##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-tert-Butyl-4,6-dinitrophenol
;
_chemical_formula_moiety     'C10 H12 N2 O5'
_chemical_formula_sum     'C10 H12 N2 O5'
_chemical_formula_iupac     'C10 H12 N2 O5'
_chemical_formula_weight     240.22
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     9.974(2)
_cell_length_b     10.575(2)
_cell_length_c     11.547(2)
_cell_angle_alpha     90.00
_cell_angle_beta     112.90(3)
_cell_angle_gamma     90.00
_cell_volume     1122.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     52
_cell_measurement_theta_min     4.29
_cell_measurement_theta_max     18.06
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.06
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.422
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     504
_exptl_absorpt_coefficient_mu     0.116
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker--Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     5908
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0498
_diffrn_reflns_theta_min     2.72
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.899
_diffrn_measured_fraction_theta_full     0.899
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     5912
_reflns_number_gt     4502
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0775
_refine_ls_R_factor_gt     0.0555
_refine_ls_wR_factor_gt     0.1501
_refine_ls_wR_factor_ref     0.1647
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     5912
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.1108P)²] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.027
_refine_ls_shift/su_mean     0.003
_refine_diff_density_max     0.362
_refine_diff_density_min     -0.343
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.033(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_cell_refinement     'DENZO and COLLECT'
_computing_data_reduction
                   'DENZO and SCALEPACK (Otwinowski & Minor, 1997), and COLLECT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                'ORTEP-3 for Windows (Farrugia, 1997) and PLUTON94 (Spek, 1994)'
_computing_publication_material     SHELXL97
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1 0.08422(16) 0.24756(16) 0.01103(17) 0.0175(4) Uani d . 1 . . C
    O11 0.08686(12) 0.34527(12) -0.06166(12) 0.0252(4) Uani d . 1 . . O
    H11 0.0059 0.3778 -0.0918 0.038 Uiso calc R 1 . . H
    C2 0.21649(17) 0.17828(16) 0.07515(17) 0.0167(4) Uani d . 1 . . C
    C21 0.35876(16) 0.21422(16) 0.05852(18) 0.0199(5) Uani d . 1 . . C
    C22 0.33651(18) 0.19937(18) -0.08108(18) 0.0273(5) Uani d . 1 . . C
    H22A 0.2582 0.2530 -0.1322 0.041 Uiso calc R 1 . . H
    H22B 0.3133 0.1129 -0.1064 0.041 Uiso calc R 1 . . H
    H22C 0.4242 0.2229 -0.0913 0.041 Uiso calc R 1 . . H
    C23 0.40487(19) 0.35174(18) 0.1040(2) 0.0311(5) Uani d . 1 . . C
    H23A 0.4939 0.3718 0.0944 0.047 Uiso calc R 1 . . H
    H23B 0.4193 0.3591 0.1909 0.047 Uiso calc R 1 . . H
    H23C 0.3299 0.4093 0.0547 0.047 Uiso calc R 1 . . H
    C24 0.48590(18) 0.12544(18) 0.1379(2) 0.0291(5) Uani d . 1 . . C
    H24A 0.4601 0.0393 0.1130 0.044 Uiso calc R 1 . . H
    H24B 0.5040 0.1349 0.2254 0.044 Uiso calc R 1 . . H
    H24C 0.5720 0.1474 0.1243 0.044 Uiso calc R 1 . . H
    C3 0.21111(17) 0.07892(16) 0.15038(17) 0.0182(4) Uani d . 1 . . C
    H3 0.2946 0.0313 0.1915 0.022 Uiso calc R 1 . . H
    C4 0.08200(17) 0.04759(15) 0.16662(18) 0.0187(4) Uani d . 1 . . C
    N41 0.08388(15) -0.05678(14) 0.25181(15) 0.0225(4) Uani d . 1 . . N
    O41 0.18873(14) -0.13023(13) 0.28710(14) 0.0362(4) Uani d . 1 . . O
    O42 -0.02105(13) -0.06679(11) 0.28282(13) 0.0284(4) Uani d . 1 . . O
    C5 -0.04623(18) 0.11166(16) 0.10471(17) 0.0176(4) Uani d . 1 . . C
    H5 -0.1311 0.0898 0.1152 0.021 Uiso calc R 1 . . H
    C6 -0.04398(16) 0.20999(15) 0.02624(17) 0.0179(4) Uani d . 1 . . C
    N61 -0.18396(15) 0.27369(15) -0.04410(15) 0.0231(4) Uani d . 1 . . N
    O61 -0.29647(11) 0.22493(13) -0.04595(12) 0.0320(4) Uani d . 1 . . O
    O62 -0.18238(12) 0.37669(12) -0.09758(13) 0.0306(4) Uani d . 1 . . O
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
    C1 0.0198(9) 0.0146(9) 0.0188(12) -0.0009(9) 0.0085(8) -0.0030(8)
    O11 0.0178(6) 0.0247(8) 0.0322(9) 0.0036(6) 0.0087(6) 0.0090(6)
    C2 0.0177(9) 0.0173(9) 0.0157(12) -0.0001(8) 0.0071(8) -0.0029(8)
    C21 0.0120(8) 0.0214(10) 0.0258(13) 0.0017(8) 0.0067(8) -0.0004(8)
    C22 0.0183(9) 0.0354(12) 0.0305(14) 0.0011(9) 0.0122(9) 0.0051(9)
    C23 0.0267(10) 0.0317(12) 0.0373(15) -0.0066(10) 0.0151(10) -0.0009(10)
    C24 0.0185(10) 0.0364(12) 0.0338(14) 0.0041(9) 0.0118(9) 0.0052(9)
    C3 0.0154(9) 0.0186(10) 0.0180(12) 0.0030(8) 0.0036(8) -0.0051(7)
    C4 0.0212(9) 0.0140(9) 0.0214(12) -0.0030(8) 0.0088(8) -0.0044(8)
    N41 0.0255(8) 0.0208(8) 0.0196(11) -0.0044(8) 0.0072(8) -0.0028(7)
    O41 0.0333(8) 0.0328(8) 0.0439(11) 0.0107(7) 0.0163(7) 0.0148(7)
    O42 0.0298(7) 0.0277(7) 0.0330(9) -0.0074(6) 0.0180(7) 0.0012(6)
    C5 0.0168(9) 0.0208(10) 0.0159(12) -0.0030(8) 0.0072(8) -0.0054(8)
    C6 0.0129(8) 0.0181(9) 0.0191(12) 0.0056(8) 0.0022(8) -0.0012(8)
    N61 0.0176(8) 0.0264(10) 0.0249(11) 0.0027(8) 0.0077(7) -0.0015(7)
    O61 0.0148(6) 0.0453(9) 0.0369(10) -0.0020(7) 0.0113(6) 0.0051(7)
    O62 0.0221(7) 0.0243(8) 0.0430(10) 0.0055(6) 0.0102(7) 0.0087(7)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 O11 . 1.338(2) ?
    C1 C6 . 1.414(2) ?
    C1 C2 . 1.437(2) ?
    O11 H11 . 0.82 ?
    C2 C3 . 1.378(2) ?
    C2 C21 . 1.551(2) ?
    C21 C22 . 1.547(3) ?
    C21 C23 . 1.554(3) ?
    C21 C24 . 1.557(3) ?
    C22 H22A . 0.96 ?
    C22 H22B . 0.96 ?
    C22 H22C . 0.96 ?
    C23 H23A . 0.96 ?
    C23 H23B . 0.96 ?
    C23 H23C . 0.96 ?
    C24 H24A . 0.96 ?
    C24 H24B . 0.96 ?
    C24 H24C . 0.96 ?
    C3 C4 . 1.411(2) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.376(2) ?
    C4 N41 . 1.474(2) ?
    N41 O42 . 1.2355(18) ?
    N41 O41 . 1.2375(18) ?
    C5 C6 . 1.385(2) ?
    C5 H5 . 0.93 ?
    C6 N61 . 1.477(2) ?
    N61 O61 . 1.2276(16) ?
    N61 O62 . 1.2552(18) ?
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_3
    _geom_angle
    _geom_angle_publ_flag
    O11 C1 C6 . . 122.31(14) ?
    O11 C1 C2 . . 118.60(14) ?
    C6 C1 C2 . . 119.08(15) ?
    C1 O11 H11 . . 109.5 ?
    C3 C2 C1 . . 117.42(15) ?
    C3 C2 C21 . . 121.79(15) ?
    C1 C2 C21 . . 120.79(15) ?
    C22 C21 C2 . . 109.68(14) ?
    C22 C21 C23 . . 110.52(15) ?
    C2 C21 C23 . . 110.63(15) ?
    C22 C21 C24 . . 107.82(15) ?
    C2 C21 C24 . . 110.72(15) ?
    C23 C21 C24 . . 107.41(15) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C21 C23 H23A . . 109.5 ?
    C21 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C21 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C21 C24 H24A . . 109.5 ?
    C21 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C21 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C2 C3 C4 . . 121.63(16) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C5 C4 C3 . . 121.80(16) ?
    C5 C4 N41 . . 118.90(15) ?
    C3 C4 N41 . . 119.30(15) ?
    O42 N41 O41 . . 123.60(15) ?
    O42 N41 C4 . . 117.74(14) ?
    O41 N41 C4 . . 118.66(14) ?
    C4 C5 C6 . . 117.45(16) ?
    C4 C5 H5 . . 121.3 ?
    C6 C5 H5 . . 121.3 ?
    C5 C6 C1 . . 122.54(15) ?
    C5 C6 N61 . . 116.73(15) ?
    C1 C6 N61 . . 120.72(15) ?
    O61 N61 O62 . . 122.85(14) ?
    O61 N61 C6 . . 118.70(15) ?
    O62 N61 C6 . . 118.44(14) ?
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
    O11 H11 O62 . 0.82 1.85 2.5743(17) 146
    O11 H11 O42 4_565 0.82 2.42 2.8926(19) 118
data_global
_journal_date_recd_electronic     2004-06-10
_journal_date_accepted     2004-06-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      8
_journal_page_first     o1288
_journal_page_last     o1289
_journal_paper_category     EO
_publ_contact_author
;
Dr Daniel E. Lynch
School of Science and the Environment
Coventry University
Coventry CV1 5FB
UK
;
_publ_contact_author_email     apx106@coventry.ac.uk
_publ_contact_author_fax     ' 44 (0)24 7683 8702 '
_publ_contact_author_phone     ' 44 (0)24 7683 8019 '
_publ_section_title
;
2-tert-Butyl-4,6-dinitrophenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Daniel E. Lynch'
;
School of Science and the Environment
Coventry University
Coventry CV1 5FB
England
;
    'Ian McClenaghan'
;
Key Organics Ltd
Highfield Industrial Estate
Camelford
Cornwall PL32 9QZ
England
;
