# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mexi_II
_database_code_depnum_ccdc_archive 'CCDC 1478423'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N O, Cl'
_chemical_formula_sum            'C11 H18 Cl N O'
_chemical_formula_weight         215.71

loop_
_atom_type_symbol000
_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 0.0000 0.0000 '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 0.0060 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn
_symmetry_space_group_name_Hall  '-P 2n 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   35.116(2)
_cell_length_b                   7.7402(5)
_cell_length_c                   9.1539(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2488.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9641
_cell_measurement_theta_min      2.320
_cell_measurement_theta_max      33.225

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8966
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
Saint Plus, Bruker AXS, Madison, WI, USA.  
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30104
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2192
_reflns_number_gt                2166
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
 Structure solved by direct methods to reveal all non-H atoms. H atoms 
 added at calculated positions and refined with a riding model. All non-H
 atoms refined anisotropically.
;

_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)+(0.0000P)²+3.7677P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2192
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.452
_refine_ls_restrained_S_all      1.452
_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
Cl1 Cl -0.048627(18) 0.30618(9) -0.06061(7) 0.02427(18) Uani 1 1 d . . .
O1 O 0.11762(5) 0.2571(2) 0.0012(2) 0.0211(4) Uani 1 1 d . . .
N1 N 0.04088(6) 0.3287(3) -0.0960(2) 0.0219(5) Uani 1 1 d . . .
H1A H 0.0526 0.4179 -0.0494 0.033 Uiso 1 1 calc R . .
H1B H 0.0152 0.3382 -0.0847 0.033 Uiso 1 1 calc R . .
H1C H 0.0467 0.3320 -0.1928 0.033 Uiso 1 1 calc R . .
C11 C 0.15581(7) 0.2627(3) -0.0421(3) 0.0191(6) Uani 1 1 d . . .
C12 C 0.18186(8) 0.1516(4) 0.0220(3) 0.0249(6) Uani 1 1 d . . .
C13 C 0.22004(8) 0.1677(4) -0.0203(3) 0.0341(7) Uani 1 1 d . . .
H13 H 0.2387 0.0943 0.0220 0.041 Uiso 1 1 calc R . .
C14 C 0.23080(8) 0.2888(4) -0.1227(4) 0.0395(8) Uani 1 1 d . . .
H14 H 0.2567 0.2966 -0.1517 0.047 Uiso 1 1 calc R . .
C15 C 0.20416(9) 0.3992(4) -0.1836(4) 0.0350(8) Uani 1 1 d . . .
H15 H 0.2120 0.4826 -0.2536 0.042 Uiso 1 1 calc R . .
C16 C 0.16605(8) 0.3891(4) -0.1432(3) 0.0258(6) Uani 1 1 d . . .
C17 C 0.16981(9) 0.0199(4) 0.1336(4) 0.0415(8) Uani 1 1 d . . .
H17A H 0.1504 0.0702 0.1977 0.062 Uiso 1 1 calc R . .
H17B H 0.1919 -0.0147 0.1920 0.062 Uiso 1 1 calc R . .
H17C H 0.1593 -0.0815 0.0839 0.062 Uiso 1 1 calc R . .
C18 C 0.13683(9) 0.5119(5) -0.2045(4) 0.0390(8) Uani 1 1 d . . .
H18A H 0.1194 0.4487 -0.2689 0.059 Uiso 1 1 calc R . .
H18B H 0.1497 0.6029 -0.2601 0.059 Uiso 1 1 calc R . .
H18C H 0.1224 0.5639 -0.1242 0.059 Uiso 1 1 calc R . .
C19 C 0.09523(7) 0.1306(4) -0.0729(3) 0.0223(6) Uani 1 1 d . . .
H19A H 0.1032 0.0130 -0.0432 0.027 Uiso 1 1 calc R . .
H19B H 0.0986 0.1416 -0.1799 0.027 Uiso 1 1 calc R . .
C20 C 0.05416(7) 0.1611(3) -0.0322(3) 0.0214(6) Uani 1 1 d . . .
H20 H 0.0385 0.0661 -0.0758 0.026 Uiso 1 1 calc R . .
C21 C 0.04687(8) 0.1639(4) 0.1313(3) 0.0313(7) Uani 1 1 d . . .
H21A H 0.0621 0.2557 0.1763 0.047 Uiso 1 1 calc R . .
H21B H 0.0540 0.0523 0.1736 0.047 Uiso 1 1 calc R . .
H21C H 0.0198 0.1856 0.1494 0.047 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0242(3) 0.0254(3) 0.0231(3) -0.0025(3) 0.0013(3) -0.0007(3)
O1 0.0209(9) 0.0220(9) 0.0205(9) -0.0046(8) 0.0006(8) -0.0008(8)
N1 0.0194(11) 0.0262(12) 0.0202(11) -0.0013(10) 0.0004(9) 0.0021(10)
C11 0.0189(12) 0.0206(13) 0.0177(13) -0.0034(11) -0.0008(11) 0.0011(10)
C12 0.0300(15) 0.0222(15) 0.0223(14) -0.0053(12) -0.0046(12) 0.0035(12)
C13 0.0264(15) 0.0377(18) 0.0383(18) -0.0127(15) -0.0093(13) 0.0098(13)
C14 0.0217(15) 0.044(2) 0.053(2) -0.0209(18) 0.0052(14) -0.0079(14)
C15 0.0354(17) 0.0352(18) 0.0343(17) -0.0042(15) 0.0089(14) -0.0142(14)
C16 0.0300(15) 0.0248(15) 0.0226(14) -0.0032(12) -0.0015(12) -0.0055(12)
C17 0.0481(19) 0.0376(19) 0.0388(18) 0.0096(16) -0.0104(16) 0.0089(16)
C18 0.0441(18) 0.0358(18) 0.0372(18) 0.0166(15) -0.0044(15) -0.0047(16)
C19 0.0251(14) 0.0224(14) 0.0195(13) -0.0059(12) 0.0006(11) 0.0011(11)
C20 0.0237(14) 0.0197(14) 0.0209(14) -0.0001(11) 0.0023(11) -0.0031(11)
C21 0.0315(15) 0.0366(17) 0.0256(15) 0.0056(14) 0.0075(13) 0.0027(14)

_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 C11 1.399(3) . ?
O1 C19 1.427(3) . ?
N1 C20 1.498(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C11 C12 1.386(4) . ?
C11 C16 1.394(4) . ?
C12 C13 1.401(4) . ?
C12 C17 1.504(4) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C18 1.507(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.508(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.518(4) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C11 O1 C19 114.51(19) . . ?
C20 N1 H1A 109.5 . . ?
C20 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C20 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C12 C11 C16 123.1(2) . . ?
C12 C11 O1 119.6(2) . . ?
C16 C11 O1 117.2(2) . . ?
C11 C12 C13 117.4(3) . . ?
C11 C12 C17 121.5(3) . . ?
C13 C12 C17 121.2(3) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 117.7(3) . . ?
C15 C16 C18 121.4(3) . . ?
C11 C16 C18 121.0(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C20 107.6(2) . . ?
O1 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O1 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
N1 C20 C19 109.7(2) . . ?
N1 C20 C21 108.6(2) . . ?
C19 C20 C21 114.0(2) . . ?
N1 C20 H20 108.1 . . ?
C19 C20 H20 108.1 . . ?
C21 C20 H20 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.053
