#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:35:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180188 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/84/7108414.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_7108414
loop_
_publ_author_name
'Na Wu'
'Antonios Messinis'
'Andrei S. Batsanov'
'Zhen Yang'
'Andrew Whiting'
'Todd B. Marder'
_publ_section_title
;
 Palladium(II)-catalysed tandem cyclization of electron-deficient aromatic
 enynes
;
_journal_name_full               Chem.Commun.
_journal_page_first              9986
_journal_paper_doi               10.1039/c2cc35114e
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_chemical_name_common            1-Butylindeno(2,1-c)pyran-3,9-dione
_chemical_name_systematic
;
1-Butylindeno[2,1-c]pyran-3,9-dione
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-09-06
_audit_creation_method
;
Olex2 1.1-beta (compiled 2011.08.31 svn.r1945, GUI svn.r3824)
;
_cell_angle_alpha                96.461(2)
_cell_angle_beta                 93.246(2)
_cell_angle_gamma                110.029(2)
_cell_formula_units_Z            2
_cell_length_a                   5.3708(2)
_cell_length_b                   7.2029(3)
_cell_length_c                   16.9507(8)
_cell_measurement_reflns_used    1676
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.79
_cell_measurement_theta_min      2.43
_cell_volume                     608.98(5)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5759
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.22
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             268
_exptl_crystal_preparation
; Single-crystal to single-crystal phase transition in 2 stages
(ca 280K & ca 240K)
;
_exptl_crystal_recrystallization_method 'solvent diffusion: Et2O + n-hexane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0370
_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)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                1491
_reflns_number_total             2151
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc35114e.txt
_cod_data_source_block           2a
_cod_original_cell_volume        608.98(4)
_cod_database_code               7108414
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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
O1 O 0.3331(2) 0.67093(18) 0.29843(7) 0.0236(3) Uani 1 1 d .
O2 O 0.5366(2) 0.71270(19) 0.42052(7) 0.0289(3) Uani 1 1 d .
O3 O -0.2151(2) 0.86789(19) 0.14982(7) 0.0275(3) Uani 1 1 d .
C1 C 0.3900(4) 0.7650(3) 0.37911(10) 0.0231(4) Uani 1 1 d .
C2 C 0.2712(3) 0.9115(3) 0.40094(10) 0.0231(4) Uani 1 1 d .
H2 H 0.3046 0.9803 0.4538 0.028 Uiso 1 1 d R
C3 C 0.1122(3) 0.9510(3) 0.34607(10) 0.0206(4) Uani 1 1 d .
C4 C -0.0241(3) 1.0975(3) 0.35064(10) 0.0208(4) Uani 1 1 d .
C5 C -0.0283(4) 1.2378(3) 0.41299(11) 0.0252(4) Uani 1 1 d .
H5 H 0.0681 1.2520 0.4634 0.030 Uiso 1 1 d R
C6 C -0.1772(4) 1.3568(3) 0.39975(11) 0.0270(5) Uani 1 1 d .
H6 H -0.1855 1.4520 0.4422 0.032 Uiso 1 1 d R
C7 C -0.3154(4) 1.3399(3) 0.32539(11) 0.0257(5) Uani 1 1 d .
H7 H -0.4145 1.4244 0.3178 0.031 Uiso 1 1 d R
C8 C -0.3092(4) 1.2009(3) 0.26266(11) 0.0237(4) Uani 1 1 d .
H8 H -0.4023 1.1890 0.2119 0.028 Uiso 1 1 d R
C9 C -0.1631(3) 1.0795(3) 0.27606(10) 0.0202(4) Uani 1 1 d .
C10 C -0.1218(3) 0.9212(3) 0.21951(10) 0.0212(4) Uani 1 1 d .
C11 C 0.0560(3) 0.8461(3) 0.26607(10) 0.0203(4) Uani 1 1 d .
C12 C 0.1700(3) 0.7116(3) 0.24340(10) 0.0212(4) Uani 1 1 d .
C13 C 0.1431(4) 0.6016(3) 0.16156(10) 0.0271(5) Uani 1 1 d .
H13A H 0.2245 0.7004 0.1258 0.032 Uiso 1 1 d R
H13B H -0.0491 0.5401 0.1430 0.032 Uiso 1 1 d R
C14 C 0.2644(4) 0.4394(3) 0.15111(10) 0.0238(4) Uani 1 1 d .
H14A H 0.4586 0.4989 0.1669 0.029 Uiso 1 1 d R
H14B H 0.1864 0.3390 0.1866 0.029 Uiso 1 1 d R
C15 C 0.2150(4) 0.3371(3) 0.06527(11) 0.0308(5) Uani 1 1 d .
H15A H 0.2864 0.4391 0.0298 0.037 Uiso 1 1 d R
H15B H 0.0205 0.2744 0.0504 0.037 Uiso 1 1 d R
C16 C 0.3418(4) 0.1780(3) 0.05116(11) 0.0312(5) Uani 1 1 d .
H16A H 0.3027 0.1179 -0.0050 0.041(3) Uiso 1 1 d R
H16B H 0.2692 0.0745 0.0851 0.041(3) Uiso 1 1 d R
H16C H 0.5351 0.2393 0.0644 0.041(3) Uiso 1 1 d R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0266(7) 0.0250(7) 0.0218(7) -0.0002(6) -0.0015(5) 0.0141(6)
O2 0.0320(8) 0.0337(8) 0.0265(7) 0.0030(6) -0.0032(6) 0.0200(7)
O3 0.0341(8) 0.0309(8) 0.0196(7) -0.0005(6) -0.0022(6) 0.0159(6)
C1 0.0240(10) 0.0232(10) 0.0209(10) 0.0009(9) 0.0008(8) 0.0074(9)
C2 0.0248(10) 0.0241(10) 0.0208(10) -0.0009(8) 0.0004(8) 0.0107(9)
C3 0.0205(10) 0.0192(10) 0.0214(10) 0.0018(8) 0.0029(7) 0.0061(8)
C4 0.0214(10) 0.0190(10) 0.0224(10) 0.0028(8) 0.0029(8) 0.0074(8)
C5 0.0284(11) 0.0245(11) 0.0231(10) 0.0001(9) 0.0003(8) 0.0113(9)
C6 0.0322(11) 0.0206(11) 0.0284(11) -0.0044(9) 0.0014(9) 0.0122(9)
C7 0.0266(11) 0.0223(10) 0.0323(11) 0.0046(9) 0.0042(8) 0.0134(9)
C8 0.0247(10) 0.0230(10) 0.0244(10) 0.0054(9) 0.0011(8) 0.0090(9)
C9 0.0209(10) 0.0191(10) 0.0211(10) 0.0032(8) 0.0022(7) 0.0075(8)
C10 0.0210(10) 0.0216(10) 0.0205(10) 0.0035(8) 0.0028(8) 0.0066(8)
C11 0.0205(10) 0.0209(10) 0.0192(9) 0.0021(8) 0.0010(7) 0.0073(8)
C12 0.0197(10) 0.0219(10) 0.0226(10) 0.0030(8) 0.0019(7) 0.0082(8)
C13 0.0314(11) 0.0302(11) 0.0221(10) -0.0026(9) 0.0000(8) 0.0164(9)
C14 0.0260(10) 0.0223(10) 0.0238(10) 0.0020(8) 0.0029(8) 0.0098(8)
C15 0.0349(12) 0.0352(12) 0.0254(11) -0.0031(9) -0.0013(8) 0.0194(10)
C16 0.0413(12) 0.0342(12) 0.0221(10) -0.0037(9) 0.0016(9) 0.0211(10)
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
C12 O1 C1 123.11(13)
O2 C1 O1 115.30(15)
O2 C1 C2 128.03(17)
O1 C1 C2 116.66(15)
C3 C2 C1 119.63(17)
C2 C3 C11 120.94(16)
C2 C3 C4 131.19(17)
C11 C3 C4 107.85(14)
C5 C4 C9 120.68(17)
C5 C4 C3 130.91(16)
C9 C4 C3 108.40(15)
C6 C5 C4 118.08(17)
C5 C6 C7 121.45(17)
C8 C7 C6 120.55(17)
C7 C8 C9 118.13(16)
C8 C9 C4 121.10(17)
C8 C9 C10 128.99(15)
C4 C9 C10 109.90(15)
O3 C10 C11 128.33(16)
O3 C10 C9 126.65(16)
C11 C10 C9 105.02(14)
C12 C11 C3 120.68(15)
C12 C11 C10 130.43(16)
C3 C11 C10 108.81(14)
C11 C12 O1 118.92(16)
C11 C12 C13 126.38(16)
O1 C12 C13 114.68(15)
C12 C13 C14 117.56(15)
C13 C14 C15 111.58(15)
C14 C15 C16 113.51(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.367(2)
O1 C1 1.423(2)
O2 C1 1.206(2)
O3 C10 1.222(2)
C1 C2 1.435(2)
C2 C3 1.346(2)
C3 C11 1.438(2)
C3 C4 1.473(2)
C4 C5 1.385(2)
C4 C9 1.401(2)
C5 C6 1.384(2)
C6 C7 1.397(3)
C7 C8 1.386(3)
C8 C9 1.388(2)
C9 C10 1.490(2)
C10 C11 1.481(2)
C11 C12 1.345(2)
C12 C13 1.492(2)
C13 C14 1.519(2)
C14 C15 1.520(2)
C15 C16 1.525(2)
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
O1 C12 C13 C14 8.3(2)
C12 C13 C14 C15 178.49(16)
C13 C14 C15 C16 177.91(17)
