# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_2_ZnOAc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  Complex of Zn-acetate with (E)-3-{[2-(2-aminoethyl)pyridine]-
  phenylmethylidene}-1,4-dihydro-2H-1-phenylpyrrolo[2,3-b]quinoxalin-
  2-one and acetonitrile solvent molecules in the ratio 1:1:1
;
_chemical_name_common            ?

_chemical_melting_point          ?
_chemical_melting_point_lt       473
_chemical_melting_point_gt       471
_chemical_formula_moiety         'C32 H25 N5 O3 Zn1 . C2 H3 N1'
_chemical_formula_sum            'C34 H28 N6 O3 Zn'
_chemical_formula_weight         633.99

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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   ' P 2(1)/n '

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

_cell_length_a                   13.78516(8)
_cell_length_b                   14.11066(8)
_cell_length_c                   15.45815(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3577(5)
_cell_angle_gamma                90.00
_cell_volume                     2948.00(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    43078
_cell_measurement_theta_min      3.1293
_cell_measurement_theta_max      76.6725

_exptl_crystal_description       block
_exptl_crystal_colour            'yellow, light orange'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    1.535
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5140
_exptl_absorpt_correction_T_max  0.7288
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
 (compiled Jul 11 2012,15:38:31)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            60993
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         76.87
_reflns_number_total             6207
_reflns_number_gt                6188
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    
; SIR92 (A. Altomare, G. Cascarano, 
C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, 
J. Appl. Cryst., 27 (1994) 435)
;
_computing_structure_refinement  
;
SHELXL-97 (M. Sheldrick, Acta Cryst. A64 (2008) 112)
;
_computing_molecular_graphics    
;
ORTEP-3 for Windows (L. Farrugia, J. Appl. Cryst., 32 (1999) 837) 
and Mercury 2.3 (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, 
G. P. Shields, R. Taylor, M. Towler, J. van de Streek, J. Appl. Cryst., 
39 (2006) 453)
;
_computing_publication_material  
;
SHELXL-97 (M. Sheldrick, Acta Cryst. A64 (2008) 112)
;

_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. 

 Among 3 least-squares restraints there are DFIX restraints for 3 C-H bond 
 lengths of the acetonitryl methyl group (C48-H481, C48-H482, C48-H483).  
 For the disordered methyl group of the acetate anion, with two sites rotated 
 by 60 degrees from one another, the SHELXL HFIX 123 procedure was applied with 
 C-H bond lengths constrained to 0.98 Angstrom).  
;

_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)+(0.0531P)²+3.0688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6207
_refine_ls_number_parameters     406
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.438858(17) 0.239609(17) 0.594702(16) 0.01891(9) Uani 1 1 d . . .
N1 N 0.53610(11) 0.55713(11) 0.74375(10) 0.0174(3) Uani 1 1 d . . .
C2 C 0.46399(13) 0.50513(13) 0.77917(12) 0.0179(3) Uani 1 1 d . . .
C3 C 0.44301(12) 0.41871(12) 0.72686(11) 0.0163(3) Uani 1 1 d . . .
C3A C 0.50202(12) 0.42162(12) 0.66203(11) 0.0150(3) Uani 1 1 d . . .
N4 N 0.51108(10) 0.36204(10) 0.59734(9) 0.0152(3) Uani 1 1 d . . .
C4A C 0.57416(12) 0.38889(12) 0.54170(11) 0.0160(3) Uani 1 1 d . . .
C5 C 0.58664(13) 0.32939(13) 0.47187(12) 0.0191(3) Uani 1 1 d . . .
H5 H 0.5522 0.2708 0.4631 0.023 Uiso 1 1 calc R . .
C6 C 0.64857(14) 0.35556(13) 0.41591(12) 0.0210(4) Uani 1 1 d . . .
H6 H 0.6565 0.3149 0.3688 0.025 Uiso 1 1 calc R . .
C7 C 0.69979(13) 0.44182(13) 0.42828(12) 0.0207(4) Uani 1 1 d . . .
H7 H 0.7422 0.4594 0.3894 0.025 Uiso 1 1 calc R . .
C8 C 0.68891(13) 0.50123(13) 0.49654(12) 0.0193(3) Uani 1 1 d . . .
H8 H 0.7238 0.5596 0.5044 0.023 Uiso 1 1 calc R . .
C8A C 0.62649(12) 0.47600(12) 0.55463(11) 0.0162(3) Uani 1 1 d . . .
N9 N 0.61861(11) 0.53738(10) 0.62296(10) 0.0170(3) Uani 1 1 d . . .
C9A C 0.55896(12) 0.50935(12) 0.67269(11) 0.0154(3) Uani 1 1 d . . .
O2 O 0.43233(10) 0.53331(10) 0.84278(9) 0.0256(3) Uani 1 1 d . . .
C11 C 0.58054(13) 0.64333(13) 0.78034(11) 0.0181(3) Uani 1 1 d . . .
C12 C 0.68257(13) 0.65500(13) 0.79208(12) 0.0203(4) Uani 1 1 d . . .
H12 H 0.7224 0.6068 0.7741 0.024 Uiso 1 1 calc R . .
C13 C 0.72571(15) 0.73819(15) 0.83045(13) 0.0250(4) Uani 1 1 d . . .
H13 H 0.7953 0.7465 0.8389 0.030 Uiso 1 1 calc R . .
C14 C 0.66790(16) 0.80863(15) 0.85633(14) 0.0292(4) Uani 1 1 d . . .
H14 H 0.6977 0.8651 0.8826 0.035 Uiso 1 1 calc R . .
C15 C 0.56648(17) 0.79682(15) 0.84400(15) 0.0314(5) Uani 1 1 d . . .
H15 H 0.5268 0.8454 0.8616 0.038 Uiso 1 1 calc R . .
C16 C 0.52204(15) 0.71387(15) 0.80577(14) 0.0265(4) Uani 1 1 d . . .
H16 H 0.4524 0.7059 0.7973 0.032 Uiso 1 1 calc R . .
C30 C 0.37033(12) 0.34889(13) 0.73666(11) 0.0163(3) Uani 1 1 d . . .
C31 C 0.30327(13) 0.36612(12) 0.80098(12) 0.0188(3) Uani 1 1 d . . .
C32 C 0.33755(16) 0.35714(14) 0.89132(13) 0.0269(4) Uani 1 1 d . . .
H32 H 0.4051 0.3427 0.9137 0.032 Uiso 1 1 calc R . .
C33 C 0.2726(2) 0.36938(15) 0.94914(14) 0.0352(5) Uani 1 1 d . . .
H33 H 0.2961 0.3634 1.0109 0.042 Uiso 1 1 calc R . .
C34 C 0.17403(19) 0.39017(15) 0.91686(17) 0.0360(5) Uani 1 1 d . . .
H34 H 0.1300 0.3982 0.9565 0.043 Uiso 1 1 calc R . .
C35 C 0.13974(16) 0.39928(14) 0.82746(16) 0.0320(5) Uani 1 1 d . . .
H35 H 0.0720 0.4135 0.8055 0.038 Uiso 1 1 calc R . .
C36 C 0.20401(14) 0.38772(13) 0.76884(14) 0.0235(4) Uani 1 1 d . . .
H36 H 0.1802 0.3946 0.7072 0.028 Uiso 1 1 calc R . .
N30 N 0.36102(11) 0.27162(11) 0.68889(10) 0.0184(3) Uani 1 1 d . . .
C37 C 0.28317(14) 0.20224(13) 0.69721(12) 0.0219(4) Uani 1 1 d . . .
H37A H 0.2181 0.2344 0.6869 0.026 Uiso 1 1 calc R . .
H37B H 0.2959 0.1760 0.7578 0.026 Uiso 1 1 calc R . .
C38 C 0.28061(14) 0.12164(13) 0.63082(12) 0.0202(4) Uani 1 1 d . . .
H38A H 0.3474 0.0932 0.6381 0.024 Uiso 1 1 calc R . .
H38B H 0.2346 0.0719 0.6433 0.024 Uiso 1 1 calc R . .
C39 C 0.24835(14) 0.15445(13) 0.53719(12) 0.0195(3) Uani 1 1 d . . .
C40 C 0.15735(15) 0.12901(16) 0.48701(14) 0.0285(4) Uani 1 1 d . . .
H40 H 0.1146 0.0876 0.5104 0.034 Uiso 1 1 calc R . .
C41 C 0.12970(17) 0.1648(2) 0.40228(15) 0.0373(5) Uani 1 1 d . . .
H41 H 0.0677 0.1480 0.3669 0.045 Uiso 1 1 calc R . .
C42 C 0.19293(17) 0.22544(18) 0.36920(14) 0.0347(5) Uani 1 1 d . . .
H42 H 0.1744 0.2519 0.3118 0.042 Uiso 1 1 calc R . .
C43 C 0.28340(16) 0.24626(14) 0.42201(13) 0.0255(4) Uani 1 1 d . . .
H43 H 0.3277 0.2866 0.3995 0.031 Uiso 1 1 calc R . .
N44 N 0.31114(11) 0.21149(11) 0.50428(10) 0.0193(3) Uani 1 1 d . . .
O3 O 0.51364(11) 0.12878(10) 0.56951(10) 0.0281(3) Uani 1 1 d . . .
O4 O 0.56221(15) 0.12221(15) 0.71356(12) 0.0479(5) Uani 1 1 d . . .
C45 C 0.55918(14) 0.08772(15) 0.63991(14) 0.0261(4) Uani 1 1 d . . .
C46 C 0.60949(17) -0.00467(16) 0.62688(16) 0.0331(5) Uani 1 1 d . . .
H46A H 0.5983 -0.0197 0.5638 0.050 Uiso 0.50 1 calc PR . .
H46B H 0.5821 -0.0554 0.6582 0.050 Uiso 0.50 1 calc PR . .
H46C H 0.6807 0.0010 0.6502 0.050 Uiso 0.50 1 calc PR . .
H46D H 0.6424 -0.0297 0.6843 0.050 Uiso 0.50 1 calc PR . .
H46E H 0.6586 0.0060 0.5899 0.050 Uiso 0.50 1 calc PR . .
H46F H 0.5601 -0.0504 0.5979 0.050 Uiso 0.50 1 calc PR . .
N47 N 0.60549(18) 0.1081(2) 0.03776(16) 0.0563(7) Uani 1 1 d . . .
C47 C 0.5499(2) 0.1100(2) -0.02720(17) 0.0434(6) Uani 1 1 d . . .
C48 C 0.4766(3) 0.1124(3) -0.1089(2) 0.0585(8) Uani 1 1 d D . .
H481 H 0.524(3) 0.121(3) -0.148(2) 0.088 Uiso 1 1 d D . .
H482 H 0.440(3) 0.0515(19) -0.117(3) 0.088 Uiso 1 1 d D . .
H483 H 0.427(3) 0.163(2) -0.111(3) 0.088 Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.9540(14) . ?
Zn1 N4 1.9904(14) . ?
Zn1 N30 2.0225(15) . ?
Zn1 N44 2.0595(16) . ?
N1 C9A 1.377(2) . ?
N1 C11 1.428(2) . ?
N1 C2 1.428(2) . ?
C2 O2 1.218(2) . ?
C2 C3 1.460(2) . ?
C3 C3A 1.410(2) . ?
C3 C30 1.434(2) . ?
C3A N4 1.331(2) . ?
C3A C9A 1.458(2) . ?
N4 C4A 1.391(2) . ?
C4A C5 1.405(2) . ?
C4A C8A 1.419(2) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.406(2) . ?
C8 H8 0.9500 . ?
C8A N9 1.387(2) . ?
N9 C9A 1.293(2) . ?
C11 C16 1.386(3) . ?
C11 C12 1.392(2) . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C30 N30 1.309(2) . ?
C30 C31 1.505(2) . ?
C31 C32 1.389(3) . ?
C31 C36 1.394(3) . ?
C32 C33 1.395(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.376(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.396(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N30 C37 1.477(2) . ?
C37 C38 1.528(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.501(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 N44 1.353(2) . ?
C39 C40 1.386(3) . ?
C40 C41 1.386(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.389(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.381(3) . ?
C42 H42 0.9500 . ?
C43 N44 1.346(3) . ?
C43 H43 0.9500 . ?
O3 C45 1.283(3) . ?
O4 C45 1.231(3) . ?
C45 C46 1.509(3) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C46 H46D 0.9800 . ?
C46 H46E 0.9800 . ?
C46 H46F 0.9800 . ?
N47 C47 1.137(4) . ?
C47 C48 1.454(4) . ?
C48 H481 0.977(19) . ?
C48 H482 0.989(19) . ?
C48 H483 0.983(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Zn1 N4 114.67(6) . . ?
O3 Zn1 N30 134.24(6) . . ?
N4 Zn1 N30 97.21(6) . . ?
O3 Zn1 N44 97.16(6) . . ?
N4 Zn1 N44 122.58(6) . . ?
N30 Zn1 N44 91.59(6) . . ?
C9A N1 C11 125.83(15) . . ?
C9A N1 C2 109.88(14) . . ?
C11 N1 C2 124.22(14) . . ?
O2 C2 N1 121.91(16) . . ?
O2 C2 C3 131.00(17) . . ?
N1 C2 C3 107.07(14) . . ?
C3A C3 C30 127.43(16) . . ?
C3A C3 C2 106.86(15) . . ?
C30 C3 C2 125.55(15) . . ?
N4 C3A C3 131.92(16) . . ?
N4 C3A C9A 119.55(15) . . ?
C3 C3A C9A 108.52(15) . . ?
C3A N4 C4A 117.08(14) . . ?
C3A N4 Zn1 116.30(11) . . ?
C4A N4 Zn1 126.51(12) . . ?
N4 C4A C5 119.91(16) . . ?
N4 C4A C8A 120.74(15) . . ?
C5 C4A C8A 119.36(16) . . ?
C6 C5 C4A 120.41(17) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C5 C6 C7 120.28(17) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.31(17) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C8A 120.48(17) . . ?
C7 C8 H8 119.8 . . ?
C8A C8 H8 119.8 . . ?
N9 C8A C8 118.55(16) . . ?
N9 C8A C4A 122.30(15) . . ?
C8 C8A C4A 119.15(16) . . ?
C9A N9 C8A 114.58(15) . . ?
N9 C9A N1 126.61(16) . . ?
N9 C9A C3A 125.73(16) . . ?
N1 C9A C3A 107.65(14) . . ?
C16 C11 C12 120.50(17) . . ?
C16 C11 N1 119.74(16) . . ?
C12 C11 N1 119.74(16) . . ?
C11 C12 C13 119.36(18) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.45(18) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.89(18) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.41(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.38(18) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
N30 C30 C3 120.37(15) . . ?
N30 C30 C31 120.17(15) . . ?
C3 C30 C31 119.45(15) . . ?
C32 C31 C36 119.59(18) . . ?
C32 C31 C30 121.19(17) . . ?
C36 C31 C30 119.17(16) . . ?
C31 C32 C33 119.9(2) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 C32 120.3(2) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C35 C34 C33 120.06(19) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 120.3(2) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C31 C36 C35 119.9(2) . . ?
C31 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C30 N30 C37 119.69(15) . . ?
C30 N30 Zn1 125.81(12) . . ?
C37 N30 Zn1 114.35(11) . . ?
N30 C37 C38 110.86(14) . . ?
N30 C37 H37A 109.5 . . ?
C38 C37 H37A 109.5 . . ?
N30 C37 H37B 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 108.1 . . ?
C39 C38 C37 112.42(15) . . ?
C39 C38 H38A 109.1 . . ?
C37 C38 H38A 109.1 . . ?
C39 C38 H38B 109.1 . . ?
C37 C38 H38B 109.1 . . ?
H38A C38 H38B 107.9 . . ?
N44 C39 C40 121.29(17) . . ?
N44 C39 C38 117.14(16) . . ?
C40 C39 C38 121.56(17) . . ?
C41 C40 C39 119.00(19) . . ?
C41 C40 H40 120.5 . . ?
C39 C40 H40 120.5 . . ?
C40 C41 C42 119.8(2) . . ?
C40 C41 H41 120.1 . . ?
C42 C41 H41 120.1 . . ?
C43 C42 C41 118.2(2) . . ?
C43 C42 H42 120.9 . . ?
C41 C42 H42 120.9 . . ?
N44 C43 C42 122.43(19) . . ?
N44 C43 H43 118.8 . . ?
C42 C43 H43 118.8 . . ?
C43 N44 C39 119.23(16) . . ?
C43 N44 Zn1 128.08(13) . . ?
C39 N44 Zn1 112.60(12) . . ?
C45 O3 Zn1 112.44(13) . . ?
O4 C45 O3 121.9(2) . . ?
O4 C45 C46 122.2(2) . . ?
O3 C45 C46 115.98(18) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C46 H46D 109.5 . . ?
H46A C46 H46D 141.1 . . ?
H46B C46 H46D 56.3 . . ?
H46C C46 H46D 56.3 . . ?
C45 C46 H46E 109.5 . . ?
H46A C46 H46E 56.3 . . ?
H46B C46 H46E 141.1 . . ?
H46C C46 H46E 56.3 . . ?
H46D C46 H46E 109.5 . . ?
C45 C46 H46F 109.5 . . ?
H46A C46 H46F 56.3 . . ?
H46B C46 H46F 56.3 . . ?
H46C C46 H46F 141.1 . . ?
H46D C46 H46F 109.5 . . ?
H46E C46 H46F 109.5 . . ?
N47 C47 C48 178.4(3) . . ?
C47 C48 H481 96(3) . . ?
C47 C48 H482 110(2) . . ?
H481 C48 H482 115(4) . . ?
C47 C48 H483 114(3) . . ?
H481 C48 H483 115(4) . . ?
H482 C48 H483 107(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
C9A N1 C2 O2 179.76(17) . . . . ?
C11 N1 C2 O2 2.6(3) . . . . ?
C9A N1 C2 C3 1.14(19) . . . . ?
C11 N1 C2 C3 -175.99(15) . . . . ?
O2 C2 C3 C3A -178.79(19) . . . . ?
N1 C2 C3 C3A -0.33(19) . . . . ?
O2 C2 C3 C30 5.5(3) . . . . ?
N1 C2 C3 C30 -176.04(16) . . . . ?
C30 C3 C3A N4 -3.6(3) . . . . ?
C2 C3 C3A N4 -179.24(17) . . . . ?
C30 C3 C3A C9A 175.07(16) . . . . ?
C2 C3 C3A C9A -0.54(19) . . . . ?
C3 C3A N4 C4A 177.24(17) . . . . ?
C9A C3A N4 C4A -1.3(2) . . . . ?
C3 C3A N4 Zn1 -6.3(2) . . . . ?
C9A C3A N4 Zn1 175.07(11) . . . . ?
O3 Zn1 N4 C3A -137.60(12) . . . . ?
N30 Zn1 N4 C3A 8.71(13) . . . . ?
N44 Zn1 N4 C3A 105.26(13) . . . . ?
O3 Zn1 N4 C4A 38.43(15) . . . . ?
N30 Zn1 N4 C4A -175.27(14) . . . . ?
N44 Zn1 N4 C4A -78.71(15) . . . . ?
C3A N4 C4A C5 -179.69(15) . . . . ?
Zn1 N4 C4A C5 4.3(2) . . . . ?
C3A N4 C4A C8A 0.4(2) . . . . ?
Zn1 N4 C4A C8A -175.62(12) . . . . ?
N4 C4A C5 C6 179.60(16) . . . . ?
C8A C4A C5 C6 -0.5(3) . . . . ?
C4A C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C8A 0.1(3) . . . . ?
C7 C8 C8A N9 179.28(16) . . . . ?
C7 C8 C8A C4A -0.5(3) . . . . ?
N4 C4A C8A N9 0.8(2) . . . . ?
C5 C4A C8A N9 -179.09(16) . . . . ?
N4 C4A C8A C8 -179.40(15) . . . . ?
C5 C4A C8A C8 0.7(2) . . . . ?
C8 C8A N9 C9A 179.30(15) . . . . ?
C4A C8A N9 C9A -0.9(2) . . . . ?
C8A N9 C9A N1 -178.71(16) . . . . ?
C8A N9 C9A C3A -0.1(2) . . . . ?
C11 N1 C9A N9 -5.6(3) . . . . ?
C2 N1 C9A N9 177.35(16) . . . . ?
C11 N1 C9A C3A 175.61(15) . . . . ?
C2 N1 C9A C3A -1.46(19) . . . . ?
N4 C3A C9A N9 1.3(3) . . . . ?
C3 C3A C9A N9 -177.58(16) . . . . ?
N4 C3A C9A N1 -179.87(15) . . . . ?
C3 C3A C9A N1 1.24(19) . . . . ?
C9A N1 C11 C16 138.20(19) . . . . ?
C2 N1 C11 C16 -45.1(3) . . . . ?
C9A N1 C11 C12 -43.3(3) . . . . ?
C2 N1 C11 C12 133.40(18) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
N1 C11 C12 C13 -177.97(16) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
N1 C11 C16 C15 178.06(19) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C3A C3 C30 N30 8.5(3) . . . . ?
C2 C3 C30 N30 -176.69(17) . . . . ?
C3A C3 C30 C31 -170.20(17) . . . . ?
C2 C3 C30 C31 4.6(3) . . . . ?
N30 C30 C31 C32 106.3(2) . . . . ?
C3 C30 C31 C32 -75.0(2) . . . . ?
N30 C30 C31 C36 -71.1(2) . . . . ?
C3 C30 C31 C36 107.56(19) . . . . ?
C36 C31 C32 C33 0.2(3) . . . . ?
C30 C31 C32 C33 -177.13(18) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C32 C33 C34 C35 -0.3(3) . . . . ?
C33 C34 C35 C36 -0.1(3) . . . . ?
C32 C31 C36 C35 -0.6(3) . . . . ?
C30 C31 C36 C35 176.84(17) . . . . ?
C34 C35 C36 C31 0.5(3) . . . . ?
C3 C30 N30 C37 -177.55(16) . . . . ?
C31 C30 N30 C37 1.1(3) . . . . ?
C3 C30 N30 Zn1 -2.2(2) . . . . ?
C31 C30 N30 Zn1 176.45(12) . . . . ?
O3 Zn1 N30 C30 130.06(15) . . . . ?
N4 Zn1 N30 C30 -5.22(16) . . . . ?
N44 Zn1 N30 C30 -128.34(15) . . . . ?
O3 Zn1 N30 C37 -54.41(16) . . . . ?
N4 Zn1 N30 C37 170.32(13) . . . . ?
N44 Zn1 N30 C37 47.19(13) . . . . ?
C30 N30 C37 C38 175.72(16) . . . . ?
Zn1 N30 C37 C38 -0.11(19) . . . . ?
N30 C37 C38 C39 -66.7(2) . . . . ?
C37 C38 C39 N44 68.9(2) . . . . ?
C37 C38 C39 C40 -109.9(2) . . . . ?
N44 C39 C40 C41 -1.6(3) . . . . ?
C38 C39 C40 C41 177.2(2) . . . . ?
C39 C40 C41 C42 -0.2(4) . . . . ?
C40 C41 C42 C43 1.5(4) . . . . ?
C41 C42 C43 N44 -1.3(4) . . . . ?
C42 C43 N44 C39 -0.4(3) . . . . ?
C42 C43 N44 Zn1 -176.58(17) . . . . ?
C40 C39 N44 C43 1.9(3) . . . . ?
C38 C39 N44 C43 -176.92(17) . . . . ?
C40 C39 N44 Zn1 178.60(15) . . . . ?
C38 C39 N44 Zn1 -0.2(2) . . . . ?
O3 Zn1 N44 C43 -96.58(17) . . . . ?
N4 Zn1 N44 C43 28.83(19) . . . . ?
N30 Zn1 N44 C43 128.44(17) . . . . ?
O3 Zn1 N44 C39 87.04(13) . . . . ?
N4 Zn1 N44 C39 -147.56(12) . . . . ?
N30 Zn1 N44 C39 -47.95(13) . . . . ?
N4 Zn1 O3 C45 93.84(14) . . . . ?
N30 Zn1 O3 C45 -35.97(17) . . . . ?
N44 Zn1 O3 C45 -135.26(14) . . . . ?
Zn1 O3 C45 O4 -7.2(3) . . . . ?
Zn1 O3 C45 C46 173.42(14) . . . . ?

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
_geom_hbond_publ_flag
C48 H481 O4 0.98(2) 2.31(3) 3.197(4) 151(3) 1_554 ?
C38 H38B O2 0.99 2.42 3.288(2) 146.6 2_546 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.87
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.061

_database_code_depnum_ccdc_archive 'CCDC 1006387'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_(rac)-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (E)-3-{[2-(2-aminoethyl)pyridine]-phenylmethylidene}-1,4-dihydro-2H-1-
  phenylpyrrolo[2,3-b]quinoxalin-2-one, racemate of two symmetrically 
  independent conformers   
;
_chemical_name_common            ?
_chemical_melting_point          432
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H23 N5 O'
_chemical_formula_weight         469.53

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C c  '

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

_cell_length_a                   12.65632(9)
_cell_length_b                   19.63117(11)
_cell_length_c                   19.20284(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.3451(6)
_cell_angle_gamma                90.00
_cell_volume                     4731.96(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    120.05(10)
_cell_measurement_reflns_used    50610
_cell_measurement_theta_min      4.1770
_cell_measurement_theta_max      76.5996

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7224
_exptl_absorpt_correction_T_max  0.7793
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120.05(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            70316
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.18
_diffrn_reflns_theta_max         76.80
_reflns_number_total             9907
_reflns_number_gt                9840
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    
; SIR92 (A. Altomare, G. Cascarano, 
C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, 
J. Appl. Cryst., 27 (1994) 435)
;
_computing_structure_refinement  
;
SHELXL-97 (M. Sheldrick, Acta Cryst. A64 (2008) 112)
;
_computing_molecular_graphics    
;
ORTEP-3 for Windows (L. Farrugia, J. Appl. Cryst., 32 (1999) 837) 
and Mercury 2.3 (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, 
G. P. Shields, R. Taylor, M. Towler, J. van de Streek, J. Appl. Cryst., 
39 (2006) 453)
;
_computing_publication_material  
;
SHELXL-97 (M. Sheldrick, Acta Cryst. A64 (2008) 112)
;

_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.
 
 Among 4 least-squares restraints there are 2 DFIX parameters for N30A-H30A 
 and N30B-H30B bond lengths and 2 values for x and z coordinates of the origin 
 in Cc space group.  
;

_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)+(0.0462P)²+1.0346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(11)
_refine_ls_number_reflns         9907
_refine_ls_number_parameters     655
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.24696(7) 0.82350(5) -0.03163(5) 0.02548(18) Uani 1 1 d . . .
C2A C 0.21108(9) 0.88307(5) -0.07059(6) 0.0247(2) Uani 1 1 d . . .
O2A O 0.11709(6) 0.89854(4) -0.08184(4) 0.02929(17) Uani 1 1 d . . .
C3A C 0.30575(9) 0.91564(6) -0.09084(5) 0.0247(2) Uani 1 1 d . . .
C3AA C 0.39540(9) 0.87611(5) -0.06244(5) 0.0233(2) Uani 1 1 d . . .
N4A N 0.49678(8) 0.88607(5) -0.06675(5) 0.02459(18) Uani 1 1 d . . .
C4AA C 0.56395(9) 0.83585(5) -0.03606(6) 0.0245(2) Uani 1 1 d . . .
C5A C 0.67344(9) 0.84118(6) -0.04063(6) 0.0291(2) Uani 1 1 d . . .
H5A H 0.6999 0.8793 -0.0635 0.035 Uiso 1 1 calc R . .
C6A C 0.74277(10) 0.79159(6) -0.01222(6) 0.0316(2) Uani 1 1 d . . .
H6A H 0.8167 0.7955 -0.0158 0.038 Uiso 1 1 calc R . .
C7A C 0.70447(10) 0.73530(6) 0.02195(7) 0.0320(2) Uani 1 1 d . . .
H7A H 0.7526 0.7010 0.0411 0.038 Uiso 1 1 calc R . .
C8A C 0.59756(10) 0.72937(6) 0.02800(6) 0.0297(2) Uani 1 1 d . . .
H8A H 0.5729 0.6916 0.0523 0.036 Uiso 1 1 calc R . .
C8AA C 0.52449(9) 0.77885(6) -0.00156(5) 0.0249(2) Uani 1 1 d . . .
N9A N 0.41656(8) 0.76990(5) 0.00336(5) 0.02575(19) Uani 1 1 d . . .
C9AA C 0.35689(9) 0.81770(5) -0.02683(5) 0.0236(2) Uani 1 1 d . . .
C11A C 0.17730(9) 0.77943(6) 0.00008(6) 0.0257(2) Uani 1 1 d . . .
C12A C 0.18550(10) 0.70927(6) -0.00674(7) 0.0302(2) Uani 1 1 d . . .
H12A H 0.2369 0.6903 -0.0332 0.036 Uiso 1 1 calc R . .
C13A C 0.11822(10) 0.66700(6) 0.02529(7) 0.0338(2) Uani 1 1 d . . .
H13A H 0.1236 0.6190 0.0209 0.041 Uiso 1 1 calc R . .
C14A C 0.04295(10) 0.69480(6) 0.06379(7) 0.0337(2) Uani 1 1 d . . .
H14A H -0.0021 0.6657 0.0863 0.040 Uiso 1 1 calc R . .
C15A C 0.03340(9) 0.76507(6) 0.06948(7) 0.0318(2) Uani 1 1 d . . .
H15A H -0.0192 0.7839 0.0950 0.038 Uiso 1 1 calc R . .
C16A C 0.10091(9) 0.80763(6) 0.03779(6) 0.0287(2) Uani 1 1 d . . .
H16A H 0.0950 0.8557 0.0418 0.034 Uiso 1 1 calc R . .
C30A C 0.30919(10) 0.97227(6) -0.13432(6) 0.0267(2) Uani 1 1 d . . .
C31A C 0.21033(9) 1.00637(6) -0.16717(6) 0.0298(2) Uani 1 1 d . . .
C32A C 0.17584(11) 0.99722(8) -0.23797(7) 0.0418(3) Uani 1 1 d . . .
H32A H 0.2170 0.9707 -0.2660 0.050 Uiso 1 1 calc R . .
C33A C 0.08106(12) 1.02680(10) -0.26795(8) 0.0522(4) Uani 1 1 d . . .
H33A H 0.0573 1.0201 -0.3164 0.063 Uiso 1 1 calc R . .
C34A C 0.02153(12) 1.06567(9) -0.22787(8) 0.0491(4) Uani 1 1 d . . .
H34A H -0.0426 1.0864 -0.2488 0.059 Uiso 1 1 calc R . .
C35A C 0.05469(12) 1.07450(9) -0.15752(8) 0.0483(4) Uani 1 1 d . . .
H35A H 0.0132 1.1010 -0.1298 0.058 Uiso 1 1 calc R . .
C36A C 0.14870(12) 1.04472(8) -0.12697(7) 0.0416(3) Uani 1 1 d . . .
H36A H 0.1710 1.0506 -0.0782 0.050 Uiso 1 1 calc R . .
N30A N 0.40330(9) 0.99454(5) -0.14807(5) 0.0310(2) Uani 1 1 d D . .
H30A H 0.4583(11) 0.9687(8) -0.1303(8) 0.037 Uiso 1 1 d D . .
C37A C 0.42193(11) 1.05205(7) -0.19378(7) 0.0363(3) Uani 1 1 d . . .
H37A H 0.3699 1.0887 -0.1885 0.044 Uiso 1 1 calc R . .
H37B H 0.4122 1.0371 -0.2434 0.044 Uiso 1 1 calc R . .
C38A C 0.53425(12) 1.07881(7) -0.17432(7) 0.0380(3) Uani 1 1 d . . .
H38A H 0.5433 1.1205 -0.2020 0.046 Uiso 1 1 calc R . .
H38B H 0.5438 1.0917 -0.1241 0.046 Uiso 1 1 calc R . .
C39A C 0.62010(10) 1.02814(6) -0.18697(6) 0.0317(2) Uani 1 1 d . . .
C40A C 0.71936(12) 1.02757(9) -0.14602(8) 0.0461(3) Uani 1 1 d . . .
H40A H 0.7340 1.0580 -0.1075 0.055 Uiso 1 1 calc R . .
C41A C 0.79620(12) 0.98220(10) -0.16202(9) 0.0551(4) Uani 1 1 d . . .
H41A H 0.8648 0.9816 -0.1353 0.066 Uiso 1 1 calc R . .
C42A C 0.77197(12) 0.93791(8) -0.21717(8) 0.0470(3) Uani 1 1 d . . .
H42A H 0.8233 0.9063 -0.2295 0.056 Uiso 1 1 calc R . .
C43A C 0.67135(11) 0.94061(7) -0.25419(8) 0.0395(3) Uani 1 1 d . . .
H43A H 0.6542 0.9095 -0.2918 0.047 Uiso 1 1 calc R . .
N44A N 0.59630(8) 0.98483(5) -0.23985(6) 0.0336(2) Uani 1 1 d . . .
N1B N 0.74830(7) 0.93585(5) 0.10875(5) 0.02477(18) Uani 1 1 d . . .
C2B C 0.78168(8) 0.87421(5) 0.14446(6) 0.0241(2) Uani 1 1 d . . .
O2B O 0.87430(6) 0.85545(4) 0.15195(4) 0.02795(16) Uani 1 1 d . . .
C3B C 0.68641(8) 0.84329(5) 0.16641(6) 0.0249(2) Uani 1 1 d . . .
C3AB C 0.59812(8) 0.88555(5) 0.14071(5) 0.0231(2) Uani 1 1 d . . .
N4B N 0.49646(7) 0.87732(5) 0.14507(5) 0.02410(18) Uani 1 1 d . . .
C4AB C 0.43176(9) 0.92888(5) 0.11464(5) 0.0240(2) Uani 1 1 d . . .
C5B C 0.32133(9) 0.92515(6) 0.11805(6) 0.0275(2) Uani 1 1 d . . .
H5B H 0.2928 0.8872 0.1401 0.033 Uiso 1 1 calc R . .
C6B C 0.25451(9) 0.97621(7) 0.08955(6) 0.0310(2) Uani 1 1 d . . .
H6B H 0.1803 0.9738 0.0928 0.037 Uiso 1 1 calc R . .
C7B C 0.29557(10) 1.03169(6) 0.05581(6) 0.0313(2) Uani 1 1 d . . .
H7B H 0.2491 1.0669 0.0368 0.038 Uiso 1 1 calc R . .
C8B C 0.40265(9) 1.03566(6) 0.04997(6) 0.0289(2) Uani 1 1 d . . .
H8B H 0.4291 1.0727 0.0255 0.035 Uiso 1 1 calc R . .
C8AB C 0.47328(9) 0.98512(5) 0.08012(5) 0.0242(2) Uani 1 1 d . . .
N9B N 0.58126(7) 0.99219(5) 0.07510(5) 0.02478(18) Uani 1 1 d . . .
C9AB C 0.63890(8) 0.94339(5) 0.10537(5) 0.0228(2) Uani 1 1 d . . .
C11B C 0.81973(9) 0.97949(6) 0.07833(6) 0.0252(2) Uani 1 1 d . . .
C12B C 0.89187(9) 0.95188(6) 0.03722(6) 0.0267(2) Uani 1 1 d . . .
H12B H 0.8927 0.9042 0.0289 0.032 Uiso 1 1 calc R . .
C13B C 0.96275(9) 0.99427(6) 0.00829(6) 0.0301(2) Uani 1 1 d . . .
H13B H 1.0123 0.9755 -0.0196 0.036 Uiso 1 1 calc R . .
C14B C 0.96106(10) 1.06408(6) 0.02027(7) 0.0328(2) Uani 1 1 d . . .
H14B H 1.0093 1.0930 0.0003 0.039 Uiso 1 1 calc R . .
C15B C 0.88917(10) 1.09159(6) 0.06131(7) 0.0340(3) Uani 1 1 d . . .
H15B H 0.8883 1.1393 0.0694 0.041 Uiso 1 1 calc R . .
C16B C 0.81826(10) 1.04930(6) 0.09064(7) 0.0302(2) Uani 1 1 d . . .
H16B H 0.7691 1.0680 0.1189 0.036 Uiso 1 1 calc R . .
C30B C 0.68229(9) 0.78112(6) 0.20099(6) 0.0263(2) Uani 1 1 d . . .
C31B C 0.78184(9) 0.74467(6) 0.22970(6) 0.0273(2) Uani 1 1 d . . .
C32B C 0.84997(10) 0.77403(6) 0.28410(6) 0.0308(2) Uani 1 1 d . . .
H32B H 0.8324 0.8164 0.3035 0.037 Uiso 1 1 calc R . .
C33B C 0.94382(10) 0.74088(7) 0.30988(7) 0.0359(3) Uani 1 1 d . . .
H33B H 0.9902 0.7605 0.3473 0.043 Uiso 1 1 calc R . .
C34B C 0.97020(10) 0.67964(7) 0.28150(7) 0.0359(3) Uani 1 1 d . . .
H34B H 1.0353 0.6579 0.2989 0.043 Uiso 1 1 calc R . .
C35B C 0.90257(10) 0.64965(7) 0.22790(7) 0.0346(3) Uani 1 1 d . . .
H35B H 0.9207 0.6072 0.2088 0.042 Uiso 1 1 calc R . .
C36B C 0.80776(10) 0.68215(6) 0.20215(6) 0.0315(2) Uani 1 1 d . . .
H36B H 0.7606 0.6616 0.1657 0.038 Uiso 1 1 calc R . .
N30B N 0.58890(8) 0.75301(5) 0.20876(6) 0.0311(2) Uani 1 1 d D . .
H30B H 0.5294(11) 0.7745(8) 0.1903(8) 0.037 Uiso 1 1 d D . .
C37B C 0.57144(10) 0.69337(7) 0.25189(8) 0.0374(3) Uani 1 1 d . . .
H37C H 0.6410 0.6740 0.2717 0.045 Uiso 1 1 calc R . .
H37D H 0.5321 0.6581 0.2222 0.045 Uiso 1 1 calc R . .
C38B C 0.50881(11) 0.71249(8) 0.31099(7) 0.0424(3) Uani 1 1 d . . .
H38C H 0.5041 0.6722 0.3414 0.051 Uiso 1 1 calc R . .
H38D H 0.5481 0.7484 0.3398 0.051 Uiso 1 1 calc R . .
C39B C 0.39778(10) 0.73767(7) 0.28640(7) 0.0357(3) Uani 1 1 d . . .
C40B C 0.33623(12) 0.76669(9) 0.33334(8) 0.0500(4) Uani 1 1 d . . .
H40B H 0.3645 0.7728 0.3812 0.060 Uiso 1 1 calc R . .
C41B C 0.23307(13) 0.78654(10) 0.30938(11) 0.0591(4) Uani 1 1 d . . .
H41B H 0.1891 0.8061 0.3406 0.071 Uiso 1 1 calc R . .
C42B C 0.19509(12) 0.77741(8) 0.23918(10) 0.0498(4) Uani 1 1 d . . .
H42B H 0.1245 0.7903 0.2212 0.060 Uiso 1 1 calc R . .
C43B C 0.26177(11) 0.74935(8) 0.19621(8) 0.0433(3) Uani 1 1 d . . .
H43B H 0.2358 0.7436 0.1479 0.052 Uiso 1 1 calc R . .
N44B N 0.36200(9) 0.72947(7) 0.21859(6) 0.0393(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C9AA 1.3872(14) . ?
N1A C11A 1.4261(14) . ?
N1A C2A 1.4306(14) . ?
C2A O2A 1.2200(14) . ?
C2A C3A 1.4542(15) . ?
C3A C30A 1.3943(15) . ?
C3A C3AA 1.4245(15) . ?
C3AA N4A 1.3109(14) . ?
C3AA C9AA 1.4509(14) . ?
N4A C4AA 1.3833(14) . ?
C4AA C5A 1.4036(16) . ?
C4AA C8AA 1.4231(15) . ?
C5A C6A 1.3757(17) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.4029(18) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.3777(17) . ?
C7A H7A 0.9500 . ?
C8A C8AA 1.4096(15) . ?
C8A H8A 0.9500 . ?
C8AA N9A 1.3924(14) . ?
N9A C9AA 1.2942(14) . ?
C11A C12A 1.3887(16) . ?
C11A C16A 1.3945(16) . ?
C12A C13A 1.3878(17) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3900(18) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3903(18) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.3898(17) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C30A N30A 1.3266(16) . ?
C30A C31A 1.4866(16) . ?
C31A C32A 1.3854(17) . ?
C31A C36A 1.3874(17) . ?
C32A C33A 1.390(2) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.375(2) . ?
C33A H33A 0.9500 . ?
C34A C35A 1.373(2) . ?
C34A H34A 0.9500 . ?
C35A C36A 1.3868(19) . ?
C35A H35A 0.9500 . ?
C36A H36A 0.9500 . ?
N30A C37A 1.4677(14) . ?
N30A H30A 0.894(13) . ?
C37A C38A 1.517(2) . ?
C37A H37A 0.9900 . ?
C37A H37B 0.9900 . ?
C38A C39A 1.5154(18) . ?
C38A H38A 0.9900 . ?
C38A H38B 0.9900 . ?
C39A N44A 1.3292(17) . ?
C39A C40A 1.3943(19) . ?
C40A C41A 1.382(2) . ?
C40A H40A 0.9500 . ?
C41A C42A 1.374(3) . ?
C41A H41A 0.9500 . ?
C42A C43A 1.378(2) . ?
C42A H42A 0.9500 . ?
C43A N44A 1.3411(17) . ?
C43A H43A 0.9500 . ?
N1B C9AB 1.3857(14) . ?
N1B C11B 1.4240(14) . ?
N1B C2B 1.4280(13) . ?
C2B O2B 1.2196(14) . ?
C2B C3B 1.4595(15) . ?
C3B C30B 1.3935(15) . ?
C3B C3AB 1.4280(15) . ?
C3AB N4B 1.3100(14) . ?
C3AB C9AB 1.4512(14) . ?
N4B C4AB 1.3835(14) . ?
C4AB C5B 1.4094(15) . ?
C4AB C8AB 1.4226(15) . ?
C5B C6B 1.3788(17) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.4007(18) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.3764(17) . ?
C7B H7B 0.9500 . ?
C8B C8AB 1.4094(15) . ?
C8B H8B 0.9500 . ?
C8AB N9B 1.3893(14) . ?
N9B C9AB 1.2959(14) . ?
C11B C12B 1.3910(15) . ?
C11B C16B 1.3911(16) . ?
C12B C13B 1.3905(16) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3903(17) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3870(17) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3933(16) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C30B N30B 1.3300(15) . ?
C30B C31B 1.4919(15) . ?
C31B C32B 1.3917(17) . ?
C31B C36B 1.3922(16) . ?
C32B C33B 1.3889(17) . ?
C32B H32B 0.9500 . ?
C33B C34B 1.378(2) . ?
C33B H33B 0.9500 . ?
C34B C35B 1.383(2) . ?
C34B H34B 0.9500 . ?
C35B C36B 1.3928(17) . ?
C35B H35B 0.9500 . ?
C36B H36B 0.9500 . ?
N30B C37B 1.4671(14) . ?
N30B H30B 0.896(13) . ?
C37B C38B 1.512(2) . ?
C37B H37C 0.9900 . ?
C37B H37D 0.9900 . ?
C38B C39B 1.5074(19) . ?
C38B H38C 0.9900 . ?
C38B H38D 0.9900 . ?
C39B N44B 1.3325(18) . ?
C39B C40B 1.387(2) . ?
C40B C41B 1.384(2) . ?
C40B H40B 0.9500 . ?
C41B C42B 1.384(3) . ?
C41B H41B 0.9500 . ?
C42B C43B 1.369(2) . ?
C42B H42B 0.9500 . ?
C43B N44B 1.3442(17) . ?
C43B H43B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9AA N1A C11A 126.26(9) . . ?
C9AA N1A C2A 110.51(9) . . ?
C11A N1A C2A 123.15(9) . . ?
O2A C2A N1A 122.23(10) . . ?
O2A C2A C3A 131.39(10) . . ?
N1A C2A C3A 106.38(9) . . ?
C30A C3A C3AA 125.40(10) . . ?
C30A C3A C2A 126.92(10) . . ?
C3AA C3A C2A 107.53(9) . . ?
N4A C3AA C3A 129.26(10) . . ?
N4A C3AA C9AA 122.56(10) . . ?
C3A C3AA C9AA 108.17(10) . . ?
C3AA N4A C4AA 114.83(9) . . ?
N4A C4AA C5A 118.57(10) . . ?
N4A C4AA C8AA 121.71(10) . . ?
C5A C4AA C8AA 119.71(10) . . ?
C6A C5A C4AA 120.49(11) . . ?
C6A C5A H5A 119.8 . . ?
C4AA C5A H5A 119.8 . . ?
C5A C6A C7A 120.12(11) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A H6A 119.9 . . ?
C8A C7A C6A 120.52(11) . . ?
C8A C7A H7A 119.7 . . ?
C6A C7A H7A 119.7 . . ?
C7A C8A C8AA 120.57(11) . . ?
C7A C8A H8A 119.7 . . ?
C8AA C8A H8A 119.7 . . ?
N9A C8AA C8A 118.98(10) . . ?
N9A C8AA C4AA 122.44(10) . . ?
C8A C8AA C4AA 118.57(10) . . ?
C9AA N9A C8AA 113.55(9) . . ?
N9A C9AA N1A 127.74(10) . . ?
N9A C9AA C3AA 124.90(10) . . ?
N1A C9AA C3AA 107.36(9) . . ?
C12A C11A C16A 120.52(10) . . ?
C12A C11A N1A 120.24(10) . . ?
C16A C11A N1A 119.24(10) . . ?
C13A C12A C11A 119.59(11) . . ?
C13A C12A H12A 120.2 . . ?
C11A C12A H12A 120.2 . . ?
C12A C13A C14A 120.14(11) . . ?
C12A C13A H13A 119.9 . . ?
C14A C13A H13A 119.9 . . ?
C13A C14A C15A 120.25(11) . . ?
C13A C14A H14A 119.9 . . ?
C15A C14A H14A 119.9 . . ?
C16A C15A C14A 119.85(11) . . ?
C16A C15A H15A 120.1 . . ?
C14A C15A H15A 120.1 . . ?
C15A C16A C11A 119.64(11) . . ?
C15A C16A H16A 120.2 . . ?
C11A C16A H16A 120.2 . . ?
N30A C30A C3A 118.65(10) . . ?
N30A C30A C31A 119.71(10) . . ?
C3A C30A C31A 121.60(11) . . ?
C32A C31A C36A 119.16(12) . . ?
C32A C31A C30A 120.04(11) . . ?
C36A C31A C30A 120.72(11) . . ?
C31A C32A C33A 119.96(13) . . ?
C31A C32A H32A 120.0 . . ?
C33A C32A H32A 120.0 . . ?
C34A C33A C32A 120.38(14) . . ?
C34A C33A H33A 119.8 . . ?
C32A C33A H33A 119.8 . . ?
C35A C34A C33A 120.01(13) . . ?
C35A C34A H34A 120.0 . . ?
C33A C34A H34A 120.0 . . ?
C34A C35A C36A 120.05(14) . . ?
C34A C35A H35A 120.0 . . ?
C36A C35A H35A 120.0 . . ?
C35A C36A C31A 120.42(13) . . ?
C35A C36A H36A 119.8 . . ?
C31A C36A H36A 119.8 . . ?
C30A N30A C37A 126.12(11) . . ?
C30A N30A H30A 114.4(10) . . ?
C37A N30A H30A 119.3(10) . . ?
N30A C37A C38A 109.65(11) . . ?
N30A C37A H37A 109.7 . . ?
C38A C37A H37A 109.7 . . ?
N30A C37A H37B 109.7 . . ?
C38A C37A H37B 109.7 . . ?
H37A C37A H37B 108.2 . . ?
C39A C38A C37A 113.69(11) . . ?
C39A C38A H38A 108.8 . . ?
C37A C38A H38A 108.8 . . ?
C39A C38A H38B 108.8 . . ?
C37A C38A H38B 108.8 . . ?
H38A C38A H38B 107.7 . . ?
N44A C39A C40A 121.71(13) . . ?
N44A C39A C38A 116.44(11) . . ?
C40A C39A C38A 121.85(13) . . ?
C41A C40A C39A 119.26(14) . . ?
C41A C40A H40A 120.4 . . ?
C39A C40A H40A 120.4 . . ?
C42A C41A C40A 119.01(14) . . ?
C42A C41A H41A 120.5 . . ?
C40A C41A H41A 120.5 . . ?
C41A C42A C43A 118.28(14) . . ?
C41A C42A H42A 120.9 . . ?
C43A C42A H42A 120.9 . . ?
N44A C43A C42A 123.44(14) . . ?
N44A C43A H43A 118.3 . . ?
C42A C43A H43A 118.3 . . ?
C39A N44A C43A 118.27(12) . . ?
C9AB N1B C11B 126.83(9) . . ?
C9AB N1B C2B 110.22(9) . . ?
C11B N1B C2B 122.85(9) . . ?
O2B C2B N1B 122.24(10) . . ?
O2B C2B C3B 131.11(10) . . ?
N1B C2B C3B 106.65(9) . . ?
C30B C3B C3AB 126.74(10) . . ?
C30B C3B C2B 125.77(10) . . ?
C3AB C3B C2B 107.30(9) . . ?
N4B C3AB C3B 129.63(10) . . ?
N4B C3AB C9AB 122.50(10) . . ?
C3B C3AB C9AB 107.87(9) . . ?
C3AB N4B C4AB 114.58(9) . . ?
N4B C4AB C5B 118.64(10) . . ?
N4B C4AB C8AB 122.05(10) . . ?
C5B C4AB C8AB 119.31(10) . . ?
C6B C5B C4AB 120.36(11) . . ?
C6B C5B H5B 119.8 . . ?
C4AB C5B H5B 119.8 . . ?
C5B C6B C7B 120.25(11) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B H6B 119.9 . . ?
C8B C7B C6B 120.62(11) . . ?
C8B C7B H7B 119.7 . . ?
C6B C7B H7B 119.7 . . ?
C7B C8B C8AB 120.39(11) . . ?
C7B C8B H8B 119.8 . . ?
C8AB C8B H8B 119.8 . . ?
N9B C8AB C8B 118.62(10) . . ?
N9B C8AB C4AB 122.35(10) . . ?
C8B C8AB C4AB 119.03(10) . . ?
C9AB N9B C8AB 113.41(9) . . ?
N9B C9AB N1B 127.00(10) . . ?
N9B C9AB C3AB 125.09(10) . . ?
N1B C9AB C3AB 107.90(9) . . ?
C12B C11B C16B 120.29(10) . . ?
C12B C11B N1B 119.71(10) . . ?
C16B C11B N1B 119.99(10) . . ?
C13B C12B C11B 119.82(10) . . ?
C13B C12B H12B 120.1 . . ?
C11B C12B H12B 120.1 . . ?
C14B C13B C12B 119.97(11) . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C15B C14B C13B 120.19(11) . . ?
C15B C14B H14B 119.9 . . ?
C13B C14B H14B 119.9 . . ?
C14B C15B C16B 120.06(11) . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C11B C16B C15B 119.67(11) . . ?
C11B C16B H16B 120.2 . . ?
C15B C16B H16B 120.2 . . ?
N30B C30B C3B 120.32(10) . . ?
N30B C30B C31B 118.69(10) . . ?
C3B C30B C31B 120.99(10) . . ?
C32B C31B C36B 119.79(11) . . ?
C32B C31B C30B 119.46(10) . . ?
C36B C31B C30B 120.75(10) . . ?
C33B C32B C31B 119.55(12) . . ?
C33B C32B H32B 120.2 . . ?
C31B C32B H32B 120.2 . . ?
C34B C33B C32B 120.46(12) . . ?
C34B C33B H33B 119.8 . . ?
C32B C33B H33B 119.8 . . ?
C33B C34B C35B 120.49(11) . . ?
C33B C34B H34B 119.8 . . ?
C35B C34B H34B 119.8 . . ?
C34B C35B C36B 119.49(12) . . ?
C34B C35B H35B 120.3 . . ?
C36B C35B H35B 120.3 . . ?
C31B C36B C35B 120.21(11) . . ?
C31B C36B H36B 119.9 . . ?
C35B C36B H36B 119.9 . . ?
C30B N30B C37B 126.49(10) . . ?
C30B N30B H30B 118.3(10) . . ?
C37B N30B H30B 114.8(10) . . ?
N30B C37B C38B 110.90(11) . . ?
N30B C37B H37C 109.5 . . ?
C38B C37B H37C 109.5 . . ?
N30B C37B H37D 109.5 . . ?
C38B C37B H37D 109.5 . . ?
H37C C37B H37D 108.0 . . ?
C39B C38B C37B 113.79(11) . . ?
C39B C38B H38C 108.8 . . ?
C37B C38B H38C 108.8 . . ?
C39B C38B H38D 108.8 . . ?
C37B C38B H38D 108.8 . . ?
H38C C38B H38D 107.7 . . ?
N44B C39B C40B 122.39(13) . . ?
N44B C39B C38B 116.95(12) . . ?
C40B C39B C38B 120.65(13) . . ?
C41B C40B C39B 118.96(15) . . ?
C41B C40B H40B 120.5 . . ?
C39B C40B H40B 120.5 . . ?
C40B C41B C42B 118.88(15) . . ?
C40B C41B H41B 120.6 . . ?
C42B C41B H41B 120.6 . . ?
C43B C42B C41B 118.36(14) . . ?
C43B C42B H42B 120.8 . . ?
C41B C42B H42B 120.8 . . ?
N44B C43B C42B 123.59(15) . . ?
N44B C43B H43B 118.2 . . ?
C42B C43B H43B 118.2 . . ?
C39B N44B C43B 117.80(13) . . ?

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
C9AA N1A C2A O2A 179.71(10) . . . . ?
C11A N1A C2A O2A -3.24(16) . . . . ?
C9AA N1A C2A C3A 0.02(11) . . . . ?
C11A N1A C2A C3A 177.07(9) . . . . ?
O2A C2A C3A C30A -5.30(19) . . . . ?
N1A C2A C3A C30A 174.35(10) . . . . ?
O2A C2A C3A C3AA 179.03(11) . . . . ?
N1A C2A C3A C3AA -1.32(11) . . . . ?
C30A C3A C3AA N4A 4.71(18) . . . . ?
C2A C3A C3AA N4A -179.53(10) . . . . ?
C30A C3A C3AA C9AA -173.66(10) . . . . ?
C2A C3A C3AA C9AA 2.09(11) . . . . ?
C3A C3AA N4A C4AA -176.84(10) . . . . ?
C9AA C3AA N4A C4AA 1.33(14) . . . . ?
C3AA N4A C4AA C5A 177.60(9) . . . . ?
C3AA N4A C4AA C8AA -1.14(14) . . . . ?
N4A C4AA C5A C6A -178.54(10) . . . . ?
C8AA C4AA C5A C6A 0.23(16) . . . . ?
C4AA C5A C6A C7A -0.32(17) . . . . ?
C5A C6A C7A C8A -0.60(18) . . . . ?
C6A C7A C8A C8AA 1.60(18) . . . . ?
C7A C8A C8AA N9A 177.68(11) . . . . ?
C7A C8A C8AA C4AA -1.65(16) . . . . ?
N4A C4AA C8AA N9A 0.16(16) . . . . ?
C5A C4AA C8AA N9A -178.57(10) . . . . ?
N4A C4AA C8AA C8A 179.47(10) . . . . ?
C5A C4AA C8AA C8A 0.74(15) . . . . ?
C8A C8AA N9A C9AA -178.66(10) . . . . ?
C4AA C8AA N9A C9AA 0.64(15) . . . . ?
C8AA N9A C9AA N1A 179.56(10) . . . . ?
C8AA N9A C9AA C3AA -0.47(15) . . . . ?
C11A N1A C9AA N9A 4.29(18) . . . . ?
C2A N1A C9AA N9A -178.76(10) . . . . ?
C11A N1A C9AA C3AA -175.67(10) . . . . ?
C2A N1A C9AA C3AA 1.27(11) . . . . ?
N4A C3AA C9AA N9A -0.56(16) . . . . ?
C3A C3AA C9AA N9A 177.94(10) . . . . ?
N4A C3AA C9AA N1A 179.41(9) . . . . ?
C3A C3AA C9AA N1A -2.09(11) . . . . ?
C9AA N1A C11A C12A -48.75(16) . . . . ?
C2A N1A C11A C12A 134.68(11) . . . . ?
C9AA N1A C11A C16A 131.39(12) . . . . ?
C2A N1A C11A C16A -45.19(15) . . . . ?
C16A C11A C12A C13A -1.09(18) . . . . ?
N1A C11A C12A C13A 179.04(11) . . . . ?
C11A C12A C13A C14A 0.15(19) . . . . ?
C12A C13A C14A C15A 1.09(19) . . . . ?
C13A C14A C15A C16A -1.38(19) . . . . ?
C14A C15A C16A C11A 0.45(18) . . . . ?
C12A C11A C16A C15A 0.79(18) . . . . ?
N1A C11A C16A C15A -179.34(10) . . . . ?
C3AA C3A C30A N30A -3.99(17) . . . . ?
C2A C3A C30A N30A -178.93(10) . . . . ?
C3AA C3A C30A C31A 173.92(10) . . . . ?
C2A C3A C30A C31A -1.02(17) . . . . ?
N30A C30A C31A C32A 72.80(16) . . . . ?
C3A C30A C31A C32A -105.09(14) . . . . ?
N30A C30A C31A C36A -110.52(14) . . . . ?
C3A C30A C31A C36A 71.59(16) . . . . ?
C36A C31A C32A C33A 0.6(2) . . . . ?
C30A C31A C32A C33A 177.29(14) . . . . ?
C31A C32A C33A C34A 0.6(3) . . . . ?
C32A C33A C34A C35A -1.1(3) . . . . ?
C33A C34A C35A C36A 0.6(3) . . . . ?
C34A C35A C36A C31A 0.6(2) . . . . ?
C32A C31A C36A C35A -1.1(2) . . . . ?
C30A C31A C36A C35A -177.82(13) . . . . ?
C3A C30A N30A C37A 178.45(11) . . . . ?
C31A C30A N30A C37A 0.50(18) . . . . ?
C30A N30A C37A C38A 157.72(11) . . . . ?
N30A C37A C38A C39A 64.53(14) . . . . ?
C37A C38A C39A N44A 31.05(15) . . . . ?
C37A C38A C39A C40A -149.85(12) . . . . ?
N44A C39A C40A C41A 2.0(2) . . . . ?
C38A C39A C40A C41A -177.09(13) . . . . ?
C39A C40A C41A C42A -1.2(2) . . . . ?
C40A C41A C42A C43A -0.2(2) . . . . ?
C41A C42A C43A N44A 1.0(2) . . . . ?
C40A C39A N44A C43A -1.20(18) . . . . ?
C38A C39A N44A C43A 177.90(11) . . . . ?
C42A C43A N44A C39A -0.28(19) . . . . ?
C9AB N1B C2B O2B 177.60(10) . . . . ?
C11B N1B C2B O2B 0.99(16) . . . . ?
C9AB N1B C2B C3B -2.04(11) . . . . ?
C11B N1B C2B C3B -178.66(9) . . . . ?
O2B C2B C3B C30B -1.92(19) . . . . ?
N1B C2B C3B C30B 177.68(10) . . . . ?
O2B C2B C3B C3AB -177.13(11) . . . . ?
N1B C2B C3B C3AB 2.47(11) . . . . ?
C30B C3B C3AB N4B 2.12(19) . . . . ?
C2B C3B C3AB N4B 177.27(10) . . . . ?
C30B C3B C3AB C9AB -177.16(11) . . . . ?
C2B C3B C3AB C9AB -2.01(11) . . . . ?
C3B C3AB N4B C4AB 179.48(10) . . . . ?
C9AB C3AB N4B C4AB -1.33(14) . . . . ?
C3AB N4B C4AB C5B -178.68(9) . . . . ?
C3AB N4B C4AB C8AB 1.43(14) . . . . ?
N4B C4AB C5B C6B 178.72(10) . . . . ?
C8AB C4AB C5B C6B -1.38(15) . . . . ?
C4AB C5B C6B C7B 1.16(17) . . . . ?
C5B C6B C7B C8B 0.70(18) . . . . ?
C6B C7B C8B C8AB -2.31(17) . . . . ?
C7B C8B C8AB N9B -177.86(10) . . . . ?
C7B C8B C8AB C4AB 2.04(16) . . . . ?
N4B C4AB C8AB N9B -0.42(15) . . . . ?
C5B C4AB C8AB N9B 179.69(9) . . . . ?
N4B C4AB C8AB C8B 179.69(9) . . . . ?
C5B C4AB C8AB C8B -0.21(15) . . . . ?
C8B C8AB N9B C9AB 179.15(10) . . . . ?
C4AB C8AB N9B C9AB -0.75(14) . . . . ?
C8AB N9B C9AB N1B 179.38(10) . . . . ?
C8AB N9B C9AB C3AB 0.89(15) . . . . ?
C11B N1B C9AB N9B -1.45(17) . . . . ?
C2B N1B C9AB N9B -177.90(10) . . . . ?
C11B N1B C9AB C3AB 177.25(10) . . . . ?
C2B N1B C9AB C3AB 0.81(11) . . . . ?
N4B C3AB C9AB N9B 0.18(17) . . . . ?
C3B C3AB C9AB N9B 179.52(10) . . . . ?
N4B C3AB C9AB N1B -178.56(9) . . . . ?
C3B C3AB C9AB N1B 0.78(11) . . . . ?
C9AB N1B C11B C12B -129.51(11) . . . . ?
C2B N1B C11B C12B 46.52(15) . . . . ?
C9AB N1B C11B C16B 51.46(16) . . . . ?
C2B N1B C11B C16B -132.51(12) . . . . ?
C16B C11B C12B C13B -0.04(17) . . . . ?
N1B C11B C12B C13B -179.07(11) . . . . ?
C11B C12B C13B C14B -0.26(18) . . . . ?
C12B C13B C14B C15B 0.32(19) . . . . ?
C13B C14B C15B C16B -0.1(2) . . . . ?
C12B C11B C16B C15B 0.28(18) . . . . ?
N1B C11B C16B C15B 179.31(11) . . . . ?
C14B C15B C16B C11B -0.23(19) . . . . ?
C3AB C3B C30B N30B 4.74(18) . . . . ?
C2B C3B C30B N30B -169.55(11) . . . . ?
C3AB C3B C30B C31B -175.49(10) . . . . ?
C2B C3B C30B C31B 10.22(17) . . . . ?
N30B C30B C31B C32B -115.23(12) . . . . ?
C3B C30B C31B C32B 65.00(15) . . . . ?
N30B C30B C31B C36B 65.50(15) . . . . ?
C3B C30B C31B C36B -114.27(13) . . . . ?
C36B C31B C32B C33B 0.66(17) . . . . ?
C30B C31B C32B C33B -178.61(10) . . . . ?
C31B C32B C33B C34B 0.63(18) . . . . ?
C32B C33B C34B C35B -1.30(19) . . . . ?
C33B C34B C35B C36B 0.66(18) . . . . ?
C32B C31B C36B C35B -1.30(17) . . . . ?
C30B C31B C36B C35B 177.97(11) . . . . ?
C34B C35B C36B C31B 0.64(18) . . . . ?
C3B C30B N30B C37B -170.87(12) . . . . ?
C31B C30B N30B C37B 9.36(18) . . . . ?
C30B N30B C37B C38B 115.87(14) . . . . ?
N30B C37B C38B C39B 63.55(15) . . . . ?
C37B C38B C39B N44B 10.94(17) . . . . ?
C37B C38B C39B C40B -170.26(13) . . . . ?
N44B C39B C40B C41B 1.5(2) . . . . ?
C38B C39B C40B C41B -177.27(15) . . . . ?
C39B C40B C41B C42B -0.7(3) . . . . ?
C40B C41B C42B C43B -0.4(3) . . . . ?
C41B C42B C43B N44B 0.7(2) . . . . ?
C40B C39B N44B C43B -1.1(2) . . . . ?
C38B C39B N44B C43B 177.63(12) . . . . ?
C42B C43B N44B C39B 0.0(2) . . . . ?

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
_geom_hbond_publ_flag
N30A H30A N4A 0.89(1) 2.05(2) 2.811(1) 142(1) . ?
N30B H30B N4B 0.90(13) 2.22(2) 2.908(1) 134(1) . ?
N30B H30B N44B 0.90(1) 2.42(2) 2.939(2) 117(1) . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        76.80
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.032

_database_code_depnum_ccdc_archive 'CCDC 1006388'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pS-2_pR-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (E)-3-{[2-(2-aminoethyl)pyridine]-phenylmethylidene}-1,4-dihydro-2H-1-
  phenylpyrrolo[2,3-b]quinoxalin-2-one; non centrosymmetric structure 
  containing the molecules with (pR):(pS) configuration ratio = 0.828:0.172  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_melting_point_lt       443
_chemical_melting_point_gt       444
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24.32 N5 O1.66'
_chemical_formula_weight         481.42

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 2(1) '

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

_cell_length_a                   5.75094(3)
_cell_length_b                   17.80093(8)
_cell_length_c                   11.63481(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.7275(5)
_cell_angle_gamma                90.00
_cell_volume                     1177.289(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    119.9(2)
_cell_measurement_reflns_used    38908
_cell_measurement_theta_min      3.8406
_cell_measurement_theta_max      76.7258

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             505
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7933
_exptl_absorpt_correction_T_max  0.8737
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
 (compiled Jul 11 2012,15:38:31)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      119.9(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            46913
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         8.10
_diffrn_reflns_theta_max         76.93
_reflns_number_total             4946
_reflns_number_gt                4941
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    
; SIR92 (A. Altomare, G. Cascarano, 
C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, 
J. Appl. Cryst., 27 (1994) 435)
;
_computing_structure_refinement  
;
SHELXL-97 (M. Sheldrick, Acta Cryst. A64 (2008) 112)
;
_computing_molecular_graphics    
;
ORTEP-3 for Windows (L. Farrugia, J. Appl. Cryst., 32 (1999) 837) 
and Mercury 2.3 (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, 
G. P. Shields, R. Taylor, M. Towler, J. van de Streek, J. Appl. Cryst., 
39 (2006) 453)
;
_computing_publication_material  
;
SHELXL-97 (M. Sheldrick, Acta Cryst. A64 (2008) 112)
;

_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. 

 Among 8 least-squares restraints there are 7 DFIX restraints for N30-H30, 
 O45-H451, O45-H452 and for C-H of disordered methylene group (C37-H371, 
 C37-H372 and C37-H37A, C37-H37B) bond lengths and the fixed value for y 
 coordinates of the origin in P2(1) space group. For the disordered pyridine
 ring: C39C^N44C and C39D^N44D, the SHELXL AFIX 66 constraints were applied 
 with the fixed bond lengths and angles at the values of 1.3900 Angstroms and 
 120 degrees, respectively. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.3667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         4946
_refine_ls_number_parameters     361
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0035(2) 0.88209(8) 0.74385(12) 0.0236(3) Uani 1 1 d . . .
C2 C 0.1220(3) 0.84532(9) 0.66373(14) 0.0236(3) Uani 1 1 d . . .
O2 O 0.2778(2) 0.87616(7) 0.62154(11) 0.0291(3) Uani 1 1 d . . .
C3 C 0.0306(3) 0.76873(9) 0.65145(13) 0.0228(3) Uani 1 1 d . . .
C3A C -0.1400(3) 0.76129(9) 0.72778(13) 0.0217(3) Uani 1 1 d . . .
N4 N -0.2639(2) 0.70256(8) 0.75041(11) 0.0223(3) Uani 1 1 d . . .
C4A C -0.4203(3) 0.71583(8) 0.82723(13) 0.0218(3) Uani 1 1 d . . .
C5 C -0.5688(3) 0.65685(9) 0.85364(14) 0.0254(3) Uani 1 1 d . . .
H5 H -0.5571(4) 0.6092(12) 0.8196(9) 0.030 Uiso 1 1 calc R . .
C6 C -0.7305(3) 0.66810(10) 0.92845(15) 0.0285(3) Uani 1 1 d . . .
H6 H -0.835(2) 0.6259(10) 0.9460(4) 0.034 Uiso 1 1 calc R . .
C7 C -0.7482(3) 0.73892(10) 0.97997(15) 0.0286(3) Uani 1 1 d . . .
H7 H -0.865(3) 0.7470(2) 1.0343(13) 0.034 Uiso 1 1 calc R . .
C8 C -0.6057(3) 0.79705(10) 0.95606(14) 0.0256(3) Uani 1 1 d . . .
H8 H -0.6188(4) 0.8434(12) 0.9907(9) 0.031 Uiso 1 1 calc R . .
C8A C -0.4394(3) 0.78726(9) 0.87954(14) 0.0224(3) Uani 1 1 d . . .
N9 N -0.3028(2) 0.84818(7) 0.85669(11) 0.0222(3) Uani 1 1 d . . .
C9A C -0.1623(3) 0.83360(8) 0.78216(13) 0.0208(3) Uani 1 1 d . . .
C11 C 0.0317(3) 0.95907(8) 0.77710(13) 0.0221(3) Uani 1 1 d . . .
C12 C -0.1565(3) 1.00868(9) 0.75971(14) 0.0251(3) Uani 1 1 d . . .
H12 H -0.306(4) 0.9922(4) 0.7261(8) 0.030 Uiso 1 1 calc R . .
C13 C -0.1193(3) 1.08351(10) 0.79322(16) 0.0303(4) Uani 1 1 d . . .
H13 H -0.246(3) 1.1179(9) 0.7822(3) 0.036 Uiso 1 1 calc R . .
C14 C 0.1031(3) 1.10792(10) 0.84264(16) 0.0315(4) Uani 1 1 d . . .
H14 H 0.1278(7) 1.1603(14) 0.8663(6) 0.038 Uiso 1 1 calc R . .
C15 C 0.2900(3) 1.05774(10) 0.85827(16) 0.0319(4) Uani 1 1 d . . .
H15 H 0.456(4) 1.0759(4) 0.8949(9) 0.038 Uiso 1 1 calc R . .
C16 C 0.2546(3) 0.98293(9) 0.82479(15) 0.0266(3) Uani 1 1 d . . .
H16 H 0.390(3) 0.9465(8) 0.8352(3) 0.032 Uiso 1 1 calc R . .
C30 C 0.0986(3) 0.71248(9) 0.57989(13) 0.0228(3) Uani 1 1 d . . .
C31 C 0.2356(3) 0.72882(9) 0.48412(13) 0.0223(3) Uani 1 1 d . . .
C32 C 0.1486(3) 0.78156(9) 0.39999(14) 0.0247(3) Uani 1 1 d . . .
H32 H 0.001(3) 0.8096(6) 0.4067(2) 0.030 Uiso 1 1 calc R . .
C33 C 0.2679(3) 0.79520(10) 0.30652(15) 0.0284(3) Uani 1 1 d . . .
H33 H 0.2019(16) 0.8329(9) 0.2438(15) 0.034 Uiso 1 1 calc R . .
C35 C 0.5650(3) 0.70603(10) 0.38352(15) 0.0282(3) Uani 1 1 d . . .
H35 H 0.717(3) 0.6790(6) 0.37800(19) 0.034 Uiso 1 1 calc R . .
C34 C 0.4769(3) 0.75757(10) 0.29841(15) 0.0293(3) Uani 1 1 d . . .
H34 H 0.563(2) 0.7676(3) 0.2320(16) 0.035 Uiso 1 1 calc R . .
C36 C 0.4457(3) 0.69146(9) 0.47596(14) 0.0254(3) Uani 1 1 d . . .
H36 H 0.5069(15) 0.6561(9) 0.5338(14) 0.030 Uiso 1 1 calc R . .
N30 N 0.0288(3) 0.64250(7) 0.59491(11) 0.0250(3) Uani 1 1 d D A .
H30 H -0.057(3) 0.6389(13) 0.6493(14) 0.030 Uiso 1 1 d D . .
C37 C 0.0591(4) 0.57698(10) 0.52247(15) 0.0331(4) Uani 1 1 d D . .
H371 H 0.032(5) 0.591(2) 0.4410(12) 0.040 Uiso 0.828(4) 1 d PD . .
H372 H 0.217(3) 0.5554(16) 0.533(3) 0.040 Uiso 0.828(4) 1 d PD . .
H37A H -0.105(7) 0.569(8) 0.490(12) 0.040 Uiso 0.172(4) 1 d PD . .
H37B H 0.12(2) 0.595(9) 0.453(7) 0.040 Uiso 0.172(4) 1 d PD . .
C38C C -0.0956(4) 0.51395(11) 0.55001(17) 0.0262(5) Uani 0.828(4) 1 d P A 1
H38A H -0.2618 0.5303 0.5333 0.031 Uiso 0.828(4) 1 calc PR A 1
H38B H -0.0759 0.4709 0.4985 0.031 Uiso 0.828(4) 1 calc PR A 1
C39C C -0.0441(2) 0.48917(7) 0.67153(8) 0.0254(5) Uani 0.828(4) 1 d PG A 1
C40C C -0.1955(2) 0.50389(8) 0.75123(13) 0.0332(5) Uani 0.828(4) 1 d PG A 1
H40C H -0.3420 0.5280 0.7266 0.040 Uiso 0.828(4) 1 calc PR A 1
C41C C -0.1327(3) 0.48332(10) 0.86703(11) 0.0421(6) Uani 0.828(4) 1 d PG A 1
H41C H -0.2362 0.4934 0.9215 0.050 Uiso 0.828(4) 1 calc PR A 1
C42C C 0.0815(3) 0.44804(10) 0.90313(8) 0.0410(7) Uani 0.828(4) 1 d PG A 1
H42C H 0.1245 0.4340 0.9823 0.049 Uiso 0.828(4) 1 calc PR A 1
C43C C 0.2330(2) 0.43333(9) 0.82343(12) 0.0419(6) Uani 0.828(4) 1 d PG A 1
H43C H 0.3794 0.4092 0.8481 0.050 Uiso 0.828(4) 1 calc PR A 1
N44C N 0.1702(2) 0.45390(8) 0.70763(11) 0.0338(5) Uani 0.828(4) 1 d PG A 1
C38D C 0.1448(4) 0.51079(13) 0.56314(13) 0.026(2) Uiso 0.172(4) 1 d PG A 2
H38C H 0.3146 0.5095 0.5570 0.031 Uiso 0.172(4) 1 calc PR A 2
H38D H 0.0675 0.4709 0.5116 0.031 Uiso 0.172(4) 1 calc PR A 2
C39D C 0.1175(13) 0.4915(2) 0.6859(5) 0.033(2) Uiso 0.172(4) 1 d PG A 2
C40D C 0.2561(12) 0.4431(2) 0.7611(9) 0.0442(19) Uiso 0.172(4) 1 d PG A 2
H40D H 0.3953 0.4223 0.7394 0.053 Uiso 0.172(4) 1 calc PR A 2
C41D C 0.1911(12) 0.4251(3) 0.8681(7) 0.0442(19) Uiso 0.172(4) 1 d PG A 2
H41D H 0.2859 0.3920 0.9195 0.053 Uiso 0.172(4) 1 calc PR A 2
C42D C -0.0125(15) 0.4555(3) 0.8998(6) 0.0442(19) Uiso 0.172(4) 1 d PG A 2
H42D H -0.0569 0.4432 0.9729 0.053 Uiso 0.172(4) 1 calc PR A 2
C43D C -0.1511(12) 0.5039(3) 0.8246(8) 0.0442(19) Uiso 0.172(4) 1 d PG A 2
H43D H -0.2903 0.5247 0.8463 0.053 Uiso 0.172(4) 1 calc PR A 2
N44D N -0.0861(9) 0.5219(3) 0.7176(7) 0.0442(19) Uiso 0.172(4) 1 d PG A 2
O45 O 0.6705(4) 0.91018(15) 0.51405(18) 0.0464(9) Uani 0.661(7) 1 d PGD B 2
H451 H 0.5189 0.8990 0.5223 0.058(11) Uiso 0.661(7) 1 d PGD B 2
H452 H 0.6686 0.9091 0.4319 0.074(14) Uiso 0.661(7) 1 d PGD B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9A 1.379(2) . ?
N1 C2 1.4221(19) . ?
N1 C11 1.4300(19) . ?
C2 O2 1.216(2) . ?
C2 C3 1.460(2) . ?
C3 C30 1.396(2) . ?
C3 C3A 1.426(2) . ?
C3A N4 1.314(2) . ?
C3A C9A 1.448(2) . ?
N4 C4A 1.3813(19) . ?
C4A C5 1.416(2) . ?
C4A C8A 1.421(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9434 . ?
C6 C7 1.406(2) . ?
C6 H6 1.0020 . ?
C7 C8 1.374(2) . ?
C7 H7 1.0009 . ?
C8 C8A 1.412(2) . ?
C8 H8 0.9272 . ?
C8A N9 1.388(2) . ?
N9 C9A 1.298(2) . ?
C11 C16 1.384(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.395(2) . ?
C12 H12 0.9355 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9469 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9764 . ?
C15 C16 1.394(2) . ?
C15 H15 1.0358 . ?
C16 H16 1.0082 . ?
C30 N30 1.328(2) . ?
C30 C31 1.488(2) . ?
C31 C32 1.393(2) . ?
C31 C36 1.395(2) . ?
C32 C33 1.392(2) . ?
C32 H32 0.9987 . ?
C33 C34 1.392(3) . ?
C33 H33 1.0204 . ?
C35 C36 1.385(2) . ?
C35 C34 1.388(3) . ?
C35 H35 1.0098 . ?
C34 H34 0.9931 . ?
C36 H36 0.9495 . ?
N30 C37 1.465(2) . ?
N30 H30 0.861(10) . ?
C37 C38D 1.336(3) . ?
C37 C38C 1.497(3) . ?
C37 H371 0.971(10) . ?
C37 H372 0.978(10) . ?
C37 H37A 0.970(11) . ?
C37 H37B 0.969(11) . ?
C38C C39C 1.468(2) . ?
C38C H37A 1.19(15) . ?
C38C H38A 0.9900 . ?
C38C H38B 0.9900 . ?
C39C C40C 1.3900 . ?
C39C N44C 1.3900 . ?
C40C C41C 1.3900 . ?
C40C H40C 0.9500 . ?
C41C C42C 1.3900 . ?
C41C H41C 0.9500 . ?
C42C C43C 1.3900 . ?
C42C H42C 0.9500 . ?
C43C N44C 1.3900 . ?
C43C H43C 0.9500 . ?
C38D C39D 1.500(5) . ?
C38D H372 0.98(3) . ?
C38D H38C 0.9900 . ?
C38D H38D 0.9900 . ?
C39D C40D 1.3900 . ?
C39D N44D 1.3900 . ?
C40D C41D 1.3900 . ?
C40D H40D 0.9500 . ?
C41D C42D 1.3900 . ?
C41D H41D 0.9500 . ?
C42D C43D 1.3900 . ?
C42D H42D 0.9500 . ?
C43D N44D 1.3900 . ?
C43D H43D 0.9500 . ?
O45 H451 0.9133 . ?
O45 H452 0.9542 . ?

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
C9A N1 C2 110.53(13) . . ?
C9A N1 C11 125.86(13) . . ?
C2 N1 C11 123.60(13) . . ?
O2 C2 N1 122.35(15) . . ?
O2 C2 C3 131.18(15) . . ?
N1 C2 C3 106.42(13) . . ?
C30 C3 C3A 125.91(15) . . ?
C30 C3 C2 126.78(14) . . ?
C3A C3 C2 107.30(13) . . ?
N4 C3A C3 130.08(14) . . ?
N4 C3A C9A 122.22(14) . . ?
C3 C3A C9A 107.70(13) . . ?
C3A N4 C4A 114.82(13) . . ?
N4 C4A C5 119.15(14) . . ?
N4 C4A C8A 122.02(13) . . ?
C5 C4A C8A 118.82(13) . . ?
C6 C5 C4A 121.00(15) . . ?
C6 C5 H5 119.5 . . ?
C4A C5 H5 119.5 . . ?
C5 C6 C7 119.85(15) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.30(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C8A 121.08(16) . . ?
C7 C8 H8 119.5 . . ?
C8A C8 H8 119.5 . . ?
N9 C8A C8 118.76(14) . . ?
N9 C8A C4A 122.28(13) . . ?
C8 C8A C4A 118.94(14) . . ?
C9A N9 C8A 113.55(13) . . ?
N9 C9A N1 126.93(14) . . ?
N9 C9A C3A 125.06(14) . . ?
N1 C9A C3A 107.97(13) . . ?
C16 C11 C12 121.18(15) . . ?
C16 C11 N1 119.12(14) . . ?
C12 C11 N1 119.69(15) . . ?
C11 C12 C13 118.92(17) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.43(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.91(16) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.07(17) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 119.48(16) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
N30 C30 C3 118.48(14) . . ?
N30 C30 C31 119.13(14) . . ?
C3 C30 C31 122.33(14) . . ?
C32 C31 C36 119.71(14) . . ?
C32 C31 C30 118.92(14) . . ?
C36 C31 C30 121.36(14) . . ?
C33 C32 C31 119.96(15) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.13(16) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C36 C35 C34 120.49(15) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C34 C33 119.68(15) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C35 C36 C31 119.99(15) . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C30 N30 C37 127.33(14) . . ?
C30 N30 H30 112.6(16) . . ?
C37 N30 H30 119.7(16) . . ?
C38D C37 N30 124.63(16) . . ?
C38D C37 C38C 57.47(14) . . ?
N30 C37 C38C 110.33(15) . . ?
C38D C37 H371 125(2) . . ?
N30 C37 H371 110(2) . . ?
C38C C37 H371 113.0(19) . . ?
C38D C37 H372 47.3(18) . . ?
N30 C37 H372 115.3(18) . . ?
C38C C37 H372 104.5(18) . . ?
H371 C37 H372 104(3) . . ?
C38D C37 H37A 107(9) . . ?
N30 C37 H37A 99(9) . . ?
C38C C37 H37A 53(9) . . ?
H371 C37 H37A 70(9) . . ?
H372 C37 H37A 145(9) . . ?
C38D C37 H37B 116(10) . . ?
N30 C37 H37B 107(10) . . ?
C38C C37 H37B 135(10) . . ?
H371 C37 H37B 29(8) . . ?
H372 C37 H37B 79(9) . . ?
H37A C37 H37B 99(10) . . ?
C39C C38C C37 113.08(16) . . ?
C39C C38C H37A 142(6) . . ?
C37 C38C H37A 40.3(6) . . ?
C39C C38C H38A 109.0 . . ?
C37 C38C H38A 109.0 . . ?
H37A C38C H38A 72.0 . . ?
C39C C38C H38B 109.0 . . ?
C37 C38C H38B 109.0 . . ?
H37A C38C H38B 106.2 . . ?
H38A C38C H38B 107.8 . . ?
C40C C39C N44C 120.0 . . ?
C40C C39C C38C 122.06(13) . . ?
N44C C39C C38C 117.83(13) . . ?
C39C C40C C41C 120.0 . . ?
C39C C40C H40C 120.0 . . ?
C41C C40C H40C 120.0 . . ?
C42C C41C C40C 120.0 . . ?
C42C C41C H41C 120.0 . . ?
C40C C41C H41C 120.0 . . ?
C41C C42C C43C 120.0 . . ?
C41C C42C H42C 120.0 . . ?
C43C C42C H42C 120.0 . . ?
C42C C43C N44C 120.0 . . ?
C42C C43C H43C 120.0 . . ?
N44C C43C H43C 120.0 . . ?
C43C N44C C39C 120.0 . . ?
C37 C38D C39D 116.9(2) . . ?
C37 C38D H372 46.9(6) . . ?
C39D C38D H372 129.1(18) . . ?
C37 C38D H38C 108.1 . . ?
C39D C38D H38C 108.1 . . ?
H372 C38D H38C 61.2 . . ?
C37 C38D H38D 108.1 . . ?
C39D C38D H38D 108.1 . . ?
H372 C38D H38D 122.8 . . ?
H38C C38D H38D 107.3 . . ?
C40D C39D N44D 120.0 . . ?
C40D C39D C38D 127.5(5) . . ?
N44D C39D C38D 112.2(5) . . ?
C39D C40D C41D 120.0 . . ?
C39D C40D H40D 120.0 . . ?
C41D C40D H40D 120.0 . . ?
C40D C41D C42D 120.0 . . ?
C40D C41D H41D 120.0 . . ?
C42D C41D H41D 120.0 . . ?
C41D C42D C43D 120.0 . . ?
C41D C42D H42D 120.0 . . ?
C43D C42D H42D 120.0 . . ?
N44D C43D C42D 120.0 . . ?
N44D C43D H43D 120.0 . . ?
C42D C43D H43D 120.0 . . ?
C43D N44D C39D 120.0 . . ?
H451 O45 H452 103.6 . . ?

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
C9A N1 C2 O2 -177.24(16) . . . . ?
C11 N1 C2 O2 3.6(2) . . . . ?
C9A N1 C2 C3 0.64(17) . . . . ?
C11 N1 C2 C3 -178.53(14) . . . . ?
O2 C2 C3 C30 -3.7(3) . . . . ?
N1 C2 C3 C30 178.70(15) . . . . ?
O2 C2 C3 C3A 175.47(17) . . . . ?
N1 C2 C3 C3A -2.15(16) . . . . ?
C30 C3 C3A N4 1.8(3) . . . . ?
C2 C3 C3A N4 -177.37(15) . . . . ?
C30 C3 C3A C9A -178.02(15) . . . . ?
C2 C3 C3A C9A 2.82(16) . . . . ?
C3 C3A N4 C4A -178.12(15) . . . . ?
C9A C3A N4 C4A 1.7(2) . . . . ?
C3A N4 C4A C5 177.49(13) . . . . ?
C3A N4 C4A C8A -1.6(2) . . . . ?
N4 C4A C5 C6 -178.89(14) . . . . ?
C8A C4A C5 C6 0.3(2) . . . . ?
C4A C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C8A 0.1(3) . . . . ?
C7 C8 C8A N9 178.82(15) . . . . ?
C7 C8 C8A C4A -0.2(2) . . . . ?
N4 C4A C8A N9 0.1(2) . . . . ?
C5 C4A C8A N9 -178.98(14) . . . . ?
N4 C4A C8A C8 179.12(14) . . . . ?
C5 C4A C8A C8 0.0(2) . . . . ?
C8 C8A N9 C9A -177.67(14) . . . . ?
C4A C8A N9 C9A 1.3(2) . . . . ?
C8A N9 C9A N1 -178.83(15) . . . . ?
C8A N9 C9A C3A -1.3(2) . . . . ?
C2 N1 C9A N9 178.96(15) . . . . ?
C11 N1 C9A N9 -1.9(3) . . . . ?
C2 N1 C9A C3A 1.11(17) . . . . ?
C11 N1 C9A C3A -179.75(14) . . . . ?
N4 C3A C9A N9 -0.2(2) . . . . ?
C3 C3A C9A N9 179.63(14) . . . . ?
N4 C3A C9A N1 177.71(14) . . . . ?
C3 C3A C9A N1 -2.46(17) . . . . ?
C9A N1 C11 C16 124.01(17) . . . . ?
C2 N1 C11 C16 -57.0(2) . . . . ?
C9A N1 C11 C12 -56.9(2) . . . . ?
C2 N1 C11 C12 122.18(16) . . . . ?
C16 C11 C12 C13 -1.2(2) . . . . ?
N1 C11 C12 C13 179.67(14) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C12 C11 C16 C15 1.4(2) . . . . ?
N1 C11 C16 C15 -179.49(15) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C3A C3 C30 N30 -11.0(2) . . . . ?
C2 C3 C30 N30 167.96(15) . . . . ?
C3A C3 C30 C31 165.83(14) . . . . ?
C2 C3 C30 C31 -15.2(3) . . . . ?
N30 C30 C31 C32 122.04(17) . . . . ?
C3 C30 C31 C32 -54.8(2) . . . . ?
N30 C30 C31 C36 -56.7(2) . . . . ?
C3 C30 C31 C36 126.42(17) . . . . ?
C36 C31 C32 C33 1.8(2) . . . . ?
C30 C31 C32 C33 -176.95(15) . . . . ?
C31 C32 C33 C34 -1.6(2) . . . . ?
C36 C35 C34 C33 0.4(3) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C34 C35 C36 C31 -0.1(2) . . . . ?
C32 C31 C36 C35 -1.0(2) . . . . ?
C30 C31 C36 C35 177.76(15) . . . . ?
C3 C30 N30 C37 173.17(17) . . . . ?
C31 C30 N30 C37 -3.8(3) . . . . ?
C30 N30 C37 C38D 130.7(2) . . . . ?
C30 N30 C37 C38C -165.48(16) . . . . ?
C38D C37 C38C C39C 58.51(15) . . . . ?
N30 C37 C38C C39C -60.3(2) . . . . ?
C37 C38C C39C C40C 108.43(16) . . . . ?
C37 C38C C39C N44C -67.74(17) . . . . ?
N44C C39C C40C C41C 0.0 . . . . ?
C38C C39C C40C C41C -176.09(15) . . . . ?
C39C C40C C41C C42C 0.0 . . . . ?
C40C C41C C42C C43C 0.0 . . . . ?
C41C C42C C43C N44C 0.0 . . . . ?
C42C C43C N44C C39C 0.0 . . . . ?
C40C C39C N44C C43C 0.0 . . . . ?
C38C C39C N44C C43C 176.26(14) . . . . ?
N30 C37 C38D C39D 25.6(4) . . . . ?
C38C C37 C38D C39D -67.8(3) . . . . ?
C37 C38D C39D C40D -154.7(2) . . . . ?
C37 C38D C39D N44D 31.8(4) . . . . ?
N44D C39D C40D C41D 0.0 . . . . ?
C38D C39D C40D C41D -173.0(3) . . . . ?
C39D C40D C41D C42D 0.0 . . . . ?
C40D C41D C42D C43D 0.0 . . . . ?
C41D C42D C43D N44D 0.0 . . . . ?
C42D C43D N44D C39D 0.0 . . . . ?
C40D C39D N44D C43D 0.0 . . . . ?
C38D C39D N44D C43D 174.00(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
_geom_hbond_publ_flag
N30 H30 N4 0.861(10) 2.124(16) 2.8592(18) 143(2) . ?
N30 H30 N44D 0.861(10) 2.25(2) 2.716(3) 114(2) . ?
O45 H451 O2 0.91 1.98 2.809(2) 150.6 . ?
O45 H452 N44C 0.95 2.14 2.969(10) 144 2_656 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        76.93
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.041

_database_code_depnum_ccdc_archive 'CCDC 1006389'
