Penicimutamides A–C: Rare Carbamate-containing Alkaloids from a Mutant of the Marine-derived Penicillium purpurogenum G59
Li, Chang-Wei; Wu, Chang-Jing; Cui, Cheng-Bin; Xu, Lan-Lan; Cao, Fei; Zhu, Huajie; RSC Adv.  (2016) –; doi:10.1039/C6RA14904A

data_7226063
_publ_section_title
;
 Penicimutamides A--C: Rare Carbamate-containing Alkaloids from a Mutant
 of the Marine-derived Penicillium purpurogenum G59
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA14904A
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_compound_source        'Penicillium purpurogenum G59'
_chemical_formula_moiety         'C21 H23 N3 O3'
_chemical_formula_sum            'C21 H23 N3 O3'
_chemical_formula_weight         365.42
_chemical_melting_point          442.0(10)
_chemical_name_systematic        'Penicimutamide A'
_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'
_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             2013-12-31
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2016-05-19 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3978(10)
_cell_length_b                   14.6540(12)
_cell_length_c                   21.3097(19)
_cell_measurement_reflns_used    10470
_cell_measurement_temperature    99.8
_cell_measurement_theta_max      70.4421
_cell_measurement_theta_min      3.6572
_cell_volume                     3559.2(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      99.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -33.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   97.0000  117.0000 51

  2 omega  -90.00  -45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -15.0000  -30.0000 45

  3 omega  -40.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   90.0000 76

  4 omega   -7.00   20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -15.0000  -30.0000 27

  5 omega  -77.00  -47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -45.0000  -60.0000 30

  6 omega  -46.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -45.0000  -60.0000 27

  7 omega   28.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   37.0000   30.0000 97

  8 omega   33.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   37.0000  -30.0000 55

  9 omega  -13.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -37.0000  -60.0000 87

 10 omega   28.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   37.0000 -120.0000 96

 11 omega  -18.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -37.0000   60.0000 95

 12 omega  101.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   37.0000  -30.0000 25

 13 omega  123.00  172.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 49

 14 omega   56.00   84.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 28

 15 omega   78.00  104.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 16 omega  109.00  174.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 65

 17 omega   78.00  104.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

 18 omega  126.00  178.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 52

 19 omega   86.00  111.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 25

 20 omega   85.00  168.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 83

 21 omega   69.00   97.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 28

 22 omega  128.00  176.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 48

 23 omega  113.00  165.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 52

 24 omega   78.00  110.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 32

 25 omega   55.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 31

 26 omega  129.00  178.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 49

 27 omega   78.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

 28 omega   85.00  110.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 25

 29 omega   55.00   87.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 32

 30 omega  114.00  177.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 63

 31 omega   81.00  108.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 27

 32 omega  137.00  177.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 40

 33 omega   55.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 26

 34 omega   64.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 25

 35 omega   85.00  111.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 26

 36 omega   86.00  111.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 25

 37 omega  100.00  160.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 60

 38 omega   40.00   84.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 44

 39 omega  121.00  176.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 55

 40 omega   92.00  118.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0784946000
_diffrn_orient_matrix_UB_12      0.0728560000
_diffrn_orient_matrix_UB_13      0.0307132000
_diffrn_orient_matrix_UB_21      0.0041211000
_diffrn_orient_matrix_UB_22      0.0572926000
_diffrn_orient_matrix_UB_23      -0.0609704000
_diffrn_orient_matrix_UB_31      -0.1098277000
_diffrn_orient_matrix_UB_32      -0.0497845000
_diffrn_orient_matrix_UB_33      -0.0237881000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26574
_diffrn_reflns_theta_full        64.98
_diffrn_reflns_theta_max         64.98
_diffrn_reflns_theta_min         3.66
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'colorless '
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1552
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+5.0575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                5752
_reflns_number_total             6072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra14904a2.cif
_cod_data_source_block           exp_1844
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '441-443' was changed to '442.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7226063
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_solvent_exptl_crystal_recrystallization_method MeOH