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#$Date: 2016-03-23 16:25:09 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179376 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/73/4327308.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_4327308
loop_
_publ_author_name
'Robert T. Stibrany'
'Chengmin Zhang'
'Thomas J. Emge'
'Harvey J. Schugar'
'Joseph A. Potenza'
'Spencer Knapp'
_publ_contact_author
;
 Joseph A. Potenza
 Department of Chemistry and Chemical Biology
 Rutgers, The State University of New Jersey
 610 Taylor Road
 Piscataway, New Jersey 08854 USA 
;
_publ_contact_author_email       potenza@rutchem.rutgers.edu
_publ_contact_author_fax         '732 445 5312'
_publ_contact_author_phone       '732 445 2115'
_publ_section_title
;
 A Tris(pyrazolyl) η6-Arene Ligand That Selects Cu(I) over Cu(II)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9713
_journal_page_last               9720
_journal_paper_doi               10.1021/ic060980+
_journal_volume                  45
_journal_year                    2006
_chemical_formula_moiety         'C42 H42 N6'
_chemical_formula_sum            'C42 H42 N6'
_chemical_formula_weight         630.82
_chemical_name_common            5
_chemical_name_systematic
; 
 1,3,5-Tris[2'-((3,5-dimethylpyrazol-1-yl)methyl)
phenyl]benzene  
;
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   24.5701(11)
_cell_length_b                   24.5701(11)
_cell_length_c                   10.1453(8)
_cell_measurement_reflns_used    604
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.96
_cell_measurement_theta_min      4.45
_cell_volume                     5304.1(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996), ORTEP32 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker SMART CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0706
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13576
_diffrn_reflns_theta_full        22.44
_diffrn_reflns_theta_max         22.44
_diffrn_reflns_theta_min         2.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       prism
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.295
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0769
_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)+(0.0324P)²+5.7391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                1253
_reflns_number_total             1530
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic0609802Bsi20060919_023840_1.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4327308
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
N1 N 0.14056(13) 0.64724(13) 0.1627(3) 0.0609(8) Uani 1 1 d .
N2 N 0.12785(13) 0.61230(13) 0.2740(3) 0.0648(8) Uani 1 1 d .
C21 C 0.19710(14) 0.59663(14) -0.1344(3) 0.0491(8) Uani 1 1 d .
C22 C 0.15796(15) 0.60302(14) -0.0445(3) 0.0538(9) Uani 1 1 d .
C23 C 0.09353(16) 0.56529(17) -0.0588(4) 0.0724(11) Uani 1 1 d .
H23 H 0.0671 0.5691 0.0014 0.087 Uiso 1 1 calc R
C24 C 0.06763(17) 0.52233(18) -0.1593(4) 0.0777(11) Uani 1 1 d .
H24 H 0.0242 0.4978 -0.1671 0.093 Uiso 1 1 calc R
C25 C 0.10582(17) 0.51585(17) -0.2478(4) 0.0734(11) Uani 1 1 d .
H25 H 0.0887 0.4868 -0.3161 0.088 Uiso 1 1 calc R
C26 C 0.16999(15) 0.55262(15) -0.2351(3) 0.0613(9) Uani 1 1 d .
H26 H 0.1959 0.5479 -0.2953 0.074 Uiso 1 1 calc R
C27 C 0.18590(15) 0.64922(16) 0.0698(3) 0.0643(10) Uani 1 1 d .
H27A H 0.2153 0.6407 0.1166 0.077 Uiso 1 1 calc R
H27B H 0.2095 0.6914 0.0342 0.077 Uiso 1 1 calc R
C3 C 0.08508(17) 0.62016(18) 0.3363(4) 0.0715(10) Uani 1 1 d .
C31 C 0.0600(2) 0.5898(2) 0.4663(4) 0.1121(16) Uani 1 1 d .
H31A H 0.0176 0.5559 0.4557 0.168 Uiso 1 1 calc R
H31B H 0.0605 0.6202 0.5266 0.168 Uiso 1 1 calc R
H31C H 0.0856 0.5737 0.5004 0.168 Uiso 1 1 calc R
C4 C 0.07025(17) 0.65919(19) 0.2652(4) 0.0809(12) Uani 1 1 d .
H4 H 0.0413 0.6713 0.2886 0.097 Uiso 1 1 calc R
C41 C 0.26723(14) 0.63337(14) -0.1263(3) 0.0478(8) Uani 1 1 d .
C42 C 0.30058(14) 0.69865(15) -0.1264(3) 0.0514(8) Uani 1 1 d .
H42 H 0.2785 0.7203 -0.1266 0.062 Uiso 1 1 calc R
C5 C 0.10637(17) 0.67625(17) 0.1544(4) 0.0701(10) Uani 1 1 d .
C51 C 0.1117(2) 0.7170(2) 0.0408(5) 0.1072(15) Uani 1 1 d .
H51A H 0.1536 0.7523 0.0368 0.161 Uiso 1 1 calc R
H51B H 0.0824 0.7317 0.0518 0.161 Uiso 1 1 calc R
H51C H 0.1024 0.6933 -0.0394 0.161 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
C5 N1 N2 112.3(3) . .
C5 N1 C27 128.0(3) . .
N2 N1 C27 119.7(3) . .
C3 N2 N1 104.7(3) . .
C22 C21 C26 118.7(3) . .
C22 C21 C41 123.3(3) . .
C26 C21 C41 118.0(3) . .
C23 C22 C21 118.7(3) . .
C23 C22 C27 121.1(3) . .
C21 C22 C27 120.3(3) . .
C24 C23 C22 121.8(4) . .
C24 C23 H23 119.1 . .
C22 C23 H23 119.1 . .
C25 C24 C23 119.8(3) . .
C25 C24 H24 120.1 . .
C23 C24 H24 120.1 . .
C24 C25 C26 119.4(4) . .
C24 C25 H25 120.3 . .
C26 C25 H25 120.3 . .
C25 C26 C21 121.7(3) . .
C25 C26 H26 119.2 . .
C21 C26 H26 119.2 . .
N1 C27 C22 114.8(3) . .
N1 C27 H27A 108.6 . .
C22 C27 H27A 108.6 . .
N1 C27 H27B 108.6 . .
C22 C27 H27B 108.6 . .
H27A C27 H27B 107.5 . .
N2 C3 C4 110.8(3) . .
N2 C3 C31 120.8(4) . .
C4 C3 C31 128.4(4) . .
C3 C31 H31A 109.5 . .
C3 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C3 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C5 C4 C3 106.6(3) . .
C5 C4 H4 126.7 . .
C3 C4 H4 126.7 . .
C42 C41 C42 117.9(3) . 2_665
C42 C41 C21 122.2(3) . .
C42 C41 C21 119.7(3) 2_665 .
C41 C42 C41 122.1(3) . 3_565
C41 C42 H42 119.0 . .
C41 C42 H42 119.0 3_565 .
N1 C5 C4 105.5(3) . .
N1 C5 C51 122.4(4) . .
C4 C5 C51 132.1(4) . .
C5 C51 H51A 109.5 . .
C5 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C5 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.349(4) .
N1 N2 1.356(3) .
N1 C27 1.442(4) .
N2 C3 1.321(4) .
C21 C22 1.390(4) .
C21 C26 1.391(4) .
C21 C41 1.495(4) .
C22 C23 1.385(4) .
C22 C27 1.525(4) .
C23 C24 1.375(5) .
C23 H23 0.9300 .
C24 C25 1.364(5) .
C24 H24 0.9300 .
C25 C26 1.376(4) .
C25 H25 0.9300 .
C26 H26 0.9300 .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C3 C4 1.386(5) .
C3 C31 1.489(5) .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
C4 C5 1.361(5) .
C4 H4 0.9300 .
C41 C42 1.389(4) .
C41 C42 1.395(4) 2_665
C42 C41 1.395(4) 3_565
C42 H42 0.9300 .
C5 C51 1.489(5) .
C51 H51A 0.9600 .
C51 H51B 0.9600 .
C51 H51C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C5 N1 N2 C3 -0.4(4) . .
C27 N1 N2 C3 -179.7(3) . .
C26 C21 C22 C23 0.0(5) . .
C41 C21 C22 C23 -178.1(3) . .
C26 C21 C22 C27 178.0(3) . .
C41 C21 C22 C27 -0.1(5) . .
C21 C22 C23 C24 -0.4(5) . .
C27 C22 C23 C24 -178.4(3) . .
C22 C23 C24 C25 0.4(6) . .
C23 C24 C25 C26 -0.1(6) . .
C24 C25 C26 C21 -0.3(5) . .
C22 C21 C26 C25 0.3(5) . .
C41 C21 C26 C25 178.5(3) . .
C5 N1 C27 C22 -83.6(4) . .
N2 N1 C27 C22 95.7(4) . .
C23 C22 C27 N1 3.5(5) . .
C21 C22 C27 N1 -174.5(3) . .
N1 N2 C3 C4 0.5(4) . .
N1 N2 C3 C31 -178.6(3) . .
N2 C3 C4 C5 -0.5(4) . .
C31 C3 C4 C5 178.5(4) . .
C22 C21 C41 C42 -57.4(4) . .
C26 C21 C41 C42 124.5(3) . .
C22 C21 C41 C42 126.5(3) . 2_665
C26 C21 C41 C42 -51.6(4) . 2_665
C42 C41 C42 C41 -0.2(6) 2_665 3_565
C21 C41 C42 C41 -176.3(2) . 3_565
N2 N1 C5 C4 0.1(4) . .
C27 N1 C5 C4 179.4(3) . .
N2 N1 C5 C51 -179.6(3) . .
C27 N1 C5 C51 -0.3(6) . .
C3 C4 C5 N1 0.3(4) . .
C3 C4 C5 C51 179.9(4) . .
