Triple dehydrofluorination as a route to amidine-functionalized, aromatic phosphorus heterocycles
Coles, Nathan Thomas; Groth, Lucie; Dettling, Lea; Frost, Daniel Sebastian; Rigo, Massimo; Neale, Samuel E.; Muller, Christian; Chemical Communications  (2022) –; doi:10.1039/D2CC05178H

data_7130946
_publ_section_title
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 Triple dehydrofluorination as a route to amidine-functionalized, aromatic
 phosphorus heterocycles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05178H
_journal_year                    2022
_chemical_formula_moiety         'C10 H12 F3 N2 P'
_chemical_formula_sum            'C10 H12 F3 N2 P'
_chemical_formula_weight         248.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-06-03 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.664(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2387(8)
_cell_length_b                   11.0061(7)
_cell_length_c                   8.6295(5)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.49
_cell_volume                     1156.72(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19732
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.572
_diffrn_reflns_theta_min         2.494
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8660
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1025 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.8660.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       Block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0452
_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/[\s^2^(Fo^2^)+(0.0569P)^2^+1.2038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3321
_reflns_number_total             3536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05178h2.cif
_cod_data_source_block           ntc-155
_cod_database_code               7130946
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C3(H3)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              60365
_shelx_hkl_checksum              69
_olex2_submission_special_instructions 'No special instructions were received'