#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/95/1519596.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_1519596
loop_
_publ_author_name
'Croft, Anna K.'
'Foley, Mark K.'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C20H24N2O5
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              876
_journal_year                    2004
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H22 N2 O4, H2 O'
_chemical_formula_sum            'C20 H24 N2 O5'
_chemical_formula_weight         372.41
_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                 103.98(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5936(18)
_cell_length_b                   7.2355(14)
_cell_length_c                   15.311(7)
_cell_measurement_reflns_used    2215
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     923.8(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & 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  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10760
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9828
_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    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.3002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                1991
_reflns_number_total             2285
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-876.cif
_cod_data_source_block           04src0621
_cod_depositor_comments
;
Citation :
Croft, Anna K. and Foley, Mark K. and Horton, Peter N. and H
ursthouse, Michael B. (2004) 
University of Southampton, Crystal Structure Report Archive.

More at:
http://ecrystals.chem.soton.ac.uk/876/
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1519596
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 0.7195(3) 0.7100(4) 0.7847(2) 0.0259(7) Uani 1 1 d . . .
H1A H 0.7424 0.7732 0.8430 0.039 Uiso 1 1 calc R . .
H1B H 0.6136 0.6516 0.7736 0.039 Uiso 1 1 calc R . .
H1C H 0.7206 0.7999 0.7370 0.039 Uiso 1 1 calc R . .
C2 C 1.1108(3) 0.0719(5) 0.8251(2) 0.0282(7) Uani 1 1 d . . .
H2A H 1.1461 0.0191 0.7741 0.042 Uiso 1 1 calc R . .
H2B H 1.0333 -0.0115 0.8422 0.042 Uiso 1 1 calc R . .
H2C H 1.2037 0.0877 0.8762 0.042 Uiso 1 1 calc R . .
C3 C 0.9671(3) 0.5565(4) 0.85669(19) 0.0217(6) Uani 1 1 d . . .
C4 C 1.0938(3) 0.4125(4) 0.85703(19) 0.0209(6) Uani 1 1 d . . .
H4 H 1.1307 0.3656 0.9201 0.025 Uiso 1 1 calc R . .
C5 C 0.9023(3) 0.2572(4) 0.73218(19) 0.0222(6) Uani 1 1 d . . .
C6 C 0.8083(3) 0.4355(4) 0.71133(19) 0.0203(6) Uani 1 1 d . . .
H6 H 0.6933 0.3998 0.7033 0.024 Uiso 1 1 calc R . .
C7 C 1.2390(3) 0.5105(4) 0.8329(2) 0.0236(6) Uani 1 1 d . . .
H7A H 1.2111 0.5371 0.7676 0.028 Uiso 1 1 calc R . .
H7B H 1.2562 0.6305 0.8649 0.028 Uiso 1 1 calc R . .
C8 C 1.3942(3) 0.4045(4) 0.85542(19) 0.0213(6) Uani 1 1 d . . .
C9 C 1.5078(3) 0.4363(4) 0.9366(2) 0.0246(6) Uani 1 1 d . . .
H9 H 1.4865 0.5255 0.9777 0.029 Uiso 1 1 calc R . .
C10 C 1.6515(3) 0.3382(4) 0.9575(2) 0.0239(6) Uani 1 1 d . . .
H10 H 1.7285 0.3633 1.0121 0.029 Uiso 1 1 calc R . .
C11 C 1.6830(3) 0.2043(4) 0.89942(19) 0.0227(6) Uani 1 1 d . . .
C12 C 1.5710(3) 0.1720(5) 0.81825(19) 0.0245(6) Uani 1 1 d . . .
H12 H 1.5912 0.0806 0.7778 0.029 Uiso 1 1 calc R . .
C13 C 1.4303(3) 0.2736(4) 0.79681(19) 0.0239(6) Uani 1 1 d . . .
H13 H 1.3565 0.2533 0.7405 0.029 Uiso 1 1 calc R . .
C14 C 0.8202(3) 0.5168(5) 0.61958(19) 0.0226(6) Uani 1 1 d . . .
H14A H 0.7745 0.4257 0.5720 0.027 Uiso 1 1 calc R . .
H14B H 0.7523 0.6289 0.6077 0.027 Uiso 1 1 calc R . .
C15 C 0.9863(3) 0.5673(4) 0.61109(18) 0.0213(6) Uani 1 1 d . . .
C16 C 1.0428(3) 0.7470(5) 0.62450(19) 0.0228(6) Uani 1 1 d . . .
H16 H 0.9763 0.8395 0.6405 0.027 Uiso 1 1 calc R . .
C17 C 1.1952(3) 0.7956(5) 0.6151(2) 0.0239(6) Uani 1 1 d . . .
H17 H 1.2320 0.9194 0.6249 0.029 Uiso 1 1 calc R . .
C18 C 1.2924(3) 0.6608(5) 0.59116(19) 0.0230(6) Uani 1 1 d . . .
C19 C 1.2378(3) 0.4789(4) 0.5777(2) 0.0237(7) Uani 1 1 d . . .
H19 H 1.3045 0.3865 0.5618 0.028 Uiso 1 1 calc R . .
C20 C 1.0872(3) 0.4331(4) 0.58762(19) 0.0235(6) Uani 1 1 d . . .
H20 H 1.0511 0.3089 0.5784 0.028 Uiso 1 1 calc R . .
N1 N 0.8415(2) 0.5686(3) 0.78538(15) 0.0206(5) Uani 1 1 d . . .
N2 N 1.0349(3) 0.2528(3) 0.79917(16) 0.0220(5) Uani 1 1 d . . .
O1 O 0.9863(2) 0.6662(3) 0.92115(14) 0.0266(5) Uani 1 1 d . . .
O2 O 0.8526(2) 0.1184(3) 0.68626(14) 0.0268(5) Uani 1 1 d . . .
O3 O 1.8192(2) 0.1010(3) 0.91797(14) 0.0296(5) Uani 1 1 d . . .
H3 H 1.8716 0.1225 0.9708 0.044 Uiso 1 1 calc R . .
O4 O 1.4422(2) 0.6997(3) 0.57784(15) 0.0274(5) Uani 1 1 d . . .
H4A H 1.4627 0.8123 0.5878 0.041 Uiso 1 1 calc R . .
O21 O 1.4609(2) 0.5504(3) 0.40975(15) 0.0304(5) Uani 1 1 d D . .
H21 H 1.470(4) 0.577(6) 0.4637(13) 0.046 Uiso 1 1 d D . .
H22 H 1.365(3) 0.572(6) 0.3822(19) 0.046 Uiso 1 1 d 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
N1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N2 C2 H2A 109.5 . .
N2 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N2 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
O1 C3 N1 122.0(3) . .
O1 C3 C4 118.7(2) . .
N1 C3 C4 119.2(3) . .
N2 C4 C3 113.5(2) . .
N2 C4 C7 113.3(2) . .
C3 C4 C7 107.7(2) . .
N2 C4 H4 107.4 . .
C3 C4 H4 107.4 . .
C7 C4 H4 107.4 . .
O2 C5 N2 121.9(3) . .
O2 C5 C6 118.5(2) . .
N2 C5 C6 119.6(3) . .
N1 C6 C5 113.8(2) . .
N1 C6 C14 114.2(3) . .
C5 C6 C14 111.5(2) . .
N1 C6 H6 105.5 . .
C5 C6 H6 105.5 . .
C14 C6 H6 105.5 . .
C8 C7 C4 115.5(3) . .
C8 C7 H7A 108.4 . .
C4 C7 H7A 108.4 . .
C8 C7 H7B 108.4 . .
C4 C7 H7B 108.4 . .
H7A C7 H7B 107.5 . .
C13 C8 C9 117.9(3) . .
C13 C8 C7 121.6(3) . .
C9 C8 C7 120.5(3) . .
C10 C9 C8 120.6(3) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C11 C10 C9 120.5(3) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
O3 C11 C10 122.8(2) . .
O3 C11 C12 117.9(3) . .
C10 C11 C12 119.3(3) . .
C13 C12 C11 119.8(3) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C12 C13 C8 121.8(3) . .
C12 C13 H13 119.1 . .
C8 C13 H13 119.1 . .
C15 C14 C6 116.2(2) . .
C15 C14 H14A 108.2 . .
C6 C14 H14A 108.2 . .
C15 C14 H14B 108.2 . .
C6 C14 H14B 108.2 . .
H14A C14 H14B 107.4 . .
C16 C15 C20 118.1(3) . .
C16 C15 C14 121.3(3) . .
C20 C15 C14 120.6(3) . .
C15 C16 C17 121.6(3) . .
C15 C16 H16 119.2 . .
C17 C16 H16 119.2 . .
C18 C17 C16 119.3(3) . .
C18 C17 H17 120.4 . .
C16 C17 H17 120.4 . .
O4 C18 C17 122.5(3) . .
O4 C18 C19 117.6(3) . .
C17 C18 C19 119.9(3) . .
C20 C19 C18 120.1(3) . .
C20 C19 H19 120.0 . .
C18 C19 H19 120.0 . .
C19 C20 C15 121.0(3) . .
C19 C20 H20 119.5 . .
C15 C20 H20 119.5 . .
C3 N1 C6 123.8(2) . .
C3 N1 C1 119.1(2) . .
C6 N1 C1 116.7(2) . .
C5 N2 C4 123.4(2) . .
C5 N2 C2 117.9(2) . .
C4 N2 C2 118.0(2) . .
C11 O3 H3 109.5 . .
C18 O4 H4A 109.5 . .
H21 O21 H22 107(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.464(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 N2 1.474(4) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 O1 1.246(4) .
C3 N1 1.340(3) .
C3 C4 1.507(4) .
C4 N2 1.469(4) .
C4 C7 1.555(4) .
C4 H4 1.0000 .
C5 O2 1.241(4) .
C5 N2 1.337(4) .
C5 C6 1.515(4) .
C6 N1 1.462(4) .
C6 C14 1.549(4) .
C6 H6 1.0000 .
C7 C8 1.504(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C13 1.390(4) .
C8 C9 1.401(4) .
C9 C10 1.393(4) .
C9 H9 0.9500 .
C10 C11 1.386(4) .
C10 H10 0.9500 .
C11 O3 1.360(3) .
C11 C12 1.396(4) .
C12 C13 1.385(4) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.509(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.386(5) .
C15 C20 1.405(4) .
C16 C17 1.397(4) .
C16 H16 0.9500 .
C17 C18 1.389(4) .
C17 H17 0.9500 .
C18 O4 1.380(3) .
C18 C19 1.396(4) .
C19 C20 1.380(4) .
C19 H19 0.9500 .
C20 H20 0.9500 .
O3 H3 0.8400 .
O4 H4A 0.8400 .
O21 H21 0.833(18) .
O21 H22 0.847(18) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.84 1.83 2.664(3) 171.0 2_847
O4 H4A O21 0.84 1.84 2.663(3) 165.9 2_856
O21 H21 O4 0.833(18) 2.03(2) 2.831(3) 162(4) .
O21 H22 O2 0.847(18) 1.937(18) 2.783(3) 177(3) 2_756
