Polyoxygenated Cyclohexenes and Their Chlorinated Derivatives from the Leaves of Uvaria cherrevensis.
Auranwiwat, Chiramet; Wongsomboon, Puttandon; Thaima, Thanaphat; Rattanajak, Roonglawan; Kamchonwongpaisan, Sumalee; Willis, Anthony C.; Laphookhieo, Surat; Pyne, Stephen G.; Limtharakul, Thunwadee; Journal of natural products 82 (2019) 101–110; doi:10.1021/acs.jnatprod.8b00794

data_1552605
_publ_section_title
;
 Polyoxygenated Cyclohexenes and Their Chlorinated Derivatives from the
 Leaves of Uvaria cherrevensis.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              101
_journal_page_last               110
_journal_paper_doi               10.1021/acs.jnatprod.8b00794
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_moiety         'C23 H22 O8, 0.352(C H2 Cl2)'
_chemical_formula_sum            'C23.352 H22.704 Cl0.704 O8'
_chemical_formula_weight         456.31
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             18-07-18
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2018-07-18 - Report on C23.35 H22.70 Cl0.70 O8 
             by Anthony C. Willis
       for   Steve Pyne and Chiramet Auranwiwat

2018-07-18 - details of refinement in _refine_special_details below

2018-07-18 - passes checkcif tests with no significant warnings 

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.6285(2)
_cell_length_b                   16.4135(1)
_cell_length_c                   5.7063(1)
_cell_measurement_reflns_used    24430
_cell_measurement_temperature    150
_cell_measurement_theta_max      74
_cell_measurement_theta_min      5
_cell_volume                     2213.05(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_sigmaI/netI    0.062
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            44994
_diffrn_reflns_theta_full        73.795
_diffrn_reflns_theta_max         73.795
_diffrn_reflns_theta_min         3.741
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.615
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             955.107
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details 'Flack (1983), 1873 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.16(10)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4477
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.0094701
_refine_ls_shift/su_mean         0.0011500
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.82P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1131
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1131
_reflns_limit_h_max              29
_reflns_limit_h_min              -29
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                4346
_reflns_number_total             4477
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.26
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0425
_oxford_refine_ls_scale          6.17(15)
_oxford_reflns_number_all        4477
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\pyn1803SNQ\Tony_pyn1803SNQ_da At 10:20 on'
_cod_data_source_file            np8b00794_si_004.cif
_cod_data_source_block           pyn1803SNQ
_cod_original_cell_volume        2213.05(4)
_cod_original_sg_symbol_Hall     'P 2 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 2 '
_cod_database_code               1552605
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S , CL(51,OCC,U'S) UNTIL CL(54) 
CONT O(1,U'S) UNTIL C(23) 
CONT C(52,OCC,U'S) UNTIL C(53) 
CONT ENANTIO 
EQUIV CL(51,OCC) CL(53,OCC) C(52,OCC) 
WEIGHT 2 CL(51,OCC) CL(53,OCC) 
EQUIV CL(52,OCC) CL(54,OCC) C(53,OCC) 
RIDE O(3,X'S) H(1,X'S) 
RIDE O(6,X'S) H(2,X'S) 
RIDE C ( 1,X'S) H( 11,X'S) 
RIDE C ( 2,X'S) H( 21,X'S) 
RIDE C ( 3,X'S) H( 31,X'S) 
RIDE C ( 5,X'S) H( 51,X'S) 
RIDE C ( 6,X'S) H( 61,X'S) 
RIDE C ( 8,X'S) H( 81,X'S) H( 82,X'S) H( 83,X'S) 
RIDE C ( 9,X'S) H( 91,X'S) H( 92,X'S) 
RIDE C ( 12,X'S) H( 121,X'S) 
RIDE C ( 13,X'S) H( 131,X'S) 
RIDE C ( 14,X'S) H( 141,X'S) 
RIDE C ( 15,X'S) H( 151,X'S) 
RIDE C ( 16,X'S) H( 161,X'S) 
RIDE C ( 19,X'S) H( 191,X'S) 
RIDE C ( 20,X'S) H( 201,X'S) 
RIDE C ( 21,X'S) H( 211,X'S) 
RIDE C ( 22,X'S) H( 221,X'S) 
RIDE C ( 23,X'S) H( 231,X'S) 
RIDE C(52,X'S) H(521,X'S) H(522,X'S) 
RIDE C(53,X'S) H(531,X'S) H(532,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
U(IJ) 0.0, .02 = CL(51) TO CL(52) 
U(IJ) 0.0, .02 = CL(52) TO CL(53) 
U(IJ) 0.0, .02 = CL(53) TO CL(54) 
REM 
U(IJ) 0.0, .002 = CL(52) TO C(52) 
U(IJ) 0.0, .002 = CL(53) TO C(53) 
REM 
DIST 1.80, .01 = CL(51) TO C(52) 
DIST 1.80, .01 = CL(53) TO C(52) 
DIST 1.80, .01 = CL(52) TO C(53) 
DIST 1.80, .01 = CL(54) TO C(53) 
ANGLE 109.5, 1 = CL(51) TO C(52) TO CL(53) 
ANGLE 109.5, 1 = CL(52) TO C(53) TO CL(54) 
REM 
LIMIT CL(52,U[33]) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;