#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:50:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180216 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/02/7110205.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_7110205
loop_
_publ_author_name
'Kazuhiro Hata'
'Zhiheng He'
'Constantin Gabriel Daniliuc'
'Kenichiro Itami'
'Armido Studer'
_publ_section_title
;
 Synthesis of dihydrobenzo[b]furans by diastereoselective acyloxyarylation
;
_journal_name_full               Chem.Commun.
_journal_page_first              463
_journal_paper_doi               10.1039/c3cc47350c
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C20 H22 O3'
_chemical_formula_weight         310.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.99680(10)
_cell_length_b                   13.43520(10)
_cell_length_c                   10.00760(10)
_cell_measurement_reflns_used    2920
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1713.03(3)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13135
_diffrn_reflns_theta_full        67.21
_diffrn_reflns_theta_max         67.21
_diffrn_reflns_theta_min         4.78
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_correction_T_min  0.8321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0455
_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)+(0.0603P)²+0.4560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                2678
_reflns_number_total             2981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47350c.txt
_cod_data_source_block           stu7111
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7110205
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.34645(7) 0.54182(8) 0.53045(10) 0.0462(3) Uani 1 1 d .
O2 O 0.12983(8) 0.66319(8) 0.42937(10) 0.0460(3) Uani 1 1 d .
O3 O 0.01127(9) 0.65864(10) 0.56568(12) 0.0625(3) Uani 1 1 d .
C1 C 0.25101(10) 0.54876(11) 0.58788(14) 0.0415(3) Uani 1 1 d .
C2 C 0.15982(11) 0.56025(11) 0.46171(14) 0.0430(3) Uani 1 1 d .
H2 H 0.0985 0.5191 0.4710 0.052 Uiso 1 1 calc R
C3 C 0.20948(11) 0.52407(11) 0.34818(14) 0.0432(3) Uani 1 1 d .
C4 C 0.31676(11) 0.51889(11) 0.39543(14) 0.0431(3) Uani 1 1 d .
C5 C 0.38611(13) 0.49549(12) 0.31125(16) 0.0520(4) Uani 1 1 d .
H5 H 0.4589 0.4917 0.3448 0.062 Uiso 1 1 calc R
C6 C 0.34320(15) 0.47796(13) 0.17582(17) 0.0587(4) Uani 1 1 d .
H6 H 0.3879 0.4627 0.1154 0.070 Uiso 1 1 calc R
C7 C 0.23580(15) 0.48230(14) 0.12657(17) 0.0618(5) Uani 1 1 d .
H7 H 0.2089 0.4693 0.0340 0.074 Uiso 1 1 calc R
C8 C 0.16788(13) 0.50560(12) 0.21249(16) 0.0530(4) Uani 1 1 d .
H8 H 0.0951 0.5088 0.1792 0.064 Uiso 1 1 calc R
C9 C 0.05302(12) 0.70249(13) 0.48602(16) 0.0501(4) Uani 1 1 d .
C10 C 0.03030(15) 0.80653(14) 0.43691(19) 0.0646(5) Uani 1 1 d .
H10A H -0.0388 0.8259 0.4505 0.097 Uiso 1 1 calc R
H10B H 0.0323 0.8103 0.3407 0.097 Uiso 1 1 calc R
H10C H 0.0826 0.8511 0.4876 0.097 Uiso 1 1 calc R
C11 C 0.23620(12) 0.45169(11) 0.65981(15) 0.0471(4) Uani 1 1 d .
C12 C 0.14779(15) 0.44068(14) 0.71829(16) 0.0590(4) Uani 1 1 d .
H12 H 0.0986 0.4926 0.7114 0.071 Uiso 1 1 calc R
C13 C 0.1319(2) 0.35441(17) 0.78611(19) 0.0766(6) Uani 1 1 d .
H13 H 0.0719 0.3480 0.8245 0.092 Uiso 1 1 calc R
C14 C 0.2026(2) 0.27825(17) 0.7980(2) 0.0900(8) Uani 1 1 d .
H14 H 0.1916 0.2199 0.8451 0.108 Uiso 1 1 calc R
C15 C 0.2901(2) 0.28741(15) 0.7403(3) 0.0900(8) Uani 1 1 d .
H15 H 0.3388 0.2349 0.7483 0.108 Uiso 1 1 calc R
C16 C 0.30739(15) 0.37389(13) 0.6702(2) 0.0654(5) Uani 1 1 d .
H16 H 0.3669 0.3792 0.6303 0.078 Uiso 1 1 calc R
C17 C 0.26736(11) 0.63674(11) 0.68572(15) 0.0449(3) Uani 1 1 d .
H17A H 0.2742 0.6974 0.6337 0.054 Uiso 1 1 calc R
H17B H 0.2048 0.6441 0.7257 0.054 Uiso 1 1 calc R
C18 C 0.36301(12) 0.62789(12) 0.80054(15) 0.0491(4) Uani 1 1 d .
H18A H 0.3550 0.5693 0.8559 0.059 Uiso 1 1 calc R
H18B H 0.4257 0.6180 0.7613 0.059 Uiso 1 1 calc R
C19 C 0.37826(15) 0.71821(16) 0.8904(2) 0.0718(6) Uani 1 1 d .
H19A H 0.3154 0.7273 0.9295 0.086 Uiso 1 1 calc R
H19B H 0.3846 0.7766 0.8340 0.086 Uiso 1 1 calc R
C20 C 0.47287(15) 0.71415(17) 1.0052(2) 0.0749(6) Uani 1 1 d .
H20A H 0.4678 0.6564 1.0617 0.112 Uiso 1 1 calc R
H20B H 0.4756 0.7740 1.0600 0.112 Uiso 1 1 calc R
H20C H 0.5361 0.7095 0.9678 0.112 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C4 O1 C1 107.82(10)
C9 O2 C2 117.79(12)
O1 C1 C11 109.05(11)
O1 C1 C17 106.22(11)
C11 C1 C17 112.09(12)
O1 C1 C2 104.76(10)
C11 C1 C2 108.74(11)
C17 C1 C2 115.53(12)
O2 C2 C3 106.07(11)
O2 C2 C1 113.67(11)
C3 C2 C1 102.13(11)
O2 C2 H2 111.5
C3 C2 H2 111.5
C1 C2 H2 111.5
C8 C3 C4 119.98(14)
C8 C3 C2 131.44(14)
C4 C3 C2 108.31(12)
O1 C4 C3 113.32(12)
O1 C4 C5 124.21(14)
C3 C4 C5 122.45(14)
C6 C5 C4 116.77(15)
C6 C5 H5 121.6
C4 C5 H5 121.6
C5 C6 C7 121.67(15)
C5 C6 H6 119.2
C7 C6 H6 119.2
C8 C7 C6 120.62(16)
C8 C7 H7 119.7
C6 C7 H7 119.7
C3 C8 C7 118.52(16)
C3 C8 H8 120.7
C7 C8 H8 120.7
O3 C9 O2 123.70(15)
O3 C9 C10 126.24(15)
O2 C9 C10 110.06(14)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C16 C11 C12 118.75(16)
C16 C11 C1 122.50(15)
C12 C11 C1 118.75(14)
C13 C12 C11 120.7(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C14 C13 C12 120.7(2)
C14 C13 H13 119.7
C12 C13 H13 119.7
C13 C14 C15 119.55(19)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C16 120.8(2)
C14 C15 H15 119.6
C16 C15 H15 119.6
C11 C16 C15 119.6(2)
C11 C16 H16 120.2
C15 C16 H16 120.2
C18 C17 C1 114.47(12)
C18 C17 H17A 108.6
C1 C17 H17A 108.6
C18 C17 H17B 108.6
C1 C17 H17B 108.6
H17A C17 H17B 107.6
C19 C18 C17 112.40(13)
C19 C18 H18A 109.1
C17 C18 H18A 109.1
C19 C18 H18B 109.1
C17 C18 H18B 109.1
H18A C18 H18B 107.9
C18 C19 C20 114.75(16)
C18 C19 H19A 108.6
C20 C19 H19A 108.6
C18 C19 H19B 108.6
C20 C19 H19B 108.6
H19A C19 H19B 107.6
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3652(17)
O1 C1 1.4694(16)
O2 C9 1.3492(18)
O2 C2 1.4559(17)
O3 C9 1.2033(19)
C1 C11 1.520(2)
C1 C17 1.523(2)
C1 C2 1.5593(19)
C2 C3 1.495(2)
C2 H2 0.9900
C3 C8 1.381(2)
C3 C4 1.383(2)
C4 C5 1.386(2)
C5 C6 1.380(2)
C5 H5 0.9400
C6 C7 1.387(3)
C6 H6 0.9400
C7 C8 1.384(2)
C7 H7 0.9400
C8 H8 0.9400
C9 C10 1.492(2)
C10 H10A 0.9700
C10 H10B 0.9700
C10 H10C 0.9700
C11 C16 1.386(2)
C11 C12 1.397(2)
C12 C13 1.379(3)
C12 H12 0.9400
C13 C14 1.364(4)
C13 H13 0.9400
C14 C15 1.380(4)
C14 H14 0.9400
C15 C16 1.398(3)
C15 H15 0.9400
C16 H16 0.9400
C17 C18 1.522(2)
C17 H17A 0.9800
C17 H17B 0.9800
C18 C19 1.500(2)
C18 H18A 0.9800
C18 H18B 0.9800
C19 C20 1.509(3)
C19 H19A 0.9800
C19 H19B 0.9800
C20 H20A 0.9700
C20 H20B 0.9700
C20 H20C 0.9700
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
C4 O1 C1 C11 98.81(13)
C4 O1 C1 C17 -140.20(12)
C4 O1 C1 C2 -17.46(14)
C9 O2 C2 C3 157.29(12)
C9 O2 C2 C1 -91.30(14)
O1 C1 C2 O2 -95.23(13)
C11 C1 C2 O2 148.30(12)
C17 C1 C2 O2 21.26(17)
O1 C1 C2 C3 18.56(13)
C11 C1 C2 C3 -97.92(13)
C17 C1 C2 C3 135.05(12)
O2 C2 C3 C8 -68.3(2)
C1 C2 C3 C8 172.45(16)
O2 C2 C3 C4 105.55(13)
C1 C2 C3 C4 -13.74(15)
C1 O1 C4 C3 9.33(16)
C1 O1 C4 C5 -172.52(14)
C8 C3 C4 O1 178.16(13)
C2 C3 C4 O1 3.52(17)
C8 C3 C4 C5 0.0(2)
C2 C3 C4 C5 -174.67(14)
O1 C4 C5 C6 -177.52(14)
C3 C4 C5 C6 0.5(2)
C4 C5 C6 C7 -0.8(2)
C5 C6 C7 C8 0.7(3)
C4 C3 C8 C7 -0.1(2)
C2 C3 C8 C7 173.10(16)
C6 C7 C8 C3 -0.2(3)
C2 O2 C9 O3 3.2(2)
C2 O2 C9 C10 -177.72(12)
O1 C1 C11 C16 2.44(19)
C17 C1 C11 C16 -114.89(16)
C2 C1 C11 C16 116.13(16)
O1 C1 C11 C12 -177.90(12)
C17 C1 C11 C12 64.77(17)
C2 C1 C11 C12 -64.20(17)
C16 C11 C12 C13 0.5(2)
C1 C11 C12 C13 -179.13(15)
C11 C12 C13 C14 0.3(3)
C12 C13 C14 C15 -0.6(3)
C13 C14 C15 C16 0.1(3)
C12 C11 C16 C15 -1.0(3)
C1 C11 C16 C15 178.62(16)
C14 C15 C16 C11 0.7(3)
O1 C1 C17 C18 -58.84(15)
C11 C1 C17 C18 60.17(17)
C2 C1 C17 C18 -174.51(12)
C1 C17 C18 C19 177.54(15)
C17 C18 C19 C20 -179.27(17)
