#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024821.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_4024821
loop_
_publ_author_name
'Christopher W. Bond'
'Alexander J. Cresswell'
'Stephen G. Davies'
'Ai M. Fletcher'
'Wataru Kurosawa'
'James A. Lee'
'Paul M. Roberts'
'Angela J. Russell'
'Andrew D. Smith'
'James E. Thomson'
_publ_contact_author_address
;Department of Chemistry
Chemistry Research laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_name        'Stephen G. Davies'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6735
_journal_page_last               6748
_journal_paper_doi               10.1021/jo9012783
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C23 H29 N1 O3'
_chemical_formula_sum            'C23 H29 N O3'
_chemical_formula_weight         367.49
_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
_audit_creation_date             09-02-24
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                96.357(3)
_cell_angle_beta                 93.842(2)
_cell_angle_gamma                103.221(3)
_cell_formula_units_Z            2
_cell_length_a                   6.1629(4)
_cell_length_b                   10.0202(7)
_cell_length_c                   16.9326(13)
_cell_measurement_reflns_used    2920
_cell_measurement_temperature    150
_cell_measurement_theta_max      26
_cell_measurement_theta_min      5
_cell_volume                     1007.06(12)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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    'USER DEFINED STRUCTURE SOLUTION'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6269
_diffrn_reflns_theta_full        25.261
_diffrn_reflns_theta_max         26.313
_diffrn_reflns_theta_min         5.134
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.000175
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.878 0.259 0.564 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0776
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0490
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2525
_reflns_number_total             3963
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0499
_oxford_refine_ls_scale          0.8721(19)
_oxford_reflns_number_all        3963
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_oxford_structure_analysis_title '2241520 SGD231'
_cod_data_source_file            jo9012783_si_016.cif
_cod_data_source_block           1
_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_original_formula_sum        'C23 H29 N1 O3'
_cod_database_code               4024821
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.5467(2) 0.34221(15) 0.28798(9) 0.0370 1.0000 Uani . . . . . . .
C2 C 0.4898(3) 0.4447(2) 0.24429(12) 0.0320 1.0000 Uani . . . . . . .
C3 C 0.3162(3) 0.5116(2) 0.28413(12) 0.0294 1.0000 Uani . . . . . . .
C4 C 0.1054(3) 0.4066(2) 0.29948(12) 0.0288 1.0000 Uani . . . . . . .
N5 N 0.1512(3) 0.31284(16) 0.35721(9) 0.0269 1.0000 Uani . . . . . . .
C6 C -0.0378(3) 0.1899(2) 0.35078(12) 0.0286 1.0000 Uani . . . . . . .
C7 C -0.0515(3) 0.09215(19) 0.27547(11) 0.0263 1.0000 Uani . . . . . . .
C8 C 0.1270(3) 0.0324(2) 0.25896(12) 0.0320 1.0000 Uani . . . . . . .
C9 C 0.1121(4) -0.0619(2) 0.19165(14) 0.0378 1.0000 Uani . . . . . . .
C10 C -0.0814(4) -0.0995(2) 0.13992(14) 0.0408 1.0000 Uani . . . . . . .
C11 C -0.2590(4) -0.0420(2) 0.15554(13) 0.0401 1.0000 Uani . . . . . . .
C12 C -0.2435(3) 0.0545(2) 0.22253(12) 0.0321 1.0000 Uani . . . . . . .
C13 C 0.1851(3) 0.3850(2) 0.43968(12) 0.0316 1.0000 Uani . . . . . . .
C14 C 0.2680(3) 0.30133(19) 0.49895(11) 0.0286 1.0000 Uani . . . . . . .
C15 C 0.4545(3) 0.2483(2) 0.48685(12) 0.0331 1.0000 Uani . . . . . . .
C16 C 0.5273(4) 0.1696(2) 0.54059(13) 0.0388 1.0000 Uani . . . . . . .
C17 C 0.4152(4) 0.1435(2) 0.60755(14) 0.0404 1.0000 Uani . . . . . . .
C18 C 0.2335(4) 0.1981(2) 0.62134(13) 0.0406 1.0000 Uani . . . . . . .
C19 C 0.1603(3) 0.2765(2) 0.56721(12) 0.0348 1.0000 Uani . . . . . . .
C20 C 0.2552(4) 0.6183(2) 0.23351(13) 0.0382 1.0000 Uani . . . . . . .
C21 C 0.1708(4) 0.5550(2) 0.14763(13) 0.0432 1.0000 Uani . . . . . . .
C22 C 0.3488(4) 0.4928(3) 0.10920(13) 0.0446 1.0000 Uani . . . . . . .
C23 C 0.4119(3) 0.3858(2) 0.15768(12) 0.0350 1.0000 Uani . . . . . . .
O24 O 0.6015(2) 0.34244(16) 0.12481(9) 0.0422 1.0000 Uani . . . . . . .
C25 C 0.5557(4) 0.2350(3) 0.06621(13) 0.0432 1.0000 Uani . . . . . . .
O26 O 0.3705(3) 0.1702(2) 0.04260(12) 0.0705 1.0000 Uani . . . . . . .
C27 C 0.7673(4) 0.2098(3) 0.03499(15) 0.0512 1.0000 Uani . . . . . . .
H21 H 0.6306 0.5192 0.2440 0.0402 1.0000 Uiso R . . . . . .
H31 H 0.3912 0.5623 0.3383 0.0383 1.0000 Uiso R . . . . . .
H41 H -0.0050 0.4574 0.3200 0.0368 1.0000 Uiso R . . . . . .
H42 H 0.0380 0.3466 0.2474 0.0370 1.0000 Uiso R . . . . . .
H62 H -0.0146 0.1404 0.3976 0.0353 1.0000 Uiso R . . . . . .
H61 H -0.1818 0.2203 0.3532 0.0346 1.0000 Uiso R . . . . . .
H81 H 0.2630 0.0575 0.2958 0.0413 1.0000 Uiso R . . . . . .
H91 H 0.2359 -0.1029 0.1803 0.0472 1.0000 Uiso R . . . . . .
H101 H -0.0920 -0.1653 0.0935 0.0495 1.0000 Uiso R . . . . . .
H111 H -0.3944 -0.0680 0.1192 0.0496 1.0000 Uiso R . . . . . .
H121 H -0.3677 0.0978 0.2330 0.0395 1.0000 Uiso R . . . . . .
H132 H 0.3022 0.4729 0.4406 0.0410 1.0000 Uiso R . . . . . .
H131 H 0.0416 0.4085 0.4560 0.0412 1.0000 Uiso R . . . . . .
H151 H 0.5318 0.2667 0.4401 0.0414 1.0000 Uiso R . . . . . .
H161 H 0.6570 0.1322 0.5308 0.0455 1.0000 Uiso R . . . . . .
H171 H 0.4658 0.0867 0.6444 0.0498 1.0000 Uiso R . . . . . .
H181 H 0.1544 0.1798 0.6685 0.0491 1.0000 Uiso R . . . . . .
H191 H 0.0323 0.3147 0.5764 0.0413 1.0000 Uiso R . . . . . .
H202 H 0.3944 0.6947 0.2332 0.0490 1.0000 Uiso R . . . . . .
H201 H 0.1338 0.6582 0.2587 0.0479 1.0000 Uiso R . . . . . .
H211 H 0.1443 0.6308 0.1172 0.0549 1.0000 Uiso R . . . . . .
H212 H 0.0291 0.4790 0.1468 0.0555 1.0000 Uiso R . . . . . .
H222 H 0.4871 0.5668 0.1101 0.0572 1.0000 Uiso R . . . . . .
H221 H 0.2958 0.4477 0.0543 0.0577 1.0000 Uiso R . . . . . .
H231 H 0.2818 0.3028 0.1545 0.0445 1.0000 Uiso R . . . . . .
H272 H 0.7345 0.1195 0.0016 0.0832 1.0000 Uiso R . . . . . .
H271 H 0.8246 0.2841 0.0034 0.0836 1.0000 Uiso R . . . . . .
H273 H 0.8775 0.2125 0.0799 0.0832 1.0000 Uiso R . . . . . .
H11 H 0.4224 0.3083 0.3092 0.0596 1.0000 Uiso R . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . H11 . 103.4 no
O1 . C2 . C3 . 111.72(16) yes
O1 . C2 . C23 . 110.92(16) yes
C3 . C2 . C23 . 111.86(16) yes
O1 . C2 . H21 . 107.3 no
C3 . C2 . H21 . 107.8 no
C23 . C2 . H21 . 106.9 no
C2 . C3 . C4 . 113.42(16) yes
C2 . C3 . C20 . 109.73(16) yes
C4 . C3 . C20 . 110.68(17) yes
C2 . C3 . H31 . 106.9 no
C4 . C3 . H31 . 107.5 no
C20 . C3 . H31 . 108.5 no
C3 . C4 . N5 . 112.93(16) yes
C3 . C4 . H41 . 108.9 no
N5 . C4 . H41 . 109.4 no
C3 . C4 . H42 . 109.2 no
N5 . C4 . H42 . 107.3 no
H41 . C4 . H42 . 109.2 no
C4 . N5 . C6 . 110.02(15) yes
C4 . N5 . C13 . 110.51(15) yes
C6 . N5 . C13 . 109.37(14) yes
N5 . C6 . C7 . 113.12(15) yes
N5 . C6 . H62 . 107.0 no
C7 . C6 . H62 . 108.7 no
N5 . C6 . H61 . 109.4 no
C7 . C6 . H61 . 109.2 no
H62 . C6 . H61 . 109.4 no
C6 . C7 . C8 . 120.36(17) yes
C6 . C7 . C12 . 121.26(16) yes
C8 . C7 . C12 . 118.32(17) yes
C7 . C8 . C9 . 120.70(19) yes
C7 . C8 . H81 . 119.3 no
C9 . C8 . H81 . 120.0 no
C8 . C9 . C10 . 120.28(19) yes
C8 . C9 . H91 . 120.5 no
C10 . C9 . H91 . 119.2 no
C9 . C10 . C11 . 119.7(2) yes
C9 . C10 . H101 . 120.2 no
C11 . C10 . H101 . 120.1 no
C10 . C11 . C12 . 120.2(2) yes
C10 . C11 . H111 . 119.7 no
C12 . C11 . H111 . 120.1 no
C11 . C12 . C7 . 120.76(18) yes
C11 . C12 . H121 . 120.5 no
C7 . C12 . H121 . 118.7 no
N5 . C13 . C14 . 112.20(15) yes
N5 . C13 . H132 . 107.4 no
C14 . C13 . H132 . 107.9 no
N5 . C13 . H131 . 110.6 no
C14 . C13 . H131 . 109.9 no
H132 . C13 . H131 . 108.9 no
C13 . C14 . C15 . 120.93(18) yes
C13 . C14 . C19 . 120.67(18) yes
C15 . C14 . C19 . 118.40(19) yes
C14 . C15 . C16 . 120.69(19) yes
C14 . C15 . H151 . 118.8 no
C16 . C15 . H151 . 120.5 no
C15 . C16 . C17 . 120.1(2) yes
C15 . C16 . H161 . 119.6 no
C17 . C16 . H161 . 120.3 no
C16 . C17 . C18 . 119.9(2) yes
C16 . C17 . H171 . 119.6 no
C18 . C17 . H171 . 120.6 no
C17 . C18 . C19 . 119.9(2) yes
C17 . C18 . H181 . 119.9 no
C19 . C18 . H181 . 120.2 no
C14 . C19 . C18 . 121.0(2) yes
C14 . C19 . H191 . 118.7 no
C18 . C19 . H191 . 120.2 no
C3 . C20 . C21 . 112.09(17) yes
C3 . C20 . H202 . 108.0 no
C21 . C20 . H202 . 109.0 no
C3 . C20 . H201 . 109.2 no
C21 . C20 . H201 . 109.1 no
H202 . C20 . H201 . 109.5 no
C20 . C21 . C22 . 109.92(19) yes
C20 . C21 . H211 . 107.9 no
C22 . C21 . H211 . 108.4 no
C20 . C21 . H212 . 110.0 no
C22 . C21 . H212 . 108.8 no
H211 . C21 . H212 . 111.8 no
C21 . C22 . C23 . 110.67(18) yes
C21 . C22 . H222 . 108.8 no
C23 . C22 . H222 . 106.2 no
C21 . C22 . H221 . 111.5 no
C23 . C22 . H221 . 108.4 no
H222 . C22 . H221 . 111.2 no
C22 . C23 . C2 . 112.31(18) yes
C22 . C23 . O24 . 108.70(17) yes
C2 . C23 . O24 . 105.99(16) yes
C22 . C23 . H231 . 110.1 no
C2 . C23 . H231 . 110.5 no
O24 . C23 . H231 . 109.1 no
C23 . O24 . C25 . 117.39(17) yes
O24 . C25 . O26 . 123.7(2) yes
O24 . C25 . C27 . 110.9(2) yes
O26 . C25 . C27 . 125.4(2) yes
C25 . C27 . H272 . 109.6 no
C25 . C27 . H271 . 107.5 no
H272 . C27 . H271 . 110.4 no
C25 . C27 . H273 . 109.4 no
H272 . C27 . H273 . 110.5 no
H271 . C27 . H273 . 109.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.422(2) yes
O1 . H11 . 0.881 no
C2 . C3 . 1.541(3) yes
C2 . C23 . 1.521(3) yes
C2 . H21 . 1.008 no
C3 . C4 . 1.531(3) yes
C3 . C20 . 1.536(3) yes
C3 . H31 . 1.023 no
C4 . N5 . 1.485(3) yes
C4 . H41 . 0.997 no
C4 . H42 . 1.015 no
N5 . C6 . 1.478(2) yes
N5 . C13 . 1.478(2) yes
C6 . C7 . 1.505(3) yes
C6 . H62 . 1.000 no
C6 . H61 . 1.003 no
C7 . C8 . 1.397(3) yes
C7 . C12 . 1.387(3) yes
C8 . C9 . 1.381(3) yes
C8 . H81 . 0.977 no
C9 . C10 . 1.383(3) yes
C9 . H91 . 0.966 no
C10 . C11 . 1.377(3) yes
C10 . H101 . 0.957 no
C11 . C12 . 1.389(3) yes
C11 . H111 . 0.969 no
C12 . H121 . 0.979 no
C13 . C14 . 1.512(3) yes
C13 . H132 . 1.001 no
C13 . H131 . 1.013 no
C14 . C15 . 1.390(3) yes
C14 . C19 . 1.389(3) yes
C15 . C16 . 1.384(3) yes
C15 . H151 . 0.964 no
C16 . C17 . 1.385(3) yes
C16 . H161 . 0.974 no
C17 . C18 . 1.376(3) yes
C17 . H171 . 0.971 no
C18 . C19 . 1.388(3) yes
C18 . H181 . 0.976 no
C19 . H191 . 0.967 no
C20 . C21 . 1.527(3) yes
C20 . H202 . 1.012 no
C20 . H201 . 1.022 no
C21 . C22 . 1.527(3) yes
C21 . H211 . 1.000 no
C21 . H212 . 1.017 no
C22 . C23 . 1.522(3) yes
C22 . H222 . 0.992 no
C22 . H221 . 0.986 no
C23 . O24 . 1.459(2) yes
C23 . H231 . 1.008 no
O24 . C25 . 1.346(3) yes
C25 . O26 . 1.195(3) yes
C25 . C27 . 1.502(3) yes
C27 . H272 . 0.983 no
C27 . H271 . 0.979 no
C27 . H273 . 0.979 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H61 . O1 1_455 147 1.00 2.55 3.435(3) yes
O1 . H11 . C4 . 122 0.88 2.38 2.949(3) yes
O1 . H11 . N5 . 156 0.88 1.91 2.744(3) yes
