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_4120916
_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         'C54 H30 Br2 N2 O8 Zn2'
_chemical_formula_sum            'C54 H30 Br2 N2 O8 Zn2'
_chemical_formula_weight         1125.36
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2013-01-23
_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                   10.5916(6)
_cell_length_b                   16.2330(8)
_cell_length_c                   18.2994(14)
_cell_measurement_reflns_used    4637
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      58.86
_cell_measurement_theta_min      2.41
_cell_volume                     3146.3(3)
_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
;
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
;
_computing_structure_solution
;
XM, 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 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10357
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        58.850
_diffrn_reflns_theta_max         58.85
_diffrn_reflns_theta_min         2.41
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.393
_exptl_absorpt_correction_T_max  0.7515
_exptl_absorpt_correction_T_min  0.3881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1137 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.5164.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.594
_exptl_crystal_description       lath
_exptl_crystal_F_000             562
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.055
_refine_diff_density_max         3.127
_refine_diff_density_min         -1.633
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.396
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.1145
_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^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3156
_refine_ls_wR_factor_ref         0.3484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1707
_reflns_number_total             2551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja407333q_si_002.cif
_cod_data_source_block           n2378
_cod_database_code               4120916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H9 of C9, H3 of C3, H13 of C13, {H14A,H14B} of C14, H8 of C8, H4 of C4
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
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(C6) ~ Ueq, Uanis(Zn1) ~ Ueq: with sigma 
of 0.002 and sigma for terminal atoms of 0.01
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)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C13(H13)
6.b X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
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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 = 2188.1 Ang^3^ [69.5%]
Total electron count / cell = 446.6
;
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.666
_shelx_hkl_checksum              85248
_shelx_res_checksum              10219
_shelxl_version_number           2012-6