#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007305.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_2007305
loop_
_publ_author_name
'Cox, P. J.'
'Anisuzzaman, A. T. Md.'
'Pryce-Jones, R. H.'
'Skellern, G. G.'
'Florence, A. J.'
'Shankland, N.'
_publ_section_title
;
 2-Amino-5-nitrobenzophenone and
 2'-Fluoro-2-methylamino-5-nitrobenzophenone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              856
_journal_page_last               859
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C13 H10 N2 O3'
_chemical_formula_sum            'C13 H10 N2 O3'
_chemical_formula_weight         242.23
_chemical_name_systematic
;
2-amino-5-nitrobenzophenone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 98.87(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7358(15)
_cell_length_b                   14.693(2)
_cell_length_c                   13.1120(12)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      2.10
_cell_volume                     1091.8(4)
_computing_molecular_graphics    'ZORTEP (Zsolani, 1997)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       'Delft Instruments FAST diffractometer'
_diffrn_measurement_method       Area-detector
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_sigmaI/netI    0.1062
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4705
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.757
_refine_ls_goodness_of_fit_obs   0.957
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.757
_refine_ls_restrained_S_obs      0.957
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_obs          0.0378
_refine_ls_shift/esd_max         0.037
_refine_ls_shift/esd_mean        0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0128P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0768
_refine_ls_wR_factor_obs         0.0718
_reflns_number_observed          1004
_reflns_number_total             1705
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    bm1214.cif
_[local]_cod_data_source_block   II
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1091.8(3)
_cod_database_code               2007305
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0242(10) 0.0369(10) 0.0380(10) -0.0002(8) 0.0014(8) 0.0000(9)
O2 0.0357(11) 0.0354(11) 0.0462(12) 0.0119(8) 0.0097(9) -0.0022(9)
O3 0.0405(11) 0.0383(11) 0.0309(11) 0.0048(8) -0.0049(9) 0.0050(9)
N1 0.0316(13) 0.0401(13) 0.0250(12) 0.0068(10) -0.0041(11) -0.0037(10)
N2 0.0309(13) 0.0262(12) 0.0315(13) -0.0026(10) 0.0049(12) 0.0032(11)
C2 0.0235(14) 0.0223(13) 0.0269(14) -0.0066(11) 0.0016(12) 0.0025(12)
C3 0.0381(15) 0.0274(14) 0.0210(13) -0.0041(12) 0.0057(12) -0.0068(12)
C4 0.0324(15) 0.0224(13) 0.0274(15) 0.0011(11) 0.0043(12) -0.0047(12)
C5 0.0245(13) 0.0175(12) 0.0240(13) -0.0012(10) 0.0024(12) 0.0028(11)
C6 0.0282(14) 0.0225(13) 0.0214(14) -0.0053(11) -0.0003(12) 0.0021(11)
C1 0.0232(14) 0.0214(13) 0.0239(14) -0.0025(11) 0.0017(12) 0.0003(11)
C7 0.031(2) 0.0189(13) 0.0303(14) -0.0035(11) 0.0096(13) 0.0044(11)
C8 0.0223(13) 0.0224(13) 0.0259(14) 0.0011(11) 0.0049(12) 0.0002(11)
C9 0.0355(15) 0.0254(13) 0.0268(14) -0.0010(12) 0.0111(12) -0.0018(12)
C10 0.0301(14) 0.0259(14) 0.036(2) -0.0037(11) 0.0029(13) -0.0043(12)
C11 0.040(2) 0.0264(14) 0.0274(15) 0.0061(12) 0.0020(13) -0.0051(12)
C12 0.039(2) 0.0302(14) 0.0264(14) 0.0061(12) 0.0097(13) -0.0001(12)
C13 0.0265(13) 0.0272(14) 0.0326(15) 0.0012(11) 0.0056(12) 0.0018(12)
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
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 -0.5359(3) 0.41489(11) 0.05411(12) 0.0334(4) Uani d . 1 O
O2 0.4664(3) 0.15099(11) 0.01306(13) 0.0388(5) Uani d . 1 O
O3 0.4238(3) 0.21949(11) 0.15571(13) 0.0377(5) Uani d . 1 O
N1 -0.4736(3) 0.35760(13) -0.13255(14) 0.0331(5) Uani d . 1 N
H1A -0.5190(3) 0.34549(13) -0.19671(14) 0.027(2) Uiso calc R 1 H
H1B -0.5581(3) 0.39209(13) -0.09989(14) 0.027(2) Uiso calc R 1 H
N2 0.3572(3) 0.20151(13) 0.0632(2) 0.0295(5) Uani d . 1 N
C1 -0.1887(4) 0.34144(14) 0.0220(2) 0.0230(6) Uani d . 1 C
C2 -0.2716(4) 0.32282(15) -0.0836(2) 0.0245(6) Uani d . 1 C
C3 -0.1347(4) 0.26626(15) -0.1384(2) 0.0287(6) Uani d . 1 C
H3 -0.1835(4) 0.25601(15) -0.2084(2) 0.027(2) Uiso calc R 1 H
C4 0.0677(4) 0.22643(15) -0.0905(2) 0.0274(6) Uani d . 1 C
H4 0.1551(4) 0.18875(15) -0.1273(2) 0.027(2) Uiso calc R 1 H
C5 0.1412(4) 0.24266(14) 0.0130(2) 0.0221(5) Uani d . 1 C
C6 0.0188(4) 0.29928(14) 0.0677(2) 0.0245(6) Uani d . 1 C
H6 0.0750(4) 0.31002(14) 0.1370(2) 0.027(2) Uiso calc R 1 H
C7 -0.3247(4) 0.39855(15) 0.0832(2) 0.0261(6) Uani d . 1 C
C8 -0.2108(4) 0.43948(14) 0.1819(2) 0.0234(5) Uani d . 1 C
C9 0.0056(4) 0.48268(15) 0.1928(2) 0.0286(6) Uani d . 1 C
H9 0.0940(4) 0.48134(15) 0.1390(2) 0.027(2) Uiso calc R 1 H
C10 0.0911(4) 0.5278(2) 0.2832(2) 0.0310(6) Uani d . 1 C
H10 0.2356(4) 0.5577(2) 0.2895(2) 0.027(2) Uiso calc R 1 H
C11 -0.0351(4) 0.5290(2) 0.3634(2) 0.0316(6) Uani d . 1 C
H11 0.0243(4) 0.5593(2) 0.4242(2) 0.027(2) Uiso calc R 1 H
C12 -0.2514(4) 0.4852(2) 0.3547(2) 0.0312(6) Uani d . 1 C
H12 -0.3370(4) 0.4852(2) 0.4094(2) 0.027(2) Uiso calc R 1 H
C13 -0.3368(4) 0.4418(2) 0.2639(2) 0.0287(6) Uani d . 1 C
H13 -0.4831(4) 0.4133(2) 0.2572(2) 0.027(2) Uiso calc R 1 H
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_publ_flag
O2 N2 O3 123.2(2) n
O2 N2 C5 118.9(2) n
O3 N2 C5 118.0(2) n
N1 C2 C3 119.3(2) n
N1 C2 C1 122.0(2) n
C3 C2 C1 118.7(2) n
C4 C3 C2 121.2(2) n
C3 C4 C5 119.3(2) n
C6 C5 C4 121.3(2) n
C6 C5 N2 119.4(2) n
C4 C5 N2 119.2(2) n
C5 C6 C1 121.4(2) n
C6 C1 C2 118.0(2) n
C6 C1 C7 120.7(2) n
C2 C1 C7 121.2(2) n
O1 C7 C1 121.4(2) n
O1 C7 C8 118.0(2) n
C1 C7 C8 120.6(2) n
C9 C8 C13 118.5(2) n
C9 C8 C7 122.9(2) n
C13 C8 C7 118.3(2) n
C10 C9 C8 120.2(2) n
C11 C10 C9 120.5(2) n
C10 C11 C12 120.3(2) n
C13 C12 C11 118.8(2) n
C12 C13 C8 121.7(2) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O3 N2 1.243(2) y
O2 N2 1.225(2) y
O1 C7 1.236(2) y
N1 C2 1.336(3) y
N2 C5 1.443(3) y
C2 C3 1.413(3) n
C2 C1 1.420(3) n
C3 C4 1.364(3) n
C4 C5 1.378(3) n
C5 C6 1.362(3) n
C6 C1 1.392(3) n
C1 C7 1.466(3) n
C7 C8 1.485(3) n
C8 C9 1.382(3) n
C8 C13 1.385(3) n
C9 C10 1.381(3) n
C10 C11 1.366(3) n
C11 C12 1.386(3) n
C12 C13 1.373(3) n
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
N1 C2 C3 C4 -177.4(2) n
C1 C2 C3 C4 3.1(3) n
C2 C3 C4 C5 -0.8(3) n
C3 C4 C5 C6 -1.6(3) n
C3 C4 C5 N2 -179.1(2) n
O2 N2 C5 C6 -179.7(2) n
O3 N2 C5 C6 0.1(3) n
O2 N2 C5 C4 -2.1(3) n
O3 N2 C5 C4 177.7(2) n
C4 C5 C6 C1 1.6(3) n
N2 C5 C6 C1 179.1(2) n
C5 C6 C1 C2 0.8(3) n
C5 C6 C1 C7 176.9(2) n
N1 C2 C1 C6 177.5(2) n
C3 C2 C1 C6 -3.0(3) n
N1 C2 C1 C7 1.3(3) n
C3 C2 C1 C7 -179.1(2) n
C6 C1 C7 O1 -159.0(2) n
C2 C1 C7 O1 17.1(3) n
C6 C1 C7 C8 21.7(3) y
C2 C1 C7 C8 -162.3(2) n
O1 C7 C8 C9 -133.4(2) n
C1 C7 C8 C9 45.9(3) y
O1 C7 C8 C13 40.4(3) n
C1 C7 C8 C13 -140.2(2) n
C13 C8 C9 C10 -0.8(3) n
C7 C8 C9 C10 173.1(2) n
C8 C9 C10 C11 1.1(3) n
C9 C10 C11 C12 -0.4(3) n
C10 C11 C12 C13 -0.8(3) n
C11 C12 C13 C8 1.1(3) n
C9 C8 C13 C12 -0.4(3) n
C7 C8 C13 C12 -174.5(2) n