# 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_argp27

_audit_creation_date             2013-07-05T00:28:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H18 Cl1 N3 O1'
_chemical_formula_sum            'C15 H18 Cl N3 O'
_chemical_formula_weight         291.77
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
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'

_cell_length_a                   5.7765(6)
_cell_length_b                   13.4566(13)
_cell_length_c                   19.456(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1512.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.1
_diffrn_reflns_number            3382
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.2
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_reflns_number_total             2569
_reflns_number_gt                1839
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 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)+(0.0158P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0064(9)
_refine_ls_number_reflns         2569
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(12)
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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 0.006 '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'

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
C1 C 0.6755(8) 0.4059(3) 0.51111(17) 0.0272(10) Uani 1 1 d . . .
C2 C 0.4693(8) 0.4488(3) 0.5286(2) 0.0331(11) Uani 1 1 d . . .
C3 C 0.3352(9) 0.4055(3) 0.58069(19) 0.0287(10) Uani 1 1 d . . .
C4 C 0.4114(7) 0.3192(3) 0.61434(17) 0.0223(9) Uani 1 1 d . . .
C5 C 0.6240(8) 0.2789(3) 0.59512(18) 0.0262(10) Uani 1 1 d . . .
C6 C 0.7570(8) 0.3211(3) 0.54374(19) 0.0275(10) Uani 1 1 d . . .
C7 C 0.2630(8) 0.2730(3) 0.6691(2) 0.0236(10) Uani 1 1 d . . .
C8 C 0.3561(7) 0.2911(2) 0.74163(17) 0.0189(8) Uani 1 1 d . . .
C9 C 0.1857(8) 0.2524(3) 0.79694(19) 0.0234(9) Uani 1 1 d . . .
C10 C 0.2625(7) 0.2402(3) 0.87207(19) 0.0246(10) Uani 1 1 d . . .
C11 C 0.1507(10) 0.1475(4) 0.9005(2) 0.0390(12) Uani 1 1 d . . .
C12 C 0.1731(10) 0.3317(4) 0.9107(2) 0.0383(12) Uani 1 1 d . . .
C13 C 0.5243(8) 0.2332(5) 0.8795(2) 0.0372(13) Uani 1 1 d . . .
C14 C 0.2941(9) 0.5459(3) 0.7647(2) 0.0367(12) Uani 1 1 d . . .
C15 C 0.5792(8) 0.4528(3) 0.7571(2) 0.0288(10) Uani 1 1 d . . .
Cl1 Cl 0.8424(2) 0.45970(8) 0.44601(5) 0.0431(4) Uani 1 1 d . . .
N1 N 0.3876(6) 0.3980(2) 0.75414(14) 0.0214(8) Uani 1 1 d . . .
N2 N 0.1959(6) 0.4575(2) 0.75834(15) 0.0295(8) Uani 1 1 d . . .
N3 N 0.5288(7) 0.5487(2) 0.76362(18) 0.0376(10) Uani 1 1 d . . .
O1 O -0.0127(5) 0.2363(2) 0.78012(12) 0.0297(7) Uani 1 1 d . . .
H8 H 0.512(7) 0.261(3) 0.7488(17) 0.036 Uiso 1 1 d . . .
H2 H 0.423(7) 0.508(2) 0.5072(15) 0.028(11) Uiso 1 1 d . . .
H3 H 0.193(7) 0.434(2) 0.5933(15) 0.018(10) Uiso 1 1 d . . .
H5 H 0.667(6) 0.210(2) 0.6156(14) 0.016(9) Uiso 1 1 d . . .
H6 H 0.907(7) 0.292(2) 0.5318(16) 0.030(11) Uiso 1 1 d . . .
H7A H 0.250(6) 0.200(2) 0.6628(16) 0.023(10) Uiso 1 1 d . . .
H7B H 0.110(7) 0.296(3) 0.6671(16) 0.024(11) Uiso 1 1 d . . .
H11A H 0.204(7) 0.131(3) 0.9518(19) 0.044(12) Uiso 1 1 d . . .
H11B H -0.015(8) 0.152(3) 0.8968(19) 0.045(14) Uiso 1 1 d . . .
H11C H 0.205(8) 0.088(3) 0.8735(18) 0.052(15) Uiso 1 1 d . . .
H12A H 0.246(8) 0.391(3) 0.8938(19) 0.051(14) Uiso 1 1 d . . .
H12B H 0.211(8) 0.321(3) 0.963(2) 0.069(15) Uiso 1 1 d . . .
H12C H -0.001(8) 0.334(3) 0.9105(18) 0.044(13) Uiso 1 1 d . . .
H13A H 0.568(6) 0.224(3) 0.9257(17) 0.029(11) Uiso 1 1 d . . .
H13B H 0.618(9) 0.180(3) 0.8518(19) 0.059(15) Uiso 1 1 d . . .
H13C H 0.603(8) 0.292(3) 0.8646(17) 0.038(13) Uiso 1 1 d . . .
H14 H 0.204(8) 0.598(3) 0.7662(18) 0.036(13) Uiso 1 1 d . . .
H15 H 0.730(7) 0.429(3) 0.7520(17) 0.027(12) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.367(6) . ?
C1 C6 1.388(5) . ?
C1 Cl1 1.749(4) . ?
C2 C3 1.402(6) . ?
C3 C4 1.405(5) . ?
C4 C5 1.393(6) . ?
C4 C7 1.502(5) . ?
C5 C6 1.382(5) . ?
C7 C8 1.529(5) . ?
C8 N1 1.469(4) . ?
C8 C9 1.549(5) . ?
C9 O1 1.212(5) . ?
C9 C10 1.536(5) . ?
C10 C11 1.510(6) . ?
C10 C13 1.522(6) . ?
C10 C12 1.532(6) . ?
C14 N2 1.324(5) . ?
C14 N3 1.357(6) . ?
C15 N3 1.328(5) . ?
C15 N1 1.331(5) . ?
N1 N2 1.369(4) . ?

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
C2 C1 C6 121.9(4) . . ?
C2 C1 Cl1 119.1(3) . . ?
C6 C1 Cl1 119.0(4) . . ?
C1 C2 C3 119.1(4) . . ?
C2 C3 C4 120.5(4) . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 C7 122.2(3) . . ?
C3 C4 C7 119.6(4) . . ?
C6 C5 C4 121.6(4) . . ?
C5 C6 C1 118.6(4) . . ?
C4 C7 C8 112.8(3) . . ?
N1 C8 C7 110.6(3) . . ?
N1 C8 C9 107.0(3) . . ?
C7 C8 C9 111.3(3) . . ?
O1 C9 C10 120.7(3) . . ?
O1 C9 C8 118.3(4) . . ?
C10 C9 C8 120.9(4) . . ?
C11 C10 C13 109.8(4) . . ?
C11 C10 C12 109.8(4) . . ?
C13 C10 C12 109.8(4) . . ?
C11 C10 C9 108.3(3) . . ?
C13 C10 C9 112.6(3) . . ?
C12 C10 C9 106.5(3) . . ?
N2 C14 N3 116.8(4) . . ?
N3 C15 N1 111.1(4) . . ?
C15 N1 N2 110.2(3) . . ?
C15 N1 C8 130.7(4) . . ?
N2 N1 C8 118.8(3) . . ?
C14 N2 N1 100.7(4) . . ?
C15 N3 C14 101.2(4) . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 969515'
