#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:18:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178429 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/50/4025026.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_4025026
loop_
_publ_author_name
'Ashraf Wilsily'
'Eric Fillion'
_publ_section_title
;
Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via
Conjugate Addition to Alkylidene and Indenylidene Meldrum's Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8583
_journal_page_last               8594
_journal_paper_doi               10.1021/jo901559d
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C18 H22 O4'
_chemical_formula_weight         302.36
_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                 90.252(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.4867(4)
_cell_length_b                   25.6129(9)
_cell_length_c                   12.1381(5)
_cell_measurement_reflns_used    8983
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.31
_cell_volume                     3260.2(2)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      180(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       Omega
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18803
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle prism fragment'
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0053(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         8012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.949
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0240P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1381
_reflns_number_gt                5726
_reflns_number_total             8012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_003.cif
_cod_data_source_block           ef1308bm
_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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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      P2(1)/c
_cod_database_code               4025026
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 0.29423(13) 0.07863(5) 0.79751(11) 0.0369(4) Uani 1 1 d . . .
C2 C 0.2008(2) 0.08630(8) 0.88291(17) 0.0346(5) Uani 1 1 d . . .
O3 O 0.10119(13) 0.11996(5) 0.84204(11) 0.0353(3) Uani 1 1 d . . .
C4 C 0.13462(19) 0.16478(7) 0.78967(16) 0.0297(4) Uani 1 1 d . . .
C5 C 0.27302(18) 0.17069(7) 0.76613(15) 0.0274(4) Uani 1 1 d . . .
C6 C 0.3415(2) 0.12102(8) 0.74388(16) 0.0317(5) Uani 1 1 d . . .
C7 C 0.1377(2) 0.03439(8) 0.9006(2) 0.0491(6) Uani 1 1 d . . .
H7X H 0.1021 0.0218 0.8306 0.074 Uiso 1 1 calc R . .
H7Y H 0.0691 0.0382 0.9545 0.074 Uiso 1 1 calc R . .
H7Z H 0.2008 0.0093 0.9281 0.074 Uiso 1 1 calc R . .
C8 C 0.2615(2) 0.10842(9) 0.98558(17) 0.0425(6) Uani 1 1 d . . .
H8X H 0.3297 0.0851 1.0107 0.064 Uiso 1 1 calc R . .
H8Y H 0.1971 0.1117 1.0434 0.064 Uiso 1 1 calc R . .
H8Z H 0.2973 0.1429 0.9694 0.064 Uiso 1 1 calc R . .
O9 O 0.05157(13) 0.19409(5) 0.76150(12) 0.0392(4) Uani 1 1 d . . .
O10 O 0.42894(14) 0.11488(5) 0.68168(12) 0.0402(4) Uani 1 1 d . . .
C11 C 0.33163(18) 0.21753(7) 0.76924(15) 0.0277(4) Uani 1 1 d . . .
C12 C 0.26498(17) 0.26544(7) 0.80830(15) 0.0271(4) Uani 1 1 d . . .
C13 C 0.18822(19) 0.29524(8) 0.73994(16) 0.0350(5) Uani 1 1 d . . .
H13 H 0.1745 0.2845 0.6659 0.042 Uiso 1 1 calc R . .
C14 C 0.13115(19) 0.34045(8) 0.77781(17) 0.0349(5) Uani 1 1 d . . .
H14 H 0.0780 0.3600 0.7294 0.042 Uiso 1 1 calc R . .
C15 C 0.14963(18) 0.35800(7) 0.88490(16) 0.0307(5) Uani 1 1 d . . .
C16 C 0.2269(2) 0.32773(8) 0.95227(17) 0.0384(5) Uani 1 1 d . . .
H16 H 0.2405 0.3383 1.0264 0.046 Uiso 1 1 calc R . .
C17 C 0.2848(2) 0.28269(8) 0.91500(16) 0.0359(5) Uani 1 1 d . . .
H17 H 0.3387 0.2634 0.9631 0.043 Uiso 1 1 calc R . .
C18 C 0.0868(2) 0.40816(8) 0.92709(17) 0.0358(5) Uani 1 1 d . . .
C19 C -0.0288(3) 0.39388(12) 0.9957(3) 0.0928(11) Uani 1 1 d . . .
H19X H -0.0026 0.3708 1.0560 0.139 Uiso 1 1 calc R . .
H19Y H -0.0917 0.3760 0.9492 0.139 Uiso 1 1 calc R . .
H19Z H -0.0668 0.4257 1.0262 0.139 Uiso 1 1 calc R . .
C20 C 0.0361(5) 0.44114(12) 0.8324(3) 0.1273(17) Uani 1 1 d . . .
H20X H -0.0136 0.4703 0.8618 0.191 Uiso 1 1 calc R . .
H20Y H -0.0185 0.4196 0.7850 0.191 Uiso 1 1 calc R . .
H20Z H 0.1077 0.4547 0.7894 0.191 Uiso 1 1 calc R . .
C21 C 0.1761(3) 0.43934(13) 0.9964(4) 0.142(2) Uani 1 1 d . . .
H21X H 0.1942 0.4204 1.0649 0.213 Uiso 1 1 calc R . .
H21Y H 0.1371 0.4731 1.0138 0.213 Uiso 1 1 calc R . .
H21Z H 0.2557 0.4450 0.9562 0.213 Uiso 1 1 calc R . .
C22 C 0.46880(19) 0.22661(8) 0.74101(19) 0.0393(5) Uani 1 1 d . . .
H22X H 0.5122 0.1929 0.7328 0.059 Uiso 1 1 calc R . .
H22Y H 0.5099 0.2467 0.8000 0.059 Uiso 1 1 calc R . .
H22Z H 0.4741 0.2461 0.6717 0.059 Uiso 1 1 calc R . .
O23 O 0.79890(13) 0.07931(5) 0.94930(12) 0.0371(4) Uani 1 1 d . . .
C24 C 0.7057(2) 0.08686(8) 0.86291(18) 0.0370(5) Uani 1 1 d . . .
O25 O 0.60489(13) 0.11941(5) 0.90380(12) 0.0374(4) Uani 1 1 d . . .
C26 C 0.63594(19) 0.16423(8) 0.95694(16) 0.0313(5) Uani 1 1 d . . .
C27 C 0.77458(18) 0.17108(7) 0.98144(15) 0.0268(4) Uani 1 1 d . . .
C28 C 0.84423(19) 0.12165(7) 1.00397(16) 0.0304(5) Uani 1 1 d . . .
C29 C 0.6453(2) 0.03435(9) 0.8445(2) 0.0552(7) Uani 1 1 d . . .
H29X H 0.6091 0.0217 0.9139 0.083 Uiso 1 1 calc R . .
H29Y H 0.7100 0.0097 0.8186 0.083 Uiso 1 1 calc R . .
H29Z H 0.5775 0.0374 0.7891 0.083 Uiso 1 1 calc R . .
C30 C 0.7660(2) 0.10937(9) 0.76088(18) 0.0457(6) Uani 1 1 d . . .
H30X H 0.7012 0.1130 0.7030 0.069 Uiso 1 1 calc R . .
H30Y H 0.8337 0.0860 0.7354 0.069 Uiso 1 1 calc R . .
H30Z H 0.8023 0.1437 0.7780 0.069 Uiso 1 1 calc R . .
O31 O 0.55171(13) 0.19295(5) 0.98483(13) 0.0409(4) Uani 1 1 d . . .
O32 O 0.93085(14) 0.11583(5) 1.06785(11) 0.0391(4) Uani 1 1 d . . .
C33 C 0.83183(18) 0.21811(7) 0.97873(15) 0.0270(4) Uani 1 1 d . . .
C34 C 0.76463(18) 0.26603(7) 0.93884(16) 0.0270(4) Uani 1 1 d . . .
C35 C 0.68530(19) 0.29502(8) 1.00570(17) 0.0360(5) Uani 1 1 d . . .
H35 H 0.6696 0.2837 1.0790 0.043 Uiso 1 1 calc R . .
C36 C 0.62842(19) 0.34025(8) 0.96740(17) 0.0351(5) Uani 1 1 d . . .
H36 H 0.5738 0.3594 1.0149 0.042 Uiso 1 1 calc R . .
C37 C 0.64930(18) 0.35842(7) 0.86083(16) 0.0299(4) Uani 1 1 d . . .
C38 C 0.7295(2) 0.32878(8) 0.79545(17) 0.0379(5) Uani 1 1 d . . .
H38 H 0.7454 0.3399 0.7221 0.046 Uiso 1 1 calc R . .
C39 C 0.7872(2) 0.28359(8) 0.83336(16) 0.0363(5) Uani 1 1 d . . .
H39 H 0.8426 0.2646 0.7864 0.044 Uiso 1 1 calc R . .
C40 C 0.58495(19) 0.40825(8) 0.81784(17) 0.0339(5) Uani 1 1 d . . .
C41 C 0.4621(3) 0.39342(11) 0.7619(3) 0.1029(14) Uani 1 1 d . . .
H41X H 0.4183 0.4250 0.7364 0.154 Uiso 1 1 calc R . .
H41Y H 0.4076 0.3747 0.8140 0.154 Uiso 1 1 calc R . .
H41Z H 0.4803 0.3708 0.6987 0.154 Uiso 1 1 calc R . .
C42 C 0.6635(3) 0.43531(14) 0.7340(4) 0.1358(19) Uani 1 1 d . . .
H42X H 0.6185 0.4666 0.7081 0.204 Uiso 1 1 calc R . .
H42Y H 0.6784 0.4118 0.6717 0.204 Uiso 1 1 calc R . .
H42Z H 0.7454 0.4455 0.7668 0.204 Uiso 1 1 calc R . .
C43 C 0.5543(6) 0.44506(13) 0.9098(3) 0.162(2) Uani 1 1 d . . .
H43X H 0.6337 0.4569 0.9447 0.243 Uiso 1 1 calc R . .
H43Y H 0.5015 0.4272 0.9644 0.243 Uiso 1 1 calc R . .
H43Z H 0.5078 0.4752 0.8804 0.243 Uiso 1 1 calc R . .
C44 C 0.96949(18) 0.22743(8) 1.00678(18) 0.0373(5) Uani 1 1 d . . .
H42'X H 0.9754 0.2470 1.0760 0.056 Uiso 1 1 calc R . .
H42'Y H 1.0097 0.2475 0.9476 0.056 Uiso 1 1 calc R . .
H42'Z H 1.0133 0.1938 1.0151 0.056 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 C2 119.03(15) . . ?
O3 C2 O1 109.13(15) . . ?
O3 C2 C7 105.10(16) . . ?
O1 C2 C7 106.43(17) . . ?
O3 C2 C8 111.27(16) . . ?
O1 C2 C8 111.04(17) . . ?
C7 C2 C8 113.56(18) . . ?
C4 O3 C2 118.59(15) . . ?
O9 C4 O3 118.28(18) . . ?
O9 C4 C5 126.13(18) . . ?
O3 C4 C5 115.44(16) . . ?
C11 C5 C6 123.08(18) . . ?
C11 C5 C4 122.00(17) . . ?
C6 C5 C4 114.87(17) . . ?
O10 C6 O1 118.51(18) . . ?
O10 C6 C5 126.70(19) . . ?
O1 C6 C5 114.73(17) . . ?
C5 C11 C12 121.80(18) . . ?
C5 C11 C22 124.72(18) . . ?
C12 C11 C22 113.40(17) . . ?
C13 C12 C17 118.03(18) . . ?
C13 C12 C11 122.41(17) . . ?
C17 C12 C11 119.48(16) . . ?
C12 C13 C14 120.95(18) . . ?
C13 C14 C15 121.57(18) . . ?
C16 C15 C14 116.76(18) . . ?
C16 C15 C18 121.53(18) . . ?
C14 C15 C18 121.71(17) . . ?
C17 C16 C15 122.06(18) . . ?
C16 C17 C12 120.62(18) . . ?
C21 C18 C19 108.7(3) . . ?
C21 C18 C20 110.3(3) . . ?
C19 C18 C20 105.7(3) . . ?
C21 C18 C15 111.60(18) . . ?
C19 C18 C15 109.07(18) . . ?
C20 C18 C15 111.26(19) . . ?
C28 O23 C24 118.88(15) . . ?
O25 C24 O23 108.89(16) . . ?
O25 C24 C29 105.13(18) . . ?
O23 C24 C29 105.73(17) . . ?
O25 C24 C30 111.96(17) . . ?
O23 C24 C30 111.26(18) . . ?
C29 C24 C30 113.48(19) . . ?
C26 O25 C24 118.71(15) . . ?
O31 C26 O25 118.55(18) . . ?
O31 C26 C27 126.12(18) . . ?
O25 C26 C27 115.20(17) . . ?
C33 C27 C28 123.22(17) . . ?
C33 C27 C26 122.29(17) . . ?
C28 C27 C26 114.45(16) . . ?
O32 C28 O23 118.64(17) . . ?
O32 C28 C27 126.44(18) . . ?
O23 C28 C27 114.85(16) . . ?
C27 C33 C34 122.20(16) . . ?
C27 C33 C44 124.42(17) . . ?
C34 C33 C44 113.24(16) . . ?
C39 C34 C35 118.45(18) . . ?
C39 C34 C33 119.10(18) . . ?
C35 C34 C33 122.37(18) . . ?
C34 C35 C36 120.86(19) . . ?
C35 C36 C37 121.53(19) . . ?
C38 C37 C36 116.55(18) . . ?
C38 C37 C40 121.89(18) . . ?
C36 C37 C40 121.55(18) . . ?
C39 C38 C37 122.24(19) . . ?
C34 C39 C38 120.36(19) . . ?
C42 C40 C43 109.8(3) . . ?
C42 C40 C41 106.6(3) . . ?
C43 C40 C41 108.1(3) . . ?
C42 C40 C37 112.17(19) . . ?
C43 C40 C37 111.46(19) . . ?
C41 C40 C37 108.57(18) . . ?
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(2) . ?
O1 C2 1.443(2) . ?
C2 O3 1.441(2) . ?
C2 C7 1.501(3) . ?
C2 C8 1.508(3) . ?
O3 C4 1.359(2) . ?
C4 O9 1.198(2) . ?
C4 C5 1.488(3) . ?
C5 C11 1.348(3) . ?
C5 C6 1.487(3) . ?
C6 O10 1.200(2) . ?
C11 C12 1.491(3) . ?
C11 C22 1.498(3) . ?
C12 C13 1.383(3) . ?
C12 C17 1.383(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.386(3) . ?
C15 C18 1.533(3) . ?
C16 C17 1.381(3) . ?
C18 C21 1.488(3) . ?
C18 C19 1.518(4) . ?
C18 C20 1.520(3) . ?
O23 C28 1.356(2) . ?
O23 C24 1.444(2) . ?
C24 O25 1.436(2) . ?
C24 C29 1.503(3) . ?
C24 C30 1.508(3) . ?
O25 C26 1.356(2) . ?
C26 O31 1.199(2) . ?
C26 C27 1.493(3) . ?
C27 C33 1.346(3) . ?
C27 C28 1.486(3) . ?
C28 O32 1.201(2) . ?
C33 C34 1.495(3) . ?
C33 C44 1.501(3) . ?
C34 C39 1.378(3) . ?
C34 C35 1.381(3) . ?
C35 C36 1.383(3) . ?
C36 C37 1.393(3) . ?
C37 C38 1.385(3) . ?
C37 C40 1.534(3) . ?
C38 C39 1.384(3) . ?
C40 C42 1.484(4) . ?
C40 C43 1.497(4) . ?
C40 C41 1.503(3) . ?
