β-Terrecyclene synthase constructs the quadrane backbone in terrecyclic acid biosynthesis.
Song, Yongxiang; Wang, Wengui; Yang, Jiafan; Gao, Dewei; Billingsley, John M.; Wang, Songtao; Zhu, Yiguang; Wang, Junfeng; Ju, Jianhua; Yan, Yan; Tang, Yi; Chemical science 15 (2024) 8750–8755; doi:10.1039/d4sc01208a

data_1571665
_publ_section_title
;
 &#x3b2;-Terrecyclene synthase constructs the quadrane backbone in
 terrecyclic acid biosynthesis.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              8750
_journal_page_last               8755
_journal_paper_doi               10.1039/d4sc01208a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2g7x2q
_audit_creation_date             2020-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-22 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.989(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.36910(10)
_cell_length_b                   12.0175(2)
_cell_length_c                   9.0830(2)
_cell_measurement_reflns_used    5095
_cell_measurement_temperature    106(2)
_cell_measurement_theta_max      73.8160
_cell_measurement_theta_min      5.1570
_cell_volume                     657.39(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      106(2)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_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    -13.00  26.00   0.50    0.50    --    0.00 -82.00  60.00   78
  2  \w    -32.00  27.00   0.50    0.50    --    0.00 -82.00   0.00  118
  3  \w    -13.00  25.00   0.50    0.50    --    0.00 -77.00 120.00   76
  4  \w    -42.00 -15.00   0.50    0.50    --    0.00 -77.00 120.00   54
  5  \w     21.00  55.00   0.50    0.50    --   40.00  65.00 -30.02   68
  6  \w     32.00  69.00   0.50    0.50    --   52.00  75.00  11.86   74
  7  \w     41.00  72.00   0.50    0.50    --   68.00  74.00 -49.07   62
  8  \w    121.00 157.00   0.50    0.50    --   68.00  74.00 -49.07   72
  9  \w     54.00  79.00   0.50    0.50    --   80.00  71.00 -61.26   50
 10  \w     78.00 179.00   0.50    0.50    --   95.80  45.00  60.00  202
 11  \w     77.00 177.00   0.50    0.50    --   95.80  45.00  30.00  200
 12  \w     42.00 125.00   0.50    0.50    --   95.80 -82.00-150.00  166
 13  \w     74.00 117.00   0.50    0.50    --   95.80  54.00  -6.05   86
 14  \w      7.00  39.00   0.50    0.50    --   95.80 -82.00-150.00   64
 15  \w     73.00 132.00   0.50    0.50    --   95.80  61.00 -30.00  118
 16  \w     71.00 161.00   0.50    0.50    --   95.80  68.00 -60.60  180
 17  \w     46.00  86.00   0.50    0.50    --   95.80 -30.00-150.00   80
 18  \w    106.00 184.00   0.50    0.50    --   95.80  30.00 -90.00  156
 19  \w     72.00  97.00   0.50    0.50    --   95.80  61.00 -90.00   50
 20  \w     74.00 180.00   0.50    0.50    --   95.80  61.00 120.00  212
 21  \w     83.00 110.00   0.50    0.50    --   95.80  52.00 -62.70   54
 22  \w    103.00 171.00   0.50    0.50    --   95.80  82.00  90.00  136
 23  \w    121.00 173.00   0.50    0.50    --   95.80  54.00  -6.05  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0312757000
_diffrn_orient_matrix_UB_12      -0.0324910000
_diffrn_orient_matrix_UB_13      0.1699190000
_diffrn_orient_matrix_UB_21      -0.2295963000
_diffrn_orient_matrix_UB_22      0.0491880000
_diffrn_orient_matrix_UB_23      -0.0156952000
_diffrn_orient_matrix_UB_31      -0.1083096000
_diffrn_orient_matrix_UB_32      -0.1138032000
_diffrn_orient_matrix_UB_33      -0.0553840000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6277
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.370
_diffrn_reflns_theta_min         5.150
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0422P)^2^+0.0844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                2496
_reflns_number_total             2560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01208a2.cif
_cod_data_source_block           songyongxiang_sx-terb2_collect
_cod_depositor_comments
'Adding full bibliography for 1571665--1571666.cif.'
_cod_database_code               1571665
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C28 H44 N2 O6 '
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2), C11(H11), C4(H4), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C10(H10A,H10B), C3(H3A,H3B)
2.c X=CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O17(H17), O13(H13)
;
_shelx_res_checksum              27305
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.123
_oxdiff_exptl_absorpt_empirical_full_min 0.907