#------------------------------------------------------------------------------
#$Date: 2019-11-04 09:21:41 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222346 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/37/4033771.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_4033771
loop_
_publ_author_name
'Martínez-García, Lucas'
'Lobato, Rubén'
'Prado, Gustavo'
'Monje, Pablo'
'Sardina, F. Javier'
'Paleo, M. Rita'
_publ_section_title
;
 C-C Bond-Forming and Bond-Breaking Processes from the Reaction of
 Diesters with Me₃SnLi. Synthesis of Complex Bridged Polycycles
 and Dialkyl Aromatic Compounds.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1887
_journal_page_last               1897
_journal_paper_doi               10.1021/acs.joc.8b02891
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H28 O4'
_chemical_formula_sum            'C24 H28 O4'
_chemical_formula_weight         380.46
_chemical_name_common            JSRL494.Rx
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             2013-01-11T11:09:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.708(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7541(5)
_cell_length_b                   14.8903(9)
_cell_length_c                   8.3727(4)
_cell_measurement_reflns_used    3938
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.47
_cell_measurement_wavelength     0.71073
_cell_volume                     1027.46(10)
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS, 2012)'
_computing_data_collection       'APEX2 v2012.10-0 (Bruker AXS, 2012)'
_computing_data_reduction        'APEX2 v2012.10-0 (Bruker AXS, 2012)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker X8 kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            24208
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_correction_T_min  0.8986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER AXS - SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.13
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0580P)²+0.2124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1890
_reflns_number_total             2550
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo8b02891_si_009.cif
_cod_data_source_block           js10waa1n
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4033771
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
C1 C 0.66380(16) 0.46875(9) 0.49193(17) 0.0174(3) Uani 1 1 d .
C2 C 0.50711(16) 0.41546(9) 0.41606(16) 0.0165(3) Uani 1 1 d .
C3 C 0.51333(17) 0.33512(10) 0.33188(18) 0.0208(3) Uani 1 1 d .
H3 H 0.6135 0.3167 0.3216 0.025 Uiso 1 1 calc R
C4 C 0.37807(17) 0.28180(10) 0.26336(17) 0.0220(3) Uani 1 1 d .
H4 H 0.3847 0.228 0.205 0.026 Uiso 1 1 calc R
C5 C 0.23224(17) 0.30774(10) 0.28072(17) 0.0216(3) Uani 1 1 d .
H5 H 0.1387 0.271 0.2366 0.026 Uiso 1 1 calc R
C6 C 0.22344(16) 0.38707(10) 0.36224(17) 0.0205(3) Uani 1 1 d .
H6 H 0.1231 0.4044 0.3735 0.025 Uiso 1 1 calc R
C7 C 0.35925(16) 0.44267(9) 0.42886(16) 0.0164(3) Uani 1 1 d .
C11 C 0.72812(16) 0.48736(10) 0.34532(18) 0.0208(3) Uani 1 1 d .
C14 C 0.6836(2) 0.56941(12) 0.0930(2) 0.0357(4) Uani 1 1 d .
H14A H 0.7937 0.5943 0.1298 0.054 Uiso 1 1 calc R
H14B H 0.6076 0.6132 0.0213 0.054 Uiso 1 1 calc R
H14C H 0.6804 0.5142 0.0284 0.054 Uiso 1 1 calc R
C21 C 0.79085(16) 0.41051(10) 0.62645(17) 0.0204(3) Uani 1 1 d .
H21A H 0.8131 0.3558 0.5708 0.024 Uiso 1 1 calc R
H21B H 0.8935 0.4447 0.6714 0.024 Uiso 1 1 calc R
C22 C 0.73630(18) 0.38302(11) 0.77292(18) 0.0253(3) Uani 1 1 d .
H22A H 0.7019 0.4372 0.8203 0.03 Uiso 1 1 calc R
H22B H 0.641 0.3429 0.7299 0.03 Uiso 1 1 calc R
C23 C 0.8674(2) 0.33537(13) 0.9131(2) 0.0375(4) Uani 1 1 d .
H23A H 0.9007 0.281 0.8677 0.056 Uiso 1 1 calc R
H23B H 0.8255 0.319 1.0038 0.056 Uiso 1 1 calc R
H23C H 0.9611 0.3753 0.9586 0.056 Uiso 1 1 calc R
O12 O 0.83943(13) 0.44978(8) 0.32194(15) 0.0358(3) Uani 1 1 d .
O13 O 0.63825(13) 0.54953(7) 0.23987(12) 0.0267(3) Uani 1 1 d .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C7 C1 C2 113.59(11) 3_666 .
C7 C1 C11 109.26(11) 3_666 .
C2 C1 C11 106.33(11) . .
C7 C1 C21 109.64(11) 3_666 .
C2 C1 C21 109.57(11) . .
C11 C1 C21 108.30(11) . .
C7 C2 C3 118.82(12) . .
C7 C2 C1 122.98(12) . .
C3 C2 C1 118.19(12) . .
C4 C3 C2 121.86(13) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C5 119.16(13) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C6 C5 C4 119.81(13) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C5 C6 C7 121.44(13) . .
C5 C6 H6 119.3 . .
C7 C6 H6 119.3 . .
C2 C7 C6 118.86(13) . .
C2 C7 C1 123.29(12) . 3_666
C6 C7 C1 117.83(12) . 3_666
O12 C11 O13 123.13(13) . .
O12 C11 C1 125.74(14) . .
O13 C11 C1 111.07(11) . .
O13 C14 H14A 109.5 . .
O13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C22 C21 C1 113.19(11) . .
C22 C21 H21A 108.9 . .
C1 C21 H21A 108.9 . .
C22 C21 H21B 108.9 . .
C1 C21 H21B 108.9 . .
H21A C21 H21B 107.8 . .
C23 C22 C21 113.00(12) . .
C23 C22 H22A 109 . .
C21 C22 H22A 109 . .
C23 C22 H22B 109 . .
C21 C22 H22B 109 . .
H22A C22 H22B 107.8 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C11 O13 C14 115.76(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C7 1.5200(19) 3_666
C1 C2 1.5255(18) .
C1 C11 1.5384(18) .
C1 C21 1.5533(19) .
C2 C7 1.3946(18) .
C2 C3 1.399(2) .
C3 C4 1.380(2) .
C3 H3 0.95 .
C4 C5 1.388(2) .
C4 H4 0.95 .
C5 C6 1.379(2) .
C5 H5 0.95 .
C6 C7 1.4009(19) .
C6 H6 0.95 .
C7 C1 1.5200(19) 3_666
C11 O12 1.1957(17) .
C11 O13 1.3367(18) .
C14 O13 1.4444(17) .
C14 H14A 0.98 .
C14 H14B 0.98 .
C14 H14C 0.98 .
C21 C22 1.5147(19) .
C21 H21A 0.99 .
C21 H21B 0.99 .
C22 C23 1.513(2) .
C22 H22A 0.99 .
C22 H22B 0.99 .
C23 H23A 0.98 .
C23 H23B 0.98 .
C23 H23C 0.98 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 C1 C2 C7 -4.21(19) 3_666 .
C11 C1 C2 C7 -124.41(13) . .
C21 C1 C2 C7 118.77(13) . .
C7 C1 C2 C3 176.63(11) 3_666 .
C11 C1 C2 C3 56.43(15) . .
C21 C1 C2 C3 -60.39(15) . .
C7 C2 C3 C4 -0.8(2) . .
C1 C2 C3 C4 178.38(12) . .
C2 C3 C4 C5 -1.1(2) . .
C3 C4 C5 C6 1.5(2) . .
C4 C5 C6 C7 -0.1(2) . .
C3 C2 C7 C6 2.22(19) . .
C1 C2 C7 C6 -176.94(11) . .
C3 C2 C7 C1 -176.23(12) . 3_666
C1 C2 C7 C1 4.6(2) . 3_666
C5 C6 C7 C2 -1.8(2) . .
C5 C6 C7 C1 176.73(12) . 3_666
C7 C1 C11 O12 132.76(15) 3_666 .
C2 C1 C11 O12 -104.28(17) . .
C21 C1 C11 O12 13.4(2) . .
C7 C1 C11 O13 -49.98(15) 3_666 .
C2 C1 C11 O13 72.98(14) . .
C21 C1 C11 O13 -169.35(11) . .
C7 C1 C21 C22 64.29(15) 3_666 .
C2 C1 C21 C22 -60.99(15) . .
C11 C1 C21 C22 -176.57(12) . .
C1 C21 C22 C23 -173.49(13) . .
O12 C11 O13 C14 0.0(2) . .
C1 C11 O13 C14 -177.37(12) . .
