# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_zu1cult
_database_code_depnum_ccdc_archive 'CCDC 1908430'
loop_
_audit_author_name
_audit_author_address
'Herman Sung'
;the Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2019-04-07 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;
_audit_creation_date             2017-09-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'(2-(4-(Hydroxymethyl)-4,5-dihydrooxazol-2-yl)phenyl)diphenylphosphine oxide'
_chemical_formula_moiety         'C22 H20 N O3 P'
_chemical_formula_sum            'C22 H20 N O3 P'
_chemical_formula_weight         377.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P O N3 C24 H22'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5956(3)
_cell_length_b                   9.7344(4)
_cell_length_c                   10.4231(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.158(3)
_cell_angle_gamma                90
_cell_volume                     972.12(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.7480
_cell_measurement_theta_min      4.2780
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5136
_diffrn_reflns_point_group_measured_fraction_full 0.688
_diffrn_reflns_point_group_measured_fraction_max 0.687
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.488
_diffrn_reflns_theta_min         4.248
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    127.00 175.00   1.00   10.00    --  110.57  45.00 120.00   48
  2  ω    -66.00  37.00   1.00    3.00    --  -40.57  77.00-180.00  103
  3  ω    -70.00  31.00   1.00    3.00    --  -40.57  57.00 -30.00  101
  4  ω    -69.00  33.00   1.00    3.00    --  -40.57  77.00  60.00  102
  5  ω     84.00 111.00   1.00   10.00    --  110.57  45.00 120.00   27
  6  ω     67.00 169.00   1.00   10.00    --  110.57  15.00  60.00  102
  7  ω     81.00 163.00   1.00   10.00    --  110.57  61.00 -90.00   82
  8  ω     40.00 138.00   1.00   10.00    --  110.57 -45.00  90.00   98
  9  ω     64.00 138.00   1.00   10.00    --  110.57 -77.00 150.00   74
 10  ω     34.00 115.00   1.00   10.00    --  110.57-111.00 -30.00   81
 11  ω     37.00 108.00   1.00   10.00    --  110.57 -94.00  90.00   71
 12  ω     37.00 128.00   1.00   10.00    --  110.57 -45.00 -60.00   91
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0589447000
_diffrn_orient_matrix_UB_12      -0.0085016000
_diffrn_orient_matrix_UB_13      0.1343434000
_diffrn_orient_matrix_UB_21      0.1495068000
_diffrn_orient_matrix_UB_22      -0.0062451000
_diffrn_orient_matrix_UB_23      0.0615277000
_diffrn_orient_matrix_UB_31      0.0027243000
_diffrn_orient_matrix_UB_32      0.1579164000
_diffrn_orient_matrix_UB_33      0.0096196000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.306
_reflns_Friedel_fraction_full    0.342
_reflns_Friedel_fraction_max     0.344
_reflns_number_gt                2247
_reflns_number_total             2411
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(3)
_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     245
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0327
_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     
'w=1/[σ²(Fo²)+(0.0450P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0770
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
P1 P 0.26475(6) 0.32121(7) 0.34604(6) 0.01929(16) Uani 1 1 d . . . . .
O1 O 0.2186(2) 0.1857(2) 0.2933(2) 0.0249(5) Uani 1 1 d . . . . .
O2 O 0.5752(2) 0.0617(2) 0.1995(2) 0.0305(5) Uani 1 1 d . . . . .
O3 O 0.2331(2) 0.0163(2) 0.0917(2) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.2359 0.0744 0.1514 0.040 Uiso 1 1 calc GR . . . .
N1 N 0.4471(2) 0.2329(3) 0.1050(2) 0.0241(5) Uani 1 1 d . . . . .
C1 C 0.4495(3) 0.3320(3) 0.3934(2) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.4925(3) 0.4041(3) 0.5039(3) 0.0250(6) Uani 1 1 d . . . . .
H2 H 0.4245 0.4476 0.5528 0.030 Uiso 1 1 calc R . . . .
C3 C 0.6325(3) 0.4140(3) 0.5443(3) 0.0299(7) Uani 1 1 d . . . . .
H3A H 0.6600 0.4656 0.6187 0.036 Uiso 1 1 calc R . . . .
C4 C 0.7320(3) 0.3476(4) 0.4747(3) 0.0328(8) Uani 1 1 d . . . . .
H4 H 0.8280 0.3531 0.5020 0.039 Uiso 1 1 calc R . . . .
C5 C 0.6915(3) 0.2735(3) 0.3659(3) 0.0283(7) Uani 1 1 d . . . . .
H5 H 0.7599 0.2272 0.3196 0.034 Uiso 1 1 calc R . . . .
C6 C 0.5507(3) 0.2658(3) 0.3227(3) 0.0214(6) Uani 1 1 d . . . . .
C7 C 0.5180(3) 0.1892(3) 0.2021(3) 0.0215(6) Uani 1 1 d . . . . .
C8 C 0.5370(3) 0.0083(4) 0.0715(3) 0.0311(7) Uani 1 1 d . . . . .
H8A H 0.4862 -0.0799 0.0768 0.037 Uiso 1 1 calc R . . . .
H8B H 0.6208 -0.0058 0.0218 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4426(3) 0.1203(4) 0.0101(3) 0.0288(7) Uani 1 1 d . . . . .
H9 H 0.4825 0.1529 -0.0711 0.035 Uiso 1 1 calc R . . . .
C10 C 0.2918(3) 0.0738(4) -0.0180(3) 0.0304(7) Uani 1 1 d . . . . .
H10A H 0.2349 0.1535 -0.0481 0.036 Uiso 1 1 calc R . . . .
H10B H 0.2891 0.0047 -0.0878 0.036 Uiso 1 1 calc R . . . .
C11 C 0.2269(3) 0.4632(3) 0.2382(3) 0.0219(6) Uani 1 1 d . . . . .
C12 C 0.1263(3) 0.4435(3) 0.1374(3) 0.0261(6) Uani 1 1 d . . . . .
H12 H 0.0819 0.3569 0.1255 0.031 Uiso 1 1 calc R . . . .
C13 C 0.0922(3) 0.5520(4) 0.0548(3) 0.0323(7) Uani 1 1 d . . . . .
H13 H 0.0233 0.5393 -0.0133 0.039 Uiso 1 1 calc R . . . .
C14 C 0.1572(3) 0.6779(4) 0.0706(3) 0.0301(7) Uani 1 1 d . . . . .
H14 H 0.1346 0.7509 0.0126 0.036 Uiso 1 1 calc R . . . .
C15 C 0.2563(3) 0.6975(4) 0.1722(3) 0.0277(6) Uani 1 1 d . . . . .
H15 H 0.2993 0.7848 0.1847 0.033 Uiso 1 1 calc R . . . .
C16 C 0.2916(3) 0.5905(3) 0.2542(3) 0.0238(6) Uani 1 1 d . . . . .
H16 H 0.3606 0.6037 0.3220 0.029 Uiso 1 1 calc R . . . .
C21 C 0.1747(3) 0.3561(3) 0.4913(3) 0.0232(7) Uani 1 1 d . . . . .
C22 C 0.1603(3) 0.2459(4) 0.5747(3) 0.0283(7) Uani 1 1 d . . . . .
H22 H 0.2003 0.1594 0.5560 0.034 Uiso 1 1 calc R . . . .
C23 C 0.0875(3) 0.2622(4) 0.6855(3) 0.0307(7) Uani 1 1 d . . . . .
H23 H 0.0765 0.1869 0.7421 0.037 Uiso 1 1 calc R . . . .
C24 C 0.0310(3) 0.3901(4) 0.7127(3) 0.0276(7) Uani 1 1 d . . . . .
H24 H -0.0183 0.4021 0.7885 0.033 Uiso 1 1 calc R . . . .
C25 C 0.0460(3) 0.4988(4) 0.6307(3) 0.0281(7) Uani 1 1 d . . . . .
H25 H 0.0074 0.5857 0.6503 0.034 Uiso 1 1 calc R . . . .
C26 C 0.1176(3) 0.4825(3) 0.5187(3) 0.0250(6) Uani 1 1 d . . . . .
H26 H 0.1270 0.5576 0.4617 0.030 Uiso 1 1 calc R . . . .


_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
P1 O1 1.487(2) . ?
P1 C1 1.817(3) . ?
P1 C11 1.806(3) . ?
P1 C21 1.816(3) . ?
O2 C7 1.358(4) . ?
O2 C8 1.460(4) . ?
O3 C10 1.418(4) . ?
N1 C7 1.261(4) . ?
N1 C9 1.475(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.406(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.390(5) . ?
C4 C5 1.382(5) . ?
C5 C6 1.402(4) . ?
C6 C7 1.481(4) . ?
C8 C9 1.535(5) . ?
C9 C10 1.529(4) . ?
C11 C12 1.400(4) . ?
C11 C16 1.392(4) . ?
C12 C13 1.390(5) . ?
C13 C14 1.382(5) . ?
C14 C15 1.396(5) . ?
C15 C16 1.378(5) . ?
C21 C22 1.392(5) . ?
C21 C26 1.383(4) . ?
C22 C23 1.391(5) . ?
C23 C24 1.393(5) . ?
C24 C25 1.373(5) . ?
C25 C26 1.396(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
O1 P1 C1 114.69(13) . . ?
O1 P1 C11 113.78(13) . . ?
O1 P1 C21 109.17(13) . . ?
C11 P1 C1 106.54(13) . . ?
C11 P1 C21 106.70(13) . . ?
C21 P1 C1 105.36(12) . . ?
C7 O2 C8 105.2(2) . . ?
C7 N1 C9 106.4(3) . . ?
C2 C1 P1 119.6(2) . . ?
C2 C1 C6 118.9(2) . . ?
C6 C1 P1 121.5(2) . . ?
C3 C2 C1 121.6(3) . . ?
C2 C3 C4 119.4(3) . . ?
C5 C4 C3 120.0(3) . . ?
C4 C5 C6 120.9(3) . . ?
C1 C6 C7 123.7(2) . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 117.0(3) . . ?
O2 C7 C6 114.2(2) . . ?
N1 C7 O2 119.6(3) . . ?
N1 C7 C6 126.2(3) . . ?
O2 C8 C9 103.9(2) . . ?
N1 C9 C8 104.7(2) . . ?
N1 C9 C10 109.9(2) . . ?
C10 C9 C8 113.6(3) . . ?
O3 C10 C9 112.1(2) . . ?
C12 C11 P1 118.0(2) . . ?
C16 C11 P1 122.2(2) . . ?
C16 C11 C12 119.8(3) . . ?
C13 C12 C11 119.3(3) . . ?
C14 C13 C12 120.7(3) . . ?
C13 C14 C15 119.7(3) . . ?
C16 C15 C14 120.1(3) . . ?
C15 C16 C11 120.4(3) . . ?
C22 C21 P1 116.4(2) . . ?
C26 C21 P1 123.4(2) . . ?
C26 C21 C22 120.1(3) . . ?
C23 C22 C21 120.2(3) . . ?
C22 C23 C24 119.3(3) . . ?
C25 C24 C23 120.4(3) . . ?
C24 C25 C26 120.4(3) . . ?
C21 C26 C25 119.6(3) . . ?

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
O3 H3 O1 0.84 1.85 2.681(3) 170.6 .

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
P1 C1 C2 C3 179.4(2) . . . . ?
P1 C1 C6 C5 -177.9(2) . . . . ?
P1 C1 C6 C7 3.4(4) . . . . ?
P1 C11 C12 C13 178.3(2) . . . . ?
P1 C11 C16 C15 -177.8(2) . . . . ?
P1 C21 C22 C23 -177.3(2) . . . . ?
P1 C21 C26 C25 177.8(2) . . . . ?
O1 P1 C1 C2 -141.2(2) . . . . ?
O1 P1 C1 C6 37.0(3) . . . . ?
O1 P1 C11 C12 18.4(3) . . . . ?
O1 P1 C11 C16 -163.1(2) . . . . ?
O1 P1 C21 C22 41.2(2) . . . . ?
O1 P1 C21 C26 -136.4(2) . . . . ?
O2 C8 C9 N1 5.2(3) . . . . ?
O2 C8 C9 C10 -114.7(3) . . . . ?
N1 C9 C10 O3 -64.3(3) . . . . ?
C1 P1 C11 C12 145.8(2) . . . . ?
C1 P1 C11 C16 -35.7(3) . . . . ?
C1 P1 C21 C22 -82.4(2) . . . . ?
C1 P1 C21 C26 99.9(2) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C1 C6 C7 O2 -130.5(3) . . . . ?
C1 C6 C7 N1 51.2(4) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C4 C5 C6 C7 177.4(3) . . . . ?
C5 C6 C7 O2 50.7(4) . . . . ?
C5 C6 C7 N1 -127.5(3) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C7 O2 C8 C9 -4.1(3) . . . . ?
C7 N1 C9 C8 -4.6(3) . . . . ?
C7 N1 C9 C10 117.8(3) . . . . ?
C8 O2 C7 N1 1.4(3) . . . . ?
C8 O2 C7 C6 -177.0(2) . . . . ?
C8 C9 C10 O3 52.6(4) . . . . ?
C9 N1 C7 O2 2.2(3) . . . . ?
C9 N1 C7 C6 -179.7(3) . . . . ?
C11 P1 C1 C2 92.0(3) . . . . ?
C11 P1 C1 C6 -89.8(3) . . . . ?
C11 P1 C21 C22 164.6(2) . . . . ?
C11 P1 C21 C26 -13.1(3) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
C12 C13 C14 C15 -1.3(5) . . . . ?
C13 C14 C15 C16 1.7(5) . . . . ?
C14 C15 C16 C11 -1.4(4) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C21 P1 C1 C2 -21.1(3) . . . . ?
C21 P1 C1 C6 157.1(2) . . . . ?
C21 P1 C11 C12 -102.1(2) . . . . ?
C21 P1 C11 C16 76.4(3) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
C22 C21 C26 C25 0.3(4) . . . . ?
C22 C23 C24 C25 0.5(5) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C24 C25 C26 C21 -0.6(4) . . . . ?
C26 C21 C22 C23 0.5(4) . . . . ?

_olex2_date_sample_data_collection 2017-09-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.690
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, hexane'
####################################################################### 
# 
# 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_huang1cult
_database_code_depnum_ccdc_archive 'CCDC 1908431'
loop_
_audit_author_name
_audit_author_address
'Herman Sung'
;the Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2019-04-07 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;
_audit_creation_date             2019-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
(2,2'-(propane-2,2-diyl)bis(4,5-dihydrooxazole-4,2-diyl))dimethanol
_chemical_formula_moiety         'C25 H26 N2 O4'
_chemical_formula_sum            'C25 H26 N2 O4'
_chemical_formula_weight         418.48
_chemical_absolute_configuration .
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.1435(3)
_cell_length_b                   10.3089(2)
_cell_length_c                   8.5206(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.293(3)
_cell_angle_gamma                90
_cell_volume                     1023.82(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1283
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.1370
_cell_measurement_theta_min      7.0960
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0055
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1521
_diffrn_reflns_point_group_measured_fraction_full 0.663
_diffrn_reflns_point_group_measured_fraction_max 0.661
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         5.730
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     96.00 122.00   1.00    3.00    --  106.99 -45.00-120.00   26
  2  ω    -19.00  30.00   1.00    2.00    --  -40.57  37.00 -90.00   49
  3  ω    -58.00 -24.00   1.00    2.00    --  -40.57  37.00 -90.00   34
  4  ω      1.00  83.00   1.00    2.00    --   40.57 -99.00  30.00   82
  5  ω      8.00  52.00   1.00    2.00    --   40.57 -99.00-180.00   44
  6  ω     34.00  93.00   1.00    3.00    --  106.99 -45.00-120.00   59
  7  ω     24.00  96.00   1.00    3.00    --  106.99 -94.00 150.00   72
  8  ω     87.00 173.00   1.00    3.00    --  106.99  61.00  30.00   86
  9  ω    102.00 177.00   1.00    3.00    --  106.99  61.00 -60.00   75
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0682142000
_diffrn_orient_matrix_UB_12      0.0550387000
_diffrn_orient_matrix_UB_13      0.1127187000
_diffrn_orient_matrix_UB_21      -0.0942679000
_diffrn_orient_matrix_UB_22      -0.1024176000
_diffrn_orient_matrix_UB_23      -0.0649472000
_diffrn_orient_matrix_UB_31      0.0627154000
_diffrn_orient_matrix_UB_32      -0.0938265000
_diffrn_orient_matrix_UB_33      0.1362386000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.284
_reflns_Friedel_fraction_full    0.315
_reflns_Friedel_fraction_max     0.311
_reflns_number_gt                1215
_reflns_number_total             1226
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0230
_refine_ls_restrained_S_all      1.025
_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)+(0.0450P)²+0.2810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0612
_refine_special_details          ?

# start Validation Reply Form
_vrf_PLAT915_huang1cult          
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         31 %     
RESPONSE: This is a racemic compound
;
# end Validation Reply Form

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
2.d Idealised tetrahedral OH refined as rotating group:
 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
O1 O 0.41713(10) -0.12830(14) 0.23854(14) 0.0238(3) Uani 1 1 d . . . . .
H1 H 0.4093 -0.1014 0.3278 0.036 Uiso 1 1 calc GR . . . .
O2 O 0.62523(10) 0.16894(12) 0.33999(13) 0.0180(3) Uani 1 1 d . . . . .
N1 N 0.62940(11) -0.01580(15) 0.48384(16) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.53236(14) -0.16637(19) 0.2600(2) 0.0211(4) Uani 1 1 d . . . . .
H1A H 0.5394 -0.2021 0.1555 0.025 Uiso 1 1 calc R . . . .
H1B H 0.5512 -0.2369 0.3422 0.025 Uiso 1 1 calc R . . . .
C2 C 0.61965(15) -0.05860(19) 0.3145(2) 0.0181(4) Uani 1 1 d . . . . .
H2 H 0.6962 -0.0911 0.3096 0.022 Uiso 1 1 calc R . . . .
C3 C 0.59280(16) 0.0671(2) 0.2162(2) 0.0210(4) Uani 1 1 d . . . . .
H3A H 0.6382 0.0734 0.1366 0.025 Uiso 1 1 calc R . . . .
H3B H 0.5102 0.0725 0.1568 0.025 Uiso 1 1 calc R . . . .
C4 C 0.63325(13) 0.10734(18) 0.48349(19) 0.0132(4) Uani 1 1 d . . . . .
C5 C 0.5000 0.3754(3) 0.5000 0.0143(5) Uani 1 2 d S T P . .
C6 C 0.58660(14) 0.30258(17) 0.63543(19) 0.0138(4) Uani 1 1 d . . . . .
C7 C 0.64838(13) 0.18915(17) 0.63114(19) 0.0137(4) Uani 1 1 d . . . . .
C8 C 0.72711(14) 0.14568(17) 0.7752(2) 0.0155(4) Uani 1 1 d . . . . .
H8 H 0.7682 0.0675 0.7739 0.019 Uiso 1 1 calc R . . . .
C9 C 0.74577(14) 0.21504(18) 0.9193(2) 0.0174(4) Uani 1 1 d . . . . .
H9 H 0.8007 0.1852 1.0154 0.021 Uiso 1 1 calc R . . . .
C10 C 0.68450(14) 0.32818(18) 0.9242(2) 0.0183(4) Uani 1 1 d . . . . .
H10 H 0.6973 0.3760 1.0230 0.022 Uiso 1 1 calc R . . . .
C11 C 0.60436(13) 0.37039(18) 0.7831(2) 0.0166(4) Uani 1 1 d . . . . .
C12 C 0.52985(15) 0.48928(19) 0.7607(2) 0.0207(4) Uani 1 1 d . . . . .
H12A H 0.5741 0.5684 0.7523 0.025 Uiso 1 1 calc R . . . .
H12B H 0.4952 0.4996 0.8521 0.025 Uiso 1 1 calc R . . . .
C13 C 0.43741(14) 0.46143(18) 0.59847(19) 0.0176(4) Uani 1 1 d . . . . .
H13A H 0.4096 0.5430 0.5392 0.021 Uiso 1 1 calc R . . . .
H13B H 0.3714 0.4147 0.6185 0.021 Uiso 1 1 calc R . . . .


_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 C1 1.415(2) . ?
O2 C3 1.462(2) . ?
O2 C4 1.357(2) . ?
N1 C2 1.482(2) . ?
N1 C4 1.270(2) . ?
C1 C2 1.516(3) . ?
C2 C3 1.527(3) . ?
C4 C7 1.483(2) . ?
C5 C6 1.523(2) 2_656 ?
C5 C6 1.523(2) . ?
C5 C13 1.558(2) . ?
C5 C13 1.558(2) 2_656 ?
C6 C7 1.395(3) . ?
C6 C11 1.402(2) . ?
C7 C8 1.401(2) . ?
C8 C9 1.384(2) . ?
C9 C10 1.390(3) . ?
C10 C11 1.388(2) . ?
C11 C12 1.503(3) . ?
C12 C13 1.543(2) . ?

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 O2 C3 104.51(13) . . ?
C4 N1 C2 106.75(15) . . ?
O1 C1 C2 114.69(15) . . ?
N1 C2 C1 111.98(14) . . ?
N1 C2 C3 103.16(14) . . ?
C1 C2 C3 115.50(15) . . ?
O2 C3 C2 103.95(12) . . ?
O2 C4 C7 117.32(15) . . ?
N1 C4 O2 118.45(15) . . ?
N1 C4 C7 124.22(15) . . ?
C6 C5 C6 121.0(2) 2_656 . ?
C6 C5 C13 110.56(8) 2_656 . ?
C6 C5 C13 102.13(9) . . ?
C6 C5 C13 102.13(9) 2_656 2_656 ?
C6 C5 C13 110.56(8) . 2_656 ?
C13 C5 C13 110.6(2) . 2_656 ?
C7 C6 C5 130.93(15) . . ?
C7 C6 C11 119.53(15) . . ?
C11 C6 C5 109.50(15) . . ?
C6 C7 C4 124.02(15) . . ?
C6 C7 C8 119.00(15) . . ?
C8 C7 C4 116.95(15) . . ?
C9 C8 C7 120.92(15) . . ?
C8 C9 C10 120.28(15) . . ?
C11 C10 C9 119.23(15) . . ?
C6 C11 C12 110.92(14) . . ?
C10 C11 C6 121.00(16) . . ?
C10 C11 C12 128.05(15) . . ?
C11 C12 C13 102.86(14) . . ?
C12 C13 C5 104.24(12) . . ?

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
O1 H1 N1 0.84 2.00 2.8302(19) 169.9 2_656

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
O1 C1 C2 N1 68.64(19) . . . . ?
O1 C1 C2 C3 -49.1(2) . . . . ?
O2 C4 C7 C6 44.1(2) . . . . ?
O2 C4 C7 C8 -138.17(15) . . . . ?
N1 C2 C3 O2 17.12(15) . . . . ?
N1 C4 C7 C6 -137.13(17) . . . . ?
N1 C4 C7 C8 40.6(2) . . . . ?
C1 C2 C3 O2 139.63(14) . . . . ?
C2 N1 C4 O2 1.6(2) . . . . ?
C2 N1 C4 C7 -177.10(14) . . . . ?
C3 O2 C4 N1 10.01(19) . . . . ?
C3 O2 C4 C7 -171.19(14) . . . . ?
C4 O2 C3 C2 -16.31(15) . . . . ?
C4 N1 C2 C1 -136.77(16) . . . . ?
C4 N1 C2 C3 -11.93(17) . . . . ?
C4 C7 C8 C9 -179.25(15) . . . . ?
C5 C6 C7 C4 -4.9(3) . . . . ?
C5 C6 C7 C8 177.41(15) . . . . ?
C5 C6 C11 C10 -176.37(14) . . . . ?
C5 C6 C11 C12 1.88(18) . . . . ?
C6 C5 C6 C7 38.40(15) 2_656 . . . ?
C6 C5 C6 C11 -143.94(13) 2_656 . . . ?
C6 C5 C13 C12 30.96(18) . . . . ?
C6 C5 C13 C12 160.95(15) 2_656 . . . ?
C6 C7 C8 C9 -1.4(2) . . . . ?
C6 C11 C12 C13 18.04(19) . . . . ?
C7 C6 C11 C10 1.6(2) . . . . ?
C7 C6 C11 C12 179.84(15) . . . . ?
C7 C8 C9 C10 1.4(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C6 -1.7(2) . . . . ?
C9 C10 C11 C12 -179.58(17) . . . . ?
C10 C11 C12 C13 -163.86(17) . . . . ?
C11 C6 C7 C4 177.60(15) . . . . ?
C11 C6 C7 C8 0.0(2) . . . . ?
C11 C12 C13 C5 -30.05(18) . . . . ?
C13 C5 C6 C7 161.61(17) . . . . ?
C13 C5 C6 C7 -80.7(2) 2_656 . . . ?
C13 C5 C6 C11 -20.73(18) . . . . ?
C13 C5 C6 C11 96.94(16) 2_656 . . . ?
C13 C5 C13 C12 -86.70(13) 2_656 . . . ?

_olex2_date_sample_data_collection 2019-01-08
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.157
_oxdiff_exptl_absorpt_empirical_full_min 0.777
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, hexane'
