Enantioselective Recognition of Ammonium Carbamates in a Chiral Metal-Organic Framework.
Martell, Jeffrey D.; Porter-Zasada, Leo B; Forse, Alexander C.; Siegelman, Rebecca L.; Gonzalez, Miguel I.; Oktawiec, Julia; Runcevski, Tomce; Xu, Jiawei; Srebro-Hooper, Monika; Milner, Phillip J.; Colwell, Kristen A.; Autschbach, Jochen; Reimer, Jeffrey A.; Long, Jeffrey R.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b09983

data_4126641
_publ_section_title
;
 Enantioselective Recognition of Ammonium Carbamates in a Chiral
 Metal-Organic Framework.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b09983
_journal_year                    2017
_chemical_formula_moiety         'C28 H34 N4 O10 Zn2'
_chemical_formula_sum            'C28 H34 N4 O10 Zn2'
_chemical_formula_weight         717.33
_chemical_name_common            Zn2(dobpdc)(dach-CO2)2
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-10-11
_audit_creation_method
;
Olex2 1.2
(compiled Aug 10 2017 17:28:52 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   20.6012(7)
_cell_length_b                   20.6012(7)
_cell_length_c                   6.8939(3)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.056
_cell_measurement_theta_min      2.845
_cell_volume                     2533.85(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.8856
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        32.097
_diffrn_reflns_theta_max         34.076
_diffrn_reflns_theta_min         2.464
_diffrn_source
;
Advanced Light Source, station 11.3.1
;
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.658
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1467 before and 0.0949 after correction.
The Ratio of minimum to maximum transmission is 0.7739.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_primary    'pale yellow'
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1110
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     169
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0566
_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/[\s^2^(Fo^2^)+(0.0577P)^2^+7.3863P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3358
_reflns_number_total             3597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b09983_si_001.cif
_cod_data_source_block           rls133s
_cod_original_cell_volume        2533.8(2)
_cod_database_code               4126641
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.764
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.59(3)
 0.41(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H)
  groups, All N(H,H,H,H,H,H) groups
3. Restrained distances
 C9B-C10B \\sim C9A-C10A \\sim C11-C10B \\sim C11-C10A \\sim C12A-C11 \\sim
C12B-C11 \\sim C13B-C12B ~
 C13A-C12A \\sim C14-C13B \\sim C14-C13A \\sim C9B-C14 \\sim C9A-C14
 with sigma of 0.02
 N1-C9B \\sim N1-C9A
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 N1, N2, C11, C14, C9A, C10A, C12A, C13A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, N2, C11, C14, C9B, C10B, C12B, C13B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H1B(0.47) H1A(0.53) H2BD(0.47) H2BE(0.47) H2BF(0.47) H2AA(0.53)
 H2AB(0.53) H2AC(0.53) H11A(0.53) H11B(0.53) H11C(0.47) H11D(0.47) H14A(0.53)
 H14B(0.53) H14C(0.47) H14D(0.47) C9A(0.53) H9A(0.53) C10A(0.53) H10A(0.53)
 C12A(0.53) H12A(0.53) H12B(0.53) C13A(0.53) H13A(0.53) H13B(0.53) C9B(0.47)
 H9B(0.47) C10B(0.47) H10B(0.47) C12B(0.47) H12C(0.47) H12D(0.47) C13B(0.47)
 H13C(0.47) H13D(0.47)
6.a Ternary CH refined with riding coordinates:
 C9A(H9A), C10A(H10A), C9B(H9B), C10B(H10B)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D), C14(H14A,H14B), C14(H14C,H14D), C12A(H12A,
 H12B), C13A(H13A,H13B), C12B(H12C,H12D), C13B(H13C,H13D)
6.c Me refined with riding coordinates:
 N2(H2BD,H2BE,H2BF), N2(H2AA,H2AB,H2AC)
6.d Aromatic/amide H refined with riding coordinates:
 N1(H1B), N1(H1A), C3(H3), C5(H5), C6(H6)
;
_shelx_res_checksum              99718
_shelx_hkl_checksum              56257
_olex2_submission_special_instructions 'No special instructions were received'