.6(5) . . ?
C7 C6 N3 118.4(4) . . ?
C12 N4 C13 113.0(3) . . ?
C12 N4 H4 123.5 . . ?
C13 N4 H4 123.5 . . ?
O4 C12 N4 127.7(4) . . ?
O4 C12 C11 125.6(4) . . ?
N4 C12 C11 106.7(4) . . ?
O3 N3 O2 124.3(5) . . ?
O3 N3 C6 118.0(6) . . ?
O2 N3 C6 117.6(5) . . ?
C14 C13 C18 122.0(4) . . ?
C14 C13 N4 128.9(4) . . ?
C18 C13 N4 109.2(3) . . ?
C18 C17 C16 118.7(4) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C13 C14 C15 117.2(5) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C6 C7 C8 119.0(4) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C15 C16 C17 120.4(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C15 C14 121.7(4) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?

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
C1 O1 C9 C4 -8.5(5) . . . . ?
C1 O1 C9 C8 172.1(3) . . . . ?
O1 C9 C4 C5 -179.1(3) . . . . ?
C8 C9 C4 C5 0.2(5) . . . . ?
O1 C9 C4 C3 -0.4(5) . . . . ?
C8 C9 C4 C3 178.8(3) . . . . ?
C2 C3 C4 C5 -169.0(3) . . . . ?
C11 C3 C4 C5 66.0(4) . . . . ?
C2 C3 C4 C9 12.5(4) . . . . ?
C11 C3 C4 C9 -112.6(3) . . . . ?
C9 O1 C1 N1 -176.4(3) . . . . ?
C9 O1 C1 C2 3.4(5) . . . . ?
C9 C4 C5 C6 2.4(5) . . . . ?
C3 C4 C5 C6 -176.3(3) . . . . ?
N1 C1 C2 C10 1.8(6) . . . . ?
O1 C1 C2 C10 -178.0(3) . . . . ?
N1 C1 C2 C3 -169.4(3) . . . . ?
O1 C1 C2 C3 10.9(5) . . . . ?
N2 C10 C2 C1 -166(10) . . . . ?
N2 C10 C2 C3 6(10) . . . . ?
C4 C3 C2 C1 -17.8(5) . . . . ?
C11 C3 C2 C1 107.9(4) . . . . ?
C4 C3 C2 C10 171.0(3) . . . . ?
C11 C3 C2 C10 -63.3(4) . . . . ?
C17 C18 C11 C12 -175.9(3) . . . . ?
C13 C18 C11 C12 2.2(3) . . . . ?
C17 C18 C11 C3 62.6(4) . . . . ?
C13 C18 C11 C3 -119.3(3) . . . . ?
C2 C3 C11 C18 -74.4(3) . . . . ?
C4 C3 C11 C18 49.6(4) . . . . ?
C2 C3 C11 C12 168.5(3) . . . . ?
C4 C3 C11 C12 -67.5(4) . . . . ?
C4 C9 C8 C7 -2.2(6) . . . . ?
O1 C9 C8 C7 177.2(3) . . . . ?
C4 C5 C6 C7 -3.0(6) . . . . ?
C4 C5 C6 N3 176.4(4) . . . . ?
C13 N4 C12 O4 178.9(4) . . . . ?
C13 N4 C12 C11 0.8(4) . . . . ?
C18 C11 C12 O4 -179.9(4) . . . . ?
C3 C11 C12 O4 -55.7(5) . . . . ?
C18 C11 C12 N4 -1.8(3) . . . . ?
C3 C11 C12 N4 122.4(3) . . . . ?
C5 C6 N3 O3 -171.7(4) . . . . ?
C7 C6 N3 O3 7.8(7) . . . . ?
C5 C6 N3 O2 5.4(7) . . . . ?
C7 C6 N3 O2 -175.2(5) . . . . ?
C17 C18 C13 C14 -2.5(5) . . . . ?
C11 C18 C13 C14 179.2(3) . . . . ?
C17 C18 C13 N4 176.5(3) . . . . ?
C11 C18 C13 N4 -1.8(4) . . . . ?
C12 N4 C13 C14 179.6(4) . . . . ?
C12 N4 C13 C18 0.7(4) . . . . ?
C13 C18 C17 C16 2.2(5) . . . . ?
C11 C18 C17 C16 -179.9(3) . . . . ?
C18 C13 C14 C15 1.2(6) . . . . ?
N4 C13 C14 C15 -177.6(4) . . . . ?
C5 C6 C7 C8 0.9(6) . . . . ?
N3 C6 C7 C8 -178.5(4) . . . . ?
C9 C8 C7 C6 1.6(6) . . . . ?
C18 C17 C16 C15 -0.8(6) . . . . ?
C17 C16 C15 C14 -0.5(7) . . . . ?
C13 C14 C15 C16 0.3(7) . . . . ?

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
N1 H1A N2 0.86 2.16 2.999(4) 166.1 2_656
N1 H1B O4 0.86 2.07 2.884(4) 157.8 1_545
N4 H4 O3 0.86 2.21 3.071(5) 175.7 2_575
C16 H16 N2 0.93 2.54 3.386(6) 151.5 1_455

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_melting_point          273
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
