Domino intramolecular Diels-Alder reactions to construct a 6/6/5/5 fused tetracyclic framework
Gaoyuan Zhao; Min He; Huilin Li; Shuangshuang Duan; Ziyun Yuan; Xingang Xie; Xuegong She; Chem.Commun. 51 (2015) 17321–; doi:10.1039/C5cc06923H

data_7118115
_publ_section_title
;
 Domino intramolecular Diels-Alder reactions to construct a 6/6/5/5 fused
 tetracyclic framework
;
_journal_name_full               Chem.Commun.
_journal_page_first              17321
_journal_paper_doi               10.1039/C5cc06923H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C14 H20 O3'
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_weight         236.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2015-04-13 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.581(16)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   15.8905(18)
_cell_length_b                   6.1745(5)
_cell_length_c                   19.186(4)
_cell_measurement_reflns_used    1020
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7090
_cell_measurement_theta_min      3.5500
_cell_volume                     1821.8(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.7104
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0452578000
_diffrn_orient_matrix_UB_12      0.0048858000
_diffrn_orient_matrix_UB_13      0.0164453000
_diffrn_orient_matrix_UB_21      -0.0088931000
_diffrn_orient_matrix_UB_22      0.0067263000
_diffrn_orient_matrix_UB_23      0.0343424000
_diffrn_orient_matrix_UB_31      0.0014064000
_diffrn_orient_matrix_UB_32      -0.1145882000
_diffrn_orient_matrix_UB_33      0.0027051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.1352
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7814
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.984
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2400
_exptl_crystal_size_mid          0.1200
_exptl_crystal_size_min          0.1000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   3.9(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         5859
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0739
_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^)+(0.0363P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.487
_reflns_Friedel_fraction_full    0.619
_reflns_Friedel_fraction_max     0.592
_reflns_number_gt                2809
_reflns_number_total             5859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc06923h2.cif
_cod_data_source_block           zhaogy1023
_cod_original_cell_volume        1821.8(4)
_cod_database_code               7118115
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15),
 C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
  C31(H31), C32(H32), C33(H33), C36(H36), C37(H37), C39(H39), C42(H42)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C11(H11A,H11B), C12(H12A,H12B), C16(H16A,H16B),
 C17(H17A,H17B), C21(H21A,H21B), C22(H22A,H22B), C29(H29A,H29B), C30(H30A,H30B),
  C34(H34A,H34B), C35(H35A,H35B)
2.c Idealised Me refined as rotating group:
 C1E(H1EA,H1EB,H1EC), C14(H14A,H14B,H14C), C40(H40A,H40B,H40C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O6(H6A), O8(H8A)
;
_shelx_res_checksum              50982
_shelx_hkl_checksum              47288