#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/09/2010998.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_2010998
loop_
_publ_author_name
'Marcus, Sebastian T.'
'Gahan, Lawrence R.'
'Bernhardt, Paul V.'
_publ_section_title
;
 The NiII, HgII and CuII complexes of 12-membered-ring
 mixed-donor macrocycles
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              655
_journal_page_last               658
_journal_paper_doi               10.1107/S0108270100003942
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          '[Cu(NO3 )(C8 H19 N3 O)(H2 O)](NO3 )'
_chemical_formula_moiety         'C8 H21 CuN4 O5 + , NO3 - '
_chemical_formula_sum            'C8 H21 Cu N5 O8'
_chemical_formula_weight         378.84
_chemical_name_systematic
;
aqua(1,7-dioxa-4-thia-10-azacyclododecane)nitratocopper(II) nitrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.627(8)
_cell_angle_beta                 112.107(9)
_cell_angle_gamma                99.509(9)
_cell_formula_units_Z            2
_cell_length_a                   8.6167(9)
_cell_length_b                   9.3975(8)
_cell_length_c                   10.1180(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     737.05(14)
_computing_cell_refinement       'SET4 in CAD4 Manual  (Enraf-Nonius, 1988)'
_computing_data_collection       'CAD4 Manual (Enraf-Nonius, 1988)'
_computing_data_reduction        'XTAL3.2 (Hall et al., 1992)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'ω-2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0248
_diffrn_reflns_av_sigmaI/netI    .0157
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2774
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        <5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  .632
_exptl_absorpt_correction_T_min  .401
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             394
_exptl_crystal_size_max          .60
_exptl_crystal_size_mid          .60
_exptl_crystal_size_min          .30
_refine_diff_density_max         .355
_refine_diff_density_min         -.265
_refine_ls_extinction_coef       .096(3)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          .0275
_refine_ls_R_factor_gt           .0243
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0343P)²+0.4836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0677
_reflns_number_gt                2392
_reflns_number_total             2586
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1589.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.4836P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.4836P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        737.05(12)
_cod_database_code               2010998
_cod_database_fobs_code          2010998
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 .21252(3) .31381(3) .28989(3) .02718(12) Uani d . 1 . . Cu
N1 .4259(2) .3414(2) .2459(2) .0323(4) Uani d . 1 . . N
H1 .4852 .4361 .2790 .039 Uiso d R 1 . . H
N2 .2809(2) .13935(19) .3690(2) .0324(4) Uani d . 1 . . N
H2 .3292 .1633 .4674 .039 Uiso d R 1 . . H
N3 -.0304(2) .2185(2) .2627(2) .0358(4) Uani d . 1 . . N
H3 -.0734 .2846 .3028 .043 Uiso d R 1 . . H
O1 .1719(2) .51182(16) .26897(18) .0363(4) Uani d . 1 . . O
O2 .0888(2) .22036(17) .04050(17) .0363(4) Uani d . 1 . . O
H21 .1158 .5411 .3073 .044 Uiso d R 1 . . H
H22 .2444 .5720 .2825 .044 Uiso d R 1 . . H
C1 .2013(3) .3174(3) -.0028(3) .0417(6) Uani d . 1 . . C
H1A .1890 .4175 .0144 .050 Uiso d R 1 . . H
H1B .1748 .2892 -.1051 .050 Uiso d R 1 . . H
C2 .3804(3) .3044(3) .0871(3) .0414(6) Uani d . 1 . . C
H2A .3916 .2050 .0642 .050 Uiso d R 1 . . H
H2B .4609 .3695 .0621 .050 Uiso d R 1 . . H
C3 .5307(3) .2438(3) .3283(3) .0401(5) Uani d . 1 . . C
H3A .5948 .2912 .4286 .048 Uiso d R 1 . . H
H3B .6118 .2239 .2874 .048 Uiso d R 1 . . H
C4 .4125(3) .1017(3) .3205(3) .0409(5) Uani d . 1 . . C
H4A .3585 .0481 .2219 .049 Uiso d R 1 . . H
H4B .4769 .0408 .3823 .049 Uiso d R 1 . . H
C5 .1237(3) .0239(2) .3266(3) .0409(5) Uani d . 1 . . C
H5A .1456 -.0504 .3873 .049 Uiso d R 1 . . H
H5B .0864 -.0225 .2265 .049 Uiso d R 1 . . H
C6 -.0126(3) .0955(3) .3451(3) .0428(6) Uani d . 1 . . C
H6A -.1210 .0246 .3095 .051 Uiso d R 1 . . H
H6B .0195 .1322 .4469 .051 Uiso d R 1 . . H
C7 -.1451(3) .1706(3) .1063(3) .0458(6) Uani d . 1 . . C
H7A -.2583 .1877 .0903 .055 Uiso d R 1 . . H
H7B -.1566 .0662 .0795 .055 Uiso d R 1 . . H
C8 -.0768(3) .2509(3) .0112(3) .0429(6) Uani d . 1 . . C
H8A -.1519 .2168 -.0901 .051 Uiso d R 1 . . H
H8B -.0677 .3554 .0342 .051 Uiso d R 1 . . H
N4 .1509(2) .4333(2) .6302(2) .0361(4) Uani d . 1 . . N
O3 .2037(2) .5294(2) .73981(19) .0467(4) Uani d . 1 . . O
O4 -.0026(2) .3634(2) .5789(2) .0533(5) Uani d . 1 . . O
O5 .2479(2) .4077(2) .56979(19) .0444(4) Uani d . 1 . . O
N5 .4988(2) .2483(2) .7541(2) .0384(5) Uani d . 1 . . N
O6 .5639(2) .25468(19) .66193(18) .0443(4) Uani d . 1 . . O
O7 .3773(3) .1476(2) .7311(3) .0823(8) Uani d . 1 . . O
O8 .5587(3) .3456(3) .8614(2) .0633(6) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu .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_publ_flag
O1 Cu1 N2 163.92(7) yes
O1 Cu1 N1 96.37(7) yes
N2 Cu1 N1 86.73(7) yes
O1 Cu1 N3 96.54(7) yes
N2 Cu1 N3 86.40(8) yes
N1 Cu1 N3 156.15(8) yes
O1 Cu1 O2 95.29(6) yes
N2 Cu1 O2 100.79(7) yes
N1 Cu1 O2 79.83(7) yes
N3 Cu1 O2 79.07(7) yes
O1 Cu1 O5 81.64(6) yes
N2 Cu1 O5 83.03(6) yes
N1 Cu1 O5 118.63(6) yes
N3 Cu1 O5 83.11(7) yes
O2 Cu1 O5 161.46(5) yes
C3 N1 C2 111.98(18) ?
C3 N1 Cu1 105.46(13) ?
C2 N1 Cu1 111.26(14) ?
C4 N2 C5 115.95(18) ?
C4 N2 Cu1 108.32(13) ?
C5 N2 Cu1 107.86(14) ?
C6 N3 C7 113.13(19) ?
C6 N3 Cu1 105.76(14) ?
C7 N3 Cu1 111.33(14) ?
C8 O2 C1 116.32(19) ?
C8 O2 Cu1 97.41(13) ?
C1 O2 Cu1 98.62(13) ?
O2 C1 C2 106.39(19) ?
N1 C2 C1 112.69(19) ?
N1 C3 C4 108.98(19) ?
N2 C4 C3 107.58(19) ?
N2 C5 C6 107.65(18) ?
N3 C6 C5 108.79(18) ?
N3 C7 C8 111.87(19) ?
O2 C8 C7 106.0(2) ?
O3 N4 O5 120.5(2) ?
O3 N4 O4 119.46(19) ?
O5 N4 O4 120.0(2) ?
N4 O5 Cu1 136.44(14) ?
O7 N5 O8 123.3(2) ?
O7 N5 O6 118.5(2) ?
O8 N5 O6 118.2(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.9663(15) yes
Cu1 N2 . 1.9742(18) yes
Cu1 N1 . 2.0312(18) yes
Cu1 N3 . 2.0393(18) yes
Cu1 O2 . 2.3465(16) yes
Cu1 O5 . 2.7682(17) yes
N1 C3 . 1.486(3) ?
N1 C2 . 1.493(3) ?
N2 C4 . 1.472(3) ?
N2 C5 . 1.477(3) ?
N3 C6 . 1.484(3) ?
N3 C7 . 1.490(3) ?
O2 C8 . 1.428(3) ?
O2 C1 . 1.438(3) ?
C1 C2 . 1.501(4) ?
C3 C4 . 1.515(3) ?
C5 C6 . 1.506(4) ?
C7 C8 . 1.504(4) ?
N4 O3 . 1.241(3) ?
N4 O5 . 1.247(2) ?
N4 O4 . 1.257(3) ?
N5 O7 . 1.222(3) ?
N5 O8 . 1.228(3) ?
N5 O6 . 1.257(3) ?
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 H1 O5 2_666 .91 2.36 3.153(3) 145.2
N1 H1 O8 2_666 .91 2.61 3.234(3) 126.7
N2 H2 O6 . .91 2.19 2.994(3) 146.7
N2 H2 O7 . .91 2.56 3.428(4) 158.6
N2 H2 N5 . .91 2.68 3.582(3) 174.3
N3 H3 O3 2_566 .91 2.22 3.000(3) 143.2
N3 H3 O4 . .91 2.62 3.257(3) 127.3
O1 H21 O4 2_566 .79 2.00 2.788(2) 172.1
O1 H21 O3 2_566 .79 2.57 3.162(2) 133.2
O1 H21 N4 2_566 .79 2.64 3.398(2) 160.7
O1 H22 O6 2_666 .73 1.98 2.709(2) 173.5
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
O1 Cu1 N1 C3 150.35(14)
N2 Cu1 N1 C3 -13.81(15)
N3 Cu1 N1 C3 -87.3(2)
O2 Cu1 N1 C3 -115.40(15)
O5 Cu1 N1 C3 66.42(16)
O1 Cu1 N1 C2 -88.04(15)
N2 Cu1 N1 C2 107.80(16)
N3 Cu1 N1 C2 34.4(3)
O2 Cu1 N1 C2 6.22(14)
O5 Cu1 N1 C2 -171.96(14)
O1 Cu1 N2 C4 -116.4(2)
N1 Cu1 N2 C4 -14.67(15)
N3 Cu1 N2 C4 142.48(16)
O2 Cu1 N2 C4 64.33(15)
O5 Cu1 N2 C4 -134.04(15)
O1 Cu1 N2 C5 117.4(2)
N1 Cu1 N2 C5 -140.89(15)
N3 Cu1 N2 C5 16.26(14)
O2 Cu1 N2 C5 -61.89(15)
O5 Cu1 N2 C5 99.74(14)
O1 Cu1 N3 C6 -151.71(14)
N2 Cu1 N3 C6 12.42(14)
N1 Cu1 N3 C6 85.9(2)
O2 Cu1 N3 C6 114.14(14)
O5 Cu1 N3 C6 -70.99(14)
O1 Cu1 N3 C7 85.03(16)
N2 Cu1 N3 C7 -110.84(16)
N1 Cu1 N3 C7 -37.3(3)
O2 Cu1 N3 C7 -9.12(15)
O5 Cu1 N3 C7 165.75(16)
O1 Cu1 O2 C8 -57.47(14)
N2 Cu1 O2 C8 122.34(14)
N1 Cu1 O2 C8 -153.01(14)
N3 Cu1 O2 C8 38.19(14)
O5 Cu1 O2 C8 22.0(2)
O1 Cu1 O2 C1 60.69(14)
N2 Cu1 O2 C1 -119.50(14)
N1 Cu1 O2 C1 -34.85(13)
N3 Cu1 O2 C1 156.35(14)
O5 Cu1 O2 C1 140.12(18)
C8 O2 C1 C2 158.04(19)
Cu1 O2 C1 C2 55.31(19)
C3 N1 C2 C1 141.5(2)
Cu1 N1 C2 C1 23.7(2)
O2 C1 C2 N1 -58.0(3)
C2 N1 C3 C4 -81.9(2)
Cu1 N1 C3 C4 39.2(2)
C5 N2 C4 C3 161.1(2)
Cu1 N2 C4 C3 39.8(2)
N1 C3 C4 N2 -53.5(2)
C4 N2 C5 C6 -163.2(2)
Cu1 N2 C5 C6 -41.6(2)
C7 N3 C6 C5 83.6(2)
Cu1 N3 C6 C5 -38.5(2)
N2 C5 C6 N3 54.1(3)
C6 N3 C7 C8 -140.1(2)
Cu1 N3 C7 C8 -21.2(2)
C1 O2 C8 C7 -161.99(19)
Cu1 O2 C8 C7 -58.53(18)
N3 C7 C8 O2 58.9(2)
O3 N4 O5 Cu1 -148.60(17)
O4 N4 O5 Cu1 30.2(3)
O1 Cu1 O5 N4 71.5(2)
N2 Cu1 O5 N4 -113.4(2)
N1 Cu1 O5 N4 164.2(2)
N3 Cu1 O5 N4 -26.2(2)
O2 Cu1 O5 N4 -10.2(3)
