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


data_bca5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H36 N4 O4'
_chemical_formula_sum            'C36 H36 N4 O4'
_chemical_formula_weight         588.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'


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

_cell_length_a                   10.899(3)
_cell_length_b                   10.055(3)
_cell_length_c                   27.255(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2986.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)


_cell_measurement_reflns_used    1927
_cell_measurement_theta_min      1.6209
_cell_measurement_theta_max      44.3892


_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.692

_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3280


_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_source_voltage           40.0000
_diffrn_source_current           20.0000
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Saturn944 (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measurement_method       dtprofit.ref

_diffrn_reflns_reduction_process 'Lp corrections applied'





_diffrn_reflns_number            8920
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.20
_diffrn_reflns_theta_max         62.24
_reflns_number_total             2253
_reflns_number_gt                1985
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SIR2002
_computing_structure_refinement  SHELXL-97
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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)+(0.1550P)²+0.9273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2253
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.2208
_refine_ls_wR_factor_gt          0.1720
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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 0.45088(14) 0.18237(16) 0.52514(6) 0.0545(6) Uani 1 1 d . . .
N1 N 0.64100(17) 0.11765(19) 0.50055(7) 0.0487(6) Uani 1 1 d . . .
O2 O 0.73183(17) 0.1323(2) 0.38052(7) 0.0673(7) Uani 1 1 d . . .
N2 N 0.56817(17) 0.0089(2) 0.40283(7) 0.0510(6) Uani 1 1 d . . .
C1 C 0.5420(2) 0.1105(2) 0.53058(9) 0.0461(7) Uani 1 1 d . . .
C2 C 0.5461(2) 0.0042(2) 0.57029(9) 0.0483(7) Uani 1 1 d . . .
H2A H 0.5659 -0.0806 0.5553 0.058 Uiso 1 1 calc R . .
H2B H 0.6113 0.0256 0.5932 0.058 Uiso 1 1 calc R . .
C3 C 0.7531(2) 0.0395(3) 0.50813(9) 0.0547(7) Uani 1 1 d . . .
H3A H 0.8056 0.0509 0.4797 0.066 Uiso 1 1 calc R . .
H3B H 0.7307 -0.0538 0.5098 0.066 Uiso 1 1 calc R . .
C4 C 0.8268(2) 0.0736(2) 0.55365(9) 0.0505(7) Uani 1 1 d . . .
C5 C 0.9225(2) -0.0111(3) 0.56701(11) 0.0626(8) Uani 1 1 d . . .
H5 H 0.9404 -0.0847 0.5477 0.075 Uiso 1 1 calc R . .
C6 C 0.9907(3) 0.0133(3) 0.60854(13) 0.0774(10) Uani 1 1 d . . .
H6 H 1.0539 -0.0443 0.6172 0.093 Uiso 1 1 calc R . .
C7 C 0.9656(3) 0.1230(3) 0.63747(12) 0.0732(9) Uani 1 1 d . . .
H7 H 1.0116 0.1392 0.6656 0.088 Uiso 1 1 calc R . .
C8 C 0.8728(3) 0.2076(3) 0.62451(10) 0.0646(8) Uani 1 1 d . . .
H8 H 0.8557 0.2815 0.6439 0.077 Uiso 1 1 calc R . .
C9 C 0.8043(2) 0.1836(2) 0.58275(9) 0.0542(7) Uani 1 1 d . . .
H9 H 0.7420 0.2424 0.5741 0.065 Uiso 1 1 calc R . .
C10 C 0.6479(2) 0.1105(2) 0.40953(9) 0.0518(7) Uani 1 1 d . . .
C11 C 0.6369(2) 0.1962(2) 0.45537(9) 0.0538(7) Uani 1 1 d . . .
H11A H 0.7033 0.2604 0.4558 0.065 Uiso 1 1 calc R . .
H11B H 0.5602 0.2450 0.4542 0.065 Uiso 1 1 calc R . .
C12 C 0.5861(3) -0.0850(3) 0.36241(9) 0.0601(8) Uani 1 1 d . . .
H12A H 0.5721 -0.1746 0.3743 0.072 Uiso 1 1 calc R . .
H12B H 0.6703 -0.0795 0.3511 0.072 Uiso 1 1 calc R . .
C13 C 0.5013(2) -0.0578(3) 0.32001(10) 0.0619(8) Uani 1 1 d . . .
C14 C 0.5141(3) 0.0555(3) 0.29191(11) 0.0735(9) Uani 1 1 d . . .
H14 H 0.5772 0.1145 0.2991 0.088 Uiso 1 1 calc R . .
C15 C 0.4361(4) 0.0836(5) 0.25364(13) 0.0977(13) Uani 1 1 d . . .
H15 H 0.4469 0.1604 0.2351 0.117 Uiso 1 1 calc R . .
C16 C 0.3431(4) -0.0019(7) 0.24309(17) 0.126(2) Uani 1 1 d . . .
H16 H 0.2905 0.0172 0.2172 0.151 Uiso 1 1 calc R . .
C17 C 0.3257(4) -0.1145(7) 0.26965(17) 0.132(2) Uani 1 1 d . . .
H17 H 0.2619 -0.1722 0.2620 0.159 Uiso 1 1 calc R . .
C18 C 0.4053(4) -0.1427(5) 0.30880(14) 0.1037(13) Uani 1 1 d . . .
H18 H 0.3933 -0.2191 0.3274 0.124 Uiso 1 1 calc R . .


_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 1.237(3) . ?
N1 C1 1.356(3) . ?
N1 C11 1.463(3) . ?
N1 C3 1.468(3) . ?
O2 C10 1.229(3) . ?
N2 C10 1.353(3) . ?
N2 C2 1.451(3) 5_656 ?
N2 C12 1.464(3) . ?
C1 C2 1.522(3) . ?
C2 N2 1.451(3) 5_656 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.517(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.383(4) . ?
C4 C5 1.395(4) . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.522(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.504(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.380(5) . ?
C13 C18 1.385(5) . ?
C14 C15 1.375(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.404(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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 N1 C11 120.8(2) . . ?
C1 N1 C3 123.3(2) . . ?
C11 N1 C3 115.66(19) . . ?
C10 N2 C2 123.5(2) . 5_656 ?
C10 N2 C12 120.2(2) . . ?
C2 N2 C12 115.83(19) 5_656 . ?
O1 C1 N1 122.4(2) . . ?
O1 C1 C2 121.3(2) . . ?
N1 C1 C2 116.3(2) . . ?
N2 C2 C1 113.41(19) 5_656 . ?
N2 C2 H2A 108.9 5_656 . ?
C1 C2 H2A 108.9 . . ?
N2 C2 H2B 108.9 5_656 . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N1 C3 C4 115.7(2) . . ?
N1 C3 H3A 108.3 . . ?
C4 C3 H3A 108.3 . . ?
N1 C3 H3B 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C9 C4 C5 118.1(2) . . ?
C9 C4 C3 123.8(2) . . ?
C5 C4 C3 118.1(2) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
O2 C10 N2 121.7(2) . . ?
O2 C10 C11 119.0(2) . . ?
N2 C10 C11 119.1(2) . . ?
N1 C11 C10 112.5(2) . . ?
N1 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N2 C12 C13 112.3(2) . . ?
N2 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C18 117.6(3) . . ?
C14 C13 C12 120.9(2) . . ?
C18 C13 C12 121.5(3) . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C16 C15 C14 119.4(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.2(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C13 C18 C17 120.7(4) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?

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
C11 N1 C1 O1 -9.9(3) . . . . ?
C3 N1 C1 O1 176.0(2) . . . . ?
C11 N1 C1 C2 167.35(19) . . . . ?
C3 N1 C1 C2 -6.7(3) . . . . ?
O1 C1 C2 N2 4.4(3) . . . 5_656 ?
N1 C1 C2 N2 -172.91(19) . . . 5_656 ?
C1 N1 C3 C4 -66.6(3) . . . . ?
C11 N1 C3 C4 119.0(2) . . . . ?
N1 C3 C4 C9 -10.1(4) . . . . ?
N1 C3 C4 C5 169.7(2) . . . . ?
C9 C4 C5 C6 1.3(4) . . . . ?
C3 C4 C5 C6 -178.5(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C7 C8 C9 C4 0.8(4) . . . . ?
C5 C4 C9 C8 -1.4(4) . . . . ?
C3 C4 C9 C8 178.4(2) . . . . ?
C2 N2 C10 O2 -166.5(2) 5_656 . . . ?
C12 N2 C10 O2 4.9(4) . . . . ?
C2 N2 C10 C11 16.3(3) 5_656 . . . ?
C12 N2 C10 C11 -172.3(2) . . . . ?
C1 N1 C11 C10 -114.7(2) . . . . ?
C3 N1 C11 C10 59.8(3) . . . . ?
O2 C10 C11 N1 -122.1(2) . . . . ?
N2 C10 C11 N1 55.2(3) . . . . ?
C10 N2 C12 C13 -102.3(3) . . . . ?
C2 N2 C12 C13 69.8(3) 5_656 . . . ?
N2 C12 C13 C14 68.1(3) . . . . ?
N2 C12 C13 C18 -109.6(3) . . . . ?
C18 C13 C14 C15 -0.9(5) . . . . ?
C12 C13 C14 C15 -178.6(3) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 0.2(8) . . . . ?
C14 C13 C18 C17 1.1(5) . . . . ?
C12 C13 C18 C17 178.8(3) . . . . ?
C16 C17 C18 C13 -0.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        62.24
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 971028'
