Overcoming Strain-Induced Rearrangement Reactions: A Mild Dehydrative Aromatization Protocol for Synthesis of Highly Distorted p-Phenylenes.
Mitra, Nirmal K.; Meudom, Rolande; Corzo, Hector H.; Gorden, John D.; Merner, Bradley L.; Journal of the American Chemical Society 138 (2016) 3235–3240; doi:10.1021/jacs.6b00538

data_4130120
_publ_section_title
;
 Overcoming Strain-Induced Rearrangement Reactions: A Mild Dehydrative
 Aromatization Protocol for Synthesis of Highly Distorted p-Phenylenes.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3235
_journal_page_last               3240
_journal_paper_doi               10.1021/jacs.6b00538
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C22 H20 O2'
_chemical_formula_sum            'C22 H20 O2'
_chemical_formula_weight         316.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.735(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5333(3)
_cell_length_b                   7.8729(2)
_cell_length_c                   16.2274(4)
_cell_measurement_reflns_used    9689
_cell_measurement_temperature    180.45
_cell_measurement_theta_max      36.54
_cell_measurement_theta_min      2.59
_cell_volume                     1600.48(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2007)'
_diffrn_ambient_temperature      180.45
_diffrn_measured_fraction_theta_full 0.9773
_diffrn_measured_fraction_theta_max 0.9765
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47977
_diffrn_reflns_theta_full        37.1721
_diffrn_reflns_theta_max         37.17
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.8959.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.3130
_exptl_crystal_description       rod
_exptl_crystal_F_000             672.3188
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.7002
_refine_diff_density_min         -0.4724
_refine_diff_density_rms         0.1082
_refine_ls_d_res_high            0.5881
_refine_ls_d_res_low             10.0631
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     217
_refine_ls_number_reflns         8058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0987
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+0.7188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1560
_refine_ls_wR_factor_ref         0.1826
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -21
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              -15
_reflns_number_gt                5924
_reflns_number_total             8058
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja6b00538_si_003.cif
_cod_data_source_block           Merner121114_0m
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4130120
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C4(H4a,H4b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C14(H14), C13(H13), C16(H16), C20(H20), C12(H12), C17(H17),
 C18(H18), C19(H19), C11(H11), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'