##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for 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. 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/  #
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#                                                                            #
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data_global
_audit_creation_method     'SHELXL97 CIF, edited IUCr template'
_journal_date_recd_electronic     2007-02-05
_journal_date_accepted     2007-05-13
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2007
_journal_volume     63
_journal_issue      7
_journal_page_first     o392
_journal_page_last     o394
_journal_paper_category     FO
_journal_coeditor_code     FA3076
_publ_contact_author_name     'Dr P.A. Crooks'
_publ_contact_author_address
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
_publ_contact_author_email     pcrooks@uky.edu
_publ_contact_author_fax     '859 257 2585'
_publ_contact_author_phone     '859 257 1718'
_publ_section_title
;
(4-Methoxy-3-nitrobenzylideneamino)guanidinium chloride
;
loop_
    _publ_author_name
    _publ_author_address
    'Ring, Joshua R.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington
KY 40506
USA
;
    'Crooks, Peter A.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(4-Methoxy-3-nitrobenzylideneamino)guanidinium chloride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H12 N5 O3 +, Cl -'
_chemical_formula_sum     'C9 H12 Cl N5 O3'
_chemical_formula_iupac     'C9 H12 N5 O3 +, Cl -'
_chemical_formula_weight     273.69
_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     16.7260(4)
_cell_length_b     5.13840(10)
_cell_length_c     14.0045(5)
_cell_angle_alpha     90.00
_cell_angle_beta     93.1793(13)
_cell_angle_gamma     90.00
_cell_volume     1201.76(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3023
_cell_measurement_theta_min     1.0
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     'irregular block'
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.513
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     0.33
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.923
_exptl_absorpt_correction_T_max     0.976
_exptl_special_details
;
;
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean     18
_diffrn_reflns_number     4859
_diffrn_reflns_av_R_equivalents     0.024
_diffrn_reflns_av_sigmaI/netI     0.034
_diffrn_reflns_theta_min     1.22
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     .995
_diffrn_measured_fraction_theta_full     .995
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2744
_reflns_number_gt     2220
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.055
_refine_ls_R_factor_gt     0.041
_refine_ls_wR_factor_gt     0.102
_refine_ls_wR_factor_ref     0.111
_refine_ls_goodness_of_fit_ref     1.07
_refine_ls_restrained_S_all     1.07
_refine_ls_number_reflns     2744
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0574P)²+0.6173P] 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     0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     .35
_refine_diff_density_min     -.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' .1484 .1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1999)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 1995)'
_computing_publication_material
;
SHELX97-2 (Sheldrick, 1997) and local procedures
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.59641(3) 0.07437(9) 1.11857(3) 0.02220(14) Uani d . 1 . .
    C C1 0.76199(10) 0.2368(3) 0.83533(12) 0.0173(3) Uani d . 1 . .
    C C2 0.77609(10) 0.2913(4) 0.93282(12) 0.0186(4) Uani d . 1 . .
    H H2 0.7486 0.1981 0.9796 0.022 Uiso calc R 1 . .
    C C3 0.83035(10) 0.4821(4) 0.95963(11) 0.0193(4) Uani d . 1 . .
    C C4 0.87253(10) 0.6281(3) 0.89483(12) 0.0189(4) Uani d . 1 . .
    C C5 0.85614(10) 0.5785(4) 0.79767(12) 0.0197(4) Uani d . 1 . .
    H H5 0.8825 0.6756 0.7510 0.024 Uiso calc R 1 . .
    C C6 0.80136(10) 0.3871(4) 0.76958(12) 0.0195(4) Uani d . 1 . .
    H H6 0.7903 0.3573 0.7032 0.023 Uiso calc R 1 . .
    C C7 0.70580(10) 0.0348(4) 0.80221(12) 0.0183(4) Uani d . 1 . .
    H H7 0.6938 0.0126 0.7356 0.022 Uiso calc R 1 . .
    N N8 0.67259(8) -0.1127(3) 0.86196(10) 0.0180(3) Uani d . 1 . .
    N N9 0.61946(8) -0.2926(3) 0.82169(10) 0.0185(3) Uani d . 1 . .
    H H9 0.6080 -0.2945 0.7596 0.022 Uiso calc R 1 . .
    C C10 0.58556(10) -0.4654(4) 0.87971(12) 0.0186(4) Uani d . 1 . .
    N N11 0.54255(9) -0.6545(3) 0.83821(11) 0.0224(3) Uani d . 1 . .
    H H11A 0.5191(4) -0.7661(19) 0.8725(6) 0.027 Uiso d . 1 . .
    H H11B 0.53819(12) -0.6653(4) 0.7771(10) 0.027 Uiso d . 1 . .
    N N12 0.59436(9) -0.4392(3) 0.97324(10) 0.0205(3) Uani d . 1 . .
    H H12A 0.5729(4) -0.5416(19) 1.0080(7) 0.025 Uiso d . 1 . .
    H H12B 0.6212(5) -0.321(2) 0.9963(4) 0.025 Uiso d . 1 . .
    N N13 0.84128(9) 0.5450(3) 1.06182(10) 0.0219(3) Uani d . 1 . .
    O O14 0.78203(9) 0.6130(4) 1.10253(10) 0.0408(4) Uani d . 1 . .
    O O15 0.90798(8) 0.5240(3) 1.10144(9) 0.0323(3) Uani d . 1 . .
    O O16 0.92256(7) 0.8137(3) 0.93170(9) 0.0231(3) Uani d . 1 . .
    C C17 0.96690(11) 0.9628(4) 0.86592(13) 0.0258(4) Uani d . 1 . .
    H H17A 1.0002 0.8458 0.8297 0.039 Uiso calc R 1 . .
    H H17B 1.0012 1.0883 0.9015 0.039 Uiso calc R 1 . .
    H H17C 0.9296 1.0562 0.8217 0.039 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
    Cl1 0.0288(2) 0.0232(2) 0.0145(2) -0.00187(18) 0.00039(16) 0.00218(17)
    C1 0.0180(8) 0.0190(9) 0.0150(8) 0.0020(7) 0.0010(6) 0.0006(7)
    C2 0.0195(8) 0.0210(9) 0.0155(8) 0.0007(7) 0.0019(6) 0.0028(7)
    C3 0.0230(9) 0.0228(9) 0.0122(8) 0.0034(7) 0.0004(7) -0.0010(7)
    C4 0.0184(8) 0.0190(9) 0.0193(8) 0.0008(7) 0.0006(7) 0.0001(7)
    C5 0.0212(8) 0.0224(9) 0.0157(8) 0.0016(7) 0.0032(7) 0.0032(7)
    C6 0.0219(8) 0.0234(9) 0.0131(7) 0.0032(7) 0.0012(6) -0.0002(7)
    C7 0.0199(8) 0.0224(9) 0.0126(8) 0.0022(7) 0.0003(6) -0.0003(7)
    N8 0.0180(7) 0.0213(8) 0.0145(7) 0.0000(6) 0.0005(5) -0.0014(6)
    N9 0.0215(7) 0.0220(8) 0.0116(6) -0.0031(6) -0.0016(5) -0.0005(6)
    C10 0.0167(8) 0.0213(9) 0.0177(8) 0.0019(7) 0.0008(6) 0.0008(7)
    N11 0.0261(8) 0.0232(8) 0.0179(7) -0.0031(6) 0.0017(6) 0.0003(6)
    N12 0.0249(8) 0.0225(8) 0.0143(7) -0.0039(6) 0.0020(6) 0.0015(6)
    N13 0.0265(8) 0.0243(8) 0.0147(7) -0.0034(6) -0.0003(6) 0.0006(6)
    O14 0.0352(8) 0.0666(12) 0.0214(7) -0.0008(8) 0.0083(6) -0.0131(7)
    O15 0.0329(8) 0.0430(9) 0.0201(7) -0.0003(7) -0.0074(6) 0.0012(6)
    O16 0.0262(6) 0.0241(7) 0.0190(6) -0.0059(5) 0.0006(5) 0.0004(5)
    C17 0.0252(9) 0.0277(10) 0.0244(9) -0.0064(8) -0.0002(7) 0.0049(8)
_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 C6 . 1.395(2) ?
    C1 C2 . 1.401(2) ?
    C1 C7 . 1.459(2) Y
    C2 C3 . 1.374(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.398(2) ?
    C3 N13 . 1.469(2) y
    C4 O16 . 1.352(2) y
    C4 C5 . 1.396(2) ?
    C5 C6 . 1.386(3) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 N8 . 1.279(2) y
    C7 H7 . 0.9500 ?
    N8 N9 . 1.381(2) y
    N9 C10 . 1.350(2) y
    N9 H9 . 0.8800 ?
    C10 N12 . 1.317(2) y
    C10 N11 . 1.324(2) y
    N11 H11A . 0.856(17) ?
    N11 H11B . 0.856(17) ?
    N12 H12A . 0.813(18) ?
    N12 H12B . 0.813(18) ?
    N13 O14 . 1.221(2) y
    N13 O15 . 1.223(2) ?
    O16 C17 . 1.436(2) y
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
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
    C6 C1 C2 . . 118.21(16) ?
    C6 C1 C7 . . 120.24(15) ?
    C2 C1 C7 . . 121.52(15) y
    C3 C2 C1 . . 118.81(16) ?
    C3 C2 H2 . . 120.6 ?
    C1 C2 H2 . . 120.6 ?
    C2 C3 C4 . . 123.70(15) ?
    C2 C3 N13 . . 117.91(15) ?
    C4 C3 N13 . . 118.30(16) y
    O16 C4 C5 . . 125.77(16) y
    O16 C4 C3 . . 117.04(15) y
    C5 C4 C3 . . 117.10(16) ?
    C6 C5 C4 . . 119.79(16) ?
    C6 C5 H5 . . 120.1 ?
    C4 C5 H5 . . 120.1 ?
    C5 C6 C1 . . 122.30(15) ?
    C5 C6 H6 . . 118.9 ?
    C1 C6 H6 . . 118.9 ?
    N8 C7 C1 . . 120.63(15) y
    N8 C7 H7 . . 119.7 ?
    C1 C7 H7 . . 119.7 ?
    C7 N8 N9 . . 115.00(14) y
    C10 N9 N8 . . 118.48(14) y
    C10 N9 H9 . . 120.8 ?
    N8 N9 H9 . . 120.8 ?
    N12 C10 N11 . . 122.66(16) ?
    N12 C10 N9 . . 120.27(16) ?
    N11 C10 N9 . . 117.05(15) y
    C10 N11 H11A . . 120.0(6) ?
    C10 N11 H11B . . 120.0(2) ?
    H11A N11 H11B . . 120.0(6) ?
    C10 N12 H12A . . 120.0(7) ?
    C10 N12 H12B . . 120.0(5) ?
    H12A N12 H12B . . 119.9(8) ?
    O14 N13 O15 . . 123.85(15) ?
    O14 N13 C3 . . 117.22(14) ?
    O15 N13 C3 . . 118.92(15) ?
    C4 O16 C17 . . 117.53(13) ?
    O16 C17 H17A . . 109.5 ?
    O16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . -2.7(3) ?
    C7 C1 C2 C3 . . . . 179.31(16) ?
    C1 C2 C3 C4 . . . . 0.4(3) ?
    C1 C2 C3 N13 . . . . 177.02(15) ?
    C2 C3 C4 O16 . . . . 178.42(16) ?
    N13 C3 C4 O16 . . . . 1.8(2) ?
    C2 C3 C4 C5 . . . . 1.7(3) ?
    N13 C3 C4 C5 . . . . -174.92(15) ?
    O16 C4 C5 C6 . . . . -177.85(16) ?
    C3 C4 C5 C6 . . . . -1.4(3) ?
    C4 C5 C6 C1 . . . . -0.9(3) ?
    C2 C1 C6 C5 . . . . 3.0(3) ?
    C7 C1 C6 C5 . . . . -178.99(16) ?
    C6 C1 C7 N8 . . . . 176.38(16) ?
    C2 C1 C7 N8 . . . . -5.7(3) y
    C1 C7 N8 N9 . . . . 178.78(14) ?
    C7 N8 N9 C10 . . . . 176.16(15) ?
    N8 N9 C10 N12 . . . . 9.3(2) y
    N8 N9 C10 N11 . . . . -172.09(14) y
    C2 C3 N13 O14 . . . . -57.4(2) y
    C4 C3 N13 O14 . . . . 119.4(2) ?
    C2 C3 N13 O15 . . . . 121.72(19) ?
    C4 C3 N13 O15 . . . . -61.5(2) y
    C5 C4 O16 C17 . . . . -4.3(3) ?
    C3 C4 O16 C17 . . . . 179.29(16) y
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
    N9 H9 Cl1 4 0.88 2.44 3.1961(14) 144.0
    N11 H11A Cl1 3_647 0.857(9) 2.507(8) 3.2524(16) 146.0
    N11 H11B Cl1 4 0.857(14) 2.517(12) 3.2787(16) 148.6
    N12 H12A Cl1 1_545 0.814(9) 2.526(10) 3.2223(16) 144.4
    N12 H12B Cl1 . 0.812(9) 2.704(9) 3.3315(16) 135.5(7)
