# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_F3
_database_code_depnum_ccdc_archive 'CCDC 1482585'
_audit_update_record             
;
2016-05-30 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'3-amino-N-(pyridin-2-ylmethyl)-propanamide dihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H16 Cl Cu N3 O3'
_chemical_formula_weight         313.24

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   7.3116(2)
_cell_length_b                   22.4070(9)
_cell_length_c                   7.3570(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.080(2)
_cell_angle_gamma                90.00
_cell_volume                     1205.30(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5280
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      27.86

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7650
_exptl_absorpt_correction_T_max  0.8945
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5280
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         27.86
_reflns_number_total             2860
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT program (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2001)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0282P)²+0.9037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0053(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2860
_refine_ls_number_parameters     179
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0668
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


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 0.04163(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 . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 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_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
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_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
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) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.103
