#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:10:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180379 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/48/7204884.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_7204884
loop_
_publ_author_name
'Suksangpanya, Unchulee'
'Blake, Alexander J.'
'Cade, Emma L.'
'Hubberstey, Peter'
'Parker, David J.'
'Wilson, Claire'
_publ_section_title
;
 Hydrogen-bonded supramolecular architectures in
 (N-(methylpyridin-2-yl)-amidino-O-alkylurea)copper(ii) halides
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              159
_journal_paper_doi               10.1039/b405875e
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         '(C10H15N5O) Cu(II) Cl2'
_chemical_formula_sum            'C10 H15 Cl2 Cu N5 O'
_chemical_formula_weight         355.71
_chemical_melting_point          ?
_chemical_name_systematic
;
?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 103.305(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0090(6)
_cell_length_b                   8.5819(4)
_cell_length_c                   13.9542(9)
_cell_measurement_reflns_used    14135
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1399.52(13)
_computing_cell_refinement       'COLLECT; DENZO'
_computing_data_collection
'COLLECT (Hooft, 1999); DENZO (Otwinowski and Minor, 1997)'
_computing_data_reduction        'COLLECT; DENZO; SORTAV'
_computing_molecular_graphics    'CAMERON (Watkin, Pearce and Prout, 1993)'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '9.091 pixels/mm'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'phi and omega scans to fill Ewald sphere'
_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  0.0764
_diffrn_reflns_av_sigmaI/netI    0.0930
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10261
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  120
_diffrn_standards_number         'not measured'
_exptl_absorpt_coefficient_mu    1.941
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0494
_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)+(0.0459P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                2055
_reflns_number_total             3192
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b405875e.txt
_cod_data_source_block           cucytn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'unknown' was changed to '?' - the
value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               7204884
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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 0.13803(4) 0.25806(5) 0.68709(3) 0.01894(16) Uani 1 1 d . . .
Cl1 Cl 0.16356(8) 0.00075(10) 0.73170(7) 0.0228(2) Uani 1 1 d . . .
Cl2 Cl 0.23331(8) 0.26354(10) 0.52846(7) 0.0225(2) Uani 1 1 d . . .
N2 N 0.1061(2) 0.4828(3) 0.6836(2) 0.0177(7) Uani 1 1 d . . .
C1 C 0.2010(3) 0.5815(4) 0.7327(3) 0.0210(9) Uani 1 1 d . . .
H1A H 0.1768 0.6470 0.7808 0.025 Uiso 1 1 calc R . .
H1B H 0.2240 0.6486 0.6847 0.025 Uiso 1 1 calc R . .
C3 C 0.0166(3) 0.5544(4) 0.6328(3) 0.0179(8) Uani 1 1 d . . .
N31 N 0.0041(3) 0.7092(3) 0.6248(2) 0.0224(8) Uani 1 1 d . . .
H31A H 0.0581 0.7696 0.6547 0.027 Uiso 1 1 calc R . .
H31B H -0.0580 0.7483 0.5896 0.027 Uiso 1 1 calc R . .
N4 N -0.0775(2) 0.4743(3) 0.5798(2) 0.0192(7) Uani 1 1 d . . .
H4 H -0.1316 0.5301 0.5452 0.023 Uiso 1 1 calc R . .
C5 C -0.0946(3) 0.3168(4) 0.5760(3) 0.0189(8) Uani 1 1 d . . .
O51 O -0.1999(2) 0.2877(3) 0.52255(19) 0.0218(6) Uani 1 1 d . . .
C52 C -0.2326(3) 0.1266(4) 0.5005(3) 0.0231(9) Uani 1 1 d . . .
H52A H -0.2329 0.0700 0.5607 0.028 Uiso 1 1 calc R . .
H52B H -0.1794 0.0762 0.4677 0.028 Uiso 1 1 calc R . .
C53 C -0.3511(3) 0.1295(4) 0.4342(3) 0.0266(10) Uani 1 1 d . . .
H53A H -0.4037 0.1739 0.4691 0.040 Uiso 1 1 calc R . .
H53B H -0.3745 0.0252 0.4144 0.040 Uiso 1 1 calc R . .
H53C H -0.3505 0.1914 0.3770 0.040 Uiso 1 1 calc R . .
N6 N -0.0202(3) 0.2185(3) 0.6183(2) 0.0208(7) Uani 1 1 d . . .
H6 H -0.0422 0.1229 0.6162 0.025 Uiso 1 1 calc R . .
N11 N 0.2879(3) 0.3292(4) 0.7711(2) 0.0196(7) Uani 1 1 d . . .
C12 C 0.2993(3) 0.4839(4) 0.7825(3) 0.0195(8) Uani 1 1 d . . .
C13 C 0.3992(3) 0.5505(4) 0.8376(3) 0.0229(9) Uani 1 1 d . . .
H13 H 0.4048 0.6580 0.8462 0.027 Uiso 1 1 calc R . .
C14 C 0.4901(3) 0.4555(5) 0.8792(3) 0.0268(9) Uani 1 1 d . . .
H14 H 0.5581 0.4978 0.9155 0.032 Uiso 1 1 calc R . .
C15 C 0.4781(3) 0.2970(5) 0.8661(3) 0.0257(9) Uani 1 1 d . . .
H15 H 0.5386 0.2309 0.8931 0.031 Uiso 1 1 calc R . .
C16 C 0.3770(3) 0.2367(4) 0.8131(3) 0.0223(9) Uani 1 1 d . . .
H16 H 0.3693 0.1293 0.8059 0.027 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'
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
N6 Cu1 N2 89.80(12) . . ?
N6 Cu1 N11 169.34(13) . . ?
N2 Cu1 N11 81.91(12) . . ?
N6 Cu1 Cl1 91.15(9) . . ?
N2 Cu1 Cl1 164.60(9) . . ?
N11 Cu1 Cl1 95.08(9) . . ?
N6 Cu1 Cl2 98.44(10) . . ?
N2 Cu1 Cl2 94.54(9) . . ?
N11 Cu1 Cl2 88.93(9) . . ?
Cl1 Cu1 Cl2 100.52(3) . . ?
C3 N2 C1 116.2(3) . . ?
C3 N2 Cu1 127.6(2) . . ?
C1 N2 Cu1 115.6(2) . . ?
N2 C1 C12 110.1(3) . . ?
N2 C3 N31 125.3(3) . . ?
N2 C3 N4 121.9(3) . . ?
N31 C3 N4 112.7(3) . . ?
C5 N4 C3 127.5(3) . . ?
N6 C5 O51 127.5(3) . . ?
N6 C5 N4 123.8(3) . . ?
O51 C5 N4 108.7(3) . . ?
C5 O51 C52 118.2(3) . . ?
O51 C52 C53 106.6(3) . . ?
C5 N6 Cu1 127.8(3) . . ?
C12 N11 C16 118.8(3) . . ?
C12 N11 Cu1 115.1(2) . . ?
C16 N11 Cu1 126.1(3) . . ?
N11 C12 C13 121.7(3) . . ?
N11 C12 C1 117.1(3) . . ?
C13 C12 C1 121.3(3) . . ?
C14 C13 C12 119.2(4) . . ?
C15 C14 C13 118.7(4) . . ?
C16 C15 C14 119.8(4) . . ?
N11 C16 C15 121.8(4) . . ?
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 N6 1.951(3) . ?
Cu1 N2 1.965(3) . ?
Cu1 N11 2.004(3) . ?
Cu1 Cl1 2.2956(10) . ?
Cu1 Cl2 2.7161(11) . ?
N2 C3 1.298(4) . ?
N2 C1 1.458(4) . ?
C1 C12 1.484(5) . ?
C3 N31 1.339(5) . ?
C3 N4 1.383(4) . ?
N4 C5 1.366(5) . ?
C5 N6 1.271(5) . ?
C5 O51 1.336(4) . ?
O51 C52 1.450(4) . ?
C52 C53 1.508(5) . ?
N11 C12 1.340(5) . ?
N11 C16 1.352(5) . ?
C12 C13 1.390(5) . ?
C13 C14 1.379(5) . ?
C14 C15 1.376(6) . ?
C15 C16 1.370(5) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6 Cu1 N2 C3 -12.1(3) . . . . ?
N11 Cu1 N2 C3 174.6(3) . . . . ?
Cl1 Cu1 N2 C3 -105.7(4) . . . . ?
Cl2 Cu1 N2 C3 86.4(3) . . . . ?
N6 Cu1 N2 C1 177.4(3) . . . . ?
N11 Cu1 N2 C1 4.1(2) . . . . ?
Cl1 Cu1 N2 C1 83.8(4) . . . . ?
Cl2 Cu1 N2 C1 -84.2(2) . . . . ?
C3 N2 C1 C12 -176.6(3) . . . . ?
Cu1 N2 C1 C12 -4.9(4) . . . . ?
C1 N2 C3 N31 -2.0(5) . . . . ?
Cu1 N2 C3 N31 -172.5(3) . . . . ?
C1 N2 C3 N4 177.6(3) . . . . ?
Cu1 N2 C3 N4 7.1(5) . . . . ?
N2 C3 N4 C5 3.7(6) . . . . ?
N31 C3 N4 C5 -176.7(3) . . . . ?
C3 N4 C5 N6 -4.3(6) . . . . ?
C3 N4 C5 O51 175.3(3) . . . . ?
N6 C5 O51 C52 -6.5(6) . . . . ?
N4 C5 O51 C52 174.0(3) . . . . ?
C5 O51 C52 C53 -176.1(3) . . . . ?
O51 C5 N6 Cu1 174.4(3) . . . . ?
N4 C5 N6 Cu1 -6.2(6) . . . . ?
N2 Cu1 N6 C5 11.6(4) . . . . ?
N11 Cu1 N6 C5 50.4(9) . . . . ?
Cl1 Cu1 N6 C5 176.3(3) . . . . ?
Cl2 Cu1 N6 C5 -82.9(3) . . . . ?
N6 Cu1 N11 C12 -41.6(8) . . . . ?
N2 Cu1 N11 C12 -2.4(3) . . . . ?
Cl1 Cu1 N11 C12 -167.2(2) . . . . ?
Cl2 Cu1 N11 C12 92.3(3) . . . . ?
N6 Cu1 N11 C16 140.6(6) . . . . ?
N2 Cu1 N11 C16 179.8(3) . . . . ?
Cl1 Cu1 N11 C16 15.1(3) . . . . ?
Cl2 Cu1 N11 C16 -85.4(3) . . . . ?
C16 N11 C12 C13 -1.1(5) . . . . ?
Cu1 N11 C12 C13 -179.0(3) . . . . ?
C16 N11 C12 C1 178.2(3) . . . . ?
Cu1 N11 C12 C1 0.2(4) . . . . ?
N2 C1 C12 N11 3.0(5) . . . . ?
N2 C1 C12 C13 -177.8(3) . . . . ?
N11 C12 C13 C14 1.8(6) . . . . ?
C1 C12 C13 C14 -177.4(4) . . . . ?
C12 C13 C14 C15 -0.9(6) . . . . ?
C13 C14 C15 C16 -0.6(6) . . . . ?
C12 N11 C16 C15 -0.5(6) . . . . ?
Cu1 N11 C16 C15 177.2(3) . . . . ?
C14 C15 C16 N11 1.3(6) . . . . ?
