#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:16:01 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180069 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/15/7051588.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_7051588
loop_
_publ_author_name
'Jin, Guoxia'
'Jones, Cameron'
'Junk, Peter C.'
'Lippert, Kai-Alexander'
'Rose, Richard P.'
'Stasch, Andreas'
_publ_section_title
;
 Synthesis and characterisation of bulky guanidines and
 phosphaguanidines: precursors for low oxidation state metallacycles
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              64
_journal_paper_doi               10.1039/b809120j
_journal_volume                  33
_journal_year                    2009
_chemical_formula_sum            'C41 H64 Li N3 O'
_chemical_formula_weight         621.89
_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                 113.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.807(4)
_cell_length_b                   11.783(2)
_cell_length_c                   18.773(4)
_cell_measurement_temperature    150(2)
_cell_volume                     3823.7(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24208
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0501
_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)+(0.0464P)²+1.9994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                6807
_reflns_number_total             8282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809120j.txt
_cod_data_source_block           compound10
_cod_original_cell_volume        3823.8(13)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7051588
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 0.16744(6) 0.78185(8) 0.12699(6) 0.0303(2) Uani 1 1 d . . .
N1 N 0.34681(6) 0.47829(9) 0.25545(6) 0.0202(2) Uani 1 1 d . . .
C1 C 0.28366(7) 0.46980(10) 0.26921(7) 0.0179(3) Uani 1 1 d . . .
Li1 Li 0.24440(14) 0.6812(2) 0.19075(15) 0.0303(5) Uani 1 1 d . . .
N2 N 0.22969(6) 0.55361(9) 0.24904(6) 0.0199(2) Uani 1 1 d . . .
C2 C 0.35666(7) 0.58007(11) 0.22207(8) 0.0209(3) Uani 1 1 d . . .
N3 N 0.27444(6) 0.37092(9) 0.30692(6) 0.0193(2) Uani 1 1 d . . .
C3 C 0.38412(8) 0.67762(12) 0.27017(8) 0.0250(3) Uani 1 1 d . . .
C4 C 0.39213(9) 0.77962(12) 0.23624(10) 0.0319(3) Uani 1 1 d . . .
H4 H 0.4098 0.8451 0.2678 0.038 Uiso 1 1 calc R . .
C5 C 0.37481(9) 0.78739(13) 0.15740(10) 0.0337(4) Uani 1 1 d . . .
H5 H 0.3796 0.8580 0.1352 0.040 Uiso 1 1 calc R . .
C6 C 0.35063(8) 0.69199(12) 0.11135(9) 0.0283(3) Uani 1 1 d . . .
H6 H 0.3398 0.6975 0.0576 0.034 Uiso 1 1 calc R . .
C7 C 0.34170(7) 0.58746(11) 0.14219(8) 0.0225(3) Uani 1 1 d . . .
C8 C 0.40701(9) 0.66667(14) 0.35700(9) 0.0324(3) Uani 1 1 d . . .
H8 H 0.3683 0.6158 0.3651 0.039 Uiso 1 1 calc R . .
C9 C 0.48582(10) 0.60861(16) 0.39348(10) 0.0449(4) Uani 1 1 d . . .
H9A H 0.4837 0.5348 0.3686 0.067 Uiso 1 1 calc R . .
H9B H 0.4992 0.5975 0.4490 0.067 Uiso 1 1 calc R . .
H9C H 0.5251 0.6562 0.3862 0.067 Uiso 1 1 calc R . .
C10 C 0.40737(12) 0.77905(16) 0.39824(11) 0.0491(5) Uani 1 1 d . . .
H10A H 0.4484 0.8281 0.3958 0.074 Uiso 1 1 calc R . .
H10B H 0.4167 0.7641 0.4525 0.074 Uiso 1 1 calc R . .
H10C H 0.3572 0.8168 0.3727 0.074 Uiso 1 1 calc R . .
C11 C 0.31951(8) 0.48035(12) 0.09307(8) 0.0251(3) Uani 1 1 d . . .
H11 H 0.2826 0.4365 0.1089 0.030 Uiso 1 1 calc R . .
C12 C 0.39149(9) 0.40656(13) 0.11012(10) 0.0345(4) Uani 1 1 d . . .
H12A H 0.4281 0.4467 0.0937 0.052 Uiso 1 1 calc R . .
H12B H 0.3764 0.3348 0.0817 0.052 Uiso 1 1 calc R . .
H12C H 0.4159 0.3910 0.1658 0.052 Uiso 1 1 calc R . .
C13 C 0.27972(11) 0.50321(15) 0.00602(9) 0.0403(4) Uani 1 1 d . . .
H13A H 0.2351 0.5530 -0.0041 0.060 Uiso 1 1 calc R . .
H13B H 0.2623 0.4313 -0.0216 0.060 Uiso 1 1 calc R . .
H13C H 0.3163 0.5400 -0.0121 0.060 Uiso 1 1 calc R . .
C14 C 0.15191(7) 0.54181(11) 0.24018(8) 0.0209(3) Uani 1 1 d . . .
C15 C 0.12311(8) 0.61663(12) 0.28199(8) 0.0258(3) Uani 1 1 d . . .
C16 C 0.04386(9) 0.62148(14) 0.26391(10) 0.0350(4) Uani 1 1 d . . .
H16 H 0.0249 0.6728 0.2913 0.042 Uiso 1 1 calc R . .
C17 C -0.00760(9) 0.55357(15) 0.20721(11) 0.0388(4) Uani 1 1 d . . .
H17 H -0.0615 0.5586 0.1952 0.047 Uiso 1 1 calc R . .
C18 C 0.02035(8) 0.47790(13) 0.16802(9) 0.0318(3) Uani 1 1 d . . .
H18 H -0.0150 0.4299 0.1297 0.038 Uiso 1 1 calc R . .
C19 C 0.09901(8) 0.47018(11) 0.18326(8) 0.0235(3) Uani 1 1 d . . .
C20 C 0.17740(9) 0.69309(12) 0.34543(9) 0.0291(3) Uani 1 1 d . . .
H20 H 0.2309 0.6619 0.3616 0.035 Uiso 1 1 calc R . .
C21 C 0.15780(11) 0.69608(15) 0.41719(10) 0.0404(4) Uani 1 1 d . . .
H21A H 0.1098 0.7389 0.4054 0.061 Uiso 1 1 calc R . .
H21B H 0.2000 0.7328 0.4600 0.061 Uiso 1 1 calc R . .
H21C H 0.1510 0.6184 0.4321 0.061 Uiso 1 1 calc R . .
C22 C 0.17780(12) 0.81404(14) 0.31619(10) 0.0431(4) Uani 1 1 d . . .
H22A H 0.1943 0.8128 0.2728 0.065 Uiso 1 1 calc R . .
H22B H 0.2137 0.8607 0.3582 0.065 Uiso 1 1 calc R . .
H22C H 0.1256 0.8462 0.2989 0.065 Uiso 1 1 calc R . .
C23 C 0.12527(8) 0.39185(12) 0.13400(8) 0.0252(3) Uani 1 1 d . . .
H23 H 0.1824 0.3811 0.1618 0.030 Uiso 1 1 calc R . .
C24 C 0.08786(10) 0.27475(15) 0.12345(11) 0.0433(4) Uani 1 1 d . . .
H24A H 0.0318 0.2821 0.0954 0.065 Uiso 1 1 calc R . .
H24B H 0.0991 0.2406 0.1744 0.065 Uiso 1 1 calc R . .
H24C H 0.1087 0.2263 0.0938 0.065 Uiso 1 1 calc R . .
C25 C 0.11115(10) 0.44531(17) 0.05559(10) 0.0451(4) Uani 1 1 d . . .
H25A H 0.0554 0.4544 0.0260 0.068 Uiso 1 1 calc R . .
H25B H 0.1326 0.3961 0.0269 0.068 Uiso 1 1 calc R . .
H25C H 0.1363 0.5197 0.0635 0.068 Uiso 1 1 calc R . .
C26 C 0.32334(7) 0.26968(11) 0.31350(7) 0.0200(3) Uani 1 1 d . . .
H26 H 0.3075 0.2136 0.3445 0.024 Uiso 1 1 calc R . .
C27 C 0.41168(8) 0.28146(11) 0.35647(8) 0.0236(3) Uani 1 1 d . . .
H27A H 0.4324 0.3297 0.3259 0.028 Uiso 1 1 calc R . .
H27B H 0.4239 0.3183 0.4073 0.028 Uiso 1 1 calc R . .
C28 C 0.44924(8) 0.16427(12) 0.36829(9) 0.0290(3) Uani 1 1 d . . .
H28A H 0.5059 0.1718 0.3969 0.035 Uiso 1 1 calc R . .
H28B H 0.4290 0.1166 0.3996 0.035 Uiso 1 1 calc R . .
C29 C 0.43217(8) 0.10760(13) 0.29048(9) 0.0319(3) Uani 1 1 d . . .
H29A H 0.4559 0.0312 0.2989 0.038 Uiso 1 1 calc R . .
H29B H 0.4551 0.1529 0.2605 0.038 Uiso 1 1 calc R . .
C30 C 0.34492(8) 0.09736(12) 0.24470(9) 0.0285(3) Uani 1 1 d . . .
H30A H 0.3231 0.0448 0.2720 0.034 Uiso 1 1 calc R . .
H30B H 0.3348 0.0649 0.1930 0.034 Uiso 1 1 calc R . .
C31 C 0.30462(8) 0.21266(11) 0.23490(8) 0.0241(3) Uani 1 1 d . . .
H31A H 0.3217 0.2623 0.2021 0.029 Uiso 1 1 calc R . .
H31B H 0.2480 0.2021 0.2084 0.029 Uiso 1 1 calc R . .
C32 C 0.24710(7) 0.38595(11) 0.37010(8) 0.0219(3) Uani 1 1 d . . .
H32 H 0.2224 0.4626 0.3624 0.026 Uiso 1 1 calc R . .
C33 C 0.31255(8) 0.38698(13) 0.45109(8) 0.0276(3) Uani 1 1 d . . .
H33A H 0.3382 0.3118 0.4620 0.033 Uiso 1 1 calc R . .
H33B H 0.3516 0.4444 0.4528 0.033 Uiso 1 1 calc R . .
C34 C 0.28127(10) 0.41446(15) 0.51290(9) 0.0375(4) Uani 1 1 d . . .
H34A H 0.3240 0.4107 0.5648 0.045 Uiso 1 1 calc R . .
H34B H 0.2604 0.4927 0.5050 0.045 Uiso 1 1 calc R . .
C35 C 0.21800(10) 0.33211(15) 0.50960(10) 0.0411(4) Uani 1 1 d . . .
H35A H 0.1961 0.3559 0.5473 0.049 Uiso 1 1 calc R . .
H35B H 0.2405 0.2555 0.5245 0.049 Uiso 1 1 calc R . .
C36 C 0.15360(10) 0.32719(15) 0.42883(10) 0.0380(4) Uani 1 1 d . . .
H36A H 0.1262 0.4009 0.4170 0.046 Uiso 1 1 calc R . .
H36B H 0.1158 0.2680 0.4278 0.046 Uiso 1 1 calc R . .
C37 C 0.18467(8) 0.30079(13) 0.36639(9) 0.0288(3) Uani 1 1 d . . .
H37A H 0.2065 0.2231 0.3742 0.035 Uiso 1 1 calc R . .
H37B H 0.1418 0.3040 0.3146 0.035 Uiso 1 1 calc R . .
C38 C 0.17887(9) 0.90136(13) 0.11905(10) 0.0373(4) Uani 1 1 d . . .
H38A H 0.2090 0.9136 0.0868 0.045 Uiso 1 1 calc R . .
H38B H 0.2070 0.9364 0.1705 0.045 Uiso 1 1 calc R . .
C39 C 0.10013(13) 0.95136(19) 0.0811(2) 0.0900(10) Uani 1 1 d . . .
H39A H 0.0966 1.0230 0.1071 0.108 Uiso 1 1 calc R . .
H39B H 0.0883 0.9677 0.0259 0.108 Uiso 1 1 calc R . .
C40 C 0.04660(11) 0.86827(18) 0.08799(17) 0.0687(7) Uani 1 1 d . . .
H40A H -0.0031 0.8708 0.0423 0.082 Uiso 1 1 calc R . .
H40B H 0.0366 0.8819 0.1353 0.082 Uiso 1 1 calc R . .
C41 C 0.08580(9) 0.75771(15) 0.09263(11) 0.0426(4) Uani 1 1 d . . .
H41A H 0.0715 0.7037 0.1251 0.051 Uiso 1 1 calc R . .
H41B H 0.0712 0.7245 0.0403 0.051 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'
Li Li -0.0003 0.0001 '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 0.0060 '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
C41 O1 C38 108.84(11) . . ?
C41 O1 Li1 125.13(12) . . ?
C38 O1 Li1 124.79(12) . . ?
C1 N1 C2 116.26(11) . . ?
N1 C1 N2 121.56(11) . . ?
N1 C1 N3 117.46(11) . . ?
N2 C1 N3 120.98(11) . . ?
O1 Li1 N2 126.81(14) . . ?
O1 Li1 C2 152.62(14) . . ?
N2 Li1 C2 76.93(9) . . ?
O1 Li1 C3 139.85(13) . . ?
N2 Li1 C3 90.02(10) . . ?
C2 Li1 C3 34.74(6) . . ?
O1 Li1 C7 121.04(13) . . ?
N2 Li1 C7 98.34(11) . . ?
C2 Li1 C7 32.98(6) . . ?
C3 Li1 C7 58.11(7) . . ?
C1 N2 C14 125.91(11) . . ?
C1 N2 Li1 117.59(11) . . ?
C14 N2 Li1 112.37(11) . . ?
N1 C2 C7 121.41(12) . . ?
N1 C2 C3 119.08(12) . . ?
C7 C2 C3 119.49(12) . . ?
N1 C2 Li1 106.85(10) . . ?
C7 C2 Li1 85.28(11) . . ?
C3 C2 Li1 79.07(10) . . ?
C1 N3 C32 117.05(10) . . ?
C1 N3 C26 120.82(10) . . ?
C32 N3 C26 115.51(10) . . ?
C4 C3 C2 118.82(13) . . ?
C4 C3 C8 121.81(13) . . ?
C2 C3 C8 119.32(13) . . ?
C4 C3 Li1 89.43(11) . . ?
C2 C3 Li1 66.18(9) . . ?
C8 C3 Li1 115.83(11) . . ?
C5 C4 C3 121.43(14) . . ?
C6 C5 C4 119.66(14) . . ?
C5 C6 C7 121.40(14) . . ?
C6 C7 C2 119.11(13) . . ?
C6 C7 C11 121.91(13) . . ?
C2 C7 C11 118.93(12) . . ?
C6 C7 Li1 89.24(10) . . ?
C2 C7 Li1 61.74(9) . . ?
C11 C7 Li1 120.26(10) . . ?
C3 C8 C9 109.49(13) . . ?
C3 C8 C10 114.31(14) . . ?
C9 C8 C10 110.49(14) . . ?
C7 C11 C13 113.79(12) . . ?
C7 C11 C12 109.59(12) . . ?
C13 C11 C12 110.06(13) . . ?
N2 C14 C19 122.30(12) . . ?
N2 C14 C15 118.43(12) . . ?
C19 C14 C15 118.61(12) . . ?
C16 C15 C14 119.64(13) . . ?
C16 C15 C20 119.34(13) . . ?
C14 C15 C20 121.01(12) . . ?
C17 C16 C15 121.52(14) . . ?
C16 C17 C18 119.10(14) . . ?
C17 C18 C19 121.81(14) . . ?
C18 C19 C14 119.26(13) . . ?
C18 C19 C23 119.17(13) . . ?
C14 C19 C23 121.39(12) . . ?
C15 C20 C22 111.58(13) . . ?
C15 C20 C21 112.49(13) . . ?
C22 C20 C21 109.36(13) . . ?
C19 C23 C25 111.20(12) . . ?
C19 C23 C24 112.60(12) . . ?
C25 C23 C24 110.62(14) . . ?
N3 C26 C31 111.94(11) . . ?
N3 C26 C27 118.49(11) . . ?
C31 C26 C27 109.59(11) . . ?
C28 C27 C26 109.65(11) . . ?
C29 C28 C27 110.31(12) . . ?
C28 C29 C30 110.39(12) . . ?
C29 C30 C31 111.63(12) . . ?
C26 C31 C30 111.01(11) . . ?
N3 C32 C37 112.92(11) . . ?
N3 C32 C33 113.54(11) . . ?
C37 C32 C33 110.69(11) . . ?
C34 C33 C32 110.83(12) . . ?
C35 C34 C33 111.33(14) . . ?
C34 C35 C36 111.59(13) . . ?
C35 C36 C37 112.04(13) . . ?
C32 C37 C36 110.48(13) . . ?
O1 C38 C39 105.98(14) . . ?
C40 C39 C38 106.60(17) . . ?
C39 C40 C41 104.63(16) . . ?
O1 C41 C40 105.70(14) . . ?
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 C41 1.4401(19) . ?
O1 C38 1.4412(18) . ?
O1 Li1 1.889(3) . ?
N1 C1 1.3149(16) . ?
N1 C2 1.3989(17) . ?
C1 N2 1.3587(16) . ?
C1 N3 1.4092(16) . ?
Li1 N2 1.943(3) . ?
Li1 C2 2.290(3) . ?
Li1 C3 2.458(3) . ?
Li1 C7 2.591(3) . ?
N2 C14 1.4125(16) . ?
C2 C7 1.4154(19) . ?
C2 C3 1.4269(19) . ?
N3 C32 1.4776(16) . ?
N3 C26 1.4816(16) . ?
C3 C4 1.396(2) . ?
C3 C8 1.519(2) . ?
C4 C5 1.388(2) . ?
C5 C6 1.381(2) . ?
C6 C7 1.3991(19) . ?
C7 C11 1.5212(19) . ?
C8 C9 1.528(2) . ?
C8 C10 1.533(2) . ?
C11 C13 1.530(2) . ?
C11 C12 1.533(2) . ?
C14 C19 1.4165(19) . ?
C14 C15 1.4219(19) . ?
C15 C16 1.393(2) . ?
C15 C20 1.521(2) . ?
C16 C17 1.378(2) . ?
C17 C18 1.385(2) . ?
C18 C19 1.3947(19) . ?
C19 C23 1.5202(19) . ?
C20 C22 1.528(2) . ?
C20 C21 1.531(2) . ?
C23 C25 1.525(2) . ?
C23 C24 1.526(2) . ?
C26 C31 1.5307(19) . ?
C26 C27 1.5408(19) . ?
C27 C28 1.5269(19) . ?
C28 C29 1.521(2) . ?
C29 C30 1.528(2) . ?
C30 C31 1.5311(19) . ?
C32 C37 1.5249(19) . ?
C32 C33 1.534(2) . ?
C33 C34 1.528(2) . ?
C34 C35 1.518(2) . ?
C35 C36 1.524(3) . ?
C36 C37 1.534(2) . ?
C38 C39 1.489(3) . ?
C39 C40 1.446(3) . ?
C40 C41 1.482(3) . ?
