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_7155871
_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 O3'
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40
_chemical_name_systematic
((1R,2R)-2-(4-methoxyphenoxy)-1-phenylcyclopropyl)(pyrrolidin-1-yl)methanone
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-08-26 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.287(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9367(4)
_cell_length_b                   14.2449(4)
_cell_length_c                   11.4918(3)
_cell_measurement_reflns_used    8142
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8320
_cell_measurement_theta_min      5.0710
_cell_volume                     1808.06(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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 0.999
_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    -38.00  28.00   1.00    2.00    --  -41.85  38.00  60.00   66
  2  \w    -67.00 -19.00   1.00    2.00    --  -41.85 -38.00 120.00   48
  3  \w    -32.00  65.00   1.00    2.00    --   41.85 -38.00-150.00   97
  4  \w     37.00 131.00   1.00    9.00    --  106.96 -45.00 -30.00   94
  5  \w     63.00  96.00   1.00    2.00    --   41.85-125.00   0.00   33
  6  \w     55.00  99.00   1.00    9.00    --  106.96 -95.00 -30.00   44
  7  \w     57.00 121.00   1.00    9.00    --  106.96-125.00 150.00   64
  8  \w     80.00 176.00   1.00    9.00    --  106.96  30.00 150.00   96
  9  \w    107.00 177.00   1.00    9.00    --  106.96 125.00 -60.00   70
 10  \w    125.00 156.00   1.00    9.00    --  106.96 125.00 -90.00   31
 11  \w     53.00  79.00   1.00    2.00    --   41.85-125.00-180.00   26
 12  \w     84.00 109.00   1.00    9.00    --  106.96 -95.00-180.00   25
 13  \w    106.00 132.00   1.00    9.00    --  106.96 -45.00 -30.00   26
 14  \w     30.00  56.00   1.00    9.00    --  106.96 -95.00-180.00   26
 15  \w     84.00 109.00   1.00    9.00    --  106.96 -95.00 -60.00   25
 16  \w     34.00  60.00   1.00    9.00    --  112.00 -95.00 150.00   26
 17  \w     68.00  94.00   1.00    9.00    --  112.00 -95.00 150.00   26
 18  \w     69.00 114.00   1.00    9.00    --  112.00 -61.00 -90.00   45
 19  \w    144.00 178.00   1.00    9.00    --  112.00  30.00-120.00   34
 20  \w     63.00 115.00   1.00    9.00    --  112.00-111.00 -60.00   52
 21  \w     45.00  80.00   1.00    9.00    --  112.00-111.00-150.00   35
 22  \w     90.00 116.00   1.00    9.00    --  112.00-111.00-150.00   26
 23  \w    113.00 139.00   1.00    9.00    --  112.00 111.00   0.00   26
 24  \w    143.00 168.00   1.00    9.00    --  112.00 111.00   0.00   25
 25  \w    111.00 137.00   1.00    9.00    --  112.00 111.00 -30.00   26
 26  \w    139.00 178.00   1.00    9.00    --  112.00 111.00  60.00   39
 27  \w     55.00  98.00   1.00    9.00    --  112.00 -30.00 -30.00   43
;
_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      0.0840080000
_diffrn_orient_matrix_UB_12      0.0175392000
_diffrn_orient_matrix_UB_13      -0.0717249000
_diffrn_orient_matrix_UB_21      0.0190583000
_diffrn_orient_matrix_UB_22      -0.1066126000
_diffrn_orient_matrix_UB_23      -0.0058798000
_diffrn_orient_matrix_UB_31      -0.1097319000
_diffrn_orient_matrix_UB_32      -0.0049041000
_diffrn_orient_matrix_UB_33      -0.1256668000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11506
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         4.002
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.239
_exptl_crystal_description       irregular
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Compound was crystallized from Hexane-EtOAc mixture'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1068P)^2^+0.3423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             3304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01785e2.cif
_cod_data_source_block           anna_23082017_ypm30_3
_cod_original_cell_volume        1808.07(10)
_cod_database_code               7155871
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C21H23NO3
_reflns_odcompleteness_completeness 99.86
_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:
 C2(H2A,H2B), C5(H5A,H5B), C8(H8A,H8B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C14(H14), C11(H11),
 C13(H13), C10(H10)
2.d Fitted hexagon refined as free rotating group:
 C15(C16,C17,C18,C19,C20)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              22969
_olex2_date_sample_data_collection 2017-08-25
_olex2_exptl_crystal_mounting_method
'Mounted on the glass stick by acrylic glue'
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.655