#------------------------------------------------------------------------------
#$Date: 2016-11-08 22:09:00 +0200 (Tue, 08 Nov 2016) $
#$Revision: 188248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/06/7040678.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_7040678
loop_
_publ_author_name
'Jackson, Graham E.'
'Elmagbari, Fatin M.'
'Hammouda, Ahmed N.'
'Bonomo, Raffaele P.'
_publ_section_title
;
 Solution equilibria and the X-ray structure of Cu(ii) complexation with
 3-amino-N-(pyridin-2-ylmethyl)propanamide, a pseudo-mimic of human serum
 albumin.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17010
_journal_page_last               17019
_journal_paper_doi               10.1039/c6dt02974d
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C9 H16 Cl Cu N3 O3'
_chemical_formula_weight         313.24
_chemical_name_systematic
'3-amino-N-(pyridin-2-ylmethyl)-propanamide dihydrate'
_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
_audit_update_record
;
2016-05-30 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.080(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3116(2)
_cell_length_b                   22.4070(9)
_cell_length_c                   7.3570(2)
_cell_measurement_reflns_used    5280
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      3.33
_cell_volume                     1205.30(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT program (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° φ scans 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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5280
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         3.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.034
_exptl_absorpt_correction_T_max  0.8945
_exptl_absorpt_correction_T_min  0.7650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.0053(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0267
_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)+(0.0282P)²+0.9037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0668
_reflns_number_gt                2422
_reflns_number_total             2860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt02974d3.cif
_cod_data_source_block           F3
_cod_depositor_comments          'Adding full bibliography for 7040678.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7040678
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
Cu1 Cu 0.04163(3) 0.287098(10) 0.39076(3) 0.01483(9) Uani 1 1 d .
Cl1 Cl 0.23637(6) 0.26031(2) 0.68759(6) 0.01638(12) Uani 1 1 d .
O1 O -0.39621(19) 0.40472(6) 0.46350(19) 0.0203(3) Uani 1 1 d .
O2 O 0.2480(2) 0.45651(8) 0.0386(2) 0.0333(4) Uani 1 1 d D
H2C H 0.302(3) 0.4659(13) -0.0780(18) 0.046(8) Uiso 1 1 d D
H2D H 0.337(3) 0.4763(12) 0.115(3) 0.054(9) Uiso 1 1 d D
O3 O -0.4855(2) 0.50854(7) 0.2722(2) 0.0264(3) Uani 1 1 d D
H3A H -0.446(4) 0.4750(8) 0.345(3) 0.052(9) Uiso 1 1 d D
H3B H -0.531(4) 0.5374(11) 0.359(3) 0.060(9) Uiso 1 1 d D
N1 N 0.1811(2) 0.36305(8) 0.3706(2) 0.0177(3) Uani 1 1 d D
H1C H 0.175(3) 0.3770(9) 0.2590(12) 0.019(6) Uiso 1 1 d D
H1D H 0.2975(10) 0.3573(11) 0.395(3) 0.031(7) Uiso 1 1 d D
N2 N -0.1928(2) 0.32711(7) 0.4450(2) 0.0154(3) Uani 1 1 d .
N3 N -0.1052(2) 0.21411(7) 0.4305(2) 0.0142(3) Uani 1 1 d .
C1 C 0.1130(3) 0.40787(9) 0.5014(3) 0.0206(4) Uani 1 1 d .
H1A H 0.1971 0.4425 0.5025 0.025 Uiso 1 1 calc R
H1B H 0.1127 0.3903 0.6249 0.025 Uiso 1 1 calc R
C2 C -0.0786(3) 0.42911(9) 0.4549(3) 0.0222(4) Uani 1 1 d .
H2A H -0.1109 0.4612 0.5417 0.027 Uiso 1 1 calc R
H2B H -0.0740 0.4475 0.3326 0.027 Uiso 1 1 calc R
C3 C -0.2335(3) 0.38426(9) 0.4550(3) 0.0160(4) Uani 1 1 d .
C4 C -0.3495(3) 0.28651(8) 0.4511(3) 0.0157(4) Uani 1 1 d .
H4A H -0.4286 0.2934 0.3437 0.019 Uiso 1 1 calc R
H4B H -0.4227 0.2946 0.5615 0.019 Uiso 1 1 calc R
C5 C -0.2856(3) 0.22284(8) 0.4527(2) 0.0143(4) Uani 1 1 d .
C6 C -0.4044(3) 0.17498(9) 0.4763(3) 0.0181(4) Uani 1 1 d .
H6 H -0.5321 0.1815 0.4886 0.022 Uiso 1 1 calc R
C7 C -0.3340(3) 0.11770(9) 0.4815(3) 0.0207(4) Uani 1 1 d .
H7 H -0.4130 0.0845 0.4980 0.025 Uiso 1 1 calc R
C8 C -0.1467(3) 0.10906(9) 0.4624(3) 0.0193(4) Uani 1 1 d .
H8 H -0.0957 0.0701 0.4666 0.023 Uiso 1 1 calc R
C9 C -0.0372(3) 0.15816(9) 0.4373(3) 0.0174(4) Uani 1 1 d .
H9 H 0.0909 0.1525 0.4243 0.021 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
N2 Cu1 N3 82.77(6) . .
N2 Cu1 N1 94.11(7) . .
N3 Cu1 N1 175.16(7) . .
N2 Cu1 Cl1 150.50(5) . 4_565
N3 Cu1 Cl1 92.88(5) . 4_565
N1 Cu1 Cl1 91.64(5) . 4_565
N2 Cu1 Cl1 113.45(5) . .
N3 Cu1 Cl1 88.98(5) . .
N1 Cu1 Cl1 88.88(5) . .
Cl1 Cu1 Cl1 95.549(15) 4_565 .
Cu1 Cl1 Cu1 107.579(19) 4_566 .
H2C O2 H2D 98(2) . .
H3A O3 H3B 105(2) . .
C1 N1 Cu1 111.09(12) . .
C1 N1 H1C 110.6(15) . .
Cu1 N1 H1C 110.5(15) . .
C1 N1 H1D 107.3(17) . .
Cu1 N1 H1D 110.8(17) . .
H1C N1 H1D 106(2) . .
C3 N2 C4 115.18(16) . .
C3 N2 Cu1 130.46(13) . .
C4 N2 Cu1 113.80(12) . .
C5 N3 C9 119.47(16) . .
C5 N3 Cu1 115.51(13) . .
C9 N3 Cu1 125.01(13) . .
N1 C1 C2 112.17(17) . .
N1 C1 H1A 109.2 . .
C2 C1 H1A 109.2 . .
N1 C1 H1B 109.2 . .
C2 C1 H1B 109.2 . .
H1A C1 H1B 107.9 . .
C3 C2 C1 118.81(17) . .
C3 C2 H2A 107.6 . .
C1 C2 H2A 107.6 . .
C3 C2 H2B 107.6 . .
C1 C2 H2B 107.6 . .
H2A C2 H2B 107.0 . .
O1 C3 N2 124.25(18) . .
O1 C3 C2 117.31(17) . .
N2 C3 C2 118.44(17) . .
N2 C4 C5 110.29(15) . .
N2 C4 H4A 109.6 . .
C5 C4 H4A 109.6 . .
N2 C4 H4B 109.6 . .
C5 C4 H4B 109.6 . .
H4A C4 H4B 108.1 . .
N3 C5 C6 121.08(17) . .
N3 C5 C4 116.31(16) . .
C6 C5 C4 122.61(17) . .
C7 C6 C5 119.11(18) . .
C7 C6 H6 120.4 . .
C5 C6 H6 120.4 . .
C6 C7 C8 119.52(19) . .
C6 C7 H7 120.2 . .
C8 C7 H7 120.2 . .
C9 C8 C7 118.45(19) . .
C9 C8 H8 120.8 . .
C7 C8 H8 120.8 . .
N3 C9 C8 122.33(18) . .
N3 C9 H9 118.8 . .
C8 C9 H9 118.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.9755(16) .
Cu1 N3 1.9781(16) .
Cu1 N1 1.9895(17) .
Cu1 Cl1 2.3229(5) 4_565
Cu1 Cl1 2.6735(5) .
Cl1 Cu1 2.3229(5) 4_566
O1 C3 1.276(2) .
O2 H2C 0.968(3) .
O2 H2D 0.968(3) .
O3 H3A 0.968(3) .
O3 H3B 0.968(3) .
N1 C1 1.478(3) .
N1 H1C 0.879(3) .
N1 H1D 0.879(3) .
N2 C3 1.317(2) .
N2 C4 1.464(2) .
N3 C5 1.343(2) .
N3 C9 1.349(2) .
C1 C2 1.519(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.514(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C4 C5 1.501(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.391(3) .
C6 C7 1.383(3) .
C6 H6 0.9500 .
C7 C8 1.390(3) .
C7 H7 0.9500 .
C8 C9 1.373(3) .
C8 H8 0.9500 .
C9 H9 0.9500 .
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_4
N2 Cu1 Cl1 Cu1 48.85(5) . 4_566
N3 Cu1 Cl1 Cu1 -32.82(5) . 4_566
N1 Cu1 Cl1 Cu1 142.84(5) . 4_566
Cl1 Cu1 Cl1 Cu1 -125.62(3) 4_565 4_566
N2 Cu1 N1 C1 35.38(14) . .
N3 Cu1 N1 C1 -14.3(9) . .
Cl1 Cu1 N1 C1 -173.57(13) 4_565 .
Cl1 Cu1 N1 C1 -78.05(13) . .
N3 Cu1 N2 C3 178.59(18) . .
N1 Cu1 N2 C3 2.30(18) . .
Cl1 Cu1 N2 C3 -98.37(18) 4_565 .
Cl1 Cu1 N2 C3 92.87(17) . .
N3 Cu1 N2 C4 -10.51(13) . .
N1 Cu1 N2 C4 173.20(13) . .
Cl1 Cu1 N2 C4 72.53(17) 4_565 .
Cl1 Cu1 N2 C4 -96.23(12) . .
N2 Cu1 N3 C5 7.08(14) . .
N1 Cu1 N3 C5 57.1(9) . .
Cl1 Cu1 N3 C5 -143.61(13) 4_565 .
Cl1 Cu1 N3 C5 120.88(13) . .
N2 Cu1 N3 C9 -172.60(17) . .
N1 Cu1 N3 C9 -122.6(8) . .
Cl1 Cu1 N3 C9 36.70(16) 4_565 .
Cl1 Cu1 N3 C9 -58.80(16) . .
Cu1 N1 C1 C2 -67.99(19) . .
N1 C1 C2 C3 62.1(2) . .
C4 N2 C3 O1 -2.2(3) . .
Cu1 N2 C3 O1 168.62(14) . .
C4 N2 C3 C2 178.32(17) . .
Cu1 N2 C3 C2 -10.9(3) . .
C1 C2 C3 O1 161.91(18) . .
C1 C2 C3 N2 -18.6(3) . .
C3 N2 C4 C5 -175.83(16) . .
Cu1 N2 C4 C5 11.81(19) . .
C9 N3 C5 C6 -2.2(3) . .
Cu1 N3 C5 C6 178.07(14) . .
C9 N3 C5 C4 177.54(17) . .
Cu1 N3 C5 C4 -2.2(2) . .
N2 C4 C5 N3 -6.3(2) . .
N2 C4 C5 C6 173.46(17) . .
N3 C5 C6 C7 1.7(3) . .
C4 C5 C6 C7 -178.08(18) . .
C5 C6 C7 C8 -0.3(3) . .
C6 C7 C8 C9 -0.5(3) . .
C5 N3 C9 C8 1.4(3) . .
Cu1 N3 C9 C8 -178.90(15) . .
C7 C8 C9 N3 -0.1(3) . .
