# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_19dmf_100k
_database_code_depnum_ccdc_archive 'CCDC 1876822'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2018-12-04 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
_audit_creation_date             2018-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 Cl N2 O2, C4 H9 N O'
_chemical_formula_sum            'C16 H18 Cl N3 O3'
_chemical_formula_weight         335.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 N2 O2 Cl1'
_chemical_oxdiff_usercomment     '0.3 mm loop'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0839(3)
_cell_length_b                   10.8648(6)
_cell_length_c                   10.9553(6)
_cell_angle_alpha                90.615(5)
_cell_angle_beta                 94.232(4)
_cell_angle_gamma                107.982(5)
_cell_volume                     799.30(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4259
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.6280
_cell_measurement_theta_min      3.0160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9552
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.666
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.20   0.30   15.00    --   29.89  54.00-120.00  624
  2  ω    -69.00 118.20   0.30   15.00    --   29.89  54.00  60.00  624
  3  ω    -69.00 118.20   0.30   15.00    --   29.89  54.00  60.00  624
  4  ω    -65.00 118.00   0.30   15.00    --   29.89  54.00   0.00  610
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0937886000
_diffrn_orient_matrix_UB_12      0.0101359000
_diffrn_orient_matrix_UB_13      0.0030945000
_diffrn_orient_matrix_UB_21      -0.0485245000
_diffrn_orient_matrix_UB_22      -0.0665713000
_diffrn_orient_matrix_UB_23      -0.0147183000
_diffrn_orient_matrix_UB_31      0.0020940000
_diffrn_orient_matrix_UB_32      -0.0135057000
_diffrn_orient_matrix_UB_33      0.0631977000
_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              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2457
_reflns_number_total             2799
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0776P)²+0.3610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1368
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C12(H12), C5(H5), C4(H4), C9(H9), C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.06300(7) 0.80874(6) -0.08417(5) 0.0391(2) Uani 1 1 d . . . . .
O1 O 0.3166(2) 0.75217(15) 0.20112(14) 0.0320(4) Uani 1 1 d . . . . .
O2 O 0.7778(2) 0.71638(16) 0.52669(14) 0.0349(4) Uani 1 1 d . . . . .
O3 O 0.4394(2) 0.59252(15) 0.61443(13) 0.0375(4) Uani 1 1 d . . . . .
N1 N 0.6517(2) 0.85072(16) 0.04921(15) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.4743(2) 0.83799(15) 0.00415(15) 0.0260(4) Uani 1 1 d . . . . .
N3 N 0.2223(3) 0.51963(17) 0.75520(16) 0.0328(4) Uani 1 1 d . . . . .
C7 C 0.4551(3) 0.86433(18) -0.12161(18) 0.0259(4) Uani 1 1 d . . . . .
C6 C 0.6698(3) 0.82020(18) 0.17153(18) 0.0253(4) Uani 1 1 d . . . . .
C1 C 0.5065(3) 0.77048(19) 0.24573(18) 0.0258(4) Uani 1 1 d . . . . .
C2 C 0.5424(3) 0.73594(19) 0.36464(18) 0.0286(5) Uani 1 1 d . . . . .
H2A H 0.4365 0.7021 0.4125 0.034 Uiso 1 1 calc R . . . .
C3 C 0.7367(3) 0.7517(2) 0.41297(18) 0.0289(5) Uani 1 1 d . . . . .
C12 C 0.6148(3) 0.90148(19) -0.19583(19) 0.0291(5) Uani 1 1 d . . . . .
H12 H 0.7439 0.9140 -0.1620 0.035 Uiso 1 1 calc R . . . .
C8 C 0.2638(3) 0.84887(19) -0.17511(19) 0.0281(4) Uani 1 1 d . . . . .
C5 C 0.8631(3) 0.8371(2) 0.22422(18) 0.0289(5) Uani 1 1 d . . . . .
H5 H 0.9704 0.8710 0.1774 0.035 Uiso 1 1 calc R . . . .
C4 C 0.8988(3) 0.8053(2) 0.34214(19) 0.0304(5) Uani 1 1 d . . . . .
H4 H 1.0286 0.8189 0.3753 0.037 Uiso 1 1 calc R . . . .
C9 C 0.2285(3) 0.8664(2) -0.29875(19) 0.0315(5) Uani 1 1 d . . . . .
H9 H 0.0998 0.8552 -0.3328 0.038 Uiso 1 1 calc R . . . .
C11 C 0.5809(3) 0.9195(2) -0.31917(19) 0.0333(5) Uani 1 1 d . . . . .
H11 H 0.6875 0.9442 -0.3679 0.040 Uiso 1 1 calc R . . . .
C14 C 0.4082(3) 0.56204(19) 0.72183(19) 0.0313(5) Uani 1 1 d . . . . .
C10 C 0.3882(3) 0.9010(2) -0.37094(19) 0.0333(5) Uani 1 1 d . . . . .
H10 H 0.3665 0.9119 -0.4543 0.040 Uiso 1 1 calc R . . . .
C13 C 0.5777(3) 0.5699(2) 0.8161(2) 0.0377(5) Uani 1 1 d . . . . .
H13A H 0.5694 0.4845 0.8424 0.056 Uiso 1 1 calc GR . . . .
H13B H 0.5698 0.6227 0.8852 0.056 Uiso 1 1 calc GR . . . .
H13C H 0.7020 0.6075 0.7809 0.056 Uiso 1 1 calc GR . . . .
C15 C 0.0560(3) 0.5100(2) 0.6640(2) 0.0396(5) Uani 1 1 d . . . . .
H15A H 0.0361 0.5932 0.6566 0.059 Uiso 1 1 calc GR . . . .
H15B H -0.0627 0.4486 0.6893 0.059 Uiso 1 1 calc GR . . . .
H15C H 0.0855 0.4820 0.5863 0.059 Uiso 1 1 calc GR . . . .
C16 C 0.1738(4) 0.4862(2) 0.8802(2) 0.0423(6) Uani 1 1 d . . . . .
H16A H 0.2581 0.4389 0.9145 0.063 Uiso 1 1 calc GR . . . .
H16B H 0.0371 0.4337 0.8795 0.063 Uiso 1 1 calc GR . . . .
H16C H 0.1944 0.5639 0.9288 0.063 Uiso 1 1 calc GR . . . .
H1 H 0.326(5) 0.783(3) 0.124(3) 0.080(11) Uiso 1 1 d . . . . .
H2 H 0.675(5) 0.680(3) 0.551(3) 0.058(9) 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
Cl1 C8 1.744(2) . ?
O1 C1 1.351(2) . ?
O1 H1 0.91(4) . ?
O2 C3 1.345(2) . ?
O2 H2 0.78(3) . ?
O3 C14 1.243(3) . ?
N1 N2 1.281(2) . ?
N1 C6 1.390(3) . ?
N2 C7 1.416(3) . ?
N3 C14 1.334(3) . ?
N3 C15 1.465(3) . ?
N3 C16 1.459(3) . ?
C7 C12 1.402(3) . ?
C7 C8 1.396(3) . ?
C6 C1 1.433(3) . ?
C6 C5 1.403(3) . ?
C1 C2 1.387(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.396(3) . ?
C3 C4 1.410(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.382(3) . ?
C8 C9 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.367(3) . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.393(3) . ?
C14 C13 1.506(3) . ?
C10 H10 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 105(2) . . ?
C3 O2 H2 106(2) . . ?
N2 N1 C6 115.64(16) . . ?
N1 N2 C7 115.62(16) . . ?
C14 N3 C15 119.24(18) . . ?
C14 N3 C16 123.51(19) . . ?
C16 N3 C15 117.21(18) . . ?
C12 C7 N2 124.13(18) . . ?
C8 C7 N2 117.52(17) . . ?
C8 C7 C12 118.33(18) . . ?
N1 C6 C1 124.94(18) . . ?
N1 C6 C5 116.80(17) . . ?
C5 C6 C1 118.24(18) . . ?
O1 C1 C6 121.41(18) . . ?
O1 C1 C2 118.90(17) . . ?
C2 C1 C6 119.65(18) . . ?
C1 C2 H2A 119.8 . . ?
C1 C2 C3 120.38(18) . . ?
C3 C2 H2A 119.8 . . ?
O2 C3 C2 122.34(18) . . ?
O2 C3 C4 117.37(18) . . ?
C2 C3 C4 120.29(18) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.17(19) . . ?
C11 C12 H12 119.9 . . ?
C7 C8 Cl1 119.47(16) . . ?
C9 C8 Cl1 118.68(16) . . ?
C9 C8 C7 121.84(19) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.09(18) . . ?
C4 C5 H5 119.0 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.28(18) . . ?
C5 C4 H4 120.4 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.91(19) . . ?
C10 C9 H9 120.5 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.43(19) . . ?
C10 C11 H11 119.8 . . ?
O3 C14 N3 120.25(19) . . ?
O3 C14 C13 121.0(2) . . ?
N3 C14 C13 118.7(2) . . ?
C9 C10 C11 120.31(19) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.879
####################################################################### 
# 
# 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_rx4_etoh_100k
_database_code_depnum_ccdc_archive 'CCDC 1876826'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2018-11-02 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
_audit_creation_date             2018-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N3 O4'
_chemical_formula_sum            'C12 H9 N3 O4'
_chemical_formula_weight         259.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 N3 O4'
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'

_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                   11.8236(6)
_cell_length_b                   8.6618(3)
_cell_length_c                   12.0259(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.493(6)
_cell_angle_gamma                90
_cell_volume                     1129.53(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3636
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.8530
_cell_measurement_theta_min      2.9540
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.985
_diffrn_reflns_theta_max         24.985
_diffrn_reflns_theta_min         2.990
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.20   0.30   20.00    --   29.89  54.00 -90.00  624
  2  ω    -69.00 103.50   0.30   20.00    --   29.89  54.00 150.00  575
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0340830000
_diffrn_orient_matrix_UB_12      -0.0072679000
_diffrn_orient_matrix_UB_13      -0.0367066000
_diffrn_orient_matrix_UB_21      0.0456720000
_diffrn_orient_matrix_UB_22      -0.0431187000
_diffrn_orient_matrix_UB_23      0.0464707000
_diffrn_orient_matrix_UB_31      -0.0320900000
_diffrn_orient_matrix_UB_32      -0.0692311000
_diffrn_orient_matrix_UB_33      -0.0251285000
_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              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1779
_reflns_number_total             1984
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         1984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.4059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C2(H2B), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.36228(9) 0.60294(10) 0.23393(8) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.37477(9) 0.09252(11) 0.37934(9) 0.0264(3) Uani 1 1 d . . . . .
O3 O 0.41353(10) 0.90738(12) 0.13813(10) 0.0383(3) Uani 1 1 d . . . . .
N2 N 0.56801(11) 0.75196(12) 0.32457(10) 0.0211(3) Uani 1 1 d . . . . .
N1 N 0.61843(10) 0.62987(13) 0.39154(10) 0.0215(3) Uani 1 1 d . . . . .
O4 O 0.46671(12) 1.12139(13) 0.08184(11) 0.0455(3) Uani 1 1 d . . . . .
N3 N 0.48849(12) 1.01196(13) 0.15153(11) 0.0280(3) Uani 1 1 d . . . . .
C4 C 0.42576(12) 0.22863(15) 0.37565(12) 0.0212(3) Uani 1 1 d . . . . .
C1 C 0.55011(12) 0.50501(15) 0.38099(12) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.55399(13) 0.24402(15) 0.45512(12) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.5966 0.1605 0.5056 0.028 Uiso 1 1 calc R . . . .
C6 C 0.41883(12) 0.48908(15) 0.30062(12) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.36093(12) 0.34740(16) 0.30148(12) 0.0221(3) Uani 1 1 d . . . . .
H5 H 0.2763 0.3336 0.2504 0.027 Uiso 1 1 calc R . . . .
C7 C 0.64193(12) 0.88228(15) 0.33746(12) 0.0210(3) Uani 1 1 d . . . . .
C8 C 0.75618(13) 0.89178(16) 0.43625(12) 0.0239(3) Uani 1 1 d . . . . .
H8 H 0.7822 0.8097 0.4933 0.029 Uiso 1 1 calc R . . . .
C2 C 0.61289(13) 0.37745(15) 0.45736(12) 0.0223(3) Uani 1 1 d . . . . .
H2B H 0.6973 0.3877 0.5102 0.027 Uiso 1 1 calc R . . . .
C12 C 0.60771(13) 1.00627(15) 0.25522(12) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.83138(13) 1.01893(17) 0.45166(13) 0.0278(3) Uani 1 1 d . . . . .
H9 H 0.9072 1.0248 0.5207 0.033 Uiso 1 1 calc R . . . .
C10 C 0.79766(14) 1.13819(17) 0.36776(13) 0.0296(3) Uani 1 1 d . . . . .
H10 H 0.8512 1.2237 0.3779 0.036 Uiso 1 1 calc R . . . .
C11 C 0.68592(14) 1.13171(17) 0.26960(13) 0.0279(3) Uani 1 1 d . . . . .
H11 H 0.6622 1.2129 0.2117 0.034 Uiso 1 1 calc R . . . .
H2A H 0.4873(18) 0.747(2) 0.2710(17) 0.041(5) Uiso 1 1 d . . . . .
H2 H 0.288(2) 0.094(2) 0.335(2) 0.062(6) 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
O1 C6 1.2788(16) . ?
O2 C4 1.3329(16) . ?
O2 H2 0.95(2) . ?
O3 N3 1.2321(16) . ?
N2 N1 1.3189(15) . ?
N2 C7 1.3979(17) . ?
N2 H2A 0.915(19) . ?
N1 C1 1.3254(17) . ?
O4 N3 1.2228(16) . ?
N3 C12 1.4639(18) . ?
C4 C3 1.4403(19) . ?
C4 C5 1.3771(19) . ?
C1 C6 1.4719(19) . ?
C1 C2 1.4393(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.3440(19) . ?
C6 C5 1.4073(19) . ?
C5 H5 0.9500 . ?
C7 C8 1.4013(19) . ?
C7 C12 1.4058(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(2) . ?
C2 H2B 0.9500 . ?
C12 C11 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(2) . ?
C11 H11 0.9500 . ?

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
C4 O2 H2 111.9(13) . . ?
N1 N2 C7 117.99(11) . . ?
N1 N2 H2A 118.7(11) . . ?
C7 N2 H2A 123.3(11) . . ?
N2 N1 C1 119.07(11) . . ?
O3 N3 C12 119.00(11) . . ?
O4 N3 O3 122.43(12) . . ?
O4 N3 C12 118.56(12) . . ?
O2 C4 C3 115.48(12) . . ?
O2 C4 C5 122.68(12) . . ?
C5 C4 C3 121.84(12) . . ?
N1 C1 C6 125.61(12) . . ?
N1 C1 C2 115.20(12) . . ?
C2 C1 C6 119.19(12) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.53(13) . . ?
C2 C3 H3 120.2 . . ?
O1 C6 C1 119.36(12) . . ?
O1 C6 C5 122.88(12) . . ?
C5 C6 C1 117.75(11) . . ?
C4 C5 C6 120.62(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N2 C7 C8 119.36(12) . . ?
N2 C7 C12 123.16(12) . . ?
C8 C7 C12 117.48(12) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.81(13) . . ?
C9 C8 H8 119.6 . . ?
C1 C2 H2B 119.5 . . ?
C3 C2 C1 121.06(12) . . ?
C3 C2 H2B 119.5 . . ?
C7 C12 N3 122.30(12) . . ?
C11 C12 N3 116.48(12) . . ?
C11 C12 C7 121.21(13) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.90(13) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.49(13) . . ?
C11 C10 H10 120.3 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.05(13) . . ?
C10 C11 H11 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
O1 C6 C5 C4 -179.55(12) . . . . ?
O2 C4 C3 C2 -179.98(12) . . . . ?
O2 C4 C5 C6 -179.92(12) . . . . ?
O3 N3 C12 C7 2.7(2) . . . . ?
O3 N3 C12 C11 -176.51(12) . . . . ?
N2 N1 C1 C6 -0.93(19) . . . . ?
N2 N1 C1 C2 179.88(11) . . . . ?
N2 C7 C8 C9 -179.97(12) . . . . ?
N2 C7 C12 N3 2.8(2) . . . . ?
N2 C7 C12 C11 -178.02(12) . . . . ?
N1 N2 C7 C8 -13.29(18) . . . . ?
N1 N2 C7 C12 166.47(12) . . . . ?
N1 C1 C6 O1 -0.2(2) . . . . ?
N1 C1 C6 C5 -179.91(12) . . . . ?
N1 C1 C2 C3 -179.87(12) . . . . ?
O4 N3 C12 C7 -177.85(13) . . . . ?
O4 N3 C12 C11 2.93(19) . . . . ?
N3 C12 C11 C10 177.30(12) . . . . ?
C4 C3 C2 C1 -0.4(2) . . . . ?
C1 C6 C5 C4 0.18(19) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C6 C1 C2 C3 0.88(19) . . . . ?
C5 C4 C3 C2 -0.2(2) . . . . ?
C7 N2 N1 C1 179.93(11) . . . . ?
C7 C8 C9 C10 -2.1(2) . . . . ?
C7 C12 C11 C10 -1.9(2) . . . . ?
C8 C7 C12 N3 -177.45(12) . . . . ?
C8 C7 C12 C11 1.74(19) . . . . ?
C8 C9 C10 C11 1.9(2) . . . . ?
C2 C1 C6 O1 178.99(12) . . . . ?
C2 C1 C6 C5 -0.75(18) . . . . ?
C12 C7 C8 C9 0.26(19) . . . . ?
C9 C10 C11 C12 0.1(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.185
_oxdiff_exptl_absorpt_empirical_full_min 0.904
####################################################################### 
# 
# 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_dd16_100k_0m
_database_code_depnum_ccdc_archive 'CCDC 1876827'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2018-11-02 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
_audit_creation_date             2018-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N3 O2, C3 H7 N O'
_chemical_formula_sum            'C16 H16 N4 O3'
_chemical_formula_weight         312.33
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0323(3)
_cell_length_b                   8.6204(4)
_cell_length_c                   13.7182(6)
_cell_angle_alpha                105.738(2)
_cell_angle_beta                 94.770(2)
_cell_angle_gamma                103.820(2)
_cell_volume                     767.47(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5882
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0383 before and 0.0307 after correction. The Ratio of minimum to maximum transmission is 0.9504. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10582
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.562
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2416
_reflns_number_total             2711
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.1256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1020
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14), C3(H3), C4(H4), C6(H6), C5(H5), C12(H12)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.4, Nqual =  -1, Ralpha = 0.100
;
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 0.27793(13) 0.37291(10) 0.25626(7) 0.0224(2) Uani 1 1 d . . . . .
O3 O 0.72325(13) 1.02099(11) 0.05878(6) 0.0239(2) Uani 1 1 d . . . . .
O2 O 0.56376(14) 0.72534(11) 0.07032(6) 0.0250(2) Uani 1 1 d . . . . .
N1 N 0.28305(14) 0.51874(12) 0.44829(7) 0.0178(2) Uani 1 1 d . . . . .
N2 N 0.36527(14) 0.66392(12) 0.44224(8) 0.0183(2) Uani 1 1 d . . . . .
N4 N 0.85495(15) 1.11083(12) -0.06829(7) 0.0200(2) Uani 1 1 d . . . . .
N3 N 0.0875(2) 0.09081(14) 0.40093(9) 0.0362(3) Uani 1 1 d . . . . .
C8 C 0.40986(17) 0.66969(15) 0.34625(9) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.42163(17) 0.55294(15) 0.16516(9) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.3928 0.4599 0.1049 0.023 Uiso 1 1 calc R . . . .
C11 C 0.51678(17) 0.71160(15) 0.16150(9) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.36843(17) 0.52943(15) 0.25608(9) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.50759(17) 0.82816(15) 0.34000(9) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.5366 0.9222 0.3997 0.024 Uiso 1 1 calc R . . . .
C14 C 0.75133(18) 0.99638(15) -0.03190(9) 0.0201(3) Uani 1 1 d . . . . .
H14 H 0.6940 0.8873 -0.0782 0.024 Uiso 1 1 calc R . . . .
C2 C 0.14877(17) 0.35692(15) 0.55583(9) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.09530(17) 0.33928(15) 0.64865(9) 0.0193(3) Uani 1 1 d . . . . .
H3 H 0.0358 0.2316 0.6544 0.023 Uiso 1 1 calc R . . . .
C4 C 0.12992(18) 0.48054(16) 0.73220(9) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.0940 0.4698 0.7958 0.026 Uiso 1 1 calc R . . . .
C7 C 0.23689(16) 0.51543(15) 0.54622(9) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.11553(19) 0.20998(15) 0.46864(9) 0.0230(3) Uani 1 1 d . . . . .
C6 C 0.27080(18) 0.65643(15) 0.63188(9) 0.0220(3) Uani 1 1 d . . . . .
H6 H 0.3307 0.7645 0.6269 0.026 Uiso 1 1 calc R . . . .
C5 C 0.21720(19) 0.63868(16) 0.72386(9) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.2400 0.7349 0.7818 0.029 Uiso 1 1 calc R . . . .
C16 C 0.8847(2) 1.07175(17) -0.17524(9) 0.0252(3) Uani 1 1 d . . . . .
H16A H 1.0265 1.0876 -0.1786 0.038 Uiso 1 1 calc GR . . . .
H16B H 0.8354 1.1463 -0.2073 0.038 Uiso 1 1 calc GR . . . .
H16C H 0.8124 0.9551 -0.2117 0.038 Uiso 1 1 calc GR . . . .
C12 C 0.56242(18) 0.85099(15) 0.25002(9) 0.0204(3) Uani 1 1 d . . . . .
H12 H 0.6300 0.9590 0.2476 0.024 Uiso 1 1 calc R . . . .
C15 C 0.9444(2) 1.28069(16) -0.00148(10) 0.0285(3) Uani 1 1 d . . . . .
H15A H 0.8523 1.3490 -0.0048 0.043 Uiso 1 1 calc GR . . . .
H15B H 1.0677 1.3289 -0.0239 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.9735 1.2786 0.0692 0.043 Uiso 1 1 calc GR . . . .
H1 H 0.256(3) 0.384(3) 0.3186(15) 0.051(5) Uiso 1 1 d . . . . .
H2 H 0.622(3) 0.836(3) 0.0774(14) 0.050(5) 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
O1 C9 1.3481(14) . ?
O1 H1 0.87(2) . ?
O3 C14 1.2447(14) . ?
O2 C11 1.3485(14) . ?
O2 H2 0.92(2) . ?
N1 N2 1.2752(15) . ?
N1 C7 1.4141(15) . ?
N2 C8 1.3898(15) . ?
N4 C14 1.3182(16) . ?
N4 C16 1.4583(15) . ?
N4 C15 1.4546(15) . ?
N3 C1 1.1455(17) . ?
C8 C9 1.4273(17) . ?
C8 C13 1.4038(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3880(17) . ?
C10 C9 1.3839(17) . ?
C11 C12 1.4074(17) . ?
C13 H13 0.9500 . ?
C13 C12 1.3732(16) . ?
C14 H14 0.9500 . ?
C2 C3 1.3940(16) . ?
C2 C7 1.4054(17) . ?
C2 C1 1.4422(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3822(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3945(18) . ?
C7 C6 1.3983(17) . ?
C6 H6 0.9500 . ?
C6 C5 1.3834(17) . ?
C5 H5 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C12 H12 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C9 O1 H1 104.5(13) . . ?
C11 O2 H2 108.9(11) . . ?
N2 N1 C7 114.84(10) . . ?
N1 N2 C8 115.60(10) . . ?
C14 N4 C16 121.57(10) . . ?
C14 N4 C15 120.25(10) . . ?
C15 N4 C16 118.18(10) . . ?
N2 C8 C9 125.66(11) . . ?
N2 C8 C13 115.91(10) . . ?
C13 C8 C9 118.41(11) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.40(11) . . ?
O2 C11 C10 117.20(10) . . ?
O2 C11 C12 122.00(10) . . ?
C10 C11 C12 120.79(11) . . ?
O1 C9 C8 121.97(11) . . ?
O1 C9 C10 118.35(10) . . ?
C10 C9 C8 119.68(11) . . ?
C8 C13 H13 119.1 . . ?
C12 C13 C8 121.84(11) . . ?
C12 C13 H13 119.1 . . ?
O3 C14 N4 124.69(11) . . ?
O3 C14 H14 117.7 . . ?
N4 C14 H14 117.7 . . ?
C3 C2 C7 121.05(11) . . ?
C3 C2 C1 119.48(11) . . ?
C7 C2 C1 119.47(11) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.12(11) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.50(11) . . ?
C5 C4 H4 119.7 . . ?
C2 C7 N1 116.24(10) . . ?
C6 C7 N1 124.98(11) . . ?
C6 C7 C2 118.77(11) . . ?
N3 C1 C2 178.26(13) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.08(11) . . ?
C5 C6 H6 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.47(11) . . ?
C6 C5 H5 119.8 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.86(11) . . ?
C13 C12 H12 120.6 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O2 C11 C12 C13 179.07(11) . . . . ?
N1 N2 C8 C9 1.14(17) . . . . ?
N1 N2 C8 C13 -177.53(10) . . . . ?
N1 C7 C6 C5 179.14(11) . . . . ?
N2 N1 C7 C2 -179.09(10) . . . . ?
N2 N1 C7 C6 1.50(17) . . . . ?
N2 C8 C9 O1 0.30(19) . . . . ?
N2 C8 C9 C10 -179.80(11) . . . . ?
N2 C8 C13 C12 179.16(10) . . . . ?
C8 C13 C12 C11 0.83(18) . . . . ?
C10 C11 C12 C13 -1.31(18) . . . . ?
C11 C10 C9 O1 -179.39(11) . . . . ?
C11 C10 C9 C8 0.70(18) . . . . ?
C9 C8 C13 C12 0.39(18) . . . . ?
C9 C10 C11 O2 -179.82(10) . . . . ?
C9 C10 C11 C12 0.54(18) . . . . ?
C13 C8 C9 O1 178.94(11) . . . . ?
C13 C8 C9 C10 -1.16(17) . . . . ?
C2 C3 C4 C5 -0.01(19) . . . . ?
C2 C7 C6 C5 -0.26(18) . . . . ?
C3 C2 C7 N1 -179.34(10) . . . . ?
C3 C2 C7 C6 0.11(18) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C7 N1 N2 C8 -179.38(9) . . . . ?
C7 C2 C3 C4 0.02(18) . . . . ?
C7 C6 C5 C4 0.28(19) . . . . ?
C1 C2 C3 C4 179.20(11) . . . . ?
C1 C2 C7 N1 1.48(17) . . . . ?
C1 C2 C7 C6 -179.07(11) . . . . ?
C16 N4 C14 O3 178.77(11) . . . . ?
C15 N4 C14 O3 -0.75(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dd-100k
_database_code_depnum_ccdc_archive 'CCDC 1876825'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2018-12-04 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
_audit_creation_date             2018-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 Br N2 O2, H2 O'
_chemical_formula_sum            'C12 H11 Br N2 O3'
_chemical_formula_weight         311.14
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     '0.2 mm loop'
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'
Br Br -0.2901 2.4595 '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/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                   3.93930(10)
_cell_length_b                   13.8586(4)
_cell_length_c                   21.9545(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.737(3)
_cell_angle_gamma                90
_cell_volume                     1196.02(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3808
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.8440
_cell_measurement_theta_min      3.0410
_shelx_estimated_absorpt_T_max   0.683
_shelx_estimated_absorpt_T_min   0.546
_exptl_absorpt_coefficient_mu    3.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8806
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.940
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.20   0.30   20.00    --   29.89  54.00-180.00  624
  2  ω    -69.00 118.20   0.30   20.00    --   29.89  54.00 -60.00  624
  3  ω    -69.00  20.10   0.30   20.00    --   29.89  54.00  60.00  297
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0112007000
_diffrn_orient_matrix_UB_12      0.0507143000
_diffrn_orient_matrix_UB_13      -0.0040534000
_diffrn_orient_matrix_UB_21      -0.0707313000
_diffrn_orient_matrix_UB_22      -0.0069817000
_diffrn_orient_matrix_UB_23      -0.0302272000
_diffrn_orient_matrix_UB_31      -0.1655726000
_diffrn_orient_matrix_UB_32      -0.0004454000
_diffrn_orient_matrix_UB_33      0.0108699000
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1881
_reflns_number_total             2110
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.101
_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)+(0.0318P)²+1.6498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C5(H5), C12(H12), C11(H11), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Br1 Br 0.21238(7) 0.29144(2) 0.73050(2) 0.02057(12) Uani 1 1 d . . . . .
O2 O 0.5188(5) 0.33827(14) 0.57987(9) 0.0198(4) Uani 1 1 d . . . . .
O1 O 0.9246(6) 0.34085(17) 0.38036(10) 0.0240(5) Uani 1 1 d . . . . .
O3 O 0.0156(7) 0.47303(16) 0.60717(11) 0.0282(5) Uani 1 1 d . . . . .
N1 N 0.2648(6) 0.17811(18) 0.61166(11) 0.0173(5) Uani 1 1 d . . . . .
N2 N 0.3331(6) 0.13949(17) 0.55983(11) 0.0176(5) Uani 1 1 d . . . . .
C3 C -0.0955(7) 0.1124(2) 0.75746(14) 0.0203(6) Uani 1 1 d . . . . .
H3 H -0.1258 0.1408 0.7961 0.024 Uiso 1 1 calc R . . . .
C1 C 0.1043(7) 0.1235(2) 0.65563(13) 0.0170(6) Uani 1 1 d . . . . .
C4 C -0.2041(7) 0.0184(2) 0.74526(15) 0.0214(6) Uani 1 1 d . . . . .
H4 H -0.3075 -0.0178 0.7758 0.026 Uiso 1 1 calc R . . . .
C6 C -0.0112(7) 0.0294(2) 0.64355(14) 0.0193(6) Uani 1 1 d . . . . .
H6 H 0.0137 0.0013 0.6046 0.023 Uiso 1 1 calc R . . . .
C5 C -0.1612(7) -0.0226(2) 0.68831(14) 0.0207(6) Uani 1 1 d . . . . .
H5 H -0.2357 -0.0868 0.6802 0.025 Uiso 1 1 calc R . . . .
C8 C 0.5728(7) 0.2964(2) 0.52852(14) 0.0171(6) Uani 1 1 d . . . . .
C10 C 0.7837(7) 0.2982(2) 0.42715(14) 0.0178(6) Uani 1 1 d . . . . .
C7 C 0.4844(7) 0.1950(2) 0.51933(13) 0.0168(6) Uani 1 1 d . . . . .
C2 C 0.0570(7) 0.1640(2) 0.71268(14) 0.0185(6) Uani 1 1 d . . . . .
C12 C 0.5545(7) 0.1491(2) 0.46319(13) 0.0189(6) Uani 1 1 d . . . . .
H12 H 0.4976 0.0830 0.4571 0.023 Uiso 1 1 calc R . . . .
C11 C 0.7008(8) 0.1984(2) 0.41853(14) 0.0208(6) Uani 1 1 d . . . . .
H11 H 0.7482 0.1668 0.3816 0.025 Uiso 1 1 calc R . . . .
C9 C 0.7224(7) 0.3457(2) 0.48067(13) 0.0186(6) Uani 1 1 d . . . . .
H9 H 0.7812 0.4119 0.4853 0.022 Uiso 1 1 calc R . . . .
H1A H 0.308(8) 0.232(3) 0.6169(15) 0.018(9) Uiso 1 1 d . . . . .
H3A H -0.175(13) 0.437(3) 0.600(2) 0.068(15) Uiso 1 1 d . . . . .
H3B H 0.205(11) 0.437(3) 0.6019(19) 0.050(12) Uiso 1 1 d . . . . .
H1 H 0.946(10) 0.402(3) 0.3867(18) 0.042(11) 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
Br1 C2 1.901(3) . ?
O2 C8 1.298(4) . ?
O1 C10 1.337(4) . ?
O1 H1 0.87(4) . ?
O3 H3A 0.91(5) . ?
O3 H3B 0.91(5) . ?
N1 N2 1.301(3) . ?
N1 C1 1.408(4) . ?
N1 H1A 0.77(3) . ?
N2 C7 1.344(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(4) . ?
C3 C2 1.384(4) . ?
C1 C6 1.401(4) . ?
C1 C2 1.396(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.382(4) . ?
C5 H5 0.9500 . ?
C8 C7 1.458(4) . ?
C8 C9 1.414(4) . ?
C10 C11 1.431(4) . ?
C10 C9 1.382(4) . ?
C7 C12 1.430(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.354(4) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?

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
C10 O1 H1 111(3) . . ?
H3A O3 H3B 111(4) . . ?
N2 N1 C1 120.4(2) . . ?
N2 N1 H1A 118(3) . . ?
C1 N1 H1A 121(2) . . ?
N1 N2 C7 118.0(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C6 C1 N1 121.7(3) . . ?
C2 C1 N1 119.4(3) . . ?
C2 C1 C6 118.9(3) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
O2 C8 C7 120.0(3) . . ?
O2 C8 C9 121.9(3) . . ?
C9 C8 C7 118.0(3) . . ?
O1 C10 C11 115.4(3) . . ?
O1 C10 C9 123.2(3) . . ?
C9 C10 C11 121.5(3) . . ?
N2 C7 C8 124.9(3) . . ?
N2 C7 C12 115.7(2) . . ?
C12 C7 C8 119.4(3) . . ?
C3 C2 Br1 118.9(2) . . ?
C3 C2 C1 121.3(3) . . ?
C1 C2 Br1 119.9(2) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.876
####################################################################### 
# 
# 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_19_thf-meoh_rt
_database_code_depnum_ccdc_archive 'CCDC 1876823'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2018-11-02 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
_audit_creation_date             2018-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 Cl N2 O2, H2 O'
_chemical_formula_sum            'C12 H11 Cl N2 O3'
_chemical_formula_weight         266.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H14 N2 O2 Cl1'
_chemical_oxdiff_usercomment     '0.3 mm loop'
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/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                   3.9592(2)
_cell_length_b                   13.8353(7)
_cell_length_c                   22.1033(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.241(5)
_cell_angle_gamma                90
_cell_volume                     1208.81(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      24.3330
_cell_measurement_theta_min      3.0680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7717
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.945
_diffrn_ambient_temperature      298.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.20   0.30   12.00    --   29.89  54.00-180.00  624
  2  ω    -69.00 118.20   0.30   12.00    --   29.89  54.00  30.00  624
  3  ω    -69.00 -39.00   0.30   12.00    --   29.89  54.00 -60.00  100
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0990633000
_diffrn_orient_matrix_UB_12      -0.0426335000
_diffrn_orient_matrix_UB_13      0.0007704000
_diffrn_orient_matrix_UB_21      -0.0260566000
_diffrn_orient_matrix_UB_22      0.0082527000
_diffrn_orient_matrix_UB_23      0.0310698000
_diffrn_orient_matrix_UB_31      -0.1473726000
_diffrn_orient_matrix_UB_32      0.0272110000
_diffrn_orient_matrix_UB_33      -0.0082210000
_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              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1569
_reflns_number_total             2131
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1124P)²+0.1642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C11(H11), C6(H6), C3(H3), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.8321(2) 0.28580(5) 0.27435(4) 0.0707(4) Uani 1 1 d . . . . .
O2 O 0.4857(5) 0.33772(14) 0.42009(9) 0.0581(6) Uani 1 1 d . . . . .
O1 O 0.0964(6) 0.33929(16) 0.61922(9) 0.0637(6) Uani 1 1 d . . . . .
O3 O 0.9868(7) 0.47421(16) 0.39320(11) 0.0722(7) Uani 1 1 d . . . . .
N1 N 0.7437(6) 0.17930(17) 0.38754(10) 0.0492(6) Uani 1 1 d . . . . .
N2 N 0.6778(6) 0.13983(16) 0.43923(10) 0.0507(6) Uani 1 1 d . . . . .
C1 C 0.9003(6) 0.12500(18) 0.34358(12) 0.0472(6) Uani 1 1 d . . . . .
C8 C 0.4376(7) 0.29578(18) 0.47112(13) 0.0480(6) Uani 1 1 d . . . . .
C7 C 0.5303(7) 0.19480(19) 0.48019(12) 0.0485(7) Uani 1 1 d . . . . .
C10 C 0.2349(7) 0.29727(19) 0.57248(12) 0.0501(7) Uani 1 1 d . . . . .
C9 C 0.2893(7) 0.3441(2) 0.51918(12) 0.0527(7) Uani 1 1 d . . . . .
H9 H 0.2274 0.4087 0.5147 0.063 Uiso 1 1 calc R . . . .
C2 C 0.9594(7) 0.16692(19) 0.28813(13) 0.0511(7) Uani 1 1 d . . . . .
C12 C 0.4651(7) 0.1497(2) 0.53635(12) 0.0556(7) Uani 1 1 d . . . . .
H12 H 0.5212 0.0849 0.5421 0.067 Uiso 1 1 calc R . . . .
C11 C 0.3253(8) 0.1980(2) 0.58115(13) 0.0561(7) Uani 1 1 d . . . . .
H11 H 0.2874 0.1672 0.6176 0.067 Uiso 1 1 calc R . . . .
C6 C 1.0007(7) 0.0289(2) 0.35354(13) 0.0542(7) Uani 1 1 d . . . . .
H6 H 0.9679 -0.0003 0.3907 0.065 Uiso 1 1 calc R . . . .
C3 C 1.1083(7) 0.1156(2) 0.24335(13) 0.0600(8) Uani 1 1 d . . . . .
H3 H 1.1454 0.1446 0.2063 0.072 Uiso 1 1 calc R . . . .
C5 C 1.1467(8) -0.0222(2) 0.30893(15) 0.0612(8) Uani 1 1 d . . . . .
H5 H 1.2092 -0.0863 0.3157 0.073 Uiso 1 1 calc R . . . .
C4 C 1.2019(8) 0.0206(2) 0.25397(14) 0.0641(8) Uani 1 1 d . . . . .
H4 H 1.3024 -0.0146 0.2240 0.077 Uiso 1 1 calc R . . . .
H1A H 0.693(9) 0.250(3) 0.3789(17) 0.083(10) Uiso 1 1 d . . . . .
H3A H 0.816(11) 0.432(3) 0.396(2) 0.103(14) Uiso 1 1 d . . . . .
H3B H 1.195(14) 0.436(4) 0.401(2) 0.138(17) Uiso 1 1 d . . . . .
H1 H 0.043(11) 0.404(3) 0.611(2) 0.114(15) 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
Cl1 C2 1.742(3) . ?
O2 C8 1.292(3) . ?
O1 C10 1.330(3) . ?
O1 H1 0.94(4) . ?
O3 H3A 0.90(5) . ?
O3 H3B 0.99(6) . ?
N1 N2 1.306(3) . ?
N1 C1 1.400(3) . ?
N1 H1A 1.02(4) . ?
N2 C7 1.341(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.402(4) . ?
C8 C7 1.455(4) . ?
C8 C9 1.412(4) . ?
C7 C12 1.426(4) . ?
C10 C9 1.372(4) . ?
C10 C11 1.429(4) . ?
C9 H9 0.9300 . ?
C2 C3 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.340(4) . ?
C11 H11 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.368(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.380(4) . ?
C4 H4 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
C10 O1 H1 112(3) . . ?
H3A O3 H3B 105(4) . . ?
N2 N1 C1 120.1(2) . . ?
N2 N1 H1A 121(2) . . ?
C1 N1 H1A 118(2) . . ?
N1 N2 C7 118.0(2) . . ?
N1 C1 C6 122.2(2) . . ?
C2 C1 N1 119.5(2) . . ?
C2 C1 C6 118.3(2) . . ?
O2 C8 C7 120.2(2) . . ?
O2 C8 C9 122.2(2) . . ?
C9 C8 C7 117.6(2) . . ?
N2 C7 C8 124.6(2) . . ?
N2 C7 C12 116.5(2) . . ?
C12 C7 C8 118.9(2) . . ?
O1 C10 C9 123.5(2) . . ?
O1 C10 C11 115.3(2) . . ?
C9 C10 C11 121.3(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C1 C2 Cl1 119.2(2) . . ?
C3 C2 Cl1 119.5(2) . . ?
C3 C2 C1 121.3(3) . . ?
C7 C12 H12 119.1 . . ?
C11 C12 C7 121.9(3) . . ?
C11 C12 H12 119.1 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.876
_oxdiff_exptl_absorpt_empirical_full_min 0.826
####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1876824'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2018-11-02 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
_audit_creation_date             2018-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N3 O2'
_chemical_formula_sum            'C13 H9 N3 O2'
_chemical_formula_weight         239.23
_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'
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                   10.0695(11)
_cell_length_b                   4.4780(5)
_cell_length_c                   23.887(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.333(3)
_cell_angle_gamma                90
_cell_volume                     1076.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4251
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.096
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15398
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.522
_diffrn_reflns_theta_min         2.024
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1626
_reflns_number_total             2226
_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       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker, SAINT'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+0.7227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1544
_refine_special_details          'ω scan'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C8(H8), C5(H5), C3(H3), C11(H11), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O2 O 0.22107(15) -0.4068(4) 0.61671(7) 0.0283(4) Uani 1 1 d . . . . .
O1 O 0.55891(16) 0.2241(4) 0.54938(6) 0.0338(4) Uani 1 1 d . . . . .
N1 N 0.61471(17) 0.4300(4) 0.66434(7) 0.0228(4) Uani 1 1 d . . . . .
N2 N 0.68157(17) 0.5329(4) 0.62425(7) 0.0239(4) Uani 1 1 d . . . . .
N3 N 0.82462(19) 0.6209(5) 0.49701(8) 0.0337(5) Uani 1 1 d . . . . .
C7 C 0.7816(2) 0.7421(5) 0.64013(9) 0.0228(5) Uani 1 1 d . . . . .
C4 C 0.3184(2) -0.1996(5) 0.62522(9) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.4412(2) 0.1064(5) 0.69124(9) 0.0238(5) Uani 1 1 d . . . . .
H2A H 0.4585 0.1719 0.7287 0.029 Uiso 1 1 calc R . . . .
C12 C 0.8619(2) 0.8379(5) 0.59704(9) 0.0239(5) Uani 1 1 d . . . . .
C8 C 0.8051(2) 0.8552(5) 0.69432(9) 0.0245(5) Uani 1 1 d . . . . .
H8 H 0.7514 0.7934 0.7240 0.029 Uiso 1 1 calc R . . . .
C6 C 0.4896(2) 0.1219(5) 0.59230(9) 0.0239(5) Uani 1 1 d . . . . .
C5 C 0.3907(2) -0.0890(5) 0.58177(9) 0.0252(5) Uani 1 1 d . . . . .
H5 H 0.3726 -0.1576 0.5446 0.030 Uiso 1 1 calc R . . . .
C3 C 0.3432(2) -0.1004(5) 0.68045(9) 0.0240(5) Uani 1 1 d . . . . .
H3 H 0.2927 -0.1761 0.7100 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5168(2) 0.2241(5) 0.64817(9) 0.0224(5) Uani 1 1 d . . . . .
C11 C 0.9651(2) 1.0415(5) 0.60777(10) 0.0272(5) Uani 1 1 d . . . . .
H11 H 1.0194 1.1043 0.5784 0.033 Uiso 1 1 calc R . . . .
C9 C 0.9072(2) 1.0576(5) 0.70434(9) 0.0257(5) Uani 1 1 d . . . . .
H9 H 0.9228 1.1344 0.7411 0.031 Uiso 1 1 calc R . . . .
C13 C 0.8400(2) 0.7185(5) 0.54127(10) 0.0274(5) Uani 1 1 d . . . . .
C10 C 0.9877(2) 1.1508(5) 0.66158(9) 0.0278(5) Uani 1 1 d . . . . .
H10 H 1.0577 1.2888 0.6693 0.033 Uiso 1 1 calc R . . . .
H1 H 0.627(3) 0.400(8) 0.5694(13) 0.070(10) Uiso 1 1 d . . . . .
H2 H 0.213(3) -0.448(8) 0.5790(14) 0.067(10) 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
O2 C4 1.359(3) . ?
O2 H2 0.92(3) . ?
O1 C6 1.344(3) . ?
O1 H1 1.14(4) . ?
N1 N2 1.279(3) . ?
N1 C1 1.393(3) . ?
N2 C7 1.416(3) . ?
N3 C13 1.148(3) . ?
C7 C12 1.402(3) . ?
C7 C8 1.401(3) . ?
C4 C5 1.384(3) . ?
C4 C3 1.405(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.370(3) . ?
C2 C1 1.407(3) . ?
C12 C11 1.398(3) . ?
C12 C13 1.444(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C6 C5 1.388(3) . ?
C6 C1 1.427(3) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(3) . ?
C10 H10 0.9500 . ?

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
C4 O2 H2 109(2) . . ?
C6 O1 H1 103.9(16) . . ?
N2 N1 C1 114.77(18) . . ?
N1 N2 C7 115.36(18) . . ?
C12 C7 N2 115.55(19) . . ?
C8 C7 N2 125.32(19) . . ?
C8 C7 C12 119.1(2) . . ?
O2 C4 C5 122.1(2) . . ?
O2 C4 C3 117.15(19) . . ?
C5 C4 C3 120.8(2) . . ?
C3 C2 H2A 119.3 . . ?
C3 C2 C1 121.5(2) . . ?
C1 C2 H2A 119.3 . . ?
C7 C12 C13 119.51(19) . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 C13 119.7(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.2 . . ?
O1 C6 C5 118.99(19) . . ?
O1 C6 C1 121.2(2) . . ?
C5 C6 C1 119.8(2) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.3 . . ?
N1 C1 C2 116.30(19) . . ?
N1 C1 C6 125.33(19) . . ?
C2 C1 C6 118.4(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.5(2) . . ?
C10 C11 H11 120.2 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.3(2) . . ?
C10 C9 H9 119.4 . . ?
N3 C13 C12 178.8(2) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?

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
O2 C4 C5 C6 -179.78(19) . . . . ?
O2 C4 C3 C2 179.43(19) . . . . ?
O1 C6 C5 C4 179.6(2) . . . . ?
O1 C6 C1 N1 -0.7(3) . . . . ?
O1 C6 C1 C2 -179.54(19) . . . . ?
N1 N2 C7 C12 175.25(19) . . . . ?
N1 N2 C7 C8 -4.5(3) . . . . ?
N2 N1 C1 C2 -179.96(18) . . . . ?
N2 N1 C1 C6 1.2(3) . . . . ?
N2 C7 C12 C11 -179.20(19) . . . . ?
N2 C7 C12 C13 -0.9(3) . . . . ?
N2 C7 C8 C9 179.5(2) . . . . ?
C7 C12 C11 C10 -0.4(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C12 C11 C10 C9 -0.2(3) . . . . ?
C8 C7 C12 C11 0.6(3) . . . . ?
C8 C7 C12 C13 178.9(2) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C5 C6 C1 N1 178.7(2) . . . . ?
C5 C6 C1 C2 -0.1(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C2 C1 N1 -179.19(19) . . . . ?
C3 C2 C1 C6 -0.2(3) . . . . ?
C1 N1 N2 C7 -179.90(17) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C13 C12 C11 C10 -178.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
