#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/73/4027349.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_4027349
loop_
_publ_author_name
'Dongxu Shu'
'Xiaoxun Li'
'Min Zhang'
'Patrick J. Robichaux'
'Ilia A. Guzei'
'Weiping Tang'
_publ_contact_author_address
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI  53706
USA
;
_publ_contact_author_email       iguzei@chem.wisc.edu
_publ_contact_author_fax         608-262-0381
_publ_contact_author_name
;
Guzei, Ilia A. 
;
_publ_contact_author_phone       608-263-4694
_publ_section_title
;
 Rhodium-Catalyzed Carbonylation of Cyclopropyl Substituted Propargyl
 Esters: A Tandem 1,3-Acyloxy Migration [5 + 1] Cycloaddition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6463
_journal_page_last               6472
_journal_paper_doi               10.1021/jo300973r
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H24 O3'
_chemical_formula_sum            'C16 H24 O3'
_chemical_formula_weight         264.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10
and processed with modiCIfer-03272007. 
;
_audit_update_record
;
2010-12-14 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.8150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5042(2)
_cell_length_b                   6.09200(10)
_cell_length_c                   24.0074(4)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      68.8124
_cell_measurement_theta_min      3.7013
_cell_volume                     1528.37(5)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.50° ω and 0.5 ° φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23125
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         69.54
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.9238
_exptl_absorpt_correction_T_min  0.8217
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0361
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                2621
_reflns_number_total             2835
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo300973r_si_002.cif
_cod_data_source_block           tang04
_cod_original_sg_symbol_Hall     '-P 2yn      '
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4027349
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.37789(7) 0.01560(12) 0.05270(3) 0.0214(2) Uani 1 1 d .
O2 O 0.37147(6) 0.28081(11) 0.11788(3) 0.0171(2) Uani 1 1 d .
O3 O 0.80571(7) 0.07364(13) 0.10449(3) 0.0265(2) Uani 1 1 d .
C1 C 0.10643(10) 0.20700(18) 0.03990(5) 0.0236(3) Uani 1 1 d .
H1A H 0.1296 0.3629 0.0417 0.035 Uiso 1 1 calc R
H1B H 0.0138 0.1917 0.0408 0.035 Uiso 1 1 calc R
H1C H 0.1315 0.1434 0.0051 0.035 Uiso 1 1 calc R
C2 C 0.14447(10) -0.15956(17) 0.08660(5) 0.0226(3) Uani 1 1 d .
H2A H 0.1694 -0.2186 0.0513 0.034 Uiso 1 1 calc R
H2B H 0.0523 -0.1801 0.0880 0.034 Uiso 1 1 calc R
H2C H 0.1913 -0.2369 0.1181 0.034 Uiso 1 1 calc R
C3 C 0.13573(10) 0.18157(19) 0.14479(5) 0.0231(3) Uani 1 1 d .
H3A H 0.1845 0.1107 0.1768 0.035 Uiso 1 1 calc R
H3B H 0.0441 0.1555 0.1465 0.035 Uiso 1 1 calc R
H3C H 0.1526 0.3398 0.1459 0.035 Uiso 1 1 calc R
C4 C 0.17638(9) 0.08591(16) 0.09041(4) 0.0181(3) Uani 1 1 d .
C5 C 0.31856(9) 0.11622(16) 0.08456(4) 0.0154(2) Uani 1 1 d .
C6 C 0.49798(9) 0.34104(16) 0.10896(4) 0.0159(2) Uani 1 1 d .
C7 C 0.51458(10) 0.52655(17) 0.08173(4) 0.0194(3) Uani 1 1 d .
H7 H 0.4431 0.6167 0.0700 0.023 Uiso 1 1 calc R
C8 C 0.64609(10) 0.59418(18) 0.06948(5) 0.0230(3) Uani 1 1 d .
H8A H 0.6903 0.6700 0.1024 0.028 Uiso 1 1 calc R
H8B H 0.6400 0.6972 0.0374 0.028 Uiso 1 1 calc R
C9 C 0.72210(10) 0.39036(18) 0.05561(5) 0.0227(3) Uani 1 1 d .
H9A H 0.6873 0.3347 0.0184 0.027 Uiso 1 1 calc R
H9B H 0.8122 0.4335 0.0531 0.027 Uiso 1 1 calc R
C10 C 0.71931(9) 0.20676(17) 0.09780(4) 0.0191(3) Uani 1 1 d .
C11 C 0.60461(9) 0.19840(16) 0.13120(4) 0.0166(2) Uani 1 1 d .
C12 C 0.61881(9) 0.07702(16) 0.17817(4) 0.0186(3) Uani 1 1 d .
H12 H 0.6956 -0.0066 0.1819 0.022 Uiso 1 1 calc R
C13 C 0.53798(10) 0.04555(17) 0.22643(4) 0.0208(3) Uani 1 1 d .
C14 C 0.47411(11) 0.25776(18) 0.24394(5) 0.0249(3) Uani 1 1 d .
H14A H 0.5397 0.3699 0.2533 0.037 Uiso 1 1 calc R
H14B H 0.4282 0.2289 0.2767 0.037 Uiso 1 1 calc R
H14C H 0.4137 0.3099 0.2130 0.037 Uiso 1 1 calc R
C15 C 0.43776(11) -0.13371(18) 0.21073(5) 0.0241(3) Uani 1 1 d .
H15A H 0.3791 -0.0841 0.1789 0.036 Uiso 1 1 calc R
H15B H 0.3894 -0.1630 0.2428 0.036 Uiso 1 1 calc R
H15C H 0.4809 -0.2683 0.2005 0.036 Uiso 1 1 calc R
C16 C 0.62758(12) -0.0347(2) 0.27697(5) 0.0293(3) Uani 1 1 d .
H16A H 0.6675 -0.1734 0.2675 0.044 Uiso 1 1 calc R
H16B H 0.5782 -0.0574 0.3090 0.044 Uiso 1 1 calc R
H16C H 0.6941 0.0755 0.2866 0.044 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 0.0181 0.0091 '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 0.0492 0.0322 '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_publ_flag
C5 O2 C6 115.74(7) yes
C4 C1 H1A 109.5 ?
C4 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C4 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C4 C2 H2A 109.5 ?
C4 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
C4 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
C4 C3 H3A 109.5 ?
C4 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C4 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
C5 C4 C3 113.14(8) ?
C5 C4 C2 108.83(8) ?
C3 C4 C2 110.14(9) ?
C5 C4 C1 105.24(8) ?
C3 C4 C1 109.71(9) ?
C2 C4 C1 109.64(9) ?
O1 C5 O2 122.73(9) ?
O1 C5 C4 124.91(9) ?
O2 C5 C4 112.28(8) ?
C7 C6 O2 117.89(9) ?
C7 C6 C11 123.22(9) ?
O2 C6 C11 118.87(8) ?
C6 C7 C8 120.06(9) ?
C6 C7 H7 120.0 ?
C8 C7 H7 120.0 ?
C7 C8 C9 109.33(8) ?
C7 C8 H8A 109.8 ?
C9 C8 H8A 109.8 ?
C7 C8 H8B 109.8 ?
C9 C8 H8B 109.8 ?
H8A C8 H8B 108.3 ?
C10 C9 C8 114.12(9) ?
C10 C9 H9A 108.7 ?
C8 C9 H9A 108.7 ?
C10 C9 H9B 108.7 ?
C8 C9 H9B 108.7 ?
H9A C9 H9B 107.6 ?
O3 C10 C9 121.16(10) ?
O3 C10 C11 122.07(10) ?
C9 C10 C11 116.77(9) ?
C12 C11 C6 130.08(10) ?
C12 C11 C10 115.86(9) ?
C6 C11 C10 113.85(9) ?
C11 C12 C13 133.42(10) ?
C11 C12 H12 113.3 ?
C13 C12 H12 113.3 ?
C12 C13 C14 113.39(9) ?
C12 C13 C15 108.97(9) ?
C14 C13 C15 110.98(9) ?
C12 C13 C16 107.31(9) ?
C14 C13 C16 107.53(9) ?
C15 C13 C16 108.47(9) ?
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 ?
C13 C15 H15A 109.5 ?
C13 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C13 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C13 C16 H16A 109.5 ?
C13 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C13 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.2024(13) yes
O2 C5 1.3653(12) yes
O2 C6 1.4156(12) yes
O3 C10 1.2156(13) yes
C1 C4 1.5407(14) ?
C1 H1A 0.9800 ?
C1 H1B 0.9800 ?
C1 H1C 0.9800 ?
C2 C4 1.5332(14) ?
C2 H2A 0.9800 ?
C2 H2B 0.9800 ?
C2 H2C 0.9800 ?
C3 C4 1.5295(14) ?
C3 H3A 0.9800 ?
C3 H3B 0.9800 ?
C3 H3C 0.9800 ?
C4 C5 1.5254(13) ?
C6 C7 1.3260(15) ?
C6 C11 1.4743(14) ?
C7 C8 1.4989(15) ?
C7 H7 0.9500 ?
C8 C9 1.5310(15) ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 C10 1.5112(15) ?
C9 H9A 0.9900 ?
C9 H9B 0.9900 ?
C10 C11 1.5144(14) ?
C11 C12 1.3441(14) ?
C12 C13 1.5162(14) ?
C12 H12 0.9500 ?
C13 C14 1.5347(15) ?
C13 C15 1.5371(15) ?
C13 C16 1.5381(15) ?
C14 H14A 0.9800 ?
C14 H14B 0.9800 ?
C14 H14C 0.9800 ?
C15 H15A 0.9800 ?
C15 H15B 0.9800 ?
C15 H15C 0.9800 ?
C16 H16A 0.9800 ?
C16 H16B 0.9800 ?
C16 H16C 0.9800 ?
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 O2 C5 O1 5.77(13)
C6 O2 C5 C4 -171.10(8)
C3 C4 C5 O1 162.66(10)
C2 C4 C5 O1 39.89(13)
C1 C4 C5 O1 -77.56(12)
C3 C4 C5 O2 -20.55(12)
C2 C4 C5 O2 -143.32(9)
C1 C4 C5 O2 99.23(9)
C5 O2 C6 C7 104.54(10)
C5 O2 C6 C11 -76.72(11)
O2 C6 C7 C8 -177.95(9)
C11 C6 C7 C8 3.37(15)
C6 C7 C8 C9 37.00(13)
C7 C8 C9 C10 -50.22(12)
C8 C9 C10 O3 -153.63(10)
C8 C9 C10 C11 26.02(12)
C7 C6 C11 C12 144.47(12)
O2 C6 C11 C12 -34.20(15)
C7 C6 C11 C10 -29.96(14)
O2 C6 C11 C10 151.37(8)
O3 C10 C11 C12 17.44(14)
C9 C10 C11 C12 -162.21(9)
O3 C10 C11 C6 -167.30(9)
C9 C10 C11 C6 13.06(12)
C6 C11 C12 C13 -2.93(19)
C10 C11 C12 C13 171.41(10)
C11 C12 C13 C14 -38.60(16)
C11 C12 C13 C15 85.54(13)
C11 C12 C13 C16 -157.20(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659512
