# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'O-Pil Kwon'
_publ_contact_author_email       opilkwon@ajou.ac.kr
loop_
_publ_author_name
'Eun-Young Choi'
M.Jazbinsek
'Seung-Heon Lee'
P.Gunter
'Hoseop Yun'
'Soonwon Lee'
'O-Pil Kwon'

data_2cc
_database_code_depnum_ccdc_archive 'CCDC 822382'
#TrackingRef '- 2CC-1.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18.50 H17 N2 O'
_chemical_formula_weight         282.84

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'Cc '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.050(3)
_cell_length_b                   14.200(3)
_cell_length_c                   10.068(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.397(16)
_cell_angle_gamma                90.00
_cell_volume                     1572.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11296
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.36

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             598
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'not measured'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11305
_diffrn_reflns_av_R_equivalents  0.1357
_diffrn_reflns_av_sigmaI/netI    0.1011
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         28.36
_reflns_number_total             3518
_reflns_number_gt                1449
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0629P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0013(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   7(3)
_refine_ls_number_reflns         3518
_refine_ls_number_parameters     205
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1835
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1798
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_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
O1 O 0.7067(4) 0.5746(3) 0.7523(3) 0.1236(15) Uani 1 1 d . . .
N1 N 0.2908(4) 0.7947(3) -0.5394(4) 0.1029(14) Uani 1 1 d . . .
N2 N 0.3293(5) 0.5271(4) -0.3246(5) 0.1255(17) Uani 1 1 d . . .
C1 C 0.6709(4) 0.6182(4) 0.6345(4) 0.0806(14) Uani 1 1 d . . .
C2 C 0.6200(4) 0.5622(3) 0.5318(4) 0.0923(15) Uani 1 1 d . . .
H2 H 0.6123 0.4977 0.5446 0.111 Uiso 1 1 calc R . .
C3 C 0.6841(4) 0.7124(4) 0.6159(4) 0.0717(12) Uani 1 1 d . . .
H3 H 0.7180 0.7501 0.6852 0.086 Uiso 1 1 calc R . .
C4 C 0.5808(4) 0.6020(4) 0.4106(4) 0.0819(14) Uani 1 1 d . . .
H4 H 0.5451 0.5640 0.3425 0.098 Uiso 1 1 calc R . .
C5 C 0.6467(4) 0.7514(3) 0.4935(4) 0.0712(12) Uani 1 1 d . . .
H5 H 0.6573 0.8156 0.4807 0.085 Uiso 1 1 calc R . .
C6 C 0.5936(3) 0.6974(3) 0.3885(3) 0.0611(12) Uani 1 1 d . . .
C7 C 0.5585(3) 0.7428(3) 0.2618(3) 0.0666(12) Uani 1 1 d . . .
H7 H 0.5683 0.8079 0.2605 0.080 Uiso 1 1 calc R . .
C8 C 0.5136(4) 0.7037(3) 0.1459(4) 0.0684(11) Uani 1 1 d . . .
H8 H 0.5003 0.6390 0.1449 0.082 Uiso 1 1 calc R . .
C9 C 0.4848(4) 0.7545(3) 0.0233(4) 0.0635(11) Uani 1 1 d . . .
C10 C 0.4992(4) 0.8578(3) 0.0212(4) 0.0792(13) Uani 1 1 d . . .
H10A H 0.5736 0.8741 0.0754 0.095 Uiso 1 1 calc R . .
H10B H 0.4322 0.8860 0.0625 0.095 Uiso 1 1 calc R . .
C11 C 0.4399(3) 0.7072(3) -0.0888(3) 0.0642(11) Uani 1 1 d . . .
H11 H 0.4324 0.6421 -0.0852 0.077 Uiso 1 1 calc R . .
C12 C 0.5037(6) 0.8998(4) -0.1130(5) 0.116(2) Uani 1 1 d . . .
C13 C 0.4106(5) 0.8585(4) -0.2150(5) 0.0998(17) Uani 1 1 d . . .
H13A H 0.3314 0.8840 -0.2008 0.120 Uiso 1 1 calc R . .
H13B H 0.4294 0.8777 -0.3031 0.120 Uiso 1 1 calc R . .
C14 C 0.4041(3) 0.7545(3) -0.2107(4) 0.0645(12) Uani 1 1 d . . .
C15 C 0.4981(10) 1.0052(5) -0.1092(7) 0.215(5) Uani 1 1 d . . .
H15A H 0.4239 1.0245 -0.0745 0.323 Uiso 1 1 calc R . .
H15B H 0.5004 1.0297 -0.1978 0.323 Uiso 1 1 calc R . .
H15C H 0.5662 1.0290 -0.0529 0.323 Uiso 1 1 calc R . .
C16 C 0.6143(11) 0.8968(9) -0.1599(9) 0.109(4) Uani 0.50 1 d P . .
H16A H 0.6096 0.9246 -0.2471 0.164 Uiso 0.50 1 calc PR . .
H16B H 0.6402 0.8325 -0.1650 0.164 Uiso 0.50 1 calc PR . .
H16C H 0.6716 0.9311 -0.1008 0.164 Uiso 0.50 1 calc PR . .
C17 C 0.3582(3) 0.7063(4) -0.3224(3) 0.0730(14) Uani 1 1 d . . .
C18 C 0.3219(4) 0.7543(4) -0.4439(4) 0.0794(14) Uani 1 1 d . . .
C19 C 0.3433(5) 0.6073(5) -0.3247(5) 0.0880(15) Uani 1 1 d . . .
H1O H 0.725(5) 0.627(4) 0.813(6) 0.13(2) Uiso 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
O1 0.188(4) 0.115(3) 0.057(2) 0.026(2) -0.039(2) -0.023(3)
N1 0.104(3) 0.142(4) 0.056(2) 0.007(2) -0.0251(18) -0.009(3)
N2 0.145(4) 0.119(4) 0.105(4) -0.010(3) -0.028(3) 0.000(4)
C1 0.096(3) 0.098(4) 0.045(2) 0.016(3) -0.010(2) -0.012(3)
C2 0.136(4) 0.074(3) 0.061(3) 0.014(3) -0.020(3) -0.024(3)
C3 0.074(3) 0.092(4) 0.046(3) -0.010(2) -0.0100(19) 0.006(3)
C4 0.100(3) 0.090(4) 0.052(3) -0.001(2) -0.014(2) -0.016(3)
C5 0.075(3) 0.085(3) 0.051(2) -0.007(2) -0.008(2) 0.004(3)
C6 0.063(2) 0.073(3) 0.046(2) 0.000(2) -0.0030(17) 0.005(3)
C7 0.069(3) 0.077(3) 0.052(2) -0.001(2) -0.008(2) 0.003(2)
C8 0.071(2) 0.081(3) 0.051(2) 0.000(3) -0.0054(17) 0.011(3)
C9 0.058(2) 0.081(3) 0.049(2) 0.002(2) -0.0058(16) 0.003(2)
C10 0.091(3) 0.089(3) 0.053(2) 0.009(2) -0.019(2) -0.005(3)
C11 0.066(2) 0.072(3) 0.051(2) -0.003(2) -0.0090(18) 0.005(3)
C12 0.176(6) 0.094(4) 0.068(3) 0.019(3) -0.035(4) -0.051(4)
C13 0.116(4) 0.106(4) 0.069(3) 0.012(3) -0.035(3) -0.015(3)
C14 0.054(2) 0.083(4) 0.053(2) 0.004(2) -0.0113(17) -0.001(2)
C15 0.402(14) 0.088(4) 0.128(5) 0.041(4) -0.121(7) -0.087(6)
C16 0.107(7) 0.146(11) 0.072(6) -0.008(6) 0.002(5) -0.031(7)
C17 0.061(2) 0.101(4) 0.053(3) -0.004(3) -0.014(2) 0.008(3)
C18 0.069(3) 0.110(4) 0.055(3) -0.003(2) -0.016(2) -0.006(2)
C19 0.090(3) 0.106(5) 0.062(3) -0.006(3) -0.025(2) 0.005(4)

_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
O1 C1 1.363(5) . ?
O1 H1O 0.97(6) . ?
N1 C18 1.144(5) . ?
N2 C19 1.149(7) . ?
C1 C3 1.360(6) . ?
C1 C2 1.380(6) . ?
C2 C4 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C5 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(5) . ?
C7 C8 1.344(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.440(5) . ?
C8 H8 0.9300 . ?
C9 C11 1.365(5) . ?
C9 C10 1.476(6) . ?
C10 C12 1.482(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C14 1.422(5) . ?
C11 H11 0.9300 . ?
C12 C16 1.351(12) . ?
C12 C15 1.498(9) . ?
C12 C13 1.503(6) . ?
C13 C14 1.478(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C17 1.373(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C19 1.415(8) . ?
C17 C18 1.425(6) . ?

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
C1 O1 H1O 103(3) . . ?
C3 C1 O1 122.7(4) . . ?
C3 C1 C2 120.3(4) . . ?
O1 C1 C2 117.0(5) . . ?
C4 C2 C1 120.0(4) . . ?
C4 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C3 C5 119.4(4) . . ?
C1 C3 H3 120.3 . . ?
C5 C3 H3 120.3 . . ?
C2 C4 C6 121.0(4) . . ?
C2 C4 H4 119.5 . . ?
C6 C4 H4 119.5 . . ?
C3 C5 C6 121.9(4) . . ?
C3 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C4 C6 C5 117.4(4) . . ?
C4 C6 C7 123.7(4) . . ?
C5 C6 C7 118.8(4) . . ?
C8 C7 C6 128.7(4) . . ?
C8 C7 H7 115.6 . . ?
C6 C7 H7 115.6 . . ?
C7 C8 C9 124.8(4) . . ?
C7 C8 H8 117.6 . . ?
C9 C8 H8 117.6 . . ?
C11 C9 C8 119.7(4) . . ?
C11 C9 C10 120.6(4) . . ?
C8 C9 C10 119.6(3) . . ?
C9 C10 C12 115.2(4) . . ?
C9 C10 H10A 108.5 . . ?
C12 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C12 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C9 C11 C14 122.0(4) . . ?
C9 C11 H11 119.0 . . ?
C14 C11 H11 119.0 . . ?
C16 C12 C10 114.5(6) . . ?
C16 C12 C15 94.7(7) . . ?
C10 C12 C15 112.0(5) . . ?
C16 C12 C13 109.4(6) . . ?
C10 C12 C13 112.7(5) . . ?
C15 C12 C13 112.3(5) . . ?
C14 C13 C12 113.7(4) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C17 C14 C11 121.5(4) . . ?
C17 C14 C13 119.3(4) . . ?
C11 C14 C13 119.1(4) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 C19 122.9(4) . . ?
C14 C17 C18 121.2(5) . . ?
C19 C17 C18 116.0(4) . . ?
N1 C18 C17 177.9(6) . . ?
N2 C19 C17 178.5(7) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.030