# 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_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 834062'
_audit_update_record             
;
2011-07-13 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_iucr_compatibility_tag          ?


#==============================================================================

# 4. CRTSTAL DATA AND OTHER EXPERIMENTAL DETAILS


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
N-hydroxy-3-(2?-chlorobenzoyl)-5-nitro-1H-indole
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 Cl N2 O4'
_chemical_formula_sum            'C15 H9 Cl N2 O4'
_chemical_formula_weight         316.69

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   12.899(2)
_cell_length_b                   7.780(2)
_cell_length_c                   13.9240(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.602(9)
_cell_angle_gamma                90.00
_cell_volume                     1392.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      11
_cell_measurement_theta_max      14

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CAD-4
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  14400
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2529
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.27
_reflns_number_total             2529
_reflns_number_gt                1979
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CAD-4
_computing_cell_refinement       CAD-4
_computing_data_reduction        CAD-4
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.6894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2529
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# 5. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11847(17) 0.1786(3) 0.78745(15) 0.0469(5) Uani 1 1 d . . .
Cl1 Cl 0.20136(5) 0.10382(9) 0.70419(4) 0.0596(2) Uani 1 1 d . . .
C2 C 0.0123(2) 0.1657(4) 0.7651(2) 0.0616(7) Uani 1 1 d . . .
C3 C -0.0548(2) 0.2196(4) 0.8306(2) 0.0701(8) Uani 1 1 d . . .
C4 C -0.0179(2) 0.2856(4) 0.9179(2) 0.0640(7) Uani 1 1 d . . .
C5 C 0.08830(18) 0.2976(3) 0.94073(18) 0.0516(6) Uani 1 1 d . . .
C6 C 0.15825(16) 0.2446(3) 0.87601(14) 0.0407(5) Uani 1 1 d . . .
C7 C 0.27297(15) 0.2604(3) 0.90195(13) 0.0382(5) Uani 1 1 d . . .
O1 O 0.32946(11) 0.3414(2) 0.85051(10) 0.0495(4) Uani 1 1 d . . .
C8 C 0.31534(14) 0.1824(3) 0.99024(13) 0.0357(4) Uani 1 1 d . . .
C9 C 0.42201(14) 0.1931(3) 1.03152(13) 0.0348(4) Uani 1 1 d . . .
C10 C 0.51278(16) 0.2663(3) 1.00228(16) 0.0415(5) Uani 1 1 d . . .
C11 C 0.60190(16) 0.2446(3) 1.06303(16) 0.0456(5) Uani 1 1 d . . .
N1 N 0.69956(16) 0.3162(3) 1.03318(18) 0.0604(6) Uani 1 1 d . . .
O3 O 0.69786(15) 0.3917(3) 0.95634(17) 0.0837(6) Uani 1 1 d . . .
O4 O 0.77884(14) 0.2976(3) 1.08658(17) 0.0915(7) Uani 1 1 d . . .
C12 C 0.60532(18) 0.1564(3) 1.14975(18) 0.0504(6) Uani 1 1 d . . .
C13 C 0.51720(17) 0.0829(3) 1.17998(16) 0.0455(5) Uani 1 1 d . . .
C14 C 0.42671(15) 0.1018(3) 1.11924(13) 0.0362(4) Uani 1 1 d . . .
N2 N 0.32831(12) 0.0408(2) 1.12894(11) 0.0374(4) Uani 1 1 d . . .
O2 O 0.30065(12) -0.0559(2) 1.20537(11) 0.0493(4) Uani 1 1 d . . .
C15 C 0.26220(15) 0.0861(3) 1.05367(13) 0.0366(4) Uani 1 1 d . . .
H2 H -0.012(2) 0.122(4) 0.706(2) 0.089(10) Uiso 1 1 d . . .
H3 H -0.126(2) 0.209(4) 0.814(2) 0.083(9) Uiso 1 1 d . . .
H4 H -0.060(2) 0.322(4) 0.9635(19) 0.069(8) Uiso 1 1 d . . .
H5 H 0.1154(18) 0.342(3) 1.0014(18) 0.056(7) Uiso 1 1 d . . .
H10 H 0.5153(16) 0.329(3) 0.9433(16) 0.048(6) Uiso 1 1 d . . .
H12 H 0.6688(19) 0.148(3) 1.1876(17) 0.060(7) Uiso 1 1 d . . .
H13 H 0.5181(17) 0.020(3) 1.2390(17) 0.057(7) Uiso 1 1 d . . .
H20 H 0.301(2) 0.021(4) 1.257(2) 0.087(10) Uiso 1 1 d . . .
H15 H 0.1906(17) 0.050(3) 1.0510(14) 0.043(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
C1 C2 1.384(3) . ?
C1 C6 1.395(3) . ?
C1 Cl1 1.739(2) . ?
C2 C3 1.373(4) . ?
C2 H2 0.93(3) . ?
C3 C4 1.369(4) . ?
C3 H3 0.93(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.92(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.95(2) . ?
C6 C7 1.500(3) . ?
C7 O1 1.235(2) . ?
C7 C8 1.439(3) . ?
C8 C15 1.381(3) . ?
C8 C9 1.450(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.410(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.96(2) . ?
C11 C12 1.387(3) . ?
C11 N1 1.467(3) . ?
N1 O3 1.219(3) . ?
N1 O4 1.224(3) . ?
C12 C13 1.368(3) . ?
C12 H12 0.94(2) . ?
C13 C14 1.393(3) . ?
C13 H13 0.96(2) . ?
C14 N2 1.372(2) . ?
N2 C15 1.344(2) . ?
N2 O2 1.374(2) . ?
O2 H20 0.93(3) . ?
C15 H15 0.96(2) . ?

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
C2 C1 C6 120.9(2) . . ?
C2 C1 Cl1 118.42(19) . . ?
C6 C1 Cl1 120.67(17) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 121.2(19) . . ?
C1 C2 H2 119.2(19) . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 121.3(18) . . ?
C2 C3 H3 117.9(18) . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 123.1(17) . . ?
C5 C4 H4 117.1(17) . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 120.9(14) . . ?
C6 C5 H5 118.2(14) . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 C7 119.97(19) . . ?
C1 C6 C7 121.93(19) . . ?
O1 C7 C8 120.64(18) . . ?
O1 C7 C6 121.26(18) . . ?
C8 C7 C6 118.08(17) . . ?
C15 C8 C7 126.95(18) . . ?
C15 C8 C9 106.34(17) . . ?
C7 C8 C9 126.70(18) . . ?
C10 C9 C14 118.74(18) . . ?
C10 C9 C8 134.50(19) . . ?
C14 C9 C8 106.74(17) . . ?
C11 C10 C9 116.7(2) . . ?
C11 C10 H10 120.2(13) . . ?
C9 C10 H10 123.1(13) . . ?
C10 C11 C12 124.1(2) . . ?
C10 C11 N1 118.1(2) . . ?
C12 C11 N1 117.8(2) . . ?
O3 N1 O4 123.0(2) . . ?
O3 N1 C11 118.4(2) . . ?
O4 N1 C11 118.5(2) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 120.3(15) . . ?
C11 C12 H12 119.3(15) . . ?
C12 C13 C14 116.4(2) . . ?
C12 C13 H13 121.7(14) . . ?
C14 C13 H13 121.9(14) . . ?
N2 C14 C13 129.82(19) . . ?
N2 C14 C9 106.48(16) . . ?
C13 C14 C9 123.69(19) . . ?
C15 N2 C14 111.50(16) . . ?
C15 N2 O2 124.05(16) . . ?
C14 N2 O2 124.45(15) . . ?
N2 O2 H20 104.9(19) . . ?
N2 C15 C8 108.94(17) . . ?
N2 C15 H15 120.0(12) . . ?
C8 C15 H15 131.0(12) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.27
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.038


