Esterification of Carboxylic Acids with Difluoromethyl Diazomethane and Interrupted Esterification with Trifluoromethyl Diazomethane: A Fluorine Effect.
Peng, Shan-Qing; Zhang, Xiao-Wei; Zhang, Long; Hu, Xiang-Guo; Organic letters 19 (2017) 5689–5692; doi:10.1021/acs.orglett.7b02866

data_1547603
_publ_section_title
;
 Esterification of Carboxylic Acids with Difluoromethyl Diazomethane and
 Interrupted Esterification with Trifluoromethyl Diazomethane: A Fluorine
 Effect.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5689
_journal_page_last               5692
_journal_paper_doi               10.1021/acs.orglett.7b02866
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H20 F3 N O2'
_chemical_formula_sum            'C24 H20 F3 N O2'
_chemical_formula_weight         411.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-23
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
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????
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_cell_angle_alpha                90.371(6)
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_cell_length_a                   9.715(4)
_cell_length_b                   9.964(4)
_cell_length_c                   21.348(7)
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_cell_volume                     1989.9(13)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)''
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
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_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23476
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
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_diffrn_reflns_theta_max         25.200
_diffrn_reflns_theta_min         2.301
_diffrn_source                   'Sealed Tube'
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_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
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_refine_ls_number_reflns         7149
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+1.7025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1329
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_reflns_number_gt                6105
_reflns_number_total             7149
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_depositor_comments
'Adding full bibliography for 1547602--1547605.cif.'
_cod_original_cell_volume        1990.0(13)
_cod_database_code               1547603
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_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), C21A(H21C,H21D)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C3A(H3A), C4A(H4A),
  C5A(H5A), C6A(H6A), C7A(H7A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A),
 C13A(H13A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
;
_shelx_res_checksum              32635
_shelx_hkl_checksum              95072
_olex2_submission_special_instructions 'No special instructions were received'