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

#######################################################################
#
#                 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_teste4

_audit_creation_date             2011-01-25T12:15:26-00:00
_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        
;
 1-(dimethylethyl)-5-(4-iodinephenyl)-3-(trifluoromethyl)-1H-pyrazole
;
_chemical_name_common            'iodinephenyl trifluoromethyl pyrazole'
_chemical_formula_moiety         'C14 H14 F3 I N2'
_chemical_formula_sum            'C14 H14 F3 I N2'
_chemical_formula_weight         394.17
_chemical_melting_point          413K

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma
_symmetry_space_group_name_Hall  '-P 2ac 2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   9.3152(7)
_cell_length_b                   9.5241(7)
_cell_length_c                   17.5001(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1552.59(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4034
_cell_measurement_theta_min      2.4345
_cell_measurement_theta_max      26.118

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.632
_exptl_crystal_size_mid          0.442
_exptl_crystal_size_min          0.385
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

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

_exptl_absorpt_coefficient_mu    2.085
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.5117
_exptl_absorpt_correction_T_max  0.6895

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.012
_diffrn_reflns_number            12700
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             1875
_reflns_number_gt                1444
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.0527P)²+1.6649P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0056(7)
_refine_ls_number_reflns         1875
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
I I 1.51380(5) 0.25 0.27129(3) 0.1033(3) Uani 1 2 d S . .
N1 N 0.9766(3) 0.25 0.5768(2) 0.0441(8) Uani 1 2 d S . .
N2 N 0.8395(4) 0.25 0.6010(2) 0.0477(8) Uani 1 2 d S . .
C3 C 0.7629(4) 0.25 0.5372(2) 0.0479(9) Uani 1 2 d S . .
C11 C 1.0943(5) 0.25 0.6353(3) 0.0578(8) Uani 1 2 d S . .
C5 C 0.9848(4) 0.25 0.4981(2) 0.0433(9) Uani 1 2 d S . .
C51 C 1.1160(4) 0.25 0.4504(2) 0.0443(9) Uani 1 2 d S . .
C4 C 0.8461(5) 0.25 0.4728(2) 0.0490(10) Uani 1 2 d S . .
H4 H 0.8148 0.25 0.4223 0.059 Uiso 1 2 calc SR . .
C53 C 1.2851(4) 0.3750(4) 0.37225(18) 0.0628(9) Uani 1 1 d . . .
H53 H 1.323 0.4592 0.3545 0.075 Uiso 1 1 calc R . .
C52 C 1.1721(4) 0.3752(4) 0.42343(18) 0.0547(7) Uani 1 1 d . . .
H52 H 1.1336 0.4601 0.4399 0.066 Uiso 1 1 calc R . .
F1 F 0.5473(3) 0.1458(4) 0.5044(3) 0.1519(18) Uani 1 1 d . . .
C31 C 0.6028(5) 0.25 0.5419(3) 0.0578(8) Uani 1 2 d S . .
F2 F 0.5533(4) 0.25 0.6071(3) 0.207(4) Uani 1 2 d S . .
C54 C 1.3406(5) 0.25 0.3480(2) 0.0580(12) Uani 1 2 d S . .
C12 C 1.0293(7) 0.25 0.7135(3) 0.133(5) Uani 1 2 d S . .
H12A H 0.9711 0.1676 0.7198 0.199 Uiso 0.5 1 calc PR . .
H12B H 0.9708 0.3322 0.7198 0.199 Uiso 0.5 1 calc PR . .
H12C H 1.1042 0.2502 0.7512 0.199 Uiso 1 2 calc SR . .
C13 C 1.1865(5) 0.3791(6) 0.6242(3) 0.0968(15) Uani 1 1 d . . .
H13A H 1.2278 0.3777 0.574 0.145 Uiso 1 1 calc R . .
H13B H 1.2617 0.3799 0.6617 0.145 Uiso 1 1 calc R . .
H13C H 1.1284 0.4617 0.6299 0.145 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.0847(4) 0.1564(6) 0.0689(3) 0 0.0369(2) 0
N1 0.0366(16) 0.056(2) 0.0397(17) 0 -0.0018(13) 0
N2 0.0368(16) 0.058(2) 0.0485(18) 0 -0.0020(14) 0
C3 0.040(2) 0.052(2) 0.052(2) 0 -0.0024(17) 0
C11 0.0427(16) 0.078(2) 0.0531(17) 0 -0.0088(13) 0
C5 0.045(2) 0.047(2) 0.0381(18) 0 -0.0033(15) 0
C51 0.044(2) 0.052(2) 0.0371(18) 0 -0.0023(15) 0
C4 0.049(2) 0.055(3) 0.043(2) 0 -0.0074(17) 0
C53 0.068(2) 0.069(2) 0.0522(17) 0.0054(16) 0.0103(15) -0.0135(18)
C52 0.0606(18) 0.0487(17) 0.0547(17) -0.0006(14) 0.0077(14) -0.0017(15)
F1 0.0570(15) 0.140(3) 0.259(5) -0.068(3) -0.018(2) -0.0241(18)
C31 0.0427(16) 0.078(2) 0.0531(17) 0 -0.0088(13) 0
F2 0.0413(18) 0.502(14) 0.079(3) 0 0.0096(19) 0
C54 0.050(2) 0.083(4) 0.040(2) 0 0.0044(18) 0
C12 0.073(4) 0.285(15) 0.040(3) 0 -0.008(3) 0
C13 0.091(3) 0.108(4) 0.092(3) 0.006(3) -0.041(3) -0.029(3)


#----------------------------------------------------------------------------#
#                   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
I C54 2.098(4) . ?
N1 N2 1.346(5) . ?
N1 C5 1.380(5) . ?
N1 C11 1.499(5) . ?
N2 C3 1.325(5) . ?
C3 C4 1.368(6) . ?
C3 C31 1.493(6) . ?
C11 C12 1.498(8) . ?
C11 C13 1.512(5) 8_565 ?
C11 C13 1.512(5) . ?
C5 C4 1.366(6) . ?
C5 C51 1.479(6) . ?
C51 C52 1.385(4) 8_565 ?
C51 C52 1.385(4) . ?
C4 H4 0.93 . ?
C53 C54 1.365(4) . ?
C53 C52 1.382(4) . ?
C53 H53 0.93 . ?
C52 H52 0.93 . ?
F1 C31 1.297(4) . ?
C31 F2 1.232(6) . ?
C31 F1 1.297(4) 8_565 ?
C54 C53 1.365(4) 8_565 ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 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
N2 N1 C5 111.5(3) . . ?
N2 N1 C11 118.7(3) . . ?
C5 N1 C11 129.8(3) . . ?
C3 N2 N1 104.3(3) . . ?
N2 C3 C4 112.9(4) . . ?
N2 C3 C31 119.4(4) . . ?
C4 C3 C31 127.7(4) . . ?
C12 C11 N1 109.1(4) . . ?
C12 C11 C13 110.3(3) . 8_565 ?
N1 C11 C13 109.1(3) . 8_565 ?
C12 C11 C13 110.3(3) . . ?
N1 C11 C13 109.1(3) . . ?
C13 C11 C13 108.8(5) 8_565 . ?
C4 C5 N1 105.8(4) . . ?
C4 C5 C51 126.7(4) . . ?
N1 C5 C51 127.5(3) . . ?
C52 C51 C52 118.9(4) 8_565 . ?
C52 C51 C5 120.3(2) 8_565 . ?
C52 C51 C5 120.3(2) . . ?
C5 C4 C3 105.6(4) . . ?
C5 C4 H4 127.2 . . ?
C3 C4 H4 127.2 . . ?
C54 C53 C52 119.4(3) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
C53 C52 C51 120.5(3) . . ?
C53 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
F2 C31 F1 108.6(4) . . ?
F2 C31 F1 108.6(4) . 8_565 ?
F1 C31 F1 99.9(5) . 8_565 ?
F2 C31 C3 115.1(4) . . ?
F1 C31 C3 111.7(3) . . ?
F1 C31 C3 111.7(3) 8_565 . ?
C53 C54 C53 121.3(4) . 8_565 ?
C53 C54 I 119.3(2) . . ?
C53 C54 I 119.3(2) 8_565 . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C5 N1 N2 C3 0.0000(10) . . . . ?
C11 N1 N2 C3 180 . . . . ?
N1 N2 C3 C4 0.0000(10) . . . . ?
N1 N2 C3 C31 180.0000(10) . . . . ?
N2 N1 C11 C12 0.000(2) . . . . ?
C5 N1 C11 C12 180.000(2) . . . . ?
N2 N1 C11 C13 120.6(3) . . . 8_565 ?
C5 N1 C11 C13 -59.4(3) . . . 8_565 ?
N2 N1 C11 C13 -120.6(3) . . . . ?
C5 N1 C11 C13 59.4(3) . . . . ?
N2 N1 C5 C4 0.0000(10) . . . . ?
C11 N1 C5 C4 180.0000(10) . . . . ?
N2 N1 C5 C51 180 . . . . ?
C11 N1 C5 C51 0.0000(10) . . . . ?
C4 C5 C51 C52 -85.5(3) . . . 8_565 ?
N1 C5 C51 C52 94.5(3) . . . 8_565 ?
C4 C5 C51 C52 85.5(3) . . . . ?
N1 C5 C51 C52 -94.5(3) . . . . ?
N1 C5 C4 C3 0.0000(10) . . . . ?
C51 C5 C4 C3 180 . . . . ?
N2 C3 C4 C5 0.0000(10) . . . . ?
C31 C3 C4 C5 180.0000(10) . . . . ?
C54 C53 C52 C51 0.4(5) . . . . ?
C52 C51 C52 C53 -1.9(6) 8_565 . . . ?
C5 C51 C52 C53 -173.0(3) . . . . ?
N2 C3 C31 F2 0.0000(10) . . . . ?
C4 C3 C31 F2 180.0000(10) . . . . ?
N2 C3 C31 F1 -124.5(4) . . . . ?
C4 C3 C31 F1 55.5(4) . . . . ?
N2 C3 C31 F1 124.5(4) . . . 8_565 ?
C4 C3 C31 F1 -55.5(4) . . . 8_565 ?
C52 C53 C54 C53 1.1(7) . . . 8_565 ?
C52 C53 C54 I -179.2(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 993665'
#######################################################################
#
#                 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_pca21

_audit_creation_date             2008-11-28T16:13:48-00:00
_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        
;
 2-methyl-7-trichloromethylpyrazolo [1,5-a] pyrimidine
;
_chemical_name_common            'methyl trichloromethylpyrazolo pyrimidine'
_chemical_formula_moiety         'C8 H6 Cl3 N3'
_chemical_formula_sum            'C8 H6 Cl3 N3'
_chemical_formula_weight         250.51
_chemical_melting_point          94-96C
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca21
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.307(2)
_cell_length_b                   9.4510(14)
_cell_length_c                   6.9446(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1004.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    350
_cell_measurement_theta_min      2.5325
_cell_measurement_theta_max      21.4725

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

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

_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
 XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;
_exptl_absorpt_correction_T_min  0.7502
_exptl_absorpt_correction_T_max  0.8951

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        mone
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_number            9557
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2091
_reflns_number_gt                1457
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.0636P)²+0.4908P] 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_number_reflns         2091
_refine_ls_number_parameters     127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.135
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.004
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(3)
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.44781(5) 0.56131(9) 0.1776(7) 0.0723(4) Uani 1 1 d . . .
Cl2 Cl 0.48086(16) 0.8192(2) 0.37694(15) 0.0715(8) Uani 1 1 d . . .
Cl3 Cl 0.48185(17) 0.8126(3) -0.03856(19) 0.0709(8) Uani 1 1 d . . .
C8 C 0.51012(18) 0.7185(3) 0.171(2) 0.0495(8) Uani 1 1 d . . .
C2 C 0.7217(2) 1.0025(3) 0.1660(18) 0.0453(8) Uani 1 1 d . . .
C7 C 0.6069(2) 0.6873(3) 0.179(2) 0.0526(11) Uani 1 1 d . . .
C6 C 0.6424(3) 0.5573(4) 0.195(3) 0.088(3) Uani 1 1 d . . .
H6 H 0.6066 0.4783 0.2075 0.106 Uiso 1 1 calc R . .
C1 C 0.7238(3) 1.1595(4) 0.161(3) 0.0653(14) Uani 1 1 d . . .
H1A H 0.6651 1.1953 0.1569 0.098 Uiso 1 1 calc R . .
H1B H 0.7549 1.1904 0.0485 0.098 Uiso 1 1 calc R . .
H1C H 0.7526 1.1944 0.2742 0.098 Uiso 1 1 calc R . .
C4 C 0.75522(19) 0.7764(4) 0.171(3) 0.0590(10) Uani 1 1 d . . .
C3 C 0.7915(2) 0.9091(4) 0.1700(18) 0.0515(8) Uani 1 1 d . . .
H3 H 0.8507 0.9317 0.1714 0.062 Uiso 1 1 calc R . .
C5 C 0.7329(3) 0.5413(5) 0.194(4) 0.130(5) Uani 1 1 d . . .
H5 H 0.755 0.45 0.2053 0.156 Uiso 1 1 calc R . .
N2 N 0.66413(15) 0.7981(3) 0.1693(19) 0.0474(7) Uani 1 1 d . . .
N1 N 0.64379(16) 0.9372(2) 0.1668(15) 0.0436(6) Uani 1 1 d . . .
N3 N 0.7896(2) 0.6460(4) 0.179(3) 0.1032(19) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0366(4) 0.0506(5) 0.1297(11) 0.0023(19) 0.0024(19) -0.0138(3)
Cl2 0.0453(15) 0.0797(16) 0.090(2) -0.0183(13) 0.0142(13) -0.0091(11)
Cl3 0.0456(16) 0.0804(16) 0.0867(18) 0.0160(13) -0.0166(13) -0.0113(11)
C8 0.0277(14) 0.0445(16) 0.076(2) -0.002(6) -0.001(6) -0.0026(12)
C2 0.0404(15) 0.0442(16) 0.051(2) -0.006(5) 0.000(5) -0.0093(13)
C7 0.0285(14) 0.0414(16) 0.088(3) -0.007(5) -0.003(6) -0.0028(12)
C6 0.0367(18) 0.0417(18) 0.186(10) -0.002(6) -0.002(6) -0.0010(15)
C1 0.0513(19) 0.053(2) 0.092(4) 0.003(6) 0.009(6) -0.0137(16)
C4 0.0252(14) 0.0537(19) 0.098(3) -0.001(7) 0.004(7) 0.0002(13)
C3 0.0301(14) 0.061(2) 0.064(2) 0.003(7) 0.003(6) -0.0096(13)
C5 0.043(2) 0.042(2) 0.306(15) -0.002(10) -0.021(11) 0.0095(18)
N2 0.0273(12) 0.0399(13) 0.075(2) -0.002(4) -0.005(5) -0.0026(10)
N1 0.0344(12) 0.0385(12) 0.0580(18) 0.001(4) 0.001(4) -0.0039(10)
N3 0.0329(15) 0.0518(19) 0.225(6) -0.011(10) -0.006(8) 0.0066(14)


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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.766(3) . ?
Cl2 C8 1.775(12) . ?
Cl3 C8 1.760(13) . ?
C8 C7 1.511(4) . ?
C2 N1 1.343(4) . ?
C2 C3 1.386(5) . ?
C2 C1 1.485(5) . ?
C7 C6 1.349(6) . ?
C7 N2 1.367(4) . ?
C6 C5 1.393(6) . ?
C6 H6 0.93 . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C4 N3 1.341(5) . ?
C4 C3 1.372(5) . ?
C4 N2 1.409(4) . ?
C3 H3 0.93 . ?
C5 N3 1.321(7) . ?
C5 H5 0.93 . ?
N2 N1 1.351(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
C7 C8 Cl3 111.6(9) . . ?
C7 C8 Cl1 111.4(2) . . ?
Cl3 C8 Cl1 108.3(6) . . ?
C7 C8 Cl2 108.9(9) . . ?
Cl3 C8 Cl2 109.46(18) . . ?
Cl1 C8 Cl2 107.1(6) . . ?
N1 C2 C3 113.1(3) . . ?
N1 C2 C1 118.5(3) . . ?
C3 C2 C1 128.3(3) . . ?
C6 C7 N2 116.4(3) . . ?
C6 C7 C8 125.2(3) . . ?
N2 C7 C8 118.5(3) . . ?
C7 C6 C5 119.9(4) . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C4 C3 132.9(3) . . ?
N3 C4 N2 121.5(3) . . ?
C3 C4 N2 105.5(3) . . ?
C4 C3 C2 105.6(3) . . ?
C4 C3 H3 127.2 . . ?
C2 C3 H3 127.2 . . ?
N3 C5 C6 125.0(5) . . ?
N3 C5 H5 117.5 . . ?
C6 C5 H5 117.5 . . ?
N1 N2 C7 126.8(2) . . ?
N1 N2 C4 111.7(2) . . ?
C7 N2 C4 121.4(3) . . ?
C2 N1 N2 104.0(2) . . ?
C5 N3 C4 115.7(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
Cl3 C8 C7 C6 -123.5(17) . . . . ?
Cl1 C8 C7 C6 -2(2) . . . . ?
Cl2 C8 C7 C6 115.6(17) . . . . ?
Cl3 C8 C7 N2 57.1(17) . . . . ?
Cl1 C8 C7 N2 178.2(12) . . . . ?
Cl2 C8 C7 N2 -63.9(17) . . . . ?
N2 C7 C6 C5 -3(3) . . . . ?
C8 C7 C6 C5 178(2) . . . . ?
N3 C4 C3 C2 -178(2) . . . . ?
N2 C4 C3 C2 -0.4(15) . . . . ?
N1 C2 C3 C4 0.7(13) . . . . ?
C1 C2 C3 C4 -179.3(18) . . . . ?
C7 C6 C5 N3 0(4) . . . . ?
C6 C7 N2 N1 -174.7(14) . . . . ?
C8 C7 N2 N1 5(2) . . . . ?
C6 C7 N2 C4 2(3) . . . . ?
C8 C7 N2 C4 -178.6(15) . . . . ?
N3 C4 N2 N1 178.2(17) . . . . ?
C3 C4 N2 N1 0.0(18) . . . . ?
N3 C4 N2 C7 1(3) . . . . ?
C3 C4 N2 C7 -177.1(14) . . . . ?
C3 C2 N1 N2 -0.7(14) . . . . ?
C1 C2 N1 N2 179.3(12) . . . . ?
C7 N2 N1 C2 177.2(15) . . . . ?
C4 N2 N1 C2 0.4(17) . . . . ?
C6 C5 N3 C4 3(4) . . . . ?
C3 C4 N3 C5 174(2) . . . . ?
N2 C4 N3 C5 -3(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 734995'
#######################################################################
#
#                 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_teste1

_audit_creation_date             2012-09-18T09:36:02-00:00
_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        
;
        4-iodo-5-methylisoxazol-3-amine
;
_chemical_name_common            4-iodo-5-methylisoxazol-3-amine
_chemical_formula_moiety         'C4 H5 I N2 O'
_chemical_formula_sum            'C4 H5 I N2 O'
_chemical_formula_weight         224
_chemical_melting_point          none

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5261(3)
_cell_length_b                   7.3488(3)
_cell_length_c                   7.6401(3)
_cell_angle_alpha                96.998(3)
_cell_angle_beta                 100.396(3)
_cell_angle_gamma                113.411(3)
_cell_volume                     323.04(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3700
_cell_measurement_theta_min      3.0925
_cell_measurement_theta_max      25.102

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    2.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             208
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

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

_exptl_absorpt_coefficient_mu    4.861
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.4011
_exptl_absorpt_correction_T_max  0.5292

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_number            9332
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_full        27.13
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             1432
_reflns_number_gt                1291
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.0298P)²+0.0242P] 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_extinction_coef       none
_refine_ls_number_reflns         1432
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0511
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.101

#----------------------------------------------------------------------------#
#                   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'
I I -0.4742 1.8119 '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
I1 I 0.51287(3) 0.35436(3) 0.71091(3) 0.05163(10) Uani 1 1 d . . .
O1 O 0.4707(4) -0.2151(3) 0.7884(3) 0.0506(5) Uani 1 1 d . . .
C4 C 0.5460(5) 0.0978(4) 0.7596(3) 0.0369(6) Uani 1 1 d . . .
N2 N 0.7118(4) -0.0973(4) 0.8687(4) 0.0514(7) Uani 1 1 d . . .
N31 N 0.9620(4) 0.2467(5) 0.9148(4) 0.0624(8) Uani 1 1 d . . .
H31A H 1.0763 0.2277 0.9705 0.075 Uiso 1 1 calc R . .
H31B H 0.9817 0.3663 0.9003 0.075 Uiso 1 1 calc R . .
C5 C 0.3812(5) -0.0919(5) 0.7251(4) 0.0400(6) Uani 1 1 d . . .
C3 C 0.7512(5) 0.0886(5) 0.8501(4) 0.0416(6) Uani 1 1 d . . .
C51 C 0.1307(5) -0.1869(5) 0.6347(5) 0.0555(8) Uani 1 1 d . . .
H51A H 0.0684 -0.3303 0.6301 0.083 Uiso 1 1 calc R . .
H51B H 0.1083 -0.164 0.5131 0.083 Uiso 1 1 calc R . .
H51C H 0.0536 -0.128 0.7023 0.083 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04722(14) 0.04047(14) 0.07047(18) 0.02136(11) 0.00662(10) 0.02287(10)
O1 0.0512(12) 0.0383(12) 0.0633(14) 0.0116(10) 0.0066(10) 0.0234(10)
C4 0.0402(14) 0.0385(15) 0.0364(14) 0.0095(11) 0.0069(11) 0.0219(13)
N2 0.0481(15) 0.0490(16) 0.0614(17) 0.0129(13) 0.0029(12) 0.0294(13)
N31 0.0361(14) 0.0576(19) 0.085(2) 0.0207(15) -0.0052(13) 0.0182(13)
C5 0.0425(15) 0.0408(16) 0.0400(15) 0.0084(12) 0.0069(12) 0.0228(13)
C3 0.0400(15) 0.0449(17) 0.0426(15) 0.0090(13) 0.0058(12) 0.0230(14)
C51 0.0428(17) 0.0474(19) 0.067(2) 0.0099(16) 0.0050(15) 0.0145(15)


#----------------------------------------------------------------------------#
#                   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
I1 C4 2.051(3) . ?
O1 C5 1.348(3) . ?
O1 N2 1.429(3) . ?
C4 C5 1.337(4) . ?
C4 C3 1.423(4) . ?
N2 C3 1.317(4) . ?
N31 C3 1.353(4) . ?
N31 H31A 0.86 . ?
N31 H31B 0.86 . ?
C5 C51 1.485(4) . ?
C51 H51A 0.96 . ?
C51 H51B 0.96 . ?
C51 H51C 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
C5 O1 N2 108.5(2) . . ?
C5 C4 C3 105.3(3) . . ?
C5 C4 I1 128.3(2) . . ?
C3 C4 I1 126.3(2) . . ?
C3 N2 O1 104.8(2) . . ?
C3 N31 H31A 120 . . ?
C3 N31 H31B 120 . . ?
H31A N31 H31B 120 . . ?
C4 C5 O1 110.1(2) . . ?
C4 C5 C51 133.2(3) . . ?
O1 C5 C51 116.8(3) . . ?
N2 C3 N31 122.4(3) . . ?
N2 C3 C4 111.3(3) . . ?
N31 C3 C4 126.3(3) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?

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
C5 O1 N2 C3 0.5(3) . . . . ?
C3 C4 C5 O1 0.2(3) . . . . ?
I1 C4 C5 O1 -175.88(18) . . . . ?
C3 C4 C5 C51 -179.8(3) . . . . ?
I1 C4 C5 C51 4.1(5) . . . . ?
N2 O1 C5 C4 -0.4(3) . . . . ?
N2 O1 C5 C51 179.5(3) . . . . ?
O1 N2 C3 N31 178.2(3) . . . . ?
O1 N2 C3 C4 -0.4(3) . . . . ?
C5 C4 C3 N2 0.1(3) . . . . ?
I1 C4 C3 N2 176.3(2) . . . . ?
C5 C4 C3 N31 -178.4(3) . . . . ?
I1 C4 C3 N31 -2.2(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 993666'
#######################################################################
#
#                 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_p-1

_audit_creation_date             2012-04-17T09:22:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-phenyl-1-(1,1-dimethylethyl06,7-dihydro-1H-
_chemical_formula_moiety         'C15 H16 N4 O'
_chemical_formula_sum            'C15 H16 N4 O'
_chemical_formula_weight         268.32
_chemical_melting_point          none

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2936(4)
_cell_length_b                   8.6404(5)
_cell_length_c                   13.6969(7)
_cell_angle_alpha                104.214(3)
_cell_angle_beta                 95.590(3)
_cell_angle_gamma                105.184(3)
_cell_volume                     686.33(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6247
_cell_measurement_theta_min      2.546
_cell_measurement_theta_max      27.0935

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_T_max  0.9789

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_number            17893
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         27.18
_diffrn_reflns_theta_full        27.18
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             3015
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.0469P)²+0.1421P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.010(3)
_refine_ls_number_reflns         3015
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.103
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.03

#----------------------------------------------------------------------------#
#                   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 0.18086(17) 0.58424(12) 0.34667(7) 0.0346(2) Uani 1 1 d . . .
N6 N 0.1170(2) 0.38260(14) 0.07296(8) 0.0470(3) Uani 1 1 d . . .
H6 H 0.0646 0.3827 0.0126 0.056 Uiso 1 1 calc R . .
N5 N 0.2219(2) 0.26466(14) 0.07570(8) 0.0453(3) Uani 1 1 d . . .
O71 O -0.02192(18) 0.59596(12) 0.13135(6) 0.0499(3) Uani 1 1 d . . .
C44 C 0.6492(3) -0.1061(2) 0.15343(11) 0.0552(4) Uani 1 1 d . . .
H44 H 0.7264 -0.185 0.1494 0.066 Uiso 1 1 calc R . .
C43 C 0.4477(3) -0.14419(18) 0.08976(11) 0.0517(4) Uani 1 1 d . . .
H43 H 0.3889 -0.2493 0.0429 0.062 Uiso 1 1 calc R . .
C42 C 0.3329(2) -0.02748(17) 0.09513(10) 0.0443(3) Uani 1 1 d . . .
H42 H 0.1969 -0.0542 0.0521 0.053 Uiso 1 1 calc R . .
C41 C 0.4198(2) 0.12994(16) 0.16472(9) 0.0375(3) Uani 1 1 d . . .
C4 C 0.3039(2) 0.25827(15) 0.16513(9) 0.0365(3) Uani 1 1 d . . .
C3A C 0.2818(2) 0.37314(15) 0.25590(8) 0.0333(3) Uani 1 1 d . . .
C7A C 0.1768(2) 0.49357(14) 0.24934(8) 0.0329(3) Uani 1 1 d . . .
C1 C 0.1025(2) 0.73367(15) 0.38492(9) 0.0376(3) Uani 1 1 d . . .
C12 C 0.2176(3) 0.86991(17) 0.33940(11) 0.0518(4) Uani 1 1 d . . .
H12A H 0.1764 0.8318 0.2663 0.078 Uiso 1 1 calc R . .
H12B H 0.3766 0.8962 0.358 0.078 Uiso 1 1 calc R . .
H12C H 0.1724 0.968 0.3651 0.078 Uiso 1 1 calc R . .
C11 C 0.1666(3) 0.79382(19) 0.50107(10) 0.0558(4) Uani 1 1 d . . .
H11A H 0.0939 0.7072 0.5296 0.084 Uiso 1 1 calc R . .
H11B H 0.1206 0.8915 0.5267 0.084 Uiso 1 1 calc R . .
H11C H 0.3257 0.8206 0.52 0.084 Uiso 1 1 calc R . .
N2 N 0.28233(19) 0.52473(14) 0.41469(7) 0.0404(3) Uani 1 1 d . . .
C3 C 0.3413(2) 0.39837(16) 0.36130(9) 0.0388(3) Uani 1 1 d . . .
H3 H 0.413 0.3343 0.3898 0.047 Uiso 1 1 calc R . .
C7 C 0.0814(2) 0.50092(16) 0.15048(9) 0.0378(3) Uani 1 1 d . . .
C45 C 0.7355(3) 0.0490(2) 0.22283(11) 0.0552(4) Uani 1 1 d . . .
H45 H 0.8713 0.0748 0.2658 0.066 Uiso 1 1 calc R . .
C46 C 0.6218(2) 0.16691(18) 0.22914(10) 0.0466(3) Uani 1 1 d . . .
H46 H 0.6808 0.2713 0.2767 0.056 Uiso 1 1 calc R . .
C13 C -0.1501(2) 0.6813(2) 0.35535(12) 0.0547(4) Uani 1 1 d . . .
H13A H -0.2157 0.5954 0.3859 0.082 Uiso 1 1 calc R . .
H13B H -0.1911 0.6393 0.2823 0.082 Uiso 1 1 calc R . .
H13C H -0.2033 0.776 0.3792 0.082 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0431(6) 0.0384(5) 0.0240(5) 0.0074(4) 0.0035(4) 0.0167(5)
N6 0.0721(8) 0.0517(7) 0.0234(5) 0.0067(4) -0.0015(5) 0.0362(6)
N5 0.0656(8) 0.0476(6) 0.0296(5) 0.0075(5) 0.0040(5) 0.0331(6)
O71 0.0732(7) 0.0550(6) 0.0304(5) 0.0095(4) -0.0002(4) 0.0397(5)
C44 0.0755(11) 0.0633(9) 0.0504(8) 0.0244(7) 0.0248(8) 0.0474(9)
C43 0.0739(10) 0.0441(8) 0.0452(7) 0.0120(6) 0.0185(7) 0.0285(7)
C42 0.0557(8) 0.0432(7) 0.0372(6) 0.0101(5) 0.0080(6) 0.0210(6)
C41 0.0481(7) 0.0405(7) 0.0311(6) 0.0133(5) 0.0102(5) 0.0211(6)
C4 0.0439(7) 0.0378(6) 0.0293(6) 0.0085(5) 0.0047(5) 0.0163(5)
C3A 0.0359(6) 0.0359(6) 0.0286(6) 0.0095(5) 0.0022(5) 0.0125(5)
C7A 0.0383(6) 0.0349(6) 0.0250(5) 0.0064(4) 0.0029(4) 0.0128(5)
C1 0.0464(7) 0.0365(6) 0.0302(6) 0.0050(5) 0.0071(5) 0.0166(5)
C12 0.0679(10) 0.0389(7) 0.0475(8) 0.0105(6) 0.0150(7) 0.0138(7)
C11 0.0809(11) 0.0542(9) 0.0322(7) 0.0015(6) 0.0084(7) 0.0301(8)
N2 0.0501(6) 0.0485(6) 0.0264(5) 0.0118(4) 0.0027(4) 0.0210(5)
C3 0.0457(7) 0.0454(7) 0.0300(6) 0.0131(5) 0.0032(5) 0.0203(6)
C7 0.0484(7) 0.0404(7) 0.0265(6) 0.0072(5) 0.0014(5) 0.0201(6)
C45 0.0578(9) 0.0716(10) 0.0485(8) 0.0200(7) 0.0086(7) 0.0374(8)
C46 0.0525(8) 0.0490(8) 0.0414(7) 0.0103(6) 0.0051(6) 0.0238(7)
C13 0.0486(8) 0.0565(9) 0.0588(9) 0.0076(7) 0.0115(7) 0.0226(7)


#----------------------------------------------------------------------------#
#                   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 N2 1.3533(14) . ?
N1 C7A 1.3645(14) . ?
N1 C1 1.4954(15) . ?
N6 N5 1.3574(15) . ?
N6 C7 1.3624(15) . ?
N6 H6 0.86 . ?
N5 C4 1.3017(15) . ?
O71 C7 1.2319(14) . ?
C44 C45 1.374(2) . ?
C44 C43 1.380(2) . ?
C44 H44 0.93 . ?
C43 C42 1.3783(19) . ?
C43 H43 0.93 . ?
C42 C41 1.3892(18) . ?
C42 H42 0.93 . ?
C41 C46 1.3882(19) . ?
C41 C4 1.4779(17) . ?
C4 C3A 1.4318(16) . ?
C3A C7A 1.3863(16) . ?
C3A C3 1.4033(16) . ?
C7A C7 1.4498(16) . ?
C1 C12 1.5167(19) . ?
C1 C13 1.5180(19) . ?
C1 C11 1.5241(17) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
N2 C3 1.3181(16) . ?
C3 H3 0.93 . ?
C45 C46 1.3810(19) . ?
C45 H45 0.93 . ?
C46 H46 0.93 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 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
N2 N1 C7A 110.01(10) . . ?
N2 N1 C1 119.29(9) . . ?
C7A N1 C1 130.65(10) . . ?
N5 N6 C7 130.37(10) . . ?
N5 N6 H6 114.8 . . ?
C7 N6 H6 114.8 . . ?
C4 N5 N6 117.52(10) . . ?
C45 C44 C43 119.73(13) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C42 C43 C44 120.41(14) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C43 C42 C41 120.15(13) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C46 C41 C42 119.11(12) . . ?
C46 C41 C4 120.96(11) . . ?
C42 C41 C4 119.83(11) . . ?
N5 C4 C3A 120.03(11) . . ?
N5 C4 C41 115.81(10) . . ?
C3A C4 C41 124.15(10) . . ?
C7A C3A C3 104.36(10) . . ?
C7A C3A C4 120.44(10) . . ?
C3 C3A C4 135.19(11) . . ?
N1 C7A C3A 107.53(10) . . ?
N1 C7A C7 132.12(11) . . ?
C3A C7A C7 120.31(10) . . ?
N1 C1 C12 108.59(10) . . ?
N1 C1 C13 108.35(10) . . ?
C12 C1 C13 112.35(12) . . ?
N1 C1 C11 108.44(10) . . ?
C12 C1 C11 109.69(11) . . ?
C13 C1 C11 109.32(12) . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 N2 N1 106.92(9) . . ?
N2 C3 C3A 111.17(11) . . ?
N2 C3 H3 124.4 . . ?
C3A C3 H3 124.4 . . ?
O71 C7 N6 120.13(11) . . ?
O71 C7 C7A 128.56(11) . . ?
N6 C7 C7A 111.30(10) . . ?
C44 C45 C46 120.42(14) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C41 120.18(13) . . ?
C45 C46 H46 119.9 . . ?
C41 C46 H46 119.9 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C7 N6 N5 C4 0.3(2) . . . . ?
C45 C44 C43 C42 0.2(2) . . . . ?
C44 C43 C42 C41 0.2(2) . . . . ?
C43 C42 C41 C46 -0.7(2) . . . . ?
C43 C42 C41 C4 175.74(12) . . . . ?
N6 N5 C4 C3A -0.06(19) . . . . ?
N6 N5 C4 C41 -179.06(12) . . . . ?
C46 C41 C4 N5 136.34(14) . . . . ?
C42 C41 C4 N5 -40.03(18) . . . . ?
C46 C41 C4 C3A -42.62(19) . . . . ?
C42 C41 C4 C3A 141.01(13) . . . . ?
N5 C4 C3A C7A -1.13(19) . . . . ?
C41 C4 C3A C7A 177.79(12) . . . . ?
N5 C4 C3A C3 177.68(14) . . . . ?
C41 C4 C3A C3 -3.4(2) . . . . ?
N2 N1 C7A C3A -0.63(14) . . . . ?
C1 N1 C7A C3A 176.63(11) . . . . ?
N2 N1 C7A C7 177.09(13) . . . . ?
C1 N1 C7A C7 -5.6(2) . . . . ?
C3 C3A C7A N1 1.03(14) . . . . ?
C4 C3A C7A N1 -179.83(11) . . . . ?
C3 C3A C7A C7 -177.02(12) . . . . ?
C4 C3A C7A C7 2.12(19) . . . . ?
N2 N1 C1 C12 121.16(12) . . . . ?
C7A N1 C1 C12 -55.89(17) . . . . ?
N2 N1 C1 C13 -116.54(12) . . . . ?
C7A N1 C1 C13 66.41(16) . . . . ?
N2 N1 C1 C11 2.02(16) . . . . ?
C7A N1 C1 C11 -175.03(13) . . . . ?
C7A N1 N2 C3 -0.08(14) . . . . ?
C1 N1 N2 C3 -177.69(11) . . . . ?
N1 N2 C3 C3A 0.76(15) . . . . ?
C7A C3A C3 N2 -1.13(15) . . . . ?
C4 C3A C3 N2 179.93(14) . . . . ?
N5 N6 C7 O71 -178.99(14) . . . . ?
N5 N6 C7 C7A 0.7(2) . . . . ?
N1 C7A C7 O71 0.3(2) . . . . ?
C3A C7A C7 O71 177.81(13) . . . . ?
N1 C7A C7 N6 -179.29(13) . . . . ?
C3A C7A C7 N6 -1.79(18) . . . . ?
C43 C44 C45 C46 -0.1(2) . . . . ?
C44 C45 C46 C41 -0.5(2) . . . . ?
C42 C41 C46 C45 0.9(2) . . . . ?
C4 C41 C46 C45 -175.54(13) . . . . ?

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
N6 H6 O71 0.86 2.02 2.8653(14) 165.9 2_565

_database_code_depnum_ccdc_archive 'CCDC 914132'
#######################################################################
#
#                 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_eslmarcos69a22_0m

_audit_creation_date             2008-03-24T15:35:16-00:00
_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        
;
        (E)-1,1,1-trichloro-4-phenylamino-3-buten-2-one
;
_chemical_name_common            trichloro-4-phenylamino-3-buten-2-one
_chemical_formula_moiety         'C10 H8 Cl3 N O'
_chemical_formula_sum            'C10 H8 Cl3 N O'
_chemical_formula_weight         264.52
_chemical_melting_point          102-104C

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(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                   11.3649(3)
_cell_length_b                   6.0949(2)
_cell_length_c                   16.6562(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.811(2)
_cell_angle_gamma                90
_cell_volume                     1133.26(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    200
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      21.3705

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

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.55
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;

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

_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.854664
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_number            9428
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         24.84
_diffrn_reflns_theta_full        24.84
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             1926
_reflns_number_gt                1487
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.0290P)²+6.9665P] 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         1926
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.267
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.24382(14) 1.1979(3) 0.80647(9) 0.0600(5) Uani 1 1 d . . .
Cl2 Cl 1.36780(14) 0.8498(3) 0.90461(11) 0.0606(5) Uani 1 1 d . . .
Cl3 Cl 1.3096(2) 1.2420(3) 0.98094(11) 0.0822(7) Uani 1 1 d . . .
C1 C 1.2595(5) 1.0556(10) 0.9010(3) 0.0416(13) Uani 1 1 d . . .
C3 C 1.1057(5) 0.7545(12) 0.8992(4) 0.0537(17) Uani 1 1 d . . .
H3 H 1.1635 0.6413 0.9005 0.064 Uiso 1 1 calc R . .
C2 C 1.1329(5) 0.9762(12) 0.9069(4) 0.0549(17) Uani 1 1 d . . .
C4 C 0.9720(10) 0.7161(12) 0.8884(4) 0.087(3) Uani 1 1 d . . .
H4 H 0.9205 0.8397 0.8854 0.104 Uiso 1 1 calc R . .
C51 C 0.8015(5) 0.5094(14) 0.8625(3) 0.0558(19) Uani 1 1 d . . .
C53 C 0.6034(6) 0.6037(12) 0.7998(4) 0.0538(17) Uani 1 1 d . . .
H53 H 0.5478 0.7033 0.7695 0.065 Uiso 1 1 calc R . .
C56 C 0.7595(7) 0.3106(13) 0.8872(4) 0.066(2) Uani 1 1 d . . .
H56 H 0.8135 0.2078 0.9171 0.079 Uiso 1 1 calc R . .
C54 C 0.5642(6) 0.4101(13) 0.8252(4) 0.064(2) Uani 1 1 d . . .
H54 H 0.4813 0.3756 0.8125 0.076 Uiso 1 1 calc R . .
C52 C 0.7219(6) 0.6561(11) 0.8175(3) 0.0492(15) Uani 1 1 d . . .
H52 H 0.7496 0.791 0.7994 0.059 Uiso 1 1 calc R . .
C55 C 0.6413(7) 0.2657(13) 0.8683(4) 0.0646(19) Uani 1 1 d . . .
H55 H 0.6121 0.131 0.8856 0.078 Uiso 1 1 calc R . .
N5 N 0.9282(6) 0.5352(13) 0.8836(4) 0.0777(19) Uani 1 1 d . . .
H5 H 0.9745 0.4189 0.8931 0.093 Uiso 1 1 calc R . .
O21 O 1.0612(5) 1.1241(10) 0.9143(5) 0.116(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0539(9) 0.0802(12) 0.0440(8) 0.0121(8) 0.0047(7) -0.0165(9)
Cl2 0.0410(8) 0.0711(12) 0.0686(11) -0.0090(9) 0.0072(7) 0.0107(8)
Cl3 0.1183(17) 0.0638(12) 0.0514(10) -0.0195(9) -0.0175(10) 0.0131(12)
C1 0.042(3) 0.042(3) 0.040(3) -0.005(3) 0.006(2) 0.001(3)
C3 0.033(3) 0.075(5) 0.047(3) 0.011(3) -0.008(3) -0.020(3)
C2 0.037(3) 0.064(5) 0.064(4) 0.021(3) 0.010(3) 0.009(3)
C4 0.181(10) 0.039(4) 0.053(4) 0.012(3) 0.053(5) -0.008(5)
C51 0.024(3) 0.109(6) 0.034(3) -0.020(4) 0.003(2) 0.001(3)
C53 0.049(4) 0.068(5) 0.043(3) 0.004(3) 0.006(3) 0.013(3)
C56 0.085(5) 0.077(5) 0.038(3) 0.010(3) 0.015(3) 0.030(5)
C54 0.049(4) 0.083(6) 0.062(4) -0.008(4) 0.019(3) -0.018(4)
C52 0.058(4) 0.050(4) 0.042(3) -0.002(3) 0.015(3) -0.015(3)
C55 0.089(6) 0.054(4) 0.056(4) -0.001(3) 0.028(4) -0.012(4)
N5 0.083(5) 0.088(5) 0.062(4) -0.010(4) 0.014(3) -0.001(4)
O21 0.074(4) 0.092(4) 0.201(7) 0.079(5) 0.077(4) 0.045(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
Cl1 C1 1.778(6) . ?
Cl2 C1 1.751(6) . ?
Cl3 C1 1.761(6) . ?
C1 C2 1.538(8) . ?
C3 C2 1.387(10) . ?
C3 C4 1.514(12) . ?
C3 H3 0.95 . ?
C2 O21 1.237(8) . ?
C4 N5 1.206(9) . ?
C4 H4 0.95 . ?
C51 C52 1.388(9) . ?
C51 C56 1.392(11) . ?
C51 N5 1.425(8) . ?
C53 C54 1.356(10) . ?
C53 C52 1.362(8) . ?
C53 H53 0.95 . ?
C56 C55 1.349(10) . ?
C56 H56 0.95 . ?
C54 C55 1.350(10) . ?
C54 H54 0.95 . ?
C52 H52 0.95 . ?
C55 H55 0.95 . ?
N5 H5 0.88 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Cl2 115.6(4) . . ?
C2 C1 Cl3 109.2(4) . . ?
Cl2 C1 Cl3 108.1(3) . . ?
C2 C1 Cl1 105.7(4) . . ?
Cl2 C1 Cl1 109.4(3) . . ?
Cl3 C1 Cl1 108.6(3) . . ?
C2 C3 C4 111.3(6) . . ?
C2 C3 H3 124.4 . . ?
C4 C3 H3 124.4 . . ?
O21 C2 C3 125.4(7) . . ?
O21 C2 C1 114.8(6) . . ?
C3 C2 C1 119.7(6) . . ?
N5 C4 C3 122.8(9) . . ?
N5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C52 C51 C56 119.7(6) . . ?
C52 C51 N5 126.0(7) . . ?
C56 C51 N5 114.2(7) . . ?
C54 C53 C52 120.4(6) . . ?
C54 C53 H53 119.8 . . ?
C52 C53 H53 119.8 . . ?
C55 C56 C51 119.3(7) . . ?
C55 C56 H56 120.4 . . ?
C51 C56 H56 120.4 . . ?
C55 C54 C53 121.0(7) . . ?
C55 C54 H54 119.5 . . ?
C53 C54 H54 119.5 . . ?
C53 C52 C51 118.9(6) . . ?
C53 C52 H52 120.5 . . ?
C51 C52 H52 120.5 . . ?
C56 C55 C54 120.7(7) . . ?
C56 C55 H55 119.6 . . ?
C54 C55 H55 119.6 . . ?
C4 N5 C51 120.2(9) . . ?
C4 N5 H5 119.9 . . ?
C51 N5 H5 119.9 . . ?

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
C4 C3 C2 O21 8.3(10) . . . . ?
C4 C3 C2 C1 -167.7(5) . . . . ?
Cl2 C1 C2 O21 171.6(6) . . . . ?
Cl3 C1 C2 O21 49.5(7) . . . . ?
Cl1 C1 C2 O21 -67.2(7) . . . . ?
Cl2 C1 C2 C3 -11.9(8) . . . . ?
Cl3 C1 C2 C3 -134.1(6) . . . . ?
Cl1 C1 C2 C3 109.2(6) . . . . ?
C2 C3 C4 N5 -177.2(7) . . . . ?
C52 C51 C56 C55 -1.3(9) . . . . ?
N5 C51 C56 C55 -178.0(6) . . . . ?
C52 C53 C54 C55 0.0(10) . . . . ?
C54 C53 C52 C51 -0.6(9) . . . . ?
C56 C51 C52 C53 1.2(9) . . . . ?
N5 C51 C52 C53 177.6(6) . . . . ?
C51 C56 C55 C54 0.7(10) . . . . ?
C53 C54 C55 C56 0.0(11) . . . . ?
C3 C4 N5 C51 -171.5(5) . . . . ?
C52 C51 N5 C4 25.8(10) . . . . ?
C56 C51 N5 C4 -157.7(7) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 680898'
#######################################################################
#
#                 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_p-1

_audit_creation_date             2009-04-23T21:01:20-00:00
_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        
;
 1-tert-butyl-5-(4-(1-tert-butyl-1H-pyrazol-5-yl)phenyl-1H-pyrazole
;
_chemical_name_common            'tert-butyl pyrazole'
_chemical_formula_moiety         'C10 H13 N2'
_chemical_formula_sum            'C10 H13 N2'
_chemical_formula_weight         161.22
_chemical_melting_point          194-195

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.90930(10)
_cell_length_b                   7.91880(10)
_cell_length_c                   10.0033(2)
_cell_angle_alpha                67.3110(10)
_cell_angle_beta                 89.2900(10)
_cell_angle_gamma                65.6060(10)
_cell_volume                     452.795(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3231
_cell_measurement_theta_min      2.241
_cell_measurement_theta_max      27.6845

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

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.582
_exptl_crystal_size_mid          0.474
_exptl_crystal_size_min          0.204
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             174

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

_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
 XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;
_exptl_absorpt_correction_T_min  0.9495
_exptl_absorpt_correction_T_max  0.9978

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_number            8313
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2173
_reflns_number_gt                1799
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.0795P)²+0.0696P] 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         2173
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   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'

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 0.26118(16) 0.29887(16) 0.71566(11) 0.0364(3) Uani 1 1 d . . .
N2 N 0.40642(19) 0.28939(19) 0.62280(12) 0.0445(3) Uani 1 1 d . . .
C51 C 0.11906(18) 0.06322(17) 0.89364(12) 0.0325(3) Uani 1 1 d . . .
C5 C 0.25113(18) 0.11719(18) 0.78164(12) 0.0327(3) Uani 1 1 d . . .
C11 C 0.1570(2) 0.4912(2) 0.73735(15) 0.0448(3) Uani 1 1 d . . .
C53 C 0.0693(2) -0.0578(2) 1.14669(13) 0.0405(3) Uani 1 1 d . . .
C52 C 0.18754(19) 0.0033(2) 1.04153(13) 0.0403(3) Uani 1 1 d . . .
C3 C 0.4831(2) 0.1038(2) 0.62942(15) 0.0441(3) Uani 1 1 d . . .
H3 H 0.5861 0.0547 0.576 0.053 Uiso 1 1 calc R . .
C4 C 0.3918(2) -0.0097(2) 0.72563(14) 0.0413(3) Uani 1 1 d . . .
H4 H 0.4199 -0.1439 0.7477 0.05 Uiso 1 1 calc R . .
C113 C 0.1361(3) 0.6690(3) 0.59442(19) 0.0705(5) Uani 1 1 d . . .
H11A H 0.0448 0.6795 0.5172 0.106 Uiso 1 1 calc R . .
H11B H 0.2763 0.6457 0.5687 0.106 Uiso 1 1 calc R . .
H11C H 0.0742 0.7934 0.6076 0.106 Uiso 1 1 calc R . .
C111 C -0.0684(3) 0.5291(3) 0.7717(2) 0.0710(5) Uani 1 1 d . . .
H11D H -0.1552 0.5401 0.6918 0.107 Uiso 1 1 calc R . .
H11E H -0.1329 0.6537 0.7846 0.107 Uiso 1 1 calc R . .
H11F H -0.0594 0.4177 0.8603 0.107 Uiso 1 1 calc R . .
C112 C 0.3003(3) 0.4724(3) 0.8612(2) 0.0713(5) Uani 1 1 d . . .
H11G H 0.3116 0.3605 0.9504 0.107 Uiso 1 1 calc R . .
H11H H 0.2386 0.5964 0.8748 0.107 Uiso 1 1 calc R . .
H11I H 0.4412 0.4483 0.8366 0.107 Uiso 1 1 calc R . .
H43 H 0.121(3) -0.103(2) 1.2542(18) 0.054(4) Uiso 1 1 d . . .
H52 H 0.317(3) 0.006(2) 1.0732(17) 0.050(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0410(5) 0.0389(6) 0.0331(5) -0.0137(4) 0.0154(4) -0.0224(4)
N2 0.0500(6) 0.0554(7) 0.0391(6) -0.0208(5) 0.0230(5) -0.0327(5)
C51 0.0317(5) 0.0334(6) 0.0320(6) -0.0098(4) 0.0080(4) -0.0175(4)
C5 0.0324(5) 0.0381(6) 0.0301(5) -0.0123(5) 0.0072(4) -0.0196(5)
C11 0.0537(8) 0.0343(6) 0.0428(7) -0.0131(5) 0.0141(6) -0.0190(6)
C53 0.0403(6) 0.0541(8) 0.0295(6) -0.0117(5) 0.0056(5) -0.0283(6)
C52 0.0358(6) 0.0537(8) 0.0343(6) -0.0127(5) 0.0055(5) -0.0279(6)
C3 0.0428(7) 0.0605(8) 0.0426(7) -0.0291(6) 0.0192(5) -0.0284(6)
C4 0.0427(6) 0.0442(7) 0.0469(7) -0.0246(6) 0.0149(5) -0.0232(6)
C113 0.0956(14) 0.0426(8) 0.0589(10) -0.0079(7) 0.0222(9) -0.0302(9)
C111 0.0621(10) 0.0461(9) 0.0943(14) -0.0279(9) 0.0357(9) -0.0162(7)
C112 0.0930(14) 0.0534(9) 0.0676(11) -0.0322(8) 0.0019(10) -0.0259(9)


#----------------------------------------------------------------------------#
#                   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 N2 1.3580(13) . ?
N1 C5 1.3635(15) . ?
N1 C11 1.4933(16) . ?
N2 C3 1.3142(19) . ?
C51 C52 1.3886(16) . ?
C51 C53 1.3892(15) 2_557 ?
C51 C5 1.4826(15) . ?
C5 C4 1.3720(17) . ?
C11 C112 1.517(2) . ?
C11 C111 1.521(2) . ?
C11 C113 1.527(2) . ?
C53 C52 1.3862(16) . ?
C53 C51 1.3892(15) 2_557 ?
C53 H43 1.010(16) . ?
C52 H52 0.963(16) . ?
C3 C4 1.3852(18) . ?
C3 H3 0.93 . ?
C4 H4 0.93 . ?
C113 H11A 0.96 . ?
C113 H11B 0.96 . ?
C113 H11C 0.96 . ?
C111 H11D 0.96 . ?
C111 H11E 0.96 . ?
C111 H11F 0.96 . ?
C112 H11G 0.96 . ?
C112 H11H 0.96 . ?
C112 H11I 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
N2 N1 C5 110.99(10) . . ?
N2 N1 C11 117.16(10) . . ?
C5 N1 C11 131.64(10) . . ?
C3 N2 N1 105.41(10) . . ?
C52 C51 C53 118.57(10) . 2_557 ?
C52 C51 C5 121.14(10) . . ?
C53 C51 C5 120.13(10) 2_557 . ?
N1 C5 C4 106.26(10) . . ?
N1 C5 C51 127.59(11) . . ?
C4 C5 C51 126.15(11) . . ?
N1 C11 C112 108.08(12) . . ?
N1 C11 C111 110.72(11) . . ?
C112 C11 C111 111.29(15) . . ?
N1 C11 C113 108.37(11) . . ?
C112 C11 C113 110.31(14) . . ?
C111 C11 C113 108.03(14) . . ?
C52 C53 C51 120.58(11) . 2_557 ?
C52 C53 H43 120.6(9) . . ?
C51 C53 H43 118.8(9) 2_557 . ?
C53 C52 C51 120.84(10) . . ?
C53 C52 H52 118.5(9) . . ?
C51 C52 H52 120.7(9) . . ?
N2 C3 C4 111.74(12) . . ?
N2 C3 H3 124.1 . . ?
C4 C3 H3 124.1 . . ?
C5 C4 C3 105.58(12) . . ?
C5 C4 H4 127.2 . . ?
C3 C4 H4 127.2 . . ?
C11 C113 H11A 109.5 . . ?
C11 C113 H11B 109.5 . . ?
H11A C113 H11B 109.5 . . ?
C11 C113 H11C 109.5 . . ?
H11A C113 H11C 109.5 . . ?
H11B C113 H11C 109.5 . . ?
C11 C111 H11D 109.5 . . ?
C11 C111 H11E 109.5 . . ?
H11D C111 H11E 109.5 . . ?
C11 C111 H11F 109.5 . . ?
H11D C111 H11F 109.5 . . ?
H11E C111 H11F 109.5 . . ?
C11 C112 H11G 109.5 . . ?
C11 C112 H11H 109.5 . . ?
H11G C112 H11H 109.5 . . ?
C11 C112 H11I 109.5 . . ?
H11G C112 H11I 109.5 . . ?
H11H C112 H11I 109.5 . . ?

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
C5 N1 N2 C3 1.04(14) . . . . ?
C11 N1 N2 C3 176.35(11) . . . . ?
N2 N1 C5 C4 -1.37(13) . . . . ?
C11 N1 C5 C4 -175.78(12) . . . . ?
N2 N1 C5 C51 177.59(10) . . . . ?
C11 N1 C5 C51 3.2(2) . . . . ?
C52 C51 C5 N1 -82.02(16) . . . . ?
C53 C51 C5 N1 102.57(15) 2_557 . . . ?
C52 C51 C5 C4 96.74(15) . . . . ?
C53 C51 C5 C4 -78.66(16) 2_557 . . . ?
N2 N1 C11 C112 -87.54(14) . . . . ?
C5 N1 C11 C112 86.59(17) . . . . ?
N2 N1 C11 C111 150.32(13) . . . . ?
C5 N1 C11 C111 -35.54(19) . . . . ?
N2 N1 C11 C113 32.00(16) . . . . ?
C5 N1 C11 C113 -153.86(14) . . . . ?
C51 C53 C52 C51 0.9(2) 2_557 . . . ?
C53 C51 C52 C53 -0.9(2) 2_557 . . . ?
C5 C51 C52 C53 -176.37(12) . . . . ?
N1 N2 C3 C4 -0.31(15) . . . . ?
N1 C5 C4 C3 1.11(13) . . . . ?
C51 C5 C4 C3 -177.87(11) . . . . ?
N2 C3 C4 C5 -0.51(15) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 993672'
