#------------------------------------------------------------------------------
#$Date: 2015-12-09 09:32:22 +0200 (Wed, 09 Dec 2015) $
#$Revision: 170916 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/34/7223430.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_7223430
loop_
_publ_author_name
'Kankala, Shravankumar'
'pagadala, ramakanth'
'Maddila, Suresh'
'Vasam, Chandra Sekhar'
'Jonnalagadda, Sreekantha Babu'
_publ_section_title
;
 Silver(I)-N-heterocyclic carbene catalyzed multicomponent reactions: a
 facile synthesis of multisubstituted pyridines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA16582B
_journal_year                    2015
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_chemical_name_common
2-amino-4-(4-methoxyphenyl)-3,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
_chemical_name_systematic
2-amino-4-(4-methoxyphenyl)-3,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2014-09-01T11:44:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-09-03 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7449(9)
_cell_length_b                   10.7620(7)
_cell_length_c                   18.2213(12)
_cell_measurement_reflns_used    37338
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2.33
_cell_measurement_wavelength     0.71073
_cell_volume                     3087.5(3)
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_laue_measured_fraction_full 1
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37338
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         2.235
_diffrn_source                   tube
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.13
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0717P)²+1.9992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1728
_reflns_number_gt                3082
_reflns_number_total             3725
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ra16582b2.cif
_cod_data_source_block           shelx
_cod_database_code               7223430
_shelx_estimated_absorpt_t_min   0.97
_shelx_estimated_absorpt_t_max   0.979
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'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_calc_flag
C1 C 0.79876(11) 0.34984(17) 0.25878(10) 0.0308(4) Uani 1 d
C2 C 0.73410(11) 0.36426(17) 0.31127(10) 0.0307(4) Uani 1 d
C3 C 0.75791(11) 0.40114(17) 0.38177(9) 0.0305(4) Uani 1 d
C4 C 0.84461(11) 0.42099(17) 0.39633(10) 0.0310(4) Uani 1 d
C5 C 0.90535(11) 0.40448(17) 0.34031(10) 0.0311(4) Uani 1 d
C6 C 0.69572(11) 0.42255(17) 0.44231(10) 0.0315(4) Uani 1 d
C7 C 0.64793(12) 0.32581(18) 0.47150(10) 0.0354(4) Uani 1 d
H7 H 0.6535 0.2448 0.4513 0.043 Uiso 1 calc
C8 C 0.59208(12) 0.34516(19) 0.52968(11) 0.0387(4) Uani 1 d
H8 H 0.5604 0.2779 0.5495 0.046 Uiso 1 calc
C9 C 0.58330(12) 0.4643(2) 0.55839(10) 0.0394(4) Uani 1 d
C10 C 0.62888(13) 0.5614(2) 0.52862(12) 0.0433(5) Uani 1 d
H10 H 0.6215 0.6431 0.5474 0.052 Uiso 1 calc
C11 C 0.68539(12) 0.5407(2) 0.47144(12) 0.0401(4) Uani 1 d
H11 H 0.7173 0.6081 0.4521 0.048 Uiso 1 calc
C12 C 0.87351(11) 0.4559(2) 0.46772(11) 0.0390(4) Uani 1 d
C13 C 0.77803(12) 0.31257(19) 0.18112(10) 0.0373(4) Uani 1 d
H13A H 0.8303 0.3184 0.1511 0.045 Uiso 1 calc
H13B H 0.7364 0.3723 0.1608 0.045 Uiso 1 calc
C14 C 0.74162(14) 0.1804(2) 0.17395(12) 0.0456(5) Uani 1 d
H14A H 0.7498 0.1519 0.1228 0.055 Uiso 1 calc
H14B H 0.7747 0.1243 0.2062 0.055 Uiso 1 calc
C15 C 0.64834(14) 0.1680(2) 0.19333(12) 0.0454(5) Uani 1 d
H15A H 0.6306 0.0811 0.1843 0.055 Uiso 1 calc
H15B H 0.6151 0.2219 0.16 0.055 Uiso 1 calc
C16 C 0.62613(13) 0.2017(2) 0.27200(11) 0.0438(5) Uani 1 d
H16A H 0.6597 0.1487 0.3056 0.053 Uiso 1 calc
H16B H 0.5653 0.1832 0.2805 0.053 Uiso 1 calc
C17 C 0.64275(11) 0.33888(19) 0.29113(11) 0.0367(4) Uani 1 d
H17A H 0.6271 0.3912 0.2485 0.044 Uiso 1 calc
H17B H 0.6059 0.363 0.3328 0.044 Uiso 1 calc
C18 C 0.48740(19) 0.3930(3) 0.64995(14) 0.0646(8) Uani 1 d
H18A H 0.4523 0.4253 0.69 0.097 Uiso 1 calc
H18B H 0.5286 0.3335 0.6696 0.097 Uiso 1 calc
H18C H 0.4511 0.3515 0.6138 0.097 Uiso 1 calc
N1 N 0.88154(9) 0.36804(15) 0.27244(8) 0.0326(3) Uani 1 d
N2 N 0.90063(12) 0.4848(2) 0.52340(10) 0.0586(6) Uani 1 d
N3 N 0.98929(10) 0.42277(19) 0.35104(10) 0.0421(4) Uani 1 d
O1 O 0.53127(11) 0.49291(16) 0.61567(9) 0.0528(4) Uani 1 d
H1N H 1.0278(17) 0.408(2) 0.3115(15) 0.052(7) Uiso 1 d
H2N H 1.0108(17) 0.450(2) 0.3920(16) 0.054(7) Uiso 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 0 '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 0.006 '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
N1 C1 C2 124.16(16)
N1 C1 C13 115.07(16)
C2 C1 C13 120.78(15)
C3 C2 C1 117.59(16)
C3 C2 C17 122.09(16)
C1 C2 C17 120.32(16)
C2 C3 C4 118.52(16)
C2 C3 C6 123.21(15)
C4 C3 C6 118.26(15)
C3 C4 C5 120.15(16)
C3 C4 C12 121.39(16)
C5 C4 C12 118.45(15)
N3 C5 N1 116.53(16)
N3 C5 C4 122.72(16)
N1 C5 C4 120.75(15)
C11 C6 C7 118.47(17)
C11 C6 C3 120.06(17)
C7 C6 C3 121.46(16)
C6 C7 C8 121.38(18)
C6 C7 H7 119.3
C8 C7 H7 119.3
C9 C8 C7 119.11(19)
C9 C8 H8 120.4
C7 C8 H8 120.4
O1 C9 C10 116.30(19)
O1 C9 C8 123.8(2)
C10 C9 C8 119.92(18)
C9 C10 C11 120.47(19)
C9 C10 H10 119.8
C11 C10 H10 119.8
C6 C11 C10 120.62(19)
C6 C11 H11 119.7
C10 C11 H11 119.7
N2 C12 C4 176.6(2)
C1 C13 C14 113.98(17)
C1 C13 H13A 108.8
C14 C13 H13A 108.8
C1 C13 H13B 108.8
C14 C13 H13B 108.8
H13A C13 H13B 107.7
C15 C14 C13 114.98(18)
C15 C14 H14A 108.5
C13 C14 H14A 108.5
C15 C14 H14B 108.5
C13 C14 H14B 108.5
H14A C14 H14B 107.5
C14 C15 C16 114.93(17)
C14 C15 H15A 108.5
C16 C15 H15A 108.5
C14 C15 H15B 108.5
C16 C15 H15B 108.5
H15A C15 H15B 107.5
C15 C16 C17 113.80(17)
C15 C16 H16A 108.8
C17 C16 H16A 108.8
C15 C16 H16B 108.8
C17 C16 H16B 108.8
H16A C16 H16B 107.7
C2 C17 C16 113.00(16)
C2 C17 H17A 109
C16 C17 H17A 109
C2 C17 H17B 109
C16 C17 H17B 109
H17A C17 H17B 107.8
O1 C18 H18A 109.5
O1 C18 H18B 109.5
H18A C18 H18B 109.5
O1 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C1 N1 C5 118.82(15)
C5 N3 H1N 119.1(16)
C5 N3 H2N 123.6(18)
H1N N3 H2N 117(2)
C9 O1 C18 117.25(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.341(2)
C1 C2 1.405(2)
C1 C13 1.507(2)
C2 C3 1.396(2)
C2 C17 1.509(2)
C3 C4 1.407(2)
C3 C6 1.493(2)
C4 C5 1.410(2)
C4 C12 1.428(3)
C5 N3 1.350(2)
C5 N1 1.350(2)
C6 C11 1.388(3)
C6 C7 1.390(3)
C7 C8 1.393(3)
C7 H7 0.95
C8 C9 1.392(3)
C8 H8 0.95
C9 O1 1.362(2)
C9 C10 1.379(3)
C10 C11 1.388(3)
C10 H10 0.95
C11 H11 0.95
C12 N2 1.144(3)
C13 C14 1.539(3)
C13 H13A 0.99
C13 H13B 0.99
C14 C15 1.516(3)
C14 H14A 0.99
C14 H14B 0.99
C15 C16 1.519(3)
C15 H15A 0.99
C15 H15B 0.99
C16 C17 1.539(3)
C16 H16A 0.99
C16 H16B 0.99
C17 H17A 0.99
C17 H17B 0.99
C18 O1 1.422(3)
C18 H18A 0.98
C18 H18B 0.98
C18 H18C 0.98
N3 H1N 0.96(3)
N3 H2N 0.87(3)
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
N1 C1 C2 C3 0.7(3)
C13 C1 C2 C3 -178.86(17)
N1 C1 C2 C17 -178.63(17)
C13 C1 C2 C17 1.8(3)
C1 C2 C3 C4 -0.3(3)
C17 C2 C3 C4 178.98(17)
C1 C2 C3 C6 178.66(17)
C17 C2 C3 C6 -2.0(3)
C2 C3 C4 C5 0.4(3)
C6 C3 C4 C5 -178.63(16)
C2 C3 C4 C12 -178.50(18)
C6 C3 C4 C12 2.4(3)
C3 C4 C5 N3 179.68(18)
C12 C4 C5 N3 -1.4(3)
C3 C4 C5 N1 -0.8(3)
C12 C4 C5 N1 178.11(18)
C2 C3 C6 C11 -115.1(2)
C4 C3 C6 C11 63.9(2)
C2 C3 C6 C7 65.8(2)
C4 C3 C6 C7 -115.2(2)
C11 C6 C7 C8 -1.4(3)
C3 C6 C7 C8 177.75(17)
C6 C7 C8 C9 0.9(3)
C7 C8 C9 O1 -179.23(18)
C7 C8 C9 C10 0.7(3)
O1 C9 C10 C11 178.15(18)
C8 C9 C10 C11 -1.8(3)
C7 C6 C11 C10 0.3(3)
C3 C6 C11 C10 -178.85(18)
C9 C10 C11 C6 1.3(3)
N1 C1 C13 C14 114.29(19)
C2 C1 C13 C14 -66.1(2)
C1 C13 C14 C15 79.1(2)
C13 C14 C15 C16 -61.4(3)
C14 C15 C16 C17 63.8(3)
C3 C2 C17 C16 -114.2(2)
C1 C2 C17 C16 65.1(2)
C15 C16 C17 C2 -82.9(2)
C2 C1 N1 C5 -1.1(3)
C13 C1 N1 C5 178.48(16)
N3 C5 N1 C1 -179.33(17)
C4 C5 N1 C1 1.2(3)
C10 C9 O1 C18 -176.5(2)
C8 C9 O1 C18 3.5(3)
