BF3-Promoted Divergent Reactions between Tryptophols and Propargylic Alcohols.
Huang, Kai; Sheng, Guorong; Lu, Ping; Wang, Yanguang; Organic letters 19 (2017) 4114–4117; doi:10.1021/acs.orglett.7b01769

data_1547124
_publ_section_title
;
 BF3-Promoted Divergent Reactions between Tryptophols and Propargylic
 Alcohols.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4114
_journal_page_last               4117
_journal_paper_doi               10.1021/acs.orglett.7b01769
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C32 H23 Br2 N O'
_chemical_formula_sum            'C32 H23 Br2 N O'
_chemical_formula_weight         597.31
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.697(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7055(6)
_cell_length_b                   25.8797(14)
_cell_length_c                   13.0746(11)
_cell_measurement_reflns_used    3571
_cell_measurement_temperature    170.1
_cell_measurement_theta_max      29.5215
_cell_measurement_theta_min      3.1708
_cell_volume                     2483.9(3)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.1
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -15.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.9996   38.0000  -90.0000 90

  2 omega  -90.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -77.0000  -30.0000 108

  3 omega  -38.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183   77.0000   90.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0091216000
_diffrn_orient_matrix_UB_12      -0.0170594000
_diffrn_orient_matrix_UB_13      -0.0439350000
_diffrn_orient_matrix_UB_21      -0.0478684000
_diffrn_orient_matrix_UB_22      -0.0177034000
_diffrn_orient_matrix_UB_23      0.0234222000
_diffrn_orient_matrix_UB_31      -0.0828068000
_diffrn_orient_matrix_UB_32      0.0121075000
_diffrn_orient_matrix_UB_33      -0.0276374000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14992
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.18
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    3.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70615
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+1.2829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                3460
_reflns_number_total             4530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b01769_si_003.cif
_cod_data_source_block           170110_hk4_50
_cod_database_code               1547124
_chemical_oxdiff_formula         'c10 h10 n2 o8 Br1'
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C13(H13), C15(H15), C16(H16),
 C20(H20), C22(H22), C23(H23), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 1484017446.27
_olex2_submission_special_instructions 'No special instructions were received'