Sc(OTf)3-Catalyzed [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Phthalazinium Dicyanomethanides.
Liu, Honglei; Yuan, Chunhao; Wu, Yang; Xiao, Yumei; Guo, Hongchao; Organic letters 17 (2015) 4220–4223; doi:10.1021/acs.orglett.5b02003

data_1555206
_publ_section_title
;
 Sc(OTf)3-Catalyzed [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters
 with Phthalazinium Dicyanomethanides.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4220
_journal_page_last               4223
_journal_paper_doi               10.1021/acs.orglett.5b02003
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H24 N4 O4'
_chemical_formula_sum            'C26 H24 N4 O4'
_chemical_formula_weight         456.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.07(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0718(18)
_cell_length_b                   20.806(4)
_cell_length_c                   12.975(3)
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      2.5445
_cell_volume                     2341.1(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0006
_diffrn_orient_matrix_UB_12      0.0504
_diffrn_orient_matrix_UB_13      0.1037
_diffrn_orient_matrix_UB_21      0.0480
_diffrn_orient_matrix_UB_22      0.0013
_diffrn_orient_matrix_UB_23      -0.0009
_diffrn_orient_matrix_UB_31      -0.0023
_diffrn_orient_matrix_UB_32      0.0796
_diffrn_orient_matrix_UB_33      -0.0124
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7812
_diffrn_reflns_point_group_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.733
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.628
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8569
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1129 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   2.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0311P)^2^+0.7631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.484
_reflns_Friedel_fraction_full    0.515
_reflns_Friedel_fraction_max     0.479
_reflns_number_gt                3747
_reflns_number_total             3950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02003_si_002.cif
_cod_data_source_block           sa3396
_cod_original_cell_volume        2341.2(9)
_cod_database_code               1555206
_shelxl_version_number           2013-4
_diffrn_number_total             2730
_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:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              71663
_shelx_hkl_checksum              9716