Strategies toward the Total Synthesis of Calyciphylline B-type Alkaloids: A Computational Perspective Aided by DFT Analysis.
Chattopadhyay, Amit Kumar; Berger, Gilles; Hanessian, Stephen; The Journal of organic chemistry 81 (2016) 5074–5086; doi:10.1021/acs.joc.6b00638

data_4036821
_publ_section_title
;
 Strategies toward the Total Synthesis of Calyciphylline B-type Alkaloids:
 A Computational Perspective Aided by DFT Analysis.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5074
_journal_page_last               5086
_journal_paper_doi               10.1021/acs.joc.6b00638
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H29 N O'
_chemical_formula_sum            'C21 H29 N O'
_chemical_formula_weight         311.45
_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'
_atom_sites_solution_hydrogens   geom
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_cell_length_c                   26.483(7)
_cell_measurement_reflns_used    8017
_cell_measurement_temperature    100
_cell_measurement_theta_max      42.120
_cell_measurement_theta_min      2.898
_cell_volume                     1725.0(8)
_computing_cell_refinement
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
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_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
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_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.2757
_diffrn_reflns_av_unetI/netI     0.1462
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       6
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_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.058
_diffrn_reflns_theta_min         2.903
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
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_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.4789
_exptl_absorpt_correction_type   multi-scan
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'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1566 before and 0.1207 after correction. The Ratio of minimum to maximum transmission is 0.6375. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.221
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_refine_ls_abs_structure_details
;
 Flack x determined using 546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(7)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1597
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1660
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1859
_reflns_number_total             3525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00638_si_005.cif
_cod_data_source_block           coumpound_34
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1725.1(8)
_cod_database_code               4036821
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.959
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C10(H10), C13(H13), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C4(H4a,H4b), C5(H5a,H5b), C11(H11a,H11b), C12(H12a,H12b),
 C14(H14a,H14b), C15(H15a,H15b), C19(H19a,H19b)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20)
2.d X=CH2 refined with riding coordinates:
 C21(H21a,H21b)
2.e Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c)
;
_shelx_res_checksum              63889
_shelx_hkl_checksum              53733
_olex2_submission_special_instructions 'No special instructions were received'