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#$Date: 2017-07-22 05:03:12 +0300 (Sat, 22 Jul 2017) $
#$Revision: 198909 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/37/7043741.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_7043741
loop_
_publ_author_name
'Soudry, Hannah'
'Desmarets, Christophe'
'Gontard, Geoffrey'
'Edgington, Tiffany'
'Cooksy, Andrew L.'
'Amouri, Hani'
_publ_section_title
;
 Chiral two bladed ML2 metallamacrocycles: design, structures and solution
 behavior
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01151B
_journal_year                    2017
_chemical_formula_moiety         'C68 H68 N8 O4 Zn, 2(B F4), 2(C2 H3 N)'
_chemical_formula_sum            'C72 H74 B2 F8 N10 O4 Zn'
_chemical_formula_weight         1382.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-22 deposited with the CCDC.
2017-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.179(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   35.9399(12)
_cell_length_b                   9.2811(3)
_cell_length_c                   21.8244(7)
_cell_measurement_reflns_used    3043
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      59.48
_cell_measurement_theta_min      4.18
_cell_volume                     6741.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(1)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         micro-source
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24622
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.615
_diffrn_reflns_theta_min         4.174
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         5906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0480
_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)+(0.0607P)²+3.2110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                4037
_reflns_number_total             5906
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt01151b2.cif
_cod_data_source_block           Compound_2
_cod_database_code               7043741
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Zn1 Zn 0.5000 0.59402(6) 0.2500 0.03312(17) Uani 1 2 d S T P
F1 F 0.41052(6) 0.0443(2) 0.42476(11) 0.0709(6) Uani 1 1 d . . .
F2 F 0.37390(7) 0.2041(3) 0.45724(13) 0.0951(8) Uani 1 1 d . . .
F3 F 0.34669(7) 0.0975(2) 0.35847(10) 0.0755(6) Uani 1 1 d . . .
F4 F 0.35890(7) -0.0335(3) 0.44934(12) 0.0883(8) Uani 1 1 d . . .
O1 O 0.36994(5) 0.4924(2) 0.24851(9) 0.0359(5) Uani 1 1 d . . .
O2 O 0.35559(5) 0.6255(2) 0.10750(9) 0.0377(5) Uani 1 1 d . . .
N1 N 0.45897(6) 0.7102(2) 0.26978(10) 0.0312(5) Uani 1 1 d . . .
N2 N 0.41073(6) 0.7596(2) 0.30699(10) 0.0296(5) Uani 1 1 d . . .
N3 N 0.41794(6) 0.4232(3) 0.07893(11) 0.0357(6) Uani 1 1 d . . .
N4 N 0.46972(6) 0.4746(3) 0.17134(11) 0.0375(6) Uani 1 1 d . . .
N5 N 0.44551(10) 0.4882(4) 0.44131(16) 0.0705(9) Uani 1 1 d . . .
B1 B 0.37277(11) 0.0799(4) 0.42321(19) 0.0474(9) Uani 1 1 d . . .
C1 C 0.44020(7) 0.8375(3) 0.24014(13) 0.0320(6) Uani 1 1 d . . .
C2 C 0.44691(9) 0.9262(3) 0.19410(15) 0.0426(8) Uani 1 1 d . . .
H2 H 0.4674 0.9059 0.1778 0.051 Uiso 1 1 calc R U .
C3 C 0.42235(10) 1.0453(4) 0.17318(16) 0.0513(9) Uani 1 1 d . . .
H3 H 0.4258 1.1072 0.1411 0.062 Uiso 1 1 calc R U .
C4 C 0.39265(9) 1.0778(3) 0.19757(16) 0.0468(8) Uani 1 1 d . . .
H4 H 0.3767 1.1617 0.1820 0.056 Uiso 1 1 calc R U .
C5 C 0.38573(8) 0.9917(3) 0.24362(14) 0.0380(7) Uani 1 1 d . . .
H5 H 0.3657 1.0142 0.2607 0.046 Uiso 1 1 calc R U .
C6 C 0.40987(8) 0.8698(3) 0.26351(13) 0.0304(6) Uani 1 1 d . . .
C7 C 0.43975(7) 0.6682(3) 0.30820(13) 0.0318(6) Uani 1 1 d . . .
H7 H 0.4460 0.5823 0.3338 0.038 Uiso 1 1 calc R U .
C8 C 0.37883(7) 0.7297(3) 0.33316(13) 0.0320(6) Uani 1 1 d . . .
H8A H 0.3756 0.8137 0.3587 0.038 Uiso 1 1 calc R U .
H8B H 0.3865 0.6454 0.3631 0.038 Uiso 1 1 calc R U .
C9 C 0.33969(7) 0.6996(3) 0.27593(13) 0.0299(6) Uani 1 1 d . . .
C10 C 0.30706(8) 0.7910(3) 0.26052(13) 0.0336(7) Uani 1 1 d . . .
H10 H 0.3082 0.8683 0.2897 0.040 Uiso 1 1 calc R U .
C11 C 0.27252(8) 0.7736(3) 0.20353(14) 0.0362(7) Uani 1 1 d . . .
C12 C 0.27157(8) 0.6630(3) 0.15893(13) 0.0373(7) Uani 1 1 d . . .
C13 C 0.30437(8) 0.5696(3) 0.17331(13) 0.0347(7) Uani 1 1 d . . .
C14 C 0.33754(7) 0.5859(3) 0.23313(13) 0.0309(6) Uani 1 1 d . . .
C15 C 0.23742(8) 0.8760(4) 0.18862(15) 0.0464(8) Uani 1 1 d . . .
H15A H 0.2439 0.9493 0.2234 0.070 Uiso 1 1 calc R U .
H15B H 0.2136 0.8222 0.1869 0.070 Uiso 1 1 calc R U .
H15C H 0.2320 0.9229 0.1459 0.070 Uiso 1 1 calc R U .
C16 C 0.23612(9) 0.6508(4) 0.09417(15) 0.0553(9) Uani 1 1 d . . .
H16A H 0.2415 0.5762 0.0668 0.083 Uiso 1 1 calc R U .
H16B H 0.2317 0.7434 0.0709 0.083 Uiso 1 1 calc R U .
H16C H 0.2121 0.6249 0.1027 0.083 Uiso 1 1 calc R U .
C17 C 0.36585(9) 0.3702(3) 0.28559(16) 0.0459(8) Uani 1 1 d . . .
H17A H 0.3619 0.4031 0.3253 0.069 Uiso 1 1 calc R U .
H17B H 0.3902 0.3112 0.2985 0.069 Uiso 1 1 calc R U .
H17C H 0.3427 0.3126 0.2583 0.069 Uiso 1 1 calc R U .
C18 C 0.30841(8) 0.4618(3) 0.12530(13) 0.0344(7) Uani 1 1 d . . .
C19 C 0.28963(8) 0.3272(3) 0.11344(13) 0.0382(7) Uani 1 1 d . . .
C20 C 0.29871(8) 0.2266(3) 0.07331(13) 0.0370(7) Uani 1 1 d . . .
C21 C 0.32681(8) 0.2623(3) 0.04593(13) 0.0372(7) Uani 1 1 d . . .
H21 H 0.3335 0.1930 0.0197 0.045 Uiso 1 1 calc R U .
C22 C 0.34537(8) 0.3960(3) 0.05583(13) 0.0343(7) Uani 1 1 d . . .
C23 C 0.33544(7) 0.4949(3) 0.09468(13) 0.0337(7) Uani 1 1 d . . .
C24 C 0.25986(10) 0.2881(4) 0.14456(16) 0.0555(9) Uani 1 1 d . . .
H24A H 0.2338 0.2655 0.1097 0.083 Uiso 1 1 calc R U .
H24B H 0.2568 0.3696 0.1708 0.083 Uiso 1 1 calc R U .
H24C H 0.2697 0.2040 0.1733 0.083 Uiso 1 1 calc R U .
C25 C 0.27998(10) 0.0785(3) 0.06215(16) 0.0494(8) Uani 1 1 d . . .
H25A H 0.2867 0.0296 0.1048 0.074 Uiso 1 1 calc R U .
H25B H 0.2903 0.0224 0.0339 0.074 Uiso 1 1 calc R U .
H25C H 0.2507 0.0874 0.0405 0.074 Uiso 1 1 calc R U .
C26 C 0.33363(10) 0.7497(4) 0.07604(18) 0.0567(9) Uani 1 1 d . . .
H26A H 0.3304 0.7502 0.0294 0.085 Uiso 1 1 calc R U .
H26B H 0.3482 0.8363 0.0979 0.085 Uiso 1 1 calc R U .
H26C H 0.3071 0.7482 0.0791 0.085 Uiso 1 1 calc R U .
C27 C 0.37673(8) 0.4311(4) 0.02745(13) 0.0404(8) Uani 1 1 d . . .
H27A H 0.3743 0.3625 -0.0086 0.049 Uiso 1 1 calc R U .
H27B H 0.3719 0.5293 0.0083 0.049 Uiso 1 1 calc R U .
C28 C 0.44765(8) 0.3221(3) 0.08430(13) 0.0348(7) Uani 1 1 d . . .
C29 C 0.44858(10) 0.2052(3) 0.04492(15) 0.0441(8) Uani 1 1 d . . .
H29 H 0.4267 0.1827 0.0051 0.053 Uiso 1 1 calc R U .
C30 C 0.48302(11) 0.1247(4) 0.06728(17) 0.0539(9) Uani 1 1 d . . .
H30 H 0.4849 0.0440 0.0419 0.065 Uiso 1 1 calc R U .
C31 C 0.51552(10) 0.1560(4) 0.12580(17) 0.0519(9) Uani 1 1 d . . .
H31 H 0.5387 0.0963 0.1391 0.062 Uiso 1 1 calc R U .
C32 C 0.51444(9) 0.2711(3) 0.16424(16) 0.0434(8) Uani 1 1 d . . .
H32 H 0.5364 0.2927 0.2041 0.052 Uiso 1 1 calc R U .
C33 C 0.47987(8) 0.3552(3) 0.14271(14) 0.0329(6) Uani 1 1 d . . .
C34 C 0.43273(8) 0.5094(3) 0.13161(14) 0.0414(7) Uani 1 1 d . . .
H34 H 0.4182 0.5878 0.1397 0.050 Uiso 1 1 calc R U .
C35 C 0.45568(10) 0.3995(4) 0.47952(17) 0.0521(9) Uani 1 1 d . . .
C36 C 0.46895(11) 0.2870(4) 0.52832(17) 0.0642(10) Uani 1 1 d . . .
H36A H 0.4884 0.2255 0.5191 0.096 Uiso 1 1 calc R U .
H36B H 0.4458 0.2290 0.5268 0.096 Uiso 1 1 calc R U .
H36C H 0.4817 0.3299 0.5724 0.096 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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
N4 Zn1 N4 112.19(14) . 2_655
N4 Zn1 N1 108.79(9) . 2_655
N4 Zn1 N1 106.21(9) 2_655 2_655
N4 Zn1 N1 106.21(9) . .
N4 Zn1 N1 108.79(9) 2_655 .
N1 Zn1 N1 114.77(13) 2_655 .
C14 O1 C17 112.1(2) . .
C23 O2 C26 117.4(2) . .
C7 N1 C1 105.4(2) . .
C7 N1 Zn1 125.31(19) . .
C1 N1 Zn1 128.62(17) . .
C7 N2 C6 107.3(2) . .
C7 N2 C8 125.6(2) . .
C6 N2 C8 125.4(2) . .
C34 N3 C28 106.7(2) . .
C34 N3 C27 125.5(2) . .
C28 N3 C27 127.7(2) . .
C34 N4 C33 105.7(2) . .
C34 N4 Zn1 121.1(2) . .
C33 N4 Zn1 133.11(18) . .
F2 B1 F4 111.2(3) . .
F2 B1 F3 109.0(3) . .
F4 B1 F3 107.6(3) . .
F2 B1 F1 111.1(3) . .
F4 B1 F1 108.2(3) . .
F3 B1 F1 109.5(3) . .
C2 C1 N1 130.8(2) . .
C2 C1 C6 120.6(3) . .
N1 C1 C6 108.7(2) . .
C3 C2 C1 116.7(3) . .
C2 C3 C4 122.2(3) . .
C5 C4 C3 121.9(3) . .
C4 C5 C6 115.8(3) . .
N2 C6 C5 131.5(2) . .
N2 C6 C1 105.8(2) . .
C5 C6 C1 122.7(3) . .
N1 C7 N2 112.8(2) . .
N2 C8 C9 109.2(2) . .
C10 C9 C14 118.4(2) . .
C10 C9 C8 121.8(2) . .
C14 C9 C8 119.5(2) . .
C9 C10 C11 122.2(3) . .
C10 C11 C12 118.8(3) . .
C10 C11 C15 120.5(3) . .
C12 C11 C15 120.6(3) . .
C13 C12 C11 119.9(2) . .
C13 C12 C16 120.4(3) . .
C11 C12 C16 119.6(3) . .
C12 C13 C14 119.3(2) . .
C12 C13 C18 123.6(2) . .
C14 C13 C18 116.8(2) . .
O1 C14 C9 118.9(2) . .
O1 C14 C13 119.9(2) . .
C9 C14 C13 121.2(2) . .
C19 C18 C23 118.7(3) . .
C19 C18 C13 124.1(2) . .
C23 C18 C13 117.0(3) . .
C18 C19 C20 120.1(3) . .
C18 C19 C24 120.4(3) . .
C20 C19 C24 119.5(3) . .
C21 C20 C19 119.1(3) . .
C21 C20 C25 119.9(3) . .
C19 C20 C25 120.9(3) . .
C22 C21 C20 122.0(3) . .
C23 C22 C21 117.9(2) . .
C23 C22 C27 120.8(3) . .
C21 C22 C27 121.2(3) . .
C22 C23 O2 117.9(2) . .
C22 C23 C18 122.1(3) . .
O2 C23 C18 119.8(2) . .
N3 C27 C22 111.3(2) . .
C29 C28 N3 132.0(3) . .
C29 C28 C33 122.1(3) . .
N3 C28 C33 105.9(2) . .
C30 C29 C28 115.8(3) . .
C29 C30 C31 123.0(3) . .
C32 C31 C30 121.0(3) . .
C31 C32 C33 117.4(3) . .
N4 C33 C32 130.5(3) . .
N4 C33 C28 108.6(2) . .
C32 C33 C28 120.8(3) . .
N4 C34 N3 113.1(3) . .
N5 C35 C36 179.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N4 1.988(2) .
Zn1 N4 1.988(2) 2_655
Zn1 N1 2.001(2) 2_655
Zn1 N1 2.001(2) .
F1 B1 1.384(4) .
F2 B1 1.364(4) .
F3 B1 1.379(4) .
F4 B1 1.377(4) .
O1 C14 1.387(3) .
O1 C17 1.433(4) .
O2 C23 1.386(3) .
O2 C26 1.419(4) .
N1 C7 1.330(3) .
N1 C1 1.392(3) .
N2 C7 1.337(3) .
N2 C6 1.388(3) .
N2 C8 1.487(3) .
N3 C34 1.336(4) .
N3 C28 1.393(3) .
N3 C27 1.485(3) .
N4 C34 1.324(3) .
N4 C33 1.387(4) .
N5 C35 1.130(4) .
C1 C2 1.389(4) .
C1 C6 1.399(4) .
C2 C3 1.380(4) .
C3 C4 1.394(4) .
C4 C5 1.378(4) .
C5 C6 1.392(4) .
C8 C9 1.513(3) .
C9 C10 1.382(4) .
C9 C14 1.392(4) .
C10 C11 1.396(4) .
C11 C12 1.406(4) .
C11 C15 1.514(4) .
C12 C13 1.400(4) .
C12 C16 1.508(4) .
C13 C14 1.405(4) .
C13 C18 1.495(4) .
C18 C19 1.397(4) .
C18 C23 1.405(4) .
C19 C20 1.401(4) .
C19 C24 1.512(4) .
C20 C21 1.394(4) .
C20 C25 1.509(4) .
C21 C22 1.386(4) .
C22 C23 1.384(4) .
C22 C27 1.512(4) .
C28 C29 1.392(4) .
C28 C33 1.395(4) .
C29 C30 1.368(4) .
C30 C31 1.398(5) .
C31 C32 1.369(4) .
C32 C33 1.390(4) .
C35 C36 1.438(5) .
