Halodifluoroacetates as formylation reagents for various amines via unprecedented quadruple cleavage
Ma, Xingxing; Deng, Shuilin; Song, Qiuling; Organic Chemistry Frontiers 5 (2018) 3505–; doi:10.1039/C8QO00727F

data_1554394
_publ_section_title
;
 Halodifluoroacetates as formylation reagents for various amines via
 unprecedented quadruple cleavage
;
_journal_issue                   24
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3505
_journal_paper_doi               10.1039/C8QO00727F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C17 H13 F2 N O2'
_chemical_formula_sum            'C17 H13 F2 N O2'
_chemical_formula_weight         301.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc1z3lm9
_audit_creation_date             2018-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2018-01-30 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3324(7)
_cell_length_b                   18.0049(15)
_cell_length_c                   18.9382(19)
_cell_measurement_reflns_used    2586
_cell_measurement_temperature    296.32(10)
_cell_measurement_theta_max      27.0210
_cell_measurement_theta_min      4.2820
_cell_volume                     2841.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.32(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0074197000
_diffrn_orient_matrix_UB_12      0.0359432000
_diffrn_orient_matrix_UB_13      -0.0150166000
_diffrn_orient_matrix_UB_21      0.0472188000
_diffrn_orient_matrix_UB_22      -0.0114007000
_diffrn_orient_matrix_UB_23      -0.0292245000
_diffrn_orient_matrix_UB_31      -0.0703699000
_diffrn_orient_matrix_UB_32      -0.0114136000
_diffrn_orient_matrix_UB_33      -0.0180243000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13379
_diffrn_reflns_theta_full        24.9946
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.94
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4086
_exptl_crystal_description       block
_exptl_crystal_F_000             1248.8184
_refine_diff_density_max         0.2258
_refine_diff_density_min         -0.2810
_refine_diff_density_rms         0.0672
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             5.1686
_refine_ls_goodness_of_fit_ref   1.0611
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0611
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.1281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                1797
_reflns_number_total             2487
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8qo00727f3.cif
_cod_data_source_block           exp_4915
_cod_database_code               1554394
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C14(H14), C20(H20), C16(H16), C17(H17), C19(H19), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.864
_oxdiff_exptl_absorpt_empirical_full_min 0.618