Enantioselective Synthesis of 4- and 6-Azaindolines by a Cation-Directed Cyclization.
Lamb, Alan D.; Davey, Peter D.; Driver, Russell W.; Thompson, Amber L.; Smith, Martin D.; Organic letters 18 (2016) 5372–5375; doi:10.1021/acs.orglett.6b02744

data_1555859
_publ_section_title
;
 Enantioselective Synthesis of 4- and 6-Azaindolines by a Cation-Directed
 Cyclization.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5372
_journal_page_last               5375
_journal_paper_doi               10.1021/acs.orglett.6b02744
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 Br1 N2 O4'
_chemical_formula_sum            'C21 H23 Br N2 O4'
_chemical_formula_weight         447.33
_chemical_melting_point          ?
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2014-01-16
_audit_creation_method           CRYSTALS_ver_14.52
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2019(1)
_cell_length_b                   15.5905(1)
_cell_length_c                   21.6362(1)
_cell_measurement_reflns_used    52753
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      3
_cell_volume                     4115.93(5)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            91277
_diffrn_reflns_theta_full        76.789
_diffrn_reflns_theta_max         76.789
_diffrn_reflns_theta_min         3.494
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.967
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_brown
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.49
_refine_ls_abs_structure_details 'Flack (1983), 3831 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.030(7)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         8640
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0205
_refine_ls_shift/su_max          0.0012212
_refine_ls_shift/su_mean         0.0000684
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.13P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0513
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0513
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                8451
_reflns_number_total             8640
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.90
_oxford_diffrn_Wilson_scale      0.16
_oxford_refine_ls_r_factor_ref   0.0212
_oxford_refine_ls_scale          2.609(8)
_oxford_reflns_number_all        8640
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6418b
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE N   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 462,X'S) H   ( 463,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) H   ( 472,X'S) H   ( 473,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 543,X'S) H   ( 542,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 533,X'S) H   ( 532,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE N   (   9,X'S) H   (  91,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 173,X'S) H   ( 172,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 163,X'S) H   ( 162,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE C   (  23,X'S) H   ( 233,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   ( 153,X'S) H   (1532,X'S) H   (1531,X'S) H   (1533,X'S) 
RIDE C   ( 154,X'S) H   (1542,X'S) H   (1541,X'S) H   (1543,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
SAME  O(51)  C(52)  C(53)  C(54)  AND 
CONT  O(51)  C(52)  C(54)  C(53)  AND 
CONT  O(51)  C(52)  C(153)  C(154)  AND 
CONT  O(51)  C(52)  C(154)  C(153) 
SIMU  0.01   O(51)  C(52)  C(53)  C(54)  AND 
CONT  O(51)  C(52)  C(54)  C(53)  AND 
CONT  O(51)  C(52)  C(153)  C(154)  AND 
CONT  O(51)  C(52)  C(154)  C(153) 
DELU  0.01   O(51)  C(52)  C(53)  C(54)  AND 
CONT  O(51)  C(52)  C(54)  C(53)  AND 
CONT  O(51)  C(52)  C(153)  C(154)  AND 
CONT  O(51)  C(52)  C(154)  C(153) 
END                                                                             
;
_cod_data_source_file            ol6b02744_si_002.cif
_cod_data_source_block           3_absolute
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C21 H23 Br1 N2 O4'
_cod_database_code               1555859