#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/15/7051580.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_7051580
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            'C37 H57 N3'
_chemical_formula_weight         543.86
_chemical_name_systematic
;
?
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.43(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.265(3)
_cell_length_b                   17.424(4)
_cell_length_c                   15.775(3)
_cell_measurement_temperature    123(2)
_cell_volume                     3371.1(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1167
_diffrn_reflns_av_sigmaI/netI    0.1204
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38325
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         7339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1568
_refine_ls_R_factor_gt           0.0629
_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)+(0.0714P)²+0.2073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1584
_reflns_number_gt                3776
_reflns_number_total             7339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809120j.txt
_cod_data_source_block           compound1
_cod_original_cell_volume        3371.2(12)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7051580
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_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
N1 N 0.22396(14) 0.20766(9) 0.33542(10) 0.0210(4) Uani 1 1 d . . .
H1 H 0.1845 0.2484 0.3230 0.025 Uiso 1 1 calc R . .
C1 C 0.20302(17) 0.17672(11) 0.41446(13) 0.0185(5) Uani 1 1 d . . .
N2 N 0.14525(14) 0.21321(9) 0.46933(10) 0.0216(4) Uani 1 1 d . . .
C2 C 0.29811(18) 0.18558(10) 0.27009(13) 0.0221(5) Uani 1 1 d . . .
N3 N 0.24750(14) 0.10519(9) 0.43213(10) 0.0199(4) Uani 1 1 d . . .
C3 C 0.25244(19) 0.16641(11) 0.19072(13) 0.0254(5) Uani 1 1 d . . .
C4 C 0.3234(2) 0.14914(12) 0.12456(14) 0.0326(6) Uani 1 1 d . . .
H4 H 0.2942 0.1366 0.0703 0.039 Uiso 1 1 calc R . .
C5 C 0.4349(2) 0.14989(13) 0.13642(15) 0.0377(6) Uani 1 1 d . . .
H5 H 0.4820 0.1377 0.0908 0.045 Uiso 1 1 calc R . .
C6 C 0.4774(2) 0.16845(13) 0.21455(15) 0.0353(6) Uani 1 1 d . . .
H6 H 0.5543 0.1682 0.2223 0.042 Uiso 1 1 calc R . .
C7 C 0.41118(18) 0.18766(11) 0.28302(14) 0.0258(5) Uani 1 1 d . . .
C8 C 0.13036(19) 0.16342(12) 0.17678(14) 0.0324(6) Uani 1 1 d . . .
H8 H 0.0957 0.1576 0.2336 0.039 Uiso 1 1 calc R . .
C9 C 0.0959(3) 0.09436(15) 0.1229(2) 0.0634(9) Uani 1 1 d . . .
H9A H 0.0175 0.0855 0.1293 0.095 Uiso 1 1 calc R . .
H9B H 0.1361 0.0488 0.1417 0.095 Uiso 1 1 calc R . .
H9C H 0.1120 0.1046 0.0632 0.095 Uiso 1 1 calc R . .
C10 C 0.0866(2) 0.23547(15) 0.1376(2) 0.0599(8) Uani 1 1 d . . .
H10A H 0.1023 0.2791 0.1750 0.090 Uiso 1 1 calc R . .
H10B H 0.0076 0.2307 0.1295 0.090 Uiso 1 1 calc R . .
H10C H 0.1213 0.2438 0.0826 0.090 Uiso 1 1 calc R . .
C11 C 0.46455(18) 0.21352(12) 0.36551(14) 0.0304(6) Uani 1 1 d . . .
H11 H 0.4065 0.2177 0.4094 0.036 Uiso 1 1 calc R . .
C12 C 0.5161(2) 0.29293(13) 0.35451(17) 0.0487(7) Uani 1 1 d . . .
H12A H 0.5736 0.2902 0.3118 0.073 Uiso 1 1 calc R . .
H12B H 0.5476 0.3098 0.4086 0.073 Uiso 1 1 calc R . .
H12C H 0.4602 0.3296 0.3361 0.073 Uiso 1 1 calc R . .
C13 C 0.55112(19) 0.15741(13) 0.39804(16) 0.0379(6) Uani 1 1 d . . .
H13A H 0.5178 0.1070 0.4074 0.057 Uiso 1 1 calc R . .
H13B H 0.5819 0.1765 0.4515 0.057 Uiso 1 1 calc R . .
H13C H 0.6092 0.1527 0.3560 0.057 Uiso 1 1 calc R . .
C14 C 0.09869(18) 0.28499(11) 0.44564(12) 0.0213(5) Uani 1 1 d . . .
C15 C -0.00594(18) 0.28559(11) 0.40860(13) 0.0229(5) Uani 1 1 d . . .
C16 C -0.05543(19) 0.35580(12) 0.39124(13) 0.0279(5) Uani 1 1 d . . .
H16 H -0.1264 0.3566 0.3667 0.033 Uiso 1 1 calc R . .
C17 C -0.0034(2) 0.42419(12) 0.40901(14) 0.0308(6) Uani 1 1 d . . .
H17 H -0.0382 0.4716 0.3967 0.037 Uiso 1 1 calc R . .
C18 C 0.0995(2) 0.42323(12) 0.44475(13) 0.0288(6) Uani 1 1 d . . .
H18 H 0.1350 0.4705 0.4568 0.035 Uiso 1 1 calc R . .
C19 C 0.15270(18) 0.35447(11) 0.46357(13) 0.0236(5) Uani 1 1 d . . .
C20 C -0.06580(18) 0.21081(12) 0.39082(13) 0.0263(5) Uani 1 1 d . . .
H20 H -0.0096 0.1710 0.3781 0.032 Uiso 1 1 calc R . .
C21 C -0.1435(2) 0.21421(13) 0.31532(15) 0.0386(6) Uani 1 1 d . . .
H21A H -0.2048 0.2481 0.3286 0.058 Uiso 1 1 calc R . .
H21B H -0.1710 0.1626 0.3029 0.058 Uiso 1 1 calc R . .
H21C H -0.1049 0.2341 0.2658 0.058 Uiso 1 1 calc R . .
C22 C -0.1264(2) 0.18479(14) 0.46975(15) 0.0450(7) Uani 1 1 d . . .
H22A H -0.0745 0.1787 0.5168 0.068 Uiso 1 1 calc R . .
H22B H -0.1625 0.1356 0.4584 0.068 Uiso 1 1 calc R . .
H22C H -0.1812 0.2233 0.4848 0.068 Uiso 1 1 calc R . .
C23 C 0.26334(18) 0.35359(12) 0.50655(14) 0.0288(5) Uani 1 1 d . . .
H23 H 0.3018 0.3060 0.4878 0.035 Uiso 1 1 calc R . .
C24 C 0.2508(2) 0.34886(15) 0.60260(14) 0.0418(7) Uani 1 1 d . . .
H24A H 0.2147 0.3954 0.6232 0.063 Uiso 1 1 calc R . .
H24B H 0.3229 0.3443 0.6293 0.063 Uiso 1 1 calc R . .
H24C H 0.2067 0.3039 0.6170 0.063 Uiso 1 1 calc R . .
C25 C 0.3346(2) 0.42197(15) 0.48221(18) 0.0511(7) Uani 1 1 d . . .
H25A H 0.3348 0.4276 0.4204 0.077 Uiso 1 1 calc R . .
H25B H 0.4092 0.4134 0.5027 0.077 Uiso 1 1 calc R . .
H25C H 0.3054 0.4688 0.5080 0.077 Uiso 1 1 calc R . .
C26 C 0.23162(17) 0.04380(11) 0.36763(13) 0.0218(5) Uani 1 1 d . . .
H26 H 0.2156 0.0707 0.3129 0.026 Uiso 1 1 calc R . .
C27 C 0.13386(18) -0.00852(11) 0.38414(14) 0.0260(5) Uani 1 1 d . . .
H27A H 0.1459 -0.0370 0.4377 0.031 Uiso 1 1 calc R . .
H27B H 0.0674 0.0231 0.3906 0.031 Uiso 1 1 calc R . .
C28 C 0.11694(18) -0.06547(12) 0.31152(15) 0.0312(6) Uani 1 1 d . . .
H28A H 0.0567 -0.1009 0.3258 0.037 Uiso 1 1 calc R . .
H28B H 0.0959 -0.0372 0.2595 0.037 Uiso 1 1 calc R . .
C29 C 0.21983(19) -0.11152(12) 0.29496(16) 0.0365(6) Uani 1 1 d . . .
H29A H 0.2081 -0.1451 0.2451 0.044 Uiso 1 1 calc R . .
H29B H 0.2358 -0.1447 0.3445 0.044 Uiso 1 1 calc R . .
C30 C 0.31662(19) -0.05903(12) 0.27890(15) 0.0323(6) Uani 1 1 d . . .
H30A H 0.3038 -0.0295 0.2261 0.039 Uiso 1 1 calc R . .
H30B H 0.3831 -0.0904 0.2712 0.039 Uiso 1 1 calc R . .
C31 C 0.33419(18) -0.00343(11) 0.35270(14) 0.0275(5) Uani 1 1 d . . .
H31A H 0.3528 -0.0326 0.4047 0.033 Uiso 1 1 calc R . .
H31B H 0.3959 0.0312 0.3399 0.033 Uiso 1 1 calc R . .
C32 C 0.25887(17) 0.07930(11) 0.52132(13) 0.0218(5) Uani 1 1 d . . .
H32 H 0.2914 0.0268 0.5183 0.026 Uiso 1 1 calc R . .
C33 C 0.15446(17) 0.07044(12) 0.57412(13) 0.0257(5) Uani 1 1 d . . .
H33A H 0.1229 0.1216 0.5860 0.031 Uiso 1 1 calc R . .
H33B H 0.0998 0.0400 0.5421 0.031 Uiso 1 1 calc R . .
C34 C 0.18281(19) 0.02990(12) 0.65731(14) 0.0294(6) Uani 1 1 d . . .
H34A H 0.1158 0.0230 0.6910 0.035 Uiso 1 1 calc R . .
H34B H 0.2130 -0.0216 0.6450 0.035 Uiso 1 1 calc R . .
C35 C 0.26552(19) 0.07593(12) 0.70838(14) 0.0324(6) Uani 1 1 d . . .
H35A H 0.2854 0.0473 0.7605 0.039 Uiso 1 1 calc R . .
H35B H 0.2328 0.1254 0.7255 0.039 Uiso 1 1 calc R . .
C36 C 0.36798(19) 0.09097(13) 0.65633(14) 0.0309(6) Uani 1 1 d . . .
H36A H 0.4066 0.0419 0.6469 0.037 Uiso 1 1 calc R . .
H36B H 0.4174 0.1253 0.6887 0.037 Uiso 1 1 calc R . .
C37 C 0.34151(18) 0.12776(12) 0.57056(13) 0.0265(5) Uani 1 1 d . . .
H37A H 0.3115 0.1798 0.5796 0.032 Uiso 1 1 calc R . .
H37B H 0.4092 0.1327 0.5372 0.032 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'
N N 0.0061 0.0033 '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
C1 N1 C2 131.81(17) . . ?
N2 C1 N1 121.26(17) . . ?
N2 C1 N3 121.66(18) . . ?
N1 C1 N3 117.08(17) . . ?
C1 N2 C14 118.56(17) . . ?
C7 C2 C3 121.5(2) . . ?
C7 C2 N1 121.45(19) . . ?
C3 C2 N1 116.94(19) . . ?
C1 N3 C32 119.84(15) . . ?
C1 N3 C26 117.32(16) . . ?
C32 N3 C26 116.16(15) . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 C8 120.4(2) . . ?
C2 C3 C8 121.61(19) . . ?
C5 C4 C3 121.3(2) . . ?
C6 C5 C4 119.6(2) . . ?
C5 C6 C7 122.1(2) . . ?
C6 C7 C2 117.5(2) . . ?
C6 C7 C11 118.9(2) . . ?
C2 C7 C11 123.5(2) . . ?
C10 C8 C3 112.48(19) . . ?
C10 C8 C9 109.5(2) . . ?
C3 C8 C9 112.1(2) . . ?
C7 C11 C13 113.02(18) . . ?
C7 C11 C12 110.25(19) . . ?
C13 C11 C12 109.23(19) . . ?
C15 C14 C19 120.25(18) . . ?
C15 C14 N2 118.59(17) . . ?
C19 C14 N2 121.04(19) . . ?
C16 C15 C14 118.92(19) . . ?
C16 C15 C20 120.5(2) . . ?
C14 C15 C20 120.55(17) . . ?
C17 C16 C15 121.2(2) . . ?
C18 C17 C16 119.6(2) . . ?
C17 C18 C19 121.5(2) . . ?
C18 C19 C14 118.5(2) . . ?
C18 C19 C23 121.37(19) . . ?
C14 C19 C23 120.05(18) . . ?
C15 C20 C21 114.20(17) . . ?
C15 C20 C22 110.00(17) . . ?
C21 C20 C22 110.16(19) . . ?
C19 C23 C24 110.40(18) . . ?
C19 C23 C25 113.11(19) . . ?
C24 C23 C25 110.7(2) . . ?
N3 C26 C31 112.97(17) . . ?
N3 C26 C27 114.24(17) . . ?
C31 C26 C27 110.71(16) . . ?
C28 C27 C26 111.19(18) . . ?
C29 C28 C27 111.31(19) . . ?
C28 C29 C30 111.18(18) . . ?
C29 C30 C31 111.10(18) . . ?
C26 C31 C30 110.39(18) . . ?
N3 C32 C37 111.82(16) . . ?
N3 C32 C33 118.08(17) . . ?
C37 C32 C33 109.38(17) . . ?
C34 C33 C32 109.02(18) . . ?
C35 C34 C33 110.98(18) . . ?
C34 C35 C36 110.73(19) . . ?
C35 C36 C37 112.15(19) . . ?
C32 C37 C36 110.72(17) . . ?
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
N1 C1 1.384(3) . ?
N1 C2 1.432(3) . ?
C1 N2 1.290(2) . ?
C1 N3 1.388(2) . ?
N2 C14 1.424(2) . ?
C2 C7 1.401(3) . ?
C2 C3 1.408(3) . ?
N3 C32 1.483(3) . ?
N3 C26 1.488(2) . ?
C3 C4 1.396(3) . ?
C3 C8 1.513(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.373(3) . ?
C6 C7 1.397(3) . ?
C7 C11 1.521(3) . ?
C8 C10 1.497(3) . ?
C8 C9 1.531(3) . ?
C11 C13 1.529(3) . ?
C11 C12 1.532(3) . ?
C14 C15 1.406(3) . ?
C14 C19 1.408(3) . ?
C15 C16 1.392(3) . ?
C15 C20 1.521(3) . ?
C16 C17 1.380(3) . ?
C17 C18 1.378(3) . ?
C18 C19 1.395(3) . ?
C19 C23 1.512(3) . ?
C20 C21 1.521(3) . ?
C20 C22 1.524(3) . ?
C23 C24 1.526(3) . ?
C23 C25 1.528(3) . ?
C26 C31 1.523(3) . ?
C26 C27 1.530(3) . ?
C27 C28 1.528(3) . ?
C28 C29 1.520(3) . ?
C29 C30 1.521(3) . ?
C30 C31 1.528(3) . ?
C32 C37 1.527(3) . ?
C32 C33 1.541(3) . ?
C33 C34 1.528(3) . ?
C34 C35 1.520(3) . ?
C35 C36 1.529(3) . ?
C36 C37 1.530(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28582381
