# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  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.
#
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#  fide research purposes only. It may contain copyright material
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data_test1
_audit_creation_date             2014-04-01
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4813)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        Isopropanol
_chemical_formula_moiety         'C3 H8 O'
_chemical_formula_sum            'C3 H8 O'
_chemical_formula_weight         60.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7267(18)
_cell_length_b                   21.838(6)
_cell_length_c                   8.408(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.243(8)
_cell_angle_gamma                90
_cell_volume                     1411.5(6)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    85
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      14.94
_cell_measurement_theta_min      3.73
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.052
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.4837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0990 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.6501.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method 
'Crystallised at high-pressure in a diamond anvil cell'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
The data collection nominally covered a full sphere of reciprocal space by
a combination of φ scans. Each image (3.0 s exposure) covering -0.50\ degrees.
The crystal to detector distance was 5.00 cm
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.290
_diffrn_reflns_Laue_measured_fraction_max 0.603
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6526
_diffrn_reflns_point_group_measured_fraction_full 0.290
_diffrn_reflns_point_group_measured_fraction_max 0.603
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         15.340
_diffrn_reflns_theta_min         2.216
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.290
_diffrn_measured_fraction_theta_max 0.603
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  IuS_Ag_high_pressure
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_collimation    'Multilayer mirrors'
_diffrn_radiation_monochromator  'Bruker Helios multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_target            Ag
_diffrn_source_type              'Incoatec IuS'
_diffrn_special_details          
'Resolution, completeness and redundancy compromised as crystal held in diamond anvil cell'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                503
_reflns_number_total             743
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         743
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+2.4683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C16A \\sim C11A \\sim C14A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C16) = Uanis(C16A)
Uanis(C14) = Uanis(C14A)
Uanis(C11) = Uanis(C11A)
3. Others
 Sof(C16A)=Sof(H16d)=Sof(H16e)=Sof(H16f)=Sof(C14A)=Sof(H14A)=Sof(C11A)=
 Sof(H11d)=Sof(H11e)=Sof(H11f)=1-FVAR(1)
 Sof(C11)=Sof(H11a)=Sof(H11b)=Sof(H11c)=Sof(C14)=Sof(H14)=Sof(C16)=Sof(H16a)=
 Sof(H16b)=Sof(H16c)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C14(H14), C17(H17), C2(H2a), C14A(H14A)
4.b Tetrahedral OH refined with riding coordinates:
 O3(H3)
4.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c),
 C11(H11a,H11b,H11c), C16(H16a,H16b,H16c), C3(H3a,H3b,H3c), C4(H4a,H4b,H4c),
 C16A(H16d,H16e,H16f), C11A(H11d,H11e,H11f)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.7621(7) 0.6018(2) 0.9415(8) 0.0454(18) Uani 1 1 d . . . . .
H2 H -0.7372 0.5655 0.9655 0.068 Uiso 1 1 calc GR . . . .
O3 O -0.8181(5) 0.3986(2) 0.8283(8) 0.0413(18) Uani 1 1 d . . . . .
H3 H -0.7388 0.3735 0.8703 0.062 Uiso 1 1 calc R . . A 2
O4 O -0.7419(6) 0.4874(2) 1.0746(9) 0.0447(19) Uani 1 1 d . . . . .
H4 H -0.7510 0.4571 1.0133 0.067 Uiso 1 1 calc GR . . . .
C6 C -0.8585(9) 0.6092(4) 0.7504(14) 0.040(3) Uani 1 1 d . . . . .
H6 H -0.7780 0.6061 0.6998 0.048 Uiso 1 1 calc R . . . .
C7 C -0.4379(8) 0.5103(4) 1.2595(14) 0.049(3) Uani 1 1 d . . . . .
H7A H -0.4574 0.5536 1.2408 0.073 Uiso 1 1 calc GR . . . .
H7B H -0.4130 0.4935 1.1686 0.073 Uiso 1 1 calc GR . . . .
H7C H -0.3411 0.5030 1.3767 0.073 Uiso 1 1 calc GR . . . .
C8 C -0.5708(8) 0.4151(4) 1.3024(12) 0.044(3) Uani 1 1 d . . . . .
H8A H -0.5442 0.3920 1.2213 0.067 Uiso 1 1 calc GR . . . .
H8B H -0.6757 0.3996 1.2980 0.067 Uiso 1 1 calc GR . . . .
H8C H -0.4768 0.4113 1.4231 0.067 Uiso 1 1 calc GR . . . .
C9 C -0.9408(9) 0.6709(4) 0.7074(14) 0.062(3) Uani 1 1 d . . . . .
H9A H -1.0301 0.6728 0.7433 0.093 Uiso 1 1 calc GR . . . .
H9B H -0.9911 0.6781 0.5799 0.093 Uiso 1 1 calc GR . . . .
H9C H -0.8544 0.7015 0.7714 0.093 Uiso 1 1 calc GR . . . .
C10 C -0.9918(8) 0.5580(4) 0.6720(13) 0.048(3) Uani 1 1 d . . . . .
H10A H -0.9332 0.5192 0.6986 0.072 Uiso 1 1 calc GR . . . .
H10B H -1.0580 0.5631 0.5435 0.072 Uiso 1 1 calc GR . . . .
H10C H -1.0686 0.5595 0.7243 0.072 Uiso 1 1 calc GR . . . .
C11 C -1.124(8) 0.405(2) 0.730(8) 0.041(8) Uani 0.51(4) 1 d . . P B 1
H11A H -1.1487 0.4166 0.6103 0.062 Uiso 0.51(4) 1 calc GR . P B 1
H11B H -1.1001 0.4405 0.8042 0.062 Uiso 0.51(4) 1 calc GR . P B 1
H11C H -1.2233 0.3837 0.7248 0.062 Uiso 0.51(4) 1 calc GR . P B 1
C14 C -0.961(7) 0.361(3) 0.813(7) 0.056(9) Uani 0.51(4) 1 d . . P B 1
H14 H -0.9816 0.3315 0.7161 0.067 Uiso 0.51(4) 1 calc R . P B 1
C16 C -0.919(5) 0.324(2) 0.965(6) 0.058(8) Uani 0.51(4) 1 d . . P B 1
H16A H -0.8939 0.3501 1.0670 0.088 Uiso 0.51(4) 1 calc GR . P B 1
H16B H -0.8182 0.2999 0.9903 0.088 Uiso 0.51(4) 1 calc GR . P B 1
H16C H -1.0148 0.2979 0.9430 0.088 Uiso 0.51(4) 1 calc GR . P B 1
C17 C -0.5951(9) 0.4806(4) 1.2480(14) 0.049(3) Uani 1 1 d . . . . .
H17 H -0.6229 0.5022 1.3333 0.059 Uiso 1 1 calc R . . . .
O1 O -0.4700(5) 0.6723(3) 1.0564(9) 0.0411(18) Uani 1 1 d . . . . .
H1 H -0.5402 0.6462 1.0500 0.062 Uiso 1 1 calc GR . . . .
C2 C -0.4413(9) 0.7143(4) 1.1979(14) 0.036(3) Uani 1 1 d . . . . .
H2A H -0.3415 0.7403 1.2199 0.043 Uiso 1 1 calc R . . . .
C3 C -0.5984(8) 0.7542(4) 1.1387(14) 0.050(3) Uani 1 1 d . . . . .
H3A H -0.6190 0.7758 1.0308 0.075 Uiso 1 1 calc GR . . . .
H3B H -0.5793 0.7831 1.2323 0.075 Uiso 1 1 calc GR . . . .
H3C H -0.6976 0.7293 1.1148 0.075 Uiso 1 1 calc GR . . . .
C4 C -0.3991(9) 0.6793(4) 1.3691(15) 0.054(3) Uani 1 1 d . . . . .
H4A H -0.4983 0.6554 1.3517 0.081 Uiso 1 1 calc GR . . . .
H4B H -0.3702 0.7076 1.4666 0.081 Uiso 1 1 calc GR . . . .
H4C H -0.3022 0.6526 1.3976 0.081 Uiso 1 1 calc GR . . . .
C16A C -0.944(6) 0.308(2) 0.880(8) 0.058(8) Uani 0.49(4) 1 d . . P B 2
H16D H -0.8326 0.2969 0.9773 0.088 Uiso 0.49(4) 1 calc GR . P B 2
H16E H -0.9567 0.2918 0.7689 0.088 Uiso 0.49(4) 1 calc GR . P B 2
H16F H -1.0343 0.2927 0.9032 0.088 Uiso 0.49(4) 1 calc GR . P B 2
C14A C -0.957(7) 0.379(2) 0.867(8) 0.056(9) Uani 0.49(4) 1 d . . P B 2
H14A H -0.9560 0.3996 0.9712 0.067 Uiso 0.49(4) 1 calc R . P B 2
C11A C -1.125(8) 0.385(2) 0.696(9) 0.041(8) Uani 0.49(4) 1 d . . P B 2
H11D H -1.1142 0.3653 0.5993 0.062 Uiso 0.49(4) 1 calc GR . P B 2
H11E H -1.1542 0.4270 0.6679 0.062 Uiso 0.49(4) 1 calc GR . P B 2
H11F H -1.2155 0.3646 0.7114 0.062 Uiso 0.49(4) 1 calc GR . P B 2

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
O2 0.055(3) 0.034(5) 0.035(6) 0.013(3) 0.011(3) 0.009(3)
O3 0.026(3) 0.051(5) 0.050(6) 0.011(3) 0.020(3) 0.003(2)
O4 0.039(3) 0.040(5) 0.041(6) -0.004(3) 0.008(3) 0.002(3)
C6 0.039(4) 0.031(8) 0.054(11) 0.013(4) 0.025(5) 0.005(5)
C7 0.040(4) 0.049(7) 0.048(10) 0.010(4) 0.013(5) -0.003(4)
C8 0.039(4) 0.052(8) 0.032(9) 0.010(4) 0.009(5) -0.006(4)
C9 0.049(5) 0.063(9) 0.052(11) 0.008(5) 0.005(5) -0.010(5)
C10 0.040(4) 0.055(8) 0.039(10) -0.006(4) 0.011(5) 0.001(4)
C11 0.038(5) 0.04(3) 0.05(2) -0.009(14) 0.024(11) 0.003(17)
C14 0.036(6) 0.04(2) 0.07(3) 0.010(12) 0.008(15) -0.004(14)
C16 0.047(11) 0.06(2) 0.07(3) -0.003(14) 0.029(18) -0.011(11)
C17 0.041(5) 0.047(9) 0.044(11) 0.008(4) 0.007(5) -0.004(4)
O1 0.038(3) 0.040(5) 0.045(6) -0.010(3) 0.019(3) -0.014(2)
C2 0.041(5) 0.040(8) 0.029(11) -0.008(5) 0.019(5) -0.015(4)
C3 0.051(5) 0.040(8) 0.065(10) -0.002(4) 0.032(5) 0.012(4)
C4 0.058(5) 0.063(9) 0.050(12) -0.005(5) 0.032(6) -0.008(5)
C16A 0.047(11) 0.06(2) 0.07(3) -0.003(14) 0.029(18) -0.011(11)
C14A 0.036(6) 0.04(2) 0.07(3) 0.010(12) 0.008(15) -0.004(14)
C11A 0.038(5) 0.04(3) 0.05(2) -0.009(14) 0.024(11) 0.003(17)

_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
O2 C6 1.427(10) . ?
O3 C14 1.45(6) . ?
O3 C14A 1.46(7) . ?
O4 C17 1.421(9) . ?
C6 C9 1.488(11) . ?
C6 C10 1.521(10) . ?
C7 C17 1.478(9) . ?
C8 C17 1.488(10) . ?
C11 C14 1.58(10) . ?
C14 C16 1.40(10) . ?
O1 C2 1.428(11) . ?
C2 C3 1.497(10) . ?
C2 C4 1.514(14) . ?
C16A C14A 1.56(9) . ?
C14A C11A 1.49(10) . ?

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
O2 C6 C9 109.7(7) . . ?
O2 C6 C10 109.1(7) . . ?
C9 C6 C10 112.2(6) . . ?
O3 C14 C11 104(5) . . ?
C16 C14 O3 113(4) . . ?
C16 C14 C11 123(7) . . ?
O4 C17 C7 112.3(8) . . ?
O4 C17 C8 110.1(6) . . ?
C7 C17 C8 114.1(6) . . ?
O1 C2 C3 108.9(8) . . ?
O1 C2 C4 109.5(10) . . ?
C3 C2 C4 112.5(7) . . ?
O3 C14A C16A 105(5) . . ?
O3 C14A C11A 108(6) . . ?
C11A C14A C16A 99(5) . . ?

_shelx_res_file                  
;
TITL Test1 in P21/c #14
CELL 0.56086 8.7267 21.838 8.4077 90 118.243 90
ZERR 16 0.0018 0.0057 0.0025 0 0.008 0
LATT 1
SYMM -X,0.5+Y,0.5-Z

SFAC C H O
UNIT 48 128 16
SIMU 0.01 0.02 1.7 C16A C11A C14A
EADP C16 C16A
EADP C14 C14A
EADP C11 C11A

L.S. 18 0 0
PLAN  10
SIZE 0.1 0.25 0.25
TEMP 23
REM reset to P21/c #14
BOND
fmap 2
acta
OMIT 3 1 2
OMIT 1 0 0
OMIT -2 9 6
REM <HKL>Test1.hkl</HKL>

WGHT    0.047600    2.468300
FVAR       0.24061   0.50997
O2    3   -0.762118    0.601773    0.941515    11.00000    0.05532    0.03392 =
         0.03494    0.01256    0.01149    0.00949
AFIX 147
H2    2   -0.737246    0.565541    0.965487    11.00000   -1.50000
AFIX   0

O3    3   -0.818116    0.398596    0.828258    11.00000    0.02583    0.05076 =
         0.05000    0.01117    0.02006    0.00335
PART 2
AFIX  83
H3    2   -0.738794    0.373522    0.870338    11.00000   -1.50000
AFIX   0

PART 0
O4    3   -0.741861    0.487403    1.074587    11.00000    0.03888    0.03990 =
         0.04137   -0.00391    0.00758    0.00171
AFIX 147
H4    2   -0.751048    0.457053    1.013266    11.00000   -1.50000
AFIX   0

C6    1   -0.858454    0.609235    0.750438    11.00000    0.03944    0.03108 =
         0.05379    0.01278    0.02508    0.00548
AFIX  13
H6    2   -0.778041    0.606148    0.699847    11.00000   -1.20000
AFIX   0

C7    1   -0.437869    0.510275    1.259518    11.00000    0.04021    0.04913 =
         0.04775    0.00987    0.01298   -0.00259
AFIX 137
H7A   2   -0.457369    0.553553    1.240800    11.00000   -1.50000
H7B   2   -0.413045    0.493548    1.168587    11.00000   -1.50000
H7C   2   -0.341081    0.502975    1.376667    11.00000   -1.50000
AFIX   0
C8    1   -0.570802    0.415062    1.302424    11.00000    0.03931    0.05242 =
         0.03245    0.00954    0.00948   -0.00629
AFIX 137
H8A   2   -0.544247    0.392007    1.221331    11.00000   -1.50000
H8B   2   -0.675702    0.399551    1.297954    11.00000   -1.50000
H8C   2   -0.476798    0.411315    1.423123    11.00000   -1.50000
AFIX   0

C9    1   -0.940794    0.670896    0.707439    11.00000    0.04866    0.06297 =
         0.05159    0.00830    0.00469   -0.00962
AFIX 137
H9A   2   -1.030051    0.672808    0.743297    11.00000   -1.50000
H9B   2   -0.991098    0.678133    0.579929    11.00000   -1.50000
H9C   2   -0.854352    0.701527    0.771351    11.00000   -1.50000
AFIX   0
C10   1   -0.991844    0.558041    0.671973    11.00000    0.03959    0.05533 =
         0.03899   -0.00619    0.01070    0.00129
AFIX 137
H10A  2   -0.933177    0.519244    0.698593    11.00000   -1.50000
H10B  2   -1.057971    0.563057    0.543516    11.00000   -1.50000
H10C  2   -1.068577    0.559510    0.724284    11.00000   -1.50000
AFIX   0

PART 1
C11   1   -1.124303    0.404675    0.729880    21.00000    0.03791    0.03520 =
         0.05365   -0.00862    0.02372    0.00275
AFIX 137
H11A  2   -1.148673    0.416566    0.610267    21.00000   -1.50000
H11B  2   -1.100053    0.440472    0.804249    21.00000   -1.50000
H11C  2   -1.223261    0.383738    0.724776    21.00000   -1.50000
AFIX   0
C14   1   -0.961097    0.360614    0.812815    21.00000    0.03630    0.04447 =
         0.06733    0.00960    0.00774   -0.00419
AFIX  13
H14   2   -0.981570    0.331471    0.716122    21.00000   -1.20000
AFIX   0
C16   1   -0.918671    0.324282    0.965240    21.00000    0.04745    0.05559 =
         0.07289   -0.00259    0.02899   -0.01077
AFIX 137
H16A  2   -0.893946    0.350105    1.066981    21.00000   -1.50000
H16B  2   -0.818191    0.299917    0.990282    21.00000   -1.50000
H16C  2   -1.014782    0.297911    0.942982    21.00000   -1.50000
AFIX   0

PART 0
C17   1   -0.595071    0.480638    1.247974    11.00000    0.04125    0.04670 =
         0.04422    0.00814    0.00740   -0.00355
AFIX  13
H17   2   -0.622914    0.502194    1.333310    11.00000   -1.20000
AFIX   0

O1    3   -0.470001    0.672286    1.056397    11.00000    0.03762    0.03960 =
         0.04547   -0.00967    0.01914   -0.01390
AFIX 147
H1    2   -0.540214    0.646167    1.049980    11.00000   -1.50000
AFIX   0
C2    1   -0.441252    0.714350    1.197935    11.00000    0.04111    0.03999 =
         0.02874   -0.00826    0.01920   -0.01515
AFIX  13
H2A   2   -0.341489    0.740275    1.219907    11.00000   -1.20000
AFIX   0
C3    1   -0.598369    0.754233    1.138653    11.00000    0.05078    0.04013 =
         0.06538   -0.00246    0.03217    0.01182
AFIX 137
H3A   2   -0.619042    0.775814    1.030837    11.00000   -1.50000
H3B   2   -0.579259    0.783145    1.232257    11.00000   -1.50000
H3C   2   -0.697581    0.729321    1.114840    11.00000   -1.50000
AFIX   0
C4    1   -0.399130    0.679268    1.369116    11.00000    0.05787    0.06252 =
         0.05050   -0.00528    0.03227   -0.00758
AFIX 137
H4A   2   -0.498337    0.655444    1.351684    11.00000   -1.50000
H4B   2   -0.370152    0.707565    1.466616    11.00000   -1.50000
H4C   2   -0.302195    0.652554    1.397577    11.00000   -1.50000
AFIX   0

PART 2
C16A  1   -0.943905    0.308396    0.880335   -21.00000    0.04745    0.05559 =
         0.07289   -0.00259    0.02899   -0.01077
AFIX 137
H16D  2   -0.832618    0.296873    0.977267   -21.00000   -1.50000
H16E  2   -0.956702    0.291826    0.768939   -21.00000   -1.50000
H16F  2   -1.034336    0.292655    0.903210   -21.00000   -1.50000
AFIX   0
C14A  1   -0.956957    0.379404    0.866709   -21.00000    0.03630    0.04447 =
         0.06733    0.00960    0.00774   -0.00419
AFIX  13
H14A  2   -0.955997    0.399642    0.971210   -21.00000   -1.20000
AFIX   0
C11A  1   -1.125272    0.384530    0.696071   -21.00000    0.03791    0.03520 =
         0.05365   -0.00862    0.02372    0.00275
AFIX 137
H11D  2   -1.114214    0.365293    0.599334   -21.00000   -1.50000
H11E  2   -1.154190    0.426956    0.667893   -21.00000   -1.50000
H11F  2   -1.215523    0.364635    0.711384   -21.00000   -1.50000
AFIX   0
HKLF 4

REM  Test1 in P21/c #14
REM R1 =  0.0585 for     503 Fo > 4sig(Fo)  and  0.1056 for all     743 data
REM    168 parameters refined using     12 restraints

END

WGHT      0.0475      2.4743

REM Highest difference peak  0.145,  deepest hole -0.143,  1-sigma level  0.034
Q1    1  -0.6786  0.6351  0.9267  11.00000  0.05    0.14
Q2    1  -0.6339  0.3519  0.9249  11.00000  0.05    0.14
Q3    1  -0.5940  0.3981  1.0296  11.00000  0.05    0.13
Q4    1  -0.9071  0.4272  0.7627  11.00000  0.05    0.13
Q5    1  -0.7005  0.6673  1.0131  11.00000  0.05    0.12
Q6    1  -1.0000  0.5000  1.0000  10.50000  0.05    0.12
Q7    1  -0.7839  0.5336  1.0643  11.00000  0.05    0.12
Q8    1  -0.6352  0.6177  0.7714  11.00000  0.05    0.11
Q9    1  -0.4175  0.7056  1.0261  11.00000  0.05    0.11
Q10   1  -0.6439  0.7830  0.8775  11.00000  0.05    0.11
;
_shelx_res_checksum              73606
_database_code_depnum_ccdc_archive 'CCDC 1002746'
#######################################################################
#
#                 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_test1
_audit_creation_date             2014-04-01
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4813)
;
_chemical_name_common            ?
_chemical_name_systematic        Isopropanol
_chemical_formula_moiety         'C3 H8 O'
_chemical_formula_sum            'C3 H8 O'
_chemical_formula_weight         60.09
_chemical_melting_point          ?
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 0.0000 0.0000 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   6.542(3)
_cell_length_b                   13.415(14)
_cell_length_c                   14.469(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.79(2)
_cell_angle_gamma                90.00
_cell_volume                     1251.3(17)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    959
_cell_measurement_temperature    180
_cell_measurement_theta_max      20.48
_cell_measurement_theta_min      2.86
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1093 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.7945.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.957
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method 
'Crystallised via in-situ cryo-crystallisation on the diffractometer'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3272
_diffrn_reflns_theta_full        21.77
_diffrn_reflns_theta_max         21.77
_diffrn_reflns_theta_min         2.08
_diffrn_ambient_temperature      180
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_special_details          
'Completeness and redundancy limited as only omega scans possible as sample mounted vertically on the omega circle to avoid icing of the Lindemann tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                977
_reflns_number_total             1369
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0598P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1231
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c),
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
O1 O 2.2802(2) 0.77911(11) 0.07133(12) 0.0522(5) Uani 1 d . . .
H1 H 2.3726 0.7633 0.0424 0.078 Uiso 1 calc . . GR
O2 O 2.5908(2) 0.75536(14) 0.47184(11) 0.0599(6) Uani 1 d . . .
H2 H 2.6938 0.7847 0.4990 0.090 Uiso 1 calc . . GR
O3 O 1.9478(2) 0.65336(13) 0.05277(12) 0.0573(6) Uani 1 d . . .
H3 H 2.0411 0.6949 0.0602 0.086 Uiso 1 calc . . GR
C4 C 1.9557(4) 0.59676(18) 0.13605(19) 0.0567(7) Uani 1 d . . .
H4 H 1.9630 0.6425 0.1893 0.068 Uiso 1 calc . . R
C5 C 2.5558(3) 0.78163(18) 0.37570(18) 0.0508(7) Uani 1 d . . .
H5 H 2.5488 0.8544 0.3701 0.061 Uiso 1 calc . . R
C6 C 2.2483(4) 0.88420(18) 0.06467(18) 0.0541(7) Uani 1 d . . .
H6 H 2.2242 0.9033 -0.0017 0.065 Uiso 1 calc . . R
C7 C 2.3496(4) 0.7383(2) 0.33377(19) 0.0745(9) Uani 1 d . . .
H7A H 2.3529 0.6673 0.3425 0.112 Uiso 1 calc . . GR
H7B H 2.3206 0.7531 0.2679 0.112 Uiso 1 calc . . GR
H7C H 2.2434 0.7665 0.3640 0.112 Uiso 1 calc . . GR
C8 C 2.0563(4) 0.90684(19) 0.1050(2) 0.0687(8) Uani 1 d . . .
H8A H 1.9388 0.8753 0.0676 0.103 Uiso 1 calc . . GR
H8B H 2.0347 0.9776 0.1052 0.103 Uiso 1 calc . . GR
H8C H 2.0727 0.8821 0.1681 0.103 Uiso 1 calc . . GR
C9 C 2.1412(4) 0.5317(2) 0.1514(2) 0.0738(9) Uani 1 d . . .
H9A H 2.1308 0.4834 0.1018 0.111 Uiso 1 calc . . GR
H9B H 2.1498 0.4979 0.2105 0.111 Uiso 1 calc . . GR
H9C H 2.2634 0.5714 0.1519 0.111 Uiso 1 calc . . GR
C10 C 1.7551(4) 0.5395(2) 0.1257(2) 0.0918(11) Uani 1 d . . .
H10A H 1.6407 0.5853 0.1160 0.138 Uiso 1 calc . . GR
H10B H 1.7515 0.5015 0.1816 0.138 Uiso 1 calc . . GR
H10C H 1.7453 0.4953 0.0729 0.138 Uiso 1 calc . . GR
C11 C 2.4354(4) 0.9381(2) 0.1137(2) 0.0822(10) Uani 1 d . . .
H11A H 2.4548 0.9237 0.1796 0.123 Uiso 1 calc . . GR
H11B H 2.4165 1.0085 0.1042 0.123 Uiso 1 calc . . GR
H11C H 2.5553 0.9167 0.0889 0.123 Uiso 1 calc . . GR
C12 C 2.7311(4) 0.7439(2) 0.3304(2) 0.0785(9) Uani 1 d . . .
H12A H 2.8586 0.7743 0.3598 0.118 Uiso 1 calc . . GR
H12B H 2.7053 0.7606 0.2649 0.118 Uiso 1 calc . . GR
H12C H 2.7415 0.6729 0.3374 0.118 Uiso 1 calc . . GR

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
O1 0.0457(12) 0.0499(11) 0.0648(13) 0.0032(9) 0.0206(8) 0.0014(8)
O2 0.0419(12) 0.0845(15) 0.0529(12) -0.0002(10) 0.0068(8) -0.0122(9)
O3 0.0438(12) 0.0598(13) 0.0664(13) 0.0108(10) 0.0042(8) -0.0038(8)
C4 0.0529(18) 0.0631(18) 0.0559(18) -0.0006(15) 0.0141(13) -0.0043(14)
C5 0.0469(17) 0.0537(16) 0.0533(18) 0.0022(14) 0.0127(13) 0.0015(12)
C6 0.0584(18) 0.0502(17) 0.0554(17) 0.0037(14) 0.0152(14) 0.0068(13)
C7 0.062(2) 0.095(2) 0.0606(19) 0.0112(17) -0.0069(15) -0.0160(16)
C8 0.0546(19) 0.071(2) 0.083(2) -0.0062(17) 0.0168(15) 0.0134(14)
C9 0.073(2) 0.075(2) 0.073(2) 0.0127(17) 0.0102(15) 0.0170(15)
C10 0.063(2) 0.113(3) 0.096(3) 0.029(2) 0.0059(18) -0.0324(17)
C11 0.070(2) 0.0606(18) 0.121(3) -0.0165(19) 0.0288(19) -0.0138(15)
C12 0.079(2) 0.083(2) 0.082(2) -0.0025(19) 0.0363(17) 0.0110(16)

_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 C6 1.426(3) . ?
O2 C5 1.415(3) . ?
O3 C4 1.418(3) . ?
C4 C9 1.481(3) . ?
C4 C10 1.506(3) . ?
C5 C7 1.499(3) . ?
C5 C12 1.503(3) . ?
C6 C8 1.504(3) . ?
C6 C11 1.493(3) . ?

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
O3 C4 C9 110.7(2) . . ?
O3 C4 C10 106.5(2) . . ?
C9 C4 C10 113.1(2) . . ?
O2 C5 C7 106.57(19) . . ?
O2 C5 C12 109.7(2) . . ?
C7 C5 C12 113.2(2) . . ?
O1 C6 C8 107.19(19) . . ?
O1 C6 C11 110.4(2) . . ?
C11 C6 C8 112.9(2) . . ?

_database_code_depnum_ccdc_archive 'CCDC 1002747'
