Substrate-controlled switchable asymmetric annulations to access polyheterocyclic skeletons.
Wang, Kai-Kai; Wang, Pan; Ouyang, Qin; Du, Wei; Chen, Ying-Chun; Chemical communications (Cambridge, England) 52 (2016) 11104–11107; doi:10.1039/c6cc06148f

data_7125022
_publ_section_title
;
 Substrate-controlled switchable asymmetric annulations to access
 polyheterocyclic skeletons.
;
_journal_issue                   74
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11104
_journal_page_last               11107
_journal_paper_doi               10.1039/c6cc06148f
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H21 Br N2 O4'
_chemical_formula_sum            'C29 H21 Br N2 O4'
_chemical_formula_weight         541.39
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-26 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.08473(14)
_cell_length_b                   16.7619(4)
_cell_length_c                   22.0850(6)
_cell_measurement_reflns_used    6583
_cell_measurement_temperature    292.4(3)
_cell_measurement_theta_max      72.1870
_cell_measurement_theta_min      5.2680
_cell_volume                     2622.67(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.4(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000   60.0000 84

  2 omega    1.00   75.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  -60.0000 74

  3 omega   19.00  103.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -30.0000 84

  4 omega  -32.00   63.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000 -180.0000 95

  5 omega   19.00  103.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -60.0000 84

  6 omega  -31.00   53.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -90.0000 84

  7 omega   39.00  109.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

  8 omega   38.00   91.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

  9 omega   38.00   91.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 10 omega   38.00   91.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 11 omega   40.00   98.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 12 omega   40.00   98.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 13 omega   38.00   91.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 14 omega   39.00  109.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 15 omega   37.00  144.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -16.0000  -84.0000 107

 16 omega   19.00  103.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   60.0000 84

 17 omega   17.00  105.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000 -150.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0488998000
_diffrn_orient_matrix_UB_12      0.0245742000
_diffrn_orient_matrix_UB_13      -0.0653274000
_diffrn_orient_matrix_UB_21      -0.0027556000
_diffrn_orient_matrix_UB_22      0.0882910000
_diffrn_orient_matrix_UB_23      0.0193673000
_diffrn_orient_matrix_UB_31      0.2119481000
_diffrn_orient_matrix_UB_32      0.0068428000
_diffrn_orient_matrix_UB_33      -0.0148316000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.494
_diffrn_reflns_theta_min         5.278
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.825
_refine_diff_density_min         -1.363
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details
;
 Flack x determined using 1737 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.044(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1444P)^2^+1.2789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2211
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4641
_reflns_number_total             5097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06148f2.cif
_cod_data_source_block           3t
_cod_original_cell_volume        2622.68(10)
_cod_database_code               7125022
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00O(H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00L(H00L), C00M(H00M), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C010(H010)
2.c Idealised Me refined as rotating group:
 C00R(H00B,H00E,H00F), C00Z(H00G,H00H,H00I)
;
_shelx_res_checksum              2539
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-15
_olex2_submission_special_instructions 'No special instructions were received'