Iridium catalyzed acceptor/acceptor carbene insertion into N-H bonds in water.
Ramakrishna, Kankanala; Sivasankar, Chinnappan; Organic & biomolecular chemistry 15 (2017) 2392–2396; doi:10.1039/c7ob00177k

data_7155505
_publ_section_title
;
 Iridium catalyzed acceptor/acceptor carbene insertion into N-H bonds in
 water.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2392
_journal_page_last               2396
_journal_paper_doi               10.1039/c7ob00177k
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C11 H12 N2 O6'
_chemical_formula_sum            'C11 H12 N2 O6'
_chemical_formula_weight         268.23
_chemical_name_systematic        'dimethyl 2-((4-nitrophenyl)amino)malonate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-28
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_audit_update_record
;
2016-10-28 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.539(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8685(4)
_cell_length_b                   15.9375(7)
_cell_length_c                   10.1120(4)
_cell_measurement_reflns_used    2084
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0078
_cell_measurement_theta_min      4.3142
_cell_volume                     1237.84(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details
;
  1 omega  -16.00   23.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  -90.0000 39

  2 omega  -12.00   15.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000   30.0000 27

  3 omega   -8.00   18.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000   90.0000 26

  4 omega  -25.00   22.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  150.0000 47

  5 omega  -61.00   41.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   19.0000  -60.0000 102

  6 omega  -65.00  -39.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000  150.0000 26

  7 omega   12.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   57.0000  120.0000 54
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0030076000
_diffrn_orient_matrix_UB_12      0.0434590000
_diffrn_orient_matrix_UB_13      0.0154941000
_diffrn_orient_matrix_UB_21      -0.0775731000
_diffrn_orient_matrix_UB_22      -0.0039953000
_diffrn_orient_matrix_UB_23      0.0244430000
_diffrn_orient_matrix_UB_31      0.0500191000
_diffrn_orient_matrix_UB_32      -0.0087637000
_diffrn_orient_matrix_UB_33      0.0657538000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7603
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.072
_diffrn_reflns_theta_min         4.323
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0624P)^2^+0.4067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2138
_reflns_number_total             2846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00177k2.cif
_cod_data_source_block           cs-rk-nw59-g
_cod_depositor_comments          'Adding full bibliography for 7155505.cif.'
_cod_original_cell_volume        1237.83(10)
_cod_database_code               7155505
_chemical_oxdiff_formula         'C20 H25 O2 N1'
_chemical_oxdiff_usercomment     'COLOURLESS BLOCK, 295K, 0.55 0.35 0.15'
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              61623
_shelx_shelxl_version_number     2014/7