Evolution of a Unified, Stereodivergent Approach to the Synthesis of Communesin F and Perophoramidine.
Han, Seo-Jung; Vogt, Florian; May, Jeremy A.; Krishnan, Shyam; Gatti, Michele; Virgil, Scott C.; Stoltz, Brian M.; The Journal of organic chemistry 80 (2014) 528–; doi:10.1021/jo502534g

data_4030304
_publ_section_title
;
 Evolution of a Unified, Stereodivergent Approach to the Synthesis of
 Communesin F and Perophoramidine.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              528
_journal_paper_doi               10.1021/jo502534g
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety
'2(C23 H23 Br N3 O4), 0.81(C H2 Cl2), 0.19(H2 O)'
_chemical_formula_sum            'C46.4 H47.2 Br2 Cl0.8 N6 O8.2'
_chemical_formula_weight         1008.40
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2012-10-29
_audit_creation_method
;
  Olex2 1.2
  (compiled Oct 26 2012 17:09:49, GUI svn.r4371)
 SHELXL-2012,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 96.873(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6618(8)
_cell_length_b                   17.4368(7)
_cell_length_c                   13.5068(5)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.69
_cell_measurement_theta_min      2.32
_cell_volume                     4129.7(3)
_computing_cell_refinement       'SAINT V8.27B (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2012.4-3 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.27B (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_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.
 and SHELXTL (Bruker-AXS, 2007)
;
_computing_structure_refinement  'SHELXL-2012/6 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            213592
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         37.587
_diffrn_reflns_theta_min         2.144
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0662 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.8480.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       plate
_exptl_crystal_F_000             2067
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         3.944
_refine_diff_density_min         -2.054
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.308
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     592
_refine_ls_number_reflns         21060
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      3.309
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14742
_reflns_number_total             21060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502534g_si_013.cif
_cod_data_source_block           sjh01
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_source_target' value 'MO' changed to 'Mo' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030304--4030313.cif.
;
_cod_original_formula_sum        'C46.40 H47.20 Br2 Cl0.80 N6 O8.20'
_cod_database_code               4030304
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H4A of C4A, H3A of C3A, H2A of C2A, {H3AA,H3AB} of N3A, {H10A,H10B} of C10A,
   {H11A,H11B} of C11A, {H14A,H14B} of C14A, {H15A,H15B} of C15A, H18A of C18A,
  H19A of C19A, H20A of C20A, H21A of C21A, {H3BA,H3BB} of N3B, H2B of C2B, H3B
  of C3B, H4B of C4B, {H10C,H10D} of C10B, {H11C,H11D} of C11B, {H14C,H14D} of
  C14B, {H15C,H15D} of C15B, H18B of C18B, H19B of C19B, H20B of C20B, H21B of
  C21B, {H1A,H1B} of C1
 At 1.5 times of:
  {H9AA,H9AB,H9AC} of C9A, {H23A,H23B,H23C} of C23A, {H9BA,H9BB,H9BC} of C9B,
  {H23D,H23E,H23F} of C23B, {H1C,H1D} of O1
2. Restrained distances
 O1-H1C
 0.84 with sigma of 0.01
 O1-H1D
 0.84 with sigma of 0.01
 H1C-H1D
 1.34 with sigma of 0.02
3. Others
 Sof(Cl1)=Sof(C1)=Sof(H1A)=Sof(H1B)=1-Sof(C1)=1-Sof(C1)=1-Sof(C1)
4.a Secondary CH2 refined with riding coordinates:
 N3A(H3AA,H3AB), C10A(H10A,H10B), C11A(H11A,H11B), C14A(H14A,H14B), C15A(H15A,
 H15B), N3B(H3BA,H3BB), C10B(H10C,H10D), C11B(H11C,H11D), C14B(H14C,H14D),
 C15B(H15C,H15D), C1(H1A,H1B)
4.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A),
 C2B(H2B), C3B(H3B), C4B(H4B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B)
4.c Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C23A(H23A,H23B,H23C), C9B(H9BA,H9BB,H9BC), C23B(H23D,
 H23E,H23F)
;
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.448
_shelx_hkl_checksum              84687
_shelx_res_checksum              66924
_shelxl_version_number           2012-6