# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1589617'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_date             2016-02-26T09:53:11-00:00
_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        
;
        ethyl 2-(5-(4-nitrophenyl)isoxazol-4-yl)-2-oxoacetate
;
_chemical_name_common            'ethyl 2-(5-(4-nitrophenyl)isoxazol-4-yl)-2-ox'
_chemical_formula_moiety         'C13 H10 N2 O6'
_chemical_formula_sum            'C13 H10 N2 O6'
_chemical_formula_weight         290.23
_chemical_melting_point          none

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6326(13)
_cell_length_b                   14.5578(13)
_cell_length_c                   7.3585(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.635(3)
_cell_angle_gamma                90
_cell_volume                     1296.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.918
_cell_measurement_theta_max      24.84

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_special_details           
;
 none
;

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

_exptl_absorpt_coefficient_mu    0.12
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_T_max  0.9887

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

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_number            87599
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_full        30.58
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3988
_reflns_number_gt                2971
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   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)+(0.0964P)²+0.4367P] 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         3988
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1774
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.042

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.34502(10) 0.51702(9) 0.25844(16) 0.0510(3) Uani 1 1 d . . .
O43 O 0.69463(10) 0.78833(9) 0.5020(2) 0.0586(4) Uani 1 1 d . . .
O41 O 0.50967(11) 0.74539(9) 0.5829(2) 0.0589(4) Uani 1 1 d . . .
O42 O 0.71555(11) 0.63897(9) 0.4504(2) 0.0597(4) Uani 1 1 d . . .
N2 N 0.42424(13) 0.50657(11) 0.1570(2) 0.0534(4) Uani 1 1 d . . .
C4 C 0.47912(12) 0.61585(9) 0.38300(19) 0.0356(3) Uani 1 1 d . . .
C41 C 0.54340(12) 0.69231(10) 0.4862(2) 0.0380(3) Uani 1 1 d . . .
C42 C 0.66189(12) 0.70282(11) 0.4735(2) 0.0404(3) Uani 1 1 d . . .
C5 C 0.37914(12) 0.58282(10) 0.39092(19) 0.0380(3) Uani 1 1 d . . .
O541 O 0.11513(17) 0.67235(16) 0.9859(3) 0.0972(6) Uani 1 1 d . . .
C3 C 0.50124(14) 0.56463(10) 0.2325(2) 0.0424(3) Uani 1 1 d . . .
H3 H 0.5644 0.5723 0.1932 0.051 Uiso 1 1 calc R . .
C51 C 0.30289(12) 0.60068(10) 0.5044(2) 0.0392(3) Uani 1 1 d . . .
C53 C 0.26787(14) 0.64804(12) 0.7951(2) 0.0472(4) Uani 1 1 d . . .
H53 H 0.2925 0.6704 0.9185 0.057 Uiso 1 1 calc R . .
C52 C 0.34092(13) 0.63346(11) 0.6892(2) 0.0435(3) Uani 1 1 d . . .
H52 H 0.4157 0.6456 0.7419 0.052 Uiso 1 1 calc R . .
C54 C 0.15785(14) 0.62862(12) 0.7131(3) 0.0488(4) Uani 1 1 d . . .
C56 C 0.19126(14) 0.58108(14) 0.4267(3) 0.0544(4) Uani 1 1 d . . .
H56 H 0.1659 0.5582 0.3039 0.065 Uiso 1 1 calc R . .
C55 C 0.11804(15) 0.59566(15) 0.5318(3) 0.0597(5) Uani 1 1 d . . .
H55 H 0.0432 0.5833 0.4806 0.072 Uiso 1 1 calc R . .
C44 C 0.80710(16) 0.80893(17) 0.4988(4) 0.0715(6) Uani 1 1 d . . .
H44A H 0.8093 0.8165 0.369 0.086 Uiso 1 1 calc R . .
H44B H 0.856 0.7588 0.5555 0.086 Uiso 1 1 calc R . .
C45 C 0.84309(17) 0.89357(17) 0.6056(3) 0.0702(6) Uani 1 1 d . . .
H45A H 0.9172 0.9078 0.6051 0.105 Uiso 1 1 calc R . .
H45B H 0.8408 0.8855 0.7339 0.105 Uiso 1 1 calc R . .
H45C H 0.7948 0.943 0.5478 0.105 Uiso 1 1 calc R . .
N451 N 0.08027(15) 0.64200(14) 0.8255(3) 0.0691(5) Uani 1 1 d . . .
O542 O -0.01560(15) 0.6192(2) 0.7544(3) 0.1268(10) Uani 1 1 d . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3466(18) . ?
O1 N2 1.4177(19) . ?
O43 C42 1.310(2) . ?
O43 C44 1.459(2) . ?
O41 C41 1.2078(18) . ?
O42 C42 1.1908(19) . ?
N2 C3 1.288(2) . ?
C4 C5 1.368(2) . ?
C4 C3 1.428(2) . ?
C4 C41 1.457(2) . ?
C41 C42 1.534(2) . ?
C5 C51 1.467(2) . ?
O541 N451 1.218(3) . ?
C51 C56 1.391(2) . ?
C51 C52 1.391(2) . ?
C53 C54 1.377(2) . ?
C53 C52 1.384(2) . ?
C54 C55 1.370(3) . ?
C54 N451 1.465(2) . ?
C56 C55 1.382(3) . ?
C44 C45 1.462(3) . ?
N451 O542 1.220(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 O1 N2 109.25(12) . . ?
C42 O43 C44 117.20(15) . . ?
C3 N2 O1 105.20(12) . . ?
C5 C4 C3 103.75(13) . . ?
C5 C4 C41 129.04(13) . . ?
C3 C4 C41 126.86(13) . . ?
O41 C41 C4 123.92(14) . . ?
O41 C41 C42 119.15(13) . . ?
C4 C41 C42 116.90(12) . . ?
O42 C42 O43 126.75(15) . . ?
O42 C42 C41 122.42(14) . . ?
O43 C42 C41 110.73(13) . . ?
O1 C5 C4 109.10(13) . . ?
O1 C5 C51 114.32(13) . . ?
C4 C5 C51 136.58(13) . . ?
N2 C3 C4 112.69(15) . . ?
C56 C51 C52 119.89(14) . . ?
C56 C51 C5 118.87(14) . . ?
C52 C51 C5 121.20(13) . . ?
C54 C53 C52 118.29(15) . . ?
C53 C52 C51 120.25(15) . . ?
C55 C54 C53 122.81(16) . . ?
C55 C54 N451 118.54(17) . . ?
C53 C54 N451 118.65(17) . . ?
C55 C56 C51 120.03(16) . . ?
C54 C55 C56 118.74(16) . . ?
O43 C44 C45 108.60(17) . . ?
O542 N451 O541 123.6(2) . . ?
O542 N451 C54 117.6(2) . . ?
O541 N451 C54 118.72(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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1589620'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_date             2016-03-16T17:29:23-00:00
_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        
;
        ethyl 4-formyl-5-(4-nitrophenyl)isozaxole-3-carboxylate
;
_chemical_name_common            
'ethyl 4-formyl-5-(4-nitrophenyl)isozaxole-3-carboxylate'
_chemical_formula_moiety         'C13 H10 N2 O6'
_chemical_formula_sum            'C13 H10 N2 O6'
_chemical_formula_weight         290.23
_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                   5.8104(5)
_cell_length_b                   8.2881(8)
_cell_length_c                   13.1190(12)
_cell_angle_alpha                89.312(3)
_cell_angle_beta                 82.695(3)
_cell_angle_gamma                85.322(3)
_cell_volume                     624.56(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7233
_cell_measurement_theta_min      2.464
_cell_measurement_theta_max      30.346

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_special_details           
;
 none
;

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

_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.9348
_exptl_absorpt_correction_T_max  0.9691

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

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_number            6648
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_full        29.98
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3625
_reflns_number_gt                2149
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   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)+(0.0564P)²+0.0840P] 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         3625
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.056
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.069

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8431(2) 0.65307(16) 0.44238(10) 0.0233(3) Uani 1 1 d . . .
O32 O 1.1222(2) 0.80434(17) 0.16572(11) 0.0282(4) Uani 1 1 d . . .
O42 O 0.2463(2) 0.99076(16) 0.39248(11) 0.0282(4) Uani 1 1 d . . .
O31 O 0.7960(3) 0.96750(19) 0.16051(12) 0.0360(4) Uani 1 1 d . . .
O542 O 0.1631(3) 0.4726(2) 0.88019(12) 0.0382(4) Uani 1 1 d . . .
O541 O -0.1005(3) 0.6623(2) 0.85223(13) 0.0457(5) Uani 1 1 d . . .
N2 N 0.9688(3) 0.6922(2) 0.34828(13) 0.0239(4) Uani 1 1 d . . .
N541 N 0.0872(3) 0.5855(2) 0.82968(13) 0.0295(4) Uani 1 1 d . . .
C51 C 0.4891(3) 0.7034(2) 0.55103(15) 0.0188(4) Uani 1 1 d . . .
C53 C 0.1322(3) 0.7360(2) 0.66725(16) 0.0234(4) Uani 1 1 d . . .
H53 H -0.022 0.7837 0.6845 0.028 Uiso 1 1 calc R . .
C5 C 0.6322(3) 0.7390(2) 0.45429(15) 0.0194(4) Uani 1 1 d . . .
C56 C 0.5861(3) 0.5972(2) 0.62112(15) 0.0207(4) Uani 1 1 d . . .
H56 H 0.7414 0.5508 0.6053 0.025 Uiso 1 1 calc R . .
C4 C 0.6137(3) 0.8349(2) 0.36860(15) 0.0198(4) Uani 1 1 d . . .
C3 C 0.8323(3) 0.7987(2) 0.30629(15) 0.0213(4) Uani 1 1 d . . .
C52 C 0.2616(3) 0.7726(2) 0.57482(15) 0.0214(4) Uani 1 1 d . . .
H52 H 0.1954 0.8448 0.5277 0.026 Uiso 1 1 calc R . .
C55 C 0.4568(3) 0.5594(2) 0.71350(15) 0.0225(4) Uani 1 1 d . . .
H55 H 0.5213 0.4877 0.7614 0.027 Uiso 1 1 calc R . .
C54 C 0.2315(3) 0.6291(2) 0.73371(15) 0.0221(4) Uani 1 1 d . . .
C31 C 0.9127(3) 0.8680(2) 0.20270(15) 0.0238(4) Uani 1 1 d . . .
C41 C 0.4261(3) 0.9494(2) 0.33969(16) 0.0251(5) Uani 1 1 d . . .
H41 H 0.4488 0.9953 0.2728 0.03 Uiso 1 1 calc R . .
C33 C 1.2008(4) 0.8516(3) 0.05982(16) 0.0328(5) Uani 1 1 d . . .
H33A H 1.2362 0.9665 0.0573 0.039 Uiso 1 1 calc R . .
H33B H 1.0778 0.8381 0.0156 0.039 Uiso 1 1 calc R . .
C34 C 1.4132(4) 0.7458(3) 0.02328(18) 0.0396(6) Uani 1 1 d . . .
H34A H 1.4699 0.7748 -0.0476 0.059 Uiso 1 1 calc R . .
H34B H 1.3761 0.6325 0.0259 0.059 Uiso 1 1 calc R . .
H34C H 1.5339 0.7604 0.0674 0.059 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.358(2) . ?
O1 N2 1.4009(19) . ?
O32 C31 1.322(2) . ?
O32 C33 1.465(2) . ?
O42 C41 1.205(2) . ?
O31 C31 1.200(2) . ?
O542 N541 1.225(2) . ?
O541 N541 1.221(2) . ?
N2 C3 1.303(3) . ?
N541 C54 1.479(2) . ?
C51 C52 1.396(3) . ?
C51 C56 1.404(3) . ?
C51 C5 1.467(3) . ?
C53 C54 1.380(3) . ?
C53 C52 1.387(3) . ?
C5 C4 1.380(3) . ?
C56 C55 1.389(3) . ?
C4 C3 1.432(3) . ?
C4 C41 1.469(3) . ?
C3 C31 1.503(3) . ?
C55 C54 1.382(3) . ?
C33 C34 1.485(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 O1 N2 109.98(14) . . ?
C31 O32 C33 114.59(16) . . ?
C3 N2 O1 105.15(15) . . ?
O541 N541 O542 124.55(17) . . ?
O541 N541 C54 117.97(18) . . ?
O542 N541 C54 117.47(17) . . ?
C52 C51 C56 119.70(17) . . ?
C52 C51 C5 121.85(18) . . ?
C56 C51 C5 118.46(17) . . ?
C54 C53 C52 118.79(18) . . ?
O1 C5 C4 108.73(15) . . ?
O1 C5 C51 113.20(16) . . ?
C4 C5 C51 138.06(18) . . ?
C55 C56 C51 120.49(17) . . ?
C5 C4 C3 103.30(17) . . ?
C5 C4 C41 132.28(17) . . ?
C3 C4 C41 124.42(18) . . ?
N2 C3 C4 112.84(17) . . ?
N2 C3 C31 119.62(17) . . ?
C4 C3 C31 127.53(18) . . ?
C53 C52 C51 120.05(19) . . ?
C54 C55 C56 118.05(18) . . ?
C53 C54 C55 122.91(17) . . ?
C53 C54 N541 118.06(17) . . ?
C55 C54 N541 119.02(18) . . ?
O31 C31 O32 125.72(18) . . ?
O31 C31 C3 122.77(18) . . ?
O32 C31 C3 111.51(18) . . ?
O42 C41 C4 126.39(19) . . ?
O32 C33 C34 107.65(18) . . ?

####################################################################### 
# 
# 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_p-1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1589618'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_date             2015-11-24T09:56:13-00:00
_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        
;
ethyl 4-(4-nitrobenzoyl)isoxazol-5-carboxylate
;
_chemical_name_common            
'ethyl 4-(4-nitrobenzoyl)isoxazol-5-carboxylate'
_chemical_formula_moiety         'C13 H10 N2 O6'
_chemical_formula_sum            'C13 H10 N2 O6'
_chemical_formula_weight         290.23
_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                   6.6907(15)
_cell_length_b                   8.7715(16)
_cell_length_c                   12.002(4)
_cell_angle_alpha                97.212(18)
_cell_angle_beta                 93.54(2)
_cell_angle_gamma                107.759(18)
_cell_volume                     661.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9520
_cell_measurement_theta_min      3.731
_cell_measurement_theta_max      72.237

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_special_details           
;
 none
;

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

_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  0.8234

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

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_number            20722
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         72.58
_diffrn_reflns_theta_full        72.58
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2633
_reflns_number_gt                1815
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   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)+(0.0871P)²+0.2087P] 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       0.035(6)
_refine_ls_number_reflns         2633
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.06
_refine_ls_wR_factor_ref         0.1853
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3366(3) 0.6470(2) 1.03853(14) 0.0764(6) Uani 1 1 d . . .
O41 O 0.0730(3) 0.6050(2) 0.68629(16) 0.0860(6) Uani 1 1 d . . .
O52 O 0.1010(4) 0.2812(2) 0.85824(16) 0.0902(7) Uani 1 1 d . . .
O51 O 0.1828(4) 0.3247(3) 1.04585(18) 0.0963(7) Uani 1 1 d . . .
O451 O 0.7366(4) 0.1351(3) 0.4990(2) 0.1049(8) Uani 1 1 d . . .
O452 O 0.5144(4) 0.1279(3) 0.3578(2) 0.1155(9) Uani 1 1 d . . .
N2 N 0.4072(4) 0.8034(3) 1.0109(2) 0.0833(7) Uani 1 1 d . . .
N451 N 0.5874(5) 0.1686(3) 0.4571(2) 0.0851(7) Uani 1 1 d . . .
C47 C 0.4931(4) 0.4296(3) 0.70467(19) 0.0618(6) Uani 1 1 d . . .
H47 H 0.5559 0.4779 0.7771 0.074 Uiso 1 1 calc R . .
C42 C 0.3090(4) 0.4539(3) 0.66366(18) 0.0554(6) Uani 1 1 d . . .
C41 C 0.2092(4) 0.5606(3) 0.7301(2) 0.0593(6) Uani 1 1 d . . .
C5 C 0.2643(4) 0.5410(3) 0.9416(2) 0.0608(6) Uani 1 1 d . . .
C43 C 0.2158(4) 0.3816(3) 0.5555(2) 0.0665(7) Uani 1 1 d . . .
H43 H 0.0914 0.397 0.5281 0.08 Uiso 1 1 calc R . .
C51 C 0.1784(4) 0.3703(3) 0.9562(2) 0.0690(7) Uani 1 1 d . . .
C4 C 0.2825(4) 0.6210(3) 0.85203(19) 0.0582(6) Uani 1 1 d . . .
C44 C 0.3051(5) 0.2882(3) 0.4890(2) 0.0737(7) Uani 1 1 d . . .
H44 H 0.2433 0.2404 0.4163 0.088 Uiso 1 1 calc R . .
C3 C 0.3727(4) 0.7852(3) 0.9020(2) 0.0730(7) Uani 1 1 d . . .
H3 H 0.4037 0.871 0.8609 0.088 Uiso 1 1 calc R . .
C46 C 0.5840(4) 0.3335(3) 0.6381(2) 0.0676(7) Uani 1 1 d . . .
H46 H 0.7066 0.3152 0.6652 0.081 Uiso 1 1 calc R . .
C45 C 0.4882(4) 0.2660(3) 0.5311(2) 0.0661(7) Uani 1 1 d . . .
C53 C 0.0232(8) 0.1064(4) 0.8580(4) 0.1330(16) Uani 1 1 d . . .
H53A H 0.0974 0.0788 0.9205 0.16 Uiso 1 1 calc R . .
H53B H -0.1258 0.0738 0.8682 0.16 Uiso 1 1 calc R . .
C54 C 0.0527(9) 0.0234(4) 0.7573(4) 0.1364(16) Uani 1 1 d . . .
H54A H 0.0046 -0.0909 0.7598 0.205 Uiso 1 1 calc R . .
H54B H 0.1999 0.0569 0.7466 0.205 Uiso 1 1 calc R . .
H54C H -0.026 0.0468 0.6957 0.205 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.355(3) . ?
O1 N2 1.397(3) . ?
O41 C41 1.211(3) . ?
O52 C51 1.307(3) . ?
O52 C53 1.461(4) . ?
O51 C51 1.196(3) . ?
O451 N451 1.221(3) . ?
O452 N451 1.225(3) . ?
N2 C3 1.294(3) . ?
N451 C45 1.479(4) . ?
C47 C42 1.384(3) . ?
C47 C46 1.387(4) . ?
C42 C43 1.389(3) . ?
C42 C41 1.489(3) . ?
C41 C4 1.491(3) . ?
C5 C4 1.348(3) . ?
C5 C51 1.468(4) . ?
C43 C44 1.364(4) . ?
C4 C3 1.417(3) . ?
C44 C45 1.374(4) . ?
C46 C45 1.373(3) . ?
C53 C54 1.388(5) . ?

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 108.34(19) . . ?
C51 O52 C53 116.1(3) . . ?
C3 N2 O1 105.3(2) . . ?
O451 N451 O452 124.6(3) . . ?
O451 N451 C45 117.8(3) . . ?
O452 N451 C45 117.6(3) . . ?
C42 C47 C46 120.2(2) . . ?
C47 C42 C43 119.7(2) . . ?
C47 C42 C41 122.3(2) . . ?
C43 C42 C41 118.0(2) . . ?
O41 C41 C42 121.4(2) . . ?
O41 C41 C4 118.4(2) . . ?
C42 C41 C4 120.11(19) . . ?
C4 C5 O1 110.2(2) . . ?
C4 C5 C51 134.5(2) . . ?
O1 C5 C51 115.2(2) . . ?
C44 C43 C42 120.6(2) . . ?
O51 C51 O52 127.0(3) . . ?
O51 C51 C5 123.2(3) . . ?
O52 C51 C5 109.7(2) . . ?
C5 C4 C3 103.1(2) . . ?
C5 C4 C41 130.4(2) . . ?
C3 C4 C41 126.2(2) . . ?
C43 C44 C45 118.8(2) . . ?
N2 C3 C4 113.0(2) . . ?
C45 C46 C47 118.2(2) . . ?
C46 C45 C44 122.5(2) . . ?
C46 C45 N451 119.1(3) . . ?
C44 C45 N451 118.4(2) . . ?
C54 C53 O52 110.9(3) . . ?

####################################################################### 
# 
# 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_p21c_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1589619'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_date             2016-03-14T10:36:42-00:00
_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        
;
        ethyl4-(4-nitrobenzoyl)isoxazole-3-carboxylate
;
_chemical_name_common            
ethyl4-(4-nitrobenzoyl)isoxazole-3-carboxylate
_chemical_formula_moiety         'C13 H10 N2 O6'
_chemical_formula_sum            'C13 H10 N2 O6'
_chemical_formula_weight         290.23
_chemical_melting_point          none

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3487(2)
_cell_length_b                   17.1804(4)
_cell_length_c                   10.4508(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.1670(10)
_cell_angle_gamma                90
_cell_volume                     1306.07(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9842
_cell_measurement_theta_min      4.274
_cell_measurement_theta_max      72.186

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_special_details           
;
 none
;

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

_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.6907
_exptl_absorpt_correction_T_max  0.7624

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

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_number            22262
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.99
_diffrn_reflns_theta_max         72.24
_diffrn_reflns_theta_full        72.24
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2565
_reflns_number_gt                2260
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   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)+(0.0533P)²+0.3949P] 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         2565
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.84444(15) 0.43890(7) 1.03870(10) 0.0507(3) Uani 1 1 d . . .
O31 O 0.49635(17) 0.59672(7) 0.76124(10) 0.0538(3) Uani 1 1 d . . .
O32 O 0.57181(16) 0.64059(6) 0.96413(10) 0.0523(3) Uani 1 1 d . . .
O41 O 0.71333(19) 0.39164(7) 0.64253(11) 0.0634(4) Uani 1 1 d . . .
N2 N 0.74125(17) 0.50775(8) 1.03408(11) 0.0451(3) Uani 1 1 d . . .
O452 O 0.8929(2) 0.69188(9) 0.24553(12) 0.0788(4) Uani 1 1 d . . .
N451 N 0.91860(19) 0.70310(8) 0.36231(13) 0.0514(3) Uani 1 1 d . . .
O451 O 0.9781(2) 0.76394(8) 0.41128(14) 0.0795(4) Uani 1 1 d . . .
C42 C 0.79180(18) 0.52184(8) 0.60566(12) 0.0351(3) Uani 1 1 d . . .
C3 C 0.69621(19) 0.52285(8) 0.91083(13) 0.0373(3) Uani 1 1 d . . .
C4 C 0.76382(19) 0.46551(8) 0.83108(13) 0.0379(3) Uani 1 1 d . . .
C31 C 0.57667(19) 0.59093(8) 0.86876(13) 0.0391(3) Uani 1 1 d . . .
C47 C 0.7367(2) 0.51691(9) 0.47260(13) 0.0409(3) Uani 1 1 d . . .
H47 H 0.6717 0.4735 0.438 0.049 Uiso 1 1 calc R . .
C45 C 0.87498(19) 0.63932(8) 0.44670(14) 0.0395(3) Uani 1 1 d . . .
C44 C 0.9335(2) 0.64562(8) 0.57759(14) 0.0432(3) Uani 1 1 d . . .
H44 H 1 0.6888 0.6114 0.052 Uiso 1 1 calc R . .
C43 C 0.8908(2) 0.58623(8) 0.65720(13) 0.0407(3) Uani 1 1 d . . .
H43 H 0.9284 0.5893 0.7459 0.049 Uiso 1 1 calc R . .
C41 C 0.74953(19) 0.45551(8) 0.68833(14) 0.0395(3) Uani 1 1 d . . .
C46 C 0.7778(2) 0.57588(9) 0.39194(13) 0.0439(3) Uani 1 1 d . . .
H46 H 0.7411 0.573 0.3032 0.053 Uiso 1 1 calc R . .
C5 C 0.8533(2) 0.41555(9) 0.91764(14) 0.0456(4) Uani 1 1 d . . .
H5 H 0.9132 0.3708 0.896 0.055 Uiso 1 1 calc R . .
C33 C 0.4598(2) 0.71040(9) 0.93570(15) 0.0515(4) Uani 1 1 d . . .
H33A H 0.3361 0.6965 0.8973 0.062 Uiso 1 1 calc R . .
H33B H 0.513 0.7438 0.876 0.062 Uiso 1 1 calc R . .
C34 C 0.4567(3) 0.75105(10) 1.06206(17) 0.0619(5) Uani 1 1 d . . .
H34A H 0.3843 0.7976 1.0482 0.093 Uiso 1 1 calc R . .
H34B H 0.58 0.7644 1.0989 0.093 Uiso 1 1 calc R . .
H34C H 0.404 0.7173 1.1201 0.093 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3376(18) . ?
O1 N2 1.4021(17) . ?
O31 C31 1.1968(17) . ?
O32 C31 1.3164(17) . ?
O32 C33 1.4611(18) . ?
O41 C41 1.2115(17) . ?
N2 C3 1.3096(18) . ?
O452 N451 1.2234(18) . ?
N451 O451 1.2174(19) . ?
N451 C45 1.4703(18) . ?
C42 C43 1.3898(19) . ?
C42 C47 1.3946(18) . ?
C42 C41 1.4892(19) . ?
C3 C4 1.4246(19) . ?
C3 C31 1.491(2) . ?
C4 C5 1.348(2) . ?
C4 C41 1.4906(19) . ?
C47 C46 1.379(2) . ?
C45 C44 1.379(2) . ?
C45 C46 1.382(2) . ?
C44 C43 1.381(2) . ?
C33 C34 1.497(2) . ?

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 108.61(11) . . ?
C31 O32 C33 116.95(11) . . ?
C3 N2 O1 105.12(11) . . ?
O451 N451 O452 123.35(14) . . ?
O451 N451 C45 118.93(13) . . ?
O452 N451 C45 117.72(14) . . ?
C43 C42 C47 119.78(13) . . ?
C43 C42 C41 121.67(12) . . ?
C47 C42 C41 118.49(12) . . ?
N2 C3 C4 112.21(13) . . ?
N2 C3 C31 120.10(13) . . ?
C4 C3 C31 127.57(12) . . ?
C5 C4 C3 103.01(12) . . ?
C5 C4 C41 123.80(13) . . ?
C3 C4 C41 133.19(12) . . ?
O31 C31 O32 126.45(14) . . ?
O31 C31 C3 122.23(13) . . ?
O32 C31 C3 111.31(11) . . ?
C46 C47 C42 120.48(13) . . ?
C44 C45 C46 122.88(13) . . ?
C44 C45 N451 118.21(13) . . ?
C46 C45 N451 118.91(13) . . ?
C45 C44 C43 118.31(13) . . ?
C44 C43 C42 120.39(13) . . ?
O41 C41 C42 121.07(13) . . ?
O41 C41 C4 118.69(13) . . ?
C42 C41 C4 120.10(11) . . ?
C47 C46 C45 118.15(13) . . ?
O1 C5 C4 111.04(14) . . ?
O32 C33 C34 106.39(13) . . ?

