Controlling Asymmetric Remote and Cascade 1,3-Dipolar Cycloaddition Reactions by Organocatalysis.
Poulsen, Pernille H.; Vergura, Stefania; Monleón, Alicia; Jørgensen, Danny Kaare Bech; Jørgensen, Karl Anker; Journal of the American Chemical Society 138 (2016) 6412–6415; doi:10.1021/jacs.6b03546

data_4130435
_publ_section_title
;
 Controlling Asymmetric Remote and Cascade 1,3-Dipolar Cycloaddition
 Reactions by Organocatalysis.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6412
_journal_page_last               6415
_journal_paper_doi               10.1021/jacs.6b03546
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H34 Br2 N2 O3'
_chemical_formula_sum            'C34 H34 Br2 N2 O3'
_chemical_formula_weight         678.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.724(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3093(4)
_cell_length_b                   6.24868(15)
_cell_length_c                   29.0192(8)
_cell_measurement_reflns_used    13483
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      27.5350
_cell_measurement_theta_min      2.2120
_cell_volume                     3061.65(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -25.00 119.00   1.00   25.00    --   18.61  77.00   0.00  144
  2  \w    -25.00 119.00   1.00   25.00    --   18.61  77.00-120.00  144
  3  \w    -63.00  81.00   1.00   25.00    --  -19.62  77.00 120.00  144
  4  \w    -82.00  62.00   1.00   25.00    --   18.61 -77.00 -30.00  144
  5  \w     62.00 111.00   1.00   25.00    --   18.61 144.00  41.00   49
  6  \w     34.00 118.00   1.00   25.00    --   18.61-178.00 -60.00   84
  7  \w    -25.00 119.00   1.00   25.00    --   18.61  77.00 150.00  144
  8  \w     35.00 120.00   1.00   25.00    --   18.61 178.00 150.00   85
  9  \w     34.00  80.00   1.00   25.00    --  -19.62-178.00 -90.00   46
 10  \w    -23.00  80.00   1.00   25.00    --   18.61  57.00  60.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0066242000
_diffrn_orient_matrix_UB_12      -0.1108470000
_diffrn_orient_matrix_UB_13      0.0026339000
_diffrn_orient_matrix_UB_21      -0.0042350000
_diffrn_orient_matrix_UB_22      0.0182858000
_diffrn_orient_matrix_UB_23      0.0234404000
_diffrn_orient_matrix_UB_31      -0.0412890000
_diffrn_orient_matrix_UB_32      0.0158771000
_diffrn_orient_matrix_UB_33      -0.0084651000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            33393
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.762
_diffrn_reflns_theta_min         1.534
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       needle
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.612
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 2642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         7311
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0687P)^2^+5.8300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                6551
_reflns_number_total             7311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03546_si_002.cif
_cod_data_source_block           2016_03_08_mette
_cod_original_cell_volume        3061.65(13)
_cod_database_code               4130435
_chemical_oxdiff_formula         'C20 O3 N2'
_reflns_odcompleteness_completeness 99.94
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00N(H00N), C00R(H00R), C00T(H00T), C00V(H00V)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00C), C015(H01D,H01E)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00A(H00A), C00F(H00F), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00P(H00P), C00Q(H00Q), C00S(H00S), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C014(H014)
2.d Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C)
2.e Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_shelx_res_checksum              14991
_shelx_hkl_checksum              13024
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.776