# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LASSBio_1601
_database_code_depnum_ccdc_archive 'CCDC 1040619'

_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;


_publcif_datablock.id            {f4648ea8-3c9e-4c02-be9f-3a23ac18e148}

_diffrn_measurement_device_type  'Huber 4+2 circles'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_radiation_wavelength     1.54056
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Stoe STADI-P'
_exptl_crystal_colour            white
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         100
_cell_measurement_temperature    298(2)
_diffrn_radiation_monochromator  Si(111)
_exptl_absorpt_correction_T_min  ?
_exptl_special_details           ?
_atom_sites_solution_hydrogens   geom

##########################################
# 3. OVERALL SOLUTION/REFINEMENT DETAILS #
##########################################

_refine_special_details          
;
A Rietveld refinement was performed with the TOPAS package using the fundamental
parameters approach as reflection profiles (convolution of appropriate source
emission profiles with axial instrument contributions as well as crystallite
microstructure effects). In order to describe small peak half width and shape
anisotropy effects, the approach of Le Bail and Jouanneaux was implemented
into the TOPAS program and the according parameters were allowed to refine
freely.
;

_computing_molecular_graphics    'Mercury 3.3.1'
_computing_publication_material  'Mercury 3.3.1'
_audit_creation_method           'TOPAS ACADEMIC 5 + PLATON'
_computing_data_reduction        'Topas Academic v.5'
_computing_cell_refinement       'Topas Academic v.5'
_computing_data_collection       WinXPOW
_pd_calc_method                  'Rietveld Refinement'
_computing_structure_solution    'DASH v3.3.2'
_computing_structure_refinement  'TOPAS ACADEMIC 5'
_refine_ls_structure_factor_coef Inet
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_mean         0.0001
_refine_ls_shift/su_max          0.0001
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_constraints    0
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_all   0.832
_refine_ls_R_I_factor            0.00666
_pd_spec_mounting                'acetate-cellulose foils'
_pd_spec_mount_mode              transmission
_pd_meas_scan_method             step
_pd_proc_ls_background_function  '20-term Chebyschev polynomial'
_pd_proc_ls_profile_function     'Fundamental parameters approach'
_pd_proc_2theta_range_min        4.615
_pd_proc_2theta_range_max        80.395
_pd_proc_2theta_range_inc        0.005
_pd_proc_ls_prof_wR_expected     0.02408
_pd_proc_ls_prof_R_factor        0.01489
_pd_proc_ls_prof_wR_factor       0.02005
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_weighting_scheme      sigma



# if regions of the data are excluded, the reason(s) are supplied here:
_pd_proc_info_excluded_regions   none



#####################
# 4. SAMPLE DETAILS #
#####################

_pd_char_colour                  white
_pd_char_particle_morphology     ?

_chemical_name_systematic        (E)-N'-benzylidenecyclohexanecarbohydrazide
_chemical_name_common            LASSBio-1601
_chemical_formula_moiety         'C14 H18 N2 O'
_chemical_formula_sum            'C14 H18 N2 O'

_chemical_formula_weight         230.31

_exptl_crystal_F_000             248
_exptl_crystal_density_diffrn    1.2010
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_cell_special_details            Triclinic

_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
;

_pd_meas_number_of_points        3990
_pd_proc_number_of_points        3990

_reflns_number_total             410
_reflns_limit_h_min              0
_reflns_limit_h_max              3
_reflns_limit_k_min              -7
_reflns_limit_k_max              7
_reflns_limit_l_min              -10
_reflns_limit_l_max              10
_reflns_d_resolution_high        12.47181
_reflns_d_resolution_low         1.48848



###################
# 5. CRYSTAL DATA #
###################

# PLATON
loop_
_symmetry_equiv_pos_as_xyz
'-x, -y, -z'
'x, y, z'
_chemical_name_mineral           NAH1601
_cell_length_a                   4.7774(3)
_cell_length_b                   10.8468(6)
_cell_length_c                   15.7986(11)
_cell_angle_alpha                52.351(5)
_cell_angle_beta                 99.385(5)
_cell_angle_gamma                99.707(3)
_cell_volume                     637.03(8)
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 1'
_cell_formula_units_Z            2

# PLATON
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
_atom_site_U_iso_or_equiv

C1 C 2 0.780(5) 0.547(4) 0.357(2) 1 3.0(12) 0.03812
C2 C 2 0.605(5) 0.591(3) 0.2555(18) 1 3.0(12) 0.03812
O3 O 2 0.943(3) 0.444(2) 0.4055(12) 1 3.0(12) 0.03812
N4 N 2 0.724(3) 0.617(2) 0.4004(18) 1 3.0(12) 0.03812
C5 C 2 0.741(4) 0.745(3) 0.1603(15) 1 3.0(12) 0.03812
C6 C 2 0.595(5) 0.458(2) 0.2466(18) 1 3.0(12) 0.03812
N8 N 2 0.527(3) 0.724(2) 0.3512(16) 1 3.0(12) 0.03812
C10 C 2 0.592(4) 0.788(3) 0.0529(16) 1 3.0(12) 0.03812
C13 C 2 0.449(4) 0.503(3) 0.1392(15) 1 3.0(12) 0.03812
C16 C 2 0.501(4) 0.785(3) 0.397(2) 1 3.0(12) 0.03812
C17 C 2 0.585(4) 0.654(2) 0.0450(15) 1 3.0(12) 0.03812
C22 C 2 0.305(5) 0.907(4) 0.350(2) 1 3.0(12) 0.03812
C26 C 2 0.185(4) 0.977(3) 0.2462(19) 1 3.0(12) 0.03812
C27 C 2 0.270(4) 0.964(3) 0.4053(16) 1 3.0(12) 0.03812
C28 C 2 -0.001(4) 1.092(3) 0.2009(18) 1 3.0(12) 0.03812
C30 C 2 0.078(4) 1.075(3) 0.3632(18) 1 3.0(12) 0.03812
C32 C 2 -0.057(4) 1.140(3) 0.2604(19) 1 3.0(12) 0.03812
H7 H 2 0.422(5) -0.389(3) -0.7468(18) 1 3.6(14) 0.04574
H9 H 2 0.802(3) -0.420(2) -0.5338(18) 1 3.6(14) 0.04574
H11 H 2 0.929(4) -0.261(3) -0.8348(15) 1 3.6(14) 0.04574
H12 H 2 0.693(4) -0.176(3) -0.8370(15) 1 3.6(14) 0.04574
H14 H 2 0.470(5) -0.628(2) -0.6976(18) 1 3.6(14) 0.04574
H15 H 2 0.769(5) -0.574(2) -0.7439(18) 1 3.6(14) 0.04574
H18 H 2 0.728(4) -0.134(3) -0.9995(16) 1 3.6(14) 0.04574
H19 H 2 0.421(4) -0.182(3) -0.9607(16) 1 3.6(14) 0.04574
H20 H 2 0.245(4) -0.489(3) -0.8656(15) 1 3.6(14) 0.04574
H21 H 2 0.457(4) -0.586(3) -0.8638(15) 1 3.6(14) 0.04574
H23 H 2 0.601(4) -0.244(3) -0.535(2) 1 3.6(14) 0.04574
H24 H 2 0.764(4) -0.375(2) -0.9536(15) 1 3.6(14) 0.04574
H25 H 2 0.467(4) -0.327(2) -1.0170(15) 1 3.6(14) 0.04574
H29 H 2 0.232(4) -0.068(3) -0.7888(19) 1 3.6(14) 0.04574
H31 H 2 0.338(4) -0.073(3) -0.5233(16) 1 3.6(14) 0.04574
H33 H 2 -0.077(4) 0.129(3) -0.8716(18) 1 3.6(14) 0.04574
H34 H 2 0.028(4) 0.124(3) -0.6075(18) 1 3.6(14) 0.04574
H35 H 2 -0.178(4) 0.224(3) -0.7806(19) 1 3.6(14) 0.04574

#######################
# 6. BONDS AND ANGLES #
#######################

# PLATON
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.50(4) . 1_555 n
C1 O3 1.22(4) . 1_555 n
C1 N4 1.37(6) . 1_555 n
C2 C5 1.54(3) . 1_555 n
C2 C6 1.52(5) . 1_555 n
N4 N8 1.37(2) . 1_555 n
C5 C10 1.53(3) . 1_555 n
C6 C13 1.52(3) . 1_555 n
N8 C16 1.27(5) . 1_555 n
C10 C17 1.53(5) . 1_555 n
C13 C17 1.52(2) . 1_555 n
C16 C22 1.47(4) . 1_555 n
C22 C26 1.38(4) . 1_555 n
C22 C27 1.38(6) . 1_555 n
C26 C28 1.39(4) . 1_555 n
C27 C30 1.39(4) . 1_555 n
C28 C32 1.40(5) . 1_555 n
C30 C32 1.40(3) . 1_555 n

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O3 123(3) 1_555 . 1_555 n
C2 C1 N4 116(3) 1_555 . 1_555 n
O3 C1 N4 120(3) 1_555 . 1_555 n
C1 C2 C5 109(2) 1_555 . 1_555 n
C1 C2 C6 108(2) 1_555 . 1_555 n
C5 C2 C6 112(2) 1_555 . 1_555 n
C1 N4 N8 121(2) 1_555 . 1_555 n
C2 C5 C10 111(2) 1_555 . 1_555 n
C2 C6 C13 111(2) 1_555 . 1_555 n
N4 N8 C16 115(2) 1_555 . 1_555 n
C5 C10 C17 111(2) 1_555 . 1_555 n
C6 C13 C17 112(2) 1_555 . 1_555 n
N8 C16 C22 121(3) 1_555 . 1_555 n
C10 C17 C13 111(2) 1_555 . 1_555 n
C16 C22 C26 120(3) 1_555 . 1_555 n
C16 C22 C27 119(3) 1_555 . 1_555 n
C26 C22 C27 120(3) 1_555 . 1_555 n
C22 C26 C28 121(3) 1_555 . 1_555 n
C22 C27 C30 120(3) 1_555 . 1_555 n
C26 C28 C32 119(2) 1_555 . 1_555 n
C27 C30 C32 120(2) 1_555 . 1_555 n
C28 C32 C30 120(2) 1_555 . 1_555 n
