Functionalized cyclobutenes via multicomponent thermal [2 + 2] cycloaddition reactions.
Sheldrake, Helen M.; Wallace, Timothy W.; Wilson, Craig P.; Organic letters 7 (2005) 4233–4236; doi:10.1021/ol051675f

data_1506704
_publ_section_title
;
 Functionalized cyclobutenes via multicomponent thermal [2 + 2]
 cycloaddition reactions.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4233
_journal_page_last               4236
_journal_paper_doi               10.1021/ol051675f
_journal_volume                  7
_journal_year                    2005
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H28 I1 N1 O4'
_chemical_formula_sum            'C15 H28 I N O4'
_chemical_formula_weight         413.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2005-06-09T13:52:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 110.5200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.3881(4)
_cell_length_b                   9.8190(3)
_cell_length_c                   22.3540(6)
_cell_measurement_reflns_used    7561
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      1.018
_cell_measurement_wavelength     0.71073
_cell_volume                     3779.99(18)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.39233E-2
_diffrn_orient_matrix_UB_12      0.755941E-1
_diffrn_orient_matrix_UB_13      0.309558E-1
_diffrn_orient_matrix_UB_21      0.473453E-1
_diffrn_orient_matrix_UB_22      -0.434049E-1
_diffrn_orient_matrix_UB_23      0.311815E-1
_diffrn_orient_matrix_UB_31      0.333891E-1
_diffrn_orient_matrix_UB_32      0.526651E-1
_diffrn_orient_matrix_UB_33      -0.187344E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31732
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        26.1
_diffrn_reflns_theta_max         26.1
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    1.708
_exptl_absorpt_correction_T_max  0.8755
_exptl_absorpt_correction_T_min  0.7263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.08
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         7461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0196P)^2^+8.6621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                5755
_reflns_number_total             7461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051675fsi20050715_023944.cif
_cod_data_source_block           salt
_cod_original_cell_volume        3779.99(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1506704