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#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/25/4112569.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_4112569
loop_
_publ_author_name
'May Xiao-Wu Jiang'
'Manish Rawat'
'William D. Wulff'
_publ_section_title
;
 Contingency and Serendipity in the Reactions of Fischer Carbene Complexes
 with Conjugated Triynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5970
_journal_page_last               5971
_journal_paper_doi               10.1021/ja049836i
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C17 H13 O2'
_chemical_formula_weight         249.27
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.06(3)
_cell_angle_beta                 80.54(3)
_cell_angle_gamma                86.94(3)
_cell_formula_units_Z            2
_cell_length_a                   6.0219(12)
_cell_length_b                   9.4637(19)
_cell_length_c                   11.002(2)
_cell_measurement_temperature    293(2)
_cell_volume                     616.4(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.908
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3938
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.087
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             262
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1139P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                2185
_reflns_number_total             2760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja049836isi20040110_120541.cif
_cod_data_source_block           wu001
_cod_original_cell_volume        616.5(2)
_cod_database_code               4112569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.5562(3) 0.18358(17) 0.16042(13) 0.0326(3) Uani 1 1 d
H1A H 0.407(3) 0.167(2) 0.1331(18) 0.047(5) Uiso 1 1 d
H1B H 0.615(3) 0.270(2) 0.1104(17) 0.046(5) Uiso 1 1 d
C2 C 0.7213(3) 0.05569(16) 0.13924(14) 0.0349(4) Uani 1 1 d
H2A H 0.643(3) -0.034(2) 0.1723(16) 0.036(4) Uiso 1 1 d
H2B H 0.768(3) 0.0486(19) 0.0448(16) 0.035(4) Uiso 1 1 d
C3 C 0.9223(3) 0.07191(16) 0.20389(14) 0.0332(3) Uani 1 1 d
H3A H 1.043(3) -0.005(2) 0.1857(16) 0.041(5) Uiso 1 1 d
H3B H 0.992(3) 0.1641(19) 0.1736(15) 0.030(4) Uiso 1 1 d
C4 C 0.8481(2) 0.07336(15) 0.34343(13) 0.0283(3) Uani 1 1 d
H4A H 0.967(3) 0.1058(18) 0.3811(16) 0.033(4) Uiso 1 1 d
H4B H 0.812(3) -0.0259(19) 0.3802(16) 0.035(4) Uiso 1 1 d
C5 C 0.6395(2) 0.16768(13) 0.37707(12) 0.0237(3) Uani 1 1 d
C6 C 0.5786(2) 0.19803(13) 0.50912(11) 0.0233(3) Uani 1 1 d
C7 C 0.3778(2) 0.29524(13) 0.54901(11) 0.0212(3) Uani 1 1 d
C8 C 0.2567(2) 0.35315(13) 0.46303(11) 0.0215(3) Uani 1 1 d
C9 C 0.3112(2) 0.31517(13) 0.33094(11) 0.0227(3) Uani 1 1 d
C10 C 0.5100(2) 0.21830(13) 0.29388(11) 0.0242(3) Uani 1 1 d
C11 C 0.3193(2) 0.32086(13) 0.68198(11) 0.0220(3) Uani 1 1 d
C12 C 0.1019(2) 0.29749(14) 0.74401(12) 0.0265(3) Uani 1 1 d
H12 H -0.011(3) 0.2615(18) 0.7010(14) 0.030(4) Uiso 1 1 d
C13 C 0.0470(3) 0.31930(16) 0.86960(13) 0.0330(3) Uani 1 1 d
H13 H -0.100(3) 0.299(2) 0.9085(17) 0.042(5) Uiso 1 1 d
C14 C 0.2064(3) 0.36767(17) 0.93282(13) 0.0351(4) Uani 1 1 d
H14 H 0.166(3) 0.382(2) 1.0178(19) 0.051(5) Uiso 1 1 d
C15 C 0.4209(3) 0.39301(16) 0.87096(13) 0.0337(3) Uani 1 1 d
H15 H 0.537(3) 0.428(2) 0.9139(18) 0.046(5) Uiso 1 1 d
C16 C 0.4797(2) 0.36792(14) 0.74644(12) 0.0272(3) Uani 1 1 d
H16 H 0.633(3) 0.3843(19) 0.7056(15) 0.035(4) Uiso 1 1 d
C17 C 0.0737(2) 0.45509(13) 0.49098(11) 0.0229(3) Uani 1 1 d
O18 O 0.68824(18) 0.14332(12) 0.58529(9) 0.0372(3) Uani 1 1 d
O19 O 0.19402(17) 0.36337(11) 0.25632(8) 0.0312(3) Uani 1 1 d
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
_geom_angle_site_symmetry_1
C10 C1 C2 111.88(12) .
C3 C2 C1 109.84(12) .
C2 C3 C4 110.70(12) .
C5 C4 C3 112.12(12) .
C10 C5 C6 121.05(11) .
C10 C5 C4 122.64(12) .
C6 C5 C4 116.27(11) .
O18 C6 C5 120.48(11) .
O18 C6 C7 120.14(11) .
C5 C6 C7 119.36(11) .
C8 C7 C11 123.04(11) .
C8 C7 C6 119.08(11) .
C11 C7 C6 117.87(11) .
C7 C8 C17 122.85(11) .
C7 C8 C9 121.19(11) .
C17 C8 C9 115.95(11) .
O19 C9 C10 121.23(11) .
O19 C9 C8 120.14(11) .
C10 C9 C8 118.63(11) .
C5 C10 C9 120.45(11) .
C5 C10 C1 123.23(12) .
C9 C10 C1 116.32(11) .
C12 C11 C16 119.40(12) .
C12 C11 C7 119.86(12) .
C16 C11 C7 120.75(12) .
C11 C12 C13 120.07(13) .
C14 C13 C12 120.26(14) .
C15 C14 C13 119.70(13) .
C14 C15 C16 120.62(14) .
C15 C16 C11 119.92(13) .
C17 C17 C8 176.42(18) 2_566
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C10 1.5045(18) .
C1 C2 1.530(2) .
C2 C3 1.520(2) .
C3 C4 1.528(2) .
C4 C5 1.5116(18) .
C5 C10 1.3452(19) .
C5 C6 1.4829(18) .
C6 O18 1.2215(16) .
C6 C7 1.5047(17) .
C7 C8 1.3563(17) .
C7 C11 1.4810(16) .
C8 C17 1.4337(18) .
C8 C9 1.5005(17) .
C9 O19 1.2186(16) .
C9 C10 1.4878(18) .
C11 C12 1.3943(19) .
C11 C16 1.3961(19) .
C12 C13 1.3939(19) .
C13 C14 1.387(2) .
C14 C15 1.382(2) .
C15 C16 1.3910(19) .
C17 C17 1.198(3) 2_566
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_4
C10 C1 C2 C3 -47.17(17) .
C1 C2 C3 C4 63.14(16) .
C2 C3 C4 C5 -45.16(16) .
C3 C4 C5 C10 13.34(19) .
C3 C4 C5 C6 -168.84(12) .
C10 C5 C6 O18 174.75(13) .
C4 C5 C6 O18 -3.11(19) .
C10 C5 C6 C7 -4.27(19) .
C4 C5 C6 C7 177.87(11) .
O18 C6 C7 C8 -179.07(12) .
C5 C6 C7 C8 -0.04(18) .
O18 C6 C7 C11 -0.23(19) .
C5 C6 C7 C11 178.80(11) .
C11 C7 C8 C17 6.1(2) .
C6 C7 C8 C17 -175.12(11) .
C11 C7 C8 C9 -175.09(11) .
C6 C7 C8 C9 3.69(18) .
C7 C8 C9 O19 176.63(12) .
C17 C8 C9 O19 -4.48(18) .
C7 C8 C9 C10 -3.42(18) .
C17 C8 C9 C10 175.47(11) .
C6 C5 C10 C9 4.6(2) .
C4 C5 C10 C9 -177.69(11) .
C6 C5 C10 C1 -176.21(12) .
C4 C5 C10 C1 1.5(2) .
O19 C9 C10 C5 179.04(12) .
C8 C9 C10 C5 -0.91(19) .
O19 C9 C10 C1 -0.22(19) .
C8 C9 C10 C1 179.83(11) .
C2 C1 C10 C5 15.8(2) .
C2 C1 C10 C9 -164.94(12) .
C8 C7 C11 C12 52.72(18) .
C6 C7 C11 C12 -126.07(13) .
C8 C7 C11 C16 -127.46(14) .
C6 C7 C11 C16 53.74(16) .
C16 C11 C12 C13 -0.84(19) .
C7 C11 C12 C13 178.99(11) .
C11 C12 C13 C14 1.6(2) .
C12 C13 C14 C15 -0.6(2) .
C13 C14 C15 C16 -1.2(2) .
C14 C15 C16 C11 2.0(2) .
C12 C11 C16 C15 -0.94(19) .
C7 C11 C16 C15 179.24(12) .
C7 C8 C17 C17 129(3) 2_566
C9 C8 C17 C17 -50(3) 2_566
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139119106
