#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:10:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180379 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/48/7204885.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_7204885
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_sum            'C10 H17 Cl2 Cu N5 O2'
_chemical_formula_weight         373.73
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens
;
C-H placed geometrically, N-H and O-H located by deltaF
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.282(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.810(2)
_cell_length_b                   8.2394(12)
_cell_length_c                   16.073(2)
_cell_measurement_reflns_used    2489
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.6
_cell_volume                     1515.7(4)
_computing_cell_refinement       'Bruker SAINT version 6.02a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.054 (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_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  0.034
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6978
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.801
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment
;
C-H riding on parent atom, N-H and O-H refined with restraints
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3326
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0371
_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)+(0.0507P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                2400
_reflns_number_total             3548
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b405875e.txt
_cod_data_source_block           CUPYIM
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1515.6(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7204885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
Cu Cu 0.30265(3) 0.40543(4) 0.40883(2) 0.01886(12) Uani 1 1 d . . .
C100 C 0.4396(2) 0.3209(4) 0.58171(18) 0.0215(6) Uani 1 1 d . . .
H10A H 0.4166 0.2349 0.6154 0.026 Uiso 1 1 calc R . .
H10B H 0.4923 0.3932 0.6206 0.026 Uiso 1 1 calc R . .
N101 N 0.33595(19) 0.4109(3) 0.53563(15) 0.0184(5) Uani 1 1 d . . .
C102 C 0.2746(2) 0.4792(4) 0.58341(18) 0.0194(6) Uani 1 1 d . . .
N103 N 0.1770(2) 0.5745(3) 0.54732(16) 0.0224(6) Uani 1 1 d D . .
H103 H 0.144(3) 0.628(3) 0.5816(16) 0.027 Uiso 1 1 d D . .
C104 C 0.1358(2) 0.6173(4) 0.46328(19) 0.0219(6) Uani 1 1 d . . .
N105 N 0.1763(2) 0.5638(3) 0.40162(16) 0.0234(6) Uani 1 1 d D . .
H105 H 0.140(2) 0.602(4) 0.3519(11) 0.028 Uiso 1 1 d D . .
N121 N 0.2985(2) 0.4702(3) 0.66942(16) 0.0268(6) Uani 1 1 d D . .
H12A H 0.340(3) 0.390(3) 0.6977(19) 0.032 Uiso 1 1 d D . .
H12B H 0.251(2) 0.514(4) 0.6964(19) 0.032 Uiso 1 1 d D . .
O141 O 0.04833(18) 0.7248(3) 0.45837(13) 0.0281(5) Uani 1 1 d . . .
C142 C -0.0162(3) 0.7847(4) 0.37468(19) 0.0264(7) Uani 1 1 d . . .
H14A H -0.0507 0.6954 0.3377 0.032 Uiso 1 1 calc R . .
H14B H 0.0349 0.8449 0.3470 0.032 Uiso 1 1 calc R . .
C143 C -0.1102(3) 0.8941(4) 0.3927(2) 0.0321(8) Uani 1 1 d . . .
H14C H -0.1524 0.8373 0.4277 0.048 Uiso 1 1 calc R . .
H14D H -0.1631 0.9249 0.3396 0.048 Uiso 1 1 calc R . .
H14E H -0.0749 0.9895 0.4224 0.048 Uiso 1 1 calc R . .
N201 N 0.4512(2) 0.2725(3) 0.43449(15) 0.0195(5) Uani 1 1 d . . .
C211 C 0.5012(2) 0.2489(3) 0.51822(18) 0.0183(6) Uani 1 1 d . . .
C212 C 0.6051(3) 0.1611(4) 0.5470(2) 0.0242(7) Uani 1 1 d . . .
H212 H 0.6382 0.1473 0.6054 0.029 Uiso 1 1 calc R . .
C213 C 0.6575(3) 0.0950(4) 0.4861(2) 0.0263(7) Uani 1 1 d . . .
H213 H 0.7266 0.0361 0.5033 0.032 Uiso 1 1 calc R . .
C214 C 0.6059(3) 0.1177(4) 0.3997(2) 0.0260(7) Uani 1 1 d . . .
H214 H 0.6396 0.0738 0.3582 0.031 Uiso 1 1 calc R . .
C215 C 0.5033(3) 0.2067(4) 0.3757(2) 0.0253(7) Uani 1 1 d . . .
H215 H 0.4690 0.2219 0.3176 0.030 Uiso 1 1 calc R . .
Cl1 Cl 0.29553(7) 0.44112(10) 0.26517(5) 0.02731(19) Uani 1 1 d . . .
Cl2 Cl 0.07892(6) 0.66595(10) 0.70847(5) 0.02628(18) Uani 1 1 d . . .
O1W O 0.17291(18) 0.1838(3) 0.38416(14) 0.0261(5) Uani 1 1 d D . .
H1WA H 0.179(3) 0.128(4) 0.3437(16) 0.039 Uiso 1 1 d D . .
H1WB H 0.1091(17) 0.229(4) 0.366(2) 0.039 Uiso 1 1 d D . .
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
N105 Cu N101 90.04(10) . . y
N105 Cu N201 168.52(10) . . y
N101 Cu N201 81.97(9) . . y
N105 Cu Cl1 90.96(8) . . y
N101 Cu Cl1 167.49(7) . . y
N201 Cu Cl1 95.09(7) . . y
N105 Cu O1W 92.99(9) . . y
N101 Cu O1W 98.45(9) . . y
N201 Cu O1W 96.31(9) . . y
Cl1 Cu O1W 93.95(6) . . y
N101 C100 C211 109.8(2) . . ?
N101 C100 H10A 109.7 . . ?
C211 C100 H10A 109.7 . . ?
N101 C100 H10B 109.7 . . ?
C211 C100 H10B 109.7 . . ?
H10A C100 H10B 108.2 . . ?
C102 N101 C100 115.9(2) . . ?
C102 N101 Cu 128.12(19) . . ?
C100 N101 Cu 115.96(17) . . ?
N101 C102 N121 125.1(3) . . ?
N101 C102 N103 121.2(3) . . ?
N121 C102 N103 113.6(3) . . ?
C104 N103 C102 127.8(3) . . ?
C104 N103 H103 113(2) . . ?
C102 N103 H103 118(2) . . ?
N105 C104 O141 127.4(3) . . ?
N105 C104 N103 124.6(3) . . ?
O141 C104 N103 108.0(2) . . ?
C104 N105 Cu 127.3(2) . . ?
C104 N105 H105 113(2) . . ?
Cu N105 H105 119(2) . . ?
C102 N121 H12A 122(2) . . ?
C102 N121 H12B 120(2) . . ?
H12A N121 H12B 113(3) . . ?
C104 O141 C142 119.7(2) . . ?
O141 C142 C143 105.4(2) . . ?
O141 C142 H14A 110.7 . . ?
C143 C142 H14A 110.7 . . ?
O141 C142 H14B 110.7 . . ?
C143 C142 H14B 110.7 . . ?
H14A C142 H14B 108.8 . . ?
C142 C143 H14C 109.5 . . ?
C142 C143 H14D 109.5 . . ?
H14C C143 H14D 109.5 . . ?
C142 C143 H14E 109.5 . . ?
H14C C143 H14E 109.5 . . ?
H14D C143 H14E 109.5 . . ?
C211 N201 C215 118.4(3) . . ?
C211 N201 Cu 115.31(19) . . ?
C215 N201 Cu 126.3(2) . . ?
N201 C211 C212 122.6(3) . . ?
N201 C211 C100 117.0(2) . . ?
C212 C211 C100 120.5(3) . . ?
C213 C212 C211 118.4(3) . . ?
C213 C212 H212 120.8 . . ?
C211 C212 H212 120.8 . . ?
C214 C213 C212 119.3(3) . . ?
C214 C213 H213 120.3 . . ?
C212 C213 H213 120.3 . . ?
C213 C214 C215 119.3(3) . . ?
C213 C214 H214 120.4 . . ?
C215 C214 H214 120.4 . . ?
N201 C215 C214 122.1(3) . . ?
N201 C215 H215 118.9 . . ?
C214 C215 H215 118.9 . . ?
Cu O1W H1WA 113(3) . . ?
Cu O1W H1WB 102(3) . . ?
H1WA O1W H1WB 103(3) . . ?
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
Cu N105 1.964(2) . y
Cu N101 1.979(2) . y
Cu N201 2.022(2) . y
Cu Cl1 2.3086(8) . y
Cu O1W 2.354(2) . y
C100 N101 1.466(3) . ?
C100 C211 1.512(4) . ?
C100 H10A 0.9700 . ?
C100 H10B 0.9700 . ?
N101 C102 1.306(4) . ?
C102 N121 1.343(4) . ?
C102 N103 1.396(4) . ?
N103 C104 1.364(4) . ?
N103 H103 0.868(10) . ?
C104 N105 1.280(4) . ?
C104 O141 1.348(3) . ?
N105 H105 0.868(10) . ?
N121 H12A 0.875(10) . ?
N121 H12B 0.868(10) . ?
O141 C142 1.459(3) . ?
C142 C143 1.513(4) . ?
C142 H14A 0.9700 . ?
C142 H14B 0.9700 . ?
C143 H14C 0.9600 . ?
C143 H14D 0.9600 . ?
C143 H14E 0.9600 . ?
N201 C211 1.344(4) . ?
N201 C215 1.361(4) . ?
C211 C212 1.402(4) . ?
C212 C213 1.392(4) . ?
C212 H212 0.9300 . ?
C213 C214 1.385(4) . ?
C213 H213 0.9300 . ?
C214 C215 1.387(4) . ?
C214 H214 0.9300 . ?
C215 H215 0.9300 . ?
O1W H1WA 0.813(10) . ?
O1W H1WB 0.824(10) . ?
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
C211 C100 N101 C102 179.9(2) . . . . ?
C211 C100 N101 Cu 2.6(3) . . . . ?
N105 Cu N101 C102 9.7(3) . . . . ?
N201 Cu N101 C102 -178.6(3) . . . . ?
Cl1 Cu N101 C102 104.3(4) . . . . ?
O1W Cu N101 C102 -83.3(3) . . . . ?
N105 Cu N101 C100 -173.4(2) . . . . ?
N201 Cu N101 C100 -1.63(19) . . . . ?
Cl1 Cu N101 C100 -78.8(4) . . . . ?
O1W Cu N101 C100 93.61(19) . . . . ?
C100 N101 C102 N121 -1.1(4) . . . . ?
Cu N101 C102 N121 175.8(2) . . . . ?
C100 N101 C102 N103 177.0(3) . . . . ?
Cu N101 C102 N103 -6.1(4) . . . . ?
N101 C102 N103 C104 -3.8(5) . . . . ?
N121 C102 N103 C104 174.6(3) . . . . ?
C102 N103 C104 N105 6.2(5) . . . . ?
C102 N103 C104 O141 -173.0(3) . . . . ?
O141 C104 N105 Cu -179.3(2) . . . . ?
N103 C104 N105 Cu 1.7(5) . . . . ?
N101 Cu N105 C104 -7.5(3) . . . . ?
N201 Cu N105 C104 -53.1(7) . . . . ?
Cl1 Cu N105 C104 -175.0(3) . . . . ?
O1W Cu N105 C104 91.0(3) . . . . ?
N105 C104 O141 C142 4.1(5) . . . . ?
N103 C104 O141 C142 -176.7(2) . . . . ?
C104 O141 C142 C143 177.1(3) . . . . ?
N105 Cu N201 C211 46.4(6) . . . . ?
N101 Cu N201 C211 0.2(2) . . . . ?
Cl1 Cu N201 C211 167.98(19) . . . . ?
O1W Cu N201 C211 -97.5(2) . . . . ?
N105 Cu N201 C215 -133.5(5) . . . . ?
N101 Cu N201 C215 -179.8(3) . . . . ?
Cl1 Cu N201 C215 -12.0(2) . . . . ?
O1W Cu N201 C215 82.5(2) . . . . ?
C215 N201 C211 C212 0.7(4) . . . . ?
Cu N201 C211 C212 -179.3(2) . . . . ?
C215 N201 C211 C100 -178.8(3) . . . . ?
Cu N201 C211 C100 1.2(3) . . . . ?
N101 C100 C211 N201 -2.4(4) . . . . ?
N101 C100 C211 C212 178.1(2) . . . . ?
N201 C211 C212 C213 -0.5(4) . . . . ?
C100 C211 C212 C213 179.0(3) . . . . ?
C211 C212 C213 C214 -0.1(4) . . . . ?
C212 C213 C214 C215 0.4(5) . . . . ?
C211 N201 C215 C214 -0.4(4) . . . . ?
Cu N201 C215 C214 179.6(2) . . . . ?
C213 C214 C215 N201 -0.2(5) . . . . ?
