#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008183.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_2008183
loop_
_publ_author_name
'Garcia, J. Gabriel'
'Billodeaux, Damon R.'
'Fronczek, Frank R.'
_publ_section_title
;
 Two 3-substituted 5-nitroindoles
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9900007
_journal_paper_doi               10.1107/S0108270199099783
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          'C11 H11 Br N2 O2'
_chemical_formula_moiety         'C11 H11 Br N2 O2'
_chemical_formula_sum            'C11 H11 Br N2 O2'
_chemical_formula_weight         283.1
_chemical_name_systematic
;
3-(3-bromopropyl)-5-nitro-1H-indole
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 106.983(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.2326(3)
_cell_length_b                   16.766(2)
_cell_length_c                   6.6130(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      43
_cell_measurement_theta_min      33
_cell_volume                     554.86(9)
_computing_cell_refinement       'CAD-4 Operations Manual'
_computing_data_collection
'CAD-4 Operations Manual (Enraf-Nonius, 1977)'
_computing_data_reduction        'PROCESS in MolEN (Fair, 1990)'
_computing_molecular_graphics    ORTEPII_(Johnson,_1976)
_computing_publication_material  CIF_in_MolEN
_computing_structure_refinement  LSFM_in_MolEN
_computing_structure_solution    direct_methods_(SIR;_Burla_et_al.,_1989)
_diffrn_ambient_temperature      298
_diffrn_measurement_device       Enraf_Nonius_CAD-4
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         sealed_tube
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4694
_diffrn_reflns_theta_max         76
_diffrn_standards_decay_%        0.2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.98
_exptl_absorpt_correction_T_max  0.37
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_type   \y_scans_(North_et_al.,_1968)
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    none
_exptl_crystal_description       fragment
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.63
_refine_ls_abs_structure_details
;
Refinement of the antipodal structure under identical circumstances yielded
R = 0.040, wR = 0.055, S = 3.056.
;
_refine_ls_extinction_coef       1.39E-5(3)
_refine_ls_extinction_method     isotropic_(Zachariasen,_1963)
_refine_ls_goodness_of_fit_obs   1.978
_refine_ls_hydrogen_treatment    refined_isotropically
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2312
_refine_ls_R_factor_obs          0.025
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 4Fo²/[σ²(Fo²) + 0.0004Fo⁴]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.036
_reflns_number_observed          2312
_reflns_number_total             2314
_reflns_observed_criterion       I>0
_cod_data_source_file            qa0079.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 4Fo^2^/[\s^2^(Fo^2^) +
0.0004Fo^4^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        554.90(10)
_cod_original_sg_symbol_Hall     'P 2y1'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2008183
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
Br 0.90568(5) 0 -0.08162(3) 0.06900(10) Uani ?
O1 0.4514(3) 0.20520(10) 0.8484(3) 0.0587(7) Uani ?
O2 0.3563(3) 0.33020(10) 0.8239(3) 0.0667(8) Uani ?
N1 0.9996(3) 0.28670(10) 0.1697(3) 0.0526(8) Uani ?
N2 0.4624(3) 0.27160(10) 0.7739(3) 0.0440(7) Uani ?
C1 1.1036(4) 0.2110(2) 0.1862(3) 0.0503(9) Uani ?
C2 1.0321(3) 0.16870(10) 0.3368(3) 0.0419(8) Uani ?
C3 0.8738(3) 0.22160(10) 0.4209(3) 0.0363(7) Uani ?
C4 0.8579(4) 0.29550(10) 0.3119(3) 0.0423(8) Uani ?
C5 0.7132(4) 0.36030(10) 0.3534(4) 0.0476(9) Uani ?
C6 0.5876(4) 0.35220(10) 0.5092(4) 0.0451(9) Uani ?
C7 0.6063(3) 0.27950(10) 0.6173(3) 0.0376(8) Uani ?
C8 0.7450(3) 0.21450(10) 0.5767(3) 0.0369(7) Uani ?
C9 1.1022(4) 0.08380(10) 0.3995(3) 0.0459(9) Uani ?
C10 0.8616(4) 0.02730(10) 0.3380(3) 0.0452(8) Uani ?
C11 0.6999(4) 0.03110(10) 0.1093(3) 0.0466(9) Uani ?
H1N 1.026(6) 0.318(2) 0.070(4) 0.060(8) Uiso ?
H1 1.230(6) 0.196(2) 0.107(4) 0.059(8) Uiso ?
H5 0.729(8) 0.413(3) 0.277(6) 0.12(2) Uiso ?
H6 0.493(5) 0.396(2) 0.542(4) 0.049(6) Uiso ?
H8 0.738(5) 0.1660(10) 0.637(4) 0.042(6) Uiso ?
H9a 1.187(5) 0.080(2) 0.569(4) 0.056(7) Uiso ?
H9b 1.245(5) 0.062(2) 0.326(4) 0.048(6) Uiso ?
H10a 0.746(5) 0.040(2) 0.428(4) 0.062(8) Uiso ?
H10b 0.918(5) -0.032(2) 0.384(4) 0.059(8) Uiso ?
H11a 0.551(4) 0.005(3) 0.083(3) 0.052(7) Uiso ?
H11b 0.655(5) 0.085(2) 0.069(4) 0.051(7) Uiso ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 International_Tables_Vol_IV_Table_2.3.1
H 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1
N 0.029 0.018 International_Tables_Vol_IV_Table_2.3.1
O 0.047 0.032 International_Tables_Vol_IV_Table_2.3.1
Br -0.767 1.283 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 5 1
2 4 3
-3 -6 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C4 109.1(2) yes
C1 N1 H1N 117(2) ?
C4 N1 H1N 133(2) ?
O1 N2 O2 122.9(2) yes
O1 N2 C7 117.6(2) yes
O2 N2 C7 119.5(2) yes
N1 C1 C2 110.6(2) yes
N1 C1 H1 120.0(10) ?
C2 C1 H1 128.0(10) ?
C1 C2 C3 106.0(2) ?
C1 C2 C9 126.9(2) ?
C3 C2 C9 127.1(2) ?
C2 C3 C4 107.3(2) ?
C2 C3 C8 134.1(2) ?
C4 C3 C8 118.7(2) ?
N1 C4 C3 106.9(2) ?
N1 C4 C5 130.9(2) ?
C3 C4 C5 122.2(2) ?
C4 C5 C6 118.3(2) ?
C4 C5 H5 116(2) ?
C6 C5 H5 125(2) ?
C5 C6 C7 119.2(2) ?
C5 C6 H6 119.0(10) ?
C7 C6 H6 121.0(10) ?
N2 C7 C6 117.9(2) ?
N2 C7 C8 118.6(2) ?
C6 C7 C8 123.4(2) ?
C3 C8 C7 118.3(2) ?
C3 C8 H8 119.0(10) ?
C7 C8 H8 122.0(10) ?
C2 C9 C10 113.50(10) ?
C2 C9 H9a 109.0(10) ?
C2 C9 H9b 110.0(10) ?
C10 C9 H9a 107.0(10) ?
C10 C9 H9b 107.0(10) ?
H9a C9 H9b 108.0(10) ?
C9 C10 C11 114.7(2) ?
C9 C10 H10a 108.0(10) ?
C9 C10 H10b 111.0(10) ?
C11 C10 H10a 109.0(10) ?
C11 C10 H10b 111.0(10) ?
H10a C10 H10b 101(2) ?
Br C11 C10 112.60(10) yes
Br C11 H11a 111(2) ?
Br C11 H11b 102.0(10) ?
C10 C11 H11a 112.0(10) ?
C10 C11 H11b 110.0(10) ?
H11a C11 H11b 106(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C11 1.955(2) yes
O1 N2 1.227(3) yes
O2 N2 1.220(3) yes
N1 C1 1.373(3) yes
N1 C4 1.365(3) yes
N1 H1N 0.88(3) ?
N2 C7 1.454(3) ?
C1 C2 1.361(3) yes
C1 H1 0.99(3) ?
C2 C3 1.432(3) ?
C2 C9 1.498(3) ?
C3 C4 1.424(3) ?
C3 C8 1.391(3) ?
C4 C5 1.396(3) ?
C5 C6 1.382(4) ?
C5 H5 1.03(4) ?
C6 C7 1.402(3) ?
C6 H6 0.95(3) ?
C7 C8 1.377(3) ?
C8 H8 0.92(3) ?
C9 C10 1.533(3) ?
C9 H9a 1.08(2) ?
C9 H9b 1.07(3) ?
C10 C11 1.503(3) ?
C10 H10a 0.99(3) ?
C10 H10b 1.05(3) ?
C11 H11a 0.86(3) ?
C11 H11b 0.95(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
_geom_torsion_publ_flag
C4 N1 C1 C2 0.4(3) ?
C1 N1 C4 C3 -0.3(2) ?
C1 N1 C4 C5 -178.9(2) ?
O1 N2 C7 C6 171.0(2) ?
O1 N2 C7 C8 -6.6(3) yes
O2 N2 C7 C6 -8.3(3) ?
O2 N2 C7 C8 174.2(2) ?
N1 C1 C2 C3 -0.3(2) ?
N1 C1 C2 C9 179.0(2) ?
C1 C2 C3 C4 0.1(3) ?
C1 C2 C3 C8 -179.6(2) ?
C9 C2 C3 C4 -179.2(2) ?
C9 C2 C3 C8 1.1(3) ?
C1 C2 C9 C10 -111.5(2) yes
C3 C2 C9 C10 67.7(3) ?
C2 C3 C4 N1 0.2(2) ?
C2 C3 C4 C5 178.9(2) ?
C8 C3 C4 N1 179.9(2) ?
C8 C3 C4 C5 -1.4(3) ?
C2 C3 C8 C7 -179.9(2) ?
C4 C3 C8 C7 0.5(3) ?
N1 C4 C5 C6 -180.0(4) ?
C3 C4 C5 C6 1.6(3) ?
C4 C5 C6 C7 -0.9(3) ?
C5 C6 C7 N2 -177.4(2) ?
C5 C6 C7 C8 0.1(4) ?
N2 C7 C8 C3 177.6(2) ?
C6 C7 C8 C3 0.2(3) ?
C2 C9 C10 C11 52.6(2) yes
C9 C10 C11 Br 62.4(2) yes
