# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ACHINA
_database_code_depnum_ccdc_archive 'CCDC 988858'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
Ethyl 2-(1-benzyl-4-(4-methoxyphenyl)-1H-1,2,3-triazol-5-yl)-2-oxoacetate
;
_chemical_formula_moiety         'C20 H19 N3 O4'
_chemical_formula_sum            'C20 H19 N3 O4'
_chemical_formula_iupac          'C20 H19 N3 O4'
_chemical_formula_weight         365.38

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2922(6)
_cell_length_b                   9.4246(7)
_cell_length_c                   12.9343(10)
_cell_angle_alpha                111.004(2)
_cell_angle_beta                 99.018(3)
_cell_angle_gamma                97.623(2)
_cell_volume                     912.24(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3299
_cell_measurement_theta_min      1.729
_cell_measurement_theta_max      27.230
_cell_measurement_temperature    296(2)
_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.970
_exptl_special_details           
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.77
_diffrn_reflns_number            14140
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         27.230
_diffrn_reflns_theta_full        27.230
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             4016
_reflns_number_gt                3299
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         4016
_refine_ls_number_parameters     249
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+0.2677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.131(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.89719(16) -0.02911(13) 0.21123(9) 0.0572(3) Uani 1 1 d D . . . .
O2 O 0.93912(18) -0.13576(14) 0.03570(11) 0.0678(4) Uani 1 1 d . . . . .
O3 O 0.69561(14) 0.03169(13) -0.00492(9) 0.0574(3) Uani 1 1 d . . . . .
O4 O 1.56414(17) 0.2433(2) 0.47612(11) 0.0788(4) Uani 1 1 d . . . . .
N1 N 0.92934(17) 0.47083(15) 0.30574(10) 0.0495(3) Uani 1 1 d . . . . .
N2 N 0.79076(18) 0.47683(15) 0.24387(11) 0.0524(3) Uani 1 1 d . . . . .
N3 N 0.73641(15) 0.34026(14) 0.15706(10) 0.0429(3) Uani 1 1 d . . . . .
C1A C 0.9745(11) -0.1138(5) 0.3581(3) 0.0942(12) Uani 0.719(11) 1 d D . P A 1
H1A H 1.037543 -0.012062 0.406964 0.141 Uiso 0.719(11) 1 calc R U P A 1
H1B H 1.019845 -0.190142 0.379808 0.141 Uiso 0.719(11) 1 calc R U P A 1
H1C H 0.860231 -0.120824 0.364531 0.141 Uiso 0.719(11) 1 calc R U P A 1
C2A C 0.9834(16) -0.1417(11) 0.2416(7) 0.0942(12) Uani 0.719(11) 1 d D . P A 1
H2A H 0.928580 -0.247290 0.191845 0.113 Uiso 0.719(11) 1 calc R U P A 1
H2B H 1.098705 -0.125423 0.234959 0.113 Uiso 0.719(11) 1 calc R U P A 1
C1B C 1.069(3) -0.0907(13) 0.3504(8) 0.0942(12) Uani 0.281(11) 1 d D . P A 2
H1D H 1.174590 -0.037573 0.348588 0.141 Uiso 0.281(11) 1 calc R U P A 2
H1E H 1.083915 -0.176166 0.372003 0.141 Uiso 0.281(11) 1 calc R U P A 2
H1F H 1.019789 -0.020088 0.404412 0.141 Uiso 0.281(11) 1 calc R U P A 2
C2B C 0.961(4) -0.147(3) 0.2406(17) 0.0942(12) Uani 0.281(11) 1 d D . P A 2
H2C H 0.867599 -0.223996 0.237294 0.113 Uiso 0.281(11) 1 calc R U P A 2
H2D H 1.021243 -0.199154 0.184519 0.113 Uiso 0.281(11) 1 calc R U P A 2
C3 C 0.89208(19) -0.04003(17) 0.10655(12) 0.0450(3) Uani 1 1 d . . . . .
C4 C 0.80242(17) 0.08012(16) 0.08155(12) 0.0405(3) Uani 1 1 d . . . . .
C5 C 0.84109(17) 0.24126(16) 0.16276(11) 0.0378(3) Uani 1 1 d . . . . .
C6 C 0.96564(18) 0.32810(16) 0.25877(11) 0.0398(3) Uani 1 1 d . . . . .
C7 C 1.11941(17) 0.29621(16) 0.31129(11) 0.0402(3) Uani 1 1 d . . . . .
C8 C 1.22540(19) 0.22204(18) 0.24779(12) 0.0465(4) Uani 1 1 d . . . . .
H8 H 1.195927 0.185458 0.169000 0.056 Uiso 1 1 calc R U . . .
C9 C 1.3745(2) 0.2014(2) 0.29960(13) 0.0536(4) Uani 1 1 d . . . . .
H9 H 1.444335 0.151063 0.255787 0.064 Uiso 1 1 calc R U . . .
C10 C 1.4193(2) 0.2558(2) 0.41651(13) 0.0536(4) Uani 1 1 d . . . . .
C11 C 1.3134(2) 0.3284(2) 0.48115(13) 0.0575(4) Uani 1 1 d . . . . .
H11 H 1.342303 0.363299 0.559870 0.069 Uiso 1 1 calc R U . . .
C12 C 1.1656(2) 0.34911(19) 0.42919(12) 0.0504(4) Uani 1 1 d . . . . .
H12 H 1.095673 0.398954 0.473209 0.060 Uiso 1 1 calc R U . . .
C13 C 1.6897(3) 0.1986(4) 0.4175(2) 0.0975(8) Uani 1 1 d . . . . .
H13A H 1.656724 0.090717 0.368263 0.146 Uiso 1 1 calc R U . . .
H13B H 1.791587 0.214929 0.470954 0.146 Uiso 1 1 calc R U . . .
H13C H 1.706790 0.259683 0.373071 0.146 Uiso 1 1 calc R U . . .
C14 C 0.58683(18) 0.3217(2) 0.07231(13) 0.0486(4) Uani 1 1 d . . . . .
H14A H 0.523266 0.398745 0.105946 0.058 Uiso 1 1 calc R U . . .
H14B H 0.517595 0.219932 0.051032 0.058 Uiso 1 1 calc R U . . .
C15 C 0.62686(17) 0.33886(17) -0.03277(12) 0.0436(3) Uani 1 1 d . . . . .
C16 C 0.5324(2) 0.2444(2) -0.13827(16) 0.0697(5) Uani 1 1 d . . . . .
H16 H 0.447147 0.164440 -0.145360 0.084 Uiso 1 1 calc R U . . .
C17 C 0.5620(3) 0.2662(3) -0.23451(17) 0.0804(6) Uani 1 1 d . . . . .
H17 H 0.495802 0.201661 -0.305332 0.096 Uiso 1 1 calc R U . . .
C18 C 0.6872(2) 0.3811(2) -0.22616(15) 0.0637(5) Uani 1 1 d . . . . .
H18 H 0.706871 0.395605 -0.290851 0.076 Uiso 1 1 calc R U . . .
C19 C 0.7830(2) 0.4743(2) -0.12259(16) 0.0630(5) Uani 1 1 d . . . . .
H19 H 0.869438 0.552622 -0.116371 0.076 Uiso 1 1 calc R U . . .
C20 C 0.7534(2) 0.4540(2) -0.02636(14) 0.0556(4) Uani 1 1 d . . . . .
H20 H 0.820186 0.519267 0.044087 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3139(18) . ?
O1 C2B 1.436(17) . ?
O1 C2A 1.484(7) . ?
O2 C3 1.1910(18) . ?
O3 C4 1.2083(17) . ?
O4 C10 1.3648(19) . ?
O4 C13 1.405(3) . ?
N1 N2 1.3136(18) . ?
N1 C6 1.3595(19) . ?
N2 N3 1.3312(18) . ?
N3 C5 1.3688(17) . ?
N3 C14 1.4662(18) . ?
C1A C2A 1.449(11) . ?
C1A H1A 0.9600 . ?
C1A H1B 0.9600 . ?
C1A H1C 0.9600 . ?
C2A H2A 0.9700 . ?
C2A H2B 0.9700 . ?
C1B C2B 1.425(18) . ?
C1B H1D 0.9600 . ?
C1B H1E 0.9600 . ?
C1B H1F 0.9600 . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3 C4 1.533(2) . ?
C4 C5 1.461(2) . ?
C5 C6 1.3869(19) . ?
C6 C7 1.4677(19) . ?
C7 C8 1.383(2) . ?
C7 C12 1.3935(19) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(2) . ?
C11 C12 1.375(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.506(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.370(2) . ?
C15 C20 1.376(2) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.355(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
C3 O1 C2B 116.2(10) . . ?
C3 O1 C2A 114.1(4) . . ?
C10 O4 C13 118.00(15) . . ?
N2 N1 C6 109.23(12) . . ?
N1 N2 N3 108.18(11) . . ?
N2 N3 C5 110.42(12) . . ?
N2 N3 C14 118.14(12) . . ?
C5 N3 C14 131.38(12) . . ?
C2A C1A H1A 109.5 . . ?
C2A C1A H1B 109.5 . . ?
H1A C1A H1B 109.5 . . ?
C2A C1A H1C 109.5 . . ?
H1A C1A H1C 109.5 . . ?
H1B C1A H1C 109.5 . . ?
C1A C2A O1 106.1(7) . . ?
C1A C2A H2A 110.5 . . ?
O1 C2A H2A 110.5 . . ?
C1A C2A H2B 110.5 . . ?
O1 C2A H2B 110.5 . . ?
H2A C2A H2B 108.7 . . ?
C2B C1B H1D 109.5 . . ?
C2B C1B H1E 109.5 . . ?
H1D C1B H1E 109.5 . . ?
C2B C1B H1F 109.5 . . ?
H1D C1B H1F 109.5 . . ?
H1E C1B H1F 109.5 . . ?
C1B C2B O1 114.1(16) . . ?
C1B C2B H2C 108.7 . . ?
O1 C2B H2C 108.7 . . ?
C1B C2B H2D 108.7 . . ?
O1 C2B H2D 108.7 . . ?
H2C C2B H2D 107.6 . . ?
O2 C3 O1 126.11(14) . . ?
O2 C3 C4 122.55(14) . . ?
O1 C3 C4 111.15(12) . . ?
O3 C4 C5 123.39(13) . . ?
O3 C4 C3 116.18(13) . . ?
C5 C4 C3 120.35(12) . . ?
N3 C5 C6 104.36(12) . . ?
N3 C5 C4 121.06(12) . . ?
C6 C5 C4 134.46(13) . . ?
N1 C6 C5 107.80(12) . . ?
N1 C6 C7 118.97(12) . . ?
C5 C6 C7 133.20(13) . . ?
C8 C7 C12 118.47(13) . . ?
C8 C7 C6 122.09(12) . . ?
C12 C7 C6 119.35(13) . . ?
C9 C8 C7 121.06(13) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 119.82(14) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
O4 C10 C9 124.58(15) . . ?
O4 C10 C11 115.67(14) . . ?
C9 C10 C11 119.76(14) . . ?
C12 C11 C10 120.16(14) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 120.72(14) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.79(12) . . ?
N3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C20 117.58(15) . . ?
C16 C15 C14 120.80(15) . . ?
C20 C15 C14 121.55(14) . . ?
C15 C16 C17 120.99(17) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.44(18) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.29(17) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 120.59(17) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 121.11(16) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?

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
C6 N1 N2 N3 -0.18(17) . . . . ?
N1 N2 N3 C5 0.71(16) . . . . ?
N1 N2 N3 C14 -176.85(12) . . . . ?
C3 O1 C2A C1A -179.2(7) . . . . ?
C3 O1 C2B C1B 138.7(19) . . . . ?
C2B O1 C3 O2 -2.1(14) . . . . ?
C2A O1 C3 O2 5.3(6) . . . . ?
C2B O1 C3 C4 173.0(14) . . . . ?
C2A O1 C3 C4 -179.6(5) . . . . ?
O2 C3 C4 O3 44.2(2) . . . . ?
O1 C3 C4 O3 -131.09(14) . . . . ?
O2 C3 C4 C5 -138.95(16) . . . . ?
O1 C3 C4 C5 45.74(18) . . . . ?
N2 N3 C5 C6 -0.93(15) . . . . ?
C14 N3 C5 C6 176.21(14) . . . . ?
N2 N3 C5 C4 175.62(12) . . . . ?
C14 N3 C5 C4 -7.2(2) . . . . ?
O3 C4 C5 N3 13.2(2) . . . . ?
C3 C4 C5 N3 -163.42(12) . . . . ?
O3 C4 C5 C6 -171.52(15) . . . . ?
C3 C4 C5 C6 11.9(2) . . . . ?
N2 N1 C6 C5 -0.40(16) . . . . ?
N2 N1 C6 C7 177.72(12) . . . . ?
N3 C5 C6 N1 0.79(15) . . . . ?
C4 C5 C6 N1 -175.06(14) . . . . ?
N3 C5 C6 C7 -176.95(14) . . . . ?
C4 C5 C6 C7 7.2(3) . . . . ?
N1 C6 C7 C8 -134.62(15) . . . . ?
C5 C6 C7 C8 42.9(2) . . . . ?
N1 C6 C7 C12 41.9(2) . . . . ?
C5 C6 C7 C12 -140.54(16) . . . . ?
C12 C7 C8 C9 -0.4(2) . . . . ?
C6 C7 C8 C9 176.13(15) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C13 O4 C10 C9 12.3(3) . . . . ?
C13 O4 C10 C11 -167.9(2) . . . . ?
C8 C9 C10 O4 -179.16(17) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
O4 C10 C11 C12 178.90(17) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C8 C7 C12 C11 0.2(2) . . . . ?
C6 C7 C12 C11 -176.47(15) . . . . ?
N2 N3 C14 C15 99.51(16) . . . . ?
C5 N3 C14 C15 -77.45(19) . . . . ?
N3 C14 C15 C16 140.33(17) . . . . ?
N3 C14 C15 C20 -42.9(2) . . . . ?
C20 C15 C16 C17 -1.1(3) . . . . ?
C14 C15 C16 C17 175.80(19) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C16 C15 C20 C19 0.6(3) . . . . ?
C14 C15 C20 C19 -176.26(15) . . . . ?
C18 C19 C20 C15 0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14 H14B O3 0.97 2.58 3.542(2) 172.5 2_655 yes

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_BNAEEM
_database_code_depnum_ccdc_archive 'CCDC 988859'
loop_
_audit_author_name
_audit_author_address
'Dr nawaz tahir'
;University of sargodha
Pakistan
;
_audit_update_record             
;
2020-04-01 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
Ethyl 2-(1-benzyl-4-(4-flourophenyl)-1H-1,2,3-triazol-5-yl)-2-oxoacetate
;
_chemical_formula_moiety         'C19 H16 F N3 O3'
_chemical_formula_sum            'C19 H16 F N3 O3'
_chemical_formula_iupac          'C19 H16 F N3 O3'
_chemical_formula_weight         353.35

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   28.5939(14)
_cell_length_b                   7.5267(4)
_cell_length_c                   19.3890(8)
_cell_angle_alpha                90
_cell_angle_beta                 121.9640(10)
_cell_angle_gamma                90
_cell_volume                     3540.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2645
_cell_measurement_theta_min      1.664
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.980
_exptl_special_details           
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.84
_diffrn_reflns_number            14823
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.679
_diffrn_reflns_theta_max         26.952
_diffrn_reflns_theta_full        26.952
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3806
_reflns_number_gt                2426
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1614
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         3806
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+1.6543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19077(6) 0.9982(2) 0.05614(9) 0.0548(4) Uani 1 1 d . . . . .
O2 O 0.24684(7) 0.9731(2) 0.00865(11) 0.0686(5) Uani 1 1 d . . . . .
O3 O 0.31233(6) 0.7802(2) 0.14926(9) 0.0599(4) Uani 1 1 d . . . . .
N1 N 0.17784(8) 0.4887(3) 0.15797(12) 0.0564(5) Uani 1 1 d . . . . .
N2 N 0.22769(8) 0.4679(3) 0.22165(12) 0.0563(5) Uani 1 1 d . . . . .
N3 N 0.26195(7) 0.5678(2) 0.21169(10) 0.0443(4) Uani 1 1 d . . . . .
C1 C 0.10662(12) 1.1631(4) -0.0095(2) 0.0914(10) Uani 1 1 d . . . . .
H1A H 0.087181 1.052407 -0.020795 0.137 Uiso 1 1 calc R U . . .
H1B H 0.084499 1.246644 -0.051882 0.137 Uiso 1 1 calc R U . . .
H1C H 0.114035 1.208955 0.041588 0.137 Uiso 1 1 calc R U . . .
C2 C 0.15870(11) 1.1344(4) -0.00531(17) 0.0759(8) Uani 1 1 d . . . . .
H2A H 0.179433 1.244451 0.009001 0.091 Uiso 1 1 calc R U . . .
H2B H 0.151403 1.096010 -0.057885 0.091 Uiso 1 1 calc R U . . .
C3 C 0.23216(9) 0.9284(3) 0.05334(12) 0.0464(5) Uani 1 1 d . . . . .
C4 C 0.26312(8) 0.7837(3) 0.11784(12) 0.0425(5) Uani 1 1 d . . . . .
C5 C 0.23397(8) 0.6597(3) 0.14037(11) 0.0394(5) Uani 1 1 d . . . . .
C6 C 0.17968(8) 0.6050(3) 0.10603(12) 0.0426(5) Uani 1 1 d . . . . .
F1A F -0.01624(8) 0.6883(4) -0.05305(16) 0.1232(12) Uani 0.824(4) 1 d . . P A 1
C7A C 0.12848(15) 0.6383(6) 0.0272(3) 0.0448(9) Uani 0.824(4) 1 d G . P A 1
C8A C 0.0786(2) 0.6521(7) 0.0233(2) 0.0625(9) Uani 0.824(4) 1 d G . P A 1
H8A H 0.077651 0.639598 0.070234 0.075 Uiso 0.824(4) 1 calc R U P A 1
C9A C 0.03028(15) 0.6845(7) -0.0508(2) 0.0748(11) Uani 0.824(4) 1 d G . P A 1
C10A C 0.03176(13) 0.7031(7) -0.1209(2) 0.0760(12) Uani 0.824(4) 1 d G . P A 1
H10A H -0.000596 0.724776 -0.170506 0.091 Uiso 0.824(4) 1 calc R U P A 1
C11A C 0.08160(17) 0.6893(8) -0.1170(3) 0.0692(11) Uani 0.824(4) 1 d G . P A 1
H11A H 0.082589 0.701804 -0.163920 0.083 Uiso 0.824(4) 1 calc R U P A 1
C12A C 0.12996(13) 0.6569(7) -0.0429(4) 0.0509(10) Uani 0.824(4) 1 d G . P A 1
H12A H 0.163307 0.647729 -0.040257 0.061 Uiso 0.824(4) 1 calc R U P A 1
F1B F 0.0661(6) 0.691(2) -0.1840(6) 0.135(6) Uani 0.176(4) 1 d . . P A 2
C7B C 0.1311(8) 0.670(4) 0.0311(15) 0.0448(9) Uani 0.176(4) 1 d G . P A 2
C8B C 0.0860(11) 0.655(4) 0.0396(12) 0.0625(9) Uani 0.176(4) 1 d G . P A 2
H8B H 0.091312 0.643252 0.091112 0.075 Uiso 0.176(4) 1 calc R U P A 2
C9B C 0.0328(9) 0.656(4) -0.0287(15) 0.0748(11) Uani 0.176(4) 1 d G . P A 2
H9B H 0.002659 0.645691 -0.022975 0.090 Uiso 0.176(4) 1 calc R U P A 2
C10B C 0.0248(8) 0.673(4) -0.1056(12) 0.0760(12) Uani 0.176(4) 1 d G . P A 2
H10B H -0.010705 0.674058 -0.151376 0.091 Uiso 0.176(4) 1 calc R U P A 2
C11B C 0.0699(10) 0.689(4) -0.1142(14) 0.0692(11) Uani 0.176(4) 1 d G . P A 2
C12B C 0.1231(8) 0.687(4) -0.0459(19) 0.0509(10) Uani 0.176(4) 1 d G . P A 2
H12B H 0.153237 0.697547 -0.051607 0.061 Uiso 0.176(4) 1 calc R U P A 2
C13 C 0.32016(8) 0.5672(3) 0.27605(12) 0.0504(5) Uani 1 1 d . . . . .
H13A H 0.323377 0.532201 0.326546 0.060 Uiso 1 1 calc R U . A 1
H13B H 0.334342 0.687186 0.283040 0.060 Uiso 1 1 calc R U . A 1
C14A C 0.35544(17) 0.4455(5) 0.26065(18) 0.0476(5) Uani 0.824(4) 1 d G . P A 1
C15A C 0.41194(19) 0.4759(6) 0.3062(2) 0.0879(15) Uani 0.824(4) 1 d G . P A 1
H15A H 0.426095 0.570222 0.342637 0.105 Uiso 0.824(4) 1 calc R U P A 1
C16A C 0.44730(13) 0.3653(7) 0.2972(2) 0.1133(19) Uani 0.824(4) 1 d G . P A 1
H16A H 0.485106 0.385666 0.327605 0.136 Uiso 0.824(4) 1 calc R U P A 1
C17A C 0.42615(14) 0.2244(6) 0.2426(2) 0.0930(10) Uani 0.824(4) 1 d G . P A 1
H17A H 0.449803 0.150368 0.236614 0.112 Uiso 0.824(4) 1 calc R U P A 1
C18A C 0.36964(15) 0.1939(4) 0.1971(2) 0.0674(10) Uani 0.824(4) 1 d G . P A 1
H18A H 0.355490 0.099626 0.160656 0.081 Uiso 0.824(4) 1 calc R U P A 1
C19A C 0.33429(12) 0.3045(4) 0.20614(18) 0.0567(8) Uani 0.824(4) 1 d G . P A 1
H19A H 0.296479 0.284182 0.175687 0.068 Uiso 0.824(4) 1 calc R U P A 1
C14B C 0.3555(9) 0.451(2) 0.2598(10) 0.0476(5) Uani 0.176(4) 1 d G . P A 2
C15B C 0.4069(10) 0.509(3) 0.2775(12) 0.0879(15) Uani 0.176(4) 1 d G . P A 2
H15B H 0.418093 0.624897 0.294518 0.105 Uiso 0.176(4) 1 calc R U P A 2
C16B C 0.4416(7) 0.392(4) 0.2697(14) 0.1133(19) Uani 0.176(4) 1 d G . P A 2
H16B H 0.475962 0.430646 0.281482 0.136 Uiso 0.176(4) 1 calc R U P A 2
C17B C 0.4248(8) 0.219(3) 0.2442(13) 0.0930(10) Uani 0.176(4) 1 d G . P A 2
H17B H 0.448009 0.140726 0.238976 0.112 Uiso 0.176(4) 1 calc R U P A 2
C18B C 0.3734(8) 0.161(2) 0.2265(10) 0.0674(10) Uani 0.176(4) 1 d G . P A 2
H18B H 0.362188 0.045054 0.209506 0.081 Uiso 0.176(4) 1 calc R U P A 2
C19B C 0.3387(7) 0.278(2) 0.2344(9) 0.0567(8) Uani 0.176(4) 1 d G . P A 2
H19B H 0.304318 0.239304 0.222541 0.068 Uiso 0.176(4) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.322(2) . ?
O1 C2 1.468(3) . ?
O2 C3 1.194(2) . ?
O3 C4 1.202(2) . ?
N1 N2 1.310(3) . ?
N1 C6 1.356(3) . ?
N2 N3 1.327(2) . ?
N3 C5 1.364(3) . ?
N3 C13 1.459(3) . ?
C1 C2 1.464(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(3) . ?
C4 C5 1.463(3) . ?
C5 C6 1.389(3) . ?
C6 C7B 1.465(19) . ?
C6 C7A 1.474(4) . ?
F1A C9A 1.308(4) . ?
C7A C8A 1.3900 . ?
C7A C12A 1.3900 . ?
C8A C9A 1.3900 . ?
C8A H8A 0.9300 . ?
C9A C10A 1.3900 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9300 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9300 . ?
F1B C11B 1.30(2) . ?
C7B C8B 1.3900 . ?
C7B C12B 1.3900 . ?
C8B C9B 1.3900 . ?
C8B H8B 0.9300 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9300 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9300 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9300 . ?
C13 C14B 1.488(17) . ?
C13 C14A 1.505(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14A C15A 1.3900 . ?
C14A C19A 1.3900 . ?
C15A C16A 1.3900 . ?
C15A H15A 0.9300 . ?
C16A C17A 1.3900 . ?
C16A H16A 0.9300 . ?
C17A C18A 1.3900 . ?
C17A H17A 0.9300 . ?
C18A C19A 1.3900 . ?
C18A H18A 0.9300 . ?
C19A H19A 0.9300 . ?
C14B C15B 1.3900 . ?
C14B C19B 1.3900 . ?
C15B C16B 1.3900 . ?
C15B H15B 0.9300 . ?
C16B C17B 1.3900 . ?
C16B H16B 0.9300 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9300 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9300 . ?
C19B H19B 0.9300 . ?

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
C3 O1 C2 115.63(17) . . ?
N2 N1 C6 109.04(17) . . ?
N1 N2 N3 108.28(16) . . ?
N2 N3 C5 110.67(16) . . ?
N2 N3 C13 117.99(17) . . ?
C5 N3 C13 131.31(17) . . ?
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 . . ?
C1 C2 O1 109.1(2) . . ?
C1 C2 H2A 109.9 . . ?
O1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
O1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O2 C3 O1 125.7(2) . . ?
O2 C3 C4 121.2(2) . . ?
O1 C3 C4 113.01(16) . . ?
O3 C4 C5 122.28(19) . . ?
O3 C4 C3 116.32(18) . . ?
C5 C4 C3 121.40(18) . . ?
N3 C5 C6 104.02(16) . . ?
N3 C5 C4 120.34(17) . . ?
C6 C5 C4 135.63(19) . . ?
N1 C6 C5 107.97(18) . . ?
N1 C6 C7B 124.3(12) . . ?
C5 C6 C7B 127.5(11) . . ?
N1 C6 C7A 118.2(3) . . ?
C5 C6 C7A 133.7(3) . . ?
C8A C7A C12A 120.0 . . ?
C8A C7A C6 119.8(4) . . ?
C12A C7A C6 120.2(4) . . ?
C7A C8A C9A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
F1A C9A C8A 118.4(3) . . ?
F1A C9A C10A 121.5(3) . . ?
C8A C9A C10A 120.0 . . ?
C11A C10A C9A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C10A C11A C12A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A C7A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C7A C12A H12A 120.0 . . ?
C8B C7B C12B 120.0 . . ?
C8B C7B C6 107.8(19) . . ?
C12B C7B C6 129(2) . . ?
C7B C8B C9B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
F1B C11B C10B 123.6(18) . . ?
F1B C11B C12B 116.2(19) . . ?
C10B C11B C12B 120.0 . . ?
C11B C12B C7B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C7B C12B H12B 120.0 . . ?
N3 C13 C14B 114.6(7) . . ?
N3 C13 C14A 114.4(2) . . ?
N3 C13 H13A 108.7 . . ?
C14A C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
C14A C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15A C14A C19A 120.0 . . ?
C15A C14A C13 116.7(3) . . ?
C19A C14A C13 123.2(3) . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A C19A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C15B C14B C19B 120.0 . . ?
C15B C14B C13 120.9(14) . . ?
C19B C14B C13 118.8(14) . . ?
C14B C15B C16B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C17B C16B C15B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C14B C19B H19B 120.0 . . ?

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
C6 N1 N2 N3 -0.4(2) . . . . ?
N1 N2 N3 C5 1.2(2) . . . . ?
N1 N2 N3 C13 179.38(18) . . . . ?
C3 O1 C2 C1 164.6(2) . . . . ?
C2 O1 C3 O2 4.2(3) . . . . ?
C2 O1 C3 C4 -178.58(19) . . . . ?
O2 C3 C4 O3 35.7(3) . . . . ?
O1 C3 C4 O3 -141.74(19) . . . . ?
O2 C3 C4 C5 -145.4(2) . . . . ?
O1 C3 C4 C5 37.2(3) . . . . ?
N2 N3 C5 C6 -1.5(2) . . . . ?
C13 N3 C5 C6 -179.3(2) . . . . ?
N2 N3 C5 C4 177.87(17) . . . . ?
C13 N3 C5 C4 0.0(3) . . . . ?
O3 C4 C5 N3 17.6(3) . . . . ?
C3 C4 C5 N3 -161.27(17) . . . . ?
O3 C4 C5 C6 -163.4(2) . . . . ?
C3 C4 C5 C6 17.8(3) . . . . ?
N2 N1 C6 C5 -0.5(2) . . . . ?
N2 N1 C6 C7B -175.4(16) . . . . ?
N2 N1 C6 C7A 175.8(3) . . . . ?
N3 C5 C6 N1 1.2(2) . . . . ?
C4 C5 C6 N1 -178.0(2) . . . . ?
N3 C5 C6 C7B 175.8(17) . . . . ?
C4 C5 C6 C7B -3.4(17) . . . . ?
N3 C5 C6 C7A -174.3(4) . . . . ?
C4 C5 C6 C7A 6.6(5) . . . . ?
N1 C6 C7A C8A 39.9(4) . . . . ?
C5 C6 C7A C8A -145.1(3) . . . . ?
N1 C6 C7A C12A -140.5(3) . . . . ?
C5 C6 C7A C12A 34.6(5) . . . . ?
C12A C7A C8A C9A 0.0 . . . . ?
C6 C7A C8A C9A 179.7(4) . . . . ?
C7A C8A C9A F1A 176.8(5) . . . . ?
C7A C8A C9A C10A 0.0 . . . . ?
F1A C9A C10A C11A -176.7(5) . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C9A C10A C11A C12A 0.0 . . . . ?
C10A C11A C12A C7A 0.0 . . . . ?
C8A C7A C12A C11A 0.0 . . . . ?
C6 C7A C12A C11A -179.7(4) . . . . ?
N1 C6 C7B C8B 23.9(19) . . . . ?
C5 C6 C7B C8B -149.9(11) . . . . ?
N1 C6 C7B C12B -134.9(17) . . . . ?
C5 C6 C7B C12B 51(3) . . . . ?
C12B C7B C8B C9B 0.0 . . . . ?
C6 C7B C8B C9B -161(2) . . . . ?
C7B C8B C9B C10B 0.0 . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C9B C10B C11B F1B 175(3) . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
F1B C11B C12B C7B -175(3) . . . . ?
C10B C11B C12B C7B 0.0 . . . . ?
C8B C7B C12B C11B 0.0 . . . . ?
C6 C7B C12B C11B 157(3) . . . . ?
N2 N3 C13 C14B 100.0(8) . . . . ?
C5 N3 C13 C14B -82.3(8) . . . . ?
N2 N3 C13 C14A 98.2(3) . . . . ?
C5 N3 C13 C14A -84.1(3) . . . . ?
N3 C13 C14A C15A 161.9(2) . . . . ?
N3 C13 C14A C19A -20.3(3) . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?
C13 C14A C15A C16A 177.9(3) . . . . ?
C14A C15A C16A C17A 0.0 . . . . ?
C15A C16A C17A C18A 0.0 . . . . ?
C16A C17A C18A C19A 0.0 . . . . ?
C17A C18A C19A C14A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C13 C14A C19A C18A -177.8(3) . . . . ?
N3 C13 C14B C15B 137.5(9) . . . . ?
N3 C13 C14B C19B -49.0(11) . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C13 C14B C15B C16B 173.5(13) . . . . ?
C14B C15B C16B C17B 0.0 . . . . ?
C15B C16B C17B C18B 0.0 . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C17B C18B C19B C14B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
C13 C14B C19B C18B -173.6(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13A^a O1 0.97 2.53 3.468(3) 164.1 4_545 yes
C13 H13B^a N1 0.97 2.65 3.410(3) 135.9 4 yes

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_NWB
_database_code_depnum_ccdc_archive 'CCDC 988864'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
Ethyl 2-(1-benzyl-4-(4-chlorophenyl)-1H-1,2,3-triazol-5-yl)-2-oxoacetate
;
_chemical_formula_moiety         'C20 H18 Cl N3 O3'
_chemical_formula_sum            'C20 H18 Cl N3 O3'
_chemical_formula_iupac          'C20 H18 Cl N3 O3'
_chemical_formula_weight         383.82

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3157(6)
_cell_length_b                   9.5082(8)
_cell_length_c                   13.1245(10)
_cell_angle_alpha                68.898(4)
_cell_angle_beta                 86.538(4)
_cell_angle_gamma                85.332(4)
_cell_volume                     964.38(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2645
_cell_measurement_theta_min      1.664
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.945
_exptl_special_details           
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.11
_diffrn_reflns_number            13504
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.664
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3701
_reflns_number_gt                2645
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         3701
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.4819P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.50945(16) 0.66095(18) 0.09789(10) 0.1494(6) Uani 1 1 d . . . . .
O1 O 0.1585(2) 0.46950(19) 0.28166(14) 0.0655(5) Uani 1 1 d . . . . .
O2 O 0.0658(2) 0.3642(2) 0.45355(15) 0.0765(6) Uani 1 1 d . . . . .
O3 O 0.3090(2) 0.5409(2) 0.48032(16) 0.0712(5) Uani 1 1 d . . . . .
N1 N 0.1358(4) 0.9579(3) 0.2004(2) 0.0796(7) Uani 1 1 d . . . . .
N2 N 0.2590(4) 0.9761(3) 0.2508(2) 0.0853(8) Uani 1 1 d . . . . .
N3 N 0.2965(3) 0.8459(2) 0.33068(18) 0.0672(6) Uani 1 1 d . . . . .
C1 C 0.1055(8) 0.3983(6) 0.1359(4) 0.156(2) Uani 1 1 d . . . . .
H1A H 0.042608 0.491087 0.101520 0.234 Uiso 1 1 calc R U . . .
H1B H 0.068718 0.320570 0.114075 0.234 Uiso 1 1 calc R U . . .
H1C H 0.217106 0.412245 0.114085 0.234 Uiso 1 1 calc R U . . .
C2 C 0.0878(5) 0.3557(4) 0.2508(3) 0.0917(10) Uani 1 1 d . . . . .
H2A H 0.142535 0.257380 0.286253 0.110 Uiso 1 1 calc R U . . .
H2B H -0.025559 0.349918 0.273034 0.110 Uiso 1 1 calc R U . . .
C3 C 0.1348(3) 0.4596(3) 0.38327(19) 0.0533(6) Uani 1 1 d . . . . .
C4 C 0.2201(3) 0.5818(3) 0.40489(19) 0.0526(6) Uani 1 1 d . . . . .
C5 C 0.1963(3) 0.7384(3) 0.33159(19) 0.0551(6) Uani 1 1 d . . . . .
C6 C 0.0933(3) 0.8129(3) 0.24795(19) 0.0589(6) Uani 1 1 d . . . . .
C7 C -0.0497(3) 0.7671(3) 0.21034(18) 0.0578(6) Uani 1 1 d . . . . .
C8 C -0.1623(3) 0.6831(3) 0.28378(19) 0.0604(6) Uani 1 1 d . . . . .
H8 H -0.143756 0.649673 0.358175 0.072 Uiso 1 1 calc R U . . .
C9 C -0.3009(4) 0.6479(4) 0.2495(2) 0.0743(8) Uani 1 1 d . . . . .
H9 H -0.374237 0.588845 0.299887 0.089 Uiso 1 1 calc R U . . .
C10 C -0.3300(4) 0.7004(4) 0.1404(3) 0.0838(9) Uani 1 1 d . . . . .
C11 C -0.2206(5) 0.7844(4) 0.0650(2) 0.0893(10) Uani 1 1 d . . . . .
H11 H -0.241350 0.819516 -0.009137 0.107 Uiso 1 1 calc R U . . .
C12 C -0.0804(4) 0.8159(3) 0.0999(2) 0.0759(8) Uani 1 1 d . . . . .
H12 H -0.005038 0.870831 0.048923 0.091 Uiso 1 1 calc R U . . .
C13 C 0.4279(3) 0.8398(4) 0.4013(3) 0.0797(9) Uani 1 1 d . . . . .
H13A H 0.492157 0.925951 0.365457 0.096 Uiso 1 1 calc R U . . .
H13B H 0.496943 0.749265 0.409971 0.096 Uiso 1 1 calc R U . . .
C14 C 0.3744(3) 0.8399(3) 0.5120(2) 0.0638(7) Uani 1 1 d . . . . .
C15 C 0.4576(4) 0.7495(4) 0.6019(3) 0.0906(10) Uani 1 1 d . . . . .
H15 H 0.541082 0.682721 0.593642 0.109 Uiso 1 1 calc R U . . .
C16 C 0.4208(4) 0.7552(4) 0.7029(3) 0.0918(10) Uani 1 1 d . . . . .
H16 H 0.481527 0.693879 0.761697 0.110 Uiso 1 1 calc R U . . .
C17 C 0.2986(3) 0.8475(3) 0.7201(3) 0.0725(7) Uani 1 1 d . . . . .
C18 C 0.2137(3) 0.9370(4) 0.6316(3) 0.0766(8) Uani 1 1 d . . . . .
H18 H 0.129132 1.001921 0.641120 0.092 Uiso 1 1 calc R U . . .
C19 C 0.2497(3) 0.9340(3) 0.5290(2) 0.0711(7) Uani 1 1 d . . . . .
H19 H 0.189253 0.996178 0.470358 0.085 Uiso 1 1 calc R U . . .
C20 C 0.2633(5) 0.8545(5) 0.8319(3) 0.1124(13) Uani 1 1 d . . . . .
H20A H 0.282884 0.755793 0.886152 0.169 Uiso 1 1 calc R U . . .
H20B H 0.152470 0.888619 0.837694 0.169 Uiso 1 1 calc R U . . .
H20C H 0.332094 0.923443 0.843313 0.169 Uiso 1 1 calc R U . . .


_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 C10 1.738(3) . ?
O1 C3 1.306(3) . ?
O1 C2 1.459(3) . ?
O2 C3 1.192(3) . ?
O3 C4 1.201(3) . ?
N1 N2 1.308(4) . ?
N1 C6 1.359(3) . ?
N2 N3 1.331(3) . ?
N3 C5 1.366(3) . ?
N3 C13 1.460(4) . ?
C1 C2 1.415(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.526(3) . ?
C4 C5 1.458(3) . ?
C5 C6 1.377(4) . ?
C6 C7 1.469(4) . ?
C7 C8 1.379(3) . ?
C7 C12 1.386(3) . ?
C8 C9 1.370(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(5) . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.494(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.371(4) . ?
C14 C19 1.374(4) . ?
C15 C16 1.362(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.350(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(4) . ?
C17 C20 1.503(5) . ?
C18 C19 1.372(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C3 O1 C2 116.5(2) . . ?
N2 N1 C6 108.8(2) . . ?
N1 N2 N3 108.3(2) . . ?
N2 N3 C5 110.4(2) . . ?
N2 N3 C13 118.4(2) . . ?
C5 N3 C13 131.2(2) . . ?
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 . . ?
C1 C2 O1 107.8(3) . . ?
C1 C2 H2A 110.1 . . ?
O1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
O1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 126.4(2) . . ?
O2 C3 C4 122.7(2) . . ?
O1 C3 C4 110.76(19) . . ?
O3 C4 C5 123.7(2) . . ?
O3 C4 C3 117.0(2) . . ?
C5 C4 C3 119.3(2) . . ?
N3 C5 C6 104.2(2) . . ?
N3 C5 C4 121.6(2) . . ?
C6 C5 C4 134.0(2) . . ?
N1 C6 C5 108.3(2) . . ?
N1 C6 C7 119.1(2) . . ?
C5 C6 C7 132.4(2) . . ?
C8 C7 C12 118.1(3) . . ?
C8 C7 C6 121.1(2) . . ?
C12 C7 C6 120.6(2) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 Cl1 119.0(3) . . ?
C11 C10 Cl1 120.1(2) . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
N3 C13 C14 114.5(2) . . ?
N3 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
N3 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 117.0(3) . . ?
C15 C14 C13 119.7(3) . . ?
C19 C14 C13 123.2(3) . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 117.3(3) . . ?
C16 C17 C20 120.7(3) . . ?
C18 C17 C20 121.9(3) . . ?
C17 C18 C19 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C14 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 N1 N2 N3 -0.4(3) . . . . ?
N1 N2 N3 C5 0.9(3) . . . . ?
N1 N2 N3 C13 -177.9(2) . . . . ?
C3 O1 C2 C1 171.4(4) . . . . ?
C2 O1 C3 O2 2.5(4) . . . . ?
C2 O1 C3 C4 178.0(2) . . . . ?
O2 C3 C4 O3 48.6(3) . . . . ?
O1 C3 C4 O3 -127.0(2) . . . . ?
O2 C3 C4 C5 -134.1(3) . . . . ?
O1 C3 C4 C5 50.2(3) . . . . ?
N2 N3 C5 C6 -1.0(3) . . . . ?
C13 N3 C5 C6 177.6(3) . . . . ?
N2 N3 C5 C4 174.5(2) . . . . ?
C13 N3 C5 C4 -6.8(4) . . . . ?
O3 C4 C5 N3 12.8(4) . . . . ?
C3 C4 C5 N3 -164.3(2) . . . . ?
O3 C4 C5 C6 -173.2(3) . . . . ?
C3 C4 C5 C6 9.7(4) . . . . ?
N2 N1 C6 C5 -0.2(3) . . . . ?
N2 N1 C6 C7 175.9(2) . . . . ?
N3 C5 C6 N1 0.7(3) . . . . ?
C4 C5 C6 N1 -174.0(2) . . . . ?
N3 C5 C6 C7 -174.7(2) . . . . ?
C4 C5 C6 C7 10.6(5) . . . . ?
N1 C6 C7 C8 -134.2(3) . . . . ?
C5 C6 C7 C8 40.9(4) . . . . ?
N1 C6 C7 C12 41.5(4) . . . . ?
C5 C6 C7 C12 -143.5(3) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
C6 C7 C8 C9 175.9(3) . . . . ?
C7 C8 C9 C10 -1.7(5) . . . . ?
C8 C9 C10 C11 1.7(5) . . . . ?
C8 C9 C10 Cl1 -177.7(2) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
Cl1 C10 C11 C12 179.2(3) . . . . ?
C10 C11 C12 C7 -1.5(5) . . . . ?
C8 C7 C12 C11 1.4(4) . . . . ?
C6 C7 C12 C11 -174.3(3) . . . . ?
N2 N3 C13 C14 104.1(3) . . . . ?
C5 N3 C13 C14 -74.4(4) . . . . ?
N3 C13 C14 C15 140.1(3) . . . . ?
N3 C13 C14 C19 -44.1(4) . . . . ?
C19 C14 C15 C16 -1.5(5) . . . . ?
C13 C14 C15 C16 174.6(3) . . . . ?
C14 C15 C16 C17 1.5(6) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C15 C16 C17 C20 -178.4(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C20 C17 C18 C19 177.8(3) . . . . ?
C17 C18 C19 C14 -0.3(5) . . . . ?
C15 C14 C19 C18 0.9(4) . . . . ?
C13 C14 C19 C18 -175.1(3) . . . . ?

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.505
_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_DNAEEM
_database_code_depnum_ccdc_archive 'CCDC 988860'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
Ethyl 2-(1-(4-methylbenzyl)-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate
;
_chemical_formula_moiety         'C20 H19 N3 O3'
_chemical_formula_sum            'C20 H19 N3 O3'
_chemical_formula_iupac          'C20 H19 N3 O3'
_chemical_formula_weight         349.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.2517(3)
_cell_length_b                   17.9945(9)
_cell_length_c                   12.2748(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.877(2)
_cell_angle_gamma                90
_cell_volume                     1795.61(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2801
_cell_measurement_theta_min      2.029
_cell_measurement_theta_max      27.465
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.970
_exptl_special_details           
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            16244
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.029
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_full        27.465
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             4114
_reflns_number_gt                2801
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         4114
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0766P)²+0.4720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.77274(16) 0.37923(7) 0.45265(12) 0.0593(4) Uani 1 1 d . . . . .
O2 O 0.6996(2) 0.49576(8) 0.48494(14) 0.0749(5) Uani 1 1 d . . . . .
O3 O 0.4675(2) 0.46585(8) 0.29288(13) 0.0721(4) Uani 1 1 d . . . . .
N1 N 0.3346(2) 0.23921(9) 0.41336(16) 0.0641(5) Uani 1 1 d . . . . .
N2 N 0.2636(2) 0.25488(10) 0.31187(16) 0.0681(5) Uani 1 1 d . . . . .
N3 N 0.31731(19) 0.32117(9) 0.28530(13) 0.0543(4) Uani 1 1 d . . . . .
C1 C 1.0207(4) 0.32365(18) 0.5357(3) 0.1181(12) Uani 1 1 d . . . . .
H1A H 1.043118 0.311098 0.463698 0.177 Uiso 1 1 calc R U . . .
H1B H 0.960417 0.283971 0.562465 0.177 Uiso 1 1 calc R U . . .
H1C H 1.122507 0.331075 0.585498 0.177 Uiso 1 1 calc R U . . .
C2 C 0.9264(3) 0.38971(14) 0.5288(2) 0.0835(8) Uani 1 1 d . . . . .
H2A H 0.987910 0.430174 0.503206 0.100 Uiso 1 1 calc R U . . .
H2B H 0.903649 0.402604 0.601375 0.100 Uiso 1 1 calc R U . . .
C3 C 0.6721(2) 0.43636(10) 0.44285(16) 0.0514(4) Uani 1 1 d . . . . .
C4 C 0.5138(2) 0.41935(10) 0.36271(15) 0.0498(4) Uani 1 1 d . . . . .
C5 C 0.4287(2) 0.34885(10) 0.37034(14) 0.0457(4) Uani 1 1 d . . . . .
C6 C 0.4375(2) 0.29537(9) 0.45198(15) 0.0483(4) Uani 1 1 d . . . . .
C7 C 0.5323(2) 0.29220(10) 0.56448(15) 0.0473(4) Uani 1 1 d . . . . .
C8 C 0.6190(3) 0.22779(11) 0.60027(18) 0.0602(5) Uani 1 1 d . . . . .
H8 H 0.615638 0.187263 0.552911 0.072 Uiso 1 1 calc R U . . .
C9 C 0.7086(3) 0.22377(14) 0.7043(2) 0.0745(7) Uani 1 1 d . . . . .
H9 H 0.766788 0.180681 0.727361 0.089 Uiso 1 1 calc R U . . .
C10 C 0.7134(3) 0.28289(16) 0.7751(2) 0.0819(7) Uani 1 1 d . . . . .
H10 H 0.774674 0.279963 0.846000 0.098 Uiso 1 1 calc R U . . .
C11 C 0.6274(3) 0.34656(14) 0.74103(18) 0.0759(7) Uani 1 1 d . . . . .
H11 H 0.630192 0.386556 0.789293 0.091 Uiso 1 1 calc R U . . .
C12 C 0.5373(3) 0.35155(11) 0.63617(16) 0.0592(5) Uani 1 1 d . . . . .
H12 H 0.479681 0.394869 0.613578 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2615(3) 0.34937(13) 0.17316(16) 0.0640(5) Uani 1 1 d . . . . .
H13A H 0.243845 0.307568 0.122620 0.077 Uiso 1 1 calc R U . . .
H13B H 0.347911 0.379825 0.151934 0.077 Uiso 1 1 calc R U . . .
C14 C 0.1057(2) 0.39458(11) 0.16037(16) 0.0562(5) Uani 1 1 d . . . . .
C15 C 0.0024(3) 0.39399(12) 0.05994(18) 0.0646(6) Uani 1 1 d . . . . .
H15 H 0.025113 0.363455 0.003313 0.078 Uiso 1 1 calc R U . . .
C16 C -0.1366(3) 0.43928(14) 0.0432(2) 0.0760(7) Uani 1 1 d . . . . .
H16 H -0.205580 0.438790 -0.025199 0.091 Uiso 1 1 calc R U . . .
C17 C -0.1739(3) 0.48458(13) 0.1253(2) 0.0725(6) Uani 1 1 d . . . . .
C18 C -0.0732(3) 0.48266(14) 0.2251(2) 0.0783(7) Uani 1 1 d . . . . .
H18 H -0.098829 0.511499 0.282710 0.094 Uiso 1 1 calc R U . . .
C19 C 0.0655(3) 0.43912(14) 0.2430(2) 0.0738(6) Uani 1 1 d . . . . .
H19 H 0.133210 0.439719 0.311882 0.089 Uiso 1 1 calc R U . . .
C20 C -0.3205(4) 0.53609(19) 0.1046(3) 0.1114(11) Uani 1 1 d . . . . .
H20A H -0.357741 0.540927 0.026454 0.167 Uiso 1 1 calc R U . . .
H20B H -0.289504 0.584024 0.135699 0.167 Uiso 1 1 calc R U . . .
H20C H -0.407484 0.516036 0.138591 0.167 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.314(2) . ?
O1 C2 1.452(3) . ?
O2 C3 1.192(2) . ?
O3 C4 1.212(2) . ?
N1 N2 1.313(3) . ?
N1 C6 1.352(2) . ?
N2 N3 1.332(2) . ?
N3 C5 1.361(2) . ?
N3 C13 1.465(3) . ?
C1 C2 1.415(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(3) . ?
C4 C5 1.461(3) . ?
C5 C6 1.382(2) . ?
C6 C7 1.467(3) . ?
C7 C12 1.380(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.364(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.506(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.373(3) . ?
C14 C19 1.377(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(4) . ?
C17 C20 1.511(4) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C3 O1 C2 115.19(16) . . ?
N2 N1 C6 108.87(16) . . ?
N1 N2 N3 108.13(16) . . ?
N2 N3 C5 110.43(16) . . ?
N2 N3 C13 118.41(17) . . ?
C5 N3 C13 130.98(17) . . ?
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 . . ?
C1 C2 O1 109.9(2) . . ?
C1 C2 H2A 109.7 . . ?
O1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
O1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O2 C3 O1 126.24(19) . . ?
O2 C3 C4 122.56(18) . . ?
O1 C3 C4 111.09(15) . . ?
O3 C4 C5 123.26(18) . . ?
O3 C4 C3 116.65(17) . . ?
C5 C4 C3 120.05(15) . . ?
N3 C5 C6 104.23(15) . . ?
N3 C5 C4 122.50(16) . . ?
C6 C5 C4 133.23(17) . . ?
N1 C6 C5 108.31(17) . . ?
N1 C6 C7 120.15(16) . . ?
C5 C6 C7 131.52(16) . . ?
C12 C7 C8 119.05(18) . . ?
C12 C7 C6 121.54(16) . . ?
C8 C7 C6 119.42(17) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.90(19) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
N3 C13 C14 114.22(17) . . ?
N3 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 118.3(2) . . ?
C15 C14 C13 118.46(19) . . ?
C19 C14 C13 123.13(18) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 117.9(2) . . ?
C18 C17 C20 121.0(3) . . ?
C16 C17 C20 121.0(3) . . ?
C17 C18 C19 121.5(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 N1 N2 N3 -1.1(2) . . . . ?
N1 N2 N3 C5 1.3(2) . . . . ?
N1 N2 N3 C13 176.97(17) . . . . ?
C3 O1 C2 C1 177.5(2) . . . . ?
C2 O1 C3 O2 4.6(3) . . . . ?
C2 O1 C3 C4 -179.11(18) . . . . ?
O2 C3 C4 O3 44.1(3) . . . . ?
O1 C3 C4 O3 -132.29(18) . . . . ?
O2 C3 C4 C5 -137.7(2) . . . . ?
O1 C3 C4 C5 45.9(2) . . . . ?
N2 N3 C5 C6 -1.0(2) . . . . ?
C13 N3 C5 C6 -175.92(19) . . . . ?
N2 N3 C5 C4 177.24(16) . . . . ?
C13 N3 C5 C4 2.3(3) . . . . ?
O3 C4 C5 N3 17.2(3) . . . . ?
C3 C4 C5 N3 -160.86(17) . . . . ?
O3 C4 C5 C6 -165.2(2) . . . . ?
C3 C4 C5 C6 16.8(3) . . . . ?
N2 N1 C6 C5 0.5(2) . . . . ?
N2 N1 C6 C7 179.58(17) . . . . ?
N3 C5 C6 N1 0.3(2) . . . . ?
C4 C5 C6 N1 -177.64(19) . . . . ?
N3 C5 C6 C7 -178.65(18) . . . . ?
C4 C5 C6 C7 3.4(3) . . . . ?
N1 C6 C7 C12 -131.4(2) . . . . ?
C5 C6 C7 C12 47.5(3) . . . . ?
N1 C6 C7 C8 48.3(3) . . . . ?
C5 C6 C7 C8 -132.8(2) . . . . ?
C12 C7 C8 C9 -0.6(3) . . . . ?
C6 C7 C8 C9 179.64(19) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C7 0.2(4) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
C6 C7 C12 C11 180.0(2) . . . . ?
N2 N3 C13 C14 90.0(2) . . . . ?
C5 N3 C13 C14 -95.4(2) . . . . ?
N3 C13 C14 C15 -149.65(19) . . . . ?
N3 C13 C14 C19 33.4(3) . . . . ?
C19 C14 C15 C16 1.7(3) . . . . ?
C13 C14 C15 C16 -175.5(2) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 -1.7(3) . . . . ?
C15 C16 C17 C20 177.1(2) . . . . ?
C16 C17 C18 C19 2.5(4) . . . . ?
C20 C17 C18 C19 -176.3(3) . . . . ?
C17 C18 C19 C14 -1.3(4) . . . . ?
C15 C14 C19 C18 -0.9(4) . . . . ?
C13 C14 C19 C18 176.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13B O3 0.97 2.40 2.930(3) 113.6 . yes

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.038

