#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:26:34 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230872 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/63/7156334.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7156334
loop_
_publ_author_name
'Ieronimo, Gabriella'
'Palmisano, Giovanni'
'Maspero, Angelo'
'Marzorati, Alessandro'
'Scapinello, Luca'
'Masciocchi, Norberto'
'Cravotto, Giancarlo'
'Barge, Alessandro'
'Simonetti, Marco'
'Ameta, Keshav Lalit'
'Nicholas, Kenneth M.'
'Penoni, Andrea'
_publ_section_title
;
 A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6853
_journal_page_last               6859
_journal_paper_doi               10.1039/c8ob01471j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C15 H9 Cl N2 O4'
_chemical_formula_sum            'C15 H9 Cl N2 O4'
_chemical_formula_weight         316.69
_chemical_name_common
N-hydroxy-3-(2?-chlorobenzoyl)-5-nitro-1H-indole
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-07-13 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.602(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.899(2)
_cell_length_b                   7.780(2)
_cell_length_c                   13.9240(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      11
_cell_volume                     1392.8(4)
_computing_cell_refinement       CAD-4
_computing_data_collection       CAD-4
_computing_data_reduction        CAD-4
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CAD-4
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2529
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  14400
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.6894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                1979
_reflns_number_total             2529
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob01471j2.cif
_cod_data_source_block           Compound_4
_cod_depositor_comments          'Adding full bibliography for 7156334.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7156334
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'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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)
