#------------------------------------------------------------------------------
#$Date: 2025-08-20 18:06:18 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301834 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/02/4120244.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_4120244
loop_
_publ_author_name
'Yuli Wang'
'Wanli Zhang'
'Shengming Ma'
_publ_section_title
;
 A Room-Temperature Catalytic Asymmetric Synthesis of Allenes with
 ECNU-Phos
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11517
_journal_page_last               11520
_journal_paper_doi               10.1021/ja406135t
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C14 H15 I O2'
_chemical_formula_weight         342.16
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   8.378(2)
_cell_length_b                   9.574(3)
_cell_length_c                   17.660(5)
_cell_measurement_temperature    296(2)
_cell_volume                     1416.5(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16292
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    2.249
_exptl_absorpt_correction_T_max  0.6876
_exptl_absorpt_correction_T_min  0.4518
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0191
_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)+(0.0205P)²+0.6072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0444
_refine_ls_wR_factor_ref         0.0454
_reflns_number_gt                2363
_reflns_number_total             2474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja406135t_si_002.cif
_cod_data_source_block           z
_cod_original_cell_volume        1416.5(6)
_cod_database_code               4120244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_refinement_flags
I1 I 1.25235(2) 0.041008(19) 0.093286(9) 0.05175(7) Uani 1 1 d .
O1 O 0.6091(2) 0.0309(4) 0.11714(15) 0.0634(7) Uani 1 1 d .
O2 O 0.7667(3) 0.1062(2) 0.02338(10) 0.0526(5) Uani 1 1 d .
C1 C 0.9705(5) -0.1077(4) -0.06561(19) 0.0588(9) Uani 1 1 d .
H1A H 0.9375 -0.1573 -0.0232 0.071 Uiso 1 1 calc R
C2 C 1.0093(5) -0.1783(4) -0.1313(2) 0.0696(10) Uani 1 1 d .
H2A H 1.0035 -0.2753 -0.1329 0.084 Uiso 1 1 calc R
C3 C 1.0566(5) -0.1049(4) -0.1944(2) 0.0701(10) Uani 1 1 d .
H3A H 1.0813 -0.1520 -0.2390 0.084 Uiso 1 1 calc R
C4 C 1.0674(5) 0.0378(4) -0.19162(19) 0.0704(10) Uani 1 1 d .
H4A H 1.1004 0.0873 -0.2341 0.085 Uiso 1 1 calc R
C5 C 1.0296(4) 0.1083(4) -0.12596(18) 0.0571(8) Uani 1 1 d .
H5A H 1.0374 0.2051 -0.1245 0.069 Uiso 1 1 calc R
C6 C 0.9805(3) 0.0368(3) -0.06260(16) 0.0436(6) Uani 1 1 d .
C7 C 0.9386(3) 0.1147(3) 0.00901(15) 0.0432(6) Uani 1 1 d .
H7A H 0.9702 0.2128 0.0040 0.052 Uiso 1 1 calc R
C8 C 1.0084(3) 0.0549(3) 0.08044(15) 0.0409(6) Uani 1 1 d .
C9 C 0.8960(4) 0.0163(4) 0.12877(19) 0.0437(8) Uani 1 1 d .
C10 C 0.7419(4) 0.0489(3) 0.09256(14) 0.0484(6) Uani 1 1 d .
C11 C 0.9076(4) -0.0468(4) 0.20606(16) 0.0511(7) Uani 1 1 d .
H11A H 0.9957 -0.1126 0.2069 0.061 Uiso 1 1 calc R
H11B H 0.8104 -0.0982 0.2166 0.061 Uiso 1 1 calc R
C12 C 0.9329(4) 0.0610(4) 0.26772(16) 0.0564(8) Uani 1 1 d .
H12A H 1.0283 0.1143 0.2563 0.068 Uiso 1 1 calc R
H12B H 0.8433 0.1252 0.2677 0.068 Uiso 1 1 calc R
C13 C 0.9496(6) -0.0017(4) 0.34593(17) 0.0716(11) Uani 1 1 d .
H13A H 0.8511 -0.0492 0.3589 0.086 Uiso 1 1 calc R
H13B H 1.0341 -0.0709 0.3450 0.086 Uiso 1 1 calc R
C14 C 0.9864(6) 0.1048(6) 0.4065(2) 0.0922(15) Uani 1 1 d .
H14A H 0.9954 0.0588 0.4546 0.138 Uiso 1 1 calc R
H14B H 0.9020 0.1725 0.4086 0.138 Uiso 1 1 calc R
H14C H 1.0852 0.1507 0.3947 0.138 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'
I I -0.4742 1.8119 '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
C10 O2 C7 109.3(2)
C2 C1 C6 120.4(3)
C2 C1 H1A 119.8
C6 C1 H1A 119.8
C3 C2 C1 119.8(3)
C3 C2 H2A 120.1
C1 C2 H2A 120.1
C4 C3 C2 120.0(3)
C4 C3 H3A 120.0
C2 C3 H3A 120.0
C3 C4 C5 120.2(3)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C6 C5 C4 120.7(3)
C6 C5 H5A 119.7
C4 C5 H5A 119.7
C5 C6 C1 118.9(3)
C5 C6 C7 120.4(3)
C1 C6 C7 120.7(3)
O2 C7 C8 102.5(2)
O2 C7 C6 110.3(2)
C8 C7 C6 115.1(2)
O2 C7 H7A 109.6
C8 C7 H7A 109.6
C6 C7 H7A 109.6
C9 C8 C7 111.7(2)
C9 C8 I1 128.1(2)
C7 C8 I1 120.19(19)
C8 C9 C10 106.5(3)
C8 C9 C11 130.9(3)
C10 C9 C11 122.6(3)
O1 C10 O2 121.6(3)
O1 C10 C9 128.4(3)
O2 C10 C9 110.0(3)
C9 C11 C12 113.0(3)
C9 C11 H11A 109.0
C12 C11 H11A 109.0
C9 C11 H11B 109.0
C12 C11 H11B 109.0
H11A C11 H11B 107.8
C13 C12 C11 113.5(3)
C13 C12 H12A 108.9
C11 C12 H12A 108.9
C13 C12 H12B 108.9
C11 C12 H12B 108.9
H12A C12 H12B 107.7
C14 C13 C12 113.5(3)
C14 C13 H13A 108.9
C12 C13 H13A 108.9
C14 C13 H13B 108.9
C12 C13 H13B 108.9
H13A C13 H13B 107.7
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C8 2.060(2)
O1 C10 1.207(4)
O2 C10 1.355(3)
O2 C7 1.464(4)
C1 C2 1.382(5)
C1 C6 1.387(5)
C1 H1A 0.9300
C2 C3 1.376(5)
C2 H2A 0.9300
C3 C4 1.370(6)
C3 H3A 0.9300
C4 C5 1.378(5)
C4 H4A 0.9300
C5 C6 1.374(4)
C5 H5A 0.9300
C6 C7 1.510(4)
C7 C8 1.504(4)
C7 H7A 0.9800
C8 C9 1.324(4)
C9 C10 1.475(4)
C9 C11 1.496(5)
C11 C12 1.515(4)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.512(4)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.509(6)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
C6 C1 C2 C3 -0.7(7)
C1 C2 C3 C4 1.0(7)
C2 C3 C4 C5 -0.6(6)
C3 C4 C5 C6 -0.1(6)
C4 C5 C6 C1 0.4(5)
C4 C5 C6 C7 -179.7(3)
C2 C1 C6 C5 0.0(6)
C2 C1 C6 C7 -179.9(3)
C10 O2 C7 C8 -0.4(3)
C10 O2 C7 C6 122.6(2)
C5 C6 C7 O2 110.8(3)
C1 C6 C7 O2 -69.3(4)
C5 C6 C7 C8 -133.9(3)
C1 C6 C7 C8 46.0(4)
O2 C7 C8 C9 0.5(3)
C6 C7 C8 C9 -119.3(3)
O2 C7 C8 I1 -179.64(17)
C6 C7 C8 I1 60.6(3)
C7 C8 C9 C10 -0.3(4)
I1 C8 C9 C10 179.8(2)
C7 C8 C9 C11 -179.6(3)
I1 C8 C9 C11 0.5(6)
C7 O2 C10 O1 -179.9(3)
C7 O2 C10 C9 0.3(3)
C8 C9 C10 O1 -179.8(3)
C11 C9 C10 O1 -0.5(4)
C8 C9 C10 O2 0.0(3)
C11 C9 C10 O2 179.4(3)
C8 C9 C11 C12 83.3(4)
C10 C9 C11 C12 -95.9(4)
C9 C11 C12 C13 -178.4(3)
C11 C12 C13 C14 175.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122347
