Turning on catalysis: incorporation of a hydrogen-bond-donating squaramide moiety into a zr metal-organic framework.
McGuirk, C. Michael; Katz, Michael J.; Stern, Charlotte L.; Sarjeant, Amy A.; Hupp, Joseph T.; Farha, Omar K.; Mirkin, Chad A.; Journal of the American Chemical Society 137 (2015) 919–925; doi:10.1021/ja511403t

data_4123292
_publ_section_title
;
 Turning on catalysis: incorporation of a hydrogen-bond-donating
 squaramide moiety into a zr metal-organic framework.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              919
_journal_page_last               925
_journal_paper_doi               10.1021/ja511403t
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C28 H18 F6 N2 O6, C2 H6 O S'
_chemical_formula_sum            'C30 H24 F6 N2 O7 S'
_chemical_formula_weight         670.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2014-08-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.455(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6680(4)
_cell_length_b                   35.2141(14)
_cell_length_c                   7.6499(3)
_cell_measurement_reflns_used    9760
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.389
_cell_measurement_theta_min      2.510
_cell_volume                     2865.11(19)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13880
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.428
_diffrn_reflns_theta_min         2.509
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0354 before and 0.0284 after correction.
The Ratio of minimum to maximum transmission is 0.9091.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         4961
_refine_ls_number_restraints     666
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0318P)^2^+3.6874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4523
_reflns_number_total             4961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511403t_si_002.cif
_cod_data_source_block           n3683
_cod_depositor_comments
'Adding full bibliography for 4123292--4123293.cif.'
_cod_database_code               4123292
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.826
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C22-C21 \\sim C23-C22 \\sim C24-C23 \\sim C25-C24 \\sim C26-C25 \\sim C26-C21
\\sim C26A-C21A \\sim C22A-
 C21A \\sim C23A-C22A \\sim C24A-C23A \\sim C25A-C24A \\sim C26A-C25A
 with sigma of 0.02
 N2-C21A \\sim N2-C21
 with sigma of 0.02
 C27-C23 \\sim C27A-C23A \\sim C28-C25 \\sim C28A-C25A
 with sigma of 0.02
 F2-C27 \\sim F1-C27 \\sim F2A-C27A \\sim F3-C27 \\sim F3A-C27A \\sim F1A-C27A
\\sim F5A-C28A \\sim F6A-
 C28A \\sim F4A-C28A \\sim F6-C28 \\sim F4-C28
 with sigma of 0.02
 F6A-F5A \\sim F2A-F1A \\sim F2-F1 \\sim F5A-F4A \\sim F1-F3 \\sim F1A-F3A
\\sim F4-F6 \\sim F4A-F6A \\sim F3-
 F2 \\sim F3A-F2A
 with sigma of 0.02
 S1-O7 \\sim S1A-O7
 with sigma of 0.02
 S1-C29 \\sim S1-C30 \\sim S1A-C30 \\sim S1A-C29A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(S1) = Uanis(O7) = Uanis(C30) = Uanis(S1A) = Uanis(C29A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=
 Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(C28A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F5A)=
 Sof(F6A)=Sof(F4A)=1-FVAR(1)
 Sof(F3)=Sof(C21)=Sof(F1)=Sof(F2)=Sof(C26)=Sof(H26)=Sof(F6)=Sof(C22)=Sof(H22)=
 Sof(F4)=Sof(C25)=Sof(C23)=Sof(C24)=Sof(H24)=Sof(C27)=Sof(C28)=Sof(F5)=FVAR(1)
 Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(S1A)=Sof(C29A)=Sof(H29D)=Sof(H29E)=
 Sof(H29F)=1-FVAR(2)
 Sof(S1)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=
 FVAR(2)
6.a Me refined with riding coordinates:
 C30(H30A,H30B,H30C), C30(H30D,H30E,H30F)
6.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C17(H17), C18(H18), C14(H14), C15(H15), C6(H6), C8(H8), C26(H26),
 C22(H22), C24(H24), C22A(H22A), C24A(H24A), C26A(H26A)
6.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C29(H29A,H29B,H29C), C29A(H29D,H29E,
 H29F)
;
_shelx_res_checksum              53911
_shelx_hkl_checksum              86134
_olex2_submission_original_sample_id 3-112-225
_olex2_submission_special_instructions 'No special instructions were received'