#------------------------------------------------------------------------------
#$Date: 2019-11-25 08:34:05 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240529 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/98/4129881.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_4129881
loop_
_publ_author_name
'Duprey, Jean-Louis H A'
'Carr-Smith, James'
'Horswell, Sarah L.'
'Kowalski, Jarosław'
'Tucker, James H. R.'
_publ_section_title
;
 Macrocyclic Metal Complex-DNA Conjugates for Electrochemical Sensing of
 Single Nucleobase Changes in DNA.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              746
_journal_page_last               749
_journal_paper_doi               10.1021/jacs.5b11319
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C18 H30 Cu N4 O8'
_chemical_formula_sum            'C18 H30 Cu N4 O8'
_chemical_formula_weight         494.00
_chemical_name_systematic
; 
6,13-bis[carbo(3-hydroxypropoxy)]-1,4,8,11-tetraazacyclotetradeca-4,6,11,13-tetraenato(2-)-k4N(1,4,8,11)copper(II)
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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                 95.4710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.85260(10)
_cell_length_b                   26.9297(5)
_cell_length_c                   8.29640(10)
_cell_measurement_reflns_used    6083
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.92
_cell_measurement_theta_min      3.28
_cell_volume                     1079.23(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9309
_diffrn_reflns_theta_full        66.13
_diffrn_reflns_theta_max         66.13
_diffrn_reflns_theta_min         3.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.896
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
' SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction '
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         1835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.2715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0885
_reflns_number_gt                1730
_reflns_number_total             1835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b11319_si_002.cif
_cod_data_source_block           2CuL
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file
'/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4129881
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_group
Cu1 Cu 0.5000 0.5000 0.5000 0.03417(16) Uani 1 2 d S .
N1 N 0.2989(3) 0.44223(5) 0.42148(18) 0.0411(3) Uani 1 1 d . .
C2 C 0.1301(3) 0.41645(6) 0.5003(2) 0.0390(4) Uani 1 1 d . .
C3 C 0.0652(3) 0.42696(6) 0.6592(2) 0.0364(4) Uani 1 1 d . .
C4 C 0.1815(4) 0.46681(6) 0.7536(2) 0.0397(4) Uani 1 1 d . .
N5 N 0.3533(4) 0.49929(4) 0.7061(2) 0.0391(4) Uani 1 1 d . .
C7 C 0.319(2) 0.4364(4) 0.2377(11) 0.0441(17) Uani 0.432(14) 1 d P 1
H7A H 0.2902 0.4020 0.2061 0.053 Uiso 0.432(14) 1 calc PR 1
H7B H 0.1775 0.4564 0.1777 0.053 Uiso 0.432(14) 1 calc PR 1
C6 C 0.402(2) 0.5469(3) 0.7981(9) 0.0422(17) Uani 0.432(14) 1 d P 1
H6A H 0.2627 0.5714 0.7620 0.051 Uiso 0.432(14) 1 calc PR 1
H6B H 0.3961 0.5415 0.9133 0.051 Uiso 0.432(14) 1 calc PR 1
C7' C 0.3949(16) 0.4217(3) 0.2771(9) 0.0444(14) Uani 0.568(14) 1 d P 2
H7A' H 0.2471 0.4040 0.2147 0.053 Uiso 0.568(14) 1 calc PR 2
H7B' H 0.5479 0.3991 0.3038 0.053 Uiso 0.568(14) 1 calc PR 2
C6' C 0.5106(17) 0.5330(3) 0.8189(6) 0.0460(14) Uani 0.568(14) 1 d P 2
H6A' H 0.6705 0.5160 0.8718 0.055 Uiso 0.568(14) 1 calc PR 2
H6B' H 0.3956 0.5441 0.9014 0.055 Uiso 0.568(14) 1 calc PR 2
C8 C -0.1187(4) 0.39430(6) 0.7379(2) 0.0402(4) Uani 1 1 d . .
O9 O -0.1844(3) 0.39919(5) 0.87484(17) 0.0567(4) Uani 1 1 d . .
O10 O -0.2146(3) 0.35655(5) 0.64177(16) 0.0502(3) Uani 1 1 d . .
C11 C -0.4098(4) 0.32266(7) 0.7033(2) 0.0446(4) Uani 1 1 d . .
C12 C -0.5163(4) 0.29024(7) 0.5635(3) 0.0472(4) Uani 1 1 d . .
C13 C -0.3045(4) 0.25532(8) 0.5053(2) 0.0482(4) Uani 1 1 d . .
O14 O -0.2098(3) 0.21983(6) 0.6247(2) 0.0561(4) Uani 1 1 d . .
O1W O -0.6981(3) 0.16634(6) 0.6393(2) 0.0539(4) Uani 1 1 d . .
H2 H 0.047(4) 0.3900(8) 0.451(3) 0.040(5) Uiso 1 1 d . .
H4 H 0.114(4) 0.4694(7) 0.862(2) 0.045(5) Uiso 1 1 d . .
H11A H -0.306(4) 0.3018(8) 0.797(2) 0.046(5) Uiso 1 1 d . .
H11B H -0.549(5) 0.3416(9) 0.744(3) 0.055(6) Uiso 1 1 d . .
H12A H -0.663(5) 0.2703(9) 0.595(3) 0.057(6) Uiso 1 1 d . .
H12B H -0.583(5) 0.3091(9) 0.472(3) 0.057(6) Uiso 1 1 d . .
H13A H -0.139(5) 0.2739(8) 0.478(3) 0.057(6) Uiso 1 1 d . .
H13B H -0.383(5) 0.2391(9) 0.409(3) 0.052(6) Uiso 1 1 d . .
H14 H -0.330(6) 0.2029(9) 0.646(3) 0.055(7) Uiso 1 1 d . .
H1W H -0.837(7) 0.1817(11) 0.627(3) 0.075(9) Uiso 1 1 d . .
H2W H -0.715(6) 0.1497(11) 0.566(3) 0.073(9) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
N5 Cu1 N5 180.000(1) . 3_666
N5 Cu1 N1 94.29(6) . .
N5 Cu1 N1 85.71(6) 3_666 .
N5 Cu1 N1 85.71(6) . 3_666
N5 Cu1 N1 94.29(6) 3_666 3_666
N1 Cu1 N1 180.00(5) . 3_666
C2 N1 C7' 119.0(3) . .
C2 N1 C7 123.0(3) . .
C7' N1 C7 23.4(2) . .
C2 N1 Cu1 126.05(12) . .
C7' N1 Cu1 113.6(3) . .
C7 N1 Cu1 109.9(3) . .
N1 C2 C3 124.81(15) . .
C2 C3 C4 123.79(15) . .
C2 C3 C8 120.00(15) . .
C4 C3 C8 116.12(15) . .
N5 C4 C3 125.34(16) . .
C4 N5 C6' 122.4(2) . .
C4 N5 C6 119.8(3) . .
C6' N5 C6 25.5(2) . .
C4 N5 Cu1 125.69(12) . .
C6' N5 Cu1 110.4(2) . .
C6 N5 Cu1 113.1(3) . .
C6 C7 N1 108.1(7) 3_666 .
C7 C6 N5 105.0(7) 3_666 .
N1 C7' C6' 105.2(5) . 3_666
N5 C6' C7' 108.8(5) . 3_666
O9 C8 O10 121.90(16) . .
O9 C8 C3 125.60(16) . .
O10 C8 C3 112.50(15) . .
C8 O10 C11 117.97(14) . .
O10 C11 C12 106.47(16) . .
C11 C12 C13 114.53(16) . .
O14 C13 C12 112.43(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N5 1.9142(17) .
Cu1 N5 1.9142(17) 3_666
Cu1 N1 1.9173(14) .
Cu1 N1 1.9173(14) 3_666
N1 C2 1.297(2) .
N1 C7' 1.436(6) .
N1 C7 1.544(9) .
C2 C3 1.413(2) .
C3 C4 1.414(2) .
C3 C8 1.452(2) .
C4 N5 1.295(2) .
N5 C6' 1.465(5) .
N5 C6 1.499(6) .
C7 C6 1.486(14) 3_666
C6 C7 1.486(14) 3_666
C7' C6' 1.548(11) 3_666
C6' C7' 1.548(11) 3_666
C8 O9 1.216(2) .
C8 O10 1.348(2) .
O10 C11 1.443(2) .
C11 C12 1.503(3) .
C12 C13 1.506(3) .
C13 O14 1.421(3) .
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_4
N5 Cu1 N1 C2 -0.04(16) . .
N5 Cu1 N1 C2 179.96(16) 3_666 .
N1 Cu1 N1 C2 -96(100) 3_666 .
N5 Cu1 N1 C7' -166.6(4) . .
N5 Cu1 N1 C7' 13.4(4) 3_666 .
N1 Cu1 N1 C7' 98(100) 3_666 .
N5 Cu1 N1 C7 168.4(5) . .
N5 Cu1 N1 C7 -11.6(5) 3_666 .
N1 Cu1 N1 C7 73(100) 3_666 .
C7' N1 C2 C3 166.1(5) . .
C7 N1 C2 C3 -166.8(5) . .
Cu1 N1 C2 C3 0.2(3) . .
N1 C2 C3 C4 -1.2(3) . .
N1 C2 C3 C8 -177.55(16) . .
C2 C3 C4 N5 2.2(3) . .
C8 C3 C4 N5 178.74(17) . .
C3 C4 N5 C6' -166.8(5) . .
C3 C4 N5 C6 163.4(5) . .
C3 C4 N5 Cu1 -2.1(3) . .
N5 Cu1 N5 C4 -10(100) 3_666 .
N1 Cu1 N5 C4 0.98(17) . .
N1 Cu1 N5 C4 -179.02(17) 3_666 .
N5 Cu1 N5 C6' 156(100) 3_666 .
N1 Cu1 N5 C6' 167.2(4) . .
N1 Cu1 N5 C6' -12.8(4) 3_666 .
N5 Cu1 N5 C6 -176(100) 3_666 .
N1 Cu1 N5 C6 -165.4(5) . .
N1 Cu1 N5 C6 14.6(5) 3_666 .
C2 N1 C7 C6 -155.6(7) . 3_666
C7' N1 C7 C6 -68.1(14) . 3_666
Cu1 N1 C7 C6 35.5(10) . 3_666
C4 N5 C6 C7 155.5(6) . 3_666
C6' N5 C6 C7 52.0(11) . 3_666
Cu1 N5 C6 C7 -37.2(10) . 3_666
C2 N1 C7' C6' 158.5(5) . 3_666
C7 N1 C7' C6' 51.9(12) . 3_666
Cu1 N1 C7' C6' -33.8(8) . 3_666
C4 N5 C6' C7' -159.0(5) . 3_666
C6 N5 C6' C7' -66.8(11) . 3_666
Cu1 N5 C6' C7' 34.3(8) . 3_666
C2 C3 C8 O9 178.53(18) . .
C4 C3 C8 O9 1.9(3) . .
C2 C3 C8 O10 -1.6(2) . .
C4 C3 C8 O10 -178.22(15) . .
O9 C8 O10 C11 2.7(3) . .
C3 C8 O10 C11 -177.20(15) . .
C8 O10 C11 C12 170.71(15) . .
O10 C11 C12 C13 68.0(2) . .
C11 C12 C13 O14 63.9(2) . .
