#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/48/4024807.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_4024807
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         'C21 H25 N1'
_chemical_formula_sum            'C21 H25 N'
_chemical_formula_weight         291.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-05-14
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 93.0165(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7454(3)
_cell_length_b                   6.33680(10)
_cell_length_c                   17.3225(4)
_cell_measurement_reflns_used    3853
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1725.97(6)
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_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  0.018
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6636
_diffrn_reflns_theta_full        26.393
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         5.137
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.98
_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    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8712
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.000271
_refine_ls_structure_factor_coef Fsqd
_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: 
 31.6 45.1 21.3 4.60 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1209
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1016
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2988
_reflns_number_total             3899
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.84
_oxford_diffrn_Wilson_scale      1.04
_oxford_refine_ls_r_factor_ref   0.0477
_oxford_refine_ls_scale          1.019(4)
_oxford_reflns_number_all        3899
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_oxford_structure_analysis_title '5141710 SGD206'
_cod_data_source_file            jo9012783_si_002.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/c 1 '
_cod_original_formula_sum        'C21 H25 N1'
_cod_database_code               4024807
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
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
N1 N 0.23445(8) 0.6047(2) 0.74446(7) 0.0267 1.0000 Uani . . . . . . .
C2 C 0.31069(10) 0.4968(3) 0.77585(9) 0.0315 1.0000 Uani . . . . . . .
C3 C 0.37754(10) 0.6469(3) 0.80932(9) 0.0335 1.0000 Uani . . . . . . .
C4 C 0.38846(11) 0.8462(3) 0.77760(11) 0.0390 1.0000 Uani . . . . . . .
C5 C 0.45389(12) 0.9775(4) 0.80503(12) 0.0516 1.0000 Uani . . . . . . .
C6 C 0.50890(13) 0.9099(5) 0.86555(13) 0.0645 1.0000 Uani . . . . . . .
C7 C 0.49854(13) 0.7128(5) 0.89760(12) 0.0643 1.0000 Uani . . . . . . .
C8 C 0.43320(11) 0.5814(4) 0.86984(10) 0.0475 1.0000 Uani . . . . . . .
C9 C 0.18158(9) 0.6949(3) 0.80449(9) 0.0266 1.0000 Uani . . . . . . .
C10 C 0.13079(11) 0.5304(3) 0.84789(9) 0.0324 1.0000 Uani . . . . . . .
C11 C 0.09515(12) 0.6049(3) 0.92310(10) 0.0421 1.0000 Uani . . . . . . .
C12 C 0.02530(13) 0.7758(3) 0.91570(12) 0.0481 1.0000 Uani . . . . . . .
C13 C 0.05315(13) 0.9859(3) 0.88653(11) 0.0464 1.0000 Uani . . . . . . .
C14 C 0.07437(11) 0.9949(3) 0.80433(11) 0.0384 1.0000 Uani . . . . . . .
C15 C 0.12683(10) 0.8675(3) 0.76802(10) 0.0315 1.0000 Uani . . . . . . .
C16 C 0.18597(10) 0.4713(3) 0.68887(9) 0.0298 1.0000 Uani . . . . . . .
C17 C 0.22936(9) 0.4550(3) 0.61284(9) 0.0285 1.0000 Uani . . . . . . .
C18 C 0.23101(11) 0.2645(3) 0.57327(10) 0.0370 1.0000 Uani . . . . . . .
C19 C 0.26982(12) 0.2502(4) 0.50285(10) 0.0446 1.0000 Uani . . . . . . .
C20 C 0.30665(12) 0.4249(4) 0.47187(10) 0.0452 1.0000 Uani . . . . . . .
C21 C 0.30550(12) 0.6151(3) 0.51080(10) 0.0418 1.0000 Uani . . . . . . .
C22 C 0.26684(11) 0.6304(3) 0.58084(10) 0.0345 1.0000 Uani . . . . . . .
H21 H 0.2960 0.3904 0.8164 0.0405 1.0000 Uiso R . . . . . .
H22 H 0.3353 0.4172 0.7316 0.0403 1.0000 Uiso R . . . . . .
H41 H 0.3487 0.8901 0.7346 0.0522 1.0000 Uiso R . . . . . .
H51 H 0.4619 1.1169 0.7826 0.0713 1.0000 Uiso R . . . . . .
H61 H 0.5550 1.0027 0.8844 0.0788 1.0000 Uiso R . . . . . .
H71 H 0.5370 0.6658 0.9398 0.0795 1.0000 Uiso R . . . . . .
H81 H 0.4255 0.4415 0.8922 0.0657 1.0000 Uiso R . . . . . .
H91 H 0.2231 0.7639 0.8439 0.0338 1.0000 Uiso R . . . . . .
H101 H 0.1673 0.4059 0.8589 0.0424 1.0000 Uiso R . . . . . .
H102 H 0.0819 0.4855 0.8135 0.0432 1.0000 Uiso R . . . . . .
H112 H 0.1420 0.6712 0.9564 0.0525 1.0000 Uiso R . . . . . .
H111 H 0.0731 0.4805 0.9496 0.0519 1.0000 Uiso R . . . . . .
H121 H 0.0031 0.7946 0.9683 0.0665 1.0000 Uiso R . . . . . .
H122 H -0.0227 0.7227 0.8773 0.0666 1.0000 Uiso R . . . . . .
H131 H 0.1063 1.0273 0.9181 0.0600 1.0000 Uiso R . . . . . .
H132 H 0.0083 1.0915 0.8946 0.0597 1.0000 Uiso R . . . . . .
H141 H 0.0453 1.1077 0.7737 0.0487 1.0000 Uiso R . . . . . .
H151 H 0.1316 0.8871 0.7124 0.0415 1.0000 Uiso R . . . . . .
H161 H 0.1784 0.3236 0.7098 0.0388 1.0000 Uiso R . . . . . .
H162 H 0.1286 0.5372 0.6780 0.0381 1.0000 Uiso R . . . . . .
H181 H 0.2048 0.1424 0.5950 0.0450 1.0000 Uiso R . . . . . .
H191 H 0.2703 0.1166 0.4757 0.0581 1.0000 Uiso R . . . . . .
H201 H 0.3339 0.4151 0.4228 0.0565 1.0000 Uiso R . . . . . .
H211 H 0.3317 0.7398 0.4897 0.0497 1.0000 Uiso R . . . . . .
H221 H 0.2656 0.7641 0.6073 0.0451 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'
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 . N1 . C9 . 113.61(12) yes
C2 . N1 . C16 . 111.33(13) yes
C9 . N1 . C16 . 113.06(12) yes
N1 . C2 . C3 . 112.96(15) yes
N1 . C2 . H21 . 111.0 no
C3 . C2 . H21 . 109.5 no
N1 . C2 . H22 . 106.9 no
C3 . C2 . H22 . 108.5 no
H21 . C2 . H22 . 107.8 no
C2 . C3 . C4 . 121.18(15) yes
C2 . C3 . C8 . 119.90(18) yes
C4 . C3 . C8 . 118.79(17) yes
C3 . C4 . C5 . 120.91(19) yes
C3 . C4 . H41 . 117.8 no
C5 . C4 . H41 . 121.3 no
C4 . C5 . C6 . 119.6(2) yes
C4 . C5 . H51 . 121.1 no
C6 . C5 . H51 . 119.3 no
C5 . C6 . C7 . 120.0(2) yes
C5 . C6 . H61 . 119.2 no
C7 . C6 . H61 . 120.8 no
C6 . C7 . C8 . 120.3(2) yes
C6 . C7 . H71 . 119.9 no
C8 . C7 . H71 . 119.8 no
C3 . C8 . C7 . 120.4(2) yes
C3 . C8 . H81 . 118.9 no
C7 . C8 . H81 . 120.7 no
N1 . C9 . C10 . 114.10(13) yes
N1 . C9 . C15 . 108.38(12) yes
C10 . C9 . C15 . 113.34(13) yes
N1 . C9 . H91 . 105.8 no
C10 . C9 . H91 . 107.2 no
C15 . C9 . H91 . 107.6 no
C9 . C10 . C11 . 115.72(15) yes
C9 . C10 . H101 . 108.9 no
C11 . C10 . H101 . 108.6 no
C9 . C10 . H102 . 108.0 no
C11 . C10 . H102 . 107.2 no
H101 . C10 . H102 . 108.2 no
C10 . C11 . C12 . 116.10(15) yes
C10 . C11 . H112 . 109.2 no
C12 . C11 . H112 . 104.6 no
C10 . C11 . H111 . 107.8 no
C12 . C11 . H111 . 109.4 no
H112 . C11 . H111 . 109.5 no
C11 . C12 . C13 . 115.56(16) yes
C11 . C12 . H121 . 106.8 no
C13 . C12 . H121 . 108.9 no
C11 . C12 . H122 . 108.5 no
C13 . C12 . H122 . 106.8 no
H121 . C12 . H122 . 110.3 no
C12 . C13 . C14 . 116.33(17) yes
C12 . C13 . H131 . 107.3 no
C14 . C13 . H131 . 106.7 no
C12 . C13 . H132 . 109.3 no
C14 . C13 . H132 . 108.0 no
H131 . C13 . H132 . 109.0 no
C13 . C14 . C15 . 127.29(18) yes
C13 . C14 . H141 . 115.0 no
C15 . C14 . H141 . 117.7 no
C9 . C15 . C14 . 126.45(16) yes
C9 . C15 . H151 . 115.6 no
C14 . C15 . H151 . 117.9 no
N1 . C16 . C17 . 111.51(12) yes
N1 . C16 . H161 . 111.4 no
C17 . C16 . H161 . 108.3 no
N1 . C16 . H162 . 108.4 no
C17 . C16 . H162 . 107.9 no
H161 . C16 . H162 . 109.2 no
C16 . C17 . C18 . 120.53(15) yes
C16 . C17 . C22 . 120.80(15) yes
C18 . C17 . C22 . 118.66(15) yes
C17 . C18 . C19 . 120.53(18) yes
C17 . C18 . H181 . 119.1 no
C19 . C18 . H181 . 120.4 no
C18 . C19 . C20 . 120.21(18) yes
C18 . C19 . H191 . 119.7 no
C20 . C19 . H191 . 120.1 no
C19 . C20 . C21 . 119.75(16) yes
C19 . C20 . H201 . 120.3 no
C21 . C20 . H201 . 119.9 no
C20 . C21 . C22 . 120.33(18) yes
C20 . C21 . H211 . 120.6 no
C22 . C21 . H211 . 119.0 no
C21 . C22 . C17 . 120.53(17) yes
C21 . C22 . H221 . 119.8 no
C17 . C22 . H221 . 119.7 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
N1 . C2 . 1.461(2) yes
N1 . C9 . 1.4806(19) yes
N1 . C16 . 1.4655(19) yes
C2 . C3 . 1.512(2) yes
C2 . H21 . 1.010 no
C2 . H22 . 1.011 no
C3 . C4 . 1.391(3) yes
C3 . C8 . 1.394(2) yes
C4 . C5 . 1.389(3) yes
C4 . H41 . 0.988 no
C5 . C6 . 1.392(3) yes
C5 . H51 . 0.976 no
C6 . C7 . 1.380(4) yes
C6 . H61 . 0.977 no
C7 . C8 . 1.390(3) yes
C7 . H71 . 0.972 no
C8 . H81 . 0.978 no
C9 . C10 . 1.535(2) yes
C9 . C15 . 1.510(2) yes
C9 . H91 . 1.019 no
C10 . C11 . 1.521(2) yes
C10 . H101 . 0.989 no
C10 . H102 . 0.990 no
C11 . C12 . 1.544(3) yes
C11 . H112 . 1.004 no
C11 . H111 . 0.985 no
C12 . C13 . 1.498(3) yes
C12 . H121 . 1.000 no
C12 . H122 . 1.037 no
C13 . C14 . 1.481(3) yes
C13 . H131 . 1.009 no
C13 . H132 . 0.988 no
C14 . C15 . 1.336(2) yes
C14 . H141 . 0.988 no
C15 . H151 . 0.979 no
C16 . C17 . 1.519(2) yes
C16 . H161 . 1.013 no
C16 . H162 . 1.004 no
C17 . C18 . 1.389(2) yes
C17 . C22 . 1.388(2) yes
C18 . C19 . 1.396(2) yes
C18 . H181 . 0.962 no
C19 . C20 . 1.372(3) yes
C19 . H191 . 0.968 no
C20 . C21 . 1.381(3) yes
C20 . H201 . 0.974 no
C21 . C22 . 1.389(2) yes
C21 . H211 . 0.972 no
C22 . H221 . 0.964 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28579597
