#------------------------------------------------------------------------------
#$Date: 2015-12-06 07:32:31 +0200 (Sun, 06 Dec 2015) $
#$Revision: 170764 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/06/1540616.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_1540616
loop_
_publ_author_name
'Wagner, Frederic'
'Harms, Klaus'
'Koert, Ulrich'
_publ_section_title
;
 Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to
 Substituted Naphthalenes.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5670
_journal_page_last               5673
_journal_paper_doi               10.1021/acs.orglett.5b02952
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C15 H16 O5'
_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_weight         276.28
_chemical_name_common            FWHA041b
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                93.039(2)
_cell_angle_beta                 104.730(2)
_cell_angle_gamma                106.745(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9292(4)
_cell_length_b                   8.4053(4)
_cell_length_c                   10.7094(5)
_cell_measurement_reflns_used    7780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4869
_cell_measurement_theta_min      2.5543
_cell_volume                     654.85(6)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX2 2014.9-0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14228
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.554
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       nugget
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0560P)²+0.1765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2563
_reflns_number_total             3010
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b02952_si_001.cif
_cod_data_source_block           39
_cod_database_code               1540616
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.25225(14) 0.58491(13) 0.58887(10) 0.0117(2) Uani 1 1 d . .
H1 H 0.2941 0.6965 0.6324 0.014 Uiso 1 1 calc R U
C2 C 0.15574(14) 0.45678(13) 0.64373(10) 0.0121(2) Uani 1 1 d . .
O3 O -0.00921(11) 0.16010(9) 0.62617(8) 0.01916(19) Uani 1 1 d . .
H3 H -0.014(3) 0.207(2) 0.7024(19) 0.053(5) Uiso 1 1 d . .
C3 C 0.09026(14) 0.28976(13) 0.57721(10) 0.0128(2) Uani 1 1 d . .
C4 C 0.12540(14) 0.25636(13) 0.46098(10) 0.0132(2) Uani 1 1 d . .
H4 H 0.0808 0.1448 0.4172 0.016 Uiso 1 1 calc R U
C5 C 0.27110(14) 0.35455(13) 0.28814(10) 0.0123(2) Uani 1 1 d . .
H5 H 0.2304 0.2432 0.2444 0.015 Uiso 1 1 calc R U
O6 O 0.42239(11) 0.46462(9) 0.12627(7) 0.01474(18) Uani 1 1 d . .
C6 C 0.37118(14) 0.48244(13) 0.23706(10) 0.0122(2) Uani 1 1 d . .
O7 O 0.52793(11) 0.76782(9) 0.23875(7) 0.01614(18) Uani 1 1 d . .
C7 C 0.43124(14) 0.65183(13) 0.30062(10) 0.0126(2) Uani 1 1 d . .
C8 C 0.39117(14) 0.68533(13) 0.41409(10) 0.0125(2) Uani 1 1 d . .
H8 H 0.4314 0.7975 0.4561 0.015 Uiso 1 1 calc R U
C9 C 0.28988(13) 0.55392(12) 0.46992(9) 0.0114(2) Uani 1 1 d . .
C10 C 0.22716(14) 0.38648(13) 0.40625(10) 0.0113(2) Uani 1 1 d . .
C11 C 0.36954(15) 0.29761(13) 0.06000(10) 0.0159(2) Uani 1 1 d . .
H11A H 0.4135 0.3005 -0.0177 0.024 Uiso 1 1 calc R U
H11B H 0.2355 0.2500 0.0342 0.024 Uiso 1 1 calc R U
H11C H 0.4235 0.2281 0.1183 0.024 Uiso 1 1 calc R U
C12 C 0.59352(16) 0.93745(13) 0.30087(11) 0.0189(2) Uani 1 1 d . .
H12A H 0.6616 1.0095 0.2494 0.028 Uiso 1 1 calc R U
H12B H 0.6747 0.9448 0.3884 0.028 Uiso 1 1 calc R U
H12C H 0.4892 0.9744 0.3074 0.028 Uiso 1 1 calc R U
C1' C 0.11971(14) 0.48837(13) 0.76992(10) 0.0128(2) Uani 1 1 d . .
O1' O 0.03898(11) 0.37750(9) 0.82324(7) 0.01712(18) Uani 1 1 d . .
C2' C 0.14775(15) 0.68183(13) 0.94697(10) 0.0143(2) Uani 1 1 d . .
H2'A H 0.2200 0.6335 1.0152 0.017 Uiso 1 1 calc R U
H2'B H 0.0159 0.6305 0.9397 0.017 Uiso 1 1 calc R U
O2' O 0.18317(10) 0.64930(9) 0.82223(7) 0.01331(18) Uani 1 1 d . .
C3' C 0.20312(17) 0.86911(15) 0.98140(11) 0.0218(3) Uani 1 1 d . .
H3'A H 0.1796 0.8955 1.0644 0.033 Uiso 1 1 calc R U
H3'B H 0.1316 0.9156 0.9127 0.033 Uiso 1 1 calc R U
H3'C H 0.3341 0.9182 0.9895 0.033 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
C2 C1 C9 121.53(9)
C2 C1 H1 119.2
C9 C1 H1 119.2
C1 C2 C3 119.20(9)
C1 C2 C1' 121.64(9)
C3 C2 C1' 119.15(9)
C3 O3 H3 104.8(12)
O3 C3 C4 118.46(9)
O3 C3 C2 121.21(9)
C4 C3 C2 120.32(9)
C3 C4 C10 120.52(10)
C3 C4 H4 119.7
C10 C4 H4 119.7
C6 C5 C10 120.83(9)
C6 C5 H5 119.6
C10 C5 H5 119.6
C6 O6 C11 116.82(8)
O6 C6 C5 125.28(9)
O6 C6 C7 114.32(9)
C5 C6 C7 120.39(9)
C7 O7 C12 116.11(8)
C8 C7 O7 125.65(9)
C8 C7 C6 119.79(9)
O7 C7 C6 114.56(9)
C7 C8 C9 120.70(9)
C7 C8 H8 119.6
C9 C8 H8 119.6
C1 C9 C10 118.59(9)
C1 C9 C8 121.62(9)
C10 C9 C8 119.78(9)
C4 C10 C9 119.80(9)
C4 C10 C5 121.71(9)
C9 C10 C5 118.49(9)
O6 C11 H11A 109.5
O6 C11 H11B 109.5
H11A C11 H11B 109.5
O6 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O7 C12 H12A 109.5
O7 C12 H12B 109.5
H12A C12 H12B 109.5
O7 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O1' C1' O2' 122.27(9)
O1' C1' C2 123.52(10)
O2' C1' C2 114.22(9)
O2' C2' C3' 107.27(9)
O2' C2' H2'A 110.3
C3' C2' H2'A 110.3
O2' C2' H2'B 110.3
C3' C2' H2'B 110.3
H2'A C2' H2'B 108.5
C1' O2' C2' 114.61(8)
C2' C3' H3'A 109.5
C2' C3' H3'B 109.5
H3'A C3' H3'B 109.5
C2' C3' H3'C 109.5
H3'A C3' H3'C 109.5
H3'B C3' H3'C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3826(15)
C1 C9 1.4081(14)
C1 H1 0.9500
C2 C3 1.4261(14)
C2 C1' 1.4766(14)
O3 C3 1.3640(13)
O3 H3 0.90(2)
C3 C4 1.3748(14)
C4 C10 1.4110(15)
C4 H4 0.9500
C5 C6 1.3697(15)
C5 C10 1.4266(14)
C5 H5 0.9500
O6 C6 1.3625(12)
O6 C11 1.4332(12)
C6 C7 1.4348(14)
O7 C7 1.3687(13)
O7 C12 1.4290(12)
C7 C8 1.3670(14)
C8 C9 1.4232(14)
C8 H8 0.9500
C9 C10 1.4196(14)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C1' O1' 1.2258(13)
C1' O2' 1.3345(13)
C2' O2' 1.4610(12)
C2' C3' 1.5048(15)
C2' H2'A 0.9900
C2' H2'B 0.9900
C3' H3'A 0.9800
C3' H3'B 0.9800
C3' H3'C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O1' 0.90(2) 1.76(2) 2.5918(11) 152.6(18)
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
C9 C1 C2 C3 -1.03(15)
C9 C1 C2 C1' 178.60(9)
C1 C2 C3 O3 -178.46(9)
C1' C2 C3 O3 1.91(15)
C1 C2 C3 C4 1.06(15)
C1' C2 C3 C4 -178.57(9)
O3 C3 C4 C10 179.78(9)
C2 C3 C4 C10 0.25(16)
C11 O6 C6 C5 -1.27(15)
C11 O6 C6 C7 178.73(8)
C10 C5 C6 O6 178.97(9)
C10 C5 C6 C7 -1.02(15)
C12 O7 C7 C8 0.94(15)
C12 O7 C7 C6 -178.64(9)
O6 C6 C7 C8 -178.81(9)
C5 C6 C7 C8 1.18(15)
O6 C6 C7 O7 0.80(13)
C5 C6 C7 O7 -179.20(9)
O7 C7 C8 C9 -179.74(9)
C6 C7 C8 C9 -0.17(15)
C2 C1 C9 C10 -0.30(15)
C2 C1 C9 C8 -179.21(9)
C7 C8 C9 C1 177.91(10)
C7 C8 C9 C10 -0.98(15)
C3 C4 C10 C9 -1.59(15)
C3 C4 C10 C5 177.79(9)
C1 C9 C10 C4 1.61(15)
C8 C9 C10 C4 -179.46(9)
C1 C9 C10 C5 -177.79(9)
C8 C9 C10 C5 1.13(15)
C6 C5 C10 C4 -179.53(9)
C6 C5 C10 C9 -0.13(15)
C1 C2 C1' O1' -178.00(10)
C3 C2 C1' O1' 1.62(16)
C1 C2 C1' O2' 1.86(14)
C3 C2 C1' O2' -178.52(9)
O1' C1' O2' C2' -0.28(14)
C2 C1' O2' C2' 179.85(8)
C3' C2' O2' C1' -171.95(9)
