#------------------------------------------------------------------------------
#$Date: 2019-11-04 09:20:57 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222344 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/37/4033769.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_4033769
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         'C16 H18 O4'
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.3
_chemical_name_systematic
;
Dimethyl trans-1,4-dimethyl-1,4-dihydronaphthalene-1,4-dicarboxylate
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-10-24T11:27:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.147(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2165(9)
_cell_length_b                   11.0383(8)
_cell_length_c                   19.3944(13)
_cell_measurement_reflns_used    1986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.54
_cell_measurement_wavelength     0.71073
_cell_volume                     2793.4(3)
_computing_cell_refinement       'APPEX2 (BRUKER AXS, 2005)'
_computing_data_collection       'APPEX2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX2 (BRUKER AXS, 2005)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER APPEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            28456
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plane
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_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     185
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0375
_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)+(0.0401P)²+1.9277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                2220
_reflns_number_total             2869
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo8b02891_si_010.cif
_cod_data_source_block           JSRL297RX
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4033769
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.08540(10) 0.10573(13) 0.62900(7) 0.0172(3) Uani 1 1 d .
C2 C 0.07945(11) 0.20179(14) 0.68360(7) 0.0201(3) Uani 1 1 d .
H2 H 0.0134 0.2306 0.689 0.024 Uiso 1 1 calc R
C3 C 0.15932(11) 0.24891(14) 0.72454(7) 0.0209(3) Uani 1 1 d .
H3 H 0.1464 0.3081 0.7576 0.025 Uiso 1 1 calc R
C4 C 0.26888(11) 0.21563(13) 0.72249(7) 0.0169(3) Uani 1 1 d .
C5 C 0.27770(10) 0.10469(12) 0.67657(7) 0.0145(3) Uani 1 1 d .
C6 C 0.19322(10) 0.05459(12) 0.63330(7) 0.0152(3) Uani 1 1 d .
C7 C 0.20879(11) -0.04455(13) 0.59115(7) 0.0195(3) Uani 1 1 d .
H7 H 0.1518 -0.0791 0.5617 0.023 Uiso 1 1 calc R
C8 C 0.30542(11) -0.09335(13) 0.59135(7) 0.0204(3) Uani 1 1 d .
H8 H 0.3143 -0.1612 0.5628 0.024 Uiso 1 1 calc R
C9 C 0.38911(11) -0.04208(13) 0.63367(7) 0.0199(3) Uani 1 1 d .
H9 H 0.4559 -0.074 0.6337 0.024 Uiso 1 1 calc R
C10 C 0.37498(10) 0.05564(13) 0.67580(7) 0.0165(3) Uani 1 1 d .
H10 H 0.4325 0.09 0.7048 0.02 Uiso 1 1 calc R
C11 C 0.00650(11) 0.00655(15) 0.63642(9) 0.0267(4) Uani 1 1 d .
H11A H 0.0284 -0.0389 0.6796 0.04 Uiso 1 1 calc R
H11B H 0.0011 -0.0486 0.5964 0.04 Uiso 1 1 calc R
H11C H -0.0604 0.0438 0.638 0.04 Uiso 1 1 calc R
O1 O -0.03572(8) 0.18228(10) 0.53124(5) 0.0255(3) Uani 1 1 d .
C12 C 0.05174(10) 0.17352(13) 0.55995(7) 0.0173(3) Uani 1 1 d .
O2 O 0.13052(8) 0.22931(10) 0.53765(5) 0.0233(3) Uani 1 1 d .
C13 C 0.10409(12) 0.30776(15) 0.47748(8) 0.0262(4) Uani 1 1 d .
H13A H 0.0662 0.2613 0.4387 0.039 Uiso 1 1 calc R
H13B H 0.1669 0.3403 0.4636 0.039 Uiso 1 1 calc R
H13C H 0.0614 0.3747 0.4895 0.039 Uiso 1 1 calc R
C14 C 0.32437(12) 0.32396(13) 0.69505(8) 0.0236(3) Uani 1 1 d .
H14A H 0.2951 0.3395 0.6462 0.035 Uiso 1 1 calc R
H14B H 0.3975 0.3054 0.6984 0.035 Uiso 1 1 calc R
H14C H 0.3158 0.3959 0.7232 0.035 Uiso 1 1 calc R
C15 C 0.32272(11) 0.18601(13) 0.79663(7) 0.0180(3) Uani 1 1 d .
O3 O 0.41044(8) 0.21089(10) 0.81977(5) 0.0261(3) Uani 1 1 d .
C16 C 0.30596(14) 0.09290(16) 0.90338(8) 0.0327(4) Uani 1 1 d .
H16A H 0.3571 0.0292 0.9014 0.049 Uiso 1 1 calc R
H16B H 0.2525 0.0627 0.9286 0.049 Uiso 1 1 calc R
H16C H 0.3391 0.1638 0.9277 0.049 Uiso 1 1 calc R
O4 O 0.26051(8) 0.12683(10) 0.83313(5) 0.0244(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
C2 C1 C6 112.00(11)
C2 C1 C11 108.88(12)
C6 C1 C11 111.99(12)
C2 C1 C12 103.25(11)
C6 C1 C12 111.53(11)
C11 C1 C12 108.80(11)
C3 C2 C1 124.88(13)
C3 C2 H2 117.6
C1 C2 H2 117.6
C2 C3 C4 124.71(14)
C2 C3 H3 117.6
C4 C3 H3 117.6
C3 C4 C5 112.00(11)
C3 C4 C15 109.45(12)
C5 C4 C15 107.94(11)
C3 C4 C14 109.48(12)
C5 C4 C14 109.61(11)
C15 C4 C14 108.28(11)
C10 C5 C6 119.22(13)
C10 C5 C4 118.16(12)
C6 C5 C4 122.55(12)
C5 C6 C7 118.78(13)
C5 C6 C1 122.47(12)
C7 C6 C1 118.74(12)
C8 C7 C6 121.54(13)
C8 C7 H7 119.2
C6 C7 H7 119.2
C7 C8 C9 119.37(13)
C7 C8 H8 120.3
C9 C8 H8 120.3
C10 C9 C8 119.81(13)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C5 121.28(13)
C9 C10 H10 119.4
C5 C10 H10 119.4
C1 C11 H11A 109.5
C1 C11 H11B 109.5
H11A C11 H11B 109.5
C1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O1 C12 O2 123.50(13)
O1 C12 C1 124.44(13)
O2 C12 C1 111.91(11)
C12 O2 C13 115.74(11)
O2 C13 H13A 109.5
O2 C13 H13B 109.5
H13A C13 H13B 109.5
O2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C4 C14 H14A 109.5
C4 C14 H14B 109.5
H14A C14 H14B 109.5
C4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O3 C15 O4 123.34(13)
O3 C15 C4 125.09(13)
O4 C15 C4 111.56(12)
O4 C16 H16A 109.5
O4 C16 H16B 109.5
H16A C16 H16B 109.5
O4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 O4 C16 115.23(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.509(2)
C1 C6 1.5227(19)
C1 C11 1.534(2)
C1 C12 1.5369(19)
C2 C3 1.322(2)
C2 H2 0.95
C3 C4 1.501(2)
C3 H3 0.95
C4 C5 1.5296(19)
C4 C15 1.5348(19)
C4 C14 1.541(2)
C5 C10 1.3972(19)
C5 C6 1.3996(19)
C6 C7 1.401(2)
C7 C8 1.385(2)
C7 H7 0.95
C8 C9 1.389(2)
C8 H8 0.95
C9 C10 1.384(2)
C9 H9 0.95
C10 H10 0.95
C11 H11A 0.98
C11 H11B 0.98
C11 H11C 0.98
O1 C12 1.2045(16)
C12 O2 1.3392(17)
O2 C13 1.4505(17)
C13 H13A 0.98
C13 H13B 0.98
C13 H13C 0.98
C14 H14A 0.98
C14 H14B 0.98
C14 H14C 0.98
C15 O3 1.2064(17)
C15 O4 1.3375(18)
C16 O4 1.4482(18)
C16 H16A 0.98
C16 H16B 0.98
C16 H16C 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
C6 C1 C2 C3 8.5(2)
C11 C1 C2 C3 132.95(15)
C12 C1 C2 C3 -111.57(16)
C1 C2 C3 C4 1.0(2)
C2 C3 C4 C5 -10.1(2)
C2 C3 C4 C15 -129.79(15)
C2 C3 C4 C14 111.68(16)
C3 C4 C5 C10 -173.26(12)
C15 C4 C5 C10 -52.70(16)
C14 C4 C5 C10 65.03(16)
C3 C4 C5 C6 9.74(18)
C15 C4 C5 C6 130.30(13)
C14 C4 C5 C6 -111.97(15)
C10 C5 C6 C7 0.8(2)
C4 C5 C6 C7 177.82(12)
C10 C5 C6 C1 -177.61(12)
C4 C5 C6 C1 -0.6(2)
C2 C1 C6 C5 -8.43(18)
C11 C1 C6 C5 -131.08(14)
C12 C1 C6 C5 106.73(15)
C2 C1 C6 C7 173.11(12)
C11 C1 C6 C7 50.46(17)
C12 C1 C6 C7 -71.74(16)
C5 C6 C7 C8 -0.1(2)
C1 C6 C7 C8 178.37(13)
C6 C7 C8 C9 -0.8(2)
C7 C8 C9 C10 1.0(2)
C8 C9 C10 C5 -0.3(2)
C6 C5 C10 C9 -0.7(2)
C4 C5 C10 C9 -177.75(12)
C2 C1 C12 O1 -88.94(16)
C6 C1 C12 O1 150.62(14)
C11 C1 C12 O1 26.60(19)
C2 C1 C12 O2 86.69(13)
C6 C1 C12 O2 -33.75(16)
C11 C1 C12 O2 -157.77(12)
O1 C12 O2 C13 3.0(2)
C1 C12 O2 C13 -172.72(12)
C3 C4 C15 O3 -143.15(15)
C5 C4 C15 O3 94.71(16)
C14 C4 C15 O3 -23.87(19)
C3 C4 C15 O4 37.71(16)
C5 C4 C15 O4 -84.43(14)
C14 C4 C15 O4 156.99(12)
O3 C15 O4 C16 -0.4(2)
C4 C15 O4 C16 178.71(12)
