Copper-Catalyzed Carbamoylation of Terminal Alkynes with Formamides via Cross-Dehydrogenative Coupling
Wu, Jin-Ji; Li, Yinwu; Zhou, Hai-Yun; Wen, A-Hao; Lun, Chu-Chu; Yao, Su-Yang; Ke, Zhuofeng; Ye, Bao-Hui; ACS Catalysis  (2016) 1263–; doi:10.1021/acscatal.5b02881

data_4513805
_publ_section_title
;
 Copper-Catalyzed Carbamoylation of Terminal Alkynes with Formamides via
 Cross-Dehydrogenative Coupling
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1263
_journal_paper_doi               10.1021/acscatal.5b02881
_journal_year                    2016
_chemical_formula_moiety         'C11 H11 N O'
_chemical_formula_sum            'C11 H11 N O'
_chemical_formula_weight         173.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-26
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                90
_cell_angle_beta                 91.838(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5306(7)
_cell_length_b                   6.1547(5)
_cell_length_c                   20.6613(16)
_cell_measurement_reflns_used    754
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.0590
_cell_measurement_theta_min      3.8440
_cell_volume                     957.13(14)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.8667
_diffrn_measurement_details
;
  1 omega  -15.00   99.00   1.0000    7.5900
omega____ theta____ kappa____ phi______ frames
    -       23.5093  -19.0000 -180.0000 114

  2 omega  -99.00   13.00   1.0000    7.5900
omega____ theta____ kappa____ phi______ frames
    -      -23.6656  -77.0000 -150.0000 112
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0601837000
_diffrn_orient_matrix_UB_12      0.0090583000
_diffrn_orient_matrix_UB_13      -0.0255667000
_diffrn_orient_matrix_UB_21      -0.0678739000
_diffrn_orient_matrix_UB_22      -0.0337112000
_diffrn_orient_matrix_UB_23      -0.0223855000
_diffrn_orient_matrix_UB_31      -0.0256991000
_diffrn_orient_matrix_UB_32      0.1098812000
_diffrn_orient_matrix_UB_33      -0.0047784000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3333
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.2020
_exptl_crystal_description       block
_exptl_crystal_F_000             368.1637
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2639
_refine_diff_density_min         -0.2623
_refine_diff_density_rms         0.0664
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_refine_ls_d_res_low             5.8984
_refine_ls_goodness_of_fit_ref   1.0739
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0739
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.1910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1631
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              -8
_reflns_number_gt                1552
_reflns_number_total             2119
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            cs5b02881_si_002.cif
_cod_data_source_block           0326
_cod_original_cell_volume        957.14(13)
_cod_database_code               4513805
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'