Highly Functionalized Cyclohexenes Derived from Benzene: Sequential Tandem Addition Reactions Promoted by Tungsten.
Wilson, Katy B.; Smith, Jacob A.; Nedzbala, Hannah S.; Pert, Emmit K.; Dakermanji, Steven J.; Dickie, Diane A.; Harman, W. Dean; The Journal of organic chemistry 84 (2019) 6094–6116; doi:10.1021/acs.joc.9b00279

data_4033685
_publ_section_title
;
 Highly Functionalized Cyclohexenes Derived from Benzene: Sequential
 Tandem Addition Reactions Promoted by Tungsten.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6094
_journal_page_last               6116
_journal_paper_doi               10.1021/acs.joc.9b00279
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C23 H35 B N7 O3 P W'
_chemical_formula_weight         683.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 99.526(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1006(15)
_cell_length_b                   11.2249(14)
_cell_length_c                   20.340(3)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      29.6098
_cell_measurement_theta_min      2.4268
_cell_volume                     2724.6(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service v2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0136
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_diffrn_reflns_limit_k_max       15
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_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
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_diffrn_reflns_theta_max         29.62
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_diffrn_source                   'fine focus sealed-tube'
_exptl_absorpt_coefficient_mu    4.336
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method 'Slow evaporation of CD3CN'
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.538
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         7660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0138
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0130P)^2^+1.4628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0317
_refine_ls_wR_factor_ref         0.0328
_reflns_number_gt                7001
_reflns_number_total             7660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00279_si_001.cif
_cod_data_source_block           6A
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4033685
_shelx_res_checksum              31564
_shelx_hkl_checksum              89046