#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023447.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_4023447
loop_
_publ_author_name
'Hyeon Mo Cho'
'Haim Weissman'
'Jeffrey S. Moore'
_publ_contact_author
; 
Scott R. Wilson 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_contact_author_email       srwilson@uiuc.edu
_publ_contact_author_fax         '1  217 244 8068'
_publ_contact_author_phone       '1  217 244 1708'
_publ_section_title
;
 Synthetic Applications with Use of a Silica-Supported
 Alkyne Metathesis Catalyst
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4256
_journal_page_last               4258
_journal_paper_doi               10.1021/jo8003919
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C38 H36 O4'
_chemical_formula_sum            'C38 H36 O4'
_chemical_formula_weight         556.67
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_audit_update_record
; 
2006-04-05   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.212(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.5686(5)
_cell_length_b                   7.0838(3)
_cell_length_c                   16.6718(6)
_cell_measurement_reflns_used    5563
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.51
_cell_volume                     1560.03(10)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'APEX2 V1.0-27 (Bruker, 2004)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  ga61ias
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16221
_diffrn_reflns_theta_full        27.23
_diffrn_reflns_theta_max         27.23
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP (Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             592
_exptl_crystal_id                ga61ias
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-7 1 1) scattering planes 
roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0063(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0354
_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)+(0.0458P)²+0.3015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                2786
_reflns_number_total             3442
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8003919-File004.cif
_cod_data_source_block           ga61ias
_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_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n  '
_cod_database_code               4023447
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.18273(8) 1.72353(15) 0.84953(7) 0.0276(2) Uani 1 1 d . . .
C2 C -0.11196(8) 1.72245(15) 0.81797(6) 0.0271(2) Uani 1 1 d . . .
C3 C -0.02956(7) 1.72976(15) 0.77754(6) 0.0258(2) Uani 1 1 d . . .
C4 C -0.02161(8) 1.87926(16) 0.72498(7) 0.0319(3) Uani 1 1 d . . .
H4 H -0.0711 1.9765 0.7163 0.038 Uiso 1 1 calc R . .
C5 C 0.05737(9) 1.88819(17) 0.68519(7) 0.0359(3) Uani 1 1 d . . .
H5 H 0.0621 1.9909 0.6496 0.043 Uiso 1 1 calc R . .
C6 C 0.12922(8) 1.74657(17) 0.69764(7) 0.0337(3) Uani 1 1 d . . .
H6 H 0.1833 1.7522 0.6702 0.040 Uiso 1 1 calc R . .
C7 C 0.12357(8) 1.59640(16) 0.74965(7) 0.0296(2) Uani 1 1 d . . .
H7 H 0.1737 1.5003 0.7578 0.035 Uiso 1 1 calc R . .
C8 C 0.04436(7) 1.58628(15) 0.78995(6) 0.0254(2) Uani 1 1 d . . .
C9 C 0.10489(8) 1.29604(15) 0.85375(7) 0.0284(2) Uani 1 1 d . . .
H9B H 0.1732 1.3489 0.8761 0.034 Uiso 1 1 calc R . .
H9A H 0.1048 1.2349 0.8003 0.034 Uiso 1 1 calc R . .
C10 C 0.08064(8) 1.15162(15) 0.91292(7) 0.0290(2) Uani 1 1 d . . .
H10A H 0.0130 1.0961 0.8903 0.035 Uiso 1 1 calc R . .
H10B H 0.0799 1.2122 0.9663 0.035 Uiso 1 1 calc R . .
C11 C 0.16153(8) 0.99753(15) 0.92534(7) 0.0288(2) Uani 1 1 d . . .
H11A H 0.1625 0.9421 0.8710 0.035 Uiso 1 1 calc R . .
H11B H 0.2284 1.0564 0.9473 0.035 Uiso 1 1 calc R . .
C12 C 0.14672(8) 0.83922(15) 0.98321(7) 0.0296(2) Uani 1 1 d . . .
H12B H 0.1462 0.8918 1.0381 0.036 Uiso 1 1 calc R . .
H12A H 0.0810 0.7760 0.9614 0.036 Uiso 1 1 calc R . .
C13 C 0.23165(8) 0.69828(15) 0.99079(7) 0.0298(2) Uani 1 1 d . . .
H13A H 0.2337 0.6487 0.9357 0.036 Uiso 1 1 calc R . .
H13B H 0.2973 0.7602 1.0145 0.036 Uiso 1 1 calc R . .
C14 C 0.28399(7) 0.40464(15) 1.05734(6) 0.0256(2) Uani 1 1 d . . .
C15 C 0.36584(8) 0.38875(16) 1.02044(7) 0.0304(3) Uani 1 1 d . . .
H15 H 0.3770 0.4823 0.9827 0.036 Uiso 1 1 calc R . .
C16 C 0.43125(8) 0.23547(17) 1.03898(7) 0.0339(3) Uani 1 1 d . . .
H16 H 0.4864 0.2242 1.0130 0.041 Uiso 1 1 calc R . .
C17 C 0.41705(8) 0.09958(18) 1.09455(7) 0.0353(3) Uani 1 1 d . . .
H17 H 0.4626 -0.0037 1.1073 0.042 Uiso 1 1 calc R . .
C18 C 0.33578(8) 0.11499(17) 1.13162(7) 0.0327(3) Uani 1 1 d . . .
H18 H 0.3261 0.0217 1.1700 0.039 Uiso 1 1 calc R . .
C19 C 0.26795(7) 0.26546(15) 1.11335(6) 0.0262(2) Uani 1 1 d . . .
O1 O 0.03153(5) 1.44481(11) 0.84152(5) 0.0309(2) Uani 1 1 d . . .
O2 O 0.21513(6) 0.54696(11) 1.04304(5) 0.0317(2) Uani 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 -1.00 1.00 0.1500
0.00 -1.00 2.00 0.1900
0.00 1.00 -2.00 0.2200
-1.00 0.00 1.00 0.0700
1.00 0.00 -1.00 0.0900
0.00 0.00 1.00 0.0700
0.00 0.00 -1.00 0.0700
2.00 1.00 0.00 0.1500
-1.00 0.00 0.00 0.0800
1.00 0.00 0.00 0.0800
0.00 1.00 0.00 0.2600
1.00 -1.00 -1.00 0.1900
-1.00 -2.00 -2.00 0.2200
-2.00 2.00 1.00 0.2600
-2.00 0.00 -1.00 0.0700
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
C2 C1 C19 177.21(11) . 3_577 ?
C1 C2 C3 176.89(11) . . ?
C4 C3 C8 119.03(9) . . ?
C4 C3 C2 120.26(10) . . ?
C8 C3 C2 120.70(9) . . ?
C5 C4 C3 121.01(10) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.46(11) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.90(10) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 120.03(10) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O1 C8 C7 124.62(9) . . ?
O1 C8 C3 115.81(9) . . ?
C7 C8 C3 119.57(10) . . ?
O1 C9 C10 110.11(8) . . ?
O1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
O1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
H9B C9 H9A 108.2 . . ?
C9 C10 C11 108.40(9) . . ?
C9 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C12 C11 C10 114.67(9) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 109.38(9) . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
H12B C12 H12A 108.2 . . ?
O2 C13 C12 108.91(8) . . ?
O2 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
O2 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O2 C14 C15 124.67(10) . . ?
O2 C14 C19 115.57(9) . . ?
C15 C14 C19 119.75(10) . . ?
C16 C15 C14 119.85(10) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.90(10) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.46(10) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 121.00(11) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C14 119.02(9) . . ?
C18 C19 C1 120.29(10) . 3_577 ?
C14 C19 C1 120.69(9) . 3_577 ?
C8 O1 C9 116.62(8) . . ?
C14 O2 C13 117.77(8) . . ?
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
C1 C2 1.1958(15) . ?
C1 C19 1.4329(14) 3_577 ?
C2 C3 1.4323(14) . ?
C3 C4 1.3943(15) . ?
C3 C8 1.4096(14) . ?
C4 C5 1.3847(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3811(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3856(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3934(14) . ?
C7 H7 0.9500 . ?
C8 O1 1.3572(12) . ?
C9 O1 1.4319(12) . ?
C9 C10 1.5088(15) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C10 C11 1.5280(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5223(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5079(15) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 O2 1.4308(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O2 1.3580(12) . ?
C14 C15 1.3918(14) . ?
C14 C19 1.4087(15) . ?
C15 C16 1.3917(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3798(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3861(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.3956(15) . ?
C18 H18 0.9500 . ?
C19 C1 1.4329(14) 3_577 ?
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
C8 C3 C4 C5 0.02(17) . . . . ?
C2 C3 C4 C5 -179.78(11) . . . . ?
C3 C4 C5 C6 0.15(18) . . . . ?
C4 C5 C6 C7 -0.31(18) . . . . ?
C5 C6 C7 C8 0.30(17) . . . . ?
C6 C7 C8 O1 179.48(10) . . . . ?
C6 C7 C8 C3 -0.13(16) . . . . ?
C4 C3 C8 O1 -179.67(9) . . . . ?
C2 C3 C8 O1 0.13(15) . . . . ?
C4 C3 C8 C7 -0.03(16) . . . . ?
C2 C3 C8 C7 179.77(10) . . . . ?
O1 C9 C10 C11 -179.06(8) . . . . ?
C9 C10 C11 C12 -179.36(9) . . . . ?
C10 C11 C12 C13 -179.43(9) . . . . ?
C11 C12 C13 O2 -178.05(9) . . . . ?
O2 C14 C15 C16 -179.30(10) . . . . ?
C19 C14 C15 C16 0.08(16) . . . . ?
C14 C15 C16 C17 -0.93(17) . . . . ?
C15 C16 C17 C18 0.78(18) . . . . ?
C16 C17 C18 C19 0.22(18) . . . . ?
C17 C18 C19 C14 -1.05(17) . . . . ?
C17 C18 C19 C1 178.25(11) . . . 3_577 ?
O2 C14 C19 C18 -179.68(9) . . . . ?
C15 C14 C19 C18 0.89(16) . . . . ?
O2 C14 C19 C1 1.02(15) . . . 3_577 ?
C15 C14 C19 C1 -178.41(10) . . . 3_577 ?
C7 C8 O1 C9 -0.69(15) . . . . ?
C3 C8 O1 C9 178.92(9) . . . . ?
C10 C9 O1 C8 179.49(9) . . . . ?
C15 C14 O2 C13 -4.58(15) . . . . ?
C19 C14 O2 C13 176.02(9) . . . . ?
C12 C13 O2 C14 179.84(9) . . . . ?
