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_7125023
_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         'C23 H17 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O2'
_chemical_formula_weight         367.39
_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             2016-05-05
_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                   10.06732(18)
_cell_length_b                   10.59058(14)
_cell_length_c                   22.9703(4)
_cell_measurement_reflns_used    5700
_cell_measurement_temperature    292.6(5)
_cell_measurement_theta_max      72.3190
_cell_measurement_theta_min      5.6780
_cell_volume                     2449.06(7)
_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_reduction
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.6(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_orient_matrix_UB_11      -0.0447668000
_diffrn_orient_matrix_UB_12      0.0144130000
_diffrn_orient_matrix_UB_13      -0.0637958000
_diffrn_orient_matrix_UB_21      0.1376635000
_diffrn_orient_matrix_UB_22      -0.0447363000
_diffrn_orient_matrix_UB_23      -0.0207116000
_diffrn_orient_matrix_UB_31      -0.0494311000
_diffrn_orient_matrix_UB_32      -0.1377093000
_diffrn_orient_matrix_UB_33      0.0000188000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13639
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.606
_diffrn_reflns_theta_min         4.598
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69532
_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    0.996
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1743 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0874P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4423
_reflns_number_total             4769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06148f2.cif
_cod_data_source_block           5a
_cod_database_code               7125023
_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. Rigid bond restraints
 C00O, C00P
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C00R, C00P
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
C00O \\sim C00P: within 1.7A with sigma of 0.007 and sigma for terminal atoms
of 0.001
C00R \\sim C00P: within 1.7A with sigma of 0.007 and sigma for terminal atoms
of 0.001
4.a Ternary CH refined with riding coordinates:
 C00B(H00B)
4.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K),
 C00M(H00M), C00O(H00O), C00P(H00P), C00R(H00R)
4.c Idealised Me refined as rotating group:
 C00Q(H00A,H00C,H00E), C00S(H00G,H00J,H00L)
;
_shelx_res_checksum              40125
_shelx_fab_checksum              91074
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'