#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/78/1517824.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_1517824
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           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.8840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.476(3)
_cell_length_b                   8.8641(10)
_cell_length_c                   17.5434(19)
_cell_measurement_reflns_used    7337
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.48
_cell_volume                     3410.8(7)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13480
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    1.328
_exptl_absorpt_correction_T_max  0.8943
_exptl_absorpt_correction_T_min  0.7018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0321
_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)+(0.0467P)²+5.6208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                2660
_reflns_number_total             3121
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-405-31-42-5.cif
_cod_data_source_block           c2c
_cod_original_cell_volume        3410.8(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1517824
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.343759(14) 0.87736(3) 0.071388(19) 0.02162(12) Uani 1 1 d .
O1 O 0.51062(9) 0.3690(2) 0.36223(14) 0.0375(5) Uani 1 1 d .
O1W O 0.57297(18) 0.4889(4) 0.5327(2) 0.0915(10) Uani 1 1 d D
H1WA H 0.552(2) 0.445(6) 0.4831(19) 0.110 Uiso 1 1 d D
H1WB H 0.590(2) 0.576(4) 0.522(3) 0.110 Uiso 1 1 d D
O2 O 0.31818(9) 1.0695(2) 0.01595(11) 0.0270(4) Uani 1 1 d .
O3 O 0.32049(9) 1.0109(2) -0.10665(12) 0.0339(5) Uani 1 1 d .
O4 O 0.22689(8) 1.60139(19) -0.10774(11) 0.0244(4) Uani 1 1 d .
O5 O 0.15860(8) 1.4561(2) -0.19634(11) 0.0276(4) Uani 1 1 d .
O6 O 0.33462(9) 0.7416(2) -0.04119(12) 0.0296(4) Uani 1 1 d D
H6C H 0.3300(14) 0.820(3) -0.0689(18) 0.036 Uiso 1 1 d D
H6D H 0.3012(10) 0.696(3) -0.0607(18) 0.036 Uiso 1 1 d D
N1 N 0.36570(10) 0.6866(2) 0.13644(13) 0.0233(5) Uani 1 1 d .
N2 N 0.56634(10) -0.0719(2) 0.41220(13) 0.0220(5) Uani 1 1 d .
N3 N 0.41698(10) 0.2930(2) 0.27541(14) 0.0241(5) Uani 1 1 d D
H3N H 0.3942(12) 0.215(3) 0.2545(17) 0.029 Uiso 1 1 d D
C1 C 0.40519(14) 0.6914(3) 0.21330(17) 0.0309(7) Uani 1 1 d .
H1 H 0.4220 0.7865 0.2349 0.037 Uiso 1 1 calc R
C2 C 0.34048(12) 0.5525(3) 0.10849(17) 0.0266(6) Uani 1 1 d .
H2 H 0.3108 0.5473 0.0550 0.032 Uiso 1 1 calc R
C3 C 0.35556(12) 0.4222(3) 0.15359(17) 0.0265(6) Uani 1 1 d .
H3 H 0.3366 0.3295 0.1314 0.032 Uiso 1 1 calc R
C4 C 0.39884(12) 0.4274(3) 0.23206(16) 0.0222(5) Uani 1 1 d .
C5 C 0.42283(14) 0.5669(3) 0.26277(17) 0.0304(6) Uani 1 1 d .
H5 H 0.4510 0.5763 0.3171 0.036 Uiso 1 1 calc R
C6 C 0.29791(13) 1.2631(3) -0.08172(17) 0.0287(6) Uani 1 1 d .
H6A H 0.3343 1.3263 -0.0544 0.034 Uiso 1 1 calc R
H6B H 0.2652 1.2967 -0.0623 0.034 Uiso 1 1 calc R
C7 C 0.47256(12) 0.2702(3) 0.33522(16) 0.0244(6) Uani 1 1 d .
C8 C 0.48680(12) 0.1112(3) 0.36432(15) 0.0219(6) Uani 1 1 d .
C10 C 0.46582(13) -0.1314(3) 0.40670(17) 0.0267(6) Uani 1 1 d .
H10 H 0.4388 -0.2017 0.4168 0.032 Uiso 1 1 calc R
C11 C 0.54691(12) 0.0658(3) 0.38474(15) 0.0224(5) Uani 1 1 d .
H11 H 0.5756 0.1362 0.3789 0.027 Uiso 1 1 calc R
C12 C 0.44517(12) 0.0102(3) 0.37456(16) 0.0244(6) Uani 1 1 d .
H12 H 0.4035 0.0370 0.3600 0.029 Uiso 1 1 calc R
C13 C 0.52609(12) -0.1683(3) 0.42367(17) 0.0261(6) Uani 1 1 d .
H13 H 0.5397 -0.2661 0.4444 0.031 Uiso 1 1 calc R
C14 C 0.31334(11) 1.1014(3) -0.05665(16) 0.0233(6) Uani 1 1 d .
C15 C 0.27710(14) 1.2891(3) -0.17358(16) 0.0292(6) Uani 1 1 d .
H15A H 0.3100 1.2577 -0.1931 0.035 Uiso 1 1 calc R
H15B H 0.2410 1.2255 -0.2013 0.035 Uiso 1 1 calc R
C18 C 0.26106(13) 1.4538(3) -0.19649(17) 0.0295(6) Uani 1 1 d .
H18A H 0.2978 1.5173 -0.1720 0.035 Uiso 1 1 calc R
H18B H 0.2471 1.4651 -0.2565 0.035 Uiso 1 1 calc R
C19 C 0.21151(12) 1.5060(3) -0.16647(15) 0.0222(6) Uani 1 1 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'
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
O2 Cu1 O4 86.17(8) . 7_575
O2 Cu1 N1 173.97(8) . .
O4 Cu1 N1 88.38(8) 7_575 .
O2 Cu1 N2 89.83(8) . 2_665
O4 Cu1 N2 149.21(8) 7_575 2_665
N1 Cu1 N2 93.53(9) . 2_665
O2 Cu1 O6 96.50(7) . .
O4 Cu1 O6 120.11(7) 7_575 .
N1 Cu1 O6 88.48(8) . .
N2 Cu1 O6 90.67(8) 2_665 .
H1WA O1W H1WB 106(4) . .
C14 O2 Cu1 126.65(17) . .
C19 O4 Cu1 107.00(16) . 7_575
Cu1 O6 H6C 91(2) . .
Cu1 O6 H6D 114(2) . .
H6C O6 H6D 105(3) . .
C1 N1 C2 117.0(2) . .
C1 N1 Cu1 119.53(18) . .
C2 N1 Cu1 123.38(18) . .
C11 N2 C13 118.0(2) . .
C11 N2 Cu1 116.68(17) . 2_645
C13 N2 Cu1 125.27(18) . 2_645
C7 N3 C4 124.5(2) . .
C7 N3 H3N 119(2) . .
C4 N3 H3N 115.3(19) . .
N1 C1 C5 123.8(3) . .
N1 C1 H1 118.1 . .
C5 C1 H1 118.1 . .
N1 C2 C3 123.1(2) . .
N1 C2 H2 118.5 . .
C3 C2 H2 118.5 . .
C2 C3 C4 119.4(2) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C5 C4 C3 117.8(2) . .
C5 C4 N3 123.2(2) . .
C3 C4 N3 119.0(2) . .
C1 C5 C4 118.8(3) . .
C1 C5 H5 120.6 . .
C4 C5 H5 120.6 . .
C14 C6 C15 113.9(2) . .
C14 C6 H6A 108.8 . .
C15 C6 H6A 108.8 . .
C14 C6 H6B 108.8 . .
C15 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
O1 C7 N3 124.0(2) . .
O1 C7 C8 120.0(2) . .
N3 C7 C8 115.9(2) . .
C12 C8 C11 118.7(2) . .
C12 C8 C7 124.9(2) . .
C11 C8 C7 116.4(2) . .
C13 C10 C12 119.0(2) . .
C13 C10 H10 120.5 . .
C12 C10 H10 120.5 . .
N2 C11 C8 123.1(2) . .
N2 C11 H11 118.5 . .
C8 C11 H11 118.5 . .
C8 C12 C10 118.5(2) . .
C8 C12 H12 120.8 . .
C10 C12 H12 120.8 . .
N2 C13 C10 122.8(2) . .
N2 C13 H13 118.6 . .
C10 C13 H13 118.6 . .
O3 C14 O2 125.3(2) . .
O3 C14 C6 119.1(2) . .
O2 C14 C6 115.5(2) . .
C18 C15 C6 112.3(2) . .
C18 C15 H15A 109.1 . .
C6 C15 H15A 109.1 . .
C18 C15 H15B 109.1 . .
C6 C15 H15B 109.1 . .
H15A C15 H15B 107.9 . .
C19 C18 C15 110.5(2) . .
C19 C18 H18A 109.6 . .
C15 C18 H18A 109.6 . .
C19 C18 H18B 109.6 . .
C15 C18 H18B 109.6 . .
H18A C18 H18B 108.1 . .
O5 C19 O4 121.7(2) . .
O5 C19 C18 121.4(2) . .
O4 C19 C18 116.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.9472(18) .
Cu1 O4 1.9867(19) 7_575
Cu1 N1 2.002(2) .
Cu1 N2 2.075(2) 2_665
Cu1 O6 2.257(2) .
O1 C7 1.220(3) .
O1W H1WA 0.918(19) .
O1W H1WB 0.925(19) .
O2 C14 1.270(3) .
O3 C14 1.243(3) .
O4 C19 1.281(3) .
O4 Cu1 1.9868(19) 7_575
O5 C19 1.244(3) .
O6 H6C 0.834(17) .
O6 H6D 0.842(17) .
N1 C1 1.337(4) .
N1 C2 1.341(3) .
N2 C11 1.332(3) .
N2 C13 1.341(4) .
N2 Cu1 2.075(2) 2_645
N3 C7 1.367(3) .
N3 C4 1.396(3) .
N3 H3N 0.873(17) .
C1 C5 1.374(4) .
C1 H1 0.9500 .
C2 C3 1.373(4) .
C2 H2 0.9500 .
C3 C4 1.390(4) .
C3 H3 0.9500 .
C4 C5 1.386(4) .
C5 H5 0.9500 .
C6 C14 1.505(4) .
C6 C15 1.526(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.495(3) .
C8 C12 1.383(4) .
C8 C11 1.386(4) .
C10 C13 1.377(4) .
C10 C12 1.391(4) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 H13 0.9500 .
C15 C18 1.525(4) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C18 C19 1.510(4) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
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 0.918(19) 2.11(2) 3.016(5) 172(5) .
O1W H1WB O6 0.925(19) 2.22(3) 3.085(4) 155(5) 2_655
O6 H6C O3 0.834(17) 1.800(19) 2.618(3) 166(3) .
O6 H6D O4 0.842(17) 1.842(18) 2.683(3) 177(3) 1_545
N3 H3N O5 0.873(17) 1.992(18) 2.862(3) 175(3) 7_565
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
O4 Cu1 O2 C14 -133.8(2) 7_575
N1 Cu1 O2 C14 -159.3(7) .
N2 Cu1 O2 C14 76.7(2) 2_665
O6 Cu1 O2 C14 -13.9(2) .
O2 Cu1 N1 C1 -67.5(9) .
O4 Cu1 N1 C1 -93.0(2) 7_575
N2 Cu1 N1 C1 56.3(2) 2_665
O6 Cu1 N1 C1 146.8(2) .
O2 Cu1 N1 C2 109.0(8) .
O4 Cu1 N1 C2 83.6(2) 7_575
N2 Cu1 N1 C2 -127.2(2) 2_665
O6 Cu1 N1 C2 -36.6(2) .
C2 N1 C1 C5 2.9(4) .
Cu1 N1 C1 C5 179.7(2) .
C1 N1 C2 C3 -3.1(4) .
Cu1 N1 C2 C3 -179.7(2) .
N1 C2 C3 C4 0.1(4) .
C2 C3 C4 C5 3.1(4) .
C2 C3 C4 N3 -175.7(2) .
C7 N3 C4 C5 -25.8(4) .
C7 N3 C4 C3 152.9(3) .
N1 C1 C5 C4 0.2(5) .
C3 C4 C5 C1 -3.2(4) .
N3 C4 C5 C1 175.5(3) .
C4 N3 C7 O1 6.6(4) .
C4 N3 C7 C8 -170.2(2) .
O1 C7 C8 C12 144.9(3) .
N3 C7 C8 C12 -38.2(4) .
O1 C7 C8 C11 -32.8(4) .
N3 C7 C8 C11 144.1(2) .
C13 N2 C11 C8 -2.9(4) .
Cu1 N2 C11 C8 174.3(2) 2_645
C12 C8 C11 N2 1.5(4) .
C7 C8 C11 N2 179.4(2) .
C11 C8 C12 C10 1.4(4) .
C7 C8 C12 C10 -176.3(2) .
C13 C10 C12 C8 -2.8(4) .
C11 N2 C13 C10 1.3(4) .
Cu1 N2 C13 C10 -175.6(2) 2_645
C12 C10 C13 N2 1.5(4) .
Cu1 O2 C14 O3 4.9(4) .
Cu1 O2 C14 C6 -174.78(17) .
C15 C6 C14 O3 14.6(4) .
C15 C6 C14 O2 -165.6(2) .
C14 C6 C15 C18 179.2(2) .
C6 C15 C18 C19 -58.1(3) .
Cu1 O4 C19 O5 7.1(3) 7_575
Cu1 O4 C19 C18 -171.41(17) 7_575
C15 C18 C19 O5 -68.3(3) .
C15 C18 C19 O4 110.3(3) .
