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_4033660
_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         'C14 H16 Cl N O4'
_chemical_formula_sum            'C14 H16 Cl N O4'
_chemical_formula_weight         297.73
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4216(3)
_cell_length_b                   21.0246(9)
_cell_length_c                   18.7410(7)
_cell_measurement_reflns_used    4458
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.950
_cell_measurement_theta_min      2.912
_cell_volume                     2924.3(2)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_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_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13276
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         2.221
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2007/4 (Bruker,2007/4) was used for absorption correction.
wR2(int) was 0.0694 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.8410.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+1.1228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2590
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01392_si_003.cif
_cod_data_source_block           pbcn
_cod_database_code               4033660
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3B(H3BA,H3BB), C3A(H3AA,H3AB)
2.b Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C2C(H2C), C6C(H6C), C5C(H5C), C3C(H3C), N1C(H1C)
2.c Idealised Me refined as rotating group:
 C4B(H4BA,H4BB,H4BC), C4A(H4AA,H4AB,H4AC)
;
_shelx_res_checksum              9861
_shelx_hkl_checksum              92688
_olex2_submission_special_instructions 'No special instructions were received'