#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/69/1506939.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_1506939
loop_
_publ_author_name
'Hulin, Bernard'
'Newton, Linda S.'
'Cabral, Shawn'
'Walker, Aaron J.'
'Bordner, Jon'
_publ_section_title
;
 Three-component, stereoselective palladium-catalyzed synthesis of
 functionalized bicyclopentanoids.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4343
_journal_page_last               4345
_journal_paper_doi               10.1021/ol048140r
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C19 H23 Cl O4'
_chemical_formula_weight         350.82
_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                 90.910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7940(10)
_cell_length_b                   7.595(2)
_cell_length_c                   40.650(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1788.6(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'theta and 2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1853
_diffrn_reflns_theta_full        50.05
_diffrn_reflns_theta_max         50.05
_diffrn_reflns_theta_min         2.17
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.053
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0085(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0644
_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)+(0.1327P)²+0.4905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1833
_reflns_number_gt                1517
_reflns_number_total             1853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048140rsi20040914_024555.cif
_cod_data_source_block           x682
_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_sg_symbol_H-M      P2(1)/c
_cod_database_code               1506939
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
C1 C -0.0496(7) 0.1140(5) 0.33030(10) 0.0467(11) Uani 1 1 d .
H1 H -0.1923 0.0521 0.3242 0.080 Uiso 1 1 calc R
C2 C -0.1190(8) 0.2815(5) 0.34862(11) 0.0547(12) Uani 1 1 d .
H2A H 0.0130 0.3574 0.3527 0.080 Uiso 1 1 calc R
H2B H -0.2366 0.3465 0.3365 0.080 Uiso 1 1 calc R
C3 C -0.2123(8) 0.2083(5) 0.38047(11) 0.0565(12) Uani 1 1 d .
H3A H -0.3674 0.1628 0.3772 0.080 Uiso 1 1 calc R
H3B H -0.2150 0.2985 0.3973 0.080 Uiso 1 1 calc R
C4 C -0.0439(7) 0.0593(5) 0.39016(10) 0.0478(11) Uani 1 1 d .
H4 H 0.0740 0.1049 0.4055 0.080 Uiso 1 1 calc R
C5 C 0.0713(7) 0.0043(5) 0.35736(10) 0.0476(11) Uani 1 1 d .
H5 H 0.2364 0.0320 0.3582 0.080 Uiso 1 1 calc R
C6 C -0.1488(6) -0.1116(5) 0.40430(10) 0.0466(11) Uani 1 1 d .
H6 H -0.0316 -0.1654 0.4187 0.080 Uiso 1 1 calc R
C7 C -0.1777(8) -0.2302(5) 0.37428(11) 0.0584(13) Uani 1 1 d .
H7A H -0.1858 -0.3530 0.3807 0.080 Uiso 1 1 calc R
H7B H -0.3165 -0.2001 0.3619 0.080 Uiso 1 1 calc R
C8 C 0.0366(8) -0.1951(6) 0.35421(11) 0.0590(13) Uani 1 1 d .
H8A H 0.0123 -0.2290 0.3314 0.080 Uiso 1 1 calc R
H8B H 0.1687 -0.2587 0.3631 0.080 Uiso 1 1 calc R
C9 C 0.0864(6) 0.1375(5) 0.29941(10) 0.0442(11) Uani 1 1 d .
C10 C 0.0071(7) 0.0741(5) 0.26941(11) 0.0486(11) Uani 1 1 d .
H10 H -0.1339 0.0156 0.2685 0.080 Uiso 1 1 calc R
C11 C 0.1286(7) 0.0944(5) 0.24102(11) 0.0514(12) Uani 1 1 d .
H11 H 0.0693 0.0521 0.2212 0.080 Uiso 1 1 calc R
C12 C 0.3402(7) 0.1782(5) 0.24217(11) 0.0503(12) Uani 1 1 d .
Cl12 Cl 0.4982(2) 0.20772(18) 0.20664(3) 0.0741(6) Uani 1 1 d .
C13 C 0.4234(7) 0.2456(5) 0.27143(12) 0.0528(12) Uani 1 1 d .
H13 H 0.5630 0.3060 0.2722 0.080 Uiso 1 1 calc R
C14 C 0.2983(7) 0.2228(6) 0.29948(11) 0.0522(12) Uani 1 1 d .
H14 H 0.3576 0.2662 0.3193 0.080 Uiso 1 1 calc R
C15 C -0.3692(7) -0.0960(5) 0.42381(10) 0.0488(12) Uani 1 1 d .
H15 H -0.4944 -0.0655 0.4084 0.080 Uiso 1 1 calc R
C16 C -0.4252(7) -0.2741(6) 0.43860(11) 0.0534(12) Uani 1 1 d .
O16 O -0.2991(6) -0.3600(5) 0.45529(10) 0.0872(13) Uani 1 1 d .
O17 O -0.6388(5) -0.3240(4) 0.43044(9) 0.0737(11) Uani 1 1 d .
C18 C -0.7111(9) -0.4944(7) 0.44259(17) 0.0955(19) Uani 1 1 d .
H18A H -0.8668 -0.5173 0.4354 0.080 Uiso 1 1 calc R
H18B H -0.7034 -0.4947 0.4662 0.080 Uiso 1 1 calc R
H18C H -0.6111 -0.5841 0.4342 0.080 Uiso 1 1 calc R
C19 C -0.3683(9) 0.0408(6) 0.45140(11) 0.0526(12) Uani 1 1 d .
O19 O -0.5378(6) 0.1081(5) 0.46148(10) 0.0864(12) Uani 1 1 d .
O20 O -0.1566(6) 0.0737(4) 0.46249(7) 0.0664(10) Uani 1 1 d .
C21 C -0.1343(10) 0.2038(7) 0.48825(12) 0.0783(16) Uani 1 1 d .
H21A H 0.0254 0.2166 0.4944 0.080 Uiso 1 1 calc R
H21B H -0.2205 0.1667 0.5070 0.080 Uiso 1 1 calc R
H21C H -0.1931 0.3146 0.4805 0.080 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'
Cl Cl 0.3639 0.7018 '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
C9 C1 C2 116.9(3)
C9 C1 C5 115.0(3)
C2 C1 C5 102.8(3)
C3 C2 C1 102.2(3)
C2 C3 C4 104.8(3)
C3 C4 C6 117.4(3)
C3 C4 C5 104.8(3)
C6 C4 C5 105.6(3)
C8 C5 C1 114.7(3)
C8 C5 C4 106.2(3)
C1 C5 C4 105.7(3)
C15 C6 C7 112.4(3)
C15 C6 C4 117.8(3)
C7 C6 C4 103.7(3)
C8 C7 C6 104.2(4)
C7 C8 C5 103.6(3)
C10 C9 C14 116.5(4)
C10 C9 C1 121.6(3)
C14 C9 C1 121.9(4)
C11 C10 C9 122.4(4)
C10 C11 C12 119.4(4)
C13 C12 C11 120.0(4)
C13 C12 Cl12 119.3(3)
C11 C12 Cl12 120.7(4)
C14 C13 C12 119.3(4)
C13 C14 C9 122.4(4)
C16 C15 C6 108.9(3)
C16 C15 C19 108.3(3)
C6 C15 C19 116.3(4)
O16 C16 O17 123.3(4)
O16 C16 C15 125.7(4)
O17 C16 C15 111.1(4)
C16 O17 C18 116.3(4)
O19 C19 O20 124.7(4)
O19 C19 C15 123.6(4)
O20 C19 C15 111.7(4)
C19 O20 C21 116.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9 1.503(6)
C1 C2 1.531(6)
C1 C5 1.540(6)
C2 C3 1.517(6)
C3 C4 1.541(6)
C4 C6 1.547(6)
C4 C5 1.558(6)
C5 C8 1.532(6)
C6 C15 1.519(6)
C6 C7 1.524(6)
C7 C8 1.520(6)
C9 C10 1.383(6)
C9 C14 1.388(6)
C10 C11 1.370(6)
C11 C12 1.381(6)
C12 C13 1.375(6)
C12 Cl12 1.737(4)
C13 C14 1.372(6)
C15 C16 1.517(6)
C15 C19 1.529(6)
C16 O16 1.185(5)
C16 O17 1.331(5)
O17 C18 1.449(6)
C19 O19 1.186(5)
C19 O20 1.324(5)
O20 C21 1.444(5)
