A Bioinspired Catalytic Aerobic Functionalization of Phenols: Regioselective Construction of Aromatic C–N and C–O Bonds
Esguerra, Kenneth Virgel N.; Lumb, Jean-Philip; ACS Catalysis 7 (2017) 3477–; doi:10.1021/acscatal.7b00437

data_4514085
_publ_section_title
;
 A Bioinspired Catalytic Aerobic Functionalization of Phenols:
 Regioselective Construction of Aromatic C--N and C--O Bonds
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              3477
_journal_paper_doi               10.1021/acscatal.7b00437
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C34 H23 F2 N O5'
_chemical_formula_sum            'C34 H23 F2 N O5'
_chemical_formula_weight         563.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.572(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0098(5)
_cell_length_b                   19.2350(10)
_cell_length_c                   13.3175(7)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.827
_cell_measurement_theta_min      3.514
_cell_volume                     2563.2(2)
_computing_cell_refinement
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            66696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.795
_diffrn_reflns_theta_min         2.888
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1233 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.8412.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       Block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.39(17)
_refine_ls_extinction_coef       0.0108(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     763
_refine_ls_number_reflns         11679
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0688P)^2^+1.3713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                11585
_reflns_number_total             11679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00437_si_002.cif
_cod_data_source_block           lumb03
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4514083--4514085.cif.
;
_cod_database_code               4514085
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.855
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.61(17) 0.39(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C6A(H6A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A),
 C14A(H14A), C17A(H17A), C18A(H18A), C20A(H20A), C23A(H23A), C24A(H24A),
 C26A(H26A), C27A(H27A), C30A(H30A), C31A(H31A), C33A(H33A), C3B(H3B), C6B(H6B),
  C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B), C14B(H14B), C17B(H17B),
 C18B(H18B), C20B(H20B), C23B(H23B), C24B(H24B), C26B(H26B), C27B(H27B),
 C30B(H30B), C31B(H31B), C33B(H33B)
3.b Idealised Me refined as rotating group:
 C21A(H21A,H21B,H21C), C34A(H34A,H34B,H34C), C21B(H21D,H21E,H21F), C34B(H34D,
 H34E,H34F)
;
_shelx_res_checksum              35119
_shelx_hkl_checksum              7032
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-09-23
_olex2_date_sample_submission    2016-09-22
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id KVE3N-081-V2
_olex2_submission_special_instructions 'No special instructions were received'