# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Sukwon Hong'
'Khalil A Abboud'
'Dimitri Hirsch-Weil'
'Sebastien Inagaki'
'Hwimin Seo'
'David R Snead'

_publ_contact_author_name        'Sukwon Hong'
_publ_contact_author_email       SUKWON@UFL.EDU

_publ_section_title              
;
In Situ Generation of Novel Acyclic
Diaminocarbene-Copper Complex
;

# Attachment '3.cif'

data_dhw1
_database_code_depnum_ccdc_archive 'CCDC 711449'

_audit_update_record             
;
2007-08-24 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H28 Cl3 Cu N2'
_chemical_formula_weight         526.38

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1072(5)
_cell_length_b                   17.4430(11)
_cell_length_c                   19.5633(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2425.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    145
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0

_exptl_crystal_description       Needles
_exptl_crystal_colour            pale
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.7376
_exptl_absorpt_correction_T_max  0.8961
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker SHELXTL v6.12 (Bruker 1998)'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            9852
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         28.03
_reflns_number_total             5109
_reflns_number_gt                4548
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker SMART v5.624 (Bruker 1998)'
_computing_cell_refinement       
'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL v6.14 (Bruker 2000)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  'Bruker SHELXTL v6.14'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(11)
_refine_ls_number_reflns         5109
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.54904(5) 0.40697(2) 0.855647(15) 0.03635(10) Uani 1 1 d . . .
Cl1 Cl 0.01723(10) 0.45438(4) 0.79758(3) 0.03691(17) Uani 1 1 d . . .
Cl2 Cl 0.53516(12) 0.52596(4) 0.87348(3) 0.04514(19) Uani 1 1 d . . .
Cl3 Cl 0.57017(12) 0.28826(5) 0.84082(4) 0.0506(2) Uani 1 1 d . . .
N1 N 0.0143(3) 0.49402(12) 0.92963(9) 0.0215(4) Uani 1 1 d . . .
N2 N 0.0618(3) 0.58903(12) 0.86060(9) 0.0233(4) Uani 1 1 d . . .
C1 C 0.0311(3) 0.51448(14) 0.86452(11) 0.0243(5) Uani 1 1 d . . .
C2 C 0.0380(3) 0.55929(13) 0.97022(10) 0.0201(5) Uani 1 1 d . . .
C3 C 0.0650(3) 0.62016(14) 0.92650(10) 0.0208(5) Uani 1 1 d . . .
C4 C 0.0391(3) 0.54826(13) 1.04454(10) 0.0204(5) Uani 1 1 d . . .
C5 C -0.0479(4) 0.48165(14) 1.07007(11) 0.0233(5) Uani 1 1 d . . .
C6 C -0.0459(4) 0.46787(15) 1.14001(12) 0.0338(6) Uani 1 1 d . . .
H6A H -0.1043 0.4230 1.1575 0.041 Uiso 1 1 calc R . .
C7 C 0.0398(5) 0.51846(16) 1.18428(12) 0.0371(7) Uani 1 1 d . . .
H7A H 0.0382 0.5088 1.2321 0.045 Uiso 1 1 calc R . .
C8 C 0.1280(4) 0.58304(16) 1.15920(12) 0.0328(6) Uani 1 1 d . . .
H8A H 0.1876 0.6176 1.1898 0.039 Uiso 1 1 calc R . .
C9 C 0.1298(3) 0.59773(16) 1.08937(12) 0.0256(5) Uani 1 1 d . . .
H9A H 0.1932 0.6417 1.0723 0.031 Uiso 1 1 calc R . .
C10 C -0.1386(3) 0.42642(15) 1.02114(12) 0.0263(6) Uani 1 1 d . . .
H10A H -0.2662 0.4452 1.0096 0.032 Uiso 1 1 calc R . .
H10B H -0.1524 0.3760 1.0439 0.032 Uiso 1 1 calc R . .
C11 C -0.0264(3) 0.41602(14) 0.95523(11) 0.0242(5) Uani 1 1 d . . .
H11A H -0.1124 0.3912 0.9213 0.029 Uiso 1 1 calc R . .
C12 C 0.1532(4) 0.36730(15) 0.95807(12) 0.0251(6) Uani 1 1 d . . .
H12A H 0.2120 0.3699 0.9117 0.030 Uiso 1 1 calc R . .
C13 C 0.1015(4) 0.28388(15) 0.97041(14) 0.0353(6) Uani 1 1 d . . .
H13A H 0.2163 0.2528 0.9722 0.053 Uiso 1 1 calc R . .
H13B H 0.0211 0.2656 0.9331 0.053 Uiso 1 1 calc R . .
H13C H 0.0338 0.2794 1.0139 0.053 Uiso 1 1 calc R . .
C14 C 0.3021(4) 0.39456(16) 1.00917(14) 0.0332(6) Uani 1 1 d . . .
H14A H 0.4111 0.3602 1.0074 0.050 Uiso 1 1 calc R . .
H14B H 0.2489 0.3942 1.0554 0.050 Uiso 1 1 calc R . .
H14C H 0.3417 0.4467 0.9974 0.050 Uiso 1 1 calc R . .
C15 C 0.0833(3) 0.70293(15) 0.93325(11) 0.0231(5) Uani 1 1 d . . .
C16 C 0.1611(3) 0.74360(16) 0.87758(13) 0.0280(6) Uani 1 1 d . . .
C17 C 0.1733(4) 0.82287(17) 0.88139(15) 0.0357(7) Uani 1 1 d . . .
H17A H 0.2240 0.8505 0.8438 0.043 Uiso 1 1 calc R . .
C18 C 0.1131(4) 0.86275(17) 0.93875(16) 0.0377(7) Uani 1 1 d . . .
H18A H 0.1242 0.9170 0.9407 0.045 Uiso 1 1 calc R . .
C19 C 0.0364(4) 0.82225(15) 0.99331(15) 0.0342(6) Uani 1 1 d . . .
H19A H -0.0050 0.8490 1.0328 0.041 Uiso 1 1 calc R . .
C20 C 0.0199(3) 0.74357(15) 0.99046(13) 0.0264(5) Uani 1 1 d . . .
H20A H -0.0351 0.7167 1.0277 0.032 Uiso 1 1 calc R . .
C21 C 0.2259(4) 0.69922(17) 0.81599(13) 0.0328(7) Uani 1 1 d . . .
H21A H 0.3529 0.6783 0.8252 0.039 Uiso 1 1 calc R . .
H21B H 0.2362 0.7347 0.7766 0.039 Uiso 1 1 calc R . .
C22 C 0.0950(4) 0.63359(16) 0.79692(12) 0.0295(6) Uani 1 1 d . . .
H22A H 0.1658 0.5995 0.7649 0.035 Uiso 1 1 calc R . .
C23 C -0.0928(4) 0.65400(17) 0.76181(12) 0.0339(7) Uani 1 1 d . . .
H23A H -0.1655 0.6052 0.7571 0.041 Uiso 1 1 calc R . .
C24 C -0.2161(4) 0.70957(19) 0.80111(16) 0.0465(8) Uani 1 1 d . . .
H24A H -0.3318 0.7192 0.7753 0.070 Uiso 1 1 calc R . .
H24B H -0.1483 0.7579 0.8078 0.070 Uiso 1 1 calc R . .
H24C H -0.2479 0.6875 0.8457 0.070 Uiso 1 1 calc R . .
C25 C -0.0541(5) 0.6832(2) 0.68976(14) 0.0625(11) Uani 1 1 d . . .
H25A H -0.1733 0.6961 0.6674 0.094 Uiso 1 1 calc R . .
H25B H 0.0104 0.6433 0.6634 0.094 Uiso 1 1 calc R . .
H25C H 0.0256 0.7290 0.6921 0.094 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.03156(16) 0.0498(2) 0.02770(15) -0.00687(14) -0.00076(14) 0.00386(18)
Cl1 0.0475(4) 0.0398(4) 0.0234(3) -0.0085(2) 0.0010(3) 0.0024(3)
Cl2 0.0467(4) 0.0472(5) 0.0415(4) -0.0060(3) -0.0013(3) 0.0036(4)
Cl3 0.0551(5) 0.0529(5) 0.0439(4) -0.0148(3) 0.0043(4) 0.0071(4)
N1 0.0227(10) 0.0223(11) 0.0194(9) -0.0012(7) 0.0020(8) 0.0015(9)
N2 0.0211(9) 0.0293(13) 0.0194(8) 0.0037(8) 0.0010(8) 0.0007(10)
C1 0.0259(11) 0.0256(15) 0.0215(11) -0.0021(9) 0.0006(10) 0.0028(11)
C2 0.0170(10) 0.0212(13) 0.0221(10) 0.0001(8) 0.0017(10) -0.0008(10)
C3 0.0179(10) 0.0265(15) 0.0179(10) 0.0007(9) 0.0008(9) -0.0002(10)
C4 0.0198(10) 0.0222(14) 0.0192(10) 0.0015(8) 0.0008(9) 0.0035(11)
C5 0.0240(11) 0.0222(14) 0.0237(10) 0.0006(9) 0.0043(10) -0.0001(11)
C6 0.0429(14) 0.0315(15) 0.0269(12) 0.0090(10) 0.0087(13) -0.0020(14)
C7 0.0536(16) 0.0391(18) 0.0187(11) 0.0040(10) 0.0032(12) 0.0019(16)
C8 0.0387(14) 0.0348(18) 0.0250(12) -0.0025(11) -0.0061(11) 0.0011(13)
C9 0.0261(11) 0.0252(15) 0.0255(11) 0.0033(10) -0.0011(10) -0.0013(12)
C10 0.0260(12) 0.0239(16) 0.0290(12) -0.0004(10) 0.0074(10) -0.0046(11)
C11 0.0246(11) 0.0227(15) 0.0253(11) -0.0016(9) -0.0007(10) -0.0038(12)
C12 0.0274(13) 0.0210(16) 0.0270(12) -0.0006(10) 0.0041(10) 0.0007(11)
C13 0.0426(16) 0.0235(17) 0.0400(14) 0.0001(11) -0.0022(12) 0.0017(13)
C14 0.0276(13) 0.0311(18) 0.0409(15) -0.0005(12) -0.0049(11) 0.0027(13)
C15 0.0192(11) 0.0241(15) 0.0259(11) 0.0062(10) -0.0028(9) -0.0010(10)
C16 0.0210(11) 0.0315(18) 0.0314(13) 0.0124(11) -0.0057(10) -0.0065(11)
C17 0.0247(12) 0.036(2) 0.0463(16) 0.0203(13) -0.0107(12) -0.0091(12)
C18 0.0277(13) 0.0227(17) 0.0627(19) 0.0078(14) -0.0139(13) -0.0050(12)
C19 0.0261(12) 0.0258(16) 0.0506(15) -0.0023(11) -0.0077(13) 0.0000(13)
C20 0.0228(12) 0.0229(15) 0.0336(12) 0.0028(10) -0.0030(10) -0.0011(11)
C21 0.0235(12) 0.0440(19) 0.0309(13) 0.0131(12) 0.0017(10) -0.0047(12)
C22 0.0302(13) 0.0394(17) 0.0188(11) 0.0078(10) 0.0040(10) -0.0021(12)
C23 0.0328(14) 0.0420(19) 0.0269(12) 0.0104(11) -0.0047(11) -0.0069(13)
C24 0.0326(15) 0.052(2) 0.0553(18) 0.0008(17) -0.0157(14) 0.0067(15)
C25 0.054(2) 0.101(3) 0.0318(15) 0.0308(16) -0.0102(16) -0.015(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 Cl3 2.0963(9) . ?
Cu1 Cl2 2.1069(8) . ?
Cl1 C1 1.680(2) . ?
N1 C1 1.328(3) . ?
N1 C2 1.398(3) . ?
N1 C11 1.478(3) . ?
N2 C1 1.321(3) . ?
N2 C3 1.399(3) . ?
N2 C22 1.487(3) . ?
C2 C3 1.377(3) . ?
C2 C4 1.467(3) . ?
C3 C15 1.456(4) . ?
C4 C9 1.389(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.389(3) . ?
C5 C10 1.503(3) . ?
C6 C7 1.378(4) . ?
C7 C8 1.379(4) . ?
C8 C9 1.390(3) . ?
C10 C11 1.527(3) . ?
C11 C12 1.535(4) . ?
C12 C13 1.520(4) . ?
C12 C14 1.532(3) . ?
C15 C20 1.399(3) . ?
C15 C16 1.412(3) . ?
C16 C17 1.387(4) . ?
C16 C21 1.504(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.391(4) . ?
C19 C20 1.379(4) . ?
C21 C22 1.522(4) . ?
C22 C23 1.542(4) . ?
C23 C24 1.516(4) . ?
C23 C25 1.524(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
Cl3 Cu1 Cl2 177.88(3) . . ?
C1 N1 C2 108.36(19) . . ?
C1 N1 C11 126.1(2) . . ?
C2 N1 C11 125.49(17) . . ?
C1 N2 C3 109.34(18) . . ?
C1 N2 C22 126.12(19) . . ?
C3 N2 C22 124.5(2) . . ?
N2 C1 N1 109.6(2) . . ?
N2 C1 Cl1 125.35(17) . . ?
N1 C1 Cl1 125.1(2) . . ?
C3 C2 N1 106.97(18) . . ?
C3 C2 C4 135.8(2) . . ?
N1 C2 C4 117.2(2) . . ?
C2 C3 N2 105.7(2) . . ?
C2 C3 C15 136.1(2) . . ?
N2 C3 C15 118.04(19) . . ?
C9 C4 C5 119.52(19) . . ?
C9 C4 C2 123.1(2) . . ?
C5 C4 C2 117.2(2) . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 C10 121.4(2) . . ?
C4 C5 C10 119.44(19) . . ?
C7 C6 C5 120.8(2) . . ?
C6 C7 C8 120.0(2) . . ?
C7 C8 C9 120.3(3) . . ?
C4 C9 C8 120.1(2) . . ?
C5 C10 C11 113.0(2) . . ?
N1 C11 C10 106.20(19) . . ?
N1 C11 C12 111.05(19) . . ?
C10 C11 C12 118.00(19) . . ?
C13 C12 C14 111.1(2) . . ?
C13 C12 C11 109.6(2) . . ?
C14 C12 C11 115.3(2) . . ?
C20 C15 C16 119.2(2) . . ?
C20 C15 C3 123.1(2) . . ?
C16 C15 C3 117.6(2) . . ?
C17 C16 C15 118.9(2) . . ?
C17 C16 C21 122.5(2) . . ?
C15 C16 C21 118.6(2) . . ?
C16 C17 C18 121.6(3) . . ?
C17 C18 C19 119.1(3) . . ?
C20 C19 C18 120.5(3) . . ?
C19 C20 C15 120.6(2) . . ?
C16 C21 C22 113.3(2) . . ?
N2 C22 C21 106.55(19) . . ?
N2 C22 C23 110.88(19) . . ?
C21 C22 C23 117.7(2) . . ?
C24 C23 C25 111.1(3) . . ?
C24 C23 C22 115.0(2) . . ?
C25 C23 C22 109.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.927
_diffrn_reflns_theta_full        28.03
_diffrn_measured_fraction_theta_full 0.927
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052