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_1571666
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2g7x3r
_audit_creation_date             2023-01-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-06-22 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.45480(10)
_cell_length_b                   17.2854(3)
_cell_length_c                   12.2879(2)
_cell_measurement_reflns_used    9604
_cell_measurement_temperature    106(5)
_cell_measurement_theta_max      74.0950
_cell_measurement_theta_min      4.4220
_cell_volume                     1371.01(4)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(5)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -14.00  14.00   0.50    2.00    --    0.00 -82.00-150.00   56
  2  \w    -29.00  21.00   0.50    2.00    --    0.00 -82.00 -90.00  100
  3  \w      8.00  89.00   0.50    2.00    --    0.00  38.00  60.00  162
  4  \w    -28.00   0.00   0.50    2.00    --    0.00 -82.00  60.00   56
  5  \w    -29.00  -4.00   0.50    2.00    --    0.00 -82.00   0.00   50
  6  \w    -33.00  27.00   0.50    2.00    --    0.00 -82.00 -60.00  120
  7  \w      7.00  64.00   0.50    9.03    --   95.80 -61.00-120.00  114
  8  \w     82.00 127.00   0.50    9.03    --   95.80 -82.00 150.00   90
  9  \w      6.00 108.00   0.50    9.03    --   95.80 -30.00   0.00  204
 10  \w      9.00 126.00   0.50    9.03    --   95.80 -82.00 -30.00  234
 11  \w     13.00 112.00   0.50    9.03    --   95.80 -30.00 120.00  198
 12  \w     42.00 120.00   0.50    9.03    --   95.80 -82.00 120.00  156
 13  \w    117.00 185.00   0.50    9.03    --   95.80  30.00 -90.00  136
 14  \w     15.00  61.00   0.50    9.03    --   95.80 -61.00 -90.00   92
 15  \w     61.00 127.00   0.50    9.03    --   95.80 -82.00  60.00  132
 16  \w      6.00  94.00   0.50    9.03    --   95.80 -45.00   0.00  176
 17  \w     96.00 170.00   0.50    9.03    --   95.80  30.00 -30.00  148
 18  \w     68.00 108.00   0.50    9.03    --   95.80 -61.00 -90.00   80
 19  \w     59.00  97.00   0.50    9.03    --   95.80 -82.00-150.00   76
 20  \w     80.00 107.00   0.50    9.03    --   95.80 -45.00 120.00   54
 21  \w     94.00 127.00   0.50    9.03    --   95.80 -82.00  30.00   66
 22  \w     54.00 120.00   0.50    9.03    --   95.80 -82.00 -73.07  132
;
_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      0.0912139000
_diffrn_orient_matrix_UB_12      -0.0214948000
_diffrn_orient_matrix_UB_13      -0.1118541000
_diffrn_orient_matrix_UB_21      0.0395462000
_diffrn_orient_matrix_UB_22      0.0862300000
_diffrn_orient_matrix_UB_23      -0.0238492000
_diffrn_orient_matrix_UB_31      0.2169637000
_diffrn_orient_matrix_UB_32      -0.0067538000
_diffrn_orient_matrix_UB_33      0.0513783000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12582
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.579
_diffrn_reflns_theta_max         66.579
_diffrn_reflns_theta_min         4.415
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74029
_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    1.213
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 930 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0910
_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^)+(0.1739P)^2^+0.9992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2571
_refine_ls_wR_factor_ref         0.2585
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2330
_reflns_number_total             2425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01208a2.cif
_cod_data_source_block           songyongxiang_xs-terb_collect
_cod_depositor_comments
'Adding full bibliography for 1571665--1571666.cif.'
_cod_database_code               1571666
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C66 H60 N6 O6 '
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.801
_reflns_odcompleteness_completeness 99.86
_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. Uiso/Uaniso restraints and constraints
O1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O2 \\sim O1 \\sim O2A \\sim O1A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3. Others
 Sof(O2A)=Sof(H2AA)=Sof(O1A)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(O1)=FVAR(1)
4.a Riding coordinates:
 O2(H2), O2A(H2AA)
4.b Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C2(H2A), C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C3(H3A,H3B), C10(H10A,H10B), C12(H12A,H12B)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.709