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_1550819
_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         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_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     direct
_audit_creation_date             2018-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-21 deposited with the CCDC.    2019-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.877(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5364(3)
_cell_length_b                   20.5621(11)
_cell_length_c                   11.4782(5)
_cell_measurement_reflns_used    2194
_cell_measurement_temperature    295.3(4)
_cell_measurement_theta_max      70.8040
_cell_measurement_theta_min      4.2950
_cell_volume                     1772.27(14)
_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_environment      air
_diffrn_ambient_temperature      295.3(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.952
_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    -66.00  35.00   1.00    1.69    --  -36.42  19.00-180.00  101
  2  \w   -106.00 -18.00   1.00    1.69    --  -36.42 -38.00   0.00   88
  3  \w     18.00 106.00   1.00    1.69    --   36.42  38.00-120.00   88
  4  \w      1.00  75.00   1.00    1.69    --   36.42 -99.00 120.00   74
  5  \w     21.00  88.00   1.00    1.69    --   36.42-122.00  35.00   67
  6  \w     39.00 109.00   1.00    6.76    --  108.71 -94.00  30.00   70
  7  \w     39.00 109.00   1.00    6.76    --  108.71 -94.00 150.00   70
  8  \w    100.00 178.00   1.00    6.76    --  108.71 111.00  30.00   78
  9  \w     82.00 176.00   1.00    6.76    --  108.71  77.00 120.00   94
 10  \w     39.00 130.00   1.00    6.76    --  108.71 -30.00  30.00   91
 11  \w     39.00 130.00   1.00    6.76    --  108.71 -30.00 -60.00   91
 12  \w     39.00 109.00   1.00    6.76    --  108.71 -94.00 -60.00   70
 13  \w     41.00 135.00   1.00    6.76    --  108.71 -77.00  30.00   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_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0983911000
_diffrn_orient_matrix_UB_12      0.0179863000
_diffrn_orient_matrix_UB_13      0.1078310000
_diffrn_orient_matrix_UB_21      0.0080751000
_diffrn_orient_matrix_UB_22      0.0724420000
_diffrn_orient_matrix_UB_23      -0.0334405000
_diffrn_orient_matrix_UB_31      -0.1798113000
_diffrn_orient_matrix_UB_32      -0.0065621000
_diffrn_orient_matrix_UB_33      -0.0734763000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9024
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.208
_diffrn_reflns_theta_min         4.300
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0568
_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^)+(0.1036P)^2^+0.1648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2515
_reflns_number_total             3393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc00278b2.cif
_cod_data_source_block           ljl-zx-181113
_cod_depositor_comments
'Adding full bibliography for 1550819--1550820.cif.'
_cod_original_cell_volume        1772.25(14)
_cod_database_code               1550819
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 98.37
_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. Rigid bond restraints
 C16, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Others
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=1-FVAR(2)
 Sof(C14)=Sof(H14A)=Sof(H14B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C13(H13A,H13B)
4.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C4(H4), C23(H23), C7(H7), C21(H21), C6(H6), C22(H22), C5(H5),
 C20(H20)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              23343
_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 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.850