# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ly02

_audit_creation_date             2013-10-10T21:17:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C27 H26 N2'
_chemical_formula_moiety         'C27 H26 N2'
_chemical_formula_weight         378.5

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'

_cell_length_a                   7.4217(3)
_cell_length_b                   23.8402(8)
_cell_length_c                   11.7942(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.776(4)
_cell_angle_gamma                90
_cell_volume                     2056.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3895
_cell_measurement_theta_min      2.907
_cell_measurement_theta_max      26.993

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  CrysAlisPro, Oxford Diffraction Ltd.,
  Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.76426
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0009
_diffrn_orient_matrix_ub_11      0.0690379
_diffrn_orient_matrix_ub_12      0.0193523
_diffrn_orient_matrix_ub_13      -0.0086095
_diffrn_orient_matrix_ub_21      0.0338878
_diffrn_orient_matrix_ub_22      -0.0195151
_diffrn_orient_matrix_ub_23      -0.0366302
_diffrn_orient_matrix_ub_31      -0.0590977
_diffrn_orient_matrix_ub_32      0.011423
_diffrn_orient_matrix_ub_33      -0.0479997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_number            13457
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4047
_reflns_number_gt                3289
_reflns_threshold_expression     I>2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0739P)²+1.5065P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4047
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2007
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'

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
N11 N 0.5137(3) 0.37529(8) 0.28846(17) 0.0293(5) Uani 1 1 d . . .
C12 C 0.4162(3) 0.37384(10) 0.1822(2) 0.0276(5) Uani 1 1 d . . .
C13 C 0.3615(3) 0.42187(10) 0.1193(2) 0.0297(6) Uani 1 1 d . . .
H13 H 0.2947 0.4187 0.0434 0.036 Uiso 1 1 calc R . .
C14 C 0.4043(3) 0.47497(10) 0.1672(2) 0.0283(5) Uani 1 1 d . . .
C15 C 0.5027(4) 0.47584(10) 0.2780(2) 0.0335(6) Uani 1 1 d . . .
H15 H 0.533 0.5108 0.3151 0.04 Uiso 1 1 calc R . .
C16 C 0.5580(3) 0.42602(10) 0.3356(2) 0.0302(6) Uani 1 1 d . . .
C121 C 0.3676(3) 0.31637(10) 0.1336(2) 0.0278(5) Uani 1 1 d . . .
C122 C 0.4055(4) 0.26883(11) 0.2022(2) 0.0351(6) Uani 1 1 d . . .
H122 H 0.4654 0.2728 0.2796 0.042 Uiso 1 1 calc R . .
C123 C 0.3570(4) 0.21575(11) 0.1592(2) 0.0364(6) Uani 1 1 d . . .
H123 H 0.3835 0.1842 0.2082 0.044 Uiso 1 1 calc R . .
C124 C 0.2715(3) 0.20761(11) 0.0473(2) 0.0337(6) Uani 1 1 d . . .
C125 C 0.2354(3) 0.25469(11) -0.0216(2) 0.0337(6) Uani 1 1 d . . .
H125 H 0.1779 0.2504 -0.0994 0.04 Uiso 1 1 calc R . .
C126 C 0.2821(4) 0.30828(11) 0.0212(2) 0.0335(6) Uani 1 1 d . . .
H126 H 0.2545 0.3398 -0.0279 0.04 Uiso 1 1 calc R . .
C127 C 0.2185(4) 0.14980(11) -0.0002(3) 0.0423(7) Uani 1 1 d . . .
H12A H 0.2685 0.1213 0.0564 0.063 Uiso 1 1 calc R . .
H12B H 0.2677 0.144 -0.0714 0.063 Uiso 1 1 calc R . .
H12C H 0.0849 0.1466 -0.0165 0.063 Uiso 1 1 calc R . .
C141 C 0.3475(3) 0.52695(10) 0.1020(2) 0.0286(6) Uani 1 1 d . . .
C142 C 0.2320(4) 0.52634(11) -0.0032(2) 0.0371(6) Uani 1 1 d . . .
H142 H 0.1893 0.4912 -0.0348 0.045 Uiso 1 1 calc R . .
C143 C 0.1758(4) 0.57423(11) -0.0641(2) 0.0370(6) Uani 1 1 d . . .
H143 H 0.0989 0.5712 -0.137 0.044 Uiso 1 1 calc R . .
C144 C 0.2305(3) 0.62750(11) -0.0204(2) 0.0335(6) Uani 1 1 d . . .
C145 C 0.3486(4) 0.62854(11) 0.0854(2) 0.0367(6) Uani 1 1 d . . .
H145 H 0.3911 0.6637 0.1175 0.044 Uiso 1 1 calc R . .
C146 C 0.4051(4) 0.58004(10) 0.1445(2) 0.0342(6) Uani 1 1 d . . .
H146 H 0.4855 0.5827 0.2162 0.041 Uiso 1 1 calc R . .
N144 N 0.1704(3) 0.67566(9) -0.0781(2) 0.0430(6) Uani 1 1 d . . .
C147 C 0.0839(4) 0.67395(12) -0.1969(3) 0.0444(7) Uani 1 1 d . . .
H14A H 0.1658 0.6558 -0.2427 0.067 Uiso 1 1 calc R . .
H14B H 0.0574 0.7123 -0.225 0.067 Uiso 1 1 calc R . .
H14C H -0.0304 0.6526 -0.2039 0.067 Uiso 1 1 calc R . .
C148 C 0.2192(4) 0.72990(11) -0.0260(3) 0.0475(8) Uani 1 1 d . . .
H14D H 0.2011 0.7294 0.0544 0.071 Uiso 1 1 calc R . .
H14E H 0.1416 0.759 -0.068 0.071 Uiso 1 1 calc R . .
H14F H 0.3477 0.738 -0.0292 0.071 Uiso 1 1 calc R . .
C161 C 0.6697(3) 0.42571(11) 0.4524(2) 0.0318(6) Uani 1 1 d . . .
C162 C 0.7596(4) 0.47312(12) 0.5020(3) 0.0457(8) Uani 1 1 d . . .
H162 H 0.7426 0.5079 0.4625 0.055 Uiso 1 1 calc R . .
C163 C 0.8727(4) 0.47076(13) 0.6071(3) 0.0506(8) Uani 1 1 d . . .
H163 H 0.9313 0.5041 0.6385 0.061 Uiso 1 1 calc R . .
C164 C 0.9034(4) 0.42173(12) 0.6679(2) 0.0379(7) Uani 1 1 d . . .
C165 C 0.8051(4) 0.37505(12) 0.6232(2) 0.0447(7) Uani 1 1 d . . .
H165 H 0.8152 0.3412 0.6663 0.054 Uiso 1 1 calc R . .
C166 C 0.6926(4) 0.37666(11) 0.5172(2) 0.0409(7) Uani 1 1 d . . .
H166 H 0.6298 0.3436 0.4879 0.049 Uiso 1 1 calc R . .
C167 C 1.0379(4) 0.41820(14) 0.7786(3) 0.0499(8) Uani 1 1 d . . .
H16A H 0.973 0.4224 0.8439 0.075 Uiso 1 1 calc R . .
H16B H 1.1287 0.4482 0.7808 0.075 Uiso 1 1 calc R . .
H16C H 1.0997 0.3817 0.7833 0.075 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N11 C12 1.337(3) . ?
N11 C16 1.348(3) . ?
C12 C13 1.387(3) . ?
C12 C121 1.505(3) . ?
C13 C14 1.400(3) . ?
C13 H13 0.95 . ?
C14 C15 1.384(3) . ?
C14 C141 1.481(3) . ?
C15 C16 1.395(3) . ?
C15 H15 0.95 . ?
C16 C161 1.481(3) . ?
C121 C126 1.383(3) . ?
C121 C122 1.393(3) . ?
C122 C123 1.388(4) . ?
C122 H122 0.95 . ?
C123 C124 1.377(4) . ?
C123 H123 0.95 . ?
C124 C125 1.385(4) . ?
C124 C127 1.515(4) . ?
C125 C126 1.395(3) . ?
C125 H125 0.95 . ?
C126 H126 0.95 . ?
C127 H12A 0.98 . ?
C127 H12B 0.98 . ?
C127 H12C 0.98 . ?
C141 C142 1.384(3) . ?
C141 C146 1.401(3) . ?
C142 C143 1.375(4) . ?
C142 H142 0.95 . ?
C143 C144 1.404(4) . ?
C143 H143 0.95 . ?
C144 N144 1.370(3) . ?
C144 C145 1.399(4) . ?
C145 C146 1.378(3) . ?
C145 H145 0.95 . ?
C146 H146 0.95 . ?
N144 C147 1.439(4) . ?
N144 C148 1.451(4) . ?
C147 H14A 0.98 . ?
C147 H14B 0.98 . ?
C147 H14C 0.98 . ?
C148 H14D 0.98 . ?
C148 H14E 0.98 . ?
C148 H14F 0.98 . ?
C161 C162 1.391(4) . ?
C161 C166 1.391(4) . ?
C162 C163 1.375(4) . ?
C162 H162 0.95 . ?
C163 C164 1.370(4) . ?
C163 H163 0.95 . ?
C164 C165 1.385(4) . ?
C164 C167 1.506(4) . ?
C165 C166 1.381(4) . ?
C165 H165 0.95 . ?
C166 H166 0.95 . ?
C167 H16A 0.98 . ?
C167 H16B 0.98 . ?
C167 H16C 0.98 . ?

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
C12 N11 C16 117.7(2) . . ?
N11 C12 C13 122.9(2) . . ?
N11 C12 C121 115.9(2) . . ?
C13 C12 C121 121.2(2) . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 116.2(2) . . ?
C15 C14 C141 122.3(2) . . ?
C13 C14 C141 121.5(2) . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
N11 C16 C15 122.1(2) . . ?
N11 C16 C161 116.0(2) . . ?
C15 C16 C161 121.9(2) . . ?
C126 C121 C122 117.2(2) . . ?
C126 C121 C12 122.2(2) . . ?
C122 C121 C12 120.5(2) . . ?
C123 C122 C121 121.0(2) . . ?
C123 C122 H122 119.5 . . ?
C121 C122 H122 119.5 . . ?
C124 C123 C122 121.9(2) . . ?
C124 C123 H123 119.1 . . ?
C122 C123 H123 119.1 . . ?
C123 C124 C125 117.4(2) . . ?
C123 C124 C127 122.1(2) . . ?
C125 C124 C127 120.5(2) . . ?
C124 C125 C126 121.2(2) . . ?
C124 C125 H125 119.4 . . ?
C126 C125 H125 119.4 . . ?
C121 C126 C125 121.3(2) . . ?
C121 C126 H126 119.3 . . ?
C125 C126 H126 119.3 . . ?
C124 C127 H12A 109.5 . . ?
C124 C127 H12B 109.5 . . ?
H12A C127 H12B 109.5 . . ?
C124 C127 H12C 109.5 . . ?
H12A C127 H12C 109.5 . . ?
H12B C127 H12C 109.5 . . ?
C142 C141 C146 115.8(2) . . ?
C142 C141 C14 122.3(2) . . ?
C146 C141 C14 121.9(2) . . ?
C143 C142 C141 123.1(2) . . ?
C143 C142 H142 118.4 . . ?
C141 C142 H142 118.4 . . ?
C142 C143 C144 121.0(2) . . ?
C142 C143 H143 119.5 . . ?
C144 C143 H143 119.5 . . ?
N144 C144 C145 122.0(2) . . ?
N144 C144 C143 121.7(2) . . ?
C145 C144 C143 116.2(2) . . ?
C146 C145 C144 121.8(2) . . ?
C146 C145 H145 119.1 . . ?
C144 C145 H145 119.1 . . ?
C145 C146 C141 121.9(2) . . ?
C145 C146 H146 119 . . ?
C141 C146 H146 119 . . ?
C144 N144 C147 120.9(2) . . ?
C144 N144 C148 120.0(2) . . ?
C147 N144 C148 118.4(2) . . ?
N144 C147 H14A 109.5 . . ?
N144 C147 H14B 109.5 . . ?
H14A C147 H14B 109.5 . . ?
N144 C147 H14C 109.5 . . ?
H14A C147 H14C 109.5 . . ?
H14B C147 H14C 109.5 . . ?
N144 C148 H14D 109.5 . . ?
N144 C148 H14E 109.5 . . ?
H14D C148 H14E 109.5 . . ?
N144 C148 H14F 109.5 . . ?
H14D C148 H14F 109.5 . . ?
H14E C148 H14F 109.5 . . ?
C162 C161 C166 116.5(2) . . ?
C162 C161 C16 122.7(2) . . ?
C166 C161 C16 120.8(2) . . ?
C163 C162 C161 121.5(3) . . ?
C163 C162 H162 119.3 . . ?
C161 C162 H162 119.3 . . ?
C164 C163 C162 121.9(3) . . ?
C164 C163 H163 119.1 . . ?
C162 C163 H163 119.1 . . ?
C163 C164 C165 117.1(3) . . ?
C163 C164 C167 121.9(3) . . ?
C165 C164 C167 121.0(3) . . ?
C166 C165 C164 121.4(3) . . ?
C166 C165 H165 119.3 . . ?
C164 C165 H165 119.3 . . ?
C165 C166 C161 121.3(3) . . ?
C165 C166 H166 119.3 . . ?
C161 C166 H166 119.3 . . ?
C164 C167 H16A 109.5 . . ?
C164 C167 H16B 109.5 . . ?
H16A C167 H16B 109.5 . . ?
C164 C167 H16C 109.5 . . ?
H16A C167 H16C 109.5 . . ?
H16B C167 H16C 109.5 . . ?

#===END
_database_code_depnum_ccdc_archive 'CCDC 972818'
