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_1555494
_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         '4(H2 O), C19 H25 N O2'
_chemical_formula_sum            'C19 H33 N O6'
_chemical_formula_weight         371.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.80(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.714(4)
_cell_length_b                   6.3466(13)
_cell_length_c                   16.045(3)
_cell_measurement_reflns_used    4523
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.68
_cell_measurement_theta_min      2.065
_cell_volume                     2007.3(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0838
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.804
_diffrn_reflns_theta_max         24.804
_diffrn_reflns_theta_min         2.066
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9868
_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    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0840P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2150
_reflns_number_total             3466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00276_si_002.cif
_cod_data_source_block           cdx067b_num009
_cod_database_code               1555494
_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, All O(H,H) groups
2.a Free rotating group:
 O03(H03A,H03B), O04(H04A,H04B), O05(H05A,H05B), O06(H06A,H06B)
2.b Ternary CH refined with riding coordinates:
 C08(H08), C07(H07), C12(H12), C10(H10), C09(H09), C14(H14)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C17(H17A,H17B)
2.d Aromatic/amide H refined with riding coordinates:
 C05(H05), C02(H02), C03(H03), C04(H04)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'