N-Heterocyclic carbene-catalyzed [2+3] cyclocondensation of α-chloroaldehydes with azomethine imines
Gao, Zhong-Hua; Chen, Xiang-Yu; Cheng, Jin-Tang; Liao, Wei-Lin; Ye, Song; Chemical Communications (Cambridge, United Kingdom) 51 (2015) 9328–9331; doi:10.1039/c5cc01238d

data_7117284
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed [2+3] cyclocondensation of
 \a-chloroaldehydes with azomethine imines
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   45
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              9328
_journal_page_last               9331
_journal_paper_doi               10.1039/c5cc01238d
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H21 Br N2 O2'
_chemical_formula_sum            'C25 H21 Br N2 O2'
_chemical_formula_weight         461.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-02-10 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.81(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.912(2)
_cell_length_b                   8.3793(17)
_cell_length_c                   11.228(2)
_cell_measurement_reflns_used    3168
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4793
_cell_measurement_theta_min      2.4307
_cell_volume                     1024.4(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0011
_diffrn_orient_matrix_UB_12      -0.0142
_diffrn_orient_matrix_UB_13      0.0907
_diffrn_orient_matrix_UB_21      -0.0285
_diffrn_orient_matrix_UB_22      0.1145
_diffrn_orient_matrix_UB_23      0.0176
_diffrn_orient_matrix_UB_31      -0.0866
_diffrn_orient_matrix_UB_32      -0.0218
_diffrn_orient_matrix_UB_33      0.0015
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11644
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.694
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.031
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       Plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1646 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.005(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0239P)^2^+0.1899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0754
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                4196
_reflns_number_total             4483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7117209
_cod_data_source_file            c5cc01238d2.cif
_cod_data_source_block           sa3771
_cod_original_cell_volume        1024.4(4)
_cod_database_code               7117284
_shelxl_version_number           2013-4
_diffrn_number_total             2492
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_shelx_res_checksum              19248