Directed Nucleophilic Addition of Phenoxides to Cyclopropenes
Yamanushkin, Pavel; Lu Diaz, Michael; Edwards, Andrew Stephen; Aksenov, Nicolai A.; Rubina, Marina; Rubin, Michael; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01785E

data_7155872
_publ_section_title
;
 Directed Nucleophilic Addition of Phenoxides to Cyclopropenes
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01785E
_journal_year                    2017
_chemical_formula_moiety         'C21 H23 N O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_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     dual
_audit_creation_date             2017-08-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-08-24 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                62.334(6)
_cell_angle_beta                 83.248(5)
_cell_angle_gamma                79.062(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4667(5)
_cell_length_b                   10.5554(6)
_cell_length_c                   10.6002(6)
_cell_measurement_reflns_used    4636
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.5330
_cell_measurement_theta_min      4.6260
_cell_volume                     920.55(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     13.00  40.00   1.00    1.00    --  -38.08  77.00  30.00   27
  2  \w    -59.00  40.00   1.00    1.00    --  -38.08  38.00-180.00   99
  3  \w    -66.00  29.00   1.00    1.00    --  -38.08  38.00 -30.00   95
  4  \w    -73.00 -33.00   1.00    1.00    --  -38.08  77.00  30.00   40
  5  \w   -114.00 -19.00   1.00    1.00    --  -38.08 -57.00  30.00   95
  6  \w     44.00  71.00   1.00    1.00    --   38.08-125.00 -60.00   27
  7  \w     27.00  90.00   1.00    1.00    --   38.08-125.00-120.00   63
  8  \w    101.00 127.00   1.00    1.66    --  108.60 -45.00 -90.00   26
  9  \w     88.00 115.00   1.00    1.66    --  108.60-111.00-180.00   27
 10  \w     30.00  75.00   1.00    1.66    --  108.60 -45.00 -90.00   45
 11  \w     32.00 108.00   1.00    1.66    --  108.60 -95.00 -90.00   76
 12  \w     40.00 178.00   1.00    1.66    --  108.60 -15.00   0.00  138
 13  \w    103.00 178.00   1.00    1.66    --  108.60 111.00 -30.00   75
 14  \w    112.00 160.00   1.00    1.66    --  108.60 111.00  60.00   48
 15  \w     70.00 143.00   1.00    1.66    --  108.60 -30.00 120.00   73
 16  \w     49.00 125.00   1.00    1.66    --  108.60 -77.00  60.00   76
 17  \w     29.00  55.00   1.00    1.66    --  108.60 -95.00 150.00   26
 18  \w     29.00  56.00   1.00    1.66    --  108.60 -30.00 120.00   27
 19  \w     29.00 115.00   1.00    1.66    --  108.60-111.00  30.00   86
 20  \w    102.00 171.00   1.00    1.66    --  108.60 111.00-180.00   69
 21  \w     67.00  95.00   1.00    1.00    --   38.33-125.00 -30.00   28
 22  \w     63.00  89.00   1.00    1.66    --  108.60 178.00-180.00   26
 23  \w    125.00 150.00   1.00    1.66    --  108.60 178.00-180.00   25
 24  \w    130.00 156.00   1.00    1.66    --  108.60 111.00 -60.00   26
 25  \w     74.00 131.00   1.00    1.66    --  108.60  77.00 -30.00   57
 26  \w   -116.00  -6.00   1.00    1.00    --  -38.33 -57.00-180.00  110
 27  \w   -116.00  -6.00   1.00    1.00    --  -38.33 -57.00  90.00  110
 28  \w   -122.00  -2.00   1.00    1.00    --  -38.33 -77.00 -60.00  120
 29  \w      2.00  61.00   1.00    1.00    --   38.33  77.00-180.00   59
 30  \w      1.00  82.00   1.00    1.00    --   38.33 -99.00  30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0906967000
_diffrn_orient_matrix_UB_12      0.0597409000
_diffrn_orient_matrix_UB_13      0.0656816000
_diffrn_orient_matrix_UB_21      0.1380054000
_diffrn_orient_matrix_UB_22      -0.0844822000
_diffrn_orient_matrix_UB_23      -0.0336788000
_diffrn_orient_matrix_UB_31      0.0152211000
_diffrn_orient_matrix_UB_32      0.1307921000
_diffrn_orient_matrix_UB_33      -0.1466607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8033
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_min         4.713
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.764
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.247
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0194(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0560P)^2^+0.1907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3030
_reflns_number_total             3369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01785e2.cif
_cod_data_source_block           anna_23082017_ypm29_1
_cod_database_code               7155872
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C21H23NO4
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C3(H3A,H3B), C7(H7A,H7B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C17(H17), C13(H13), C11(H11), C14(H14), C21(H21), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              29365
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.669