Alkene Synthesis by Photocatalytic Chemoenzymatically Compatible Dehydrodecarboxylation of Carboxylic Acids and Biomass
Nguyen, Vu T.; Nguyen, Viet D.; Haug, Graham C.; Dang, Hang T.; Jin, Shengfei; Li, Zhiliang; Flores-Hansen, Carsten; Benavides, Brenda S.; Arman, Hadi D.; Larionov, Oleg V.; ACS Catalysis 9 (2019) 9485–; doi:10.1021/acscatal.9b02951

data_4514633
_publ_section_title
;
 Alkene Synthesis by Photocatalytic Chemoenzymatically Compatible
 Dehydrodecarboxylation of Carboxylic Acids and Biomass
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9485
_journal_paper_doi               10.1021/acscatal.9b02951
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C15 H17 N3 O4 S'
_chemical_formula_sum            'C15 H17 N3 O4 S'
_chemical_formula_weight         335.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.091(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3181(12)
_cell_length_b                   6.9639(4)
_cell_length_c                   17.0635(15)
_cell_measurement_reflns_used    2230
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      26.2270
_cell_measurement_theta_min      2.9980
_cell_volume                     1582.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_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      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -85.00  27.00   1.00   58.00    --    4.20 -39.00 -72.00  112
  2  \w    -97.00  17.00   1.00   58.00    --   -7.60 -39.00 -72.00  114
  3  \w    -32.00  82.00   1.00   58.00    --   -7.60  38.00-120.00  114
  4  \w    -32.00  45.00   1.00   58.00    --   -7.60  38.00  60.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0028197000
_diffrn_orient_matrix_UB_12      -0.0504750000
_diffrn_orient_matrix_UB_13      -0.0360325000
_diffrn_orient_matrix_UB_21      -0.0531830000
_diffrn_orient_matrix_UB_22      -0.0034621000
_diffrn_orient_matrix_UB_23      -0.0018010000
_diffrn_orient_matrix_UB_31      -0.0004755000
_diffrn_orient_matrix_UB_32      0.0884490000
_diffrn_orient_matrix_UB_33      -0.0206108000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17319
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.387
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2007
_reflns_number_total             2954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02951_si_005.cif
_cod_data_source_block           cd1785b
_cod_database_code               4514633
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C20H20n2O4
_chemical_oxdiff_usercomment     'Oleg sample YNS 169-8'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 99.40
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C8(H8), C5(H5), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.845