#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/28/1502832.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_1502832
loop_
_publ_author_name
'Lin, Sheng'
'Chen, Tao'
'Liu, Xiao-Hua'
'Shen, Yun-Heng'
'Li, Hui-Liang'
'Shan, Lei'
'Liu, Run-Hui'
'Xu, Xi-Ke'
'Zhang, Wei-Dong'
'Wang, Hui'
_publ_section_title
;
 Iridoids and lignans from Valeriana jatamansi.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              632
_journal_page_last               638
_journal_paper_doi               10.1021/np900795c
_journal_volume                  73
_journal_year                    2010
_chemical_formula_sum            'C10 H17 O6'
_chemical_formula_weight         233.24
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.54(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.957(14)
_cell_length_b                   13.28(3)
_cell_length_c                   7.662(17)
_cell_measurement_reflns_used    731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.025
_cell_measurement_theta_min      3.068
_cell_volume                     587(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2385
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(14)
_refine_ls_extinction_coef       0.63(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   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1835
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0595
_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)+(0.1233P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1517
_reflns_number_gt                1750
_reflns_number_total             1835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np900795c_si_002.cif
_cod_data_source_block           f81201b
_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1502832
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
O1 O 0.3806(4) 0.14325(17) 0.7408(3) 0.0513(6) Uani 1 1 d .
O2 O 0.2798(3) 0.11558(17) 0.4541(3) 0.0446(6) Uani 1 1 d .
O3 O -0.2439(3) -0.11160(17) 0.7514(3) 0.0463(6) Uani 1 1 d .
O4 O 0.2848(3) -0.10507(16) 0.5957(2) 0.0392(5) Uani 1 1 d .
C1 C 0.2448(5) 0.1016(2) 0.6161(4) 0.0372(6) Uani 1 1 d .
C3 C 0.1280(6) 0.0654(3) 0.2992(4) 0.0477(8) Uani 1 1 d .
H3A H 0.1726 -0.0047 0.2971 0.057 Uiso 1 1 calc R
H3B H 0.1444 0.0969 0.1888 0.057 Uiso 1 1 calc R
C4 C -0.1158(6) 0.0720(2) 0.3091(4) 0.0429(7) Uani 1 1 d .
C5 C -0.1612(4) 0.0253(2) 0.4740(3) 0.0352(6) Uani 1 1 d .
H5 H -0.2994 0.0560 0.4991 0.042 Uiso 1 1 calc R
C6 C -0.1960(5) -0.0897(2) 0.4533(4) 0.0380(7) Uani 1 1 d .
H6C H -0.3595 -0.1063 0.4144 0.046 Uiso 1 1 calc R
H6D H -0.1179 -0.1163 0.3664 0.046 Uiso 1 1 calc R
C7 C -0.0898(4) -0.1317(2) 0.6399(4) 0.0375(7) Uani 1 1 d .
H7A H -0.0578 -0.2039 0.6352 0.045 Uiso 1 1 calc R
C8 C 0.1352(4) -0.0707(2) 0.7017(4) 0.0338(6) Uani 1 1 d .
C9 C 0.0485(4) 0.03789(19) 0.6414(3) 0.0334(6) Uani 1 1 d .
H9A H -0.0096 0.0679 0.7383 0.040 Uiso 1 1 calc R
C10 C 0.2536(6) -0.0794(3) 0.9004(4) 0.0450(7) Uani 1 1 d .
H10A H 0.3020 -0.1477 0.9282 0.068 Uiso 1 1 calc R
H10B H 0.1473 -0.0600 0.9701 0.068 Uiso 1 1 calc R
H10C H 0.3866 -0.0359 0.9290 0.068 Uiso 1 1 calc R
C11 C -0.2789(7) 0.1175(3) 0.1829(5) 0.0649(10) Uani 1 1 d .
H11A H -0.2125 0.1415 0.0888 0.097 Uiso 1 1 calc R
H11B H -0.3411 0.1732 0.2354 0.097 Uiso 1 1 calc R
H11C H -0.4007 0.0704 0.1335 0.097 Uiso 1 1 calc R
O5 O 0.8483(4) 0.7539(2) 0.0255(3) 0.0627(7) Uani 1 1 d D
O6 O 0.2359(4) 0.7587(2) 0.3053(4) 0.0636(7) Uani 1 1 d D
H5A H 0.970(4) 0.767(3) 0.103(4) 0.053(10) Uiso 1 1 d D
H5B H 0.753(5) 0.726(3) 0.077(5) 0.064(13) Uiso 1 1 d D
H6A H 0.363(5) 0.731(3) 0.302(5) 0.052(10) Uiso 1 1 d D
H6B H 0.259(15) 0.820(3) 0.28(2) 0.34(9) 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 0.0016 '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'
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
C1 O2 C3 119.2(3)
O1 C1 O2 116.2(3)
O1 C1 C9 122.8(3)
O2 C1 C9 120.9(2)
O2 C3 C4 110.4(3)
O2 C3 H3A 109.6
C4 C3 H3A 109.6
O2 C3 H3B 109.6
C4 C3 H3B 109.6
H3A C3 H3B 108.1
C11 C4 C3 122.6(3)
C11 C4 C5 123.3(3)
C3 C4 C5 114.1(3)
C4 C5 C6 111.9(2)
C4 C5 C9 112.0(3)
C6 C5 C9 104.5(2)
C4 C5 H5 109.5
C6 C5 H5 109.5
C9 C5 H5 109.5
C7 C6 C5 104.7(2)
C7 C6 H6C 110.8
C5 C6 H6C 110.8
C7 C6 H6D 110.8
C5 C6 H6D 110.8
H6C C6 H6D 108.9
O3 C7 C6 108.5(2)
O3 C7 C8 111.1(3)
C6 C7 C8 102.8(2)
O3 C7 H7A 111.4
C6 C7 H7A 111.4
C8 C7 H7A 111.4
O4 C8 C10 110.4(3)
O4 C8 C7 106.1(3)
C10 C8 C7 114.8(2)
O4 C8 C9 109.6(2)
C10 C8 C9 113.8(2)
C7 C8 C9 101.4(2)
C1 C9 C5 116.5(3)
C1 C9 C8 110.5(3)
C5 C9 C8 106.4(2)
C1 C9 H9A 107.7
C5 C9 H9A 107.7
C8 C9 H9A 107.7
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C4 C11 H11A 109.5
C4 C11 H11B 109.5
H11A C11 H11B 109.5
C4 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
H5A O5 H5B 109(3)
H6A O6 H6B 102(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.219(4)
O2 C1 1.322(5)
O2 C3 1.460(4)
O3 C7 1.428(4)
O4 C8 1.423(4)
C1 C9 1.494(5)
C3 C4 1.475(6)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C11 1.331(5)
C4 C5 1.492(5)
C5 C6 1.543(5)
C5 C9 1.558(4)
C5 H5 0.9800
C6 C7 1.516(5)
C6 H6C 0.9700
C6 H6D 0.9700
C7 C8 1.536(4)
C7 H7A 0.9800
C8 C10 1.514(5)
C8 C9 1.561(5)
C9 H9A 0.9800
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
O5 H5A 0.833(18)
O5 H5B 0.852(18)
O6 H6A 0.849(19)
O6 H6B 0.86(2)
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
O5 H5B O1 0.852(18) 2.09(2) 2.907(5) 161(4) 2_656
O5 H5A O6 0.833(18) 1.92(2) 2.729(6) 163(4) 1_655
O6 H6A O1 0.849(19) 2.01(2) 2.845(6) 168(4) 2_656
