# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_teste1
_audit_block_doi                 10.5517/cc12bzr4
_database_code_depnum_ccdc_archive 'CCDC 993666'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4RA06040G 2014
_audit_update_record             
;
2014-03-25 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_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) . . . . ?

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

data_pbca
_database_code_depnum_ccdc_archive 'CCDC 1405887'
_audit_update_record             
;
2015-06-17 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_date             2012-09-18T09:49:02-00:00
_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-chloro-5-methylisoxazol-3-amine
;
_chemical_name_common            4-chloro-5-methylisoxazol-3-amine
_chemical_formula_moiety         'C4 H5 Cl N2 O'
_chemical_formula_sum            'C4 H5 Cl N2 O'
_chemical_formula_weight         132.55
_chemical_melting_point          none

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  -P2ac2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.9082(3)
_cell_length_b                   12.2055(7)
_cell_length_c                   14.2820(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1204.23(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5050
_cell_measurement_theta_min      2.8525
_cell_measurement_theta_max      25.2285

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.89
_exptl_crystal_size_mid          0.59
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_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    0.531
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_T_max  0.8744

#----------------------------------------------------------------------------#
#                   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  0.024
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_number            14204
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.19
_diffrn_reflns_theta_full        27.19
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             1331
_reflns_number_gt                1107
_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)+(0.0787P)²+0.5137P] 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         1331
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.302
_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'
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
N31 N -0.3912(3) 0.36140(15) 0.06311(17) 0.0734(6) Uani 1 1 d . . .
H31A H -0.4994 0.377 0.0365 0.088 Uiso 1 1 calc R . .
H31B H -0.3646 0.2946 0.0772 0.088 Uiso 1 1 calc R . .
C51 C 0.1794(4) 0.5731(2) 0.16979(18) 0.0688(7) Uani 1 1 d . . .
H51A H 0.1838 0.6511 0.1613 0.103 Uiso 1 1 calc R . .
H51B H 0.2862 0.5399 0.1376 0.103 Uiso 1 1 calc R . .
H51C H 0.1873 0.5563 0.2353 0.103 Uiso 1 1 calc R . .
Cl1 Cl 0.01813(11) 0.30952(5) 0.16221(6) 0.0859(3) Uani 1 1 d . . .
O1 O -0.1293(2) 0.60204(11) 0.09474(11) 0.0569(4) Uani 1 1 d . . .
C4 C -0.0808(3) 0.43013(15) 0.12615(14) 0.0463(5) Uani 1 1 d . . .
C5 C -0.2635(3) 0.44165(15) 0.08282(14) 0.0479(5) Uani 1 1 d . . .
N2 N -0.2969(3) 0.54458(14) 0.06289(14) 0.0593(5) Uani 1 1 d . . .
C3 C -0.0044(3) 0.53012(17) 0.13159(14) 0.0472(5) 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
N31 0.0726(13) 0.0414(10) 0.1062(16) 0.0120(10) -0.0317(12) -0.0109(9)
C51 0.0616(14) 0.0707(16) 0.0742(15) -0.0013(12) -0.0114(11) -0.0148(12)
Cl1 0.0858(5) 0.0499(4) 0.1219(7) 0.0150(3) -0.0260(4) 0.0193(3)
O1 0.0625(9) 0.0351(7) 0.0732(10) 0.0029(6) -0.0118(7) -0.0036(6)
C4 0.0493(10) 0.0389(9) 0.0508(10) 0.0015(8) -0.0007(8) 0.0072(8)
C5 0.0506(10) 0.0374(10) 0.0556(10) 0.0030(8) -0.0046(8) 0.0009(8)
N2 0.0561(10) 0.0384(8) 0.0833(12) 0.0050(8) -0.0203(9) 0.0001(8)
C3 0.0480(10) 0.0463(10) 0.0473(10) -0.0008(8) 0.0006(8) 0.0016(8)


#----------------------------------------------------------------------------#
#                   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
N31 C5 1.348(3) . ?
N31 H31A 0.86 . ?
N31 H31B 0.86 . ?
C51 C3 1.478(3) . ?
C51 H51A 0.96 . ?
C51 H51B 0.96 . ?
C51 H51C 0.96 . ?
Cl1 C4 1.7030(18) . ?
O1 C3 1.339(2) . ?
O1 N2 1.428(2) . ?
C4 C3 1.332(3) . ?
C4 C5 1.412(3) . ?
C5 N2 1.309(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
C5 N31 H31A 120 . . ?
C5 N31 H31B 120 . . ?
H31A N31 H31B 120 . . ?
C3 C51 H51A 109.5 . . ?
C3 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C3 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C3 O1 N2 109.02(14) . . ?
C3 C4 C5 106.78(17) . . ?
C3 C4 Cl1 127.96(16) . . ?
C5 C4 Cl1 125.26(15) . . ?
N2 C5 N31 122.43(19) . . ?
N2 C5 C4 110.40(17) . . ?
N31 C5 C4 127.16(18) . . ?
C5 N2 O1 105.01(15) . . ?
C4 C3 O1 108.78(17) . . ?
C4 C3 C51 133.4(2) . . ?
O1 C3 C51 117.76(19) . . ?

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

data_teste1
_database_code_depnum_ccdc_archive 'CCDC 1405888'
_audit_update_record             
;
2015-06-17 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_date             2012-09-18T09:23:19-00:00
_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-bromo-5-methylisoxazol-3-amine
;
_chemical_name_common            4-bromo-5-methylisoxazol-3-amine
_chemical_formula_moiety         'C4 H5 Br N2 O'
_chemical_formula_sum            'C4 H5 Br N2 O'
_chemical_formula_weight         177.01
_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                   6.4176(7)
_cell_length_b                   7.1023(9)
_cell_length_c                   7.5370(10)
_cell_angle_alpha                94.502(8)
_cell_angle_beta                 100.535(7)
_cell_angle_gamma                115.558(6)
_cell_volume                     299.86(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2831
_cell_measurement_theta_min      2.793
_cell_measurement_theta_max      24.2915

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.168
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.96
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             172
_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    6.75
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.147
_exptl_absorpt_correction_T_max  0.5074

#----------------------------------------------------------------------------#
#                   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  0.0279
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_number            7575
_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         2.79
_diffrn_reflns_theta_max         27.31
_diffrn_reflns_theta_full        27.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             1349
_reflns_number_gt                1110
_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)+(0.0314P)²+0.0727P] 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         1349
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.061
_refine_ls_wR_factor_gt          0.0575
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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
Br1 Br 0.47688(4) -0.34764(4) 0.29665(4) 0.06222(14) Uani 1 1 d . . .
O1 O 0.5405(3) 0.2213(3) 0.2124(3) 0.0561(4) Uani 1 1 d . . .
N2 N 0.2918(4) 0.0973(4) 0.1320(3) 0.0556(5) Uani 1 1 d . . .
N31 N 0.0244(4) -0.2623(4) 0.0910(3) 0.0656(6) Uani 1 1 d . . .
H31A H -0.0913 -0.2421 0.0345 0.079 Uiso 1 1 calc R . .
H31B H 0.0006 -0.3877 0.1078 0.079 Uiso 1 1 calc R . .
C4 C 0.4535(4) -0.1049(4) 0.2458(3) 0.0406(5) Uani 1 1 d . . .
C5 C 0.6275(4) 0.0927(4) 0.2783(3) 0.0436(5) Uani 1 1 d . . .
C3 C 0.2452(4) -0.0960(4) 0.1536(3) 0.0440(5) Uani 1 1 d . . .
C51 C 0.8840(4) 0.1903(4) 0.3686(4) 0.0574(7) Uani 1 1 d . . .
H51A H 0.9548 0.3395 0.3657 0.086 Uiso 1 1 calc R . .
H51B H 0.96 0.1255 0.3052 0.086 Uiso 1 1 calc R . .
H51C H 0.9038 0.1692 0.4937 0.086 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
Br1 0.05234(15) 0.04623(17) 0.0898(3) 0.02513(14) 0.00506(13) 0.02652(11)
O1 0.0587(9) 0.0440(10) 0.0682(12) 0.0113(9) 0.0065(8) 0.0290(8)
N2 0.0533(11) 0.0546(13) 0.0665(14) 0.0110(11) 0.0037(10) 0.0354(9)
N31 0.0448(10) 0.0610(14) 0.0868(18) 0.0137(12) -0.0012(10) 0.0268(10)
C4 0.0438(10) 0.0446(12) 0.0413(13) 0.0125(10) 0.0092(9) 0.0266(9)
C5 0.0488(11) 0.0441(13) 0.0454(14) 0.0094(10) 0.0111(10) 0.0277(10)
C3 0.0480(11) 0.0502(13) 0.0421(13) 0.0086(11) 0.0087(9) 0.0305(10)
C51 0.0469(12) 0.0502(14) 0.0677(17) 0.0096(13) 0.0059(11) 0.0186(10)


#----------------------------------------------------------------------------#
#                   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
Br1 C4 1.857(2) . ?
O1 C5 1.342(3) . ?
O1 N2 1.428(3) . ?
N2 C3 1.304(3) . ?
N31 C3 1.360(3) . ?
N31 H31A 0.86 . ?
N31 H31B 0.86 . ?
C4 C5 1.331(3) . ?
C4 C3 1.419(3) . ?
C5 C51 1.479(3) . ?
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 108.46(17) . . ?
C3 N2 O1 105.20(18) . . ?
C3 N31 H31A 120 . . ?
C3 N31 H31B 120 . . ?
H31A N31 H31B 120 . . ?
C5 C4 C3 105.9(2) . . ?
C5 C4 Br1 127.77(17) . . ?
C3 C4 Br1 126.23(17) . . ?
C4 C5 O1 109.59(19) . . ?
C4 C5 C51 133.1(2) . . ?
O1 C5 C51 117.3(2) . . ?
N2 C3 N31 122.7(2) . . ?
N2 C3 C4 110.8(2) . . ?
N31 C3 C4 126.5(2) . . ?
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 -0.2(3) . . . . ?
C3 C4 C5 O1 -0.1(3) . . . . ?
Br1 C4 C5 O1 176.62(17) . . . . ?
C3 C4 C5 C51 179.9(3) . . . . ?
Br1 C4 C5 C51 -3.4(4) . . . . ?
N2 O1 C5 C4 0.2(3) . . . . ?
N2 O1 C5 C51 -179.8(2) . . . . ?
O1 N2 C3 N31 -178.8(2) . . . . ?
O1 N2 C3 C4 0.2(3) . . . . ?
C5 C4 C3 N2 -0.1(3) . . . . ?
Br1 C4 C3 N2 -176.85(18) . . . . ?
C5 C4 C3 N31 178.9(2) . . . . ?
Br1 C4 C3 N31 2.1(4) . . . . ?

