Toward anti-Markovnikov 1-Alkyne O-Phosphoramidation: Exploiting Metal-Ligand Cooperativity in a 1,3-N,O-Chelated Cp*Ir(III) Complex.
Drover, Marcus W.; Love, Jennifer A.; Schafer, Laurel L.; Journal of the American Chemical Society 138 (2016) 8396–8399; doi:10.1021/jacs.6b05143

data_4130616
_publ_section_title
;
 Toward anti-Markovnikov 1-Alkyne O-Phosphoramidation: Exploiting
 Metal-Ligand Cooperativity in a 1,3-N,O-Chelated Cp*Ir(III) Complex.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8396
_journal_page_last               8399
_journal_paper_doi               10.1021/jacs.6b05143
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C18 H22 N O3 P'
_chemical_formula_sum            'C18 H22 N O3 P'
_chemical_formula_weight         331.33
_chemical_name_systematic
'N-2,6-dimethylphenyl O-ethoxy, O-vinylphenyl phosphoramidate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-23
_audit_creation_method
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.470(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.898(5)
_cell_length_b                   19.451(9)
_cell_length_c                   9.138(5)
_cell_measurement_reflns_used    1777
_cell_measurement_temperature    90
_cell_measurement_theta_max      25.529
_cell_measurement_theta_min      2.334
_cell_volume                     1735.3(15)
_computing_cell_refinement       'SAINT v8.34A (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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12784
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.520
_diffrn_reflns_theta_min         2.086
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0779 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.7562.
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    1.268
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0740P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2397
_reflns_number_total             3597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05143_si_002.cif
_cod_data_source_block           jl220final_a
_cod_original_cell_volume        1735.2(14)
_cod_database_code               4130616
_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.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              99278
_shelx_hkl_checksum              63803
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'