Dimethylzinc-Mediated Addition of Phenylacetylene to α-Diketones Catalyzed by Chiral Perhydro-1,3-benzoxazines.
Infante, Rebeca; Martin-Alvarez, Jose M; Andrés, Celia; Nieto, Javier; Organic letters 19 (2017) 1516–1519; doi:10.1021/acs.orglett.7b00252

data_1556018
_publ_section_title
;
 Dimethylzinc-Mediated Addition of Phenylacetylene to \a-Diketones
 Catalyzed by Chiral Perhydro-1,3-benzoxazines.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1516
_journal_page_last               1519
_journal_paper_doi               10.1021/acs.orglett.7b00252
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H17 Cl O3'
_chemical_formula_sum            'C23 H17 Cl O3'
_chemical_formula_weight         376.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.687(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5553(12)
_cell_length_b                   9.5675(3)
_cell_length_c                   22.2196(14)
_cell_measurement_reflns_used    4507
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.3610
_cell_measurement_theta_min      2.3890
_cell_volume                     3937.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.844
_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    -20.00  50.00   1.00   85.67    --    9.78 -99.00   0.00   70
  2  \w    -78.00  96.00   1.00   85.67    --    9.78   0.00  30.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0049152000
_diffrn_orient_matrix_UB_12      -0.0201723000
_diffrn_orient_matrix_UB_13      -0.0284676000
_diffrn_orient_matrix_UB_21      0.0360828000
_diffrn_orient_matrix_UB_22      0.0247366000
_diffrn_orient_matrix_UB_23      0.0154697000
_diffrn_orient_matrix_UB_31      0.0118570000
_diffrn_orient_matrix_UB_32      -0.0669148000
_diffrn_orient_matrix_UB_33      0.0143014000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13426
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.781
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.030
_diffrn_reflns_theta_min         2.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         8208
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0655
_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^)+(0.0782P)^2^+1.0868P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.710
_reflns_number_gt                4664
_reflns_number_total             8208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00252_si_001.cif
_cod_data_source_block           pclpome
_cod_database_code               1556018
_chemical_oxdiff_formula         'C23 H17 Cl O3'
_reflns_odcompleteness_completeness 98.41
_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, All O(H) groups
2. Rigid bond restraints
 C35, C36, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C22(H22), C23(H23), C25(H25), C26(H26), C36(H36), C37(H37), C38(H38),
  C39(H39), C40(H40), C42(H42), C43(H43), C45(H45), C46(H46), C52(H52),
 C53(H53), C55(H55), C56(H56)
4.b Fitted hexagon refined as free rotating group:
 C35(C36,C37,C38,C39,C40)
4.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C57(H57A,H57B,H57C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              93896
_shelx_hkl_checksum              16412
_shelx_shelxl_version_number     2014/7
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.580