#------------------------------------------------------------------------------
#$Date: 2019-03-29 01:02:01 +0200 (Fri, 29 Mar 2019) $
#$Revision: 214406 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/32/7123228.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_7123228
loop_
_publ_author_name
'Dissanayake, Komadhie'
'Ebukuyo, Peters'
'Dhahir, Yasser'
'Wheeler, Kraig'
'He, Hongshan'
_publ_section_title
;
 A BODIPY-functionalized PdII photoredox catalyst for Sonogashira C-C
 cross-coupling reactions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01365B
_journal_year                    2019
_chemical_formula_sum            'C38 H34 B2 Cl2 F4 N6 Pd'
_chemical_formula_weight         849.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-02-17 deposited with the CCDC.    2019-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3737(4)
_cell_length_b                   10.1392(2)
_cell_length_c                   18.4928(4)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.183
_cell_measurement_theta_min      4.645
_cell_volume                     3632.56(13)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26825
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         4.565
_exptl_absorpt_coefficient_mu    5.972
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker AXS'
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.072
_refine_diff_density_max         1.043
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0312
_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/[σ²(Fo²)+(0.0452P)²+11.4845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3246
_reflns_number_total             3311
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc01365b2.cif
_cod_data_source_block           15hhe10a
_cod_database_code               7123228
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.493
_shelx_estimated_absorpt_t_max   0.673
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Pd1 Pd 0.0000 0.20216(2) 0.2500 0.01688(10) Uani 1 2 d S T P
Cl1 Cl 0.06501(3) 0.04700(7) 0.19359(4) 0.02852(17) Uani 1 1 d . . .
F1 F 0.19875(9) 1.06747(17) 0.06937(10) 0.0359(4) Uani 1 1 d . . .
F2 F 0.24828(9) 0.94453(18) -0.01844(9) 0.0320(4) Uani 1 1 d . . .
N1 N 0.05017(10) 0.3536(2) 0.20059(11) 0.0166(4) Uani 1 1 d . . .
N2 N 0.23832(12) 0.8480(2) 0.10007(12) 0.0248(5) Uani 1 1 d . . .
N3 N 0.13481(12) 0.8808(2) 0.02185(12) 0.0237(5) Uani 1 1 d . . .
C1 C 0.09939(13) 0.3495(3) 0.15107(14) 0.0201(5) Uani 1 1 d . . .
H1 H 0.1155 0.2662 0.1347 0.024 Uiso 1 1 calc R U .
C2 C 0.12839(13) 0.4646(3) 0.12214(14) 0.0207(5) Uani 1 1 d . . .
H2 H 0.1636 0.4581 0.0868 0.025 Uiso 1 1 calc R U .
C3 C 0.10615(13) 0.5873(3) 0.14458(14) 0.0194(5) Uani 1 1 d . . .
C4 C 0.05359(13) 0.5943(3) 0.19780(14) 0.0180(5) Uani 1 1 d . . .
C5 C 0.02702(12) 0.4742(2) 0.22359(13) 0.0167(5) Uani 1 1 d . . .
C6 C 0.02590(14) 0.7156(3) 0.22554(15) 0.0227(6) Uani 1 1 d . . .
H6 H 0.0443 0.7972 0.2093 0.027 Uiso 1 1 calc R U .
C7 C 0.13757(14) 0.7089(3) 0.11315(15) 0.0203(5) Uani 1 1 d . . .
C8 C 0.20421(14) 0.7447(3) 0.13500(14) 0.0230(6) Uani 1 1 d . . .
C9 C 0.25088(15) 0.6880(3) 0.18682(16) 0.0276(6) Uani 1 1 d . . .
C10 C 0.31195(15) 0.7559(3) 0.17995(16) 0.0311(6) Uani 1 1 d . . .
H10 H 0.3530 0.7399 0.2069 0.037 Uiso 1 1 calc R U .
C11 C 0.30334(15) 0.8532(3) 0.12631(16) 0.0280(6) Uani 1 1 d . . .
C12 C 0.35583(15) 0.9487(3) 0.10057(17) 0.0346(7) Uani 1 1 d . . .
H12A H 0.3719 0.9222 0.0526 0.052 Uiso 1 1 calc R U .
H12B H 0.3950 0.9501 0.1344 0.052 Uiso 1 1 calc R U .
H12C H 0.3353 1.0369 0.0978 0.052 Uiso 1 1 calc R U .
C13 C 0.23942(17) 0.5772(4) 0.23945(18) 0.0362(7) Uani 1 1 d . . .
H13A H 0.2405 0.4929 0.2136 0.054 Uiso 1 1 calc R U .
H13B H 0.1944 0.5882 0.2626 0.054 Uiso 1 1 calc R U .
H13C H 0.2759 0.5785 0.2764 0.054 Uiso 1 1 calc R U .
C14 C 0.10256(14) 0.7760(3) 0.05796(15) 0.0219(5) Uani 1 1 d . . .
C15 C 0.03655(14) 0.7565(3) 0.02477(15) 0.0251(6) Uani 1 1 d . . .
C16 C 0.03140(15) 0.8473(3) -0.03010(16) 0.0296(6) Uani 1 1 d . . .
H16 H -0.0069 0.8576 -0.0619 0.035 Uiso 1 1 calc R U .
C17 C 0.09259(15) 0.9229(3) -0.03127(16) 0.0280(6) Uani 1 1 d . . .
C18 C 0.11052(17) 1.0315(3) -0.08291(18) 0.0354(7) Uani 1 1 d . . .
H18A H 0.1262 1.1090 -0.0557 0.053 Uiso 1 1 calc R U .
H18B H 0.0697 1.0547 -0.1117 0.053 Uiso 1 1 calc R U .
H18C H 0.1474 1.0018 -0.1151 0.053 Uiso 1 1 calc R U .
C19 C -0.01940(14) 0.6604(3) 0.04497(17) 0.0288(6) Uani 1 1 d . . .
H19A H -0.0395 0.6865 0.0913 0.043 Uiso 1 1 calc R U .
H19B H 0.0003 0.5717 0.0492 0.043 Uiso 1 1 calc R U .
H19C H -0.0554 0.6606 0.0075 0.043 Uiso 1 1 calc R U .
B1 B 0.20630(17) 0.9399(3) 0.04189(18) 0.0258(7) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Pd1 N1 82.12(12) . 2
N1 Pd1 Cl1 92.80(6) . .
N1 Pd1 Cl1 174.31(6) 2 .
N1 Pd1 Cl1 174.31(6) . 2
N1 Pd1 Cl1 92.80(6) 2 2
Cl1 Pd1 Cl1 92.37(3) . 2
C1 N1 C5 118.7(2) . .
C1 N1 Pd1 129.26(18) . .
C5 N1 Pd1 112.07(16) . .
C11 N2 C8 107.8(2) . .
C11 N2 B1 126.5(2) . .
C8 N2 B1 125.6(2) . .
C17 N3 C14 108.5(2) . .
C17 N3 B1 126.2(2) . .
C14 N3 B1 125.3(2) . .
N1 C1 C2 121.9(2) . .
C3 C2 C1 120.6(2) . .
C2 C3 C4 118.6(2) . .
C2 C3 C7 119.9(2) . .
C4 C3 C7 121.5(2) . .
C5 C4 C3 117.1(2) . .
C5 C4 C6 118.8(2) . .
C3 C4 C6 124.1(2) . .
N1 C5 C4 123.1(2) . .
N1 C5 C5 116.87(13) . 2
C4 C5 C5 120.02(14) . 2
C6 C6 C4 121.17(15) 2 .
C8 C7 C14 121.8(2) . .
C8 C7 C3 118.6(2) . .
C14 C7 C3 119.2(2) . .
N2 C8 C7 119.9(3) . .
N2 C8 C9 108.1(2) . .
C7 C8 C9 131.8(3) . .
C10 C9 C8 106.1(3) . .
C10 C9 C13 124.3(3) . .
C8 C9 C13 129.6(3) . .
C9 C10 C11 108.5(3) . .
N2 C11 C10 109.4(2) . .
N2 C11 C12 123.4(3) . .
C10 C11 C12 127.2(3) . .
C7 C14 N3 120.0(2) . .
C7 C14 C15 132.4(3) . .
N3 C14 C15 107.5(2) . .
C16 C15 C14 106.6(2) . .
C16 C15 C19 124.6(3) . .
C14 C15 C19 128.8(3) . .
C15 C16 C17 108.5(3) . .
N3 C17 C16 108.9(3) . .
N3 C17 C18 123.8(3) . .
C16 C17 C18 127.3(3) . .
F2 B1 F1 108.9(2) . .
F2 B1 N2 110.2(2) . .
F1 B1 N2 110.3(2) . .
F2 B1 N3 110.4(2) . .
F1 B1 N3 110.4(2) . .
N2 B1 N3 106.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N1 2.036(2) .
Pd1 N1 2.036(2) 2
Pd1 Cl1 2.2724(7) .
Pd1 Cl1 2.2725(7) 2
F1 B1 1.398(4) .
F2 B1 1.385(4) .
N1 C1 1.326(3) .
N1 C5 1.371(3) .
N2 C11 1.349(4) .
N2 C8 1.398(4) .
N2 B1 1.551(4) .
N3 C17 1.344(4) .
N3 C14 1.403(3) .
N3 B1 1.552(4) .
C1 C2 1.402(4) .
C2 C3 1.381(4) .
C3 C4 1.422(4) .
C3 C7 1.494(4) .
C4 C5 1.406(4) .
C4 C6 1.437(4) .
C5 C5 1.436(5) 2
C6 C6 1.355(6) 2
C7 C8 1.399(4) .
C7 C14 1.399(4) .
C8 C9 1.434(4) .
C9 C10 1.376(4) .
C9 C13 1.503(4) .
C10 C11 1.408(5) .
C11 C12 1.484(4) .
C14 C15 1.429(4) .
C15 C16 1.374(4) .
C15 C19 1.506(4) .
C16 C17 1.412(4) .
C17 C18 1.500(4) .
