#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/78/1517823.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_1517823
loop_
_publ_author_name
'Jacob W. Uebler'
'Amy L. Pochodylo'
'Robert L. LaDuca'
_publ_section_title
;
 Copper glutarate coordination polymers with dipyridylamide ligands:
 Effect of donor disposition and steric bulk on structure
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              31
_journal_page_last               42
_journal_volume                  405
_journal_year                    2013
_chemical_formula_sum            'C16 H19 Cu N3 O7'
_chemical_formula_weight         428.88
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.630(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6901(14)
_cell_length_b                   15.562(3)
_cell_length_c                   13.569(2)
_cell_measurement_reflns_used    4224
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.51
_cell_volume                     1767.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ 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  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7782
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    1.282
_exptl_absorpt_correction_T_max  0.6815
_exptl_absorpt_correction_T_min  0.5057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0355
_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)+(0.0369P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                2480
_reflns_number_total             3211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-405-31-42-4.cif
_cod_data_source_block           p21n
_cod_original_cell_volume        1767.1(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1517823
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
Cu1 Cu 0.03536(4) 0.19207(2) 0.14015(3) 0.02432(13) Uani 1 1 d .
O1 O -0.18324(19) 0.23030(13) 0.14635(14) 0.0250(5) Uani 1 1 d .
O1W O -0.3179(2) 0.21660(14) 0.30839(15) 0.0296(5) Uani 1 1 d D
H1WA H -0.272(3) 0.2260(19) 0.2631(18) 0.036 Uiso 1 1 d D
H1WB H -0.412(2) 0.1955(18) 0.282(2) 0.036 Uiso 1 1 d D
O2 O -0.2014(2) 0.18248(13) -0.00967(14) 0.0307(5) Uani 1 1 d .
O3 O -0.8086(2) 0.14278(13) 0.07698(14) 0.0295(5) Uani 1 1 d .
O4 O -0.6040(2) 0.14585(14) 0.21688(16) 0.0369(5) Uani 1 1 d .
O5 O -0.1616(2) -0.07048(14) 0.46204(17) 0.0411(6) Uani 1 1 d .
O6 O 0.1896(2) 0.21543(16) 0.31554(16) 0.0363(6) Uani 1 1 d D
H6A H 0.266(3) 0.1983(19) 0.293(2) 0.044 Uiso 1 1 d D
H6B H 0.229(3) 0.2503(17) 0.3657(18) 0.044 Uiso 1 1 d D
N1 N -0.0083(2) 0.07641(15) 0.19572(16) 0.0230(5) Uani 1 1 d .
N2 N -0.2346(3) 0.06947(16) 0.43470(19) 0.0297(6) Uani 1 1 d D
H2N H -0.244(3) 0.1137(15) 0.3897(19) 0.036 Uiso 1 1 d D
N3 N -0.4105(2) 0.18647(15) 0.61148(17) 0.0250(5) Uani 1 1 d .
C1 C -0.0523(3) -0.0748(2) 0.1801(2) 0.0360(8) Uani 1 1 d .
H1 H -0.0465 -0.1266 0.1442 0.043 Uiso 1 1 calc R
C2 C -0.1088(3) -0.0753(2) 0.2641(2) 0.0348(7) Uani 1 1 d .
H2 H -0.1438 -0.1275 0.2872 0.042 Uiso 1 1 calc R
C3 C -0.4362(3) 0.1240(2) 0.6737(2) 0.0319(7) Uani 1 1 d .
H3 H -0.4864 0.1380 0.7257 0.038 Uiso 1 1 calc R
C4 C -0.0034(3) 0.0017(2) 0.1477(2) 0.0293(7) Uani 1 1 d .
H4 H 0.0354 0.0016 0.0886 0.035 Uiso 1 1 calc R
C5 C -0.3917(3) 0.0406(2) 0.6637(2) 0.0359(8) Uani 1 1 d .
H5 H -0.4085 -0.0021 0.7097 0.043 Uiso 1 1 calc R
C6 C -0.5422(3) 0.15418(19) -0.0214(2) 0.0263(7) Uani 1 1 d .
H6C H -0.4907 0.1242 -0.0685 0.032 Uiso 1 1 calc R
H6D H -0.6492 0.1733 -0.0619 0.032 Uiso 1 1 calc R
C7 C -0.3445(3) 0.16514(19) 0.5365(2) 0.0261(7) Uani 1 1 d .
H7 H -0.3277 0.2091 0.4920 0.031 Uiso 1 1 calc R
C8 C -0.2651(3) 0.21344(18) 0.0538(2) 0.0233(7) Uani 1 1 d .
C9 C -0.2994(3) 0.0823(2) 0.5208(2) 0.0270(7) Uani 1 1 d .
C10 C -0.1716(3) -0.0039(2) 0.4111(2) 0.0338(7) Uani 1 1 d .
C11 C -0.4426(3) 0.23307(18) 0.0225(2) 0.0247(7) Uani 1 1 d .
H11A H -0.4641 0.2794 -0.0294 0.030 Uiso 1 1 calc R
H11B H -0.4750 0.2540 0.0828 0.030 Uiso 1 1 calc R
C12 C -0.5620(3) 0.09079(19) 0.0606(2) 0.0286(7) Uani 1 1 d .
H12A H -0.6134 0.0376 0.0274 0.034 Uiso 1 1 calc R
H12B H -0.4555 0.0754 0.1055 0.034 Uiso 1 1 calc R
C13 C -0.1152(3) 0.0005(2) 0.3162(2) 0.0263(7) Uani 1 1 d .
C14 C -0.6631(3) 0.12951(18) 0.1248(2) 0.0257(7) Uani 1 1 d .
C15 C -0.0614(3) 0.07471(19) 0.2798(2) 0.0243(6) Uani 1 1 d .
H15 H -0.0622 0.1268 0.3161 0.029 Uiso 1 1 calc R
C16 C -0.3219(3) 0.0188(2) 0.5861(2) 0.0335(8) Uani 1 1 d .
H16 H -0.2905 -0.0388 0.5784 0.040 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'
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
O3 Cu1 N3 93.33(9) 1_655 4_665
O3 Cu1 O1 155.75(8) 1_655 .
N3 Cu1 O1 90.17(8) 4_665 .
O3 Cu1 N1 92.08(9) 1_655 .
N3 Cu1 N1 169.69(9) 4_665 .
O1 Cu1 N1 88.49(8) . .
O3 Cu1 O6 102.99(7) 1_655 .
N3 Cu1 O6 87.28(9) 4_665 .
O1 Cu1 O6 101.14(7) . .
N1 Cu1 O6 82.95(8) . .
O3 Cu1 O2 97.94(7) 1_655 .
N3 Cu1 O2 94.81(8) 4_665 .
O1 Cu1 O2 57.84(7) . .
N1 Cu1 O2 93.13(7) . .
O6 Cu1 O2 158.82(7) . .
C8 O1 Cu1 100.25(16) . .
H1WA O1W H1WB 110(3) . .
C8 O2 Cu1 80.42(15) . .
C14 O3 Cu1 123.64(18) . 1_455
Cu1 O6 H6A 83(2) . .
Cu1 O6 H6B 150(2) . .
H6A O6 H6B 108(3) . .
C4 N1 C15 117.4(2) . .
C4 N1 Cu1 123.81(19) . .
C15 N1 Cu1 118.4(2) . .
C10 N2 C9 125.8(3) . .
C10 N2 H2N 117.0(19) . .
C9 N2 H2N 117.0(19) . .
C7 N3 C3 118.4(3) . .
C7 N3 Cu1 123.4(2) . 4_566
C3 N3 Cu1 118.10(19) . 4_566
C2 C1 C4 119.1(3) . .
C2 C1 H1 120.5 . .
C4 C1 H1 120.5 . .
C1 C2 C13 119.9(3) . .
C1 C2 H2 120.1 . .
C13 C2 H2 120.1 . .
N3 C3 C5 121.6(3) . .
N3 C3 H3 119.2 . .
C5 C3 H3 119.2 . .
N1 C4 C1 122.9(3) . .
N1 C4 H4 118.5 . .
C1 C4 H4 118.5 . .
C3 C5 C16 119.9(3) . .
C3 C5 H5 120.1 . .
C16 C5 H5 120.1 . .
C11 C6 C12 113.4(2) . .
C11 C6 H6C 108.9 . .
C12 C6 H6C 108.9 . .
C11 C6 H6D 108.9 . .
C12 C6 H6D 108.9 . .
H6C C6 H6D 107.7 . .
N3 C7 C9 123.2(3) . .
N3 C7 H7 118.4 . .
C9 C7 H7 118.4 . .
O2 C8 O1 121.5(2) . .
O2 C8 C11 119.6(2) . .
O1 C8 C11 118.9(2) . .
C16 C9 C7 118.4(3) . .
C16 C9 N2 125.2(3) . .
C7 C9 N2 116.4(3) . .
O5 C10 N2 123.5(3) . .
O5 C10 C13 121.9(3) . .
N2 C10 C13 114.6(3) . .
C8 C11 C6 112.0(2) . .
C8 C11 H11A 109.2 . .
C6 C11 H11A 109.2 . .
C8 C11 H11B 109.2 . .
C6 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
C14 C12 C6 110.9(2) . .
C14 C12 H12A 109.5 . .
C6 C12 H12A 109.5 . .
C14 C12 H12B 109.5 . .
C6 C12 H12B 109.5 . .
H12A C12 H12B 108.0 . .
C2 C13 C15 117.6(3) . .
C2 C13 C10 117.9(3) . .
C15 C13 C10 124.4(3) . .
O4 C14 O3 124.3(3) . .
O4 C14 C12 120.8(2) . .
O3 C14 C12 114.9(3) . .
N1 C15 C13 123.1(3) . .
N1 C15 H15 118.4 . .
C13 C15 H15 118.4 . .
C9 C16 C5 118.5(3) . .
C9 C16 H16 120.7 . .
C5 C16 H16 120.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.9465(18) 1_655
Cu1 N3 2.011(2) 4_665
Cu1 O1 2.0139(17) .
Cu1 N1 2.026(2) .
Cu1 O6 2.424(2) .
Cu1 O2 2.4768(18) .
O1 C8 1.292(3) .
O1W H1WA 0.833(17) .
O1W H1WB 0.863(16) .
O2 C8 1.240(3) .
O3 C14 1.273(3) .
O3 Cu1 1.9465(18) 1_455
O4 C14 1.243(3) .
O5 C10 1.236(4) .
O6 H6A 0.846(17) .
O6 H6B 0.866(17) .
N1 C4 1.339(4) .
N1 C15 1.341(3) .
N2 C10 1.341(4) .
N2 C9 1.441(3) .
N2 H2N 0.909(17) .
N3 C7 1.337(3) .
N3 C3 1.344(4) .
N3 Cu1 2.011(2) 4_566
C1 C2 1.357(4) .
C1 C4 1.376(4) .
C1 H1 0.9500 .
C2 C13 1.384(4) .
C2 H2 0.9500 .
C3 C5 1.371(4) .
C3 H3 0.9500 .
C4 H4 0.9500 .
C5 C16 1.392(4) .
C5 H5 0.9500 .
C6 C11 1.528(4) .
C6 C12 1.532(4) .
C6 H6C 0.9900 .
C6 H6D 0.9900 .
C7 C9 1.380(4) .
C7 H7 0.9500 .
C8 C11 1.517(3) .
C9 C16 1.377(4) .
C10 C13 1.497(4) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C14 1.518(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C15 1.386(4) .
C15 H15 0.9500 .
C16 H16 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O1 0.833(17) 1.939(18) 2.763(3) 170(3) .
O1W H1WB O4 0.863(16) 1.836(17) 2.697(3) 175(3) .
O6 H6A O4 0.846(17) 1.906(18) 2.734(3) 166(3) 1_655
O6 H6B O2 0.866(17) 1.941(18) 2.799(3) 171(3) 4_666
N2 H2N O1W 0.909(17) 1.952(19) 2.835(3) 163(3) .
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
O3 Cu1 O1 C8 -2.8(3) 1_655
N3 Cu1 O1 C8 95.75(17) 4_665
N1 Cu1 O1 C8 -94.47(17) .
O6 Cu1 O1 C8 -176.99(17) .
O2 Cu1 O1 C8 0.18(16) .
O3 Cu1 O2 C8 178.60(17) 1_655
N3 Cu1 O2 C8 -87.35(17) 4_665
O1 Cu1 O2 C8 -0.18(16) .
N1 Cu1 O2 C8 86.06(17) .
O6 Cu1 O2 C8 7.5(3) .
O3 Cu1 N1 C4 -33.3(2) 1_655
N3 Cu1 N1 C4 -155.0(4) 4_665
O1 Cu1 N1 C4 122.4(2) .
O6 Cu1 N1 C4 -136.2(2) .
O2 Cu1 N1 C4 64.7(2) .
O3 Cu1 N1 C15 153.97(18) 1_655
N3 Cu1 N1 C15 32.3(6) 4_665
O1 Cu1 N1 C15 -50.28(18) .
O6 Cu1 N1 C15 51.14(18) .
O2 Cu1 N1 C15 -107.95(18) .
C4 C1 C2 C13 -0.6(4) .
C7 N3 C3 C5 2.1(4) .
Cu1 N3 C3 C5 -175.2(2) 4_566
C15 N1 C4 C1 0.9(4) .
Cu1 N1 C4 C1 -171.8(2) .
C2 C1 C4 N1 0.4(4) .
N3 C3 C5 C16 -1.7(4) .
C3 N3 C7 C9 -0.9(4) .
Cu1 N3 C7 C9 176.27(19) 4_566
Cu1 O2 C8 O1 0.3(2) .
Cu1 O2 C8 C11 179.6(2) .
Cu1 O1 C8 O2 -0.3(3) .
Cu1 O1 C8 C11 -179.7(2) .
N3 C7 C9 C16 -0.7(4) .
N3 C7 C9 N2 178.1(2) .
C10 N2 C9 C16 -7.2(4) .
C10 N2 C9 C7 174.0(3) .
C9 N2 C10 O5 -0.1(4) .
C9 N2 C10 C13 179.1(2) .
O2 C8 C11 C6 55.5(3) .
O1 C8 C11 C6 -125.1(3) .
C12 C6 C11 C8 78.0(3) .
C11 C6 C12 C14 67.4(3) .
C1 C2 C13 C15 -0.5(4) .
C1 C2 C13 C10 -177.3(3) .
O5 C10 C13 C2 24.4(4) .
N2 C10 C13 C2 -154.9(3) .
O5 C10 C13 C15 -152.2(3) .
N2 C10 C13 C15 28.5(4) .
Cu1 O3 C14 O4 0.4(4) 1_455
Cu1 O3 C14 C12 -179.81(17) 1_455
C6 C12 C14 O4 -113.5(3) .
C6 C12 C14 O3 66.8(3) .
C4 N1 C15 C13 -2.1(4) .
Cu1 N1 C15 C13 171.06(19) .
C2 C13 C15 N1 1.9(4) .
C10 C13 C15 N1 178.5(2) .
C7 C9 C16 C5 1.2(4) .
N2 C9 C16 C5 -177.5(2) .
C3 C5 C16 C9 0.0(4) .
