# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_LASSBio_1289

_diffrn_measurement_device_type  'Stoe STADI-P powder diffractometer'
_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'
_chemical_melting_point          334
_exptl_crystal_description       powder
_exptl_crystal_colour            white
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         100
_cell_measurement_temperature    298(2)
_diffrn_radiation_monochromator  'curved Ge(111) monochromator'
_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.
Preferred orientation of the crystallites was described with a spherical
harmonics function of 4th order. 
;

_computing_molecular_graphics    'Mercury 3.3.1'
_computing_publication_material  'TOPAS ACADEMIC 5'
_audit_creation_method           'TOPAS ACADEMIC 5 + PLATON'
_computing_data_reduction        'Topas Academic v.5'
_computing_cell_refinement       'Topas Academic v.5'
_computing_data_collection       'Win X-POW'
_pd_calc_method                  'Rietveld Refinement'
_computing_structure_solution    'ab initio algorithm'
_computing_structure_refinement  'TOPAS ACADEMIC 5'
_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     138
_refine_ls_number_constraints    1
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_all   1.161
_pd_spec_mounting                '"Ultraphan" acetate foils'
_pd_spec_mount_mode              transmission
_pd_meas_scan_method             step
_pd_proc_ls_background_function  '20-term Chebyschev polynomial'
_pd_proc_ls_pref_orient_corr     '8 terms spherical harmonics'
_pd_proc_ls_profile_function     'Fundamental parameters approach'
_pd_proc_2theta_range_min        2
_pd_proc_2theta_range_max        40
_pd_proc_2theta_range_inc        0.015
_pd_proc_ls_prof_wR_expected     0.0363
_pd_proc_ls_prof_R_factor        0.0327
_pd_proc_ls_prof_wR_factor       0.0421
_refine_ls_R_I_factor            0.00620
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_weighting_scheme      sigma
_refine_ls_structure_factor_coef F



# 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     powder

_chemical_name_systematic        
(E)-N-methyl-N'-(thiophen-3-ylm-ethylene)benzo[d][1,3]dioxole-5-carbohydrazide
_chemical_name_common            LASSBio-1289
_chemical_formula_moiety         'C14 H12 N2 O3 S'
_chemical_formula_sum            'C14 H12 N2 O3 S'
_chemical_compound_source        LASSBio

_chemical_formula_weight         288.33

_exptl_crystal_F_000             600
_exptl_crystal_density_diffrn    1.44039
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_cell_special_details            Monoclinic

_exptl_absorpt_coefficient_mu    2.2504
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Correction based on shape and thickness'

_pd_meas_number_of_points        3780
_pd_proc_number_of_points        3780

_reflns_number_total             368
_reflns_limit_h_min              0
_reflns_limit_h_max              9
_reflns_limit_k_min              -7
_reflns_limit_k_max              7
_reflns_limit_l_min              -4
_reflns_limit_l_max              4
_reflns_d_resolution_high        14.50918
_reflns_d_resolution_low         1.56094



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

# PLATON
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'-x, y+1/2, -z+1/2 '
'x, -y+1/2, z+1/2 '
'-x, -y, -z '
_cell_length_a                   14.5118(3)
_cell_length_b                   12.1374(2)
_cell_length_c                   7.54977(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.1131(10)
_cell_angle_gamma                90
_cell_volume                     1329.53(4)
_cell_formula_units_Z            4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'

# 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'
S S 0.3331 0.7329 '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
N1 N 4 0.4142(10) 0.3906(13) 0.2439(18) 1 3.85(13) 0.04880
C2 C 4 0.4135(12) 0.5026(18) 0.206(2) 1 3.85(13) 0.04880
N3 N 4 0.3405(9) 0.3285(11) 0.1848(15) 1 3.85(13) 0.04880
C4 C 4 0.4957(10) 0.3394(10) 0.3329(15) 1 3.85(13) 0.04880
C5 C 4 0.3303(16) 0.5582(18) 0.130(3) 1 3.85(13) 0.04880
O6 O 4 0.4843(7) 0.5557(7) 0.2247(13) 1 3.85(13) 0.04880
C7 C 4 0.3405(13) 0.2234(14) 0.2119(17) 1 3.85(13) 0.04880
C11 C 4 0.3390(11) 0.6523(18) 0.028(2) 1 3.85(13) 0.04880
C12 C 4 0.2437(16) 0.5268(15) 0.1869(19) 1 3.85(13) 0.04880
C13 C 4 0.2607(16) 0.1572(14) 0.161(2) 1 3.85(13) 0.04880
C15 C 4 0.2617(17) 0.7114(12) -0.0289(17) 1 3.85(13) 0.04880
C17 C 4 0.1679(14) 0.586(2) 0.129(3) 1 3.85(13) 0.04880
C19 C 4 0.1784(13) 0.1978(13) 0.076(2) 1 3.85(13) 0.04880
C20 C 4 0.2507(10) 0.0493(14) 0.2083(15) 1 3.85(13) 0.04880
C21 C 4 0.1768(15) 0.6730(19) 0.019(3) 1 3.85(13) 0.04880
O23 O 4 0.0768(10) 0.5662(9) 0.1626(11) 1 3.85(13) 0.04880
C24 C 4 0.1110(12) 0.1124(14) 0.0397(15) 1 3.85(13) 0.04880
S26 S 4 0.1496(4) 0.0015(4) 0.1368(6) 1 3.85(13) 0.04880
O28 O 4 0.0925(10) 0.7188(8) -0.0200(12) 1 3.85(13) 0.04880
C29 C 4 0.0257(11) 0.6524(15) 0.0733(18) 1 3.85(13) 0.04880
H8 H 4 0.4736(10) 0.3134(10) 0.4337(15) 1 4.62(16) 0.05856
H9 H 4 0.5383(10) 0.3992(10) 0.3495(15) 1 4.62(16) 0.05856
H10 H 4 0.5159(10) 0.2847(10) 0.2494(15) 1 4.62(16) 0.05856
H14 H 4 0.3900(13) 0.1909(14) 0.2801(17) 1 4.62(16) 0.05856
H16 H 4 0.3982(11) 0.6740(18) -0.015(2) 1 4.62(16) 0.05856
H18 H 4 0.2385(16) 0.4668(15) 0.2688(19) 1 4.62(16) 0.05856
H22 H 4 0.2671(17) 0.7690(12) -0.1153(17) 1 4.62(16) 0.05856
H25 H 4 0.1712(13) 0.2725(13) 0.039(2) 1 4.62(16) 0.05856
H27 H 4 0.2921(10) 0.0127(14) 0.2911(15) 1 4.62(16) 0.05856
H30 H 4 0.0608(12) 0.1184(14) -0.0438(15) 1 4.62(16) 0.05856
H32 H 4 -0.0037(11) 0.6987(15) 0.1584(18) 1 4.62(16) 0.05856
H31 H 4 -0.0185(11) 0.6203(15) -0.0067(18) 1 4.62(16) 0.05856

#######################
# 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
N1 C2 1.39(3) . 1_555 n
N1 N3 1.38(2) . 1_555 n
N1 C4 1.49(2) . 1_555 n
C2 C5 1.49(3) . 1_555 n
C2 O6 1.22(2) . 1_555 n
N3 C7 1.29(2) . 1_555 n
C4 H8 0.89(2) . 1_555 n
C4 H9 0.96(2) . 1_555 n
C4 H10 0.97(2) . 1_555 n
C5 C11 1.38(3) . 1_555 n
C5 C12 1.39(3) . 1_555 n
C7 C13 1.46(3) . 1_555 n
C7 H14 0.96(2) . 1_555 n
C11 C15 1.39(3) . 1_555 n
C11 H16 0.96(2) . 1_555 n
C12 C17 1.38(3) . 1_555 n
C12 H18 0.96(2) . 1_555 n
C13 C19 1.43(3) . 1_555 n
C13 C20 1.37(2) . 1_555 n
C15 C21 1.37(3) . 1_555 n
C15 H22 0.96(2) . 1_555 n
C17 C21 1.35(3) . 1_555 n
C17 O23 1.37(3) . 1_555 n
C19 C24 1.45(2) . 1_555 n
C19 H25 0.95(2) . 1_555 n
C20 S26 1.66(2) . 1_555 n
C20 H27 0.97(2) . 1_555 n
C21 O28 1.37(3) . 1_555 n
O23 C29 1.44(2) . 1_555 n
C24 S26 1.63(2) . 1_555 n
C24 H30 0.96(2) . 1_555 n
O28 C29 1.45(2) . 1_555 n
C29 H32 0.96(2) . 1_555 n
C29 H31 0.96(2) . 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 N1 N3 118(1) 1_555 . 1_555 n
C2 N1 C4 120(1) 1_555 . 1_555 n
N3 N1 C4 122(1) 1_555 . 1_555 n
N1 C2 C5 122(2) 1_555 . 1_555 n
N1 C2 O6 119(2) 1_555 . 1_555 n
C5 C2 O6 119(2) 1_555 . 1_555 n
N1 N3 C7 119(1) 1_555 . 1_555 n
N1 C4 H8 104(1) 1_555 . 1_555 n
N1 C4 H9 104(1) 1_555 . 1_555 n
N1 C4 H10 104(1) 1_555 . 1_555 n
H8 C4 H9 113(2) 1_555 . 1_555 n
H8 C4 H10 116(2) 1_555 . 1_555 n
H9 C4 H10 114(2) 1_555 . 1_555 n
C2 C5 C11 120(2) 1_555 . 1_555 n
C2 C5 C12 119(2) 1_555 . 1_555 n
C11 C5 C12 119(2) 1_555 . 1_555 n
N3 C7 C13 120(1) 1_555 . 1_555 n
N3 C7 H14 119(2) 1_555 . 1_555 n
C13 C7 H14 120(2) 1_555 . 1_555 n
C5 C11 C15 121(2) 1_555 . 1_555 n
C5 C11 H16 120(2) 1_555 . 1_555 n
C15 C11 H16 118(2) 1_555 . 1_555 n
C5 C12 C17 119(2) 1_555 . 1_555 n
C5 C12 H18 119(2) 1_555 . 1_555 n
C17 C12 H18 122(2) 1_555 . 1_555 n
C7 C13 C19 126(2) 1_555 . 1_555 n
C7 C13 C20 123(2) 1_555 . 1_555 n
C19 C13 C20 111(2) 1_555 . 1_555 n
C11 C15 C21 118(2) 1_555 . 1_555 n
C11 C15 H22 121(2) 1_555 . 1_555 n
C21 C15 H22 121(2) 1_555 . 1_555 n
C12 C17 C21 121(2) 1_555 . 1_555 n
C12 C17 O23 128(2) 1_555 . 1_555 n
C21 C17 O23 111(2) 1_555 . 1_555 n
C13 C19 C24 113(1) 1_555 . 1_555 n
C13 C19 H25 123(2) 1_555 . 1_555 n
C24 C19 H25 124(2) 1_555 . 1_555 n
C13 C20 S26 110(1) 1_555 . 1_555 n
C13 C20 H27 123(2) 1_555 . 1_555 n
S26 C20 H27 126(1) 1_555 . 1_555 n
C15 C21 C17 122(2) 1_555 . 1_555 n
C15 C21 O28 127(2) 1_555 . 1_555 n
C17 C21 O28 111(2) 1_555 . 1_555 n
C17 O23 C29 106(1) 1_555 . 1_555 n
C19 C24 S26 106(1) 1_555 . 1_555 n
C19 C24 H30 125(2) 1_555 . 1_555 n
S26 C24 H30 128(2) 1_555 . 1_555 n
C20 S26 C24 98.7(8) 1_555 . 1_555 n
C21 O28 C29 106(1) 1_555 . 1_555 n
O23 C29 O28 107(1) 1_555 . 1_555 n
O23 C29 H32 110(2) 1_555 . 1_555 n
O23 C29 H31 109(2) 1_555 . 1_555 n
O28 C29 H32 108(2) 1_555 . 1_555 n
O28 C29 H31 111(2) 1_555 . 1_555 n
H32 C29 H31 111(2) 1_555 . 1_555 n

#End of data_Template


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether'
_database_code_depnum_ccdc_archive 'CCDC 1014103'
