#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024470.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024470
loop_
_publ_author_name
'Sylvaine Cren'
'Pascal Schär'
'Philippe Renaud'
'Kurt Schenk'
_publ_section_title
;
Diastereoselectivity Control of the Radical Carboazidation of Substituted
Methylenecyclohexanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2942
_journal_page_last               2946
_journal_paper_doi               10.1021/jo900088x
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C15 H27 N O'
_chemical_formula_sum            'C15 H27 N O'
_chemical_formula_weight         237.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Kurt J. Schenk'
_audit_contact_author_address
;
   Kurt J. Schenk
   LCr1 - IPMC - FSB - EPFL
   Le Cubtron, Bureau 521
   Dorigny
   CH-1015 Lausanne
;
_audit_contact_author_email      Kurt.Schenk@EPFL.CH
_audit_contact_author_fax        '+41 (0)21 693 0504'
_audit_contact_author_phone      '+41 (0)21 693 0635'
_audit_creation_date             '2nd February 2008'
_audit_creation_method           'SHELXL-97 & Stoe X-Red'
_cell_angle_alpha                99.079(15)
_cell_angle_beta                 103.830(14)
_cell_angle_gamma                94.188(14)
_cell_formula_units_Z            2
_cell_length_a                   6.7541(12)
_cell_length_b                   9.6011(17)
_cell_length_c                   11.854(2)
_cell_measurement_reflns_used    15928
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      29.53
_cell_measurement_theta_min      2.16
_cell_volume                     732.1(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'SHELXtl (Bruker, 1996)'
_computing_publication_material  'SHELXtl (Bruker, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.892
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_details      ' 180 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6921
_diffrn_reflns_theta_full        29.36
_diffrn_reflns_theta_max         29.36
_diffrn_reflns_theta_min         2.16
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.20
_diffrn_source_voltage           55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Stoe, X_Red32, Version 1.31 (2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepipipede
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.364
_exptl_crystal_size_min          0.342
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.1981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1684
_reflns_number_gt                2870
_reflns_number_total             3598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900088x_si_002.cif
_cod_data_source_block           SC5k
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024470
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2808(2) -0.13202(13) 0.48835(10) 0.0625(4) Uani 1 1 d . . .
N1 N 0.42038(19) 0.05676(13) 0.63729(10) 0.0431(3) Uani 1 1 d . . .
H1N H 0.5247 0.0810 0.6120 0.052 Uiso 1 1 calc R . .
C2 C 0.2854(2) -0.05714(16) 0.58350(13) 0.0461(4) Uani 1 1 d . . .
C3 C 0.1368(3) -0.0770(2) 0.65767(15) 0.0584(5) Uani 1 1 d . . .
H3A H 0.1229 -0.1743 0.6700 0.070 Uiso 1 1 calc R . .
H3B H 0.0027 -0.0528 0.6205 0.070 Uiso 1 1 calc R . .
C4 C 0.2321(3) 0.02436(19) 0.77399(15) 0.0560(4) Uani 1 1 d . . .
H4A H 0.3089 -0.0256 0.8320 0.067 Uiso 1 1 calc R . .
H4B H 0.1268 0.0682 0.8053 0.067 Uiso 1 1 calc R . .
C5 C 0.3764(2) 0.13745(16) 0.74337(12) 0.0420(3) Uani 1 1 d . . .
C6 C 0.5776(2) 0.19243(16) 0.84169(12) 0.0430(3) Uani 1 1 d . . .
C7 C 0.7025(2) 0.30955(15) 0.80389(12) 0.0426(3) Uani 1 1 d . . .
H7A H 0.8222 0.3464 0.8684 0.051 Uiso 1 1 calc R . .
H7B H 0.7510 0.2667 0.7373 0.051 Uiso 1 1 calc R . .
C8 C 0.5877(3) 0.43413(15) 0.76943(12) 0.0456(4) Uani 1 1 d . . .
H8 H 0.5414 0.4758 0.8383 0.055 Uiso 1 1 calc R . .
C9 C 0.3934(3) 0.37415(18) 0.67099(14) 0.0522(4) Uani 1 1 d . . .
H9A H 0.3134 0.4509 0.6515 0.063 Uiso 1 1 calc R . .
H9B H 0.4324 0.3319 0.6008 0.063 Uiso 1 1 calc R . .
C10 C 0.2620(3) 0.26246(19) 0.70836(15) 0.0520(4) Uani 1 1 d . . .
H10A H 0.1422 0.2265 0.6437 0.062 Uiso 1 1 calc R . .
H10B H 0.2145 0.3072 0.7748 0.062 Uiso 1 1 calc R . .
C11 C 0.7124(3) 0.0738(2) 0.86471(17) 0.0593(5) Uani 1 1 d . . .
H11A H 0.7489 0.0356 0.7936 0.089 Uiso 1 1 calc R . .
H11B H 0.6384 0.0001 0.8895 0.089 Uiso 1 1 calc R . .
H11C H 0.8347 0.1112 0.9256 0.089 Uiso 1 1 calc R . .
C12 C 0.5232(3) 0.2513(2) 0.95804(14) 0.0632(5) Uani 1 1 d . . .
H12A H 0.6469 0.2890 1.0177 0.095 Uiso 1 1 calc R . .
H12B H 0.4524 0.1763 0.9832 0.095 Uiso 1 1 calc R . .
H12C H 0.4365 0.3253 0.9455 0.095 Uiso 1 1 calc R . .
C13 C 0.7232(3) 0.55512(16) 0.74013(14) 0.0534(4) Uani 1 1 d . . .
C14 C 0.9041(4) 0.6135(3) 0.84717(19) 0.0867(8) Uani 1 1 d . . .
H14A H 0.9735 0.6980 0.8339 0.130 Uiso 1 1 calc R . .
H14B H 0.9981 0.5435 0.8582 0.130 Uiso 1 1 calc R . .
H14C H 0.8541 0.6356 0.9164 0.130 Uiso 1 1 calc R . .
C15 C 0.5963(4) 0.67724(19) 0.7133(2) 0.0804(7) Uani 1 1 d . . .
H15A H 0.6850 0.7574 0.7079 0.121 Uiso 1 1 calc R . .
H15B H 0.5301 0.7034 0.7755 0.121 Uiso 1 1 calc R . .
H15C H 0.4944 0.6475 0.6397 0.121 Uiso 1 1 calc R . .
C16 C 0.8081(3) 0.5040(2) 0.63358(16) 0.0632(5) Uani 1 1 d . . .
H16A H 0.8901 0.5816 0.6186 0.095 Uiso 1 1 calc R . .
H16B H 0.6961 0.4695 0.5654 0.095 Uiso 1 1 calc R . .
H16C H 0.8910 0.4290 0.6501 0.095 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.1970
1 0 0 0.2570
0 0 1 0.1810
0 0 -1 0.1830
0 -1 1 0.1440
0 1 -1 0.1980
0 1 0 0.2870
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 114.75(12) . . ?
C2 N1 H1N 122.6 . . ?
C5 N1 H1N 122.6 . . ?
O1 C2 N1 125.90(14) . . ?
O1 C2 C3 125.52(14) . . ?
N1 C2 C3 108.57(13) . . ?
C2 C3 C4 104.24(13) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 105.14(12) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C10 108.65(12) . . ?
N1 C5 C4 100.76(11) . . ?
C10 C5 C4 110.90(14) . . ?
N1 C5 C6 111.22(12) . . ?
C10 C5 C6 110.22(12) . . ?
C4 C5 C6 114.64(12) . . ?
C11 C6 C7 107.95(13) . . ?
C11 C6 C12 107.86(14) . . ?
C7 C6 C12 110.11(13) . . ?
C11 C6 C5 111.63(13) . . ?
C7 C6 C5 109.82(11) . . ?
C12 C6 C5 109.42(13) . . ?
C8 C7 C6 115.64(13) . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C7 C8 C9 108.01(12) . . ?
C7 C8 C13 114.07(14) . . ?
C9 C8 C13 114.31(13) . . ?
C7 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C13 C8 H8 106.6 . . ?
C10 C9 C8 111.47(13) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C5 113.38(13) . . ?
C9 C10 H10A 108.9 . . ?
C5 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C5 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C14 107.77(16) . . ?
C15 C13 C16 108.62(16) . . ?
C14 C13 C16 108.63(19) . . ?
C15 C13 C8 109.66(17) . . ?
C14 C13 C8 109.80(14) . . ?
C16 C13 C8 112.25(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2306(18) . ?
N1 C2 1.3381(18) . ?
N1 C5 1.4747(17) . ?
N1 H1N 0.8600 . ?
C2 C3 1.504(2) . ?
C3 C4 1.524(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.549(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.532(2) . ?
C5 C6 1.558(2) . ?
C6 C11 1.527(2) . ?
C6 C7 1.542(2) . ?
C6 C12 1.544(2) . ?
C7 C8 1.529(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.536(2) . ?
C8 C13 1.560(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.527(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C15 1.531(3) . ?
C13 C14 1.534(3) . ?
C13 C16 1.535(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.86 2.05 2.8943(17) 165.5 2_656
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 O1 172.96(17) . . . . ?
C5 N1 C2 C3 -5.9(2) . . . . ?
O1 C2 C3 C4 170.04(18) . . . . ?
N1 C2 C3 C4 -11.1(2) . . . . ?
C2 C3 C4 C5 22.5(2) . . . . ?
C2 N1 C5 C10 -96.83(16) . . . . ?
C2 N1 C5 C4 19.74(17) . . . . ?
C2 N1 C5 C6 141.67(14) . . . . ?
C3 C4 C5 N1 -24.88(17) . . . . ?
C3 C4 C5 C10 90.02(17) . . . . ?
C3 C4 C5 C6 -144.39(15) . . . . ?
N1 C5 C6 C11 -50.22(16) . . . . ?
C10 C5 C6 C11 -170.79(13) . . . . ?
C4 C5 C6 C11 63.26(17) . . . . ?
N1 C5 C6 C7 69.47(15) . . . . ?
C10 C5 C6 C7 -51.10(16) . . . . ?
C4 C5 C6 C7 -177.05(13) . . . . ?
N1 C5 C6 C12 -169.55(13) . . . . ?
C10 C5 C6 C12 69.88(16) . . . . ?
C4 C5 C6 C12 -56.07(18) . . . . ?
C11 C6 C7 C8 176.37(12) . . . . ?
C12 C6 C7 C8 -66.11(16) . . . . ?
C5 C6 C7 C8 54.45(16) . . . . ?
C6 C7 C8 C9 -55.71(16) . . . . ?
C6 C7 C8 C13 176.02(11) . . . . ?
C7 C8 C9 C10 55.16(17) . . . . ?
C13 C8 C9 C10 -176.70(14) . . . . ?
C8 C9 C10 C5 -57.90(18) . . . . ?
N1 C5 C10 C9 -67.18(16) . . . . ?
C4 C5 C10 C9 -177.04(12) . . . . ?
C6 C5 C10 C9 54.93(16) . . . . ?
C7 C8 C13 C15 -177.04(13) . . . . ?
C9 C8 C13 C15 57.97(18) . . . . ?
C7 C8 C13 C14 -58.8(2) . . . . ?
C9 C8 C13 C14 176.21(17) . . . . ?
C7 C8 C13 C16 62.13(18) . . . . ?
C9 C8 C13 C16 -62.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24539745
