Synthesis of a Highly Functionalized Core of Verrillin
Saitman, Alec; Theodorakis, Emmanuel A.; Organic Letters 15 (2013) 2410–; doi:10.1021/ol400872h

data_1512050
_publ_section_title
;
 Synthesis of a Highly Functionalized Core of Verrillin
;
_journal_issue                   10
_journal_name_full               'Organic Letters'
_journal_page_first              2410
_journal_paper_doi               10.1021/ol400872h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C21 H26 O6, 1/8(H2 O)'
_chemical_formula_sum            'C21 H26.25 O6.12'
_chemical_formula_weight         376.67
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-19
_audit_creation_method
; 
  Olex2 1.2-beta 
  (compiled Apr  9 2013 14:10:59, GUI svn.r4458) 
;
_cell_angle_alpha                90
_cell_angle_beta                 104.88(3)
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   39.940(8)
_cell_length_b                   21.107(4)
_cell_length_c                   18.631(4)
_cell_measurement_reflns_used    7294
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.86
_cell_volume                     15179(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_publication_material
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            49671
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.471
_diffrn_reflns_theta_min         1.100
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             6440
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.115
_platon_squeeze_details
;
 SQUEEZE found four voids containing one molecule of water in each.  Their
 formula was added to the formula for the unit cell and the electron density
 removed.
;
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     989
_refine_ls_number_reflns         13920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0631P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8997
_reflns_number_total             13920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol400872h_si_002.cif
_cod_data_source_block           as2236a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct' changed to 'direct'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.3.1 from
2005-06-27.

'_atom_sites_solution_secondary' value 'Difmap' changed
to 'difmap' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1512050
_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: 
 C25(H25), C41(H41), C45(H45), C59(H59), C72(H72), C89(H89), C34(H34), 
 C40(H40), C47(H47), C51(H51), C77(H77), C81(H81), C28(H28), C52(H52), C53(H53), 
  C68(H68), C87(H87), C97(H97), C63(H63), C79(H79), C80(H80), C86(H86), 
 C93(H93), C100(H100) 
2.b Secondary CH2 refined with riding coordinates: 
 C50(H50A,H50B), C61(H61A,H61B), C88(H88A,H88B), C39(H39A,H39B), C69(H69A, 
 H69B), C90(H90A,H90B), C60(H60A,H60B), C71(H71A,H71B), C85(H85A,H85B), 
 C91(H91A,H91B), C96(H96A,H96B), C107(H10O,H10P) 
2.c Aromatic/amide H refined with riding coordinates: 
 C56(H56), C58(H58), C33(H33), C55(H55), C32(H32), C35(H35), C49(H49), C66(H66) 
2.d X=CH2 refined with riding coordinates: 
 C92(H92A,H92B), C83(H83A,H83B), C104(H10G,H10H), C84(H84A,H84B) 
2.e Idealised Me refined as rotating group: 
 C70(H70A,H70B,H70C), C82(H82A,H82B,H82C), C102(H10A,H10B,H10C), C76(H76A,H76B, 
 H76C), C78(H78A,H78B,H78C), C101(H10D,H10E,H10F), C67(H67A,H67B,H67C), 
 C94(H94A,H94B,H94C), C106(H10I,H10J,H10K), C99(H99A,H99B,H99C), C105(H10L,H10M, 
 H10N), C108(H10Q,H10R,H10S) 
2.f Idealised tetrahedral OH refined as rotating group: 
 O9(H9), O6(H6), O11(H11), O20(H20) 
;
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.976
_shelx_hkl_checksum              11466
_shelx_res_checksum              52860
_shelxl_version_number           2012-9