#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:19:03 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179476 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/73/4337334.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_4337334
loop_
_publ_author_name
'Lincoln, Kimberly M.'
'Offutt, Michael E.'
'Hayden, Travis D.'
'Saunders, Ryker E.'
'Green, Kayla N.'
_publ_section_title
;
 Structural, Spectral, and Electrochemical Properties of Nickel(II),
 Copper(II), and Zinc(II) Complexes Containing 12-Membered Pyridine- and
 Pyridol-Based Tetra-aza Macrocycles.
;
_journal_issue                   3
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1406
_journal_page_last               1416
_journal_paper_doi               10.1021/ic402119s
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C11 H18 Cl N4 O Zn, Cl O4'
_chemical_formula_sum            'C11 H18 Cl2 N4 O5 Zn'
_chemical_formula_weight         422.57
_chemical_name_common            ZnpHP
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_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_date             2013-09-04
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.410(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5092(5)
_cell_length_b                   9.0075(4)
_cell_length_c                   15.4711(7)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.1704
_cell_measurement_theta_min      4.4583
_cell_volume                     1590.48(12)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      373.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            91677
_diffrn_reflns_theta_full        38.45
_diffrn_reflns_theta_max         38.45
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   mutli-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.0421
_exptl_crystal_size_mid          0.0217
_exptl_crystal_size_min          0.0194
_refine_diff_density_max         1.525
_refine_diff_density_min         -1.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         8871
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.276
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0453
_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)+(0.0586P)²+2.2207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                6731
_reflns_number_total             8871
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic402119s_si_007.cif
_cod_data_source_block           I
_cod_database_code               4337334
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 1.01888(2) 0.68364(3) 0.155186(15) 0.01626(7) Uani d . 1.0 A 1
Cl Cl1 1.13497(5) 0.49534(7) 0.13273(4) 0.02708(12) Uani d . 1.0 A 1
C C5 0.84739(15) 0.8816(2) 0.05739(12) 0.0133(3) Uani d . 1.0 A 1
C C4 0.79022(18) 1.0125(2) 0.03260(13) 0.0183(3) Uani d . 1.0 A 1
H H2 0.7146 1.0116 -0.0003 0.022 Uiso calc R 1.0 A 1
C C3 0.8462(2) 1.1461(2) 0.05707(14) 0.0232(4) Uani d . 1.0 A 1
C C2 0.9549(2) 1.1439(2) 0.10945(13) 0.0201(3) Uani d . 1.0 A 1
H H4 0.9932 1.2337 0.1287 0.024 Uiso calc R 1.0 A 1
C C1 1.00501(16) 1.0080(2) 0.13243(13) 0.0159(3) Uani d . 1.0 A 1
C C11 1.12073(17) 0.9930(3) 0.19037(14) 0.0211(4) Uani d . 1.0 A 1
H H6A 1.1855 1.0099 0.1552 0.025 Uiso calc R 1.0 A 1
H H6B 1.1258 1.0701 0.2363 0.025 Uiso calc R 1.0 A 1
C C10 1.09762(19) 0.8354(3) 0.31953(14) 0.0241(4) Uani d . 1.0 A 1
H H7A 1.1214 0.927 0.3525 0.029 Uiso calc R 1.0 A 1
H H7B 1.1375 0.7504 0.3513 0.029 Uiso calc R 1.0 A 1
C C9 0.96578(19) 0.8158(3) 0.31451(14) 0.0202(4) Uani d . 1.0 A 1
H H8A 0.9435 0.8078 0.374 0.024 Uiso calc R 1.0 A 1
H H8B 0.9254 0.9033 0.2858 0.024 Uiso calc R 1.0 A 1
C C8 0.80325(18) 0.6717(3) 0.23253(14) 0.0205(4) Uani d . 1.0 A 1
H H9A 0.7737 0.7713 0.2135 0.025 Uiso calc R 1.0 A 1
H H9B 0.7598 0.6379 0.2801 0.025 Uiso calc R 1.0 A 1
C C7 0.7834(2) 0.5637(3) 0.15660(15) 0.0218(4) Uani d . 1.0 A 1
H H10A 0.809 0.4632 0.1767 0.026 Uiso calc R 1.0 A 1
H H10B 0.6987 0.5593 0.1347 0.026 Uiso calc R 1.0 A 1
C C6 0.79441(16) 0.7322(2) 0.03163(13) 0.0162(3) Uani d . 1.0 A 1
H H11A 0.7096 0.7348 0.037 0.019 Uiso calc R 1.0 A 1
H H11B 0.8029 0.7128 -0.0302 0.019 Uiso calc R 1.0 A 1
N N4 0.95362(13) 0.88022(19) 0.10430(10) 0.0143(3) Uani d . 1.0 A 1
N N3 1.13462(15) 0.8449(2) 0.23171(12) 0.0207(3) Uani d . 1.0 A 1
H H1A 1.1628 0.7683 0.2059 0.025 Uiso d R 1.0 A 1
N N2 0.92960(16) 0.6802(2) 0.26438(12) 0.0182(3) Uani d . 1.0 A 1
H H2A 0.9794 0.6101 0.2543 0.022 Uiso d R 1.0 A 1
N N1 0.84919(15) 0.61019(19) 0.08537(11) 0.0165(3) Uani d . 1.0 A 1
H H3A 0.9155 0.5685 0.0759 0.02 Uiso d R 1.0 A 1
O O1 0.7991(2) 1.2789(2) 0.03501(16) 0.0456(7) Uani d . 1.0 A 1
H H1 0.7335 1.2672 0.0051 0.068 Uiso calc R 1.0 A 1
Cl Cl2 0.5314(4) 0.1919(8) 0.8803(4) 0.0219(11) Uani d PD 0.539(4) B 1
O O2 0.6254(3) 0.1224(6) 0.8510(3) 0.0408(12) Uani d PDU 0.539(4) B 1
O O3 0.4306(4) 0.0918(5) 0.8796(3) 0.0367(9) Uiso d PD 0.539(4) B 1
O O4 0.5099(6) 0.2702(9) 0.9581(3) 0.068(2) Uani d PDU 0.539(4) B 1
O O5 0.4624(4) 0.2444(7) 0.8066(3) 0.0426(12) Uani d PDU 0.539(4) B 1
Cl Cl2' 0.5309(4) 0.2004(9) 0.8808(4) 0.0172(9) Uani d P 0.461(4) B 2
O O2' 0.6562(3) 0.2339(4) 0.8755(2) 0.0237(8) Uiso d P 0.461(4) B 2
O O3' 0.5272(6) 0.0403(6) 0.8984(3) 0.0505(17) Uani d PU 0.461(4) B 2
O O4' 0.5608(5) 0.2579(6) 0.9630(3) 0.0307(10) Uiso d P 0.461(4) B 2
O O5' 0.4901(5) 0.3156(6) 0.8196(4) 0.0343(10) Uiso d P 0.461(4) B 2
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'
Zn Zn 0.2839 1.4301 '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
Cl1 Zn1 H1A 82.0
Cl1 Zn1 H2A 94.4
Cl1 Zn1 H3A 79.7
N4 Zn1 Cl1 143.46(5)
N4 Zn1 N3 78.62(7)
N4 Zn1 H1A 94.0
N4 Zn1 N2 97.47(7)
N4 Zn1 H2A 122.2
N4 Zn1 N1 79.22(6)
N4 Zn1 H3A 93.2
N3 Zn1 Cl1 104.69(5)
N3 Zn1 H1A 23.2
N3 Zn1 H2A 89.2
N3 Zn1 H3A 171.0
H1A Zn1 H2A 95.7
H1A Zn1 H3A 157.7
N2 Zn1 Cl1 119.04(5)
N2 Zn1 N3 84.37(7)
N2 Zn1 H1A 99.5
N2 Zn1 H2A 24.7
N2 Zn1 N1 83.96(7)
N2 Zn1 H3A 100.5
H2A Zn1 H3A 98.3
N1 Zn1 Cl1 101.96(5)
N1 Zn1 N3 153.31(7)
N1 Zn1 H1A 172.7
N1 Zn1 H2A 90.1
N1 Zn1 H3A 23.2
C4 C5 C6 121.76(16)
N4 C5 C4 121.84(17)
N4 C5 C6 116.39(16)
C5 C4 H2 120.8
C5 C4 C3 118.33(18)
C3 C4 H2 120.8
C4 C3 C2 119.5(2)
O1 C3 C4 122.9(2)
O1 C3 C2 117.5(2)
C3 C2 H4 120.9
C1 C2 C3 118.27(19)
C1 C2 H4 120.9
C2 C1 C11 122.57(18)
N4 C1 C2 121.71(17)
N4 C1 C11 115.71(18)
C1 C11 H6A 109.2
C1 C11 H6B 109.2
H6A C11 H6B 107.9
N3 C11 C1 111.99(17)
N3 C11 H6A 109.2
N3 C11 H6B 109.2
H7A C10 H7B 108.0
C9 C10 H7A 109.4
C9 C10 H7B 109.4
N3 C10 H7A 109.4
N3 C10 H7B 109.4
N3 C10 C9 111.35(16)
C10 C9 H8A 109.8
C10 C9 H8B 109.8
H8A C9 H8B 108.2
N2 C9 C10 109.55(18)
N2 C9 H8A 109.8
N2 C9 H8B 109.8
H9A C8 H9B 108.2
C7 C8 H9A 109.8
C7 C8 H9B 109.8
N2 C8 H9A 109.8
N2 C8 H9B 109.8
N2 C8 C7 109.55(18)
C8 C7 H10A 109.5
C8 C7 H10B 109.5
H10A C7 H10B 108.1
N1 C7 C8 110.80(17)
N1 C7 H10A 109.5
N1 C7 H10B 109.5
C5 C6 H11A 109.0
C5 C6 H11B 109.0
H11A C6 H11B 107.8
N1 C6 C5 112.82(15)
N1 C6 H11A 109.0
N1 C6 H11B 109.0
C5 N4 Zn1 118.81(13)
C5 N4 C1 120.13(17)
C1 N4 Zn1 119.63(13)
Zn1 N3 H1A 58.2
C11 N3 Zn1 109.71(12)
C11 N3 H1A 122.5
C10 N3 Zn1 103.24(14)
C10 N3 C11 114.97(19)
C10 N3 H1A 122.5
Zn1 N2 H2A 57.9
C9 N2 Zn1 106.11(13)
C9 N2 H2A 122.7
C8 N2 Zn1 107.29(13)
C8 N2 C9 114.61(17)
C8 N2 H2A 122.7
Zn1 N1 H3A 58.5
C7 N1 Zn1 103.09(12)
C7 N1 H3A 122.9
C6 N1 Zn1 109.91(12)
C6 N1 C7 114.21(16)
C6 N1 H3A 122.9
O2 Cl2 O3 111.8(5)
O2 Cl2 O4 136.3(5)
O2 Cl2 O5 106.0(4)
O4 Cl2 O3 95.0(5)
O5 Cl2 O3 80.5(4)
O5 Cl2 O4 112.2(6)
O3' Cl2' O2' 105.1(5)
O4' Cl2' O2' 81.1(4)
O4' Cl2' O3' 102.0(5)
O4' Cl2' O5' 111.0(6)
O5' Cl2' O2' 93.1(5)
O5' Cl2' O3' 144.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Zn1 Cl1 2.2141(6)
Zn1 N4 2.0413(17)
Zn1 N3 2.2092(19)
Zn1 H1A 1.8991
Zn1 N2 2.0876(19)
Zn1 H2A 1.7826
Zn1 N1 2.2078(17)
Zn1 H3A 1.9028
C5 C4 1.381(3)
C5 C6 1.509(3)
C5 N4 1.339(2)
C4 H2 0.95
C4 C3 1.394(3)
C3 C2 1.400(3)
C3 O1 1.340(3)
C2 H4 0.95
C2 C1 1.380(3)
C1 C11 1.512(3)
C1 N4 1.341(3)
C11 H6A 0.99
C11 H6B 0.99
C11 N3 1.479(3)
C10 H7A 0.99
C10 H7B 0.99
C10 C9 1.520(3)
C10 N3 1.478(3)
C9 H8A 0.99
C9 H8B 0.99
C9 N2 1.478(3)
C8 H9A 0.99
C8 H9B 0.99
C8 C7 1.520(3)
C8 N2 1.476(3)
C7 H10A 0.99
C7 H10B 0.99
C7 N1 1.476(3)
C6 H11A 0.99
C6 H11B 0.99
C6 N1 1.470(3)
N3 H1A 0.88
N2 H2A 0.88
N1 H3A 0.88
O1 H1 0.84
Cl2 O2 1.377(6)
Cl2 O3 1.468(7)
Cl2 O4 1.444(7)
Cl2 O5 1.385(7)
Cl2' O2' 1.486(6)
Cl2' O3' 1.470(9)
Cl2' O4' 1.375(8)
Cl2' O5' 1.441(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
Cl1 Zn1 N4 C5 96.83(15)
Cl1 Zn1 N4 C1 -96.81(15)
Cl1 Zn1 N3 C11 128.85(13)
Cl1 Zn1 N3 C10 -108.12(13)
Cl1 Zn1 N2 C9 122.08(12)
Cl1 Zn1 N2 C8 -114.97(13)
Cl1 Zn1 N1 C7 104.04(12)
Cl1 Zn1 N1 C6 -133.81(12)
C5 C4 C3 C2 -3.4(3)
C5 C4 C3 O1 178.8(3)
C5 C6 N1 Zn1 -16.70(19)
C5 C6 N1 C7 98.6(2)
C4 C5 C6 N1 -162.12(19)
C4 C5 N4 Zn1 169.73(15)
C4 C5 N4 C1 3.4(3)
C4 C3 C2 C1 2.4(3)
C3 C2 C1 C11 -178.6(2)
C3 C2 C1 N4 1.5(3)
C2 C1 C11 N3 158.7(2)
C2 C1 N4 Zn1 -170.66(16)
C2 C1 N4 C5 -4.5(3)
C1 C11 N3 Zn1 22.0(2)
C1 C11 N3 C10 -93.8(2)
C11 C1 N4 Zn1 9.5(2)
C11 C1 N4 C5 175.64(17)
C10 C9 N2 Zn1 -44.51(19)
C10 C9 N2 C8 -162.71(18)
C9 C10 N3 Zn1 -37.8(2)
C9 C10 N3 C11 81.6(2)
C8 C7 N1 Zn1 41.13(19)
C8 C7 N1 C6 -78.1(2)
C7 C8 N2 Zn1 41.42(19)
C7 C8 N2 C9 158.96(18)
C6 C5 C4 C3 -178.4(2)
C6 C5 N4 Zn1 -11.3(2)
C6 C5 N4 C1 -177.64(17)
N4 Zn1 N3 C11 -13.76(13)
N4 Zn1 N3 C10 109.27(14)
N4 Zn1 N2 C9 -59.32(13)
N4 Zn1 N2 C8 63.64(14)
N4 Zn1 N1 C7 -113.23(13)
N4 Zn1 N1 C6 8.91(13)
N4 C5 C4 C3 0.5(3)
N4 C5 C6 N1 19.0(2)
N4 C1 C11 N3 -21.4(3)
N3 Zn1 N4 C5 -163.80(15)
N3 Zn1 N4 C1 2.56(14)
N3 Zn1 N2 C9 18.39(13)
N3 Zn1 N2 C8 141.34(14)
N3 Zn1 N1 C7 -78.9(2)
N3 Zn1 N1 C6 43.2(2)
N3 C10 C9 N2 58.3(3)
N2 Zn1 N4 C5 -81.12(15)
N2 Zn1 N4 C1 85.24(15)
N2 Zn1 N3 C11 -112.56(14)
N2 Zn1 N3 C10 10.46(14)
N2 Zn1 N1 C7 -14.42(13)
N2 Zn1 N1 C6 107.72(13)
N2 C8 C7 N1 -58.3(2)
N1 Zn1 N4 C5 1.24(14)
N1 Zn1 N4 C1 167.60(15)
N1 Zn1 N3 C11 -48.1(2)
N1 Zn1 N3 C10 74.9(2)
N1 Zn1 N2 C9 -137.57(13)
N1 Zn1 N2 C8 -14.62(14)
O1 C3 C2 C1 -179.7(2)
