#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:10:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180379 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/48/7204883.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_7204883
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 Br2 Cu N5 O2'
_chemical_formula_weight         462.65
_chemical_name_systematic
;
?
;
_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
'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                 93.128(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6911(5)
_cell_length_b                   13.1827(7)
_cell_length_c                   13.2750(7)
_cell_measurement_reflns_used    6372
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.2
_cell_volume                     1518.68(14)
_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 0.981
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  '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  0.051
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10718
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.53
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    6.708
_exptl_absorpt_correction_T_max  0.462
_exptl_absorpt_correction_T_min  0.189
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    2.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.971
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_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     198
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0251
_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)+(0.0474P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0669
_reflns_number_gt                3019
_reflns_number_total             3698
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b405875e.txt
_cod_data_source_block           CUPYBR
_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        1518.7(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7204883
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_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 0.64824(3) 0.04190(2) 0.62081(2) 0.01968(8) Uani 1 1 d . . .
C100 C 0.3221(2) 0.05468(17) 0.65375(19) 0.0225(5) Uani 1 1 d . . .
H10A H 0.2943 0.0555 0.7251 0.027 Uiso 1 1 calc R . .
H10B H 0.2295 0.0351 0.6115 0.027 Uiso 1 1 calc R . .
N101 N 0.4456(2) -0.01954(14) 0.64082(15) 0.0189(4) Uani 1 1 d . . .
C102 C 0.4129(2) -0.11356(17) 0.65945(18) 0.0189(5) Uani 1 1 d . . .
N103 N 0.5223(2) -0.18989(15) 0.65172(15) 0.0201(4) Uani 1 1 d D . .
H103 H 0.493(3) -0.2534(9) 0.6580(19) 0.024 Uiso 1 1 d D . .
C104 C 0.6753(2) -0.17822(17) 0.63757(17) 0.0193(5) Uani 1 1 d . . .
N105 N 0.7399(2) -0.09293(14) 0.62339(17) 0.0226(4) Uani 1 1 d D . .
H105 H 0.8371(13) -0.097(2) 0.614(2) 0.027 Uiso 1 1 d D . .
N121 N 0.2769(2) -0.14749(16) 0.68804(17) 0.0231(4) Uani 1 1 d D . .
H12A H 0.194(2) -0.1088(17) 0.691(2) 0.028 Uiso 1 1 d D . .
H12B H 0.261(3) -0.2120(9) 0.695(2) 0.028 Uiso 1 1 d D . .
O141 O 0.74301(17) -0.26931(12) 0.64130(13) 0.0228(4) Uani 1 1 d . . .
C142 C 0.9090(3) -0.27218(19) 0.6367(2) 0.0294(6) Uani 1 1 d . . .
H14A H 0.9383 -0.2431 0.5726 0.044 Uiso 1 1 calc R . .
H14B H 0.9446 -0.3426 0.6417 0.044 Uiso 1 1 calc R . .
H14C H 0.9565 -0.2327 0.6927 0.044 Uiso 1 1 calc R . .
N201 N 0.5237(2) 0.16875(14) 0.60365(15) 0.0199(4) Uani 1 1 d . . .
C211 C 0.3746(2) 0.15808(17) 0.62390(17) 0.0193(5) Uani 1 1 d . . .
C212 C 0.2739(3) 0.24024(18) 0.62019(19) 0.0230(5) Uani 1 1 d . . .
H212 H 0.1687 0.2310 0.6339 0.028 Uiso 1 1 calc R . .
C213 C 0.3276(3) 0.33469(18) 0.59657(19) 0.0259(5) Uani 1 1 d . . .
H213 H 0.2606 0.3917 0.5949 0.031 Uiso 1 1 calc R . .
C214 C 0.4819(3) 0.34572(18) 0.5750(2) 0.0263(5) Uani 1 1 d . . .
H214 H 0.5218 0.4102 0.5580 0.032 Uiso 1 1 calc R . .
C215 C 0.5753(3) 0.26143(18) 0.57890(18) 0.0233(5) Uani 1 1 d . . .
H215 H 0.6802 0.2688 0.5635 0.028 Uiso 1 1 calc R . .
Br1 Br 0.89089(3) 0.113318(18) 0.57192(2) 0.02718(8) Uani 1 1 d . . .
Br2 Br 0.70381(3) 0.097959(17) 0.836861(19) 0.02404(8) Uani 1 1 d . . .
O1S O 1.0210(2) -0.04952(16) 0.78007(16) 0.0368(5) Uani 1 1 d D . .
H1S H 0.955(3) -0.006(2) 0.777(3) 0.055 Uiso 1 1 d D . .
C1S C 1.0715(3) -0.0649(2) 0.8814(2) 0.0370(6) Uani 1 1 d . . .
H1SA H 1.1680 -0.0279 0.8958 0.055 Uiso 1 1 calc R . .
H1SB H 1.0887 -0.1375 0.8935 0.055 Uiso 1 1 calc R . .
H1SC H 0.9931 -0.0401 0.9256 0.055 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 89.43(8) . . y
N105 Cu N201 169.85(8) . . y
N101 Cu N201 82.92(8) . . y
N105 Cu Br1 89.90(6) . . y
N101 Cu Br1 172.23(6) . . y
N201 Cu Br1 96.78(5) . . y
N101 C100 C211 109.90(18) . . ?
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 116.37(18) . . ?
C102 N101 Cu 128.70(15) . . ?
C100 N101 Cu 113.96(14) . . ?
N101 C102 N121 125.4(2) . . ?
N101 C102 N103 121.2(2) . . ?
N121 C102 N103 113.4(2) . . ?
C104 N103 C102 127.21(19) . . ?
C104 N103 H103 114.2(17) . . ?
C102 N103 H103 118.5(17) . . ?
N105 C104 O141 126.9(2) . . ?
N105 C104 N103 124.1(2) . . ?
O141 C104 N103 108.94(19) . . ?
C104 N105 Cu 128.65(16) . . ?
C104 N105 H105 113.7(18) . . ?
Cu N105 H105 117.6(18) . . ?
C102 N121 H12A 123.4(18) . . ?
C102 N121 H12B 120.5(18) . . ?
H12A N121 H12B 115(2) . . ?
C104 O141 C142 117.36(18) . . ?
O141 C142 H14A 109.5 . . ?
O141 C142 H14B 109.5 . . ?
H14A C142 H14B 109.5 . . ?
O141 C142 H14C 109.5 . . ?
H14A C142 H14C 109.5 . . ?
H14B C142 H14C 109.5 . . ?
C211 N201 C215 118.7(2) . . ?
C211 N201 Cu 114.30(15) . . ?
C215 N201 Cu 126.91(16) . . ?
N201 C211 C212 121.5(2) . . ?
N201 C211 C100 117.29(19) . . ?
C212 C211 C100 121.2(2) . . ?
C213 C212 C211 119.6(2) . . ?
C213 C212 H212 120.2 . . ?
C211 C212 H212 120.2 . . ?
C212 C213 C214 119.0(2) . . ?
C212 C213 H213 120.5 . . ?
C214 C213 H213 120.5 . . ?
C215 C214 C213 118.7(2) . . ?
C215 C214 H214 120.6 . . ?
C213 C214 H214 120.6 . . ?
N201 C215 C214 122.5(2) . . ?
N201 C215 H215 118.7 . . ?
C214 C215 H215 118.7 . . ?
C1S O1S H1S 110(2) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
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 1.9473(19) . y
Cu N101 1.9694(18) . y
Cu N201 1.9983(19) . y
Cu Br1 2.4299(4) . y
C100 N101 1.469(3) . ?
C100 C211 1.497(3) . ?
C100 H10A 0.9900 . ?
C100 H10B 0.9900 . ?
N101 C102 1.299(3) . ?
C102 N121 1.338(3) . ?
C102 N103 1.392(3) . ?
N103 C104 1.362(3) . ?
N103 H103 0.880(10) . ?
C104 N105 1.275(3) . ?
C104 O141 1.337(3) . ?
N105 H105 0.863(10) . ?
N121 H12A 0.882(10) . ?
N121 H12B 0.867(10) . ?
O141 C142 1.448(3) . ?
C142 H14A 0.9800 . ?
C142 H14B 0.9800 . ?
C142 H14C 0.9800 . ?
N201 C211 1.345(3) . ?
N201 C215 1.348(3) . ?
C211 C212 1.391(3) . ?
C212 C213 1.372(3) . ?
C212 H212 0.9500 . ?
C213 C214 1.394(3) . ?
C213 H213 0.9500 . ?
C214 C215 1.375(3) . ?
C214 H214 0.9500 . ?
C215 H215 0.9500 . ?
O1S C1S 1.407(4) . ?
O1S H1S 0.811(10) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
