#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/31/7003184.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_7003184
loop_
_publ_author_name
'Higashihara, Gou'
'Inagaki, Akiko'
'Akita, Munetaka'
_publ_section_title
;
 Syntheses of novel di- and trinucleating ligands having a
 triethylbenzene core with N,N-bidentate tethers: their complexation
 toward Pd and Rh organometallic fragments
;
_journal_issue                   14
_journal_name_full               'Dalton Transactions'
_journal_page_first              1888
_journal_page_last               1898
_journal_paper_doi               10.1039/b713503c
_journal_year                    2008
_chemical_formula_sum            'C39 H39 N9'
_chemical_formula_weight         633.79
_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                 109.579(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3126(6)
_cell_length_b                   26.385(2)
_cell_length_c                   12.2108(10)
_cell_measurement_temperature    213(2)
_cell_volume                     3434.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26954
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0375(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         7758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0711P)²+0.0064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                5702
_reflns_number_total             7758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b713503c.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        3434.0(5)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7003184
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 0.62269(9) 0.15330(4) 0.94864(9) 0.0305(2) Uani 1 1 d . . .
N2 N 0.74137(9) 0.17085(4) 0.98080(9) 0.0325(2) Uani 1 1 d . . .
N3 N 0.93441(10) 0.19261(5) 1.27943(10) 0.0462(3) Uani 1 1 d . . .
N4 N 0.35914(11) -0.05050(4) 0.64307(9) 0.0378(3) Uani 1 1 d . . .
N5 N 0.30400(10) -0.09591(4) 0.61001(9) 0.0353(2) Uani 1 1 d . . .
N6 N 0.19778(10) -0.13933(4) 0.31303(10) 0.0403(3) Uani 1 1 d . . .
N7 N 0.10784(10) 0.09219(4) 0.92194(12) 0.0465(3) Uani 1 1 d . . .
N8 N 0.20342(11) 0.10661(5) 1.01718(12) 0.0461(3) Uani 1 1 d . . .
N9 N 0.19413(19) 0.09068(6) 1.30755(17) 0.0796(5) Uani 1 1 d . . .
C1 C 0.33274(11) 0.12025(5) 0.80890(11) 0.0333(3) Uani 1 1 d . . .
C2 C 0.45174(10) 0.10539(4) 0.80846(10) 0.0296(3) Uani 1 1 d . . .
C3 C 0.47953(10) 0.05416(5) 0.79888(10) 0.0299(3) Uani 1 1 d . . .
C4 C 0.38475(11) 0.01767(4) 0.78514(10) 0.0310(3) Uani 1 1 d . . .
C5 C 0.26528(11) 0.03196(5) 0.78530(10) 0.0332(3) Uani 1 1 d . . .
C6 C 0.24069(11) 0.08305(5) 0.79866(11) 0.0348(3) Uani 1 1 d . . .
C7 C 0.30186(14) 0.17567(5) 0.81643(15) 0.0453(3) Uani 1 1 d . . .
C8 C 0.24094(16) 0.19866(7) 0.69583(18) 0.0608(5) Uani 1 1 d . . .
C9 C 0.61132(12) 0.03741(5) 0.80981(13) 0.0396(3) Uani 1 1 d . . .
C10 C 0.68822(14) 0.02301(7) 0.93414(15) 0.0515(4) Uani 1 1 d . . .
C11 C 0.16192(13) -0.00699(6) 0.76980(13) 0.0430(3) Uani 1 1 d . . .
C12 C 0.07319(17) -0.01120(9) 0.64389(16) 0.0615(5) Uani 1 1 d . . .
C13 C 0.55242(11) 0.14528(5) 0.82459(11) 0.0330(3) Uani 1 1 d . . .
C14 C 0.41080(13) -0.03744(5) 0.76657(12) 0.0377(3) Uani 1 1 d . . .
C15 C 0.11447(12) 0.09855(6) 0.80542(14) 0.0458(4) Uani 1 1 d . . .
C16 C 0.58445(12) 0.14586(5) 1.04091(11) 0.0360(3) Uani 1 1 d . . .
C17 C 0.68225(12) 0.15870(5) 1.13843(12) 0.0378(3) Uani 1 1 d . . .
C18 C 0.77790(11) 0.17421(4) 1.09653(11) 0.0313(3) Uani 1 1 d . . .
C19 C 0.90467(11) 0.19242(5) 1.16386(11) 0.0340(3) Uani 1 1 d . . .
C20 C 0.98713(13) 0.20929(6) 1.10924(14) 0.0478(4) Uani 1 1 d . . .
C21 C 1.10424(13) 0.22643(6) 1.17640(15) 0.0532(4) Uani 1 1 d . . .
C22 C 1.13643(13) 0.22653(5) 1.29514(14) 0.0476(4) Uani 1 1 d . . .
C23 C 1.04883(13) 0.20941(6) 1.34232(14) 0.0507(4) Uani 1 1 d . . .
C24 C 0.35803(17) -0.02179(6) 0.55119(13) 0.0517(4) Uani 1 1 d . . .
C25 C 0.30020(16) -0.04948(6) 0.45350(14) 0.0527(4) Uani 1 1 d . . .
C26 C 0.26823(12) -0.09543(5) 0.49356(11) 0.0374(3) Uani 1 1 d . . .
C27 C 0.20547(11) -0.13951(5) 0.42521(11) 0.0356(3) Uani 1 1 d . . .
C28 C 0.15736(13) -0.17858(6) 0.47444(13) 0.0438(3) Uani 1 1 d . . .
C29 C 0.09977(14) -0.21895(6) 0.40517(14) 0.0483(4) Uani 1 1 d . . .
C30 C 0.09061(13) -0.21906(6) 0.28933(14) 0.0464(4) Uani 1 1 d . . .
C31 C 0.14073(12) -0.17897(6) 0.24747(13) 0.0436(3) Uani 1 1 d . . .
C32 C 0.00849(16) 0.07424(7) 0.9480(2) 0.0595(5) Uani 1 1 d . . .
C33 C 0.04056(18) 0.07657(7) 1.0649(2) 0.0663(5) Uani 1 1 d . . .
C34 C 0.16220(15) 0.09671(5) 1.10599(16) 0.0512(4) Uani 1 1 d . . .
C35 C 0.24043(17) 0.10692(6) 1.22611(16) 0.0570(4) Uani 1 1 d . . .
C36 C 0.35424(18) 0.13272(8) 1.25443(18) 0.0642(5) Uani 1 1 d . . .
C37 C 0.4222(2) 0.14207(10) 1.3688(2) 0.0809(6) Uani 1 1 d . . .
C38 C 0.3718(3) 0.12481(12) 1.4533(2) 0.0982(9) Uani 1 1 d . . .
C39 C 0.2595(3) 0.10003(11) 1.4165(3) 0.0954(8) Uani 1 1 d . . .
H1 H 0.2476(16) 0.1813(6) 0.8637(15) 0.061(5) Uiso 1 1 d . . .
H2 H 0.3817(14) 0.1962(6) 0.8642(12) 0.045(4) Uiso 1 1 d . . .
H3 H 0.3049(17) 0.1988(7) 0.6503(15) 0.072(5) Uiso 1 1 d . . .
H4 H 0.2163(16) 0.2333(7) 0.7060(14) 0.066(5) Uiso 1 1 d . . .
H5 H 0.1617(19) 0.1801(8) 0.6517(17) 0.080(6) Uiso 1 1 d . . .
H6 H 0.6092(14) 0.0089(6) 0.7533(14) 0.049(4) Uiso 1 1 d . . .
H7 H 0.6540(15) 0.0641(6) 0.7809(14) 0.055(4) Uiso 1 1 d . . .
H8 H 0.7011(18) 0.0533(8) 0.9884(17) 0.078(6) Uiso 1 1 d . . .
H9 H 0.7706(17) 0.0099(6) 0.9373(14) 0.062(5) Uiso 1 1 d . . .
H10 H 0.6437(17) -0.0035(7) 0.9646(16) 0.068(5) Uiso 1 1 d . . .
H11 H 0.1971(14) -0.0413(6) 0.7953(13) 0.049(4) Uiso 1 1 d . . .
H12 H 0.1117(14) 0.0025(6) 0.8181(13) 0.046(4) Uiso 1 1 d . . .
H13 H 0.0285(18) 0.0227(8) 0.6158(16) 0.077(6) Uiso 1 1 d . . .
H14 H 0.009(2) -0.0338(8) 0.6377(17) 0.083(6) Uiso 1 1 d . . .
H15 H 0.122(2) -0.0222(8) 0.5913(18) 0.084(7) Uiso 1 1 d . . .
H16 H 0.5153(12) 0.1772(5) 0.7913(12) 0.038(4) Uiso 1 1 d . . .
H17 H 0.6164(13) 0.1354(5) 0.7877(12) 0.035(3) Uiso 1 1 d . . .
H18 H 0.5039(14) -0.0459(5) 0.7965(12) 0.043(4) Uiso 1 1 d . . .
H19 H 0.3660(13) -0.0611(6) 0.8049(12) 0.044(4) Uiso 1 1 d . . .
H20 H 0.0947(14) 0.1348(6) 0.7803(14) 0.052(4) Uiso 1 1 d . . .
H21 H 0.0432(14) 0.0771(6) 0.7522(13) 0.049(4) Uiso 1 1 d . . .
H22 H 0.4987(14) 0.1336(6) 1.0306(12) 0.048(4) Uiso 1 1 d . . .
H23 H 0.6870(15) 0.1559(6) 1.2175(14) 0.057(5) Uiso 1 1 d . . .
H24 H 0.9576(15) 0.2095(7) 1.0202(15) 0.062(5) Uiso 1 1 d . . .
H25 H 1.1647(16) 0.2390(7) 1.1384(15) 0.068(5) Uiso 1 1 d . . .
H26 H 1.2202(14) 0.2395(6) 1.3489(13) 0.055(4) Uiso 1 1 d . . .
H27 H 1.0681(15) 0.2090(7) 1.4332(16) 0.067(5) Uiso 1 1 d . . .
H28 H -0.0692(19) 0.0606(8) 0.8827(17) 0.086(6) Uiso 1 1 d . . .
H29 H -0.006(2) 0.0689(8) 1.1093(18) 0.090(7) Uiso 1 1 d . . .
H30 H 0.3835(17) 0.1452(7) 1.1943(17) 0.070(6) Uiso 1 1 d . . .
H31 H 0.4994(15) 0.1608(6) 1.3896(14) 0.050(5) Uiso 1 1 d . . .
H32 H 0.428(2) 0.1350(8) 1.524(2) 0.089(7) Uiso 1 1 d . . .
H33 H 0.226(3) 0.0863(11) 1.480(3) 0.136(10) Uiso 1 1 d . . .
H34 H 0.3973(16) 0.0122(7) 0.5636(14) 0.061(5) Uiso 1 1 d . . .
H35 H 0.2849(16) -0.0387(7) 0.3747(16) 0.070(5) Uiso 1 1 d . . .
H36 H 0.1665(15) -0.1777(6) 0.5580(15) 0.059(5) Uiso 1 1 d . . .
H37 H 0.0663(14) -0.2480(6) 0.4390(14) 0.056(4) Uiso 1 1 d . . .
H38 H 0.0496(13) -0.2464(6) 0.2395(13) 0.050(4) Uiso 1 1 d . . .
H39 H 0.1353(14) -0.1786(6) 0.1652(14) 0.052(4) Uiso 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 0.0000 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
N2 N1 C16 111.91(10) . . ?
N2 N1 C13 119.42(10) . . ?
C16 N1 C13 128.67(10) . . ?
C18 N2 N1 104.82(10) . . ?
C19 N3 C23 117.35(13) . . ?
N5 N4 C24 112.03(11) . . ?
N5 N4 C14 120.16(10) . . ?
C24 N4 C14 127.82(11) . . ?
C26 N5 N4 104.70(10) . . ?
C27 N6 C31 117.31(13) . . ?
N8 N7 C32 112.63(15) . . ?
N8 N7 C15 121.28(11) . . ?
C32 N7 C15 126.03(14) . . ?
C34 N8 N7 104.26(13) . . ?
C39 N9 C35 117.7(2) . . ?
C2 C1 C6 119.16(11) . . ?
C2 C1 C7 120.75(11) . . ?
C6 C1 C7 120.06(11) . . ?
C3 C2 C1 120.79(10) . . ?
C3 C2 C13 120.08(11) . . ?
C1 C2 C13 119.06(11) . . ?
C2 C3 C4 119.08(11) . . ?
C2 C3 C9 120.98(11) . . ?
C4 C3 C9 119.84(11) . . ?
C5 C4 C3 120.74(11) . . ?
C5 C4 C14 119.56(11) . . ?
C3 C4 C14 119.68(11) . . ?
C6 C5 C4 119.26(11) . . ?
C6 C5 C11 119.47(12) . . ?
C4 C5 C11 121.27(12) . . ?
C5 C6 C1 120.91(11) . . ?
C5 C6 C15 119.70(11) . . ?
C1 C6 C15 119.37(12) . . ?
C1 C7 C8 111.36(14) . . ?
C3 C9 C10 112.11(12) . . ?
C5 C11 C12 113.06(13) . . ?
N1 C13 C2 110.93(10) . . ?
N4 C14 C4 110.45(11) . . ?
N7 C15 C6 112.32(11) . . ?
N1 C16 C17 107.37(11) . . ?
C16 C17 C18 104.60(12) . . ?
N2 C18 C17 111.30(10) . . ?
N2 C18 C19 120.66(11) . . ?
C17 C18 C19 128.04(12) . . ?
N3 C19 C20 122.25(12) . . ?
N3 C19 C18 116.35(12) . . ?
C20 C19 C18 121.39(12) . . ?
C21 C20 C19 119.02(15) . . ?
C22 C21 C20 119.40(15) . . ?
C21 C22 C23 117.89(13) . . ?
N3 C23 C22 124.09(15) . . ?
N4 C24 C25 107.12(13) . . ?
C24 C25 C26 105.22(13) . . ?
N5 C26 C25 110.93(12) . . ?
N5 C26 C27 120.77(12) . . ?
C25 C26 C27 128.30(13) . . ?
N6 C27 C28 122.81(12) . . ?
N6 C27 C26 115.50(12) . . ?
C28 C27 C26 121.69(12) . . ?
C29 C28 C27 118.63(14) . . ?
C28 C29 C30 119.12(15) . . ?
C31 C30 C29 118.61(14) . . ?
N6 C31 C30 123.52(14) . . ?
C33 C32 N7 106.42(16) . . ?
C32 C33 C34 106.20(15) . . ?
N8 C34 C33 110.49(17) . . ?
N8 C34 C35 121.16(15) . . ?
C33 C34 C35 128.34(16) . . ?
N9 C35 C36 122.03(19) . . ?
N9 C35 C34 115.46(17) . . ?
C36 C35 C34 122.50(16) . . ?
C37 C36 C35 119.8(2) . . ?
C36 C37 C38 117.4(3) . . ?
C39 C38 C37 118.3(3) . . ?
N9 C39 C38 124.8(3) . . ?
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 N2 1.3482(13) . ?
N1 C16 1.3497(16) . ?
N1 C13 1.4711(15) . ?
N2 C18 1.3357(16) . ?
N3 C19 1.3365(17) . ?
N3 C23 1.3399(18) . ?
N4 N5 1.3488(14) . ?
N4 C24 1.3502(18) . ?
N4 C14 1.4641(16) . ?
N5 C26 1.3417(16) . ?
N6 C27 1.3431(17) . ?
N6 C31 1.3436(17) . ?
N7 N8 1.3504(18) . ?
N7 C32 1.3523(18) . ?
N7 C15 1.459(2) . ?
N8 C34 1.3419(19) . ?
N9 C39 1.311(3) . ?
N9 C35 1.340(2) . ?
C1 C2 1.4039(17) . ?
C1 C6 1.4058(17) . ?
C1 C7 1.5132(19) . ?
C2 C3 1.4016(17) . ?
C2 C13 1.5143(16) . ?
C3 C4 1.4086(16) . ?
C3 C9 1.5174(17) . ?
C4 C5 1.4037(17) . ?
C4 C14 1.5158(18) . ?
C5 C6 1.3970(18) . ?
C5 C11 1.5201(17) . ?
C6 C15 1.5140(18) . ?
C7 C8 1.527(2) . ?
C9 C10 1.523(2) . ?
C11 C12 1.533(2) . ?
C16 C17 1.3689(18) . ?
C17 C18 1.4040(18) . ?
C18 C19 1.4741(16) . ?
C19 C20 1.389(2) . ?
C20 C21 1.3799(19) . ?
C21 C22 1.371(2) . ?
C22 C23 1.379(2) . ?
C24 C25 1.364(2) . ?
C25 C26 1.400(2) . ?
C26 C27 1.4685(18) . ?
C27 C28 1.393(2) . ?
C28 C29 1.380(2) . ?
C29 C30 1.383(2) . ?
C30 C31 1.377(2) . ?
C32 C33 1.351(3) . ?
C33 C34 1.402(2) . ?
C34 C35 1.462(3) . ?
C35 C36 1.394(3) . ?
C36 C37 1.372(3) . ?
C37 C38 1.411(4) . ?
C38 C39 1.364(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21118496
