Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D<sub>3</sub>-Trishomocubanes via the Rearrangement Approach.
Kotha, Sambasivarao; Cheekatla, Subba Rao; The Journal of organic chemistry 83 (2018) 6315–6324; doi:10.1021/acs.joc.8b00449

data_4035870
_publ_section_title
;
 Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized
 D<sub>3</sub>-Trishomocubanes via the Rearrangement Approach.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6315
_journal_page_last               6324
_journal_paper_doi               10.1021/acs.joc.8b00449
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H18 O2'
_chemical_formula_sum            'C16 H18 O2'
_chemical_formula_weight         242.30
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-12
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.019(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3329(5)
_cell_length_b                   11.9990(8)
_cell_length_c                   13.2043(9)
_cell_measurement_reflns_used    2457
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0310
_cell_measurement_theta_min      2.2930
_cell_volume                     1153.11(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -88.00  39.00   0.50    8.00    --  -20.00   0.00 -36.00  254
  2  \w   -105.00 -57.50   0.50    8.00    --  -20.00   0.00 108.00   95
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0126239000
_diffrn_orient_matrix_UB_12      -0.0434808000
_diffrn_orient_matrix_UB_13      -0.0365424000
_diffrn_orient_matrix_UB_21      -0.0841848000
_diffrn_orient_matrix_UB_22      -0.0145516000
_diffrn_orient_matrix_UB_23      0.0179564000
_diffrn_orient_matrix_UB_31      -0.0474841000
_diffrn_orient_matrix_UB_32      0.0373015000
_diffrn_orient_matrix_UB_33      -0.0356495000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3694
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.301
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.3748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1652
_reflns_number_total             2000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00449_si_003.cif
_cod_data_source_block           srk-sr-452_mo
_cod_original_cell_volume        1153.10(14)
_cod_database_code               4035870
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 85.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.99
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10), C11(H11), C5(H5), C4(H4), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C15(H15A,H15B), C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.417
_oxdiff_exptl_absorpt_empirical_full_min 0.815