Synthesis and characterization of novel chiral derivatizing agents containing β-keto-anthracene adducts (KAAs) by <sup>1</sup>H-NMR: aromatic influence and chiral alcohol absolute configuration determination.
Intakaew, Neeranuth; Rithchumpon, Puracheth; Prommin, Chanatkran; Yimklan, Saranphong; Kungwan, Nawee; Thavornyutikarn, Praput; Meepowpan, Puttinan; Organic & biomolecular chemistry 17 (2019) 541–554; doi:10.1039/c8ob02662a

data_7156625
_publ_section_title
;
 Synthesis and characterization of novel chiral derivatizing agents
 containing \b-keto-anthracene adducts (KAAs) by <sup>1</sup>H-NMR:
 aromatic influence and chiral alcohol absolute configuration
 determination.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              541
_journal_page_last               554
_journal_paper_doi               10.1039/c8ob02662a
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C35 H30 O5'
_chemical_formula_sum            'C35 H30 O5'
_chemical_formula_weight         530.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-29 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3620(4)
_cell_length_b                   15.3627(7)
_cell_length_c                   16.0741(7)
_cell_measurement_reflns_used    5067
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      41.422
_cell_measurement_theta_min      5.880
_cell_volume                     2805.8(2)
_computing_cell_refinement       'SAINT V8.30C (?, 2016)'
_computing_data_reduction        'SAINT V8.30C (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20316
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.080
_diffrn_reflns_theta_max         25.080
_diffrn_reflns_theta_min         2.195
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0620 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.9277.
The \l/2 correction factor is 0.0015.
;
_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    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1461 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0522P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3915
_reflns_number_total             4982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02662a3.cif
_cod_data_source_block           602103_3695_02_0m
_cod_depositor_comments
'Adding full bibliography for 7156624--7156625.cif.'
_cod_database_code               7156625
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.960
_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 Ternary CH refined with riding coordinates:
 C10(H10), C1'(H1'), C9(H9), C1"(H1")
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C7"'(H7"'), C4(H4), C5(H5), C3"'(H3"'), C6(H6), C6"'(H6"'), C4"'(H4"'),
 C8"(H8"), C3(H3), C5"'(H5"'), C8(H8), C4"(H4"), C1(H1), C6"(H6"), C7(H7),
 C5"(H5"), C7"(H7"), C2(H2)
2.d Idealised Me refined as rotating group:
 C4'(H4'A,H4'B,H4'C), C2"(H2"A,H2"B,H2"C)
;
_olex2_submission_special_instructions 'No special instructions were received'