#------------------------------------------------------------------------------
#$Date: 2017-10-05 02:06:44 +0300 (Thu, 05 Oct 2017) $
#$Revision: 201693 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/92/7229288.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_7229288
loop_
_publ_author_name
'Bandi, Vijayalakshmi'
'Kavala, Veerababurao'
'Hsu, Che-Hao'
'Konala, Ashok'
'Villuri, Bharath Kumar'
'Kotipalli, Trimurtulu'
'Kuo, Chun-Wei'
'Yao, Ching-Fa'
_publ_section_title
;
 Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives
 from β-halo styrene derivatives and their application in the synthesis
 of trisubstituted pyridines
;
_journal_issue                   74
_journal_name_full               'RSC Adv.'
_journal_page_first              46704
_journal_paper_doi               10.1039/C7RA07128K
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C25 H17 N'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.40
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-22 deposited with the CCDC.
2017-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.820(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.492(3)
_cell_length_b                   3.9450(5)
_cell_length_c                   20.893(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1708.8(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1490
_diffrn_reflns_av_sigmaI/netI    0.1460
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12026
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         0.98
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1852
_refine_ls_R_factor_gt           0.0943
_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)+(0.1550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2358
_refine_ls_wR_factor_ref         0.2966
_reflns_number_gt                1551
_reflns_number_total             3009
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra07128k2.cif
_cod_data_source_block           15371a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7229288
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3051(2) 0.2298(12) 0.3295(2) 0.0234(12) Uani 1 1 d . . .
C2 C 0.2442(2) 0.2942(12) 0.2677(2) 0.0219(12) Uani 1 1 d . B .
C3 C 0.2482(3) 0.4571(13) 0.2104(3) 0.0289(13) Uani 1 1 d . . .
H3 H 0.2891 0.5262 0.2114 0.035 Uiso 1 1 calc R B .
C4 C 0.1932(3) 0.5183(14) 0.1522(3) 0.0323(13) Uani 1 1 d . B .
H4 H 0.1964 0.6292 0.1133 0.039 Uiso 1 1 calc R . .
C5 C 0.1344(3) 0.4205(14) 0.1502(3) 0.0360(14) Uani 1 1 d . . .
H5 H 0.0967 0.4687 0.1103 0.043 Uiso 1 1 calc R B .
C6 C 0.1291(3) 0.2511(13) 0.2060(3) 0.0315(13) Uani 1 1 d . B .
H6 H 0.0882 0.1796 0.2043 0.038 Uiso 1 1 calc R . .
C7 C 0.1845(3) 0.1879(12) 0.2642(3) 0.0273(13) Uani 1 1 d . . .
H7 H 0.1814 0.0695 0.3024 0.033 Uiso 1 1 calc R B .
C8 C 0.3099(2) 0.2882(12) 0.3979(2) 0.0225(12) Uani 1 1 d . B .
C9 C 0.2568(2) 0.4343(12) 0.4103(2) 0.0231(12) Uani 1 1 d . . .
C10 C 0.2103(2) 0.5540(13) 0.4163(2) 0.0251(12) Uani 1 1 d . B .
C11 C 0.1516(3) 0.6823(12) 0.4180(3) 0.0256(12) Uani 1 1 d . . .
C12 C 0.0944(3) 0.6580(14) 0.3597(3) 0.0318(13) Uani 1 1 d . B .
H12 H 0.0951 0.5605 0.3184 0.038 Uiso 1 1 calc R . .
C13 C 0.0364(3) 0.7727(14) 0.3604(3) 0.0415(15) Uani 1 1 d . . .
H13 H -0.0022 0.7527 0.3201 0.050 Uiso 1 1 calc R B .
C14 C 0.0353(3) 0.9171(14) 0.4206(3) 0.0383(15) Uani 1 1 d . B .
H14 H -0.0042 0.9951 0.4218 0.046 Uiso 1 1 calc R . .
C15 C 0.0919(3) 0.9465(14) 0.4786(3) 0.0342(14) Uani 1 1 d . . .
H15 H 0.0911 1.0505 0.5193 0.041 Uiso 1 1 calc R B .
C16 C 0.1493(3) 0.8274(13) 0.4783(3) 0.0298(13) Uani 1 1 d . B .
H16 H 0.1875 0.8434 0.5192 0.036 Uiso 1 1 calc R . .
C17 C 0.3689(2) 0.2174(12) 0.4536(2) 0.0239(12) Uani 1 1 d . . .
C18 C 0.3784(2) 0.2572(12) 0.5279(2) 0.0230(12) Uani 1 1 d . B .
C19 C 0.3341(3) 0.1239(12) 0.5528(3) 0.0273(12) Uani 1 1 d . . .
H19 H 0.2958 0.0185 0.5218 0.033 Uiso 1 1 calc R B .
C20 C 0.3459(3) 0.1452(14) 0.6233(3) 0.0341(14) Uani 1 1 d . B .
H20 H 0.3160 0.0515 0.6404 0.041 Uiso 1 1 calc R . .
C21 C 0.4003(3) 0.3003(14) 0.6677(3) 0.0364(14) Uani 1 1 d . . .
H21 H 0.4080 0.3145 0.7157 0.044 Uiso 1 1 calc R B .
C22 C 0.4442(3) 0.4364(14) 0.6440(3) 0.0362(14) Uani 1 1 d . B .
H22 H 0.4816 0.5480 0.6754 0.043 Uiso 1 1 calc R . .
C23 C 0.4337(3) 0.4103(13) 0.5738(3) 0.0294(13) Uani 1 1 d . . .
H23 H 0.4647 0.4979 0.5575 0.035 Uiso 1 1 calc R B .
C25 C 0.4123(3) 0.0632(14) 0.3721(3) 0.0361(14) Uani 1 1 d . . .
H25 H 0.4484 -0.0117 0.3631 0.043 Uiso 1 1 calc R A 1
N1 N 0.3567 0.1178 0.3163 0.025 Uiso 0.50 1 d P B 1
C24 C 0.4213 0.1064 0.4410 0.023 Uiso 0.50 1 d P B 1
H24 H 0.4617 0.0617 0.4777 0.028 Uiso 0.50 1 calc PR B 1
C24' C 0.3566 0.1179 0.3165 0.025 Uiso 0.50 1 d P B 2
H24' H 0.3537 0.0798 0.2705 0.030 Uiso 0.50 1 calc PR B 2
N1' N 0.4213 0.1064 0.4410 0.023 Uiso 0.50 1 d P B 2
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'
O O 0.0106 0.0060 '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
C24' C1 N1 0.101(1)
C24' C1 C8 121.3(4)
N1 C1 C8 121.4(4)
C24' C1 C2 116.7(4)
N1 C1 C2 116.6(4)
C8 C1 C2 122.0(4)
C7 C2 C3 118.8(5)
C7 C2 C1 122.8(4)
C3 C2 C1 118.4(5)
C4 C3 C2 120.2(5)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 120.4(5)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 120.6(5)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 118.9(5)
C7 C6 H6 120.5
C5 C6 H6 120.5
C2 C7 C6 121.1(5)
C2 C7 H7 119.5
C6 C7 H7 119.5
C1 C8 C17 118.7(4)
C1 C8 C9 120.5(4)
C17 C8 C9 120.7(4)
C10 C9 C8 175.9(5)
C9 C10 C11 175.0(5)
C12 C11 C16 118.1(5)
C12 C11 C10 120.3(4)
C16 C11 C10 121.6(5)
C13 C12 C11 121.5(5)
C13 C12 H12 119.2
C11 C12 H12 119.2
C12 C13 C14 119.4(6)
C12 C13 H13 120.3
C14 C13 H13 120.3
C15 C14 C13 119.6(5)
C15 C14 H14 120.2
C13 C14 H14 120.2
C16 C15 C14 121.0(5)
C16 C15 H15 119.5
C14 C15 H15 119.5
C15 C16 C11 120.3(5)
C15 C16 H16 119.9
C11 C16 H16 119.9
N1' C17 C24 0.0
N1' C17 C8 120.5(4)
C24 C17 C8 120.5(4)
N1' C17 C18 116.5(4)
C24 C17 C18 116.5(4)
C8 C17 C18 123.1(4)
C23 C18 C19 119.3(5)
C23 C18 C17 119.6(4)
C19 C18 C17 121.0(4)
C20 C19 C18 120.0(5)
C20 C19 H19 120.0
C18 C19 H19 120.0
C21 C20 C19 120.0(5)
C21 C20 H20 120.0
C19 C20 H20 120.0
C20 C21 C22 120.8(5)
C20 C21 H21 119.6
C22 C21 H21 119.6
C21 C22 C23 119.8(5)
C21 C22 H22 120.1
C23 C22 H22 120.1
C18 C23 C22 120.0(5)
C18 C23 H23 120.0
C22 C23 H23 120.0
C24' C25 N1 0.163(1)
C24' C25 C24 125.9(4)
N1 C25 C24 126.1(4)
C24' C25 N1' 125.9(4)
N1 C25 N1' 126.1(4)
C24 C25 N1' 0.0
C24' C25 H25 117.1
N1 C25 H25 117.0
C24 C25 H25 117.0
N1' C25 H25 117.0
C25 N1 C1 116.8(3)
C17 C24 C25 116.6(3)
C17 C24 H24 121.7
C25 C24 H24 121.7
C25 C24' C1 117.1(3)
C25 C24' H24' 121.5
C1 C24' H24' 121.5
C17 N1' C25 116.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C24' 1.362(5)
C1 N1 1.365(5)
C1 C8 1.409(6)
C1 C2 1.496(7)
C2 C7 1.381(7)
C2 C3 1.393(6)
C3 C4 1.379(7)
C3 H3 0.9500
C4 C5 1.364(7)
C4 H4 0.9500
C5 C6 1.388(7)
C5 H5 0.9500
C6 C7 1.385(7)
C6 H6 0.9500
C7 H7 0.9500
C8 C17 1.413(7)
C8 C9 1.437(7)
C9 C10 1.197(6)
C10 C11 1.427(7)
C11 C12 1.390(7)
C11 C16 1.405(6)
C12 C13 1.387(7)
C12 H12 0.9500
C13 C14 1.390(8)
C13 H13 0.9500
C14 C15 1.379(7)
C14 H14 0.9500
C15 C16 1.376(7)
C15 H15 0.9500
C16 H16 0.9500
C17 N1' 1.375(5)
C17 C24 1.375(5)
C17 C18 1.492(6)
C18 C23 1.381(7)
C18 C19 1.394(6)
C19 C20 1.393(6)
C19 H19 0.9500
C20 C21 1.361(7)
C20 H20 0.9500
C21 C22 1.373(7)
C21 H21 0.9500
C22 C23 1.398(7)
C22 H22 0.9500
C23 H23 0.9500
C25 C24' 1.355(5)
C25 N1 1.356(5)
C25 C24 1.383(5)
C25 N1' 1.383(5)
C25 H25 0.9500
C24 H24 0.9500
C24' H24' 0.9500
