#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024822.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_4024822
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
University of Oxford
Chemistry Research laboratory
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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-03-16
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 98.2573(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7731(2)
_cell_length_b                   22.3043(6)
_cell_length_c                   10.5826(3)
_cell_measurement_reflns_used    4469
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2049.31(9)
_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 0.989
_diffrn_measured_fraction_theta_max 0.986
_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  0.046
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8654
_diffrn_reflns_theta_full        25.547
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         5.138
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1234
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000364
_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: 
 0.321 0.144 0.977E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1124
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0481
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2632
_reflns_number_total             4631
_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   0.0451
_oxford_refine_ls_scale          0.3635(7)
_oxford_reflns_number_all        4631
_oxford_reflns_threshold_expression_ref I>2.5\s(I)
_oxford_structure_analysis_title '3161656 SGD236'
_cod_data_source_file            jo9012783_si_017.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 21/a 1 '
_cod_original_formula_sum        'C23 H29 N1 O3'
_cod_database_code               4024822
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z
x+1/2,-y+1/2,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 0.37627(16) 0.49823(7) 0.83866(14) 0.0421 1.0000 Uani . . . . . . .
C2 C 0.4232(2) 0.49827(9) 0.7363(2) 0.0353 1.0000 Uani . . . . . . .
O3 O 0.57317(15) 0.49583(6) 0.72410(13) 0.0356 1.0000 Uani . . . . . . .
C4 C 0.6845(2) 0.49203(9) 0.84203(19) 0.0331 1.0000 Uani . . . . . . .
C5 C 0.8237(2) 0.45782(9) 0.8088(2) 0.0339 1.0000 Uani . . . . . . .
C6 C 0.7804(2) 0.39452(10) 0.7607(2) 0.0362 1.0000 Uani . . . . . . .
N7 N 0.73064(19) 0.35627(8) 0.86032(17) 0.0361 1.0000 Uani . . . . . . .
C8 C 0.6439(2) 0.30373(10) 0.8047(2) 0.0416 1.0000 Uani . . . . . . .
C9 C 0.4847(2) 0.31951(10) 0.7386(2) 0.0386 1.0000 Uani . . . . . . .
C10 C 0.3745(2) 0.34298(10) 0.8082(2) 0.0411 1.0000 Uani . . . . . . .
C11 C 0.2269(2) 0.35536(11) 0.7498(2) 0.0441 1.0000 Uani . . . . . . .
C12 C 0.1851(3) 0.34506(10) 0.6201(2) 0.0443 1.0000 Uani . . . . . . .
C13 C 0.2932(3) 0.32248(10) 0.5499(2) 0.0448 1.0000 Uani . . . . . . .
C14 C 0.4412(3) 0.30941(10) 0.6088(2) 0.0436 1.0000 Uani . . . . . . .
C15 C 0.8627(2) 0.33611(10) 0.9519(2) 0.0381 1.0000 Uani . . . . . . .
C16 C 0.8213(2) 0.32295(9) 1.0826(2) 0.0380 1.0000 Uani . . . . . . .
C17 C 0.7038(2) 0.35357(10) 1.1304(2) 0.0403 1.0000 Uani . . . . . . .
C18 C 0.6780(3) 0.34536(10) 1.2554(2) 0.0454 1.0000 Uani . . . . . . .
C19 C 0.7695(3) 0.30668(12) 1.3357(2) 0.0522 1.0000 Uani . . . . . . .
C20 C 0.8856(3) 0.27547(12) 1.2886(3) 0.0581 1.0000 Uani . . . . . . .
C21 C 0.9107(3) 0.28291(11) 1.1632(2) 0.0491 1.0000 Uani . . . . . . .
C22 C 0.9069(2) 0.49297(10) 0.7145(2) 0.0393 1.0000 Uani . . . . . . .
C23 C 0.9480(2) 0.55614(10) 0.7627(2) 0.0426 1.0000 Uani . . . . . . .
C24 C 0.8059(3) 0.58983(10) 0.7925(2) 0.0429 1.0000 Uani . . . . . . .
C25 C 0.7230(2) 0.55585(10) 0.8864(2) 0.0374 1.0000 Uani . . . . . . .
O26 O 0.82204(16) 0.55424(7) 1.00642(14) 0.0419 1.0000 Uani . . . . . . .
C27 C 0.3256(2) 0.50107(11) 0.6093(2) 0.0436 1.0000 Uani . . . . . . .
H41 H 0.6348 0.4703 0.9085 0.0413 1.0000 Uiso R . . . . . .
H51 H 0.8979 0.4543 0.8912 0.0425 1.0000 Uiso R . . . . . .
H62 H 0.8724 0.3749 0.7305 0.0463 1.0000 Uiso R . . . . . .
H61 H 0.6902 0.3976 0.6888 0.0455 1.0000 Uiso R . . . . . .
H82 H 0.6334 0.2754 0.8771 0.0510 1.0000 Uiso R . . . . . .
H81 H 0.7048 0.2834 0.7418 0.0509 1.0000 Uiso R . . . . . .
H101 H 0.4056 0.3503 0.8990 0.0532 1.0000 Uiso R . . . . . .
H111 H 0.1506 0.3713 0.7991 0.0555 1.0000 Uiso R . . . . . .
H121 H 0.0817 0.3532 0.5790 0.0524 1.0000 Uiso R . . . . . .
H131 H 0.2651 0.3154 0.4592 0.0559 1.0000 Uiso R . . . . . .
H141 H 0.5176 0.2934 0.5596 0.0539 1.0000 Uiso R . . . . . .
H152 H 0.9421 0.3686 0.9640 0.0471 1.0000 Uiso R . . . . . .
H151 H 0.9086 0.2991 0.9177 0.0477 1.0000 Uiso R . . . . . .
H171 H 0.6394 0.3808 1.0736 0.0510 1.0000 Uiso R . . . . . .
H181 H 0.5950 0.3668 1.2868 0.0567 1.0000 Uiso R . . . . . .
H191 H 0.7525 0.3018 1.4235 0.0640 1.0000 Uiso R . . . . . .
H201 H 0.9507 0.2484 1.3436 0.0705 1.0000 Uiso R . . . . . .
H211 H 0.9912 0.2607 1.1304 0.0597 1.0000 Uiso R . . . . . .
H222 H 1.0044 0.4720 0.7028 0.0485 1.0000 Uiso R . . . . . .
H221 H 0.8357 0.4961 0.6299 0.0480 1.0000 Uiso R . . . . . .
H231 H 1.0230 0.5526 0.8441 0.0522 1.0000 Uiso R . . . . . .
H232 H 0.9973 0.5790 0.6979 0.0527 1.0000 Uiso R . . . . . .
H242 H 0.8343 0.6303 0.8266 0.0534 1.0000 Uiso R . . . . . .
H241 H 0.7316 0.5939 0.7110 0.0533 1.0000 Uiso R . . . . . .
H251 H 0.6236 0.5772 0.8973 0.0462 1.0000 Uiso R . . . . . .
H272 H 0.3764 0.5249 0.5506 0.0678 1.0000 Uiso R . . . . . .
H271 H 0.2264 0.5191 0.6201 0.0679 1.0000 Uiso R . . . . . .
H273 H 0.3082 0.4603 0.5760 0.0682 1.0000 Uiso R . . . . . .
H261 H 0.7685 0.5350 1.0563 0.0639 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
O1 . C2 . O3 . 123.32(19) yes
O1 . C2 . C27 . 125.59(18) yes
O3 . C2 . C27 . 111.09(18) yes
C2 . O3 . C4 . 117.44(15) yes
O3 . C4 . C5 . 106.83(15) yes
O3 . C4 . C25 . 107.37(16) yes
C5 . C4 . C25 . 112.94(16) yes
O3 . C4 . H41 . 108.7 no
C5 . C4 . H41 . 111.2 no
C25 . C4 . H41 . 109.6 no
C4 . C5 . C6 . 111.71(16) yes
C4 . C5 . C22 . 111.48(17) yes
C6 . C5 . C22 . 111.94(17) yes
C4 . C5 . H51 . 106.1 no
C6 . C5 . H51 . 108.2 no
C22 . C5 . H51 . 107.0 no
C5 . C6 . N7 . 112.47(17) yes
C5 . C6 . H62 . 109.5 no
N7 . C6 . H62 . 108.0 no
C5 . C6 . H61 . 108.4 no
N7 . C6 . H61 . 107.2 no
H62 . C6 . H61 . 111.2 no
C6 . N7 . C8 . 111.40(17) yes
C6 . N7 . C15 . 111.29(16) yes
C8 . N7 . C15 . 109.45(17) yes
N7 . C8 . C9 . 112.93(18) yes
N7 . C8 . H82 . 107.1 no
C9 . C8 . H82 . 108.6 no
N7 . C8 . H81 . 109.0 no
C9 . C8 . H81 . 109.8 no
H82 . C8 . H81 . 109.3 no
C8 . C9 . C10 . 120.5(2) yes
C8 . C9 . C14 . 121.6(2) yes
C10 . C9 . C14 . 117.9(2) yes
C9 . C10 . C11 . 120.9(2) yes
C9 . C10 . H101 . 117.7 no
C11 . C10 . H101 . 121.4 no
C10 . C11 . C12 . 120.5(2) yes
C10 . C11 . H111 . 120.4 no
C12 . C11 . H111 . 119.0 no
C11 . C12 . C13 . 119.2(2) yes
C11 . C12 . H121 . 120.9 no
C13 . C12 . H121 . 120.0 no
C12 . C13 . C14 . 120.4(2) yes
C12 . C13 . H131 . 119.7 no
C14 . C13 . H131 . 119.9 no
C9 . C14 . C13 . 121.0(2) yes
C9 . C14 . H141 . 118.4 no
C13 . C14 . H141 . 120.6 no
N7 . C15 . C16 . 113.18(17) yes
N7 . C15 . H152 . 109.3 no
C16 . C15 . H152 . 106.2 no
N7 . C15 . H151 . 109.4 no
C16 . C15 . H151 . 109.3 no
H152 . C15 . H151 . 109.4 no
C15 . C16 . C17 . 121.77(19) yes
C15 . C16 . C21 . 119.77(19) yes
C17 . C16 . C21 . 118.2(2) yes
C16 . C17 . C18 . 120.9(2) yes
C16 . C17 . H171 . 118.3 no
C18 . C17 . H171 . 120.8 no
C17 . C18 . C19 . 120.6(2) yes
C17 . C18 . H181 . 119.7 no
C19 . C18 . H181 . 119.7 no
C18 . C19 . C20 . 118.9(2) yes
C18 . C19 . H191 . 120.3 no
C20 . C19 . H191 . 120.8 no
C19 . C20 . C21 . 120.7(2) yes
C19 . C20 . H201 . 119.9 no
C21 . C20 . H201 . 119.3 no
C16 . C21 . C20 . 120.6(2) yes
C16 . C21 . H211 . 118.9 no
C20 . C21 . H211 . 120.5 no
C5 . C22 . C23 . 111.49(18) yes
C5 . C22 . H222 . 109.7 no
C23 . C22 . H222 . 108.0 no
C5 . C22 . H221 . 108.6 no
C23 . C22 . H221 . 108.6 no
H222 . C22 . H221 . 110.5 no
C22 . C23 . C24 . 111.27(18) yes
C22 . C23 . H231 . 107.9 no
C24 . C23 . H231 . 108.3 no
C22 . C23 . H232 . 110.3 no
C24 . C23 . H232 . 109.6 no
H231 . C23 . H232 . 109.4 no
C23 . C24 . C25 . 111.85(19) yes
C23 . C24 . H242 . 110.7 no
C25 . C24 . H242 . 109.6 no
C23 . C24 . H241 . 108.4 no
C25 . C24 . H241 . 107.0 no
H242 . C24 . H241 . 109.1 no
C4 . C25 . C24 . 111.81(18) yes
C4 . C25 . O26 . 109.25(16) yes
C24 . C25 . O26 . 107.85(17) yes
C4 . C25 . H251 . 108.5 no
C24 . C25 . H251 . 109.9 no
O26 . C25 . H251 . 109.5 no
C25 . O26 . H261 . 103.8 no
C2 . C27 . H272 . 110.0 no
C2 . C27 . H271 . 108.5 no
H272 . C27 . H271 . 110.2 no
C2 . C27 . H273 . 109.0 no
H272 . C27 . H273 . 109.9 no
H271 . C27 . H273 . 109.1 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 . 1.212(2) yes
C2 . O3 . 1.342(2) yes
C2 . C27 . 1.488(3) yes
O3 . C4 . 1.472(2) yes
C4 . C5 . 1.523(3) yes
C4 . C25 . 1.522(3) yes
C4 . H41 . 1.004 no
C5 . C6 . 1.530(3) yes
C5 . C22 . 1.534(3) yes
C5 . H51 . 1.014 no
C6 . N7 . 1.470(3) yes
C6 . H62 . 1.010 no
C6 . H61 . 1.018 no
N7 . C8 . 1.473(3) yes
N7 . C15 . 1.470(3) yes
C8 . C9 . 1.511(3) yes
C8 . H82 . 1.007 no
C8 . H81 . 1.018 no
C9 . C10 . 1.398(3) yes
C9 . C14 . 1.391(3) yes
C10 . C11 . 1.380(3) yes
C10 . H101 . 0.974 no
C11 . C12 . 1.387(3) yes
C11 . H111 . 0.973 no
C12 . C13 . 1.381(3) yes
C12 . H121 . 0.965 no
C13 . C14 . 1.388(3) yes
C13 . H131 . 0.969 no
C14 . H141 . 0.974 no
C15 . C16 . 1.508(3) yes
C15 . H152 . 1.000 no
C15 . H151 . 1.008 no
C16 . C17 . 1.391(3) yes
C16 . C21 . 1.396(3) yes
C17 . C18 . 1.385(3) yes
C17 . H171 . 0.975 no
C18 . C19 . 1.384(3) yes
C18 . H181 . 0.969 no
C19 . C20 . 1.385(4) yes
C19 . H191 . 0.967 no
C20 . C21 . 1.386(3) yes
C20 . H201 . 0.967 no
C21 . H211 . 0.968 no
C22 . C23 . 1.524(3) yes
C22 . H222 . 0.998 no
C22 . H221 . 1.017 no
C23 . C24 . 1.527(3) yes
C23 . H231 . 1.009 no
C23 . H232 . 1.002 no
C24 . C25 . 1.516(3) yes
C24 . H242 . 0.990 no
C24 . H241 . 1.008 no
C25 . O26 . 1.433(2) yes
C25 . H251 . 1.014 no
O26 . H261 . 0.869 no
C27 . H272 . 0.974 no
C27 . H271 . 0.979 no
C27 . H273 . 0.978 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
C5 . H51 . O26 2_767 146 1.01 2.55 3.436(3) yes
O26 . H261 . O1 2_667 171 0.87 1.95 2.811(3) yes
