#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024422.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_4024422
loop_
_publ_author_name
'Nai-Wen Tseng'
'Mark Lautens'
_publ_section_title
;
Rhodium-Catalyzed Vinylcyclopropanation/Cyclopentenation of Strained
Alkenes via a Sequential Carborhodation Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2521
_journal_page_last               2526
_journal_paper_doi               10.1021/jo900039g
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 Br O2'
_chemical_formula_sum            'C20 H23 Br O2'
_chemical_formula_weight         375.29
_chemical_name_systematic
; 
 ? 
;
_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                   6.9387(2)
_cell_length_b                   13.8095(5)
_cell_length_c                   18.6075(6)
_cell_measurement_reflns_used    8709
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1782.97(10)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2003)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.12'
_computing_publication_material  'SHELXTL V6.12'
_computing_structure_refinement  'SHELXTL V6.12(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8079
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.313
_exptl_absorpt_correction_T_max  0.635
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.079(10)
_refine_ls_extinction_coef       0.0068(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0366
_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)+(0.0354P)²+0.2211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                2538
_reflns_number_total             3765
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo900039g_si_002.cif
_cod_data_source_block           k0598
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4024422
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
Br1 Br -0.19942(5) 0.93832(3) 0.71002(2) 0.08570(18) Uani 1 1 d . . .
O1 O 0.6104(3) 0.66364(16) 0.71783(11) 0.0648(6) Uani 1 1 d . . .
O2 O 0.4918(4) 0.6180(2) 0.82412(13) 0.0941(9) Uani 1 1 d . . .
C1 C 0.7781(4) 0.58223(19) 0.58761(14) 0.0485(6) Uani 1 1 d . . .
H1A H 0.6771 0.6316 0.5836 0.058 Uiso 1 1 calc R . .
C2 C 0.6827(4) 0.4824(2) 0.58152(14) 0.0519(7) Uani 1 1 d . . .
H2A H 0.7169 0.4417 0.6227 0.062 Uiso 1 1 calc R . .
C3 C 0.4632(4) 0.4833(2) 0.56997(17) 0.0611(8) Uani 1 1 d . . .
H3A H 0.3930 0.5285 0.6010 0.073 Uiso 1 1 calc R . .
C4 C 0.3870(6) 0.3807(3) 0.57106(19) 0.0851(12) Uani 1 1 d . . .
H4A H 0.2472 0.3801 0.5726 0.102 Uiso 1 1 calc R . .
H4B H 0.4365 0.3453 0.6121 0.102 Uiso 1 1 calc R . .
C5 C 0.4627(6) 0.3369(3) 0.4994(2) 0.0893(12) Uani 1 1 d . . .
H5A H 0.5470 0.2822 0.5081 0.107 Uiso 1 1 calc R . .
H5B H 0.3572 0.3166 0.4687 0.107 Uiso 1 1 calc R . .
C6 C 0.5730(5) 0.4218(3) 0.46647(17) 0.0672(9) Uani 1 1 d . . .
H6A H 0.5925 0.4171 0.4144 0.081 Uiso 1 1 calc R . .
C7 C 0.7580(4) 0.4367(2) 0.50984(16) 0.0588(7) Uani 1 1 d . . .
H7A H 0.8239 0.3750 0.5187 0.071 Uiso 1 1 calc R . .
C8 C 0.8939(4) 0.5113(3) 0.48175(18) 0.0607(8) Uani 1 1 d . . .
H8A H 0.9641 0.5033 0.4396 0.073 Uiso 1 1 calc R . .
C9 C 0.9056(4) 0.5894(2) 0.52188(16) 0.0521(7) Uani 1 1 d . . .
C10 C 0.4521(4) 0.5069(3) 0.48988(18) 0.0653(9) Uani 1 1 d . . .
H10A H 0.3216 0.5042 0.4713 0.078 Uiso 1 1 calc R . .
H10B H 0.5108 0.5687 0.4781 0.078 Uiso 1 1 calc R . .
C11 C 1.0259(5) 0.6774(2) 0.5083(2) 0.0736(10) Uani 1 1 d . . .
H11A H 1.0969 0.6692 0.4645 0.110 Uiso 1 1 calc R . .
H11B H 1.1142 0.6865 0.5475 0.110 Uiso 1 1 calc R . .
H11C H 0.9439 0.7331 0.5043 0.110 Uiso 1 1 calc R . .
C12 C 0.8852(4) 0.5983(2) 0.65847(17) 0.0613(8) Uani 1 1 d . . .
H12A H 0.9882 0.5511 0.6621 0.074 Uiso 1 1 calc R . .
H12B H 0.9438 0.6620 0.6576 0.074 Uiso 1 1 calc R . .
C13 C 0.7602(5) 0.5905(2) 0.72420(16) 0.0654(9) Uani 1 1 d . . .
H13A H 0.7032 0.5265 0.7272 0.078 Uiso 1 1 calc R . .
H13B H 0.8361 0.6016 0.7672 0.078 Uiso 1 1 calc R . .
C14 C 0.4818(5) 0.6669(2) 0.77111(16) 0.0606(8) Uani 1 1 d . . .
C15 C 0.3226(5) 0.7358(2) 0.75588(15) 0.0551(7) Uani 1 1 d . . .
C16 C 0.1689(5) 0.7399(3) 0.80283(16) 0.0715(10) Uani 1 1 d . . .
H16A H 0.1700 0.7017 0.8440 0.086 Uiso 1 1 calc R . .
C17 C 0.0142(5) 0.7996(3) 0.7898(2) 0.0720(9) Uani 1 1 d . . .
H17A H -0.0895 0.8010 0.8215 0.086 Uiso 1 1 calc R . .
C18 C 0.0146(5) 0.8575(2) 0.72901(17) 0.0614(8) Uani 1 1 d . . .
C19 C 0.1662(5) 0.8552(2) 0.68233(17) 0.0648(9) Uani 1 1 d . . .
H19A H 0.1653 0.8945 0.6417 0.078 Uiso 1 1 calc R . .
C20 C 0.3200(5) 0.7951(2) 0.69503(15) 0.0623(8) Uani 1 1 d . . .
H20A H 0.4229 0.7939 0.6630 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'
Br Br -0.2901 2.4595 '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
C14 O1 C13 116.2(2) . . ?
C9 C1 C12 113.8(2) . . ?
C9 C1 C2 104.6(2) . . ?
C12 C1 C2 113.8(2) . . ?
C1 C2 C3 115.5(3) . . ?
C1 C2 C7 106.4(2) . . ?
C3 C2 C7 102.4(2) . . ?
C4 C3 C10 101.3(3) . . ?
C4 C3 C2 109.7(3) . . ?
C10 C3 C2 100.8(2) . . ?
C3 C4 C5 103.6(3) . . ?
C6 C5 C4 102.4(3) . . ?
C10 C6 C5 101.7(3) . . ?
C10 C6 C7 102.1(2) . . ?
C5 C6 C7 108.1(3) . . ?
C8 C7 C6 116.0(3) . . ?
C8 C7 C2 103.3(3) . . ?
C6 C7 C2 102.9(2) . . ?
C9 C8 C7 114.0(3) . . ?
C8 C9 C11 127.3(3) . . ?
C8 C9 C1 111.7(3) . . ?
C11 C9 C1 121.1(3) . . ?
C6 C10 C3 95.0(3) . . ?
C13 C12 C1 114.3(2) . . ?
O1 C13 C12 107.2(2) . . ?
O2 C14 O1 123.6(3) . . ?
O2 C14 C15 124.2(3) . . ?
O1 C14 C15 112.1(3) . . ?
C16 C15 C20 118.6(3) . . ?
C16 C15 C14 118.7(3) . . ?
C20 C15 C14 122.7(3) . . ?
C17 C16 C15 121.2(3) . . ?
C16 C17 C18 119.2(3) . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 Br1 120.0(3) . . ?
C17 C18 Br1 119.5(2) . . ?
C18 C19 C20 120.3(3) . . ?
C19 C20 C15 120.3(3) . . ?
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
Br1 C18 1.891(3) . ?
O1 C14 1.335(4) . ?
O1 C13 1.454(4) . ?
O2 C14 1.197(4) . ?
C1 C9 1.513(4) . ?
C1 C12 1.530(4) . ?
C1 C2 1.533(4) . ?
C2 C3 1.539(4) . ?
C2 C7 1.565(4) . ?
C3 C4 1.512(5) . ?
C3 C10 1.527(4) . ?
C4 C5 1.556(5) . ?
C5 C6 1.529(5) . ?
C6 C10 1.508(5) . ?
C6 C7 1.530(4) . ?
C7 C8 1.492(4) . ?
C8 C9 1.314(4) . ?
C9 C11 1.496(4) . ?
C12 C13 1.503(4) . ?
C14 C15 1.484(5) . ?
C15 C16 1.380(4) . ?
C15 C20 1.398(4) . ?
C16 C17 1.374(5) . ?
C17 C18 1.386(5) . ?
C18 C19 1.365(4) . ?
C19 C20 1.372(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658921
