#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:33:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178396 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/18/4021841.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_4021841
loop_
_publ_author_name
'Emma L. Pearson'
'Laurence C. H. Kwan'
'Craig I. Turner'
'Garth A. Jones'
'Anthony C. Willis'
'Michael N. Paddon-Row'
'Michael S. Sherburn'
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, ACT 0200, Australia
;
_publ_contact_author_email       ' sherburn@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        ' Michael S. Sherburn '
_publ_contact_author_phone       ' 61 2 6125 4988 '
_publ_section_title
;
 Intramolecular Diels-Alder Reactions of Ester Linked 1,3,9-Decatrienes:
 Cis/Trans Selectivity in Thermal and Lewis Acid Promoted Reactions
 of Ethylene-Tethered and Benzo-Tethered Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6099
_journal_page_last               6109
_journal_paper_doi               10.1021/jo0607818
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        local
_chemical_formula_moiety         'C11 H14 O4'
_chemical_formula_sum            'C11 H14 O4'
_chemical_formula_weight         210.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-04-04
_audit_creation_method           CRYSTALS_ver_12.18
_audit_update_record
;
2006-04-03 - Report on  C11 H14 O4
             by Anthony C. Willis
             for Laurence Kwan and Mick Sherburn
2006-04-03 - passes checkcif tests with minor warnings
2006-04-04 - change to 2 sigma cut-off to match she0608
;
_cell_angle_alpha                90
_cell_angle_beta                 107.7039(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8990(3)
_cell_length_b                   5.5540(1)
_cell_length_c                   17.6497(3)
_cell_measurement_reflns_used    10358
_cell_measurement_temperature    200
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     1017.79(4)
_computing_cell_refinement       'Denzo/Scalepack '
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS '
_computing_structure_refinement  'CRYSTALS (Watkin et al 2003)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' φ and ω scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19895
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.600
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0045
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.014130
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.21 0.838 0.823 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0478
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0421
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                1790
_reflns_number_total             2324
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            jo0607818si20060413_123155.cif
_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/n'
_cod_database_code               4021841
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
O1 O 0.22643(7) 0.18094(15) 0.62211(5) 0.0379 1.0000 Uani
O3 O 0.32226(8) 0.08424(16) 0.74587(5) 0.0402 1.0000 Uani
O13 O 0.30319(10) 0.37291(19) 0.46810(5) 0.0499 1.0000 Uani
O14 O 0.27424(8) 0.66816(15) 0.54821(5) 0.0423 1.0000 Uani
C2 C 0.31710(9) 0.21285(18) 0.68096(6) 0.0299 1.0000 Uani
C4 C 0.43194(12) 0.0916(3) 0.81772(7) 0.0443 1.0000 Uani
C5 C 0.50920(11) 0.3205(2) 0.82673(7) 0.0370 1.0000 Uani
C6 C 0.54420(9) 0.36892(18) 0.75089(6) 0.0311 1.0000 Uani
C7 C 0.62500(10) 0.1689(2) 0.73316(8) 0.0394 1.0000 Uani
C8 C 0.60616(11) 0.0770(2) 0.66112(8) 0.0427 1.0000 Uani
C9 C 0.50541(12) 0.1639(2) 0.58819(7) 0.0390 1.0000 Uani
C10 C 0.44733(10) 0.40333(18) 0.60231(6) 0.0319 1.0000 Uani
C11 C 0.41924(9) 0.40162(17) 0.68261(6) 0.0277 1.0000 Uani
C12 C 0.33351(11) 0.4715(2) 0.53222(6) 0.0364 1.0000 Uani
C15 C 0.16626(16) 0.7559(3) 0.48485(9) 0.0550 1.0000 Uani
H41 H 0.3924(15) 0.066(3) 0.8618(10) 0.0520 1.0000 Uiso
H42 H 0.4853(15) -0.048(3) 0.8143(9) 0.0520 1.0000 Uiso
H51 H 0.5878(14) 0.295(3) 0.8738(9) 0.0435 1.0000 Uiso
H52 H 0.4588(14) 0.458(3) 0.8374(8) 0.0435 1.0000 Uiso
H61 H 0.5920(13) 0.519(3) 0.7573(8) 0.0372 1.0000 Uiso
H71 H 0.6921(15) 0.095(3) 0.7799(9) 0.0474 1.0000 Uiso
H81 H 0.6594(15) -0.054(3) 0.6526(9) 0.0532 1.0000 Uiso
H91 H 0.4347(15) 0.044(3) 0.5688(9) 0.0498 1.0000 Uiso
H92 H 0.5412(15) 0.183(3) 0.5436(10) 0.0498 1.0000 Uiso
H101 H 0.5110(13) 0.534(3) 0.6051(8) 0.0397 1.0000 Uiso
H111 H 0.3805(12) 0.555(2) 0.6895(8) 0.0338 1.0000 Uiso
H151 H 0.1414(17) 0.894(3) 0.5046(11) 0.0613 1.0000 Uiso
H152 H 0.0930(18) 0.639(3) 0.4750(10) 0.0613 1.0000 Uiso
H153 H 0.1891(16) 0.776(3) 0.4352(11) 0.0613 1.0000 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.220
0 -1 0 0.220
1 0 1 0.020
-1 0 -1 0.030
-1 0 1 0.100
1 0 -1 0.040
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 O3 C4 122.77(8) yes
C12 O14 C15 116.37(10) yes
O3 C2 O1 117.92(9) yes
O3 C2 C11 120.76(9) yes
O1 C2 C11 121.25(9) yes
O3 C4 C5 113.61(10) yes
O3 C4 H41 103.8(9) no
C5 C4 H41 113.3(9) no
O3 C4 H42 105.7(9) no
C5 C4 H42 110.4(9) no
H41 C4 H42 109.6(13) no
C4 C5 C6 109.73(9) yes
C4 C5 H51 106.2(8) no
C6 C5 H51 111.8(8) no
C4 C5 H52 110.2(9) no
C6 C5 H52 109.5(8) no
H51 C5 H52 109.4(12) no
C5 C6 C7 111.74(9) yes
C5 C6 C11 108.20(8) yes
C7 C6 C11 111.10(9) yes
C5 C6 H61 108.5(8) no
C7 C6 H61 109.3(8) no
C11 C6 H61 107.9(8) no
C6 C7 C8 123.50(11) yes
C6 C7 H71 117.1(9) no
C8 C7 H71 119.3(9) no
C7 C8 C9 124.06(10) yes
C7 C8 H81 120.7(9) no
C9 C8 H81 115.2(9) no
C8 C9 C10 111.92(9) yes
C8 C9 H91 111.7(9) no
C10 C9 H91 108.8(9) no
C8 C9 H92 110.9(9) no
C10 C9 H92 108.9(9) no
H91 C9 H92 104.4(13) no
C9 C10 C11 110.73(9) yes
C9 C10 C12 111.29(9) yes
C11 C10 C12 114.36(8) yes
C9 C10 H101 109.1(8) no
C11 C10 H101 106.8(8) no
C12 C10 H101 104.2(8) no
C10 C11 C6 110.34(8) yes
C10 C11 C2 109.62(8) yes
C6 C11 C2 113.80(8) yes
C10 C11 H111 109.0(7) no
C6 C11 H111 108.7(7) no
C2 C11 H111 105.2(7) no
C10 C12 O14 111.09(9) yes
C10 C12 O13 125.16(11) yes
O14 C12 O13 123.60(11) yes
O14 C15 H151 104.7(11) no
O14 C15 H152 109.5(10) no
H151 C15 H152 107.2(15) no
O14 C15 H153 111.1(10) no
H151 C15 H153 115.4(16) no
H152 C15 H153 108.7(14) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.2094(13) yes
O3 C2 1.3367(13) yes
O3 C4 1.4549(14) yes
O13 C12 1.2092(14) yes
O14 C12 1.3420(14) yes
O14 C15 1.4397(15) yes
C2 C11 1.5231(13) yes
C4 C5 1.5065(17) yes
C4 H41 1.008(16) no
C4 H42 0.980(17) no
C5 C6 1.5232(16) yes
C5 H51 1.005(14) no
C5 H52 0.991(15) no
C6 C7 1.5085(15) yes
C6 C11 1.5304(14) yes
C6 H61 0.972(15) no
C7 C8 1.3267(18) yes
C7 H71 1.009(16) no
C8 C9 1.4954(18) yes
C8 H81 0.971(17) no
C9 C10 1.5254(14) yes
C9 H91 0.996(16) no
C9 H92 0.984(16) no
C10 C11 1.5381(14) yes
C10 C12 1.5098(15) yes
C10 H101 0.995(14) no
C11 H111 0.976(14) no
C15 H151 0.917(18) no
C15 H152 1.004(19) no
C15 H153 0.987(19) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C4 3.229(2) 3_556 no
O1 O14 3.240(1) 1_545 no
O1 C15 3.302(2) 1_545 no
O1 O3 3.388(1) 3_556 no
O1 C5 3.582(2) 3_546 no
O3 C2 3.070(1) 3_546 no
O3 O3 3.2177(9) 3_556 no
O3 O3 3.2177(9) 3_546 no
O3 C11 3.402(2) 3_546 no
O13 C10 3.541(2) 2_666 no
O13 C5 3.576(1) 4_454 no
C2 C4 3.440(2) 3_556 no
C9 C9 3.577(2) 2_656 no
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_publ_flag
O1 C2 O3 C4 174.4(1) no
O1 C2 C11 C6 -163.2(1) no
O1 C2 C11 C10 -39.1(1) no
O3 C2 C11 C6 19.7(1) no
O3 C2 C11 C10 143.8(1) no
O3 C4 C5 C6 -51.5(1) no
O13 C12 O14 C15 2.3(2) no
O13 C12 C10 C9 -10.9(2) no
O13 C12 C10 C11 -137.3(1) no
O14 C12 C10 C9 173.3(1) no
O14 C12 C10 C11 46.9(1) no
C2 O3 C4 C5 24.5(2) no
C2 C11 C6 C5 -45.6(1) no
C2 C11 C6 C7 77.4(1) no
C2 C11 C10 C9 -64.1(1) no
C2 C11 C10 C12 62.6(1) no
C4 O3 C2 C11 -8.3(2) no
C4 C5 C6 C7 -60.9(1) no
C4 C5 C6 C11 61.7(1) no
C5 C6 C7 C8 136.6(1) no
C5 C6 C11 C10 -169.34(8) no
C6 C7 C8 C9 1.8(2) no
C6 C11 C10 C9 62.0(1) no
C6 C11 C10 C12 -171.33(8) no
C7 C6 C11 C10 -46.3(1) no
C7 C8 C9 C10 12.7(2) no
C8 C7 C6 C11 15.6(2) no
C8 C9 C10 C11 -43.7(1) no
C8 C9 C10 C12 -172.1(1) no
C10 C12 O14 C15 178.1(1) no
