#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/74/2237409.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237409
loop_
_publ_author_name
'Stibrany, Robert T.'
'Potenza, Joseph A.'
_publ_section_title
;
 rac-Dichlorido[3-ethoxy-3-(1-ethyl-1H-benzimidazol-2-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole]copper(II)
;
_journal_coeditor_code           TK5184
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m92
_journal_page_last               m93
_journal_paper_doi               10.1107/S1600536812051641
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Cu Cl2 (C21 H22 N4 O)]'
_chemical_formula_moiety         'C21 H22 Cl2 Cu N4 O'
_chemical_formula_sum            'C21 H22 Cl2 Cu N4 O'
_chemical_formula_weight         480.87
_chemical_name_systematic
;
rac-Dichlorido[3-ethoxy-3-(1-ethyl-1H-benzimidazol-2-yl)-2,3-
dihydro-1H-pyrrolo[1,2-a]benzimidazole]copper(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.973(4)
_cell_angle_beta                 92.373(4)
_cell_angle_gamma                113.778(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9409(17)
_cell_length_b                   9.5209(18)
_cell_length_c                   14.323(3)
_cell_measurement_reflns_used    897
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      50.748
_cell_measurement_theta_min      4.967
_cell_volume                     1049.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10062
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.316
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000; Blessing, 1995)'
_exptl_crystal_colour            yellow-green
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cleaved plate'
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0437
_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)+(0.0832P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                3380
_reflns_number_total             4126
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5184.cif
_cod_data_source_block           I
_cod_original_cell_volume        1049.3(3)
_cod_database_code               2237409
_cod_database_fobs_code          2237409
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cu Cu -0.05985(4) 1.12548(4) 0.28616(3) 0.04148(15) Uani d . 1 1
Cl Cl1 -0.11321(11) 1.17616(13) 0.15011(7) 0.0642(3) Uani d . 1 1
Cl Cl2 -0.17411(11) 1.26316(11) 0.38646(7) 0.0588(2) Uani d . 1 1
O O1 0.0067(3) 0.7244(3) 0.15123(16) 0.0505(5) Uani d . 1 1
N N11 0.3553(3) 1.0483(3) 0.21160(19) 0.0420(6) Uani d . 1 1
N N13 0.1575(3) 1.1244(3) 0.25783(17) 0.0375(5) Uani d . 1 1
N N21 -0.0518(3) 0.7479(3) 0.36364(18) 0.0410(5) Uani d . 1 1
N N23 -0.1091(3) 0.9408(3) 0.33722(18) 0.0411(5) Uani d . 1 1
C C1 0.0961(3) 0.8415(3) 0.2462(2) 0.0385(6) Uani d . 1 1
C C3 -0.0847(5) 0.7703(5) 0.0917(3) 0.0678(10) Uani d . 1 1
H H3A -0.0093 0.8600 0.0729 0.081 Uiso calc R 1 1
H H3B -0.1594 0.8052 0.1287 0.081 Uiso calc R 1 1
C C4 -0.1818(6) 0.6250(7) 0.0011(3) 0.1055(19) Uani d . 1 1
H H4A -0.1073 0.5879 -0.0329 0.158 Uiso calc R 1 1
H H4B -0.2395 0.6545 -0.0421 0.158 Uiso calc R 1 1
H H4C -0.2607 0.5393 0.0203 0.158 Uiso calc R 1 1
C C11 0.4096(3) 1.2079(3) 0.2130(2) 0.0397(6) Uani d . 1 1
C C12 0.2047(3) 1.0057(3) 0.2399(2) 0.0365(6) Uani d . 1 1
C C13 0.2862(3) 1.2549(3) 0.2426(2) 0.0369(6) Uani d . 1 1
C C14 0.3060(4) 1.4126(4) 0.2565(2) 0.0466(7) Uani d . 1 1
H H14 0.2250 1.4460 0.2777 0.056 Uiso calc R 1 1
C C15 0.4509(4) 1.5166(4) 0.2374(3) 0.0513(8) Uani d . 1 1
H H15 0.4679 1.6228 0.2455 0.062 Uiso calc R 1 1
C C16 0.5728(4) 1.4675(4) 0.2062(2) 0.0516(8) Uani d . 1 1
H H16 0.6685 1.5415 0.1933 0.062 Uiso calc R 1 1
C C17 0.5561(4) 1.3137(4) 0.1939(2) 0.0483(7) Uani d . 1 1
H H17 0.6383 1.2816 0.1738 0.058 Uiso calc R 1 1
C C18 0.4450(4) 0.9499(4) 0.1798(3) 0.0625(10) Uani d D 1 1
H H18A 0.5629 1.0211 0.1924 0.075 Uiso calc R 1 1
H H18B 0.4279 0.8787 0.2189 0.075 Uiso calc R 1 1
C C19 0.3921(9) 0.8517(9) 0.0753(4) 0.145(3) Uani d D 1 1
H H19A 0.2790 0.7719 0.0638 0.217 Uiso calc R 1 1
H H19B 0.4620 0.7976 0.0563 0.217 Uiso calc R 1 1
H H19C 0.4004 0.9206 0.0365 0.217 Uiso calc R 1 1
C C21 -0.1714(3) 0.7566(3) 0.4191(2) 0.0407(6) Uani d . 1 1
C C22 -0.0218(3) 0.8560(3) 0.3164(2) 0.0375(6) Uani d . 1 1
C C23 -0.2082(3) 0.8786(3) 0.4025(2) 0.0397(6) Uani d . 1 1
C C24 -0.3296(4) 0.9138(4) 0.4451(3) 0.0535(8) Uani d . 1 1
H H24 -0.3543 0.9952 0.4356 0.064 Uiso calc R 1 1
C C25 -0.4141(4) 0.8241(4) 0.5026(3) 0.0575(8) Uani d . 1 1
H H25 -0.4979 0.8445 0.5314 0.069 Uiso calc R 1 1
C C26 -0.3756(4) 0.7040(4) 0.5180(2) 0.0526(8) Uani d . 1 1
H H26 -0.4345 0.6463 0.5572 0.063 Uiso calc R 1 1
C C27 -0.2544(4) 0.6675(4) 0.4778(2) 0.0497(7) Uani d . 1 1
H H27 -0.2288 0.5876 0.4890 0.060 Uiso calc R 1 1
C C28 0.0448(4) 0.6532(4) 0.3416(3) 0.0513(8) Uani d . 1 1
H H28A -0.0222 0.5433 0.2962 0.062 Uiso calc R 1 1
H H28B 0.0945 0.6486 0.4015 0.062 Uiso calc R 1 1
C C29 0.1774(4) 0.7556(4) 0.2925(3) 0.0492(7) Uani d . 1 1
H H29A 0.2095 0.6860 0.2417 0.059 Uiso calc R 1 1
H H29B 0.2755 0.8354 0.3416 0.059 Uiso calc R 1 1
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'
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_publ_flag
N23 Cu N13 90.45(9) y
N23 Cu Cl1 141.12(8) y
N13 Cu Cl1 94.14(7) y
N23 Cu Cl2 100.17(7) y
N13 Cu Cl2 143.67(8) y
Cl1 Cu Cl2 98.64(4) y
C3 O1 C1 116.9(2) ?
C12 N11 C11 106.7(2) ?
C12 N11 C18 129.1(3) ?
C11 N11 C18 124.2(2) ?
C12 N13 C13 106.1(2) ?
C12 N13 Cu 130.38(19) ?
C13 N13 Cu 123.17(18) ?
C22 N21 C21 107.9(2) ?
C22 N21 C28 114.1(2) ?
C21 N21 C28 138.0(3) ?
C22 N23 C23 104.6(2) ?
C22 N23 Cu 118.62(19) ?
C23 N23 Cu 136.46(19) ?
O1 C1 C12 112.2(2) ?
O1 C1 C22 110.5(2) ?
C12 C1 C22 110.3(2) ?
O1 C1 C29 104.6(2) ?
C12 C1 C29 118.8(2) ?
C22 C1 C29 99.6(2) ?
O1 C3 C4 107.8(4) ?
O1 C3 H3A 110.1 ?
C4 C3 H3A 110.1 ?
O1 C3 H3B 110.1 ?
C4 C3 H3B 110.1 ?
H3A C3 H3B 108.5 ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
C13 C11 C17 122.0(3) ?
C13 C11 N11 106.4(2) ?
C17 C11 N11 131.6(3) ?
N13 C12 N11 112.2(2) ?
N13 C12 C1 122.2(2) ?
N11 C12 C1 125.5(2) ?
C11 C13 C14 120.9(3) ?
C11 C13 N13 108.6(2) ?
C14 C13 N13 130.4(3) ?
C15 C14 C13 116.8(3) ?
C15 C14 H14 121.6 ?
C13 C14 H14 121.6 ?
C14 C15 C16 121.9(3) ?
C14 C15 H15 119.1 ?
C16 C15 H15 119.1 ?
C17 C16 C15 121.9(3) ?
C17 C16 H16 119.0 ?
C15 C16 H16 119.0 ?
C16 C17 C11 116.5(3) ?
C16 C17 H17 121.8 ?
C11 C17 H17 121.8 ?
C19 C18 N11 112.5(4) ?
C19 C18 H18A 109.1 ?
N11 C18 H18A 109.1 ?
C19 C18 H18B 109.1 ?
N11 C18 H18B 109.1 ?
H18A C18 H18B 107.8 ?
C18 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C18 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
N21 C21 C27 132.3(3) ?
N21 C21 C23 105.3(2) ?
C27 C21 C23 122.3(3) ?
N23 C22 N21 113.5(3) ?
N23 C22 C1 135.6(3) ?
N21 C22 C1 110.7(2) ?
C24 C23 C21 120.1(3) ?
C24 C23 N23 131.1(3) ?
C21 C23 N23 108.8(2) ?
C23 C24 C25 117.9(3) ?
C23 C24 H24 121.1 ?
C25 C24 H24 121.1 ?
C24 C25 C26 121.0(3) ?
C24 C25 H25 119.5 ?
C26 C25 H25 119.5 ?
C27 C26 C25 122.5(3) ?
C27 C26 H26 118.8 ?
C25 C26 H26 118.8 ?
C26 C27 C21 116.2(3) ?
C26 C27 H27 121.9 ?
C21 C27 H27 121.9 ?
N21 C28 C29 100.3(2) ?
N21 C28 H28A 111.7 ?
C29 C28 H28A 111.7 ?
N21 C28 H28B 111.7 ?
C29 C28 H28B 111.7 ?
H28A C28 H28B 109.5 ?
C28 C29 C1 106.2(2) ?
C28 C29 H29A 110.5 ?
C1 C29 H29A 110.5 ?
C28 C29 H29B 110.5 ?
C1 C29 H29B 110.5 ?
H29A C29 H29B 108.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu N23 1.993(2) y
Cu N13 2.005(2) y
Cu Cl1 2.2169(9) y
Cu Cl2 2.2198(9) y
O1 C3 1.426(4) ?
O1 C1 1.428(3) ?
N11 C12 1.357(3) ?
N11 C11 1.390(4) ?
N11 C18 1.454(4) ?
N13 C12 1.321(4) ?
N13 C13 1.393(4) ?
N21 C22 1.338(3) ?
N21 C21 1.373(4) ?
N21 C28 1.464(4) ?
N23 C22 1.318(4) ?
N23 C23 1.407(3) ?
C1 C12 1.504(4) ?
C1 C22 1.505(4) ?
C1 C29 1.546(4) ?
C3 C4 1.498(6) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
C11 C13 1.386(4) ?
C11 C17 1.390(4) ?
C13 C14 1.391(4) ?
C14 C15 1.373(4) ?
C14 H14 0.9300 ?
C15 C16 1.391(5) ?
C15 H15 0.9300 ?
C16 C17 1.366(5) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 C19 1.452(6) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C21 C27 1.392(4) ?
C21 C23 1.405(4) ?
C23 C24 1.375(4) ?
C24 C25 1.386(5) ?
C24 H24 0.9300 ?
C25 C26 1.391(5) ?
C25 H25 0.9300 ?
C26 C27 1.365(5) ?
C26 H26 0.9300 ?
C27 H27 0.9300 ?
C28 C29 1.545(4) ?
C28 H28A 0.9700 ?
C28 H28B 0.9700 ?
C29 H29A 0.9700 ?
C29 H29B 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4B Cg1 2_575 0.96 2.99 3.910(5) 160
C17 H17 Cl1 1_655 0.93 2.78 3.694(4) 169
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
N23 Cu N13 C12 25.1(3)
Cl1 Cu N13 C12 -116.3(2)
Cl2 Cu N13 C12 133.1(2)
N23 Cu N13 C13 -162.5(2)
Cl1 Cu N13 C13 56.1(2)
Cl2 Cu N13 C13 -54.5(3)
N13 Cu N23 C22 -15.8(2)
Cl1 Cu N23 C22 81.4(2)
Cl2 Cu N23 C22 -160.9(2)
N13 Cu N23 C23 156.1(3)
Cl1 Cu N23 C23 -106.8(3)
Cl2 Cu N23 C23 11.0(3)
C3 O1 C1 C12 -51.1(3)
C3 O1 C1 C22 72.5(3)
C3 O1 C1 C29 178.8(3)
C1 O1 C3 C4 -174.3(3)
C12 N11 C11 C13 -0.1(3)
C18 N11 C11 C13 176.9(3)
C12 N11 C11 C17 177.8(3)
C18 N11 C11 C17 -5.2(5)
C13 N13 C12 N11 -1.3(3)
Cu N13 C12 N11 172.07(19)
C13 N13 C12 C1 -178.6(3)
Cu N13 C12 C1 -5.2(4)
C11 N11 C12 N13 0.9(3)
C18 N11 C12 N13 -175.9(3)
C11 N11 C12 C1 178.1(3)
C18 N11 C12 C1 1.3(5)
O1 C1 C12 N13 97.8(3)
C22 C1 C12 N13 -25.9(4)
C29 C1 C12 N13 -139.9(3)
O1 C1 C12 N11 -79.1(3)
C22 C1 C12 N11 157.2(3)
C29 C1 C12 N11 43.2(4)
C17 C11 C13 C14 -1.4(5)
N11 C11 C13 C14 176.7(3)
C17 C11 C13 N13 -178.8(3)
N11 C11 C13 N13 -0.7(3)
C12 N13 C13 C11 1.2(3)
Cu N13 C13 C11 -172.76(18)
C12 N13 C13 C14 -175.9(3)
Cu N13 C13 C14 10.1(4)
C11 C13 C14 C15 1.4(5)
N13 C13 C14 C15 178.2(3)
C13 C14 C15 C16 -0.4(5)
C14 C15 C16 C17 -0.8(5)
C15 C16 C17 C11 0.8(5)
C13 C11 C17 C16 0.3(5)
N11 C11 C17 C16 -177.3(3)
C12 N11 C18 C19 83.6(5)
C11 N11 C18 C19 -92.7(5)
C22 N21 C21 C27 176.2(3)
C28 N21 C21 C27 -2.1(6)
C22 N21 C21 C23 -0.8(3)
C28 N21 C21 C23 -179.1(3)
C23 N23 C22 N21 -1.5(3)
Cu N23 C22 N21 172.72(19)
C23 N23 C22 C1 173.0(3)
Cu N23 C22 C1 -12.8(4)
C21 N21 C22 N23 1.5(3)
C28 N21 C22 N23 -179.8(3)
C21 N21 C22 C1 -174.4(2)
C28 N21 C22 C1 4.3(3)
O1 C1 C22 N23 -86.1(4)
C12 C1 C22 N23 38.5(4)
C29 C1 C22 N23 164.2(3)
O1 C1 C22 N21 88.5(3)
C12 C1 C22 N21 -146.9(2)
C29 C1 C22 N21 -21.1(3)
N21 C21 C23 C24 177.6(3)
C27 C21 C23 C24 0.2(5)
N21 C21 C23 N23 -0.1(3)
C27 C21 C23 N23 -177.5(3)
C22 N23 C23 C24 -176.4(3)
Cu N23 C23 C24 11.0(5)
C22 N23 C23 C21 0.9(3)
Cu N23 C23 C21 -171.7(2)
C21 C23 C24 C25 -0.9(5)
N23 C23 C24 C25 176.1(3)
C23 C24 C25 C26 1.0(5)
C24 C25 C26 C27 -0.2(5)
C25 C26 C27 C21 -0.6(5)
N21 C21 C27 C26 -176.0(3)
C23 C21 C27 C26 0.6(4)
C22 N21 C28 C29 14.7(3)
C21 N21 C28 C29 -167.1(3)
N21 C28 C29 C1 -27.3(3)
O1 C1 C29 C28 -84.9(3)
C12 C1 C29 C28 149.1(3)
C22 C1 C29 C28 29.4(3)
