#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:00:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180526 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/95/7219533.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_7219533
loop_
_publ_author_name
'LIKHAR, PRAVIN R'
'D, Shankar'
'K, Jaipal'
'Balasubramanian, Sridhar'
'Lingamallu, Giribabu'
_publ_section_title
;
 Intramolecular Cyclization Assisted Oxidative Addition: Synthesis of
 Octahedral Cycloplatinated Methyl Complexes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA17066K
_journal_year                    2015
_chemical_formula_moiety         'C22 H22 N2 O3'
_chemical_formula_sum            'C22 H22 N2 O3'
_chemical_formula_weight         362.42
_chemical_name_systematic
; 
(E)-N-phenyl-3-(3,4,5-trimethoxystyryl)pyridine-2-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-18 deposited with the CCDC.
2015-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.402(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.269(3)
_cell_length_b                   7.994(3)
_cell_length_c                   32.597(13)
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.05
_cell_volume                     1882.3(13)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD 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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9054
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0516
_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)+(0.0559P)²+0.2829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                2476
_reflns_number_total             3196
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4ra17066k2.cif
_cod_data_source_block           ak44
_cod_original_cell_volume        1882.4(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7219533
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 1.0565(3) 0.0808(2) 0.43818(6) 0.0468(5) Uani 1 1 d .
C2 C 1.3344(3) -0.0534(3) 0.44734(7) 0.0603(6) Uani 1 1 d .
H2 H 1.4266 -0.1065 0.4647 0.072 Uiso 1 1 calc R
C3 C 1.3559(3) -0.0407(3) 0.40653(7) 0.0616(6) Uani 1 1 d .
H3 H 1.4632 -0.0792 0.3966 0.074 Uiso 1 1 calc R
C4 C 1.2156(3) 0.0304(3) 0.38018(7) 0.0563(6) Uani 1 1 d .
H4 H 1.2266 0.0368 0.3521 0.068 Uiso 1 1 calc R
C5 C 1.0597(3) 0.0917(2) 0.39525(6) 0.0461(5) Uani 1 1 d .
C6 C 0.8613(3) 0.3165(3) 0.45292(6) 0.0494(6) Uani 1 1 d .
C7 C 0.6856(4) 0.3678(3) 0.45943(7) 0.0647(7) Uani 1 1 d .
H7 H 0.5972 0.2895 0.4651 0.078 Uiso 1 1 calc R
C8 C 0.6417(4) 0.5358(3) 0.45744(8) 0.0768(8) Uani 1 1 d .
H8 H 0.5239 0.5700 0.4624 0.092 Uiso 1 1 calc R
C9 C 0.7678(4) 0.6525(3) 0.44834(8) 0.0745(8) Uani 1 1 d .
H9 H 0.7363 0.7652 0.4469 0.089 Uiso 1 1 calc R
C10 C 0.9409(4) 0.6016(3) 0.44133(7) 0.0685(7) Uani 1 1 d .
H10 H 1.0276 0.6800 0.4348 0.082 Uiso 1 1 calc R
C11 C 0.9876(3) 0.4346(3) 0.44388(6) 0.0567(6) Uani 1 1 d .
H11 H 1.1064 0.4015 0.4394 0.068 Uiso 1 1 calc R
C12 C 0.9001(3) 0.1591(2) 0.36887(6) 0.0497(5) Uani 1 1 d .
H12 H 0.7950 0.1815 0.3818 0.060 Uiso 1 1 calc R
C13 C 0.8880(3) 0.1916(2) 0.32910(6) 0.0462(5) Uani 1 1 d .
H13 H 0.9910 0.1677 0.3156 0.055 Uiso 1 1 calc R
C14 C 0.7253(3) 0.2626(2) 0.30423(6) 0.0410(5) Uani 1 1 d .
C15 C 0.7108(3) 0.2504(2) 0.26161(6) 0.0426(5) Uani 1 1 d .
H15 H 0.8016 0.1941 0.2491 0.051 Uiso 1 1 calc R
C16 C 0.5611(3) 0.3217(2) 0.23727(6) 0.0412(5) Uani 1 1 d .
C17 C 0.4293(3) 0.4101(2) 0.25548(6) 0.0429(5) Uani 1 1 d .
C18 C 0.4416(3) 0.4189(2) 0.29821(6) 0.0457(5) Uani 1 1 d .
C19 C 0.5883(3) 0.3456(2) 0.32237(6) 0.0470(5) Uani 1 1 d .
H19 H 0.5949 0.3521 0.3510 0.056 Uiso 1 1 calc R
C20 C 0.3088(4) 0.5222(4) 0.35625(8) 0.0839(9) Uani 1 1 d .
H20A H 0.3011 0.4133 0.3683 0.126 Uiso 1 1 calc R
H20B H 0.2062 0.5891 0.3628 0.126 Uiso 1 1 calc R
H20C H 0.4226 0.5748 0.3671 0.126 Uiso 1 1 calc R
C21 C 0.1177(3) 0.4169(3) 0.22648(8) 0.0673(7) Uani 1 1 d .
H21A H 0.1285 0.3072 0.2150 0.101 Uiso 1 1 calc R
H21B H 0.0327 0.4823 0.2084 0.101 Uiso 1 1 calc R
H21C H 0.0726 0.4080 0.2530 0.101 Uiso 1 1 calc R
C22 C 0.6617(3) 0.2275(3) 0.17478(7) 0.0712(7) Uani 1 1 d .
H22A H 0.7822 0.2756 0.1816 0.107 Uiso 1 1 calc R
H22B H 0.6276 0.2348 0.1455 0.107 Uiso 1 1 calc R
H22C H 0.6637 0.1123 0.1831 0.107 Uiso 1 1 calc R
N1 N 0.9062(3) 0.1453(2) 0.45583(6) 0.0541(5) Uani 1 1 d .
N2 N 1.1883(3) 0.0062(2) 0.46363(5) 0.0546(5) Uani 1 1 d .
O1 O 0.3033(2) 0.50683(19) 0.31310(5) 0.0649(5) Uani 1 1 d .
O2 O 0.29322(19) 0.49544(17) 0.23099(4) 0.0530(4) Uani 1 1 d .
O3 O 0.5327(2) 0.31478(18) 0.19533(4) 0.0526(4) Uani 1 1 d .
H1N H 0.880(3) 0.102(3) 0.4786(7) 0.057(7) Uiso 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'
O O 0.0106 0.0060 '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
N2 C1 N1 116.83(18)
N2 C1 C5 123.74(18)
N1 C1 C5 119.39(18)
N2 C2 C3 123.3(2)
N2 C2 H2 118.4
C3 C2 H2 118.4
C2 C3 C4 118.8(2)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 120.4(2)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C1 116.11(18)
C4 C5 C12 123.43(18)
C1 C5 C12 120.42(18)
C11 C6 C7 118.8(2)
C11 C6 N1 121.9(2)
C7 C6 N1 119.3(2)
C6 C7 C8 119.7(3)
C6 C7 H7 120.2
C8 C7 H7 120.2
C9 C8 C7 121.2(3)
C9 C8 H8 119.4
C7 C8 H8 119.4
C8 C9 C10 119.1(2)
C8 C9 H9 120.4
C10 C9 H9 120.4
C9 C10 C11 120.3(3)
C9 C10 H10 119.9
C11 C10 H10 119.9
C6 C11 C10 120.9(2)
C6 C11 H11 119.6
C10 C11 H11 119.6
C13 C12 C5 127.7(2)
C13 C12 H12 116.2
C5 C12 H12 116.2
C12 C13 C14 125.5(2)
C12 C13 H13 117.3
C14 C13 H13 117.3
C19 C14 C15 119.01(18)
C19 C14 C13 121.49(18)
C15 C14 C13 119.48(17)
C14 C15 C16 120.61(18)
C14 C15 H15 119.7
C16 C15 H15 119.7
O3 C16 C17 114.76(17)
O3 C16 C15 125.21(18)
C17 C16 C15 120.03(18)
C16 C17 O2 119.51(18)
C16 C17 C18 119.27(18)
O2 C17 C18 121.14(18)
O1 C18 C19 124.72(18)
O1 C18 C17 114.67(18)
C19 C18 C17 120.60(18)
C14 C19 C18 120.39(18)
C14 C19 H19 119.8
C18 C19 H19 119.8
O1 C20 H20A 109.5
O1 C20 H20B 109.5
H20A C20 H20B 109.5
O1 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
O2 C21 H21A 109.5
O2 C21 H21B 109.5
H21A C21 H21B 109.5
O2 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
O3 C22 H22A 109.5
O3 C22 H22B 109.5
H22A C22 H22B 109.5
O3 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C1 N1 C6 121.32(19)
C1 N1 H1N 117.9(14)
C6 N1 H1N 112.2(14)
C2 N2 C1 117.54(18)
C18 O1 C20 117.54(17)
C17 O2 C21 114.89(15)
C16 O3 C22 117.82(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.336(2)
C1 N1 1.389(3)
C1 C5 1.405(3)
C2 N2 1.328(3)
C2 C3 1.360(3)
C2 H2 0.9300
C3 C4 1.381(3)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C12 1.468(3)
C6 C11 1.372(3)
C6 C7 1.380(3)
C6 N1 1.408(3)
C7 C8 1.381(3)
C7 H7 0.9300
C8 C9 1.363(4)
C8 H8 0.9300
C9 C10 1.366(3)
C9 H9 0.9300
C10 C11 1.378(3)
C10 H10 0.9300
C11 H11 0.9300
C12 C13 1.316(3)
C12 H12 0.9300
C13 C14 1.471(3)
C13 H13 0.9300
C14 C19 1.383(3)
C14 C15 1.385(3)
C15 C16 1.395(3)
C15 H15 0.9300
C16 O3 1.361(2)
C16 C17 1.377(3)
C17 O2 1.380(2)
C17 C18 1.388(3)
C18 O1 1.359(2)
C18 C19 1.384(3)
C19 H19 0.9300
C20 O1 1.408(3)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 O2 1.415(3)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 O3 1.398(2)
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
N1 H1N 0.86(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N2 0.86(2) 2.18(2) 3.039(3) 180(2) 3_756
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N2 C2 C3 C4 -3.2(4)
C2 C3 C4 C5 2.0(4)
C3 C4 C5 C1 1.5(3)
C3 C4 C5 C12 -176.0(2)
N2 C1 C5 C4 -4.4(3)
N1 C1 C5 C4 177.86(19)
N2 C1 C5 C12 173.22(19)
N1 C1 C5 C12 -4.5(3)
C11 C6 C7 C8 -1.1(3)
N1 C6 C7 C8 178.7(2)
C6 C7 C8 C9 1.3(4)
C7 C8 C9 C10 -0.4(4)
C8 C9 C10 C11 -0.7(4)
C7 C6 C11 C10 0.1(3)
N1 C6 C11 C10 -179.7(2)
C9 C10 C11 C6 0.8(3)
C4 C5 C12 C13 -9.4(3)
C1 C5 C12 C13 173.2(2)
C5 C12 C13 C14 -178.67(19)
C12 C13 C14 C19 18.7(3)
C12 C13 C14 C15 -163.1(2)
C19 C14 C15 C16 0.5(3)
C13 C14 C15 C16 -177.77(17)
C14 C15 C16 O3 -179.07(17)
C14 C15 C16 C17 2.2(3)
O3 C16 C17 O2 -5.9(3)
C15 C16 C17 O2 172.94(16)
O3 C16 C17 C18 177.44(16)
C15 C16 C17 C18 -3.7(3)
C16 C17 C18 O1 -179.00(17)
O2 C17 C18 O1 4.4(3)
C16 C17 C18 C19 2.6(3)
O2 C17 C18 C19 -174.04(17)
C15 C14 C19 C18 -1.7(3)
C13 C14 C19 C18 176.56(18)
O1 C18 C19 C14 -178.11(18)
C17 C18 C19 C14 0.2(3)
N2 C1 N1 C6 120.4(2)
C5 C1 N1 C6 -61.7(3)
C11 C6 N1 C1 -19.4(3)
C7 C6 N1 C1 160.7(2)
C3 C2 N2 C1 0.6(3)
N1 C1 N2 C2 -178.81(19)
C5 C1 N2 C2 3.4(3)
C19 C18 O1 C20 -0.9(3)
C17 C18 O1 C20 -179.3(2)
C16 C17 O2 C21 103.4(2)
C18 C17 O2 C21 -80.0(2)
C17 C16 O3 C22 179.74(18)
C15 C16 O3 C22 1.0(3)
