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_7043866
_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         'C26 H36 N3 P S'
_chemical_formula_sum            'C26 H36 N3 P S'
_chemical_formula_weight         453.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-30 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                99.675(4)
_cell_angle_beta                 90.025(4)
_cell_angle_gamma                92.645(4)
_cell_formula_units_Z            4
_cell_length_a                   9.4412(16)
_cell_length_b                   15.818(3)
_cell_length_c                   17.317(3)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.39
_cell_volume                     2546.5(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            55378
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.096
_diffrn_reflns_theta_min         1.193
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0531 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.9303. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         14925
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+1.1846P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11017
_reflns_number_total             14925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt01859b2.cif
_cod_data_source_block           4a
_cod_original_cell_volume        2546.5(7)
_cod_database_code               7043866
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.962
_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 body (RIGU) restrains
 C11A, C12A, C13A, C14A, C15A, C16A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=1-FVAR(1)
 Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(H15)=Sof(C16)=Sof(H16)=FVAR(1)
 Sof(H10A)=1-FVAR(2)
 Sof(H10)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C10(H10A), C30(H30), C33(H33), C36(H36)
4.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C25(H25A,H25B), C49(H49A,H49B), C51(H51A,H51B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
 C16A(H16A), C29(H29), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42),
 C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
4.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C24(H24A,
 H24B,H24C), C26(H26A,H26B,H26C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C50(H50A,H50B,H50C), C52(H52A,H52B,
 H52C)
;
_shelx_res_checksum              78200
_olex2_submission_special_instructions 'No special instructions were received'