#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:35:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180188 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/84/7108415.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_7108415
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_melting_point          497.7(5)
_chemical_name_common            1-tert-butylindeno(2,1-c)pyran-3,9-dione
_chemical_name_systematic
;
1-tert-butylindeno[2,1-c]pyran-3,9-dione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-12-01
_audit_creation_method
' Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2272(14)
_cell_length_b                   14.8729(17)
_cell_length_c                   6.6914(8)
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.681
_cell_measurement_theta_min      2.156
_cell_volume                     1216.9(2)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.630 (Bruker, 2003)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1022
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5934
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_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_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0469
_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)+(0.0589P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                840
_reflns_number_total             1169
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc35114e.txt
_cod_data_source_block           2c
_cod_database_code               7108415
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x, -y+1/2, -z'
5 '-x, -y, -z'
6 'x, y, -z-1/2'
7 'x, -y-1/2, z-1/2'
8 '-x, y-1/2, 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 0.57641(14) 0.48408(13) 0.2500 0.0208(5) Uani 1 2 d S
O2 O 0.40774(15) 0.53785(15) 0.2500 0.0316(6) Uani 1 2 d S
O3 O 0.93440(15) 0.56500(14) 0.2500 0.0243(5) Uani 1 2 d S
C1 C 0.5042(2) 0.5575(2) 0.2500 0.0224(7) Uani 1 2 d S
C2 C 0.5525(2) 0.6448(2) 0.2500 0.0204(6) Uani 1 2 d S
H2 H 0.5076 0.6969 0.2500 0.025 Uiso 1 2 calc SR
C3 C 0.6625(2) 0.65280(19) 0.2500 0.0180(6) Uani 1 2 d S
C4 C 0.7309(2) 0.73380(18) 0.2500 0.0180(6) Uani 1 2 d S
C5 C 0.7032(2) 0.82455(19) 0.2500 0.0205(6) Uani 1 2 d S
H5 H 0.6287 0.8429 0.2500 0.025 Uiso 1 2 calc SR
C6 C 0.7864(2) 0.8874(2) 0.2500 0.0217(7) Uani 1 2 d S
H6 H 0.7686 0.9496 0.2500 0.026 Uiso 1 2 calc SR
C7 C 0.8958(2) 0.8615(2) 0.2500 0.0239(7) Uani 1 2 d S
H7 H 0.9516 0.9060 0.2500 0.029 Uiso 1 2 calc SR
C8 C 0.9241(2) 0.77072(19) 0.2500 0.0205(7) Uani 1 2 d S
H8 H 0.9986 0.7526 0.2500 0.025 Uiso 1 2 calc SR
C9 C 0.8408(2) 0.7077(2) 0.2500 0.0184(6) Uani 1 2 d S
C10 C 0.8489(2) 0.6078(2) 0.2500 0.0174(6) Uani 1 2 d S
C11 C 0.7329(2) 0.57468(18) 0.2500 0.0173(6) Uani 1 2 d S
C12 C 0.6884(2) 0.49149(19) 0.2500 0.0178(6) Uani 1 2 d S
C13 C 0.7439(2) 0.40025(18) 0.2500 0.0192(6) Uani 1 2 d S
C14 C 0.6597(2) 0.3238(2) 0.2500 0.0265(7) Uani 1 2 d S
H14A H 0.6110 0.3276 0.3661 0.040 Uiso 1 1 d R
H14B H 0.6978 0.2659 0.2500 0.040 Uiso 1 2 d SR
C15 C 0.81465(15) 0.39230(14) 0.4403(3) 0.0239(5) Uani 1 1 d .
H15A H 0.8685 0.4411 0.4428 0.036 Uiso 1 1 d R
H15B H 0.8527 0.3343 0.4404 0.036 Uiso 1 1 d R
H15C H 0.7677 0.3965 0.5587 0.036 Uiso 1 1 d 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'
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_3
C12 O1 C1 124.4(2) .
O1 C1 C2 116.6(2) .
O2 C1 O1 115.1(3) .
O2 C1 C2 128.3(3) .
C1 C2 H2 120.2 .
C3 C2 C1 119.5(3) .
C3 C2 H2 120.2 .
C2 C3 C4 129.8(3) .
C2 C3 C11 121.4(3) .
C11 C3 C4 108.7(2) .
C5 C4 C3 131.2(3) .
C5 C4 C9 120.2(3) .
C9 C4 C3 108.6(2) .
C4 C5 H5 120.8 .
C6 C5 C4 118.5(3) .
C6 C5 H5 120.8 .
C5 C6 H6 119.3 .
C5 C6 C7 121.3(3) .
C7 C6 H6 119.3 .
C6 C7 H7 119.8 .
C6 C7 C8 120.5(3) .
C8 C7 H7 119.8 .
C7 C8 H8 120.9 .
C9 C8 C7 118.2(3) .
C9 C8 H8 120.9 .
C4 C9 C10 109.9(2) .
C8 C9 C4 121.3(3) .
C8 C9 C10 128.8(2) .
O3 C10 C9 125.1(2) .
O3 C10 C11 129.5(3) .
C9 C10 C11 105.4(2) .
C3 C11 C10 107.4(2) .
C12 C11 C3 119.7(2) .
C12 C11 C10 132.9(3) .
O1 C12 C13 112.0(2) .
C11 C12 O1 118.3(2) .
C11 C12 C13 129.7(2) .
C12 C13 C14 111.2(2) .
C12 C13 C15 108.61(15) .
C12 C13 C15 108.60(15) 6_556
C14 C13 C15 108.63(15) 6_556
C14 C13 C15 108.63(15) .
C15 C13 C15 111.2(2) 6_556
C13 C14 H14A 111.5 .
C13 C14 H14B 109.4 .
H14A C14 H14A 104.8 6_556
H14A C14 H14B 109.8 .
C13 C15 H15A 109.5 .
C13 C15 H15B 109.5 .
C13 C15 H15C 109.5 .
H15A C15 H15B 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.404(3) .
O1 C12 1.374(3) .
O2 C1 1.215(3) .
O3 C10 1.224(3) .
C1 C2 1.426(4) .
C2 H2 0.9500 .
C2 C3 1.351(4) .
C3 C4 1.466(4) .
C3 C11 1.446(4) .
C4 C5 1.392(4) .
C4 C9 1.399(4) .
C5 H5 0.9500 .
C5 C6 1.383(4) .
C6 H6 0.9500 .
C6 C7 1.392(4) .
C7 H7 0.9500 .
C7 C8 1.394(4) .
C8 H8 0.9500 .
C8 C9 1.385(4) .
C9 C10 1.489(4) .
C10 C11 1.501(4) .
C11 C12 1.352(4) .
C12 C13 1.517(4) .
C13 C14 1.534(4) .
C13 C15 1.544(2) 6_556
C13 C15 1.544(2) .
C14 H14A 0.9800 .
C14 H14B 0.9799 .
C15 H15A 0.9800 .
C15 H15B 0.9799 .
C15 H15C 0.9800 .
