#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:35:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180146 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/43/7104352.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_7104352
loop_
_publ_author_name
'Tejedor, David'
'Méndez-Abt, Gabriela'
'González-Platas, Javier'
'Ramírez, Miguel A'
'García-Tellado, Fernando'
_publ_section_title
;
 Ambiphilic allenes: synthesis and reactivity.
;
_journal_issue                   17
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2368
_journal_page_last               2370
_journal_paper_doi               10.1039/b819613c
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C29 H22 O6'
_chemical_formula_sum            'C29 H22 O6'
_chemical_formula_weight         466.47
_chemical_name_common
;
(E)-((E)-4-(2-methoxy-2-oxothylidene)-2-(methoxycarbonyl)-3-
phenylcyclobut-2-enylidene)(phenyl)methyl benzoate
;
_chemical_name_systematic
;
(E)-((E)-4-(2-methoxy-2-oxothylidene)-2-(methoxycarbonyl)-3-
phenylcyclobut-2-enylidene)(phenyl)methyl benzoate
;
_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                 96.400(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7690(10)
_cell_length_b                   9.6780(10)
_cell_length_c                   23.3110(10)
_cell_measurement_temperature    293(2)
_cell_volume                     2414.4(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Altomare et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27643
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.949
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3454
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0699
_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)+(0.0945P)²+2.9129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.1955
_reflns_number_gt                2959
_reflns_number_total             3454
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b819613c.txt
_cod_data_source_block           dt743c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7104352
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3840(2) 1.0725(2) 0.20002(9) 0.0389(6) Uani 1 1 d . . .
O2 O 0.2904(3) 1.2736(3) 0.21757(12) 0.0698(9) Uani 1 1 d . . .
O3A O 0.0791(11) 0.6919(16) 0.2655(7) 0.062(4) Uani 0.297(10) 1 d P A 1
O4A O 0.275(2) 0.640(3) 0.3023(7) 0.0625(17) Uani 0.297(10) 1 d PD A 1
O3B O 0.1091(7) 0.6256(7) 0.2425(3) 0.080(2) Uani 0.703(10) 1 d P A 2
O4B O 0.2566(8) 0.6610(11) 0.3174(3) 0.0625(17) Uani 0.703(10) 1 d PD A 2
O5 O 0.2284(2) 0.9354(3) 0.00934(10) 0.0578(7) Uani 1 1 d . . .
O6 O 0.0363(3) 0.8448(3) 0.00422(12) 0.0697(8) Uani 1 1 d . . .
C1 C 0.2354(3) 0.9517(3) 0.14067(12) 0.0328(7) Uani 1 1 d . . .
C2 C 0.1521(3) 0.8793(3) 0.09532(14) 0.0361(8) Uani 1 1 d . . .
C3 C 0.1107(3) 0.7869(3) 0.13312(15) 0.0387(8) Uani 1 1 d . . .
C4 C 0.1972(3) 0.8455(3) 0.18197(13) 0.0351(7) Uani 1 1 d . . .
C5 C 0.3112(3) 1.0607(3) 0.14580(13) 0.0335(7) Uani 1 1 d . . .
C6 C 0.3652(3) 1.1854(4) 0.23279(14) 0.0421(8) Uani 1 1 d . . .
C7 C 0.4455(3) 1.1810(3) 0.28868(14) 0.0401(8) Uani 1 1 d . . .
C8 C 0.4351(4) 1.2868(4) 0.32811(15) 0.0519(10) Uani 1 1 d . . .
H8 H 0.3818 1.3609 0.3187 0.062 Uiso 1 1 calc R . .
C9 C 0.5048(4) 1.2808(5) 0.38150(16) 0.0608(11) Uani 1 1 d . . .
H9 H 0.4981 1.3512 0.4081 0.073 Uiso 1 1 calc R . .
C10 C 0.5833(4) 1.1724(5) 0.39541(16) 0.0610(11) Uani 1 1 d . . .
H10 H 0.6293 1.1694 0.4316 0.073 Uiso 1 1 calc R . .
C11 C 0.5952(4) 1.0680(5) 0.35675(16) 0.0579(10) Uani 1 1 d . . .
H11 H 0.6495 0.9948 0.3665 0.069 Uiso 1 1 calc R . .
C12 C 0.5266(3) 1.0719(4) 0.30351(14) 0.0466(9) Uani 1 1 d . . .
H12 H 0.5344 1.0011 0.2772 0.056 Uiso 1 1 calc R . .
C13 C 0.3370(3) 1.1610(3) 0.10170(13) 0.0337(7) Uani 1 1 d . . .
C14 C 0.2406(3) 1.2141(4) 0.06392(14) 0.0438(8) Uani 1 1 d . . .
H14 H 0.1585 1.1897 0.0679 0.053 Uiso 1 1 calc R . .
C15 C 0.2656(4) 1.3033(4) 0.02038(16) 0.0526(10) Uani 1 1 d . . .
H15 H 0.2003 1.3374 -0.0052 0.063 Uiso 1 1 calc R . .
C16 C 0.3860(4) 1.3416(4) 0.01466(16) 0.0558(10) Uani 1 1 d . . .
H16 H 0.4026 1.4013 -0.0148 0.067 Uiso 1 1 calc R . .
C17 C 0.4814(4) 1.2919(4) 0.05244(18) 0.0584(11) Uani 1 1 d . . .
H17 H 0.5630 1.3185 0.0486 0.070 Uiso 1 1 calc R . .
C18 C 0.4586(3) 1.2030(4) 0.09615(15) 0.0457(9) Uani 1 1 d . . .
H18 H 0.5244 1.1711 0.1220 0.055 Uiso 1 1 calc R . .
C19 C 0.2413(3) 0.8140(4) 0.23628(14) 0.0416(8) Uani 1 1 d . A .
H19 H 0.3025 0.8723 0.2541 0.050 Uiso 1 1 calc R . .
C20 C 0.2040(3) 0.6986(4) 0.27062(17) 0.0522(10) Uani 1 1 d D . .
C21A C 0.018(2) 0.591(2) 0.2994(10) 0.099(3) Uani 0.297(10) 1 d P A 1
H21A H 0.0794 0.5338 0.3205 0.149 Uiso 0.297(10) 1 calc PR A 1
H21B H -0.0377 0.5351 0.2740 0.149 Uiso 0.297(10) 1 calc PR A 1
H21C H -0.0295 0.6388 0.3259 0.149 Uiso 0.297(10) 1 calc PR A 1
C21B C 0.0694(8) 0.5012(10) 0.2698(4) 0.099(3) Uani 0.703(10) 1 d P A 2
H21D H 0.1386 0.4386 0.2764 0.149 Uiso 0.703(10) 1 calc PR A 2
H21E H 0.0032 0.4582 0.2452 0.149 Uiso 0.703(10) 1 calc PR A 2
H21F H 0.0402 0.5246 0.3060 0.149 Uiso 0.703(10) 1 calc PR A 2
C22 C 0.1303(3) 0.8852(3) 0.03171(15) 0.0425(8) Uani 1 1 d . . .
C23 C 0.2165(5) 0.9553(6) -0.05191(17) 0.0834(15) Uani 1 1 d . . .
H23A H 0.1868 0.8717 -0.0709 0.125 Uiso 1 1 calc R . .
H23B H 0.2965 0.9789 -0.0637 0.125 Uiso 1 1 calc R . .
H23C H 0.1584 1.0288 -0.0623 0.125 Uiso 1 1 calc R . .
C24 C 0.0226(3) 0.6702(3) 0.12465(16) 0.0461(9) Uani 1 1 d D . .
C25 C -0.0917(3) 0.6725(4) 0.14145(19) 0.0628(11) Uani 1 1 d D . .
H25 H -0.1170 0.7511 0.1599 0.075 Uiso 1 1 calc R . .
C26 C -0.1740(4) 0.5639(4) 0.13276(19) 0.0631(11) Uani 1 1 d D . .
H26 H -0.2525 0.5706 0.1456 0.076 Uiso 1 1 calc R . .
C27 C -0.1435(4) 0.4514(5) 0.1067(3) 0.0857(16) Uani 1 1 d D . .
H27 H -0.1929 0.3726 0.1068 0.103 Uiso 1 1 calc R . .
C28 C -0.0350(5) 0.4513(5) 0.0784(3) 0.0902(16) Uani 1 1 d D . .
H28 H -0.0190 0.3790 0.0540 0.108 Uiso 1 1 calc R . .
C29 C 0.0480(4) 0.5612(5) 0.0875(2) 0.0761(13) Uani 1 1 d D . .
H29 H 0.1203 0.5628 0.0691 0.091 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 0.0033 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C5 117.6(2) . . ?
C20 O3A C21A 119.8(12) . . ?
C20 O3B C21B 117.8(5) . . ?
C22 O5 C23 117.2(3) . . ?
C5 C1 C2 139.0(3) . . ?
C5 C1 C4 134.1(3) . . ?
C2 C1 C4 86.9(2) . . ?
C3 C2 C22 130.3(3) . . ?
C3 C2 C1 93.7(3) . . ?
C22 C2 C1 135.5(3) . . ?
C2 C3 C24 131.9(3) . . ?
C2 C3 C4 91.3(2) . . ?
C24 C3 C4 136.7(3) . . ?
C19 C4 C1 132.2(3) . . ?
C19 C4 C3 139.2(3) . . ?
C1 C4 C3 87.9(2) . . ?
C1 C5 O1 114.7(3) . . ?
C1 C5 C13 128.7(3) . . ?
O1 C5 C13 116.4(2) . . ?
O2 C6 O1 122.8(3) . . ?
O2 C6 C7 126.0(3) . . ?
O1 C6 C7 111.2(3) . . ?
C12 C7 C8 119.4(3) . . ?
C12 C7 C6 122.0(3) . . ?
C8 C7 C6 118.6(3) . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C7 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 118.7(3) . . ?
C14 C13 C5 120.4(3) . . ?
C18 C13 C5 120.9(3) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C4 C19 C20 127.2(3) . . ?
C4 C19 H19 116.4 . . ?
C20 C19 H19 116.4 . . ?
O4A C20 O4B 22.5(10) . . ?
O4A C20 O3A 128.5(15) . . ?
O4B C20 O3A 115.1(7) . . ?
O4A C20 O3B 117.8(17) . . ?
O4B C20 O3B 121.7(7) . . ?
O3A C20 O3B 39.9(6) . . ?
O4A C20 C19 121.8(16) . . ?
O4B C20 C19 126.0(6) . . ?
O3A C20 C19 108.9(6) . . ?
O3B C20 C19 112.0(4) . . ?
O3B C21B H21D 109.5 . . ?
O3B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
O3B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
O6 C22 O5 124.9(3) . . ?
O6 C22 C2 123.6(3) . . ?
O5 C22 C2 111.5(3) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 116.1(3) . . ?
C25 C24 C3 123.4(3) . . ?
C29 C24 C3 119.3(3) . . ?
C24 C25 C26 123.1(4) . . ?
C24 C25 H25 118.5 . . ?
C26 C25 H25 118.5 . . ?
C27 C26 C25 120.9(4) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 119.0(4) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C29 C28 C27 118.8(4) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 C24 120.1(4) . . ?
C28 C29 H29 120.0 . . ?
C24 C29 H29 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.361(4) . ?
O1 C5 1.415(4) . ?
O2 C6 1.200(4) . ?
O3A C20 1.339(12) . ?
O3A C21A 1.46(2) . ?
O4A C20 1.152(18) . ?
O3B C20 1.351(7) . ?
O3B C21B 1.448(8) . ?
O4B C20 1.227(8) . ?
O5 C22 1.322(4) . ?
O5 C23 1.432(5) . ?
O6 C22 1.202(4) . ?
C1 C5 1.330(4) . ?
C1 C2 1.484(4) . ?
C1 C4 1.497(4) . ?
C2 C3 1.365(5) . ?
C2 C22 1.476(5) . ?
C3 C24 1.473(5) . ?
C3 C4 1.500(4) . ?
C4 C19 1.337(5) . ?
C5 C13 1.463(4) . ?
C6 C7 1.482(5) . ?
C7 C12 1.389(5) . ?
C7 C8 1.389(5) . ?
C8 C9 1.381(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 C18 1.391(4) . ?
C14 C15 1.381(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.457(5) . ?
C19 H19 0.9300 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.333(5) . ?
C24 C29 1.411(6) . ?
C25 C26 1.375(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.307(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.404(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.390(6) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12 O1 0.9300 2.3900 2.712(4) 100.00 . yes
C14 H14 O6 0.9300 2.5600 3.269(5) 133.00 3_575 yes
C19 H19 O1 0.9300 2.5200 3.103(4) 121.00 . yes
C28 H28 O6 0.9300 2.5500 3.451(6) 163.00 3_565 yes
