#------------------------------------------------------------------------------
#$Date: 2019-11-08 01:08:57 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/98/7049874.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_7049874
loop_
_publ_author_name
'Lee, Wei-Li'
'Hsu, Tse-Wei'
'Hung, Wei-Cheng'
'Fang, Jim-Min'
_publ_section_title
;
 A copper(ii)-dipicolylamine-coumarin sensor for maltosyltransferase
 assay.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8026
_journal_page_last               8029
_journal_paper_doi               10.1039/c9dt01339c
_journal_volume                  48
_journal_year                    2019
_chemical_formula_sum            'C48 H46 Cu2 N8 O12'
_chemical_formula_weight         1054.01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-01 deposited with the CCDC.    2019-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                118.519(3)
_cell_angle_beta                 96.302(3)
_cell_angle_gamma                110.063(3)
_cell_formula_units_Z            1
_cell_length_a                   11.7538(10)
_cell_length_b                   12.8198(12)
_cell_length_c                   13.1515(12)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      3.10
_cell_volume                     1543.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41650
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.465
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: H2O/MeOH'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.318
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0869P)²+5.6056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4724
_reflns_number_total             5378
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt01339c2.cif
_cod_data_source_block           dog
_cod_depositor_comments          'Adding full bibliography for 7049874.cif.'
_cod_original_cell_volume        1543.1(2)
_cod_database_code               7049874
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.6538
_shelx_estimated_absorpt_t_max   0.7454
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.35820(4) 0.95748(4) 0.45816(4) 0.01327(15) Uani 1 1 d . .
O1 O 0.8298(3) 1.2671(3) 0.1549(3) 0.0296(7) Uani 1 1 d . .
O2 O 0.6624(3) 1.1642(3) 0.1898(2) 0.0189(6) Uani 1 1 d . .
O3 O 0.5183(2) 1.1122(3) 0.5695(2) 0.0186(6) Uani 1 1 d . .
N1 N 0.3000(3) 0.9738(3) 0.2865(3) 0.0143(6) Uani 1 1 d . .
N2 N 0.2546(3) 1.0603(3) 0.5111(3) 0.0151(6) Uani 1 1 d . .
N3 N 0.2039(3) 0.7800(3) 0.3446(3) 0.0125(6) Uani 1 1 d . .
C1 C 0.7505(4) 1.1601(4) 0.1285(4) 0.0201(8) Uani 1 1 d . .
C2 C 0.7378(4) 1.0313(4) 0.0401(4) 0.0197(8) Uani 1 1 d . .
H2 H 0.7978 1.0263 -0.0027 0.024 Uiso 1 1 calc R U
C3 C 0.6439(4) 0.9166(4) 0.0151(3) 0.0168(8) Uani 1 1 d . .
C4 C 0.6308(4) 0.7837(4) -0.0806(4) 0.0267(9) Uani 1 1 d . .
H4A H 0.5578 0.7131 -0.0854 0.040 Uiso 1 1 calc R U
H4B H 0.6165 0.7736 -0.1603 0.040 Uiso 1 1 calc R U
H4C H 0.7095 0.7773 -0.0589 0.040 Uiso 1 1 calc R U
C5 C 0.5537(4) 0.9246(4) 0.0815(3) 0.0145(7) Uani 1 1 d . .
C6 C 0.5663(3) 1.0497(4) 0.1673(3) 0.0139(7) Uani 1 1 d . .
C7 C 0.4852(3) 1.0705(4) 0.2360(3) 0.0144(7) Uani 1 1 d . .
H7 H 0.4974 1.1580 0.2927 0.017 Uiso 1 1 calc R U
C8 C 0.3850(3) 0.9595(4) 0.2198(3) 0.0134(7) Uani 1 1 d . .
C9 C 0.3717(4) 0.8316(4) 0.1356(3) 0.0185(8) Uani 1 1 d . .
H9 H 0.3052 0.7557 0.1252 0.022 Uiso 1 1 calc R U
C10 C 0.4532(4) 0.8146(4) 0.0681(3) 0.0183(8) Uani 1 1 d . .
H10 H 0.4415 0.7272 0.0116 0.022 Uiso 1 1 calc R U
C11 C 0.3082(4) 1.1084(4) 0.3603(4) 0.0187(8) Uani 1 1 d . .
H11A H 0.2704 1.1287 0.3052 0.022 Uiso 1 1 calc R U
H11B H 0.3995 1.1752 0.4047 0.022 Uiso 1 1 calc R U
C12 C 0.2385(4) 1.1175(4) 0.4508(3) 0.0169(8) Uani 1 1 d . .
C13 C 0.1655(4) 1.1865(4) 0.4751(4) 0.0235(9) Uani 1 1 d . .
H13 H 0.1520 1.2228 0.4293 0.028 Uiso 1 1 calc R U
C14 C 0.1131(4) 1.2011(4) 0.5671(4) 0.0245(9) Uani 1 1 d . .
H14 H 0.0639 1.2490 0.5864 0.029 Uiso 1 1 calc R U
C15 C 0.1325(4) 1.1457(4) 0.6306(4) 0.0217(8) Uani 1 1 d . .
H15 H 0.0973 1.1556 0.6944 0.026 Uiso 1 1 calc R U
C16 C 0.2041(4) 1.0751(4) 0.6009(3) 0.0197(8) Uani 1 1 d . .
C17 C 0.2274(5) 1.0128(5) 0.6676(4) 0.0321(10) Uani 1 1 d . .
H17A H 0.1857 1.0308 0.7304 0.048 Uiso 1 1 calc R U
H17B H 0.1918 0.9163 0.6093 0.048 Uiso 1 1 calc R U
H17C H 0.3200 1.0504 0.7067 0.048 Uiso 1 1 calc R U
C18 C 0.1665(4) 0.8679(4) 0.2195(3) 0.0162(8) Uani 1 1 d . .
H18A H 0.1499 0.8292 0.1307 0.019 Uiso 1 1 calc R U
H18B H 0.1081 0.9085 0.2438 0.019 Uiso 1 1 calc R U
C19 C 0.1335(3) 0.7558(4) 0.2407(3) 0.0144(7) Uani 1 1 d . .
C20 C 0.0298(4) 0.6343(4) 0.1545(4) 0.0224(9) Uani 1 1 d . .
H20 H -0.0161 0.6194 0.0809 0.027 Uiso 1 1 calc R U
C21 C -0.0065(4) 0.5341(4) 0.1767(4) 0.0285(10) Uani 1 1 d . .
H21 H -0.0789 0.4503 0.1200 0.034 Uiso 1 1 calc R U
C22 C 0.0659(4) 0.5596(4) 0.2840(4) 0.0231(9) Uani 1 1 d . .
H22 H 0.0429 0.4925 0.3012 0.028 Uiso 1 1 calc R U
C23 C 0.1706(4) 0.6812(4) 0.3657(3) 0.0164(8) Uani 1 1 d . .
C24 C 0.2521(4) 0.7078(4) 0.4797(4) 0.0232(9) Uani 1 1 d . .
H24A H 0.2172 0.6286 0.4830 0.035 Uiso 1 1 calc R U
H24B H 0.3402 0.7289 0.4785 0.035 Uiso 1 1 calc R U
H24C H 0.2521 0.7832 0.5520 0.035 Uiso 1 1 calc R U
O4 O 0.8630(6) 0.7964(7) 0.1029(5) 0.0895(18) Uani 1 1 d . .
O5 O 0.7376(6) 0.5613(8) -0.0122(7) 0.114(3) Uani 1 1 d . .
O6 O 0.8818(8) 0.6811(10) -0.0669(7) 0.131(3) Uani 1 1 d . .
N4 N 0.8241(8) 0.6755(9) 0.0035(7) 0.089(2) 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'
Cu Cu 0.3201 1.2651 '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'
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
O3 Cu1 O3 77.09(12) . 2_676
O3 Cu1 N3 171.27(11) . .
O3 Cu1 N3 95.13(11) 2_676 .
O3 Cu1 N2 93.09(12) . .
O3 Cu1 N2 170.12(12) 2_676 .
N3 Cu1 N2 94.59(12) . .
O3 Cu1 N1 106.06(11) . .
O3 Cu1 N1 105.77(11) 2_676 .
N3 Cu1 N1 79.68(11) . .
N2 Cu1 N1 77.77(11) . .
O3 Cu1 Cu1 38.70(8) . 2_676
O3 Cu1 Cu1 38.39(8) 2_676 2_676
N3 Cu1 Cu1 133.40(9) . 2_676
N2 Cu1 Cu1 131.78(9) . 2_676
N1 Cu1 Cu1 110.52(8) . 2_676
C6 O2 C1 121.5(3) . .
Cu1 O3 Cu1 102.91(12) . 2_676
C8 N1 C18 115.2(3) . .
C8 N1 C11 117.2(3) . .
C18 N1 C11 112.8(3) . .
C8 N1 Cu1 111.0(2) . .
C18 N1 Cu1 102.0(2) . .
C11 N1 Cu1 95.8(2) . .
C16 N2 C12 119.5(3) . .
C16 N2 Cu1 124.4(3) . .
C12 N2 Cu1 116.0(3) . .
C19 N3 C23 118.7(3) . .
C19 N3 Cu1 118.6(2) . .
C23 N3 Cu1 122.6(2) . .
O1 C1 O2 115.6(4) . .
O1 C1 C2 127.2(4) . .
O2 C1 C2 117.2(3) . .
C3 C2 C1 122.9(4) . .
C3 C2 H2 118.6 . .
C1 C2 H2 118.6 . .
C2 C3 C5 118.4(4) . .
C2 C3 C4 121.5(4) . .
C5 C3 C4 120.1(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C6 C5 C10 116.3(3) . .
C6 C5 C3 118.6(3) . .
C10 C5 C3 125.1(3) . .
O2 C6 C7 114.6(3) . .
O2 C6 C5 121.3(3) . .
C7 C6 C5 124.1(3) . .
C6 C7 C8 118.5(3) . .
C6 C7 H7 120.7 . .
C8 C7 H7 120.7 . .
C7 C8 N1 121.3(3) . .
C7 C8 C9 118.6(3) . .
N1 C8 C9 120.1(3) . .
C10 C9 C8 121.3(3) . .
C10 C9 H9 119.4 . .
C8 C9 H9 119.4 . .
C9 C10 C5 121.1(3) . .
C9 C10 H10 119.4 . .
C5 C10 H10 119.4 . .
N1 C11 C12 111.1(3) . .
N1 C11 H11A 109.4 . .
C12 C11 H11A 109.4 . .
N1 C11 H11B 109.4 . .
C12 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
N2 C12 C13 121.7(4) . .
N2 C12 C11 116.7(3) . .
C13 C12 C11 121.5(3) . .
C14 C13 C12 118.6(4) . .
C14 C13 H13 120.7 . .
C12 C13 H13 120.7 . .
C15 C14 C13 119.5(4) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
C14 C15 C16 119.6(4) . .
C14 C15 H15 120.2 . .
C16 C15 H15 120.2 . .
N2 C16 C15 121.0(4) . .
N2 C16 C17 117.7(4) . .
C15 C16 C17 121.4(4) . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N1 C18 C19 115.0(3) . .
N1 C18 H18A 108.5 . .
C19 C18 H18A 108.5 . .
N1 C18 H18B 108.5 . .
C19 C18 H18B 108.5 . .
H18A C18 H18B 107.5 . .
N3 C19 C20 122.5(3) . .
N3 C19 C18 118.9(3) . .
C20 C19 C18 118.6(3) . .
C19 C20 C21 119.1(4) . .
C19 C20 H20 120.4 . .
C21 C20 H20 120.4 . .
C22 C21 C20 118.2(4) . .
C22 C21 H21 120.9 . .
C20 C21 H21 120.9 . .
C23 C22 C21 120.5(4) . .
C23 C22 H22 119.7 . .
C21 C22 H22 119.7 . .
N3 C23 C22 120.9(3) . .
N3 C23 C24 118.3(3) . .
C22 C23 C24 120.8(3) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
O6 N4 O4 110.6(9) . .
O6 N4 O5 125.5(9) . .
O4 N4 O5 123.8(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.918(3) .
Cu1 O3 1.931(3) 2_676
Cu1 N3 2.007(3) .
Cu1 N2 2.029(3) .
Cu1 N1 2.413(3) .
Cu1 Cu1 3.0110(9) 2_676
O1 C1 1.212(5) .
O2 C6 1.376(4) .
O2 C1 1.380(5) .
O3 Cu1 1.931(3) 2_676
N1 C8 1.401(5) .
N1 C18 1.475(5) .
N1 C11 1.481(5) .
N2 C16 1.341(5) .
N2 C12 1.348(5) .
N3 C19 1.349(5) .
N3 C23 1.361(5) .
C1 C2 1.435(6) .
C2 C3 1.353(6) .
C2 H2 0.9500 .
C3 C5 1.446(5) .
C3 C4 1.497(5) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C6 1.392(5) .
C5 C10 1.411(5) .
C6 C7 1.389(5) .
C7 C8 1.401(5) .
C7 H7 0.9500 .
C8 C9 1.411(5) .
C9 C10 1.378(6) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 C12 1.499(5) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.390(6) .
C13 C14 1.381(6) .
C13 H13 0.9500 .
C14 C15 1.374(6) .
C14 H14 0.9500 .
C15 C16 1.392(6) .
C15 H15 0.9500 .
C16 C17 1.501(6) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C19 1.522(5) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.380(5) .
C20 C21 1.388(6) .
C20 H20 0.9500 .
C21 C22 1.388(6) .
C21 H21 0.9500 .
C22 C23 1.376(6) .
C22 H22 0.9500 .
C23 C24 1.502(5) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
O4 N4 1.330(9) .
O5 N4 1.365(10) .
O6 N4 1.220(9) .
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
C6 O2 C1 O1 179.2(3)
C6 O2 C1 C2 0.1(5)
O1 C1 C2 C3 -178.6(4)
O2 C1 C2 C3 0.4(6)
C1 C2 C3 C5 -0.8(6)
C1 C2 C3 C4 178.0(4)
C2 C3 C5 C6 0.7(5)
C4 C3 C5 C6 -178.1(3)
C2 C3 C5 C10 -178.2(4)
C4 C3 C5 C10 3.1(6)
C1 O2 C6 C7 -179.8(3)
C1 O2 C6 C5 -0.2(5)
C10 C5 C6 O2 178.7(3)
C3 C5 C6 O2 -0.2(5)
C10 C5 C6 C7 -1.7(5)
C3 C5 C6 C7 179.4(3)
O2 C6 C7 C8 -179.6(3)
C5 C6 C7 C8 0.8(5)
C6 C7 C8 N1 179.9(3)
C6 C7 C8 C9 0.8(5)
C18 N1 C8 C7 145.1(3)
C11 N1 C8 C7 8.9(5)
Cu1 N1 C8 C7 -99.6(3)
C18 N1 C8 C9 -35.7(5)
C11 N1 C8 C9 -171.9(3)
Cu1 N1 C8 C9 79.5(4)
C7 C8 C9 C10 -1.4(5)
N1 C8 C9 C10 179.4(3)
C8 C9 C10 C5 0.5(6)
C6 C5 C10 C9 1.0(5)
C3 C5 C10 C9 179.8(4)
C8 N1 C11 C12 -165.0(3)
C18 N1 C11 C12 57.8(4)
Cu1 N1 C11 C12 -47.8(3)
C16 N2 C12 C13 -3.1(6)
Cu1 N2 C12 C13 177.6(3)
C16 N2 C12 C11 174.2(3)
Cu1 N2 C12 C11 -5.1(4)
N1 C11 C12 N2 42.4(5)
N1 C11 C12 C13 -140.2(4)
N2 C12 C13 C14 2.8(6)
C11 C12 C13 C14 -174.4(4)
C12 C13 C14 C15 -1.0(6)
C13 C14 C15 C16 -0.4(6)
C12 N2 C16 C15 1.7(6)
Cu1 N2 C16 C15 -179.1(3)
C12 N2 C16 C17 -178.4(4)
Cu1 N2 C16 C17 0.8(5)
C14 C15 C16 N2 0.1(6)
C14 C15 C16 C17 -179.8(4)
C8 N1 C18 C19 95.2(4)
C11 N1 C18 C19 -126.7(3)
Cu1 N1 C18 C19 -25.1(3)
C23 N3 C19 C20 -0.6(5)
Cu1 N3 C19 C20 176.6(3)
C23 N3 C19 C18 177.2(3)
Cu1 N3 C19 C18 -5.5(4)
N1 C18 C19 N3 23.8(5)
N1 C18 C19 C20 -158.3(3)
N3 C19 C20 C21 2.1(6)
C18 C19 C20 C21 -175.7(4)
C19 C20 C21 C22 -1.7(7)
C20 C21 C22 C23 0.0(7)
C19 N3 C23 C22 -1.2(5)
Cu1 N3 C23 C22 -178.3(3)
C19 N3 C23 C24 178.1(3)
Cu1 N3 C23 C24 0.9(5)
C21 C22 C23 N3 1.5(6)
C21 C22 C23 C24 -177.8(4)
