#------------------------------------------------------------------------------
#$Date: 2019-11-25 21:10:18 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241823 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/16/4131647.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_4131647
loop_
_publ_author_name
'Liu, Lujia'
'Zhou, Tian-You'
'Telfer, Shane G.'
_publ_section_title
;
 Modulating the Performance of an Asymmetric Organocatalyst by Tuning Its
 Spatial Environment in a Metal-Organic Framework.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13936
_journal_page_last               13943
_journal_paper_doi               10.1021/jacs.7b07921
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C64 H50 N O14.5 Zn4'
_chemical_formula_weight         1326.53
_space_group_crystal_system      cubic
_space_group_IT_number           200
_space_group_name_Hall           '-P 2 2 3'
_space_group_name_H-M_alt        'P m -3'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   29.9444(6)
_cell_length_b                   29.9444(6)
_cell_length_c                   29.9444(6)
_cell_measurement_reflns_used    6110
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      71.83
_cell_measurement_theta_min      8.51
_cell_volume                     26850.2(9)
_computing_cell_refinement       'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_molecular_graphics    'OLEX (Dolomanov, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            103365
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.080
_diffrn_reflns_theta_min         6.611
_diffrn_source                   'Rigaku MM007 rotating anode'
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4062
_exptl_crystal_size_max          0.803
_exptl_crystal_size_mid          0.803
_exptl_crystal_size_min          0.736
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         9316
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0681
_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)+(0.0867P)²+21.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.1946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7621
_reflns_number_total             9316
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b07921_si_002.cif
_cod_data_source_block           MUF-77-methyl-1-BOC
_cod_original_cell_volume        26850.2(16)
_cod_original_formula_sum        'C64 H50 N O14.50 Zn4'
_cod_database_code               4131647
_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.
;
_shelx_estimated_absorpt_t_min   0.568
_shelx_estimated_absorpt_t_max   0.593
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
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
Zn1 Zn 0.05326(2) 0.17750(2) 0.5000 0.04364(16) Uani 1 2 d S T P . .
Zn2 Zn 0.0000 0.25170(2) 0.44679(2) 0.04564(16) Uani 1 2 d S T P . .
O1 O 0.0000 0.21453(10) 0.5000 0.0415(7) Uani 1 4 d S T P . .
O2 O 0.03724(11) 0.11503(9) 0.5000 0.0723(9) Uani 1 2 d S T P . .
O3 O 0.0000 0.31396(10) 0.46316(13) 0.0925(12) Uani 1 2 d S T P . .
O4 O 0.08911(8) 0.18794(8) 0.44752(8) 0.0731(6) Uani 1 1 d . . . . .
O5 O 0.05288(8) 0.24165(8) 0.41127(8) 0.0733(6) Uani 1 1 d . . . . .
C1 C 0.0000 0.09606(19) 0.5000 0.0599(15) Uani 1 4 d S T P . .
C2 C 0.0000 0.04623(19) 0.5000 0.0640(16) Uani 1 4 d S T P . .
C3 C 0.03942(18) 0.02280(15) 0.5000 0.0947(19) Uani 1 2 d S T P . .
H3 H 0.0664 0.0382 0.5000 0.114 Uiso 1 2 calc R U P . .
C4 C 0.0000 0.3327(2) 0.5000 0.0705(18) Uani 1 4 d S T P . .
C5 C 0.0000 0.3823(2) 0.5000 0.095(3) Uani 1 4 d DS T P . .
C6 C 0.0167(2) 0.4056(2) 0.4643(2) 0.140(7) Uani 0.5 1 d D . P A .
C7 C 0.0174(2) 0.4517(2) 0.4647(2) 0.159(9) Uani 0.5 1 d D . P . .
C8 C 0.0000 0.4753(3) 0.5000 0.138(5) Uani 1 4 d DS T P . .
H6 H 0.0278(5) 0.3905(2) 0.4396(3) 0.166 Uiso 0.5 1 d D U P . .
H7 H 0.0298(5) 0.4669(2) 0.4406(3) 0.166 Uiso 0.375 1 d D U P . .
C9 C 0.08468(11) 0.21482(11) 0.41586(11) 0.0644(8) Uani 1 1 d . . . . .
C10 C 0.12040(12) 0.21501(12) 0.38109(12) 0.0768(10) Uani 1 1 d . . . . .
C11 C 0.15383(15) 0.18309(15) 0.38186(14) 0.1032(16) Uani 1 1 d . . . . .
H11 H 0.1540 0.1618 0.4044 0.124 Uiso 1 1 calc R U . . .
C12 C 0.18695(16) 0.18238(15) 0.34960(15) 0.1154(19) Uani 1 1 d . . . . .
H12 H 0.2089 0.1605 0.3503 0.138 Uiso 1 1 calc R U . . .
C13 C 0.18717(14) 0.21438(14) 0.31638(14) 0.0932(14) Uani 1 1 d . . . . .
C14 C 0.15391(13) 0.24675(13) 0.31596(13) 0.0871(12) Uani 1 1 d . . . . .
C15 C 0.12041(13) 0.24704(13) 0.34767(12) 0.0838(11) Uani 1 1 d . . . . .
H15 H 0.0980 0.2685 0.3466 0.101 Uiso 1 1 calc R U . . .
C16 C 0.21738(13) 0.22328(14) 0.27757(13) 0.0913(13) Uani 1 1 d . . . . .
C17 C 0.20157(13) 0.26144(14) 0.25548(14) 0.0919(14) Uani 1 1 d . . . . .
C18 C 0.15929(14) 0.27952(14) 0.27785(14) 0.0961(14) Uani 1 1 d . . . . .
C19 C 0.16739(18) 0.32629(15) 0.29843(18) 0.128(2) Uani 1 1 d . . . . .
H19A H 0.1410 0.3359 0.3139 0.192 Uiso 1 1 calc R U . . .
H19B H 0.1742 0.3472 0.2751 0.192 Uiso 1 1 calc R U . . .
H19C H 0.1919 0.3248 0.3190 0.192 Uiso 1 1 calc R U . . .
C20 C 0.11813(16) 0.27672(19) 0.24758(16) 0.125(2) Uani 1 1 d . . . . .
H20A H 0.1125 0.2461 0.2400 0.188 Uiso 1 1 calc R U . . .
H20B H 0.1234 0.2935 0.2208 0.188 Uiso 1 1 calc R U . . .
H20C H 0.0927 0.2888 0.2629 0.188 Uiso 1 1 calc R U . . .
N51 N 0.0260(4) 0.4789(4) 0.4261(3) 0.100 Uiso 0.125 1 d G U P A -1
H51 H 0.0257 0.5068 0.4292 0.120 Uiso 0.125 1 d G U P A -1
O53 O 0.0626(4) 0.4252(3) 0.3852(5) 0.100 Uiso 0.125 1 d G U P A -1
O60 O 0.0184(4) 0.5918(3) 0.3402(4) 0.100 Uiso 0.125 1 d G U P A -1
O61 O 0.0163(3) 0.5162(3) 0.3291(3) 0.100 Uiso 0.125 1 d G U P A -1
N58 N 0.0677(3) 0.5447(3) 0.3738(3) 0.100 Uiso 0.125 1 d G U P A -1
C52 C 0.0573(3) 0.4641(3) 0.3961(4) 0.100 Uiso 0.125 1 d G U P A -1
C54 C 0.0878(3) 0.5003(3) 0.3779(3) 0.100 Uiso 0.125 1 d G U P A -1
H54 H 0.0973 0.4891 0.3486 0.150 Uiso 0.125 1 d G U P A -1
C55 C 0.1278(3) 0.5089(5) 0.4091(4) 0.100 Uiso 0.125 1 d G U P A -1
H55A H 0.1173 0.5090 0.4415 0.150 Uiso 0.125 1 d G U P A -1
H55B H 0.1503 0.4861 0.4044 0.150 Uiso 0.125 1 d G U P A -1
C56 C 0.1414(3) 0.5566(5) 0.3976(5) 0.100 Uiso 0.125 1 d G U P A -1
H56A H 0.1595 0.5709 0.4204 0.150 Uiso 0.125 1 d G U P A -1
H56B H 0.1573 0.5562 0.3683 0.150 Uiso 0.125 1 d G U P A -1
C57 C 0.0969(4) 0.5803(4) 0.3913(4) 0.100 Uiso 0.125 1 d G U P A -1
H57A H 0.0842 0.5906 0.4192 0.150 Uiso 0.125 1 d G U P A -1
H57B H 0.0983 0.6065 0.3687 0.150 Uiso 0.125 1 d G U P A -1
C59 C 0.0326(3) 0.5544(3) 0.3467(3) 0.100 Uiso 0.125 1 d G U P A -1
C62 C -0.0296(3) 0.5140(4) 0.3105(4) 0.100 Uiso 0.125 1 d G U P A -1
C63 C -0.0625(3) 0.5287(4) 0.3456(5) 0.100 Uiso 0.125 1 d G U P A -1
H63A H -0.0613 0.5615 0.3519 0.150 Uiso 0.125 1 d G U P A -1
H63B H -0.0587 0.5106 0.3746 0.150 Uiso 0.125 1 d G U P A -1
H63C H -0.0932 0.5228 0.3367 0.150 Uiso 0.125 1 d G U P A -1
C64 C -0.0329(4) 0.5410(5) 0.2677(4) 0.100 Uiso 0.125 1 d G U P A -1
H64A H -0.0311 0.5737 0.2753 0.150 Uiso 0.125 1 d G U P A -1
H64B H -0.0654 0.5351 0.2534 0.150 Uiso 0.125 1 d G U P A -1
H64C H -0.0097 0.5311 0.2469 0.150 Uiso 0.125 1 d G U P A -1
C65 C -0.0345(4) 0.4645(4) 0.3003(5) 0.100 Uiso 0.125 1 d G U P A -1
H65A H -0.0651 0.4590 0.2899 0.150 Uiso 0.125 1 d G U P A -1
H65B H -0.0300 0.4471 0.3277 0.150 Uiso 0.125 1 d G U P A -1
H65C H -0.0122 0.4555 0.2753 0.150 Uiso 0.125 1 d G U P A -1
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'
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'
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
O4 Zn1 O4 109.15(15) . 14_556
O4 Zn1 O2 107.16(9) . .
O4 Zn1 O2 107.16(9) 14_556 .
O4 Zn1 O1 111.38(7) . .
O4 Zn1 O1 111.38(7) 14_556 .
O2 Zn1 O1 110.43(12) . .
O3 Zn2 O5 106.90(9) . 16
O3 Zn2 O5 106.91(9) . .
O5 Zn2 O5 110.17(15) 16 .
O3 Zn2 O1 110.20(13) . .
O5 Zn2 O1 111.24(7) 16 .
O5 Zn2 O1 111.24(7) . .
Zn1 O1 Zn1 110.38(15) . 3_556
Zn1 O1 Zn2 109.080(10) . 14_556
Zn1 O1 Zn2 109.080(10) 3_556 14_556
Zn1 O1 Zn2 109.079(10) . .
Zn1 O1 Zn2 109.079(10) 3_556 .
Zn2 O1 Zn2 110.13(15) 14_556 .
C1 O2 Zn1 131.4(3) . .
C4 O3 Zn2 131.7(4) . .
C9 O4 Zn1 131.5(2) . .
C9 O5 Zn2 131.5(2) . .
O2 C1 O2 126.0(5) 3_556 .
O2 C1 C2 117.0(3) 3_556 .
O2 C1 C2 117.0(3) . .
C3 C2 C3 118.5(6) . 3_556
C3 C2 C1 120.7(3) . .
C3 C2 C1 120.7(3) 3_556 .
C3 C3 C2 120.7(3) 15 .
O3 C4 O3 126.1(6) . 14_556
O3 C4 C5 117.0(3) . .
O3 C4 C5 117.0(3) 14_556 .
C6 C5 C6 102.3(7) . 14_556
C6 C5 C6 118.7(7) . 3_556
C6 C5 C6 42.9(6) 14_556 3_556
C6 C5 C6 42.9(6) . 16
C6 C5 C6 118.8(7) 14_556 16
C6 C5 C6 102.3(7) 3_556 16
C6 C5 C4 120.6(4) . .
C6 C5 C4 120.6(4) 14_556 .
C6 C5 C4 120.6(4) 3_556 .
C6 C5 C4 120.6(4) 16 .
C6 C6 C5 68.6(3) 16 .
C6 C6 C7 90.8(3) 16 .
C5 C6 C7 120.6(4) . .
C6 C6 C7 53.5(3) 16 16
C5 C6 C7 100.8(4) . 16
C7 C6 C7 37.3(5) . 16
C7 C7 C8 67.7(3) 16 .
C7 C7 C6 89.2(3) 16 .
C8 C7 C6 120.9(4) . .
C7 C7 N51 100.3(5) 16 .
C8 C7 N51 113.3(8) . .
C6 C7 N51 124.3(6) . .
C7 C7 C6 53.5(3) 16 16
C8 C7 C6 101.1(5) . 16
C6 C7 C6 35.7(5) . 16
N51 C7 C6 123.9(6) . 16
C7 C8 C7 44.6(6) . 16
C7 C8 C7 100.6(7) . 14_556
C7 C8 C7 118.2(8) 16 14_556
C7 C8 C7 118.2(8) . 3_556
C7 C8 C7 100.6(7) 16 3_556
C7 C8 C7 44.6(6) 14_556 3_556
C7 C8 C8 120.9(4) . 13_566
C7 C8 C8 120.9(4) 16 13_566
C7 C8 C8 120.9(4) 14_556 13_566
C7 C8 C8 120.9(4) 3_556 13_566
O4 C9 O5 125.2(3) . .
O4 C9 C10 117.1(3) . .
O5 C9 C10 117.7(3) . .
C11 C10 C15 119.3(3) . .
C11 C10 C9 120.3(3) . .
C15 C10 C9 120.4(3) . .
C10 C11 C12 121.1(3) . .
C13 C12 C11 119.7(3) . .
C12 C13 C14 119.1(3) . .
C12 C13 C16 133.3(3) . .
C14 C13 C16 107.6(3) . .
C15 C14 C13 121.2(3) . .
C15 C14 C18 126.3(3) . .
C13 C14 C18 112.5(3) . .
C14 C15 C10 119.5(3) . .
C17 C16 C17 119.4(3) 5 .
C17 C16 C13 132.7(3) 5 .
C17 C16 C13 107.9(3) . .
C16 C17 C16 120.6(3) 9 .
C16 C17 C18 128.2(3) 9 .
C16 C17 C18 111.2(3) . .
C14 C18 C17 100.9(3) . .
C14 C18 C20 109.0(4) . .
C17 C18 C20 112.8(4) . .
C14 C18 C19 107.6(4) . .
C17 C18 C19 111.4(4) . .
C20 C18 C19 114.3(4) . .
C52 N51 C7 117.8(8) . .
C59 O61 C62 121.2 . .
C59 N58 C54 124.2 . .
C59 N58 C57 121.1 . .
C54 N58 C57 112.5 . .
O53 C52 N51 124.8 . .
O53 C52 C54 120.5 . .
N51 C52 C54 114.6 . .
N58 C54 C52 115.5 . .
N58 C54 C55 102.6 . .
C52 C54 C55 111.6 . .
C56 C55 C54 103.1 . .
C57 C56 C55 103.4 . .
N58 C57 C56 103.0 . .
O60 C59 O61 126.3 . .
O60 C59 N58 124.3 . .
O61 C59 N58 109.4 . .
O61 C62 C63 109.4 . .
O61 C62 C64 110.8 . .
C63 C62 C64 113.0 . .
O61 C62 C65 101.9 . .
C63 C62 C65 111.1 . .
C64 C62 C65 110.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O4 1.929(2) .
Zn1 O4 1.929(2) 14_556
Zn1 O2 1.931(3) .
Zn1 O1 1.9424(18) .
Zn2 O3 1.928(3) .
Zn2 O5 1.931(2) 16
Zn2 O5 1.931(2) .
Zn2 O1 1.9436(18) .
O1 Zn1 1.9424(18) 3_556
O1 Zn2 1.9436(18) 14_556
O2 C1 1.252(4) .
O3 C4 1.238(4) .
O4 C9 1.251(4) .
O5 C9 1.253(4) .
C1 O2 1.252(4) 3_556
C1 C2 1.492(8) .
C2 C3 1.373(6) .
C2 C3 1.373(6) 3_556
C3 C3 1.365(9) 15
C4 O3 1.238(4) 14_556
C4 C5 1.485(8) .
C5 C6 1.371(7) .
C5 C6 1.371(7) 14_556
C5 C6 1.371(7) 3_556
C5 C6 1.371(7) 16
C6 C6 1.002(13) 16
C6 C7 1.381(10) .
C6 C7 1.718(10) 16
C7 C7 1.042(13) 16
C7 C8 1.374(7) .
C7 N51 1.435(10) .
C7 C6 1.718(10) 16
C8 C7 1.374(7) 16
C8 C7 1.374(7) 14_556
C8 C7 1.374(7) 3_556
C8 C8 1.478(15) 13_566
C9 C10 1.493(4) .
C10 C11 1.384(5) .
C10 C15 1.386(4) .
C11 C12 1.385(5) .
C12 C13 1.381(5) .
C13 C14 1.390(5) .
C13 C16 1.497(5) .
C14 C15 1.381(5) .
C14 C18 1.514(5) .
C16 C17 1.399(5) 5
C16 C17 1.403(5) .
C17 C16 1.399(5) 9
C17 C18 1.531(5) .
C18 C20 1.532(7) .
C18 C19 1.549(7) .
N51 C52 1.3723 .
O53 C52 1.2189 .
O60 C59 1.2131 .
O61 C59 1.3502 .
O61 C62 1.4839 .
N58 C59 1.3585 .
N58 C54 1.4653 .
N58 C57 1.4764 .
C52 C54 1.5189 .
C54 C55 1.5395 .
C55 C56 1.5252 .
C56 C57 1.5202 .
C62 C63 1.5057 .
C62 C64 1.5197 .
C62 C65 1.5208 .
