One-pot Crabb? homologation-radical cascade cyclisation with memory of chirality
Shovan Mondal; Malek Nechab; Nicolas Vanthuyne; Michele P. Bertrand; Chem.Commun. 48 (2012) 2549–; doi:10.1039/c2cc17830c

data_7107423
_publ_section_title
;
 One-pot Crabb? homologation-radical cascade cyclisation with memory of
 chirality
;
_journal_name_full               Chem.Commun.
_journal_page_first              2549
_journal_paper_doi               10.1039/c2cc17830c
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H17 N O3'
_chemical_formula_sum            'C18 H17 N O3'
_chemical_formula_weight         295.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.89431(12)
_cell_length_b                   8.01643(17)
_cell_length_c                   30.0923(6)
_cell_measurement_reflns_used    6983
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.3357
_cell_measurement_theta_min      5.5139
_cell_volume                     1421.90(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.0143
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1 omega -103.00 -36.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- -33.7678 -179.0000 -150.0000 67

2 omega -80.00 -43.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- -33.7678 -179.0000 -60.0000 37

3 omega -102.00 -32.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- -33.7678 179.0000 120.0000 70

4 omega 11.00 37.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- 33.7678 77.0000 -120.0000 26

5 omega 60.00 96.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- 33.7678 77.0000 -120.0000 36

6 omega 32.00 88.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -25.0000 -90.0000 56

7 omega 34.00 60.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -38.0000 90.0000 26

8 omega 74.00 99.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 38.0000 -30.0000 25

9 omega 57.00 109.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 -60.0000 52

10 omega 32.00 90.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -25.0000 150.0000 58

11 omega 113.00 142.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 -60.0000 29

12 omega 102.00 127.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 112.0000 0.0000 25

13 omega 142.00 169.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 112.0000 0.0000 27

14 omega 71.00 170.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 77.0000 -120.0000 99

15 omega 31.00 65.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -38.0000 120.0000 34

16 omega 113.00 162.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 51.0000 -60.0000 49

17 omega 76.00 112.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -112.0000 -120.0000 36

18 omega 48.00 74.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -38.0000 150.0000 26

19 omega 116.00 171.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 38.0000 -30.0000 55

20 omega -110.00 -32.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- -33.7678 179.0000 0.0000 78

21 omega 13.00 103.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- 33.7678 57.0000 -150.0000 90

22 omega 13.00 103.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- 33.7678 57.0000 0.0000 90

23 omega 13.00 103.00 1.0000 1.6500
omega____ theta____ kappa____ phi______ frames
- 33.7678 57.0000 120.0000 90

24 omega 70.00 140.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 77.0000 -150.0000 70

25 omega 28.00 138.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -92.0000 -60.0000 110

26 omega 70.00 170.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 77.0000 -180.0000 100

27 omega 77.00 167.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 64.0000 -30.0000 90

28 omega 74.00 172.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 38.0000 90.0000 98

29 omega 30.00 130.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -77.0000 60.0000 100

30 omega 70.00 170.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 77.0000 120.0000 100

31 omega 78.00 170.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 51.0000 30.0000 92

;
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2404766000
_diffrn_orient_matrix_UB_12      -0.0745119000
_diffrn_orient_matrix_UB_13      0.0028175000
_diffrn_orient_matrix_UB_21      0.0189325000
_diffrn_orient_matrix_UB_22      0.0058309000
_diffrn_orient_matrix_UB_23      -0.0510387000
_diffrn_orient_matrix_UB_31      0.1006769000
_diffrn_orient_matrix_UB_32      0.1770138000
_diffrn_orient_matrix_UB_33      0.0028856000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_sigmaI/netI    0.0917
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12903
_diffrn_reflns_theta_full        67.446
_diffrn_reflns_theta_max         67.446
_diffrn_reflns_theta_min         5.711
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details 'Flack (1983), 1023 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.03(18)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9910
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.0005291
_refine_ls_shift/su_mean         0.0000685
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.15P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0809
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0809
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              35
_reflns_limit_l_min              0
_reflns_number_gt                2488
_reflns_number_total             2544
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.43
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0324
_oxford_refine_ls_scale          9.9(4)
_oxford_reflns_number_all        2544
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c2cc17830c.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               7107423
_cell_oxdiff_length_a            5.8936(3)
_cell_oxdiff_length_b            8.0176(4)
_cell_oxdiff_length_c            30.0915(12)
_cell_oxdiff_angle_alpha         90.018(3)
_cell_oxdiff_angle_beta          90.009(3)
_cell_oxdiff_angle_gamma         90.015(4)
_cell_oxdiff_volume              1421.90(10)
_cell_oxdiff_measurement_reflns_used 6984
_montpellier_reflns_maxres       0.83
_montpellier_reflns_completeness_maxres 99.68
_montpellier_reflns_redundancy_maxres 8.39
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT ENANTIO
RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S)
RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S)
RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S)
RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
RIDE C ( 17,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S)
RIDE C ( 20,X'S) H ( 201,X'S)
RIDE C ( 21,X'S) H ( 211,X'S)
RIDE C ( 22,X'S) H ( 221,X'S) H ( 222,X'S) H ( 223,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;