#------------------------------------------------------------------------------
#$Date: 2016-08-12 16:10:48 +0300 (Fri, 12 Aug 2016) $
#$Revision: 185775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119136.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_7119136
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         'C38 H62 Li4 N2 O4'
_chemical_formula_sum            'C38 H62 Li4 N2 O4'
_chemical_formula_weight         638.66
_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             2015-06-04T16:40:16-00:00
_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                104.353(4)
_cell_angle_beta                 93.696(4)
_cell_angle_gamma                116.282(4)
_cell_formula_units_Z            1
_cell_length_a                   8.7871(10)
_cell_length_b                   9.5833(11)
_cell_length_c                   13.1959(13)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.22
_cell_measurement_theta_min      2.49
_cell_measurement_wavelength     0.71073
_cell_volume                     945.63(19)
_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    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0259
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23990
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.912
_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    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0460P)²+0.5119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                3319
_reflns_number_total             3853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc02638a2.cif
_cod_data_source_block           qd020615
_cod_original_cell_volume        945.63(18)
_cod_database_code               7119136
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
C1 C 0.08593(16) 0.83008(16) 0.27857(10) 0.0198(3) Uani 1 1 d . . .
C2 C 0.15032(18) 0.93600(17) 0.20584(11) 0.0238(3) Uani 1 1 d . . .
H2A H 0.19 0.8938 0.1424 0.029 Uiso 1 1 calc R . .
H2B H 0.0918 1.0005 0.1953 0.029 Uiso 1 1 calc R . .
C3 C 0.25960(17) 0.98641(16) 0.31371(11) 0.0234(3) Uani 1 1 d . . .
H3A H 0.268 1.0817 0.3694 0.028 Uiso 1 1 calc R . .
H3B H 0.3663 0.975 0.3165 0.028 Uiso 1 1 calc R . .
C4 C 0.09739(16) 0.67671(16) 0.24999(10) 0.0190(3) Uani 1 1 d . . .
C5 C 0.01434(17) 0.55588(16) 0.15036(11) 0.0221(3) Uani 1 1 d . . .
H5 H -0.0466 0.5755 0.0981 0.027 Uiso 1 1 calc R . .
C6 C 0.01916(18) 0.40831(17) 0.12639(11) 0.0249(3) Uani 1 1 d . . .
H6 H -0.0383 0.3291 0.0583 0.03 Uiso 1 1 calc R . .
C7 C 0.10662(19) 0.37531(17) 0.20053(12) 0.0265(3) Uani 1 1 d . . .
H7 H 0.1097 0.2744 0.184 0.032 Uiso 1 1 calc R . .
C8 C 0.18977(19) 0.49285(18) 0.29961(12) 0.0269(3) Uani 1 1 d . . .
H8 H 0.2503 0.4721 0.3514 0.032 Uiso 1 1 calc R . .
C9 C 0.18535(18) 0.63993(17) 0.32365(11) 0.0238(3) Uani 1 1 d . . .
H9 H 0.2434 0.7184 0.3919 0.029 Uiso 1 1 calc R . .
C10 C -0.08476(19) 1.11988(17) 0.36647(11) 0.0262(3) Uani 1 1 d . . .
H10A H -0.1494 1.0857 0.2937 0.039 Uiso 1 1 calc R . .
H10B H 0.0383 1.1571 0.3654 0.039 Uiso 1 1 calc R . .
H10C H -0.0989 1.2095 0.4118 0.039 Uiso 1 1 calc R . .
C11 C -0.33437(18) 0.92939(19) 0.40711(12) 0.0260(3) Uani 1 1 d D . .
H11A H -0.386(2) 0.8335(16) 0.4334(14) 0.039 Uiso 1 1 d D . .
H11B H -0.357(2) 1.0157(17) 0.4513(13) 0.039 Uiso 1 1 d D . .
H11C H -0.399(2) 0.902(2) 0.3345(9) 0.039 Uiso 1 1 d D . .
C12 C -0.50597(17) 0.68628(17) 0.11053(11) 0.0233(3) Uani 1 1 d . . .
H12A H -0.5538 0.6725 0.1754 0.028 Uiso 1 1 calc R . .
H12B H -0.5676 0.5808 0.0525 0.028 Uiso 1 1 calc R . .
C13 C -0.5240(2) 0.82040(19) 0.07781(12) 0.0301(3) Uani 1 1 d . . .
H13A H -0.5317 0.8985 0.1397 0.036 Uiso 1 1 calc R . .
H13B H -0.6284 0.7736 0.0213 0.036 Uiso 1 1 calc R . .
C14 C -0.3585(2) 0.90466(18) 0.03594(12) 0.0329(4) Uani 1 1 d . . .
H14A H -0.3866 0.898 -0.0396 0.039 Uiso 1 1 calc R . .
H14B H -0.289 1.0211 0.0792 0.039 Uiso 1 1 calc R . .
C15 C -0.26220(19) 0.80894(19) 0.04706(11) 0.0285(3) Uani 1 1 d . . .
H15A H -0.2894 0.7213 -0.0204 0.034 Uiso 1 1 calc R . .
H15B H -0.1355 0.8821 0.0662 0.034 Uiso 1 1 calc R . .
C16 C -0.2615(2) 0.57255(19) 0.40445(12) 0.0338(4) Uani 1 1 d . . .
H16A H -0.2983 0.6289 0.4634 0.041 Uiso 1 1 calc R . .
H16B H -0.1335 0.6244 0.4195 0.041 Uiso 1 1 calc R . .
C17 C -0.3388(2) 0.39387(19) 0.39353(13) 0.0361(4) Uani 1 1 d . . .
H17A H -0.4542 0.3524 0.4131 0.043 Uiso 1 1 calc R . .
H17B H -0.2623 0.3718 0.4381 0.043 Uiso 1 1 calc R . .
C18 C -0.3525(2) 0.31860(18) 0.27475(12) 0.0321(3) Uani 1 1 d . . .
H18A H -0.24 0.3283 0.2594 0.039 Uiso 1 1 calc R . .
H18B H -0.4415 0.202 0.2487 0.039 Uiso 1 1 calc R . .
C19 C -0.40499(18) 0.42195(16) 0.22575(11) 0.0253(3) Uani 1 1 d . . .
H19A H -0.3638 0.4273 0.158 0.03 Uiso 1 1 calc R . .
H19B H -0.5326 0.3757 0.2111 0.03 Uiso 1 1 calc R . .
N1 N -0.15089(14) 0.98161(14) 0.40900(9) 0.0208(2) Uani 1 1 d . . .
O1 O -0.32258(12) 0.74054(12) 0.13115(7) 0.0240(2) Uani 1 1 d . . .
O2 O -0.32414(12) 0.58247(11) 0.30387(7) 0.0236(2) Uani 1 1 d . . .
Li1 Li 0.0484(3) 0.9345(3) 0.43109(18) 0.0232(5) Uani 1 1 d . . .
Li2 Li -0.1840(3) 0.7884(3) 0.27285(18) 0.0222(5) 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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C4 C1 C2 116.04(11) . .
C4 C1 C3 115.09(11) . .
C2 C1 C3 59.02(9) . .
C4 C1 Li1 123.12(11) . .
C2 C1 Li1 118.90(11) . .
C3 C1 Li1 82.55(10) . .
C4 C1 Li2 112.88(10) . .
C2 C1 Li2 102.49(10) . .
C3 C1 Li2 131.88(11) . .
Li1 C1 Li2 68.29(9) . .
C3 C2 C1 60.62(9) . .
C2 C3 C1 60.36(9) . .
C5 C4 C9 116.29(12) . .
C5 C4 C1 122.21(12) . .
C9 C4 C1 121.42(12) . .
C6 C5 C4 121.60(13) . .
C7 C6 C5 120.87(13) . .
C6 C7 C8 118.62(13) . .
C9 C8 C7 120.64(13) . .
C8 C9 C4 121.99(13) . .
N1 C11 Li1 46.41(8) . 2_576
O1 C12 C13 105.05(11) . .
C12 C13 C14 104.22(11) . .
C15 C14 C13 103.82(12) . .
O1 C15 C14 104.97(11) . .
O2 C16 C17 106.34(12) . .
C16 C17 C18 101.94(12) . .
C19 C18 C17 101.90(12) . .
O2 C19 C18 105.52(11) . .
C11 N1 C10 107.20(11) . .
C11 N1 Li1 147.39(12) . .
C10 N1 Li1 104.99(11) . .
C11 N1 Li1 102.51(10) . 2_576
C10 N1 Li1 108.71(11) . 2_576
Li1 N1 Li1 71.46(11) . 2_576
C11 N1 Li2 96.80(10) . .
C10 N1 Li2 100.69(10) . .
Li1 N1 Li2 72.07(9) . .
Li1 N1 Li2 137.75(10) 2_576 .
C15 O1 C12 104.22(10) . .
C15 O1 Li2 127.42(11) . .
C12 O1 Li2 124.23(10) . .
C19 O2 C16 109.28(10) . .
C19 O2 Li2 124.60(10) . .
C16 O2 Li2 115.60(11) . .
N1 Li1 N1 108.54(11) . 2_576
N1 Li1 C1 108.37(11) . .
N1 Li1 C1 142.91(12) 2_576 .
N1 Li1 Li1 54.89(9) . 2_576
N1 Li1 Li1 53.65(9) 2_576 2_576
C1 Li1 Li1 162.94(17) . 2_576
N1 Li1 Li2 56.23(8) . .
N1 Li1 Li2 155.36(13) 2_576 .
C1 Li1 Li2 57.52(8) . .
Li1 Li1 Li2 108.18(14) 2_576 .
N1 Li1 C11 132.94(11) . 2_576
N1 Li1 C11 31.08(5) 2_576 2_576
C1 Li1 C11 114.00(10) . 2_576
Li1 Li1 C11 80.78(11) 2_576 2_576
Li2 Li1 C11 170.79(12) . 2_576
O2 Li2 O1 99.65(11) . .
O2 Li2 N1 106.39(11) . .
O1 Li2 N1 122.18(12) . .
O2 Li2 C1 109.37(11) . .
O1 Li2 C1 117.35(11) . .
N1 Li2 C1 101.22(10) . .
O2 Li2 Li1 100.59(11) . .
O1 Li2 Li1 159.74(13) . .
N1 Li2 Li1 51.71(8) . .
C1 Li2 Li1 54.20(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C4 1.4744(18) .
C1 C2 1.5218(18) .
C1 C3 1.5257(18) .
C1 Li1 2.131(3) .
C1 Li2 2.216(3) .
C2 C3 1.5012(19) .
C4 C5 1.4054(19) .
C4 C9 1.4074(19) .
C5 C6 1.3910(19) .
C6 C7 1.386(2) .
C7 C8 1.389(2) .
C8 C9 1.385(2) .
C10 N1 1.4619(18) .
C11 N1 1.4576(17) .
C11 Li1 2.757(3) 2_576
C12 O1 1.4396(16) .
C12 C13 1.520(2) .
C13 C14 1.535(2) .
C14 C15 1.523(2) .
C15 O1 1.4391(16) .
C16 O2 1.4449(17) .
C16 C17 1.500(2) .
C17 C18 1.526(2) .
C18 C19 1.515(2) .
C19 O2 1.4441(16) .
N1 Li1 2.014(3) .
N1 Li1 2.045(3) 2_576
N1 Li2 2.133(3) .
O1 Li2 1.994(2) .
O2 Li2 1.973(2) .
Li1 N1 2.045(3) 2_576
Li1 Li1 2.371(4) 2_576
Li1 Li2 2.441(3) .
Li1 C11 2.757(3) 2_576
