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_4514084
_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         'C33 H25 N O4'
_chemical_formula_sum            'C33 H25 N O4'
_chemical_formula_weight         499.54
_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
_audit_creation_date             2016-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                88.5410(10)
_cell_angle_beta                 87.5980(10)
_cell_angle_gamma                85.0970(10)
_cell_formula_units_Z            4
_cell_length_a                   9.7185(3)
_cell_length_b                   15.9184(4)
_cell_length_c                   15.9702(4)
_cell_measurement_reflns_used    5514
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.781
_cell_measurement_theta_min      3.382
_cell_volume                     2458.84(12)
_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  'ShelXL (Sheldrick, 2015)'
_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 0.988
_diffrn_measured_fraction_theta_max 0.984
_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_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11060
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.779
_diffrn_reflns_theta_min         2.410
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1089 before and 0.0528 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1827 before and 0.0673 after correction.
 The Ratio of minimum to maximum transmission is 0.82.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 95978 reflections, Rint = 0.0598
 (76532 with I > 3sig(I), Rint = 0.0580)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0204(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     691
_refine_ls_number_reflns         11060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0533P)^2^+1.2977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10193
_reflns_number_total             11060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00437_si_003.cif
_cod_data_source_block           lumb172
_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               4514084
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.922
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7595(11) 0.2405(11)
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), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A),
 C15A(H15A), C16A(H16A), C18A(H18A), C19A(H19A), C22A(H22A), C23A(H23A),
 C24A(H24A), C25A(H25A), C28A(H28A), C29A(H29A), C30A(H30A), C31A(H31A),
 C3B(H3B), C6B(H6B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B),
 C15B(H15B), C16B(H16B), C18B(H18B), C19B(H19B), C22B(H22B), C23B(H23B),
 C24B(H24B), C25B(H25B), C28B(H28B), C29B(H29B), C30B(H30B), C31B(H31B)
3.b Idealised Me refined as rotating group:
 C26A(H26A,H26B,H26C), C33A(H33A,H33B,H33C), C26B(H26D,H26E,H26F), C33B(H33D,
 H33E,H33F)
;
_shelx_res_checksum              79243
_shelx_hkl_checksum              71134
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'