#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/95/1519588.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_1519588
loop_
_publ_author_name
'Marson, Charles M.'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 3-benzyl-6-ethyl-7-(hydroxymethyl)-1,8-dioxa-4-azacycloundecane-5,9,11-trione
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              892
_journal_year                    2004
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H23 N O6'
_chemical_formula_sum            'C18 H23 N O6'
_chemical_formula_weight         349.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.70(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.713(4)
_cell_length_b                   6.582(4)
_cell_length_c                   15.739(7)
_cell_measurement_reflns_used    2032
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     883.9(8)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3834
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_correction_T_min  0.9432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.059(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.380
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3834
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.379
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0180P)²+0.1542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                3081
_reflns_number_total             3834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-892.cif
_cod_data_source_block           04src1124
_cod_depositor_comments
;
Citation :
Marson, Charles M. and Coles, Simon J. and Hursthouse, Michael B. (2004) 
University of Southampton, Crystal Structure Report Archive. 

More at:
http://ecrystals.chem.soton.ac.uk/892/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1519588
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2646(3) 0.2188(4) 0.26490(17) 0.0292(6) Uani 1 1 d . . .
C2 C 0.0914(3) 0.2235(4) 0.22181(16) 0.0287(6) Uani 1 1 d . . .
H2 H 0.0490 0.0832 0.2252 0.034 Uiso 1 1 calc R . .
C3 C 0.0700(3) 0.2788(4) 0.12533(17) 0.0350(7) Uani 1 1 d . . .
H3A H -0.0422 0.3058 0.1015 0.042 Uiso 1 1 calc R . .
H3B H 0.1293 0.4045 0.1194 0.042 Uiso 1 1 calc R . .
C4 C 0.1262(4) 0.1103(5) 0.0738(2) 0.0473(8) Uani 1 1 d . . .
H4A H 0.2391 0.0903 0.0944 0.071 Uiso 1 1 calc R . .
H4B H 0.1053 0.1473 0.0122 0.071 Uiso 1 1 calc R . .
H4C H 0.0706 -0.0157 0.0814 0.071 Uiso 1 1 calc R . .
C5 C -0.0002(3) 0.3658(4) 0.27106(16) 0.0288(6) Uani 1 1 d . . .
H5 H -0.1123 0.3216 0.2577 0.035 Uiso 1 1 calc R . .
C6 C 0.0032(3) 0.5912(4) 0.25300(19) 0.0352(6) Uani 1 1 d . . .
H6A H -0.0445 0.6151 0.1912 0.042 Uiso 1 1 calc R . .
H6B H -0.0623 0.6619 0.2883 0.042 Uiso 1 1 calc R . .
C7 C 0.0176(3) 0.1729(4) 0.40121(17) 0.0298(6) Uani 1 1 d . . .
C8 C 0.0958(3) 0.1620(4) 0.49688(17) 0.0338(6) Uani 1 1 d . . .
H8A H 0.1337 0.2981 0.5183 0.041 Uiso 1 1 calc R . .
H8B H 0.0201 0.1135 0.5315 0.041 Uiso 1 1 calc R . .
C9 C 0.2311(3) 0.0165(4) 0.50499(17) 0.0332(6) Uani 1 1 d . . .
C10 C 0.4502(3) -0.0486(4) 0.44083(18) 0.0351(6) Uani 1 1 d . . .
H10A H 0.4097 -0.1893 0.4397 0.042 Uiso 1 1 calc R . .
H10B H 0.5508 -0.0416 0.4833 0.042 Uiso 1 1 calc R . .
C11 C 0.4736(3) 0.0134(4) 0.35089(17) 0.0290(6) Uani 1 1 d . . .
H11 H 0.5320 0.1450 0.3552 0.035 Uiso 1 1 calc R . .
C12 C 0.5683(3) -0.1503(4) 0.31574(17) 0.0332(6) Uani 1 1 d . . .
H12A H 0.6726 -0.1599 0.3547 0.040 Uiso 1 1 calc R . .
H12B H 0.5151 -0.2826 0.3179 0.040 Uiso 1 1 calc R . .
C13 C 0.5914(3) -0.1166(4) 0.22453(17) 0.0325(6) Uani 1 1 d . . .
C14 C 0.5938(3) -0.2822(5) 0.17060(19) 0.0385(7) Uani 1 1 d . . .
H14 H 0.5741 -0.4143 0.1903 0.046 Uiso 1 1 calc R . .
C15 C 0.6245(3) -0.2573(5) 0.0880(2) 0.0459(8) Uani 1 1 d . . .
H15 H 0.6274 -0.3726 0.0520 0.055 Uiso 1 1 calc R . .
C16 C 0.6509(3) -0.0668(5) 0.0580(2) 0.0459(8) Uani 1 1 d . . .
H16 H 0.6728 -0.0499 0.0017 0.055 Uiso 1 1 calc R . .
C17 C 0.6452(3) 0.0996(5) 0.1107(2) 0.0438(7) Uani 1 1 d . . .
H17 H 0.6615 0.2320 0.0901 0.053 Uiso 1 1 calc R . .
C18 C 0.6157(3) 0.0750(4) 0.19335(19) 0.0370(7) Uani 1 1 d . . .
H18 H 0.6121 0.1907 0.2290 0.044 Uiso 1 1 calc R . .
N1 N 0.3203(2) 0.0392(3) 0.29420(14) 0.0290(5) Uani 1 1 d . . .
O1 O 0.34634(19) 0.3744(3) 0.27137(12) 0.0371(5) Uani 1 1 d . . .
O2 O 0.1549(2) 0.6783(3) 0.27084(15) 0.0467(6) Uani 1 1 d . . .
H2A H 0.2215 0.5892 0.2657 0.070 Uiso 1 1 calc R . .
O3 O 0.05707(19) 0.3434(3) 0.36495(11) 0.0294(4) Uani 1 1 d . . .
O4 O -0.0631(2) 0.0409(3) 0.36339(12) 0.0333(4) Uani 1 1 d . . .
O5 O 0.2399(2) -0.1468(3) 0.54011(13) 0.0432(5) Uani 1 1 d . . .
O6 O 0.33888(19) 0.0915(3) 0.46430(12) 0.0331(4) Uani 1 1 d . . .
H1N H 0.258(3) -0.067(5) 0.2880(17) 0.035(8) Uiso 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 N1 123.0(2) . .
O1 C1 C2 121.4(2) . .
N1 C1 C2 115.6(2) . .
C1 C2 C3 110.8(2) . .
C1 C2 C5 110.9(2) . .
C3 C2 C5 112.5(2) . .
C1 C2 H2 107.5 . .
C3 C2 H2 107.5 . .
C5 C2 H2 107.5 . .
C4 C3 C2 111.7(2) . .
C4 C3 H3A 109.3 . .
C2 C3 H3A 109.3 . .
C4 C3 H3B 109.3 . .
C2 C3 H3B 109.3 . .
H3A C3 H3B 107.9 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O3 C5 C6 105.8(2) . .
O3 C5 C2 109.93(19) . .
C6 C5 C2 118.1(2) . .
O3 C5 H5 107.5 . .
C6 C5 H5 107.5 . .
C2 C5 H5 107.5 . .
O2 C6 C5 114.4(2) . .
O2 C6 H6A 108.7 . .
C5 C6 H6A 108.7 . .
O2 C6 H6B 108.7 . .
C5 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
O4 C7 O3 125.0(2) . .
O4 C7 C8 123.8(2) . .
O3 C7 C8 111.1(2) . .
C9 C8 C7 107.4(2) . .
C9 C8 H8A 110.2 . .
C7 C8 H8A 110.2 . .
C9 C8 H8B 110.2 . .
C7 C8 H8B 110.2 . .
H8A C8 H8B 108.5 . .
O5 C9 O6 124.4(2) . .
O5 C9 C8 125.7(3) . .
O6 C9 C8 109.8(2) . .
O6 C10 C11 106.9(2) . .
O6 C10 H10A 110.3 . .
C11 C10 H10A 110.3 . .
O6 C10 H10B 110.3 . .
C11 C10 H10B 110.3 . .
H10A C10 H10B 108.6 . .
N1 C11 C10 108.7(2) . .
N1 C11 C12 110.8(2) . .
C10 C11 C12 109.3(2) . .
N1 C11 H11 109.3 . .
C10 C11 H11 109.3 . .
C12 C11 H11 109.3 . .
C13 C12 C11 115.3(2) . .
C13 C12 H12A 108.4 . .
C11 C12 H12A 108.4 . .
C13 C12 H12B 108.4 . .
C11 C12 H12B 108.4 . .
H12A C12 H12B 107.5 . .
C14 C13 C18 118.5(3) . .
C14 C13 C12 119.3(3) . .
C18 C13 C12 122.1(2) . .
C13 C14 C15 120.7(3) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.6 . .
C16 C15 C14 120.4(3) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C17 C16 C15 119.3(3) . .
C17 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C16 C17 C18 120.4(3) . .
C16 C17 H17 119.8 . .
C18 C17 H17 119.8 . .
C13 C18 C17 120.7(3) . .
C13 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C1 N1 C11 122.9(2) . .
C1 N1 H1N 119.7(18) . .
C11 N1 H1N 116.4(18) . .
C6 O2 H2A 109.5 . .
C7 O3 C5 116.76(19) . .
C9 O6 C10 117.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.240(3) .
C1 N1 1.325(3) .
C1 C2 1.524(3) .
C2 C3 1.536(4) .
C2 C5 1.538(4) .
C2 H2 1.0000 .
C3 C4 1.513(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 O3 1.468(3) .
C5 C6 1.512(4) .
C5 H5 1.0000 .
C6 O2 1.416(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 O4 1.198(3) .
C7 O3 1.335(3) .
C7 C8 1.523(4) .
C8 C9 1.504(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 O5 1.204(3) .
C9 O6 1.334(3) .
C10 O6 1.440(3) .
C10 C11 1.526(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 N1 1.457(3) .
C11 C12 1.528(4) .
C11 H11 1.0000 .
C12 C13 1.506(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.384(4) .
C13 C18 1.385(4) .
C14 C15 1.389(4) .
C14 H14 0.9500 .
C15 C16 1.375(5) .
C15 H15 0.9500 .
C16 C17 1.380(4) .
C16 H16 0.9500 .
C17 C18 1.386(4) .
C17 H17 0.9500 .
C18 H18 0.9500 .
N1 H1N 0.88(3) .
O2 H2A 0.8400 .
