Stereocontrolled Preparation of Diversely Trifunctionalized Cyclobutanes.
Chang, Zong; Guillot, Régis; Boddaert, Thomas; Aitken, David J.; The Journal of organic chemistry 84 (2019) 10518–10525; doi:10.1021/acs.joc.9b01463

data_4034031
_publ_section_title
;
 Stereocontrolled Preparation of Diversely Trifunctionalized Cyclobutanes.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10518
_journal_page_last               10525
_journal_paper_doi               10.1021/acs.joc.9b01463
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H22 N2 O8'
_chemical_formula_sum            'C18 H22 N2 O8'
_chemical_formula_weight         394.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3084(3)
_cell_length_b                   14.0286(8)
_cell_length_c                   25.1623(13)
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      66.70
_cell_measurement_theta_min      3.51
_cell_volume                     1873.82(18)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27592
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.690
_diffrn_reflns_theta_max         66.690
_diffrn_reflns_theta_min         3.513
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Apex3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.59(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0337P)^2^+0.3637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3163
_reflns_number_total             3328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01463_si_002.cif
_cod_data_source_block           XRay1
_cod_database_code               4034031
_shelx_estimated_absorpt_t_min   0.891
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              30588
_shelx_hkl_checksum              96273