#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:00:03 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293750 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571926.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_1571926
loop_
_publ_author_name
'Biswas, Soumen'
'Empel, Claire'
'Sanchez-Palestino, Luis Mario'
'Arman, Hadi'
'Koenigs, Rene M.'
'Doyle, Michael P.'
_publ_section_title
;
 Denitrogenative dismantling of heteroaromatics by nucleophilic
 substitution reactions with diazomethyl compounds.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              11065
_journal_page_last               11071
_journal_paper_doi               10.1039/d4sc01578a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C14 H11 F3 O3'
_chemical_formula_sum            'C14 H11 F3 O3'
_chemical_formula_weight         284.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-02
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-07-29 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                97.571(3)
_cell_angle_beta                 107.127(4)
_cell_angle_gamma                95.412(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1427(3)
_cell_length_b                   9.1744(4)
_cell_length_c                   9.7896(4)
_cell_measurement_reflns_used    6959
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      75.7210
_cell_measurement_theta_min      4.7990
_cell_volume                     601.69(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 111.00   0.50    0.60    --  106.29-125.00 150.00  150
  2  ω     36.00 111.00   0.50    0.60    --  106.29-125.00 120.00  150
  3  ω     33.00 105.00   0.50    0.60    --  106.29 -94.00   0.00  144
  4  ω     33.00 105.00   0.50    0.60    --  106.29 -94.00 120.00  144
  5  ω     36.00 111.00   0.50    0.60    --  106.29-125.00 -30.00  150
  6  ω     33.00 105.00   0.50    0.60    --  106.29 -94.00 -60.00  144
  7  ω     33.00 105.00   0.50    0.60    --  106.29 -94.00-180.00  144
  8  ω     33.00 101.00   0.50    0.60    --  106.29 -77.00-180.00  136
  9  ω     33.00  71.00   0.50    0.60    --  106.29 -61.00-120.00   76
 10  ω    -26.00  62.00   0.50    0.15    --   45.90 -57.00-120.00  176
 11  ω     33.00  71.00   0.50    0.60    --  106.29 -61.00 120.00   76
 12  ω    -29.00  33.00   0.50    0.15    --   45.90 -24.00 105.00  124
 13  ω     92.00 178.00   0.50    0.60    --  106.29  24.00 -90.00  172
 14  ω     31.00 120.00   0.50    0.15    --   45.90  37.00 -60.00  178
 15  ω     31.00 120.00   0.50    0.15    --   45.90  37.00   0.00  178
 16  ω     32.00 122.00   0.50    0.15    --   45.90  24.00 -90.00  180
 17  ω     31.00 120.00   0.50    0.15    --   45.90  37.00-120.00  178
 18  ω     31.00 120.00   0.50    0.15    --   45.90  37.00-150.00  178
 19  ω     31.00 120.00   0.50    0.15    --   45.90  37.00-180.00  178
 20  ω    -43.00  28.00   0.50    0.15    --  -45.90  37.00 -60.00  142
 21  ω    -33.00  30.00   0.50    0.15    --  -45.90  24.00 -90.00  126
 22  ω    -30.00  30.00   0.50    0.15    --  -45.90  19.00  60.00  120
 23  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00 150.00   64
 24  ω   -101.00 -19.00   0.50    0.60    --  -91.75  77.00  60.00  164
 25  ω    -71.00 -19.00   0.50    0.60    --  -91.75  61.00 -30.00  104
 26  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00 -30.00   64
 27  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00 -90.00   64
 28  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00-180.00   64
 29  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00-120.00   64
 30  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00  90.00   64
 31  ω    -85.00 -22.00   0.50    0.60    --  -91.75 125.00 150.00  126
 32  ω   -122.00 -31.00   0.50    0.15    --  -45.90 -24.00 105.00  182
 33  ω   -120.00 -31.00   0.50    0.15    --  -45.90 -37.00  30.00  178
 34  ω   -120.00 -31.00   0.50    0.15    --  -45.90 -37.00 -30.00  178
 35  ω   -120.00 -31.00   0.50    0.15    --  -45.90 -37.00 -90.00  178
 36  ω   -164.00 -77.00   0.50    0.60    --  -91.75 -45.00   0.00  174
 37  ω   -164.00 -77.00   0.50    0.60    --  -91.75 -45.00  60.00  174
 38  ω   -167.00 -77.00   0.50    0.60    --  -91.75 -24.00 105.00  180
 39  ω   -164.00-100.00   0.50    0.60    --  -91.75 -94.00 -90.00  128
 40  ω   -164.00-100.00   0.50    0.60    --  -91.75 -94.00-120.00  128
 41  ω   -164.00-100.00   0.50    0.60    --  -91.75 -94.00-150.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2263709000
_diffrn_orient_matrix_UB_12      -0.0437319000
_diffrn_orient_matrix_UB_13      -0.0524841000
_diffrn_orient_matrix_UB_21      -0.0267797000
_diffrn_orient_matrix_UB_22      0.1638379000
_diffrn_orient_matrix_UB_23      -0.0067646000
_diffrn_orient_matrix_UB_31      0.0013897000
_diffrn_orient_matrix_UB_32      -0.0227552000
_diffrn_orient_matrix_UB_33      -0.1584312000
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9968
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.802
_diffrn_reflns_theta_min         4.795
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
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            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0365
_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)+(0.0625P)²+0.1901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2023
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01578a2.cif
_cod_data_source_block           hpd718_auto
_cod_depositor_comments
'Adding full bibliography for 1571926--1571927.cif.'
_cod_database_code               1571926
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     SB2-167A
_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   0.897
_shelx_estimated_absorpt_t_min   0.868
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H7 of C7, H5 of C5, H6 of C6, H4 of C4, H1A of C1
 At 1.5 times of:
  All C(H,H,H) groups, H1 of C12
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1A), C7(H7), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_exptl_crystal_mounting_method 'nylo loop'
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.737
loop_
_space_group_symop_operation_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_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
F3 F 0.42414(12) 0.24668(10) 0.08987(9) 0.0281(2) Uani 1 1 d . . . . .
F2 F 0.71335(13) 0.30098(11) 0.07302(9) 0.0308(2) Uani 1 1 d . . . . .
F1 F 0.65235(15) 0.11530(10) 0.17494(10) 0.0351(3) Uani 1 1 d . . . . .
O3 O 0.91808(15) 0.19911(11) 0.69283(10) 0.0229(2) Uani 1 1 d . . . . .
O1 O 0.87135(15) 0.57863(11) 0.78297(11) 0.0232(2) Uani 1 1 d . . . . .
O2 O 1.00049(16) 0.35283(11) 0.90666(10) 0.0251(3) Uani 1 1 d . . . . .
C2 C 0.7868(2) 0.44330(15) 0.54887(15) 0.0200(3) Uani 1 1 d . . . . .
C9 C 0.6758(2) 0.35466(16) 0.30497(15) 0.0211(3) Uani 1 1 d . . . . .
C10 C 0.8594(2) 0.45086(15) 0.69461(15) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.9331(2) 0.32879(15) 0.77572(15) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.7164(2) 0.71485(16) 0.52442(15) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.761778 0.752562 0.625428 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7199(2) 0.56698(16) 0.47353(15) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.7557(2) 0.31468(16) 0.43529(15) 0.0214(3) Uani 1 1 d . . . . .
H1A H 0.786682 0.218515 0.450716 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5803(2) 0.60397(16) 0.22395(16) 0.0231(3) Uani 1 1 d . . . . .
H7 H 0.534343 0.566729 0.122851 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6177(2) 0.25495(16) 0.16266(15) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.6517(2) 0.51198(16) 0.32297(15) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.5774(2) 0.75218(17) 0.27581(16) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.528811 0.816789 0.209348 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6448(2) 0.80690(16) 0.42404(16) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.642056 0.908499 0.457260 0.030 Uiso 1 1 calc R U . . .
C13 C 0.8348(2) 0.00924(17) 0.82652(16) 0.0268(3) Uani 1 1 d . . . . .
H13A H 0.709067 -0.018832 0.748085 0.040 Uiso 1 1 calc R U . . .
H13B H 0.817156 0.081042 0.903643 0.040 Uiso 1 1 calc R U . . .
H13C H 0.877761 -0.079311 0.865599 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9890(2) 0.07810(16) 0.76850(16) 0.0240(3) Uani 1 1 d . . . . .
H12A H 1.111447 0.116845 0.849609 0.029 Uiso 1 1 calc R U . . .
H12B H 1.020829 0.001500 0.700891 0.029 Uiso 1 1 calc R U . . .
H1 H 0.921(3) 0.563(2) 0.874(2) 0.036 Uiso 1 1 d . U . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -2 -5 0.0460
2 -2 -6 0.0515
-2 6 -2 0.0646
-2 1 6 0.0397
2 -6 1 0.0206
-1 -1 -5 0.0513
-4 -2 -1 0.0418
-1 0 6 0.0363
4 2 -2 0.0556
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
C11 O3 C12 116.11(11) . . ?
C10 C2 C3 125.68(13) . . ?
C10 C2 C1 128.29(13) . . ?
C1 C2 C3 106.03(12) . . ?
C1 C9 C14 125.65(13) . . ?
C1 C9 C8 110.30(12) . . ?
C8 C9 C14 124.04(13) . . ?
O1 C10 C2 119.83(13) . . ?
O1 C10 C11 112.72(12) . . ?
C2 C10 C11 127.45(13) . . ?
O3 C11 C10 114.78(12) . . ?
O2 C11 O3 124.91(13) . . ?
O2 C11 C10 120.32(12) . . ?
C3 C4 C5 118.54(13) . . ?
C4 C3 C2 132.02(13) . . ?
C4 C3 C8 120.25(13) . . ?
C8 C3 C2 107.72(12) . . ?
C9 C1 C2 108.98(13) . . ?
C8 C7 C6 118.54(13) . . ?
F3 C14 F2 105.18(11) . . ?
F3 C14 C9 112.36(12) . . ?
F2 C14 C9 112.77(12) . . ?
F1 C14 F3 106.54(12) . . ?
F1 C14 F2 106.73(11) . . ?
F1 C14 C9 112.71(12) . . ?
C3 C8 C9 106.96(12) . . ?
C7 C8 C9 132.17(13) . . ?
C7 C8 C3 120.88(13) . . ?
C7 C6 C5 120.77(13) . . ?
C6 C5 C4 121.02(13) . . ?
O3 C12 C13 110.74(12) . . ?
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
F3 C14 1.3457(17) . ?
F2 C14 1.3458(17) . ?
F1 C14 1.3416(17) . ?
O3 C11 1.3250(17) . ?
O3 C12 1.4627(17) . ?
O1 C10 1.3417(17) . ?
O2 C11 1.2106(17) . ?
C2 C10 1.357(2) . ?
C2 C3 1.4747(19) . ?
C2 C1 1.4620(19) . ?
C9 C1 1.350(2) . ?
C9 C14 1.4838(19) . ?
C9 C8 1.4634(19) . ?
C10 C11 1.504(2) . ?
C4 C3 1.387(2) . ?
C4 C5 1.394(2) . ?
C3 C8 1.414(2) . ?
C7 C8 1.385(2) . ?
C7 C6 1.392(2) . ?
C6 C5 1.393(2) . ?
C13 C12 1.505(2) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.1518 -2.4762 -5.2959 -0.1009 -0.4275 0.8984
1.9920 -1.8040 -5.7062 -0.0726 -0.3103 0.9479
-1.6561 5.5055 -1.8467 0.2311 0.9588 0.1650
-1.6973 0.7656 6.1313 0.0289 0.1294 -0.9912
1.9355 -5.5862 0.7630 -0.2339 -0.9722 0.0089
-0.9683 -1.1703 -5.0965 0.5379 -0.1313 0.8327
-3.6494 -2.0393 -0.8132 0.9580 -0.2309 0.1702
-0.5844 0.4755 6.0913 -0.2082 0.0524 -0.9767
4.2205 1.9258 -2.4151 -0.9129 0.2188 0.3447
