#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:23:22 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179662 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/15/4511577.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_4511577
loop_
_publ_author_name
'Kerr, Andrew T.'
'Cahill, Christopher L.'
_publ_section_title
;
 CuPYDC Metalloligands and Postsynthetic Rearrangement/Metalation as
 Routes to Bimetallic Uranyl Containing Hybrid Materials: Syntheses,
 Structures, and Fluorescence
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4094
_journal_paper_doi               10.1021/cg5007132
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C14 H12 Cu N2 O13 U'
_chemical_formula_weight         716.82
_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_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90.275(6)
_cell_angle_beta                 113.058(6)
_cell_angle_gamma                110.556(6)
_cell_formula_units_Z            2
_cell_length_a                   9.344(4)
_cell_length_b                   10.249(4)
_cell_length_c                   11.295(5)
_cell_measurement_reflns_used    13632
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.463
_cell_measurement_theta_min      5.098
_cell_volume                     919.1(7)
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_collection       'APEX, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR92 (Gualardi, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13629
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         30.485
_diffrn_reflns_theta_min         1.987
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_source_type              'Bruker ApexII'
_exptl_absorpt_coefficient_mu    10.033
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5349
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    2.590
_exptl_crystal_description       Prisim
_exptl_crystal_F_000             668
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.971
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0181P)²+0.4131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0450
_refine_ls_wR_factor_ref         0.0478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4513
_reflns_number_total             5083
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5007132_si_002.cif
_cod_data_source_block           Compound_3
_cod_depositor_comments
'Adding full bibliography for 4511575--4511577.cif.'
_cod_original_cell_volume        919.2(7)
_cod_database_code               4511577
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
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
C1 C 1.0631(4) 0.3990(4) -0.3653(3) 0.0139(7) Uani 1 1 d . .
C2 C 0.9952(4) 0.2540(4) -0.3313(3) 0.0155(7) Uani 1 1 d . .
C3 C 0.9837(4) 0.2336(4) -0.2134(3) 0.0142(7) Uani 1 1 d . .
C4 C 0.8335(5) -0.0078(4) -0.2862(4) 0.0263(9) Uani 1 1 d . .
H4 H 0.7735 -0.0958 -0.2726 0.032 Uiso 1 1 calc R U
C5 C 0.8516(6) 0.0040(4) -0.4018(4) 0.0314(10) Uani 1 1 d . .
H5 H 0.8103 -0.0760 -0.4633 0.038 Uiso 1 1 calc R U
C6 C 0.9317(5) 0.1357(4) -0.4248(4) 0.0250(9) Uani 1 1 d . .
H6 H 0.9432 0.1455 -0.5028 0.030 Uiso 1 1 calc R U
C7 C 1.0711(4) 0.3464(4) -0.0937(3) 0.0147(7) Uani 1 1 d . .
C8 C 0.4821(5) 0.1636(4) -0.2260(4) 0.0185(8) Uani 1 1 d . .
C9 C 0.3878(4) 0.0218(4) -0.1997(3) 0.0153(7) Uani 1 1 d . .
C10 C 0.3770(5) -0.1000(4) -0.2653(4) 0.0214(8) Uani 1 1 d . .
H10 H 0.4304 -0.0923 -0.3207 0.026 Uiso 1 1 calc R U
C11 C 0.2099(5) -0.2412(4) -0.1637(4) 0.0201(8) Uani 1 1 d . .
H11 H 0.1488 -0.3300 -0.1522 0.024 Uiso 1 1 calc R U
C12 C 0.2879(5) -0.2302(4) -0.2476(4) 0.0236(9) Uani 1 1 d . .
H12 H 0.2794 -0.3113 -0.2917 0.028 Uiso 1 1 calc R U
C13 C 0.3107(4) 0.0034(4) -0.1150(3) 0.0154(7) Uani 1 1 d . .
C14 C 0.3210(5) 0.1225(4) -0.0274(4) 0.0200(8) Uani 1 1 d . .
N1 N 0.9002(4) 0.1045(3) -0.1936(3) 0.0181(6) Uani 1 1 d . .
N2 N 0.2218(4) -0.1258(3) -0.0995(3) 0.0167(6) Uani 1 1 d . .
O1 O 1.3652(3) 0.6814(3) -0.4983(3) 0.0228(6) Uani 1 1 d . .
O2 O 1.1826(3) 0.3201(3) -0.6389(3) 0.0228(6) Uani 1 1 d . .
O3 O 1.4868(3) 0.4587(3) -0.3934(2) 0.0157(5) Uani 1 1 d . .
O4 O 1.1846(3) 0.4252(3) -0.3952(3) 0.0226(6) Uani 1 1 d . .
O5 O 0.9896(3) 0.4807(3) -0.3684(2) 0.0173(5) Uani 1 1 d . .
O6 O 1.1875(3) 0.4546(3) -0.0867(2) 0.0209(6) Uani 1 1 d . .
O7 O 1.0189(3) 0.3152(3) -0.0035(2) 0.0206(6) Uani 1 1 d . .
O8 O 0.6408(3) 0.2108(3) -0.1681(3) 0.0282(7) Uani 1 1 d . .
O9 O 0.3951(3) 0.2161(3) -0.3072(3) 0.0290(7) Uani 1 1 d . .
O10 O 0.2510(4) 0.0834(3) 0.0499(3) 0.0267(6) Uani 1 1 d . .
O11 O 0.3977(4) 0.2461(3) -0.0321(3) 0.0302(7) Uani 1 1 d . .
OW1 O 1.1995(4) 0.5427(3) -0.7901(3) 0.0203(6) Uani 1 1 d . .
OW2 O 1.5055(5) 0.5110(4) -0.1424(4) 0.0450(9) Uani 1 1 d . .
Cu1 Cu 0.85044(6) 0.11988(5) -0.04099(4) 0.02026(10) Uani 1 1 d . .
U1 U 1.27649(2) 0.50039(2) -0.56635(2) 0.01175(4) Uani 1 1 d . .
H3 H 1.457(5) 0.393(4) -0.381(4) 0.016(13) Uiso 1 1 d . .
HW1A H 1.246(7) 0.621(6) -0.802(6) 0.07(2) Uiso 1 1 d . .
HW1B H 1.145(6) 0.480(5) -0.849(5) 0.028(13) Uiso 1 1 d . .
HW2A H 1.606(10) 0.485(8) -0.089(8) 0.13(3) Uiso 1 1 d . .
HW2B H 1.521(7) 0.526(6) -0.234(6) 0.08(2) 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 0.0033 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'
U U -9.6767 9.6646 '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
O5 C1 O4 124.6(3) . .
O5 C1 C2 118.5(3) . .
O4 C1 C2 116.8(3) . .
C3 C2 C6 118.1(3) . .
C3 C2 C1 123.0(3) . .
C6 C2 C1 118.8(3) . .
N1 C3 C2 121.4(3) . .
N1 C3 C7 113.6(3) . .
C2 C3 C7 124.8(3) . .
N1 C4 C5 121.4(4) . .
N1 C4 H4 119.3 . .
C5 C4 H4 119.3 . .
C6 C5 C4 119.1(4) . .
C6 C5 H5 120.4 . .
C4 C5 H5 120.4 . .
C5 C6 C2 119.8(4) . .
C5 C6 H6 120.1 . .
C2 C6 H6 120.1 . .
O6 C7 O7 125.5(3) . .
O6 C7 C3 119.3(3) . .
O7 C7 C3 115.1(3) . .
O9 C8 O8 127.4(3) . .
O9 C8 C9 115.9(3) . .
O8 C8 C9 116.5(3) . .
C13 C9 C10 117.3(3) . .
C13 C9 C8 124.6(3) . .
C10 C9 C8 118.1(3) . .
C12 C10 C9 119.8(3) . .
C12 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
N2 C11 C12 120.6(3) . .
N2 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C10 C12 C11 119.9(4) . .
C10 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
N2 C13 C9 122.2(3) . .
N2 C13 C14 113.0(3) . .
C9 C13 C14 124.8(3) . .
O11 C14 O10 124.9(4) . .
O11 C14 C13 119.9(3) . .
O10 C14 C13 115.2(3) . .
C4 N1 C3 119.9(3) . .
C4 N1 Cu1 127.6(3) . .
C3 N1 Cu1 110.8(2) . .
C11 N2 C13 120.1(3) . .
C11 N2 Cu1 126.1(3) . 2_655
C13 N2 Cu1 113.1(2) . 2_655
U1 O3 U1 111.30(11) 2_864 .
U1 O3 H3 111(4) 2_864 .
U1 O3 H3 111(4) . .
C1 O4 U1 142.8(2) . .
C1 O5 U1 145.3(2) . 2_764
C7 O7 Cu1 113.4(2) . .
C8 O8 Cu1 136.3(2) . .
C14 O10 Cu1 115.4(2) . 2_655
U1 OW1 HW1A 118(4) . .
U1 OW1 HW1B 121(3) . .
HW1A OW1 HW1B 120(5) . .
HW2A OW2 HW2B 101(5) . .
O10 Cu1 N2 83.10(12) 2_655 2_655
O10 Cu1 N1 94.34(12) 2_655 .
N2 Cu1 N1 174.54(13) 2_655 .
O10 Cu1 O7 161.95(12) 2_655 .
N2 Cu1 O7 100.55(11) 2_655 .
N1 Cu1 O7 83.38(11) . .
O10 Cu1 O8 110.98(11) 2_655 .
N2 Cu1 O8 87.66(11) 2_655 .
N1 Cu1 O8 88.77(12) . .
O7 Cu1 O8 86.92(11) . .
O1 U1 O2 178.13(12) . .
O1 U1 O3 87.44(11) . 2_864
O2 U1 O3 93.17(11) . 2_864
O1 U1 O3 90.83(11) . .
O2 U1 O3 91.04(11) . .
O3 U1 O3 68.70(11) 2_864 .
O1 U1 O5 86.06(10) . 2_764
O2 U1 O5 92.49(10) . 2_764
O3 U1 O5 147.46(9) 2_864 2_764
O3 U1 O5 143.18(9) . 2_764
O1 U1 OW1 94.45(12) . .
O2 U1 OW1 84.03(12) . .
O3 U1 OW1 73.80(9) 2_864 .
O3 U1 OW1 141.82(9) . .
O5 U1 OW1 74.97(9) 2_764 .
O1 U1 O4 93.40(11) . .
O2 U1 O4 87.34(11) . .
O3 U1 O4 138.05(9) 2_864 .
O3 U1 O4 69.36(9) . .
O5 U1 O4 74.21(8) 2_764 .
OW1 U1 O4 147.54(9) . .
O1 U1 U1 88.96(9) . 2_864
O2 U1 U1 92.54(8) . 2_864
O3 U1 U1 34.42(7) 2_864 2_864
O3 U1 U1 34.28(6) . 2_864
O5 U1 U1 174.42(6) 2_764 2_864
OW1 U1 U1 107.95(7) . 2_864
O4 U1 U1 103.64(6) . 2_864
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O5 1.248(4) .
C1 O4 1.251(4) .
C1 C2 1.514(5) .
C2 C3 1.388(5) .
C2 C6 1.389(5) .
C3 N1 1.351(4) .
C3 C7 1.513(5) .
C4 N1 1.334(5) .
C4 C5 1.382(6) .
C4 H4 0.9300 .
C5 C6 1.377(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 O6 1.226(4) .
C7 O7 1.288(4) .
C8 O9 1.233(5) .
C8 O8 1.262(4) .
C8 C9 1.512(5) .
C9 C13 1.384(5) .
C9 C10 1.401(5) .
C10 C12 1.366(5) .
C10 H10 0.9300 .
C11 N2 1.332(4) .
C11 C12 1.387(5) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 N2 1.348(4) .
C13 C14 1.520(5) .
C14 O11 1.230(4) .
C14 O10 1.272(4) .
N1 Cu1 1.972(3) .
N2 Cu1 1.960(3) 2_655
O1 U1 1.769(3) .
O2 U1 1.772(3) .
O3 U1 2.327(3) 2_864
O3 U1 2.335(3) .
O3 H3 0.67(4) .
O4 U1 2.432(3) .
O5 U1 2.380(3) 2_764
O7 Cu1 1.980(3) .
O8 Cu1 2.420(3) .
O10 Cu1 1.946(3) 2_655
OW1 U1 2.428(3) .
OW1 HW1A 0.81(6) .
OW1 HW1B 0.78(5) .
OW2 HW2A 1.03(8) .
OW2 HW2B 1.11(6) .
Cu1 O10 1.946(3) 2_655
Cu1 N2 1.960(3) 2_655
U1 O3 2.327(3) 2_864
U1 O5 2.380(3) 2_764
U1 U1 3.8489(17) 2_864
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O10 0.93 2.62 3.097(5) 112.4 2_655
C5 H5 O9 0.93 2.57 3.398(5) 148.7 2_654
C11 H11 O5 0.93 2.65 3.130(5) 112.8 1_445
C11 H11 O6 0.93 2.43 3.199(5) 139.6 1_445
C12 H12 O4 0.93 2.63 3.532(5) 163.3 1_445
C12 H12 O5 0.93 2.59 3.098(5) 114.6 1_445
O3 H3 O9 0.67(4) 1.99(4) 2.654(4) 169(5) 1_655
OW1 HW1A O8 0.81(6) 1.79(6) 2.598(4) 175(6) 2_764
OW1 HW1B O7 0.78(5) 2.06(5) 2.845(4) 175(5) 1_554
OW2 HW2A O6 1.03(8) 2.05(8) 2.918(5) 141(6) 2_865
OW2 HW2B O3 1.11(6) 1.78(6) 2.808(4) 151(5) .
C4 H4 O10 0.93 2.62 3.097(5) 112.4 2_655
C5 H5 O9 0.93 2.57 3.398(5) 148.7 2_654
C11 H11 O5 0.93 2.65 3.130(5) 112.8 1_445
C11 H11 O6 0.93 2.43 3.199(5) 139.6 1_445
C12 H12 O4 0.93 2.63 3.532(5) 163.3 1_445
C12 H12 O5 0.93 2.59 3.098(5) 114.6 1_445
O3 H3 O9 0.67(4) 1.99(4) 2.654(4) 169(5) 1_655
OW1 HW1A O8 0.81(6) 1.79(6) 2.598(4) 175(6) 2_764
OW1 HW1B O7 0.78(5) 2.06(5) 2.845(4) 175(5) 1_554
OW2 HW2A O6 1.03(8) 2.05(8) 2.918(5) 141(6) 2_865
OW2 HW2B O3 1.11(6) 1.78(6) 2.808(4) 151(5) .
