#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/98/1529856.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_1529856
loop_
_publ_author_name
'Zhu, Yuelu'
'Li, Cheng'
'Zhang, Jidong'
'She, Mengyao'
'Sun, Wei'
'Wan, Kerou'
'Wang, Yaqi'
'Yin, Bin'
'Liu, Ping'
'Li, Jianli'
_publ_section_title
;
 A Facile FeCl3/I2-Catalyzed Aerobic Oxidative Coupling Reaction:
 Synthesis of Tetrasubstituted Imidazoles from Amidines and Chalcones.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3872
_journal_page_last               3875
_journal_paper_doi               10.1021/acs.orglett.5b01854
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C29 H21 Br N2 O'
_chemical_formula_weight         493.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.826(5)
_cell_angle_beta                 103.604(5)
_cell_angle_gamma                112.844(5)
_cell_formula_units_Z            2
_cell_length_a                   9.724(3)
_cell_length_b                   11.142(3)
_cell_length_c                   12.910(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1205.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.1045
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6362
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    1.729
_exptl_absorpt_correction_T_max  0.6718
_exptl_absorpt_correction_T_min  0.5829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.2146
_reflns_number_gt                2124
_reflns_number_total             4576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01854_si_002.cif
_cod_data_source_block           xb8062_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1529856
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.31791(9) -0.08292(10) -0.45331(6) 0.0991(5) Uani 1 1 d .
O1 O 0.8593(4) 0.3113(4) -0.0117(3) 0.0562(11) Uani 1 1 d .
N1 N 0.8951(5) -0.0226(5) 0.1374(4) 0.0453(12) Uani 1 1 d .
N2 N 0.7760(5) 0.0369(4) 0.0004(3) 0.0395(11) Uani 1 1 d .
C1 C 0.7110(7) -0.0222(6) -0.1989(4) 0.0528(15) Uani 1 1 d .
H1 H 0.8035 -0.0312 -0.1927 0.063 Uiso 1 1 calc R
C2 C 0.5976(8) -0.0545(6) -0.3035(5) 0.0608(17) Uani 1 1 d .
H2 H 0.6128 -0.0910 -0.3672 0.073 Uiso 1 1 calc R
C3 C 0.4679(7) -0.0334(6) -0.3127(5) 0.0577(16) Uani 1 1 d .
C4 C 0.4422(6) 0.0215(5) -0.2207(5) 0.0476(15) Uani 1 1 d .
H4 H 0.3552 0.0395 -0.2281 0.057 Uiso 1 1 calc R
C5 C 0.5466(6) 0.0497(5) -0.1173(4) 0.0442(14) Uani 1 1 d .
H5 H 0.5297 0.0864 -0.0544 0.053 Uiso 1 1 calc R
C6 C 0.6772(7) 0.0235(5) -0.1065(4) 0.0441(14) Uani 1 1 d .
C7 C 0.7934(7) -0.2901(6) 0.0006(5) 0.0507(15) Uani 1 1 d .
H7 H 0.8945 -0.2499 0.0517 0.061 Uiso 1 1 calc R
C8 C 0.7224(7) -0.4262(7) -0.0486(5) 0.0602(17) Uani 1 1 d .
H8 H 0.7770 -0.4766 -0.0305 0.072 Uiso 1 1 calc R
C9 C 0.5752(8) -0.4899(6) -0.1228(5) 0.0556(16) Uani 1 1 d .
C10 C 0.4904(8) -0.4137(6) -0.1492(5) 0.0643(18) Uani 1 1 d .
H10 H 0.3881 -0.4559 -0.1987 0.077 Uiso 1 1 calc R
C11 C 0.5620(8) -0.2766(6) -0.1003(5) 0.0596(17) Uani 1 1 d .
H11 H 0.5072 -0.2261 -0.1173 0.072 Uiso 1 1 calc R
C12 C 0.7165(6) -0.2112(5) -0.0250(4) 0.0449(14) Uani 1 1 d .
C13 C 0.4996(9) -0.6414(6) -0.1753(6) 0.081(2) Uani 1 1 d .
H13A H 0.5294 -0.6592 -0.2397 0.121 Uiso 1 1 calc R
H13B H 0.3869 -0.6763 -0.1964 0.121 Uiso 1 1 calc R
H13C H 0.5346 -0.6845 -0.1230 0.121 Uiso 1 1 calc R
C14 C 0.7954(6) -0.0670(6) 0.0360(4) 0.0465(14) Uani 1 1 d .
C15 C 1.0610(8) 0.1319(7) 0.3678(5) 0.0631(17) Uani 1 1 d .
H15 H 0.9849 0.0439 0.3549 0.076 Uiso 1 1 calc R
C16 C 1.1689(9) 0.1988(9) 0.4717(6) 0.082(2) Uani 1 1 d .
H16 H 1.1638 0.1579 0.5292 0.098 Uiso 1 1 calc R
C17 C 1.2846(9) 0.3270(10) 0.4899(6) 0.094(3) Uani 1 1 d .
H17 H 1.3601 0.3727 0.5595 0.113 Uiso 1 1 calc R
C18 C 1.2886(9) 0.3873(8) 0.4054(6) 0.095(3) Uani 1 1 d .
H18 H 1.3647 0.4755 0.4193 0.114 Uiso 1 1 calc R
C19 C 1.1825(6) 0.3205(6) 0.3002(5) 0.0622(18) Uani 1 1 d .
H19 H 1.1912 0.3608 0.2426 0.075 Uiso 1 1 calc R
C20 C 1.0626(7) 0.1925(6) 0.2813(4) 0.0515(15) Uani 1 1 d .
C21 C 0.9420(6) 0.1145(6) 0.1709(4) 0.0421(13) Uani 1 1 d .
C22 C 0.8520(6) 0.3549(6) 0.2647(5) 0.0509(15) Uani 1 1 d .
H22 H 0.7978 0.2642 0.2616 0.061 Uiso 1 1 calc R
C23 C 0.8786(8) 0.4547(8) 0.3556(5) 0.0702(19) Uani 1 1 d .
H23 H 0.8405 0.4313 0.4128 0.084 Uiso 1 1 calc R
C24 C 0.9614(10) 0.5882(8) 0.3609(7) 0.088(2) Uani 1 1 d .
H24 H 0.9805 0.6555 0.4223 0.106 Uiso 1 1 calc R
C25 C 1.0160(9) 0.6224(7) 0.2756(7) 0.087(2) Uani 1 1 d .
H25 H 1.0729 0.7130 0.2796 0.104 Uiso 1 1 calc R
C26 C 0.9874(8) 0.5248(6) 0.1861(5) 0.0641(18) Uani 1 1 d .
H26 H 1.0233 0.5492 0.1282 0.077 Uiso 1 1 calc R
C27 C 0.9053(6) 0.3892(6) 0.1790(4) 0.0448(14) Uani 1 1 d .
C28 C 0.8755(6) 0.2869(6) 0.0785(4) 0.0428(14) Uani 1 1 d .
C29 C 0.8662(6) 0.1547(5) 0.0879(4) 0.0424(13) 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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C14 N1 C21 106.8(4)
C14 N2 C29 107.4(4)
C14 N2 C6 125.3(4)
C29 N2 C6 127.3(4)
C6 C1 C2 116.7(5)
C3 C2 C1 121.5(6)
C2 C3 C4 121.0(5)
C2 C3 Br1 119.8(5)
C4 C3 Br1 119.2(5)
C3 C4 C5 119.3(5)
C4 C5 C6 120.2(5)
C1 C6 C5 121.0(5)
C1 C6 N2 118.2(5)
C5 C6 N2 120.8(5)
C8 C7 C12 120.8(5)
C9 C8 C7 122.0(6)
C8 C9 C10 119.2(6)
C8 C9 C13 120.6(6)
C10 C9 C13 120.2(6)
C11 C10 C9 118.9(6)
C10 C11 C12 121.3(6)
C7 C12 C11 117.8(5)
C7 C12 C14 118.0(5)
C11 C12 C14 123.9(5)
N1 C14 N2 111.0(5)
N1 C14 C12 121.8(5)
N2 C14 C12 127.2(5)
C16 C15 C20 121.6(7)
C15 C16 C17 119.3(7)
C18 C17 C16 119.8(7)
C17 C18 C19 121.6(7)
C18 C19 C20 119.2(6)
C19 C20 C15 118.4(5)
C19 C20 C21 122.7(5)
C15 C20 C21 118.8(5)
N1 C21 C29 110.0(5)
N1 C21 C20 118.3(5)
C29 C21 C20 131.7(5)
C27 C22 C23 120.3(6)
C24 C23 C22 119.7(7)
C23 C24 C25 120.0(7)
C26 C25 C24 120.2(7)
C25 C26 C27 121.0(7)
C22 C27 C26 118.8(6)
C22 C27 C28 122.5(5)
C26 C27 C28 118.7(5)
O1 C28 C29 119.9(5)
O1 C28 C27 121.0(5)
C29 C28 C27 119.0(5)
C21 C29 N2 104.7(4)
C21 C29 C28 132.8(5)
N2 C29 C28 122.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.884(6)
O1 C28 1.224(6)
N1 C14 1.315(6)
N1 C21 1.375(7)
N2 C14 1.371(7)
N2 C29 1.398(6)
N2 C6 1.432(6)
C1 C6 1.386(8)
C1 C2 1.418(7)
C2 C3 1.352(8)
C3 C4 1.372(8)
C4 C5 1.378(7)
C5 C6 1.391(7)
C7 C8 1.365(8)
C7 C12 1.387(7)
C8 C9 1.352(8)
C9 C10 1.420(8)
C9 C13 1.517(8)
C10 C11 1.374(8)
C11 C12 1.407(8)
C12 C14 1.470(8)
C15 C16 1.371(9)
C15 C20 1.391(8)
C16 C17 1.374(10)
C17 C18 1.366(10)
C18 C19 1.378(9)
C19 C20 1.386(8)
C20 C21 1.484(7)
C21 C29 1.387(7)
C22 C27 1.372(8)
C22 C23 1.383(8)
C23 C24 1.370(9)
C24 C25 1.373(11)
C25 C26 1.351(9)
C26 C27 1.385(8)
C27 C28 1.476(8)
C28 C29 1.467(7)
