Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Vincenzo Schettino'
_publ_contact_author_address     
;
Dipartimento di Chimca
Universita di Firenze
Via della Lastruccia 3
Sesto Fiorentino
Firenze
I-50019
ITALY
;

_publ_contact_author_email       VINCENZO.SCHETTINO@UNIFI.IT

_publ_section_title              
;
CRYSTAL AND MOLECULAR STRUCTURE OF CUPRIZONE
;
loop_
_publ_author_name
'Vincenzo Schettino'
'Bruno Bruni'
'Gianni Cardini'
'Angela Casini'
'Massimo Di Vaira'
'L. Messori'
;
M.Muniz-Miranda
;
'Marco Pagliani'

data_cupri
_database_code_depnum_ccdc_archive 'CCDC 662398'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H11 N2 O'
_chemical_formula_sum            'C7 H11 N2 O'
_chemical_formula_weight         139.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 2(1)/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   7.143(2)
_cell_length_b                   6.409(1)
_cell_length_c                   15.748(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.14(3)
_cell_angle_gamma                90.00
_cell_volume                     720.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    609
_cell_measurement_theta_min      6.3
_cell_measurement_theta_max      58.8

_exptl_crystal_description       'thin rod'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 1986) '

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Oxford Diffraction, Enhance ULTRA assembly'
_diffrn_measurement_device_type  'Oxford Diffraction Excalibur PX Ultra CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3908
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.20
_diffrn_reflns_theta_max         69.75
_diffrn_reflns_theta_full        69.75
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_reflns_number_total             1284
_reflns_number_gt                1070
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis CCD '
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1650P)^2^+0.7275P] where P=(Fo^2^+2Fc^2^)/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         1284
_refine_ls_number_parameters     96
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2523
_refine_ls_wR_factor_gt          0.2484
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.104

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
O1 O 0.0733(6) 0.0148(4) 0.1065(2) 0.0311(8) Uani 1 1 d . . .
N1 N 0.0915(6) -0.2570(6) 0.0129(3) 0.0319(10) Uani 1 1 d D . .
H1 H 0.047(8) -0.3088(19) -0.0467(19) 0.038 Uiso 1 1 d D . .
N2 N 0.1333(6) -0.4130(6) 0.0729(3) 0.0325(10) Uani 1 1 d D . .
C1 C 0.0445(7) -0.0609(8) 0.0363(3) 0.0306(11) Uani 1 1 d D . .
C2 C 0.2823(7) -0.3925(7) 0.1167(3) 0.0303(11) Uani 1 1 d . . .
C3 C 0.4279(8) -0.2220(8) 0.1086(3) 0.0380(12) Uani 1 1 d . . .
H31 H 0.4137 -0.1220 0.1560 0.046 Uiso 1 1 calc R . .
H32 H 0.4076 -0.1452 0.0548 0.046 Uiso 1 1 calc R . .
C4 C 0.6282(8) -0.3129(10) 0.1097(4) 0.0469(14) Uani 1 1 d . . .
H41 H 0.6537 -0.3782 0.0540 0.056 Uiso 1 1 calc R . .
H42 H 0.7185 -0.1972 0.1174 0.056 Uiso 1 1 calc R . .
C5 C 0.6617(8) -0.4763(9) 0.1800(4) 0.0430(14) Uani 1 1 d . . .
H51 H 0.7879 -0.5378 0.1732 0.052 Uiso 1 1 calc R . .
H52 H 0.6568 -0.4072 0.2362 0.052 Uiso 1 1 calc R . .
C6 C 0.5153(9) -0.6489(9) 0.1765(4) 0.0455(14) Uani 1 1 d . . .
H61 H 0.5361 -0.7469 0.2242 0.055 Uiso 1 1 calc R . .
H62 H 0.5292 -0.7276 0.1228 0.055 Uiso 1 1 calc R . .
C7 C 0.3174(8) -0.5600(8) 0.1819(3) 0.0381(13) Uani 1 1 d . . .
H71 H 0.2259 -0.6743 0.1734 0.046 Uiso 1 1 calc R . .
H72 H 0.2974 -0.5014 0.2393 0.046 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0455(18) 0.0211(15) 0.0268(15) -0.0015(12) -0.0051(15) 0.0008(14)
N1 0.046(2) 0.0180(17) 0.0321(19) -0.0020(14) -0.0047(17) -0.0017(17)
N2 0.042(2) 0.0199(18) 0.035(2) -0.0013(16) -0.0056(19) -0.0012(18)
C1 0.034(3) 0.028(2) 0.030(2) -0.0016(19) -0.002(2) -0.004(2)
C2 0.040(3) 0.020(2) 0.031(2) -0.0076(19) 0.001(2) 0.001(2)
C3 0.039(3) 0.033(2) 0.042(3) -0.008(2) 0.002(2) -0.003(2)
C4 0.036(3) 0.053(3) 0.052(3) -0.002(3) 0.004(2) -0.005(3)
C5 0.032(3) 0.051(3) 0.046(3) -0.001(3) -0.010(2) 0.001(2)
C6 0.051(3) 0.034(3) 0.051(3) -0.003(2) -0.015(3) 0.001(2)
C7 0.044(3) 0.031(2) 0.039(3) -0.001(2) -0.011(2) -0.001(2)

_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
O1 C1 1.225(6) . ?
N1 C1 1.353(6) . ?
N1 N2 1.407(6) . ?
N1 H1 1.044(11) . ?
N2 C2 1.274(7) . ?
C1 C1 1.522(10) 3 ?
C2 C7 1.505(7) . ?
C2 C3 1.515(7) . ?
C3 C4 1.545(8) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C5 1.542(8) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.523(8) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.527(9) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?

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
C1 N1 N2 122.0(4) . . ?
C1 N1 H1 117.8(9) . . ?
N2 N1 H1 116.2(8) . . ?
C2 N2 N1 117.8(4) . . ?
O1 C1 N1 125.0(5) . . ?
O1 C1 C1 123.0(6) . 3 ?
N1 C1 C1 112.0(5) . 3 ?
N2 C2 C7 115.7(5) . . ?
N2 C2 C3 127.0(5) . . ?
C7 C2 C3 117.3(4) . . ?
C2 C3 C4 111.3(4) . . ?
C2 C3 H31 109.4 . . ?
C4 C3 H31 109.4 . . ?
C2 C3 H32 109.4 . . ?
C4 C3 H32 109.4 . . ?
H31 C3 H32 108.0 . . ?
C5 C4 C3 114.0(5) . . ?
C5 C4 H41 108.8 . . ?
C3 C4 H41 108.8 . . ?
C5 C4 H42 108.8 . . ?
C3 C4 H42 108.8 . . ?
H41 C4 H42 107.6 . . ?
C6 C5 C4 111.2(5) . . ?
C6 C5 H51 109.4 . . ?
C4 C5 H51 109.4 . . ?
C6 C5 H52 109.4 . . ?
C4 C5 H52 109.4 . . ?
H51 C5 H52 108.0 . . ?
C5 C6 C7 111.3(5) . . ?
C5 C6 H61 109.4 . . ?
C7 C6 H61 109.4 . . ?
C5 C6 H62 109.4 . . ?
C7 C6 H62 109.4 . . ?
H61 C6 H62 108.0 . . ?
C2 C7 C6 112.4(5) . . ?
C2 C7 H71 109.1 . . ?
C6 C7 H71 109.1 . . ?
C2 C7 H72 109.1 . . ?
C6 C7 H72 109.1 . . ?
H71 C7 H72 107.9 . . ?

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
C1 N1 N2 C2 -67.9(6) . . . . ?
N2 N1 C1 O1 17.4(8) . . . . ?
N2 N1 C1 C1 -164.5(5) . . . 3 ?
N1 N2 C2 C7 178.1(4) . . . . ?
N1 N2 C2 C3 -3.4(7) . . . . ?
N2 C2 C3 C4 -134.5(6) . . . . ?
C7 C2 C3 C4 43.9(6) . . . . ?
C2 C3 C4 C5 -45.8(6) . . . . ?
C3 C4 C5 C6 53.3(7) . . . . ?
C4 C5 C6 C7 -55.9(6) . . . . ?
N2 C2 C7 C6 130.3(5) . . . . ?
C3 C2 C7 C6 -48.3(6) . . . . ?
C5 C6 C7 C2 53.0(6) . . . . ?

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