#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/53/1505388.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_1505388
loop_
_publ_author_name
'Liu, Feng'
'Loh, Teck-Peng'
_publ_section_title
;
 Highly stereoselective prins cyclization of (Z)- and (E)-gamma-brominated
 homoallylic alcohols to 2,4,5,6-tetrasubstituted tetrahydropyrans.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2063
_journal_page_last               2066
_journal_paper_doi               10.1021/ol070506n
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C19 H26 Br2 O'
_chemical_formula_weight         430.22
_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                 105.932(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4511(4)
_cell_length_b                   18.9558(7)
_cell_length_c                   9.7638(4)
_cell_measurement_reflns_used    7660
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.29
_cell_volume                     1860.00(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      273(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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23668
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    4.359
_exptl_absorpt_correction_T_max  0.4760
_exptl_absorpt_correction_T_min  0.2745
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0264
_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)+(0.0241P)²+0.7700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0599
_reflns_number_gt                4417
_reflns_number_total             5664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070506nsi20070228_070731.cif
_cod_data_source_block           ltp19m
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1860.00(12)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1505388
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
Br1 Br 0.637653(19) 0.136059(9) 0.961111(17) 0.03279(5) Uani 1 1 d
Br2 Br 0.47619(2) 0.055222(10) 0.643885(19) 0.03853(6) Uani 1 1 d
O1 O 0.47769(10) 0.28135(6) 0.83437(11) 0.0226(2) Uani 1 1 d
C1 C 0.2766(3) 0.42996(12) 0.5655(3) 0.0506(6) Uani 1 1 d
H1 H 0.359(2) 0.4331(10) 0.6090(19) 0.021(5) Uiso 1 1 d
C2 C 0.2280(5) 0.45500(13) 0.4230(4) 0.0736(10) Uani 1 1 d
H2 H 0.299(3) 0.4691(14) 0.411(3) 0.057(8) Uiso 1 1 d
C3 C 0.0966(4) 0.44825(15) 0.3531(3) 0.0751(10) Uani 1 1 d
H3 H 0.062(3) 0.4665(17) 0.252(4) 0.094(10) Uiso 1 1 d
C4 C 0.0110(4) 0.41821(15) 0.4160(3) 0.0682(8) Uani 1 1 d
H4 H -0.091(4) 0.4168(19) 0.364(4) 0.107(12) Uiso 1 1 d
C5 C 0.0559(2) 0.39303(13) 0.5529(2) 0.0472(5) Uani 1 1 d
H5 H -0.006(3) 0.3720(14) 0.600(3) 0.065(8) Uiso 1 1 d
C6 C 0.1898(2) 0.39855(10) 0.63031(19) 0.0341(4) Uani 1 1 d
C7 C 0.23445(19) 0.37021(11) 0.77986(19) 0.0330(4) Uani 1 1 d
H7A H 0.316(2) 0.3886(11) 0.825(2) 0.032(5) Uiso 1 1 d
H7B H 0.172(2) 0.3849(11) 0.834(2) 0.037(5) Uiso 1 1 d
C8 C 0.24331(17) 0.28943(10) 0.78482(19) 0.0302(4) Uani 1 1 d
H8A H 0.256(2) 0.2711(11) 0.881(2) 0.037(5) Uiso 1 1 d
H8B H 0.162(2) 0.2686(11) 0.726(2) 0.033(5) Uiso 1 1 d
C9 C 0.35623(16) 0.26058(9) 0.73164(16) 0.0248(3) Uani 1 1 d
H9 H 0.3525(18) 0.2840(10) 0.6421(19) 0.025(5) Uiso 1 1 d
C10 C 0.35289(17) 0.18067(10) 0.71463(18) 0.0277(3) Uani 1 1 d
H10A H 0.2717(19) 0.1678(11) 0.641(2) 0.030(5) Uiso 1 1 d
H10B H 0.3514(18) 0.1577(10) 0.801(2) 0.025(5) Uiso 1 1 d
C11 C 0.47535(18) 0.15738(9) 0.67258(16) 0.0265(3) Uani 1 1 d
H11 H 0.4738(18) 0.1764(10) 0.584(2) 0.026(5) Uiso 1 1 d
C12 C 0.60314(17) 0.18339(9) 0.77547(16) 0.0243(3) Uani 1 1 d
H12 H 0.6794(17) 0.1722(10) 0.7456(18) 0.021(4) Uiso 1 1 d
C13 C 0.59382(15) 0.26334(8) 0.79169(15) 0.0212(3) Uani 1 1 d
H13 H 0.5837(17) 0.2831(9) 0.6960(18) 0.019(4) Uiso 1 1 d
C14 C 0.71187(15) 0.29955(9) 0.89480(16) 0.0235(3) Uani 1 1 d
H14 H 0.7140(17) 0.2852(10) 0.9912(19) 0.022(4) Uiso 1 1 d
C15 C 0.84465(17) 0.27793(11) 0.8683(2) 0.0310(4) Uani 1 1 d
H15A H 0.841(2) 0.2897(12) 0.770(2) 0.038(6) Uiso 1 1 d
H15B H 0.858(2) 0.2288(12) 0.881(2) 0.039(6) Uiso 1 1 d
C16 C 0.96091(18) 0.31676(12) 0.9699(2) 0.0374(4) Uani 1 1 d
H16A H 1.043(2) 0.3000(12) 0.950(2) 0.048(6) Uiso 1 1 d
H16B H 0.964(2) 0.3031(12) 1.066(3) 0.047(6) Uiso 1 1 d
C17 C 0.9437(2) 0.39602(12) 0.9568(2) 0.0391(4) Uani 1 1 d
H17A H 0.947(2) 0.4115(11) 0.862(2) 0.035(5) Uiso 1 1 d
H17B H 1.021(3) 0.4203(13) 1.021(3) 0.057(7) Uiso 1 1 d
C18 C 0.81305(19) 0.41837(11) 0.9850(2) 0.0366(4) Uani 1 1 d
H18A H 0.800(2) 0.4691(13) 0.973(2) 0.051(7) Uiso 1 1 d
H18B H 0.817(2) 0.4073(12) 1.082(2) 0.042(6) Uiso 1 1 d
C19 C 0.69555(18) 0.37981(10) 0.88534(19) 0.0289(4) Uani 1 1 d
H19A H 0.688(2) 0.3939(12) 0.787(2) 0.040(6) Uiso 1 1 d
H19B H 0.615(2) 0.3939(11) 0.902(2) 0.029(5) Uiso 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'
Br Br -0.2901 2.4595 '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
C13 O1 C9 112.86(11)
C6 C1 C2 119.3(3)
C3 C2 C1 119.9(3)
C4 C3 C2 121.1(3)
C3 C4 C5 120.0(3)
C4 C5 C6 121.5(3)
C1 C6 C5 118.2(2)
C1 C6 C7 122.2(2)
C5 C6 C7 119.65(19)
C6 C7 C8 112.77(15)
C9 C8 C7 113.28(15)
O1 C9 C8 106.44(13)
O1 C9 C10 109.71(13)
C8 C9 C10 113.54(15)
C11 C10 C9 108.90(14)
C10 C11 C12 112.47(13)
C10 C11 Br2 111.40(12)
C12 C11 Br2 112.26(12)
C11 C12 C13 108.74(13)
C11 C12 Br1 111.58(11)
C13 C12 Br1 110.96(10)
O1 C13 C14 107.34(12)
O1 C13 C12 110.51(13)
C14 C13 C12 116.83(13)
C13 C14 C19 110.55(13)
C13 C14 C15 111.94(13)
C19 C14 C15 110.24(14)
C16 C15 C14 110.87(15)
C17 C16 C15 111.60(16)
C16 C17 C18 110.60(17)
C17 C18 C19 110.79(16)
C18 C19 C14 112.35(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.9651(15)
Br2 C11 1.9571(17)
O1 C13 1.4286(18)
O1 C9 1.4399(18)
C1 C6 1.376(3)
C1 C2 1.425(4)
C2 C3 1.361(5)
C3 C4 1.343(5)
C4 C5 1.375(3)
C5 C6 1.400(3)
C6 C7 1.505(3)
C7 C8 1.534(3)
C8 C9 1.516(2)
C9 C10 1.523(2)
C10 C11 1.513(2)
C11 C12 1.516(2)
C12 C13 1.530(2)
C13 C14 1.525(2)
C14 C19 1.531(2)
C14 C15 1.535(2)
C15 C16 1.530(3)
C16 C17 1.514(3)
C17 C18 1.525(3)
C18 C19 1.528(3)
