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_1552603
_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         'C16 H17 Cl1 O6'
_chemical_formula_sum            'C16 H17 Cl O6'
_chemical_formula_weight         340.76
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             18-07-17
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2018-07-17 - Report on C16 H17 Cl O6 
             by Anthony C. Willis
       for   Steve Pyne and Chiramet Auranwiwat

This is a re-collection  of pyn1806B

2018-07-17 - details of refinement in _refine_special_details below

2018-07-17 - passes checkcif tests with no significant warnings 

;
_cell_angle_alpha                90
_cell_angle_beta                 95.528(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5080(5)
_cell_length_b                   5.3369(2)
_cell_length_c                   22.2879(9)
_cell_measurement_reflns_used    9051
_cell_measurement_temperature    150
_cell_measurement_theta_max      73
_cell_measurement_theta_min      4
_cell_volume                     1599.28(11)
_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 1.000
_diffrn_measured_fraction_theta_max 0.994
_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  0.049
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16146
_diffrn_reflns_theta_full        72.644
_diffrn_reflns_theta_max         74.127
_diffrn_reflns_theta_min         3.676
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.379
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.64
_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    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.44
_refine_ls_abs_structure_details 'Flack (1983), 1055 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.0020308
_refine_ls_shift/su_mean         0.0000911
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.12P)^2^ + 0.74P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1611
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1611
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              5
_reflns_limit_k_min              -6
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2737
_reflns_number_total             2862
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.36
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0573
_oxford_refine_ls_scale          6.1(3)
_oxford_reflns_number_all        2862
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\pyn1810SNQ\Tony_pyn1810SNQ_da At 11:46 on'
_cod_data_source_file            np8b00794_si_005.cif
_cod_data_source_block           pyn1810SNQ
_cod_original_sg_symbol_H-M      'I 1 2 1 '
_cod_original_formula_sum        'C16 H17 Cl1 O6'
_cod_database_code               1552603
_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, U'S H(1,X'S) H(2,X'S) 
CONT ENANTIO 
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   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,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   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 0.85 0.02 = O(1) TO H(1) 
DIST 0.85 0.02 = O(2) TO H(2) 
ANGLE 109 2 = C(4) TO O(1) TO H(1) 
ANGLE 109 2 = C(5) TO O(2) TO H(2) 
REM 
DIST  2.30, 0.05 =  H(2) TO H(141,2,1,1,1,1) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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