Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer frameworks for palladium(ii): synthesis, characterization and catalytic performance in Heck coupling
Mahmood, Qaiser; Yue, Erlin; Zhang, Wenjuan; Solan, Gregory A.; Liang, Tongling; Sun, Wen-Hua; Organic Chemistry Frontiers 3 (2016) 1668–; doi:10.1039/C6QO00469E

data_1553533
_publ_section_title
;
 Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer
 frameworks for palladium(ii): synthesis, characterization and catalytic
 performance in Heck coupling
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1668
_journal_paper_doi               10.1039/C6QO00469E
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C24 H21 N O'
_chemical_formula_sum            'C24 H21 N O'
_chemical_formula_weight         339.42
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-27 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.79(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.2943(19)
_cell_length_b                   18.714(4)
_cell_length_c                   20.557(4)
_cell_measurement_reflns_used    10313
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4837
_cell_measurement_theta_min      1.9916
_cell_volume                     3557.3(13)
_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  'XH (Sheldrick, 2008)'
_computing_structure_solution    ????
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0409
	          2theta: -19.9462
scan:
	Number of images: 240
	           Slice: -110.0000 - 10.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0409
	          2theta: -19.9462
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0599
_diffrn_orient_matrix_UB_12      -0.0056
_diffrn_orient_matrix_UB_13      0.0899
_diffrn_orient_matrix_UB_21      -0.0087
_diffrn_orient_matrix_UB_22      -0.0527
_diffrn_orient_matrix_UB_23      0.0025
_diffrn_orient_matrix_UB_31      0.0425
_diffrn_orient_matrix_UB_32      -0.0081
_diffrn_orient_matrix_UB_33      -0.0228
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19024
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6173
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0700
_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^)+(0.0369P)^2^+5.1762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1456
_reflns_number_gt                5618
_reflns_number_total             6173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00469e2.cif
_cod_data_source_block           1
_cod_original_cell_volume        3557.2(12)
_cod_database_code               1553533
_diffrn_number_total             8250
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Riding coordinates:
 N2(H2A)
3.b Ternary CH refined with riding coordinates:
 C15(H15), C39(H39)
3.c Secondary CH2 refined with riding coordinates:
 C47(H47A,H47B), C23(H23A,H23B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C42(H42), C35(H35), C11(H11), C4(H4), C28(H28), C18(H18), C3(H3),
 C9(H9), C34(H34), C8(H8), C43(H43), C27(H27), C10(H10), C25(H25), C32(H32),
 C1(H1A), C33(H33), C2(H2), C44(H44), C26(H26), C19(H19), C20(H20)
3.e Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C16(H16A,H16B,H16C), C48(H48A,H48B,H48C), C24(H24A,H24B,
 H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'