Aromatizing Olefin Metathesis by Ligand Isolation inside a Metal- Organic Framework
Nicolaas A. Vermeulen; Olga Karagiaridi; Amy A. Sarjeant; Charlotte L. Stern; Joseph T. Hupp; Omar K. Farha; J. Fraser Stoddart; Journal of the American Chemical Society 135 (2013) 14916–14919; doi:10.1021/ja407333q

data_4120917
_publ_contact_author_name
;
;
_publ_section_title
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 Aromatizing Olefin Metathesis by Ligand Isolation inside a Metal- Organic
 Framework
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_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14916
_journal_page_last               14919
_journal_paper_doi               10.1021/ja407333q
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C58 H36 Br2 N2 O8 Zn2'
_chemical_formula_sum            'C58 H36 Br2 N2 O8 Zn2'
_chemical_formula_weight         1179.45
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           47
_space_group_name_Hall           '-P 2 2'
_space_group_name_H-M_alt        'P m m m'
_symmetry_space_group_name_Hall  '-P 2 2'
_symmetry_space_group_name_H-M   'P m m m'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-02-01
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   10.2939(11)
_cell_length_b                   16.4035(15)
_cell_length_c                   18.242(3)
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.28
_cell_measurement_theta_min      4.30
_cell_volume                     3080.3(7)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.680
_diffrn_measured_fraction_theta_max 0.928
_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  0.0821
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_Laue_measured_fraction_full 0.680
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5116
_diffrn_reflns_point_group_measured_fraction_full 0.680
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         55.98
_diffrn_reflns_theta_min         2.42
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.435
_exptl_absorpt_correction_T_max  0.7521
_exptl_absorpt_correction_T_min  0.4471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.5945.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.636
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.055
_refine_diff_density_max         1.091
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.400
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.1189
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3123
_refine_ls_wR_factor_ref         0.3484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1168
_reflns_number_total             2156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja407333q_si_003.cif
_cod_data_source_block           n2402
_cod_original_cell_volume        3080.2(6)
_cod_database_code               4120917
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H15 of C15, {H14A,H14B} of C14, H13 of C13, H9 of C9, H8 of C8, H4 of C4,
  H3 of C3
 At 1.5 times of:
  {H16A,H16B} of C16
2. Restrained distances
 C13-C12
 1.481 with sigma of 0.0001
 C13-C14
 1.329 with sigma of 0.0001
 C12-C14
 2.502 with sigma of 0.0001
 C9-C15 - C9-C10 - C9-C8 - C11-C10 - C12-C11 - C13-C12 - C14-C13 - C16-C15 -
 N1-C8 - C9-C8 - C9-C10 - C9-C15
 with sigma of 0.01
 N1-C9 - C8-C10
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.01 
and sigma for terminal atoms of 0.02
Uanis(C1) - Ueq, Uanis(C2) - Ueq, Uanis(C3) - Ueq: with sigma of 0.01 
and sigma for terminal atoms of 0.02
5. others
 Fixed Sof: C8(0.5) H8(0.5) C9(0.5) H9(0.5) C13(0.25) H13(0.25) C14(0.25)
 H14A(0.25) H14B(0.25) C15(0.25) H15(0.25) C16(0.25) H16A(0.25) H16B(0.25)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C13(H13), C15(H15)
6.b X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B)
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_smtbx_masks_special_details
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 1877.3 Ang^3^ [60.9%]
Total electron count / cell = 218.3
;
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.658
_shelx_hkl_checksum              51156
_shelx_res_checksum              23245
_shelxl_version_number           2012-9