Synthesis of Bicyclo[3.1.0]hexanes by (3+2) Annulation of Cyclopropenes with Aminocyclopropanes
Muriel, Bastian; Gagnebin, Alec; Waser, Jerome; Chemical Science  (2019) –; doi:10.1039/C9SC03790J

data_1552391
_publ_section_title
;
 Synthesis of Bicyclo[3.1.0]hexanes by (3+2) Annulation of Cyclopropenes
 with Aminocyclopropanes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03790J
_journal_year                    2019
_chemical_formula_moiety         'C26 H31 N O4'
_chemical_formula_sum            'C26 H31 N O4'
_chemical_formula_weight         421.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-05 deposited with the CCDC.    2019-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.11470(19)
_cell_length_b                   12.70487(14)
_cell_length_c                   22.6264(2)
_cell_measurement_reflns_used    10757
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.4270
_cell_measurement_theta_min      4.7430
_cell_volume                     4632.42(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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   -113.00 -19.00   1.00   10.00    --  -43.01 -57.00  30.00   94
  2  \w   -122.00 -88.00   1.00   10.00    --  -43.01 -99.00-180.00   34
  3  \w   -123.00 -82.00   1.00   10.00    --  -43.01 -99.00 120.00   41
  4  \w    -87.00 -24.00   1.00   10.00    --  -43.01 125.00-120.00   63
  5  \w    -67.00  28.00   1.00   10.00    --  -43.01  57.00-180.00   95
  6  \w     86.00 151.00   1.00   40.00    --  105.68  45.00  60.00   65
  7  \w    148.00 174.00   1.00   40.00    --  105.68  30.00 -60.00   26
  8  \w     35.00 118.00   1.00   40.00    --  105.68-125.00-150.00   83
  9  \w     50.00 116.00   1.00   40.00    --  105.68-125.00 -30.00   66
 10  \w     98.00 138.00   1.00   40.00    --  105.68 -77.00 120.00   40
 11  \w     49.00  97.00   1.00   40.00    --  105.68-125.00 150.00   48
 12  \w     49.00  75.00   1.00   40.00    --  105.68 -77.00 120.00   26
 13  \w     49.00 138.00   1.00   40.00    --  105.68 -77.00 -60.00   89
 14  \w     80.00 176.00   1.00   40.00    --  105.68  77.00 -30.00   96
 15  \w     78.00 174.00   1.00   40.00    --  105.68  77.00   0.00   96
 16  \w     67.00 112.00   1.00   40.00    --  105.68-125.00  90.00   45
 17  \w     79.00 119.00   1.00   40.00    --  105.68  61.00 -90.00   40
 18  \w    141.00 174.00   1.00   40.00    --  105.68  61.00 -90.00   33
 19  \w     77.00 174.00   1.00   40.00    --  105.68  61.00  90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0097645000
_diffrn_orient_matrix_UB_12      -0.0038315000
_diffrn_orient_matrix_UB_13      0.0676931000
_diffrn_orient_matrix_UB_21      0.0894830000
_diffrn_orient_matrix_UB_22      -0.0406947000
_diffrn_orient_matrix_UB_23      -0.0072723000
_diffrn_orient_matrix_UB_31      0.0322070000
_diffrn_orient_matrix_UB_32      0.1141638000
_diffrn_orient_matrix_UB_33      -0.0003007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            33970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.601
_diffrn_reflns_theta_min         3.907
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics 
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       plate
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0481P)^2^+1.3873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3975
_reflns_number_total             4653
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03790j2.cif
_cod_data_source_block           bm3-459-pb
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1552391
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C26 H31 N1 O4'
_reflns_odcompleteness_completeness 99.94
_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 Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C)
;
_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 2.912
_oxdiff_exptl_absorpt_empirical_full_min 0.715