#------------------------------------------------------------------------------
#$Date: 2016-02-19 15:29:56 +0100 (vie 19 de feb de 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/92/2009244.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_2009244
loop_
_publ_author_name
'Ghosh, Sutapa'
'Zheng, Yaguo'
'Uckun, Fatih M.'
_publ_section_title
;
 Five analogs of the active metabolite of leflunomide
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2117
_journal_page_last               2122
_journal_paper_doi               10.1107/S0108270199011142
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C11 H9 Br N2 O2'
_chemical_formula_sum            'C11 H9 Br N2 O2'
_chemical_formula_weight         281.11
_chemical_name_systematic
;
 α-cyano-β-hydroxy-N-(4-bromophenyl)but-2-enamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                77.394(2)
_cell_angle_beta                 86.404(2)
_cell_angle_gamma                88.065(2)
_cell_formula_units_Z            2
_cell_length_a                   4.9906(2)
_cell_length_b                   9.3735(3)
_cell_length_c                   11.88690(10)
_cell_measurement_reflns_used    1833
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      1.76
_cell_volume                     541.47(3)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1996b)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device_type  'Siemens SMART  CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2741
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    3.781
_exptl_absorpt_correction_T_max  0.9455
_exptl_absorpt_correction_T_min  0.2996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996a)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.271
_refine_diff_density_min         -0.990
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1065P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1655
_reflns_number_gt                1473
_reflns_number_total             1836
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            da1089.cif
_cod_data_source_block           LFM_A1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_sg_symbol_H-M      P-1
_cod_database_code               2009244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_adp_type
_atom_site_type_symbol
Br4 -0.38475(15) -0.17096(7) 0.42548(6) 0.0445(3) Uani Br
O7 -0.1944(9) 0.2496(5) -0.1311(4) 0.0364(10) Uani O
O9 -0.1387(9) 0.4055(5) -0.3288(4) 0.0396(11) Uani O
N1 0.0738(10) 0.2731(5) 0.0115(4) 0.0271(11) Uani N
N11 0.5175(11) 0.5689(6) -0.1223(5) 0.0369(13) Uani N
C1 -0.0390(11) 0.1656(6) 0.1040(5) 0.0264(12) Uani C
C2 0.0661(13) 0.1540(7) 0.2109(5) 0.0362(15) Uani C
C3 -0.0329(14) 0.0547(7) 0.3061(6) 0.0374(15) Uani C
C4 -0.2380(12) -0.0336(6) 0.2946(5) 0.0299(13) Uani C
C5 -0.3443(14) -0.0261(7) 0.1888(6) 0.0404(16) Uani C
C6 -0.2410(13) 0.0737(7) 0.0931(6) 0.0360(15) Uani C
C7 -0.0048(12) 0.3108(6) -0.0978(5) 0.0275(13) Uani C
C8 0.1364(11) 0.4272(6) -0.1808(5) 0.0265(13) Uani C
C9 0.0627(13) 0.4677(7) -0.2922(6) 0.0344(14) Uani C
C10 0.1994(14) 0.5805(7) -0.3825(6) 0.0390(15) Uani C
C11 0.3502(12) 0.5050(6) -0.1490(5) 0.0280(13) Uani C
H1 0.194(11) 0.327(6) 0.035(5) 0.011(13) Uiso H
H2 0.2083 0.2154 0.2185 0.043 Uiso H
H3 0.0402 0.0474 0.3791 0.045 Uiso H
H5 -0.4858 -0.0882 0.1817 0.048 Uiso H
H6 -0.3102 0.0786 0.0197 0.043 Uiso H
H9 -0.2005 0.3389 -0.2752 0.029(17) Uiso H
H10A 0.1106 0.5908 -0.4551 0.058 Uiso H
H10B 0.3878 0.5511 -0.3936 0.058 Uiso H
H10C 0.1902 0.6741 -0.3584 0.058 Uiso 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
_atom_site_aniso_type_symbol
Br4 0.0520(5) 0.0422(4) 0.0324(4) -0.0104(3) 0.0094(3) 0.0053(3) Br
O7 0.036(2) 0.044(3) 0.029(2) -0.0142(19) -0.007(2) -0.0043(19) O
O9 0.041(3) 0.053(3) 0.022(2) -0.017(2) -0.004(2) -0.001(2) O
N1 0.025(3) 0.033(3) 0.023(3) -0.010(2) 0.000(2) -0.005(2) N
N11 0.038(3) 0.045(3) 0.026(3) -0.011(3) -0.001(2) -0.002(2) N
C1 0.022(3) 0.031(3) 0.024(3) -0.001(2) 0.002(2) -0.003(2) C
C2 0.039(4) 0.039(4) 0.027(3) -0.010(3) -0.002(3) 0.002(3) C
C3 0.041(4) 0.041(4) 0.028(3) -0.006(3) -0.003(3) -0.004(3) C
C4 0.030(3) 0.028(3) 0.028(3) -0.004(2) 0.006(3) -0.001(2) C
C5 0.041(4) 0.040(4) 0.041(4) -0.016(3) -0.001(3) -0.007(3) C
C6 0.042(4) 0.039(4) 0.024(3) -0.009(3) -0.001(3) 0.001(3) C
C7 0.026(3) 0.034(3) 0.026(3) 0.000(2) 0.002(3) -0.014(3) C
C8 0.025(3) 0.032(3) 0.022(3) 0.000(2) 0.000(2) -0.007(2) C
C9 0.031(3) 0.044(4) 0.028(3) 0.003(3) 0.001(3) -0.008(3) C
C10 0.042(4) 0.045(4) 0.028(3) -0.011(3) 0.003(3) -0.003(3) C
C11 0.029(3) 0.031(3) 0.021(3) -0.003(3) 0.005(2) -0.001(2) C
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'
Br Br -0.2901 2.4595 '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
C7 N1 C1 127.5(5) yes
C6 C1 C2 119.1(6) no
C6 C1 N1 124.2(5) yes
C2 C1 N1 116.6(5) yes
C3 C2 C1 120.9(6) no
C4 C3 C2 119.3(6) no
C3 C4 C5 121.2(6) yes
C3 C4 Br4 120.5(5) yes
C5 C4 Br4 118.3(4) no
C4 C5 C6 119.0(6) no
C1 C6 C5 120.5(6) no
O7 C7 N1 122.2(6) yes
O7 C7 C8 118.7(5) yes
N1 C7 C8 119.2(5) yes
C9 C8 C11 117.1(6) yes
C9 C8 C7 120.7(5) yes
C11 C8 C7 122.1(5) yes
O9 C9 C8 121.6(6) yes
O9 C9 C10 114.1(5) yes
C8 C9 C10 124.3(6) yes
N11 C11 C8 178.5(7) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br4 C4 . . 1.913(6) yes
O7 C7 . . 1.250(7) yes
O9 C9 . . 1.321(7) yes
N1 C7 . . 1.349(8) yes
N1 C1 . . 1.421(8) yes
N11 C11 . . 1.143(8) yes
C1 C6 . . 1.378(8) no
C1 C2 . . 1.386(9) no
C2 C3 . . 1.376(9) no
C3 C4 . . 1.370(9) no
C4 C5 . . 1.381(9) no
C5 C6 . . 1.389(9) no
C7 C8 . . 1.468(9) yes
C8 C9 . . 1.366(9) yes
C8 C11 . . 1.427(8) yes
C9 C10 . . 1.482(9) yes
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
_geom_hbond_publ_flag
O9 H9 O7 . 0.84 1.74 2.487(6) 147.6 yes
N1 H1 N11 2_665 0.89(6) 2.20(6) 3.079(7) 170(5) yes
