ortho-Phenylenes: Unusual Conjugated Oligomers with a Surprisingly Long Effective Conjugation Length
Jian He; Jason L. Crase; Shriya H. Wadumethrige; Khushabu Thakur; Lin Dai; Shouzhong Zou; Rajendra Rathore; C. Scott Hartley; Journal of the American Chemical Society 132 (2010) 13848–13857; doi:10.1021/ja106050s

data_4103164
_publ_section_title
;
 ortho-Phenylenes: Unusual Conjugated Oligomers with a Surprisingly Long
 Effective Conjugation Length
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13848
_journal_page_last               13857
_journal_paper_doi               10.1021/ja106050s
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C42 H38 O6, C2 H3 N'
_chemical_formula_sum            'C44 H41 N O6'
_chemical_formula_weight         679.78
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.5803(17)
_cell_angle_beta                 82.0708(17)
_cell_angle_gamma                81.3866(17)
_cell_formula_units_Z            2
_cell_length_a                   9.3709(2)
_cell_length_b                   12.4562(2)
_cell_length_c                   15.7073(3)
_cell_measurement_reflns_used    29629
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.8975
_cell_measurement_theta_min      3.6588
_cell_volume                     1759.70(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program. 
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. 
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
1 omega  -67.00   35.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996   37.0000  -60.0000 102

2 omega  -57.00   33.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996   37.0000 -180.0000 90

3 omega  -83.00  -58.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996  125.0000 -180.0000 25

4 omega  -67.00   21.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996   77.0000   30.0000 88

5 omega  -29.00   -4.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996  125.0000 -180.0000 25

6 omega  100.00  174.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  125.0000  120.0000 74

7 omega   26.00   65.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  -45.0000    0.0000 39

8 omega   26.00   66.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  -45.0000  -90.0000 40

9 omega  142.00  176.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  125.0000 -180.0000 34

10 omega   85.00  111.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747 -103.0000  -88.0000 26

11 omega  101.00  176.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  103.0000  -91.0000 75

12 omega   28.00  132.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  -77.0000 -180.0000 104

13 omega   78.00  164.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000 -150.0000 86

14 omega  103.00  128.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  125.0000   90.0000 25

15 omega   80.00  160.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   45.0000  -90.0000 80

16 omega   87.00  162.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   45.0000 -180.0000 75

17 omega   33.00  112.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747 -112.0000  140.0000 79

18 omega -120.00   -7.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996  -77.0000  -60.0000 113

19 omega -120.00   -7.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996  -77.0000   30.0000 113

20 omega -120.00   -7.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996  -77.0000 -180.0000 113

21 omega -120.00   -7.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996  -77.0000   90.0000 113

22 omega -117.00  -15.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-      -40.7996  -37.0000 -120.0000 102

23 omega -134.00  -22.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      -55.5000  -77.0000  -30.0000 112

24 omega -134.00  -22.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      -55.5000  -77.0000 -120.0000 112

25 omega   74.00  176.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   45.0000   90.0000 102

26 omega   68.00  178.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000 -180.0000 110

27 omega   74.00  176.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   45.0000   30.0000 102

28 omega   26.00   77.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  -45.0000 -150.0000 51

29 omega   94.00  176.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747  125.0000  -30.0000 82

30 omega   68.00  178.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000 -120.0000 110

31 omega   74.00  176.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   45.0000  150.0000 102

32 omega   74.00  176.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   45.0000  -30.0000 102

33 omega   23.00   98.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-       40.7996 -125.0000  150.0000 75

34 omega   15.00  117.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-       40.7996   37.0000  -90.0000 102

35 omega   23.00   98.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-       40.7996 -125.0000   90.0000 75

36 omega   15.00  117.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-       40.7996   37.0000  120.0000 102

37 omega   15.00  117.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-       40.7996   37.0000   90.0000 102

38 omega -134.00  -22.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      -55.5000  -77.0000  120.0000 112

39 omega -134.00  -22.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      -55.5000  -77.0000 -180.0000 112

40 omega -134.00  -22.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      -55.5000  -77.0000   60.0000 112

41 omega   68.00  178.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000   30.0000 110

42 omega   68.00  178.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000  150.0000 110

43 omega   68.00  178.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000  -90.0000 110

44 omega   68.00  178.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000  -30.0000 110

45 omega   68.00  178.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000 -150.0000 110

46 omega   68.00  178.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747   77.0000   90.0000 110

47 omega   23.00  116.00   1.0000    9.4200
omega____ theta____ kappa____ phi______ frames
-      101.1747 -112.0000  140.0000 93

48 omega    8.00  117.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-       40.7996   71.0000  102.0000 109

49 omega   15.00  117.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-       40.7996   37.0000  -60.0000 102

50 omega  -49.00   76.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
-       40.7996    0.0000 -180.0000 125
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0623
_diffrn_orient_matrix_UB_12      0.0853304
_diffrn_orient_matrix_UB_13      -0.0770662
_diffrn_orient_matrix_UB_21      -0.1050631
_diffrn_orient_matrix_UB_22      -0.0240496
_diffrn_orient_matrix_UB_23      -0.058886
_diffrn_orient_matrix_UB_31      -0.1142932
_diffrn_orient_matrix_UB_32      0.0918136
_diffrn_orient_matrix_UB_33      0.0283164
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            47217
_diffrn_reflns_theta_full        71.04
_diffrn_reflns_theta_max         71.04
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.91161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         6722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.5650P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                5988
_reflns_number_total             6722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106050s_si_003.cif
_cod_data_source_block           RAJ18L
_cod_original_cell_volume        1759.69(6)
_cod_database_code               4103164