#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/78/4517845.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_4517845
loop_
_publ_author_name
'Pisarek, Joanna'
'Malinska, Maura'
_publ_section_title
;
 Structure and Morphology of Indole Analogue Crystals.
;
_journal_issue                   28
_journal_name_full               'ACS omega'
_journal_page_first              17141
_journal_page_last               17151
_journal_paper_doi               10.1021/acsomega.0c01020
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C8 H6 N2 O2'
_chemical_formula_sum            'C8 H6 N2 O2'
_chemical_formula_weight         162.15
_chemical_name_systematic        5-Nitroindole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-02
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.730(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.75839(9)
_cell_length_b                   12.0667(3)
_cell_length_c                   15.8045(4)
_cell_measurement_reflns_used    7708
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.3100
_cell_measurement_theta_min      2.5580
_cell_volume                     716.70(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0026
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     49.00  99.00   1.00   50.00    --   27.00 160.00  90.00   50
  2  ω    -17.00 100.00   1.00   50.00    --   27.00  19.00 120.00  117
  3  ω      6.00  96.00   1.00   50.00    --   27.00  57.00 -30.00   90
  4  ω     49.00  99.00   1.00   50.00    --   27.00 160.00  30.00   50
  5  ω    -42.00  47.00   1.00   50.00    --   27.00 -57.00  90.00   89
  6  ω      6.00  96.00   1.00   50.00    --   27.00  57.00-180.00   90
  7  ω    -57.00  43.00   1.00   50.00    --  -27.15  77.00   0.00  100
  8  ω     -3.00  97.00   1.00   50.00    --   27.00  77.00  60.00  100
  9  ω     21.00 103.00   1.00   50.00    --   27.00-160.00 120.00   82
 10  ω      6.00  96.00   1.00   50.00    --   27.00  57.00-120.00   90
 11  ω    -97.00 -87.00   1.00   50.00    --  -27.15 -77.00 120.00   10
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0765021000
_diffrn_orient_matrix_UB_12      -0.0210608000
_diffrn_orient_matrix_UB_13      0.0374946000
_diffrn_orient_matrix_UB_21      -0.1682371000
_diffrn_orient_matrix_UB_22      0.0211629000
_diffrn_orient_matrix_UB_23      -0.0128740000
_diffrn_orient_matrix_UB_31      -0.0383877000
_diffrn_orient_matrix_UB_32      -0.0506593000
_diffrn_orient_matrix_UB_33      -0.0210007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15431
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.503
_diffrn_reflns_theta_min         2.124
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.649
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0380
_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)+(0.0628P)²+0.1681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2156
_reflns_number_total             2392
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c01020_si_001.cif
_cod_data_source_block           5nI
_cod_depositor_comments
'Adding full bibliography for 4517840--4517846.cif.'
_cod_database_code               4517845
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H6N2O2
_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.
;
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.931
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C4(H4), C6(H6), C3(H3), C2(H2)
;
_olex2_date_sample_data_collection 2017-11-08
_olex2_submission_original_sample_id 5-Nitroindole
_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.382
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'
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
N2 N 0.3364(2) 0.29670(6) 0.06790(5) 0.01743(16) Uani 1 1 d . . . . .
C5 C 0.1822(2) 0.26377(7) -0.01281(5) 0.01448(16) Uani 1 1 d . . . . .
N1 N -0.23639(19) 0.15725(6) -0.23674(5) 0.01739(16) Uani 1 1 d . . . . .
H1 H -0.340605 0.191447 -0.279535 0.021 Uiso 1 1 calc R . . . .
C9 C 0.0404(2) 0.12250(7) -0.11259(5) 0.01370(16) Uani 1 1 d . . . . .
O2 O 0.3380(2) 0.39544(6) 0.08783(5) 0.02865(18) Uani 1 1 d . . . . .
C8 C -0.1085(2) 0.20696(7) -0.16517(5) 0.01401(16) Uani 1 1 d . . . . .
C7 C -0.1121(2) 0.31881(7) -0.14208(5) 0.01607(16) Uani 1 1 d . . . . .
H7 H -0.213517 0.373360 -0.178400 0.019 Uiso 1 1 calc R . . . .
O1 O 0.4647(2) 0.22398(6) 0.11465(4) 0.02447(17) Uani 1 1 d . . . . .
C4 C 0.1893(2) 0.15232(7) -0.03444(5) 0.01419(16) Uani 1 1 d . . . . .
H4 H 0.291411 0.098502 0.002412 0.017 Uiso 1 1 calc R . . . .
C6 C 0.0364(2) 0.34734(7) -0.06496(5) 0.01650(17) Uani 1 1 d . . . . .
H6 H 0.040312 0.422526 -0.047133 0.020 Uiso 1 1 calc R . . . .
C3 C -0.0061(2) 0.01981(7) -0.15672(5) 0.01729(17) Uani 1 1 d . . . . .
H3 H 0.066664 -0.051555 -0.137928 0.021 Uiso 1 1 calc R . . . .
C2 C -0.1763(2) 0.04488(7) -0.23132(5) 0.01917(18) Uani 1 1 d . . . . .
H2 H -0.243311 -0.007669 -0.273344 0.023 Uiso 1 1 calc R . . . .
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'
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
O2 N2 C5 119.38(7) . . ?
O2 N2 O1 122.07(7) . . ?
O1 N2 C5 118.56(7) . . ?
C4 C5 N2 118.27(7) . . ?
C4 C5 C6 123.92(7) . . ?
C6 C5 N2 117.81(7) . . ?
C8 N1 C2 109.03(7) . . ?
C8 C9 C3 106.88(7) . . ?
C4 C9 C8 118.78(7) . . ?
C4 C9 C3 134.34(7) . . ?
N1 C8 C9 107.52(7) . . ?
N1 C8 C7 129.58(7) . . ?
C7 C8 C9 122.90(7) . . ?
C6 C7 C8 117.84(7) . . ?
C5 C4 C9 117.30(7) . . ?
C7 C6 C5 119.26(8) . . ?
C2 C3 C9 106.34(7) . . ?
C3 C2 N1 110.24(7) . . ?
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
N2 C5 1.4498(10) . ?
N2 O2 1.2323(10) . ?
N2 O1 1.2407(10) . ?
C5 C4 1.3879(11) . ?
C5 C6 1.4090(11) . ?
N1 C8 1.3624(10) . ?
N1 C2 1.3771(11) . ?
C9 C8 1.4250(11) . ?
C9 C4 1.3967(11) . ?
C9 C3 1.4316(11) . ?
C8 C7 1.3982(11) . ?
C7 C6 1.3778(11) . ?
C3 C2 1.3680(12) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 22523
