#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/50/7115020.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_7115020
loop_
_publ_author_name
'Dunn, Peter J.'
'Higginson, Paul'
'Sridharan, Visuvanthar'
'Graham, Alison B.'
'Grigg, Ronald'
'Thornton-Pett, Mark'
_publ_section_title
;
 A novel route to substituted 4-methylene-4,5-dihydroisoxazoles mediated
 by hafnium(iv) chloride
;
_journal_issue                   19
_journal_name_full               'Chemical Communications'
_journal_page_first              1968
_journal_paper_doi               10.1039/b105561p
_journal_year                    2001
_chemical_formula_sum            'C11 H11 N O'
_chemical_formula_weight         173.21
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.3331(2)
_cell_length_b                   7.3853(2)
_cell_length_c                   20.0230(9)
_cell_measurement_temperature    150(2)
_cell_volume                     1823.77(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WC (Thornton-Pett, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD area detector diffractometer'
_diffrn_measurement_method
;
Detector set at 30mm from sample with different 2theta offsets 
1 degree phi exposures for chi=0 degree settings
1 degree omega exposures for chi=90 degree settings
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10086
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Using multiple and symmetry-related data measurements via the program SORTAV
See R.H. Blessing, Acta Cryst (1995), A51, 33-38 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.4825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                1390
_reflns_number_total             1787
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b105561p.txt
_cod_data_source_block           ag05
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7115020
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
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
O1 O 0.56863(9) 0.19278(16) 0.49390(6) 0.0434(3) Uani 1 1 d .
N2 N 0.64413(11) 0.23022(18) 0.44220(7) 0.0388(4) Uani 1 1 d .
C3 C 0.74058(13) 0.1964(2) 0.46361(7) 0.0318(4) Uani 1 1 d .
C31 C 0.83612(14) 0.2256(2) 0.41958(8) 0.0406(4) Uani 1 1 d .
H31A H 0.8118 0.2719 0.3762 0.061 Uiso 1 1 calc R
H31B H 0.8744 0.1106 0.4132 0.061 Uiso 1 1 calc R
H31C H 0.8851 0.3136 0.4404 0.061 Uiso 1 1 calc R
C4 C 0.74306(12) 0.13189(19) 0.53248(7) 0.0288(3) Uani 1 1 d .
C5 C 0.62588(12) 0.1191(2) 0.55096(8) 0.0343(4) Uani 1 1 d .
H5A H 0.6047 -0.0084 0.5589 0.041 Uiso 1 1 calc R
H5B H 0.6105 0.1906 0.5917 0.041 Uiso 1 1 calc R
C6 C 0.83383(12) 0.10289(19) 0.56807(7) 0.0286(4) Uani 1 1 d .
H6 H 0.9002 0.1209 0.5449 0.034 Uiso 1 1 calc R
C7 C 0.84323(12) 0.04696(19) 0.63800(7) 0.0291(4) Uani 1 1 d .
C8 C 0.75813(13) -0.0307(2) 0.67430(8) 0.0335(4) Uani 1 1 d .
H8 H 0.6899 -0.0491 0.6534 0.040 Uiso 1 1 calc R
C9 C 0.77224(14) -0.0809(2) 0.74033(8) 0.0383(4) Uani 1 1 d .
H9 H 0.7139 -0.1349 0.7640 0.046 Uiso 1 1 calc R
C10 C 0.86991(14) -0.0536(2) 0.77198(8) 0.0416(4) Uani 1 1 d .
H10 H 0.8790 -0.0883 0.8173 0.050 Uiso 1 1 calc R
C11 C 0.95524(14) 0.0251(2) 0.73712(8) 0.0414(4) Uani 1 1 d .
H11 H 1.0225 0.0463 0.7589 0.050 Uiso 1 1 calc R
C12 C 0.94228(13) 0.0727(2) 0.67076(8) 0.0346(4) Uani 1 1 d .
H12 H 1.0016 0.1236 0.6470 0.042 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 0.0345(6) 0.0527(8) 0.0431(7) 0.0056(5) -0.0069(5) 0.0009(5)
N2 0.0432(9) 0.0380(8) 0.0351(8) -0.0002(6) -0.0058(6) -0.0015(6)
C3 0.0389(9) 0.0278(8) 0.0287(8) -0.0037(6) -0.0044(7) -0.0005(6)
C31 0.0490(11) 0.0430(10) 0.0298(9) 0.0007(7) 0.0015(7) 0.0012(7)
C4 0.0350(8) 0.0228(7) 0.0286(8) -0.0033(6) -0.0004(7) -0.0020(6)
C5 0.0339(9) 0.0337(8) 0.0352(9) -0.0013(6) -0.0039(7) -0.0012(6)
C6 0.0314(8) 0.0260(8) 0.0284(8) -0.0005(6) 0.0019(6) -0.0003(6)
C7 0.0352(8) 0.0236(7) 0.0286(8) -0.0019(6) 0.0005(6) 0.0021(6)
C8 0.0399(9) 0.0290(8) 0.0317(8) -0.0006(6) -0.0009(7) -0.0028(6)
C9 0.0495(10) 0.0322(9) 0.0332(9) 0.0045(6) 0.0059(8) -0.0008(7)
C10 0.0563(11) 0.0389(9) 0.0296(8) 0.0046(6) -0.0009(8) 0.0095(8)
C11 0.0397(9) 0.0484(10) 0.0362(9) 0.0017(7) -0.0080(7) 0.0068(7)
C12 0.0330(8) 0.0372(9) 0.0337(9) 0.0010(6) -0.0006(7) 0.0029(6)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 O1 C5 109.18(11)
C3 N2 O1 108.97(12)
N2 C3 C4 113.39(14)
N2 C3 C31 120.38(14)
C4 C3 C31 126.23(14)
C6 C4 C3 124.77(14)
C6 C4 C5 131.59(14)
C3 C4 C5 103.56(13)
O1 C5 C4 104.59(12)
C4 C6 C7 128.15(14)
C8 C7 C12 117.82(14)
C8 C7 C6 123.56(14)
C12 C7 C6 118.62(14)
C9 C8 C7 120.78(15)
C10 C9 C8 120.70(15)
C9 C10 C11 119.52(15)
C12 C11 C10 120.06(16)
C11 C12 C7 121.10(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.4196(18)
O1 C5 1.4492(18)
N2 C3 1.289(2)
C3 C4 1.459(2)
C3 C31 1.487(2)
C4 C6 1.344(2)
C4 C5 1.495(2)
C6 C7 1.464(2)
C7 C8 1.399(2)
C7 C12 1.400(2)
C8 C9 1.384(2)
C9 C10 1.376(2)
C10 C11 1.390(2)
C11 C12 1.384(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101135780
