# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 915054'
_audit_update_record             
;
2012-12-10 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
#TrackingRef 'akso.cif'


_audit_creation_method           SHELXL-97
_pub_contact_author_name         'Chiranjeev Sharma Neupane'
_pub1_contact_author_e-mail      awasthisatish@yahoo.com
_pub1_contact_author_phone       +91-11-27667794
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 Cl F N O3'
_chemical_formula_sum            'C15 H15 Cl F N O3'
_chemical_formula_weight         311.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.3931(6)
_cell_length_b                   11.4141(7)
_cell_length_c                   12.5948(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.798(6)
_cell_angle_gamma                90.00
_cell_volume                     1467.64(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.2867
_cell_measurement_theta_max      29.1611

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87464
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12618
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3003
_reflns_number_gt                2639
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0532P)²+0.4144P] 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       ?
_refine_ls_number_reflns         3003
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

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
Cl Cl 0.00821(5) 0.34448(5) 0.58305(5) 0.0682(2) Uani 1 1 d . . .
O1 O -0.58783(12) 0.14752(12) 0.37121(9) 0.0506(3) Uani 1 1 d . . .
N N -0.40107(11) 0.16595(11) 0.68774(9) 0.0312(3) Uani 1 1 d . . .
C1 C -0.52305(14) 0.12478(13) 0.66063(12) 0.0330(3) Uani 1 1 d . . .
H1 H -0.5630 0.0984 0.7163 0.040 Uiso 1 1 calc R . .
O3 O -0.76172(11) 0.04219(13) 0.63678(10) 0.0533(3) Uani 1 1 d . . .
C8 C -0.33593(14) 0.20402(12) 0.60739(11) 0.0302(3) Uani 1 1 d . . .
C3 C -0.53555(15) 0.15231(13) 0.46751(12) 0.0351(3) Uani 1 1 d . . .
C2 C -0.59441(14) 0.11810(13) 0.55741(12) 0.0340(3) Uani 1 1 d . . .
C7 C -0.20866(15) 0.24945(13) 0.63384(12) 0.0355(3) Uani 1 1 d . . .
H7 H -0.1663 0.2544 0.7056 0.043 Uiso 1 1 calc R . .
C13 C -0.33511(15) 0.16343(15) 0.80247(12) 0.0364(4) Uani 1 1 d . . .
H13A H -0.4006 0.1589 0.8480 0.044 Uiso 1 1 calc R . .
H13B H -0.2863 0.2355 0.8198 0.044 Uiso 1 1 calc R . .
C9 C -0.40012(15) 0.19708(13) 0.49896(12) 0.0325(3) Uani 1 1 d . . .
F F -0.14901(13) 0.31742(13) 0.36762(10) 0.0756(4) Uani 1 1 d . . .
C6 C -0.14760(16) 0.28640(15) 0.55263(14) 0.0421(4) Uani 1 1 d . . .
C4 C -0.33447(17) 0.23574(15) 0.41833(13) 0.0432(4) Uani 1 1 d . . .
H4 H -0.3752 0.2317 0.3461 0.052 Uiso 1 1 calc R . .
O2 O -0.80679(13) 0.07050(16) 0.45873(11) 0.0741(5) Uani 1 1 d . . .
C5 C -0.21158(18) 0.27902(16) 0.44560(14) 0.0475(4) Uani 1 1 d . . .
C10 C -0.73088(16) 0.07564(15) 0.54262(14) 0.0409(4) Uani 1 1 d . . .
C14 C -0.24291(19) 0.06031(17) 0.82633(15) 0.0520(5) Uani 1 1 d . . .
H14A H -0.1727 0.0685 0.7858 0.062 Uiso 1 1 calc R . .
H14B H -0.2900 -0.0114 0.8032 0.062 Uiso 1 1 calc R . .
C11 C -0.89349(16) 0.00121(18) 0.63475(17) 0.0535(5) Uani 1 1 d . . .
H11A H -0.9153 -0.0604 0.5814 0.064 Uiso 1 1 calc R . .
H11B H -0.9554 0.0649 0.6161 0.064 Uiso 1 1 calc R . .
C15 C -0.1853(2) 0.0524(2) 0.94583(18) 0.0716(7) Uani 1 1 d . . .
H15A H -0.1273 -0.0136 0.9587 0.107 Uiso 1 1 calc R . .
H15B H -0.2546 0.0431 0.9859 0.107 Uiso 1 1 calc R . .
H15C H -0.1374 0.1228 0.9686 0.107 Uiso 1 1 calc R . .
C12 C -0.8995(2) -0.0444(2) 0.74472(19) 0.0734(6) Uani 1 1 d . . .
H12A H -0.9865 -0.0718 0.7460 0.110 Uiso 1 1 calc R . .
H12B H -0.8773 0.0172 0.7969 0.110 Uiso 1 1 calc R . .
H12C H -0.8386 -0.1079 0.7620 0.110 Uiso 1 1 calc R . .


_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
Cl C6 1.7251(17) . ?
O1 C3 1.2339(18) . ?
N C1 1.3351(19) . ?
N C8 1.3886(19) . ?
N C13 1.4790(18) . ?
C1 C2 1.373(2) . ?
C1 H1 0.9300 . ?
O3 C10 1.341(2) . ?
O3 C11 1.443(2) . ?
C8 C7 1.401(2) . ?
C8 C9 1.405(2) . ?
C3 C2 1.438(2) . ?
C3 C9 1.480(2) . ?
C2 C10 1.477(2) . ?
C7 C6 1.367(2) . ?
C7 H7 0.9300 . ?
C13 C14 1.512(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C9 C4 1.397(2) . ?
F C5 1.3487(19) . ?
C6 C5 1.389(2) . ?
C4 C5 1.352(3) . ?
C4 H4 0.9300 . ?
O2 C10 1.196(2) . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C11 C12 1.492(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C1 N C8 119.54(12) . . ?
C1 N C13 119.15(12) . . ?
C8 N C13 121.20(12) . . ?
N C1 C2 125.48(14) . . ?
N C1 H1 117.3 . . ?
C2 C1 H1 117.3 . . ?
C10 O3 C11 117.39(14) . . ?
N C8 C7 120.65(13) . . ?
N C8 C9 118.89(13) . . ?
C7 C8 C9 120.46(14) . . ?
O1 C3 C2 126.01(15) . . ?
O1 C3 C9 120.00(15) . . ?
C2 C3 C9 113.99(12) . . ?
C1 C2 C3 119.76(14) . . ?
C1 C2 C10 118.24(15) . . ?
C3 C2 C10 121.99(14) . . ?
C6 C7 C8 119.07(14) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
N C13 C14 111.71(13) . . ?
N C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C4 C9 C8 118.76(14) . . ?
C4 C9 C3 118.96(14) . . ?
C8 C9 C3 122.28(14) . . ?
C7 C6 C5 120.14(15) . . ?
C7 C6 Cl 120.02(13) . . ?
C5 C6 Cl 119.83(13) . . ?
C5 C4 C9 119.83(15) . . ?
C5 C4 H4 120.1 . . ?
C9 C4 H4 120.1 . . ?
F C5 C4 119.67(16) . . ?
F C5 C6 118.58(16) . . ?
C4 C5 C6 121.74(15) . . ?
O2 C10 O3 122.70(16) . . ?
O2 C10 C2 125.90(17) . . ?
O3 C10 C2 111.40(13) . . ?
C13 C14 C15 111.20(17) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O3 C11 C12 107.54(16) . . ?
O3 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 . . ?

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
C8 N C1 C2 -1.4(2) . . . . ?
C13 N C1 C2 -177.75(14) . . . . ?
C1 N C8 C7 178.92(13) . . . . ?
C13 N C8 C7 -4.8(2) . . . . ?
C1 N C8 C9 -0.6(2) . . . . ?
C13 N C8 C9 175.66(13) . . . . ?
N C1 C2 C3 3.0(2) . . . . ?
N C1 C2 C10 -176.91(14) . . . . ?
O1 C3 C2 C1 177.98(15) . . . . ?
C9 C3 C2 C1 -2.3(2) . . . . ?
O1 C3 C2 C10 -2.1(2) . . . . ?
C9 C3 C2 C10 177.55(13) . . . . ?
N C8 C7 C6 -179.83(14) . . . . ?
C9 C8 C7 C6 -0.3(2) . . . . ?
C1 N C13 C14 99.41(16) . . . . ?
C8 N C13 C14 -76.87(18) . . . . ?
N C8 C9 C4 179.83(13) . . . . ?
C7 C8 C9 C4 0.3(2) . . . . ?
N C8 C9 C3 1.0(2) . . . . ?
C7 C8 C9 C3 -178.55(13) . . . . ?
O1 C3 C9 C4 1.4(2) . . . . ?
C2 C3 C9 C4 -178.36(13) . . . . ?
O1 C3 C9 C8 -179.80(14) . . . . ?
C2 C3 C9 C8 0.5(2) . . . . ?
C8 C7 C6 C5 0.2(2) . . . . ?
C8 C7 C6 Cl 179.14(12) . . . . ?
C8 C9 C4 C5 -0.1(2) . . . . ?
C3 C9 C4 C5 178.75(15) . . . . ?
C9 C4 C5 F -179.30(15) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C7 C6 C5 F 179.30(15) . . . . ?
Cl C6 C5 F 0.3(2) . . . . ?
C7 C6 C5 C4 0.0(3) . . . . ?
Cl C6 C5 C4 -178.99(14) . . . . ?
C11 O3 C10 O2 -1.4(3) . . . . ?
C11 O3 C10 C2 178.57(14) . . . . ?
C1 C2 C10 O2 176.08(18) . . . . ?
C3 C2 C10 O2 -3.8(3) . . . . ?
C1 C2 C10 O3 -3.9(2) . . . . ?
C3 C2 C10 O3 176.19(14) . . . . ?
N C13 C14 C15 -174.91(15) . . . . ?
C10 O3 C11 C12 173.12(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.036


####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 916682'
_audit_update_record             
;
2012-12-20 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
#TrackingRef 'joc-6.cif'


_audit_creation_method           SHELXL-97

loop_
_pub_contact_author_name
'Chiranjeev Sharma Neupane'
'Ashawani Kumar Singh'
'Satish Kumar Awasthi'
_pub1_contact_author_e-mail      awasthisatish@yahoo.com
_pub1_contact_author_phone       +91-11-27667794
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Cl2 N1 O4'
_chemical_formula_sum            'C14 H15 Cl2 N1 O4'
_chemical_formula_weight         332.17

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   14.5283(9)
_cell_length_b                   6.1794(4)
_cell_length_c                   17.9542(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.022(7)
_cell_angle_gamma                90.00
_cell_volume                     1582.13(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4227
_cell_measurement_theta_min      3.2740
_cell_measurement_theta_max      28.9222

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12132
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3241
_reflns_number_gt                2662
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1573P)²+1.1559P] 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       ?
_refine_ls_number_reflns         3236
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.2059
_refine_ls_wR_factor_gt          0.1889
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_restrained_S_all      0.824
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.030

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.05294(5) 0.19244(16) 0.58011(6) 0.0861(4) Uani 1 1 d . . .
Cl2 Cl 0.25808(10) 0.81523(15) 0.48362(6) 0.1015(4) Uani 1 1 d . . .
O3 O 0.19082(12) -0.5133(3) 0.79574(11) 0.0545(5) Uani 1 1 d . . .
N N 0.23064(13) 0.0447(3) 0.67323(11) 0.0460(5) Uani 1 1 d . . .
H0 H 0.1745 -0.0021 0.6716 0.055 Uiso 1 1 calc . . .
O2 O 0.36825(14) -0.5218(4) 0.83423(14) 0.0803(7) Uani 1 1 d . . .
O4 O 0.12528(14) -0.2534(4) 0.71855(14) 0.0740(7) Uani 1 1 d . . .
C13 C 0.1652(2) 0.4986(4) 0.54026(15) 0.0581(7) Uani 1 1 d . . .
H13 H 0.1112 0.5557 0.5104 0.070 Uiso 1 1 calc R . .
C6 C 0.19490(16) -0.3367(4) 0.75487(14) 0.0454(6) Uani 1 1 d . . .
C12 C 0.2504(2) 0.5922(4) 0.54151(16) 0.0596(7) Uani 1 1 d . . .
C7 C 0.28928(16) -0.2494(4) 0.75703(13) 0.0451(6) Uani 1 1 d . . .
C8 C 0.29939(16) -0.0659(4) 0.71660(13) 0.0465(6) Uani 1 1 d . . .
H8 H 0.3600 -0.0135 0.7197 0.056 Uiso 1 1 calc R . .
C3 C 0.37776(18) -0.3427(5) 0.79758(17) 0.0578(7) Uani 1 1 d . . .
C9 C 0.23992(16) 0.2286(4) 0.63011(13) 0.0420(5) Uani 1 1 d . . .
C11 C 0.3302(2) 0.5104(5) 0.58619(17) 0.0642(8) Uani 1 1 d . . .
H11 H 0.3878 0.5764 0.5864 0.077 Uiso 1 1 calc R . .
O1 O 0.45337(16) -0.2658(6) 0.7970(2) 0.1141(12) Uani 1 1 d . . .
C14 C 0.16067(18) 0.3169(4) 0.58444(15) 0.0494(6) Uani 1 1 d . . .
C5 C 0.0987(2) -0.6015(6) 0.79723(19) 0.0663(8) Uani 1 1 d . . .
H5A H 0.0705 -0.6570 0.7476 0.080 Uiso 1 1 calc R . .
H5B H 0.0582 -0.4897 0.8111 0.080 Uiso 1 1 calc R . .
C2 C 0.4507(2) -0.6240(8) 0.8770(3) 0.0998(14) Uani 1 1 d . . .
H2A H 0.4915 -0.5170 0.9059 0.120 Uiso 1 1 calc R . .
H2B H 0.4852 -0.6974 0.8431 0.120 Uiso 1 1 calc R . .
C10 C 0.32508(19) 0.3312(4) 0.63053(16) 0.0542(6) Uani 1 1 d . . .
H10 H 0.3793 0.2779 0.6612 0.065 Uiso 1 1 calc R . .
C4 C 0.1104(3) -0.7773(7) 0.8537(2) 0.0844(11) Uani 1 1 d . . .
H4A H 0.0503 -0.8390 0.8558 0.127 Uiso 1 1 calc R . .
H4B H 0.1380 -0.7205 0.9027 0.127 Uiso 1 1 calc R . .
H4C H 0.1505 -0.8870 0.8395 0.127 Uiso 1 1 calc R . .
C1 C 0.4186(3) -0.7807(9) 0.9283(3) 0.1184(19) Uani 1 1 d . . .
H1A H 0.4717 -0.8537 0.9576 0.178 Uiso 1 1 calc R . .
H1B H 0.3778 -0.8847 0.8990 0.178 Uiso 1 1 calc R . .
H1C H 0.3852 -0.7058 0.9617 0.178 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.732(3) . ?
Cl2 C12 1.742(3) . ?
O3 C6 1.322(3) . ?
O3 C5 1.450(3) . ?
N C8 1.332(3) . ?
N C9 1.396(3) . ?
N H0 0.8601 . ?
O2 C3 1.309(3) . ?
O2 C2 1.440(3) . ?
O4 C6 1.209(3) . ?
C13 C12 1.363(4) . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C6 C7 1.467(3) . ?
C12 C11 1.374(5) . ?
C7 C8 1.369(4) . ?
C7 C3 1.469(3) . ?
C8 H8 0.9300 . ?
C3 O1 1.198(4) . ?
C9 C14 1.391(3) . ?
C9 C10 1.389(3) . ?
C11 C10 1.374(4) . ?
C11 H11 0.9300 . ?
C5 C4 1.474(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 C1 1.473(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 H10 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O3 C5 117.4(2) . . ?
C8 N C9 126.9(2) . . ?
C8 N H0 116.5 . . ?
C9 N H0 116.5 . . ?
C3 O2 C2 118.8(3) . . ?
C12 C13 C14 118.5(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.8 . . ?
O4 C6 O3 121.9(2) . . ?
O4 C6 C7 122.6(2) . . ?
O3 C6 C7 115.4(2) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 Cl2 119.1(2) . . ?
C11 C12 Cl2 119.8(2) . . ?
C8 C7 C3 114.5(2) . . ?
C8 C7 C6 119.0(2) . . ?
C3 C7 C6 126.4(2) . . ?
N C8 C7 126.2(2) . . ?
N C8 H8 116.9 . . ?
C7 C8 H8 116.9 . . ?
O1 C3 O2 121.6(2) . . ?
O1 C3 C7 123.9(3) . . ?
O2 C3 C7 114.5(2) . . ?
C14 C9 C10 117.4(2) . . ?
C14 C9 N 119.3(2) . . ?
C10 C9 N 123.3(2) . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C9 C14 C13 122.1(2) . . ?
C9 C14 Cl1 119.43(19) . . ?
C13 C14 Cl1 118.4(2) . . ?
O3 C5 C4 107.7(2) . . ?
O3 C5 H5A 110.2 . . ?
C4 C5 H5A 110.2 . . ?
O3 C5 H5B 110.2 . . ?
C4 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
O2 C2 C1 106.9(3) . . ?
O2 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
O2 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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 O3 C6 O4 -1.6(4) . . . . ?
C5 O3 C6 C7 178.1(2) . . . . ?
C14 C13 C12 C11 -0.8(4) . . . . ?
C14 C13 C12 Cl2 177.7(2) . . . . ?
O4 C6 C7 C8 0.2(4) . . . . ?
O3 C6 C7 C8 -179.5(2) . . . . ?
O4 C6 C7 C3 -178.1(3) . . . . ?
O3 C6 C7 C3 2.1(4) . . . . ?
C9 N C8 C7 -178.2(2) . . . . ?
C3 C7 C8 N 177.6(2) . . . . ?
C6 C7 C8 N -0.9(4) . . . . ?
C2 O2 C3 O1 2.2(6) . . . . ?
C2 O2 C3 C7 -178.9(3) . . . . ?
C8 C7 C3 O1 1.0(5) . . . . ?
C6 C7 C3 O1 179.3(3) . . . . ?
C8 C7 C3 O2 -177.9(3) . . . . ?
C6 C7 C3 O2 0.5(4) . . . . ?
C8 N C9 C14 176.3(2) . . . . ?
C8 N C9 C10 -4.1(4) . . . . ?
C13 C12 C11 C10 0.1(5) . . . . ?
Cl2 C12 C11 C10 -178.3(2) . . . . ?
C10 C9 C14 C13 0.5(4) . . . . ?
N C9 C14 C13 -179.9(2) . . . . ?
C10 C9 C14 Cl1 178.6(2) . . . . ?
N C9 C14 Cl1 -1.8(3) . . . . ?
C12 C13 C14 C9 0.5(4) . . . . ?
C12 C13 C14 Cl1 -177.7(2) . . . . ?
C6 O3 C5 C4 -172.5(3) . . . . ?
C3 O2 C2 C1 164.3(4) . . . . ?
C12 C11 C10 C9 0.9(4) . . . . ?
C14 C9 C10 C11 -1.2(4) . . . . ?
N C9 C10 C11 179.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.040


####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 920032'
_audit_update_record             
;
2013-01-15 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
#TrackingRef 'joc-2-2.cif'


_audit_creation_method           SHELXL-97


loop_
_pub_contact_author_name
'Chiranjeev Sharma Neupane'
'Ashawani Kumar Singh'
'Satish Kumar Awasthi'
_publ_contact_author_e-mail      awasthisatish@yahoo.com
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N O6'
_chemical_formula_sum            'C16 H21 N O6'
_chemical_formula_weight         323.34

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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   4.5426(5)
_cell_length_b                   16.585(2)
_cell_length_c                   22.273(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.979(12)
_cell_angle_gamma                90.00
_cell_volume                     1675.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1929
_cell_measurement_theta_min      3.6566
_cell_measurement_theta_max      29.1255

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13399
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3307
_reflns_number_gt                2388
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0744P)²+0.3842P] 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       ?
_refine_ls_number_reflns         3307
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.007

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
O6 O -0.1633(4) 0.15489(11) 0.95579(9) 0.0587(5) Uani 1 1 d . . .
O2 O 0.5896(5) -0.03633(11) 0.80324(9) 0.0667(6) Uani 1 1 d . . .
O5 O -0.2451(4) 0.29504(11) 0.90749(9) 0.0596(6) Uani 1 1 d . . .
O3 O 0.1164(5) 0.06621(11) 0.91006(9) 0.0677(6) Uani 1 1 d . . .
O4 O -0.1113(5) 0.31147(12) 0.81446(10) 0.0767(7) Uani 1 1 d . . .
O1 O 0.9035(5) 0.19617(13) 0.64279(11) 0.0847(8) Uani 1 1 d . . .
N N 0.3794(4) 0.11009(12) 0.81154(9) 0.0462(5) Uani 1 1 d . . .
H0 H 0.3629 0.0725 0.8378 0.055 Uiso 1 1 calc . . .
C6 C 0.6791(6) 0.01645(15) 0.76092(12) 0.0488(7) Uani 1 1 d . . .
C7 C 0.5682(5) 0.09451(15) 0.76483(11) 0.0424(6) Uani 1 1 d . . .
C9 C 0.2241(5) 0.17656(14) 0.81940(11) 0.0437(6) Uani 1 1 d . . .
H9 H 0.2391 0.2165 0.7904 0.052 Uiso 1 1 calc R . .
C10 C 0.0444(5) 0.19328(14) 0.86512(11) 0.0425(6) Uani 1 1 d . . .
C8 C 0.6489(5) 0.15215(16) 0.72482(12) 0.0516(7) Uani 1 1 d . . .
H8 H 0.5772 0.2044 0.7280 0.062 Uiso 1 1 calc R . .
C12 C 0.0055(5) 0.13291(15) 0.91157(12) 0.0468(6) Uani 1 1 d . . .
C11 C -0.1090(5) 0.27089(15) 0.85945(12) 0.0483(7) Uani 1 1 d . . .
C3 C 0.8370(6) 0.13332(17) 0.67953(13) 0.0547(7) Uani 1 1 d . . .
C5 C 0.8681(6) -0.00127(17) 0.71613(13) 0.0594(8) Uani 1 1 d . . .
H5 H 0.9444 -0.0531 0.7134 0.071 Uiso 1 1 calc R . .
C13 C -0.2294(7) 0.09314(17) 0.99883(13) 0.0639(8) Uani 1 1 d . . .
H13A H -0.0485 0.0710 1.0171 0.077 Uiso 1 1 calc R . .
H13B H -0.3401 0.0498 0.9791 0.077 Uiso 1 1 calc R . .
C4 C 0.9457(6) 0.05672(18) 0.67531(13) 0.0587(8) Uani 1 1 d . . .
H4 H 1.0713 0.0437 0.6451 0.070 Uiso 1 1 calc R . .
C15 C -0.4015(7) 0.37075(17) 0.90207(15) 0.0710(9) Uani 1 1 d . . .
H15A H -0.5474 0.3687 0.8687 0.085 Uiso 1 1 calc R . .
H15B H -0.2653 0.4143 0.8950 0.085 Uiso 1 1 calc R . .
C1 C 1.0893(7) 0.1796(2) 0.59502(15) 0.0864(11) Uani 1 1 d . . .
H1A H 1.1200 0.2281 0.5727 0.130 Uiso 1 1 calc R . .
H1B H 0.9982 0.1397 0.5689 0.130 Uiso 1 1 calc R . .
H1C H 1.2755 0.1597 0.6111 0.130 Uiso 1 1 calc R . .
C14 C -0.4059(8) 0.1310(2) 1.04535(15) 0.0838(11) Uani 1 1 d . . .
H14A H -0.4541 0.0912 1.0746 0.126 Uiso 1 1 calc R . .
H14B H -0.5842 0.1528 1.0268 0.126 Uiso 1 1 calc R . .
H14C H -0.2939 0.1735 1.0648 0.126 Uiso 1 1 calc R . .
C16 C -0.5465(9) 0.3839(3) 0.95920(18) 0.1052(14) Uani 1 1 d . . .
H16A H -0.6529 0.4340 0.9572 0.158 Uiso 1 1 calc R . .
H16B H -0.3999 0.3859 0.9918 0.158 Uiso 1 1 calc R . .
H16C H -0.6809 0.3405 0.9657 0.158 Uiso 1 1 calc R . .
C2 C 0.7040(11) -0.11531(19) 0.80161(18) 0.1115(16) Uani 1 1 d . . .
H2A H 0.6263 -0.1466 0.8334 0.167 Uiso 1 1 calc R . .
H2B H 0.9150 -0.1134 0.8067 0.167 Uiso 1 1 calc R . .
H2C H 0.6484 -0.1397 0.7636 0.167 Uiso 1 1 calc R . .


_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
O6 C12 1.330(3) . ?
O6 C13 1.445(3) . ?
O2 C6 1.364(3) . ?
O2 C2 1.410(3) . ?
O5 C11 1.325(3) . ?
O5 C15 1.445(3) . ?
O3 C12 1.217(3) . ?
O4 C11 1.207(3) . ?
O1 C3 1.369(3) . ?
O1 C1 1.419(3) . ?
N C9 1.325(3) . ?
N C7 1.406(3) . ?
N H0 0.8600 . ?
C6 C5 1.381(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.370(4) . ?
C9 C10 1.366(3) . ?
C9 H9 0.9300 . ?
C10 C12 1.457(3) . ?
C10 C11 1.466(3) . ?
C8 C3 1.391(4) . ?
C8 H8 0.9300 . ?
C3 C4 1.368(4) . ?
C5 C4 1.382(4) . ?
C5 H5 0.9300 . ?
C13 C14 1.482(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C4 H4 0.9300 . ?
C15 C16 1.479(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
C12 O6 C13 116.4(2) . . ?
C6 O2 C2 117.1(2) . . ?
C11 O5 C15 116.3(2) . . ?
C3 O1 C1 117.3(2) . . ?
C9 N C7 126.9(2) . . ?
C9 N H0 116.6 . . ?
C7 N H0 116.6 . . ?
O2 C6 C5 125.6(2) . . ?
O2 C6 C7 115.6(2) . . ?
C5 C6 C7 118.9(2) . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 N 123.2(2) . . ?
C6 C7 N 117.0(2) . . ?
N C9 C10 127.6(2) . . ?
N C9 H9 116.2 . . ?
C10 C9 H9 116.2 . . ?
C9 C10 C12 119.3(2) . . ?
C9 C10 C11 114.4(2) . . ?
C12 C10 C11 126.2(2) . . ?
C7 C8 C3 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
O3 C12 O6 121.7(2) . . ?
O3 C12 C10 122.6(2) . . ?
O6 C12 C10 115.7(2) . . ?
O4 C11 O5 121.2(2) . . ?
O4 C11 C10 123.0(2) . . ?
O5 C11 C10 115.8(2) . . ?
C4 C3 O1 125.1(2) . . ?
C4 C3 C8 119.7(3) . . ?
O1 C3 C8 115.2(2) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
O6 C13 C14 107.6(2) . . ?
O6 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
O6 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
O5 C15 C16 107.2(3) . . ?
O5 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O5 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
C2 O2 C6 C5 1.1(5) . . . . ?
C2 O2 C6 C7 -178.3(3) . . . . ?
O2 C6 C7 C8 179.1(2) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
O2 C6 C7 N 0.2(3) . . . . ?
C5 C6 C7 N -179.3(2) . . . . ?
C9 N C7 C8 9.5(4) . . . . ?
C9 N C7 C6 -171.7(2) . . . . ?
C7 N C9 C10 -178.6(2) . . . . ?
N C9 C10 C12 -1.2(4) . . . . ?
N C9 C10 C11 -177.1(2) . . . . ?
C6 C7 C8 C3 1.1(4) . . . . ?
N C7 C8 C3 179.9(2) . . . . ?
C13 O6 C12 O3 -5.4(4) . . . . ?
C13 O6 C12 C10 173.8(2) . . . . ?
C9 C10 C12 O3 -3.4(4) . . . . ?
C11 C10 C12 O3 172.0(3) . . . . ?
C9 C10 C12 O6 177.4(2) . . . . ?
C11 C10 C12 O6 -7.2(4) . . . . ?
C15 O5 C11 O4 1.7(4) . . . . ?
C15 O5 C11 C10 -178.9(2) . . . . ?
C9 C10 C11 O4 10.2(4) . . . . ?
C12 C10 C11 O4 -165.4(3) . . . . ?
C9 C10 C11 O5 -169.1(2) . . . . ?
C12 C10 C11 O5 15.2(4) . . . . ?
C1 O1 C3 C4 2.9(5) . . . . ?
C1 O1 C3 C8 -178.6(3) . . . . ?
C7 C8 C3 C4 -0.8(4) . . . . ?
C7 C8 C3 O1 -179.4(2) . . . . ?
O2 C6 C5 C4 -180.0(3) . . . . ?
C7 C6 C5 C4 -0.5(4) . . . . ?
C12 O6 C13 C14 177.3(3) . . . . ?
O1 C3 C4 C5 178.3(3) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C11 O5 C15 C16 177.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037


####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 920439'
_audit_update_record             
;
2013-01-17 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
#TrackingRef 'joc-03.cif'


_audit_creation_method           SHELXL-97
_pub_contact_author_name         
'Chiranjeev Sharma Neupane, Ashawani Kumar Singh and Dr. Satish Kumar awasthi'
_pub1_contact_author_address     
;
Chemical Biology Laboratory
Department of Chemistry
University of Delhi
New Delhi, Delhi 110007
India
;
_pub1_contact_author_e-mail      awasthisatish@yahoo.com
_pub1_contact_author_phone       +91-11-27667794
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 Cl N O4'
_chemical_formula_sum            'C15 H18 Cl N O4'
_chemical_formula_weight         311.75

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 0.0000 0.0000 '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 0.0060 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.2728(6)
_cell_length_b                   9.4396(11)
_cell_length_c                   26.241(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1553.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1370
_cell_measurement_theta_min      3.0989
_cell_measurement_theta_max      29.0341

_exptl_crystal_description       prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .28
_exptl_crystal_size_min          .25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6111
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3045
_reflns_number_gt                2512
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0558P)²+0.1869P] 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       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.01(10)
_refine_ls_number_reflns         3045
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.088
_refine_ls_shift/su_mean         0.016

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
Cl Cl 0.95663(13) 0.05368(9) 0.75686(3) 0.0636(3) Uani 1 1 d . . .
O3 O 0.2612(3) -0.1366(2) 0.88854(7) 0.0538(5) Uani 1 1 d . . .
O4 O 0.5254(3) -0.0887(3) 0.83548(8) 0.0666(6) Uani 1 1 d . . .
O2 O 0.2511(4) -0.0143(3) 0.97371(8) 0.0758(7) Uani 1 1 d . . .
N N 0.8164(3) 0.0974(2) 0.86198(8) 0.0443(5) Uani 1 1 d . . .
H0 H 0.7698 0.0406 0.8389 0.053 Uiso 1 1 calc . . .
C5 C 0.9986(4) 0.1760(3) 0.84946(10) 0.0390(6) Uani 1 1 d . . .
C7 C 1.2590(4) 0.2400(3) 0.78535(11) 0.0474(7) Uani 1 1 d . . .
H7 H 1.3093 0.2307 0.7522 0.057 Uiso 1 1 calc R . .
O1 O 0.5053(4) 0.1314(3) 0.99654(9) 0.0962(10) Uani 1 1 d . . .
C6 C 1.0819(4) 0.1654(3) 0.80050(10) 0.0424(6) Uani 1 1 d . . .
C13 C 0.4393(4) -0.0699(3) 0.87637(10) 0.0456(6) Uani 1 1 d . . .
C9 C 0.5255(4) 0.0247(3) 0.91525(9) 0.0417(6) Uani 1 1 d . . .
C10 C 0.4302(5) 0.0533(3) 0.96570(11) 0.0504(7) Uani 1 1 d . . .
C4 C 1.1023(5) 0.2649(3) 0.88314(11) 0.0507(7) Uani 1 1 d . . .
H4 H 1.0519 0.2746 0.9163 0.061 Uiso 1 1 calc R . .
C11 C 0.1432(6) 0.0048(4) 1.02185(13) 0.0684(10) Uani 1 1 d . . .
H11A H 0.0687 0.0948 1.0225 0.082 Uiso 1 1 calc R . .
H11B H 0.2445 0.0026 1.0498 0.082 Uiso 1 1 calc R . .
C2 C 1.3627(4) 0.3287(3) 0.81911(12) 0.0497(7) Uani 1 1 d . . .
C14 C 0.1757(5) -0.2351(4) 0.85197(12) 0.0614(8) Uani 1 1 d . . .
H14A H 0.2808 -0.3069 0.8436 0.074 Uiso 1 1 calc R . .
H14B H 0.1354 -0.1862 0.8209 0.074 Uiso 1 1 calc R . .
C8 C 0.7078(4) 0.1001(3) 0.90516(10) 0.0430(6) Uani 1 1 d . . .
H8 H 0.7594 0.1583 0.9310 0.052 Uiso 1 1 calc R . .
C15 C -0.0146(5) -0.3011(4) 0.87626(15) 0.0765(11) Uani 1 1 d . . .
H15A H -0.0772 -0.3682 0.8532 0.115 Uiso 1 1 calc R . .
H15B H -0.1170 -0.2289 0.8843 0.115 Uiso 1 1 calc R . .
H15C H 0.0277 -0.3488 0.9070 0.115 Uiso 1 1 calc R . .
C1 C 1.5579(5) 0.4113(4) 0.80277(14) 0.0712(10) Uani 1 1 d . . .
H1A H 1.5900 0.3902 0.7678 0.107 Uiso 1 1 calc R . .
H1B H 1.6768 0.3852 0.8238 0.107 Uiso 1 1 calc R . .
H1C H 1.5307 0.5109 0.8063 0.107 Uiso 1 1 calc R . .
C3 C 1.2798(5) 0.3391(3) 0.86784(12) 0.0547(8) Uani 1 1 d . . .
H3 H 1.3468 0.3985 0.8911 0.066 Uiso 1 1 calc R . .
C12 C -0.0091(6) -0.1135(4) 1.02614(15) 0.0946(14) Uani 1 1 d . . .
H12A H -0.0853 -0.1060 1.0577 0.142 Uiso 1 1 calc R . .
H12B H 0.0670 -0.2017 1.0252 0.142 Uiso 1 1 calc R . .
H12C H -0.1080 -0.1098 0.9983 0.142 Uiso 1 1 calc R . .


_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
Cl C6 1.744(3) . ?
O3 C13 1.322(3) . ?
O3 C14 1.440(3) . ?
O4 C13 1.214(3) . ?
O2 C10 1.309(4) . ?
O2 C11 1.444(4) . ?
N C8 1.323(3) . ?
N C5 1.402(3) . ?
N H0 0.8600 . ?
C5 C4 1.381(4) . ?
C5 C6 1.390(4) . ?
C7 C6 1.374(4) . ?
C7 C2 1.382(4) . ?
C7 H7 0.9300 . ?
O1 C10 1.192(4) . ?
C13 C9 1.460(4) . ?
C9 C8 1.373(4) . ?
C9 C10 1.477(4) . ?
C4 C3 1.375(4) . ?
C4 H4 0.9300 . ?
C11 C12 1.473(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 C3 1.384(4) . ?
C2 C1 1.514(4) . ?
C14 C15 1.490(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C8 H8 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 H3 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C13 O3 C14 117.5(2) . . ?
C10 O2 C11 118.8(3) . . ?
C8 N C5 127.6(2) . . ?
C8 N H0 116.2 . . ?
C5 N H0 116.2 . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 N 123.7(2) . . ?
C6 C5 N 119.0(2) . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C7 C6 C5 122.3(3) . . ?
C7 C6 Cl 119.0(2) . . ?
C5 C6 Cl 118.7(2) . . ?
O4 C13 O3 121.3(3) . . ?
O4 C13 C9 122.9(3) . . ?
O3 C13 C9 115.8(2) . . ?
C8 C9 C13 119.4(2) . . ?
C8 C9 C10 114.5(2) . . ?
C13 C9 C10 126.0(2) . . ?
O1 C10 O2 122.1(3) . . ?
O1 C10 C9 124.2(3) . . ?
O2 C10 C9 113.7(3) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O2 C11 C12 106.0(3) . . ?
O2 C11 H11A 110.5 . . ?
C12 C11 H11A 110.5 . . ?
O2 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C3 C2 C7 117.3(3) . . ?
C3 C2 C1 122.0(3) . . ?
C7 C2 C1 120.8(3) . . ?
O3 C14 C15 106.5(3) . . ?
O3 C14 H14A 110.4 . . ?
C15 C14 H14A 110.4 . . ?
O3 C14 H14B 110.4 . . ?
C15 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
N C8 C9 125.7(3) . . ?
N C8 H8 117.1 . . ?
C9 C8 H8 117.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C3 C4 122.5(3) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
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 . . ?

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
C8 N C5 C4 4.4(4) . . . . ?
C8 N C5 C6 -175.6(3) . . . . ?
C2 C7 C6 C5 0.5(4) . . . . ?
C2 C7 C6 Cl -179.6(2) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
N C5 C6 C7 179.5(2) . . . . ?
C4 C5 C6 Cl 179.7(2) . . . . ?
N C5 C6 Cl -0.4(3) . . . . ?
C14 O3 C13 O4 1.5(4) . . . . ?
C14 O3 C13 C9 -177.6(2) . . . . ?
O4 C13 C9 C8 2.3(4) . . . . ?
O3 C13 C9 C8 -178.7(2) . . . . ?
O4 C13 C9 C10 179.9(3) . . . . ?
O3 C13 C9 C10 -1.0(4) . . . . ?
C11 O2 C10 O1 -1.1(5) . . . . ?
C11 O2 C10 C9 179.8(3) . . . . ?
C8 C9 C10 O1 -2.3(4) . . . . ?
C13 C9 C10 O1 180.0(3) . . . . ?
C8 C9 C10 O2 176.9(3) . . . . ?
C13 C9 C10 O2 -0.9(4) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
N C5 C4 C3 -179.7(2) . . . . ?
C10 O2 C11 C12 -162.9(3) . . . . ?
C6 C7 C2 C3 -0.4(4) . . . . ?
C6 C7 C2 C1 180.0(2) . . . . ?
C13 O3 C14 C15 176.5(3) . . . . ?
C5 N C8 C9 177.6(2) . . . . ?
C13 C9 C8 N 0.9(4) . . . . ?
C10 C9 C8 N -177.0(3) . . . . ?
C7 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C4 179.9(3) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034


