Exploration of the Differences Between Amine and Thiolate Addition to Acetylenedicarboxylates.
Crumbie, Robyn L.; Chalmers, Gareth; Bhadbhade, Mohan; Griffith, Renate; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b01392

data_4033659
_publ_section_title
;
 Exploration of the Differences Between Amine and Thiolate Addition to
 Acetylenedicarboxylates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01392
_journal_year                    2019
_chemical_formula_moiety         'C15 H17 Cl O4 S'
_chemical_formula_sum            'C15 H17 Cl O4 S'
_chemical_formula_weight         328.79
_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   geom
_audit_creation_date             2014-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.80(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.662(12)
_cell_length_b                   5.317(4)
_cell_length_c                   26.00(3)
_cell_measurement_reflns_used    3353
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.181
_cell_measurement_theta_min      3.190
_cell_volume                     1584(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_max 0.993
_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  0.0576
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11046
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.700
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0997 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.8317.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0091(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0747P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1318
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1729
_reflns_number_total             2777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01392_si_004.cif
_cod_data_source_block           renate3_p21byn
_cod_database_code               4033659
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.922
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1B(0.047) H2C(0.053) H3AA(0.054) H3AB(0.054) H3BA(0.075)
 H3BB(0.075) H3C(0.058) H4AA(0.102) H4AB(0.102) H4AC(0.102) H4BA(0.105)
 H4BB(0.105) H4BC(0.105) H5C(0.054) H6C(0.049) H7CA(0.054) H7CB(0.054)
 Fixed X: H1B(0.76) H2C(0.3973) H3AA(0.5385) H3AB(0.6689) H3BA(0.9371)
 H3BB(0.8417) H3C(0.265) H4AA(0.4658) H4AB(0.5398) H4AC(0.5952) H4BA(1.0537)
 H4BB(1.0329) H4BC(0.9599) H5C(0.2193) H6C(0.3515) H7CA(0.5113) H7CB(0.4316)
 Fixed Y: H1B(0.5754) H2C(1.2469) H3AA(0.9579) H3AB(0.8588) H3BA(0.3735)
 H3BB(0.1531) H3C(1.0135) H4AA(0.5521) H4AB(0.6231) H4AC(0.4442) H4BA(0.1643)
 H4BB(-0.01) H4BC(-0.0585) H5C(0.5387) H6C(0.7721) H7CA(1.3118) H7CB(1.2773)
 Fixed Z: H1B(0.1493) H2C(0.1686) H3AA(0.2478) H3AB(0.2692) H3BA(0.0254)
 H3BB(0.022) H3C(0.2059) H4AA(0.2514) H4AB(0.3078) H4AC(0.2694) H4BA(0.0969)
 H4BB(0.0459) H4BC(0.0912) H5C(0.0831) H6C(0.0461) H7CA(0.1057) H7CB(0.0491)
;
_shelx_res_checksum              91247
_shelx_hkl_checksum              48001
_olex2_submission_special_instructions 'No special instructions were received'