#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/80/2208089.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2208089
loop_
_publ_author_name
'Rademeyer, Melanie'
_publ_section_title
;
 Tetrakis(benzylammonium) tetranitratocuprate(II) dinitrate
;
_journal_coeditor_code           IS2001
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m269
_journal_page_last               m271
_journal_paper_doi               10.1107/S1600536806000201
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '(C7 H10 N1)4 [Cu (N1 O4)3] (N O3)2'
_chemical_formula_moiety         '4C7 H10 N + , Cu N4 O12 2- , 2N O3 -'
_chemical_formula_sum            'C28 H40 Cu N10 O18'
_chemical_formula_weight         868.24
_chemical_name_systematic
;
Tetrakis(benzylammonium) tetranitratocuprate(II) dinitrate
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.93(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.79(3)
_cell_length_b                   5.749(9)
_cell_length_c                   21.293(14)
_cell_measurement_reflns_used    476
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      2
_cell_volume                     3733(7)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
'PLATON (Spek, 2003) and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Oxford Excalibur2'
_diffrn_measurement_method       ω/2θ
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17698
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.96
_diffrn_reflns_theta_min         4.39
_diffrn_standards_decay_%        <2
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.7140
_exptl_absorpt_correction_T_min  0.7140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1804
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.739
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0433
_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)+(0.071P)²+0.4182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                4603
_reflns_number_total             5929
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2208089
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 -0.00078(4) 0.51036(19) 0.84279(5) 0.0355(3) Uani d . 1 O
O4 -0.06425(4) 0.4501(2) 0.73340(6) 0.0375(3) Uani d . 1 O
C7 0.22386(7) 0.0182(3) 0.69590(10) 0.0456(4) Uani d . 1 C
H7 0.2195 -0.1129 0.7198 0.055 Uiso calc R 1 H
N4 -0.08162(5) 0.6563(3) 0.73080(6) 0.0351(3) Uani d . 1 N
O6 -0.12115(4) 0.6739(3) 0.71617(7) 0.0534(4) Uani d . 1 O
O5 -0.05672(5) 0.8235(2) 0.74217(7) 0.0485(3) Uani d . 1 O
C6 0.26161(7) 0.0378(4) 0.66773(11) 0.0548(5) Uani d . 1 C
H6 0.2825 -0.0802 0.6729 0.066 Uiso calc R 1 H
C9 -0.11423(5) -0.0697(3) 0.55755(8) 0.0365(3) Uani d . 1 C
N1 0.11133(5) 0.1578(3) 0.68094(8) 0.0439(3) Uani d . 1 N
H1A 0.0894 0.1502 0.7040 0.066 Uiso calc R 1 H
H1B 0.1117 0.0291 0.6578 0.066 Uiso calc R 1 H
H1C 0.1076 0.2810 0.6554 0.066 Uiso calc R 1 H
C2 0.19256(5) 0.1928(3) 0.68870(8) 0.0361(3) Uani d . 1 C
C3 0.19970(6) 0.3858(3) 0.65233(10) 0.0463(4) Uani d . 1 C
H3 0.1789 0.5042 0.6469 0.056 Uiso calc R 1 H
C14 -0.11807(6) 0.1150(4) 0.59834(9) 0.0425(4) Uani d . 1 C
H14 -0.0981 0.1304 0.6351 0.051 Uiso calc R 1 H
C13 -0.15124(7) 0.2761(4) 0.58474(11) 0.0515(5) Uani d . 1 C
H13 -0.1536 0.3993 0.6124 0.062 Uiso calc R 1 H
C1 0.15359(6) 0.1795(4) 0.72360(9) 0.0462(4) Uani d . 1 C
H1D 0.1570 0.0467 0.7520 0.055 Uiso calc R 1 H
H1E 0.1527 0.3183 0.7493 0.055 Uiso calc R 1 H
C4 0.23723(7) 0.4035(4) 0.62421(11) 0.0542(5) Uani d . 1 C
H4 0.2415 0.5331 0.5997 0.065 Uiso calc R 1 H
N2 -0.04000(4) -0.1950(3) 0.53864(7) 0.0360(3) Uani d . 1 N
H2A -0.0192 -0.3009 0.5495 0.054 Uiso calc R 1 H
H2B -0.0294 -0.0540 0.5488 0.054 Uiso calc R 1 H
H2C -0.0487 -0.2020 0.4970 0.054 Uiso calc R 1 H
C8 -0.07757(6) -0.2415(4) 0.57272(10) 0.0489(5) Uani d . 1 C
H8A -0.0676 -0.2381 0.6180 0.059 Uiso calc R 1 H
H8B -0.0886 -0.3965 0.5620 0.059 Uiso calc R 1 H
C5 0.26852(7) 0.2301(4) 0.63217(11) 0.0547(5) Uani d . 1 C
H5 0.2940 0.2433 0.6136 0.066 Uiso calc R 1 H
O3 0.01356(4) 0.2967(2) 0.92662(6) 0.0437(3) Uani d . 1 O
N3 0.00426(4) 0.3077(2) 0.86831(6) 0.0314(3) Uani d . 1 N
O2 0.00023(5) 0.1350(2) 0.83423(7) 0.0555(4) Uani d . 1 O
C10 -0.14412(7) -0.0906(4) 0.50340(10) 0.0503(5) Uani d . 1 C
H10 -0.1421 -0.2148 0.4760 0.060 Uiso calc R 1 H
C12 -0.18063(7) 0.2548(4) 0.53067(12) 0.0587(5) Uani d . 1 C
H12 -0.2030 0.3635 0.5216 0.070 Uiso calc R 1 H
C11 -0.17716(7) 0.0723(5) 0.48965(11) 0.0628(6) Uani d . 1 C
H11 -0.1970 0.0587 0.4527 0.075 Uiso calc R 1 H
O7 0.10816(5) 0.6966(3) 0.63794(7) 0.0547(4) Uani d . 1 O
N5 0.08195(5) 0.6599(3) 0.58950(7) 0.0379(3) Uani d . 1 N
O8 0.05945(5) 0.8189(3) 0.56389(8) 0.0698(5) Uani d . 1 O
O9 0.07946(7) 0.4542(3) 0.57094(10) 0.0735(5) Uani d . 1 O
Cu1 0.0000 0.48583(5) 0.7500 0.03026(9) Uani d S 1 Cu
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N3 O1 Cu1 . . 109.82(10)
N4 O4 Cu1 . . 108.04(11)
C6 C7 C2 . . 120.41(19)
C6 C7 H7 . . 119.8
C2 C7 H7 . . 119.8
O6 N4 O5 . . 123.92(17)
O6 N4 O4 . . 118.53(15)
O5 N4 O4 . . 117.53(16)
C5 C6 C7 . . 120.49(18)
C5 C6 H6 . . 119.8
C7 C6 H6 . . 119.8
C10 C9 C14 . . 119.09(17)
C10 C9 C8 . . 121.21(19)
C14 C9 C8 . . 119.70(18)
C1 N1 H1A . . 109.5
C1 N1 H1B . . 109.5
H1A N1 H1B . . 109.5
C1 N1 H1C . . 109.5
H1A N1 H1C . . 109.5
H1B N1 H1C . . 109.5
C7 C2 C3 . . 118.66(19)
C7 C2 C1 . . 120.05(18)
C3 C2 C1 . . 121.14(17)
C4 C3 C2 . . 120.58(18)
C4 C3 H3 . . 119.7
C2 C3 H3 . . 119.7
C13 C14 C9 . . 120.46(19)
C13 C14 H14 . . 119.8
C9 C14 H14 . . 119.8
C12 C13 C14 . . 120.1(2)
C12 C13 H13 . . 120.0
C14 C13 H13 . . 120.0
N1 C1 C2 . . 113.24(16)
N1 C1 H1D . . 108.9
C2 C1 H1D . . 108.9
N1 C1 H1E . . 108.9
C2 C1 H1E . . 108.9
H1D C1 H1E . . 107.7
C3 C4 C5 . . 120.4(2)
C3 C4 H4 . . 119.8
C5 C4 H4 . . 119.8
C8 N2 H2A . . 109.5
C8 N2 H2B . . 109.5
H2A N2 H2B . . 109.5
C8 N2 H2C . . 109.5
H2A N2 H2C . . 109.5
H2B N2 H2C . . 109.5
N2 C8 C9 . . 113.14(15)
N2 C8 H8A . . 109.0
C9 C8 H8A . . 109.0
N2 C8 H8B . . 109.0
C9 C8 H8B . . 109.0
H8A C8 H8B . . 107.8
C6 C5 C4 . . 119.4(2)
C6 C5 H5 . . 120.3
C4 C5 H5 . . 120.3
O2 N3 O3 . . 122.94(15)
O2 N3 O1 . . 119.15(15)
O3 N3 O1 . . 117.91(14)
C9 C10 C11 . . 120.3(2)
C9 C10 H10 . . 119.9
C11 C10 H10 . . 119.9
C13 C12 C11 . . 120.1(2)
C13 C12 H12 . . 120.0
C11 C12 H12 . . 120.0
C12 C11 C10 . . 120.0(2)
C12 C11 H11 . . 120.0
C10 C11 H11 . . 120.0
O8 N5 O7 . . 120.45(18)
O8 N5 O9 . . 124.0(2)
O7 N5 O9 . . 115.50(17)
O4 Cu1 O4 . 2_556 168.04(8)
O4 Cu1 O1 . . 92.07(8)
O4 Cu1 O1 2_556 . 88.77(8)
O4 Cu1 O1 . 2_556 88.77(8)
O4 Cu1 O1 2_556 2_556 92.07(8)
O1 Cu1 O1 . 2_556 171.85(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 N3 . 1.286(2)
O1 Cu1 . 1.9841(18)
O4 N4 . 1.299(2)
O4 Cu1 . 1.972(2)
C7 C6 . 1.384(3)
C7 C2 . 1.385(3)
C7 H7 . 0.9300
N4 O6 . 1.218(2)
N4 O5 . 1.233(2)
C6 C5 . 1.373(4)
C6 H6 . 0.9300
C9 C10 . 1.378(3)
C9 C14 . 1.387(3)
C9 C8 . 1.501(3)
N1 C1 . 1.486(3)
N1 H1A . 0.8900
N1 H1B . 0.8900
N1 H1C . 0.8900
C2 C3 . 1.388(3)
C2 C1 . 1.498(3)
C3 C4 . 1.377(3)
C3 H3 . 0.9300
C14 C13 . 1.379(3)
C14 H14 . 0.9300
C13 C12 . 1.368(3)
C13 H13 . 0.9300
C1 H1D . 0.9700
C1 H1E . 0.9700
C4 C5 . 1.380(3)
C4 H4 . 0.9300
N2 C8 . 1.472(2)
N2 H2A . 0.8900
N2 H2B . 0.8900
N2 H2C . 0.8900
C8 H8A . 0.9700
C8 H8B . 0.9700
C5 H5 . 0.9300
O3 N3 . 1.2366(19)
N3 O2 . 1.226(2)
C10 C11 . 1.384(3)
C10 H10 . 0.9300
C12 C11 . 1.378(4)
C12 H12 . 0.9300
C11 H11 . 0.9300
O7 N5 . 1.237(2)
N5 O8 . 1.228(2)
N5 O9 . 1.246(3)
Cu1 O4 2_556 1.972(2)
Cu1 O1 2_556 1.9842(17)
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
N1 H1A O4 2_556 0.89 2.37 2.997(3) 127
N1 H1A O5 2_546 0.89 2.48 3.156(3) 133
N1 H1B O7 1_545 0.89 1.96 2.803(4) 158
N1 H1B N5 1_545 0.89 2.66 3.509(4) 159
N1 H1C O9 . 0.89 2.13 2.953(4) 153
N1 H1C O7 . 0.89 2.42 3.228(5) 151
N1 H1C N5 . 0.89 2.65 3.530(4) 169
N2 H2A O3 2_546 0.89 2.37 3.096(5) 139
N2 H2A O8 1_545 0.89 2.50 3.036(4) 120
N2 H2A O1 2_546 0.89 2.54 3.154(3) 127
N2 H2B O3 2_556 0.89 2.12 3.006(4) 172
N2 H2C O9 5_556 0.89 2.17 2.891(3) 138
N2 H2C O8 5_566 0.89 2.55 3.072(3) 118
N2 H2C O3 6 0.89 2.65 3.136(3) 116
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_site_symmetry_4
_geom_torsion
Cu1 O4 N4 O6 . 174.55(12)
Cu1 O4 N4 O5 . -4.01(16)
C2 C7 C6 C5 . -0.1(3)
C6 C7 C2 C3 . 0.5(3)
C6 C7 C2 C1 . -175.03(19)
C7 C2 C3 C4 . -0.2(3)
C1 C2 C3 C4 . 175.28(19)
C10 C9 C14 C13 . -0.3(3)
C8 C9 C14 C13 . 179.22(17)
C9 C14 C13 C12 . -0.1(3)
C7 C2 C1 N1 . -115.8(2)
C3 C2 C1 N1 . 68.7(2)
C2 C3 C4 C5 . -0.5(3)
C10 C9 C8 N2 . 81.2(3)
C14 C9 C8 N2 . -98.3(2)
C7 C6 C5 C4 . -0.6(4)
C3 C4 C5 C6 . 0.9(4)
Cu1 O1 N3 O2 . -13.76(18)
Cu1 O1 N3 O3 . 165.38(11)
C14 C9 C10 C11 . 0.8(3)
C8 C9 C10 C11 . -178.7(2)
C14 C13 C12 C11 . 0.0(3)
C13 C12 C11 C10 . 0.5(4)
C9 C10 C11 C12 . -0.9(4)
N4 O4 Cu1 O4 2_556 178.14(10)
N4 O4 Cu1 O1 . 84.25(10)
N4 O4 Cu1 O1 2_556 -87.64(10)
N3 O1 Cu1 O4 . 91.75(10)
N3 O1 Cu1 O4 2_556 -76.32(10)
