Synthesis of cyclopentadienyl alkyl ethers via Pd-catalyzed cyclotrimerization of diarylacetylenes
Cai, Ranran; Huang, Mengmeng; Cui, Xiuling; Zhang, Jianye; Du, Chenxia; Wu, Yusheng; Wu, Yangjie; RSC Advances 3 (2013) 13140–; doi:10.1039/c3ra41326h

data_7239033
_publ_section_title
;
 Synthesis of cyclopentadienyl alkyl ethers via Pd-catalyzed
 cyclotrimerization of diarylacetylenes
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              13140
_journal_paper_doi               10.1039/c3ra41326h
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C36 H28 O'
_chemical_formula_sum            'C36 H28 O'
_chemical_formula_weight         476.58
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-11-08
_audit_creation_method
;
Olex2 1.1
(compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_cell_angle_alpha                99.93(2)
_cell_angle_beta                 93.55(2)
_cell_angle_gamma                114.56(3)
_cell_formula_units_Z            2
_cell_length_a                   10.131(3)
_cell_length_b                   10.150(2)
_cell_length_c                   14.682(4)
_cell_measurement_reflns_used    2872
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      66.9185
_cell_measurement_theta_min      3.0897
_cell_volume                     1337.5(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
1 omega -1.00 24.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 100.0000 -178.0000 25

2 omega -52.00 -15.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 100.0000 -178.0000 37

3 omega -65.00 -17.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 -63.0000 0.0000 48

4 omega -85.00 -22.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 -63.0000 90.0000 63

5 omega -15.00 74.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 -57.0000 -60.0000 89

6 omega 60.00 106.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 -125.0000 -90.0000 46

7 omega 51.00 120.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 57.0000 -180.0000 69

8 omega 33.00 123.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 57.0000 90.0000 90

9 omega -4.00 50.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 -57.0000 -150.0000 54

10 omega 33.00 75.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 -57.0000 60.0000 42

11 omega 42.00 87.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -25.0000 -90.0000 45

12 omega 47.00 113.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 30.0000 66

13 omega 37.00 105.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 -60.0000 68

14 omega 101.00 172.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 111.0000 0.0000 71

15 omega 37.00 106.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 -150.0000 69

16 omega 100.00 145.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 111.0000 90.0000 45

17 omega 35.00 93.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -25.0000 30.0000 58

18 omega 121.00 147.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 178.0000 -120.0000 26

19 omega 59.00 94.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 178.0000 -120.0000 35

20 omega 145.00 177.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 77.0000 150.0000 32

21 omega 103.00 171.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 50.0000 60.0000 68

22 omega 52.00 78.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -25.0000 -180.0000 26

23 omega 38.00 74.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -25.0000 120.0000 36

24 omega 38.00 79.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -77.0000 -60.0000 41

25 omega 96.00 133.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -77.0000 -60.0000 37

26 omega 43.00 91.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -25.0000 -30.0000 48

27 omega 85.00 116.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 77.0000 150.0000 31

28 omega 61.00 87.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -50.0000 150.0000 26

29 omega 137.00 178.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 12.0000 0.0000 41

30 omega 61.00 90.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 12.0000 0.0000 29

31 omega 35.00 73.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -25.0000 -120.0000 38

32 omega 53.00 130.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -63.0000 30.0000 77

33 omega 24.00 122.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 77.0000 -30.0000 98

34 omega 33.00 123.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 57.0000 -90.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0995225000
_diffrn_orient_matrix_UB_12      -0.1528895000
_diffrn_orient_matrix_UB_13      -0.0628113000
_diffrn_orient_matrix_UB_21      -0.0945716000
_diffrn_orient_matrix_UB_22      -0.0388902000
_diffrn_orient_matrix_UB_23      0.0782802000
_diffrn_orient_matrix_UB_31      -0.0983174000
_diffrn_orient_matrix_UB_32      0.0657522000
_diffrn_orient_matrix_UB_33      -0.0393351000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10451
_diffrn_reflns_theta_full        67.14
_diffrn_reflns_theta_max         67.14
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0060(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+0.0139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                3375
_reflns_number_total             4743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra41326h.txt
_cod_data_source_block           201111153
_cod_original_cell_volume        1337.4(6)
_cod_database_code               7239033
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97