#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/49/1504987.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_1504987
loop_
_publ_author_name
'Rigby, James H.'
'Laurent, Stéphane B'
'Kamal, Zeeshan'
'Heeg, Mary Jane'
_publ_section_title
;
 Chromium(0)-promoted [6pi + 2pi] cycloadditions of allenes with
 cycloheptatriene.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5609
_journal_page_last               5612
_journal_paper_doi               10.1021/ol802401a
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C13 H16 O2'
_chemical_formula_weight         204.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.488(2)
_cell_angle_beta                 88.2290(10)
_cell_angle_gamma                78.6350(10)
_cell_formula_units_Z            4
_cell_length_a                   7.4379(2)
_cell_length_b                   10.6548(3)
_cell_length_c                   13.3291(4)
_cell_measurement_reflns_used    5542
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.35
_cell_volume                     1026.71(5)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_method       'Bruker APEX2'
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21914
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5061
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0427
_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)+(0.0592P)²+0.2803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                3982
_reflns_number_total             5061
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802401a_si_002.cif
_cod_data_source_block           dtep
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504987
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.09141(14) 0.38989(9) 0.38133(7) 0.0189(2) Uani 1 1 d D . .
H1A H -0.0097(14) 0.4386(16) 0.3903(15) 0.046(6) Uiso 1 1 d D . .
O2 O 0.06537(15) 0.09319(10) 0.03614(8) 0.0253(2) Uani 1 1 d D . .
H2A H 0.164(3) 0.106(4) 0.008(3) 0.037(11) Uiso 0.50 1 d PD A 1
H2B H 0.012(5) 0.048(3) 0.004(3) 0.044(12) Uiso 0.50 1 d PD B 2
C1 C -0.13068(17) 0.26876(12) 0.25010(9) 0.0128(2) Uani 1 1 d . . .
H1 H -0.1181 0.3597 0.2265 0.015 Uiso 1 1 calc R . .
C2 C -0.11772(17) 0.23975(12) 0.36574(9) 0.0137(2) Uani 1 1 d . . .
H2 H -0.2166 0.3010 0.3968 0.016 Uiso 1 1 calc R . .
C3 C -0.14125(17) 0.10290(12) 0.40007(9) 0.0152(3) Uani 1 1 d . . .
H3 H -0.1744 0.0795 0.4684 0.018 Uiso 1 1 calc R . .
C4 C -0.11631(17) 0.01500(12) 0.33643(10) 0.0159(3) Uani 1 1 d . . .
H4 H -0.1344 -0.0698 0.3595 0.019 Uiso 1 1 calc R . .
C5 C -0.06034(17) 0.04720(12) 0.22933(9) 0.0142(2) Uani 1 1 d . . .
H5 H 0.0194 -0.0285 0.2028 0.017 Uiso 1 1 calc R . .
C6 C -0.20729(17) 0.12276(12) 0.14934(9) 0.0153(3) Uani 1 1 d . . .
H6 H -0.2810 0.0748 0.1122 0.018 Uiso 1 1 calc R . .
C7 C -0.04784(18) 0.17912(12) 0.09521(9) 0.0152(3) Uani 1 1 d . . .
H7 H -0.0855 0.2689 0.0599 0.018 Uiso 1 1 calc R . .
C8 C 0.02084(17) 0.17215(12) 0.20467(9) 0.0130(2) Uani 1 1 d . . .
C9 C -0.30289(17) 0.23657(12) 0.20321(10) 0.0153(3) Uani 1 1 d . . .
H9A H -0.3903 0.2107 0.2557 0.018 Uiso 1 1 calc R . .
H9B H -0.3667 0.3093 0.1551 0.018 Uiso 1 1 calc R . .
C10 C 0.21222(17) 0.18302(13) 0.23351(9) 0.0156(3) Uani 1 1 d . . .
H10A H 0.2404 0.2657 0.2004 0.019 Uiso 1 1 calc R . .
H10B H 0.3029 0.1118 0.2096 0.019 Uiso 1 1 calc R . .
C11 C 0.22633(17) 0.17678(12) 0.34753(9) 0.0144(3) Uani 1 1 d . . .
C12 C 0.07054(17) 0.25711(12) 0.40069(9) 0.0148(3) Uani 1 1 d . . .
H12 H 0.0816 0.2288 0.4752 0.018 Uiso 1 1 calc R . .
C13 C 0.36638(18) 0.10304(13) 0.39941(10) 0.0182(3) Uani 1 1 d . . .
H13A H 0.3699 0.1001 0.4709 0.022 Uiso 1 1 calc R . .
H13B H 0.4632 0.0532 0.3651 0.022 Uiso 1 1 calc R . .
O3 O 0.39218(14) 0.11007(9) -0.04565(8) 0.0209(2) Uani 1 1 d D . .
H3A H 0.466(4) 0.047(2) -0.016(3) 0.033(10) Uiso 0.50 1 d PD C 1
H3B H 0.289(3) 0.120(4) -0.017(3) 0.053(13) Uiso 0.50 1 d PD D 2
O4 O 0.21874(14) 0.43250(9) -0.43092(7) 0.0220(2) Uani 1 1 d . . .
H4A H 0.2110 0.4289 -0.4932 0.026 Uiso 1 1 calc R . .
C14 C 0.52929(18) 0.20772(12) -0.24569(9) 0.0157(3) Uani 1 1 d . . .
H14 H 0.4806 0.1263 -0.2425 0.019 Uiso 1 1 calc R . .
C15 C 0.61005(17) 0.22008(12) -0.14355(9) 0.0158(3) Uani 1 1 d . . .
H15 H 0.7072 0.1422 -0.1234 0.019 Uiso 1 1 calc R . .
C16 C 0.69443(18) 0.33904(13) -0.15382(10) 0.0195(3) Uani 1 1 d . . .
H16 H 0.7864 0.3443 -0.1075 0.023 Uiso 1 1 calc R . .
C17 C 0.64254(18) 0.43669(13) -0.22649(10) 0.0181(3) Uani 1 1 d . . .
H17 H 0.6979 0.5104 -0.2313 0.022 Uiso 1 1 calc R . .
C18 C 0.49785(17) 0.43170(12) -0.30064(9) 0.0145(2) Uani 1 1 d . . .
H18 H 0.4222 0.5190 -0.3225 0.017 Uiso 1 1 calc R . .
C19 C 0.55361(19) 0.35220(13) -0.39257(10) 0.0187(3) Uani 1 1 d . . .
H10 H 0.6025 0.3935 -0.4566 0.022 Uiso 1 1 calc R . .
C20 C 0.35489(19) 0.32760(13) -0.38751(10) 0.0182(3) Uani 1 1 d . . .
H20 H 0.3435 0.2420 -0.4070 0.022 Uiso 1 1 calc R . .
C21 C 0.37685(17) 0.32742(12) -0.27306(9) 0.0141(3) Uani 1 1 d . . .
C22 C 0.6585(2) 0.22343(13) -0.33918(10) 0.0204(3) Uani 1 1 d . . .
H22A H 0.7832 0.2295 -0.3191 0.024 Uiso 1 1 calc R . .
H22B H 0.6663 0.1525 -0.3813 0.024 Uiso 1 1 calc R . .
C23 C 0.22084(18) 0.33852(13) -0.19706(10) 0.0170(3) Uani 1 1 d . . .
H23A H 0.1312 0.4196 -0.2157 0.020 Uiso 1 1 calc R . .
H23B H 0.1570 0.2652 -0.1968 0.020 Uiso 1 1 calc R . .
C24 C 0.29789(18) 0.33773(12) -0.09328(9) 0.0157(3) Uani 1 1 d . . .
C25 C 0.45821(18) 0.22932(12) -0.06189(9) 0.0158(3) Uani 1 1 d . . .
H25 H 0.5101 0.2447 0.0027 0.019 Uiso 1 1 calc R . .
C26 C 0.2368(2) 0.42778(14) -0.03421(11) 0.0261(3) Uani 1 1 d . . .
H26A H 0.1399 0.4973 -0.0564 0.031 Uiso 1 1 calc R . .
H26B H 0.2900 0.4229 0.0304 0.031 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
C2 C1 C8 107.94(10)
C2 C1 C9 115.16(10)
C8 C1 C9 99.99(9)
C3 C2 C1 110.24(10)
C3 C2 C12 109.30(10)
C1 C2 C12 109.79(10)
C4 C3 C2 121.11(11)
C3 C4 C5 121.06(11)
C4 C5 C8 116.39(10)
C4 C5 C6 119.96(11)
C8 C5 C6 81.99(9)
C9 C6 C7 100.92(10)
C9 C6 C5 102.43(10)
C7 C6 C5 86.27(9)
O2 C7 C8 114.09(11)
O2 C7 C6 113.59(10)
C8 C7 C6 83.19(9)
C10 C8 C1 113.14(10)
C10 C8 C7 125.38(10)
C1 C8 C7 102.15(10)
C10 C8 C5 124.18(10)
C1 C8 C5 99.64(9)
C7 C8 C5 86.81(9)
C6 C9 C1 98.62(10)
C8 C10 C11 110.27(10)
C13 C11 C12 120.89(12)
C13 C11 C10 122.13(12)
C12 C11 C10 116.97(10)
O1 C12 C11 107.75(10)
O1 C12 C2 111.80(10)
C11 C12 C2 111.53(10)
C15 C14 C21 107.74(10)
C15 C14 C22 115.34(11)
C21 C14 C22 99.56(10)
C16 C15 C14 109.40(10)
C16 C15 C25 110.05(11)
C14 C15 C25 109.93(10)
C17 C16 C15 121.32(12)
C16 C17 C18 120.71(12)
C17 C18 C21 117.08(10)
C17 C18 C19 118.60(11)
C21 C18 C19 81.78(9)
C22 C19 C20 101.00(11)
C22 C19 C18 101.72(10)
C20 C19 C18 86.32(10)
O4 C20 C21 112.56(11)
O4 C20 C19 115.36(11)
C21 C20 C19 83.55(9)
C23 C21 C20 124.92(11)
C23 C21 C14 113.20(10)
C20 C21 C14 102.25(10)
C23 C21 C18 124.34(11)
C20 C21 C18 87.19(9)
C14 C21 C18 99.47(10)
C19 C22 C14 98.90(10)
C24 C23 C21 108.84(10)
C26 C24 C23 123.26(12)
C26 C24 C25 121.10(12)
C23 C24 C25 115.58(11)
O3 C25 C24 108.34(10)
O3 C25 C15 109.39(10)
C24 C25 C15 111.56(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.4425(15)
O2 C7 1.4180(16)
C1 C2 1.5341(16)
C1 C8 1.5362(17)
C1 C9 1.5581(17)
C2 C3 1.5124(17)
C2 C12 1.5417(17)
C3 C4 1.3269(19)
C4 C5 1.4900(17)
C5 C8 1.5606(17)
C5 C6 1.5749(17)
C6 C9 1.5323(18)
C6 C7 1.5500(18)
C7 C8 1.5485(17)
C8 C10 1.5158(17)
C10 C11 1.5184(17)
C11 C13 1.3268(18)
C11 C12 1.5147(18)
O3 C25 1.4387(15)
O4 C20 1.4250(16)
C14 C15 1.5363(18)
C14 C21 1.5425(17)
C14 C22 1.5619(18)
C15 C16 1.5106(18)
C15 C25 1.5421(18)
C16 C17 1.3307(18)
C17 C18 1.4967(18)
C18 C21 1.5641(17)
C18 C19 1.5787(18)
C19 C22 1.5345(18)
C19 C20 1.5492(19)
C20 C21 1.5389(17)
C21 C23 1.5137(18)
C23 C24 1.5120(18)
C24 C26 1.3230(19)
C24 C25 1.5142(18)
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
C8 C1 C2 C3 -59.30(12)
C9 C1 C2 C3 51.40(14)
C8 C1 C2 C12 61.17(12)
C9 C1 C2 C12 171.87(10)
C1 C2 C3 C4 19.51(16)
C12 C2 C3 C4 -101.25(13)
C2 C3 C4 C5 1.30(18)
C3 C4 C5 C8 17.10(17)
C3 C4 C5 C6 -79.01(16)
C4 C5 C6 C9 49.58(14)
C8 C5 C6 C9 -66.33(10)
C4 C5 C6 C7 149.95(11)
C8 C5 C6 C7 34.04(8)
C9 C6 C7 O2 -178.92(10)
C5 C6 C7 O2 79.12(11)
C9 C6 C7 C8 67.72(10)
C5 C6 C7 C8 -34.23(9)
C2 C1 C8 C10 -61.59(13)
C9 C1 C8 C10 177.70(10)
C2 C1 C8 C7 161.01(10)
C9 C1 C8 C7 40.30(11)
C2 C1 C8 C5 72.22(11)
C9 C1 C8 C5 -48.49(11)
O2 C7 C8 C10 52.33(17)
C6 C7 C8 C10 165.16(12)
O2 C7 C8 C1 -177.44(10)
C6 C7 C8 C1 -64.61(10)
O2 C7 C8 C5 -78.26(12)
C6 C7 C8 C5 34.57(9)
C4 C5 C8 C10 74.86(15)
C6 C5 C8 C10 -165.59(12)
C4 C5 C8 C1 -51.81(13)
C6 C5 C8 C1 67.74(9)
C4 C5 C8 C7 -153.60(11)
C6 C5 C8 C7 -34.05(9)
C7 C6 C9 C1 -47.45(11)
C5 C6 C9 C1 41.10(11)
C2 C1 C9 C6 -111.29(11)
C8 C1 C9 C6 4.07(11)
C1 C8 C10 C11 52.11(14)
C7 C8 C10 C11 177.86(11)
C5 C8 C10 C11 -68.57(15)
C8 C10 C11 C13 133.72(13)
C8 C10 C11 C12 -45.15(14)
C13 C11 C12 O1 105.31(13)
C10 C11 C12 O1 -75.81(13)
C13 C11 C12 C2 -131.64(12)
C10 C11 C12 C2 47.24(14)
C3 C2 C12 O1 -172.71(10)
C1 C2 C12 O1 66.25(13)
C3 C2 C12 C11 66.58(13)
C1 C2 C12 C11 -54.46(13)
C21 C14 C15 C16 -62.09(13)
C22 C14 C15 C16 48.06(14)
C21 C14 C15 C25 58.86(13)
C22 C14 C15 C25 169.01(10)
C14 C15 C16 C17 22.75(18)
C25 C15 C16 C17 -98.13(15)
C15 C16 C17 C18 0.1(2)
C16 C17 C18 C21 15.52(19)
C16 C17 C18 C19 -79.99(17)
C17 C18 C19 C22 49.37(15)
C21 C18 C19 C22 -67.06(10)
C17 C18 C19 C20 149.85(11)
C21 C18 C19 C20 33.42(9)
C22 C19 C20 O4 179.30(10)
C18 C19 C20 O4 78.06(11)
C22 C19 C20 C21 67.35(10)
C18 C19 C20 C21 -33.88(9)
O4 C20 C21 C23 50.27(16)
C19 C20 C21 C23 165.09(12)
O4 C20 C21 C14 -179.70(10)
C19 C20 C21 C14 -64.88(10)
O4 C20 C21 C18 -80.61(12)
C19 C20 C21 C18 34.21(9)
C15 C14 C21 C23 -61.57(13)
C22 C14 C21 C23 177.79(11)
C15 C14 C21 C20 161.51(10)
C22 C14 C21 C20 40.87(12)
C15 C14 C21 C18 72.35(11)
C22 C14 C21 C18 -48.28(11)
C17 C18 C21 C23 77.03(15)
C19 C18 C21 C23 -164.98(12)
C17 C18 C21 C20 -151.63(11)
C19 C18 C21 C20 -33.64(9)
C17 C18 C21 C14 -49.68(13)
C19 C18 C21 C14 68.32(10)
C20 C19 C22 C14 -46.51(12)
C18 C19 C22 C14 41.97(12)
C15 C14 C22 C19 -111.53(12)
C21 C14 C22 C19 3.41(12)
C20 C21 C23 C24 -178.69(11)
C14 C21 C23 C24 55.81(14)
C18 C21 C23 C24 -64.83(15)
C21 C23 C24 C26 126.83(14)
C21 C23 C24 C25 -50.36(14)
C26 C24 C25 O3 113.38(14)
C23 C24 C25 O3 -69.36(13)
C26 C24 C25 C15 -126.15(13)
C23 C24 C25 C15 51.11(14)
C16 C15 C25 O3 -174.16(10)
C14 C15 C25 O3 65.27(13)
C16 C15 C25 C24 65.99(13)
C14 C15 C25 C24 -54.58(14)
