The synthesis of 2- and 2,7-functionalized pyrene derivatives through Ru(II)-catalyzed C-H activation
Yan-Qin He; Yu-Wu Zhong; Chem.Commun. 51 (2015) 3411–; doi:10.1039/C4cc09480H

data_7116525
_publ_section_title
;
 The synthesis of 2- and 2,7-functionalized pyrene derivatives through
 Ru(II)-catalyzed C-H activation
;
_journal_name_full               Chem.Commun.
_journal_page_first              3411
_journal_paper_doi               10.1039/C4cc09480H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         '3(C H Cl3), 2(C38 H24 N2)'
_chemical_formula_sum            'C79 H51 Cl9 N4'
_chemical_formula_weight         1375.29
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-10-22 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                111.32(3)
_cell_angle_beta                 92.12(3)
_cell_angle_gamma                99.49(3)
_cell_formula_units_Z            1
_cell_length_a                   8.6479(17)
_cell_length_b                   12.683(3)
_cell_length_c                   16.619(3)
_cell_measurement_reflns_used    5152
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4619
_cell_measurement_theta_min      1.3228
_cell_volume                     1665.5(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution
;
'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0177
_diffrn_orient_matrix_UB_12      0.0301
_diffrn_orient_matrix_UB_13      -0.1126
_diffrn_orient_matrix_UB_21      0.0788
_diffrn_orient_matrix_UB_22      0.0345
_diffrn_orient_matrix_UB_23      0.0070
_diffrn_orient_matrix_UB_31      0.0021
_diffrn_orient_matrix_UB_32      -0.0641
_diffrn_orient_matrix_UB_33      -0.0103
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            12616
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         1.756
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.57977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             706
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.1064
_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^)+(0.0841P)^2^+2.2170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2340
_refine_ls_wR_factor_ref         0.2577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4294
_reflns_number_total             5975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc09480h2.cif
_cod_data_source_block           a
_cod_original_cell_volume        1665.4(7)
_cod_database_code               7116525
_shelxl_version_number           2013-4
_diffrn_number_total             7529
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: Cl4(0.5) Cl5(0.5) Cl6(0.5) C40(0.5) H40(0.5)
3.a Riding coordinates:
 C40(H40)
3.b Ternary CH refined with riding coordinates:
 C39(H39)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C14(H14), C15(H15), C17(H17), C21(H21), C22(H22), C24(H24), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38)
;
_shelx_res_checksum              99680
_shelx_hkl_checksum              83003