#------------------------------------------------------------------------------
#$Date: 2020-12-06 15:07:24 +0200 (Sun, 06 Dec 2020) $
#$Revision: 259601 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/90/1559098.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_1559098
loop_
_publ_author_name
'Nori, Valeria'
'Dasgupta, Ayan'
'Babaahmadi, Rasool'
'Carlone, Armando'
'Ariafard, Alireza'
'Melen, Rebecca L.'
_publ_section_title
;
 Triarylborane catalysed N-alkylation of amines with aryl esters
;
_journal_issue                   22
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              7523
_journal_page_last               7530
_journal_paper_doi               10.1039/D0CY01339K
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C23 H19 F2 N'
_chemical_formula_sum            'C23 H19 F2 N'
_chemical_formula_weight         347.39
_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
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-04-15 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.764(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9007(4)
_cell_length_b                   11.1893(4)
_cell_length_c                   18.1967(7)
_cell_measurement_reflns_used    6206
_cell_measurement_temperature    199.9(2)
_cell_measurement_theta_max      29.4230
_cell_measurement_theta_min      4.2530
_cell_volume                     1808.35(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      199.9(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17487
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.819
_diffrn_reflns_theta_min         3.312
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0549P)²+0.9291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1425
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3627
_reflns_number_total             4569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cy01339k2.cif
_cod_data_source_block           rm2018
_cod_depositor_comments
'Adding full bibliography for 1559097--1559098.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1559098
_shelx_shelxl_version_number     2018/1
_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   0.971
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3006(2) 0.62092(18) 0.82842(10) 0.0486(5) Uani 1 1 d . . . . .
H1A H 0.229775 0.614408 0.865808 0.073 Uiso 1 1 calc R U . . .
H1B H 0.278790 0.691254 0.799434 0.073 Uiso 1 1 calc R U . . .
H1C H 0.400739 0.626356 0.851171 0.073 Uiso 1 1 calc R U . . .
C2 C 0.28878(17) 0.51343(15) 0.78004(8) 0.0341(3) Uani 1 1 d . . . . .
C3 C 0.20278(18) 0.41366(15) 0.78651(9) 0.0362(4) Uani 1 1 d . . . . .
C4 C 0.1015(2) 0.3840(2) 0.84662(11) 0.0516(5) Uani 1 1 d . . . . .
H4A H 0.134619 0.311044 0.870240 0.077 Uiso 1 1 calc R U . . .
H4B H 0.000200 0.374496 0.825981 0.077 Uiso 1 1 calc R U . . .
H4C H 0.104982 0.447568 0.882144 0.077 Uiso 1 1 calc R U . . .
C5 C 0.22887(17) 0.33878(14) 0.72487(9) 0.0340(3) Uani 1 1 d . . . . .
C6 C 0.1687(2) 0.22875(15) 0.70076(11) 0.0427(4) Uani 1 1 d . . . . .
H6 H 0.100688 0.188375 0.728491 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2112(2) 0.18127(16) 0.63575(12) 0.0478(4) Uani 1 1 d . . . . .
H7 H 0.170487 0.108866 0.619134 0.057 Uiso 1 1 calc R U . . .
C8 C 0.3148(2) 0.24028(15) 0.59426(10) 0.0433(4) Uani 1 1 d . . . . .
H8 H 0.342004 0.206162 0.550455 0.052 Uiso 1 1 calc R U . . .
C9 C 0.37819(19) 0.34833(15) 0.61671(9) 0.0364(3) Uani 1 1 d . . . . .
H9 H 0.447755 0.386873 0.588980 0.044 Uiso 1 1 calc R U . . .
C10 C 0.33397(17) 0.39738(13) 0.68242(8) 0.0312(3) Uani 1 1 d . . . . .
C11 C 0.46631(16) 0.60088(13) 0.69232(8) 0.0295(3) Uani 1 1 d . . . . .
H11 H 0.501623 0.645535 0.736455 0.035 Uiso 1 1 calc R U . . .
C12 C 0.60729(16) 0.55342(13) 0.65885(8) 0.0296(3) Uani 1 1 d . . . . .
C13 C 0.70466(18) 0.48026(15) 0.70151(9) 0.0353(3) Uani 1 1 d . . . . .
H13 H 0.681219 0.459874 0.748969 0.042 Uiso 1 1 calc R U . . .
C14 C 0.83602(18) 0.43736(15) 0.67430(9) 0.0382(4) Uani 1 1 d . . . . .
H14 H 0.900766 0.388199 0.702832 0.046 Uiso 1 1 calc R U . . .
C15 C 0.86825(17) 0.46910(15) 0.60433(9) 0.0361(4) Uani 1 1 d . . . . .
C16 C 0.77610(19) 0.54116(17) 0.56055(10) 0.0416(4) Uani 1 1 d . . . . .
H16 H 0.800939 0.561598 0.513317 0.050 Uiso 1 1 calc R U . . .
C17 C 0.64471(18) 0.58290(16) 0.58848(9) 0.0370(4) Uani 1 1 d . . . . .
H17 H 0.580493 0.631634 0.559369 0.044 Uiso 1 1 calc R U . . .
C18 C 0.37832(17) 0.68963(13) 0.64289(8) 0.0303(3) Uani 1 1 d . . . . .
C19 C 0.4377(2) 0.80343(15) 0.63504(10) 0.0406(4) Uani 1 1 d . . . . .
H19 H 0.526372 0.824353 0.661807 0.049 Uiso 1 1 calc R U . . .
C20 C 0.3669(2) 0.88609(16) 0.58803(11) 0.0476(4) Uani 1 1 d . . . . .
H20 H 0.406974 0.962116 0.582725 0.057 Uiso 1 1 calc R U . . .
C21 C 0.2362(2) 0.85296(17) 0.54954(10) 0.0471(5) Uani 1 1 d . . . . .
C22 C 0.1726(2) 0.74262(18) 0.55615(10) 0.0486(5) Uani 1 1 d . . . . .
H22 H 0.083155 0.722983 0.529611 0.058 Uiso 1 1 calc R U . . .
C23 C 0.24522(19) 0.66047(15) 0.60361(10) 0.0395(4) Uani 1 1 d . . . . .
H23 H 0.203655 0.584964 0.608976 0.047 Uiso 1 1 calc R U . . .
N1 N 0.37201(14) 0.50394(11) 0.71788(7) 0.0315(3) Uani 1 1 d . . . . .
F1 F 0.99712(11) 0.42745(10) 0.57745(6) 0.0494(3) Uani 1 1 d . . . . .
F2 F 0.16498(17) 0.93424(12) 0.50382(7) 0.0719(4) 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 0.0033 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'
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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 109.78(14) . . ?
C3 C2 C1 128.93(15) . . ?
N1 C2 C1 121.29(14) . . ?
C2 C3 C5 106.91(14) . . ?
C2 C3 C4 127.72(17) . . ?
C5 C3 C4 125.35(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.32(15) . . ?
C6 C5 C3 132.94(16) . . ?
C10 C5 C3 107.70(14) . . ?
C7 C6 C5 119.23(16) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 120.84(17) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 121.63(17) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 117.64(16) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
N1 C10 C9 131.51(15) . . ?
N1 C10 C5 107.14(13) . . ?
C9 C10 C5 121.33(15) . . ?
N1 C11 C18 112.79(12) . . ?
N1 C11 C12 111.85(12) . . ?
C18 C11 C12 113.33(12) . . ?
N1 C11 H11 106.1 . . ?
C18 C11 H11 106.1 . . ?
C12 C11 H11 106.1 . . ?
C17 C12 C13 118.53(14) . . ?
C17 C12 C11 122.72(14) . . ?
C13 C12 C11 118.72(13) . . ?
C14 C13 C12 120.93(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 118.39(15) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
F1 C15 C16 118.73(15) . . ?
F1 C15 C14 118.60(15) . . ?
C16 C15 C14 122.67(15) . . ?
C15 C16 C17 118.23(15) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C12 C17 C16 121.26(15) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C23 C18 C19 118.82(15) . . ?
C23 C18 C11 122.82(14) . . ?
C19 C18 C11 118.32(14) . . ?
C20 C19 C18 121.03(17) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 118.20(17) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
F2 C21 C22 118.57(19) . . ?
F2 C21 C20 118.55(18) . . ?
C22 C21 C20 122.86(17) . . ?
C21 C22 C23 118.24(17) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C18 C23 C22 120.84(17) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C10 N1 C2 108.42(13) . . ?
C10 N1 C11 128.01(12) . . ?
C2 N1 C11 123.10(13) . . ?
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 C2 1.490(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.363(2) . ?
C2 N1 1.3963(19) . ?
C3 C5 1.431(2) . ?
C3 C4 1.499(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.402(2) . ?
C5 C10 1.413(2) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(2) . ?
C9 H9 0.9300 . ?
C10 N1 1.387(2) . ?
C11 N1 1.4659(19) . ?
C11 C18 1.522(2) . ?
C11 C12 1.526(2) . ?
C11 H11 0.9800 . ?
C12 C17 1.384(2) . ?
C12 C13 1.391(2) . ?
C13 C14 1.385(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(2) . ?
C14 H14 0.9300 . ?
C15 F1 1.3586(17) . ?
C15 C16 1.368(2) . ?
C16 C17 1.386(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.382(2) . ?
C18 C19 1.390(2) . ?
C19 C20 1.383(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(3) . ?
C20 H20 0.9300 . ?
C21 F2 1.361(2) . ?
C21 C22 1.367(3) . ?
C22 C23 1.391(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
