#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/81/2208130.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_2208130
loop_
_publ_author_name
'Wei, Yi-Jun'
'Wang, Feng-Wu'
_publ_section_title
;
 Azido{2,4-dichloro-6-[2-(diethylamino)ethyliminomethyl]phenolato}copper(II)
;
_journal_coeditor_code           NC6060
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m309
_journal_page_last               m311
_journal_paper_doi               10.1107/S1600536806001565
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu (C13 H17 Cl2 N2 O) (N3)]'
_chemical_formula_moiety         'C13 H17 Cl2 Cu N5 O'
_chemical_formula_sum            'C13 H17 Cl2 Cu N5 O'
_chemical_formula_weight         393.76
_chemical_name_systematic
;
Azido{2,4-dichloro-6-[2-(diethylamino)ethyliminomethyl]phenolato}copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.32(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.723(2)
_cell_length_b                   11.506(2)
_cell_length_c                   13.192(3)
_cell_measurement_reflns_used    5676
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.36
_cell_volume                     1606.1(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7787
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    1.700
_exptl_absorpt_correction_T_max  0.8220
_exptl_absorpt_correction_T_min  0.5719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.546
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0333
_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)+(0.0534P)²+0.0366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                2882
_reflns_number_total             3383
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc6060.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208130
_cod_database_fobs_code          2208130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
Cu1 0.95385(2) 0.82628(2) 0.111644(19) 0.03184(11) Uani d . 1 Cu
Cl1 1.29279(6) 0.73493(5) 0.37898(5) 0.04521(16) Uani d . 1 Cl
Cl2 1.49254(6) 0.44477(6) 0.13109(5) 0.05553(19) Uani d . 1 Cl
O1 1.09529(14) 0.77042(13) 0.20310(12) 0.0358(3) Uani d . 1 O
N1 0.98407(17) 0.72564(16) 0.00085(13) 0.0340(4) Uani d . 1 N
N2 0.78622(17) 0.86402(16) 0.01630(15) 0.0340(4) Uani d . 1 N
N3 0.9351(2) 0.96024(18) 0.19781(17) 0.0486(5) Uani d . 1 N
N4 1.0209(2) 1.00161(16) 0.25494(15) 0.0383(4) Uani d . 1 N
N5 1.0999(2) 1.04512(19) 0.31145(18) 0.0563(6) Uani d . 1 N
C1 1.1756(2) 0.63767(18) 0.08825(17) 0.0324(5) Uani d . 1 C
C2 1.1794(2) 0.69615(17) 0.18312(16) 0.0300(4) Uani d . 1 C
C3 1.2845(2) 0.67056(17) 0.25899(17) 0.0330(5) Uani d . 1 C
C4 1.3787(2) 0.59603(19) 0.24297(18) 0.0383(5) Uani d . 1 C
H4 1.4467 0.5823 0.2949 0.046 Uiso calc R 1 H
C5 1.3721(2) 0.54099(19) 0.14878(19) 0.0399(5) Uani d . 1 C
C6 1.2731(2) 0.56025(19) 0.07263(18) 0.0377(5) Uani d . 1 C
H6 1.2692 0.5224 0.0099 0.045 Uiso calc R 1 H
C7 1.0760(2) 0.65402(18) 0.00265(17) 0.0351(5) Uani d . 1 C
H7 1.0784 0.6094 -0.0558 0.042 Uiso calc R 1 H
C8 0.8894(2) 0.7346(2) -0.09250(18) 0.0440(6) Uani d . 1 C
H8A 0.8814 0.6611 -0.1289 0.053 Uiso calc R 1 H
H8B 0.9137 0.7939 -0.1378 0.053 Uiso calc R 1 H
C9 0.7662(2) 0.7665(2) -0.05846(19) 0.0425(6) Uani d . 1 C
H9A 0.7051 0.7892 -0.1176 0.051 Uiso calc R 1 H
H9B 0.7330 0.6997 -0.0268 0.051 Uiso calc R 1 H
C10 0.8089(2) 0.9764(2) -0.0345(2) 0.0451(6) Uani d . 1 C
H10A 0.8840 0.9679 -0.0662 0.054 Uiso calc R 1 H
H10B 0.8269 1.0355 0.0183 0.054 Uiso calc R 1 H
C11 0.7025(3) 1.0202(2) -0.1155(2) 0.0633(8) Uani d . 1 C
H11A 0.6830 0.9626 -0.1683 0.095 Uiso calc R 1 H
H11B 0.7282 1.0908 -0.1450 0.095 Uiso calc R 1 H
H11C 0.6291 1.0348 -0.0844 0.095 Uiso calc R 1 H
C12 0.6768(2) 0.8757(2) 0.0717(2) 0.0454(6) Uani d . 1 C
H12A 0.6002 0.8818 0.0216 0.055 Uiso calc R 1 H
H12B 0.6858 0.9475 0.1108 0.055 Uiso calc R 1 H
C13 0.6621(3) 0.7767(3) 0.1437(2) 0.0671(8) Uani d . 1 C
H13A 0.6334 0.7087 0.1045 0.101 Uiso calc R 1 H
H13B 0.6016 0.7975 0.1867 0.101 Uiso calc R 1 H
H13C 0.7421 0.7607 0.1856 0.101 Uiso calc R 1 H
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
O1 Cu1 N1 93.64(7) y
O1 Cu1 N3 92.56(8) y
N1 Cu1 N3 164.30(9) y
O1 Cu1 N2 171.31(7) y
N1 Cu1 N2 84.35(8) y
N3 Cu1 N2 91.55(8) y
C2 O1 Cu1 127.23(14) ?
C7 N1 C8 119.09(19) ?
C7 N1 Cu1 126.42(16) ?
C8 N1 Cu1 114.50(14) ?
C12 N2 C9 110.76(18) ?
C12 N2 C10 109.94(18) ?
C9 N2 C10 111.85(19) ?
C12 N2 Cu1 113.46(15) ?
C9 N2 Cu1 105.25(13) ?
C10 N2 Cu1 105.42(13) ?
N4 N3 Cu1 122.98(16) ?
N5 N4 N3 176.9(2) ?
C6 C1 C2 120.8(2) ?
C6 C1 C7 116.2(2) ?
C2 C1 C7 122.97(19) ?
O1 C2 C3 119.59(19) ?
O1 C2 C1 124.79(19) ?
C3 C2 C1 115.62(19) ?
C4 C3 C2 123.1(2) ?
C4 C3 Cl1 118.59(18) ?
C2 C3 Cl1 118.30(17) ?
C3 C4 C5 119.6(2) ?
C3 C4 H4 120.2 ?
C5 C4 H4 120.2 ?
C6 C5 C4 120.6(2) ?
C6 C5 Cl2 120.81(19) ?
C4 C5 Cl2 118.58(18) ?
C5 C6 C1 120.2(2) ?
C5 C6 H6 119.9 ?
C1 C6 H6 119.9 ?
N1 C7 C1 124.8(2) ?
N1 C7 H7 117.6 ?
C1 C7 H7 117.6 ?
N1 C8 C9 106.71(19) ?
N1 C8 H8A 110.4 ?
C9 C8 H8A 110.4 ?
N1 C8 H8B 110.4 ?
C9 C8 H8B 110.4 ?
H8A C8 H8B 108.6 ?
N2 C9 C8 110.00(19) ?
N2 C9 H9A 109.7 ?
C8 C9 H9A 109.7 ?
N2 C9 H9B 109.7 ?
C8 C9 H9B 109.7 ?
H9A C9 H9B 108.2 ?
N2 C10 C11 116.4(2) ?
N2 C10 H10A 108.2 ?
C11 C10 H10A 108.2 ?
N2 C10 H10B 108.2 ?
C11 C10 H10B 108.2 ?
H10A C10 H10B 107.3 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
N2 C12 C13 114.3(2) ?
N2 C12 H12A 108.7 ?
C13 C12 H12A 108.7 ?
N2 C12 H12B 108.7 ?
C13 C12 H12B 108.7 ?
H12A C12 H12B 107.6 ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 1.891(2) y
Cu1 N1 1.933(2) y
Cu1 N3 1.945(2) y
Cu1 N2 2.066(2) y
Cl1 C3 1.737(2) ?
Cl2 C5 1.745(2) ?
O1 C2 1.300(3) ?
N1 C7 1.282(3) ?
N1 C8 1.467(3) ?
N2 C12 1.486(3) ?
N2 C9 1.487(3) ?
N2 C10 1.495(3) ?
N3 N4 1.190(3) ?
N4 N5 1.149(3) ?
C1 C6 1.413(3) ?
C1 C2 1.416(3) ?
C1 C7 1.435(3) ?
C2 C3 1.412(3) ?
C3 C4 1.367(3) ?
C4 C5 1.386(3) ?
C4 H4 0.9300 ?
C5 C6 1.357(3) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.508(3) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.517(3) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 C13 1.508(4) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
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
C7 H7 N5 4_575 0.93 2.53 3.448(3) 168
C10 H10B N3 . 0.97 2.61 3.149(3) 115
