#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:16:34 +0100 (vie 25 de mar de 2016) $
#$Revision: 179746 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/42/7004297.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_7004297
loop_
_publ_author_name
'Santillan, Guillermo A.'
'Carrano, Carl J.'
_publ_section_title
;
 Nickel(ii), copper(ii), and cobalt(ii) solid-state structures formed
 through hydrogen bonding with ditopic heteroscorpionate ligands
;
_journal_issue                   30
_journal_name_full               'Dalton Transactions'
_journal_page_first              3995
_journal_page_last               4005
_journal_paper_doi               10.1039/B805253K
_journal_year                    2008
_chemical_formula_sum            'C19 H20 Cu N6 O9'
_chemical_formula_weight         539.95
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.679(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.813(2)
_cell_length_b                   14.928(3)
_cell_length_c                   17.776(4)
_cell_measurement_reflns_used    5817
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      20.94
_cell_measurement_theta_min      2.31
_cell_volume                     2322.7(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      240(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33245
_diffrn_reflns_theta_full        21.00
_diffrn_reflns_theta_max         21.00
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         2476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0368
_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)+(0.0536P)²+4.7900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                2199
_reflns_number_total             2476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B805253K.txt
_cod_data_source_block           gs47a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2322.8(9)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7004297
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.10185(5) 0.60575(3) 0.33975(3) 0.0327(2) Uani 1 1 d . . .
N1 N 0.1115(4) 0.6265(2) 0.23041(19) 0.0312(9) Uani 1 1 d . . .
N2 N 0.0075(4) 0.6829(2) 0.19172(18) 0.0308(8) Uani 1 1 d . . .
N3 N -0.1168(4) 0.6297(2) 0.32842(19) 0.0328(9) Uani 1 1 d . . .
N4 N -0.1844(4) 0.6859(2) 0.27442(19) 0.0311(8) Uani 1 1 d . . .
N5 N 0.2641(6) 0.4616(3) 0.3680(2) 0.0550(11) Uani 1 1 d . . .
N6 N 0.2214(4) 0.6850(3) 0.4629(3) 0.0451(10) Uani 1 1 d . . .
O1 O 0.3526(4) 1.0513(2) 0.38546(19) 0.0547(10) Uani 1 1 d . . .
H100 H 0.405(7) 1.090(4) 0.413(3) 0.08(2) Uiso 1 1 d . . .
O2 O 0.2083(3) 1.0283(2) 0.47776(18) 0.0473(8) Uani 1 1 d . . .
O3 O 0.1276(5) 0.4432(2) 0.3562(2) 0.0657(10) Uani 1 1 d . . .
O4 O 0.3006(3) 0.5444(2) 0.36017(18) 0.0467(8) Uani 1 1 d . . .
O5 O 0.3628(6) 0.4068(3) 0.3856(3) 0.0980(15) Uani 1 1 d . . .
O6 O 0.2663(4) 0.7206(2) 0.4069(2) 0.0580(9) Uani 1 1 d . . .
O7 O 0.1164(3) 0.6248(2) 0.45094(16) 0.0437(8) Uani 1 1 d . . .
O8 O 0.2705(4) 0.7034(3) 0.5282(2) 0.0646(10) Uani 1 1 d . . .
C1 C -0.0773(5) 0.7393(3) 0.0624(2) 0.0454(12) Uani 1 1 d . . .
H1A H -0.1470 0.7732 0.0888 0.068 Uiso 1 1 calc R . .
H1B H -0.1338 0.7017 0.0253 0.068 Uiso 1 1 calc R . .
H1C H -0.0141 0.7795 0.0376 0.068 Uiso 1 1 calc R . .
C2 C 0.0199(5) 0.6831(3) 0.1169(2) 0.0345(11) Uani 1 1 d . . .
C3 C 0.1337(5) 0.6238(3) 0.1072(3) 0.0413(12) Uani 1 1 d . . .
H3A H 0.1687 0.6090 0.0614 0.050 Uiso 1 1 calc R . .
C4 C 0.1874(5) 0.5898(3) 0.1769(2) 0.0338(11) Uani 1 1 d . . .
C5 C 0.3077(5) 0.5208(3) 0.1930(3) 0.0476(13) Uani 1 1 d . . .
H5A H 0.3227 0.5088 0.2464 0.071 Uiso 1 1 calc R . .
H5B H 0.4015 0.5421 0.1769 0.071 Uiso 1 1 calc R . .
H5C H 0.2770 0.4668 0.1661 0.071 Uiso 1 1 calc R . .
C6 C -0.4408(5) 0.7443(4) 0.2242(3) 0.0558(14) Uani 1 1 d . . .
H6A H -0.5441 0.7353 0.2346 0.084 Uiso 1 1 calc R . .
H6B H -0.4320 0.7282 0.1726 0.084 Uiso 1 1 calc R . .
H6C H -0.4135 0.8062 0.2320 0.084 Uiso 1 1 calc R . .
C7 C -0.3370(5) 0.6877(3) 0.2755(2) 0.0367(11) Uani 1 1 d . . .
C8 C -0.3672(5) 0.6298(3) 0.3305(3) 0.0446(12) Uani 1 1 d . . .
H8A H -0.4633 0.6164 0.3443 0.053 Uiso 1 1 calc R . .
C9 C -0.2301(5) 0.5940(3) 0.3626(2) 0.0382(11) Uani 1 1 d . . .
C10 C -0.2016(6) 0.5269(3) 0.4239(3) 0.0558(14) Uani 1 1 d . . .
H10A H -0.0938 0.5160 0.4341 0.084 Uiso 1 1 calc R . .
H10B H -0.2531 0.4721 0.4086 0.084 Uiso 1 1 calc R . .
H10C H -0.2394 0.5492 0.4689 0.084 Uiso 1 1 calc R . .
C11 C -0.0878(4) 0.7404(3) 0.2321(2) 0.0308(10) Uani 1 1 d . . .
H11A H -0.1552 0.7734 0.1941 0.037 Uiso 1 1 calc R . .
C12 C 0.0031(4) 0.8089(3) 0.2809(2) 0.0275(10) Uani 1 1 d . . .
C13 C 0.1301(5) 0.8484(3) 0.2564(2) 0.0332(10) Uani 1 1 d . . .
H13A H 0.1637 0.8300 0.2112 0.040 Uiso 1 1 calc R . .
C14 C 0.2074(5) 0.9151(3) 0.2987(2) 0.0353(11) Uani 1 1 d . . .
H14A H 0.2925 0.9418 0.2816 0.042 Uiso 1 1 calc R . .
C15 C 0.1590(5) 0.9427(3) 0.3662(2) 0.0296(10) Uani 1 1 d . . .
C16 C 0.2407(5) 1.0111(3) 0.4157(3) 0.0347(11) Uani 1 1 d . . .
C17 C 0.0308(5) 0.9041(3) 0.3899(2) 0.0320(10) Uani 1 1 d . . .
H17A H -0.0037 0.9229 0.4349 0.038 Uiso 1 1 calc R . .
C18 C -0.0466(4) 0.8376(3) 0.3475(2) 0.0307(10) Uani 1 1 d . . .
H18A H -0.1331 0.8119 0.3639 0.037 Uiso 1 1 calc R . .
O9 O 0.4955(4) 1.1637(3) 0.4840(2) 0.0730(11) Uani 1 1 d . . .
C19 C 0.4414(6) 1.1728(5) 0.5558(3) 0.0750(18) 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
_geom_angle_publ_flag
N3 Cu1 O4 162.04(14) . . ?
N3 Cu1 N1 91.43(14) . . ?
O4 Cu1 N1 96.57(13) . . ?
N3 Cu1 O7 91.45(13) . . ?
O4 Cu1 O7 85.98(13) . . ?
N1 Cu1 O7 161.69(14) . . ?
C4 N1 N2 104.8(3) . . ?
C4 N1 Cu1 135.6(3) . . ?
N2 N1 Cu1 119.1(2) . . ?
C2 N2 N1 111.7(3) . . ?
C2 N2 C11 127.4(4) . . ?
N1 N2 C11 120.5(3) . . ?
C9 N3 N4 106.1(3) . . ?
C9 N3 Cu1 131.4(3) . . ?
N4 N3 Cu1 122.2(2) . . ?
C7 N4 N3 111.0(3) . . ?
C7 N4 C11 130.1(4) . . ?
N3 N4 C11 118.5(3) . . ?
O5 N5 O3 123.7(5) . . ?
O5 N5 O4 119.7(5) . . ?
O3 N5 O4 116.6(4) . . ?
O8 N6 O6 123.9(4) . . ?
O8 N6 O7 118.9(4) . . ?
O6 N6 O7 117.2(4) . . ?
C16 O1 H100 116(4) . . ?
N5 O4 Cu1 103.7(3) . . ?
N6 O7 Cu1 103.1(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C3 105.6(4) . . ?
N2 C2 C1 122.8(4) . . ?
C3 C2 C1 131.6(4) . . ?
C2 C3 C4 107.9(4) . . ?
C2 C3 H3A 126.0 . . ?
C4 C3 H3A 126.0 . . ?
N1 C4 C3 110.0(4) . . ?
N1 C4 C5 123.5(4) . . ?
C3 C4 C5 126.6(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C8 106.1(4) . . ?
N4 C7 C6 123.3(4) . . ?
C8 C7 C6 130.6(4) . . ?
C7 C8 C9 108.0(4) . . ?
C7 C8 H8A 126.0 . . ?
C9 C8 H8A 126.0 . . ?
N3 C9 C8 108.8(4) . . ?
N3 C9 C10 122.2(4) . . ?
C8 C9 C10 129.1(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 N4 109.6(3) . . ?
N2 C11 C12 112.7(3) . . ?
N4 C11 C12 112.8(3) . . ?
N2 C11 H11A 107.1 . . ?
N4 C11 H11A 107.1 . . ?
C12 C11 H11A 107.1 . . ?
C18 C12 C13 119.3(4) . . ?
C18 C12 C11 120.3(3) . . ?
C13 C12 C11 120.3(3) . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C17 C15 C14 119.2(4) . . ?
C17 C15 C16 117.9(4) . . ?
C14 C15 C16 122.9(4) . . ?
O2 C16 O1 123.0(4) . . ?
O2 C16 C15 122.9(4) . . ?
O1 C16 C15 114.0(4) . . ?
C15 C17 C18 120.3(4) . . ?
C15 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C12 C18 C17 120.6(4) . . ?
C12 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
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 N3 1.947(3) . ?
Cu1 O4 1.972(3) . ?
Cu1 N1 1.980(3) . ?
Cu1 O7 1.986(3) . ?
N1 C4 1.341(5) . ?
N1 N2 1.370(5) . ?
N2 C2 1.347(5) . ?
N2 C11 1.448(5) . ?
N3 C9 1.338(5) . ?
N3 N4 1.359(5) . ?
N4 C7 1.347(5) . ?
N4 C11 1.449(5) . ?
N5 O5 1.208(5) . ?
N5 O3 1.228(5) . ?
N5 O4 1.289(5) . ?
N6 O8 1.222(5) . ?
N6 O6 1.235(5) . ?
N6 O7 1.289(5) . ?
O1 C16 1.321(5) . ?
O1 H100 0.86(6) . ?
O2 C16 1.200(5) . ?
C1 C2 1.478(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.363(6) . ?
C3 C4 1.371(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.482(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.479(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.355(6) . ?
C8 C9 1.382(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.480(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.509(6) . ?
C11 H11A 0.9800 . ?
C12 C18 1.377(5) . ?
C12 C13 1.380(6) . ?
C13 C14 1.379(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.383(6) . ?
C14 H14A 0.9300 . ?
C15 C17 1.377(6) . ?
C15 C16 1.478(6) . ?
C17 C18 1.378(6) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
O9 C19 1.420(6) . ?
