#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/36/4023638.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_4023638
loop_
_publ_author_name
'Wei Li'
'Min Shi'
_publ_section_title
;
 An Efficient Method for the Synthesis of Vinylbromohydrin and
 Vinylbromoalkoxy Derivatives and Cyclocarbonylation of
 α-Allenic Alcohols Catalyzed by Palladium Chloride
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6698
_journal_page_last               6705
_journal_paper_doi               10.1021/jo8009352
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.40
_chemical_name_systematic
; 
 ? 
;
_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                 119.237(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6537(18)
_cell_length_b                   14.736(2)
_cell_length_c                   11.9299(18)
_cell_measurement_reflns_used    3040
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.041
_cell_measurement_theta_min      4.791
_cell_volume                     1787.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0891
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10351
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75123
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.311
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0694P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2607
_reflns_number_total             3882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8009352_si_001.cif
_cod_data_source_block           cd27476
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023638
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 -0.00125(12) 0.57839(8) 0.72850(11) 0.0716(4) Uani 1 1 d . . .
O2 O 0.03513(11) 0.72279(7) 0.79039(10) 0.0648(4) Uani 1 1 d . . .
C1 C 0.29521(14) 0.54531(9) 0.89990(13) 0.0458(4) Uani 1 1 d . . .
H1 H 0.3852 0.5603 0.9656 0.055 Uiso 1 1 calc R . .
C2 C 0.21767(14) 0.63203(9) 0.87562(13) 0.0458(4) Uani 1 1 d . . .
C3 C 0.07490(16) 0.63696(11) 0.79026(14) 0.0547(4) Uani 1 1 d . . .
C4 C 0.14568(16) 0.77905(10) 0.87572(15) 0.0562(4) Uani 1 1 d . . .
C5 C 0.25983(15) 0.71356(9) 0.92596(13) 0.0460(4) Uani 1 1 d . . .
C6 C 0.39394(15) 0.73983(9) 1.02391(15) 0.0534(4) Uani 1 1 d . . .
C7 C 0.4396(2) 0.71133(16) 1.15027(19) 0.0944(7) Uani 1 1 d . . .
H7A H 0.5319 0.7243 1.2004 0.122 Uiso 1 1 calc R . .
H7B H 0.4256 0.6472 1.1514 0.122 Uiso 1 1 calc R . .
H7C H 0.3928 0.7429 1.1859 0.122 Uiso 1 1 calc R . .
C8 C 0.4721(2) 0.79154(15) 0.9909(2) 0.0933(7) Uani 1 1 d . . .
H8A H 0.5565 0.8078 1.0533 0.112 Uiso 1 1 calc R . .
H8B H 0.4402 0.8100 0.9062 0.112 Uiso 1 1 calc R . .
C9 C 0.12023(19) 0.81328(12) 0.98146(17) 0.0720(5) Uani 1 1 d . . .
H9A H 0.0424 0.8501 0.9447 0.108 Uiso 1 1 calc R . .
H9B H 0.1939 0.8488 1.0413 0.108 Uiso 1 1 calc R . .
H9C H 0.1083 0.7626 1.0253 0.108 Uiso 1 1 calc R . .
C10 C 0.1541(2) 0.85562(12) 0.79512(19) 0.0798(6) Uani 1 1 d . . .
H10A H 0.1747 0.8312 0.7325 0.120 Uiso 1 1 calc R . .
H10B H 0.2216 0.8974 0.8496 0.120 Uiso 1 1 calc R . .
H10C H 0.0712 0.8867 0.7522 0.120 Uiso 1 1 calc R . .
C11 C 0.24941(14) 0.47172(10) 0.95936(14) 0.0495(4) Uani 1 1 d . . .
C12 C 0.26447(18) 0.38090(10) 0.94255(18) 0.0649(5) Uani 1 1 d . . .
H12 H 0.2964 0.3633 0.8880 0.078 Uiso 1 1 calc R . .
C13 C 0.2326(2) 0.31567(12) 1.0059(2) 0.0804(6) Uani 1 1 d . . .
H13 H 0.2428 0.2546 0.9931 0.096 Uiso 1 1 calc R . .
C14 C 0.1862(2) 0.33987(15) 1.0873(2) 0.0822(6) Uani 1 1 d . . .
H14 H 0.1659 0.2957 1.1306 0.099 Uiso 1 1 calc R . .
C15 C 0.1703(2) 0.42932(15) 1.1041(2) 0.0823(6) Uani 1 1 d . . .
H15 H 0.1383 0.4464 1.1588 0.099 Uiso 1 1 calc R . .
C16 C 0.20097(19) 0.49452(12) 1.04092(17) 0.0680(5) Uani 1 1 d . . .
H16 H 0.1890 0.5554 1.0532 0.082 Uiso 1 1 calc R . .
C17 C 0.30462(15) 0.51682(9) 0.78216(14) 0.0482(4) Uani 1 1 d . . .
C18 C 0.41688(17) 0.53539(11) 0.77563(17) 0.0599(4) Uani 1 1 d . . .
H18 H 0.4861 0.5657 0.8432 0.072 Uiso 1 1 calc R . .
C19 C 0.4284(2) 0.50973(14) 0.6702(2) 0.0796(6) Uani 1 1 d . . .
H19 H 0.5051 0.5225 0.6673 0.095 Uiso 1 1 calc R . .
C20 C 0.3271(3) 0.46555(13) 0.57005(19) 0.0831(7) Uani 1 1 d . . .
H20 H 0.3346 0.4480 0.4990 0.100 Uiso 1 1 calc R . .
C21 C 0.2153(2) 0.44732(12) 0.57486(17) 0.0757(6) Uani 1 1 d . . .
H21 H 0.1462 0.4173 0.5067 0.091 Uiso 1 1 calc R . .
C22 C 0.20320(18) 0.47276(10) 0.67942(15) 0.0623(5) Uani 1 1 d . . .
H22 H 0.1258 0.4602 0.6810 0.075 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
C3 O2 C4 110.44(11) . . ?
C2 C1 C17 111.29(11) . . ?
C2 C1 C11 112.21(12) . . ?
C17 C1 C11 115.60(11) . . ?
C2 C1 H1 105.6 . . ?
C17 C1 H1 105.6 . . ?
C11 C1 H1 105.6 . . ?
C5 C2 C3 108.24(13) . . ?
C5 C2 C1 128.74(14) . . ?
C3 C2 C1 122.99(12) . . ?
O1 C3 O2 121.66(15) . . ?
O1 C3 C2 129.69(15) . . ?
O2 C3 C2 108.65(13) . . ?
O2 C4 C5 102.81(11) . . ?
O2 C4 C9 107.85(14) . . ?
C5 C4 C9 112.00(13) . . ?
O2 C4 C10 106.89(13) . . ?
C5 C4 C10 114.21(15) . . ?
C9 C4 C10 112.29(14) . . ?
C2 C5 C6 127.73(14) . . ?
C2 C5 C4 109.85(13) . . ?
C6 C5 C4 122.27(12) . . ?
C8 C6 C7 121.08(17) . . ?
C8 C6 C5 120.60(16) . . ?
C7 C6 C5 118.32(15) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 120.0 . . ?
C6 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 117.59(15) . . ?
C12 C11 C1 121.60(14) . . ?
C16 C11 C1 120.60(13) . . ?
C11 C12 C13 120.62(18) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.78(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.12(18) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.43(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 121.45(17) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C18 C17 C22 117.96(15) . . ?
C18 C17 C1 119.81(14) . . ?
C22 C17 C1 122.23(14) . . ?
C17 C18 C19 121.02(17) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 119.64(18) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.65(19) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 120.76(18) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
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 C3 1.1987(19) . ?
O2 C3 1.3472(19) . ?
O2 C4 1.4499(19) . ?
C1 C2 1.5091(19) . ?
C1 C17 1.521(2) . ?
C1 C11 1.528(2) . ?
C1 H1 0.9800 . ?
C2 C5 1.3256(19) . ?
C2 C3 1.468(2) . ?
C4 C5 1.510(2) . ?
C4 C9 1.516(2) . ?
C4 C10 1.516(2) . ?
C5 C6 1.474(2) . ?
C6 C8 1.384(3) . ?
C6 C7 1.396(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.377(2) . ?
C11 C16 1.384(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.376(2) . ?
C17 C22 1.380(2) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.359(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H21 O1 0.93 2.47 3.262(2) 143.2 3_566
C15 H15 O1 0.93 2.57 3.424(2) 153.3 3_567
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C1 C2 C5 -111.27(16) . . . . ?
C11 C1 C2 C5 117.43(16) . . . . ?
C17 C1 C2 C3 70.87(18) . . . . ?
C11 C1 C2 C3 -60.43(18) . . . . ?
C4 O2 C3 O1 178.22(15) . . . . ?
C4 O2 C3 C2 -1.08(17) . . . . ?
C5 C2 C3 O1 -178.36(16) . . . . ?
C1 C2 C3 O1 -0.1(3) . . . . ?
C5 C2 C3 O2 0.86(17) . . . . ?
C1 C2 C3 O2 179.11(12) . . . . ?
C3 O2 C4 C5 0.87(16) . . . . ?
C3 O2 C4 C9 -117.61(14) . . . . ?
C3 O2 C4 C10 121.44(15) . . . . ?
C3 C2 C5 C6 175.27(14) . . . . ?
C1 C2 C5 C6 -2.8(2) . . . . ?
C3 C2 C5 C4 -0.29(16) . . . . ?
C1 C2 C5 C4 -178.41(14) . . . . ?
O2 C4 C5 C2 -0.32(16) . . . . ?
C9 C4 C5 C2 115.21(15) . . . . ?
C10 C4 C5 C2 -115.72(16) . . . . ?
O2 C4 C5 C6 -176.17(12) . . . . ?
C9 C4 C5 C6 -60.64(19) . . . . ?
C10 C4 C5 C6 68.43(19) . . . . ?
C2 C5 C6 C8 107.8(2) . . . . ?
C4 C5 C6 C8 -77.1(2) . . . . ?
C2 C5 C6 C7 -72.3(2) . . . . ?
C4 C5 C6 C7 102.80(19) . . . . ?
C2 C1 C11 C12 153.19(14) . . . . ?
C17 C1 C11 C12 24.1(2) . . . . ?
C2 C1 C11 C16 -32.14(19) . . . . ?
C17 C1 C11 C16 -161.23(14) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C1 C11 C12 C13 174.50(16) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C12 C11 C16 C15 0.7(3) . . . . ?
C1 C11 C16 C15 -174.16(15) . . . . ?
C2 C1 C17 C18 99.76(16) . . . . ?
C11 C1 C17 C18 -130.71(14) . . . . ?
C2 C1 C17 C22 -79.87(17) . . . . ?
C11 C1 C17 C22 49.66(19) . . . . ?
C22 C17 C18 C19 -0.8(2) . . . . ?
C1 C17 C18 C19 179.56(14) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C18 C17 C22 C21 0.9(2) . . . . ?
C1 C17 C22 C21 -179.50(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658732
