#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:19:39 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292786 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/29/7132999.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_7132999
loop_
_publ_author_name
'Das, Animesh'
'Maji, Biplab'
_publ_section_title
;
 Substrate-controlled divergent remote C-H and N-H polyfluoroarylation of
 2-aminopyrimidines with polyfluoroarenes via Pd(II)/Pd(0)
 catalysis.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5630
_journal_page_last               5633
_journal_paper_doi               10.1039/d4cc01518e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C15 H14 F5 N3'
_chemical_formula_sum            'C15 H14 F5 N3'
_chemical_formula_weight         331.29
_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     dual
_audit_creation_date             2023-11-29
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-01-22 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.511(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4951(3)
_cell_length_b                   7.6806(2)
_cell_length_c                   16.1712(5)
_cell_measurement_reflns_used    10122
_cell_measurement_temperature    100.4(9)
_cell_measurement_theta_max      67.9940
_cell_measurement_theta_min      3.7320
_cell_volume                     1471.65(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.4(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  30.00   0.50    0.30    --  -40.58  89.00 -22.00  204
  2  ω    -21.00  72.00   0.50    0.30    --   40.58 -89.00-138.00  186
  3  ω   -153.00 -78.00   0.50    1.50    --  -82.50 -89.00-138.00  150
  4  ω    -81.00 -12.00   0.50    1.50    --  -82.50  89.00 -22.00  138
  5  ω     26.00 106.00   0.50    1.50    --   96.35 -89.00-138.00  160
  6  ω    -96.00 -19.00   0.50    0.30    --  -40.58 138.00-180.00  154
  7  ω    -24.00  35.00   0.50    0.30    --  -40.58  12.00 120.00  118
  8  ω    -31.00  30.00   0.50    0.30    --  -40.58  25.00 -90.00  122
  9  ω    -25.00  43.00   0.50    0.30    --   40.58 -38.00 -60.00  136
 10  ω     22.00 107.00   0.50    0.30    --   40.58  50.00  60.00  170
 11  ω    -35.00  24.00   0.50    0.30    --   40.58 -12.00  90.00  118
 12  ω    -29.00  31.00   0.50    0.30    --   40.58 -25.00-120.00  120
 13  ω   -151.00 -61.00   0.50    1.50    --  -82.50 -59.00 150.00  180
 14  ω    -47.00 -15.00   0.50    1.50    --  -82.50  42.00 -90.00   64
 15  ω    -47.00 -15.00   0.50    1.50    --  -82.50  42.00-180.00   64
 16  ω   -156.00 -83.00   0.50    1.50    --  -82.50 -96.00  30.00  146
 17  ω    -47.00 -15.00   0.50    1.50    --  -82.50  42.00 150.00   64
 18  ω     30.00  57.00   0.50    1.50    --   96.35 -50.00  90.00   54
 19  ω     29.00  83.00   0.50    1.50    --   96.35 -68.00-120.00  108
 20  ω     30.00  57.00   0.50    1.50    --   96.35 -50.00 120.00   54
 21  ω     44.00 127.00   0.50    1.50    --   96.35-145.00-120.00  166
 22  ω     28.00  68.00   0.50    1.50    --   96.35 -59.00  30.00   80
 23  ω     30.00  57.00   0.50    1.50    --   96.35 -50.00  30.00   54
 24  ω    105.00 170.00   0.50    1.50    --   96.35  96.00   0.00  130
 25  ω     44.00 127.00   0.50    1.50    --   96.35-145.00  60.00  166
 26  ω     81.00 167.00   0.50    1.50    --   96.35  25.00 -60.00  172
 27  ω     44.00 127.00   0.50    1.50    --   96.35-145.00  90.00  166
 28  ω     33.00 110.00   0.50    1.50    --   96.35-117.00  90.00  154
 29  ω     28.00 105.00   0.50    1.50    --   96.35 -77.00 -90.00  154
 30  ω     30.00  57.00   0.50    1.50    --   96.35 -50.00 -60.00   54
 31  ω     29.00  83.00   0.50    1.50    --   96.35 -68.00  90.00  108
 32  ω    100.00 167.00   0.50    1.50    --   96.35  89.00 -22.00  134
 33  ω   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00  60.00  190
 34  ω   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00 120.00  190
 35  ω   -108.00 -17.00   0.50    0.30    --  -40.58 -64.00-120.00  182
 36  ω   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00-180.00  190
 37  ω   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00 -30.00  190
 38  ω    -25.00  43.00   0.50    0.30    --   40.58 -38.00   0.00  136
 39  ω     14.00 109.00   0.50    0.30    --   40.58  77.00  60.00  190
 40  ω     22.00 107.00   0.50    0.30    --   40.58  50.00   0.00  170
 41  ω     18.00 108.00   0.50    0.30    --   40.58  64.00-150.00  180
 42  ω     14.00 109.00   0.50    0.30    --   40.58  77.00 -90.00  190
 43  ω   -151.00 -72.00   0.50    1.50    --  -82.50 -77.00 -90.00  158
 44  ω     77.00 163.00   0.50    1.50    --   96.35  50.00-180.00  172
 45  ω     72.00 164.00   0.50    1.50    --   96.35  68.00  90.00  184
 46  ω     75.00 165.00   0.50    1.50    --   96.35  59.00 -30.00  180
 47  ω     83.00 164.00   0.50    1.50    --   96.35  33.00-120.00  162
 48  ω     80.00 164.00   0.50    1.50    --   96.35  42.00  60.00  168
 49  ω     70.00 165.00   0.50    1.50    --   96.35  77.00 120.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1245792000
_diffrn_orient_matrix_UB_12      0.0314184000
_diffrn_orient_matrix_UB_13      0.0533557000
_diffrn_orient_matrix_UB_21      0.0045820000
_diffrn_orient_matrix_UB_22      -0.1792434000
_diffrn_orient_matrix_UB_23      0.0437665000
_diffrn_orient_matrix_UB_31      0.0367369000
_diffrn_orient_matrix_UB_32      -0.0845139000
_diffrn_orient_matrix_UB_33      -0.0730836000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16716
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.072
_diffrn_reflns_theta_min         3.731
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0446
_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)+(0.0781P)²+0.4736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2323
_reflns_number_total             2682
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01518e2.cif
_cod_data_source_block           ada_ab_272_auto_1
_cod_depositor_comments
'Adding full bibliography for 7132998--7132999.cif.'
_cod_database_code               7132999
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     100K
_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_max   0.988
_shelx_estimated_absorpt_t_min   0.797
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C8(H8)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.625
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
F1 F 0.56673(9) 0.18624(13) 0.66567(7) 0.0352(3) Uani 1 1 d . . . . .
F5 F 0.84840(9) 0.62330(14) 0.74238(7) 0.0365(3) Uani 1 1 d . . . . .
F4 F 1.00209(9) 0.38176(16) 0.81991(8) 0.0438(3) Uani 1 1 d . . . . .
F2 F 0.72121(11) -0.05098(14) 0.74605(8) 0.0455(3) Uani 1 1 d . . . . .
F3 F 0.94054(11) 0.04244(16) 0.82144(8) 0.0475(3) Uani 1 1 d . . . . .
N3 N 0.37951(12) 0.90449(19) 0.53955(10) 0.0288(4) Uani 1 1 d . . . . .
H3 H 0.399618 0.990142 0.511472 0.035 Uiso 1 1 calc R . . . .
N2 N 0.55848(12) 0.79514(19) 0.56492(10) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.43099(12) 0.66940(19) 0.63290(10) 0.0306(4) Uani 1 1 d . . . . .
C10 C 0.45766(14) 0.7865(2) 0.57995(11) 0.0273(4) Uani 1 1 d . . . . .
C6 C 0.70122(15) 0.4149(2) 0.70081(11) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.67353(15) 0.2397(2) 0.70394(11) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.61507(15) 0.5470(2) 0.65849(11) 0.0275(4) Uani 1 1 d . . . . .
C5 C 0.81431(15) 0.4569(2) 0.74036(12) 0.0298(4) Uani 1 1 d . . . . .
C9 C 0.63351(15) 0.6750(2) 0.60371(12) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.704316 0.676256 0.593529 0.035 Uiso 1 1 calc R . . . .
C8 C 0.50985(15) 0.5529(2) 0.67098(12) 0.0294(4) Uani 1 1 d . . . . .
H8 H 0.493630 0.469311 0.708650 0.035 Uiso 1 1 calc R . . . .
C11 C 0.26295(14) 0.8983(2) 0.53968(12) 0.0275(4) Uani 1 1 d . . . . .
H11 H 0.263299 0.869665 0.600079 0.033 Uiso 1 1 calc R . . . .
C2 C 0.75231(17) 0.1150(2) 0.74411(12) 0.0327(4) Uani 1 1 d . . . . .
C4 C 0.89471(15) 0.3342(3) 0.78049(12) 0.0327(4) Uani 1 1 d . . . . .
C3 C 0.86334(17) 0.1624(3) 0.78186(12) 0.0352(5) Uani 1 1 d . . . . .
C14 C 0.20961(15) 1.0773(2) 0.51563(13) 0.0334(4) Uani 1 1 d . . . . .
H14A H 0.210757 1.107735 0.456422 0.040 Uiso 1 1 calc R . . . .
H14B H 0.129654 1.071120 0.513532 0.040 Uiso 1 1 calc R . . . .
C12 C 0.19835(16) 0.7548(2) 0.47813(13) 0.0342(4) Uani 1 1 d . . . . .
H12A H 0.195889 0.784096 0.417933 0.041 Uiso 1 1 calc R . . . .
H12B H 0.240335 0.644090 0.494288 0.041 Uiso 1 1 calc R . . . .
C15 C 0.26749(19) 1.2217(2) 0.57803(14) 0.0414(5) Uani 1 1 d . . . . .
H15A H 0.224921 1.330186 0.561082 0.062 Uiso 1 1 calc GR . . . .
H15B H 0.344334 1.237781 0.575816 0.062 Uiso 1 1 calc GR . . . .
H15C H 0.270563 1.190113 0.637464 0.062 Uiso 1 1 calc GR . . . .
C13 C 0.07861(18) 0.7278(3) 0.47934(15) 0.0493(6) Uani 1 1 d . . . . .
H13A H 0.048853 0.618473 0.449610 0.074 Uiso 1 1 calc GR . . . .
H13B H 0.031169 0.824862 0.449339 0.074 Uiso 1 1 calc GR . . . .
H13C H 0.078446 0.722434 0.539847 0.074 Uiso 1 1 calc GR . . . .
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'
F F 0.0727 0.0534 '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'
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
C10 N3 C11 123.43(15) . . ?
C9 N2 C10 116.03(15) . . ?
C8 N1 C10 116.43(15) . . ?
N3 C10 N2 116.95(15) . . ?
N3 C10 N1 118.02(16) . . ?
N1 C10 N2 125.03(16) . . ?
C1 C6 C7 121.74(16) . . ?
C5 C6 C1 115.74(16) . . ?
C5 C6 C7 122.52(16) . . ?
F1 C1 C6 119.98(16) . . ?
F1 C1 C2 117.40(16) . . ?
C2 C1 C6 122.62(17) . . ?
C9 C7 C6 122.41(16) . . ?
C9 C7 C8 115.12(16) . . ?
C8 C7 C6 122.47(15) . . ?
F5 C5 C6 119.94(15) . . ?
F5 C5 C4 117.39(16) . . ?
C4 C5 C6 122.65(17) . . ?
N2 C9 C7 124.01(16) . . ?
N1 C8 C7 123.35(16) . . ?
N3 C11 C14 109.07(14) . . ?
N3 C11 C12 110.06(15) . . ?
C14 C11 C12 112.69(15) . . ?
F2 C2 C1 120.29(18) . . ?
F2 C2 C3 120.11(16) . . ?
C3 C2 C1 119.60(17) . . ?
F4 C4 C5 120.45(18) . . ?
F4 C4 C3 119.99(17) . . ?
C3 C4 C5 119.53(18) . . ?
F3 C3 C2 120.12(18) . . ?
F3 C3 C4 120.02(18) . . ?
C2 C3 C4 119.85(17) . . ?
C15 C14 C11 114.30(15) . . ?
C13 C12 C11 114.13(16) . . ?
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
F1 C1 1.345(2) . ?
F5 C5 1.344(2) . ?
F4 C4 1.340(2) . ?
F2 C2 1.336(2) . ?
F3 C3 1.340(2) . ?
N3 C10 1.340(2) . ?
N3 C11 1.458(2) . ?
N2 C10 1.358(2) . ?
N2 C9 1.323(2) . ?
N1 C10 1.354(2) . ?
N1 C8 1.329(2) . ?
C6 C1 1.394(2) . ?
C6 C7 1.479(2) . ?
C6 C5 1.391(3) . ?
C1 C2 1.379(3) . ?
C7 C9 1.391(2) . ?
C7 C8 1.393(3) . ?
C5 C4 1.380(3) . ?
C11 C14 1.523(2) . ?
C11 C12 1.532(2) . ?
C2 C3 1.375(3) . ?
C4 C3 1.379(3) . ?
C14 C15 1.519(3) . ?
C12 C13 1.517(3) . ?
