#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/02/7150215.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_7150215
loop_
_publ_author_name
'Davies, Stephen G.'
'Garner, A. Christopher'
'Long, Marcus J. C.'
'Morrison, Rachel M.'
'Roberts, Paul M.'
'Savory, Edward D.'
'Smith, Andrew D.'
'Sweet, Miles J.'
'Withey, Jonathan M.'
_publ_section_title
;
 Kinetic resolution and parallel kinetic resolution of methyl
 (+/-)-5-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis
 of 5-alkyl-cispentacin derivatives.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2762
_journal_page_last               2775
_journal_paper_doi               10.1039/b506339f
_journal_volume                  3
_journal_year                    2005
_chemical_compound_source
;
?
;
_chemical_formula_moiety         ' C28 H31 N1 O2 '
_chemical_formula_sum            'C28 H31 N O2'
_chemical_formula_weight         413.56
_chemical_melting_point          ?
_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
_cell_angle_alpha                90
_cell_angle_beta                 95.1151(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0421(2)
_cell_length_b                   9.1315(2)
_cell_length_c                   25.1731(8)
_cell_measurement_reflns_used    4311
_cell_measurement_temperature    190
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     2299.17(10)
_computing_cell_refinement
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
COLLECT (Nonius BV, 1997)
;
_computing_data_reduction
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_molecular_graphics
;
CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al 2001)
;
_computing_structure_solution
;
SIR92 (Altomare et al, 1994)
;
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type
;
Enraf Nonius Kappa CCD
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8740
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' plate '
_exptl_crystal_F_000             888.357
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0124
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3301
_refine_ls_R_factor_gt           0.0873
_refine_ls_shift/su_max          0.000523
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method= Tukey and Prince
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

1.20 0.857 0.712
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0784
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                3301
_reflns_number_total             5082
_reflns_threshold_expression     >1.00σ(I)
_cod_data_source_file            b506339f.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic ' changed to 'monoclinic'
according to '/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        2299.2(1)
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        ' C28 H31 N1 O2 '
_cod_database_code               7150215
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
O1 O 0.6697(2) 0.3295(2) 0.91511(9) 0.0638 1.0000 Uani
C2 C 0.7849(3) 0.3061(3) 0.92904(11) 0.0471 1.0000 Uani
O3 O 0.8637(2) 0.4016(2) 0.95805(9) 0.0644 1.0000 Uani
C4 C 0.8010(5) 0.5399(4) 0.97028(16) 0.0890 1.0000 Uani
C5 C 0.8630(2) 0.1710(3) 0.9174(1) 0.0397 1.0000 Uani
C6 C 0.7792(3) 0.0307(3) 0.9104(1) 0.0408 1.0000 Uani
C7 C 0.7254(3) -0.0325(3) 0.9599(1) 0.0393 1.0000 Uani
C8 C 0.7831(3) -0.0048(3) 1.01124(12) 0.0543 1.0000 Uani
C9 C 0.7335(3) -0.0695(4) 1.05506(12) 0.0604 1.0000 Uani
C10 C 0.6266(3) -0.1644(3) 1.04887(12) 0.0527 1.0000 Uani
C11 C 0.5680(3) -0.1913(3) 0.99872(12) 0.0564 1.0000 Uani
C12 C 0.6174(3) -0.1270(3) 0.95452(11) 0.0498 1.0000 Uani
C13 C 0.8740(3) -0.0720(3) 0.88411(11) 0.0518 1.0000 Uani
C14 C 0.9429(3) 0.0237(3) 0.84509(12) 0.0514 1.0000 Uani
C15 C 0.9436(3) 0.1837(3) 0.8671(1) 0.0420 1.0000 Uani
N16 N 0.89485(19) 0.3004(2) 0.83009(8) 0.0368 1.0000 Uani
C17 C 0.9997(3) 0.3614(3) 0.7983(1) 0.0421 1.0000 Uani
C18 C 1.1010(3) 0.4480(3) 0.83451(11) 0.0427 1.0000 Uani
C19 C 1.0554(3) 0.5556(3) 0.86754(12) 0.0528 1.0000 Uani
C20 C 1.1436(4) 0.6404(4) 0.89956(13) 0.0664 1.0000 Uani
C21 C 1.2789(4) 0.6207(4) 0.89909(15) 0.0701 1.0000 Uani
C22 C 1.3259(3) 0.5156(4) 0.86750(17) 0.0747 1.0000 Uani
C23 C 1.2379(3) 0.4283(4) 0.83514(14) 0.0611 1.0000 Uani
C24 C 1.0636(3) 0.2493(3) 0.76285(12) 0.0559 1.0000 Uani
C25 C 0.7722(3) 0.2648(3) 0.79614(12) 0.0492 1.0000 Uani
C26 C 0.7061(3) 0.3986(3) 0.76996(11) 0.0485 1.0000 Uani
C27 C 0.6714(3) 0.5180(3) 0.79985(13) 0.0585 1.0000 Uani
C28 C 0.6035(3) 0.6357(4) 0.77632(17) 0.0732 1.0000 Uani
C29 C 0.5679(3) 0.6353(5) 0.7225(2) 0.0815 1.0000 Uani
C30 C 0.6019(4) 0.5195(5) 0.69196(15) 0.0799 1.0000 Uani
C31 C 0.6734(3) 0.4000(4) 0.71515(13) 0.0620 1.0000 Uani
H41 H 0.8632 0.6076 0.9914 0.1082 1.0000 Uiso
H42 H 0.7193 0.5242 0.9907 0.1082 1.0000 Uiso
H43 H 0.7670 0.5939 0.9358 0.1082 1.0000 Uiso
H51 H 0.9269 0.1612 0.9518 0.0501 1.0000 Uiso
H61 H 0.6910 0.0491 0.8878 0.0483 1.0000 Uiso
H81 H 0.8632 0.0630 1.0161 0.0643 1.0000 Uiso
H91 H 0.7765 -0.0467 1.0921 0.0711 1.0000 Uiso
H101 H 0.5926 -0.2144 1.0809 0.0665 1.0000 Uiso
H111 H 0.4869 -0.2593 0.9939 0.0687 1.0000 Uiso
H121 H 0.5731 -0.1495 0.9170 0.0619 1.0000 Uiso
H131 H 0.9422 -0.1161 0.9122 0.0642 1.0000 Uiso
H132 H 0.8243 -0.1589 0.8659 0.0642 1.0000 Uiso
H141 H 1.0355 -0.0146 0.8401 0.0641 1.0000 Uiso
H142 H 0.8898 0.0182 0.8082 0.0641 1.0000 Uiso
H151 H 1.0406 0.2180 0.8751 0.0551 1.0000 Uiso
H171 H 0.9549 0.4321 0.7710 0.0530 1.0000 Uiso
H191 H 0.9550 0.5741 0.8675 0.0616 1.0000 Uiso
H201 H 1.1069 0.7162 0.9251 0.0799 1.0000 Uiso
H211 H 1.3435 0.6857 0.9217 0.0851 1.0000 Uiso
H221 H 1.4278 0.5001 0.8673 0.0868 1.0000 Uiso
H231 H 1.2743 0.3494 0.8109 0.0725 1.0000 Uiso
H241 H 1.1330 0.2960 0.7418 0.0698 1.0000 Uiso
H242 H 1.1074 0.1683 0.7852 0.0698 1.0000 Uiso
H243 H 0.9934 0.2031 0.7364 0.0698 1.0000 Uiso
H251 H 0.7071 0.2139 0.8182 0.0598 1.0000 Uiso
H252 H 0.7950 0.1939 0.7672 0.0598 1.0000 Uiso
H271 H 0.6962 0.5181 0.8406 0.0702 1.0000 Uiso
H281 H 0.5835 0.7264 0.7998 0.0881 1.0000 Uiso
H291 H 0.5146 0.7205 0.7064 0.0968 1.0000 Uiso
H301 H 0.5777 0.5217 0.6521 0.0942 1.0000 Uiso
H311 H 0.7007 0.3138 0.6913 0.0762 1.0000 Uiso
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_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B
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 . 123.3(3) yes
O1 . C2 . C5 . 126.6(3) yes
O3 . C2 . C5 . 110.1(2) yes
C2 . O3 . C4 . 115.5(3) yes
O3 . C4 . H41 . 112.804 no
O3 . C4 . H42 . 111.652 no
H41 . C4 . H42 . 108.281 no
O3 . C4 . H43 . 110.743 no
H41 . C4 . H43 . 107.207 no
H42 . C4 . H43 . 105.810 no
C2 . C5 . C6 . 114.6(2) yes
C2 . C5 . C15 . 114.4(2) yes
C6 . C5 . C15 . 106.6(2) yes
C2 . C5 . H51 . 101.804 no
C6 . C5 . H51 . 108.477 no
C15 . C5 . H51 . 110.856 no
C5 . C6 . C7 . 117.1(2) yes
C5 . C6 . C13 . 101.9(2) yes
C7 . C6 . C13 . 113.8(2) yes
C5 . C6 . H61 . 111.476 no
C7 . C6 . H61 . 99.483 no
C13 . C6 . H61 . 113.660 no
C6 . C7 . C8 . 123.0(2) yes
C6 . C7 . C12 . 119.5(2) yes
C8 . C7 . C12 . 117.5(2) yes
C7 . C8 . C9 . 120.9(3) yes
C7 . C8 . H81 . 118.926 no
C9 . C8 . H81 . 120.202 no
C8 . C9 . C10 . 120.7(3) yes
C8 . C9 . H91 . 119.441 no
C10 . C9 . H91 . 119.810 no
C9 . C10 . C11 . 119.0(3) yes
C9 . C10 . H101 . 120.571 no
C11 . C10 . H101 . 120.422 no
C10 . C11 . C12 . 120.6(3) yes
C10 . C11 . H111 . 119.440 no
C12 . C11 . H111 . 119.994 no
C7 . C12 . C11 . 121.3(3) yes
C7 . C12 . H121 . 119.051 no
C11 . C12 . H121 . 119.658 no
C6 . C13 . C14 . 105.2(2) yes
C6 . C13 . H131 . 110.295 no
C14 . C13 . H131 . 110.899 no
C6 . C13 . H132 . 111.864 no
C14 . C13 . H132 . 112.752 no
H131 . C13 . H132 . 105.895 no
C13 . C14 . C15 . 107.2(2) yes
C13 . C14 . H141 . 110.940 no
C15 . C14 . H141 . 113.089 no
C13 . C14 . H142 . 108.942 no
C15 . C14 . H142 . 110.522 no
H141 . C14 . H142 . 106.128 no
C5 . C15 . C14 . 103.4(2) yes
C5 . C15 . N16 . 113.5(2) yes
C14 . C15 . N16 . 117.6(2) yes
C5 . C15 . H151 . 114.386 no
C14 . C15 . H151 . 109.254 no
N16 . C15 . H151 . 99.162 no
C15 . N16 . C17 . 113.62(19) yes
C15 . N16 . C25 . 114.93(19) yes
C17 . N16 . C25 . 111.5(2) yes
N16 . C17 . C18 . 109.8(2) yes
N16 . C17 . C24 . 114.6(2) yes
C18 . C17 . C24 . 113.7(2) yes
N16 . C17 . H171 . 108.006 no
C18 . C17 . H171 . 107.771 no
C24 . C17 . H171 . 102.295 no
C17 . C18 . C19 . 119.1(2) yes
C17 . C18 . C23 . 123.2(3) yes
C19 . C18 . C23 . 117.7(3) yes
C18 . C19 . C20 . 121.1(3) yes
C18 . C19 . H191 . 119.540 no
C20 . C19 . H191 . 119.297 no
C19 . C20 . C21 . 120.3(3) yes
C19 . C20 . H201 . 119.537 no
C21 . C20 . H201 . 120.077 no
C20 . C21 . C22 . 119.7(3) yes
C20 . C21 . H211 . 120.177 no
C22 . C21 . H211 . 120.147 no
C21 . C22 . C23 . 120.6(3) yes
C21 . C22 . H221 . 119.766 no
C23 . C22 . H221 . 119.624 no
C18 . C23 . C22 . 120.5(3) yes
C18 . C23 . H231 . 119.184 no
C22 . C23 . H231 . 120.265 no
C17 . C24 . H241 . 111.563 no
C17 . C24 . H242 . 110.498 no
H241 . C24 . H242 . 108.447 no
C17 . C24 . H243 . 110.858 no
H241 . C24 . H243 . 107.636 no
H242 . C24 . H243 . 107.699 no
N16 . C25 . C26 . 112.7(2) yes
N16 . C25 . H251 . 109.388 no
C26 . C25 . H251 . 109.383 no
N16 . C25 . H252 . 109.073 no
C26 . C25 . H252 . 108.656 no
H251 . C25 . H252 . 107.473 no
C25 . C26 . C27 . 121.3(2) yes
C25 . C26 . C31 . 119.7(3) yes
C27 . C26 . C31 . 118.8(3) yes
C26 . C27 . C28 . 121.3(3) yes
C26 . C27 . H271 . 119.265 no
C28 . C27 . H271 . 119.479 no
C27 . C28 . C29 . 119.9(4) yes
C27 . C28 . H281 . 119.096 no
C29 . C28 . H281 . 120.946 no
C28 . C29 . C30 . 120.1(3) yes
C28 . C29 . H291 . 118.519 no
C30 . C29 . H291 . 121.404 no
C29 . C30 . C31 . 120.7(3) yes
C29 . C30 . H301 . 119.464 no
C31 . C30 . H301 . 119.763 no
C26 . C31 . C30 . 119.1(4) yes
C26 . C31 . H311 . 120.895 no
C30 . C31 . H311 . 119.957 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 . 1.197(3) yes
C2 . O3 . 1.348(4) yes
C2 . C5 . 1.504(4) yes
O3 . C4 . 1.456(4) yes
C4 . H41 . 0.998 no
C4 . H42 . 1.017 no
C4 . H43 . 1.031 no
C5 . C6 . 1.534(3) yes
C5 . C15 . 1.568(4) yes
C5 . H51 . 1.034 no
C6 . C7 . 1.516(4) yes
C6 . C13 . 1.528(4) yes
C6 . H61 . 1.023 no
C7 . C8 . 1.393(4) yes
C7 . C12 . 1.382(4) yes
C8 . C9 . 1.383(4) yes
C8 . H81 . 1.014 no
C9 . C10 . 1.377(4) yes
C9 . H91 . 1.014 no
C10 . C11 . 1.367(4) yes
C10 . H101 . 1.012 no
C11 . C12 . 1.389(4) yes
C11 . H111 . 1.022 no
C12 . H121 . 1.028 no
C13 . C14 . 1.526(4) yes
C13 . H131 . 1.023 no
C13 . H132 . 1.023 no
C14 . C15 . 1.562(4) yes
C14 . H141 . 1.012 no
C14 . H142 . 1.031 no
C15 . N16 . 1.470(3) yes
C15 . H151 . 1.026 no
N16 . C17 . 1.486(3) yes
N16 . C25 . 1.472(3) yes
C17 . C18 . 1.525(4) yes
C17 . C24 . 1.536(4) yes
C17 . H171 . 1.018 no
C18 . C19 . 1.390(4) yes
C18 . C23 . 1.385(4) yes
C19 . C20 . 1.381(4) yes
C19 . H191 . 1.023 no
C20 . C21 . 1.371(5) yes
C20 . H201 . 1.035 no
C21 . C22 . 1.358(5) yes
C21 . H211 . 1.016 no
C22 . C23 . 1.397(5) yes
C22 . H221 . 1.033 no
C23 . H231 . 1.033 no
C24 . H241 . 1.007 no
C24 . H242 . 1.006 no
C24 . H243 . 1.016 no
C25 . C26 . 1.513(4) yes
C25 . H251 . 1.008 no
C25 . H252 . 1.017 no
C26 . C27 . 1.387(4) yes
C26 . C31 . 1.389(4) yes
C27 . C28 . 1.378(4) yes
C27 . H271 . 1.033 no
C28 . C29 . 1.371(6) yes
C28 . H281 . 1.048 no
C29 . C30 . 1.368(6) yes
C29 . H291 . 1.008 no
C30 . C31 . 1.405(5) yes
C30 . H301 . 1.010 no
C31 . H311 . 1.041 no
