Diastereodivergent synthesis of cyclopropanes via on-water [2 + 1] annulations of diazo compounds with electron-deficient alkenes
Li, Qing-Zhu; Zhang, Xiang; Xie, Ke; Dai, Qing-Song; Zeng, Rong; Liu, Yan-Qing; Jia, Zhi-Qiang; Feng, Xin; Li, Jun-Long; Green Chemistry 21 (2019) 2375–; doi:10.1039/C9GC00278B

data_1550820
_publ_section_title
;
 Diastereodivergent synthesis of cyclopropanes via on-water [2 + 1]
 annulations of diazo compounds with electron-deficient alkenes
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2375
_journal_paper_doi               10.1039/C9GC00278B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C24 H19 N3 O3'
_chemical_formula_sum            'C24 H19 N3 O3'
_chemical_formula_weight         397.42
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-11
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-11-29 deposited with the CCDC.    2019-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.476(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6825(10)
_cell_length_b                   10.7919(5)
_cell_length_c                   14.7575(12)
_cell_measurement_reflns_used    3810
_cell_measurement_temperature    293.06(10)
_cell_measurement_theta_max      72.2870
_cell_measurement_theta_min      4.2180
_cell_volume                     2066.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      air
_diffrn_ambient_temperature      293.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   30.0000 67

  2 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

  3 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000    0.0000 67

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   90.0000 74

  5 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -90.0000 88

  6 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  150.0000 94

  7 omega   40.00  135.00   1.0000    3.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 95

  8 omega   38.00   91.00   1.0000    3.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

  9 omega   40.00   98.00   1.0000    3.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 10 omega   87.00  178.00   1.0000    3.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 91

 11 omega  100.00  178.00   1.0000    3.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 78

 12 omega   81.00  176.00   1.0000    3.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 13 omega   90.00  175.00   1.0000    3.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 85

 14 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

 15 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

 16 omega   20.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -30.0000 69

 17 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -120.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0377809000
_diffrn_orient_matrix_UB_12      -0.0890125000
_diffrn_orient_matrix_UB_13      0.0633186000
_diffrn_orient_matrix_UB_21      0.0970130000
_diffrn_orient_matrix_UB_22      -0.0801843000
_diffrn_orient_matrix_UB_23      0.0150546000
_diffrn_orient_matrix_UB_31      0.0573449000
_diffrn_orient_matrix_UB_32      0.0774978000
_diffrn_orient_matrix_UB_33      0.0886978000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11754
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.697
_diffrn_reflns_theta_min         5.175
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0709
_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^)+(0.1298P)^2^+0.2810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1951
_refine_ls_wR_factor_ref         0.2150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3198
_reflns_number_total             4039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc00278b2.cif
_cod_data_source_block           lq-zx-180110a
_cod_depositor_comments
'Adding full bibliography for 1550819--1550820.cif.'
_cod_database_code               1550820
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C5(H5), C1(H1), C16(H16), C2(H2), C14(H14), C3(H3), C4(H4), C15(H15)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              73609
_olex2_date_sample_data_collection 2018-01-10
_olex2_submission_special_instructions 'No special instructions were received'