#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/24/4022456.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_4022456
loop_
_publ_author_name
'Richard S. Grainger'
'Richard B. Owoare'
'Patrizia Tisselli'
'Jonathan W. Steed'
_publ_section_title
;
 A Synthetic Alternative to the Type-II Intramolecular
 4 + 3 Cycloaddition Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7899
_journal_page_last               7902
_journal_paper_doi               10.1021/jo034356f
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C11 H14 O2'
_chemical_formula_weight         178.22
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 107.876(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.1341(6)
_cell_length_b                   7.6802(3)
_cell_length_c                   11.0101(3)
_cell_measurement_temperature    120(2)
_cell_volume                     1781.30(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.885
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'Nonis KappaCCD CCD diffractometer'
_diffrn_measurement_method       'phi & omega scans'
_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  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2933
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.59
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9735
_exptl_absorpt_correction_T_min  0.9315
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+1.2353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                1548
_reflns_number_total             1813
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034356fsi20030318_091819.cif
_cod_data_source_block           C:\structs\Grainger\ro289a\RO289A.CIF
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022456
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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 0.06807(4) 0.33320(13) 1.10359(8) 0.0218(3) Uani 1 1 d .
C1 C 0.09649(6) 0.17118(17) 1.08597(12) 0.0170(3) Uani 1 1 d .
H1 H 0.0930 0.0813 1.1491 0.020 Uiso 1 1 calc R
O2 O 0.07995(4) 0.22005(13) 0.75419(8) 0.0206(3) Uani 1 1 d .
C2 C 0.06432(6) 0.11143(17) 0.94674(11) 0.0150(3) Uani 1 1 d .
H2 H 0.0179 0.1036 0.9359 0.018 Uiso 1 1 calc R
C3 C 0.07179(5) 0.25406(17) 0.85618(11) 0.0154(3) Uani 1 1 d .
C4 C 0.06708(6) 0.44046(18) 0.89747(12) 0.0198(3) Uani 1 1 d .
H4A H 0.0219 0.4754 0.8748 0.024 Uiso 1 1 calc R
H4B H 0.0886 0.5190 0.8525 0.024 Uiso 1 1 calc R
C5 C 0.09843(6) 0.45654(18) 1.04273(12) 0.0216(3) Uani 1 1 d .
H5 H 0.0964 0.5780 1.0739 0.026 Uiso 1 1 calc R
C6 C 0.16558(6) 0.38945(19) 1.07764(12) 0.0223(3) Uani 1 1 d .
H6 H 0.2021 0.4567 1.0808 0.027 Uiso 1 1 calc R
C7 C 0.16523(6) 0.22061(19) 1.10331(11) 0.0192(3) Uani 1 1 d .
C8 C 0.21791(6) 0.0896(2) 1.13252(13) 0.0253(4) Uani 1 1 d .
H8A H 0.2369 0.0808 1.2263 0.030 Uiso 1 1 calc R
H8B H 0.2513 0.1316 1.0971 0.030 Uiso 1 1 calc R
C9 C 0.19670(7) -0.0923(2) 1.07877(13) 0.0255(4) Uani 1 1 d .
H9A H 0.1722 -0.1467 1.1304 0.031 Uiso 1 1 calc R
H9B H 0.2349 -0.1646 1.0884 0.031 Uiso 1 1 calc R
C10 C 0.15582(6) -0.09478(18) 0.93763(13) 0.0214(3) Uani 1 1 d .
H10A H 0.1709 -0.0018 0.8918 0.026 Uiso 1 1 calc R
H10B H 0.1622 -0.2076 0.8998 0.026 Uiso 1 1 calc R
C11 C 0.08453(6) -0.06909(17) 0.91611(12) 0.0179(3) Uani 1 1 d .
H11A H 0.0616 -0.0953 0.8256 0.022 Uiso 1 1 calc R
H11B H 0.0706 -0.1553 0.9688 0.022 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 0.0319(5) 0.0171(5) 0.0207(5) -0.0007(4) 0.0146(4) 0.0054(4)
C1 0.0241(7) 0.0139(7) 0.0149(6) 0.0013(5) 0.0089(5) 0.0039(5)
O2 0.0273(5) 0.0207(5) 0.0153(5) 0.0012(4) 0.0088(4) 0.0002(4)
C2 0.0158(6) 0.0144(7) 0.0158(6) 0.0008(5) 0.0063(5) 0.0003(5)
C3 0.0124(5) 0.0175(7) 0.0153(6) 0.0014(5) 0.0028(5) 0.0005(5)
C4 0.0257(7) 0.0148(7) 0.0195(6) 0.0026(5) 0.0080(5) 0.0023(6)
C5 0.0331(8) 0.0130(7) 0.0207(7) -0.0024(6) 0.0113(6) 0.0000(6)
C6 0.0251(7) 0.0235(8) 0.0167(6) -0.0045(6) 0.0041(5) -0.0059(6)
C7 0.0229(7) 0.0237(8) 0.0097(6) -0.0021(5) 0.0030(5) 0.0004(6)
C8 0.0210(6) 0.0325(9) 0.0196(7) 0.0023(6) 0.0022(5) 0.0051(6)
C9 0.0255(7) 0.0262(8) 0.0246(7) 0.0057(6) 0.0076(6) 0.0121(6)
C10 0.0254(7) 0.0176(7) 0.0238(7) -0.0007(6) 0.0114(6) 0.0056(6)
C11 0.0229(6) 0.0140(7) 0.0190(6) 0.0012(5) 0.0094(5) -0.0007(5)
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'
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
C1 O1 C5 102.76(9)
O1 C1 C7 103.28(10)
O1 C1 C2 107.67(10)
C7 C1 C2 109.65(10)
C3 C2 C11 114.23(10)
C3 C2 C1 108.99(10)
C11 C2 C1 114.28(10)
O2 C3 C4 121.47(12)
O2 C3 C2 121.67(12)
C4 C3 C2 116.84(10)
C3 C4 C5 109.67(11)
O1 C5 C6 102.77(11)
O1 C5 C4 107.73(11)
C6 C5 C4 109.39(10)
C7 C6 C5 108.56(12)
C6 C7 C8 130.28(13)
C6 C7 C1 106.73(12)
C8 C7 C1 122.78(12)
C7 C8 C9 113.77(11)
C8 C9 C10 114.59(11)
C11 C10 C9 114.34(11)
C2 C11 C10 116.10(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4341(15)
O1 C5 1.4403(17)
C1 C7 1.5222(18)
C1 C2 1.5483(17)
O2 C3 1.2191(15)
C2 C3 1.5240(17)
C2 C11 1.5260(18)
C3 C4 1.5152(18)
C4 C5 1.5406(18)
C5 C6 1.5072(19)
C6 C7 1.328(2)
C7 C8 1.4986(19)
C8 C9 1.533(2)
C9 C10 1.5397(18)
C10 C11 1.5347(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11745191
