#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:20:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180073 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/19/7051936.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_7051936
loop_
_publ_author_name
'Dobrzańska, Liliana'
'Kleinhans, Dewald J.'
'Barbour, Leonard J.'
_publ_section_title
;
 Influence of the metal-to-ligand ratio on the formation of metal
 organic complexes
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              813
_journal_paper_doi               10.1039/b800720a
_journal_volume                  32
_journal_year                    2008
_chemical_formula_sum            'C14 H16 Cu N6 O7'
_chemical_formula_weight         443.87
_chemical_name_common            cNO3
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.047(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.841(4)
_cell_length_b                   8.311(3)
_cell_length_c                   21.919(8)
_cell_measurement_reflns_used    1111
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.369
_cell_measurement_theta_min      2.474
_cell_volume                     1759.5(12)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0918
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10495
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    1.295
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_correction_T_min  0.8196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4040
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0659P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                2712
_reflns_number_total             4040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b800720a.txt
_cod_data_source_block           VIII
_cod_original_cell_volume        1759.4(11)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7051936
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.32405(5) 0.25469(7) 0.44455(2) 0.01635(17) Uani 1 1 d . . .
N1 N 0.2288(4) 0.3568(4) 0.50511(16) 0.0164(8) Uani 1 1 d . . .
C2 C 0.2572(4) 0.4987(5) 0.5313(2) 0.0187(10) Uani 1 1 d . . .
H2 H 0.3291 0.5673 0.5234 0.022 Uiso 1 1 calc R . .
N3 N 0.1729(4) 0.5343(4) 0.57024(16) 0.0168(8) Uani 1 1 d . . .
C4 C 0.0839(5) 0.4074(5) 0.5702(2) 0.0196(10) Uani 1 1 d . . .
H4 H 0.0124 0.3976 0.5936 0.023 Uiso 1 1 calc R . .
C5 C 0.1192(4) 0.2992(5) 0.5299(2) 0.0164(9) Uani 1 1 d . . .
H5 H 0.0751 0.1982 0.5200 0.020 Uiso 1 1 calc R . .
C6 C 0.1743(5) 0.6817(5) 0.6073(2) 0.0195(10) Uani 1 1 d . . .
H6A H 0.0787 0.7236 0.6028 0.023 Uiso 1 1 calc R . .
H6B H 0.2309 0.7645 0.5913 0.023 Uiso 1 1 calc R . .
C7 C 0.2324(5) 0.6518(5) 0.6751(2) 0.0169(9) Uani 1 1 d . . .
C8 C 0.1457(4) 0.6730(5) 0.7181(2) 0.0181(10) Uani 1 1 d . . .
H8 H 0.0523 0.7058 0.7044 0.022 Uiso 1 1 calc R . .
C9 C 0.1970(5) 0.6455(5) 0.7817(2) 0.0180(10) Uani 1 1 d . . .
C10 C 0.3338(5) 0.5993(5) 0.8010(2) 0.0231(11) Uani 1 1 d . . .
H10 H 0.3686 0.5788 0.8438 0.028 Uiso 1 1 calc R . .
C11 C 0.4200(5) 0.5829(5) 0.7583(2) 0.0243(11) Uani 1 1 d . . .
H11 H 0.5144 0.5540 0.7720 0.029 Uiso 1 1 calc R . .
C12 C 0.3686(5) 0.6085(5) 0.6958(2) 0.0215(10) Uani 1 1 d . . .
H12 H 0.4280 0.5962 0.6667 0.026 Uiso 1 1 calc R . .
C13 C 0.1021(5) 0.6693(5) 0.8275(2) 0.0210(10) Uani 1 1 d . . .
H13A H 0.1591 0.6926 0.8689 0.025 Uiso 1 1 calc R . .
H13B H 0.0431 0.7645 0.8146 0.025 Uiso 1 1 calc R . .
N14 N 0.0121(4) 0.5309(4) 0.83323(17) 0.0189(8) Uani 1 1 d . . .
C15 C -0.0029(5) 0.4620(5) 0.8867(2) 0.0190(10) Uani 1 1 d . . .
H15 H 0.0518 0.4876 0.9261 0.023 Uiso 1 1 calc R . .
N16 N -0.1031(4) 0.3542(4) 0.87793(16) 0.0195(8) Uani 1 1 d . . .
C17 C -0.1544(5) 0.3548(6) 0.8141(2) 0.0221(10) Uani 1 1 d . . .
H17 H -0.2279 0.2892 0.7933 0.027 Uiso 1 1 calc R . .
C18 C -0.0838(5) 0.4627(6) 0.7866(2) 0.0232(11) Uani 1 1 d . . .
H18 H -0.0975 0.4869 0.7435 0.028 Uiso 1 1 calc R . .
N19 N 0.1780(4) -0.0321(5) 0.44319(19) 0.0212(9) Uani 1 1 d . . .
O20 O 0.0974(3) 0.0551(4) 0.40718(17) 0.0334(9) Uani 1 1 d . . .
O21 O 0.1620(4) -0.1771(4) 0.44846(19) 0.0383(10) Uani 1 1 d . . .
O22 O 0.2868(3) 0.0327(4) 0.47660(14) 0.0200(7) Uani 1 1 d . . .
N23 N 0.2846(4) 0.5253(5) 0.37183(17) 0.0197(8) Uani 1 1 d . . .
O24 O 0.3025(4) 0.6498(4) 0.34488(16) 0.0330(9) Uani 1 1 d . . .
O25 O 0.1767(3) 0.4429(4) 0.35939(14) 0.0230(7) Uani 1 1 d . . .
O26 O 0.3834(3) 0.4728(4) 0.41584(14) 0.0191(7) Uani 1 1 d . . .
O27 O 0.5251(3) 0.2440(4) 0.51521(14) 0.0216(7) Uani 1 1 d D . .
H27A H 0.600(4) 0.162(5) 0.521(3) 0.09(2) Uiso 1 1 d D . .
H27B H 0.552(5) 0.320(5) 0.5501(18) 0.08(2) Uiso 1 1 d 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
_geom_angle_publ_flag
N1 Cu1 N16 172.96(15) . 4_665 ?
N1 Cu1 O22 91.02(13) . . ?
N16 Cu1 O22 87.38(14) 4_665 . ?
N1 Cu1 O26 91.51(13) . . ?
N16 Cu1 O26 90.77(14) 4_665 . ?
O22 Cu1 O26 173.87(12) . . ?
N1 Cu1 O27 91.27(14) . . ?
N16 Cu1 O27 95.44(14) 4_665 . ?
O22 Cu1 O27 85.40(12) . . ?
O26 Cu1 O27 88.95(12) . . ?
C2 N1 C5 104.8(4) . . ?
C2 N1 Cu1 126.5(3) . . ?
C5 N1 Cu1 128.8(3) . . ?
N1 C2 N3 111.8(4) . . ?
N1 C2 H2 124.1 . . ?
N3 C2 H2 124.1 . . ?
C2 N3 C4 107.8(4) . . ?
C2 N3 C6 126.8(4) . . ?
C4 N3 C6 125.4(4) . . ?
C5 C4 N3 105.5(4) . . ?
C5 C4 H4 127.2 . . ?
N3 C4 H4 127.2 . . ?
C4 C5 N1 110.1(4) . . ?
C4 C5 H5 125.0 . . ?
N1 C5 H5 125.0 . . ?
N3 C6 C7 111.7(4) . . ?
N3 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C12 C7 C8 119.5(4) . . ?
C12 C7 C6 121.9(4) . . ?
C8 C7 C6 118.6(4) . . ?
C7 C8 C9 119.8(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 C13 121.5(4) . . ?
C8 C9 C13 119.1(4) . . ?
C9 C10 C11 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C7 C12 C11 120.9(4) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N14 C13 C9 114.5(4) . . ?
N14 C13 H13A 108.6 . . ?
C9 C13 H13A 108.6 . . ?
N14 C13 H13B 108.6 . . ?
C9 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 N14 C18 107.5(4) . . ?
C15 N14 C13 125.4(4) . . ?
C18 N14 C13 126.7(4) . . ?
N16 C15 N14 111.6(4) . . ?
N16 C15 H15 124.2 . . ?
N14 C15 H15 124.2 . . ?
C15 N16 C17 105.1(4) . . ?
C15 N16 Cu1 125.0(3) . 4_566 ?
C17 N16 Cu1 129.3(3) . 4_566 ?
C18 C17 N16 109.5(4) . . ?
C18 C17 H17 125.2 . . ?
N16 C17 H17 125.2 . . ?
C17 C18 N14 106.3(4) . . ?
C17 C18 H18 126.9 . . ?
N14 C18 H18 126.9 . . ?
O21 N19 O20 123.9(4) . . ?
O21 N19 O22 117.7(4) . . ?
O20 N19 O22 118.5(4) . . ?
N19 O22 Cu1 111.5(3) . . ?
O24 N23 O25 123.7(4) . . ?
O24 N23 O26 119.0(4) . . ?
O25 N23 O26 117.3(4) . . ?
N23 O26 Cu1 107.9(3) . . ?
Cu1 O27 H27A 130(3) . . ?
Cu1 O27 H27B 125(3) . . ?
H27A O27 H27B 105(4) . . ?
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 N1 1.959(3) . ?
Cu1 N16 1.966(4) 4_665 ?
Cu1 O22 2.033(3) . ?
Cu1 O26 2.041(3) . ?
Cu1 O27 2.269(3) . ?
N1 C2 1.318(5) . ?
N1 C5 1.383(5) . ?
C2 N3 1.332(5) . ?
C2 H2 0.9500 . ?
N3 C4 1.371(5) . ?
N3 C6 1.469(5) . ?
C4 C5 1.353(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.508(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.378(6) . ?
C7 C8 1.398(6) . ?
C8 C9 1.408(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(6) . ?
C9 C13 1.509(6) . ?
C10 C11 1.385(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(7) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N14 1.471(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N14 C15 1.338(5) . ?
N14 C18 1.374(6) . ?
C15 N16 1.319(6) . ?
C15 H15 0.9500 . ?
N16 C17 1.393(6) . ?
N16 Cu1 1.966(4) 4_566 ?
C17 C18 1.347(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N19 O21 1.224(5) . ?
N19 O20 1.240(5) . ?
N19 O22 1.293(5) . ?
N23 O24 1.221(5) . ?
N23 O25 1.249(5) . ?
N23 O26 1.306(5) . ?
O27 H27A 0.99(4) . ?
O27 H27B 0.99(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O27 H27a O22 3_656 0.99(4) 1.96(4) 2.936(5) 167(5)
O27 H27a O21 3_656 0.99(4) 2.31(4) 3.080(5) 133(3)
O27 H27b O26 3_666 0.99(4) 1.94(4) 2.848(5) 153(3)
O27 H27b O24 3_666 0.99(4) 2.48(4) 3.327(5) 144(3)
C2 H2 O27 3_666 0.95 2.39 3.323(5) 168
C4 H4 O21 3_556 0.95 2.56 3.051(6) 112
C5 H5 O21 3_556 0.95 2.56 3.069(6) 113
C6 H6A O20 3_566 0.99 2.51 3.422(6) 153
C15 H15 O22 2_556 0.95 2.43 3.377(6) 173
C18 H18 O25 3_566 0.95 2.32 3.251(5) 168
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
O22 Cu1 N1 C2 148.8(4) . . . . ?
O26 Cu1 N1 C2 -25.6(4) . . . . ?
O27 Cu1 N1 C2 63.4(4) . . . . ?
O22 Cu1 N1 C5 -31.1(4) . . . . ?
O26 Cu1 N1 C5 154.5(4) . . . . ?
O27 Cu1 N1 C5 -116.5(4) . . . . ?
C5 N1 C2 N3 -0.4(5) . . . . ?
Cu1 N1 C2 N3 179.6(3) . . . . ?
N1 C2 N3 C4 0.5(5) . . . . ?
N1 C2 N3 C6 -179.9(4) . . . . ?
C2 N3 C4 C5 -0.4(5) . . . . ?
C6 N3 C4 C5 -180.0(4) . . . . ?
N3 C4 C5 N1 0.2(5) . . . . ?
C2 N1 C5 C4 0.2(5) . . . . ?
Cu1 N1 C5 C4 -179.9(3) . . . . ?
C2 N3 C6 C7 -106.3(5) . . . . ?
C4 N3 C6 C7 73.2(5) . . . . ?
N3 C6 C7 C12 65.6(5) . . . . ?
N3 C6 C7 C8 -116.1(4) . . . . ?
C12 C7 C8 C9 -1.8(6) . . . . ?
C6 C7 C8 C9 179.8(4) . . . . ?
C7 C8 C9 C10 0.7(7) . . . . ?
C7 C8 C9 C13 179.9(4) . . . . ?
C8 C9 C10 C11 1.1(7) . . . . ?
C13 C9 C10 C11 -178.1(4) . . . . ?
C9 C10 C11 C12 -1.7(7) . . . . ?
C8 C7 C12 C11 1.2(7) . . . . ?
C6 C7 C12 C11 179.5(4) . . . . ?
C10 C11 C12 C7 0.6(7) . . . . ?
C10 C9 C13 N14 -97.9(5) . . . . ?
C8 C9 C13 N14 83.0(5) . . . . ?
C9 C13 N14 C15 129.6(4) . . . . ?
C9 C13 N14 C18 -59.4(6) . . . . ?
C18 N14 C15 N16 -0.5(5) . . . . ?
C13 N14 C15 N16 172.0(4) . . . . ?
N14 C15 N16 C17 0.3(5) . . . . ?
N14 C15 N16 Cu1 -171.7(3) . . . 4_566 ?
C15 N16 C17 C18 0.0(5) . . . . ?
Cu1 N16 C17 C18 171.5(3) 4_566 . . . ?
N16 C17 C18 N14 -0.2(5) . . . . ?
C15 N14 C18 C17 0.4(5) . . . . ?
C13 N14 C18 C17 -171.9(4) . . . . ?
O21 N19 O22 Cu1 163.8(3) . . . . ?
O20 N19 O22 Cu1 -15.1(4) . . . . ?
N1 Cu1 O22 N19 96.5(3) . . . . ?
N16 Cu1 O22 N19 -76.6(3) 4_665 . . . ?
O27 Cu1 O22 N19 -172.3(3) . . . . ?
O24 N23 O26 Cu1 -175.1(3) . . . . ?
O25 N23 O26 Cu1 4.2(4) . . . . ?
N1 Cu1 O26 N23 -87.8(3) . . . . ?
N16 Cu1 O26 N23 85.6(3) 4_665 . . . ?
O27 Cu1 O26 N23 -179.0(2) . . . . ?
