#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029842.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_4029842
loop_
_publ_author_name
'Tang, Jian'
'Yue, Jia-Jun'
'Tao, Fei-Fei'
'Grampp, Guenter'
'Wang, Bing-Xiang'
'Li, Fang'
'Liang, Xue-Zheng'
'Shen, Yong-Miao'
'Xu, Jian-Hua'
_publ_section_title
;
 A three-component reaction by photoinduced electron transfer mechanism
 with N-protected pyrroles as neutral carbon nucleophiles.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7572
_journal_page_last               7582
_journal_paper_doi               10.1021/jo5013114
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C23 H18 N4'
_chemical_formula_sum            'C23 H18 N4'
_chemical_formula_weight         350.41
_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                84.179(4)
_cell_angle_beta                 86.210(4)
_cell_angle_gamma                79.569(4)
_cell_formula_units_Z            2
_cell_length_a                   7.943(2)
_cell_length_b                   10.527(3)
_cell_length_c                   11.702(4)
_cell_measurement_reflns_used    1070
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.31
_cell_volume                     956.2(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6989
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0522
_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)+(0.0505P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                1869
_reflns_number_total             3506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5013114_si_002.cif
_cod_data_source_block           1
_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/rss-feeds/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029837--4029842.cif.
;
_cod_original_sg_symbol_Hall     '-P 1   '
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4029842
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
C1 C 0.2626(3) 0.4425(2) 0.95085(18) 0.0546(6) Uani 1 1 d .
C2 C 0.2321(3) 0.3502(2) 1.04030(17) 0.0580(6) Uani 1 1 d .
C3 C 0.2660(3) 0.2206(2) 1.01958(18) 0.0617(6) Uani 1 1 d .
H3 H 0.2462 0.1577 1.0781 0.074 Uiso 1 1 calc R
C4 C 0.3295(3) 0.1837(2) 0.91206(17) 0.0543(6) Uani 1 1 d .
C5 C 0.3647(2) 0.2754(2) 0.82085(16) 0.0479(5) Uani 1 1 d .
C6 C 0.3272(3) 0.4050(2) 0.84419(17) 0.0535(6) Uani 1 1 d .
H6 H 0.3462 0.4687 0.7861 0.064 Uiso 1 1 calc R
C7 C 0.2202(3) 0.5776(3) 0.96775(19) 0.0653(7) Uani 1 1 d .
C8 C 0.1644(3) 0.3889(3) 1.1511(2) 0.0705(7) Uani 1 1 d .
C9 C 0.3609(3) 0.0466(3) 0.89950(18) 0.0619(7) Uani 1 1 d .
C10 C 0.4381(3) 0.23315(19) 0.70379(16) 0.0465(5) Uani 1 1 d .
C11 C 0.6099(3) 0.14140(19) 0.71768(16) 0.0455(5) Uani 1 1 d .
C12 C 0.7180(3) 0.1572(2) 0.80111(18) 0.0555(6) Uani 1 1 d .
H12 H 0.6818 0.2208 0.8514 0.067 Uiso 1 1 calc R
C13 C 0.8781(3) 0.0813(2) 0.8117(2) 0.0652(7) Uani 1 1 d .
H13 H 0.9477 0.0934 0.8691 0.078 Uiso 1 1 calc R
C14 C 0.9340(3) -0.0115(2) 0.7380(2) 0.0739(7) Uani 1 1 d .
H14 H 1.0420 -0.0626 0.7445 0.089 Uiso 1 1 calc R
C15 C 0.8297(3) -0.0289(2) 0.6543(2) 0.0819(8) Uani 1 1 d .
H15 H 0.8674 -0.0920 0.6037 0.098 Uiso 1 1 calc R
C16 C 0.6688(3) 0.0468(2) 0.6444(2) 0.0657(7) Uani 1 1 d .
H16 H 0.5993 0.0336 0.5874 0.079 Uiso 1 1 calc R
C17 C 0.4681(3) 0.3538(2) 0.62104(16) 0.0533(6) Uani 1 1 d .
H17A H 0.3593 0.4123 0.6131 0.064 Uiso 1 1 calc R
H17B H 0.5443 0.3987 0.6566 0.064 Uiso 1 1 calc R
C18 C 0.5416(3) 0.3261(2) 0.50385(17) 0.0516(6) Uani 1 1 d .
C19 C 0.4631(3) 0.3025(2) 0.40952(18) 0.0688(7) Uani 1 1 d .
H19 H 0.3469 0.3007 0.4058 0.083 Uiso 1 1 calc R
C20 C 0.5879(4) 0.2814(2) 0.3191(2) 0.0823(9) Uani 1 1 d .
H20 H 0.5700 0.2623 0.2455 0.099 Uiso 1 1 calc R
C21 C 0.7390(4) 0.2942(2) 0.3596(2) 0.0782(8) Uani 1 1 d .
H21 H 0.8437 0.2860 0.3181 0.094 Uiso 1 1 calc R
C22 C 0.8443(3) 0.3447(3) 0.5420(2) 0.0900(9) Uani 1 1 d .
H22A H 0.8032 0.4208 0.5814 0.135 Uiso 1 1 calc R
H22B H 0.9437 0.3574 0.4939 0.135 Uiso 1 1 calc R
H22C H 0.8740 0.2714 0.5973 0.135 Uiso 1 1 calc R
C23 C 0.3030(3) 0.1697(2) 0.65225(18) 0.0652(7) Uani 1 1 d .
H23A H 0.2937 0.0889 0.6962 0.098 Uiso 1 1 calc R
H23B H 0.3373 0.1541 0.5740 0.098 Uiso 1 1 calc R
H23C H 0.1940 0.2266 0.6546 0.098 Uiso 1 1 calc R
N1 N 0.1794(3) 0.6845(2) 0.98230(19) 0.0929(8) Uani 1 1 d .
N2 N 0.1076(3) 0.4217(2) 1.23733(18) 0.0959(8) Uani 1 1 d .
N3 N 0.3803(3) -0.0624(2) 0.89394(17) 0.0818(7) Uani 1 1 d .
N4 N 0.7119(3) 0.32139(17) 0.47191(15) 0.0608(5) 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
C6 C1 C2 120.7(2)
C6 C1 C7 119.5(2)
C2 C1 C7 119.77(19)
C3 C2 C1 118.45(19)
C3 C2 C8 120.8(2)
C1 C2 C8 120.8(2)
C2 C3 C4 120.6(2)
C2 C3 H3 119.7
C4 C3 H3 119.7
C3 C4 C5 121.9(2)
C3 C4 C9 116.3(2)
C5 C4 C9 121.83(19)
C6 C5 C4 116.00(18)
C6 C5 C10 122.68(18)
C4 C5 C10 121.31(18)
C1 C6 C5 122.4(2)
C1 C6 H6 118.8
C5 C6 H6 118.8
N1 C7 C1 177.0(3)
N2 C8 C2 178.2(3)
N3 C9 C4 176.7(3)
C5 C10 C11 109.98(15)
C5 C10 C23 107.44(16)
C11 C10 C23 112.70(17)
C5 C10 C17 110.20(16)
C11 C10 C17 108.44(16)
C23 C10 C17 108.07(16)
C16 C11 C12 117.3(2)
C16 C11 C10 122.37(18)
C12 C11 C10 120.19(18)
C13 C12 C11 121.8(2)
C13 C12 H12 119.1
C11 C12 H12 119.1
C14 C13 C12 119.9(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 119.5(2)
C13 C14 H14 120.3
C15 C14 H14 120.3
C14 C15 C16 120.4(2)
C14 C15 H15 119.8
C16 C15 H15 119.8
C11 C16 C15 121.1(2)
C11 C16 H16 119.5
C15 C16 H16 119.5
C18 C17 C10 115.80(17)
C18 C17 H17A 108.3
C10 C17 H17A 108.3
C18 C17 H17B 108.3
C10 C17 H17B 108.3
H17A C17 H17B 107.4
C19 C18 N4 106.8(2)
C19 C18 C17 130.0(2)
N4 C18 C17 123.24(19)
C18 C19 C20 108.4(2)
C18 C19 H19 125.8
C20 C19 H19 125.8
C21 C20 C19 107.0(2)
C21 C20 H20 126.5
C19 C20 H20 126.5
C20 C21 N4 108.6(2)
C20 C21 H21 125.7
N4 C21 H21 125.7
N4 C22 H22A 109.5
N4 C22 H22B 109.5
H22A C22 H22B 109.5
N4 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C10 C23 H23A 109.5
C10 C23 H23B 109.5
H23A C23 H23B 109.5
C10 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C21 N4 C18 109.2(2)
C21 N4 C22 123.9(2)
C18 N4 C22 126.81(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.385(3)
C1 C2 1.394(3)
C1 C7 1.432(3)
C2 C3 1.385(3)
C2 C8 1.439(3)
C3 C4 1.390(3)
C3 H3 0.9300
C4 C5 1.413(3)
C4 C9 1.440(3)
C5 C6 1.394(3)
C5 C10 1.529(3)
C6 H6 0.9300
C7 N1 1.140(3)
C8 N2 1.138(3)
C9 N3 1.138(3)
C10 C11 1.531(3)
C10 C23 1.545(3)
C10 C17 1.561(3)
C11 C16 1.377(3)
C11 C12 1.383(3)
C12 C13 1.380(3)
C12 H12 0.9300
C13 C14 1.363(3)
C13 H13 0.9300
C14 C15 1.371(3)
C14 H14 0.9300
C15 C16 1.383(3)
C15 H15 0.9300
C16 H16 0.9300
C17 C18 1.490(3)
C17 H17A 0.9700
C17 H17B 0.9700
C18 C19 1.368(3)
C18 N4 1.373(3)
C19 C20 1.408(3)
C19 H19 0.9300
C20 C21 1.352(3)
C20 H20 0.9300
C21 N4 1.368(3)
C21 H21 0.9300
C22 N4 1.445(3)
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
