#------------------------------------------------------------------------------
#$Date: 2016-02-20 04:06:23 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/99/2209978.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_2209978
loop_
_publ_author_name
'Yong-Hong Wen'
'Li-Li Xu'
'Xue-Mei Li'
'Shu-Sheng Zhang'
_publ_section_title
;
 N,N'-Bis(2-methylphenyl)oxamide
;
_journal_coeditor_code           RZ2050
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3276
_journal_page_last               o3277
_journal_paper_doi               10.1107/S1600536806025992
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H16 N2 O2'
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_name_systematic
;
N,N'-Bis(2-methylphenyl)oxamide
;
_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           SHELXL-97
_cell_angle_alpha                99.582(4)
_cell_angle_beta                 96.152(4)
_cell_angle_gamma                106.527(4)
_cell_formula_units_Z            1
_cell_length_a                   5.3504(13)
_cell_length_b                   6.7371(17)
_cell_length_c                   10.228(3)
_cell_measurement_reflns_used    798
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      3.2
_cell_volume                     343.83(16)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1934
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             142
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.171
_refine_ls_extinction_coef       0.14(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0866P)²+0.0923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                1111
_reflns_number_total             1311
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2050.cif
_cod_data_source_block           I
_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_cell_volume        343.83(15)
_cod_database_code               2209978
_cod_database_fobs_code          2209978
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_refinement_flags
_atom_site_occupancy
O O1 -0.2945(2) 0.3661(2) 0.04882(14) 0.0583(5) Uani d . 1
N N1 0.1213(3) 0.3400(2) 0.09497(16) 0.0480(5) Uani d . 1
H H1B 0.2807 0.3942 0.0824 0.058 Uiso calc R 1
C C1 0.2966(4) 0.1737(4) 0.2557(2) 0.0663(7) Uani d . 1
H H1A 0.4593 0.2759 0.2632 0.080 Uiso calc R 1
C C2 0.2722(5) 0.0162(4) 0.3290(2) 0.0717(7) Uani d . 1
H H2A 0.4200 0.0138 0.3847 0.086 Uiso calc R 1
C C3 0.0348(4) -0.1369(3) 0.32151(19) 0.0557(6) Uani d . 1
C C4 -0.1774(4) -0.1273(3) 0.2366(2) 0.0605(6) Uani d . 1
H H4A -0.3404 -0.2292 0.2293 0.073 Uiso calc R 1
C C5 -0.1573(4) 0.0278(3) 0.1621(2) 0.0564(5) Uani d . 1
H H5A -0.3045 0.0293 0.1055 0.068 Uiso calc R 1
C C6 0.0817(4) 0.1802(3) 0.17189(17) 0.0443(5) Uani d . 1
C C7 -0.0598(4) 0.4160(3) 0.03983(17) 0.0436(5) Uani d . 1
C C8 0.0099(6) -0.3095(4) 0.4012(2) 0.0764(7) Uani d . 1
H H8A 0.1778 -0.2896 0.4541 0.115 Uiso calc R 1
H H8B -0.0456 -0.4449 0.3407 0.115 Uiso calc R 1
H H8C -0.1184 -0.3037 0.4594 0.115 Uiso calc R 1
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 0.0487(8) 0.0613(9) 0.0786(10) 0.0212(6) 0.0166(6) 0.0409(7)
N1 0.0460(9) 0.0516(9) 0.0570(9) 0.0188(7) 0.0152(7) 0.0291(7)
C1 0.0499(11) 0.0807(15) 0.0791(14) 0.0181(10) 0.0114(10) 0.0495(13)
C2 0.0652(14) 0.0879(17) 0.0748(15) 0.0264(12) 0.0063(11) 0.0503(13)
C3 0.0786(14) 0.0511(11) 0.0497(11) 0.0282(10) 0.0197(9) 0.0237(9)
C4 0.0630(13) 0.0442(11) 0.0735(14) 0.0097(9) 0.0087(10) 0.0231(10)
C5 0.0577(12) 0.0465(11) 0.0644(12) 0.0134(9) -0.0012(9) 0.0214(9)
C6 0.0514(10) 0.0454(10) 0.0460(9) 0.0207(8) 0.0142(7) 0.0220(7)
C7 0.0472(10) 0.0426(9) 0.0462(9) 0.0161(7) 0.0097(7) 0.0184(7)
C8 0.112(2) 0.0605(14) 0.0680(14) 0.0308(13) 0.0183(13) 0.0356(11)
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_site_symmetry_3
_geom_angle
C7 N1 C6 . 127.64(15)
C7 N1 H1B . 116.2
C6 N1 H1B . 116.2
C6 C1 C2 . 120.4(2)
C6 C1 H1A . 119.8
C2 C1 H1A . 119.8
C3 C2 C1 . 121.7(2)
C3 C2 H2A . 119.2
C1 C2 H2A . 119.2
C2 C3 C4 . 116.88(18)
C2 C3 C8 . 121.4(2)
C4 C3 C8 . 121.7(2)
C3 C4 C5 . 122.43(19)
C3 C4 H4A . 118.8
C5 C4 H4A . 118.8
C6 C5 C4 . 119.66(18)
C6 C5 H5A . 120.2
C4 C5 H5A . 120.2
C1 C6 C5 . 118.99(17)
C1 C6 N1 . 117.84(17)
C5 C6 N1 . 123.12(17)
O1 C7 N1 . 126.80(16)
O1 C7 C7 2_565 121.19(19)
N1 C7 C7 2_565 112.01(19)
C3 C8 H8A . 109.5
C3 C8 H8B . 109.5
H8A C8 H8B . 109.5
C3 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
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 C7 . 1.222(2) yes
N1 C7 . 1.334(2) yes
N1 C6 . 1.418(2) yes
N1 H1B . 0.8600 ?
C1 C6 . 1.374(3) ?
C1 C2 . 1.382(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.375(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.377(3) ?
C3 C8 . 1.512(3) yes
C4 C5 . 1.380(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.375(3) ?
C5 H5A . 0.9300 ?
C7 C7 2_565 1.536(3) yes
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
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
N1 H1B O1 1_655 0.86 2.39 3.171(3) 151 yes
N1 H1B O1 2_565 0.86 2.26 2.676(2) 110 yes
C5 H5A O1 1_555 0.93 2.42 2.953(3) 116 yes
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_4
_geom_torsion
C6 C1 C2 C3 . -0.4(4)
C1 C2 C3 C4 . 0.5(4)
C1 C2 C3 C8 . 179.6(2)
C2 C3 C4 C5 . -0.2(3)
C8 C3 C4 C5 . -179.3(2)
C3 C4 C5 C6 . -0.2(3)
C2 C1 C6 C5 . 0.0(3)
C2 C1 C6 N1 . -177.3(2)
C4 C5 C6 C1 . 0.4(3)
C4 C5 C6 N1 . 177.52(18)
C7 N1 C6 C1 . -158.5(2)
C7 N1 C6 C5 . 24.3(3)
C6 N1 C7 O1 . 2.4(3)
C6 N1 C7 C7 2_565 -178.22(18)
