# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_gsr125
_database_code_depnum_ccdc_archive 'CCDC 1992537'
loop_
_audit_author_name
_audit_author_address
'Dr. Raghavaiah Pallepogu'
;Dr Harisingh Gour University
India
;
_audit_update_record             
;
2020-03-25 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4.75 H5 N O1.25'
_chemical_formula_weight         96.10

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   P2(1)/c

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                   18.271(3)
_cell_length_b                   8.4386(16)
_cell_length_c                   12.3780(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.240(6)
_cell_angle_gamma                90.00
_cell_volume                     1905.5(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9807
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      25.93

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47139
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_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         2.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3345
_reflns_number_gt                2699
_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)+(0.1019P)²+1.8533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3345
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.2081
_refine_ls_wR_factor_gt          0.1965
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36385(12) 0.6370(3) 0.36140(17) 0.0424(6) Uani 1 1 d . . .
N3 N 0.42870(13) 0.7432(3) 0.49281(17) 0.0453(6) Uani 1 1 d . . .
O3 O 0.17414(12) 0.5117(3) 0.31002(17) 0.0704(7) Uani 1 1 d . . .
N2 N 0.36115(14) 0.7162(3) 0.45774(18) 0.0511(6) Uani 1 1 d . . .
O4 O 0.71237(13) 0.6647(4) 0.4105(2) 0.0829(8) Uani 1 1 d . . .
C11 C 0.47491(14) 0.6804(3) 0.42154(19) 0.0360(6) Uani 1 1 d . . .
C12 C 0.43403(14) 0.6118(3) 0.33790(19) 0.0360(6) Uani 1 1 d . . .
C15 C 0.58839(14) 0.6062(3) 0.3504(2) 0.0405(6) Uani 1 1 d . . .
O5 O 0.68998(13) 0.5572(4) 0.2506(2) 0.0904(10) Uani 1 1 d . . .
C10 C 0.55448(15) 0.6911(3) 0.4254(2) 0.0384(6) Uani 1 1 d . . .
C13 C 0.46663(15) 0.5359(3) 0.2443(2) 0.0414(6) Uani 1 1 d . . .
H13A H 0.4654 0.6087 0.1836 0.050 Uiso 1 1 calc R . .
H13B H 0.4388 0.4422 0.2228 0.050 Uiso 1 1 calc R . .
C14 C 0.54566(15) 0.4905(3) 0.2762(2) 0.0439(7) Uani 1 1 d . . .
H14A H 0.5717 0.4782 0.2106 0.053 Uiso 1 1 calc R . .
H14B H 0.5454 0.3881 0.3117 0.053 Uiso 1 1 calc R . .
C19 C 0.58921(18) 0.8005(4) 0.5090(2) 0.0565(8) Uani 1 1 d . . .
H19A H 0.5993 0.7434 0.5753 0.085 Uiso 1 1 calc R . .
H19B H 0.5564 0.8866 0.5216 0.085 Uiso 1 1 calc R . .
H19C H 0.6342 0.8415 0.4838 0.085 Uiso 1 1 calc R . .
C8 C 0.29714(16) 0.5959(4) 0.3022(2) 0.0495(7) Uani 1 1 d . . .
C16 C 0.66908(17) 0.6136(4) 0.3434(2) 0.0531(8) Uani 1 1 d . . .
C4 C 0.11780(16) 0.4402(4) 0.3581(2) 0.0562(8) Uani 1 1 d . . .
N4 N -0.06307(18) 0.2107(5) 0.4821(3) 0.0877(11) Uani 1 1 d . . .
C7 C 0.23976(17) 0.5396(5) 0.3743(3) 0.0611(9) Uani 1 1 d . . .
H7A H 0.2557 0.4428 0.4106 0.073 Uiso 1 1 calc R . .
H7B H 0.2313 0.6190 0.4289 0.073 Uiso 1 1 calc R . .
O1 O -0.12015(18) 0.2056(6) 0.4263(3) 0.1372(17) Uani 1 1 d . . .
C5 C 0.12094(17) 0.3876(5) 0.4642(3) 0.0642(9) Uani 1 1 d . . .
H5 H 0.1632 0.4026 0.5085 0.077 Uiso 1 1 calc R . .
O2 O -0.05696(19) 0.1565(6) 0.5720(3) 0.1384(18) Uani 1 1 d . . .
C3 C 0.05423(18) 0.4188(5) 0.2929(3) 0.0658(10) Uani 1 1 d . . .
H3 H 0.0519 0.4552 0.2219 0.079 Uiso 1 1 calc R . .
C9 C 0.29111(19) 0.6063(5) 0.1959(3) 0.0714(11) Uani 1 1 d . . .
H9A H 0.3307 0.6409 0.1581 0.086 Uiso 1 1 calc R . .
H9B H 0.2473 0.5791 0.1587 0.086 Uiso 1 1 calc R . .
C1 C -0.00067(17) 0.2908(5) 0.4383(3) 0.0625(9) Uani 1 1 d . . .
C6 C 0.06145(18) 0.3133(5) 0.5035(3) 0.0684(10) Uani 1 1 d . . .
H6 H 0.0632 0.2779 0.5747 0.082 Uiso 1 1 calc R . .
C2 C -0.00517(18) 0.3440(5) 0.3329(3) 0.0698(10) Uani 1 1 d . . .
H2 H -0.0479 0.3295 0.2894 0.084 Uiso 1 1 calc R . .
C17 C 0.7699(3) 0.5573(7) 0.2347(4) 0.1060(15) Uiso 1 1 d . . .
H17A H 0.7909 0.6592 0.2554 0.127 Uiso 1 1 calc R . .
H17B H 0.7940 0.4761 0.2793 0.127 Uiso 1 1 calc R . .
C18 C 0.7803(3) 0.5273(7) 0.1247(4) 0.1163(17) Uiso 1 1 d . . .
H18A H 0.7551 0.4316 0.1030 0.174 Uiso 1 1 calc R . .
H18B H 0.8317 0.5157 0.1144 0.174 Uiso 1 1 calc R . .
H18C H 0.7611 0.6142 0.0818 0.174 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
N1 C12 1.348(3) . ?
N1 N2 1.370(3) . ?
N1 C8 1.429(4) . ?
N3 N2 1.305(3) . ?
N3 C11 1.362(3) . ?
O3 C4 1.359(4) . ?
O3 C7 1.421(4) . ?
O4 C16 1.195(4) . ?
C11 C12 1.370(4) . ?
C11 C10 1.455(4) . ?
C12 C13 1.478(3) . ?
C15 C10 1.351(4) . ?
C15 C16 1.483(4) . ?
C15 C14 1.525(4) . ?
O5 C16 1.319(4) . ?
O5 C17 1.485(5) . ?
C10 C19 1.500(4) . ?
C13 C14 1.524(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C8 C9 1.316(4) . ?
C8 C7 1.493(4) . ?
C4 C5 1.384(4) . ?
C4 C3 1.388(4) . ?
N4 O2 1.202(4) . ?
N4 O1 1.219(4) . ?
N4 C1 1.456(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C6 1.368(5) . ?
C5 H5 0.9300 . ?
C3 C2 1.371(5) . ?
C3 H3 0.9300 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C1 C6 1.368(4) . ?
C1 C2 1.378(5) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C17 C18 1.408(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 N1 N2 110.3(2) . . ?
C12 N1 C8 130.2(2) . . ?
N2 N1 C8 119.5(2) . . ?
N2 N3 C11 109.0(2) . . ?
C4 O3 C7 117.7(2) . . ?
N3 N2 N1 107.1(2) . . ?
N3 C11 C12 108.8(2) . . ?
N3 C11 C10 127.5(2) . . ?
C12 C11 C10 123.5(2) . . ?
N1 C12 C11 104.8(2) . . ?
N1 C12 C13 131.9(2) . . ?
C11 C12 C13 123.3(2) . . ?
C10 C15 C16 121.0(3) . . ?
C10 C15 C14 121.0(2) . . ?
C16 C15 C14 117.9(2) . . ?
C16 O5 C17 116.8(3) . . ?
C15 C10 C11 116.1(2) . . ?
C15 C10 C19 127.4(3) . . ?
C11 C10 C19 116.4(2) . . ?
C12 C13 C14 108.9(2) . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 C15 116.1(2) . . ?
C13 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C8 N1 121.1(3) . . ?
C9 C8 C7 126.6(3) . . ?
N1 C8 C7 112.2(2) . . ?
O4 C16 O5 121.5(3) . . ?
O4 C16 C15 126.5(3) . . ?
O5 C16 C15 111.9(3) . . ?
O3 C4 C5 124.5(3) . . ?
O3 C4 C3 115.7(3) . . ?
C5 C4 C3 119.9(3) . . ?
O2 N4 O1 122.9(3) . . ?
O2 N4 C1 119.2(3) . . ?
O1 N4 C1 117.9(3) . . ?
O3 C7 C8 108.5(2) . . ?
O3 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
O3 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C6 C1 C2 121.1(3) . . ?
C6 C1 N4 119.0(3) . . ?
C2 C1 N4 119.9(3) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C18 C17 O5 108.4(4) . . ?
C18 C17 H17A 110.0 . . ?
O5 C17 H17A 110.0 . . ?
C18 C17 H17B 110.0 . . ?
O5 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_dbr151a
_database_code_depnum_ccdc_archive 'CCDC 1992538'
loop_
_audit_author_name
_audit_author_address
'Dr. Raghavaiah Pallepogu'
;Dr Harisingh Gour University
India
;
_audit_update_record             
;
2020-03-25 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5.67 H6.33 N O'
_chemical_formula_weight         104.45

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2978(6)
_cell_length_b                   8.2873(8)
_cell_length_c                   14.1639(13)
_cell_angle_alpha                97.850(4)
_cell_angle_beta                 94.308(3)
_cell_angle_gamma                110.859(3)
_cell_volume                     785.86(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.39

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28797
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2764
_reflns_number_gt                2411
_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)+(0.0567P)²+0.2246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.137(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O3 O 0.43129(17) 0.81420(17) 0.21843(8) 0.0555(3) Uani 1 1 d . . .
O1 O 0.72582(18) 0.62012(17) 0.93818(8) 0.0617(4) Uani 1 1 d . . .
N1 N 0.27382(18) 0.71639(16) 0.63306(9) 0.0412(3) Uani 1 1 d . . .
O2 O 0.10625(19) 0.7413(2) 0.18767(9) 0.0773(5) Uani 1 1 d . . .
N2 N 0.0906(2) 0.71926(19) 0.64573(10) 0.0513(4) Uani 1 1 d . . .
N3 N 0.01088(19) 0.73593(18) 0.56358(10) 0.0498(4) Uani 1 1 d . . .
C6 C 0.1167(2) 0.76624(19) 0.39857(11) 0.0402(4) Uani 1 1 d . . .
C2 C 0.3070(2) 0.73003(18) 0.54168(10) 0.0387(4) Uani 1 1 d . . .
C1 C 0.1402(2) 0.74259(19) 0.49807(11) 0.0398(4) Uani 1 1 d . . .
C12 C 0.3058(2) 0.5946(2) 0.77740(11) 0.0463(4) Uani 1 1 d . . .
H12 H 0.1688 0.5410 0.7710 0.056 Uiso 1 1 calc R . .
C5 C 0.2506(2) 0.7374(2) 0.34445(11) 0.0418(4) Uani 1 1 d . . .
C13 C 0.4215(2) 0.5740(2) 0.85255(11) 0.0499(4) Uani 1 1 d . . .
H13 H 0.3621 0.5075 0.8975 0.060 Uiso 1 1 calc R . .
C11 C 0.3950(2) 0.69620(19) 0.71109(10) 0.0407(4) Uani 1 1 d . . .
C8 C 0.2493(2) 0.7620(2) 0.24292(11) 0.0473(4) Uani 1 1 d . . .
C16 C 0.5982(2) 0.7754(2) 0.72088(11) 0.0474(4) Uani 1 1 d . . .
H16 H 0.6573 0.8450 0.6771 0.057 Uiso 1 1 calc R . .
C14 C 0.6256(2) 0.6514(2) 0.86174(11) 0.0463(4) Uani 1 1 d . . .
C3 C 0.4790(2) 0.7351(2) 0.49041(11) 0.0483(4) Uani 1 1 d . . .
H3A H 0.5435 0.6627 0.5154 0.058 Uiso 1 1 calc R . .
H3B H 0.5745 0.8544 0.4990 0.058 Uiso 1 1 calc R . .
C15 C 0.7148(2) 0.7522(2) 0.79532(11) 0.0499(4) Uani 1 1 d . . .
H15 H 0.8519 0.8037 0.8009 0.060 Uiso 1 1 calc R . .
C4 C 0.3996(2) 0.6657(3) 0.38451(11) 0.0534(4) Uani 1 1 d . . .
H4A H 0.3376 0.5389 0.3753 0.064 Uiso 1 1 calc R . .
H4B H 0.5101 0.6939 0.3476 0.064 Uiso 1 1 calc R . .
C7 C -0.0452(3) 0.8275(2) 0.36799(13) 0.0568(5) Uani 1 1 d . . .
H7A H -0.0292 0.8607 0.3059 0.085 Uiso 1 1 calc R . .
H7B H -0.0388 0.9266 0.4139 0.085 Uiso 1 1 calc R . .
H7C H -0.1712 0.7344 0.3647 0.085 Uiso 1 1 calc R . .
C9 C 0.4514(3) 0.8454(3) 0.12119(13) 0.0644(5) Uani 1 1 d . . .
H9A H 0.3854 0.9234 0.1060 0.077 Uiso 1 1 calc R . .
H9B H 0.3925 0.7358 0.0760 0.077 Uiso 1 1 calc R . .
C10 C 0.6667(3) 0.9266(3) 0.11505(15) 0.0757(6) Uani 1 1 d . . .
H10A H 0.7241 1.0330 0.1614 0.114 Uiso 1 1 calc R . .
H10B H 0.6854 0.9526 0.0517 0.114 Uiso 1 1 calc R . .
H10C H 0.7297 0.8467 0.1281 0.114 Uiso 1 1 calc R . .
C17 C 0.9350(3) 0.6991(3) 0.95262(15) 0.0720(6) Uani 1 1 d . . .
H17A H 0.9866 0.6587 0.8977 0.108 Uiso 1 1 calc R . .
H17B H 0.9859 0.6679 1.0090 0.108 Uiso 1 1 calc R . .
H17C H 0.9743 0.8243 0.9610 0.108 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
O3 C8 1.3313(19) . ?
O3 C9 1.444(2) . ?
O1 C14 1.3663(19) . ?
O1 C17 1.416(2) . ?
N1 C2 1.3468(18) . ?
N1 N2 1.3705(17) . ?
N1 C11 1.4285(19) . ?
O2 C8 1.2018(19) . ?
N2 N3 1.3079(19) . ?
N3 C1 1.3649(19) . ?
C6 C5 1.352(2) . ?
C6 C1 1.455(2) . ?
C6 C7 1.501(2) . ?
C2 C1 1.367(2) . ?
C2 C3 1.488(2) . ?
C12 C13 1.376(2) . ?
C12 C11 1.390(2) . ?
C12 H12 0.9300 . ?
C5 C8 1.480(2) . ?
C5 C4 1.522(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9300 . ?
C11 C16 1.378(2) . ?
C16 C15 1.382(2) . ?
C16 H16 0.9300 . ?
C14 C15 1.388(2) . ?
C3 C4 1.521(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C15 H15 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.488(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C8 O3 C9 117.06(13) . . ?
C14 O1 C17 118.17(14) . . ?
C2 N1 N2 110.05(12) . . ?
C2 N1 C11 130.02(12) . . ?
N2 N1 C11 119.90(12) . . ?
N3 N2 N1 107.34(12) . . ?
N2 N3 C1 108.67(12) . . ?
C5 C6 C1 115.64(13) . . ?
C5 C6 C7 126.90(14) . . ?
C1 C6 C7 117.39(13) . . ?
N1 C2 C1 105.04(13) . . ?
N1 C2 C3 132.29(13) . . ?
C1 C2 C3 122.67(13) . . ?
N3 C1 C2 108.88(13) . . ?
N3 C1 C6 127.82(14) . . ?
C2 C1 C6 123.25(13) . . ?
C13 C12 C11 119.58(15) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C6 C5 C8 121.74(14) . . ?
C6 C5 C4 120.54(13) . . ?
C8 C5 C4 117.58(13) . . ?
C12 C13 C14 120.53(14) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C16 C11 C12 119.97(15) . . ?
C16 C11 N1 120.80(13) . . ?
C12 C11 N1 119.23(14) . . ?
O2 C8 O3 122.44(15) . . ?
O2 C8 C5 126.20(15) . . ?
O3 C8 C5 111.35(13) . . ?
C11 C16 C15 120.51(14) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O1 C14 C13 115.58(14) . . ?
O1 C14 C15 124.52(15) . . ?
C13 C14 C15 119.91(15) . . ?
C2 C3 C4 107.08(13) . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
C4 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
C16 C15 C14 119.48(15) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C3 C4 C5 114.75(14) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C9 C10 107.28(16) . . ?
O3 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
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 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_gsr89
_database_code_depnum_ccdc_archive 'CCDC 1992539'
loop_
_audit_author_name
_audit_author_address
'Dr. Raghavaiah Pallepogu'
;Dr Harisingh Gour University
India
;
_audit_update_record             
;
2020-03-25 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H2 Cl0.14 N0.43 O0.29'
_chemical_formula_weight         41.68

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.5916(13)
_cell_length_b                   4.0692(7)
_cell_length_c                   26.512(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.367(9)
_cell_angle_gamma                90.00
_cell_volume                     709.1(2)
_cell_formula_units_Z            14
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5302
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      24.52

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colurless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13844
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2485
_reflns_number_gt                2184
_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)+(0.0473P)²+0.0654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_number_reflns         2485
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.30692(11) 1.1466(2) 0.47147(2) 0.0772(2) Uani 1 1 d . . .
O2 O 0.6416(2) 0.0996(4) 0.10294(5) 0.0507(4) Uani 1 1 d . . .
O1 O 0.3514(2) 0.3342(5) 0.07183(6) 0.0655(5) Uani 1 1 d . . .
N1 N 0.1419(2) 0.7242(4) 0.29818(6) 0.0428(4) Uani 1 1 d . . .
N2 N 0.3292(2) 0.5883(5) 0.30841(6) 0.0504(5) Uani 1 1 d . . .
N3 N 0.3954(3) 0.5001(5) 0.26561(7) 0.0504(5) Uani 1 1 d . . .
C4 C 0.0318(3) 0.8327(6) 0.33966(7) 0.0410(5) Uani 1 1 d . . .
C8 C 0.2539(3) 0.5796(5) 0.22720(7) 0.0418(5) Uani 1 1 d . . .
C11 C 0.4672(3) 0.2606(5) 0.10718(8) 0.0450(5) Uani 1 1 d . . .
C7 C 0.0905(3) 0.7260(5) 0.24767(7) 0.0407(5) Uani 1 1 d . . .
C5 C -0.1699(3) 0.7417(6) 0.34207(8) 0.0485(6) Uani 1 1 d . . .
H5 H -0.2353 0.6162 0.3164 0.058 Uiso 1 1 calc R . .
C6 C -0.2727(3) 0.8394(7) 0.38302(8) 0.0532(6) Uani 1 1 d . . .
H6 H -0.4086 0.7828 0.3849 0.064 Uiso 1 1 calc R . .
C3 C 0.1299(3) 1.0140(6) 0.37805(8) 0.0484(5) Uani 1 1 d . . .
H3 H 0.2653 1.0736 0.3762 0.058 Uiso 1 1 calc R . .
C2 C 0.0281(3) 1.1065(7) 0.41891(8) 0.0541(6) Uani 1 1 d . . .
H2 H 0.0943 1.2265 0.4451 0.065 Uiso 1 1 calc R . .
C9 C 0.2852(3) 0.5051(6) 0.17515(8) 0.0443(5) Uani 1 1 d . . .
H9 H 0.1906 0.5850 0.1503 0.053 Uiso 1 1 calc R . .
C10 C 0.4388(3) 0.3315(6) 0.16036(8) 0.0465(5) Uani 1 1 d . . .
H10 H 0.5339 0.2499 0.1849 0.056 Uiso 1 1 calc R . .
C1 C -0.1736(4) 1.0202(6) 0.42093(8) 0.0515(6) Uani 1 1 d . . .
C14 C -0.0998(3) 0.8693(7) 0.22353(8) 0.0527(6) Uani 1 1 d . . .
H14A H -0.2090 0.7148 0.2254 0.079 Uiso 1 1 calc R . .
H14B H -0.0816 0.9184 0.1887 0.079 Uiso 1 1 calc R . .
H14C H -0.1318 1.0676 0.2409 0.079 Uiso 1 1 calc R . .
C12 C 0.6873(3) 0.0035(6) 0.05254(8) 0.0517(6) Uani 1 1 d . . .
H12A H 0.6873 0.1945 0.0306 0.062 Uiso 1 1 calc R . .
H12B H 0.5860 -0.1504 0.0384 0.062 Uiso 1 1 calc R . .
C13 C 0.8917(4) -0.1527(7) 0.05677(9) 0.0622(6) Uani 1 1 d . . .
H13A H 0.9909 0.0033 0.0702 0.093 Uiso 1 1 calc R . .
H13B H 0.9258 -0.2234 0.0239 0.093 Uiso 1 1 calc R . .
H13C H 0.8903 -0.3390 0.0790 0.093 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 C1 1.736(2) . ?
O2 C11 1.335(3) . ?
O2 C12 1.446(2) . ?
O1 C11 1.201(2) . ?
N1 C7 1.356(2) . ?
N1 N2 1.361(2) . ?
N1 C4 1.433(3) . ?
N2 N3 1.297(2) . ?
N3 C8 1.366(3) . ?
C4 C3 1.378(3) . ?
C4 C5 1.386(3) . ?
C8 C7 1.378(3) . ?
C8 C9 1.443(3) . ?
C11 C10 1.465(3) . ?
C7 C14 1.483(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.370(3) . ?
C6 H6 0.9300 . ?
C3 C2 1.370(3) . ?
C3 H3 0.9300 . ?
C2 C1 1.380(3) . ?
C2 H2 0.9300 . ?
C9 C10 1.319(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 C13 1.486(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C11 O2 C12 116.85(16) . . ?
C7 N1 N2 110.71(16) . . ?
C7 N1 C4 130.79(16) . . ?
N2 N1 C4 118.49(15) . . ?
N3 N2 N1 107.36(15) . . ?
N2 N3 C8 109.32(17) . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 N1 119.69(18) . . ?
C5 C4 N1 119.79(18) . . ?
N3 C8 C7 108.55(18) . . ?
N3 C8 C9 121.60(18) . . ?
C7 C8 C9 129.84(18) . . ?
O1 C11 O2 123.8(2) . . ?
O1 C11 C10 125.6(2) . . ?
O2 C11 C10 110.58(17) . . ?
N1 C7 C8 104.05(17) . . ?
N1 C7 C14 124.59(19) . . ?
C8 C7 C14 131.34(19) . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C10 C9 C8 124.5(2) . . ?
C10 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
C9 C10 C11 123.3(2) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C6 C1 C2 121.0(2) . . ?
C6 C1 Cl1 118.95(18) . . ?
C2 C1 Cl1 120.04(18) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C12 C13 107.30(17) . . ?
O2 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.035
