# Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Antonio Frontera'
_publ_contact_author_email       TONI.FRONTERA@UIB.ES

_publ_section_title              
;
Lone pair-pi vs pi-pi interactions in 5-fluoro-1-hexyluracil
and 1-hexyluracil: a combined crystallographic and computational study
;
_publ_requested_category         FO
loop_
_publ_author_name
'Antonio Frontera'
'Miquel Barcelo-Oliver'
'Pere M Deya'
'Carolina Estarellas'
;
A.Garcia-Raso
;
'Elies Molins'
'David Quinonero'
'Angel Terron'

# Attachment '2new.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2009-07-03 at 08:37:49
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : pm116 difabs dreduc struct

data_pm116
_database_code_depnum_ccdc_archive 'CCDC 730816'

_audit_creation_date             2009-07-03T08:37:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C10 H15 F1 N2 O2'
_chemical_formula_sum            'C10 H15 F N2 O2'
_chemical_formula_weight         214.24
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.369(5)
_cell_length_b                   8.867(2)
_cell_length_c                   11.904(7)
_cell_angle_alpha                90
_cell_angle_beta                 117.17(4)
_cell_angle_gamma                90
_cell_volume                     1161.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    16
_cell_measurement_theta_min      4.97
_cell_measurement_theta_max      11.85
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.9814

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.020861
_diffrn_orient_matrix_ub_12      0.107152
_diffrn_orient_matrix_ub_13      -0.026765
_diffrn_orient_matrix_ub_21      0.028039
_diffrn_orient_matrix_ub_22      0.031306
_diffrn_orient_matrix_ub_23      0.086116
_diffrn_orient_matrix_ub_31      0.087668
_diffrn_orient_matrix_ub_32      0.01569
_diffrn_orient_matrix_ub_33      0.010745
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        4
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
4 0 -1

_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_number            2021
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_reflns_number_total             2021
_reflns_number_gt                703
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# 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)+(0.1998P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2021
_refine_ls_number_parameters     275
_refine_ls_number_restraints     211
_refine_ls_R_factor_all          0.2321
_refine_ls_R_factor_gt           0.1013
_refine_ls_wR_factor_ref         0.416
_refine_ls_wR_factor_gt          0.3588
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
# 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'
F F 0.0171 0.0103 '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
N1 N 0.28205(13) 0.79759(19) 0.65048(13) 0.0715(6) Uani 1 1 d . . .
C2 C 0.30201(19) 0.8053(2) 0.77354(17) 0.0802(8) Uani 1 1 d . A .
O2 O 0.24049(12) 0.74031(19) 0.81327(13) 0.0961(6) Uani 1 1 d . . .
N3 N 0.39651(12) 0.8957(2) 0.84869(13) 0.0765(6) Uani 1 1 d . . .
H3 H 0.4095 0.9011 0.926 0.092 Uiso 1 1 calc R A .
C4 C 0.47479(16) 0.9801(3) 0.82049(16) 0.0742(8) Uani 1 1 d . A .
O4 O 0.55653(12) 1.05522(19) 0.89624(13) 0.0998(6) Uani 1 1 d . . .
C5 C 0.44614(16) 0.9620(3) 0.68843(18) 0.0795(8) Uani 1 1 d . . .
F5 F 0.51616(11) 1.03880(18) 0.64880(11) 0.1195(6) Uani 1 1 d . A .
C6 C 0.35357(17) 0.8798(3) 0.61306(18) 0.0803(8) Uani 1 1 d . A .
H6 H 0.335 0.877 0.5281 0.096 Uiso 1 1 calc R . .
C11 C 0.18243(16) 0.7091(2) 0.55960(18) 0.0821(8) Uani 0.3 1 d PD A 1
H11A H 0.1724 0.6197 0.6008 0.098 Uiso 0.3 1 calc PR A 1
H11B H 0.2019 0.6766 0.4931 0.098 Uiso 0.3 1 calc PR A 1
C12 C 0.0661(3) 0.7949(5) 0.5026(6) 0.0947(19) Uani 0.3 1 d PDU A 1
H12A H 0.0748 0.881 0.4571 0.114 Uiso 0.3 1 calc PR A 1
H12B H 0.0495 0.8328 0.5695 0.114 Uiso 0.3 1 calc PR A 1
C13 C -0.0406(3) 0.7006(5) 0.4131(6) 0.117(2) Uani 0.3 1 d PDU A 1
H13A H -0.0162 0.6402 0.3605 0.14 Uiso 0.3 1 calc PR A 1
H13B H -0.0645 0.6323 0.4615 0.14 Uiso 0.3 1 calc PR A 1
C14 C -0.1464(4) 0.7965(5) 0.3310(4) 0.1219(18) Uani 0.3 1 d PDU A 1
H14A H -0.1172 0.885 0.3055 0.146 Uiso 0.3 1 calc PR A 1
H14B H -0.1871 0.8303 0.3795 0.146 Uiso 0.3 1 calc PR A 1
C15 C -0.2362(4) 0.7154(6) 0.2153(3) 0.1270(19) Uani 0.3 1 d PDU A 1
H15A H -0.3175 0.7248 0.2074 0.152 Uiso 0.3 1 calc PR A 1
H15B H -0.2159 0.6091 0.2202 0.152 Uiso 0.3 1 calc PR A 1
C16 C -0.2298(6) 0.7877(8) 0.1032(3) 0.139(2) Uani 0.3 1 d PDU A 1
H16A H -0.2849 0.8715 0.0739 0.208 Uiso 0.3 1 calc PR A 1
H16B H -0.2518 0.7149 0.0366 0.208 Uiso 0.3 1 calc PR A 1
H16C H -0.1485 0.8225 0.1281 0.208 Uiso 0.3 1 calc PR A 1
C21 C 0.18243(16) 0.7091(2) 0.55960(18) 0.0821(8) Uani 0.3 1 d PD A 2
H21A H 0.1549 0.6417 0.6054 0.098 Uiso 0.3 1 calc PR A 2
H21B H 0.2131 0.647 0.5134 0.098 Uiso 0.3 1 calc PR A 2
C22 C 0.0755(4) 0.7948(6) 0.4665(6) 0.118(2) Uani 0.3 1 d PDU A 2
H22A H 0.1013 0.8669 0.4223 0.142 Uiso 0.3 1 calc PR A 2
H22B H 0.0378 0.8498 0.5098 0.142 Uiso 0.3 1 calc PR A 2
C23 C -0.0150(4) 0.6845(6) 0.3729(6) 0.1318(13) Uani 0.3 1 d PDU A 2
H23A H 0.0238 0.6316 0.3297 0.158 Uiso 0.3 1 calc PR A 2
H23B H -0.0366 0.6102 0.4191 0.158 Uiso 0.3 1 calc PR A 2
C24 C -0.1276(5) 0.7571(7) 0.2775(5) 0.132(2) Uani 0.3 1 d PDU A 2
H24A H -0.1073 0.849 0.2472 0.158 Uiso 0.3 1 calc PR A 2
H24B H -0.1796 0.7833 0.3157 0.158 Uiso 0.3 1 calc PR A 2
C25 C -0.1941(5) 0.6508(6) 0.1684(5) 0.141(2) Uani 0.3 1 d PDU A 2
H25A H -0.2225 0.563 0.1958 0.169 Uiso 0.3 1 calc PR A 2
H25B H -0.1409 0.6175 0.1335 0.169 Uiso 0.3 1 calc PR A 2
C26 C -0.3003(6) 0.7384(9) 0.0710(7) 0.150(2) Uani 0.3 1 d PDU A 2
H26A H -0.2836 0.8445 0.0839 0.225 Uiso 0.3 1 calc PR A 2
H26B H -0.3722 0.7153 0.0792 0.225 Uiso 0.3 1 calc PR A 2
H26C H -0.3125 0.7112 -0.012 0.225 Uiso 0.3 1 calc PR A 2
C31 C 0.18243(16) 0.7091(2) 0.55960(18) 0.0821(8) Uani 0.2 1 d PD A 3
H31A H 0.1608 0.6329 0.6042 0.098 Uiso 0.2 1 calc PR A 3
H31B H 0.2092 0.6575 0.5049 0.098 Uiso 0.2 1 calc PR A 3
C32 C 0.0729(4) 0.7995(6) 0.4806(5) 0.0464(18) Uani 0.2 1 d PDU A 3
H32A H 0.0986 0.8907 0.4545 0.056 Uiso 0.2 1 calc PR A 3
H32B H 0.0346 0.8296 0.5323 0.056 Uiso 0.2 1 calc PR A 3
C33 C -0.0212(4) 0.7209(6) 0.3638(5) 0.067(3) Uani 0.2 1 d PDU A 3
H33A H 0.0183 0.6805 0.3162 0.081 Uiso 0.2 1 calc PR A 3
H33B H -0.0551 0.6369 0.3894 0.081 Uiso 0.2 1 calc PR A 3
C34 C -0.1217(5) 0.8229(7) 0.2806(5) 0.0831(18) Uani 0.2 1 d PDU A 3
H34A H -0.0889 0.903 0.2496 0.1 Uiso 0.2 1 calc PR A 3
H34B H -0.1578 0.8689 0.3295 0.1 Uiso 0.2 1 calc PR A 3
C35 C -0.2184(5) 0.7402(10) 0.1702(4) 0.121(3) Uani 0.2 1 d PDU A 3
H35A H -0.2972 0.7867 0.1445 0.145 Uiso 0.2 1 calc PR A 3
H35B H -0.2227 0.6356 0.1919 0.145 Uiso 0.2 1 calc PR A 3
C36 C -0.1815(6) 0.7507(15) 0.0655(4) 0.1204(12) Uani 0.2 1 d PDU A 3
H36A H -0.166 0.8542 0.0539 0.181 Uiso 0.2 1 calc PR A 3
H36B H -0.2458 0.7124 -0.0114 0.181 Uiso 0.2 1 calc PR A 3
H36C H -0.1093 0.6923 0.0877 0.181 Uiso 0.2 1 calc PR A 3
C41 C 0.18243(16) 0.7091(2) 0.55960(18) 0.0821(8) Uani 0.2 1 d PD A 4
H41A H 0.1519 0.6427 0.6035 0.098 Uiso 0.2 1 calc PR A 4
H41B H 0.2109 0.6472 0.5113 0.098 Uiso 0.2 1 calc PR A 4
C42 C 0.0827(5) 0.8093(7) 0.4725(6) 0.1318(13) Uani 0.2 1 d PDU A 4
H42A H 0.1147 0.8802 0.4331 0.158 Uiso 0.2 1 calc PR A 4
H42B H 0.0509 0.8665 0.5203 0.158 Uiso 0.2 1 calc PR A 4
C43 C -0.0193(6) 0.7186(7) 0.3708(5) 0.1339(13) Uani 0.2 1 d PDU A 4
H43A H 0.0144 0.6275 0.3542 0.161 Uiso 0.2 1 calc PR A 4
H43B H -0.0763 0.6888 0.4018 0.161 Uiso 0.2 1 calc PR A 4
C44 C -0.0857(7) 0.8033(7) 0.2507(5) 0.1376(12) Uani 0.2 1 d PDU A 4
H44A H -0.0277 0.8504 0.2279 0.165 Uiso 0.2 1 calc PR A 4
H44B H -0.1338 0.8824 0.2625 0.165 Uiso 0.2 1 calc PR A 4
C45 C -0.1676(4) 0.7006(9) 0.1459(5) 0.1353(18) Uani 0.2 1 d PDU A 4
H45A H -0.1321 0.6009 0.1563 0.162 Uiso 0.2 1 calc PR A 4
H45B H -0.1813 0.7404 0.0646 0.162 Uiso 0.2 1 calc PR A 4
C46 C -0.2860(4) 0.6940(15) 0.1551(8) 0.138(2) Uani 0.2 1 d PDU A 4
H46A H -0.2688 0.6953 0.2423 0.206 Uiso 0.2 1 calc PR A 4
H46B H -0.3286 0.6029 0.1162 0.206 Uiso 0.2 1 calc PR A 4
H46C H -0.3353 0.7795 0.1126 0.206 Uiso 0.2 1 calc PR A 4


#----------------------------------------------------------------------------#
# 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
N1 C6 1.368(3) . ?
N1 C2 1.372(3) . ?
N1 C11 1.445(2) . ?
C2 O2 1.210(3) . ?
C2 N3 1.362(2) . ?
N3 C4 1.381(3) . ?
N3 H3 0.86 . ?
C4 O4 1.203(2) . ?
C4 C5 1.454(3) . ?
C5 C6 1.307(3) . ?
C5 F5 1.345(3) . ?
C6 H6 0.93 . ?
C11 C12 1.489(4) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.514(5) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.491(5) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 C15 1.501(5) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 C16 1.515(7) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
C22 C23 1.521(7) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 C24 1.484(6) . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C24 C25 1.509(7) . ?
C24 H24A 0.97 . ?
C24 H24B 0.97 . ?
C25 C26 1.511(7) . ?
C25 H25A 0.97 . ?
C25 H25B 0.97 . ?
C26 H26A 0.96 . ?
C26 H26B 0.96 . ?
C26 H26C 0.96 . ?
C32 C33 1.515(6) . ?
C32 H32A 0.97 . ?
C32 H32B 0.97 . ?
C33 C34 1.491(7) . ?
C33 H33A 0.97 . ?
C33 H33B 0.97 . ?
C34 C35 1.504(7) . ?
C34 H34A 0.97 . ?
C34 H34B 0.97 . ?
C35 C36 1.513(8) . ?
C35 H35A 0.97 . ?
C35 H35B 0.97 . ?
C36 H36A 0.96 . ?
C36 H36B 0.96 . ?
C36 H36C 0.96 . ?
C42 C43 1.519(7) . ?
C42 H42A 0.97 . ?
C42 H42B 0.97 . ?
C43 C44 1.486(7) . ?
C43 H43A 0.97 . ?
C43 H43B 0.97 . ?
C44 C45 1.503(7) . ?
C44 H44A 0.97 . ?
C44 H44B 0.97 . ?
C45 C46 1.518(8) . ?
C45 H45A 0.97 . ?
C45 H45B 0.97 . ?
C46 H46A 0.96 . ?
C46 H46B 0.96 . ?
C46 H46C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 119.56(16) . . ?
C6 N1 C11 120.18(17) . . ?
C2 N1 C11 120.19(19) . . ?
O2 C2 N3 121.88(19) . . ?
O2 C2 N1 123.73(18) . . ?
N3 C2 N1 114.4(2) . . ?
C2 N3 C4 130.25(17) . . ?
C2 N3 H3 114.9 . . ?
C4 N3 H3 114.9 . . ?
O4 C4 N3 124.09(19) . . ?
O4 C4 C5 125.3(2) . . ?
N3 C4 C5 110.55(16) . . ?
C6 C5 F5 123.0(2) . . ?
C6 C5 C4 120.6(2) . . ?
F5 C5 C4 116.42(17) . . ?
C5 C6 N1 124.6(2) . . ?
C5 C6 H6 117.7 . . ?
N1 C6 H6 117.7 . . ?
N1 C11 C12 112.4(2) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 112.9(3) . . ?
C11 C12 H12A 109 . . ?
C13 C12 H12A 109 . . ?
C11 C12 H12B 109 . . ?
C13 C12 H12B 109 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 111.6(4) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108 . . ?
C13 C14 C15 112.9(4) . . ?
C13 C14 H14A 109 . . ?
C15 C14 H14A 109 . . ?
C13 C14 H14B 109 . . ?
C15 C14 H14B 109 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 106.9(4) . . ?
C14 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
C14 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.6 . . ?
C23 C22 H22A 109.9 . . ?
C23 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C22 113.7(5) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 109.9(5) . . ?
C23 C24 H24A 109.7 . . ?
C25 C24 H24A 109.7 . . ?
C23 C24 H24B 109.7 . . ?
C25 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
C24 C25 C26 106.3(5) . . ?
C24 C25 H25A 110.5 . . ?
C26 C25 H25A 110.5 . . ?
C24 C25 H25B 110.5 . . ?
C26 C25 H25B 110.5 . . ?
H25A C25 H25B 108.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C33 C32 H32A 108.4 . . ?
C33 C32 H32B 108.4 . . ?
H32A C32 H32B 107.5 . . ?
C34 C33 C32 112.9(5) . . ?
C34 C33 H33A 109 . . ?
C32 C33 H33A 109 . . ?
C34 C33 H33B 109 . . ?
C32 C33 H33B 109 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 C35 112.0(5) . . ?
C33 C34 H34A 109.2 . . ?
C35 C34 H34A 109.2 . . ?
C33 C34 H34B 109.2 . . ?
C35 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C34 C35 C36 105.7(6) . . ?
C34 C35 H35A 110.6 . . ?
C36 C35 H35A 110.6 . . ?
C34 C35 H35B 110.6 . . ?
C36 C35 H35B 110.6 . . ?
H35A C35 H35B 108.7 . . ?
C43 C42 H42A 109.4 . . ?
C43 C42 H42B 109.4 . . ?
H42A C42 H42B 108 . . ?
C44 C43 C42 113.1(5) . . ?
C44 C43 H43A 109 . . ?
C42 C43 H43A 109 . . ?
C44 C43 H43B 109 . . ?
C42 C43 H43B 109 . . ?
H43A C43 H43B 107.8 . . ?
C43 C44 C45 111.1(5) . . ?
C43 C44 H44A 109.4 . . ?
C45 C44 H44A 109.4 . . ?
C43 C44 H44B 109.4 . . ?
C45 C44 H44B 109.4 . . ?
H44A C44 H44B 108 . . ?
C44 C45 C46 105.7(7) . . ?
C44 C45 H45A 110.6 . . ?
C46 C45 H45A 110.6 . . ?
C44 C45 H45B 110.6 . . ?
C46 C45 H45B 110.6 . . ?
H45A C45 H45B 108.7 . . ?

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
C6 N1 C2 O2 177.4(2) . . . . ?
C11 N1 C2 O2 0.5(3) . . . . ?
C6 N1 C2 N3 -1.2(3) . . . . ?
C11 N1 C2 N3 -178.22(17) . . . . ?
O2 C2 N3 C4 -178.8(2) . . . . ?
N1 C2 N3 C4 -0.1(3) . . . . ?
C2 N3 C4 O4 -179.2(2) . . . . ?
C2 N3 C4 C5 -0.6(3) . . . . ?
O4 C4 C5 C6 -178.7(2) . . . . ?
N3 C4 C5 C6 2.8(3) . . . . ?
O4 C4 C5 F5 -1.5(3) . . . . ?
N3 C4 C5 F5 179.98(17) . . . . ?
F5 C5 C6 N1 178.50(19) . . . . ?
C4 C5 C6 N1 -4.5(3) . . . . ?
C2 N1 C6 C5 3.6(3) . . . . ?
C11 N1 C6 C5 -179.4(2) . . . . ?
C6 N1 C11 C12 -91.6(4) . . . . ?
C2 N1 C11 C12 85.4(4) . . . . ?
N1 C11 C12 C13 -176.5(4) . . . . ?
C11 C12 C13 C14 -164.0(5) . . . . ?
C12 C13 C14 C15 160.9(5) . . . . ?
C13 C14 C15 C16 -111.4(6) . . . . ?
C22 C23 C24 C25 163.4(6) . . . . ?
C23 C24 C25 C26 -174.8(6) . . . . ?
C32 C33 C34 C35 -175.9(6) . . . . ?
C33 C34 C35 C36 -90.6(8) . . . . ?
C42 C43 C44 C45 168.4(7) . . . . ?
C43 C44 C45 C46 86.3(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O4 0.86 2 2.852(3) 171.9 3_677


# Attachment '1new.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2009-07-03 at 00:36:33
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : pm128 difabs dreduc struct

data_pm128
_database_code_depnum_ccdc_archive 'CCDC 730817'

_audit_creation_date             2009-07-03T00:36:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C10 H16 N2 O2'
_chemical_formula_sum            'C10 H16 N2 O2'
_chemical_formula_weight         196.25
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.111(4)
_cell_length_b                   13.285(8)
_cell_length_c                   13.332(6)
_cell_angle_alpha                90.66(7)
_cell_angle_beta                 102.36(5)
_cell_angle_gamma                94.35(4)
_cell_volume                     2260.9(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    17
_cell_measurement_theta_min      4.77
_cell_measurement_theta_max      8.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_T_max  0.9952

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.016774
_diffrn_orient_matrix_ub_12      -0.007181
_diffrn_orient_matrix_ub_13      0.076286
_diffrn_orient_matrix_ub_21      -0.071976
_diffrn_orient_matrix_ub_22      -0.032649
_diffrn_orient_matrix_ub_23      -0.003457
_diffrn_orient_matrix_ub_31      0.025895
_diffrn_orient_matrix_ub_32      -0.067765
_diffrn_orient_matrix_ub_33      -0.008891
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        8
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 0 0
-3 0 0

_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.2561
_diffrn_reflns_number            7328
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_reflns_number_total             7328
_reflns_number_gt                1950
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# 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)+(0.1315P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7328
_refine_ls_number_parameters     509
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.3291
_refine_ls_R_factor_gt           0.108
_refine_ls_wR_factor_ref         0.3354
_refine_ls_wR_factor_gt          0.2664
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
# 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
N1 N 0.3496(5) 0.0295(4) 0.6810(5) 0.053(2) Uani 1 1 d . . .
C2 C 0.3514(6) 0.1222(6) 0.7330(6) 0.047(2) Uani 1 1 d . . .
O2 O 0.3409(5) 0.2009(4) 0.6893(4) 0.075(2) Uani 1 1 d . . .
N3 N 0.3667(5) 0.1127(5) 0.8400(5) 0.0490(18) Uani 1 1 d . . .
H3 H 0.3692 0.1687 0.8737 0.059 Uiso 1 1 calc R . .
C4 C 0.3785(7) 0.0287(6) 0.9001(8) 0.057(2) Uani 1 1 d . . .
O4 O 0.3856(5) 0.0347(4) 0.9924(4) 0.072(2) Uani 1 1 d . . .
C5 C 0.3805(7) -0.0621(7) 0.8388(7) 0.072(3) Uani 1 1 d . . .
H5 H 0.3922 -0.1232 0.8709 0.086 Uiso 1 1 calc R . .
C6 C 0.3655(7) -0.0581(6) 0.7363(8) 0.062(3) Uani 1 1 d . . .
H6 H 0.3658 -0.1181 0.6997 0.075 Uiso 1 1 calc R . .
C7 C 0.3183(6) 0.0208(6) 0.5681(5) 0.067(3) Uani 1 1 d D . .
H7A H 0.3437 0.0823 0.5397 0.08 Uiso 1 1 calc R . .
H7B H 0.3525 -0.0344 0.5448 0.08 Uiso 1 1 calc R . .
C8 C 0.2059(6) 0.0037(7) 0.5269(6) 0.073(3) Uani 1 1 d D . .
H8A H 0.1737 0.0648 0.539 0.087 Uiso 1 1 calc R . .
H8B H 0.1785 -0.0491 0.5658 0.087 Uiso 1 1 calc R . .
C9 C 0.1725(7) -0.0243(8) 0.4181(6) 0.085(3) Uani 1 1 d D . .
H9A H 0.2019 -0.0872 0.4067 0.102 Uiso 1 1 calc R . .
H9B H 0.203 0.0268 0.3795 0.102 Uiso 1 1 calc R . .
C10 C 0.0600(7) -0.0370(9) 0.3748(7) 0.101(4) Uani 1 1 d D . .
H10A H 0.0298 -0.0868 0.4149 0.122 Uiso 1 1 calc R . .
H10B H 0.0313 0.0265 0.3854 0.122 Uiso 1 1 calc R . .
C11 C 0.0228(7) -0.0670(11) 0.2667(7) 0.137(5) Uani 1 1 d D . .
H11A H 0.0525 -0.0173 0.226 0.164 Uiso 1 1 calc R . .
H11B H 0.0507 -0.1307 0.2555 0.164 Uiso 1 1 calc R . .
C12 C -0.0897(7) -0.0784(12) 0.2273(9) 0.180(8) Uani 1 1 d D . .
H12A H -0.1194 -0.1347 0.259 0.27 Uiso 1 1 calc R . .
H12B H -0.1042 -0.0902 0.1543 0.27 Uiso 1 1 calc R . .
H12C H -0.1198 -0.018 0.2427 0.27 Uiso 1 1 calc R . .
N21 N 0.3671(5) 0.5319(5) 0.7568(5) 0.0515(19) Uani 1 1 d . . .
C22 C 0.3763(7) 0.6248(7) 0.7094(7) 0.054(2) Uani 1 1 d . . .
O22 O 0.3725(6) 0.7044(4) 0.7523(4) 0.087(2) Uani 1 1 d . . .
N23 N 0.3848(5) 0.6165(5) 0.6090(5) 0.058(2) Uani 1 1 d . . .
H23 H 0.3935 0.6724 0.5789 0.07 Uiso 1 1 calc R . .
C24 C 0.3812(7) 0.5287(6) 0.5498(7) 0.056(2) Uani 1 1 d . . .
O24 O 0.3850(5) 0.5346(4) 0.4596(5) 0.075(2) Uani 1 1 d . . .
C25 C 0.3826(8) 0.4396(6) 0.6097(7) 0.069(3) Uani 1 1 d . . .
H25 H 0.3882 0.3779 0.5786 0.083 Uiso 1 1 calc R . .
C26 C 0.3763(7) 0.4413(6) 0.7059(8) 0.066(3) Uani 1 1 d . . .
H26 H 0.3778 0.3814 0.7413 0.08 Uiso 1 1 calc R . .
C27 C 0.3507(8) 0.5310(6) 0.8608(7) 0.071(3) Uani 1 1 d D . .
H27A H 0.3855 0.5921 0.8971 0.085 Uiso 1 1 calc R . .
H27B H 0.3832 0.474 0.8954 0.085 Uiso 1 1 calc R . .
C28 C 0.2408(9) 0.5246(10) 0.8665(9) 0.137(6) Uani 1 1 d D . .
H28A H 0.2393 0.522 0.9389 0.165 Uiso 1 1 calc R . .
H28B H 0.2144 0.5883 0.8428 0.165 Uiso 1 1 calc R . .
C29 C 0.1643(10) 0.4460(11) 0.8149(12) 0.193(8) Uani 1 1 d D . .
H29A H 0.1878 0.3811 0.8381 0.232 Uiso 1 1 calc R . .
H29B H 0.162 0.4483 0.7417 0.232 Uiso 1 1 calc R . .
C30 C 0.0585(12) 0.4526(16) 0.8311(16) 0.266(13) Uani 1 1 d D . .
H30A H 0.0565 0.4325 0.9004 0.319 Uiso 1 1 calc R . .
H30B H 0.0412 0.5223 0.8248 0.319 Uiso 1 1 calc R . .
C31 C -0.0193(13) 0.3902(18) 0.7594(16) 0.39(2) Uani 1 1 d D . .
H31A H -0.004 0.3201 0.7682 0.472 Uiso 1 1 calc R . .
H31B H -0.0148 0.4079 0.69 0.472 Uiso 1 1 calc R . .
C32 C -0.1254(13) 0.400(2) 0.772(2) 0.48(3) Uani 1 1 d D . .
H32A H -0.1556 0.3361 0.788 0.719 Uiso 1 1 calc R . .
H32B H -0.1667 0.4232 0.7091 0.719 Uiso 1 1 calc R . .
H32C H -0.1242 0.4484 0.8264 0.719 Uiso 1 1 calc R . .
N41 N 0.6137(5) 0.2098(5) 0.8117(5) 0.0492(19) Uani 1 1 d . . .
C42 C 0.6122(7) 0.2990(7) 0.7603(7) 0.055(2) Uani 1 1 d . . .
O42 O 0.6178(5) 0.3816(4) 0.8052(5) 0.084(2) Uani 1 1 d . . .
N43 N 0.6045(5) 0.2887(5) 0.6573(5) 0.056(2) Uani 1 1 d . . .
H43 H 0.603 0.3437 0.6237 0.067 Uiso 1 1 calc R . .
C44 C 0.5987(7) 0.2001(6) 0.6003(7) 0.051(2) Uani 1 1 d . . .
O44 O 0.5914(5) 0.2030(4) 0.5068(5) 0.075(2) Uani 1 1 d . . .
C45 C 0.5984(7) 0.1098(6) 0.6615(7) 0.065(3) Uani 1 1 d . . .
H45 H 0.5926 0.0462 0.63 0.078 Uiso 1 1 calc R . .
C46 C 0.6065(6) 0.1184(6) 0.7618(7) 0.056(3) Uani 1 1 d . . .
H46 H 0.6074 0.06 0.7998 0.067 Uiso 1 1 calc R . .
C47 C 0.6256(7) 0.2102(7) 0.9250(6) 0.066(3) Uani 1 1 d D . .
H47A H 0.5808 0.2583 0.9446 0.08 Uiso 1 1 calc R . .
H47B H 0.6024 0.1438 0.9451 0.08 Uiso 1 1 calc R . .
C48 C 0.7328(8) 0.2362(8) 0.9800(8) 0.099(4) Uani 1 1 d D . .
H48A H 0.755 0.3022 0.9583 0.119 Uiso 1 1 calc R . .
H48B H 0.7327 0.2425 1.0525 0.119 Uiso 1 1 calc R . .
C49 C 0.8112(8) 0.1678(9) 0.9688(9) 0.128(5) Uani 1 1 d D . .
H49A H 0.8198 0.1674 0.8984 0.154 Uiso 1 1 calc R . .
H49B H 0.7878 0.0998 0.9842 0.154 Uiso 1 1 calc R . .
C50 C 0.9114(10) 0.1984(14) 1.0376(12) 0.217(9) Uani 1 1 d D . .
H50A H 0.9222 0.2714 1.0366 0.261 Uiso 1 1 calc R . .
H50B H 0.9057 0.1811 1.1068 0.261 Uiso 1 1 calc R . .
C51 C 1.0036(10) 0.1573(19) 1.0183(14) 0.324(16) Uani 1 1 d D . .
H51A H 1.0049 0.1701 0.947 0.388 Uiso 1 1 calc R . .
H51B H 0.9933 0.0847 1.0236 0.388 Uiso 1 1 calc R . .
C52 C 1.1078(10) 0.1878(17) 1.0778(15) 0.330(16) Uani 1 1 d D . .
H52A H 1.1259 0.2572 1.0655 0.495 Uiso 1 1 calc R . .
H52B H 1.1574 0.1463 1.0578 0.495 Uiso 1 1 calc R . .
H52C H 1.1091 0.1799 1.1496 0.495 Uiso 1 1 calc R . .
N61 N 0.3557(6) 0.2878(5) 0.2616(5) 0.066(2) Uani 1 1 d . . .
C62 C 0.3647(7) 0.1977(6) 0.2113(7) 0.062(3) Uani 1 1 d . . .
O62 O 0.3598(6) 0.1156(4) 0.2508(5) 0.087(2) Uani 1 1 d . . .
N63 N 0.3753(5) 0.2098(5) 0.1120(5) 0.060(2) Uani 1 1 d . . .
H63 H 0.3798 0.1554 0.0782 0.072 Uiso 1 1 calc R . .
C64 C 0.3796(7) 0.2973(7) 0.0598(7) 0.060(3) Uani 1 1 d . . .
O64 O 0.3878(5) 0.2954(4) -0.0313(5) 0.081(2) Uani 1 1 d . . .
C65 C 0.3742(7) 0.3864(6) 0.1209(7) 0.062(3) Uani 1 1 d . . .
H65 H 0.3783 0.4499 0.0926 0.075 Uiso 1 1 calc R . .
C66 C 0.3634(7) 0.3780(7) 0.2162(7) 0.068(3) Uani 1 1 d . . .
H66 H 0.361 0.4366 0.2543 0.081 Uiso 1 1 calc R . .
C67 C 0.3409(8) 0.2834(7) 0.3670(7) 0.085(3) Uani 1 1 d D . .
H67A H 0.3822 0.2314 0.4017 0.102 Uiso 1 1 calc R . .
H67B H 0.3683 0.3473 0.4019 0.102 Uiso 1 1 calc R . .
C68 C 0.2338(10) 0.2629(10) 0.3776(11) 0.180(9) Uani 1 1 d D . .
H68A H 0.2004 0.2238 0.3159 0.216 Uiso 1 1 calc R . .
H68B H 0.2389 0.2157 0.4331 0.216 Uiso 1 1 calc R . .
C69 C 0.1554(11) 0.3270(12) 0.3943(19) 0.316(18) Uani 1 1 d D . .
H69A H 0.1588 0.3827 0.3485 0.379 Uiso 1 1 calc R . .
H69B H 0.1806 0.3553 0.4634 0.379 Uiso 1 1 calc R . .
C70 C 0.0446(14) 0.299(2) 0.3856(18) 0.265(13) Uani 1 1 d D . .
H70A H 0.0068 0.3268 0.3227 0.318 Uiso 1 1 calc R . .
H70B H 0.0336 0.2261 0.3779 0.318 Uiso 1 1 calc R . .
C71 C -0.0026(13) 0.330(2) 0.4681(17) 0.37(2) Uani 1 1 d D . .
H71A H 0.017 0.4009 0.485 0.447 Uiso 1 1 calc R . .
H71B H 0.0231 0.2918 0.5286 0.447 Uiso 1 1 calc R . .
C72 C -0.1158(13) 0.3131(18) 0.439(2) 0.339(18) Uani 1 1 d D . .
H72A H -0.1346 0.2562 0.3917 0.508 Uiso 1 1 calc R . .
H72B H -0.1443 0.3721 0.4065 0.508 Uiso 1 1 calc R . .
H72C H -0.1434 0.3 0.4989 0.508 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
N1 C6 1.391(10) . ?
N1 C2 1.401(9) . ?
N1 C7 1.474(9) . ?
C2 O2 1.206(8) . ?
C2 N3 1.405(9) . ?
N3 C4 1.380(9) . ?
C4 O4 1.216(9) . ?
C4 C5 1.454(11) . ?
C5 C6 1.340(11) . ?
C7 C8 1.458(11) . ?
C8 C9 1.458(11) . ?
C9 C10 1.460(13) . ?
C10 C11 1.460(13) . ?
C11 C12 1.452(14) . ?
N21 C26 1.399(10) . ?
N21 C22 1.402(10) . ?
N21 C27 1.448(9) . ?
C22 O22 1.206(9) . ?
C22 N23 1.370(9) . ?
N23 C24 1.393(9) . ?
C24 O24 1.218(9) . ?
C24 C25 1.435(11) . ?
C25 C26 1.302(10) . ?
C27 C28 1.455(16) . ?
C28 C29 1.449(19) . ?
C29 C30 1.46(2) . ?
C30 C31 1.44(3) . ?
C31 C32 1.45(3) . ?
N41 C46 1.366(9) . ?
N41 C42 1.375(9) . ?
N41 C47 1.484(9) . ?
C42 O42 1.234(9) . ?
C42 N43 1.360(10) . ?
N43 C44 1.383(9) . ?
C44 O44 1.231(9) . ?
C44 C45 1.459(11) . ?
C45 C46 1.321(10) . ?
C47 C48 1.453(14) . ?
C48 C49 1.452(16) . ?
C49 C50 1.458(19) . ?
C50 C51 1.43(2) . ?
C51 C52 1.45(2) . ?
N61 C66 1.356(11) . ?
N61 C62 1.390(9) . ?
N61 C67 1.460(10) . ?
C62 O62 1.220(9) . ?
C62 N63 1.371(10) . ?
N63 C64 1.365(10) . ?
C64 O64 1.241(9) . ?
C64 C65 1.443(11) . ?
C65 C66 1.314(11) . ?
C67 C68 1.447(17) . ?
C68 C69 1.43(2) . ?
C69 C70 1.45(3) . ?
C70 C71 1.44(3) . ?
C71 C72 1.45(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 119.9(7) . . ?
C6 N1 C7 118.6(7) . . ?
C2 N1 C7 121.1(7) . . ?
O2 C2 N1 122.7(8) . . ?
O2 C2 N3 124.4(8) . . ?
N1 C2 N3 112.8(7) . . ?
C4 N3 C2 130.9(7) . . ?
O4 C4 N3 121.5(8) . . ?
O4 C4 C5 127.0(8) . . ?
N3 C4 C5 111.5(9) . . ?
C6 C5 C4 120.4(9) . . ?
C5 C6 N1 124.4(9) . . ?
C8 C7 N1 115.1(6) . . ?
C7 C8 C9 116.9(7) . . ?
C8 C9 C10 117.5(7) . . ?
C11 C10 C9 119.5(8) . . ?
C12 C11 C10 117.3(8) . . ?
C26 N21 C22 120.9(8) . . ?
C26 N21 C27 120.2(7) . . ?
C22 N21 C27 118.9(7) . . ?
O22 C22 N23 123.3(9) . . ?
O22 C22 N21 122.6(8) . . ?
N23 C22 N21 114.0(8) . . ?
C22 N23 C24 128.0(8) . . ?
O24 C24 N23 119.8(8) . . ?
O24 C24 C25 127.8(8) . . ?
N23 C24 C25 112.2(8) . . ?
C26 C25 C24 122.9(9) . . ?
C25 C26 N21 121.1(9) . . ?
N21 C27 C28 113.7(8) . . ?
C29 C28 C27 123.5(10) . . ?
C28 C29 C30 115.0(12) . . ?
C31 C30 C29 113.0(13) . . ?
C30 C31 C32 113.3(17) . . ?
C46 N41 C42 121.9(8) . . ?
C46 N41 C47 117.5(7) . . ?
C42 N41 C47 120.5(8) . . ?
O42 C42 N43 123.2(8) . . ?
O42 C42 N41 121.9(9) . . ?
N43 C42 N41 114.9(8) . . ?
C42 N43 C44 127.5(7) . . ?
O44 C44 N43 119.9(8) . . ?
O44 C44 C45 126.8(8) . . ?
N43 C44 C45 113.3(8) . . ?
C46 C45 C44 120.0(9) . . ?
C45 C46 N41 122.4(9) . . ?
C48 C47 N41 112.9(8) . . ?
C49 C48 C47 117.8(9) . . ?
C48 C49 C50 110.9(10) . . ?
C51 C50 C49 118.3(11) . . ?
C50 C51 C52 122.6(14) . . ?
C66 N61 C62 121.6(8) . . ?
C66 N61 C67 120.2(8) . . ?
C62 N61 C67 118.1(8) . . ?
O62 C62 N63 123.5(8) . . ?
O62 C62 N61 123.0(9) . . ?
N63 C62 N61 113.5(8) . . ?
C64 N63 C62 128.3(8) . . ?
O64 C64 N63 120.4(8) . . ?
O64 C64 C65 126.1(9) . . ?
N63 C64 C65 113.4(8) . . ?
C66 C65 C64 120.2(9) . . ?
C65 C66 N61 122.9(9) . . ?
C68 C67 N61 115.5(9) . . ?
C69 C68 C67 132.8(12) . . ?
C68 C69 C70 127.4(16) . . ?
C71 C70 C69 117.9(17) . . ?
C70 C71 C72 110.6(17) . . ?

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
C6 N1 C2 O2 178.0(8) . . . . ?
C7 N1 C2 O2 -9.7(12) . . . . ?
C6 N1 C2 N3 -1.9(10) . . . . ?
C7 N1 C2 N3 170.4(7) . . . . ?
O2 C2 N3 C4 179.1(9) . . . . ?
N1 C2 N3 C4 -1.0(12) . . . . ?
C2 N3 C4 O4 -176.0(9) . . . . ?
C2 N3 C4 C5 3.8(12) . . . . ?
O4 C4 C5 C6 176.0(10) . . . . ?
N3 C4 C5 C6 -3.8(12) . . . . ?
C4 C5 C6 N1 1.4(14) . . . . ?
C2 N1 C6 C5 1.7(13) . . . . ?
C7 N1 C6 C5 -170.8(9) . . . . ?
C6 N1 C7 C8 86.8(10) . . . . ?
C2 N1 C7 C8 -85.6(9) . . . . ?
N1 C7 C8 C9 -168.7(8) . . . . ?
C7 C8 C9 C10 -177.1(9) . . . . ?
C8 C9 C10 C11 -178.8(11) . . . . ?
C9 C10 C11 C12 -179.9(12) . . . . ?
C26 N21 C22 O22 -177.4(8) . . . . ?
C27 N21 C22 O22 1.0(13) . . . . ?
C26 N21 C22 N23 5.6(11) . . . . ?
C27 N21 C22 N23 -176.0(7) . . . . ?
O22 C22 N23 C24 -174.2(9) . . . . ?
N21 C22 N23 C24 2.8(12) . . . . ?
C22 N23 C24 O24 176.4(9) . . . . ?
C22 N23 C24 C25 -8.8(12) . . . . ?
O24 C24 C25 C26 -178.7(10) . . . . ?
N23 C24 C25 C26 7.1(14) . . . . ?
C24 C25 C26 N21 0.3(15) . . . . ?
C22 N21 C26 C25 -7.2(13) . . . . ?
C27 N21 C26 C25 174.4(9) . . . . ?
C26 N21 C27 C28 -91.8(10) . . . . ?
C22 N21 C27 C28 89.8(10) . . . . ?
N21 C27 C28 C29 54.5(16) . . . . ?
C27 C28 C29 C30 179.5(15) . . . . ?
C28 C29 C30 C31 165(2) . . . . ?
C29 C30 C31 C32 -177.0(19) . . . . ?
C46 N41 C42 O42 179.3(8) . . . . ?
C47 N41 C42 O42 -2.0(13) . . . . ?
C46 N41 C42 N43 -0.8(11) . . . . ?
C47 N41 C42 N43 177.9(7) . . . . ?
O42 C42 N43 C44 179.4(8) . . . . ?
N41 C42 N43 C44 -0.4(12) . . . . ?
C42 N43 C44 O44 179.7(9) . . . . ?
C42 N43 C44 C45 1.8(12) . . . . ?
O44 C44 C45 C46 -179.7(9) . . . . ?
N43 C44 C45 C46 -2.0(12) . . . . ?
C44 C45 C46 N41 1.1(13) . . . . ?
C42 N41 C46 C45 0.4(12) . . . . ?
C47 N41 C46 C45 -178.3(8) . . . . ?
C46 N41 C47 C48 101.5(9) . . . . ?
C42 N41 C47 C48 -77.2(10) . . . . ?
N41 C47 C48 C49 -64.3(13) . . . . ?
C47 C48 C49 C50 -173.5(12) . . . . ?
C48 C49 C50 C51 -163(2) . . . . ?
C49 C50 C51 C52 176(2) . . . . ?
C66 N61 C62 O62 178.8(10) . . . . ?
C67 N61 C62 O62 0.8(13) . . . . ?
C66 N61 C62 N63 -3.8(12) . . . . ?
C67 N61 C62 N63 178.2(8) . . . . ?
O62 C62 N63 C64 178.6(9) . . . . ?
N61 C62 N63 C64 1.2(13) . . . . ?
C62 N63 C64 O64 -178.8(9) . . . . ?
C62 N63 C64 C65 1.4(13) . . . . ?
O64 C64 C65 C66 178.6(10) . . . . ?
N63 C64 C65 C66 -1.7(13) . . . . ?
C64 C65 C66 N61 -0.8(15) . . . . ?
C62 N61 C66 C65 3.7(15) . . . . ?
C67 N61 C66 C65 -178.3(9) . . . . ?
C66 N61 C67 C68 97.1(11) . . . . ?
C62 N61 C67 C68 -84.9(11) . . . . ?
N61 C67 C68 C69 -97(2) . . . . ?
C67 C68 C69 C70 168(2) . . . . ?
C68 C69 C70 C71 132(3) . . . . ?
C69 C70 C71 C72 169(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
N3 H3 O64 0.86 2.06 2.918(9) 173 1_556
N23 H23 O44 0.86 2.04 2.900(9) 174.1 2_666
N43 H43 O24 0.86 1.99 2.843(9) 172.9 2_666
N63 H63 O4 0.86 1.97 2.833(9) 176.2 1_554

