# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_kad_0m_5agustos2_a
_database_code_depnum_ccdc_archive 'CCDC 1987294'
loop_
_audit_author_name
_audit_author_address
'Ertan Sahin'
;Ataturk Univ,
Turkey
;
_audit_update_record             
;
2020-02-29 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;

_audit_creation_date             2020-02-28T18:50:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C8 H14 Cl N3 O2'
_chemical_formula_moiety         'C8 H14 Cl N3 O2'
_chemical_formula_weight         219.67

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
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                   20.7755(3)
_cell_length_b                   8.70320(10)
_cell_length_c                   22.9649(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4152.36(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    902
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      26.36

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.10
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             1856
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.722
_shelx_estimated_absorpt_T_max   0.934

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_number            128636
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.774
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             4247
_reflns_number_gt                3607
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_device_type  'rigaku R-axis rapid S'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?



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

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+2.3583P] where P=(Fo²+2Fc²)/3'
_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       0.00
_refine_ls_number_reflns         4247
_refine_ls_number_parameters     258
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.09074(3) 0.67975(9) 0.63203(3) 0.0821(2) Uani 1 d . .
Cl1 Cl 0.07474(4) 0.28518(10) 0.40209(3) 0.0866(2) Uani 1 d . .
O2 O 0.20730(7) 0.15680(15) 0.42717(6) 0.0503(3) Uani 1 d . .
H2 H 0.2087 0.0702 0.4131 0.075 Uiso 1 calc . .
O4 O 0.22014(7) 0.78286(16) 0.67847(6) 0.0528(3) Uani 1 d . .
H4O H 0.2442 0.7171 0.665 0.079 Uiso 1 calc . .
O3 O 0.22184(7) 0.61667(17) 0.87554(6) 0.0564(4) Uani 1 d . .
H5O H 0.2465 0.6823 0.8881 0.085 Uiso 1 calc . .
O1 O 0.20749(8) 0.05957(17) 0.63065(6) 0.0616(4) Uani 1 d . .
H1 H 0.2091 -0.0273 0.6444 0.092 Uiso 1 calc . .
N5 N 0.32347(7) 0.64120(18) 0.77171(7) 0.0472(4) Uani 1 d . .
N2 N 0.30537(7) 0.15789(19) 0.50594(7) 0.0480(4) Uani 1 d . .
N4 N 0.27741(7) 0.72416(17) 0.77651(8) 0.0483(4) Uani 1 d . .
N1 N 0.26240(8) 0.0772(2) 0.52632(8) 0.0571(5) Uani 1 d . .
C6 C 0.16279(8) 0.15893(19) 0.47405(7) 0.0362(4) Uani 1 d . .
H6 H 0.1341 0.0698 0.4712 0.043 Uiso 1 calc . .
C7 C 0.19924(8) 0.15492(19) 0.53359(7) 0.0362(4) Uani 1 d . .
H7 H 0.206 0.2601 0.5476 0.043 Uiso 1 calc . .
C10 C 0.17734(8) 0.71385(19) 0.71885(7) 0.0361(4) Uani 1 d . .
H10 H 0.1474 0.7932 0.7325 0.043 Uiso 1 calc . .
C17 C 0.21327(7) 0.64850(18) 0.77278(7) 0.0352(4) Uani 1 d . .
H17 H 0.2189 0.5373 0.7684 0.042 Uiso 1 calc . .
N3 N 0.34912(8) 0.2189(2) 0.48857(9) 0.0650(5) Uani 1 d . .
C8 C 0.16563(8) 0.0599(2) 0.58109(7) 0.0406(4) Uani 1 d . .
H8 H 0.1621 -0.046 0.567 0.049 Uiso 1 calc . .
C16 C 0.18139(8) 0.6830(2) 0.83161(7) 0.0414(4) Uani 1 d . .
H16 H 0.1813 0.7947 0.8371 0.05 Uiso 1 calc . .
C5 C 0.12383(9) 0.3061(2) 0.46633(8) 0.0430(4) Uani 1 d . .
H5 H 0.1549 0.3877 0.4578 0.052 Uiso 1 calc . .
C4 C 0.08236(9) 0.3643(2) 0.51564(9) 0.0477(4) Uani 1 d . .
H4A H 0.0652 0.4636 0.5044 0.057 Uiso 1 calc . .
H4B H 0.1099 0.3808 0.5492 0.057 Uiso 1 calc . .
C2 C 0.04448(9) 0.1067(2) 0.55836(9) 0.0500(5) Uani 1 d . .
H2A H 0.0567 0.0413 0.526 0.06 Uiso 1 calc . .
H2B H 0.007 0.0613 0.5767 0.06 Uiso 1 calc . .
C11 C 0.13790(9) 0.5889(2) 0.68815(8) 0.0466(4) Uani 1 d . .
H11 H 0.1687 0.521 0.6685 0.056 Uiso 1 calc . .
C1 C 0.09950(9) 0.1094(2) 0.60242(8) 0.0488(4) Uani 1 d . .
H1A H 0.1031 0.2131 0.6175 0.059 Uiso 1 calc . .
H1B H 0.0877 0.0435 0.6348 0.059 Uiso 1 calc . .
C12 C 0.09470(9) 0.4875(2) 0.72473(10) 0.0549(5) Uani 1 d . .
H12A H 0.0764 0.4098 0.6994 0.066 Uiso 1 calc . .
H12B H 0.1215 0.4346 0.7529 0.066 Uiso 1 calc . .
C15 C 0.11388(9) 0.6239(3) 0.84389(8) 0.0564(5) Uani 1 d . .
H15A H 0.1028 0.6521 0.8835 0.068 Uiso 1 calc . .
H15B H 0.1151 0.5126 0.8422 0.068 Uiso 1 calc . .
C3 C 0.02622(9) 0.2639(3) 0.53479(10) 0.0578(5) Uani 1 d . .
H3A H 0.0023 0.3183 0.5646 0.069 Uiso 1 calc . .
H3B H -0.0023 0.2497 0.5018 0.069 Uiso 1 calc . .
C14 C 0.05937(9) 0.6786(3) 0.80406(9) 0.0578(5) Uani 1 d . .
H14A H 0.022 0.7016 0.8278 0.069 Uiso 1 calc . .
H14B H 0.0726 0.7732 0.7852 0.069 Uiso 1 calc . .
C13 C 0.04010(9) 0.5630(3) 0.75739(10) 0.0635(6) Uani 1 d . .
H13A H 0.0146 0.4831 0.7756 0.076 Uiso 1 calc . .
H13B H 0.0127 0.6148 0.7294 0.076 Uiso 1 calc . .
N6 N 0.36999(9) 0.5766(3) 0.76769(13) 0.0923(8) Uani 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
Cl2 C11 1.8017(19) . ?
Cl1 C5 1.8026(18) . ?
O2 C6 1.4194(19) . ?
O4 C10 1.418(2) . ?
O3 C16 1.434(2) . ?
O1 C8 1.432(2) . ?
N5 N6 1.122(2) . ?
N5 N4 1.204(2) . ?
N2 N3 1.126(2) . ?
N2 N1 1.229(2) . ?
N4 C17 1.489(2) . ?
N1 C7 1.486(2) . ?
C6 C5 1.525(2) . ?
C6 C7 1.563(2) . ?
C7 C8 1.537(2) . ?
C10 C11 1.533(3) . ?
C10 C17 1.554(2) . ?
C17 C16 1.534(2) . ?
C8 C1 1.521(3) . ?
C16 C15 1.521(3) . ?
C5 C4 1.511(3) . ?
C4 C3 1.522(3) . ?
C2 C3 1.519(3) . ?
C2 C1 1.527(3) . ?
C11 C12 1.514(3) . ?
C12 C13 1.510(3) . ?
C15 C14 1.531(3) . ?
C14 C13 1.524(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
N6 N5 N4 173.1(2) . . ?
N3 N2 N1 172.48(19) . . ?
N5 N4 C17 116.16(14) . . ?
N2 N1 C7 115.09(15) . . ?
O2 C6 C5 105.57(14) . . ?
O2 C6 C7 110.33(13) . . ?
C5 C6 C7 112.18(13) . . ?
N1 C7 C8 103.65(14) . . ?
N1 C7 C6 109.86(14) . . ?
C8 C7 C6 114.38(13) . . ?
O4 C10 C11 109.55(14) . . ?
O4 C10 C17 112.02(13) . . ?
C11 C10 C17 111.33(13) . . ?
N4 C17 C16 104.42(14) . . ?
N4 C17 C10 108.30(13) . . ?
C16 C17 C10 115.00(13) . . ?
O1 C8 C1 107.05(15) . . ?
O1 C8 C7 106.82(14) . . ?
C1 C8 C7 119.14(15) . . ?
O3 C16 C15 105.88(14) . . ?
O3 C16 C17 106.71(14) . . ?
C15 C16 C17 119.68(15) . . ?
C4 C5 C6 119.81(15) . . ?
C4 C5 Cl1 108.95(13) . . ?
C6 C5 Cl1 108.10(12) . . ?
C5 C4 C3 117.44(17) . . ?
C3 C2 C1 114.18(17) . . ?
C12 C11 C10 118.38(15) . . ?
C12 C11 Cl2 109.30(13) . . ?
C10 C11 Cl2 107.96(13) . . ?
C8 C1 C2 117.30(15) . . ?
C13 C12 C11 117.85(18) . . ?
C16 C15 C14 117.78(16) . . ?
C2 C3 C4 115.37(16) . . ?
C13 C14 C15 114.1(2) . . ?
C12 C13 C14 116.06(16) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_azid30_tetra_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1987602'
loop_
_audit_author_name
_audit_author_address
'Ertan Sahin'
;Ataturk Univ,
Turkey
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;

_audit_creation_date             2020-03-02T19:06:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_absolute_configuration rm

_chemical_formula_moiety         'C14 H21 N3 O6'

_chemical_formula_sum            'C14 H21 N3 O6'
_chemical_formula_weight         327.34

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

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_Int_Tables_number      92
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   12.7747(4)
_cell_length_b                   12.7747(4)
_cell_length_c                   20.7228(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3381.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4881
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.85
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless


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

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1392
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.979

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_number            69563
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.873
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             3464
_reflns_number_gt                2870
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_device_type  'Rigaku R-axis'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 2300
_diffrn_standards_decay_%        89


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

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.5154P] where P=(Fo²+2Fc²)/3'
_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       0.0018(5)
_refine_ls_number_reflns         3464
_refine_ls_number_parameters     212
_refine_ls_number_restraints     53
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         0.0
_refine_ls_abs_structure_details 
;
 Flack x determined using 980 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.027

#----------------------------------------------------------------------------#
#                   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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.44528(15) 0.19715(14) 0.14643(9) 0.0506(5) Uani 1 d . .
O5 O 0.81781(14) 0.35853(16) 0.19232(8) 0.0516(5) Uani 1 d . .
O1 O 0.46095(16) 0.56315(14) 0.15142(9) 0.0558(5) Uani 1 d . .
O2 O 0.4043(2) 0.65815(19) 0.06790(13) 0.0836(8) Uani 1 d . .
O4 O 0.3671(2) 0.1193(2) 0.06294(12) 0.0861(8) Uani 1 d . .
N2 N 0.3179(2) 0.3608(2) 0.20627(15) 0.0642(7) Uani 1 d . .
N1 N 0.34739(19) 0.3845(2) 0.15211(14) 0.0635(7) Uani 1 d . .
O6 O 0.93228(18) 0.4568(2) 0.13898(12) 0.0901(8) Uani 1 d . .
C1 C 0.7422(2) 0.3683(2) 0.14009(12) 0.0439(6) Uani 1 d . .
H1 H 0.7801 0.3689 0.099 0.053 Uiso 1 calc . .
C13 C 0.9114(2) 0.4043(2) 0.18509(14) 0.0514(7) Uani 1 d . .
C2 C 0.6780(2) 0.2684(2) 0.14410(13) 0.0472(6) Uani 1 d . .
H2A H 0.6405 0.268 0.1848 0.057 Uiso 1 calc . .
H2B H 0.7254 0.2091 0.1442 0.057 Uiso 1 calc . .
C7 C 0.6085(2) 0.4968(2) 0.09274(14) 0.0516(7) Uani 1 d . .
H7A H 0.6186 0.5692 0.0803 0.062 Uiso 1 calc . .
H7B H 0.6266 0.4537 0.0558 0.062 Uiso 1 calc . .
C5 C 0.4626(2) 0.3797(2) 0.14240(13) 0.0452(6) Uani 1 d . .
H5 H 0.4977 0.3769 0.1844 0.054 Uiso 1 calc . .
C8 C 0.6846(2) 0.4716(2) 0.14739(14) 0.0495(7) Uani 1 d . .
H8A H 0.7358 0.5275 0.1502 0.059 Uiso 1 calc . .
H8B H 0.646 0.4704 0.1877 0.059 Uiso 1 calc . .
C4 C 0.4858(2) 0.2789(2) 0.10464(13) 0.0476(6) Uani 1 d . .
H4 H 0.4455 0.2794 0.0644 0.057 Uiso 1 calc . .
C6 C 0.4929(2) 0.4804(2) 0.10774(13) 0.0474(6) Uani 1 d . .
H6 H 0.4525 0.486 0.0677 0.057 Uiso 1 calc . .
C3 C 0.5989(2) 0.2537(2) 0.08938(13) 0.0511(7) Uani 1 d . .
H3A H 0.6205 0.2971 0.0534 0.061 Uiso 1 calc . .
H3B H 0.6025 0.1814 0.0752 0.061 Uiso 1 calc . .
C9 C 0.4192(2) 0.6498(2) 0.12457(17) 0.0566(8) Uani 1 d . .
C11 C 0.3856(2) 0.1216(2) 0.11987(16) 0.0533(7) Uani 1 d . .
C12 C 0.3486(3) 0.0464(3) 0.16854(17) 0.0679(9) Uani 1 d . .
H12A H 0.3037 -0.0042 0.1484 0.102 Uiso 1 calc . .
H12B H 0.3104 0.083 0.2014 0.102 Uiso 1 calc . .
H12C H 0.4075 0.0115 0.1876 0.102 Uiso 1 calc . .
N3 N 0.2809(3) 0.3398(3) 0.25356(19) 0.1077(13) Uani 1 d . .
C10 C 0.3954(3) 0.7311(3) 0.17396(19) 0.0818(11) Uani 1 d . .
H10A H 0.3845 0.7973 0.1531 0.123 Uiso 1 calc . .
H10B H 0.453 0.7367 0.2035 0.123 Uiso 1 calc . .
H10C H 0.3333 0.7117 0.1972 0.123 Uiso 1 calc . .
C14 C 0.9808(3) 0.3847(3) 0.24055(15) 0.0663(8) Uani 1 d . .
H14A H 1.0381 0.4333 0.2396 0.099 Uiso 1 calc . .
H14B H 1.0074 0.3145 0.2383 0.099 Uiso 1 calc . .
H14C H 0.9421 0.3935 0.2799 0.099 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
O3 C11 1.348(3) . ?
O3 C4 1.452(3) . ?
O5 C13 1.339(3) . ?
O5 C1 1.456(3) . ?
O1 C9 1.349(4) . ?
O1 C6 1.450(3) . ?
O2 C9 1.194(4) . ?
O4 C11 1.203(4) . ?
N2 N3 1.121(4) . ?
N2 N1 1.222(4) . ?
N1 C5 1.487(4) . ?
O6 C13 1.198(3) . ?
C1 C8 1.518(4) . ?
C1 C2 1.520(4) . ?
C1 H1 0.98 . ?
C13 C14 1.473(4) . ?
C2 C3 1.530(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C7 C6 1.524(4) . ?
C7 C8 1.527(4) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C5 C6 1.523(4) . ?
C5 C4 1.536(4) . ?
C5 H5 0.98 . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C4 C3 1.513(4) . ?
C4 H4 0.98 . ?
C6 H6 0.98 . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C9 C10 1.490(5) . ?
C11 C12 1.470(4) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 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
C11 O3 C4 118.2(2) . . ?
C13 O5 C1 118.1(2) . . ?
C9 O1 C6 116.9(2) . . ?
N3 N2 N1 173.0(4) . . ?
N2 N1 C5 114.8(2) . . ?
O5 C1 C8 108.8(2) . . ?
O5 C1 C2 104.2(2) . . ?
C8 C1 C2 117.5(2) . . ?
O5 C1 H1 108.7 . . ?
C8 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
O6 C13 O5 122.2(3) . . ?
O6 C13 C14 125.7(3) . . ?
O5 C13 C14 112.1(2) . . ?
C1 C2 C3 114.8(2) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.5 . . ?
C6 C7 C8 115.9(2) . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N1 C5 C6 106.3(2) . . ?
N1 C5 C4 107.1(2) . . ?
C6 C5 C4 114.8(2) . . ?
N1 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C1 C8 C7 114.7(2) . . ?
C1 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C1 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
O3 C4 C3 108.2(2) . . ?
O3 C4 C5 103.3(2) . . ?
C3 C4 C5 118.0(2) . . ?
O3 C4 H4 109 . . ?
C3 C4 H4 109 . . ?
C5 C4 H4 109 . . ?
O1 C6 C5 104.5(2) . . ?
O1 C6 C7 107.5(2) . . ?
C5 C6 C7 117.3(2) . . ?
O1 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
C7 C6 H6 109.1 . . ?
C4 C3 C2 116.7(2) . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C2 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
O2 C9 O1 122.8(3) . . ?
O2 C9 C10 125.5(3) . . ?
O1 C9 C10 111.7(3) . . ?
O4 C11 O3 121.9(3) . . ?
O4 C11 C12 126.4(3) . . ?
O3 C11 C12 111.7(3) . . ?
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 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C13 O5 C1 C8 -84.0(3) . . . . ?
C13 O5 C1 C2 149.8(2) . . . . ?
C1 O5 C13 O6 3.9(4) . . . . ?
C1 O5 C13 C14 -178.0(2) . . . . ?
O5 C1 C2 C3 -174.0(2) . . . . ?
C8 C1 C2 C3 65.6(3) . . . . ?
N2 N1 C5 C6 -133.8(3) . . . . ?
N2 N1 C5 C4 103.1(3) . . . . ?
O5 C1 C8 C7 175.3(2) . . . . ?
C2 C1 C8 C7 -66.6(3) . . . . ?
C6 C7 C8 C1 103.4(3) . . . . ?
C11 O3 C4 C3 -100.6(3) . . . . ?
C11 O3 C4 C5 133.6(2) . . . . ?
N1 C5 C4 O3 -59.5(3) . . . . ?
C6 C5 C4 O3 -177.2(2) . . . . ?
N1 C5 C4 C3 -178.8(2) . . . . ?
C6 C5 C4 C3 63.5(3) . . . . ?
C9 O1 C6 C5 -141.3(2) . . . . ?
C9 O1 C6 C7 93.4(3) . . . . ?
N1 C5 C6 O1 60.1(3) . . . . ?
C4 C5 C6 O1 178.3(2) . . . . ?
N1 C5 C6 C7 178.9(2) . . . . ?
C4 C5 C6 C7 -62.9(3) . . . . ?
C8 C7 C6 O1 72.3(3) . . . . ?
C8 C7 C6 C5 -44.9(3) . . . . ?
O3 C4 C3 C2 -72.3(3) . . . . ?
C5 C4 C3 C2 44.4(3) . . . . ?
C1 C2 C3 C4 -101.4(3) . . . . ?
C6 O1 C9 O2 3.1(4) . . . . ?
C6 O1 C9 C10 -176.7(3) . . . . ?
C4 O3 C11 O4 1.4(4) . . . . ?
C4 O3 C11 C12 -178.6(2) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
