##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_1
_audit_creation_method     'from TEXRAY.INF file'
_journal_date_recd_electronic     1996-10-01
_journal_date_accepted     1997-02-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     1997
_journal_volume     53
_journal_issue     6
_journal_page_first     744
_journal_page_last     746
_journal_paper_category     FO
_journal_coeditor_code     AB1426
_publ_contact_author
;
Alan R. Kennedy
Dept. of P. & A. Chemistry
University of Strathclyde
295 Cathedral Street
Glasgow G1 1XL
Scotland
;
_publ_contact_author_email     'a.r.kennedy@ccsun.strath.ac.uk'
_publ_contact_author_fax     ' 0141 552 5664'
_publ_contact_author_phone     ' 0141 552 4400 ext 4241 '
_publ_section_title
;
N,N-Diacetyl-2,5-dimethyl-6-nitroaniline
;
_publ_section_title_footnote
;
Alternative name: 3,6-dimethyl-2-nitrophenyldiacetamide.
;
loop_
    _publ_author_name
    _publ_author_address
    'Kennedy, Alan R. '
;
Department of Pure & Applied Chemistry
University of Strathclyde
Glasgow G1 1XL
Scotland
;
    'Khalaf, Abedawn I. '
;
Department of Pure & Applied Chemistry
University of Strathclyde
Glasgow G1 1XL
Scotland
;
data_II
_chemical_formula_moiety     'C12 H14 N2 O4'
_chemical_formula_sum     'C12 H14 N2 O4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     250.25
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    '   +x,   +y,   +z'
    '1/2-x,   -y,1/2+z'
    '1/2+x,1/2-y,   -z'
    '   -x,1/2+y,1/2-z'
_cell_length_a     12.231(2)
_cell_length_b     13.643(3)
_cell_length_c     7.733(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1290.3(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     19
_cell_measurement_theta_min     9.2
_cell_measurement_theta_max     12.1
_cell_measurement_temperature     295
_exptl_crystal_description     'needle'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.288
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'none'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     none
_diffrn_ambient_temperature     295
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Rigaku AFC-7S'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     2500
_diffrn_reflns_av_R_equivalents     0.026
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_theta_min     2.5
_diffrn_reflns_theta_max     25.0
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_decay_%     -5.97
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    -4 3 2
    -4 -3 2
    -5 2 1
_refine_special_details     'none'
_reflns_number_total     2291
_reflns_number_observed     1650
_reflns_observed_criterion     'I>0.5\s(I)'
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1372
_refine_ls_R_factor_obs     0.0682
_refine_ls_wR_factor_all     0.0537
_refine_ls_wR_factor_obs     0.0456
_refine_ls_goodness_of_fit_obs     1.200
_refine_ls_number_reflns     1650
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     'w = 1/\s^2^(F)'
_refine_ls_shift/esd_max     0.0002
_refine_ls_shift/esd_mean     ?
_refine_diff_density_max     0.25
_refine_diff_density_min     -0.37
_refine_ls_extinction_method     'Zachariasen type 2 Gaussian isotropic'
_refine_ls_extinction_coef     3.0E-6(3)
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_number_in_cell
    _atom_type_oxidation_number
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 48 0 0.003 0.002 'International Tables'
    H 56 0 0.000 0.000 'International Tables'
    N 8 0 0.006 0.003 'International Tables'
    O 16 0 0.011 0.006 'International Tables'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1985)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction     'TEXSAN (Molecular Structure Corporation, 1993)'
_computing_structure_solution     'SIR (Burla et al., 1989)'
_computing_structure_refinement     TEXSAN
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     TEXSAN
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_calc_attached_atom
    O(1) 0.7667(2) 0.2440(2) 0.4446(3) 0.071(2) Uani ? ?
    O(2) 0.8728(2) 0.0902(2) 0.8592(3) 0.078(2) Uani ? ?
    O(3) 0.5350(2) 0.3286(2) 0.6157(5) 0.092(3) Uani ? ?
    O(4) 0.5899(2) 0.2426(2) 0.8290(4) 0.095(3) Uani ? ?
    N(1) 0.8108(2) 0.2278(2) 0.7238(3) 0.039(2) Uani ? ?
    N(2) 0.5994(2) 0.3107(2) 0.7300(5) 0.061(3) Uani ? ?
    C(1) 0.7982(3) 0.3327(2) 0.7404(4) 0.042(3) Uani ? ?
    C(2) 0.8905(3) 0.3916(2) 0.7472(4) 0.048(3) Uani ? ?
    C(3) 0.8739(3) 0.4916(2) 0.7717(5) 0.061(3) Uani ? ?
    C(4) 0.7719(4) 0.5314(2) 0.7849(5) 0.060(3) Uani ? ?
    C(5) 0.6781(3) 0.4750(2) 0.7690(4) 0.052(3) Uani ? ?
    C(6) 0.6949(3) 0.3752(2) 0.7489(4) 0.044(3) Uani ? ?
    C(7) 1.0039(3) 0.3493(3) 0.7323(6) 0.071(3) Uani ? ?
    C(8) 0.5659(3) 0.5207(3) 0.7836(6) 0.077(3) Uani ? ?
    C(9) 0.7897(3) 0.1892(2) 0.5594(5) 0.047(3) Uani ? ?
    C(10) 0.7936(4) 0.0809(3) 0.5289(5) 0.071(3) Uani ? ?
    C(11) 0.8394(3) 0.1724(3) 0.8717(5) 0.051(3) Uani ? ?
    C(12) 0.8254(3) 0.2220(3) 1.0412(4) 0.068(3) Uani ? ?
    H(1) 0.9364 0.5340 0.7795 0.0729 Uiso calc ?
    H(2) 0.7649 0.6005 0.8058 0.0721 Uiso calc ?
    H(3) 1.0242 0.3196 0.8401 0.0857 Uiso calc ?
    H(4) 1.0052 0.3008 0.6424 0.0857 Uiso calc ?
    H(5) 1.0547 0.4007 0.7049 0.0857 Uiso calc ?
    H(6) 0.5344 0.5271 0.6705 0.0919 Uiso calc ?
    H(7) 0.5720 0.5842 0.8361 0.0919 Uiso calc ?
    H(8) 0.5200 0.4797 0.8537 0.0919 Uiso calc ?
    H(9) 0.7713 0.0670 0.4124 0.0852 Uiso calc ?
    H(10) 0.8669 0.0577 0.5464 0.0852 Uiso calc ?
    H(11) 0.7453 0.0485 0.6082 0.0852 Uiso calc ?
    H(12) 0.8346 0.1751 1.1327 0.0815 Uiso calc ?
    H(13) 0.7535 0.2500 1.0478 0.0815 Uiso calc ?
    H(14) 0.8791 0.2729 1.0527 0.0815 Uiso calc ?
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
    O(1) 0.114(2) 0.055(2) 0.0430(10)
                                    0.012(2) -0.0070(10)
                                                       -0.0030(10)
    O(2) 0.108(2) 0.055(2) 0.071(2) 0.027(2) -0.002(2) 0.0110(10)
    O(3) 0.069(2) 0.103(2) 0.102(2) -0.004(2) -0.027(2) -0.004(2)
    O(4) 0.062(2) 0.083(2) 0.139(3) -0.014(2) 0.005(2) 0.034(2)
    N(1) 0.045(2) 0.0320(10)
                           0.040(2) 0.0010(10)
                                             -0.0010(10)
                                                       -0.0020(10)
    N(2) 0.048(2) 0.057(2) 0.078(3) 0.008(2) 0.005(2) -0.002(2)
    C(1) 0.049(2) 0.037(2) 0.040(2) 0.002(2) 0.006(2) 0.000(2)
    C(2) 0.052(2) 0.045(2) 0.048(2) -0.008(2) -0.003(2) -0.001(2)
    C(3) 0.073(3) 0.042(2) 0.068(3) -0.012(2) -0.002(2) -0.005(2)
    C(4) 0.084(3) 0.040(2) 0.056(2) 0.001(2) -0.007(2) -0.009(2)
    C(5) 0.066(3) 0.048(2) 0.043(2) 0.010(2) 0.002(2) -0.003(2)
    C(6) 0.045(2) 0.040(2) 0.046(2) -0.004(2) 0.002(2) 0.000(2)
    C(7) 0.052(2) 0.069(3) 0.093(3) -0.005(2) 0.001(2) 0.004(2)
    C(8) 0.087(3) 0.062(2) 0.081(3) 0.028(2) 0.005(3) -0.007(2)
    C(9) 0.054(2) 0.040(2) 0.048(2) 0.001(2) 0.002(2) -0.003(2)
    C(10) 0.093(3) 0.047(2) 0.073(3) 0.002(2) -0.011(2) -0.011(2)
    C(11) 0.051(2) 0.050(2) 0.053(2) 0.000(2) 0.004(2) 0.007(2)
    C(12) 0.081(3) 0.077(3) 0.045(2) 0.007(2) -0.004(2) 0.003(2)
_geom_special_details     ?
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
    O(1) C(9) ? ? 1.195(4) yes
    O(2) C(11) ? ? 1.197(4) yes
    O(3) N(2) ? ? 1.209(4) yes
    O(4) N(2) ? ? 1.209(4) yes
    N(1) C(1) ? ? 1.446(4) yes
    N(1) C(9) ? ? 1.400(4) yes
    N(1) C(11) ? ? 1.414(4) yes
    N(2) C(6) ? ? 1.470(4) yes
    C(1) C(2) ? ? 1.387(4) yes
    C(1) C(6) ? ? 1.392(4) yes
    C(2) C(3) ? ? 1.392(4) no
    C(2) C(7) ? ? 1.507(5) no
    C(3) C(4) ? ? 1.364(6) no
    C(4) C(5) ? ? 1.388(5) no
    C(5) C(6) ? ? 1.386(4) no
    C(5) C(8) ? ? 1.511(5) no
    C(9) C(10) ? ? 1.497(5) yes
    C(11) C(12) ? ? 1.485(5) yes
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C(1) N(1) C(9) ? ? ? 115.6(3) yes
    C(1) N(1) C(11) ? ? ? 118.9(3) yes
    C(9) N(1) C(11) ? ? ? 125.4(3) yes
    O(3) N(2) O(4) ? ? ? 123.8(3) yes
    O(3) N(2) C(6) ? ? ? 117.9(3) yes
    O(4) N(2) C(6) ? ? ? 118.3(3) yes
    N(1) C(1) C(2) ? ? ? 119.4(3) yes
    N(1) C(1) C(6) ? ? ? 120.9(3) yes
    C(2) C(1) C(6) ? ? ? 119.7(3) yes
    C(1) C(2) C(3) ? ? ? 117.1(3) yes
    C(1) C(2) C(7) ? ? ? 121.6(3) no
    C(3) C(2) C(7) ? ? ? 121.3(3) no
    C(2) C(3) C(4) ? ? ? 122.3(4) yes
    C(3) C(4) C(5) ? ? ? 121.9(3) yes
    C(4) C(5) C(6) ? ? ? 115.6(3) yes
    C(4) C(5) C(8) ? ? ? 121.0(3) no
    C(6) C(5) C(8) ? ? ? 123.2(4) no
    N(2) C(6) C(1) ? ? ? 117.8(3) yes
    N(2) C(6) C(5) ? ? ? 118.8(3) yes
    C(1) C(6) C(5) ? ? ? 123.3(3) yes
    O(1) C(9) N(1) ? ? ? 118.9(3) yes
    O(1) C(9) C(10) ? ? ? 120.5(3) yes
    N(1) C(9) C(10) ? ? ? 120.5(3) yes
    O(2) C(11) N(1) ? ? ? 121.3(3) yes
    O(2) C(11) C(12) ? ? ? 122.5(3) yes
    N(1) C(11) C(12) ? ? ? 116.2(3) 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
    _geom_torsion_publ_flag
    C(2) C(1) N(1) C(9) -104.0(4) yes
    C(2) C(1) N(1) C(11) 77.9(4) yes
    C(10) C(9) N(1) C(11) 1.5(5) yes
    O(1) C(9) N(1) C(11) -179.7(3) yes
    O(2) C(11) N(1) C(9) 18.0(5) yes
    C(9) N(1) C(11) C(12) -162.1(3) yes
    O(3) N(2) C(6) C(1) -122.7(4) yes
    O(4) N(2) C(6) C(1) 57.0(4) yes
