#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/49/2104966.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2104966
loop_
_publ_author_name
'Zarychta, Bartosz'
'Zaleski, Jacek'
'Kyzioł, Janusz'
'Daszkiewicz, Zdzisław'
'Jelsch, Christian'
_publ_section_title
;
 Charge-density analysis of 1-nitroindoline: refinement quality using
 free R factors and restraints
;
_journal_coeditor_code           PI5008
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              250
_journal_page_last               262
_journal_paper_doi               10.1107/S0108768111013140
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C8 H8 N2 O2'
_chemical_formula_sum            'C8 H8 N2 O2'
_chemical_formula_weight         164.154
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           MoPro
_cell_angle_alpha                116.823(8)
_cell_angle_beta                 104.589(9)
_cell_angle_gamma                91.602(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7913(3)
_cell_length_b                   8.2458(6)
_cell_length_c                   8.9223(10)
_cell_measurement_reflns_used    29060
_cell_measurement_temperature    90.00(10)
_cell_measurement_theta_max      70.78
_cell_measurement_theta_min      2.81
_cell_volume                     362.99(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'MoPro (Guillot et al., 2001; Jelsch et al., 2005)'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.00(10)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.621
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_method       ω--scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.02828
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            29060
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         70.19
_diffrn_reflns_theta_min         2.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         8768
_refine_ls_number_restraints     203
_refine_ls_restrained_S_all      1.435
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0211
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'calc w =1/[1.1712*σ^2^(Fo^2^)+0.0007*Yo^2]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0230
_refine_ls_wR_factor_ref         0.0237
_reflns_number_gt                7946
_reflns_number_total             8768
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            pi5008.cif
_cod_data_source_block           I
_cod_original_cell_volume        362.99(5)
_cod_database_code               2104966
_cod_database_fobs_code          2104966
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.78192(5) 1.08684(3) 0.27352(4) 0.01910(10) Uani d 1 . .
O O2 1.11924(5) 1.13974(3) 0.48239(3) 0.01850(10) Uani d 1 . .
N N1 1.06725(3) 0.90148(2) 0.22094(2) 0.01330(10) Uani d 1 . .
N N2 0.98503(3) 1.05034(2) 0.33008(2) 0.01380(10) Uani d 1 . .
C C1 0.96755(3) 0.79791(2) 0.03622(2) 0.01080(10) Uani d 1 . .
C C2 1.12758(3) 0.67051(2) -0.02713(2) 0.01090(10) Uani d 1 . .
C C3 1.07498(3) 0.54989(2) -0.20611(2) 0.01410(10) Uani d 1 . .
C C4 0.86148(3) 0.55753(3) -0.32114(2) 0.01590(10) Uani d 1 . .
C C5 0.70391(3) 0.68537(3) -0.25621(2) 0.01550(10) Uani d 1 . .
C C6 0.75379(3) 0.80809(2) -0.07582(2) 0.01380(10) Uani d 1 . .
C C8 1.34213(3) 0.68715(2) 0.12131(2) 0.01280(10) Uani d 1 . .
C C7 1.30992(3) 0.85638(3) 0.28538(2) 0.01400(10) Uani d 1 . .
H H3 1.1918(8) 0.4520(6) -0.2576(6) 0.03042 Uani d 1 . .
H H4 0.8181(9) 0.4646(6) -0.4610(3) 0.03331 Uani d 1 . .
H H5 0.5412(6) 0.6893(7) -0.3457(5) 0.03402 Uani d 1 . .
H H6 0.6344(7) 0.9046(6) -0.0270(6) 0.03051 Uani d 1 . .
H H8A 1.5142(4) 0.7031(8) 0.0973(5) 0.03048 Uani d 1 . .
H H8B 1.3436(9) 0.5621(4) 0.1343(6) 0.02969 Uani d 1 . .
H H7A 1.3134(10) 0.8371(8) 0.3989(5) 0.03012 Uani d 1 . .
H H7B 1.4406(8) 0.9817(5) 0.3418(7) 0.02993 Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0066 0.0034
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0114 0.0062
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 N2 O2 . . 124.25(3) ?
O1 N2 N1 . . 119.87(2) ?
O2 N2 N1 . . 115.87(2) ?
N1 C1 C2 . . 107.230(10) ?
N1 C1 C6 . . 129.82(2) ?
N1 C7 C8 . . 104.920(10) ?
N1 C7 H7A . . 108.7(3) ?
N1 C7 H7B . . 106.5(3) ?
N2 N1 C1 . . 126.03(2) ?
N2 N1 C7 . . 120.72(2) ?
C1 N1 C7 . . 112.150(10) ?
C1 C2 C8 . . 112.100(10) ?
C1 C2 C3 . . 120.03(2) ?
C1 C6 C5 . . 116.19(2) ?
C1 C6 H6 . . 122.5(3) ?
C2 C1 C6 . . 122.95(2) ?
C2 C8 C7 . . 102.910(10) ?
C2 C8 H8A . . 112.5(2) ?
C2 C8 H8B . . 112.3(2) ?
C2 C3 C4 . . 118.05(2) ?
C2 C3 H3 . . 121.7(3) ?
C3 C2 C8 . . 127.870(10) ?
C3 C4 C5 . . 121.31(2) ?
C3 C4 H4 . . 118.9(3) ?
C4 C3 H3 . . 120.3(3) ?
C4 C5 C6 . . 121.46(2) ?
C4 C5 H5 . . 120.4(3) ?
C5 C6 H6 . . 121.3(3) ?
C5 C4 H4 . . 119.7(3) ?
C6 C5 H5 . . 118.1(3) ?
C8 C7 H7A . . 116.7(3) ?
C8 C7 H7B . . 116.5(3) ?
C7 C8 H8A . . 113.8(3) ?
C7 C8 H8B . . 113.1(3) ?
H8A C8 H8B . . 102.6(4) ?
H7A C7 H7B . . 103.0(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N2 . 1.2596(4) ?
O2 N2 . 1.2354(3) ?
N1 N2 . 1.3672(3) ?
N1 C1 . 1.4149(3) ?
N1 C7 . 1.5030(3) ?
C1 C2 . 1.4368(3) ?
C1 C6 . 1.4132(3) ?
C2 C8 . 1.5213(3) ?
C2 C3 . 1.3917(3) ?
C3 C4 . 1.4176(3) ?
C3 H3 . 1.083(5) ?
C4 C5 . 1.4312(3) ?
C4 H4 . 1.084(2) ?
C5 C6 . 1.4062(3) ?
C5 H5 . 1.083(5) ?
C6 H6 . 1.082(5) ?
C8 C7 . 1.5600(3) ?
C8 H8A . 1.087(5) ?
C8 H8B . 1.089(5) ?
C7 H7A . 1.089(5) ?
C7 H7B . 1.090(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 O2 1_544 1.083(5) 2.499(4) 3.3395(3) 133.6(3)
C6 H6 O1 1_555 1.082(5) 2.306(4) 2.8779(3) 111.1(2)
C7 H7B O1 1_655 1.090(5) 2.453(4) 3.3363(3) 137.2(4)
C5 H5 O1 3_675 1.083(5) 2.656(4) 3.4361(3) 128.5(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N2 N1 C1 . . . . 12.48(2) ?
O1 N2 N1 C7 . . . . 179.51(2) ?
O2 N2 N1 C1 . . . . -168.60(2) ?
O2 N2 N1 C7 . . . . -1.57(2) ?
N1 C1 C2 C8 . . . . 0.820(10) ?
N1 C1 C2 C3 . . . . -179.830(10) ?
N1 C1 C6 C5 . . . . 179.690(10) ?
N1 C1 C6 H6 . . . . -0.1(2) ?
N1 C7 C8 C2 . . . . 7.810(10) ?
N1 C7 C8 H8A . . . . 129.8(3) ?
N1 C7 C8 H8B . . . . -113.6(3) ?
N2 N1 C1 C2 . . . . 172.710(10) ?
N2 N1 C1 C6 . . . . -7.12(2) ?
N2 N1 C7 C8 . . . . -176.820(10) ?
N2 N1 C7 H7A . . . . 57.7(3) ?
N2 N1 C7 H7B . . . . -52.8(3) ?
C1 N1 C7 C8 . . . . -8.120(10) ?
C1 N1 C7 H7A . . . . -133.6(3) ?
C1 N1 C7 H7B . . . . 115.9(3) ?
C1 C2 C8 C7 . . . . -5.570(10) ?
C1 C2 C8 H8A . . . . -128.4(3) ?
C1 C2 C8 H8B . . . . 116.4(3) ?
C1 C2 C3 C4 . . . . 0.000(14) ?
C1 C2 C3 H3 . . . . -179.70(10) ?
C1 C6 C5 C4 . . . . 0.22(2) ?
C1 C6 C5 H5 . . . . 179.80(10) ?
C2 C1 N1 C7 . . . . 4.740(10) ?
C2 C1 C6 C5 . . . . -0.120(10) ?
C2 C1 C6 H6 . . . . -179.90(10) ?
C2 C8 C7 H7A . . . . 128.2(3) ?
C2 C8 C7 H7B . . . . -109.6(3) ?
C2 C3 C4 C5 . . . . 0.11(2) ?
C2 C3 C4 H4 . . . . 179.90(10) ?
C3 C2 C1 C6 . . . . 0.000(15) ?
C3 C2 C8 C7 . . . . 175.140(10) ?
C3 C2 C8 H8A . . . . 52.3(2) ?
C3 C2 C8 H8B . . . . -62.9(2) ?
C3 C4 C5 C6 . . . . -0.22(2) ?
C3 C4 C5 H5 . . . . -179.80(10) ?
C4 C3 C2 C8 . . . . 179.230(10) ?
C4 C5 C6 H6 . . . . -180.00(10) ?
C5 C4 C3 H3 . . . . 179.80(10) ?
C6 C1 N1 C7 . . . . -175.100(10) ?
C6 C1 C2 C8 . . . . -179.340(10) ?
C6 C5 C4 H4 . . . . 180.00(10) ?
C8 C2 C3 H3 . . . . -0.5(2) ?
H3 C3 C4 H4 . . . . -0.4(3) ?
H4 C4 C5 H5 . . . . 0.4(3) ?
H5 C5 C6 H6 . . . . -0.4(3) ?
H8A C8 C7 H7A . . . . -109.8(4) ?
H8A C8 C7 H7B . . . . 12.4(4) ?
H8B C8 C7 H7A . . . . 6.8(4) ?
H8B C8 C7 H7B . . . . 129.0(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10716405
