#------------------------------------------------------------------------------
#$Date: 2015-11-06 05:41:10 +0200 (Fri, 06 Nov 2015) $
#$Revision: 170050 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/36/4513647.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_4513647
loop_
_publ_author_name
'Durá, Gema'
'Carrión, M. Carmen'
'Jalón, Félix A.'
'Manzano, Blanca R.'
'Rodríguez, Ana M.'
_publ_section_title
;
 One- and Two-Step Self-Assembly Processes in Zn(II) Supramolecular
 Frameworks with Ditopic Bis(pyrazolyl)methane Ligands. Chiral Recognition
 and Formation of Cyclic Helicates
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5174
_journal_paper_doi               10.1021/acs.cgd.5b01150
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C96 H102 N30 O24 Zn6, 3(C8 H4 O4), 6(H2 O)'
_chemical_formula_sum            'C120 H126 N30 O42 Zn6'
_chemical_formula_weight         3052.72
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   36.018(3)
_cell_length_b                   36.018(3)
_cell_length_c                   21.452(2)
_cell_measurement_reflns_used    4479
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      18.75
_cell_measurement_theta_min      2.26
_cell_volume                     24101(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT, SADABS, XPREP'
_computing_molecular_graphics    'WINGX v2013.3 (Farrugia, 2013)'
_computing_publication_material  'WINGX v2013.3 (Farrugia, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEX2 CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_laue_measured_fraction_full 0.970
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51595
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.008
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             9432
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.139
_refine_diff_density_min         -0.983
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0905
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2763
_refine_ls_wR_factor_ref         0.3167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2945
_reflns_number_total             4717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b01150_si_002.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 4513645--4513647.cif.'
_cod_original_cell_volume        24101(5)
_cod_database_code               4513647
_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   0.862
_shelx_estimated_absorpt_t_max   0.963
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'
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
Zn1 Zn 0.50830(3) 0.11357(3) 0.20458(3) 0.0581(4) Uani 1 1 d . . .
N1 N 0.4528(2) 0.1000(2) 0.2561(2) 0.0624(16) Uani 1 1 d . . .
N2 N 0.4408(2) 0.1296(2) 0.2655(2) 0.0670(17) Uani 1 1 d . . .
N3 N 0.51899(19) 0.17540(19) 0.1879(2) 0.0567(14) Uani 1 1 d . . .
N4 N 0.4918(2) 0.1898(2) 0.2090(2) 0.0630(16) Uani 1 1 d . . .
N5 N 0.47643(17) 0.08790(17) 0.1205(2) 0.0493(13) Uani 1 1 d . . .
C1 C 0.4190(4) 0.1221(4) 0.3200(4) 0.118(4) Uani 1 1 d . . .
H1 H 0.4085 0.1387 0.3369 0.141 Uiso 1 1 calc R U .
C2 C 0.4156(4) 0.0877(5) 0.3445(5) 0.124(5) Uani 1 1 d . . .
H2 H 0.4015 0.0747 0.3814 0.149 Uiso 1 1 calc R U .
C3 C 0.4374(3) 0.0734(3) 0.3042(4) 0.088(3) Uani 1 1 d . . .
H3 H 0.4404 0.0495 0.3106 0.105 Uiso 1 1 calc R U .
C4 C 0.5125(4) 0.2325(3) 0.2129(5) 0.098(3) Uani 1 1 d . . .
H4 H 0.5011 0.2492 0.2265 0.117 Uiso 1 1 calc R U .
C5 C 0.5540(4) 0.2472(3) 0.1932(6) 0.119(4) Uani 1 1 d . . .
H5 H 0.5759 0.2756 0.1896 0.143 Uiso 1 1 calc R U .
C6 C 0.5561(3) 0.2115(3) 0.1801(4) 0.087(3) Uani 1 1 d . . .
H6 H 0.5810 0.2122 0.1668 0.104 Uiso 1 1 calc R U .
C7 C 0.4476(3) 0.1616(3) 0.2178(3) 0.065(2) Uani 1 1 d . . .
H7 H 0.4351 0.1785 0.2335 0.078 Uiso 1 1 calc R U .
C11 C 0.4410(3) 0.0499(3) 0.1180(4) 0.069(2) Uani 1 1 d . . .
H11 H 0.4298 0.0356 0.1554 0.083 Uiso 1 1 calc R U .
C10 C 0.4196(3) 0.0302(3) 0.0637(4) 0.079(2) Uani 1 1 d . . .
H10 H 0.3945 0.0037 0.0641 0.095 Uiso 1 1 calc R U .
C9 C 0.4378(3) 0.0522(2) 0.0079(3) 0.068(2) Uani 1 1 d . . .
H9 H 0.4249 0.0397 -0.0299 0.081 Uiso 1 1 calc R U .
C8 C 0.4735(2) 0.0911(2) 0.0082(3) 0.0537(16) Uani 1 1 d . . .
C12 C 0.4927(2) 0.1083(2) 0.0658(3) 0.0493(15) Uani 1 1 d . . .
H12 H 0.5178 0.1347 0.0664 0.059 Uiso 1 1 calc R U .
C13 C 0.5987(3) 0.1415(4) 0.1752(4) 0.091(3) Uani 1 1 d . . .
C14 C 0.6341(2) 0.1557(3) 0.1275(3) 0.073(2) Uani 1 1 d . . .
C15 C 0.6252(3) 0.1522(4) 0.0666(4) 0.100(3) Uani 1 1 d . . .
H15 H 0.5967 0.1398 0.0544 0.121 Uiso 1 1 calc R U .
C16 C 0.6560(3) 0.1659(4) 0.0214(4) 0.118(4) Uani 1 1 d . . .
H16 H 0.6484 0.1604 -0.0204 0.141 Uiso 1 1 calc R U .
C17 C 0.4670(3) -0.0449(3) 0.1173(3) 0.0622(19) Uani 1 1 d . . .
C18 C 0.4844(2) -0.0206(2) 0.0565(3) 0.0544(17) Uani 1 1 d . . .
C19 C 0.5184(2) 0.0200(2) 0.0552(3) 0.0598(18) Uani 1 1 d . . .
H19 H 0.5309 0.0338 0.0924 0.072 Uiso 1 1 calc R U .
C20 C 0.5345(2) 0.0409(2) -0.0005(3) 0.0599(18) Uani 1 1 d . . .
H20 H 0.5579 0.0686 -0.0008 0.072 Uiso 1 1 calc R U .
O1 O 0.56393(16) 0.13101(17) 0.1580(2) 0.0650(13) Uani 1 1 d . . .
O2 O 0.6106(2) 0.1483(3) 0.2338(3) 0.139(3) Uani 1 1 d . . .
O3 O 0.49936(19) 0.05433(16) 0.2252(2) 0.0715(15) Uani 1 1 d . . .
O4 O 0.54134(15) 0.13557(15) 0.28814(19) 0.0578(12) Uani 1 1 d . . .
H3A H 0.4994 0.0488 0.2639 0.050 Uiso 1 1 d . . .
H3B H 0.4935 0.0314 0.2053 0.050 Uiso 1 1 d . . .
H4A H 0.5669 0.1393 0.2888 0.050 Uiso 1 1 d . . .
H4B H 0.5383 0.1457 0.3229 0.050 Uiso 1 1 d . . .
O5 O 0.4771(3) -0.02249(19) 0.1652(2) 0.112(3) Uani 1 1 d . . .
O6 O 0.4431(2) -0.08387(18) 0.1153(2) 0.0753(16) Uani 1 1 d . . .
O11 O 0.5472 0.2047 0.3631 0.050 Uiso 0.5 1 d . . P
H11A H 0.5748 0.2047 0.3631 0.050 Uiso 0.5 1 d . . P
H11B H 0.5510 0.2307 0.3413 0.050 Uiso 0.5 1 d . . P
O12 O 0.6037 0.2812 0.3631 0.050 Uiso 0.25 1 d . . P
H12A H 0.6312 0.2812 0.3631 0.050 Uiso 0.25 1 d . . P
H12B H 0.6075 0.3072 0.3413 0.050 Uiso 0.25 1 d . . P
O13 O 0.3561 0.1060 0.4539 0.050 Uiso 0.25 1 d . . P
H13A H 0.3837 0.1060 0.4539 0.050 Uiso 0.25 1 d . . P
H13B H 0.3599 0.1320 0.4321 0.050 Uiso 0.25 1 d . . P
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Zn1 O3 92.6(2) . .
O1 Zn1 O4 91.05(19) . .
O3 Zn1 O4 88.45(19) . .
O1 Zn1 N3 87.6(2) . .
O3 Zn1 N3 177.1(2) . .
O4 Zn1 N3 88.62(19) . .
O1 Zn1 N5 87.2(2) . .
O3 Zn1 N5 87.7(2) . .
O4 Zn1 N5 175.7(2) . .
N3 Zn1 N5 95.3(2) . .
O1 Zn1 N1 175.8(2) . .
O3 Zn1 N1 90.4(2) . .
O4 Zn1 N1 86.1(2) . .
N3 Zn1 N1 89.2(2) . .
N5 Zn1 N1 95.8(2) . .
C3 N1 N2 105.6(6) . .
C3 N1 Zn1 125.4(6) . .
N2 N1 Zn1 122.2(5) . .
C1 N2 N1 110.6(7) . .
C1 N2 C7 127.6(7) . .
N1 N2 C7 121.5(5) . .
C6 N3 N4 103.1(7) . .
C6 N3 Zn1 128.6(6) . .
N4 N3 Zn1 123.4(5) . .
C4 N4 N3 111.0(8) . .
C4 N4 C7 126.8(9) . .
N3 N4 C7 121.9(6) . .
C11 N5 C12 117.2(6) . .
C11 N5 Zn1 121.6(5) . .
C12 N5 Zn1 121.1(4) . .
C2 C1 N2 108.1(9) . .
C1 C2 C3 107.0(8) . .
N1 C3 C2 108.6(9) . .
N4 C4 C5 107.3(9) . .
C6 C5 C4 105.2(10) . .
N3 C6 C5 113.4(10) . .
N4 C7 N2 110.1(6) . .
N4 C7 C8 113.0(6) . 18_544
N2 C7 C8 110.8(7) . 18_544
N5 C11 C10 124.5(7) . .
C11 C10 C9 116.5(8) . .
C8 C9 C10 121.1(7) . .
C9 C8 C12 117.9(6) . .
C9 C8 C7 122.0(6) . 18_544
C12 C8 C7 119.9(7) . 18_544
N5 C12 C8 122.8(6) . .
O1 C13 O2 123.8(8) . .
O1 C13 C14 118.7(7) . .
O2 C13 C14 116.5(8) . .
C15 C14 C16 117.8(8) . 17_654
C15 C14 C13 120.5(7) . .
C16 C14 C13 121.4(8) 17_654 .
C14 C15 C16 123.1(9) . .
C15 C16 C14 118.8(9) . 17_654
O6 C17 O5 125.5(6) . .
O6 C17 C18 118.8(6) . .
O5 C17 C18 115.7(7) . .
C19 C18 C20 119.2(6) . 19_655
C19 C18 C17 121.8(6) . .
C20 C18 C17 118.9(6) 19_655 .
C18 C19 C20 120.8(6) . .
C19 C20 C18 120.0(6) . 19_655
C13 O1 Zn1 132.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 2.037(5) .
Zn1 O3 2.041(5) .
Zn1 O4 2.077(4) .
Zn1 N3 2.092(6) .
Zn1 N5 2.089(5) .
Zn1 N1 2.116(6) .
N1 C3 1.325(9) .
N1 N2 1.353(8) .
N2 C1 1.358(10) .
N2 C7 1.467(9) .
N3 C6 1.330(11) .
N3 N4 1.391(9) .
N4 C4 1.336(11) .
N4 C7 1.411(10) .
N5 C11 1.324(9) .
N5 C12 1.353(8) .
C1 C2 1.292(15) .
C2 C3 1.426(14) .
C4 C5 1.378(16) .
C5 C6 1.354(15) .
C7 C8 1.507(10) 18_544
C11 C10 1.382(11) .
C10 C9 1.403(12) .
C9 C8 1.348(10) .
C8 C12 1.399(9) .
C8 C7 1.507(10) 18_544
C13 O1 1.174(10) .
C13 O2 1.310(11) .
C13 C14 1.510(11) .
C14 C15 1.336(12) .
C14 C16 1.402(13) 17_654
C15 C16 1.366(13) .
C16 C14 1.402(13) 17_654
C17 O6 1.227(9) .
C17 O5 1.245(8) .
C17 C18 1.521(8) .
C18 C19 1.358(10) .
C18 C20 1.394(9) 19_655
C19 C20 1.376(9) .
C20 C18 1.394(9) 19_655
