#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:25:27 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179140 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/01/4310137.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_4310137
loop_
_publ_author_name
'Laurel A. Goj'
'Elizabeth D. Blue'
'Colleen Munro-Leighton'
'T. Brent Gunnoe'
'Jeffrey L. Petersen'
_publ_contact_author_address
;Department of Chemistry
North Carolina State University
Campus Box 8204
Raleigh, NC 27696
;
_publ_contact_author_email       brent_gunnoe@ncsu.edu
_publ_contact_author_fax         919-515-8909
_publ_contact_author_name        'T. Brent Gunnoe'
_publ_contact_author_phone       919-513-3904
_publ_section_title
;
Cleavage of X-H Bonds (X = N, O, or C) by Copper(I) Alkyl Complexes To
Form Monomeric Two-Coordinate Copper(I) Systems
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8647
_journal_page_last               8649
_journal_paper_doi               10.1021/ic0517624
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C29 H41 Cu N2 O'
_chemical_formula_weight         497.18
_chemical_name_systematic
; 
 (IPr)Cu(OEt) 
;
_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                 114.442(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8794(11)
_cell_length_b                   16.8766(14)
_cell_length_c                   14.7796(12)
_cell_measurement_temperature    295(2)
_cell_volume                     2924.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.1011
_diffrn_reflns_av_sigmaI/netI    0.1351
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20308
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1804
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0888P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.2072
_reflns_number_gt                2720
_reflns_number_total             6578
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0517624si20051011_050352_2.cif
_cod_data_source_block           bg497ccd
_cod_database_code               4310137
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
Cu1 Cu 0.30670(4) 0.16706(4) 1.06007(4) 0.0643(3) Uani 1 1 d . . .
O1 O 0.3857(3) 0.1312(2) 1.1845(2) 0.0802(10) Uani 1 1 d . . .
N1 N 0.1409(3) 0.2566(2) 0.8956(3) 0.0651(11) Uani 1 1 d . . .
N2 N 0.2522(4) 0.1916(3) 0.8506(3) 0.0937(16) Uani 1 1 d . . .
C1 C 0.2321(4) 0.2065(3) 0.9315(4) 0.0703(14) Uani 1 1 d . . .
C2 C 0.1760(5) 0.2322(4) 0.7684(4) 0.113(2) Uani 1 1 d . . .
H2 H 0.1739 0.2310 0.7047 0.136 Uiso 1 1 calc R . .
C3 C 0.1068(5) 0.2730(3) 0.7966(3) 0.0835(17) Uani 1 1 d . . .
H3 H 0.0474 0.3060 0.7575 0.100 Uiso 1 1 calc R . .
C4 C 0.3370(9) 0.1374(8) 0.8508(5) 0.132(4) Uani 1 1 d . . .
C5 C 0.3071(15) 0.0557(9) 0.8344(8) 0.180(7) Uani 1 1 d . . .
C6 C 0.3996(15) 0.0056(9) 0.8370(9) 0.227(8) Uani 1 1 d . . .
H6 H 0.3892 -0.0486 0.8255 0.272 Uiso 1 1 calc R . .
C7 C 0.5077(17) 0.0420(13) 0.8578(12) 0.237(13) Uani 1 1 d . . .
H7 H 0.5676 0.0087 0.8635 0.284 Uiso 1 1 calc R . .
C8 C 0.5289(16) 0.1164(12) 0.8692(10) 0.246(12) Uani 1 1 d . . .
H8 H 0.5996 0.1365 0.8778 0.295 Uiso 1 1 calc R . .
C9 C 0.4405(12) 0.1668(9) 0.8683(6) 0.161(6) Uani 1 1 d . . .
C10 C 0.1914(17) 0.0271(8) 0.8107(11) 0.230(8) Uani 1 1 d . . .
H10 H 0.1443 0.0705 0.8172 0.276 Uiso 1 1 calc R . .
C11 C 0.2000(15) -0.0386(8) 0.8837(10) 0.282(8) Uani 1 1 d . . .
H11A H 0.2386 -0.0833 0.8716 0.423 Uiso 1 1 calc R . .
H11B H 0.1248 -0.0541 0.8751 0.423 Uiso 1 1 calc R . .
H11C H 0.2420 -0.0199 0.9503 0.423 Uiso 1 1 calc R . .
C12 C 0.1366(14) -0.0074(8) 0.7028(9) 0.300(9) Uani 1 1 d . . .
H12A H 0.1873 -0.0456 0.6947 0.450 Uiso 1 1 calc R . .
H12B H 0.1234 0.0347 0.6557 0.450 Uiso 1 1 calc R . .
H12C H 0.0655 -0.0325 0.6918 0.450 Uiso 1 1 calc R . .
C13 C 0.4716(7) 0.2513(9) 0.8889(6) 0.156(4) Uani 1 1 d . . .
H13 H 0.4002 0.2790 0.8771 0.187 Uiso 1 1 calc R . .
C14 C 0.5189(11) 0.2915(8) 0.8182(8) 0.236(6) Uani 1 1 d . . .
H14A H 0.5286 0.3473 0.8321 0.354 Uiso 1 1 calc R . .
H14B H 0.4661 0.2836 0.7504 0.354 Uiso 1 1 calc R . .
H14C H 0.5911 0.2684 0.8288 0.354 Uiso 1 1 calc R . .
C15 C 0.5517(9) 0.2699(10) 0.9958(7) 0.262(7) Uani 1 1 d . . .
H15A H 0.5274 0.2418 1.0401 0.393 Uiso 1 1 calc R . .
H15B H 0.5508 0.3258 1.0073 0.393 Uiso 1 1 calc R . .
H15C H 0.6278 0.2538 1.0076 0.393 Uiso 1 1 calc R . .
C16 C 0.0897(4) 0.2879(3) 0.9596(4) 0.0701(14) Uani 1 1 d . . .
C17 C -0.0019(6) 0.2473(4) 0.9647(6) 0.104(2) Uani 1 1 d . . .
C18 C -0.0443(8) 0.2779(7) 1.0298(9) 0.156(4) Uani 1 1 d . . .
H18 H -0.1041 0.2523 1.0375 0.188 Uiso 1 1 calc R . .
C19 C -0.0007(12) 0.3427(9) 1.0808(8) 0.160(5) Uani 1 1 d . . .
H19 H -0.0311 0.3616 1.1238 0.192 Uiso 1 1 calc R . .
C20 C 0.0871(9) 0.3833(6) 1.0735(6) 0.134(3) Uani 1 1 d . . .
H20 H 0.1149 0.4291 1.1107 0.161 Uiso 1 1 calc R . .
C21 C 0.1351(6) 0.3564(4) 1.0106(5) 0.0926(19) Uani 1 1 d . . .
C22 C -0.0537(7) 0.1754(5) 0.8994(9) 0.169(4) Uani 1 1 d . . .
H22 H -0.0218 0.1743 0.8497 0.203 Uiso 1 1 calc R . .
C23 C -0.0165(12) 0.1003(7) 0.9572(14) 0.373(14) Uani 1 1 d . . .
H23A H -0.0505 0.0966 1.0039 0.560 Uiso 1 1 calc R . .
H23B H 0.0650 0.1001 0.9923 0.560 Uiso 1 1 calc R . .
H23C H -0.0402 0.0560 0.9126 0.560 Uiso 1 1 calc R . .
C24 C -0.1805(9) 0.1771(7) 0.8427(12) 0.267(8) Uani 1 1 d . . .
H24A H -0.2045 0.1320 0.7994 0.400 Uiso 1 1 calc R . .
H24B H -0.2023 0.2248 0.8039 0.400 Uiso 1 1 calc R . .
H24C H -0.2161 0.1758 0.8883 0.400 Uiso 1 1 calc R . .
C25 C 0.2318(7) 0.3998(5) 1.0033(7) 0.135(3) Uani 1 1 d . . .
H25 H 0.2461 0.3753 0.9494 0.162 Uiso 1 1 calc R . .
C26 C 0.3415(8) 0.3936(6) 1.0971(9) 0.243(7) Uani 1 1 d . . .
H26A H 0.3513 0.4408 1.1361 0.365 Uiso 1 1 calc R . .
H26B H 0.4049 0.3878 1.0794 0.365 Uiso 1 1 calc R . .
H26C H 0.3376 0.3484 1.1350 0.365 Uiso 1 1 calc R . .
C27 C 0.2000(9) 0.4870(6) 0.9747(8) 0.206(5) Uani 1 1 d . . .
H27A H 0.1318 0.4894 0.9142 0.309 Uiso 1 1 calc R . .
H27B H 0.2611 0.5128 0.9651 0.309 Uiso 1 1 calc R . .
H27C H 0.1873 0.5132 1.0269 0.309 Uiso 1 1 calc R . .
C28 C 0.3446(7) 0.0959(5) 1.2462(5) 0.128(3) Uani 1 1 d . . .
H28A H 0.3783 0.1225 1.3100 0.154 Uiso 1 1 calc R . .
H28B H 0.3719 0.0416 1.2567 0.154 Uiso 1 1 calc R . .
C29 C 0.2263(9) 0.0941(8) 1.2165(8) 0.230(6) Uani 1 1 d . . .
H29A H 0.1970 0.1472 1.2050 0.345 Uiso 1 1 calc R . .
H29B H 0.2095 0.0701 1.2677 0.345 Uiso 1 1 calc R . .
H29C H 0.1914 0.0639 1.1564 0.345 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 C1 176.9(2) . . ?
C28 O1 Cu1 128.1(4) . . ?
C1 N1 C3 112.7(4) . . ?
C1 N1 C16 121.3(4) . . ?
C3 N1 C16 126.0(4) . . ?
C1 N2 C2 111.0(4) . . ?
C1 N2 C4 123.2(5) . . ?
C2 N2 C4 125.7(5) . . ?
N2 C1 N1 102.8(4) . . ?
N2 C1 Cu1 129.1(4) . . ?
N1 C1 Cu1 128.1(4) . . ?
C3 C2 N2 107.8(5) . . ?
C2 C3 N1 105.7(4) . . ?
C9 C4 N2 117.5(11) . . ?
C9 C4 C5 124.5(10) . . ?
N2 C4 C5 117.9(10) . . ?
C4 C5 C6 113.5(15) . . ?
C4 C5 C10 122.4(10) . . ?
C6 C5 C10 124.0(16) . . ?
C7 C6 C5 118.1(16) . . ?
C8 C7 C6 125.7(18) . . ?
C7 C8 C9 117(2) . . ?
C4 C9 C8 120.6(16) . . ?
C4 C9 C13 123.9(9) . . ?
C8 C9 C13 115.4(17) . . ?
C5 C10 C11 107.6(15) . . ?
C5 C10 C12 110.6(16) . . ?
C11 C10 C12 108.7(12) . . ?
C9 C13 C15 115.0(11) . . ?
C9 C13 C14 115.3(10) . . ?
C15 C13 C14 108.6(10) . . ?
C21 C16 C17 124.2(6) . . ?
C21 C16 N1 117.2(5) . . ?
C17 C16 N1 118.5(6) . . ?
C18 C17 C16 116.1(8) . . ?
C18 C17 C22 122.7(8) . . ?
C16 C17 C22 121.2(7) . . ?
C19 C18 C17 120.6(10) . . ?
C18 C19 C20 122.9(11) . . ?
C19 C20 C21 120.1(9) . . ?
C16 C21 C20 116.0(8) . . ?
C16 C21 C25 123.7(6) . . ?
C20 C21 C25 120.4(8) . . ?
C23 C22 C24 110.8(9) . . ?
C23 C22 C17 111.2(11) . . ?
C24 C22 C17 115.5(8) . . ?
C21 C25 C26 113.0(9) . . ?
C21 C25 C27 110.8(7) . . ?
C26 C25 C27 110.9(7) . . ?
O1 C28 C29 118.2(7) . . ?
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
Cu1 O1 1.799(3) . ?
Cu1 C1 1.863(5) . ?
O1 C28 1.366(8) . ?
N1 C1 1.363(6) . ?
N1 C3 1.370(6) . ?
N1 C16 1.458(6) . ?
N2 C1 1.347(6) . ?
N2 C2 1.387(6) . ?
N2 C4 1.424(9) . ?
C2 C3 1.323(7) . ?
C4 C9 1.343(15) . ?
C4 C5 1.425(17) . ?
C5 C6 1.448(16) . ?
C5 C10 1.464(18) . ?
C6 C7 1.43(3) . ?
C7 C8 1.28(3) . ?
C8 C9 1.417(14) . ?
C9 C13 1.479(15) . ?
C10 C11 1.519(17) . ?
C10 C12 1.565(15) . ?
C13 C15 1.520(11) . ?
C13 C14 1.566(13) . ?
C16 C21 1.371(8) . ?
C16 C17 1.392(8) . ?
C17 C18 1.388(12) . ?
C17 C22 1.522(11) . ?
C18 C19 1.315(13) . ?
C19 C20 1.364(14) . ?
C20 C21 1.389(11) . ?
C21 C25 1.487(10) . ?
C22 C23 1.491(13) . ?
C22 C24 1.496(12) . ?
C25 C26 1.519(11) . ?
C25 C27 1.540(11) . ?
C28 C29 1.400(11) . ?
