Organocatalytic Reductive Propargylation: Scope and Applications.
Anif Pasha, Mohammed; Krishna, A. Vamshi; Ashok, Etikala; Ramachary, Dhevalapally Buchi; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02415

data_4036100
_publ_section_title
;
 Organocatalytic Reductive Propargylation: Scope and Applications.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02415
_journal_year                    2019
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         236.09
_chemical_name_systematic        DBR108_a_a
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-06
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.358(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1794(6)
_cell_length_b                   7.3034(3)
_cell_length_c                   12.8276(4)
_cell_measurement_reflns_used    9749
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      3.01
_cell_volume                     1267.90(9)
_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      293(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            50999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_min         3.010
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6888
_exptl_absorpt_correction_type   multi-scan
_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    1.259
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_preparation       'slow evaporation from chlorofrom'
_exptl_crystal_recrystallization_method 'slow evaporation from chlorofrom'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.52
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0849
_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^)+(0.0356P)^2^+0.3857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1976
_reflns_number_total             2929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02415_si_003.cif
_cod_data_source_block           dbr108_a_a
_cod_depositor_comments
;

2020-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.11(C15 H14 O3)'
_cod_original_formula_sum        'C1.62 H1.30 O0.32'
_cod_original_formula_units_Z    37
_cod_original_formula_weight     25.97
_cod_database_code               4036100
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.953
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00G), C00F(H00H), C00G(H00I), C00H(H00J)
2.c Idealised Me refined as rotating group:
 C00I(H00K,H00L,H00M)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              23248
_shelx_hkl_checksum              38454
_olex2_submission_original_sample_id methoxy
_olex2_submission_special_instructions 'No special instructions were received'