Calophyline A, a new rearranged monoterpenoid indole alkaloid from Winchia calophylla.
Li, Li-Mei; Yang, Tai; Liu, Yang; Liu, Jin; Li, Min-Hui; Wang, Yan-Tang; Yang, Shu-Xia; Zou, Qiang; Li, Guo-You; Organic letters 14 (2012) 3450–3453; doi:10.1021/ol301400e

data_1508581
_publ_section_title
;
 Calophyline A, a new rearranged monoterpenoid indole alkaloid from
 Winchia calophylla.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3450
_journal_page_last               3453
_journal_paper_doi               10.1021/ol301400e
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H22 N2 O4, 2(C H4 O)'
_chemical_formula_sum            'C23 H30 N2 O6'
_chemical_formula_weight         430.49
_chemical_name_systematic
;
 ? 
;
_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
;
'Thu Oct 28 13:42:29 2010'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1186(3)
_cell_length_b                   12.1557(3)
_cell_length_c                   16.7470(4)
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      29.1861
_cell_measurement_theta_min      2.9480
_cell_volume                     2059.86(9)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -44.00   70.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       20.0174    0.0000 -120.0000 114

  2 omega    7.00   43.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       20.0174   38.0000  -30.0000 36
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0677769000
_diffrn_orient_matrix_UB_12      -0.0119566000
_diffrn_orient_matrix_UB_13      0.0063369000
_diffrn_orient_matrix_UB_21      -0.0167633000
_diffrn_orient_matrix_UB_22      0.0315512000
_diffrn_orient_matrix_UB_23      -0.0341666000
_diffrn_orient_matrix_UB_31      0.0058737000
_diffrn_orient_matrix_UB_32      -0.0476004000
_diffrn_orient_matrix_UB_33      -0.0242561000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6506
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         29.1861
_diffrn_reflns_theta_min         2.9480
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.4(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.5433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                3509
_reflns_number_total             3860
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             1507867
_cod_data_source_file            ol301400e_si_001.cif
_cod_data_source_block           101028_s2_lgy
_cod_original_cell_volume        2059.85(8)
_cod_database_code               1508581
_chemical_oxdiff_formula         C84H88N8O16
_reflns_odcompleteness_completeness 91.75
_reflns_odcompleteness_iscentric 0
_reflns_odcompleteness_theta     26.32