#------------------------------------------------------------------------------
#$Date: 2016-08-12 16:10:48 +0300 (Fri, 12 Aug 2016) $
#$Revision: 185775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119137.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_7119137
loop_
_publ_author_name
'Quentin Dufrois'
'Laure Vendier'
'Michel Etienne'
_publ_section_title
;
 alpha-CC agostic structures and aggregation diversity in
 cyclopropyllithium derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              6781
_journal_volume                  52
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C33 H49 Li2 O3'
_chemical_formula_sum            'C33 H49 Li2 O3'
_chemical_formula_weight         507.6
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_date             2016-01-11T14:30:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-03-29 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                80.998(2)
_cell_angle_beta                 82.494(2)
_cell_angle_gamma                70.198(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5802(5)
_cell_length_b                   9.4380(5)
_cell_length_c                   20.2265(11)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.53
_cell_measurement_wavelength     0.71073
_cell_volume                     1516.79(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         micro-source
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27496
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             554
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0548
_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)+(0.0558P)²+1.2605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.134
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                4351
_reflns_number_total             5557
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc02638a2.cif
_cod_data_source_block           QD2050B
_cod_database_code               7119137
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
C30 C 0.2130(3) 0.5620(2) 0.82014(13) 0.0349(6) Uani 1 1 d . . .
H30A H 0.2172 0.6069 0.8607 0.042 Uiso 1 1 calc R . .
H30B H 0.1098 0.5352 0.8246 0.042 Uiso 1 1 calc R . .
C29 C 0.2198(3) 0.6718(3) 0.75725(15) 0.0468(7) Uani 1 1 d . . .
H29A H 0.1704 0.65 0.7201 0.056 Uiso 1 1 calc R . .
H29B H 0.1623 0.7783 0.7659 0.056 Uiso 1 1 calc R . .
C28 C 0.4043(3) 0.6401(3) 0.74234(12) 0.0393(6) Uani 1 1 d . . .
H28A H 0.448 0.6899 0.7718 0.047 Uiso 1 1 calc R . .
H28B H 0.4326 0.6737 0.6948 0.047 Uiso 1 1 calc R . .
C27 C 0.4695(3) 0.4692(2) 0.75764(11) 0.0332(5) Uani 1 1 d . . .
H27A H 0.4708 0.4206 0.7175 0.04 Uiso 1 1 calc R . .
H27B H 0.5839 0.4356 0.7719 0.04 Uiso 1 1 calc R . .
C26 C 0.2188(3) 0.2753(3) 0.96233(11) 0.0394(6) Uani 1 1 d . . .
H26A H 0.2572 0.3647 0.952 0.047 Uiso 1 1 calc R A 1
H26B H 0.3043 0.1915 0.9863 0.047 Uiso 1 1 calc R A 1
C25A C 0.0582(6) 0.3128(6) 1.0036(2) 0.0394(7) Uani 0.54 1 d P B 1
H25A H -0.0192 0.4134 0.9877 0.047 Uiso 0.54 1 calc PR B 1
H25B H 0.0726 0.3083 1.0518 0.047 Uiso 0.54 1 calc PR B 1
C24B C 0.0023(6) 0.1827(6) 0.9900(2) 0.0394(7) Uani 0.54 1 d P B 1
H24A H -0.1179 0.2025 1.0027 0.047 Uiso 0.54 1 calc PR B 1
H24B H 0.0661 0.0846 1.0141 0.047 Uiso 0.54 1 calc PR B 1
C24A C -0.0563(7) 0.2600(7) 0.9729(3) 0.0394(7) Uani 0.46 1 d P B 2
H24C H -0.1128 0.37 0.9612 0.047 Uiso 0.46 1 calc PR B 2
H24D H -0.1392 0.2111 0.9938 0.047 Uiso 0.46 1 calc PR B 2
C25B C 0.0796(8) 0.2307(8) 1.0164(3) 0.0394(7) Uani 0.46 1 d P B 2
H25C H 0.1199 0.1229 1.0358 0.047 Uiso 0.46 1 calc PR B 2
H25D H 0.0451 0.2961 1.053 0.047 Uiso 0.46 1 calc PR B 2
C23 C 0.0427(3) 0.1858(3) 0.91261(12) 0.0359(6) Uani 1 1 d . . .
H23A H 0.0648 0.0846 0.8984 0.043 Uiso 1 1 calc R B 1
H23B H -0.0494 0.2605 0.8883 0.043 Uiso 1 1 calc R B 1
C19 C 0.8568(3) -0.0328(3) 0.65219(15) 0.0496(7) Uani 1 1 d . B .
H19A H 0.8154 -0.1148 0.645 0.06 Uiso 1 1 calc R . .
H19B H 0.917 -0.0651 0.6934 0.06 Uiso 1 1 calc R . .
C20 C 0.9660(4) -0.0048(3) 0.59583(16) 0.0561(8) Uani 1 1 d . . .
H20A H 0.9505 -0.0482 0.5566 0.067 Uiso 1 1 calc R . .
H20B H 1.0832 -0.0517 0.6066 0.067 Uiso 1 1 calc R . .
C21 C 0.9235(3) 0.1649(3) 0.58049(12) 0.0371(6) Uani 1 1 d . . .
H21A H 1.0159 0.1977 0.5896 0.044 Uiso 1 1 calc R . .
H21B H 0.8997 0.1987 0.5329 0.044 Uiso 1 1 calc R . .
C22 C 0.7715(3) 0.2278(3) 0.62666(13) 0.0371(6) Uani 1 1 d . B .
H22A H 0.7972 0.281 0.6602 0.045 Uiso 1 1 calc R . .
H22B H 0.6815 0.301 0.6007 0.045 Uiso 1 1 calc R . .
C10 C 0.6051(2) 0.0451(2) 0.83529(10) 0.0213(4) Uani 1 1 d . B .
C11 C 0.6351(3) 0.1299(2) 0.88804(11) 0.0255(5) Uani 1 1 d . B .
H11A H 0.5754 0.2404 0.8859 0.031 Uiso 1 1 calc R . .
H11B H 0.6521 0.0763 0.934 0.031 Uiso 1 1 calc R . .
C12 C 0.7686(3) 0.0752(2) 0.83334(11) 0.0271(5) Uani 1 1 d . . .
H12A H 0.8677 -0.0119 0.8457 0.033 Uiso 1 1 calc R . .
H12B H 0.7911 0.1521 0.7976 0.033 Uiso 1 1 calc R . .
C13 C 0.6092(2) -0.1122(2) 0.85804(9) 0.0191(4) Uani 1 1 d . . .
C14 C 0.4914(2) -0.1465(2) 0.90716(10) 0.0224(4) Uani 1 1 d . . .
H14 H 0.408 -0.0659 0.9269 0.027 Uiso 1 1 calc R . .
C15 C 0.4924(3) -0.2938(2) 0.92777(11) 0.0280(5) Uani 1 1 d . . .
H15 H 0.4108 -0.3123 0.9613 0.034 Uiso 1 1 calc R . .
C16 C 0.6109(3) -0.4142(2) 0.89995(11) 0.0323(5) Uani 1 1 d . . .
H16 H 0.612 -0.5153 0.9141 0.039 Uiso 1 1 calc R . .
C17 C 0.7279(3) -0.3842(2) 0.85101(11) 0.0311(5) Uani 1 1 d . . .
H17 H 0.8096 -0.4658 0.8312 0.037 Uiso 1 1 calc R . .
C18 C 0.7277(2) -0.2372(2) 0.83050(10) 0.0240(5) Uani 1 1 d . . .
H18 H 0.8099 -0.2202 0.7969 0.029 Uiso 1 1 calc R . .
C1 C 0.2956(2) 0.1784(2) 0.72567(9) 0.0195(4) Uani 1 1 d . B .
C3 C 0.2180(3) 0.0584(2) 0.75732(10) 0.0246(5) Uani 1 1 d . B .
H3A H 0.2499 0.006 0.8023 0.03 Uiso 1 1 calc R . .
H3B H 0.1014 0.0757 0.7491 0.03 Uiso 1 1 calc R . .
C2 C 0.3477(3) 0.0250(2) 0.69897(10) 0.0242(5) Uani 1 1 d . . .
H2A H 0.3104 0.0221 0.6551 0.029 Uiso 1 1 calc R . .
H2B H 0.459 -0.0476 0.7083 0.029 Uiso 1 1 calc R . .
C4 C 0.1905(2) 0.3083(2) 0.68367(10) 0.0193(4) Uani 1 1 d . . .
C9 C 0.0304(2) 0.3954(2) 0.70749(10) 0.0238(4) Uani 1 1 d . . .
H9 H -0.0131 0.3671 0.7513 0.029 Uiso 1 1 calc R . .
C8 C -0.0655(3) 0.5215(2) 0.66862(12) 0.0295(5) Uani 1 1 d . . .
H8 H -0.173 0.5782 0.6862 0.035 Uiso 1 1 calc R . .
C7 C -0.0068(3) 0.5654(2) 0.60484(12) 0.0314(5) Uani 1 1 d . . .
H7 H -0.0728 0.6518 0.5784 0.038 Uiso 1 1 calc R . .
C6 C 0.1505(3) 0.4813(2) 0.57980(11) 0.0303(5) Uani 1 1 d . . .
H6 H 0.1921 0.5097 0.5357 0.036 Uiso 1 1 calc R . .
C5 C 0.2471(3) 0.3564(2) 0.61861(10) 0.0248(5) Uani 1 1 d . . .
H5 H 0.355 0.3016 0.6007 0.03 Uiso 1 1 calc R . .
C31 C 0.5416(3) 0.0609(2) 0.49533(11) 0.0260(5) Uani 1 1 d . . .
H31A H 0.5553 0.0831 0.5401 0.031 Uiso 1 1 calc R . .
H31B H 0.6538 0.0212 0.4721 0.031 Uiso 1 1 calc R . .
C32 C 0.4444(3) 0.2073(2) 0.45523(11) 0.0308(5) Uani 1 1 d . . .
H32A H 0.3313 0.246 0.4779 0.037 Uiso 1 1 calc R . .
H32B H 0.433 0.1857 0.4101 0.037 Uiso 1 1 calc R . .
C33 C 0.5268(3) 0.3294(3) 0.44756(13) 0.0422(6) Uani 1 1 d . . .
H33A H 0.534 0.3546 0.492 0.063 Uiso 1 1 calc R . .
H33B H 0.4606 0.4204 0.4206 0.063 Uiso 1 1 calc R . .
H33C H 0.6388 0.2919 0.4251 0.063 Uiso 1 1 calc R . .
Li2 Li 0.3504(4) 0.2193(4) 0.82298(16) 0.0215(7) Uani 1 1 d . . .
Li1 Li 0.5531(4) 0.1082(4) 0.73271(17) 0.0263(8) Uani 1 1 d . B .
O3 O 0.35724(17) 0.43026(15) 0.81135(7) 0.0248(3) Uani 1 1 d . B .
O2 O 0.18937(17) 0.23015(16) 0.90125(7) 0.0251(3) Uani 1 1 d . B .
O1 O 0.72092(17) 0.10315(16) 0.65954(7) 0.0282(4) 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'
Li Li -0.0003 0.0001 '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
O3 C30 C29 105.06(19) . .
C28 C29 C30 101.65(19) . .
C29 C28 C27 101.55(19) . .
O3 C27 C28 105.82(18) . .
O2 C26 C25A 106.2(3) . .
O2 C26 C25B 102.2(3) . .
C25A C26 C25B 27.2(2) . .
C26 C25A C24B 98.4(4) . .
C25A C24B C23 101.2(3) . .
C25B C24A C23 99.7(4) . .
C24A C25B C26 100.6(4) . .
O2 C23 C24A 106.0(3) . .
O2 C23 C24B 102.9(3) . .
C24A C23 C24B 29.8(2) . .
O1 C19 C20 108.6(2) . .
C19 C20 C21 107.0(2) . .
C22 C21 C20 104.56(18) . .
O1 C22 C21 107.50(18) . .
C13 C10 C12 115.95(17) . .
C13 C10 C11 115.80(16) . .
C12 C10 C11 59.09(13) . .
C13 C10 Li1 111.17(16) . .
C12 C10 Li1 100.88(16) . .
C11 C10 Li1 133.02(17) . .
C13 C10 Li2 116.14(15) . .
C12 C10 Li2 127.17(16) . .
C11 C10 Li2 90.53(14) . .
Li1 C10 Li2 67.66(13) . .
C12 C11 C10 60.21(13) . .
C12 C11 Li2 102.74(14) . .
C10 C11 Li2 55.67(12) . .
C11 C12 C10 60.70(13) . .
C14 C13 C18 115.65(18) . .
C14 C13 C10 122.00(17) . .
C18 C13 C10 122.32(18) . .
C15 C14 C13 122.32(19) . .
C16 C15 C14 120.6(2) . .
C15 C16 C17 118.6(2) . .
C16 C17 C18 121.0(2) . .
C17 C18 C13 121.86(19) . .
C4 C1 C3 116.30(17) . .
C4 C1 C2 116.11(16) . .
C3 C1 C2 59.23(13) . .
C4 C1 Li1 129.27(17) . .
C3 C1 Li1 113.02(16) . .
C2 C1 Li1 79.89(15) . .
C4 C1 Li2 117.67(15) . .
C3 C1 Li2 93.42(14) . .
C2 C1 Li2 126.11(16) . .
Li1 C1 Li2 69.37(14) . .
C2 C3 C1 60.62(13) . .
C2 C3 Li2 99.16(14) . .
C1 C3 Li2 53.08(12) . .
C3 C2 C1 60.15(13) . .
C3 C2 Li1 100.76(15) . .
C1 C2 Li1 60.71(13) . .
C5 C4 C9 116.21(18) . .
C5 C4 C1 121.80(17) . .
C9 C4 C1 121.93(18) . .
C8 C9 C4 121.7(2) . .
C7 C8 C9 120.7(2) . .
C8 C7 C6 118.9(2) . .
C5 C6 C7 120.5(2) . .
C6 C5 C4 121.96(19) . .
C32 C31 C31 113.2(2) . 2_656
C31 C32 C33 112.77(19) . .
O2 Li2 O3 99.42(15) . .
O2 Li2 C1 120.98(17) . .
O3 Li2 C1 106.69(16) . .
O2 Li2 C10 116.13(16) . .
O3 Li2 C10 112.04(16) . .
C1 Li2 C10 101.50(14) . .
O2 Li2 Li1 158.65(19) . .
O3 Li2 Li1 101.88(16) . .
C1 Li2 Li1 53.32(12) . .
C10 Li2 Li1 53.57(12) . .
O2 Li2 C11 98.81(14) . .
O3 Li2 C11 88.29(13) . .
C1 Li2 C11 133.17(15) . .
C10 Li2 C11 33.80(8) . .
Li1 Li2 C11 80.50(13) . .
O2 Li2 C3 94.39(13) . .
O3 Li2 C3 135.65(16) . .
C1 Li2 C3 33.50(8) . .
C10 Li2 C3 98.72(13) . .
Li1 Li2 C3 71.17(13) . .
C11 Li2 C3 130.90(13) . .
O1 Li1 C1 126.50(19) . .
O1 Li1 C10 123.75(18) . .
C1 Li1 C10 109.74(16) . .
O1 Li1 C2 108.55(17) . .
C1 Li1 C2 39.40(9) . .
C10 Li1 C2 115.97(17) . .
O1 Li1 Li2 156.0(2) . .
C1 Li1 Li2 57.31(12) . .
C10 Li1 Li2 58.76(12) . .
C2 Li1 Li2 87.72(14) . .
C30 O3 C27 109.06(16) . .
C30 O3 Li2 123.95(16) . .
C27 O3 Li2 117.18(15) . .
C23 O2 C26 109.42(16) . .
C23 O2 Li2 130.22(16) . .
C26 O2 Li2 120.10(16) . .
C19 O1 C22 108.11(17) . .
C19 O1 Li1 119.82(17) . .
C22 O1 Li1 126.84(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C30 O3 1.442(2) .
C30 C29 1.518(4) .
C29 C28 1.506(4) .
C28 C27 1.513(3) .
C27 O3 1.444(3) .
C26 O2 1.446(3) .
C26 C25A 1.477(5) .
C26 C25B 1.629(6) .
C25A C24B 1.534(8) .
C24B C23 1.556(5) .
C24A C25B 1.478(9) .
C24A C23 1.514(6) .
C23 O2 1.436(3) .
C19 O1 1.424(3) .
C19 C20 1.429(3) .
C20 C21 1.508(3) .
C21 C22 1.502(3) .
C22 O1 1.429(3) .
C10 C13 1.474(3) .
C10 C12 1.517(3) .
C10 C11 1.524(3) .
C10 Li1 2.129(4) .
C10 Li2 2.263(4) .
C11 C12 1.500(3) .
C11 Li2 2.740(4) .
C13 C14 1.405(3) .
C13 C18 1.407(3) .
C14 C15 1.385(3) .
C15 C16 1.381(3) .
C16 C17 1.383(3) .
C17 C18 1.384(3) .
C1 C4 1.471(3) .
C1 C3 1.519(3) .
C1 C2 1.526(3) .
C1 Li1 2.098(4) .
C1 Li2 2.201(4) .
C3 C2 1.505(3) .
C3 Li2 2.748(4) .
C2 Li1 2.368(4) .
C4 C5 1.403(3) .
C4 C9 1.407(3) .
C9 C8 1.387(3) .
C8 C7 1.376(3) .
C7 C6 1.389(3) .
C6 C5 1.382(3) .
C31 C32 1.519(3) .
C31 C31 1.523(4) 2_656
C32 C33 1.524(3) .
Li2 O2 1.952(3) .
Li2 O3 1.988(3) .
Li2 Li1 2.448(5) .
Li1 O1 1.920(4) .
