# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_global


data_5
#TrackingRef '5.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-(4-methoxyphenyl)isoquinolin-1-amine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2 O1'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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'

_cell_length_a                   13.4270(13)
_cell_length_b                   5.6126(5)
_cell_length_c                   16.7627(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.685(10)
_cell_angle_gamma                90.00
_cell_volume                     1262.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1619
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      26.74

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Crysalis PRO (Oxford Diffraction,2010)'

_exptl_special_details           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4561
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_sigmaI/netI    0.1505
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         26.74
_reflns_number_total             2551
_reflns_number_gt                874
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0110P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2551
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2057
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
H1 H 0.911(2) 0.491(4) 0.0506(17) 0.034(9) Uiso 1 1 d . . .
H5 H 1.214(2) -0.002(4) 0.0317(16) 0.024(9) Uiso 1 1 d . . .
H9 H 1.285(2) 0.804(5) 0.1963(17) 0.038(10) Uiso 1 1 d . . .
H3 H 0.777(2) -0.164(5) 0.1923(16) 0.037(9) Uiso 1 1 d . . .
H6 H 1.373(2) -0.010(5) -0.0052(18) 0.044(10) Uiso 1 1 d . . .
H2 H 0.735(2) 0.493(5) 0.077(2) 0.062(12) Uiso 1 1 d . . .
H4 H 0.948(2) -0.141(5) 0.1696(18) 0.056(11) Uiso 1 1 d . . .
H8 H 1.425(2) 0.607(5) 0.132(2) 0.061(13) Uiso 1 1 d . . .
H10 H 1.114(2) 0.814(5) 0.2227(18) 0.054(11) Uiso 1 1 d . . .
H11 H 0.535(3) 0.029(5) 0.192(2) 0.060(13) Uiso 1 1 d . . .
H7 H 1.489(2) 0.303(5) 0.055(2) 0.064(12) Uiso 1 1 d . . .
H13 H 0.629(2) -0.010(5) 0.253(2) 0.060(12) Uiso 1 1 d . . .
H12 H 0.611(3) -0.166(6) 0.162(2) 0.083(16) Uiso 1 1 d . . .
H1N H 1.074(3) 0.018(5) 0.079(2) 0.070(13) Uiso 1 1 d . . .
C1 C 0.9450(2) 0.1731(6) 0.1056(2) 0.0338(9) Uani 1 1 d . . .
C2 C 0.9050(3) -0.0121(7) 0.1476(2) 0.0439(11) Uani 1 1 d . . .
C3 C 0.8034(3) -0.0180(7) 0.1633(2) 0.0412(10) Uani 1 1 d . . .
C4 C 0.7442(2) 0.1676(6) 0.1379(2) 0.0338(9) Uani 1 1 d . . .
C5 C 0.7826(3) 0.3540(7) 0.0948(2) 0.0388(10) Uani 1 1 d . . .
C6 C 0.8827(3) 0.3585(7) 0.0789(2) 0.0402(10) Uani 1 1 d . . .
C7 C 1.1142(2) 0.3407(6) 0.1162(2) 0.0309(9) Uani 1 1 d . . .
C9 C 1.1462(3) 0.6769(7) 0.1900(2) 0.0472(11) Uani 1 1 d . . .
C10 C 1.2456(3) 0.6742(7) 0.1772(2) 0.0451(11) Uani 1 1 d . . .
C11 C 1.2838(3) 0.4964(6) 0.1283(2) 0.0380(9) Uani 1 1 d . . .
C12 C 1.3870(3) 0.4797(8) 0.1091(3) 0.0494(11) Uani 1 1 d . . .
C13 C 1.4194(3) 0.3035(8) 0.0622(3) 0.0551(12) Uani 1 1 d . . .
C14 C 1.3558(3) 0.1321(8) 0.0309(2) 0.0528(11) Uani 1 1 d . . .
C15 C 1.2555(3) 0.1432(7) 0.0477(2) 0.0422(10) Uani 1 1 d . . .
C16 C 1.2185(2) 0.3229(6) 0.0963(2) 0.0318(9) Uani 1 1 d . . .
C18 C 0.5988(4) -0.0181(10) 0.1914(3) 0.0609(14) Uani 1 1 d . . .
N1 N 1.0480(2) 0.1758(5) 0.08566(18) 0.0419(9) Uani 1 1 d . . .
N2 N 1.0805(2) 0.5127(5) 0.16110(18) 0.0422(8) Uani 1 1 d . . .
O1 O 0.64272(17) 0.1778(4) 0.15044(14) 0.0497(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0208(18) 0.040(2) 0.041(2) -0.0036(18) 0.0046(17) -0.0006(18)
C2 0.032(2) 0.037(2) 0.063(3) 0.004(2) 0.003(2) 0.0052(19)
C3 0.025(2) 0.046(2) 0.052(3) 0.014(2) 0.0030(19) -0.0059(19)
C4 0.0211(18) 0.042(2) 0.039(2) -0.0014(19) 0.0043(17) -0.0024(18)
C5 0.032(2) 0.041(3) 0.044(2) 0.002(2) 0.0056(19) 0.001(2)
C6 0.033(2) 0.045(3) 0.043(2) 0.009(2) 0.0059(19) -0.007(2)
C7 0.0224(18) 0.040(2) 0.030(2) 0.0003(18) 0.0058(16) 0.0042(18)
C9 0.043(2) 0.051(3) 0.048(3) -0.012(2) 0.000(2) 0.006(2)
C10 0.041(2) 0.043(3) 0.051(3) -0.005(2) -0.001(2) -0.004(2)
C11 0.027(2) 0.048(2) 0.040(2) 0.0031(19) 0.0011(18) -0.0013(18)
C12 0.032(2) 0.064(3) 0.052(3) 0.006(2) 0.005(2) -0.013(2)
C13 0.027(2) 0.086(4) 0.053(3) 0.006(3) 0.012(2) 0.007(3)
C14 0.045(2) 0.068(3) 0.046(3) -0.007(2) 0.009(2) 0.005(2)
C15 0.032(2) 0.049(3) 0.046(3) 0.005(2) 0.0127(19) 0.0022(19)
C16 0.0232(18) 0.038(2) 0.035(2) 0.0030(17) 0.0052(17) 0.0033(17)
C18 0.034(2) 0.089(4) 0.061(3) 0.007(3) 0.019(3) -0.005(3)
N1 0.0200(15) 0.041(2) 0.065(2) -0.0126(17) 0.0140(16) -0.0019(16)
N2 0.0331(18) 0.0490(19) 0.045(2) -0.0114(16) 0.0069(16) 0.0013(15)
O1 0.0256(13) 0.0648(18) 0.0595(19) 0.0057(14) 0.0122(14) 0.0023(14)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(4) . ?
C1 C6 1.401(4) . ?
C1 N1 1.432(3) . ?
C2 C3 1.398(4) . ?
C2 H4 0.99(3) . ?
C3 C4 1.371(4) . ?
C3 H3 1.02(3) . ?
C4 C5 1.379(4) . ?
C4 O1 1.386(3) . ?
C5 C6 1.378(4) . ?
C5 H2 1.04(3) . ?
C6 H1 0.96(3) . ?
C7 N2 1.313(4) . ?
C7 N1 1.372(4) . ?
C7 C16 1.452(4) . ?
C9 C10 1.358(5) . ?
C9 N2 1.355(4) . ?
C9 H10 1.04(3) . ?
C10 C11 1.398(5) . ?
C10 H9 0.96(3) . ?
C11 C16 1.406(4) . ?
C11 C12 1.435(5) . ?
C12 C13 1.344(5) . ?
C12 H8 0.95(3) . ?
C13 C14 1.380(5) . ?
C13 H7 0.95(3) . ?
C14 C15 1.385(5) . ?
C14 H6 1.04(3) . ?
C15 C16 1.397(4) . ?
C15 H5 1.02(2) . ?
C18 O1 1.432(5) . ?
C18 H11 0.90(3) . ?
C18 H13 1.10(3) . ?
C18 H12 0.98(3) . ?
N1 H1N 0.96(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.2(3) . . ?
C2 C1 N1 121.5(3) . . ?
C6 C1 N1 119.3(3) . . ?
C1 C2 C3 120.9(4) . . ?
C1 C2 H4 121.0(18) . . ?
C3 C2 H4 118.0(18) . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 123.6(15) . . ?
C2 C3 H3 117.5(15) . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 O1 123.2(3) . . ?
C5 C4 O1 115.6(3) . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H2 118.9(18) . . ?
C6 C5 H2 121.2(18) . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H1 120.4(17) . . ?
C1 C6 H1 119.4(17) . . ?
N2 C7 N1 118.6(3) . . ?
N2 C7 C16 122.2(3) . . ?
N1 C7 C16 119.1(3) . . ?
C10 C9 N2 124.6(4) . . ?
C10 C9 H10 120.6(17) . . ?
N2 C9 H10 114.7(17) . . ?
C9 C10 C11 118.7(4) . . ?
C9 C10 H9 118.8(17) . . ?
C11 C10 H9 122.1(18) . . ?
C10 C11 C16 118.8(3) . . ?
C10 C11 C12 123.5(4) . . ?
C16 C11 C12 117.7(4) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H8 128(2) . . ?
C11 C12 H8 112(2) . . ?
C12 C13 C14 121.9(4) . . ?
C12 C13 H7 114(2) . . ?
C14 C13 H7 124(2) . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H6 127.8(17) . . ?
C15 C14 H6 113.1(17) . . ?
C14 C15 C16 121.0(4) . . ?
C14 C15 H5 116.0(16) . . ?
C16 C15 H5 122.0(16) . . ?
C15 C16 C11 119.6(3) . . ?
C15 C16 C7 123.0(3) . . ?
C11 C16 C7 117.3(3) . . ?
O1 C18 H11 101(2) . . ?
O1 C18 H13 106.1(16) . . ?
H11 C18 H13 108(3) . . ?
O1 C18 H12 109(2) . . ?
H11 C18 H12 115(3) . . ?
H13 C18 H12 117(3) . . ?
C7 N1 C1 122.6(3) . . ?
C7 N1 H1N 115(2) . . ?
C1 N1 H1N 112(2) . . ?
C7 N2 C9 118.2(3) . . ?
C4 O1 C18 117.5(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(6) . . . . ?
N1 C1 C2 C3 -176.9(3) . . . . ?
C1 C2 C3 C4 -1.6(6) . . . . ?
C2 C3 C4 C5 2.4(6) . . . . ?
C2 C3 C4 O1 179.8(3) . . . . ?
C3 C4 C5 C6 -2.0(6) . . . . ?
O1 C4 C5 C6 -179.6(3) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
N1 C1 C6 C5 177.4(3) . . . . ?
N2 C9 C10 C11 2.6(6) . . . . ?
C9 C10 C11 C16 -1.9(6) . . . . ?
C9 C10 C11 C12 178.5(4) . . . . ?
C10 C11 C12 C13 179.6(4) . . . . ?
C16 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 -0.3(7) . . . . ?
C12 C13 C14 C15 0.7(7) . . . . ?
C13 C14 C15 C16 -0.8(6) . . . . ?
C14 C15 C16 C11 0.5(5) . . . . ?
C14 C15 C16 C7 -179.4(4) . . . . ?
C10 C11 C16 C15 -179.7(3) . . . . ?
C12 C11 C16 C15 0.0(5) . . . . ?
C10 C11 C16 C7 0.2(5) . . . . ?
C12 C11 C16 C7 179.8(3) . . . . ?
N2 C7 C16 C15 -179.1(3) . . . . ?
N1 C7 C16 C15 -0.6(5) . . . . ?
N2 C7 C16 C11 1.1(5) . . . . ?
N1 C7 C16 C11 179.6(3) . . . . ?
N2 C7 N1 C1 -4.8(5) . . . . ?
C16 C7 N1 C1 176.6(3) . . . . ?
C2 C1 N1 C7 -114.4(4) . . . . ?
C6 C1 N1 C7 68.3(4) . . . . ?
N1 C7 N2 C9 -179.0(3) . . . . ?
C16 C7 N2 C9 -0.5(5) . . . . ?
C10 C9 N2 C7 -1.4(6) . . . . ?
C3 C4 O1 C18 -0.7(5) . . . . ?
C5 C4 O1 C18 176.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        26.74
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044


_database_code_depnum_ccdc_archive 'CCDC 909445'