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#$Date: 2019-11-23 20:42:43 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234906 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/95/4349595.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_4349595
loop_
_publ_author_name
'Mahmoudi, Ghodrat'
'Safin, Damir A.'
'Mitoraj, Mariusz P.'
'Amini, Mojtaba'
'Kubicki, Maciej'
'Doert, Thomas'
'Locherer, Franziska'
'Fleck, Michel'
_publ_section_title
;
 Anion-driven tetrel bond-induced engineering of lead(ii) architectures
 with N′-(1-(2-pyridyl)ethylidene)nicotinohydrazide: experimental
 and theoretical findings
;
_journal_issue                   1
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              171
_journal_paper_doi               10.1039/C6QI00477F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C13 H11 N4 O Pb, Cl O4, O'
_chemical_formula_sum            'C13 H11 Cl N4 O6 Pb'
_chemical_formula_weight         561.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-04-14 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.0650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0724(8)
_cell_length_b                   13.9283(11)
_cell_length_c                   13.2362(10)
_cell_measurement_temperature    193(2)
_cell_volume                     1720.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_diffrn_measurement_method       'φ and ω 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  0.0254
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9073
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         2.190
_exptl_absorpt_coefficient_mu    9.996
_exptl_absorpt_correction_T_max  0.2397
_exptl_absorpt_correction_T_min  0.1154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.367
_refine_diff_density_min         -1.171
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     130
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+3.3183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0718
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2737
_reflns_number_total             3042
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6qi00477f2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4349595
_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   0.115
_shelx_estimated_absorpt_t_max   0.240
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.29045(2) 0.59875(2) 0.37139(2) 0.01724(9) Uani 1 1 d . . . . .
N1A N 0.8437(4) 0.7933(3) 0.7398(3) 0.0196(9) Uani 1 1 d . . . . .
C2A C 0.7334(5) 0.7477(3) 0.6654(4) 0.0170(10) Uani 1 1 d . . . . .
H2A H 0.6393 0.7637 0.6602 0.020 Uiso 1 1 calc R U . . .
C3A C 0.7488(5) 0.6781(3) 0.5953(4) 0.0164(10) Uani 1 1 d . . . . .
C4A C 0.8872(6) 0.6558(4) 0.6015(4) 0.0239(11) Uani 1 1 d . . . . .
H4A H 0.9024 0.6092 0.5545 0.029 Uiso 1 1 calc R U . . .
C5A C 1.0007(6) 0.7034(4) 0.6781(5) 0.0294(12) Uani 1 1 d . . . . .
H5A H 1.0959 0.6892 0.6846 0.035 Uiso 1 1 calc R U . . .
C6A C 0.9773(5) 0.7714(4) 0.7451(4) 0.0255(12) Uani 1 1 d . . . . .
H6A H 1.0571 0.8040 0.7964 0.031 Uiso 1 1 calc R U . . .
C7A C 0.6176(5) 0.6340(3) 0.5140(4) 0.0158(10) Uani 1 1 d . . . . .
O7A O 0.4989(4) 0.6754(2) 0.4963(3) 0.0209(7) Uani 1 1 d . . . . .
N8A N 0.6391(4) 0.5550(3) 0.4653(3) 0.0169(8) Uani 1 1 d . . . . .
N9A N 0.5123(4) 0.5265(3) 0.3816(3) 0.0162(8) Uani 1 1 d . . . . .
C10A C 0.5218(5) 0.4596(3) 0.3164(4) 0.0176(10) Uani 1 1 d . . . . .
C101 C 0.6559(6) 0.4098(3) 0.3275(5) 0.0247(12) Uani 1 1 d . . . . .
H10A H 0.7349 0.4352 0.3909 0.037 Uiso 1 1 calc R U . . .
H10B H 0.6766 0.4202 0.2616 0.037 Uiso 1 1 calc R U . . .
H10C H 0.6454 0.3408 0.3373 0.037 Uiso 1 1 calc R U . . .
C11A C 0.3851(6) 0.4342(3) 0.2254(4) 0.0198(10) Uani 1 1 d . . . . .
N12A N 0.2655(5) 0.4768(3) 0.2254(3) 0.0213(9) Uani 1 1 d . . . . .
C13A C 0.1406(6) 0.4548(4) 0.1470(5) 0.0297(13) Uani 1 1 d . . . . .
H13A H 0.0563 0.4842 0.1485 0.036 Uiso 1 1 calc R U . . .
C14A C 0.1275(7) 0.3914(4) 0.0638(5) 0.0330(14) Uani 1 1 d . . . . .
H14A H 0.0364 0.3768 0.0097 0.040 Uiso 1 1 calc R U . . .
C15A C 0.2514(6) 0.3495(4) 0.0611(5) 0.0306(13) Uani 1 1 d . . . . .
H15A H 0.2467 0.3075 0.0033 0.037 Uiso 1 1 calc R U . . .
C16A C 0.3825(6) 0.3696(4) 0.1442(4) 0.0269(12) Uani 1 1 d . . . . .
H16A H 0.4681 0.3400 0.1455 0.032 Uiso 1 1 calc R U . . .
Cl1B Cl 0.89237(16) 0.62213(11) 0.27814(14) 0.0389(4) Uani 1 1 d D U . . .
O1B O 0.9725(5) 0.6602(3) 0.2172(4) 0.0455(11) Uani 1 1 d D U . . .
O2B O 0.7471(8) 0.5988(8) 0.2071(9) 0.059(3) Uani 0.581(13) 1 d D U P A 1
O3B O 0.9581(9) 0.5524(8) 0.3556(9) 0.066(3) Uani 0.581(13) 1 d D U P A 1
O4B O 0.8642(13) 0.7042(6) 0.3412(9) 0.073(4) Uani 0.581(13) 1 d D U P A 1
O2'B O 0.7496(9) 0.6454(12) 0.2342(13) 0.068(4) Uani 0.419(13) 1 d D U P A 2
O3'B O 0.9202(19) 0.5199(6) 0.2794(18) 0.085(5) Uani 0.419(13) 1 d D U P A 2
O4'B O 0.9675(16) 0.6587(13) 0.3882(7) 0.084(5) Uani 0.419(13) 1 d D U P A 2
O1W1 O 0.152(2) 0.0940(9) 0.5059(15) 0.091(6) Uani 0.4 1 d . U P B 1
O1W2 O 0.250(3) 0.1071(17) 0.567(2) 0.083(7) Uani 0.3 1 d . U P C 2
O1W3 O 0.087(2) 0.0089(17) 0.5548(17) 0.085(6) Uani 0.3 1 d . U P D 3
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 '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
O7A Pb1 N9A 65.86(12) . .
O7A Pb1 N1A 81.40(13) . 4_575
N9A Pb1 N1A 81.57(13) . 4_575
O7A Pb1 N12A 130.11(12) . .
N9A Pb1 N12A 65.38(13) . .
N1A Pb1 N12A 81.80(13) 4_575 .
C2A N1A C6A 117.7(4) . .
C2A N1A Pb1 117.5(3) . 4_676
C6A N1A Pb1 124.5(3) . 4_676
N1A C2A C3A 123.5(4) . .
N1A C2A H2A 118.2 . .
C3A C2A H2A 118.2 . .
C2A C3A C4A 118.3(5) . .
C2A C3A C7A 118.6(4) . .
C4A C3A C7A 123.0(4) . .
C5A C4A C3A 117.9(5) . .
C5A C4A H4A 121.0 . .
C3A C4A H4A 121.0 . .
C6A C5A C4A 120.6(5) . .
C6A C5A H5A 119.7 . .
C4A C5A H5A 119.7 . .
N1A C6A C5A 121.9(5) . .
N1A C6A H6A 119.1 . .
C5A C6A H6A 119.1 . .
O7A C7A N8A 126.8(4) . .
O7A C7A C3A 117.8(4) . .
N8A C7A C3A 115.4(4) . .
C7A O7A Pb1 116.7(3) . .
C7A N8A N9A 110.6(4) . .
C10A N9A N8A 117.3(4) . .
C10A N9A Pb1 124.2(3) . .
N8A N9A Pb1 118.5(3) . .
N9A C10A C101 124.4(5) . .
N9A C10A C11A 115.5(4) . .
C101 C10A C11A 120.1(4) . .
C10A C101 H10A 109.5 . .
C10A C101 H10B 109.5 . .
H10A C101 H10B 109.5 . .
C10A C101 H10C 109.5 . .
H10A C101 H10C 109.5 . .
H10B C101 H10C 109.5 . .
N12A C11A C16A 121.9(5) . .
N12A C11A C10A 116.8(4) . .
C16A C11A C10A 121.3(5) . .
C13A N12A C11A 118.9(5) . .
C13A N12A Pb1 123.2(4) . .
C11A N12A Pb1 117.9(3) . .
N12A C13A C14A 123.3(6) . .
N12A C13A H13A 118.4 . .
C14A C13A H13A 118.4 . .
C13A C14A C15A 118.2(6) . .
C13A C14A H14A 120.9 . .
C15A C14A H14A 120.9 . .
C16A C15A C14A 119.3(5) . .
C16A C15A H15A 120.4 . .
C14A C15A H15A 120.4 . .
C15A C16A C11A 118.4(5) . .
C15A C16A H16A 120.8 . .
C11A C16A H16A 120.8 . .
O2'B Cl1B O1B 113.3(6) . .
O3B Cl1B O1B 117.4(4) . .
O3B Cl1B O2B 114.1(6) . .
O1B Cl1B O2B 111.2(5) . .
O2'B Cl1B O3'B 113.8(9) . .
O1B Cl1B O3'B 102.8(6) . .
O2'B Cl1B O4'B 114.1(8) . .
O1B Cl1B O4'B 104.0(6) . .
O3'B Cl1B O4'B 107.8(9) . .
O3B Cl1B O4B 105.0(6) . .
O1B Cl1B O4B 107.1(4) . .
O2B Cl1B O4B 100.1(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pb1 O7A 2.382(3) .
Pb1 N9A 2.408(4) .
Pb1 N1A 2.506(4) 4_575
Pb1 N12A 2.513(4) .
N1A C2A 1.337(6) .
N1A C6A 1.356(7) .
N1A Pb1 2.506(4) 4_676
C2A C3A 1.391(7) .
C2A H2A 0.9500 .
C3A C4A 1.400(7) .
C3A C7A 1.487(7) .
C4A C5A 1.380(8) .
C4A H4A 0.9500 .
C5A C6A 1.377(7) .
C5A H5A 0.9500 .
C6A H6A 0.9500 .
C7A O7A 1.268(6) .
C7A N8A 1.333(6) .
N8A N9A 1.398(6) .
N9A C10A 1.298(6) .
C10A C101 1.477(7) .
C10A C11A 1.492(7) .
C101 H10A 0.9800 .
C101 H10B 0.9800 .
C101 H10C 0.9800 .
C11A N12A 1.343(7) .
C11A C16A 1.395(8) .
N12A C13A 1.331(7) .
C13A C14A 1.379(8) .
C13A H13A 0.9500 .
C14A C15A 1.390(9) .
C14A H14A 0.9500 .
C15A C16A 1.393(8) .
C15A H15A 0.9500 .
C16A H16A 0.9500 .
Cl1B O2'B 1.372(7) .
Cl1B O3B 1.387(6) .
Cl1B O1B 1.440(4) .
Cl1B O2B 1.448(7) .
Cl1B O3'B 1.450(8) .
Cl1B O4'B 1.458(8) .
Cl1B O4B 1.504(7) .
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
C2A H2A O1B 0.95 2.34 3.220(6) 154.2 4_576
C6A H6A O2'B 0.95 2.48 3.029(11) 117.1 4_676
C16A H16A O4B 0.95 2.50 3.388(11) 156.2 2_645
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
C6A N1A C2A C3A 1.4(7) .
Pb1 N1A C2A C3A -172.9(4) 4_676
N1A C2A C3A C4A -1.2(7) .
N1A C2A C3A C7A -178.6(4) .
C2A C3A C4A C5A 0.8(7) .
C7A C3A C4A C5A 178.0(5) .
C3A C4A C5A C6A -0.7(8) .
C2A N1A C6A C5A -1.3(8) .
Pb1 N1A C6A C5A 172.6(4) 4_676
C4A C5A C6A N1A 0.9(9) .
C2A C3A C7A O7A 14.8(6) .
C4A C3A C7A O7A -162.5(5) .
C2A C3A C7A N8A -166.6(4) .
C4A C3A C7A N8A 16.1(7) .
N8A C7A O7A Pb1 4.2(6) .
C3A C7A O7A Pb1 -177.4(3) .
O7A C7A N8A N9A 5.7(7) .
C3A C7A N8A N9A -172.7(4) .
C7A N8A N9A C10A 169.7(4) .
C7A N8A N9A Pb1 -12.8(5) .
N8A N9A C10A C101 2.4(7) .
Pb1 N9A C10A C101 -175.0(3) .
N8A N9A C10A C11A -177.5(4) .
Pb1 N9A C10A C11A 5.1(6) .
N9A C10A C11A N12A -5.3(6) .
C101 C10A C11A N12A 174.7(4) .
N9A C10A C11A C16A 174.4(5) .
C101 C10A C11A C16A -5.6(7) .
C16A C11A N12A C13A 1.6(7) .
C10A C11A N12A C13A -178.7(4) .
C16A C11A N12A Pb1 -176.4(4) .
C10A C11A N12A Pb1 3.3(5) .
C11A N12A C13A C14A -1.3(8) .
Pb1 N12A C13A C14A 176.7(4) .
N12A C13A C14A C15A -0.8(9) .
C13A C14A C15A C16A 2.6(8) .
C14A C15A C16A C11A -2.2(8) .
N12A C11A C16A C15A 0.1(8) .
C10A C11A C16A C15A -179.6(4) .
