#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007306.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_2007306
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         'C14 H11 F N2 O3'
_chemical_formula_sum            'C14 H11 F N2 O3'
_chemical_formula_weight         274.25
_chemical_name_systematic
;
2-methylamino-9-fluoro-5-nitrobenzophenone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 94.7480(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.2150(17)
_cell_length_b                   13.6020(18)
_cell_length_c                   21.547(7)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.42
_cell_volume                     1231.1(7)
_computing_molecular_graphics    'ZORTEP (Zsolani, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.870
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  '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  0.0943
_diffrn_reflns_av_sigmaI/netI    0.2214
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5315
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.496
_refine_ls_hydrogen_treatment    H_atoms:_see_text
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.496
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      'calc w = 1/\s^2^(Fo^2^)'
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                736
_reflns_number_total             1946
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1214.cif
_[local]_cod_data_source_block   IV
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_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_database_code               2007306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
F1 0.1197(4) 0.37583(12) 0.02766(8) 0.0400(5) Uani d . 1 F
O1 0.1869(5) 0.09796(15) -0.00273(9) 0.0380(6) Uani d . 1 O
O2 0.9377(5) 0.35503(16) 0.25413(10) 0.0433(7) Uani d . 1 O
O3 0.9450(5) 0.41232(17) 0.16025(10) 0.0447(7) Uani d . 1 O
N1 0.1046(5) 0.03345(17) 0.11140(11) 0.0286(7) Uani d . 1 N
H1 0.0626 0.0256 0.0710 0.026(3) Uiso calc R 1 H
N2 0.8582(6) 0.3510(2) 0.19769(13) 0.0322(7) Uani d . 1 N
C1 0.3884(7) 0.1822(2) 0.08866(13) 0.0225(8) Uani d . 1 C
C2 0.2802(7) 0.1116(2) 0.13109(13) 0.0236(8) Uani d . 1 C
C3 0.3654(7) 0.1256(2) 0.19589(13) 0.0281(8) Uani d . 1 C
H3 0.2916 0.0802 0.2249 0.026(3) Uiso calc R 1 H
C4 0.5508(7) 0.2031(2) 0.21729(14) 0.0289(8) Uani d . 1 C
H4 0.6073 0.2107 0.2606 0.026(3) Uiso calc R 1 H
C5 0.6560(7) 0.2706(2) 0.17490(14) 0.0231(8) Uani d . 1 C
C6 0.5761(7) 0.2603(2) 0.11215(14) 0.0238(8) Uani d . 1 C
H6 0.6504 0.3073 0.0842 0.026(3) Uiso calc R 1 H
C7 0.3119(7) 0.1723(2) 0.02075(14) 0.0256(8) Uani d . 1 C
C8 0.3961(7) 0.2531(2) -0.02285(13) 0.0224(7) Uani d . 1 C
C9 0.2946(7) 0.3492(2) -0.02019(13) 0.0251(8) Uani d . 1 C
C10 0.3529(7) 0.4192(2) -0.06339(13) 0.0313(8) Uani d . 1 C
H10 0.2759 0.4844 -0.0596 0.026(3) Uiso calc R 1 H
C11 0.5245(7) 0.3936(2) -0.11234(14) 0.0363(9) Uani d . 1 C
H11 0.5712 0.4414 -0.1424 0.026(3) Uiso calc R 1 H
C12 0.6295(7) 0.2974(3) -0.11775(14) 0.0364(9) Uani d . 1 C
H12 0.7469 0.2795 -0.1518 0.026(3) Uiso calc R 1 H
C13 0.5644(7) 0.2279(2) -0.07405(13) 0.0302(8) Uani d . 1 C
H13 0.6343 0.1621 -0.0787 0.026(3) Uiso calc R 1 H
C14 -0.0218(7) -0.0399(2) 0.15307(13) 0.0325(9) Uani d . 1 C
H14A -0.1426 -0.0897 0.1282 0.070(6) Uiso calc R 1 H
H14B -0.1619 -0.0073 0.1808 0.070(6) Uiso calc R 1 H
H14C 0.1550 -0.0714 0.1779 0.070(6) Uiso calc R 1 H
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
F1 0.0455(12) 0.0370(12) 0.0389(11) 0.0060(10) 0.0108(10) -0.0005(10)
O1 0.0552(16) 0.0294(14) 0.0280(13) -0.0147(13) -0.0052(12) -0.0035(12)
O2 0.0525(16) 0.0520(17) 0.0231(13) -0.0076(13) -0.0101(12) -0.0111(13)
O3 0.0541(16) 0.0413(16) 0.0372(15) -0.0165(13) -0.0049(12) 0.0034(13)
N1 0.0352(16) 0.0299(17) 0.0202(15) -0.0003(15) -0.0021(13) 0.0049(14)
N2 0.0271(18) 0.0363(19) 0.0325(19) 0.0036(15) -0.0020(15) -0.0069(16)
C1 0.0217(19) 0.0230(19) 0.0223(19) 0.0037(16) -0.0006(15) 0.0022(16)
C2 0.0220(19) 0.022(2) 0.027(2) 0.0016(16) 0.0002(15) -0.0055(16)
C3 0.031(2) 0.031(2) 0.0220(19) 0.0026(18) 0.0018(16) 0.0006(17)
C4 0.034(2) 0.037(2) 0.0167(18) 0.0032(18) 0.0020(16) -0.0049(17)
C5 0.0206(19) 0.0253(19) 0.0227(19) 0.0049(16) -0.0034(15) -0.0050(17)
C6 0.0266(19) 0.0220(19) 0.0225(19) 0.0055(17) -0.0006(15) 0.0004(16)
C7 0.025(2) 0.024(2) 0.027(2) 0.0002(16) -0.0003(16) -0.0019(17)
C8 0.0230(19) 0.024(2) 0.0196(18) -0.0037(16) -0.0040(14) -0.0021(16)
C9 0.025(2) 0.030(2) 0.0198(18) -0.0008(17) 0.0035(15) -0.0049(16)
C10 0.038(2) 0.024(2) 0.0303(19) -0.0010(17) -0.0045(17) 0.0015(17)
C11 0.040(2) 0.038(2) 0.030(2) -0.0129(19) 0.0009(17) 0.0048(18)
C12 0.033(2) 0.045(3) 0.032(2) -0.0081(19) 0.0077(17) -0.0039(19)
C13 0.034(2) 0.029(2) 0.027(2) -0.0028(17) -0.0018(17) -0.0030(17)
C14 0.034(2) 0.026(2) 0.037(2) -0.0014(17) 0.0024(17) 0.0065(17)
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'
F F 0.0171 0.0103 '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
C2 N1 C14 124.1(3) n
O2 N2 O3 122.8(3) n
O2 N2 C5 118.1(3) n
O3 N2 C5 119.1(3) n
C6 C1 C2 118.8(3) n
C6 C1 C7 119.9(3) n
C2 C1 C7 121.2(3) n
N1 C2 C3 120.2(3) n
N1 C2 C1 121.8(3) n
C3 C2 C1 118.0(3) n
C4 C3 C2 121.6(3) n
C3 C4 C5 119.4(3) n
C6 C5 C4 120.8(3) n
C6 C5 N2 120.0(3) n
C4 C5 N2 119.1(3) n
C5 C6 C1 121.4(3) n
O1 C7 C1 122.2(3) n
O1 C7 C8 117.3(3) n
C1 C7 C8 120.5(3) n
C9 C8 C13 116.4(3) n
C9 C8 C7 125.2(2) n
C13 C8 C7 118.1(3) n
F1 C9 C10 117.9(3) n
F1 C9 C8 118.2(3) n
C10 C9 C8 123.9(3) n
C9 C10 C11 118.8(3) n
C10 C11 C12 119.7(3) n
C13 C12 C11 120.4(3) n
C12 C13 C8 120.7(3) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C9 1.365(3) y
O1 C7 1.230(3) y
O2 N2 1.236(3) y
O3 N2 1.236(3) y
N1 C2 1.343(3) y
N1 C14 1.471(3) n
N2 C5 1.447(4) y
C1 C6 1.395(4) n
C1 C2 1.427(4) n
C1 C7 1.478(4) n
C2 C3 1.425(4) n
C3 C4 1.369(4) n
C4 C5 1.393(4) n
C5 C6 1.373(4) n
C7 C8 1.507(4) n
C8 C9 1.377(4) n
C8 C13 1.403(3) n
C9 C10 1.368(4) n
C10 C11 1.372(3) n
C11 C12 1.388(4) n
C12 C13 1.378(4) 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
C14 N1 C2 C3 2.4(4) n
C14 N1 C2 C1 -178.0(3) n
C6 C1 C2 N1 -178.5(2) n
C7 C1 C2 N1 -0.1(4) n
C6 C1 C2 C3 1.2(4) n
C7 C1 C2 C3 179.6(3) n
N1 C2 C3 C4 178.3(3) n
C1 C2 C3 C4 -1.4(4) n
C2 C3 C4 C5 0.8(4) n
C3 C4 C5 C6 -0.1(4) n
C3 C4 C5 N2 -178.5(3) n
O2 N2 C5 C6 -176.5(3) n
O3 N2 C5 C6 3.3(4) n
O2 N2 C5 C4 2.0(4) n
O3 N2 C5 C4 -178.2(3) n
C4 C5 C6 C1 -0.1(4) n
N2 C5 C6 C1 178.4(2) n
C2 C1 C6 C5 -0.5(4) n
C7 C1 C6 C5 -178.9(3) n
C6 C1 C7 O1 169.4(3) n
C2 C1 C7 O1 -9.0(4) n
C6 C1 C7 C8 -8.5(4) y
C2 C1 C7 C8 173.1(3) n
O1 C7 C8 C9 124.3(3) n
C1 C7 C8 C9 -57.7(4) y
O1 C7 C8 C13 -49.0(4) n
C1 C7 C8 C13 129.0(3) n
C13 C8 C9 F1 177.6(2) n
C7 C8 C9 F1 4.2(5) n
C13 C8 C9 C10 -1.0(5) n
C7 C8 C9 C10 -174.4(3) n
F1 C9 C10 C11 -179.1(3) n
C8 C9 C10 C11 -0.5(5) n
C9 C10 C11 C12 1.3(5) n
C10 C11 C12 C13 -0.5(5) n
C11 C12 C13 C8 -1.1(5) n
C9 C8 C13 C12 1.8(5) n
C7 C8 C13 C12 175.6(3) n