#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:27:04 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135225.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_4135225
loop_
_publ_author_name
'Morstein, Johannes'
'Höfler, Denis'
'Ueno, Kohei'
'Jurss, Jonah W.'
'Walvoord, Ryan R.'
'Bruemmer, Kevin J.'
'Rezgui, Samir P.'
'Brewer, Thomas F.'
'Saitoe, Minoru'
'Michel, Brian W.'
'Chang, Christopher J.'
_publ_section_title
;
 Ligand-Directed Approach to Activity-Based Sensing: Developing
 Palladacycle Fluorescent Probes That Enable Endogenous Carbon Monoxide
 Detection.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15917
_journal_page_last               15930
_journal_paper_doi               10.1021/jacs.0c06405
_journal_volume                  142
_journal_year                    2020
_chemical_formula_sum            'C23 H26 B F2 N3 O2'
_chemical_formula_weight         425.28
_chemical_name_common            rxnCOP1
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                98.326(2)
_cell_angle_beta                 91.920(2)
_cell_angle_gamma                100.133(2)
_cell_formula_units_Z            2
_cell_length_a                   6.815
_cell_length_b                   7.825
_cell_length_c                   20.2310(10)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.71
_cell_volume                     1048.92(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'QUAZAR multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17611
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shards
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0380
_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/[σ²(Fo²)+(0.0405P)²+0.6515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                3352
_reflns_number_total             3866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0c06405_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4135223--4135225.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4135225
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0930(2) 0.8559(2) 0.69357(8) 0.0194(3) Uani 1 1 d . . .
C2 C 0.0050(2) 0.9854(2) 0.66028(9) 0.0260(4) Uani 1 1 d . . .
H2A H 0.0617 1.1047 0.6823 0.039 Uiso 1 1 calc R . .
H2B H -0.1401 0.9638 0.6636 0.039 Uiso 1 1 calc R . .
H2C H 0.0357 0.9728 0.6130 0.039 Uiso 1 1 calc R . .
C3 C 0.0339(2) 0.7902(2) 0.75161(8) 0.0211(4) Uani 1 1 d . . .
H3 H -0.0715 0.8213 0.7776 0.025 Uiso 1 1 calc R . .
C4 C 0.1536(2) 0.6720(2) 0.76528(7) 0.0177(3) Uani 1 1 d . . .
C5 C 0.1238(2) 0.5630(2) 0.82040(8) 0.0250(4) Uani 1 1 d . . .
H5A H 0.2296 0.6073 0.8559 0.038 Uiso 1 1 calc R . .
H5B H 0.1288 0.4405 0.8027 0.038 Uiso 1 1 calc R . .
H5C H -0.0064 0.5697 0.8387 0.038 Uiso 1 1 calc R . .
C6 C 0.2917(2) 0.66931(19) 0.71393(7) 0.0142(3) Uani 1 1 d . . .
C7 C 0.4463(2) 0.57249(19) 0.70137(7) 0.0128(3) Uani 1 1 d . . .
C8 C 0.5534(2) 0.58152(19) 0.64426(7) 0.0134(3) Uani 1 1 d . . .
C9 C 0.7182(2) 0.5025(2) 0.62077(7) 0.0158(3) Uani 1 1 d . . .
C10 C 0.8195(2) 0.3732(2) 0.64975(8) 0.0211(4) Uani 1 1 d . . .
H10A H 0.9488 0.3710 0.6302 0.032 Uiso 1 1 calc R . .
H10B H 0.7358 0.2561 0.6397 0.032 Uiso 1 1 calc R . .
H10C H 0.8402 0.4078 0.6984 0.032 Uiso 1 1 calc R . .
C11 C 0.7677(2) 0.5663(2) 0.56277(8) 0.0195(3) Uani 1 1 d . . .
H11 H 0.8713 0.5367 0.5355 0.023 Uiso 1 1 calc R . .
C12 C 0.6408(2) 0.6825(2) 0.55001(7) 0.0179(3) Uani 1 1 d . . .
C13 C 0.6472(3) 0.7884(2) 0.49449(8) 0.0253(4) Uani 1 1 d . . .
H13A H 0.7173 0.9085 0.5107 0.038 Uiso 1 1 calc R . .
H13B H 0.5107 0.7912 0.4784 0.038 Uiso 1 1 calc R . .
H13C H 0.7178 0.7354 0.4578 0.038 Uiso 1 1 calc R . .
C14 C 0.4971(2) 0.4697(2) 0.75387(7) 0.0138(3) Uani 1 1 d . . .
C15 C 0.5704(2) 0.56147(19) 0.81629(7) 0.0127(3) Uani 1 1 d . . .
H15 H 0.5961 0.6862 0.8222 0.015 Uiso 1 1 calc R . .
C16 C 0.6076(2) 0.47835(19) 0.87050(7) 0.0129(3) Uani 1 1 d . . .
C17 C 0.6820(2) 0.60113(19) 0.93566(7) 0.0140(3) Uani 1 1 d . . .
C18 C 0.5702(2) 0.29345(19) 0.86157(7) 0.0140(3) Uani 1 1 d . . .
C19 C 0.5911(2) 0.1889(2) 0.91797(7) 0.0157(3) Uani 1 1 d . . .
H19A H 0.4995 0.2195 0.9529 0.019 Uiso 1 1 calc R . .
H19B H 0.5509 0.0621 0.9005 0.019 Uiso 1 1 calc R . .
C20 C 0.4988(2) 0.2016(2) 0.79846(7) 0.0170(3) Uani 1 1 d . . .
H20 H 0.4744 0.0768 0.7919 0.020 Uiso 1 1 calc R . .
C21 C 0.4622(2) 0.2872(2) 0.74492(7) 0.0171(3) Uani 1 1 d . . .
H21 H 0.4137 0.2214 0.7026 0.021 Uiso 1 1 calc R . .
C22 C 0.8065(2) 0.1468(2) 1.01192(7) 0.0179(3) Uani 1 1 d . . .
H22A H 0.9419 0.1787 1.0332 0.027 Uiso 1 1 calc R . .
H22B H 0.7689 0.0186 1.0019 0.027 Uiso 1 1 calc R . .
H22C H 0.7128 0.1931 1.0423 0.027 Uiso 1 1 calc R . .
C23 C 0.9442(2) 0.1603(2) 0.90221(8) 0.0206(3) Uani 1 1 d . . .
H23A H 0.9338 0.2091 0.8606 0.031 Uiso 1 1 calc R . .
H23B H 0.9143 0.0317 0.8924 0.031 Uiso 1 1 calc R . .
H23C H 1.0800 0.1986 0.9228 0.031 Uiso 1 1 calc R . .
B1 B 0.3590(3) 0.8170(2) 0.60709(8) 0.0158(4) Uani 1 1 d . . .
N1 N 0.24776(18) 0.78288(16) 0.67060(6) 0.0153(3) Uani 1 1 d . . .
N2 N 0.51090(18) 0.69084(16) 0.59858(6) 0.0142(3) Uani 1 1 d . . .
N3 N 0.80017(18) 0.22275(17) 0.94876(6) 0.0150(3) Uani 1 1 d . . .
O1 O 0.64522(17) 0.75251(14) 0.94050(5) 0.0206(3) Uani 1 1 d . . .
O2 O 0.78036(16) 0.54639(14) 0.97997(5) 0.0200(3) Uani 1 1 d . . .
F1 F 0.22594(14) 0.78652(12) 0.55154(4) 0.0232(2) Uani 1 1 d . . .
F2 F 0.46106(14) 0.99049(11) 0.61547(4) 0.0221(2) Uani 1 1 d . . .
H1 H 0.826(3) 0.348(3) 0.9608(9) 0.029(5) Uiso 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 0.0033 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
N1 C1 C3 108.83(14) . . ?
N1 C1 C2 123.78(15) . . ?
C3 C1 C2 127.39(14) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C1 109.04(13) . . ?
C4 C3 H3 125.5 . . ?
C1 C3 H3 125.5 . . ?
C3 C4 C6 105.78(14) . . ?
C3 C4 C5 124.51(14) . . ?
C6 C4 C5 129.54(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 120.69(13) . . ?
N1 C6 C4 107.86(13) . . ?
C7 C6 C4 131.41(14) . . ?
C8 C7 C6 121.16(13) . . ?
C8 C7 C14 121.80(13) . . ?
C6 C7 C14 116.93(12) . . ?
C7 C8 N2 119.99(13) . . ?
C7 C8 C9 132.37(14) . . ?
N2 C8 C9 107.58(12) . . ?
C11 C9 C8 106.07(13) . . ?
C11 C9 C10 124.32(14) . . ?
C8 C9 C10 129.60(14) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 109.09(13) . . ?
C9 C11 H11 125.5 . . ?
C12 C11 H11 125.5 . . ?
N2 C12 C11 109.03(13) . . ?
N2 C12 C13 123.41(14) . . ?
C11 C12 C13 127.51(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C21 118.61(13) . . ?
C15 C14 C7 117.92(13) . . ?
C21 C14 C7 123.32(13) . . ?
C14 C15 C16 122.76(14) . . ?
C14 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C18 118.57(13) . . ?
C15 C16 C17 115.23(13) . . ?
C18 C16 C17 126.18(13) . . ?
O1 C17 O2 124.27(14) . . ?
O1 C17 C16 116.46(13) . . ?
O2 C17 C16 119.24(13) . . ?
C20 C18 C16 118.49(13) . . ?
C20 C18 C19 118.14(13) . . ?
C16 C18 C19 123.26(13) . . ?
N3 C19 C18 112.49(12) . . ?
N3 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
N3 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C18 122.04(14) . . ?
C21 C20 H20 119.0 . . ?
C18 C20 H20 119.0 . . ?
C14 C21 C20 119.51(14) . . ?
C14 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F1 B1 F2 109.34(13) . . ?
F1 B1 N1 110.67(13) . . ?
F2 B1 N1 109.76(12) . . ?
F1 B1 N2 110.66(12) . . ?
F2 B1 N2 109.43(13) . . ?
N1 B1 N2 106.95(12) . . ?
C1 N1 C6 108.48(13) . . ?
C1 N1 B1 126.44(13) . . ?
C6 N1 B1 125.08(12) . . ?
C12 N2 C8 108.23(12) . . ?
C12 N2 B1 125.55(13) . . ?
C8 N2 B1 125.81(12) . . ?
C23 N3 C22 111.19(12) . . ?
C23 N3 C19 112.93(12) . . ?
C22 N3 C19 110.72(12) . . ?
C23 N3 H1 112.3(11) . . ?
C22 N3 H1 107.2(11) . . ?
C19 N3 H1 102.1(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3502(19) . ?
C1 C3 1.392(2) . ?
C1 C2 1.491(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C6 1.425(2) . ?
C4 C5 1.497(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N1 1.3963(19) . ?
C6 C7 1.411(2) . ?
C7 C8 1.391(2) . ?
C7 C14 1.488(2) . ?
C8 N2 1.4027(19) . ?
C8 C9 1.437(2) . ?
C9 C11 1.370(2) . ?
C9 C10 1.495(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.404(2) . ?
C11 H11 0.9500 . ?
C12 N2 1.3465(19) . ?
C12 C13 1.487(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.389(2) . ?
C14 C21 1.390(2) . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 C18 1.408(2) . ?
C16 C17 1.528(2) . ?
C17 O1 1.2441(18) . ?
C17 O2 1.2684(18) . ?
C18 C20 1.397(2) . ?
C18 C19 1.514(2) . ?
C19 N3 1.4993(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N3 1.4876(18) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N3 1.4790(19) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
B1 F1 1.3856(19) . ?
B1 F2 1.396(2) . ?
B1 N1 1.546(2) . ?
B1 N2 1.549(2) . ?
N3 H1 0.96(2) . ?
