#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:35:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180146 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/43/7104384.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_7104384
loop_
_publ_author_name
'Hirsch-Weil, Dimitri'
'Snead, David R'
'Inagaki, Sebastien'
'Seo, Hwimin'
'Abboud, Khalil A'
'Hong, Sukwon'
_publ_section_title
;
 In situ generation of novel acyclic diaminocarbene-copper complex.
;
_journal_issue                   18
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2475
_journal_page_last               2477
_journal_paper_doi               10.1039/b821169h
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C25 H28 Cl3 Cu N2'
_chemical_formula_weight         526.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2007-08-24 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1072(5)
_cell_length_b                   17.4430(11)
_cell_length_c                   19.5633(13)
_cell_measurement_reflns_used    145
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     2425.3(3)
_computing_cell_refinement
'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)'
_computing_data_collection       'Bruker SMART v5.624 (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL v6.14 (Bruker 2000)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  'Bruker SHELXTL v6.14'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       '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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9852
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  0.8961
_exptl_absorpt_correction_T_min  0.7376
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL v6.12 (Bruker 1998)'
_exptl_crystal_colour            pale
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0345
_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)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                4548
_reflns_number_total             5109
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b821169h.txt
_cod_data_source_block           dhw1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7104384
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'
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_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'
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) . . ?
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) . ?
