# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_Chlorphen2
_database_code_depnum_ccdc_archive 'CCDC 1478493'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-06-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT355_Chlorphen2          
;
PROBLEM: Long    O-H (X0.82,N0.98A)  O6     -   H6O    ..       1.21 Ang.
RESPONSE: OH hydrogen atoms were located by difference Fourier synthesis and allowed to ride on the parent atom with a fixed isotropic displacement parameter. Refinement resulted in chemically meaningless positions.
;
_vrf_PLAT340_Chlorphen2          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0115 Ang.
RESPONSE: Relatively poor crystal quality
;
# Added during the CSD deposition process: Friday 06 May 2016 10:42 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-(p-Chlorophenoxy)propane-1,2-diol
_chemical_name_common            Chlorphenesin
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Cl2 O6'
_chemical_formula_weight         405.25

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   12.3202(14)
_cell_length_b                   4.6501(5)
_cell_length_c                   32.022(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1834.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    113
_cell_measurement_theta_min      8.399
_cell_measurement_theta_max      37.40

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.386
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13672
_diffrn_reflns_av_unetI/netI     0.1066
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3747
_reflns_number_gt                2489
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.963
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.23(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3747
_refine_ls_number_parameters     242
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_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_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
Cl1 Cl 0.79148(16) 0.5745(5) 0.64237(6) 0.0267(5) Uani 1 1 d . . . . .
O1 O 0.5275(5) -0.0712(12) 0.52236(19) 0.0215(14) Uani 1 1 d . . . . .
C1 C 0.7147(6) 0.3732(14) 0.6073(2) 0.0190(16) Uani 1 1 d . . . . .
Cl2 Cl 0.46056(17) 0.9250(5) 0.68743(6) 0.0266(5) Uani 1 1 d . . . . .
O2 O 0.4516(4) -0.1442(10) 0.43421(14) 0.0245(12) Uani 1 1 d . . . . .
C2 C 0.7659(6) 0.2080(15) 0.5779(2) 0.0205(16) Uani 1 1 d . . . . .
H2 H 0.8430 0.2009 0.5775 0.025 Uiso 1 1 calc R U . . .
O3 O 0.3359(4) -0.6797(9) 0.45955(15) 0.0226(11) Uani 1 1 d . . . . .
C3 C 0.7087(9) 0.0528(18) 0.5490(3) 0.020(2) Uani 1 1 d . . . . .
H3 H 0.7448 -0.0595 0.5285 0.024 Uiso 1 1 calc R U . . .
O4 O 0.7271(6) 1.5666(13) 0.80720(19) 0.0238(15) Uani 1 1 d . . . . .
C4 C 0.5945(8) 0.0649(18) 0.5506(3) 0.018(2) Uani 1 1 d . . . . .
O5 O 0.8010(4) 1.6124(11) 0.89537(14) 0.0226(12) Uani 1 1 d . . . . .
C5 C 0.5433(6) 0.2270(14) 0.5807(2) 0.0214(16) Uani 1 1 d . . . . .
H5 H 0.4663 0.2304 0.5819 0.026 Uiso 1 1 calc R U . . .
O6 O 0.9227(4) 2.1396(9) 0.87644(14) 0.0255(12) Uani 1 1 d . . . . .
C6 C 0.6025(6) 0.3833(18) 0.6090(2) 0.0251(19) Uani 1 1 d . . . . .
H6 H 0.5670 0.4970 0.6295 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5790(5) -0.2424(15) 0.4907(2) 0.0214(17) Uani 1 1 d . . . . .
H7A H 0.6193 -0.4029 0.5038 0.026 Uiso 1 1 calc R U . . .
H7B H 0.6312 -0.1233 0.4748 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4934(6) -0.3591(14) 0.4618(2) 0.0199(17) Uani 1 1 d . . . . .
H8 H 0.5276 -0.5128 0.4443 0.024 Uiso 1 1 calc R U . . .
C9 C 0.3983(11) -0.4910(13) 0.4845(4) 0.019(3) Uani 1 1 d . . . . .
H9A H 0.4257 -0.5980 0.5091 0.023 Uiso 1 1 calc R U . . .
H9B H 0.3508 -0.3349 0.4949 0.023 Uiso 1 1 calc R U . . .
C10 C 0.5381(7) 1.1232(15) 0.7221(2) 0.0212(16) Uani 1 1 d . . . . .
C11 C 0.6510(6) 1.1053(18) 0.7208(2) 0.0225(17) Uani 1 1 d . . . . .
H11 H 0.6862 0.9884 0.7006 0.027 Uiso 1 1 calc R U . . .
C12 C 0.7106(6) 1.2613(14) 0.7496(2) 0.0212(16) Uani 1 1 d . . . . .
H12 H 0.7876 1.2526 0.7489 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6594(8) 1.4303(18) 0.7794(3) 0.0184(19) Uani 1 1 d . . . . .
C14 C 0.5491(9) 1.4520(16) 0.7797(3) 0.020(2) Uani 1 1 d . . . . .
H14 H 0.5147 1.5749 0.7993 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4859(6) 1.2951(15) 0.7513(2) 0.0219(17) Uani 1 1 d . . . . .
H15 H 0.4089 1.3062 0.7520 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6758(6) 1.7358(14) 0.8391(2) 0.0231(17) Uani 1 1 d . . . . .
H16A H 0.6219 1.6174 0.8543 0.028 Uiso 1 1 calc R U . . .
H16B H 0.6375 1.9008 0.8263 0.028 Uiso 1 1 calc R U . . .
C17 C 0.7611(6) 1.8432(15) 0.8691(2) 0.0224(18) Uani 1 1 d . . . . .
H17 H 0.7271 1.9917 0.8875 0.027 Uiso 1 1 calc R U . . .
C18 C 0.8553(11) 1.9780(16) 0.8473(4) 0.023(3) Uani 1 1 d . . . . .
H18A H 0.901(5) 1.816(13) 0.8380(18) 0.028 Uiso 1 1 d . U . . .
H18B H 0.838(3) 2.115(7) 0.8244(9) 0.028 Uiso 1 1 d . U . . .
H5O H 0.7440 1.6039 0.9203 0.028 Uiso 1 1 d R U . . .
H6O H 0.8706 2.3544 0.8836 0.028 Uiso 1 1 d R U . . .
H2O H 0.5173 -0.0875 0.4225 0.028 Uiso 1 1 d R U . . .
H3O H 0.3791 -0.8528 0.4548 0.028 Uiso 1 1 d R U . . .


_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
Cl1 C1 1.742(7) . ?
O1 C4 1.377(11) . ?
O1 C7 1.437(9) . ?
C1 C2 1.368(9) . ?
C1 C6 1.385(11) . ?
Cl2 C10 1.730(8) . ?
O2 C8 1.429(8) . ?
C2 C3 1.370(13) . ?
O3 C9 1.414(12) . ?
C3 C4 1.409(14) . ?
O4 C13 1.375(11) . ?
O4 C16 1.436(9) . ?
C4 C5 1.378(11) . ?
O5 C17 1.449(8) . ?
C5 C6 1.372(10) . ?
O6 C18 1.457(13) . ?
C7 C8 1.505(9) . ?
C8 C9 1.509(14) . ?
C10 C15 1.388(10) . ?
C10 C11 1.394(11) . ?
C11 C12 1.384(10) . ?
C12 C13 1.388(11) . ?
C13 C14 1.362(14) . ?
C14 C15 1.402(13) . ?
C16 C17 1.509(10) . ?
C17 C18 1.493(15) . ?

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
C4 O1 C7 116.9(7) . . ?
C2 C1 C6 120.5(7) . . ?
C2 C1 Cl1 119.7(6) . . ?
C6 C1 Cl1 119.9(5) . . ?
C1 C2 C3 121.6(8) . . ?
C2 C3 C4 118.0(9) . . ?
C13 O4 C16 116.6(7) . . ?
C5 C4 O1 115.9(8) . . ?
C5 C4 C3 120.2(9) . . ?
O1 C4 C3 123.8(9) . . ?
C6 C5 C4 120.7(8) . . ?
C5 C6 C1 119.1(7) . . ?
O1 C7 C8 108.9(6) . . ?
O2 C8 C7 112.3(5) . . ?
O2 C8 C9 107.6(7) . . ?
C7 C8 C9 113.2(7) . . ?
O3 C9 C8 113.7(8) . . ?
C15 C10 C11 121.2(7) . . ?
C15 C10 Cl2 118.9(6) . . ?
C11 C10 Cl2 120.0(6) . . ?
C12 C11 C10 118.6(7) . . ?
C11 C12 C13 120.9(7) . . ?
C14 C13 O4 124.5(9) . . ?
C14 C13 C12 120.0(9) . . ?
O4 C13 C12 115.5(8) . . ?
C13 C14 C15 120.7(9) . . ?
C10 C15 C14 118.6(8) . . ?
O4 C16 C17 109.2(6) . . ?
O5 C17 C18 108.6(7) . . ?
O5 C17 C16 111.1(6) . . ?
C18 C17 C16 112.5(7) . . ?
O6 C18 C17 111.0(9) . . ?

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
O5 H5O O3 1.07 1.63 2.677(6) 165.1 2_665
O6 H6O O5 1.21 1.52 2.729(7) 175.7 1_565
O2 H2O O6 0.93 1.96 2.750(7) 141.7 3_634
O3 H3O O2 0.98 1.75 2.713(7) 166.8 1_545

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.070



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
