Bidentate Lewis Acid Catalyzed Domino Diels-Alder Reaction of Phthalazine for the Synthesis of Bridged Oligocyclic Tetrahydronaphthalenes.
Schweighauser, Luca; Bodoky, Ina; Kessler, Simon N.; Häussinger, Daniel; Donsbach, Carsten; Wegner, Hermann A.; Organic letters 18 (2016) 1330–1333; doi:10.1021/acs.orglett.6b00276

data_1555493
_publ_section_title
;
 Bidentate Lewis Acid Catalyzed Domino Diels-Alder Reaction of Phthalazine
 for the Synthesis of Bridged Oligocyclic Tetrahydronaphthalenes.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1330
_journal_page_last               1333
_journal_paper_doi               10.1021/acs.orglett.6b00276
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C17 H21 N'
_chemical_formula_sum            'C17 H21 N'
_chemical_formula_weight         239.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                75.45(3)
_cell_angle_beta                 78.72(3)
_cell_angle_gamma                70.16(3)
_cell_formula_units_Z            2
_cell_length_a                   6.0723(12)
_cell_length_b                   8.6709(17)
_cell_length_c                   14.006(3)
_cell_measurement_reflns_used    4940
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.165
_cell_measurement_theta_min      1.51
_cell_volume                     666.5(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'STOE IPDS-2T'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6366
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         1.513
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-Area'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0660P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1985
_reflns_number_total             2819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00276_si_002.cif
_cod_data_source_block           cdx067a_cut079_num007
_cod_database_code               1555493
_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:
 C04(H04), C05(H05), C06(H06), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C07(H07), C08(H08), C09(H09), C12(H12)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'