#------------------------------------------------------------------------------
#$Date: 2015-10-12 16:35:43 +0300 (Mon, 12 Oct 2015) $
#$Revision: 165892 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117915.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_7117915
loop_
_publ_author_name
'Sachin Bhausahe Wagh'
'Rai-Shung Liu'
_publ_section_title
;
 Gold-catalyzed reactions of propargylic esters with vinylazides for the
 synthesis of Z- or E-configured buta-1,3-dien-2-yl esters
;
_journal_name_full               Chem.Commun.
_journal_page_first              15462
_journal_paper_doi               10.1039/C5cc05945C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C18 H16 O3'
_chemical_formula_weight         280.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-07-10 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.2320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9279(6)
_cell_length_b                   7.9230(3)
_cell_length_c                   14.2519(6)
_cell_measurement_reflns_used    4573
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3866
_cell_measurement_theta_min      2.8883
_cell_volume                     1444.75(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10840
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         1.592
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0373P)²+0.7344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2500
_reflns_number_total             2947
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc05945c2.cif
_cod_data_source_block           mo_150443LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3866 2015-08-17 15:13:47Z robertas 
;
_cod_database_code               7117915
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.96425(7) -0.05586(12) 0.63334(6) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.68650(7) 0.07065(11) 0.97795(6) 0.0202(2) Uani 1 1 d . . . . .
O3 O 0.78798(7) 0.28915(12) 1.03531(7) 0.0244(2) Uani 1 1 d . . . . .
C1 C 1.07054(11) -0.0913(2) 0.62249(10) 0.0273(3) Uani 1 1 d . . . . .
H1 H 1.1173 -0.0196 0.6657 0.041 Uiso 1 1 calc R U . . .
H11 H 1.0811 -0.0682 0.5570 0.041 Uiso 1 1 calc R U . . .
H10 H 1.0859 -0.2102 0.6373 0.041 Uiso 1 1 calc R U . . .
C2 C 0.93735(10) -0.07243(16) 0.72227(9) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.83526(10) -0.02242(17) 0.73173(9) 0.0202(3) Uani 1 1 d . . . . .
H9 H 0.7904 0.0202 0.6784 0.024 Uiso 1 1 calc R U . . .
C4 C 0.79973(10) -0.03497(17) 0.81843(9) 0.0197(3) Uani 1 1 d . . . . .
H14 H 0.7305 -0.0002 0.8240 0.024 Uiso 1 1 calc R U . . .
C5 C 0.86429(10) -0.09845(16) 0.89863(9) 0.0184(3) Uani 1 1 d . . . . .
C6 C 0.83376(10) -0.11582(17) 0.99317(9) 0.0195(3) Uani 1 1 d . . . . .
H15 H 0.8743 -0.1942 1.0334 0.023 Uiso 1 1 calc R U . . .
C7 C 0.75814(10) -0.03925(16) 1.03216(9) 0.0192(3) Uani 1 1 d . . . . .
C8 C 0.70982(10) 0.23787(17) 0.98787(9) 0.0185(3) Uani 1 1 d . . . . .
C9 C 0.62756(10) 0.34614(17) 0.93442(9) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.53843(10) 0.28070(18) 0.88113(9) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.5289 0.1620 0.8763 0.026 Uiso 1 1 calc R U . . .
C11 C 0.46353(11) 0.38770(19) 0.83503(10) 0.0254(3) Uani 1 1 d . . . . .
H16 H 0.4027 0.3425 0.7984 0.030 Uiso 1 1 calc R U . . .
C12 C 0.47699(12) 0.56012(19) 0.84217(10) 0.0256(3) Uani 1 1 d . . . . .
H2 H 0.4251 0.6331 0.8105 0.031 Uiso 1 1 calc R U . . .
C13 C 0.64164(11) 0.52123(18) 0.94163(9) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.7026 0.5667 0.9779 0.028 Uiso 1 1 calc R U . . .
C14 C 0.56549(12) 0.62796(18) 0.89512(10) 0.0260(3) Uani 1 1 d . . . . .
H5 H 0.5741 0.7469 0.8997 0.031 Uiso 1 1 calc R U . . .
C15 C 0.74129(11) -0.06117(17) 1.13007(10) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.7861 -0.1373 1.1680 0.027 Uiso 1 1 calc R U . . .
C16 C 0.66827(12) 0.01665(19) 1.17092(10) 0.0274(3) Uani 1 1 d . . . . .
H6 H 0.6218 0.0938 1.1355 0.033 Uiso 1 1 calc R U . . .
H7 H 0.6625 -0.0049 1.2355 0.033 Uiso 1 1 calc R U . . .
C17 C 1.00241(10) -0.13553(17) 0.80016(9) 0.0211(3) Uani 1 1 d . . . . .
H13 H 1.0717 -0.1694 0.7945 0.025 Uiso 1 1 calc R U . . .
C18 C 0.96528(10) -0.14878(17) 0.88650(9) 0.0207(3) Uani 1 1 d . . . . .
H12 H 1.0100 -0.1936 0.9393 0.025 Uiso 1 1 calc R U . . .
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
C2 O1 C1 117.16(10) . .
C8 O2 C7 115.06(10) . .
O1 C1 H1 109.5 . .
O1 C1 H11 109.5 . .
H1 C1 H11 109.5 . .
O1 C1 H10 109.5 . .
H1 C1 H10 109.5 . .
H11 C1 H10 109.5 . .
O1 C2 C17 124.82(12) . .
O1 C2 C3 115.44(12) . .
C17 C2 C3 119.74(12) . .
C4 C3 C2 120.22(12) . .
C4 C3 H9 119.9 . .
C2 C3 H9 119.9 . .
C3 C4 C5 121.14(12) . .
C3 C4 H14 119.4 . .
C5 C4 H14 119.4 . .
C18 C5 C4 117.17(12) . .
C18 C5 C6 117.79(12) . .
C4 C5 C6 125.04(12) . .
C7 C6 C5 130.50(13) . .
C7 C6 H15 114.8 . .
C5 C6 H15 114.8 . .
C6 C7 O2 120.79(12) . .
C6 C7 C15 124.32(12) . .
O2 C7 C15 114.89(11) . .
O3 C8 O2 122.86(12) . .
O3 C8 C9 125.03(12) . .
O2 C8 C9 112.11(11) . .
C10 C9 C13 119.96(13) . .
C10 C9 C8 122.80(12) . .
C13 C9 C8 117.22(12) . .
C11 C10 C9 120.15(13) . .
C11 C10 H3 119.9 . .
C9 C10 H3 119.9 . .
C12 C11 C10 120.05(14) . .
C12 C11 H16 120.0 . .
C10 C11 H16 120.0 . .
C11 C12 C14 120.67(13) . .
C11 C12 H2 119.7 . .
C14 C12 H2 119.7 . .
C14 C13 C9 119.42(13) . .
C14 C13 H4 120.3 . .
C9 C13 H4 120.3 . .
C12 C14 C13 119.75(13) . .
C12 C14 H5 120.1 . .
C13 C14 H5 120.1 . .
C16 C15 C7 125.35(13) . .
C16 C15 H8 117.3 . .
C7 C15 H8 117.3 . .
C15 C16 H6 120.0 . .
C15 C16 H7 120.0 . .
H6 C16 H7 120.0 . .
C2 C17 C18 119.35(12) . .
C2 C17 H13 120.3 . .
C18 C17 H13 120.3 . .
C17 C18 C5 122.37(12) . .
C17 C18 H12 118.8 . .
C5 C18 H12 118.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.3676(15) .
O1 C1 1.4323(16) .
O2 C8 1.3616(16) .
O2 C7 1.4170(16) .
O3 C8 1.2032(16) .
C1 H1 0.9800 .
C1 H11 0.9800 .
C1 H10 0.9800 .
C2 C17 1.3865(19) .
C2 C3 1.4029(18) .
C3 C4 1.3820(18) .
C3 H9 0.9500 .
C4 C5 1.4082(18) .
C4 H14 0.9500 .
C5 C18 1.3993(18) .
C5 C6 1.4638(18) .
C6 C7 1.3372(19) .
C6 H15 0.9500 .
C7 C15 1.4532(18) .
C8 C9 1.4882(18) .
C9 C10 1.3868(19) .
C9 C13 1.4010(19) .
C10 C11 1.380(2) .
C10 H3 0.9500 .
C11 C12 1.379(2) .
C11 H16 0.9500 .
C12 C14 1.386(2) .
C12 H2 0.9500 .
C13 C14 1.392(2) .
C13 H4 0.9500 .
C14 H5 0.9500 .
C15 C16 1.330(2) .
C15 H8 0.9500 .
C16 H6 0.9500 .
C16 H7 0.9500 .
C17 C18 1.3874(19) .
C17 H13 0.9500 .
C18 H12 0.9500 .
