Nitric Oxide Inhibitory Sesquiterpenoids and Its Dimers from Artemisia freyniana.
Zhang, Chen; Wen, Ran; Ma, Xiao-Li; Zeng, Ke-Wu; Xue, Yang; Zhang, Pu-Ming; Zhao, Ming-Bo; Jiang, Yong; Liu, Guo-Qing; Tu, Peng-Fei; Journal of natural products  (2018) –; doi:10.1021/acs.jnatprod.7b00947

data_1549030
_publ_section_title
;
 Nitric Oxide Inhibitory Sesquiterpenoids and Its Dimers from Artemisia
 freyniana.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.7b00947
_journal_year                    2018
_chemical_formula_moiety         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.83018(8)
_cell_length_b                   26.1293(3)
_cell_length_c                   7.49108(9)
_cell_measurement_reflns_used    7979
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.9820
_cell_measurement_theta_min      1.7180
_cell_volume                     1336.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -90.00  64.00   1.00    1.00    --    0.00  45.00 270.00  154
  2  \w   -135.00  45.00   1.00    1.00    --  -45.00  45.00  60.00  180
  3  \w   -135.00 -15.00   1.00    1.00    --  -45.00  60.00  60.00  120
  4  \w    -77.00  44.00   1.00    1.00    --  -45.00  60.00 180.00  121
  5  \w   -180.00 -18.00   1.00    1.00    --  -90.00  60.00 120.00  162
  6  \w   -180.00 -32.00   1.00    1.00    --  -90.00  60.00 180.00  148
  7  \w   -146.00 -11.00   1.00    1.00    --  -90.00  45.00  60.00  135
  8  \w   -150.00 -30.00   1.00    1.00    --  -90.00  60.00  60.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0025094000
_diffrn_orient_matrix_UB_12      0.0578815000
_diffrn_orient_matrix_UB_13      0.0387236000
_diffrn_orient_matrix_UB_21      -0.0019561000
_diffrn_orient_matrix_UB_22      0.0111468000
_diffrn_orient_matrix_UB_23      -0.2019124000
_diffrn_orient_matrix_UB_31      -0.2256245000
_diffrn_orient_matrix_UB_32      -0.0007878000
_diffrn_orient_matrix_UB_33      0.0013744000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10436
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.624
_diffrn_reflns_theta_min         3.383
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 834 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.4250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2178
_reflns_number_total             2395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00947_si_001.cif
_cod_data_source_block           e2-8
_cod_database_code               1549030
_reflns_odcompleteness_completeness 97.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.d Tetrahedral OH refined with riding coordinates:
 O3(H3)
2.e X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.f Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              27666
_shelx_hkl_checksum              33052
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.689
_oxdiff_exptl_absorpt_empirical_full_min 0.492