#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/55/4025504.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_4025504
loop_
_publ_author_name
'Paresh Nath Chatterjee'
'Sujit Roy'
_publ_section_title
;
 Propargylic Activation Across a Heterobimetallic Ir-Sn Catalyst:
 Nucleophilic Substitution and Indene Formation with Propargylic Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4413
_journal_page_last               4423
_journal_paper_doi               10.1021/jo100189z
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C20 H22 O3'
_chemical_formula_weight         310.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 115.609(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8477(7)
_cell_length_b                   8.6798(6)
_cell_length_c                   15.4329(8)
_cell_measurement_temperature    120(2)
_cell_volume                     1672.74(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8837
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_correction_T_min  0.9681
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0307
_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/[σ²(Fo²)+(0.0450P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2425
_reflns_number_total             2953
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100189z_si_004.cif
_cod_data_source_block           in_07_12
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        1672.74(17)
_cod_database_code               4025504
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06203(6) 0.51330(10) 0.24678(6) 0.0292(2) Uani 1 1 d . . .
O2 O 0.29487(7) 0.79666(10) 0.52030(6) 0.0319(2) Uani 1 1 d . . .
O3 O 0.42690(6) 0.51312(10) 0.32263(6) 0.0295(2) Uani 1 1 d . . .
C1 C 0.24535(9) 0.51369(13) 0.28680(8) 0.0207(3) Uani 1 1 d . . .
C2 C 0.16144(9) 0.56554(14) 0.30739(8) 0.0221(3) Uani 1 1 d . . .
C3 C 0.18041(10) 0.66198(14) 0.38464(8) 0.0247(3) Uani 1 1 d . . .
H3 H 0.1224 0.6990 0.3961 0.030 Uiso 1 1 calc R . .
C4 C 0.28480(10) 0.70402(13) 0.44513(8) 0.0237(3) Uani 1 1 d . . .
C5 C 0.36991(10) 0.65475(13) 0.42795(8) 0.0237(3) Uani 1 1 d . . .
H5 H 0.4413 0.6830 0.4698 0.028 Uiso 1 1 calc R . .
C6 C 0.34832(9) 0.56250(14) 0.34753(8) 0.0221(3) Uani 1 1 d . . .
C7 C 0.22494(9) 0.40640(13) 0.20586(8) 0.0204(3) Uani 1 1 d . . .
C8 C 0.17572(9) 0.43363(14) 0.11142(8) 0.0244(3) Uani 1 1 d . . .
H8 H 0.1522 0.5328 0.0844 0.029 Uiso 1 1 calc R . .
C9 C 0.16154(9) 0.28932(15) 0.05226(8) 0.0254(3) Uani 1 1 d . . .
C10 C 0.21086(9) 0.16929(14) 0.13038(8) 0.0220(3) Uani 1 1 d . . .
C11 C 0.25153(8) 0.24128(14) 0.22043(8) 0.0203(3) Uani 1 1 d . . .
C12 C 0.30502(9) 0.15682(14) 0.30380(8) 0.0249(3) Uani 1 1 d . . .
H12 H 0.3342 0.2060 0.3648 0.030 Uiso 1 1 calc R . .
C13 C 0.31508(11) -0.00093(15) 0.29640(10) 0.0314(3) Uani 1 1 d . . .
H13 H 0.3521 -0.0602 0.3530 0.038 Uiso 1 1 calc R . .
C14 C 0.27189(10) -0.07361(15) 0.20752(10) 0.0322(3) Uani 1 1 d . . .
H14 H 0.2779 -0.1822 0.2040 0.039 Uiso 1 1 calc R . .
C15 C 0.21979(10) 0.01158(14) 0.12357(9) 0.0277(3) Uani 1 1 d . . .
H15 H 0.1909 -0.0378 0.0626 0.033 Uiso 1 1 calc R . .
C16 C -0.02651(10) 0.56471(18) 0.26364(10) 0.0355(3) Uani 1 1 d . . .
H16A H -0.0139 0.5385 0.3294 0.053 Uiso 1 1 calc R . .
H16B H -0.0922 0.5143 0.2181 0.053 Uiso 1 1 calc R . .
H16C H -0.0341 0.6766 0.2549 0.053 Uiso 1 1 calc R . .
C17 C 0.39967(11) 0.84298(16) 0.58653(9) 0.0356(3) Uani 1 1 d . . .
H17A H 0.4431 0.7515 0.6158 0.053 Uiso 1 1 calc R . .
H17B H 0.3950 0.9072 0.6368 0.053 Uiso 1 1 calc R . .
H17C H 0.4330 0.9020 0.5526 0.053 Uiso 1 1 calc R . .
C18 C 0.52403(10) 0.59980(16) 0.35833(9) 0.0318(3) Uani 1 1 d . . .
H18A H 0.5073 0.7097 0.3467 0.048 Uiso 1 1 calc R . .
H18B H 0.5673 0.5674 0.3253 0.048 Uiso 1 1 calc R . .
H18C H 0.5642 0.5818 0.4275 0.048 Uiso 1 1 calc R . .
C19 C 0.04313(10) 0.25712(19) -0.01260(9) 0.0390(4) Uani 1 1 d . . .
H19A H 0.0362 0.1569 -0.0440 0.059 Uiso 1 1 calc R . .
H19B H 0.0147 0.3379 -0.0615 0.059 Uiso 1 1 calc R . .
H19C H 0.0029 0.2559 0.0263 0.059 Uiso 1 1 calc R . .
C20 C 0.22393(10) 0.30076(16) -0.00931(9) 0.0310(3) Uani 1 1 d . . .
H20A H 0.3001 0.3170 0.0326 0.046 Uiso 1 1 calc R . .
H20B H 0.1964 0.3875 -0.0540 0.046 Uiso 1 1 calc R . .
H20C H 0.2150 0.2050 -0.0457 0.046 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C16 117.50(9) . . ?
C4 O2 C17 118.23(10) . . ?
C6 O3 C18 117.19(9) . . ?
C6 C1 C2 117.21(10) . . ?
C6 C1 C7 121.67(10) . . ?
C2 C1 C7 121.08(10) . . ?
O1 C2 C3 123.39(10) . . ?
O1 C2 C1 115.24(10) . . ?
C3 C2 C1 121.36(11) . . ?
C2 C3 C4 119.49(11) . . ?
O2 C4 C5 124.15(11) . . ?
O2 C4 C3 114.80(10) . . ?
C5 C4 C3 121.05(11) . . ?
C4 C5 C6 118.36(11) . . ?
O3 C6 C1 115.01(10) . . ?
O3 C6 C5 122.54(10) . . ?
C1 C6 C5 122.45(10) . . ?
C8 C7 C11 108.34(10) . . ?
C8 C7 C1 128.97(11) . . ?
C11 C7 C1 122.55(10) . . ?
C7 C8 C9 112.58(11) . . ?
C8 C9 C10 101.12(9) . . ?
C8 C9 C19 111.62(10) . . ?
C10 C9 C19 112.42(11) . . ?
C8 C9 C20 111.00(10) . . ?
C10 C9 C20 110.83(10) . . ?
C19 C9 C20 109.64(10) . . ?
C15 C10 C11 120.42(11) . . ?
C15 C10 C9 130.16(11) . . ?
C11 C10 C9 109.42(10) . . ?
C12 C11 C10 120.65(11) . . ?
C12 C11 C7 130.93(11) . . ?
C10 C11 C7 108.41(10) . . ?
C11 C12 C13 118.61(12) . . ?
C12 C13 C14 120.96(12) . . ?
C13 C14 C15 120.45(12) . . ?
C10 C15 C14 118.85(12) . . ?
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 C2 1.3647(14) . ?
O1 C16 1.4303(14) . ?
O2 C4 1.3682(14) . ?
O2 C17 1.4249(16) . ?
O3 C6 1.3699(14) . ?
O3 C18 1.4276(15) . ?
C1 C6 1.3914(17) . ?
C1 C2 1.4047(15) . ?
C1 C7 1.4840(16) . ?
C2 C3 1.3857(16) . ?
C3 C4 1.3884(17) . ?
C4 C5 1.3829(16) . ?
C5 C6 1.3965(16) . ?
C7 C8 1.3364(16) . ?
C7 C11 1.4726(17) . ?
C8 C9 1.5120(17) . ?
C9 C10 1.5145(16) . ?
C9 C19 1.5328(18) . ?
C9 C20 1.5391(16) . ?
C10 C15 1.3826(17) . ?
C10 C11 1.4008(16) . ?
C11 C12 1.3848(16) . ?
C12 C13 1.3860(18) . ?
C13 C14 1.3885(19) . ?
C14 C15 1.3921(18) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659227
