# Electronic Supplementary Material (ESI) for Dalton Transactions
# 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
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# 
#  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_Kuwar1948

_audit_creation_date             2013-07-17T17:49:31-00:00
_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_name_common            'Kuwar 1948'
_chemical_formula_moiety         'C18 H24 N2 O2'
_chemical_formula_sum            'C18 H24 N2 O2'
_chemical_formula_weight         300.39
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

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

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
_space_group_IT_number           92
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,3/4-z
-x,-y,1/2+z
1/2-x,1/2+y,1/4-z
y,x,-z
1/2+y,1/2-x,3/4+z
1/2-y,1/2+x,1/4+z
-y,-x,1/2-z

_cell_length_a                   7.5161(6)
_cell_length_b                   7.5161(6)
_cell_length_c                   29.023(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1639.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    944
_cell_measurement_theta_min      1.018
_cell_measurement_theta_max      25.028
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       'rectangular chunk'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler.  
 The data collection strategy was set up to measure an octant of 
 reciprocal space with a redundancy factor of 4.6, which means that 
 90% of these reflections were measured at least 4.6 times.  Phi and 
 omega scans with a frame width of 0.5 degree were used.
 Data integration was done with Denzo, and scaling and merging
 of the data was done with Scalepack.
;

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

_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.906178E-1
_diffrn_orient_matrix_ub_12      0.974076E-1
_diffrn_orient_matrix_ub_13      0.3538E-3
_diffrn_orient_matrix_ub_21      -0.89121E-1
_diffrn_orient_matrix_ub_22      -0.821391E-1
_diffrn_orient_matrix_ub_23      -0.142133E-1
_diffrn_orient_matrix_ub_31      -0.393389E-1
_diffrn_orient_matrix_ub_32      -0.382965E-1
_diffrn_orient_matrix_ub_33      0.31385E-1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_theta_min         2.799
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_number            10916
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_ful 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             1434
_reflns_number_gt                1170
_reflns_threshold_expression     'I > 2\s(I)'

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;The molecule contains a crystallographic two-fold rotation axis.

 The N-H and O-H hydrogen atoms were located on electron density maps
 and refined isotropically. The O-H group is involved in an intermolecular
 hydrogen bond with a nitrogen atom and the N-H group is involved in an
 intramolecular hydrogen bond with the oxygen atom. 

 For the methyl group, the hydrogen atoms were
 added at calculated positions using a riding model with 
 U(H) = 1.5 * Ueq(bonded carbon atom).  The torsion angle, which defines 
 the orientation of this methyl group about the C-C bond, was refined. 
 The rest of the hydrogen atoms were included in the model at calculated
 positions using a riding model with U(H) = 1.2 * Ueq(bonded atom).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+1.6408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1434
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.059
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 
;
 Flack x determined using 374 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_diff_density_max         0.5
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   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'
H H 0 0 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3605(5) 0.7843(5) 0.08233(14) 0.0402(10) Uani 1 d . .
C2 C 0.3999(6) 0.7326(6) 0.12724(14) 0.0441(10) Uani 1 d . .
H2 H 0.3315 0.6407 0.1411 0.053 Uiso 1 calc . .
C3 C 0.5338(6) 0.8094(7) 0.15214(15) 0.0524(12) Uani 1 d . .
H3 H 0.5574 0.7711 0.1827 0.063 Uiso 1 calc . .
C4 C 0.6343(6) 0.9429(7) 0.13253(15) 0.0513(12) Uani 1 d . .
H4 H 0.7275 0.9971 0.1496 0.062 Uiso 1 calc . .
C5 C 0.5994(5) 0.9978(6) 0.08790(14) 0.0457(11) Uani 1 d . .
H5 H 0.669 1.0897 0.0745 0.055 Uiso 1 calc . .
C6 C 0.4630(5) 0.9196(5) 0.06252(13) 0.0401(10) Uani 1 d . .
C7 C 0.2087(6) 0.6942(6) 0.05723(16) 0.0480(11) Uani 1 d . .
H7 H 0.1643 0.5983 0.0782 0.058 Uiso 1 calc . .
C8 C 0.0518(6) 0.8155(6) 0.04808(16) 0.0510(11) Uani 1 d . .
H8A H 0.0905 0.9164 0.0292 0.076 Uiso 1 calc . .
H8B H 0.0044 0.8593 0.0774 0.076 Uiso 1 calc . .
H8C H -0.041 0.7492 0.0317 0.076 Uiso 1 calc . .
C9 C 0.3973(6) 0.4643(7) 0.02271(15) 0.0521(12) Uani 1 d . .
H9A H 0.3433 0.3652 0.0403 0.063 Uiso 1 calc . .
H9B H 0.4975 0.5127 0.041 0.063 Uiso 1 calc . .
N N 0.2618(5) 0.6065(5) 0.01476(12) 0.0477(9) Uani 1 d . .
H1N H 0.326(7) 0.711(7) -0.0060(17) 0.074(15) Uiso 1 d . .
O O 0.4254(4) 0.9693(4) 0.01849(9) 0.0526(9) Uani 1 d . .
H1O H 0.498(10) 1.063(10) 0.007(2) 0.13(3) Uiso 1 d . .

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
C1 0.039(2) 0.032(2) 0.050(2) -0.0004(18) -0.0024(18) 0.0047(18)
C2 0.042(2) 0.042(2) 0.047(2) 0.009(2) 0.0073(19) 0.007(2)
C3 0.047(3) 0.062(3) 0.048(2) 0.003(2) -0.005(2) 0.016(2)
C4 0.039(2) 0.060(3) 0.055(3) -0.015(2) -0.007(2) 0.008(2)
C5 0.037(2) 0.044(2) 0.056(2) -0.007(2) 0.0070(19) -0.0061(19)
C6 0.042(2) 0.037(2) 0.040(2) -0.0037(17) 0.0031(18) 0.0026(18)
C7 0.045(2) 0.039(2) 0.060(3) -0.006(2) -0.009(2) -0.001(2)
C8 0.041(2) 0.046(3) 0.065(3) -0.006(2) -0.011(2) 0.008(2)
C9 0.043(3) 0.052(3) 0.061(3) -0.012(2) -0.002(2) 0.008(2)
N 0.039(2) 0.051(2) 0.053(2) -0.0073(17) -0.0030(17) 0.0086(18)
O 0.065(2) 0.0514(18) 0.0413(16) 0.0070(14) -0.0008(15) -0.0057(17)


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.392(5) . ?
C1 C6 1.399(6) . ?
C1 C7 1.514(6) . ?
C2 C3 1.367(6) . ?
C2 H2 0.95 . ?
C3 C4 1.379(7) . ?
C3 H3 0.95 . ?
C4 C5 1.385(6) . ?
C4 H4 0.95 . ?
C5 C6 1.393(6) . ?
C5 H5 0.95 . ?
C6 O 1.361(5) . ?
C7 N 1.454(5) . ?
C7 C8 1.514(6) . ?
C7 H7 1 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 N 1.494(6) . ?
C9 C9 1.498(8) 5 ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
N H1N 1.10(5) . ?
O H1O 0.95(7) . ?

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 118.1(4) . . ?
C2 C1 C7 119.1(4) . . ?
C6 C1 C7 122.9(4) . . ?
C3 C2 C1 122.3(4) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
O C6 C5 122.2(4) . . ?
O C6 C1 118.1(4) . . ?
C5 C6 C1 119.7(3) . . ?
N C7 C1 113.8(4) . . ?
N C7 C8 109.8(4) . . ?
C1 C7 C8 113.7(3) . . ?
N C7 H7 106.3 . . ?
C1 C7 H7 106.3 . . ?
C8 C7 H7 106.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N C9 C9 109.5(5) . 5 ?
N C9 H9A 109.8 . . ?
C9 C9 H9A 109.8 5 . ?
N C9 H9B 109.8 . . ?
C9 C9 H9B 109.8 5 . ?
H9A C9 H9B 108.2 . . ?
C7 N C9 112.4(3) . . ?
C7 N H1N 105(3) . . ?
C9 N H1N 107(3) . . ?
C6 O H1O 114(4) . . ?

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
C6 C1 C2 C3 0.1(6) . . . . ?
C7 C1 C2 C3 -179.3(4) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 O -179.6(4) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C2 C1 C6 O 179.5(4) . . . . ?
C7 C1 C6 O -1.1(6) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
C7 C1 C6 C5 179.3(4) . . . . ?
C2 C1 C7 N -121.1(4) . . . . ?
C6 C1 C7 N 59.5(5) . . . . ?
C2 C1 C7 C8 112.3(5) . . . . ?
C6 C1 C7 C8 -67.1(5) . . . . ?
C1 C7 N C9 60.1(5) . . . . ?
C8 C7 N C9 -171.2(4) . . . . ?
C9 C9 N C7 -172.2(3) 5 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A O 0.98 2.57 3.156(6) 118.6 .
N H1N O 1.10(5) 2.20(5) 2.993(5) 127(3) .
O H1O N 0.95(7) 1.81(7) 2.760(5) 171(7) 5_565

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 952233'