Exploration of Ring Rearrangement Metathesis Reaction: A General and Flexible Approach for the Rapid Construction [5,n]-Fused Bicyclic Systems en Route to Linear Triquinanes.
Acharyya, Ranjan Kumar; Rej, Rohan Kalyan; Nanda, Samik; The Journal of organic chemistry 83 (2018) 2087–2103; doi:10.1021/acs.joc.7b03021

data_4033448
_publ_section_title
;
 Exploration of Ring Rearrangement Metathesis Reaction: A General and
 Flexible Approach for the Rapid Construction [5,n]-Fused Bicyclic Systems
 en Route to Linear Triquinanes.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2087
_journal_page_last               2103
_journal_paper_doi               10.1021/acs.joc.7b03021
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C14 H22 O2'
_chemical_formula_sum            'C14 H0.12 O2'
_chemical_formula_weight         200.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.89(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.435(5)
_cell_length_b                   23.467(11)
_cell_length_c                   11.844(5)
_cell_measurement_reflns_used    1188
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      17.68
_cell_measurement_theta_min      2.78
_cell_volume                     2609(2)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      299.59
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.9088
_diffrn_reflns_av_unetI/netI     1.1429
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35476
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.938
_diffrn_reflns_theta_min         2.779
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.020
_exptl_crystal_F_000             801
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         11829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.902
_refine_ls_R_factor_all          0.5598
_refine_ls_R_factor_gt           0.1736
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0671P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2831
_refine_ls_wR_factor_ref         0.4532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1778
_reflns_number_total             11829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03021_si_003.cif
_cod_data_source_block           mo_snrka526_0m
_cod_depositor_comments
'Adding full bibliography for 4033447--4033448.cif.'
_cod_database_code               4033448
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00O), C00E(H00J), C00F(H00K), C00H(H00Z),
 C00I(H00), C00J(H00Q), C00K(H00L), C00P(H00P), C00Q(H00R), C00T(H0AA),
 C00V(H00V), C011(H011), C012(H012), C014(H014), C015(H015), C017(H017),
 C01B(H1AA), C01F(H01F)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00B,H00C), C00S(H00S,H00T), C00W(H00M,H00N), C01C(H01A,H01B), C01J(H5AA,
 HF), C01K(H01K,H01L), C01N(H6AA,HG), C01P(H01Z,HI)
2.c Aromatic/amide H refined with riding coordinates:
 C00X(H00Y), C013(H013), C016(H016), C018(H018), C01D(H2AA), C01H(H01H),
 C01L(H01W), C01S(H01S)
2.d Idealised Me refined as rotating group:
 C00M(H00D,H00E,H00F), C00U(H00U,H00W,H00X), C00Z(H00G,H00H,H00I), C010(H01T,
 H01U,H01V), C019(H01,H,HA), C01E(H01G,H01I,H01J), C01G(H3AA,HB,HC), C01I(H4AA,
 HD,HE), C01M(H01M,H01N,H01O), C01O(H01X,H01Y,HH), C01Q(H01C,H01D,H01E),
 C01R(H01P,H01Q,H01R)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O003(H003), O004(H004), O005(H005), O006(H006),
 O007(H007), O008(H008)
;
_shelx_res_checksum              98481
_shelx_hkl_checksum              67333
_olex2_submission_special_instructions 'No special instructions were received'