#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:31:40 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235107 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/35/1553539.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1553539
loop_
_publ_author_name
'Mahmood, Qaiser'
'Yue, Erlin'
'Zhang, Wenjuan'
'Solan, Gregory A.'
'Liang, Tongling'
'Sun, Wen-Hua'
_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_sum            'C40 H33 N3 O0'
_chemical_formula_weight         555.69
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-07-28 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.37(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.910(2)
_cell_length_b                   32.793(7)
_cell_length_c                   9.4655(19)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4851
_cell_measurement_theta_min      1.8631
_cell_volume                     3393.6(14)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23288
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_platon_squeeze_details          ' ?'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         7780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+1.2942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1510
_reflns_number_gt                6204
_reflns_number_total             7780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00469e2.cif
_cod_data_source_block           L1
_cod_original_cell_volume        3393.6(12)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1553539
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.50060(13) 0.14548(4) 0.45846(16) 0.0295(3) Uani 1 1 d .
C15 C 0.63445(15) 0.21782(5) 0.48448(18) 0.0270(3) Uani 1 1 d .
C16 C 0.66883(15) 0.18148(5) 0.42822(18) 0.0281(3) Uani 1 1 d .
N3 N 0.49391(14) 0.05761(4) 0.19361(18) 0.0363(3) Uani 1 1 d .
C12 C 0.46851(15) 0.17968(5) 0.50688(18) 0.0279(3) Uani 1 1 d .
C13 C 0.52645(15) 0.21809(5) 0.51004(18) 0.0281(3) Uani 1 1 d .
C14 C 0.47020(15) 0.25511(5) 0.53963(19) 0.0307(4) Uani 1 1 d .
C32 C 0.72066(15) 0.25246(5) 0.53899(19) 0.0284(3) Uani 1 1 d .
H32 H 0.7253 0.2661 0.6296 0.034 Uiso 1 1 calc R
N2 N 0.78913(13) 0.26541(4) 0.47399(16) 0.0312(3) Uani 1 1 d .
C6 C 0.33024(15) 0.21188(5) 0.61497(19) 0.0329(4) Uani 1 1 d .
C11 C 0.37239(15) 0.17665(5) 0.56650(19) 0.0312(4) Uani 1 1 d .
C21 C 0.59476(15) 0.14620(5) 0.41266(18) 0.0281(3) Uani 1 1 d .
C1 C 0.50132(16) 0.29415(5) 0.5044(2) 0.0356(4) Uani 1 1 d .
H1 H 0.5596 0.2965 0.4595 0.043 Uiso 1 1 calc R
C5 C 0.37601(15) 0.25210(5) 0.59439(19) 0.0332(4) Uani 1 1 d .
C33 C 0.87820(15) 0.29562(5) 0.55234(19) 0.0288(3) Uani 1 1 d .
C34 C 0.97644(15) 0.28619(5) 0.69090(19) 0.0303(4) Uani 1 1 d .
C7 C 0.24090(17) 0.20724(6) 0.6760(2) 0.0416(4) Uani 1 1 d .
H7 H 0.2112 0.2306 0.7096 0.050 Uiso 1 1 calc R
C38 C 0.87045(16) 0.33343(5) 0.4799(2) 0.0338(4) Uani 1 1 d .
C17 C 0.77069(16) 0.17819(5) 0.3869(2) 0.0324(4) Uani 1 1 d .
H17 H 0.8256 0.2005 0.4051 0.039 Uiso 1 1 calc R
C19 C 0.71366(17) 0.10944(5) 0.2989(2) 0.0376(4) Uani 1 1 d .
H19 H 0.7274 0.0858 0.2500 0.045 Uiso 1 1 calc R
C29 C 0.48740(19) -0.01657(5) 0.1705(2) 0.0395(4) Uani 1 1 d .
C18 C 0.79070(17) 0.14334(5) 0.3214(2) 0.0371(4) Uani 1 1 d .
H18 H 0.8575 0.1420 0.2907 0.045 Uiso 1 1 calc R
C22 C 0.54289(17) 0.07250(5) 0.3284(2) 0.0338(4) Uani 1 1 d .
C10 C 0.32475(17) 0.13831(6) 0.5794(2) 0.0390(4) Uani 1 1 d .
H10 H 0.3531 0.1146 0.5462 0.047 Uiso 1 1 calc R
C20 C 0.61905(16) 0.10991(5) 0.34613(19) 0.0313(4) Uani 1 1 d .
C3 C 0.36181(18) 0.32590(6) 0.5945(2) 0.0443(5) Uani 1 1 d .
H3 H 0.3274 0.3498 0.6176 0.053 Uiso 1 1 calc R
C35 C 1.06565(16) 0.31582(6) 0.7559(2) 0.0381(4) Uani 1 1 d .
H35 H 1.1326 0.3102 0.8502 0.046 Uiso 1 1 calc R
C24 C 0.42674(18) 0.02031(5) 0.1652(2) 0.0380(4) Uani 1 1 d .
C2 C 0.44928(18) 0.32916(6) 0.5333(2) 0.0420(5) Uani 1 1 d .
H2 H 0.4734 0.3552 0.5114 0.050 Uiso 1 1 calc R
C37 C 0.96231(18) 0.36190(5) 0.5499(2) 0.0394(4) Uani 1 1 d .
H37 H 0.9582 0.3877 0.5027 0.047 Uiso 1 1 calc R
C8 C 0.19577(18) 0.16933(7) 0.6879(2) 0.0470(5) Uani 1 1 d .
H8 H 0.1355 0.1669 0.7296 0.056 Uiso 1 1 calc R
C36 C 1.05921(17) 0.35329(6) 0.6865(2) 0.0411(4) Uani 1 1 d .
H36 H 1.1213 0.3731 0.7328 0.049 Uiso 1 1 calc R
C40 C 0.98807(17) 0.24521(5) 0.7684(2) 0.0378(4) Uani 1 1 d .
H40A H 0.9274 0.2431 0.8139 0.057 Uiso 1 1 calc R
H40B H 1.0704 0.2424 0.8493 0.057 Uiso 1 1 calc R
H40C H 0.9740 0.2235 0.6921 0.057 Uiso 1 1 calc R
C9 C 0.23724(18) 0.13478(6) 0.6398(3) 0.0474(5) Uani 1 1 d .
H9 H 0.2055 0.1087 0.6483 0.057 Uiso 1 1 calc R
C4 C 0.32433(17) 0.28815(6) 0.6221(2) 0.0403(4) Uani 1 1 d .
H4 H 0.2621 0.2864 0.6608 0.048 Uiso 1 1 calc R
C30 C 0.6235(2) -0.01826(6) 0.2260(3) 0.0518(5) Uani 1 1 d .
H30A H 0.6520 0.0042 0.1805 0.078 Uiso 1 1 calc R
H30B H 0.6477 -0.0443 0.1955 0.078 Uiso 1 1 calc R
H30C H 0.6602 -0.0159 0.3384 0.078 Uiso 1 1 calc R
C28 C 0.4167(2) -0.05167(6) 0.1205(2) 0.0478(5) Uani 1 1 d .
H28 H 0.4560 -0.0770 0.1226 0.057 Uiso 1 1 calc R
C25 C 0.2997(2) 0.02197(6) 0.1136(3) 0.0499(5) Uani 1 1 d .
C26 C 0.2334(2) -0.01407(7) 0.0681(3) 0.0603(6) Uani 1 1 d .
H26 H 0.1470 -0.0136 0.0363 0.072 Uiso 1 1 calc R
C39 C 0.7640(2) 0.34269(6) 0.3316(2) 0.0517(5) Uani 1 1 d .
H39A H 0.7496 0.3195 0.2613 0.078 Uiso 1 1 calc R
H39B H 0.7821 0.3670 0.2844 0.078 Uiso 1 1 calc R
H39C H 0.6908 0.3476 0.3525 0.078 Uiso 1 1 calc R
C27 C 0.2916(2) -0.05048(6) 0.0685(3) 0.0566(6) Uani 1 1 d .
H27 H 0.2451 -0.0747 0.0328 0.068 Uiso 1 1 calc R
C23 C 0.5395(2) 0.05357(5) 0.4713(2) 0.0490(5) Uani 1 1 d .
H23A H 0.4575 0.0428 0.4487 0.074 Uiso 1 1 calc R
H23B H 0.5597 0.0742 0.5524 0.074 Uiso 1 1 calc R
H23C H 0.5993 0.0313 0.5059 0.074 Uiso 1 1 calc R
C31 C 0.2367(2) 0.06196(7) 0.1080(4) 0.0766(8) Uani 1 1 d .
H31A H 0.2468 0.0796 0.0302 0.115 Uiso 1 1 calc R
H31B H 0.2728 0.0752 0.2089 0.115 Uiso 1 1 calc R
H31C H 0.1494 0.0572 0.0812 0.115 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 N1 C21 119.07(14)
C13 C15 C16 119.21(14)
C13 C15 C32 119.52(14)
C16 C15 C32 120.53(14)
C17 C16 C21 118.11(14)
C17 C16 C15 124.66(15)
C21 C16 C15 117.24(15)
C22 N3 C24 121.21(15)
N1 C12 C13 123.35(15)
N1 C12 C11 116.91(14)
C13 C12 C11 119.67(14)
C15 C13 C12 117.35(14)
C15 C13 C14 123.98(15)
C12 C13 C14 118.68(15)
C1 C14 C5 118.16(15)
C1 C14 C13 121.60(16)
C5 C14 C13 120.08(15)
N2 C32 C15 125.18(15)
C32 N2 C33 117.86(14)
C7 C6 C11 118.11(16)
C7 C6 C5 122.19(16)
C11 C6 C5 119.64(15)
C10 C11 C6 119.86(16)
C10 C11 C12 119.86(15)
C6 C11 C12 120.26(15)
N1 C21 C16 122.54(14)
N1 C21 C20 117.72(14)
C16 C21 C20 119.74(15)
C2 C1 C14 121.78(18)
C4 C5 C14 118.68(17)
C4 C5 C6 121.17(17)
C14 C5 C6 120.10(15)
C38 C33 C34 121.38(15)
C38 C33 N2 117.98(15)
C34 C33 N2 120.39(15)
C35 C34 C33 117.86(16)
C35 C34 C40 120.01(16)
C33 C34 C40 122.12(15)
C8 C7 C6 121.00(18)
C37 C38 C33 118.32(16)
C37 C38 C39 121.50(16)
C33 C38 C39 120.18(15)
C18 C17 C16 120.76(16)
C20 C19 C18 121.03(16)
C28 C29 C24 117.88(19)
C28 C29 C30 120.95(18)
C24 C29 C30 121.16(17)
C17 C18 C19 120.70(16)
N3 C22 C20 116.38(15)
N3 C22 C23 125.38(16)
C20 C22 C23 118.00(16)
C9 C10 C11 120.63(18)
C19 C20 C21 119.40(15)
C19 C20 C22 119.73(15)
C21 C20 C22 120.87(15)
C4 C3 C2 120.30(17)
C36 C35 C34 121.54(17)
C25 C24 C29 121.28(17)
C25 C24 N3 118.80(16)
C29 C24 N3 119.41(17)
C3 C2 C1 119.35(18)
C36 C37 C38 121.15(17)
C7 C8 C9 120.71(18)
C37 C36 C35 119.75(17)
C10 C9 C8 119.69(19)
C3 C4 C5 121.50(18)
C27 C28 C29 121.51(19)
C26 C25 C24 118.65(19)
C26 C25 C31 121.1(2)
C24 C25 C31 120.27(18)
C27 C26 C25 120.7(2)
C28 C27 C26 119.92(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C12 1.324(2)
N1 C21 1.353(2)
C15 C13 1.400(2)
C15 C16 1.430(2)
C15 C32 1.480(2)
C16 C17 1.419(2)
C16 C21 1.427(2)
N3 C22 1.271(2)
N3 C24 1.427(2)
C12 C13 1.431(2)
C12 C11 1.467(2)
C13 C14 1.466(2)
C14 C1 1.409(2)
C14 C5 1.414(2)
C32 N2 1.274(2)
N2 C33 1.426(2)
C6 C7 1.406(2)
C6 C11 1.407(2)
C6 C5 1.469(2)
C11 C10 1.405(2)
C21 C20 1.429(2)
C1 C2 1.383(2)
C5 C4 1.405(2)
C33 C38 1.402(2)
C33 C34 1.403(2)
C34 C35 1.390(2)
C34 C40 1.511(2)
C7 C8 1.376(3)
C38 C37 1.390(2)
C38 C39 1.503(3)
C17 C18 1.366(2)
C19 C20 1.368(2)
C19 C18 1.403(2)
C29 C28 1.393(3)
C29 C24 1.400(2)
C29 C30 1.494(3)
C22 C20 1.495(2)
C22 C23 1.503(2)
C10 C9 1.378(3)
C3 C4 1.376(3)
C3 C2 1.382(3)
C35 C36 1.381(3)
C24 C25 1.394(3)
C37 C36 1.379(3)
C8 C9 1.383(3)
C28 C27 1.371(3)
C25 C26 1.392(3)
C25 C31 1.502(3)
C26 C27 1.380(3)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.500 0.000 302.0 62.0
2 0.000 1.000 0.500 302.1 62.0
