Exploring the chemistry of backbone amino(chloro)phosphanyl-substituted imidazole-2-thiones
Koner, Abhishek; Serin, Spencer C.; Schnakenburg, Gregor; Patrick, Brian O.; Gates, Derek P.; Streubel, Rainer; Dalton Trans.  (2017) –; doi:10.1039/C7DT01859B

data_7043867
_publ_section_title
;
 Exploring the chemistry of backbone amino(chloro)phosphanyl-substituted
 imidazole-2-thiones
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01859B
_journal_year                    2017
_chemical_formula_moiety         '2(C H2 Cl2), C38 H42 N3 P S'
_chemical_formula_sum            'C40 H46 Cl4 N3 P S'
_chemical_formula_weight         773.63
_chemical_name_systematic        ABK-344
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-06-30 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.164(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.390(2)
_cell_length_b                   14.3808(14)
_cell_length_c                   27.503(3)
_cell_measurement_reflns_used    7382
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      2.34
_cell_volume                     8031.8(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing \w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21514
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.245
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         1.487
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4315
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1597 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.5785.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             3248
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.213
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         6815
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0706
_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^)+(0.1494P)^2^+22.2540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5392
_reflns_number_total             6815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt01859b2.cif
_cod_data_source_block           4b
_cod_database_code               7043867
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.955
_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. Rigid bond restraints
 C22, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C40(H40A,H40B), C35(H35A,H35B), C37(H37A,H37B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C15(H15), C17(H17), C27(H27), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C36(H36A,H36B,H36C), C38(H38A,
 H38B,H38C)
;
_shelx_res_checksum              39560
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'