# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_exp_207-jsl-11a
_database_code_depnum_ccdc_archive 'CCDC 1901738'
loop_
_audit_author_name
_audit_author_address
'J SUBBALAKSHMI'
;BITS Pilani Hyderabad Campus 
India
;
_audit_update_record             
;
2019-03-07 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_audit_creation_date             2019-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.15037(8)
_cell_length_b                   15.2072(2)
_cell_length_c                   13.27838(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.9346(13)
_cell_angle_gamma                90
_cell_volume                     1215.08(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5124
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9560
_cell_measurement_theta_min      4.4650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6120
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.094
_diffrn_reflns_theta_min         4.476
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  19.00   0.50    7.00    --    0.00  82.00 120.00   60
  2  ω     59.00  89.00   0.50    7.00    --    0.00  82.00 120.00   60
  3  ω     -6.00  19.00   0.50    7.00    --    0.00 -19.00 -90.00   50
  4  ω    -79.00 -36.00   0.50    7.00    --    0.00 -19.00 -90.00   86
  5  ω     80.00 133.00   0.50    7.00    --   95.80  45.00 -90.00  106
  6  ω    141.00 167.00   0.50    7.00    --   95.80  45.00 -90.00   52
  7  ω     86.00 125.00   0.50    7.00    --   95.80 -77.00 -60.00   78
  8  ω     45.00 112.00   0.50    7.00    --   95.80 -82.00 -90.00  134
  9  ω      7.00 123.00   0.50    7.00    --   95.80 -77.00 120.00  232
 10  ω      8.00  34.00   0.50    7.00    --   95.80 -82.00 -90.00   52
 11  ω     73.00 178.00   0.50    7.00    --   95.80  61.00 120.00  210
 12  ω     70.00 105.00   0.50    7.00    --   95.80 -82.00  90.00   70
 13  ω     86.00 179.00   0.50    7.00    --   95.80  30.00-150.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0080109000
_diffrn_orient_matrix_UB_12      -0.0991903000
_diffrn_orient_matrix_UB_13      0.0222909000
_diffrn_orient_matrix_UB_21      -0.2515172000
_diffrn_orient_matrix_UB_22      0.0067509000
_diffrn_orient_matrix_UB_23      -0.0038911000
_diffrn_orient_matrix_UB_31      -0.0470583000
_diffrn_orient_matrix_UB_32      -0.0192598000
_diffrn_orient_matrix_UB_33      -0.1164532000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2349
_reflns_number_total             2399
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.5922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0855
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B), C14(H14A,H14B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C1(H1), C5(H5), C4(H4)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.07069(12) 0.57167(5) 0.10533(6) 0.01631(18) Uani 1 1 d . . . . .
O2 O -0.15230(13) 0.57975(5) 0.42644(6) 0.01864(19) Uani 1 1 d . . . . .
H2 H -0.224101 0.611075 0.457879 0.028 Uiso 1 1 calc GR . . . .
N003 N 0.10456(14) 0.55354(6) 0.27209(7) 0.0135(2) Uani 1 1 d . . . . .
N2 N 1.11712(17) 0.82824(7) 0.05800(8) 0.0224(2) Uani 1 1 d . . . . .
N1 N 1.09307(17) 0.90539(7) 0.37791(8) 0.0249(2) Uani 1 1 d . . . . .
C6 C 0.74441(17) 0.76038(7) 0.21125(8) 0.0145(2) Uani 1 1 d . . . . .
C3 C 0.37028(17) 0.65044(7) 0.20573(8) 0.0140(2) Uani 1 1 d . . . . .
C2 C 0.45088(17) 0.70419(7) 0.29162(8) 0.0146(2) Uani 1 1 d . . . . .
H2A H 0.380461 0.703624 0.347215 0.018 Uiso 1 1 calc R . . . .
C1 C 0.63251(18) 0.75753(7) 0.29429(8) 0.0150(2) Uani 1 1 d . . . . .
H1 H 0.682941 0.792474 0.351863 0.018 Uiso 1 1 calc R . . . .
C5 C 0.65861(18) 0.70768(7) 0.12426(8) 0.0153(2) Uani 1 1 d . . . . .
H5 H 0.727082 0.708786 0.068040 0.018 Uiso 1 1 calc R . . . .
C7 C 0.18306(17) 0.59211(7) 0.19879(8) 0.0136(2) Uani 1 1 d . . . . .
C4 C 0.47608(18) 0.65492(7) 0.12129(8) 0.0154(2) Uani 1 1 d . . . . .
H4 H 0.421528 0.621685 0.062724 0.018 Uiso 1 1 calc R . . . .
C13 C 0.19698(18) 0.55176(7) 0.38324(8) 0.0148(2) Uani 1 1 d . . . . .
H13A H 0.350959 0.570527 0.395719 0.018 Uiso 1 1 calc R . . . .
H13B H 0.193642 0.491882 0.408048 0.018 Uiso 1 1 calc R . . . .
C8 C 0.93632(18) 0.81532(7) 0.21514(9) 0.0158(2) Uani 1 1 d . . . . .
C11 C -0.09625(18) 0.50185(8) 0.22844(8) 0.0175(2) Uani 1 1 d . . . . .
H11A H -0.229858 0.530258 0.240375 0.021 Uiso 1 1 calc R . . . .
H11B H -0.087526 0.442768 0.256514 0.021 Uiso 1 1 calc R . . . .
C14 C 0.07012(19) 0.61056(8) 0.44287(8) 0.0175(2) Uani 1 1 d . . . . .
H14A H 0.137567 0.608727 0.515647 0.021 Uiso 1 1 calc R . . . .
H14B H 0.072998 0.670838 0.419293 0.021 Uiso 1 1 calc R . . . .
C10 C 1.03848(18) 0.82278(7) 0.12983(9) 0.0172(2) Uani 1 1 d . . . . .
C12 C -0.08826(18) 0.50138(8) 0.11459(8) 0.0175(2) Uani 1 1 d . . . . .
H12A H -0.036896 0.445055 0.094354 0.021 Uiso 1 1 calc R . . . .
H12B H -0.233476 0.513813 0.072343 0.021 Uiso 1 1 calc R . . . .
C9 C 1.02568(18) 0.86512(8) 0.30393(9) 0.0181(2) Uani 1 1 d . . . . .


_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 C7 1.3265(13) . ?
O1 C12 1.4708(13) . ?
O2 H2 0.8200 . ?
O2 C14 1.4195(14) . ?
N003 C7 1.3111(14) . ?
N003 C13 1.4681(13) . ?
N003 C11 1.4775(13) . ?
N2 C10 1.1583(16) . ?
N1 C9 1.1590(16) . ?
C6 C1 1.4160(15) . ?
C6 C5 1.4153(16) . ?
C6 C8 1.4383(15) . ?
C3 C2 1.4074(15) . ?
C3 C7 1.4413(15) . ?
C3 C4 1.4095(15) . ?
C2 H2A 0.9300 . ?
C2 C1 1.3751(15) . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.3737(15) . ?
C4 H4 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5135(15) . ?
C8 C10 1.4089(16) . ?
C8 C9 1.4134(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5226(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C7 O1 C12 108.59(8) . . ?
C14 O2 H2 109.5 . . ?
C7 N003 C13 128.99(9) . . ?
C7 N003 C11 110.67(9) . . ?
C13 N003 C11 120.20(9) . . ?
C1 C6 C8 121.14(10) . . ?
C5 C6 C1 117.32(10) . . ?
C5 C6 C8 121.53(10) . . ?
C2 C3 C7 123.51(10) . . ?
C2 C3 C4 118.25(10) . . ?
C4 C3 C7 118.23(10) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 C3 120.77(10) . . ?
C1 C2 H2A 119.6 . . ?
C6 C1 H1 119.3 . . ?
C2 C1 C6 121.40(10) . . ?
C2 C1 H1 119.3 . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.24(10) . . ?
C4 C5 H5 119.4 . . ?
O1 C7 C3 117.31(9) . . ?
N003 C7 O1 112.90(9) . . ?
N003 C7 C3 129.78(10) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.95(10) . . ?
C5 C4 H4 119.5 . . ?
N003 C13 H13A 109.1 . . ?
N003 C13 H13B 109.1 . . ?
N003 C13 C14 112.38(9) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C10 C8 C6 121.13(10) . . ?
C10 C8 C9 117.80(10) . . ?
C9 C8 C6 121.05(10) . . ?
N003 C11 H11A 111.5 . . ?
N003 C11 H11B 111.5 . . ?
N003 C11 C12 101.31(8) . . ?
H11A C11 H11B 109.3 . . ?
C12 C11 H11A 111.5 . . ?
C12 C11 H11B 111.5 . . ?
O2 C14 C13 108.02(9) . . ?
O2 C14 H14A 110.1 . . ?
O2 C14 H14B 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
N2 C10 C8 178.16(12) . . ?
O1 C12 C11 103.77(8) . . ?
O1 C12 H12A 111.0 . . ?
O1 C12 H12B 111.0 . . ?
C11 C12 H12A 111.0 . . ?
C11 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
N1 C9 C8 177.87(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.740
_oxdiff_exptl_absorpt_empirical_full_min 0.550
####################################################################### 
# 
# 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_C:
_database_code_depnum_ccdc_archive 'CCDC 1914412'
loop_
_audit_author_name
_audit_author_address
'J SUBBALAKSHMI'
;BITS Pilani Hyderabad Campus 
India
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H9 N3 O'
_chemical_formula_sum            'C12 H9 N3 O'
_chemical_compound_source        Synthesis
_chemical_melting_point          ?

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         101.3
_chemical_formula_weight         211.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_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.
;

_cell_length_a                   6.3852(3)
_cell_length_b                   7.1557(6)
_cell_length_c                   11.6848(3)
_cell_angle_alpha                93.971(5)
_cell_angle_beta                 93.665(3)
_cell_angle_gamma                111.132(6)
_cell_volume                     494.52(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4457
_cell_measurement_theta_min      6.6810
_cell_measurement_theta_max      78.9950
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.772
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              Rigaku
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5568
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.809
_diffrn_reflns_theta_max         79.544
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2009
_reflns_number_gt                1865
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+0.5592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2009
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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_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
O001 O 0.0230(2) 0.1005(2) 0.87816(11) 0.0192(3) Uani 1 1 d . . . . .
N002 N -0.0938(3) 0.0977(2) 0.69749(14) 0.0166(4) Uani 1 1 d . . . . .
N003 N 1.1022(3) 0.7782(3) 0.53166(14) 0.0228(4) Uani 1 1 d . . . . .
N004 N 1.2941(3) 0.7372(3) 0.89547(14) 0.0220(4) Uani 1 1 d . . . . .
C005 C 1.0554(3) 0.7105(3) 0.61796(16) 0.0173(4) Uani 1 1 d . . . . .
C006 C 0.0774(3) 0.1573(3) 0.77576(16) 0.0148(4) Uani 1 1 d . . . . .
C007 C 0.9929(3) 0.6310(3) 0.72268(16) 0.0161(4) Uani 1 1 d . . . . .
C008 C 0.4719(3) 0.3338(3) 0.85684(16) 0.0170(4) Uani 1 1 d . . . . .
H008 H 0.429578 0.298518 0.929369 0.020 Uiso 1 1 calc R U . . .
C009 C 0.5993(3) 0.4357(3) 0.63928(16) 0.0169(4) Uani 1 1 d . . . . .
H009 H 0.641799 0.467239 0.566245 0.020 Uiso 1 1 calc R U . . .
C00A C 1.1601(3) 0.6908(3) 0.81718(16) 0.0167(4) Uani 1 1 d . . . . .
C00B C 0.7642(3) 0.5051(3) 0.73546(16) 0.0157(4) Uani 1 1 d . . . . .
C00C C 0.6936(3) 0.4460(3) 0.84415(16) 0.0162(4) Uani 1 1 d . . . . .
H00C H 0.799147 0.483899 0.908281 0.019 Uiso 1 1 calc R U . . .
C00D C 0.3781(3) 0.3229(3) 0.65183(16) 0.0174(4) Uani 1 1 d . . . . .
H00D H 0.273169 0.279805 0.587413 0.021 Uiso 1 1 calc R U . . .
C00E C -0.2206(3) -0.0190(3) 0.87002(16) 0.0176(4) Uani 1 1 d . . . . .
H00A H -0.296121 0.043496 0.920847 0.021 Uiso 1 1 calc R U . . .
H00B H -0.247527 -0.154411 0.890264 0.021 Uiso 1 1 calc R U . . .
C00F C 0.3086(3) 0.2719(3) 0.76121(16) 0.0160(4) Uani 1 1 d . . . . .
C00G C -0.3039(3) -0.0225(3) 0.74376(16) 0.0162(4) Uani 1 1 d . . . . .
H00E H -0.366177 -0.158538 0.705885 0.019 Uiso 1 1 calc R U . . .
H00F H -0.415938 0.039422 0.736664 0.019 Uiso 1 1 calc R U . . .
H9 H -0.089(5) 0.129(4) 0.625(3) 0.039(8) Uiso 1 1 d . . . . .


_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
O001 C006 1.318(2) . ?
O001 C00E 1.473(2) . ?
N002 C006 1.302(2) . ?
N002 C00G 1.468(2) . ?
N002 H9 0.89(3) . ?
N003 C005 1.159(3) . ?
N004 C00A 1.154(2) . ?
C005 C007 1.406(3) . ?
C006 C00F 1.435(2) . ?
C007 C00A 1.413(2) . ?
C007 C00B 1.436(2) . ?
C008 C00C 1.376(3) . ?
C008 C00F 1.408(3) . ?
C008 H008 0.9300 . ?
C009 C00D 1.375(3) . ?
C009 C00B 1.419(3) . ?
C009 H009 0.9300 . ?
C00B C00C 1.416(3) . ?
C00C H00C 0.9300 . ?
C00D C00F 1.408(3) . ?
C00D H00D 0.9300 . ?
C00E C00G 1.531(3) . ?
C00E H00A 0.9700 . ?
C00E H00B 0.9700 . ?
C00G H00E 0.9700 . ?
C00G H00F 0.9700 . ?

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
C006 O001 C00E 108.75(14) . . ?
C006 N002 C00G 111.94(15) . . ?
C006 N002 H9 125.4(19) . . ?
C00G N002 H9 122.6(19) . . ?
N003 C005 C007 178.1(2) . . ?
N002 C006 O001 113.43(16) . . ?
N002 C006 C00F 127.47(16) . . ?
O001 C006 C00F 119.10(16) . . ?
C005 C007 C00A 117.40(16) . . ?
C005 C007 C00B 121.32(16) . . ?
C00A C007 C00B 121.15(16) . . ?
C00C C008 C00F 120.71(17) . . ?
C00C C008 H008 119.6 . . ?
C00F C008 H008 119.6 . . ?
C00D C009 C00B 121.36(17) . . ?
C00D C009 H009 119.3 . . ?
C00B C009 H009 119.3 . . ?
N004 C00A C007 178.8(2) . . ?
C00C C00B C009 117.25(16) . . ?
C00C C00B C007 121.62(16) . . ?
C009 C00B C007 121.12(16) . . ?
C008 C00C C00B 121.36(17) . . ?
C008 C00C H00C 119.3 . . ?
C00B C00C H00C 119.3 . . ?
C009 C00D C00F 120.70(17) . . ?
C009 C00D H00D 119.6 . . ?
C00F C00D H00D 119.6 . . ?
O001 C00E C00G 104.72(14) . . ?
O001 C00E H00A 110.8 . . ?
C00G C00E H00A 110.8 . . ?
O001 C00E H00B 110.8 . . ?
C00G C00E H00B 110.8 . . ?
H00A C00E H00B 108.9 . . ?
C008 C00F C00D 118.53(17) . . ?
C008 C00F C006 120.21(17) . . ?
C00D C00F C006 121.25(17) . . ?
N002 C00G C00E 101.15(14) . . ?
N002 C00G H00E 111.5 . . ?
C00E C00G H00E 111.5 . . ?
N002 C00G H00F 111.5 . . ?
C00E C00G H00F 111.5 . . ?
H00E C00G H00F 109.4 . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_exp_342-j14r
_database_code_depnum_ccdc_archive 'CCDC 1935036'
loop_
_audit_author_name
_audit_author_address
'SYED ANWARHUSSAINI'
;BITS Pilani, Hyderabad Campus 
India
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_audit_creation_date             2019-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 Cl2 N4 O'
_chemical_formula_sum            'C15 H16 Cl2 N4 O'
_chemical_formula_weight         339.22
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.5950(7)
_cell_length_b                   16.6928(8)
_cell_length_c                   7.6628(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.088(5)
_cell_angle_gamma                90
_cell_volume                     1590.85(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5527
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.7420
_cell_measurement_theta_min      3.2730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17497
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.997
_diffrn_reflns_theta_min         3.167
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00 -18.00   0.50   45.03    --   -3.50 -37.00 120.00   86
  2  ω    -91.00   4.00   0.50   45.03    --   -3.50 -37.00-180.00  190
  3  ω    -29.00  -3.00   0.50   45.03    --    3.50 -37.00-120.00   52
  4  ω    -65.00 -36.00   0.50   45.03    --    3.50 -37.00-120.00   58
  5  ω      9.00  34.00   0.50   45.03    --    3.50 -82.00 -30.00   50
  6  ω    -85.00  -6.00   0.50   45.03    --    3.50 -82.00 -30.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067177000
_diffrn_orient_matrix_UB_12      0.0046507000
_diffrn_orient_matrix_UB_13      0.0895911000
_diffrn_orient_matrix_UB_21      0.0457185000
_diffrn_orient_matrix_UB_22      -0.0244350000
_diffrn_orient_matrix_UB_23      0.0266634000
_diffrn_orient_matrix_UB_31      0.0334786000
_diffrn_orient_matrix_UB_32      0.0344354000
_diffrn_orient_matrix_UB_33      0.0068086000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3509
_reflns_number_total             4485
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+2.1780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1547
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C2(H2), N4(H4), C4(H4A), C1(H1)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.45569(4) 0.11404(3) 0.44849(8) 0.02131(15) Uani 1 1 d . . . . .
Cl2 Cl 1.02261(6) 0.76331(4) 0.41557(9) 0.03161(18) Uani 1 1 d . . . . .
C13 C 0.66643(19) 0.06632(14) 0.3599(3) 0.0190(4) Uani 1 1 d . . . . .
H13 H 0.610995 0.032549 0.380460 0.023 Uiso 1 1 calc R . . . .
N2 N 0.65245(15) 0.14446(12) 0.3647(3) 0.0171(4) Uani 1 1 d . . . . .
O1 O 0.91141(15) 0.50493(11) 0.2349(3) 0.0276(4) Uani 1 1 d . . . . .
N3 N 0.75702(16) 0.03492(12) 0.3267(3) 0.0191(4) Uani 1 1 d . . . . .
C15 C 0.7728(2) -0.05156(15) 0.3185(4) 0.0270(5) Uani 1 1 d . . . . .
H15A H 0.708789 -0.078545 0.340117 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.832098 -0.067118 0.406502 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.787727 -0.065888 0.203513 0.041 Uiso 1 1 calc GR . . . .
C5 C 0.65260(19) 0.46718(14) 0.3837(3) 0.0191(5) Uani 1 1 d . . . . .
H5 H 0.631392 0.519074 0.405884 0.023 Uiso 1 1 calc R . . . .
N1 N 0.36329(18) 0.30844(13) 0.4984(3) 0.0256(5) Uani 1 1 d . . . . .
C9 C 0.8604(2) 0.66408(15) 0.2821(3) 0.0213(5) Uani 1 1 d . . . . .
H9A H 0.816070 0.711367 0.255481 0.026 Uiso 1 1 calc R . . . .
H9B H 0.897872 0.653977 0.182994 0.026 Uiso 1 1 calc R . . . .
C11 C 0.44191(19) 0.28305(14) 0.4607(3) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.71433(19) 0.31156(14) 0.3185(3) 0.0202(5) Uani 1 1 d . . . . .
H2 H 0.735784 0.259766 0.296021 0.024 Uiso 1 1 calc R . . . .
C3 C 0.61656(18) 0.32384(14) 0.3821(3) 0.0156(4) Uani 1 1 d . . . . .
C12 C 0.56269(18) 0.17739(14) 0.4041(3) 0.0168(4) Uani 1 1 d . . . . .
C10 C 0.9412(2) 0.67839(16) 0.4471(3) 0.0242(5) Uani 1 1 d . . . . .
H10A H 0.986308 0.631437 0.472862 0.029 Uiso 1 1 calc R . . . .
H10B H 0.903826 0.687800 0.546661 0.029 Uiso 1 1 calc R . . . .
C7 C 0.82467(19) 0.52017(14) 0.2850(3) 0.0183(4) Uani 1 1 d . . . . .
N4 N 0.79303(16) 0.59593(12) 0.3077(3) 0.0204(4) Uani 1 1 d . . . . .
H4 H 0.731103 0.604198 0.338195 0.025 Uiso 1 1 calc R . . . .
C6 C 0.74983(18) 0.45462(14) 0.3206(3) 0.0162(4) Uani 1 1 d . . . . .
C4 C 0.58785(19) 0.40335(14) 0.4135(3) 0.0197(5) Uani 1 1 d . . . . .
H4A H 0.523688 0.413238 0.455317 0.024 Uiso 1 1 calc R . . . .
C8 C 0.54315(18) 0.25821(14) 0.4142(3) 0.0161(4) Uani 1 1 d . . . . .
C1 C 0.77882(19) 0.37581(14) 0.2892(3) 0.0202(5) Uani 1 1 d . . . . .
H1 H 0.843100 0.366210 0.247516 0.024 Uiso 1 1 calc R . . . .
C14 C 0.8464(2) 0.08499(17) 0.2939(4) 0.0301(6) Uani 1 1 d . . . . .
H14A H 0.823783 0.118492 0.193078 0.045 Uiso 1 1 calc GR . . . .
H14B H 0.904893 0.051611 0.271553 0.045 Uiso 1 1 calc GR . . . .
H14C H 0.869641 0.117901 0.395543 0.045 Uiso 1 1 calc GR . . . .


_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 C12 1.788(2) . ?
Cl2 C10 1.788(3) . ?
C13 N2 1.317(3) . ?
C13 N3 1.317(3) . ?
N2 C12 1.334(3) . ?
O1 C7 1.240(3) . ?
N3 C15 1.460(3) . ?
N3 C14 1.456(3) . ?
C5 C6 1.402(3) . ?
C5 C4 1.382(3) . ?
N1 C11 1.155(3) . ?
C9 C10 1.511(4) . ?
C9 N4 1.451(3) . ?
C11 C8 1.438(3) . ?
C2 C3 1.409(3) . ?
C2 C1 1.385(3) . ?
C3 C4 1.406(3) . ?
C3 C8 1.479(3) . ?
C12 C8 1.376(3) . ?
C7 N4 1.345(3) . ?
C7 C6 1.497(3) . ?
C6 C1 1.396(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C13 N2 121.6(2) . . ?
C13 N2 C12 122.4(2) . . ?
C13 N3 C15 122.0(2) . . ?
C13 N3 C14 121.5(2) . . ?
C14 N3 C15 116.5(2) . . ?
C4 C5 C6 120.8(2) . . ?
N4 C9 C10 110.0(2) . . ?
N1 C11 C8 175.2(3) . . ?
C1 C2 C3 120.7(2) . . ?
C2 C3 C8 123.6(2) . . ?
C4 C3 C2 117.3(2) . . ?
C4 C3 C8 119.1(2) . . ?
N2 C12 Cl1 119.39(18) . . ?
N2 C12 C8 125.6(2) . . ?
C8 C12 Cl1 114.98(17) . . ?
C9 C10 Cl2 109.67(18) . . ?
O1 C7 N4 121.7(2) . . ?
O1 C7 C6 121.1(2) . . ?
N4 C7 C6 117.1(2) . . ?
C7 N4 C9 121.9(2) . . ?
C5 C6 C7 124.3(2) . . ?
C1 C6 C5 117.8(2) . . ?
C1 C6 C7 117.9(2) . . ?
C5 C4 C3 121.7(2) . . ?
C11 C8 C3 115.4(2) . . ?
C12 C8 C11 118.1(2) . . ?
C12 C8 C3 126.5(2) . . ?
C2 C1 C6 121.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.881
