# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Sundeep Rayat'
'Olajide Alawode'
'John Desper'

_publ_contact_author_name        'Sundeep Rayat'
_publ_contact_author_address     
;
Department of Chemistry
213 CBC Building
Kansas State University
Manhattan, KS 66506-0401
USA
;

_publ_contact_author_email       SUNDEEP@KSU.EDU

_publ_section_title              
;
Intermolecular interactions in the crystal structures of substituted tetrazolones
;

# Attachment 'allXray.cif'

data_oa0701m
_database_code_depnum_ccdc_archive 'CCDC 714340'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
HG-I1 N-(m-methoxyphenyl)tetrazolone
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C8 H8 N4 O2
;
_chemical_formula_sum            'C8 H8 N4 O2'
_chemical_formula_weight         192.18

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   12.414(11)
_cell_length_b                   19.068(16)
_cell_length_c                   7.190(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.28(2)
_cell_angle_gamma                90.00
_cell_volume                     1680(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4682
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      32.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26044
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         33.60
_reflns_number_total             6508
_reflns_number_gt                3772
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6508
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1707
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11_1 N 0.58202(8) 0.27149(5) 0.28509(15) 0.0284(2) Uani 1 1 d . . .
N12_1 N 0.49816(10) 0.31342(6) 0.20502(16) 0.0356(3) Uani 1 1 d . . .
N13_1 N 0.52788(10) 0.37630(6) 0.23570(17) 0.0395(3) Uani 1 1 d . . .
N14_1 N 0.62954(10) 0.37639(6) 0.33446(16) 0.0347(3) Uani 1 1 d . . .
H14_1 H 0.6652(13) 0.4168(9) 0.375(2) 0.042 Uiso 1 1 d . . .
C15_1 C 0.66785(11) 0.31135(6) 0.37184(18) 0.0293(3) Uani 1 1 d . . .
O15_1 O 0.75581(8) 0.29280(5) 0.46115(15) 0.0390(2) Uani 1 1 d . . .
C21_1 C 0.64290(11) 0.08487(6) 0.35410(18) 0.0309(3) Uani 1 1 d . . .
O21_1 O 0.73052(8) 0.04844(5) 0.44315(16) 0.0429(3) Uani 1 1 d . . .
C22_1 C 0.65604(11) 0.15667(6) 0.35876(18) 0.0303(3) Uani 1 1 d . . .
H22_1 H 0.7225 0.1772 0.4179 0.036 Uiso 1 1 calc R . .
C23_1 C 0.57072(10) 0.19796(6) 0.27585(17) 0.0263(2) Uani 1 1 d . . .
C24_1 C 0.47309(11) 0.16932(7) 0.18526(19) 0.0336(3) Uani 1 1 d . . .
H24_1 H 0.4149 0.1985 0.1284 0.040 Uiso 1 1 calc R . .
C25_1 C 0.46351(12) 0.09807(7) 0.1806(2) 0.0389(3) Uani 1 1 d . . .
H25_1 H 0.3978 0.0775 0.1181 0.047 Uiso 1 1 calc R . .
C26_1 C 0.54720(11) 0.05482(7) 0.2648(2) 0.0355(3) Uani 1 1 d . . .
H26_1 H 0.5388 0.0053 0.2611 0.043 Uiso 1 1 calc R . .
C27_1 C 0.71757(13) -0.02449(7) 0.4646(2) 0.0445(4) Uani 1 1 d . . .
H27A_1 H 0.7859 -0.0446 0.5304 0.067 Uiso 1 1 calc R . .
H27B_1 H 0.6989 -0.0463 0.3401 0.067 Uiso 1 1 calc R . .
H27C_1 H 0.6589 -0.0332 0.5380 0.067 Uiso 1 1 calc R . .
N11_2 N 0.92496(9) 0.50782(5) 0.67779(15) 0.0296(2) Uani 1 1 d . . .
N12_2 N 1.00518(10) 0.46592(6) 0.77011(17) 0.0390(3) Uani 1 1 d . . .
N13_2 N 0.97721(10) 0.40321(6) 0.73563(18) 0.0400(3) Uani 1 1 d . . .
N14_2 N 0.87958(9) 0.40262(5) 0.62272(16) 0.0340(3) Uani 1 1 d . . .
H14_2 H 0.8408(14) 0.3607(9) 0.574(2) 0.041 Uiso 1 1 d . . .
C15_2 C 0.84292(11) 0.46791(6) 0.58146(18) 0.0308(3) Uani 1 1 d . . .
O15_2 O 0.75756(9) 0.48614(5) 0.48175(16) 0.0453(3) Uani 1 1 d . . .
C21_2 C 0.86212(11) 0.69495(6) 0.62067(18) 0.0296(3) Uani 1 1 d . . .
O21_2 O 0.77412(8) 0.73163(5) 0.53551(15) 0.0429(3) Uani 1 1 d . . .
C22_2 C 0.85143(11) 0.62309(6) 0.60616(18) 0.0310(3) Uani 1 1 d . . .
H22_2 H 0.7869 0.6027 0.5387 0.037 Uiso 1 1 calc R . .
C23_2 C 0.93564(10) 0.58136(6) 0.69094(16) 0.0275(2) Uani 1 1 d . . .
C24_2 C 1.03151(11) 0.60959(7) 0.78931(19) 0.0340(3) Uani 1 1 d . . .
H24_2 H 1.0890 0.5802 0.8474 0.041 Uiso 1 1 calc R . .
C25_2 C 1.04024(12) 0.68104(7) 0.7997(2) 0.0363(3) Uani 1 1 d . . .
H25_2 H 1.1052 0.7013 0.8659 0.044 Uiso 1 1 calc R . .
C26_2 C 0.95704(11) 0.72468(7) 0.71625(19) 0.0341(3) Uani 1 1 d . . .
H26_2 H 0.9649 0.7742 0.7244 0.041 Uiso 1 1 calc R . .
C27_2 C 0.77595(13) 0.80514(7) 0.5602(2) 0.0407(3) Uani 1 1 d . . .
H27A_2 H 0.7082 0.8254 0.4926 0.061 Uiso 1 1 calc R . .
H27B_2 H 0.8384 0.8249 0.5104 0.061 Uiso 1 1 calc R . .
H27C_2 H 0.7825 0.8161 0.6947 0.061 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11_1 N12_1 1.3643(16) . ?
N11_1 C15_1 1.3740(17) . ?
N11_1 C23_1 1.4096(18) . ?
N12_1 N13_1 1.2634(18) . ?
N13_1 N14_1 1.3447(19) . ?
N14_1 C15_1 1.3398(18) . ?
N14_1 H14_1 0.912(17) . ?
C15_1 O15_1 1.2263(18) . ?
C21_1 O21_1 1.3606(17) . ?
C21_1 C22_1 1.379(2) . ?
C21_1 C26_1 1.381(2) . ?
O21_1 C27_1 1.4111(19) . ?
C22_1 C23_1 1.3761(19) . ?
C22_1 H22_1 0.9500 . ?
C23_1 C24_1 1.3918(19) . ?
C24_1 C25_1 1.364(2) . ?
C24_1 H24_1 0.9500 . ?
C25_1 C26_1 1.387(2) . ?
C25_1 H25_1 0.9500 . ?
C26_1 H26_1 0.9500 . ?
C27_1 H27A_1 0.9800 . ?
C27_1 H27B_1 0.9800 . ?
C27_1 H27C_1 0.9800 . ?
N11_2 N12_2 1.3629(17) . ?
N11_2 C15_2 1.3671(18) . ?
N11_2 C23_2 1.4103(19) . ?
N12_2 N13_2 1.2586(18) . ?
N13_2 N14_2 1.3457(19) . ?
N14_2 C15_2 1.3421(18) . ?
N14_2 H14_2 0.968(16) . ?
C15_2 O15_2 1.2300(18) . ?
C21_2 O21_2 1.3571(17) . ?
C21_2 C22_2 1.3790(19) . ?
C21_2 C26_2 1.3860(19) . ?
O21_2 C27_2 1.4126(19) . ?
C22_2 C23_2 1.3755(19) . ?
C22_2 H22_2 0.9500 . ?
C23_2 C24_2 1.3910(19) . ?
C24_2 C25_2 1.368(2) . ?
C24_2 H24_2 0.9500 . ?
C25_2 C26_2 1.385(2) . ?
C25_2 H25_2 0.9500 . ?
C26_2 H26_2 0.9500 . ?
C27_2 H27A_2 0.9800 . ?
C27_2 H27B_2 0.9800 . ?
C27_2 H27C_2 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12_1 N11_1 C15_1 110.53(12) . . ?
N12_1 N11_1 C23_1 119.97(11) . . ?
C15_1 N11_1 C23_1 129.46(11) . . ?
N13_1 N12_1 N11_1 107.51(12) . . ?
N12_1 N13_1 N14_1 108.43(11) . . ?
C15_1 N14_1 N13_1 112.17(11) . . ?
C15_1 N14_1 H14_1 125.5(11) . . ?
N13_1 N14_1 H14_1 122.3(11) . . ?
O15_1 C15_1 N14_1 129.01(12) . . ?
O15_1 C15_1 N11_1 129.65(12) . . ?
N14_1 C15_1 N11_1 101.34(12) . . ?
O21_1 C21_1 C22_1 114.40(12) . . ?
O21_1 C21_1 C26_1 124.73(13) . . ?
C22_1 C21_1 C26_1 120.86(12) . . ?
C21_1 O21_1 C27_1 117.25(11) . . ?
C23_1 C22_1 C21_1 118.55(12) . . ?
C23_1 C22_1 H22_1 120.7 . . ?
C21_1 C22_1 H22_1 120.7 . . ?
C22_1 C23_1 C24_1 121.98(12) . . ?
C22_1 C23_1 N11_1 119.00(11) . . ?
C24_1 C23_1 N11_1 119.01(11) . . ?
C25_1 C24_1 C23_1 117.93(12) . . ?
C25_1 C24_1 H24_1 121.0 . . ?
C23_1 C24_1 H24_1 121.0 . . ?
C24_1 C25_1 C26_1 121.70(13) . . ?
C24_1 C25_1 H25_1 119.2 . . ?
C26_1 C25_1 H25_1 119.2 . . ?
C21_1 C26_1 C25_1 118.96(13) . . ?
C21_1 C26_1 H26_1 120.5 . . ?
C25_1 C26_1 H26_1 120.5 . . ?
O21_1 C27_1 H27A_1 109.5 . . ?
O21_1 C27_1 H27B_1 109.5 . . ?
H27A_1 C27_1 H27B_1 109.5 . . ?
O21_1 C27_1 H27C_1 109.5 . . ?
H27A_1 C27_1 H27C_1 109.5 . . ?
H27B_1 C27_1 H27C_1 109.5 . . ?
N12_2 N11_2 C15_2 110.29(12) . . ?
N12_2 N11_2 C23_2 119.79(11) . . ?
C15_2 N11_2 C23_2 129.93(11) . . ?
N13_2 N12_2 N11_2 107.71(12) . . ?
N12_2 N13_2 N14_2 108.66(11) . . ?
C15_2 N14_2 N13_2 111.47(11) . . ?
C15_2 N14_2 H14_2 123.7(10) . . ?
N13_2 N14_2 H14_2 124.8(10) . . ?
O15_2 C15_2 N14_2 128.36(12) . . ?
O15_2 C15_2 N11_2 129.75(12) . . ?
N14_2 C15_2 N11_2 101.88(12) . . ?
O21_2 C21_2 C22_2 114.66(12) . . ?
O21_2 C21_2 C26_2 124.84(12) . . ?
C22_2 C21_2 C26_2 120.51(12) . . ?
C21_2 O21_2 C27_2 117.33(11) . . ?
C23_2 C22_2 C21_2 118.96(12) . . ?
C23_2 C22_2 H22_2 120.5 . . ?
C21_2 C22_2 H22_2 120.5 . . ?
C22_2 C23_2 C24_2 121.90(13) . . ?
C22_2 C23_2 N11_2 119.27(11) . . ?
C24_2 C23_2 N11_2 118.83(11) . . ?
C25_2 C24_2 C23_2 117.83(12) . . ?
C25_2 C24_2 H24_2 121.1 . . ?
C23_2 C24_2 H24_2 121.1 . . ?
C24_2 C25_2 C26_2 121.85(13) . . ?
C24_2 C25_2 H25_2 119.1 . . ?
C26_2 C25_2 H25_2 119.1 . . ?
C25_2 C26_2 C21_2 118.95(13) . . ?
C25_2 C26_2 H26_2 120.5 . . ?
C21_2 C26_2 H26_2 120.5 . . ?
O21_2 C27_2 H27A_2 109.5 . . ?
O21_2 C27_2 H27B_2 109.5 . . ?
H27A_2 C27_2 H27B_2 109.5 . . ?
O21_2 C27_2 H27C_2 109.5 . . ?
H27A_2 C27_2 H27C_2 109.5 . . ?
H27B_2 C27_2 H27C_2 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15_1 N11_1 N12_1 N13_1 0.70(15) . . . . ?
C23_1 N11_1 N12_1 N13_1 178.78(11) . . . . ?
N11_1 N12_1 N13_1 N14_1 -0.05(15) . . . . ?
N12_1 N13_1 N14_1 C15_1 -0.63(16) . . . . ?
N13_1 N14_1 C15_1 O15_1 -178.47(14) . . . . ?
N13_1 N14_1 C15_1 N11_1 0.99(14) . . . . ?
N12_1 N11_1 C15_1 O15_1 178.45(14) . . . . ?
C23_1 N11_1 C15_1 O15_1 0.6(2) . . . . ?
N12_1 N11_1 C15_1 N14_1 -1.01(14) . . . . ?
C23_1 N11_1 C15_1 N14_1 -178.85(12) . . . . ?
C22_1 C21_1 O21_1 C27_1 172.14(12) . . . . ?
C26_1 C21_1 O21_1 C27_1 -7.8(2) . . . . ?
O21_1 C21_1 C22_1 C23_1 -178.59(11) . . . . ?
C26_1 C21_1 C22_1 C23_1 1.4(2) . . . . ?
C21_1 C22_1 C23_1 C24_1 -1.17(19) . . . . ?
C21_1 C22_1 C23_1 N11_1 177.99(11) . . . . ?
N12_1 N11_1 C23_1 C22_1 -179.53(11) . . . . ?
C15_1 N11_1 C23_1 C22_1 -1.86(19) . . . . ?
N12_1 N11_1 C23_1 C24_1 -0.35(18) . . . . ?
C15_1 N11_1 C23_1 C24_1 177.33(12) . . . . ?
C22_1 C23_1 C24_1 C25_1 0.1(2) . . . . ?
N11_1 C23_1 C24_1 C25_1 -179.03(12) . . . . ?
C23_1 C24_1 C25_1 C26_1 0.8(2) . . . . ?
O21_1 C21_1 C26_1 C25_1 179.42(13) . . . . ?
C22_1 C21_1 C26_1 C25_1 -0.5(2) . . . . ?
C24_1 C25_1 C26_1 C21_1 -0.6(2) . . . . ?
C15_2 N11_2 N12_2 N13_2 0.15(16) . . . . ?
C23_2 N11_2 N12_2 N13_2 -179.55(12) . . . . ?
N11_2 N12_2 N13_2 N14_2 -0.28(16) . . . . ?
N12_2 N13_2 N14_2 C15_2 0.32(17) . . . . ?
N13_2 N14_2 C15_2 O15_2 179.50(14) . . . . ?
N13_2 N14_2 C15_2 N11_2 -0.21(15) . . . . ?
N12_2 N11_2 C15_2 O15_2 -179.67(15) . . . . ?
C23_2 N11_2 C15_2 O15_2 0.0(2) . . . . ?
N12_2 N11_2 C15_2 N14_2 0.04(14) . . . . ?
C23_2 N11_2 C15_2 N14_2 179.71(12) . . . . ?
C22_2 C21_2 O21_2 C27_2 174.28(12) . . . . ?
C26_2 C21_2 O21_2 C27_2 -5.7(2) . . . . ?
O21_2 C21_2 C22_2 C23_2 -178.84(11) . . . . ?
C26_2 C21_2 C22_2 C23_2 1.2(2) . . . . ?
C21_2 C22_2 C23_2 C24_2 -0.6(2) . . . . ?
C21_2 C22_2 C23_2 N11_2 179.56(12) . . . . ?
N12_2 N11_2 C23_2 C22_2 -176.29(12) . . . . ?
C15_2 N11_2 C23_2 C22_2 4.1(2) . . . . ?
N12_2 N11_2 C23_2 C24_2 3.85(17) . . . . ?
C15_2 N11_2 C23_2 C24_2 -175.79(13) . . . . ?
C22_2 C23_2 C24_2 C25_2 -0.1(2) . . . . ?
N11_2 C23_2 C24_2 C25_2 179.77(12) . . . . ?
C23_2 C24_2 C25_2 C26_2 0.2(2) . . . . ?
C24_2 C25_2 C26_2 C21_2 0.4(2) . . . . ?
O21_2 C21_2 C26_2 C25_2 178.93(13) . . . . ?
C22_2 C21_2 C26_2 C25_2 -1.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N14_1 H14_1 O15_2 0.912(17) 1.836(17) 2.736(2) 168.4(16) .
N14_2 H14_2 O15_1 0.968(16) 1.782(17) 2.742(2) 170.9(15) .

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        33.60
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.059

#===END
data_oa0802m
_database_code_depnum_ccdc_archive 'CCDC 714341'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1-(4-methoxyphenyl)-1,5-dihydro-5H-tetrazolone
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 N4 O2'
_chemical_formula_sum            'C8 H8 N4 O2'
_chemical_formula_weight         192.18

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1689(3)
_cell_length_b                   6.9582(2)
_cell_length_c                   12.1607(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.7990(10)
_cell_angle_gamma                90.00
_cell_volume                     831.91(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5255
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      33.12

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9747
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         33.14
_reflns_number_total             3139
_reflns_number_gt                2760
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3139
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.26670(6) 0.62031(9) 0.12803(5) 0.01675(13) Uani 1 1 d . . .
N12 N 0.16018(6) 0.65394(10) 0.03502(5) 0.02099(14) Uani 1 1 d . . .
N13 N 0.20357(7) 0.63548(11) -0.05432(6) 0.02278(15) Uani 1 1 d . . .
N14 N 0.33787(6) 0.59200(10) -0.02148(5) 0.02060(14) Uani 1 1 d . . .
H14 H 0.3858(12) 0.5622(17) -0.0714(10) 0.025 Uiso 1 1 d . . .
C15 C 0.38244(7) 0.57825(10) 0.09385(6) 0.01737(14) Uani 1 1 d . . .
O15 O 0.49690(5) 0.53755(9) 0.15220(5) 0.02222(14) Uani 1 1 d . . .
C21 C 0.24563(7) 0.61735(10) 0.23922(6) 0.01563(14) Uani 1 1 d . . .
C22 C 0.11425(7) 0.58535(11) 0.25065(6) 0.01828(14) Uani 1 1 d . . .
H22 H 0.0413 0.5638 0.1853 0.022 Uiso 1 1 calc R . .
C23 C 0.09123(7) 0.58536(11) 0.35784(6) 0.01951(15) Uani 1 1 d . . .
H23 H 0.0020 0.5643 0.3662 0.023 Uiso 1 1 calc R . .
C24 C 0.19866(7) 0.61628(10) 0.45408(6) 0.01738(14) Uani 1 1 d . . .
O24 O 0.16287(6) 0.61789(10) 0.55476(5) 0.02392(14) Uani 1 1 d . . .
C25 C 0.33011(7) 0.64447(11) 0.44240(6) 0.01798(14) Uani 1 1 d . . .
H25 H 0.4035 0.6629 0.5078 0.022 Uiso 1 1 calc R . .
C26 C 0.35341(7) 0.64556(10) 0.33411(6) 0.01738(14) Uani 1 1 d . . .
H26 H 0.4426 0.6655 0.3254 0.021 Uiso 1 1 calc R . .
C27 C 0.26852(9) 0.64091(15) 0.65631(7) 0.02812(18) Uani 1 1 d . . .
H27A H 0.2294 0.6401 0.7221 0.042 Uiso 1 1 calc R . .
H27B H 0.3152 0.7634 0.6536 0.042 Uiso 1 1 calc R . .
H27C H 0.3337 0.5351 0.6632 0.042 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.3717(8) . ?
N11 C15 1.3761(9) . ?
N11 C21 1.4221(9) . ?
N12 N13 1.2792(9) . ?
N13 N14 1.3556(9) . ?
N14 C15 1.3627(9) . ?
N14 H14 0.895(12) . ?
C15 O15 1.2315(8) . ?
C21 C26 1.3876(10) . ?
C21 C22 1.3959(9) . ?
C22 C23 1.3819(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.3987(10) . ?
C23 H23 0.9500 . ?
C24 O24 1.3635(8) . ?
C24 C25 1.3937(10) . ?
O24 C27 1.4238(10) . ?
C25 C26 1.3963(10) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 110.08(6) . . ?
N12 N11 C21 120.50(6) . . ?
C15 N11 C21 129.22(6) . . ?
N13 N12 N11 108.19(6) . . ?
N12 N13 N14 108.20(6) . . ?
N13 N14 C15 111.35(6) . . ?
N13 N14 H14 122.3(8) . . ?
C15 N14 H14 125.9(8) . . ?
O15 C15 N14 128.77(7) . . ?
O15 C15 N11 129.07(7) . . ?
N14 C15 N11 102.16(6) . . ?
C26 C21 C22 120.83(7) . . ?
C26 C21 N11 120.65(6) . . ?
C22 C21 N11 118.51(6) . . ?
C23 C22 C21 119.40(7) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.33(6) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
O24 C24 C25 124.98(7) . . ?
O24 C24 C23 114.97(6) . . ?
C25 C24 C23 120.05(7) . . ?
C24 O24 C27 117.67(6) . . ?
C24 C25 C26 119.68(7) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 119.69(6) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
O24 C27 H27A 109.5 . . ?
O24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 -0.14(9) . . . . ?
C21 N11 N12 N13 -175.42(6) . . . . ?
N11 N12 N13 N14 -0.63(9) . . . . ?
N12 N13 N14 C15 1.21(9) . . . . ?
N13 N14 C15 O15 178.45(8) . . . . ?
N13 N14 C15 N11 -1.21(8) . . . . ?
N12 N11 C15 O15 -178.84(8) . . . . ?
C21 N11 C15 O15 -4.09(13) . . . . ?
N12 N11 C15 N14 0.81(8) . . . . ?
C21 N11 C15 N14 175.57(7) . . . . ?
N12 N11 C21 C26 -159.12(7) . . . . ?
C15 N11 C21 C26 26.60(11) . . . . ?
N12 N11 C21 C22 20.92(9) . . . . ?
C15 N11 C21 C22 -153.36(8) . . . . ?
C26 C21 C22 C23 1.19(11) . . . . ?
N11 C21 C22 C23 -178.85(6) . . . . ?
C21 C22 C23 C24 -0.29(11) . . . . ?
C22 C23 C24 O24 178.41(7) . . . . ?
C22 C23 C24 C25 -0.95(11) . . . . ?
C25 C24 O24 C27 -3.17(11) . . . . ?
C23 C24 O24 C27 177.50(7) . . . . ?
O24 C24 C25 C26 -178.00(7) . . . . ?
C23 C24 C25 C26 1.30(11) . . . . ?
C22 C21 C26 C25 -0.84(10) . . . . ?
N11 C21 C26 C25 179.20(6) . . . . ?
C24 C25 C26 C21 -0.41(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N14 H14 O15 0.895(12) 1.863(12) 2.7435(8) 167.9(11) 3_665

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        33.14
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.054

#===END
data_oa0803m
_database_code_depnum_ccdc_archive 'CCDC 714342'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
HG864A 2-(3-methoxyphenyl)-5-methyl-tetrazolone
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 N4 O2'
_chemical_formula_sum            'C9 H10 N4 O2'
_chemical_formula_weight         206.21

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.8329(5)
_cell_length_b                   13.1354(8)
_cell_length_c                   16.0027(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1856.69(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5776
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      32.88

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24903
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         33.06
_reflns_number_total             3437
_reflns_number_gt                2672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3437
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.37691(9) 0.11595(6) 0.56216(5) 0.01596(16) Uani 1 1 d . . .
N12 N 0.41024(10) 0.10909(7) 0.64582(5) 0.01992(18) Uani 1 1 d . . .
N13 N 0.28686(10) 0.09315(7) 0.68532(5) 0.02019(18) Uani 1 1 d . . .
N14 N 0.17212(9) 0.08893(7) 0.62921(5) 0.01662(17) Uani 1 1 d . . .
C15 C 0.22262(10) 0.10358(7) 0.54918(6) 0.01525(18) Uani 1 1 d . . .
O15 O 0.14916(8) 0.10444(6) 0.48463(4) 0.01996(16) Uani 1 1 d . . .
C16 C 0.01749(11) 0.06842(9) 0.65424(6) 0.0222(2) Uani 1 1 d . . .
H16A H -0.0371 0.1329 0.6610 0.033 Uiso 1 1 calc R . .
H16B H 0.0174 0.0313 0.7074 0.033 Uiso 1 1 calc R . .
H16C H -0.0325 0.0272 0.6113 0.033 Uiso 1 1 calc R . .
C21 C 0.49455(10) 0.13013(7) 0.50264(6) 0.01508(17) Uani 1 1 d . . .
C22 C 0.45627(10) 0.14563(8) 0.41952(6) 0.01780(19) Uani 1 1 d . . .
H22 H 0.3531 0.1484 0.4030 0.021 Uiso 1 1 calc R . .
C23 C 0.57120(11) 0.15704(8) 0.36061(6) 0.01706(19) Uani 1 1 d . . .
O23 O 0.52277(8) 0.17061(7) 0.28019(4) 0.02428(19) Uani 1 1 d . . .
C24 C 0.72252(11) 0.15421(8) 0.38482(6) 0.01807(19) Uani 1 1 d . . .
H24 H 0.8008 0.1623 0.3447 0.022 Uiso 1 1 calc R . .
C25 C 0.75733(11) 0.13933(8) 0.46892(6) 0.0194(2) Uani 1 1 d . . .
H25 H 0.8605 0.1377 0.4857 0.023 Uiso 1 1 calc R . .
C26 C 0.64516(11) 0.12691(8) 0.52867(6) 0.01813(19) Uani 1 1 d . . .
H26 H 0.6702 0.1165 0.5858 0.022 Uiso 1 1 calc R . .
C27 C 0.63719(12) 0.17761(9) 0.21718(6) 0.0242(2) Uani 1 1 d . . .
H27A H 0.5893 0.1835 0.1622 0.036 Uiso 1 1 calc R . .
H27B H 0.7005 0.1164 0.2187 0.036 Uiso 1 1 calc R . .
H27C H 0.7001 0.2377 0.2275 0.036 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.3737(11) . ?
N11 C15 1.3881(12) . ?
N11 C21 1.4219(12) . ?
N12 N13 1.2770(12) . ?
N13 N14 1.3552(11) . ?
N14 C15 1.3697(11) . ?
N14 C16 1.4486(13) . ?
C15 O15 1.2199(11) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 C22 1.3874(13) . ?
C21 C26 1.3947(13) . ?
C22 C23 1.3936(13) . ?
C22 H22 0.9500 . ?
C23 O23 1.3678(11) . ?
C23 C24 1.3921(13) . ?
O23 C27 1.4306(12) . ?
C24 C25 1.3942(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.3865(14) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 110.40(8) . . ?
N12 N11 C21 120.32(8) . . ?
C15 N11 C21 129.24(8) . . ?
N13 N12 N11 108.07(8) . . ?
N12 N13 N14 108.48(8) . . ?
N13 N14 C15 111.73(8) . . ?
N13 N14 C16 121.97(8) . . ?
C15 N14 C16 126.28(8) . . ?
O15 C15 N14 128.31(9) . . ?
O15 C15 N11 130.38(9) . . ?
N14 C15 N11 101.32(7) . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C21 C26 121.55(9) . . ?
C22 C21 N11 118.90(8) . . ?
C26 C21 N11 119.54(8) . . ?
C21 C22 C23 119.13(8) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
O23 C23 C24 124.45(8) . . ?
O23 C23 C22 115.00(8) . . ?
C24 C23 C22 120.55(9) . . ?
C23 O23 C27 116.78(8) . . ?
C23 C24 C25 118.96(9) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 121.64(9) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C21 118.17(9) . . ?
C25 C26 H26 120.9 . . ?
C21 C26 H26 120.9 . . ?
O23 C27 H27A 109.5 . . ?
O23 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O23 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 0.11(11) . . . . ?
C21 N11 N12 N13 -177.82(8) . . . . ?
N11 N12 N13 N14 0.22(11) . . . . ?
N12 N13 N14 C15 -0.48(11) . . . . ?
N12 N13 N14 C16 177.99(9) . . . . ?
N13 N14 C15 O15 -179.95(10) . . . . ?
C16 N14 C15 O15 1.65(17) . . . . ?
N13 N14 C15 N11 0.51(10) . . . . ?
C16 N14 C15 N11 -177.88(9) . . . . ?
N12 N11 C15 O15 -179.90(10) . . . . ?
C21 N11 C15 O15 -2.20(17) . . . . ?
N12 N11 C15 N14 -0.37(10) . . . . ?
C21 N11 C15 N14 177.32(9) . . . . ?
N12 N11 C21 C22 -174.45(9) . . . . ?
C15 N11 C21 C22 8.05(15) . . . . ?
N12 N11 C21 C26 6.37(14) . . . . ?
C15 N11 C21 C26 -171.13(10) . . . . ?
C26 C21 C22 C23 0.75(15) . . . . ?
N11 C21 C22 C23 -178.41(9) . . . . ?
C21 C22 C23 O23 179.17(9) . . . . ?
C21 C22 C23 C24 -0.79(15) . . . . ?
C24 C23 O23 C27 2.95(15) . . . . ?
C22 C23 O23 C27 -177.01(9) . . . . ?
O23 C23 C24 C25 -179.67(10) . . . . ?
C22 C23 C24 C25 0.28(15) . . . . ?
C23 C24 C25 C26 0.28(15) . . . . ?
C24 C25 C26 C21 -0.31(15) . . . . ?
C22 C21 C26 C25 -0.21(15) . . . . ?
N11 C21 C26 C25 178.95(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        33.06
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.055

#===END
data_oa0801m
_database_code_depnum_ccdc_archive 'CCDC 714343'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1-(4-methoxyphenyl)-4-methyl-1,5-dihydro-5H-tetrazolone
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 N4 O2'
_chemical_formula_sum            'C9 H10 N4 O2'
_chemical_formula_weight         206.21

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8317(3)
_cell_length_b                   13.8861(13)
_cell_length_c                   17.7714(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     945.57(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3490
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      32.63

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7843
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         32.56
_reflns_number_total             2031
_reflns_number_gt                1830
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.4515(3) 0.51022(8) 0.49670(5) 0.0188(2) Uani 1 1 d . . .
N12 N 0.3553(4) 0.53620(9) 0.56787(6) 0.0252(3) Uani 1 1 d . . .
N13 N 0.4437(4) 0.46835(9) 0.61256(6) 0.0267(3) Uani 1 1 d . . .
N14 N 0.5974(3) 0.39757(8) 0.57173(6) 0.0207(2) Uani 1 1 d . . .
C15 C 0.6113(4) 0.42094(10) 0.49677(7) 0.0190(2) Uani 1 1 d . . .
O15 O 0.7347(3) 0.37537(7) 0.44478(5) 0.0266(2) Uani 1 1 d . . .
C16 C 0.7378(5) 0.31118(11) 0.60642(8) 0.0272(3) Uani 1 1 d . . .
H16A H 0.8924 0.2784 0.5707 0.041 Uiso 1 1 calc R . .
H16B H 0.5458 0.2681 0.6203 0.041 Uiso 1 1 calc R . .
H16C H 0.8700 0.3288 0.6516 0.041 Uiso 1 1 calc R . .
C21 C 0.4094(3) 0.57385(9) 0.43480(6) 0.0171(2) Uani 1 1 d . . .
C22 C 0.5237(4) 0.66786(9) 0.44163(7) 0.0189(2) Uani 1 1 d . . .
H22 H 0.6296 0.6888 0.4871 0.023 Uiso 1 1 calc R . .
C23 C 0.4838(4) 0.73183(10) 0.38194(7) 0.0190(2) Uani 1 1 d . . .
H23 H 0.5591 0.7968 0.3865 0.023 Uiso 1 1 calc R . .
C24 C 0.3319(4) 0.69930(9) 0.31557(6) 0.0186(2) Uani 1 1 d . . .
O24 O 0.2758(3) 0.75562(7) 0.25375(5) 0.0242(2) Uani 1 1 d . . .
C25 C 0.2224(4) 0.60349(10) 0.30865(7) 0.0202(2) Uani 1 1 d . . .
H25 H 0.1236 0.5816 0.2627 0.024 Uiso 1 1 calc R . .
C26 C 0.2578(4) 0.54083(9) 0.36854(6) 0.0191(2) Uani 1 1 d . . .
H26 H 0.1796 0.4761 0.3645 0.023 Uiso 1 1 calc R . .
C27 C 0.4063(5) 0.85185(11) 0.25550(9) 0.0275(3) Uani 1 1 d . . .
H27A H 0.3597 0.8832 0.2071 0.041 Uiso 1 1 calc R . .
H27B H 0.6584 0.8507 0.2647 0.041 Uiso 1 1 calc R . .
H27C H 0.2903 0.8877 0.2959 0.041 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.3660(14) . ?
N11 C15 1.3826(17) . ?
N11 C21 1.4201(15) . ?
N12 N13 1.2779(17) . ?
N13 N14 1.3562(17) . ?
N14 C15 1.3721(16) . ?
N14 C16 1.4520(18) . ?
C15 O15 1.2157(15) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 C22 1.3824(18) . ?
C21 C26 1.3909(16) . ?
C22 C23 1.3920(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.3906(17) . ?
C23 H23 0.9500 . ?
C24 O24 1.3657(15) . ?
C24 C25 1.4004(19) . ?
O24 C27 1.4270(18) . ?
C25 C26 1.3813(18) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 110.82(10) . . ?
N12 N11 C21 121.49(11) . . ?
C15 N11 C21 127.51(10) . . ?
N13 N12 N11 108.01(11) . . ?
N12 N13 N14 108.48(10) . . ?
N13 N14 C15 111.40(11) . . ?
N13 N14 C16 122.17(11) . . ?
C15 N14 C16 126.39(12) . . ?
O15 C15 N14 129.04(13) . . ?
O15 C15 N11 129.67(11) . . ?
N14 C15 N11 101.29(10) . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C21 C26 121.20(11) . . ?
C22 C21 N11 118.92(11) . . ?
C26 C21 N11 119.88(12) . . ?
C21 C22 C23 120.06(11) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 119.01(12) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
O24 C24 C23 124.21(12) . . ?
O24 C24 C25 115.23(11) . . ?
C23 C24 C25 120.56(11) . . ?
C24 O24 C27 117.62(11) . . ?
C26 C25 C24 120.09(11) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 119.06(12) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
O24 C27 H27A 109.5 . . ?
O24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 -0.31(17) . . . . ?
C21 N11 N12 N13 -175.68(13) . . . . ?
N11 N12 N13 N14 -0.03(18) . . . . ?
N12 N13 N14 C15 0.36(18) . . . . ?
N12 N13 N14 C16 178.05(14) . . . . ?
N13 N14 C15 O15 178.82(15) . . . . ?
C16 N14 C15 O15 1.2(3) . . . . ?
N13 N14 C15 N11 -0.51(15) . . . . ?
C16 N14 C15 N11 -178.09(14) . . . . ?
N12 N11 C15 O15 -178.83(15) . . . . ?
C21 N11 C15 O15 -3.8(2) . . . . ?
N12 N11 C15 N14 0.49(15) . . . . ?
C21 N11 C15 N14 175.52(13) . . . . ?
N12 N11 C21 C22 48.16(19) . . . . ?
C15 N11 C21 C22 -126.39(14) . . . . ?
N12 N11 C21 C26 -132.36(14) . . . . ?
C15 N11 C21 C26 53.1(2) . . . . ?
C26 C21 C22 C23 0.9(2) . . . . ?
N11 C21 C22 C23 -179.64(12) . . . . ?
C21 C22 C23 C24 -0.8(2) . . . . ?
C22 C23 C24 O24 179.22(13) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C23 C24 O24 C27 5.1(2) . . . . ?
C25 C24 O24 C27 -175.31(13) . . . . ?
O24 C24 C25 C26 -178.21(13) . . . . ?
C23 C24 C25 C26 1.4(2) . . . . ?
C24 C25 C26 C21 -1.3(2) . . . . ?
C22 C21 C26 C25 0.2(2) . . . . ?
N11 C21 C26 C25 -179.32(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        32.56
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.051


