A Photochemical Route to 3- and 4-Hydroxy Derivatives of 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry.
Chang, Zong; Boyaud, France; Guillot, Régis; Boddaert, Thomas; Aitken, David J.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02559

data_4033290
_publ_section_title
;
 A Photochemical Route to 3- and 4-Hydroxy Derivatives of
 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02559
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         '4(C22 H33 N3 O6), H2 O'
_chemical_formula_sum            'C88 H134 N12 O25'
_chemical_formula_weight         1760.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 93.390(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   36.124(12)
_cell_length_b                   9.409(3)
_cell_length_c                   14.680(4)
_cell_measurement_reflns_used    1889
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      18.91
_cell_measurement_theta_min      2.26
_cell_volume                     4981(3)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.799
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2621
_diffrn_reflns_av_unetI/netI     0.3549
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            51989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.353
_diffrn_reflns_theta_min         1.738
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       plate
_exptl_crystal_F_000             1892
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         9370
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.2605
_refine_ls_R_factor_gt           0.0727
_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^)+(0.0508P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.697
_reflns_number_gt                3619
_reflns_number_total             9370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02559_si_002.cif
_cod_data_source_block           8
_cod_database_code               4033290
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              22090
_shelx_hkl_checksum              51657