Multifunctional 1,3-diphenylguanidine for carboxylative cyclization of homopropargyl amines with CO2 under ambient temperature and pressure
Gao, Xiao-Tong; Xie, Shi-Liang; Zhou, Feng; Wu, Hai-Hong; Zhou, Jian; Chemical Communications  (2019) –; doi:10.1039/C9CC07671A

data_7124350
_publ_section_title
;
 Multifunctional 1,3-diphenylguanidine for carboxylative cyclization of
 homopropargyl amines with CO2 under ambient temperature and pressure
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07671A
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'F6 Sb, C26 H26 Ag N6'
_chemical_formula_sum            'C26 H26 Ag F6 N6 Sb'
_chemical_formula_weight         766.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-30 deposited with the CCDC.    2019-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7369(6)
_cell_length_b                   31.5086(13)
_cell_length_c                   5.9773(2)
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      43.34
_cell_measurement_theta_min      4.89
_cell_volume                     2775.49(19)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1534
_diffrn_reflns_av_unetI/netI     0.1249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            22100
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.953
_diffrn_reflns_theta_min         2.880
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.462
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1537 before and 0.0851 after correction. The Ratio of minimum to maximum transmission is 0.5511. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.912
_refine_diff_density_min         -1.434
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0812P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1822
_reflns_Friedel_coverage         0.536
_reflns_Friedel_fraction_full    0.670
_reflns_Friedel_fraction_max     0.654
_reflns_number_gt                2208
_reflns_number_total             4443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07671a2.cif
_cod_data_source_block           mj19077_0m
_cod_database_code               7124350
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.764
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N4(H4), N5(H5A), N6(H6A), C3(H3A), C4(H4A), C5(H5), C6(H6),
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              6805
_olex2_submission_special_instructions 'No special instructions were received'