Synthesis of the guanacastepene A-B hydrazulene ring system through photochemical ring transposition.
McGowan, Craig A.; Schmieder, Ann-Kathrin; Roberts, Lee; Greaney, Michael F.; Organic & biomolecular chemistry 5 (2007) 1522–1524; doi:10.1039/b704865c

data_7151126
_publ_section_title
;
 Synthesis of the guanacastepene A-B hydrazulene ring system through
 photochemical ring transposition.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1522
_journal_page_last               1524
_journal_paper_doi               10.1039/b704865c
_journal_volume                  5
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_compound_source
;
?
;
_chemical_formula_moiety         ' C13 H18 O4 '
_chemical_formula_sum            'C13 H18 O4'
_chemical_formula_weight         238.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             04-03-17
_audit_creation_method           CRYSTALS_ver_12.20
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2231(3)
_cell_length_b                   9.3503(4)
_cell_length_c                   17.2474(6)
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    150
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     1164.86(8)
_computing_cell_refinement
;
SAINT (Siemens ,1995)
;
_computing_data_collection
;
SMART (Siemens, 1993)
;
_computing_data_reduction
;
SAINT (Siemens ,1995)
;
_computing_molecular_graphics
;
CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al 2003)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al 2003)
;
_computing_structure_solution
;
SIR92 (Altomare et al, 1994)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type
;
Bruker SMART
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8602
_diffrn_reflns_theta_full        27.437
_diffrn_reflns_theta_max         28.881
_diffrn_reflns_theta_min         2.362
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS
(Siemens, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       ' lath '
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     None
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_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1693
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.000192
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
p=P(6)*max(Fo^2^,0)+ (1-P(6))Fc^2^
Method = SHELXL 97 (Sheldrick, 1997)
W =1. /'[Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta)']
P(i) are: 0.456E-01 0.00 0.00 0.00 0.00 0.333
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1074
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1074
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                1320
_reflns_number_total             1693
_reflns_threshold_expression     I>2.00u(I)
_cod_data_source_file            b704865c.txt
_cod_data_source_block           cm036p
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        ' C13 H18 O4 '
_cod_database_code               7151126