#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:20:51 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178946 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/75/4117569.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4117569
loop_
_publ_author_name
'Yi-Feng Wang'
'Xu Zhu'
'Shunsuke Chiba'
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_contact_author_email       shunsuke@ntu.edu.sg
_publ_contact_author_fax         '+65 6791 1961'
_publ_contact_author_phone       '+65 6513 8013'
_publ_section_title
;
 Copper-Catalyzed Aerobic [3+2]-Annulation of N-Alkenyl Amidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3679
_journal_page_last               3682
_journal_paper_doi               10.1021/ja2120629
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C27 H26 N2'
_chemical_formula_sum            'C27 H26 N2'
_chemical_formula_weight         378.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8508(3)
_cell_length_b                   19.2961(6)
_cell_length_c                   10.3465(3)
_cell_measurement_reflns_used    5286
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.11
_cell_volume                     1929.77(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12941
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0712P)²+0.4449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                3969
_reflns_number_total             4755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2120629_si_004.cif
_cod_data_source_block           2q_chiba184s
_cod_database_code               4117569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.30880(13) 0.08796(7) 0.46636(12) 0.0158(3) Uani 1 1 d .
H1 H 0.2470 0.1079 0.3941 0.019 Uiso 1 1 calc R
C2 C 0.28649(14) 0.02093(7) 0.50697(13) 0.0186(3) Uani 1 1 d .
H2 H 0.2104 -0.0052 0.4612 0.022 Uiso 1 1 calc R
C3 C 0.37506(15) -0.00803(7) 0.61423(12) 0.0196(3) Uani 1 1 d .
H3 H 0.3592 -0.0537 0.6421 0.024 Uiso 1 1 calc R
C4 C 0.48691(15) 0.03005(7) 0.68062(12) 0.0200(3) Uani 1 1 d .
H4 H 0.5466 0.0106 0.7548 0.024 Uiso 1 1 calc R
C5 C 0.51156(13) 0.09640(7) 0.63881(12) 0.0164(3) Uani 1 1 d .
H5 H 0.5894 0.1218 0.6830 0.020 Uiso 1 1 calc R
C6 C 0.42197(13) 0.12587(6) 0.53170(11) 0.0139(2) Uani 1 1 d .
C7 C 0.45119(12) 0.19492(6) 0.48159(11) 0.0130(2) Uani 1 1 d .
C8 C 0.56024(13) 0.28475(6) 0.41317(12) 0.0145(2) Uani 1 1 d .
H8 H 0.5898 0.2778 0.3269 0.017 Uiso 1 1 calc R
C9 C 0.64836(13) 0.34276(7) 0.48642(12) 0.0180(3) Uani 1 1 d .
H9A H 0.6503 0.3819 0.4249 0.022 Uiso 1 1 calc R
H9B H 0.7444 0.3257 0.5139 0.022 Uiso 1 1 calc R
C10 C 0.59807(14) 0.36982(8) 0.60844(13) 0.0225(3) Uani 1 1 d .
H10A H 0.6134 0.4205 0.6146 0.027 Uiso 1 1 calc R
H10B H 0.6550 0.3485 0.6878 0.027 Uiso 1 1 calc R
C11 C 0.44505(13) 0.35513(7) 0.60911(11) 0.0159(3) Uani 1 1 d .
H11A H 0.4105 0.3901 0.6648 0.019 Uiso 1 1 calc R
H11B H 0.4371 0.3091 0.6492 0.019 Uiso 1 1 calc R
C12 C 0.35318(12) 0.35642(6) 0.47067(11) 0.0120(2) Uani 1 1 d .
H12 H 0.3526 0.4035 0.4300 0.014 Uiso 1 1 calc R
C13 C 0.40350(12) 0.30136(6) 0.38418(11) 0.0120(2) Uani 1 1 d .
H13 H 0.3708 0.3122 0.2887 0.014 Uiso 1 1 calc R
C14 C 0.22786(12) 0.25181(6) 0.49305(11) 0.0122(2) Uani 1 1 d .
H14A H 0.2568 0.2406 0.5877 0.015 Uiso 1 1 calc R
H14B H 0.1431 0.2253 0.4566 0.015 Uiso 1 1 calc R
C15 C 0.20323(12) 0.33115(6) 0.47249(11) 0.0109(2) Uani 1 1 d .
C16 C 0.13751(12) 0.36641(6) 0.57749(11) 0.0122(2) Uani 1 1 d .
C17 C 0.14003(13) 0.43875(7) 0.58602(11) 0.0151(3) Uani 1 1 d .
H17 H 0.1919 0.4645 0.5341 0.018 Uiso 1 1 calc R
C18 C 0.06795(14) 0.47378(7) 0.66917(12) 0.0177(3) Uani 1 1 d .
H18 H 0.0719 0.5229 0.6747 0.021 Uiso 1 1 calc R
C19 C -0.00987(14) 0.43662(7) 0.74414(12) 0.0181(3) Uani 1 1 d .
H19 H -0.0614 0.4603 0.7992 0.022 Uiso 1 1 calc R
C20 C -0.01187(13) 0.36491(7) 0.73817(12) 0.0167(3) Uani 1 1 d .
H20 H -0.0642 0.3394 0.7901 0.020 Uiso 1 1 calc R
C21 C 0.06236(12) 0.32977(7) 0.65640(11) 0.0139(2) Uani 1 1 d .
H21 H 0.0617 0.2805 0.6544 0.017 Uiso 1 1 calc R
C22 C 0.09936(12) 0.34156(6) 0.34140(11) 0.0115(2) Uani 1 1 d .
C23 C 0.12641(13) 0.37923(6) 0.23405(11) 0.0135(2) Uani 1 1 d .
H23 H 0.2137 0.4011 0.2393 0.016 Uiso 1 1 calc R
C24 C 0.02585(13) 0.38510(7) 0.11856(11) 0.0156(3) Uani 1 1 d .
H24 H 0.0458 0.4110 0.0464 0.019 Uiso 1 1 calc R
C25 C -0.10208(13) 0.35363(7) 0.10823(12) 0.0162(3) Uani 1 1 d .
H25 H -0.1690 0.3570 0.0290 0.019 Uiso 1 1 calc R
C26 C -0.13135(13) 0.31693(7) 0.21574(12) 0.0157(3) Uani 1 1 d .
H26 H -0.2192 0.2956 0.2105 0.019 Uiso 1 1 calc R
C27 C -0.03218(13) 0.31157(6) 0.33026(11) 0.0137(2) Uani 1 1 d .
H27 H -0.0539 0.2869 0.4032 0.016 Uiso 1 1 calc R
N1 N 0.34012(10) 0.23618(5) 0.42009(9) 0.0117(2) Uani 1 1 d .
N2 N 0.57426(11) 0.21757(6) 0.48361(10) 0.0160(2) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 119.98(12)
C2 C1 H1 120.0
C6 C1 H1 120.0
C3 C2 C1 120.25(12)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 119.84(12)
C2 C3 H3 120.1
C4 C3 H3 120.1
C5 C4 C3 120.20(12)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.06(12)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 119.65(11)
C1 C6 C7 119.63(11)
C5 C6 C7 120.60(11)
N2 C7 N1 117.72(11)
N2 C7 C6 123.22(11)
N1 C7 C6 118.90(11)
N2 C8 C9 114.06(10)
N2 C8 C13 105.75(9)
C9 C8 C13 113.26(10)
N2 C8 H8 107.8
C9 C8 H8 107.8
C13 C8 H8 107.8
C8 C9 C10 114.55(11)
C8 C9 H9A 108.6
C10 C9 H9A 108.6
C8 C9 H9B 108.6
C10 C9 H9B 108.6
H9A C9 H9B 107.6
C9 C10 C11 114.46(10)
C9 C10 H10A 108.6
C11 C10 H10A 108.6
C9 C10 H10B 108.6
C11 C10 H10B 108.6
H10A C10 H10B 107.6
C10 C11 C12 113.22(10)
C10 C11 H11A 108.9
C12 C11 H11A 108.9
C10 C11 H11B 108.9
C12 C11 H11B 108.9
H11A C11 H11B 107.7
C13 C12 C11 109.51(10)
C13 C12 C15 101.79(9)
C11 C12 C15 111.83(9)
C13 C12 H12 111.1
C11 C12 H12 111.1
C15 C12 H12 111.1
N1 C13 C12 104.03(9)
N1 C13 C8 103.19(9)
C12 C13 C8 116.96(9)
N1 C13 H13 110.7
C12 C13 H13 110.7
C8 C13 H13 110.7
N1 C14 C15 103.98(9)
N1 C14 H14A 111.0
C15 C14 H14A 111.0
N1 C14 H14B 111.0
C15 C14 H14B 111.0
H14A C14 H14B 109.0
C16 C15 C22 105.45(9)
C16 C15 C14 114.62(9)
C22 C15 C14 107.86(9)
C16 C15 C12 113.69(9)
C22 C15 C12 114.64(9)
C14 C15 C12 100.72(9)
C21 C16 C17 118.27(11)
C21 C16 C15 122.40(11)
C17 C16 C15 118.99(10)
C18 C17 C16 121.25(12)
C18 C17 H17 119.4
C16 C17 H17 119.4
C19 C18 C17 119.77(12)
C19 C18 H18 120.1
C17 C18 H18 120.1
C20 C19 C18 119.66(11)
C20 C19 H19 120.2
C18 C19 H19 120.2
C19 C20 C21 120.51(12)
C19 C20 H20 119.7
C21 C20 H20 119.7
C16 C21 C20 120.49(12)
C16 C21 H21 119.8
C20 C21 H21 119.8
C23 C22 C27 117.67(11)
C23 C22 C15 124.76(11)
C27 C22 C15 117.57(10)
C22 C23 C24 120.57(11)
C22 C23 H23 119.7
C24 C23 H23 119.7
C25 C24 C23 120.89(11)
C25 C24 H24 119.6
C23 C24 H24 119.6
C24 C25 C26 119.10(11)
C24 C25 H25 120.5
C26 C25 H25 120.5
C27 C26 C25 119.96(12)
C27 C26 H26 120.0
C25 C26 H26 120.0
C26 C27 C22 121.78(11)
C26 C27 H27 119.1
C22 C27 H27 119.1
C7 N1 C13 105.42(9)
C7 N1 C14 118.48(9)
C13 N1 C14 110.24(9)
C7 N2 C8 106.95(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3904(18)
C1 C6 1.3943(18)
C1 H1 0.9500
C2 C3 1.3899(19)
C2 H2 0.9500
C3 C4 1.391(2)
C3 H3 0.9500
C4 C5 1.3878(19)
C4 H4 0.9500
C5 C6 1.3975(17)
C5 H5 0.9500
C6 C7 1.4780(17)
C7 N2 1.2851(16)
C7 N1 1.4027(15)
C8 N2 1.4806(16)
C8 C9 1.5254(18)
C8 C13 1.5486(16)
C8 H8 1.0000
C9 C10 1.5341(18)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.5352(18)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.5399(16)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.5317(16)
C12 C15 1.5591(16)
C12 H12 1.0000
C13 N1 1.4830(15)
C13 H13 1.0000
C14 N1 1.4851(15)
C14 C15 1.5583(16)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.5276(16)
C15 C22 1.5465(15)
C16 C21 1.3956(16)
C16 C17 1.3986(17)
C17 C18 1.3917(17)
C17 H17 0.9500
C18 C19 1.3902(19)
C18 H18 0.9500
C19 C20 1.3852(19)
C19 H19 0.9500
C20 C21 1.3960(17)
C20 H20 0.9500
C21 H21 0.9500
C22 C23 1.3954(16)
C22 C27 1.4033(17)
C23 C24 1.4019(16)
C23 H23 0.9500
C24 C25 1.3843(18)
C24 H24 0.9500
C25 C26 1.3948(17)
C25 H25 0.9500
C26 C27 1.3866(16)
C26 H26 0.9500
C27 H27 0.9500
