#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/45/7204513.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204513
loop_
_publ_author_name
'Lee, Connie K. Y.'
'Easton, Christopher J.'
'Gebara-Coghlan, Mariana'
'Radom, Leo'
'Scott, Anthony P.'
'Simpson, Gregory W.'
'Willis, Anthony C.'
_publ_section_title
;
 Substituent effects in isoxazoles: identification of 4-substituted
 isoxazoles as Michael acceptors
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2031
_journal_paper_doi               10.1039/b207808b
_journal_year                    2002
_chemical_formula_moiety         'C6 H7 N O3 '
_chemical_formula_sum            'C6 H7 N O3'
_chemical_formula_weight         141.13
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             2000-06-29
_audit_creation_method           'by teXsan v1.8'
_audit_update_record
;
2000-06-30 - Report on C6 H7 N O3
by Anthony C. Willis
for Connie K. Y. Lee and Christopher J. Easton
2000-06-30 - passes checkcif tests with 1 minor warning
;
_cell_angle_alpha                90
_cell_angle_beta                 111.428(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8027(3)
_cell_length_b                   11.2422(5)
_cell_length_c                   8.4806(4)
_cell_measurement_reflns_used    9111
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      4.08
_cell_volume                     692.49(5)
_computing_cell_refinement
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1994)
;
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_UB_11      0.00000
_diffrn_orient_matrix_UB_12      0.00000
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.00000
_diffrn_orient_matrix_UB_31      0.00000
_diffrn_orient_matrix_UB_32      0.00000
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.05880
_diffrn_reflns_av_sigmaI/netI    0.140
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14023
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         4.45
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  .994
_exptl_absorpt_correction_T_min  .888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)

1   0   0  0.0200
-1   0   0  0.1000
1  -1   0  0.0100
0   1   0  0.1500
0  -1   0  0.1400
0  -1   1  0.0800
0   1  -1  0.1200
0   1   2  0.1200
0  -1  -2  0.1600
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.876
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     115
_refine_ls_number_reflns         904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.0030
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w = 1/[σ²(Fo)]
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0475
_refine_ls_wR_factor_ref         0.0402
_reflns_number_gt                904
_reflns_number_total             1573
_reflns_threshold_expression     I>2.00σ(I)
_cod_data_source_file            b207808b.txt
_cod_data_source_block           ckl3
_cod_original_sg_symbol_H-M      'P 21/c     '
_cod_original_formula_sum        'C6 H7 N O3 '
_cod_database_code               7204513
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,1/2+y,1/2-z'
'   -x,   -y,   -z'
'   +x,1/2-y,1/2+z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_refinement_flags
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
O(1) 0.8648(2) 0.1281(1) 0.5621(2) 0.0494(4) 1.000 . Uani d ?
O(2) 0.4879(2) -0.1816(1) 0.3079(2) 0.0541(4) 1.000 . Uani d ?
O(3) 0.4321(2) -0.0083(1) 0.1671(1) 0.0496(4) 1.000 . Uani d ?
N(1) 0.9201(2) 0.0232(1) 0.6625(2) 0.0490(5) 1.000 . Uani d ?
C(1) 0.8053(2) -0.0596(2) 0.5783(2) 0.0407(5) 1.000 . Uani d ?
C(2) 0.6744(2) -0.0143(1) 0.4248(2) 0.0339(5) 1.000 . Uani d ?
C(3) 0.7203(3) 0.1010(2) 0.4239(2) 0.0416(5) 1.000 . Uani d ?
C(4) 0.8238(4) -0.1823(2) 0.6479(3) 0.0631(7) 1.000 . Uani d ?
C(5) 0.5243(2) -0.0779(2) 0.2973(2) 0.0385(5) 1.000 . Uani d ?
C(6) 0.2800(3) -0.0635(3) 0.0316(3) 0.0626(7) 1.000 . Uani d ?
H(1) 0.663(3) 0.167(2) 0.341(2) 0.065(6) 1.000 . Uiso d ?
H(2) 0.931(3) -0.190(2) 0.744(3) 0.101(5) 1.000 . Uiso d ?
H(3) 0.712(3) -0.206(2) 0.667(3) 0.101 1.000 . Uiso d ?
H(4) 0.835(3) -0.242(2) 0.570(3) 0.101 1.000 . Uiso d ?
H(5) 0.327(3) -0.129(2) -0.023(3) 0.089(4) 1.000 . Uiso d ?
H(6) 0.196(3) -0.092(2) 0.077(3) 0.089 1.000 . Uiso d ?
H(7) 0.218(3) 0.004(2) -0.058(3) 0.089 1.000 . Uiso d ?
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) 0.0452(8) 0.0485(8) 0.0453(8) -0.0063(6) 0.0054(7) -0.0036(6)
O(2) 0.0623(9) 0.0397(8) 0.0523(9) -0.0083(7) 0.0112(7) -0.0075(6)
O(3) 0.0444(8) 0.0553(8) 0.0366(8) -0.0047(7) -0.0001(6) 0.0012(6)
N(1) 0.0401(9) 0.060(1) 0.0398(9) 0.0000(8) 0.0056(8) 0.0035(8)
C(1) 0.036(1) 0.046(1) 0.038(1) 0.0039(9) 0.0117(9) 0.0035(9)
C(2) 0.0322(9) 0.036(1) 0.032(1) 0.0028(8) 0.0091(8) -0.0005(8)
C(3) 0.037(1) 0.044(1) 0.037(1) 0.0003(9) 0.0058(9) -0.0017(9)
C(4) 0.061(1) 0.055(1) 0.064(2) 0.010(1) 0.012(1) 0.024(1)
C(5) 0.038(1) 0.042(1) 0.034(1) 0.0029(9) 0.0115(9) -0.0035(8)
C(6) 0.050(1) 0.085(2) 0.038(1) -0.014(1) -0.001(1) -0.008(1)
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 24 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 28 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 4 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0 12 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N(1) O(1) C(3) 108.1(1) . . . yes
C(5) O(3) C(6) 116.2(2) . . . yes
O(1) N(1) C(1) 105.3(1) . . . yes
N(1) C(1) C(2) 111.4(2) . . . yes
N(1) C(1) C(4) 119.7(2) . . . yes
C(2) C(1) C(4) 128.9(2) . . . yes
C(1) C(2) C(3) 104.3(2) . . . yes
C(1) C(2) C(5) 128.0(2) . . . yes
C(3) C(2) C(5) 127.7(2) . . . yes
O(1) C(3) C(2) 111.0(2) . . . yes
O(1) C(3) H(1) 117(1) . . . no
C(2) C(3) H(1) 132(1) . . . no
C(1) C(4) H(2) 111(2) . . . no
C(1) C(4) H(3) 111(1) . . . no
C(1) C(4) H(4) 113(2) . . . no
H(2) C(4) H(3) 114(2) . . . no
H(2) C(4) H(4) 105(2) . . . no
H(3) C(4) H(4) 103(2) . . . no
O(2) C(5) O(3) 123.9(2) . . . yes
O(2) C(5) C(2) 124.3(2) . . . yes
O(3) C(5) C(2) 111.8(2) . . . yes
O(3) C(6) H(5) 110(1) . . . no
O(3) C(6) H(6) 109(2) . . . no
O(3) C(6) H(7) 107(1) . . . no
H(5) C(6) H(6) 111(2) . . . no
H(5) C(6) H(7) 110(2) . . . no
H(6) C(6) H(7) 110(2) . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) N(1) 1.427(2) . . yes
O(1) C(3) 1.331(2) . . yes
O(2) C(5) 1.211(2) . . yes
O(3) C(5) 1.330(2) . . yes
O(3) C(6) 1.455(2) . . yes
N(1) C(1) 1.308(2) . . yes
C(1) C(2) 1.423(2) . . yes
C(1) C(4) 1.487(3) . . yes
C(2) C(3) 1.345(2) . . yes
C(2) C(5) 1.459(2) . . yes
C(3) H(1) 1.01(2) . . no
C(4) H(2) 0.93(3) . . no
C(4) H(3) 0.98(3) . . no
C(4) H(4) 0.97(3) . . no
C(6) H(5) 1.01(2) . . no
C(6) H(6) 0.93(3) . . no
C(6) H(7) 1.06(3) . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) C(1) 3.299(2) . 3_756 no
O(1) O(2) 3.372(2) . 3_656 no
O(1) N(1) 3.417(2) . 3_756 no
O(1) C(4) 3.482(2) . 2_756 no
O(1) C(4) 3.551(3) . 3_756 no
O(2) C(3) 3.185(2) . 2_645 no
O(2) C(3) 3.366(2) . 3_656 no
O(3) C(6) 3.362(3) . 3_655 no
O(3) O(3) 3.375(2) . 3_655 no
O(3) C(1) 3.405(2) . 3_656 no
O(3) N(1) 3.545(2) . 3_656 no
N(1) C(3) 3.444(2) . 3_756 no
N(1) N(1) 3.454(3) . 3_756 no
N(1) C(1) 3.482(2) . 3_756 no
N(1) C(6) 3.494(3) . 1_656 no
N(1) C(2) 3.504(2) . 3_756 no
N(1) C(6) 3.512(3) . 3_656 no
C(1) C(5) 3.478(2) . 3_656 no
C(2) C(2) 3.418(3) . 3_656 no
C(2) C(5) 3.421(2) . 3_656 no
C(3) C(5) 3.549(3) . 3_656 no
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
O(1) N(1) C(1) C(2) . . . . 0.0(2) no
O(1) N(1) C(1) C(4) . . . . 180.0(2) no
O(1) C(3) C(2) C(1) . . . . -0.2(2) no
O(1) C(3) C(2) C(5) . . . . 179.6(2) no
O(2) C(5) O(3) C(6) . . . . -0.3(3) no
O(2) C(5) C(2) C(1) . . . . 1.6(3) no
O(2) C(5) C(2) C(3) . . . . -178.2(2) no
O(3) C(5) C(2) C(1) . . . . -178.2(2) no
O(3) C(5) C(2) C(3) . . . . 2.0(2) no
N(1) O(1) C(3) C(2) . . . . 0.2(2) no
N(1) C(1) C(2) C(3) . . . . 0.1(2) no
N(1) C(1) C(2) C(5) . . . . -179.7(2) no
C(1) N(1) O(1) C(3) . . . . -0.1(2) no
C(2) C(5) O(3) C(6) . . . . 179.4(2) no
C(3) C(2) C(1) C(4) . . . . -179.8(2) no
C(4) C(1) C(2) C(5) . . . . 0.4(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4416933
