# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_7218
_database_code_depnum_ccdc_archive 'CCDC 1825398'
_audit_update_record             
;
2018-02-23 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;
_audit_creation_date             2018-02-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C15 H11 N3 O3'
_chemical_formula_sum            'C15 H11 N3 O3'
_chemical_formula_weight         281.27
_chemical_oxdiff_formula         'C23 H14 N2 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.00330 0.00160 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.01060 0.00600 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.00610 0.00330 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.8053(18)
_cell_length_b                   8.2606(17)
_cell_length_c                   11.869(2)
_cell_angle_alpha                91.064(17)
_cell_angle_beta                 108.89(2)
_cell_angle_gamma                113.92(2)
_cell_volume                     651.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    916
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9384
_cell_measurement_theta_min      2.9446
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4329
_exptl_crystal_description       irregular
_exptl_crystal_F_000             292.1382
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5672
_diffrn_reflns_theta_full        29.0056
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         2.95
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00   11.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -      -18.3513  -77.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -86.00  -55.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -      -18.3513  -77.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   23.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -      -18.3513  -99.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   40.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263  -57.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00   62.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263   57.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  6 omega   70.00   98.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263  178.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00   89.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263   57.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
  8 omega  -52.00   19.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263  -38.0000 -120.0000 71
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0878554000
_diffrn_orient_matrix_UB_12      0.0809461000
_diffrn_orient_matrix_UB_13      0.0102562000
_diffrn_orient_matrix_UB_21      0.0332397000
_diffrn_orient_matrix_UB_22      -0.0442613000
_diffrn_orient_matrix_UB_23      -0.0340362000
_diffrn_orient_matrix_UB_31      -0.0506083000
_diffrn_orient_matrix_UB_32      0.0240199000
_diffrn_orient_matrix_UB_33      -0.0533940000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1505
_reflns_number_total             2992
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.4258
_refine_diff_density_min         -0.4612
_refine_diff_density_rms         0.1180
_refine_ls_d_res_high            0.7329
_refine_ls_d_res_low             6.9117
_refine_ls_goodness_of_fit_ref   1.0545
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.0545
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1402
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1AA(0.053) H9(0.048) H13(0.054) H11(0.058) H3(0.057) H12(0.061)
 H6(0.062) H5(0.067) H15a(0.1) H15b(0.1) H15c(0.1) H4(0.067)
 Fixed X: H1AA(0.9446) H9(0.7245) H13(0.7233) H11(0.7709) H3(0.4686)
 H12(0.7501) H6(1.0314) H5(0.9248) H15a(0.9461) H15b(0.8211) H15c(0.7167)
 H4(0.65)
 Fixed Y: H1AA(0.6155) H9(0.0982) H13(0.5707) H11(0.261) H3(0.2601)
 H12(0.5196) H6(0.7807) H5(0.7451) H15a(0.0579) H15b(-0.1509) H15c(-0.0319)
 H4(0.4885)
 Fixed Z: H1AA(0.245) H9(0.288) H13(0.3684) H11(0.6214) H3(-0.1819)
 H12(0.5628) H6(0.0632) H5(-0.1434) H15a(0.675) H15b(0.635) H15c(0.6556) H4(-
 0.2638)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O 0.3558(3) 0.0615(3) 0.1410(2) 0.0650(7) Uani 1.000000 .
O2 O 0.3098(3) 0.0455(3) -0.05037(19) 0.0614(6) Uani 1.000000 .
O3 O 0.7393(3) -0.1307(3) 0.4200(2) 0.0681(7) Uani 1.000000 .
N1 N 0.8513(3) 0.5365(3) 0.1870(2) 0.0426(6) Uani 1.000000 .
N2 N 0.7081(3) 0.3774(3) 0.19185(19) 0.0377(6) Uani 1.000000 .
N3 N 0.4061(3) 0.1197(3) 0.0567(2) 0.0461(6) Uani 1.000000 .
C1 C 0.5823(4) 0.2836(3) 0.0784(2) 0.0373(7) Uani 1.000000 .
C2 C 0.6427(4) 0.3823(3) -0.0053(2) 0.0358(6) Uani 1.000000 .
C3 C 0.5797(4) 0.3627(4) -0.1320(3) 0.0474(8) Uani 1.000000 .
C4 C 0.6886(5) 0.4990(5) -0.1796(3) 0.0551(8) Uani 1.000000 .
C5 C 0.8564(5) 0.6553(4) -0.1064(3) 0.0569(9) Uani 1.000000 .
C6 C 0.9197(4) 0.6779(4) 0.0155(3) 0.0505(8) Uani 1.000000 .
C7 C 0.8101(4) 0.5397(3) 0.0670(3) 0.0392(7) Uani 1.000000 .
C8 C 0.7191(4) 0.3377(3) 0.3112(2) 0.0382(7) Uani 1.000000 .
C9 C 0.7306(4) 0.1823(3) 0.3439(2) 0.0393(7) Uani 1.000000 .
C10 C 0.7503(4) 0.1528(3) 0.4616(2) 0.0386(7) Uani 1.000000 .
C11 C 0.7572(4) 0.2800(4) 0.5427(2) 0.0474(8) Uani 1.000000 .
C12 C 0.7461(4) 0.4350(4) 0.5081(3) 0.0504(8) Uani 1.000000 .
C13 C 0.7286(4) 0.4655(3) 0.3918(3) 0.0442(7) Uani 1.000000 .
C14 C 0.7662(4) -0.0144(4) 0.4964(3) 0.0478(8) Uani 1.000000 .
C15 C 0.8166(5) -0.0378(4) 0.6269(3) 0.0656(10) Uani 1.000000 .
H3 H 0.468600 0.260100 -0.181900 0.057000 Uiso 1.000000 .
H4 H 0.650000 0.488500 -0.263800 0.067000 Uiso 1.000000 .
H5 H 0.924800 0.745100 -0.143400 0.067000 Uiso 1.000000 .
H6 H 1.031400 0.780700 0.063200 0.062000 Uiso 1.000000 .
H9 H 0.724500 0.098200 0.288000 0.048000 Uiso 1.000000 .
H11 H 0.770900 0.261000 0.621400 0.058000 Uiso 1.000000 .
H12 H 0.750100 0.519600 0.562800 0.061000 Uiso 1.000000 .
H13 H 0.723300 0.570700 0.368400 0.054000 Uiso 1.000000 .
H15a H 0.946100 0.057900 0.675000 0.100000 Uiso 1.000000 .
H15b H 0.821100 -0.150900 0.635000 0.100000 Uiso 1.000000 .
H15c H 0.716700 -0.031900 0.655600 0.100000 Uiso 1.000000 .


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 N3 1.227(3) . ?
O2 N3 1.239(3) . ?
O3 C14 1.213(3) . ?
N1 N2 1.354(3) . ?
N1 C7 1.357(3) . ?
N2 C1 1.366(3) . ?
N2 C8 1.443(3) . ?
N3 C1 1.427(3) . ?
C1 C2 1.377(3) . ?
C2 C3 1.407(4) . ?
C2 C7 1.410(3) . ?
C3 C4 1.367(4) . ?
C4 C5 1.410(4) . ?
C5 C6 1.350(4) . ?
C6 C7 1.408(4) . ?
C8 C9 1.377(3) . ?
C8 C13 1.375(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.384(3) . ?
C10 C14 1.490(4) . ?
C11 C12 1.380(4) . ?
C12 C13 1.381(4) . ?
C14 C15 1.506(4) . ?

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 N1 N2 104.5(2) . . ?
C1 N2 N1 111.0(2) . . ?
C8 N2 N1 116.1(2) . . ?
C8 N2 C1 132.9(2) . . ?
O2 N3 O1 123.7(2) . . ?
C1 N3 O1 120.4(2) . . ?
C1 N3 O2 115.9(3) . . ?
N3 C1 N2 122.8(2) . . ?
C2 C1 N2 109.0(2) . . ?
C2 C1 N3 127.9(3) . . ?
C3 C2 C1 137.0(3) . . ?
C7 C2 C1 103.2(2) . . ?
C7 C2 C3 119.8(3) . . ?
C4 C3 C2 117.4(3) . . ?
C5 C4 C3 122.2(3) . . ?
C6 C5 C4 121.6(3) . . ?
C7 C6 C5 117.3(3) . . ?
C2 C7 N1 112.3(2) . . ?
C6 C7 N1 126.1(3) . . ?
C6 C7 C2 121.6(3) . . ?
C9 C8 N2 120.8(2) . . ?
C13 C8 N2 117.2(2) . . ?
C13 C8 C9 121.9(3) . . ?
C10 C9 C8 119.1(3) . . ?
C11 C10 C9 119.3(2) . . ?
C14 C10 C9 118.6(2) . . ?
C14 C10 C11 122.1(3) . . ?
C12 C11 C10 120.6(3) . . ?
C13 C12 C11 120.2(3) . . ?
C12 C13 C8 118.9(2) . . ?
C10 C14 O3 120.0(3) . . ?
C15 C14 O3 120.2(3) . . ?
C15 C14 C10 119.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        1-(3-(3-nitro-2H-indazol-2-yl)phenyl)ethanone
_exptl_crystal_colour            Yellow
_chemical_melting_point          443.15
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
