#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:45:47 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152857.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_7152857
loop_
_publ_author_name
'Webber, Matthew J'
'Warren, Sarah A'
'Grainger, Damian M'
'Weston, Matthew'
'Clark, Stacy'
'Woodhead, Steven J'
'Powell, Lyn'
'Stokes, Stephen'
'Alanine, Alexander'
'Stonehouse, Jeffrey P'
'Frampton, Christopher S'
'White, Andrew J P'
'Spivey, Alan C'
_publ_section_title
;
 Towards the enantioselective synthesis of (-)-euonyminol--preparation of
 a fully functionalised lower-rim model.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2514
_journal_page_last               2533
_journal_paper_doi               10.1039/c3ob27187k
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C19 H29 N O6'
_chemical_formula_sum            'C19 H29 N O6'
_chemical_formula_weight         367.43
_chemical_name_systematic
;
?
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.328(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6847(2)
_cell_length_b                   12.1746(3)
_cell_length_c                   14.6780(3)
_cell_measurement_reflns_used    16759
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.4662
_cell_measurement_theta_min      3.0170
_cell_volume                     1901.09(7)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28509
_diffrn_reflns_theta_full        72.55
_diffrn_reflns_theta_max         72.55
_diffrn_reflns_theta_min         4.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3756
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0370
_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)+(0.0533P)²+0.4969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                3397
_reflns_number_total             3756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob27187k.txt
_cod_data_source_block           31
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 7152853--7152857.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7152857
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.93227(11) 0.59413(11) 0.39407(9) 0.0333(3) Uani 1 1 d .
H1A H 0.9728 0.5299 0.4260 0.040 Uiso 1 1 calc R
H1B H 0.9999 0.6404 0.3727 0.040 Uiso 1 1 calc R
C2 C 0.86471(12) 0.66051(11) 0.46358(9) 0.0340(3) Uani 1 1 d .
H2A H 0.9248 0.6649 0.5199 0.041 Uiso 1 1 calc R
C3 C 0.75003(11) 0.59758(10) 0.49175(8) 0.0296(3) Uani 1 1 d .
H3A H 0.6997 0.6484 0.5276 0.036 Uiso 1 1 calc R
C4 C 0.66365(11) 0.55237(10) 0.41087(8) 0.0260(2) Uani 1 1 d .
H4A H 0.6002 0.5025 0.4351 0.031 Uiso 1 1 calc R
C5 C 0.73341(11) 0.48920(9) 0.34071(8) 0.0260(3) Uani 1 1 d .
C6 C 0.64977(11) 0.45166(9) 0.25558(8) 0.0259(2) Uani 1 1 d .
H6A H 0.6414 0.5096 0.2071 0.031 Uiso 1 1 calc R
C7 C 0.72809(12) 0.35319(10) 0.22785(8) 0.0284(3) Uani 1 1 d .
H7A H 0.6777 0.3041 0.1838 0.034 Uiso 1 1 calc R
C8 C 0.84814(13) 0.39443(11) 0.18768(9) 0.0338(3) Uani 1 1 d .
H8A H 0.9016 0.3283 0.1799 0.041 Uiso 1 1 calc R
C9 C 0.92593(12) 0.47187(11) 0.25418(9) 0.0338(3) Uani 1 1 d .
H9A H 0.9826 0.5155 0.2186 0.041 Uiso 1 1 calc R
H9B H 0.9794 0.4264 0.2981 0.041 Uiso 1 1 calc R
C10 C 0.84918(11) 0.55239(10) 0.30941(9) 0.0295(3) Uani 1 1 d .
C11 C 0.83459(15) 0.77964(12) 0.43585(11) 0.0422(3) Uani 1 1 d .
H11A H 0.7916 0.8157 0.4839 0.063 Uiso 1 1 calc R
H11B H 0.7800 0.7806 0.3784 0.063 Uiso 1 1 calc R
H11C H 0.9128 0.8188 0.4275 0.063 Uiso 1 1 calc R
O12 O 0.79920(8) 0.51204(8) 0.55133(6) 0.0325(2) Uani 1 1 d .
C13 C 0.70813(14) 0.45489(14) 0.59697(10) 0.0428(3) Uani 1 1 d .
H13A H 0.6453 0.5069 0.6155 0.064 Uiso 1 1 calc R
H13B H 0.7491 0.4183 0.6513 0.064 Uiso 1 1 calc R
H13C H 0.6669 0.3998 0.5557 0.064 Uiso 1 1 calc R
O14 O 0.60002(8) 0.64471(7) 0.36875(6) 0.0311(2) Uani 1 1 d D
H14 H 0.5494(15) 0.6209(16) 0.3204(8) 0.055(5) Uiso 1 1 d D
O15 O 0.77995(8) 0.38812(6) 0.38425(6) 0.0267(2) Uani 1 1 d .
C16 C 0.75440(11) 0.29817(10) 0.32205(8) 0.0277(3) Uani 1 1 d .
C17 C 0.63785(12) 0.23284(9) 0.34388(8) 0.0284(3) Uani 1 1 d .
O17 O 0.58464(9) 0.16856(7) 0.29058(6) 0.0352(2) Uani 1 1 d .
O18 O 0.60955(9) 0.24682(7) 0.42952(6) 0.0323(2) Uani 1 1 d .
C19 C 0.50203(14) 0.18498(12) 0.45409(10) 0.0405(3) Uani 1 1 d .
H19A H 0.4306 0.1977 0.4085 0.061 Uiso 1 1 calc R
H19B H 0.4800 0.2088 0.5144 0.061 Uiso 1 1 calc R
H19C H 0.5226 0.1065 0.4561 0.061 Uiso 1 1 calc R
C20 C 0.86412(13) 0.21727(11) 0.33453(10) 0.0357(3) Uani 1 1 d .
H20A H 0.9419 0.2545 0.3216 0.054 Uiso 1 1 calc R
H20B H 0.8482 0.1554 0.2923 0.054 Uiso 1 1 calc R
H20C H 0.8726 0.1901 0.3976 0.054 Uiso 1 1 calc R
O21 O 0.53152(7) 0.42063(7) 0.28429(6) 0.0278(2) Uani 1 1 d .
C22 C 0.43879(13) 0.39645(11) 0.21068(9) 0.0340(3) Uani 1 1 d .
H22A H 0.4268 0.4606 0.1705 0.051 Uiso 1 1 calc R
H22B H 0.3592 0.3782 0.2353 0.051 Uiso 1 1 calc R
H22C H 0.4667 0.3339 0.1757 0.051 Uiso 1 1 calc R
C23 C 0.81682(15) 0.44307(13) 0.09181(10) 0.0438(3) Uani 1 1 d .
H23A H 0.7670 0.3901 0.0535 0.066 Uiso 1 1 calc R
H23B H 0.8949 0.4592 0.0643 0.066 Uiso 1 1 calc R
H23C H 0.7685 0.5109 0.0964 0.066 Uiso 1 1 calc R
C24 C 0.81028(12) 0.64556(11) 0.24830(9) 0.0321(3) Uani 1 1 d .
N25 N 0.78917(12) 0.71607(10) 0.19746(9) 0.0419(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C10 115.96(10)
C11 C2 C1 114.97(12)
C11 C2 C3 113.02(11)
C1 C2 C3 110.68(10)
O12 C3 C2 105.76(10)
O12 C3 C4 111.86(10)
C2 C3 C4 114.09(10)
O14 C4 C5 110.28(9)
O14 C4 C3 106.31(9)
C5 C4 C3 113.83(10)
O15 C5 C4 107.30(9)
O15 C5 C6 104.79(9)
C4 C5 C6 114.40(9)
O15 C5 C10 107.37(9)
C4 C5 C10 113.47(10)
C6 C5 C10 108.90(9)
O21 C6 C5 107.71(9)
O21 C6 C7 113.09(10)
C5 C6 C7 99.05(9)
C6 C7 C16 99.20(9)
C6 C7 C8 109.83(10)
C16 C7 C8 113.31(10)
C23 C8 C9 113.76(11)
C23 C8 C7 110.94(11)
C9 C8 C7 112.01(10)
C8 C9 C10 115.85(10)
C24 C10 C1 110.08(10)
C24 C10 C9 107.41(10)
C1 C10 C9 109.60(10)
C24 C10 C5 111.72(10)
C1 C10 C5 109.70(10)
C9 C10 C5 108.27(10)
C13 O12 C3 114.74(10)
C16 O15 C5 109.22(8)
O15 C16 C20 108.47(10)
O15 C16 C17 111.86(9)
C20 C16 C17 105.59(10)
O15 C16 C7 104.33(9)
C20 C16 C7 117.52(10)
C17 C16 C7 109.20(10)
O17 C17 O18 123.98(11)
O17 C17 C16 122.76(11)
O18 C17 C16 112.99(10)
C17 O18 C19 115.10(10)
C6 O21 C22 113.86(9)
N25 C24 C10 174.24(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5336(19)
C1 C10 1.5446(18)
C2 C11 1.532(2)
C2 C3 1.5341(18)
C3 O12 1.4283(15)
C3 C4 1.5364(16)
C4 O14 1.4248(14)
C4 C5 1.5330(16)
C5 O15 1.4529(14)
C5 C6 1.5367(17)
C5 C10 1.5616(16)
C6 O21 1.4197(14)
C6 C7 1.5384(16)
C7 C16 1.5387(17)
C7 C8 1.5444(17)
C8 C23 1.5347(19)
C8 C9 1.5433(19)
C9 C10 1.5537(17)
C10 C24 1.4814(18)
O12 C13 1.4145(17)
O15 C16 1.4356(14)
C16 C20 1.5292(17)
C16 C17 1.5362(17)
C17 O17 1.2105(16)
C17 O18 1.3308(15)
O18 C19 1.4469(16)
O21 C22 1.4272(15)
C24 N25 1.1461(18)
