Direct biosynthetic cyclization of a distorted paracyclophane highlighted by double isotopic labelling of l-tyrosine.
Ear, Alexandre; Amand, Séverine; Blanchard, Florent; Blond, Alain; Dubost, Lionel; Buisson, Didier; Nay, Bastien; Organic & biomolecular chemistry 13 (2015) 3662–3666; doi:10.1039/c5ob00114e

data_7154329
_publ_section_title
;
 Direct biosynthetic cyclization of a distorted paracyclophane highlighted
 by double isotopic labelling of l-tyrosine.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3662
_journal_page_last               3666
_journal_paper_doi               10.1039/c5ob00114e
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C64 H81 N3 O12'
_chemical_formula_weight         1084.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 120.418(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   34.802(2)
_cell_length_b                   8.7586(5)
_cell_length_c                   22.5029(16)
_cell_measurement_reflns_used    6040
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      2.3
_cell_volume                     5915.1(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
'partial \c, three-axis goniometer diffractometer'
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  'Confocal Max-Flux Osmic optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26382
_diffrn_reflns_point_group_measured_fraction_full 0.840
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         2.277
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku micromax 007HF 1.2kW'
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     711
_refine_ls_number_reflns         9069
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0658
_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^)+(0.0858P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1897
_reflns_Friedel_coverage         0.566
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.651
_reflns_number_gt                5371
_reflns_number_total             9069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00114e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7154329.cif.'
_cod_original_cell_volume        5915.2(8)
_cod_database_code               7154329
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.930
_shelxl_version_number           2014/6
_shelx_res_checksum              13919
_shelx_hkl_checksum              13180