# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_jhc1703
_database_code_depnum_ccdc_archive 'CCDC 1837708'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 O4'
_chemical_formula_sum            'C11 H10 O4'
_chemical_formula_weight         206.19
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 O4'
_chemical_oxdiff_usercomment     'Liam Hughes lmhfurfural'
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.22158(15)
_cell_length_b                   9.60997(16)
_cell_length_c                   13.4791(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     935.44(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    109.95(10)
_cell_measurement_theta_max      70.8130
_cell_measurement_theta_min      5.6500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.0529
1 1 0 0.0299
1 0 2 0.0952
-1 0 -2 0.0952
0 -1 1 0.1076
0 1 -1 0.1076
-2 1 1 0.0809
-2 2 5 0.1164
2 -5 -5 0.0929
2 -5 5 0.1101

_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.083
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -1.0000 -0.0000 -0.0905 0.1800 0.1750
1.0000 1.0000 0.0000 0.0905 -0.1800 -0.1750
1.0000 -0.0000 2.0000 0.2955 -0.1015 -0.0028
-1.0000 0.0000 -2.0000 -0.2955 0.1015 0.0028
0.0000 -1.0000 1.0000 0.1008 0.0321 0.1659
-0.0000 1.0000 -1.0000 -0.1008 -0.0321 -0.1659
-2.0000 1.0000 1.0000 -0.0670 0.4490 -0.1229
-2.0000 2.0000 5.0000 0.3529 0.6486 -0.2577
2.0000 -5.0000 -5.0000 -0.3629 -0.6913 0.7368
2.0000 -5.0000 5.0000 0.6787 -0.2279 0.7991

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2614
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.022
_diffrn_reflns_theta_max         67.022
_diffrn_reflns_theta_min         5.654
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  51.00   1.00    1.00    --    0.00  57.00  60.00   46
  2  ω     39.00  88.00   1.00    1.00    --   54.00  57.00 150.00   49
  3  ω    100.00 130.00   1.00    1.00    --  108.00 111.00 150.00   30
  4  ω    118.00 158.00   1.00    1.00    --  108.00 111.00  90.00   40
  5  ω    103.00 177.00   1.00    1.00    --  108.00 111.00  60.00   74
  6  ω     83.00 175.00   1.00    1.00    --  108.00  37.00-120.00   92
  7  ω     66.00 121.00   1.00    1.00    --   54.00  57.00-180.00   55
  8  ω     14.00  76.00   1.00    1.00    --   54.00 -77.00-150.00   62
  9  ω     73.00 110.00   1.00    1.00    --  108.00-111.00-180.00   37
 10  ω     40.00  87.00   1.00    1.00    --  108.00-111.00  30.00   47
 11  ω    -10.00  30.00   1.00    1.00    --    0.00  57.00-180.00   40
 12  ω     40.00  66.00   1.00    1.00    --   54.40 -57.00-180.00   26
 13  ω    -16.00  57.00   1.00    1.00    --   54.40 -77.00 150.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0872353000
_diffrn_orient_matrix_UB_12      0.0033126000
_diffrn_orient_matrix_UB_13      0.1041546000
_diffrn_orient_matrix_UB_21      -0.1942161000
_diffrn_orient_matrix_UB_22      0.0142366000
_diffrn_orient_matrix_UB_23      0.0463448000
_diffrn_orient_matrix_UB_31      -0.0153106000
_diffrn_orient_matrix_UB_32      -0.1597147000
_diffrn_orient_matrix_UB_33      0.0062315000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.493
_reflns_Friedel_fraction_full    0.720
_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                1435
_reflns_number_total             1484
_reflns_odcompleteness_completeness 99.51
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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         0.201
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.075
_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)+(0.0407P)²+0.1195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0646
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.2481(2) 0.53472(17) 0.38101(13) 0.0175(4) Uani 1 1 d . . . . .
C2 C 0.2511(3) 0.58930(18) 0.27447(14) 0.0197(4) Uani 1 1 d . . . . .
H2 H 0.286(3) 0.687(2) 0.2714(14) 0.017(5) Uiso 1 1 d . . . . .
C3 C 0.0810(3) 0.4336(2) 0.18377(16) 0.0241(4) Uani 1 1 d . . . . .
H3A H -0.013(3) 0.375(2) 0.2140(17) 0.029(6) Uiso 1 1 d . . . . .
H3B H 0.055(3) 0.450(2) 0.1106(17) 0.029(6) Uiso 1 1 d . . . . .
C4 C 0.2780(3) 0.38232(19) 0.20386(13) 0.0182(4) Uani 1 1 d . . . . .
H4 H 0.334(3) 0.335(2) 0.1434(15) 0.017(5) Uiso 1 1 d . . . . .
C5 C 0.2929(3) 0.29602(18) 0.29821(12) 0.0168(4) Uani 1 1 d . . . . .
H5A H 0.203(3) 0.217(2) 0.2954(15) 0.029(6) Uiso 1 1 d . . . . .
H5B H 0.419(3) 0.258(2) 0.3012(15) 0.020(5) Uiso 1 1 d . . . . .
C6 C 0.2588(2) 0.38080(17) 0.39079(12) 0.0151(4) Uani 1 1 d . . . . .
C7 C 0.2407(2) 0.32609(17) 0.48201(13) 0.0164(4) Uani 1 1 d . . . . .
H7 H 0.215(3) 0.389(2) 0.5375(14) 0.018(5) Uiso 1 1 d . . . . .
C8 C 0.2523(2) 0.18152(17) 0.50794(12) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.2925(3) 0.05999(19) 0.46034(14) 0.0190(4) Uani 1 1 d . . . . .
H9 H 0.328(3) 0.051(2) 0.3953(17) 0.025(6) Uiso 1 1 d . . . . .
C10 C 0.2785(3) -0.04844(19) 0.53135(14) 0.0218(4) Uani 1 1 d . . . . .
H10 H 0.298(3) -0.148(2) 0.5211(16) 0.027(6) Uiso 1 1 d . . . . .
C11 C 0.2323(3) 0.0122(2) 0.61710(14) 0.0219(4) Uani 1 1 d . . . . .
H11 H 0.204(3) -0.016(2) 0.6812(17) 0.031(6) Uiso 1 1 d . . . . .
O1 O 0.2361(2) 0.61595(12) 0.45023(9) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.37751(17) 0.51223(13) 0.21717(10) 0.0189(3) Uani 1 1 d . . . . .
O3 O 0.07499(18) 0.56894(14) 0.23086(10) 0.0245(3) Uani 1 1 d . . . . .
O4 O 0.2154(2) 0.15301(13) 0.60665(9) 0.0206(3) Uani 1 1 d . . . . .


_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 1.529(2) . ?
C1 C6 1.487(2) . ?
C1 O1 1.220(2) . ?
C2 H2 0.98(2) . ?
C2 O2 1.407(2) . ?
C2 O3 1.415(2) . ?
C3 H3A 0.97(2) . ?
C3 H3B 1.02(2) . ?
C3 C4 1.530(3) . ?
C3 O3 1.447(3) . ?
C4 H4 1.02(2) . ?
C4 C5 1.522(2) . ?
C4 O2 1.452(2) . ?
C5 H5A 1.00(2) . ?
C5 H5B 0.99(2) . ?
C5 C6 1.511(2) . ?
C6 C7 1.344(2) . ?
C7 H7 0.981(19) . ?
C7 C8 1.435(2) . ?
C8 C9 1.364(2) . ?
C8 O4 1.384(2) . ?
C9 H9 0.92(2) . ?
C9 C10 1.418(3) . ?
C10 H10 0.98(2) . ?
C10 C11 1.337(3) . ?
C11 H11 0.93(2) . ?
C11 O4 1.366(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
C6 C1 C2 115.07(14) . . ?
O1 C1 C2 120.00(14) . . ?
O1 C1 C6 124.92(16) . . ?
C1 C2 H2 112.0(12) . . ?
O2 C2 C1 110.14(14) . . ?
O2 C2 H2 108.5(12) . . ?
O2 C2 O3 106.41(14) . . ?
O3 C2 C1 109.28(15) . . ?
O3 C2 H2 110.3(12) . . ?
H3A C3 H3B 111.3(19) . . ?
C4 C3 H3A 113.0(14) . . ?
C4 C3 H3B 113.3(13) . . ?
O3 C3 H3A 108.3(13) . . ?
O3 C3 H3B 106.5(13) . . ?
O3 C3 C4 103.87(15) . . ?
C3 C4 H4 111.9(12) . . ?
C5 C4 C3 112.92(15) . . ?
C5 C4 H4 113.5(11) . . ?
O2 C4 C3 101.82(14) . . ?
O2 C4 H4 106.5(11) . . ?
O2 C4 C5 109.29(14) . . ?
C4 C5 H5A 109.5(12) . . ?
C4 C5 H5B 107.7(12) . . ?
H5A C5 H5B 108.8(17) . . ?
C6 C5 C4 112.63(14) . . ?
C6 C5 H5A 109.5(12) . . ?
C6 C5 H5B 108.6(12) . . ?
C1 C6 C5 118.15(15) . . ?
C7 C6 C1 117.73(15) . . ?
C7 C6 C5 124.11(15) . . ?
C6 C7 H7 118.3(11) . . ?
C6 C7 C8 126.59(16) . . ?
C8 C7 H7 115.1(11) . . ?
C9 C8 C7 136.62(16) . . ?
C9 C8 O4 108.89(15) . . ?
O4 C8 C7 114.49(15) . . ?
C8 C9 H9 126.2(14) . . ?
C8 C9 C10 107.24(16) . . ?
C10 C9 H9 126.4(14) . . ?
C9 C10 H10 127.8(13) . . ?
C11 C10 C9 106.32(16) . . ?
C11 C10 H10 125.8(13) . . ?
C10 C11 H11 137.1(14) . . ?
C10 C11 O4 111.40(16) . . ?
O4 C11 H11 111.4(14) . . ?
C2 O2 C4 101.50(13) . . ?
C2 O3 C3 106.23(14) . . ?
C11 O4 C8 106.14(14) . . ?

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
C1 C2 O2 C4 73.93(16) . . . . ?
C1 C2 O3 C3 -90.75(17) . . . . ?
C1 C6 C7 C8 -177.97(16) . . . . ?
C2 C1 C6 C5 6.8(2) . . . . ?
C2 C1 C6 C7 -174.42(16) . . . . ?
C3 C4 C5 C6 -67.2(2) . . . . ?
C3 C4 O2 C2 41.63(16) . . . . ?
C4 C3 O3 C2 -0.98(18) . . . . ?
C4 C5 C6 C1 -10.1(2) . . . . ?
C4 C5 C6 C7 171.18(18) . . . . ?
C5 C4 O2 C2 -78.03(16) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C1 C2 O2 -39.7(2) . . . . ?
C6 C1 C2 O3 76.88(19) . . . . ?
C6 C7 C8 C9 5.0(4) . . . . ?
C6 C7 C8 O4 -175.66(18) . . . . ?
C7 C8 C9 C10 180.0(2) . . . . ?
C7 C8 O4 C11 179.85(16) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C8 O4 C11 -0.6(2) . . . . ?
C9 C10 C11 O4 0.0(2) . . . . ?
C10 C11 O4 C8 0.4(2) . . . . ?
O1 C1 C2 O2 140.88(17) . . . . ?
O1 C1 C2 O3 -102.56(19) . . . . ?
O1 C1 C6 C5 -173.80(17) . . . . ?
O1 C1 C6 C7 5.0(3) . . . . ?
O2 C2 O3 C3 28.15(18) . . . . ?
O2 C4 C5 C6 45.4(2) . . . . ?
O3 C2 O2 C4 -44.40(16) . . . . ?
O3 C3 C4 C5 92.03(17) . . . . ?
O3 C3 C4 O2 -25.02(17) . . . . ?
O4 C8 C9 C10 0.6(2) . . . . ?

_olex2_date_sample_data_collection 2017-04-18
_olex2_date_sample_submission    2017-04-05
_olex2_submission_original_sample_id lmhfurfural
_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 1.129
_oxdiff_exptl_absorpt_empirical_full_min 0.866
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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 
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data_jhc1707
_database_code_depnum_ccdc_archive 'CCDC 1837793'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O5'
_chemical_formula_sum            'C13 H11 N O5'
_chemical_formula_weight         261.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H11 N1 O5'
_chemical_oxdiff_usercomment     'Liam Hughes lmh4NO'
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           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                   8.36693(18)
_cell_length_b                   7.08624(14)
_cell_length_c                   19.5336(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.2815(18)
_cell_angle_gamma                90
_cell_volume                     1156.25(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5349
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.3430
_cell_measurement_theta_min      6.6300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 2 -5 0.0403
1 0 5 0.0116
-1 0 -5 0.0136
4 2 -5 0.0379
-3 -3 5 0.0429
1 -4 -3 0.0945
4 -3 -4 0.0850
-4 2 6 0.0318

_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.025
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.0000 2.0000 -5.0000 0.0741 -0.5099 -0.9427
1.0000 -0.0000 5.0000 -0.4358 -0.0895 -0.0174
-1.0000 0.0000 -5.0000 0.4358 0.0895 0.0174
4.0000 2.0000 -5.0000 0.1486 -0.4808 -0.7767
-3.0000 -3.0000 5.0000 -0.2658 0.6641 0.5928
1.0000 -4.0000 -3.0000 -0.0285 0.8569 -0.3268
4.0000 -3.0000 -4.0000 -0.1371 0.5693 -0.8365
-4.0000 2.0000 6.0000 -0.0501 -0.3810 0.8781

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12361
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.535
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    2.00    --    0.00  57.00 -90.00   90
  2  ω    -69.00  21.00   1.00    2.00    --    0.00 -57.00 -60.00   90
  3  ω    -69.00  21.00   1.00    2.00    --    0.00 -57.00-120.00   90
  4  ω    -18.00  80.00   1.00    8.00    --   54.00 -37.00  90.00   98
  5  ω     28.00 126.00   1.00    8.00    --   54.00  37.00 150.00   98
  6  ω    -18.00  80.00   1.00    8.00    --   54.00 -37.00   0.00   98
  7  ω    -18.00  80.00   1.00    8.00    --   54.00 -37.00 -90.00   98
  8  ω      1.00  96.00   1.00    8.00    --   54.00 -99.00   0.00   95
  9  ω     35.00 125.00   1.00    8.00    --   54.00-147.00-103.00   90
 10  ω     33.00 123.00   1.00    8.00    --   54.00  57.00-120.00   90
 11  ω    100.00 178.00   1.00    8.00    --  108.00 111.00  30.00   78
 12  ω     36.00 146.00   1.00    8.00    --  108.00 -91.00  60.00  110
 13  ω     57.00 151.00   1.00    8.00    --  108.00 178.00  30.00   94
 14  ω     36.00 116.00   1.00    8.00    --  108.00-111.00-180.00   80
 15  ω     35.00 178.00   1.00    8.00    --  108.00 -12.00  60.00  143
 16  ω     40.00 130.00   1.00    8.00    --  108.00 -63.00 -30.00   90
 17  ω     35.00 142.00   1.00    8.00    --  108.00 -25.00 -30.00  107
 18  ω     57.00 151.00   1.00    8.00    --  108.00 178.00 -30.00   94
 19  ω     36.00 116.00   1.00    8.00    --  108.00-111.00   0.00   80
 20  ω    100.00 178.00   1.00    8.00    --  108.00 111.00-120.00   78
 21  ω     36.00 134.00   1.00    8.00    --  108.00 -37.00  90.00   98
 22  ω     36.00 134.00   1.00    8.00    --  108.00 -37.00 -60.00   98
 23  ω    -39.00  26.00   1.00    2.00    --    0.00  94.00  65.00   65
 24  ω    -57.00  -1.00   1.00    2.00    --    0.00 124.00 141.00   56
 25  ω     24.00 124.00   1.00    8.00    --   54.00  77.00  30.00  100
 26  ω     24.00 124.00   1.00    8.00    --   54.00  77.00 150.00  100
 27  ω    -15.00  75.00   1.00    8.00    --   54.00 -57.00-120.00   90
 28  ω     24.00 124.00   1.00    8.00    --   54.00  77.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0745152000
_diffrn_orient_matrix_UB_12      0.0426779000
_diffrn_orient_matrix_UB_13      -0.0722572000
_diffrn_orient_matrix_UB_21      -0.0290959000
_diffrn_orient_matrix_UB_22      -0.2124247000
_diffrn_orient_matrix_UB_23      -0.0120900000
_diffrn_orient_matrix_UB_31      -0.1659812000
_diffrn_orient_matrix_UB_32      0.0179143000
_diffrn_orient_matrix_UB_33      0.0297190000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3812
_reflns_number_total             4125
_reflns_odcompleteness_completeness 99.96
_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 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.1835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C16(H16A,H16B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C20(H20), C22(H22), C23(H23),
 C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.7261(4) 0.6356(5) 0.38871(15) 0.0314(7) Uani 1 1 d . . . . .
C2 C 0.6797(4) 0.6307(5) 0.46275(16) 0.0347(7) Uani 1 1 d . . . . .
H2 H 0.6059 0.7338 0.4720 0.042 Uiso 1 1 calc R . . . .
C3 C 0.8743(4) 0.4542(5) 0.52026(16) 0.0371(7) Uani 1 1 d . . . . .
H3A H 0.8750 0.4290 0.5691 0.045 Uiso 1 1 calc R . . . .
H3B H 0.9806 0.4319 0.5046 0.045 Uiso 1 1 calc R . . . .
C4 C 0.7516(4) 0.3334(4) 0.48123(15) 0.0340(7) Uani 1 1 d . . . . .
H4 H 0.7306 0.2181 0.5069 0.041 Uiso 1 1 calc R . . . .
C5 C 0.7977(4) 0.2856(4) 0.40894(14) 0.0282(6) Uani 1 1 d . . . . .
H5A H 0.9041 0.2310 0.4112 0.034 Uiso 1 1 calc R . . . .
H5B H 0.7239 0.1916 0.3895 0.034 Uiso 1 1 calc R . . . .
C6 C 0.7953(3) 0.4563(4) 0.36225(14) 0.0259(6) Uani 1 1 d . . . . .
C7 C 0.8524(3) 0.4635(4) 0.29939(14) 0.0274(6) Uani 1 1 d . . . . .
H7 H 0.8375 0.5789 0.2772 0.033 Uiso 1 1 calc R . . . .
C8 C 0.9341(3) 0.3206(4) 0.25963(14) 0.0239(6) Uani 1 1 d . . . . .
C9 C 0.9416(3) 0.1272(4) 0.27524(14) 0.0262(6) Uani 1 1 d . . . . .
H9 H 0.8896 0.0813 0.3126 0.031 Uiso 1 1 calc R . . . .
C10 C 1.0253(3) 0.0047(4) 0.23566(14) 0.0255(6) Uani 1 1 d . . . . .
H10 H 1.0298 -0.1233 0.2462 0.031 Uiso 1 1 calc R . . . .
C11 C 1.1020(3) 0.0742(4) 0.18032(14) 0.0231(6) Uani 1 1 d . . . . .
C12 C 1.0966(3) 0.2634(4) 0.16251(15) 0.0258(6) Uani 1 1 d . . . . .
H12 H 1.1487 0.3079 0.1249 0.031 Uiso 1 1 calc R . . . .
C13 C 1.0112(3) 0.3838(4) 0.20249(15) 0.0275(7) Uani 1 1 d . . . . .
H13 H 1.0049 0.5110 0.1909 0.033 Uiso 1 1 calc R . . . .
N1 N 1.1924(3) -0.0557(3) 0.13856(12) 0.0268(5) Uani 1 1 d . . . . .
O1 O 0.7092(3) 0.7786(3) 0.35507(12) 0.0494(7) Uani 1 1 d . . . . .
O2 O 0.8223(3) 0.6453(3) 0.50513(11) 0.0378(5) Uani 1 1 d . . . . .
O3 O 0.6121(3) 0.4547(3) 0.47773(12) 0.0415(6) Uani 1 1 d . . . . .
O4 O 1.2027(3) -0.2217(3) 0.15616(11) 0.0358(5) Uani 1 1 d . . . . .
O5 O 1.2536(2) 0.0067(3) 0.08786(10) 0.0316(5) Uani 1 1 d . . . . .
C14 C 0.2914(3) 0.3258(4) 0.88716(14) 0.0250(6) Uani 1 1 d . . . . .
C15 C 0.2510(3) 0.3185(4) 0.96165(15) 0.0290(7) Uani 1 1 d . . . . .
H15 H 0.2458 0.1876 0.9776 0.035 Uiso 1 1 calc R . . . .
C16 C 0.1367(4) 0.5981(4) 0.99077(15) 0.0295(7) Uani 1 1 d . . . . .
H16A H 0.1064 0.6139 1.0376 0.035 Uiso 1 1 calc R . . . .
H16B H 0.0816 0.6920 0.9620 0.035 Uiso 1 1 calc R . . . .
C17 C 0.3161(3) 0.6134(4) 0.98640(14) 0.0249(6) Uani 1 1 d . . . . .
H17 H 0.3615 0.7002 1.0214 0.030 Uiso 1 1 calc R . . . .
C18 C 0.3684(3) 0.6684(4) 0.91544(13) 0.0240(6) Uani 1 1 d . . . . .
H18A H 0.3032 0.7733 0.8983 0.029 Uiso 1 1 calc R . . . .
H18B H 0.4787 0.7111 0.9197 0.029 Uiso 1 1 calc R . . . .
C19 C 0.3551(3) 0.5094(4) 0.86385(14) 0.0227(6) Uani 1 1 d . . . . .
C20 C 0.4048(3) 0.5140(4) 0.79960(14) 0.0238(6) Uani 1 1 d . . . . .
H20 H 0.3853 0.4038 0.7747 0.029 Uiso 1 1 calc R . . . .
C21 C 0.4843(3) 0.6625(4) 0.76222(14) 0.0236(6) Uani 1 1 d . . . . .
C22 C 0.4971(3) 0.8517(4) 0.78244(15) 0.0270(6) Uani 1 1 d . . . . .
H22 H 0.4499 0.8912 0.8220 0.032 Uiso 1 1 calc R . . . .
C23 C 0.5787(3) 0.9803(4) 0.74464(15) 0.0291(7) Uani 1 1 d . . . . .
H23 H 0.5860 1.1060 0.7582 0.035 Uiso 1 1 calc R . . . .
C24 C 0.6495(3) 0.9195(4) 0.68633(14) 0.0248(6) Uani 1 1 d . . . . .
C25 C 0.6380(3) 0.7345(4) 0.66370(15) 0.0286(7) Uani 1 1 d . . . . .
H25 H 0.6852 0.6963 0.6240 0.034 Uiso 1 1 calc R . . . .
C26 C 0.5541(4) 0.6087(4) 0.70188(14) 0.0285(7) Uani 1 1 d . . . . .
H26 H 0.5438 0.4844 0.6870 0.034 Uiso 1 1 calc R . . . .
N2 N 0.7408(3) 1.0535(4) 0.64711(13) 0.0308(6) Uani 1 1 d . . . . .
O6 O 0.2704(3) 0.1868(3) 0.85068(11) 0.0362(5) Uani 1 1 d . . . . .
O7 O 0.1006(2) 0.4098(3) 0.96626(11) 0.0330(5) Uani 1 1 d . . . . .
O8 O 0.3640(2) 0.4212(3) 1.00199(10) 0.0303(5) Uani 1 1 d . . . . .
O9 O 0.7457(3) 1.2191(3) 0.66550(13) 0.0572(8) Uani 1 1 d . . . . .
O10 O 0.8110(3) 0.9952(3) 0.59847(11) 0.0431(6) Uani 1 1 d . . . . .


_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 1.519(4) . ?
C1 C6 1.501(4) . ?
C1 O1 1.212(4) . ?
C2 H2 0.9800 . ?
C2 O2 1.416(4) . ?
C2 O3 1.407(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.509(5) . ?
C3 O2 1.447(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.523(4) . ?
C4 O3 1.448(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.514(4) . ?
C6 C7 1.344(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.469(4) . ?
C8 C9 1.405(4) . ?
C8 C13 1.394(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(4) . ?
C11 C12 1.385(4) . ?
C11 N1 1.468(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9300 . ?
N1 O4 1.227(3) . ?
N1 O5 1.224(3) . ?
C14 C15 1.513(4) . ?
C14 C19 1.487(4) . ?
C14 O6 1.223(3) . ?
C15 H15 0.9800 . ?
C15 O7 1.423(3) . ?
C15 O8 1.400(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.512(4) . ?
C16 O7 1.444(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.528(4) . ?
C17 O8 1.447(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.512(4) . ?
C19 C20 1.345(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.462(4) . ?
C21 C22 1.400(4) . ?
C21 C26 1.398(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(4) . ?
C24 C25 1.385(4) . ?
C24 N2 1.462(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.379(4) . ?
C26 H26 0.9300 . ?
N2 O9 1.227(3) . ?
N2 O10 1.218(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
C6 C1 C2 115.7(3) . . ?
O1 C1 C2 120.5(3) . . ?
O1 C1 C6 123.8(3) . . ?
C1 C2 H2 110.9 . . ?
O2 C2 C1 107.6(2) . . ?
O2 C2 H2 110.9 . . ?
O3 C2 C1 110.2(3) . . ?
O3 C2 H2 110.9 . . ?
O3 C2 O2 106.2(3) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
O2 C3 H3A 111.0 . . ?
O2 C3 H3B 111.0 . . ?
O2 C3 C4 103.9(3) . . ?
C3 C4 H4 110.6 . . ?
C3 C4 C5 113.2(3) . . ?
C5 C4 H4 110.6 . . ?
O3 C4 C3 102.1(3) . . ?
O3 C4 H4 110.6 . . ?
O3 C4 C5 109.5(2) . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.7(2) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C1 C6 C5 117.4(2) . . ?
C7 C6 C1 116.5(3) . . ?
C7 C6 C5 126.0(3) . . ?
C6 C7 H7 114.4 . . ?
C6 C7 C8 131.1(3) . . ?
C8 C7 H7 114.4 . . ?
C9 C8 C7 125.0(3) . . ?
C13 C8 C7 116.9(3) . . ?
C13 C8 C9 118.1(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 122.2(3) . . ?
C10 C11 N1 119.3(3) . . ?
C12 C11 N1 118.5(3) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.8(3) . . ?
C13 C12 H12 121.1 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 122.1(3) . . ?
C12 C13 H13 119.0 . . ?
O4 N1 C11 118.4(2) . . ?
O5 N1 C11 118.4(2) . . ?
O5 N1 O4 123.2(3) . . ?
C2 O2 C3 106.5(2) . . ?
C2 O3 C4 101.7(2) . . ?
C19 C14 C15 115.3(2) . . ?
O6 C14 C15 120.0(3) . . ?
O6 C14 C19 124.6(3) . . ?
C14 C15 H15 110.8 . . ?
O7 C15 C14 107.0(2) . . ?
O7 C15 H15 110.8 . . ?
O8 C15 C14 110.0(2) . . ?
O8 C15 H15 110.8 . . ?
O8 C15 O7 107.4(2) . . ?
H16A C16 H16B 109.0 . . ?
C17 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
O7 C16 H16A 111.0 . . ?
O7 C16 H16B 111.0 . . ?
O7 C16 C17 103.7(2) . . ?
C16 C17 H17 110.6 . . ?
C16 C17 C18 114.0(2) . . ?
C18 C17 H17 110.6 . . ?
O8 C17 C16 100.6(2) . . ?
O8 C17 H17 110.6 . . ?
O8 C17 C18 109.9(2) . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.6(2) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C14 C19 C18 117.5(2) . . ?
C20 C19 C14 116.3(3) . . ?
C20 C19 C18 126.1(3) . . ?
C19 C20 H20 114.5 . . ?
C19 C20 C21 131.1(3) . . ?
C21 C20 H20 114.5 . . ?
C22 C21 C20 125.3(3) . . ?
C26 C21 C20 116.7(3) . . ?
C26 C21 C22 118.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.0(3) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C25 122.2(3) . . ?
C23 C24 N2 119.4(3) . . ?
C25 C24 N2 118.4(3) . . ?
C24 C25 H25 121.1 . . ?
C26 C25 C24 117.9(3) . . ?
C26 C25 H25 121.1 . . ?
C21 C26 H26 119.0 . . ?
C25 C26 C21 122.0(3) . . ?
C25 C26 H26 119.0 . . ?
O9 N2 C24 118.5(3) . . ?
O10 N2 C24 118.6(3) . . ?
O10 N2 O9 122.9(3) . . ?
C15 O7 C16 105.8(2) . . ?
C15 O8 C17 101.6(2) . . ?

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
C1 C2 O2 C3 -92.5(3) . . . . ?
C1 C2 O3 C4 73.5(3) . . . . ?
C1 C6 C7 C8 176.5(3) . . . . ?
C2 C1 C6 C5 5.5(4) . . . . ?
C2 C1 C6 C7 -173.3(3) . . . . ?
C3 C4 C5 C6 -68.2(3) . . . . ?
C3 C4 O3 C2 42.1(3) . . . . ?
C4 C3 O2 C2 1.6(3) . . . . ?
C4 C5 C6 C1 -9.1(4) . . . . ?
C4 C5 C6 C7 169.6(3) . . . . ?
C5 C4 O3 C2 -78.1(3) . . . . ?
C5 C6 C7 C8 -2.2(5) . . . . ?
C6 C1 C2 O2 76.7(3) . . . . ?
C6 C1 C2 O3 -38.6(4) . . . . ?
C6 C7 C8 C9 13.7(5) . . . . ?
C6 C7 C8 C13 -165.7(3) . . . . ?
C7 C8 C9 C10 -178.2(3) . . . . ?
C7 C8 C13 C12 177.8(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C8 C13 C12 -1.6(4) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C9 C10 C11 N1 179.4(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C10 C11 N1 O4 -3.3(4) . . . . ?
C10 C11 N1 O5 176.7(2) . . . . ?
C11 C12 C13 C8 0.9(4) . . . . ?
C12 C11 N1 O4 176.9(3) . . . . ?
C12 C11 N1 O5 -3.1(4) . . . . ?
C13 C8 C9 C10 1.1(4) . . . . ?
N1 C11 C12 C13 -179.9(2) . . . . ?
O1 C1 C2 O2 -102.0(3) . . . . ?
O1 C1 C2 O3 142.7(3) . . . . ?
O1 C1 C6 C5 -175.8(3) . . . . ?
O1 C1 C6 C7 5.4(5) . . . . ?
O2 C2 O3 C4 -42.7(3) . . . . ?
O2 C3 C4 C5 90.8(3) . . . . ?
O2 C3 C4 O3 -26.8(3) . . . . ?
O3 C2 O2 C3 25.5(3) . . . . ?
O3 C4 C5 C6 45.1(3) . . . . ?
C14 C15 O7 C16 -99.6(3) . . . . ?
C14 C15 O8 C17 75.6(3) . . . . ?
C14 C19 C20 C21 -174.5(3) . . . . ?
C15 C14 C19 C18 -1.6(4) . . . . ?
C15 C14 C19 C20 174.4(2) . . . . ?
C16 C17 C18 C19 -75.2(3) . . . . ?
C16 C17 O8 C15 44.8(3) . . . . ?
C17 C16 O7 C15 10.2(3) . . . . ?
C17 C18 C19 C14 1.2(3) . . . . ?
C17 C18 C19 C20 -174.3(3) . . . . ?
C18 C17 O8 C15 -75.7(3) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C19 C14 C15 O7 78.7(3) . . . . ?
C19 C14 C15 O8 -37.7(3) . . . . ?
C19 C20 C21 C22 -13.9(5) . . . . ?
C19 C20 C21 C26 165.3(3) . . . . ?
C20 C21 C22 C23 178.1(3) . . . . ?
C20 C21 C26 C25 -177.3(3) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C21 C26 C25 2.0(4) . . . . ?
C22 C23 C24 C25 1.6(5) . . . . ?
C22 C23 C24 N2 -178.0(3) . . . . ?
C23 C24 C25 C26 -0.8(5) . . . . ?
C23 C24 N2 O9 -3.3(4) . . . . ?
C23 C24 N2 O10 175.3(3) . . . . ?
C24 C25 C26 C21 -1.0(4) . . . . ?
C25 C24 N2 O9 177.1(3) . . . . ?
C25 C24 N2 O10 -4.3(4) . . . . ?
C26 C21 C22 C23 -1.2(4) . . . . ?
N2 C24 C25 C26 178.8(3) . . . . ?
O6 C14 C15 O7 -101.1(3) . . . . ?
O6 C14 C15 O8 142.6(3) . . . . ?
O6 C14 C19 C18 178.1(3) . . . . ?
O6 C14 C19 C20 -5.9(4) . . . . ?
O7 C15 O8 C17 -40.5(3) . . . . ?
O7 C16 C17 C18 83.8(3) . . . . ?
O7 C16 C17 O8 -33.8(3) . . . . ?
O8 C15 O7 C16 18.5(3) . . . . ?
O8 C17 C18 C19 36.9(3) . . . . ?

_olex2_date_sample_data_collection 2017-04-24
_olex2_exptl_crystal_mounting_method 'oil on 100 micrometre micromount'
_olex2_submission_original_sample_id lmh4NO
_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 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.885
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_jhc1711
_database_code_depnum_ccdc_archive 'CCDC 1837710'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H14 O3'
_chemical_oxdiff_usercomment     'Liam lmhtranscinnamaldehyde from MeOH'
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'
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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'

_cell_length_a                   13.5583(2)
_cell_length_b                   13.5583(2)
_cell_length_c                   45.7998(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7291.3(2)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    42176
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      71.0440
_cell_measurement_theta_min      3.7450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 0 0.1493
2 -1 0 0.1373
0 -1 -2 0.0550
0 1 2 0.0740
0 -1 2 0.0525
0 1 -2 0.0718
0 0 -1 0.0472
0 0 1 0.0412

_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.088
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 1.0004 0.0000 0.0827 0.1934 -0.0861
2.0000 -1.0004 -0.0000 -0.0827 -0.1934 0.0861
0.0007 -1.0003 -1.9997 -0.0631 0.0758 0.1098
-0.0007 1.0003 1.9997 0.0631 -0.0758 -0.1098
0.0006 -1.0004 2.0000 0.0621 0.0311 0.1299
-0.0006 1.0004 -2.0000 -0.0621 -0.0311 -0.1299
0.0000 0.0000 -0.9999 -0.0313 0.0112 -0.0050
-0.0000 -0.0000 0.9999 0.0313 -0.0112 0.0050

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            86742
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.056
_diffrn_reflns_theta_max         67.056
_diffrn_reflns_theta_min         3.765
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00 150.00   90
  2  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00 -90.00   90
  3  ω     75.00 124.00   1.00    4.00    --   54.00 156.00  89.00   49
  4  ω    -15.00  75.00   1.00    4.00    --   54.00 -57.00-120.00   90
  5  ω     23.00 111.00   1.00    4.00    --   54.00-125.00  90.00   88
  6  ω     33.00 123.00   1.00    4.00    --   54.00  57.00 150.00   90
  7  ω     33.00 123.00   1.00    4.00    --   54.00  57.00 -60.00   90
  8  ω    -15.00  75.00   1.00    4.00    --   54.00 -57.00 150.00   90
  9  ω     33.00 123.00   1.00    4.00    --   54.00  57.00  30.00   90
 10  ω     86.00 176.00   1.00    8.00    --  108.00  63.00  30.00   90
 11  ω     86.00 176.00   1.00    8.00    --  108.00  63.00 -90.00   90
 12  ω    100.00 178.00   1.00    8.00    --  108.00 111.00 120.00   78
 13  ω     36.00 116.00   1.00    8.00    --  108.00-111.00  60.00   80
 14  ω     86.00 178.00   1.00    8.00    --  108.00  50.00  90.00   92
 15  ω     86.00 176.00   1.00    8.00    --  108.00  63.00 -30.00   90
 16  ω     86.00 178.00   1.00    8.00    --  108.00  50.00-150.00   92
 17  ω     86.00 178.00   1.00    8.00    --  108.00  50.00 -60.00   92
 18  ω     78.00 178.00   1.00    8.00    --  108.00  77.00-120.00  100
 19  ω     38.00 130.00   1.00    8.00    --  108.00 -50.00-120.00   92
 20  ω    -54.00   3.00   1.00    1.00    --    0.00 119.00 -66.00   57
 21  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00  30.00   90
 22  ω     24.00 124.00   1.00    4.00    --   54.00  77.00 -30.00  100
 23  ω    -18.00  80.00   1.00    4.00    --   54.00 -37.00   0.00   98
 24  ω     33.00 123.00   1.00    4.00    --   54.00  57.00  90.00   90
 25  ω     24.00 124.00   1.00    4.00    --   54.00  77.00-150.00  100
 26  ω     36.00 116.00   1.00    8.00    --  108.00-111.00-120.00   80
 27  ω     86.00 139.00   1.00    8.00    --  108.00  50.00-180.00   53
 28  ω     36.00 116.00   1.00    8.00    --  108.00-111.00 -60.00   80
 29  ω     86.00 178.00   1.00    8.00    --  108.00  50.00 120.00   92
 30  ω     78.00 178.00   1.00    8.00    --  108.00  77.00   0.00  100
 31  ω     38.00 138.00   1.00    8.00    --  108.00 -77.00  60.00  100
 32  ω     74.00 178.00   1.00    8.00    --  108.00  25.00-180.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0411218000
_diffrn_orient_matrix_UB_12      0.0004753000
_diffrn_orient_matrix_UB_13      0.0313234000
_diffrn_orient_matrix_UB_21      -0.1234490000
_diffrn_orient_matrix_UB_22      -0.0534799000
_diffrn_orient_matrix_UB_23      -0.0111709000
_diffrn_orient_matrix_UB_31      -0.0168746000
_diffrn_orient_matrix_UB_32      -0.1198076000
_diffrn_orient_matrix_UB_33      0.0050207000
_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_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                8577
_reflns_number_total             8674
_reflns_odcompleteness_completeness 99.91
_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 1.171.38.46 (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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 3928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         8674
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0909
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0978P)²+26.2792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2298
_refine_ls_wR_factor_ref         0.2302
_refine_special_details          
;
The crystal exhibited merohedral twinning with refined occupancies of
0.668:0.332(5).  
The asymmetric unit contained four molecules in two pairs.  Within 
each pair there is an approximate translation in the ab plane although
the axe are different for each pair.  No higher symmetry could
be determined.  The ADP of some of the equivalent atoms in the paired
moledules were constrained to be equal (i.e. C2 & C17, C4 & C19,
C31 & C46, C34 & C49, C36 & C51, C37 & C52, C43 & C58, C44 & C59).
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.669(5)
 0.331(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C51) = Uanis(C36)
Uanis(C52) = Uanis(C37)
Uanis(C49) = Uanis(C34)
Uanis(C44) = Uanis(C59)
Uanis(C43) = Uanis(C58)
Uanis(C19) = Uanis(C4)
Uanis(C17) = Uanis(C2)
Uanis(C31) = Uanis(C46)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C17(H17), C19(H19), C32(H32), C34(H34), C47(H47), C49(H49)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C18(H18A,H18B), C20(H20A,H20B), C33(H33A,H33B),
 C35(H35A,H35B), C48(H48A,H48B), C50(H50A,H50B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
  C37(H37), C38(H38), C39(H39), C41(H41), C42(H42), C43(H43), C44(H44),
 C45(H45), C52(H52), C53(H53), C54(H54), C56(H56), C57(H57), C58(H58), C59(H59),
  C60(H60)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.3301(10) 0.5067(9) 0.4698(2) 0.024(2) Uani 1 1 d . . . . .
C2 C 0.4060(10) 0.4561(10) 0.4744(2) 0.0257(18) Uani 1 1 d . . . . .
H2 H 0.4865 0.5175 0.4778 0.031 Uiso 1 1 calc R . . . .
C3 C 0.3052(10) 0.2751(11) 0.4554(3) 0.032(3) Uani 1 1 d . . . . .
H3A H 0.3317 0.2190 0.4552 0.039 Uiso 1 1 calc R . . . .
H3B H 0.2434 0.2520 0.4409 0.039 Uiso 1 1 calc R . . . .
C4 C 0.2650(9) 0.2849(10) 0.4858(3) 0.0241(18) Uani 1 1 d . . . . .
H4 H 0.2430 0.2144 0.4974 0.029 Uiso 1 1 calc R . . . .
C5 C 0.1692(9) 0.3123(9) 0.4857(3) 0.027(3) Uani 1 1 d . . . . .
H5A H 0.1417 0.3087 0.5059 0.033 Uiso 1 1 calc R . . . .
H5B H 0.1049 0.2548 0.4739 0.033 Uiso 1 1 calc R . . . .
C6 C 0.2100(9) 0.4323(9) 0.4729(2) 0.019(2) Uani 1 1 d . . . . .
C7 C 0.1363(8) 0.4686(9) 0.4675(2) 0.017(2) Uani 1 1 d . . . . .
H7 H 0.1679 0.5426 0.4593 0.021 Uiso 1 1 calc R . . . .
C8 C 0.0142(9) 0.4091(10) 0.4725(2) 0.022(2) Uani 1 1 d . . . . .
H8 H -0.0213 0.3338 0.4801 0.026 Uiso 1 1 calc R . . . .
C9 C -0.0497(10) 0.4555(9) 0.4670(2) 0.022(2) Uani 1 1 d . . . . .
H9 H -0.0117 0.5298 0.4588 0.026 Uiso 1 1 calc R . . . .
C10 C -0.1692(10) 0.4067(10) 0.4720(2) 0.022(2) Uani 1 1 d . . . . .
C11 C -0.2316(11) 0.3076(12) 0.4883(3) 0.033(3) Uani 1 1 d . . . . .
H11 H -0.1946 0.2710 0.4969 0.039 Uiso 1 1 calc R . . . .
C12 C -0.3483(10) 0.2626(9) 0.4920(3) 0.026(2) Uani 1 1 d . . . . .
H12 H -0.3904 0.1954 0.5032 0.031 Uiso 1 1 calc R . . . .
C13 C -0.4035(10) 0.3142(10) 0.4796(2) 0.026(2) Uani 1 1 d . . . . .
H13 H -0.4837 0.2803 0.4815 0.032 Uiso 1 1 calc R . . . .
C14 C -0.3425(9) 0.4152(10) 0.4644(2) 0.024(2) Uani 1 1 d . . . . .
H14 H -0.3798 0.4534 0.4570 0.029 Uiso 1 1 calc R . . . .
C15 C -0.2262(9) 0.4607(9) 0.4600(2) 0.022(2) Uani 1 1 d . . . . .
H15 H -0.1848 0.5284 0.4488 0.026 Uiso 1 1 calc R . . . .
O1 O 0.3722(7) 0.6084(7) 0.4616(2) 0.034(2) Uani 1 1 d . . . . .
O2 O 0.3988(7) 0.3895(7) 0.44941(18) 0.0312(19) Uani 1 1 d . . . . .
O3 O 0.3657(7) 0.3817(6) 0.49809(16) 0.0242(16) Uani 1 1 d . . . . .
C16 C 0.8153(10) 1.0087(9) 0.4677(2) 0.023(2) Uani 1 1 d . . . . .
C17 C 0.8855(9) 0.9522(10) 0.4716(3) 0.0257(18) Uani 1 1 d . . . . .
H17 H 0.9668 1.0108 0.4754 0.031 Uiso 1 1 calc R . . . .
C18 C 0.7823(11) 0.7750(11) 0.4506(3) 0.032(3) Uani 1 1 d . . . . .
H18A H 0.8084 0.7187 0.4496 0.038 Uiso 1 1 calc R . . . .
H18B H 0.7209 0.7544 0.4361 0.038 Uiso 1 1 calc R . . . .
C19 C 0.7411(9) 0.7810(10) 0.4818(3) 0.0241(18) Uani 1 1 d . . . . .
H19 H 0.7178 0.7083 0.4925 0.029 Uiso 1 1 calc R . . . .
C20 C 0.6479(9) 0.8101(10) 0.4832(3) 0.023(2) Uani 1 1 d . . . . .
H20A H 0.6210 0.8028 0.5036 0.028 Uiso 1 1 calc R . . . .
H20B H 0.5828 0.7554 0.4711 0.028 Uiso 1 1 calc R . . . .
C21 C 0.6888(9) 0.9327(10) 0.4722(3) 0.025(2) Uani 1 1 d . . . . .
C22 C 0.6215(11) 0.9743(10) 0.4681(2) 0.025(2) Uani 1 1 d . . . . .
H22 H 0.6556 1.0513 0.4618 0.030 Uiso 1 1 calc R . . . .
C23 C 0.4988(9) 0.9130(9) 0.4722(2) 0.020(2) Uani 1 1 d . . . . .
H23 H 0.4632 0.8377 0.4797 0.024 Uiso 1 1 calc R . . . .
C24 C 0.4346(11) 0.9591(10) 0.4656(3) 0.029(3) Uani 1 1 d . . . . .
H24 H 0.4727 1.0335 0.4575 0.035 Uiso 1 1 calc R . . . .
C25 C 0.3109(10) 0.9062(10) 0.4698(2) 0.021(2) Uani 1 1 d . . . . .
C26 C 0.2421(8) 0.8021(9) 0.4843(2) 0.020(2) Uani 1 1 d . . . . .
H26 H 0.2748 0.7604 0.4924 0.024 Uiso 1 1 calc R . . . .
C27 C 0.1273(10) 0.7618(11) 0.4865(2) 0.027(3) Uani 1 1 d . . . . .
H27 H 0.0814 0.6912 0.4962 0.032 Uiso 1 1 calc R . . . .
C28 C 0.0748(9) 0.8199(11) 0.4753(2) 0.030(3) Uani 1 1 d . . . . .
H28 H -0.0045 0.7912 0.4778 0.035 Uiso 1 1 calc R . . . .
C29 C 0.1406(11) 0.9179(11) 0.4609(2) 0.030(3) Uani 1 1 d . . . . .
H29 H 0.1058 0.9575 0.4527 0.036 Uiso 1 1 calc R . . . .
C30 C 0.2581(11) 0.9638(10) 0.4574(2) 0.025(2) Uani 1 1 d . . . . .
H30 H 0.3018 1.0328 0.4469 0.030 Uiso 1 1 calc R . . . .
O4 O 0.8586(7) 1.1065(7) 0.46041(19) 0.0299(19) Uani 1 1 d . . . . .
O5 O 0.8772(7) 0.8910(8) 0.44558(17) 0.0319(19) Uani 1 1 d . . . . .
O6 O 0.8441(6) 0.8717(7) 0.49411(16) 0.0254(16) Uani 1 1 d . . . . .
C31 C 0.1919(9) 0.6912(9) 0.5585(2) 0.0213(17) Uani 1 1 d . . . . .
C32 C 0.1216(9) 0.5648(9) 0.5539(2) 0.022(2) Uani 1 1 d . . . . .
H32 H 0.0409 0.5429 0.5495 0.027 Uiso 1 1 calc R . . . .
C33 C 0.2226(10) 0.4966(10) 0.5776(3) 0.035(3) Uani 1 1 d . . . . .
H33A H 0.1991 0.4154 0.5806 0.041 Uiso 1 1 calc R . . . .
H33B H 0.2825 0.5432 0.5920 0.041 Uiso 1 1 calc R . . . .
C34 C 0.2657(9) 0.5341(10) 0.5464(2) 0.0240(17) Uani 1 1 d . . . . .
H34 H 0.2891 0.4827 0.5369 0.029 Uiso 1 1 calc R . . . .
C35 C 0.3583(10) 0.6595(10) 0.5442(3) 0.026(3) Uani 1 1 d . . . . .
H35A H 0.4237 0.6726 0.5565 0.031 Uiso 1 1 calc R . . . .
H35B H 0.3852 0.6766 0.5238 0.031 Uiso 1 1 calc R . . . .
C36 C 0.3174(8) 0.7403(8) 0.5536(2) 0.0155(14) Uani 1 1 d . . . . .
C37 C 0.3886(9) 0.8542(9) 0.5578(2) 0.0199(15) Uani 1 1 d . . . . .
H37 H 0.3551 0.8982 0.5637 0.024 Uiso 1 1 calc R . . . .
C38 C 0.5093(9) 0.9126(8) 0.5541(3) 0.025(2) Uani 1 1 d . . . . .
H38 H 0.5465 0.8721 0.5482 0.030 Uiso 1 1 calc R . . . .
C39 C 0.5714(9) 1.0281(9) 0.55913(19) 0.017(2) Uani 1 1 d . . . . .
H39 H 0.5309 1.0644 0.5656 0.020 Uiso 1 1 calc R . . . .
C40 C 0.6954(8) 1.0999(10) 0.5552(2) 0.021(2) Uani 1 1 d . . . . .
C41 C 0.7598(10) 1.0626(9) 0.5414(2) 0.024(2) Uani 1 1 d . . . . .
H41 H 0.7246 0.9878 0.5335 0.028 Uiso 1 1 calc R . . . .
C42 C 0.8786(10) 1.1349(11) 0.5388(3) 0.032(3) Uani 1 1 d . . . . .
H42 H 0.9232 1.1088 0.5291 0.039 Uiso 1 1 calc R . . . .
C43 C 0.9302(10) 1.2439(10) 0.5504(3) 0.0295(18) Uani 1 1 d . . . . .
H43 H 1.0100 1.2930 0.5484 0.035 Uiso 1 1 calc R . . . .
C44 C 0.8671(10) 1.2800(10) 0.5645(2) 0.030(2) Uani 1 1 d . . . . .
H44 H 0.9030 1.3536 0.5731 0.036 Uiso 1 1 calc R . . . .
C45 C 0.7509(10) 1.2109(9) 0.5666(2) 0.025(2) Uani 1 1 d . . . . .
H45 H 0.7072 1.2390 0.5759 0.030 Uiso 1 1 calc R . . . .
O7 O 0.1485(7) 0.7492(8) 0.5650(2) 0.037(2) Uani 1 1 d . . . . .
O8 O 0.1271(7) 0.5141(7) 0.58035(18) 0.0338(19) Uani 1 1 d . . . . .
O9 O 0.1635(7) 0.5271(7) 0.53219(17) 0.0310(18) Uani 1 1 d . . . . .
C46 C -0.3175(10) 0.6847(9) 0.5582(2) 0.0213(17) Uani 1 1 d . . . . .
C47 C -0.3971(10) 0.5559(9) 0.5529(2) 0.025(2) Uani 1 1 d . . . . .
H47 H -0.4776 0.5375 0.5499 0.030 Uiso 1 1 calc R . . . .
C48 C -0.2962(11) 0.4779(10) 0.5711(3) 0.033(3) Uani 1 1 d . . . . .
H48A H -0.3225 0.3954 0.5715 0.039 Uiso 1 1 calc R . . . .
H48B H -0.2341 0.5172 0.5855 0.039 Uiso 1 1 calc R . . . .
C49 C -0.2568(9) 0.5272(10) 0.5406(2) 0.0240(17) Uani 1 1 d . . . . .
H49 H -0.2365 0.4768 0.5293 0.029 Uiso 1 1 calc R . . . .
C50 C -0.1594(9) 0.6465(10) 0.5398(2) 0.022(2) Uani 1 1 d . . . . .
H50A H -0.1338 0.6683 0.5194 0.027 Uiso 1 1 calc R . . . .
H50B H -0.0949 0.6515 0.5511 0.027 Uiso 1 1 calc R . . . .
C51 C -0.1943(8) 0.7283(9) 0.5525(2) 0.0155(14) Uani 1 1 d . . . . .
C52 C -0.1224(9) 0.8390(9) 0.5583(2) 0.0199(15) Uani 1 1 d . . . . .
H52 H -0.1546 0.8813 0.5662 0.024 Uiso 1 1 calc R . . . .
C53 C -0.0007(8) 0.8996(9) 0.5535(2) 0.019(2) Uani 1 1 d . . . . .
H53 H 0.0342 0.8601 0.5454 0.023 Uiso 1 1 calc R . . . .
C54 C 0.0637(9) 1.0095(9) 0.5603(2) 0.017(2) Uani 1 1 d . . . . .
H54 H 0.0265 1.0454 0.5691 0.021 Uiso 1 1 calc R . . . .
C55 C 0.1851(9) 1.0794(10) 0.5553(2) 0.023(2) Uani 1 1 d . . . . .
C56 C 0.2465(9) 1.0425(9) 0.5380(2) 0.018(2) Uani 1 1 d . . . . .
H56 H 0.2078 0.9688 0.5294 0.021 Uiso 1 1 calc R . . . .
C57 C 0.3613(10) 1.1113(11) 0.5332(2) 0.031(3) Uani 1 1 d . . . . .
H57 H 0.4016 1.0848 0.5217 0.037 Uiso 1 1 calc R . . . .
C58 C 0.4187(10) 1.2205(10) 0.5454(3) 0.0295(18) Uani 1 1 d . . . . .
H58 H 0.4973 1.2692 0.5414 0.035 Uiso 1 1 calc R . . . .
C59 C 0.3610(10) 1.2593(10) 0.5636(2) 0.030(2) Uani 1 1 d . . . . .
H59 H 0.4002 1.3317 0.5728 0.036 Uiso 1 1 calc R . . . .
C60 C 0.2463(9) 1.1888(9) 0.5675(2) 0.021(2) Uani 1 1 d . . . . .
H60 H 0.2060 1.2154 0.5790 0.026 Uiso 1 1 calc R . . . .
O10 O -0.3618(8) 0.7412(8) 0.5655(2) 0.035(2) Uani 1 1 d . . . . .
O11 O -0.3880(7) 0.4983(6) 0.57698(18) 0.0298(19) Uani 1 1 d . . . . .
O12 O -0.3570(7) 0.5195(7) 0.52862(17) 0.0271(18) Uani 1 1 d . . . . .


_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 1.509(16) . ?
C1 C6 1.431(16) . ?
C1 O1 1.257(14) . ?
C2 H2 1.0000 . ?
C2 O2 1.431(14) . ?
C2 O3 1.394(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.525(17) . ?
C3 O2 1.458(15) . ?
C4 H4 1.0000 . ?
C4 C5 1.519(14) . ?
C4 O3 1.454(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.547(14) . ?
C6 C7 1.341(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.452(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.325(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.429(16) . ?
C10 C11 1.394(18) . ?
C10 C15 1.414(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.502(16) . ?
C16 C21 1.510(15) . ?
C16 O4 1.197(14) . ?
C17 H17 1.0000 . ?
C17 O5 1.424(14) . ?
C17 O6 1.398(14) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.550(17) . ?
C18 O5 1.469(16) . ?
C19 H19 1.0000 . ?
C19 C20 1.503(15) . ?
C19 O6 1.436(13) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.549(16) . ?
C21 C22 1.305(17) . ?
C22 H22 0.9500 . ?
C22 C23 1.452(16) . ?
C23 H23 0.9500 . ?
C23 C24 1.334(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.470(17) . ?
C25 C26 1.411(15) . ?
C25 C30 1.415(15) . ?
C26 H26 0.9500 . ?
C26 C27 1.372(15) . ?
C27 H27 0.9500 . ?
C27 C28 1.397(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.346(18) . ?
C29 H29 0.9500 . ?
C29 C30 1.400(18) . ?
C30 H30 0.9500 . ?
C31 C32 1.503(15) . ?
C31 C36 1.501(14) . ?
C31 O7 1.231(15) . ?
C32 H32 1.0000 . ?
C32 O8 1.414(14) . ?
C32 O9 1.364(14) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.529(17) . ?
C33 O8 1.434(15) . ?
C34 H34 1.0000 . ?
C34 C35 1.530(16) . ?
C34 O9 1.490(13) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.518(14) . ?
C36 C37 1.365(14) . ?
C37 H37 0.9500 . ?
C37 C38 1.429(15) . ?
C38 H38 0.9500 . ?
C38 C39 1.377(15) . ?
C39 H39 0.9500 . ?
C39 C40 1.474(14) . ?
C40 C41 1.363(15) . ?
C40 C45 1.403(16) . ?
C41 H41 0.9500 . ?
C41 C42 1.410(17) . ?
C42 H42 0.9500 . ?
C42 C43 1.386(17) . ?
C43 H43 0.9500 . ?
C43 C44 1.344(19) . ?
C44 H44 0.9500 . ?
C44 C45 1.376(17) . ?
C45 H45 0.9500 . ?
C46 C47 1.545(15) . ?
C46 C51 1.490(14) . ?
C46 O10 1.233(14) . ?
C47 H47 1.0000 . ?
C47 O11 1.391(14) . ?
C47 O12 1.431(14) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.526(17) . ?
C48 O11 1.430(15) . ?
C49 H49 1.0000 . ?
C49 C50 1.492(15) . ?
C49 O12 1.419(14) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.523(15) . ?
C51 C52 1.345(15) . ?
C52 H52 0.9500 . ?
C52 C53 1.445(14) . ?
C53 H53 0.9500 . ?
C53 C54 1.333(15) . ?
C54 H54 0.9500 . ?
C54 C55 1.448(15) . ?
C55 C56 1.411(15) . ?
C55 C60 1.403(16) . ?
C56 H56 0.9500 . ?
C56 C57 1.374(16) . ?
C57 H57 0.9500 . ?
C57 C58 1.398(17) . ?
C58 H58 0.9500 . ?
C58 C59 1.413(18) . ?
C59 H59 0.9500 . ?
C59 C60 1.370(16) . ?
C60 H60 0.9500 . ?

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
C6 C1 C2 117.3(10) . . ?
O1 C1 C2 120.1(11) . . ?
O1 C1 C6 122.4(11) . . ?
C1 C2 H2 110.6 . . ?
O2 C2 C1 109.1(9) . . ?
O2 C2 H2 110.6 . . ?
O3 C2 C1 109.2(9) . . ?
O3 C2 H2 110.6 . . ?
O3 C2 O2 106.7(9) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
O2 C3 H3A 111.0 . . ?
O2 C3 H3B 111.0 . . ?
O2 C3 C4 103.8(9) . . ?
C3 C4 H4 110.6 . . ?
C5 C4 C3 113.9(10) . . ?
C5 C4 H4 110.6 . . ?
O3 C4 C3 102.6(9) . . ?
O3 C4 H4 110.6 . . ?
O3 C4 C5 108.2(9) . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.0(9) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C1 C6 C5 117.5(9) . . ?
C7 C6 C1 121.1(10) . . ?
C7 C6 C5 121.1(9) . . ?
C6 C7 H7 115.9 . . ?
C6 C7 C8 128.2(10) . . ?
C8 C7 H7 115.9 . . ?
C7 C8 H8 118.6 . . ?
C9 C8 C7 122.7(10) . . ?
C9 C8 H8 118.6 . . ?
C8 C9 H9 116.2 . . ?
C8 C9 C10 127.6(10) . . ?
C10 C9 H9 116.2 . . ?
C11 C10 C9 122.1(10) . . ?
C11 C10 C15 118.9(11) . . ?
C15 C10 C9 119.0(10) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(11) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(11) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(11) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(11) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.3(11) . . ?
C14 C15 H15 119.8 . . ?
C2 O2 C3 105.6(9) . . ?
C2 O3 C4 101.7(8) . . ?
C17 C16 C21 115.4(9) . . ?
O4 C16 C17 120.8(11) . . ?
O4 C16 C21 123.7(10) . . ?
C16 C17 H17 110.1 . . ?
O5 C17 C16 108.1(9) . . ?
O5 C17 H17 110.1 . . ?
O6 C17 C16 112.1(9) . . ?
O6 C17 H17 110.1 . . ?
O6 C17 O5 106.2(9) . . ?
H18A C18 H18B 109.0 . . ?
C19 C18 H18A 111.1 . . ?
C19 C18 H18B 111.1 . . ?
O5 C18 H18A 111.1 . . ?
O5 C18 H18B 111.1 . . ?
O5 C18 C19 103.5(9) . . ?
C18 C19 H19 110.2 . . ?
C20 C19 C18 115.2(9) . . ?
C20 C19 H19 110.2 . . ?
O6 C19 C18 100.7(9) . . ?
O6 C19 H19 110.2 . . ?
O6 C19 C20 110.0(9) . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C19 C20 C21 111.8(9) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C16 C21 C20 116.9(9) . . ?
C22 C21 C16 119.1(11) . . ?
C22 C21 C20 123.9(10) . . ?
C21 C22 H22 117.2 . . ?
C21 C22 C23 125.6(11) . . ?
C23 C22 H22 117.2 . . ?
C22 C23 H23 119.0 . . ?
C24 C23 C22 122.1(11) . . ?
C24 C23 H23 119.0 . . ?
C23 C24 H24 116.7 . . ?
C23 C24 C25 126.6(11) . . ?
C25 C24 H24 116.7 . . ?
C26 C25 C24 124.8(10) . . ?
C26 C25 C30 118.5(10) . . ?
C30 C25 C24 116.7(10) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 C25 119.0(11) . . ?
C27 C26 H26 120.5 . . ?
C26 C27 H27 118.5 . . ?
C26 C27 C28 123.0(11) . . ?
C28 C27 H27 118.5 . . ?
C27 C28 H28 121.1 . . ?
C29 C28 C27 117.7(11) . . ?
C29 C28 H28 121.1 . . ?
C28 C29 H29 118.7 . . ?
C28 C29 C30 122.6(11) . . ?
C30 C29 H29 118.7 . . ?
C25 C30 H30 120.4 . . ?
C29 C30 C25 119.2(11) . . ?
C29 C30 H30 120.4 . . ?
C17 O5 C18 105.3(9) . . ?
C17 O6 C19 102.6(8) . . ?
C36 C31 C32 114.6(9) . . ?
O7 C31 C32 122.0(10) . . ?
O7 C31 C36 123.4(10) . . ?
C31 C32 H32 110.0 . . ?
O8 C32 C31 106.1(9) . . ?
O8 C32 H32 110.0 . . ?
O9 C32 C31 112.6(9) . . ?
O9 C32 H32 110.0 . . ?
O9 C32 O8 108.0(9) . . ?
H33A C33 H33B 108.9 . . ?
C34 C33 H33A 110.8 . . ?
C34 C33 H33B 110.8 . . ?
O8 C33 H33A 110.8 . . ?
O8 C33 H33B 110.8 . . ?
O8 C33 C34 104.6(9) . . ?
C33 C34 H34 112.0 . . ?
C33 C34 C35 113.4(9) . . ?
C35 C34 H34 112.0 . . ?
O9 C34 C33 101.5(8) . . ?
O9 C34 H34 112.0 . . ?
O9 C34 C35 105.2(9) . . ?
C34 C35 H35A 109.0 . . ?
C34 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 C34 112.9(9) . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C31 C36 C35 117.7(9) . . ?
C37 C36 C31 119.0(9) . . ?
C37 C36 C35 123.4(9) . . ?
C36 C37 H37 117.4 . . ?
C36 C37 C38 125.2(10) . . ?
C38 C37 H37 117.4 . . ?
C37 C38 H38 120.4 . . ?
C39 C38 C37 119.2(10) . . ?
C39 C38 H38 120.4 . . ?
C38 C39 H39 117.4 . . ?
C38 C39 C40 125.2(10) . . ?
C40 C39 H39 117.4 . . ?
C41 C40 C39 122.9(11) . . ?
C41 C40 C45 118.1(10) . . ?
C45 C40 C39 119.1(10) . . ?
C40 C41 H41 119.9 . . ?
C40 C41 C42 120.1(11) . . ?
C42 C41 H41 119.9 . . ?
C41 C42 H42 120.0 . . ?
C43 C42 C41 120.1(11) . . ?
C43 C42 H42 120.0 . . ?
C42 C43 H43 120.1 . . ?
C44 C43 C42 119.8(11) . . ?
C44 C43 H43 120.1 . . ?
C43 C44 H44 119.8 . . ?
C43 C44 C45 120.4(11) . . ?
C45 C44 H44 119.8 . . ?
C40 C45 H45 119.3 . . ?
C44 C45 C40 121.4(11) . . ?
C44 C45 H45 119.3 . . ?
C32 O8 C33 106.1(9) . . ?
C32 O9 C34 101.8(8) . . ?
C51 C46 C47 115.6(9) . . ?
O10 C46 C47 117.6(10) . . ?
O10 C46 C51 126.7(10) . . ?
C46 C47 H47 111.2 . . ?
O11 C47 C46 107.7(9) . . ?
O11 C47 H47 111.2 . . ?
O11 C47 O12 105.5(8) . . ?
O12 C47 C46 109.8(9) . . ?
O12 C47 H47 111.2 . . ?
H48A C48 H48B 109.0 . . ?
C49 C48 H48A 111.0 . . ?
C49 C48 H48B 111.0 . . ?
O11 C48 H48A 111.0 . . ?
O11 C48 H48B 111.0 . . ?
O11 C48 C49 103.6(9) . . ?
C48 C49 H49 109.3 . . ?
C50 C49 C48 115.0(10) . . ?
C50 C49 H49 109.3 . . ?
O12 C49 C48 102.1(9) . . ?
O12 C49 H49 109.3 . . ?
O12 C49 C50 111.5(10) . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 C51 110.5(9) . . ?
H50A C50 H50B 108.1 . . ?
C51 C50 H50A 109.5 . . ?
C51 C50 H50B 109.5 . . ?
C46 C51 C50 118.2(8) . . ?
C52 C51 C46 116.9(9) . . ?
C52 C51 C50 124.9(9) . . ?
C51 C52 H52 116.9 . . ?
C51 C52 C53 126.1(10) . . ?
C53 C52 H52 116.9 . . ?
C52 C53 H53 119.2 . . ?
C54 C53 C52 121.6(9) . . ?
C54 C53 H53 119.2 . . ?
C53 C54 H54 116.9 . . ?
C53 C54 C55 126.2(10) . . ?
C55 C54 H54 116.9 . . ?
C56 C55 C54 122.3(10) . . ?
C60 C55 C54 120.5(10) . . ?
C60 C55 C56 117.1(10) . . ?
C55 C56 H56 119.4 . . ?
C57 C56 C55 121.2(10) . . ?
C57 C56 H56 119.4 . . ?
C56 C57 H57 120.1 . . ?
C56 C57 C58 119.8(10) . . ?
C58 C57 H57 120.1 . . ?
C57 C58 H58 119.6 . . ?
C57 C58 C59 120.7(11) . . ?
C59 C58 H58 119.6 . . ?
C58 C59 H59 121.2 . . ?
C60 C59 C58 117.6(11) . . ?
C60 C59 H59 121.2 . . ?
C55 C60 H60 118.3 . . ?
C59 C60 C55 123.5(11) . . ?
C59 C60 H60 118.3 . . ?
C47 O11 C48 106.9(9) . . ?
C49 O12 C47 100.9(8) . . ?

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
C1 C2 O2 C3 -89.6(11) . . . . ?
C1 C2 O3 C4 73.9(10) . . . . ?
C1 C6 C7 C8 -172.8(10) . . . . ?
C2 C1 C6 C5 9.8(14) . . . . ?
C2 C1 C6 C7 -175.9(10) . . . . ?
C3 C4 C5 C6 -65.5(13) . . . . ?
C3 C4 O3 C2 41.2(10) . . . . ?
C4 C3 O2 C2 -1.4(11) . . . . ?
C4 C5 C6 C1 -13.9(14) . . . . ?
C4 C5 C6 C7 171.8(10) . . . . ?
C5 C4 O3 C2 -79.5(11) . . . . ?
C5 C6 C7 C8 1.3(17) . . . . ?
C6 C1 C2 O2 75.7(12) . . . . ?
C6 C1 C2 O3 -40.7(13) . . . . ?
C6 C7 C8 C9 177.8(10) . . . . ?
C7 C8 C9 C10 -177.8(10) . . . . ?
C8 C9 C10 C11 11.3(17) . . . . ?
C8 C9 C10 C15 -168.9(11) . . . . ?
C9 C10 C11 C12 -178.8(11) . . . . ?
C9 C10 C15 C14 180.0(10) . . . . ?
C10 C11 C12 C13 0.4(18) . . . . ?
C11 C10 C15 C14 -0.2(16) . . . . ?
C11 C12 C13 C14 -3.3(17) . . . . ?
C12 C13 C14 C15 4.4(16) . . . . ?
C13 C14 C15 C10 -2.7(16) . . . . ?
C15 C10 C11 C12 1.3(17) . . . . ?
O1 C1 C2 O2 -99.8(12) . . . . ?
O1 C1 C2 O3 143.9(10) . . . . ?
O1 C1 C6 C5 -174.9(10) . . . . ?
O1 C1 C6 C7 -0.6(16) . . . . ?
O2 C2 O3 C4 -44.0(10) . . . . ?
O2 C3 C4 C5 92.5(11) . . . . ?
O2 C3 C4 O3 -24.1(10) . . . . ?
O3 C2 O2 C3 28.3(11) . . . . ?
O3 C4 C5 C6 47.8(13) . . . . ?
C16 C17 O5 C18 -92.7(11) . . . . ?
C16 C17 O6 C19 71.6(11) . . . . ?
C16 C21 C22 C23 -178.6(9) . . . . ?
C17 C16 C21 C20 5.6(15) . . . . ?
C17 C16 C21 C22 -177.3(10) . . . . ?
C18 C19 C20 C21 -65.7(13) . . . . ?
C18 C19 O6 C17 43.7(10) . . . . ?
C19 C18 O5 C17 0.2(11) . . . . ?
C19 C20 C21 C16 -11.2(14) . . . . ?
C19 C20 C21 C22 171.8(11) . . . . ?
C20 C19 O6 C17 -78.3(11) . . . . ?
C20 C21 C22 C23 -1.6(18) . . . . ?
C21 C16 C17 O5 80.2(12) . . . . ?
C21 C16 C17 O6 -36.5(14) . . . . ?
C21 C22 C23 C24 -175.6(11) . . . . ?
C22 C23 C24 C25 -178.0(10) . . . . ?
C23 C24 C25 C26 7.2(18) . . . . ?
C23 C24 C25 C30 -171.1(11) . . . . ?
C24 C25 C26 C27 -179.8(10) . . . . ?
C24 C25 C30 C29 -179.4(10) . . . . ?
C25 C26 C27 C28 -0.6(17) . . . . ?
C26 C25 C30 C29 2.2(16) . . . . ?
C26 C27 C28 C29 2.1(17) . . . . ?
C27 C28 C29 C30 -1.4(17) . . . . ?
C28 C29 C30 C25 -0.7(17) . . . . ?
C30 C25 C26 C27 -1.5(15) . . . . ?
O4 C16 C17 O5 -97.4(12) . . . . ?
O4 C16 C17 O6 145.9(11) . . . . ?
O4 C16 C21 C20 -176.9(11) . . . . ?
O4 C16 C21 C22 0.3(18) . . . . ?
O5 C17 O6 C19 -46.2(10) . . . . ?
O5 C18 C19 C20 91.7(11) . . . . ?
O5 C18 C19 O6 -26.5(10) . . . . ?
O6 C17 O5 C18 27.7(11) . . . . ?
O6 C19 C20 C21 47.3(13) . . . . ?
C31 C32 O8 C33 -90.9(10) . . . . ?
C31 C32 O9 C34 73.8(11) . . . . ?
C31 C36 C37 C38 179.9(10) . . . . ?
C32 C31 C36 C35 1.3(13) . . . . ?
C32 C31 C36 C37 -178.8(9) . . . . ?
C33 C34 C35 C36 -62.1(13) . . . . ?
C33 C34 O9 C32 37.9(11) . . . . ?
C34 C33 O8 C32 -3.9(11) . . . . ?
C34 C35 C36 C31 -10.5(14) . . . . ?
C34 C35 C36 C37 169.6(10) . . . . ?
C35 C34 O9 C32 -80.4(10) . . . . ?
C35 C36 C37 C38 -0.2(17) . . . . ?
C36 C31 C32 O8 83.7(10) . . . . ?
C36 C31 C32 O9 -34.3(13) . . . . ?
C36 C37 C38 C39 -179.8(10) . . . . ?
C37 C38 C39 C40 -177.8(10) . . . . ?
C38 C39 C40 C41 11.5(16) . . . . ?
C38 C39 C40 C45 -167.4(10) . . . . ?
C39 C40 C41 C42 -178.9(10) . . . . ?
C39 C40 C45 C44 177.5(10) . . . . ?
C40 C41 C42 C43 0.3(19) . . . . ?
C41 C40 C45 C44 -1.4(16) . . . . ?
C41 C42 C43 C44 1.0(19) . . . . ?
C42 C43 C44 C45 -2.4(19) . . . . ?
C43 C44 C45 C40 2.7(18) . . . . ?
C45 C40 C41 C42 0.0(17) . . . . ?
O7 C31 C32 O8 -98.2(12) . . . . ?
O7 C31 C32 O9 143.8(11) . . . . ?
O7 C31 C36 C35 -176.8(10) . . . . ?
O7 C31 C36 C37 3.1(16) . . . . ?
O8 C32 O9 C34 -43.0(11) . . . . ?
O8 C33 C34 C35 91.9(11) . . . . ?
O8 C33 C34 O9 -20.4(11) . . . . ?
O9 C32 O8 C33 30.1(12) . . . . ?
O9 C34 C35 C36 48.0(12) . . . . ?
C46 C47 O11 C48 -88.5(11) . . . . ?
C46 C47 O12 C49 70.4(11) . . . . ?
C46 C51 C52 C53 -177.7(10) . . . . ?
C47 C46 C51 C50 5.3(13) . . . . ?
C47 C46 C51 C52 -176.8(9) . . . . ?
C48 C49 C50 C51 -65.8(13) . . . . ?
C48 C49 O12 C47 42.2(10) . . . . ?
C49 C48 O11 C47 -1.7(11) . . . . ?
C49 C50 C51 C46 -11.1(13) . . . . ?
C49 C50 C51 C52 171.1(10) . . . . ?
C50 C49 O12 C47 -81.1(10) . . . . ?
C50 C51 C52 C53 0.0(17) . . . . ?
C51 C46 C47 O11 78.7(11) . . . . ?
C51 C46 C47 O12 -35.7(13) . . . . ?
C51 C52 C53 C54 -179.2(11) . . . . ?
C52 C53 C54 C55 -177.3(10) . . . . ?
C53 C54 C55 C56 11.1(17) . . . . ?
C53 C54 C55 C60 -170.0(11) . . . . ?
C54 C55 C56 C57 178.9(10) . . . . ?
C54 C55 C60 C59 -179.9(11) . . . . ?
C55 C56 C57 C58 -0.9(17) . . . . ?
C56 C55 C60 C59 -0.9(17) . . . . ?
C56 C57 C58 C59 2.8(18) . . . . ?
C57 C58 C59 C60 -3.6(17) . . . . ?
C58 C59 C60 C55 2.7(17) . . . . ?
C60 C55 C56 C57 -0.1(16) . . . . ?
O10 C46 C47 O11 -103.8(12) . . . . ?
O10 C46 C47 O12 141.9(10) . . . . ?
O10 C46 C51 C50 -172.0(11) . . . . ?
O10 C46 C51 C52 5.9(16) . . . . ?
O11 C47 O12 C49 -45.4(11) . . . . ?
O11 C48 C49 C50 95.2(11) . . . . ?
O11 C48 C49 O12 -25.7(11) . . . . ?
O12 C47 O11 C48 28.8(11) . . . . ?
O12 C49 C50 C51 49.9(12) . . . . ?

_olex2_date_sample_data_collection 2017-04-28
_olex2_date_sample_submission    2017-04-05
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id lmhTranscinnamaldehyde
_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 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.825
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.669(5)
2 0.331(5)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_jhc1702
_database_code_depnum_ccdc_archive 'CCDC 1837712'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 O3 S'
_chemical_formula_sum            'C11 H10 O3 S'
_chemical_formula_weight         222.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 O3 S'
_chemical_oxdiff_usercomment     'Liam lmh2-thiophene'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.32713(7)
_cell_length_b                   10.32552(10)
_cell_length_c                   15.23806(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     995.516(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6187
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.9670
_cell_measurement_theta_min      4.3050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.763
_exptl_absorpt_correction_T_max  0.716
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             464
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0968
0 -1 1 0.0968
1 -2 0 0.0947
-1 2 0 0.0947
-4 2 1 0.0650
2 1 5 0.0881
-3 0 -5 0.0929
1 -5 -3 0.1190
0 1 5 0.1166
1 5 5 0.1049
-4 -3 1 0.1047
-3 2 5 0.0881
3 -4 -4 0.0940

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.189
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0002 0.9995 -1.0006 -0.1537 0.0939 -0.0035
0.0002 -0.9995 1.0006 0.1537 -0.0939 0.0035
0.9996 -1.9992 0.0003 0.2346 -0.1007 -0.2884
-0.9996 1.9992 -0.0003 -0.2346 0.1007 0.2884
-3.9984 1.9986 1.0036 -0.4162 -0.2828 0.8915
2.0007 1.0014 4.9951 0.5009 0.5123 -0.0280
-3.0004 -0.0020 -4.9946 -0.6618 -0.5299 0.2633
0.9987 -4.9991 -2.9964 0.2155 -0.5289 -0.6177
0.0013 1.0009 4.9979 0.3265 0.2404 0.3363
1.0013 5.0001 4.9931 0.1189 0.8496 0.3667
-3.9987 -3.0000 1.0078 -0.0477 -0.8744 0.6259
-2.9977 1.9998 5.0012 -0.0088 -0.0492 0.9359
2.9979 -3.9990 -3.9998 0.2362 -0.1630 -0.9856

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8921
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.871
_diffrn_reflns_theta_max         66.871
_diffrn_reflns_theta_min         5.174
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00-150.00   90
  2  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00  60.00   90
  3  ω    -18.00  80.00   1.00    1.00    --   54.00 -37.00 120.00   98
  4  ω     23.00 111.00   1.00    1.00    --   54.00-125.00  30.00   88
  5  ω     33.00 123.00   1.00    1.00    --   54.00  57.00 -60.00   90
  6  ω     33.00 123.00   1.00    1.00    --   54.00  57.00  60.00   90
  7  ω    101.00 178.00   1.00    1.00    --  108.00  95.00  -3.00   77
  8  ω     40.00 130.00   1.00    1.00    --  108.00 -63.00-120.00   90
  9  ω     86.00 178.00   1.00    1.00    --  108.00  50.00  30.00   92
 10  ω     38.00 138.00   1.00    1.00    --  108.00 -77.00  30.00  100
 11  ω    100.00 178.00   1.00    1.00    --  108.00 111.00 -60.00   78
 12  ω     35.00 142.00   1.00    1.00    --  108.00 -25.00  30.00  107
 13  ω    -70.00  30.00   1.00    1.00    --    0.00 -77.00 -30.00  100
 14  ω     33.00 123.00   1.00    1.00    --   54.00  55.00 128.00   90
 15  ω    -15.00  75.00   1.00    1.00    --   54.00 -57.00  60.00   90
 16  ω     33.00 123.00   1.00    1.00    --   54.00  57.00-150.00   90
 17  ω     82.00 178.00   1.00    1.00    --  108.00  37.00  90.00   96
 18  ω     74.00 178.00   1.00    1.00    --  108.00  25.00 -60.00  104
 19  ω     36.00 178.00   1.00    1.00    --  108.00  12.00-150.00  142
 20  ω     78.00 178.00   1.00    1.00    --  108.00  77.00-150.00  100
 21  ω     36.00 116.00   1.00    1.00    --  108.00-111.00-120.00   80
 22  ω    -40.00  25.00   1.00    1.00    --    0.00  95.00  -3.00   65
 23  ω    -15.00  28.00   1.00    1.00    --   54.00 -57.00 -90.00   43
 24  ω     33.00 123.00   1.00    1.00    --   54.00  57.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0873594000
_diffrn_orient_matrix_UB_12      -0.0736489000
_diffrn_orient_matrix_UB_13      0.0800555000
_diffrn_orient_matrix_UB_21      0.1359965000
_diffrn_orient_matrix_UB_22      0.1183648000
_diffrn_orient_matrix_UB_23      0.0243513000
_diffrn_orient_matrix_UB_31      -0.1821533000
_diffrn_orient_matrix_UB_32      0.0531947000
_diffrn_orient_matrix_UB_33      0.0566916000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1766
_reflns_number_total             1777
_reflns_odcompleteness_completeness 99.91
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(5)
_refine_ls_extinction_coef       0.0021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.046
_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)+(0.0343P)²+0.2764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0563
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.4066(3) 0.20334(19) 0.29951(13) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.3174(3) 0.07275(19) 0.26992(12) 0.0190(4) Uani 1 1 d . . . . .
H2 H 0.4319 0.0110 0.2587 0.023 Uiso 1 1 calc R . . . .
C3 C -0.0103(3) 0.1323(2) 0.22351(12) 0.0209(4) Uani 1 1 d . . . . .
H3A H -0.1195 0.0792 0.1970 0.025 Uiso 1 1 calc R . . . .
H3B H -0.0381 0.2225 0.2100 0.025 Uiso 1 1 calc R . . . .
C4 C -0.0013(3) 0.11075(18) 0.32323(12) 0.0174(4) Uani 1 1 d . . . . .
H4 H -0.1319 0.0701 0.3441 0.021 Uiso 1 1 calc R . . . .
C5 C 0.0467(3) 0.23296(18) 0.37570(12) 0.0170(4) Uani 1 1 d . . . . .
H5A H -0.0533 0.3002 0.3598 0.020 Uiso 1 1 calc R . . . .
H5B H 0.0299 0.2150 0.4378 0.020 Uiso 1 1 calc R . . . .
C6 C 0.2694(3) 0.28050(18) 0.35859(12) 0.0156(4) Uani 1 1 d . . . . .
C7 C 0.3586(3) 0.38517(18) 0.39683(12) 0.0163(4) Uani 1 1 d . . . . .
H7 H 0.4975 0.4014 0.3802 0.020 Uiso 1 1 calc R . . . .
C8 C 0.2728(3) 0.47500(18) 0.45898(12) 0.0163(4) Uani 1 1 d . . . . .
C9 C 0.3828(3) 0.58216(17) 0.49023(13) 0.0195(4) Uani 1 1 d . . . . .
H9 H 0.5202 0.6026 0.4735 0.023 Uiso 1 1 calc R . . . .
C10 C 0.2633(4) 0.65658(18) 0.55005(14) 0.0235(5) Uani 1 1 d . . . . .
H10 H 0.3133 0.7318 0.5765 0.028 Uiso 1 1 calc R . . . .
C11 C 0.0671(3) 0.60706(19) 0.56513(13) 0.0219(4) Uani 1 1 d . . . . .
H11 H -0.0309 0.6439 0.6031 0.026 Uiso 1 1 calc R . . . .
O1 O 0.5783(2) 0.23845(14) 0.27304(10) 0.0252(3) Uani 1 1 d . . . . .
O2 O 0.1755(2) 0.02279(13) 0.33220(9) 0.0196(3) Uani 1 1 d . . . . .
O3 O 0.1971(2) 0.09412(14) 0.19255(9) 0.0215(3) Uani 1 1 d . . . . .
S1 S 0.02249(7) 0.46890(4) 0.50588(3) 0.01851(15) Uani 1 1 d . . . . .


_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 1.530(3) . ?
C1 C6 1.483(3) . ?
C1 O1 1.214(2) . ?
C2 H2 0.9800 . ?
C2 O2 1.405(2) . ?
C2 O3 1.421(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.537(3) . ?
C3 O3 1.449(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.524(2) . ?
C4 O2 1.447(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.515(3) . ?
C6 C7 1.351(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.433(3) . ?
C8 C9 1.391(3) . ?
C8 S1 1.7384(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.412(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.362(3) . ?
C11 H11 0.9300 . ?
C11 S1 1.712(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
C6 C1 C2 115.87(16) . . ?
O1 C1 C2 119.70(18) . . ?
O1 C1 C6 124.41(18) . . ?
C1 C2 H2 110.6 . . ?
O2 C2 C1 111.13(16) . . ?
O2 C2 H2 110.6 . . ?
O2 C2 O3 105.97(15) . . ?
O3 C2 C1 107.78(15) . . ?
O3 C2 H2 110.6 . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
O3 C3 H3A 110.9 . . ?
O3 C3 H3B 110.9 . . ?
O3 C3 C4 104.42(15) . . ?
C3 C4 H4 110.6 . . ?
C5 C4 C3 113.96(16) . . ?
C5 C4 H4 110.6 . . ?
O2 C4 C3 102.29(14) . . ?
O2 C4 H4 110.6 . . ?
O2 C4 C5 108.42(15) . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.31(16) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C1 C6 C5 118.36(16) . . ?
C7 C6 C1 116.54(17) . . ?
C7 C6 C5 125.00(17) . . ?
C6 C7 H7 114.9 . . ?
C6 C7 C8 130.14(18) . . ?
C8 C7 H7 114.9 . . ?
C7 C8 S1 126.41(15) . . ?
C9 C8 C7 123.46(18) . . ?
C9 C8 S1 110.13(14) . . ?
C8 C9 H9 123.7 . . ?
C8 C9 C10 112.67(18) . . ?
C10 C9 H9 123.7 . . ?
C9 C10 H10 123.4 . . ?
C11 C10 C9 113.14(18) . . ?
C11 C10 H10 123.4 . . ?
C10 C11 H11 124.0 . . ?
C10 C11 S1 111.98(16) . . ?
S1 C11 H11 124.0 . . ?
C2 O2 C4 101.52(14) . . ?
C2 O3 C3 104.91(14) . . ?
C11 S1 C8 92.08(10) . . ?

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
C1 C2 O2 C4 70.03(18) . . . . ?
C1 C2 O3 C3 -85.01(18) . . . . ?
C1 C6 C7 C8 -177.14(18) . . . . ?
C2 C1 C6 C5 -7.2(2) . . . . ?
C2 C1 C6 C7 169.39(17) . . . . ?
C3 C4 C5 C6 -67.2(2) . . . . ?
C3 C4 O2 C2 39.38(17) . . . . ?
C4 C3 O3 C2 -7.91(19) . . . . ?
C4 C5 C6 C1 -2.5(2) . . . . ?
C4 C5 C6 C7 -178.72(17) . . . . ?
C5 C4 O2 C2 -81.33(17) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C1 C2 O2 -27.5(2) . . . . ?
C6 C1 C2 O3 88.21(19) . . . . ?
C6 C7 C8 C9 -177.46(19) . . . . ?
C6 C7 C8 S1 2.3(3) . . . . ?
C7 C8 C9 C10 179.26(18) . . . . ?
C7 C8 S1 C11 -179.58(18) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C8 S1 C11 0.17(14) . . . . ?
C9 C10 C11 S1 -0.5(2) . . . . ?
C10 C11 S1 C8 0.20(16) . . . . ?
O1 C1 C2 O2 153.88(17) . . . . ?
O1 C1 C2 O3 -90.4(2) . . . . ?
O1 C1 C6 C5 171.37(18) . . . . ?
O1 C1 C6 C7 -12.1(3) . . . . ?
O2 C2 O3 C3 34.05(19) . . . . ?
O2 C4 C5 C6 46.0(2) . . . . ?
O3 C2 O2 C4 -46.79(17) . . . . ?
O3 C3 C4 C5 97.42(18) . . . . ?
O3 C3 C4 O2 -19.37(18) . . . . ?
S1 C8 C9 C10 -0.5(2) . . . . ?

_olex2_date_sample_data_collection 2017-04-05
_olex2_date_sample_submission    2017-04-05
_olex2_exptl_crystal_mounting_method 'oil on 100 micrometre micromount'
_olex2_submission_original_sample_id lmh2-thiophene
_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 1.260
_oxdiff_exptl_absorpt_empirical_full_min 0.871
####################################################################### 
# 
# 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_jhc1706
_database_code_depnum_ccdc_archive 'CCDC 1837713'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 O4'
_chemical_formula_sum            'C13 H12 O4'
_chemical_formula_weight         232.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 O4'
_chemical_oxdiff_usercomment     'Liam Hughes lmhsalicylaldehyde'
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.50457(13)
_cell_length_b                   9.59528(11)
_cell_length_c                   11.47760(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1046.75(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6165
_cell_measurement_temperature    110.10(14)
_cell_measurement_theta_max      70.9530
_cell_measurement_theta_min      4.6310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0702
1 0 -1 0.0318
3 -5 1 0.0399
0 5 4 0.0538
-3 5 -2 0.0899
-4 0 -6 0.0904
2 -6 2 0.0347

_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.102
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -0.0000 1.0000 -0.0491 0.1559 0.1325
1.0000 0.0000 -1.0000 0.0491 -0.1559 -0.1325
3.0000 -5.0000 1.0000 0.8871 0.1452 -0.3006
-0.0000 5.0000 4.0000 -0.8111 0.4427 -0.2793
-3.0000 5.0000 -2.0000 -0.8782 -0.2772 0.3234
-4.0000 0.0000 -6.0000 -0.1074 -0.6959 0.7580
2.0000 -6.0000 2.0000 0.9931 0.3182 -0.1305

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9461
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         6.011
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.10(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00  60.00   90
  2  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00 -90.00   90
  3  ω     23.00 111.00   1.00    1.00    --   54.00-125.00 -60.00   88
  4  ω    -16.00  84.00   1.00    1.00    --   54.00 -77.00  30.00  100
  5  ω     33.00 123.00   1.00    1.00    --   54.00  57.00-120.00   90
  6  ω     33.00 123.00   1.00    1.00    --   54.00  57.00-180.00   90
  7  ω     36.00 116.00   1.00    1.00    --  108.00-111.00 -60.00   80
  8  ω    100.00 178.00   1.00    1.00    --  108.00 111.00-150.00   78
  9  ω     36.00 134.00   1.00    1.00    --  108.00 -37.00-150.00   98
 10  ω     86.00 176.00   1.00    1.00    --  108.00  63.00 120.00   90
 11  ω     36.00 116.00   1.00    1.00    --  108.00-111.00-150.00   80
 12  ω    100.00 178.00   1.00    1.00    --  108.00 111.00  90.00   78
 13  ω    100.00 178.00   1.00    1.00    --  108.00 111.00 -90.00   78
 14  ω     38.00 130.00   1.00    1.00    --  108.00 -50.00 -30.00   92
 15  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00-180.00   90
 16  ω     24.00 124.00   1.00    1.00    --   54.00  77.00  90.00  100
 17  ω     24.00 124.00   1.00    1.00    --   54.00  77.00 -90.00  100
 18  ω     15.00 127.00   1.00    1.00    --   54.00  22.00  51.00  112
 19  ω     36.00 178.00   1.00    1.00    --  108.00  12.00 -90.00  142
 20  ω     86.00 178.00   1.00    1.00    --  108.00  50.00 -30.00   92
 21  ω     74.00 178.00   1.00    1.00    --  108.00  25.00  30.00  104
 22  ω     78.00 132.00   1.00    1.00    --  108.00  77.00   0.00   54
 23  ω     82.00 178.00   1.00    1.00    --  108.00  37.00  90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0402059000
_diffrn_orient_matrix_UB_12      -0.1550851000
_diffrn_orient_matrix_UB_13      -0.0089064000
_diffrn_orient_matrix_UB_21      -0.0239521000
_diffrn_orient_matrix_UB_22      -0.0170283000
_diffrn_orient_matrix_UB_23      0.1319503000
_diffrn_orient_matrix_UB_31      -0.1552799000
_diffrn_orient_matrix_UB_32      -0.0376072000
_diffrn_orient_matrix_UB_33      -0.0228144000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1817
_reflns_number_total             1872
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.46 (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         0.149
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1872
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.084
_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)+(0.0374P)²+0.1769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0615
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.30962(13) 1.00495(13) 0.67439(10) 0.0164(3) Uani 1 1 d . . . . .
O3 O 0.24221(13) 0.80476(13) 0.58813(10) 0.0144(3) Uani 1 1 d . . . . .
O1 O 0.47502(14) 0.82044(13) 0.43736(10) 0.0163(3) Uani 1 1 d . . . . .
O4 O 0.54133(13) 1.02445(12) 0.52903(10) 0.0139(3) Uani 1 1 d . . . . .
C7 C 0.66502(19) 0.83108(18) 0.67920(15) 0.0134(4) Uani 1 1 d . . . . .
C1 C 0.47364(18) 0.89201(17) 0.54358(14) 0.0116(3) Uani 1 1 d . . . . .
C11 C 0.8972(2) 1.16358(19) 0.52794(18) 0.0205(4) Uani 1 1 d . . . . .
C9 C 0.8905(2) 0.96563(19) 0.65618(17) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.68320(18) 1.03437(18) 0.55150(15) 0.0131(4) Uani 1 1 d . . . . .
C2 C 0.31895(18) 0.92834(18) 0.56925(15) 0.0125(4) Uani 1 1 d . . . . .
C6 C 0.53431(19) 0.80683(17) 0.64192(14) 0.0128(4) Uani 1 1 d . . . . .
C8 C 0.74874(19) 0.94263(18) 0.62879(14) 0.0135(4) Uani 1 1 d . . . . .
C4 C 0.2889(2) 0.76343(19) 0.70357(15) 0.0168(4) Uani 1 1 d . . . . .
C12 C 0.7557(2) 1.14400(18) 0.50062(16) 0.0174(4) Uani 1 1 d . . . . .
C5 C 0.4353(2) 0.6994(2) 0.69118(17) 0.0175(4) Uani 1 1 d . . . . .
C10 C 0.9640(2) 1.0752(2) 0.60596(18) 0.0208(4) Uani 1 1 d . . . . .
C3 C 0.2877(2) 0.9040(2) 0.76630(16) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.276(2) 0.981(2) 0.5045(16) 0.009(5) Uiso 1 1 d . . . . .
H5A H 0.428(2) 0.617(2) 0.638(2) 0.021(6) Uiso 1 1 d . . . . .
H12 H 0.706(2) 1.206(2) 0.4459(19) 0.023(5) Uiso 1 1 d . . . . .
H3A H 0.367(3) 0.913(2) 0.826(2) 0.024(6) Uiso 1 1 d . . . . .
H11 H 0.948(3) 1.238(3) 0.494(2) 0.027(6) Uiso 1 1 d . . . . .
H3B H 0.192(3) 0.921(3) 0.806(2) 0.031(6) Uiso 1 1 d . . . . .
H7 H 0.705(3) 0.774(2) 0.7403(19) 0.022(6) Uiso 1 1 d . . . . .
H5B H 0.470(3) 0.665(2) 0.768(2) 0.029(6) Uiso 1 1 d . . . . .
H9 H 0.935(2) 0.901(2) 0.709(2) 0.023(6) Uiso 1 1 d . . . . .
H4 H 0.219(2) 0.700(2) 0.7357(17) 0.018(5) Uiso 1 1 d . . . . .
H10 H 1.062(3) 1.089(3) 0.629(2) 0.031(7) Uiso 1 1 d . . . . .
H1 H 0.553(3) 0.772(3) 0.434(2) 0.046(8) Uiso 1 1 d . . . . .


_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 C2 1.416(2) . ?
O2 C3 1.447(2) . ?
O3 C2 1.409(2) . ?
O3 C4 1.453(2) . ?
O1 C1 1.399(2) . ?
O4 C1 1.434(2) . ?
O4 C13 1.376(2) . ?
C7 C6 1.334(3) . ?
C7 C8 1.454(2) . ?
C1 C2 1.539(2) . ?
C1 C6 1.508(2) . ?
C11 C12 1.394(3) . ?
C11 C10 1.387(3) . ?
C9 C8 1.401(3) . ?
C9 C10 1.388(3) . ?
C13 C8 1.396(2) . ?
C13 C12 1.387(2) . ?
C6 C5 1.506(2) . ?
C4 C5 1.528(3) . ?
C4 C3 1.529(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
C2 O2 C3 106.42(13) . . ?
C2 O3 C4 102.22(13) . . ?
C13 O4 C1 118.63(13) . . ?
C6 C7 C8 120.68(16) . . ?
O1 C1 O4 109.23(13) . . ?
O1 C1 C2 106.67(14) . . ?
O1 C1 C6 112.48(14) . . ?
O4 C1 C2 104.48(13) . . ?
O4 C1 C6 113.32(14) . . ?
C6 C1 C2 110.16(14) . . ?
C10 C11 C12 120.29(17) . . ?
C10 C9 C8 120.68(18) . . ?
O4 C13 C8 120.83(16) . . ?
O4 C13 C12 117.42(16) . . ?
C12 C13 C8 121.61(17) . . ?
O2 C2 C1 109.91(13) . . ?
O3 C2 O2 105.87(13) . . ?
O3 C2 C1 109.47(14) . . ?
C7 C6 C1 120.09(16) . . ?
C7 C6 C5 125.50(16) . . ?
C5 C6 C1 114.40(16) . . ?
C9 C8 C7 123.57(17) . . ?
C13 C8 C7 118.22(16) . . ?
C13 C8 C9 118.18(17) . . ?
O3 C4 C5 107.66(14) . . ?
O3 C4 C3 100.74(14) . . ?
C5 C4 C3 113.92(16) . . ?
C13 C12 C11 119.15(17) . . ?
C6 C5 C4 109.18(15) . . ?
C11 C10 C9 120.07(18) . . ?
O2 C3 C4 104.25(14) . . ?

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 O3 0.87(3) 1.96(3) 2.8245(18) 169(3) 3_566

_olex2_date_sample_data_collection 2017-04-24
_olex2_date_sample_submission    2017-04-05
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id lmhsalicylaldehyde
_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 1.115
_oxdiff_exptl_absorpt_empirical_full_min 0.874
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_jhc1708
_database_code_depnum_ccdc_archive 'CCDC 1837792'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 O3'
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 O3'
_chemical_oxdiff_usercomment     'Liam Hughes lmh4Methyl'
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.47958(16)
_cell_length_b                   7.89044(19)
_cell_length_c                   22.4589(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1148.25(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2604
_cell_measurement_temperature    109.9(2)
_cell_measurement_theta_max      70.8100
_cell_measurement_theta_min      7.0940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 -2 0.2184
0 5 -1 0.0729
0 -5 1 0.0626
4 1 3 0.2506
0 0 1 0.0469
0 0 -1 0.0386
0 1 -5 0.0611
0 -1 -5 0.0495
0 1 5 0.0645

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.524
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.086
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.0021 -1.0011 -1.9996 -0.0258 0.0457 0.9796
0.0015 5.0010 -0.9993 0.1976 -0.9490 -0.1362
-0.0015 -5.0010 0.9993 -0.1976 0.9490 0.1362
4.0023 1.0011 2.9991 -0.0414 -0.0532 -0.9906
0.0002 0.0000 0.9996 -0.0673 -0.0075 -0.0110
-0.0002 -0.0000 -0.9996 0.0673 0.0075 0.0110
-0.0007 1.0001 -4.9978 0.3623 -0.1540 0.0256
-0.0014 -1.0003 -4.9979 0.3102 0.2286 0.0845
0.0014 1.0003 4.9979 -0.3102 -0.2286 -0.0845

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5107
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.108
_diffrn_reflns_theta_min         3.937
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00-180.00   90
  2  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00  90.00   90
  3  ω    -16.00  84.00   1.00    1.00    --   54.00 -77.00 120.00  100
  4  ω    -19.00  98.00   1.00    1.00    --   54.00 -19.00  60.00  117
  5  ω     74.00 178.00   1.00    1.00    --  108.00  25.00  60.00  104
  6  ω    100.00 178.00   1.00    1.00    --  108.00 111.00 120.00   78
  7  ω    100.00 178.00   1.00    1.00    --  108.00 111.00  30.00   78
  8  ω     36.00 116.00   1.00    1.00    --  108.00-111.00-150.00   80
  9  ω    100.00 178.00   1.00    1.00    --  108.00 111.00 -90.00   78
 10  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00 -90.00   90
 11  ω     33.00 123.00   1.00    1.00    --   54.00  57.00  90.00   90
 12  ω     28.00 126.00   1.00    1.00    --   54.00  37.00-150.00   98
 13  ω     78.00 109.00   1.00    1.00    --  108.00  77.00-180.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0335500000
_diffrn_orient_matrix_UB_12      0.0260586000
_diffrn_orient_matrix_UB_13      -0.0672907000
_diffrn_orient_matrix_UB_21      0.0401513000
_diffrn_orient_matrix_UB_22      -0.1912578000
_diffrn_orient_matrix_UB_23      -0.0074657000
_diffrn_orient_matrix_UB_31      -0.2319613000
_diffrn_orient_matrix_UB_32      -0.0293545000
_diffrn_orient_matrix_UB_33      -0.0109620000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.575
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                1943
_reflns_number_total             2057
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.65
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 687 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.067
_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)+(0.0465P)²+0.1783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0864
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.8208(3) 0.6231(3) 0.21525(9) 0.0195(5) Uani 1 1 d . . . . .
H1A H 0.8853 0.6453 0.1771 0.023 Uiso 1 1 calc R . . . .
H1B H 0.8071 0.5016 0.2204 0.023 Uiso 1 1 calc R . . . .
C2 C 0.9467(3) 0.7011(3) 0.26605(9) 0.0173(4) Uani 1 1 d . . . . .
H2 H 1.0902 0.7191 0.2538 0.021 Uiso 1 1 calc R . . . .
C3 C 0.9373(3) 0.6043(3) 0.32440(9) 0.0170(4) Uani 1 1 d . . . . .
H3A H 1.0010 0.4940 0.3193 0.020 Uiso 1 1 calc R . . . .
H3B H 1.0141 0.6654 0.3546 0.020 Uiso 1 1 calc R . . . .
C4 C 0.7165(3) 0.5819(3) 0.34461(9) 0.0160(4) Uani 1 1 d . . . . .
C5 C 0.6434(3) 0.4498(3) 0.37597(9) 0.0184(4) Uani 1 1 d . . . . .
H5 H 0.5018 0.4477 0.3826 0.022 Uiso 1 1 calc R . . . .
C6 C 0.7631(3) 0.3083(3) 0.40087(9) 0.0182(4) Uani 1 1 d . . . . .
C7 C 0.9607(3) 0.3308(3) 0.42495(9) 0.0189(4) Uani 1 1 d . . . . .
H7 H 1.0199 0.4382 0.4249 0.023 Uiso 1 1 calc R . . . .
C8 C 1.0694(3) 0.1955(3) 0.44880(9) 0.0217(5) Uani 1 1 d . . . . .
H8 H 1.2001 0.2136 0.4646 0.026 Uiso 1 1 calc R . . . .
C9 C 0.9858(4) 0.0330(3) 0.44939(9) 0.0228(5) Uani 1 1 d . . . . .
C10 C 0.7881(4) 0.0114(3) 0.42665(10) 0.0239(5) Uani 1 1 d . . . . .
H10 H 0.7287 -0.0959 0.4272 0.029 Uiso 1 1 calc R . . . .
C11 C 0.6773(4) 0.1460(3) 0.40318(9) 0.0225(5) Uani 1 1 d . . . . .
H11 H 0.5444 0.1281 0.3888 0.027 Uiso 1 1 calc R . . . .
C12 C 0.6342(3) 0.8149(3) 0.26946(10) 0.0192(4) Uani 1 1 d . . . . .
H12 H 0.5464 0.9148 0.2640 0.023 Uiso 1 1 calc R . . . .
C13 C 0.5661(3) 0.7129(3) 0.32391(10) 0.0185(5) Uani 1 1 d . . . . .
C14 C 1.1072(4) -0.1155(3) 0.47323(11) 0.0315(6) Uani 1 1 d . . . . .
H14A H 1.1913 -0.1619 0.4421 0.047 Uiso 1 1 calc GR . . . .
H14B H 1.0137 -0.2008 0.4874 0.047 Uiso 1 1 calc GR . . . .
H14C H 1.1937 -0.0782 0.5054 0.047 Uiso 1 1 calc GR . . . .
O1 O 0.6221(2) 0.70574(19) 0.21924(7) 0.0221(4) Uani 1 1 d . . . . .
O2 O 0.8423(2) 0.86185(17) 0.27491(7) 0.0204(3) Uani 1 1 d . . . . .
O3 O 0.3971(2) 0.7356(2) 0.34599(8) 0.0266(4) Uani 1 1 d . . . . .


_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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.532(3) . ?
C1 O1 1.446(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.518(3) . ?
C2 O2 1.451(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.512(3) . ?
C4 C5 1.344(3) . ?
C4 C13 1.495(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.470(3) . ?
C6 C7 1.401(3) . ?
C6 C11 1.397(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.509(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9800 . ?
C12 C13 1.529(3) . ?
C12 O1 1.421(3) . ?
C12 O2 1.404(2) . ?
C13 O3 1.215(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
O1 C1 H1A 110.9 . . ?
O1 C1 H1B 110.9 . . ?
O1 C1 C2 104.29(16) . . ?
C1 C2 H2 110.7 . . ?
C3 C2 C1 114.79(17) . . ?
C3 C2 H2 110.7 . . ?
O2 C2 C1 101.83(16) . . ?
O2 C2 H2 110.7 . . ?
O2 C2 C3 107.61(16) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.86(16) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C5 C4 C3 125.55(19) . . ?
C5 C4 C13 118.02(19) . . ?
C13 C4 C3 116.29(17) . . ?
C4 C5 H5 116.5 . . ?
C4 C5 C6 127.0(2) . . ?
C6 C5 H5 116.5 . . ?
C7 C6 C5 122.2(2) . . ?
C11 C6 C5 120.01(19) . . ?
C11 C6 C7 117.8(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C14 121.0(2) . . ?
C10 C9 C8 117.9(2) . . ?
C10 C9 C14 121.1(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C6 C11 H11 119.7 . . ?
C10 C11 C6 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C13 C12 H12 110.9 . . ?
O1 C12 H12 110.9 . . ?
O1 C12 C13 107.45(16) . . ?
O2 C12 H12 110.9 . . ?
O2 C12 C13 110.27(18) . . ?
O2 C12 O1 106.38(16) . . ?
C4 C13 C12 115.14(17) . . ?
O3 C13 C4 124.2(2) . . ?
O3 C13 C12 120.58(19) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 O1 C1 105.87(15) . . ?
C12 O2 C2 101.84(15) . . ?

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
C1 C2 C3 C4 -55.8(2) . . . . ?
C1 C2 O2 C12 40.83(19) . . . . ?
C2 C1 O1 C12 -2.2(2) . . . . ?
C2 C3 C4 C5 148.7(2) . . . . ?
C2 C3 C4 C13 -26.8(2) . . . . ?
C3 C2 O2 C12 -80.23(19) . . . . ?
C3 C4 C5 C6 5.1(3) . . . . ?
C3 C4 C13 C12 20.0(3) . . . . ?
C3 C4 C13 O3 -163.04(19) . . . . ?
C4 C5 C6 C7 37.1(3) . . . . ?
C4 C5 C6 C11 -145.4(2) . . . . ?
C5 C4 C13 C12 -155.87(19) . . . . ?
C5 C4 C13 O3 21.1(3) . . . . ?
C5 C6 C7 C8 179.23(19) . . . . ?
C5 C6 C11 C10 -179.9(2) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C6 C11 C10 -2.3(3) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C7 C8 C9 C14 177.7(2) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C6 1.0(3) . . . . ?
C11 C6 C7 C8 1.7(3) . . . . ?
C13 C4 C5 C6 -179.50(19) . . . . ?
C13 C12 O1 C1 -89.20(18) . . . . ?
C13 C12 O2 C2 71.80(19) . . . . ?
C14 C9 C10 C11 -178.3(2) . . . . ?
O1 C1 C2 C3 92.23(19) . . . . ?
O1 C1 C2 O2 -23.7(2) . . . . ?
O1 C12 C13 C4 72.2(2) . . . . ?
O1 C12 C13 O3 -104.9(2) . . . . ?
O1 C12 O2 C2 -44.4(2) . . . . ?
O2 C2 C3 C4 56.8(2) . . . . ?
O2 C12 C13 C4 -43.3(2) . . . . ?
O2 C12 C13 O3 139.6(2) . . . . ?
O2 C12 O1 C1 28.9(2) . . . . ?

_olex2_date_sample_data_collection 2017-04-25
_olex2_date_sample_submission    2017-04-05
_olex2_exptl_crystal_mounting_method 'oil on micromount'
_olex2_submission_original_sample_id lmh4Methyl
_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 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.588
####################################################################### 
# 
# 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_jhc1705
_database_code_depnum_ccdc_archive 'CCDC 1837711'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 Cl O3'
_chemical_formula_sum            'C13 H11 Cl O3'
_chemical_formula_weight         250.67
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H11 Cl O3'
_chemical_oxdiff_usercomment     'Liam Hughs lmh4-Cl'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   5.94601(13)
_cell_length_b                   5.17983(13)
_cell_length_c                   18.2456(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.739(2)
_cell_angle_gamma                90
_cell_volume                     560.03(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1783
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.2360
_cell_measurement_theta_min      7.2810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.974
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0094
0 0 -1 0.0094
1 0 0 0.0346
-1 0 0 0.0346
0 -1 0 0.0760
0 1 0 0.0760
-1 1 0 0.0664
-1 -1 0 0.0686

_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.019
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0003 -0.0000 0.9989 -0.0017 0.0845 0.0055
-0.0003 0.0000 -0.9989 0.0017 -0.0845 -0.0055
1.0004 -0.0003 -0.0004 0.0182 0.0052 0.2593
-1.0004 0.0003 0.0004 -0.0182 -0.0052 -0.2593
-0.0009 -1.0005 -0.0006 -0.2967 -0.0070 0.0206
0.0009 1.0005 0.0006 0.2967 0.0070 -0.0206
-0.9996 1.0008 0.0011 0.2785 0.0018 -0.2800
-1.0013 -1.0002 -0.0002 -0.3149 -0.0122 -0.2387

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3274
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.864
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  71.00   1.00    4.00    --   54.00 -37.00  90.00   83
  2  ω     37.00 130.00   1.00    8.00    --  108.00 -37.00  30.00   93
  3  ω     89.00 115.00   1.00    8.00    --  108.00-111.00 -30.00   26
  4  ω     60.00  87.00   1.00    4.00    --   54.00-126.00-127.00   27
  5  ω     38.00  75.00   1.00    8.00    --  108.00-111.00 -30.00   37
  6  ω     56.00  84.00   1.00    8.00    --  108.00-111.00  30.00   28
  7  ω     39.00 114.00   1.00    8.00    --  108.00 -50.00 -60.00   75
  8  ω    110.00 178.00   1.00    8.00    --  108.00 -12.00-150.00   68
  9  ω    139.00 176.00   1.00    8.00    --  108.00 111.00  30.00   37
 10  ω    134.00 173.00   1.00    8.00    --  108.00 111.00  90.00   39
 11  ω    111.00 138.00   1.00    8.00    --  108.00 178.00 150.00   27
 12  ω     58.00 103.00   1.00    8.00    --  108.00 178.00 150.00   45
 13  ω     56.00  90.00   1.00    4.00    --   54.00  57.00 -30.00   34
 14  ω     71.00 124.00   1.00    4.00    --   54.00  77.00-120.00   53
 15  ω     75.00 123.00   1.00    4.00    --   54.00  57.00-150.00   48
 16  ω     33.00  86.00   1.00    4.00    --   54.00  77.00-180.00   53
 17  ω     35.00 102.00   1.00    8.00    --  108.00 -12.00-150.00   67
 18  ω     47.00 113.00   1.00    8.00    --  108.00-111.00-180.00   66
 19  ω     -1.00  27.00   1.00    1.00    --    0.00 -77.00-150.00   28
 20  ω      1.00  94.00   1.00    4.00    --   54.00 -99.00 -60.00   93
 21  ω     23.00  72.00   1.00    4.00    --   54.00-125.00 120.00   49
 22  ω     48.00 113.00   1.00    8.00    --  108.00 -63.00 150.00   65
 23  ω     47.00  88.00   1.00    8.00    --  108.00-111.00 120.00   41
 24  ω     37.00 139.00   1.00    8.00    --  108.00 -25.00 120.00  102
 25  ω     -2.00  41.00   1.00    1.00    --    0.00  57.00-150.00   43
 26  ω    -55.00 -28.00   1.00    1.00    --    0.00 -77.00-150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0182580000
_diffrn_orient_matrix_UB_12      0.2965307000
_diffrn_orient_matrix_UB_13      -0.0016487000
_diffrn_orient_matrix_UB_21      0.0052162000
_diffrn_orient_matrix_UB_22      0.0069527000
_diffrn_orient_matrix_UB_23      0.0845747000
_diffrn_orient_matrix_UB_31      0.2592185000
_diffrn_orient_matrix_UB_32      -0.0208637000
_diffrn_orient_matrix_UB_33      0.0054419000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                1929
_reflns_number_total             1995
_reflns_odcompleteness_completeness 99.91
_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 1.171.38.46 (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         0.248
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1995
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.038
_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)+(0.0569P)²+0.1061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0934
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
;
_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
C1 C -0.4939(5) -1.3801(7) -0.18041(19) 0.0174(7) Uani 1 1 d . . . . .
C2 C -0.4077(6) -1.4991(7) -0.10686(19) 0.0204(7) Uani 1 1 d . . . . .
H2 H -0.4879 -1.6602 -0.0982 0.025 Uiso 1 1 calc R . . . .
C3 C -0.2300(5) -1.1834(8) -0.03602(17) 0.0204(6) Uani 1 1 d . . . . .
H3A H -0.1624 -1.2265 0.0126 0.024 Uiso 1 1 calc R . . . .
H3B H -0.2495 -0.9978 -0.0395 0.024 Uiso 1 1 calc R . . . .
C4 C -0.0864(5) -1.2821(7) -0.0952(2) 0.0188(7) Uani 1 1 d . . . . .
H4 H 0.0733 -1.2851 -0.0770 0.023 Uiso 1 1 calc R . . . .
C5 C -0.1179(5) -1.1364(6) -0.16801(18) 0.0182(7) Uani 1 1 d . . . . .
H5A H -0.0931 -0.9539 -0.1586 0.022 Uiso 1 1 calc R . . . .
H5B H -0.0046 -1.1945 -0.1996 0.022 Uiso 1 1 calc R . . . .
C6 C -0.3496(5) -1.1721(7) -0.20824(17) 0.0166(6) Uani 1 1 d . . . . .
C7 C -0.4353(5) -1.0437(7) -0.26792(19) 0.0194(7) Uani 1 1 d . . . . .
H7 H -0.5797 -1.0957 -0.2852 0.023 Uiso 1 1 calc R . . . .
C8 C -0.3423(5) -0.8365(7) -0.31068(19) 0.0183(7) Uani 1 1 d . . . . .
C9 C -0.1250(5) -0.7286(7) -0.29749(18) 0.0203(7) Uani 1 1 d . . . . .
H9 H -0.0291 -0.7904 -0.2586 0.024 Uiso 1 1 calc R . . . .
C10 C -0.0520(6) -0.5339(7) -0.3410(2) 0.0208(7) Uani 1 1 d . . . . .
H10 H 0.0919 -0.4651 -0.3314 0.025 Uiso 1 1 calc R . . . .
C11 C -0.1935(6) -0.4408(7) -0.39903(19) 0.0198(7) Uani 1 1 d . . . . .
C12 C -0.4079(6) -0.5417(8) -0.41462(19) 0.0223(7) Uani 1 1 d . . . . .
H12 H -0.5019 -0.4786 -0.4538 0.027 Uiso 1 1 calc R . . . .
C13 C -0.4798(6) -0.7384(7) -0.37074(19) 0.0214(8) Uani 1 1 d . . . . .
H13 H -0.6231 -0.8076 -0.3813 0.026 Uiso 1 1 calc R . . . .
Cl1 Cl -0.09781(13) -0.19285(16) -0.45294(4) 0.0233(2) Uani 1 1 d . . . . .
O1 O -0.6729(4) -1.4542(5) -0.21043(14) 0.0236(6) Uani 1 1 d . . . . .
O2 O -0.4428(4) -1.3155(5) -0.05136(14) 0.0229(6) Uani 1 1 d . . . . .
O3 O -0.1728(4) -1.5425(4) -0.10474(14) 0.0203(5) Uani 1 1 d . . . . .


_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 1.527(5) . ?
C1 C6 1.492(5) . ?
C1 O1 1.218(4) . ?
C2 H2 0.9800 . ?
C2 O2 1.417(4) . ?
C2 O3 1.412(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.519(5) . ?
C3 O2 1.445(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.526(5) . ?
C4 O3 1.449(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.518(4) . ?
C6 C7 1.340(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.462(5) . ?
C8 C9 1.410(5) . ?
C8 C13 1.407(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(5) . ?
C11 C12 1.386(5) . ?
C11 Cl1 1.741(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9300 . ?

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
C6 C1 C2 115.5(3) . . ?
O1 C1 C2 119.1(3) . . ?
O1 C1 C6 125.5(3) . . ?
C1 C2 H2 110.7 . . ?
O2 C2 C1 107.4(3) . . ?
O2 C2 H2 110.7 . . ?
O3 C2 C1 110.4(3) . . ?
O3 C2 H2 110.7 . . ?
O3 C2 O2 106.9(3) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
O2 C3 H3A 111.0 . . ?
O2 C3 H3B 111.0 . . ?
O2 C3 C4 103.7(3) . . ?
C3 C4 H4 110.5 . . ?
C3 C4 C5 114.6(3) . . ?
C5 C4 H4 110.5 . . ?
O3 C4 C3 100.6(3) . . ?
O3 C4 H4 110.5 . . ?
O3 C4 C5 109.8(3) . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.7(3) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C1 C6 C5 116.6(3) . . ?
C7 C6 C1 116.4(3) . . ?
C7 C6 C5 127.0(3) . . ?
C6 C7 H7 114.3 . . ?
C6 C7 C8 131.5(3) . . ?
C8 C7 H7 114.3 . . ?
C9 C8 C7 125.6(3) . . ?
C13 C8 C7 117.4(3) . . ?
C13 C8 C9 117.1(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 Cl1 118.9(3) . . ?
C12 C11 Cl1 120.0(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C2 O2 C3 106.1(3) . . ?
C2 O3 C4 101.2(2) . . ?

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
C1 C2 O2 C3 -97.6(3) . . . . ?
C1 C2 O3 C4 74.3(3) . . . . ?
C1 C6 C7 C8 -178.4(3) . . . . ?
C2 C1 C6 C5 10.4(4) . . . . ?
C2 C1 C6 C7 -172.2(3) . . . . ?
C3 C4 C5 C6 -67.1(4) . . . . ?
C3 C4 O3 C2 44.9(3) . . . . ?
C4 C3 O2 C2 8.0(3) . . . . ?
C4 C5 C6 C1 -12.1(4) . . . . ?
C4 C5 C6 C7 170.8(3) . . . . ?
C5 C4 O3 C2 -76.3(3) . . . . ?
C5 C6 C7 C8 -1.3(6) . . . . ?
C6 C1 C2 O2 73.3(3) . . . . ?
C6 C1 C2 O3 -42.8(4) . . . . ?
C6 C7 C8 C9 2.1(6) . . . . ?
C6 C7 C8 C13 -178.8(4) . . . . ?
C7 C8 C9 C10 179.8(3) . . . . ?
C7 C8 C13 C12 179.8(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C8 C13 C12 -1.0(5) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C9 C10 C11 Cl1 179.6(3) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C12 C13 C8 0.5(5) . . . . ?
C13 C8 C9 C10 0.7(5) . . . . ?
Cl1 C11 C12 C13 -179.9(3) . . . . ?
O1 C1 C2 O2 -104.8(4) . . . . ?
O1 C1 C2 O3 139.0(3) . . . . ?
O1 C1 C6 C5 -171.6(3) . . . . ?
O1 C1 C6 C7 5.8(5) . . . . ?
O2 C2 O3 C4 -42.1(3) . . . . ?
O2 C3 C4 C5 85.1(3) . . . . ?
O2 C3 C4 O3 -32.7(3) . . . . ?
O3 C2 O2 C3 20.8(4) . . . . ?
O3 C4 C5 C6 45.3(4) . . . . ?

_olex2_date_sample_data_collection 2017-04-21
_olex2_date_sample_submission    2017-04-05
_olex2_exptl_crystal_mounting_method 'oil on 75 micrometre micromount'
_olex2_submission_original_sample_id lmh4-Cl
_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 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.840
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_jhc1701
_database_code_depnum_ccdc_archive 'CCDC 1837709'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 O3'
_chemical_formula_sum            'C13 H12 O3'
_chemical_formula_weight         216.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 O3'
_chemical_oxdiff_usercomment     'Rob & Liam lnh51b'
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'
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           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                   11.11016(10)
_cell_length_b                   9.04172(9)
_cell_length_c                   15.58673(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.3028(8)
_cell_angle_gamma                90
_cell_volume                     1559.06(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    14995
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.9720
_cell_measurement_theta_min      3.9860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             684
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0190
-1 0 0 0.0190
0 0 -1 0.0896
0 -1 0 0.1131
0 -1 -1 0.1144
0 5 2 0.0819
0 1 -5 0.0782
0 -1 5 0.0935
-1 3 5 0.1031

_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.038
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 0.0000 0.0000 -0.0706 0.1198 0.0049
-1.0000 -0.0000 -0.0000 0.0706 -0.1198 -0.0049
0.0000 -0.0000 -1.0000 0.0751 0.0359 -0.0541
0.0000 -1.0000 -0.0000 0.0823 0.0428 0.1430
0.0000 -1.0000 -1.0000 0.1575 0.0786 0.0889
-0.0000 5.0000 2.0000 -0.5619 -0.2856 -0.6068
0.0000 1.0000 -5.0000 0.2933 0.1367 -0.4134
-0.0000 -1.0000 5.0000 -0.2933 -0.1367 0.4134
-1.0000 3.0000 5.0000 -0.5520 -0.4275 -0.1634

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28119
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.149
_diffrn_reflns_theta_min         3.996
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00  60.00   90
  2  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00 -90.00   90
  3  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00  60.00   90
  4  ω    -15.00  75.00   1.00    1.00    --   54.00 -57.00  60.00   90
  5  ω     33.00 123.00   1.00    1.00    --   54.00  57.00  90.00   90
  6  ω     33.00 123.00   1.00    1.00    --   54.00  57.00 -30.00   90
  7  ω     24.00 124.00   1.00    1.00    --   54.00  77.00  60.00  100
  8  ω     24.00 124.00   1.00    1.00    --   54.00  77.00  30.00  100
  9  ω    -15.00  75.00   1.00    1.00    --   54.00 -57.00  90.00   90
 10  ω    -15.00  75.00   1.00    1.00    --   54.00 -57.00-180.00   90
 11  ω     24.00 124.00   1.00    1.00    --   54.00  77.00 120.00  100
 12  ω     23.00 111.00   1.00    1.00    --   54.00-125.00  90.00   88
 13  ω     78.00 178.00   1.00    1.00    --  108.00  77.00  30.00  100
 14  ω     82.00 178.00   1.00    1.00    --  108.00  37.00-180.00   96
 15  ω     78.00 178.00   1.00    1.00    --  108.00  77.00 -30.00  100
 16  ω     78.00 178.00   1.00    1.00    --  108.00  77.00   0.00  100
 17  ω     86.00 176.00   1.00    1.00    --  108.00  63.00  30.00   90
 18  ω     38.00 130.00   1.00    1.00    --  108.00 -50.00 -90.00   92
 19  ω     86.00 178.00   1.00    1.00    --  108.00  50.00-150.00   92
 20  ω     82.00 178.00   1.00    1.00    --  108.00  37.00  90.00   96
 21  ω     82.00 178.00   1.00    1.00    --  108.00  37.00  30.00   96
 22  ω    100.00 178.00   1.00    1.00    --  108.00 111.00 120.00   78
 23  ω     74.00 178.00   1.00    1.00    --  108.00  25.00 120.00  104
 24  ω     78.00 178.00   1.00    1.00    --  108.00  77.00  60.00  100
 25  ω     82.00 178.00   1.00    1.00    --  108.00  37.00   0.00   96
 26  ω     82.00 178.00   1.00    1.00    --  108.00  37.00  60.00   96
 27  ω     36.00 116.00   1.00    1.00    --  108.00-111.00  90.00   80
 28  ω     86.00 176.00   1.00    1.00    --  108.00  63.00  60.00   90
 29  ω     86.00 176.00   1.00    1.00    --  108.00  63.00   0.00   90
 30  ω     78.00 178.00   1.00    1.00    --  108.00  77.00 -60.00  100
 31  ω     86.00 178.00   1.00    1.00    --  108.00  50.00  30.00   92
 32  ω     86.00 178.00   1.00    1.00    --  108.00  50.00  60.00   92
 33  ω    -73.00  44.00   1.00    1.00    --    0.00 -19.00  60.00  117
 34  ω    -72.00  26.00   1.00    1.00    --    0.00 -37.00 150.00   98
 35  ω    -72.00  26.00   1.00    1.00    --    0.00 -37.00   0.00   98
 36  ω    -15.00  75.00   1.00    1.00    --   54.00 -57.00 -60.00   90
 37  ω     24.00 124.00   1.00    1.00    --   54.00  77.00  88.00  100
 38  ω     24.00 124.00   1.00    1.00    --   54.00  77.00 150.00  100
 39  ω     24.00 124.00   1.00    1.00    --   54.00  77.00 -90.00  100
 40  ω     24.00 124.00   1.00    1.00    --   54.00  77.00-120.00  100
 41  ω     24.00 124.00   1.00    1.00    --   54.00  77.00-180.00  100
 42  ω     24.00 124.00   1.00    1.00    --   54.00  77.00   0.00  100
 43  ω     24.00 124.00   1.00    1.00    --   54.00  77.00 -30.00  100
 44  ω     24.00 124.00   1.00    1.00    --   54.00  77.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0706225000
_diffrn_orient_matrix_UB_12      -0.0823272000
_diffrn_orient_matrix_UB_13      -0.0751280000
_diffrn_orient_matrix_UB_21      0.1198175000
_diffrn_orient_matrix_UB_22      -0.0427649000
_diffrn_orient_matrix_UB_23      -0.0358839000
_diffrn_orient_matrix_UB_31      0.0048557000
_diffrn_orient_matrix_UB_32      -0.1429949000
_diffrn_orient_matrix_UB_33      0.0540850000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                5564
_reflns_number_total             5845
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 2415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_coef       0.00114(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         5845
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.2583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0692
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C15(H15), C17(H17), C28(H28), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C16(H16A,H16B), C18(H18A,H18B), C29(H29A,H29B),
 C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C20(H20), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C33(H33), C35(H35), C36(H36), C37(H37),
  C38(H38), C39(H39)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 1.09979(17) 0.5712(2) 0.87516(12) 0.0172(4) Uani 1 1 d . . . . .
C2 C 1.22891(17) 0.5352(2) 0.90876(13) 0.0191(4) Uani 1 1 d . . . . .
H2 H 1.2846 0.6096 0.8895 0.023 Uiso 1 1 calc R . . . .
C3 C 1.22465(19) 0.2897(2) 0.94279(14) 0.0227(4) Uani 1 1 d . . . . .
H3A H 1.2940 0.2320 0.9656 0.027 Uiso 1 1 calc R . . . .
H3B H 1.1618 0.2230 0.9190 0.027 Uiso 1 1 calc R . . . .
C4 C 1.17866(18) 0.3879(2) 1.01274(13) 0.0209(4) Uani 1 1 d . . . . .
H4 H 1.2038 0.3485 1.0702 0.025 Uiso 1 1 calc R . . . .
C5 C 1.04267(17) 0.4131(2) 1.00183(13) 0.0204(4) Uani 1 1 d . . . . .
H5A H 1.0020 0.3181 0.9980 0.024 Uiso 1 1 calc R . . . .
H5B H 1.0184 0.4638 1.0523 0.024 Uiso 1 1 calc R . . . .
C6 C 1.00300(17) 0.5033(2) 0.92228(12) 0.0164(4) Uani 1 1 d . . . . .
C7 C 0.88900(17) 0.5312(2) 0.88984(12) 0.0179(4) Uani 1 1 d . . . . .
H7 H 0.8831 0.5851 0.8388 0.022 Uiso 1 1 calc R . . . .
C8 C 0.77202(17) 0.4921(2) 0.92038(12) 0.0176(4) Uani 1 1 d . . . . .
C9 C 0.75606(18) 0.4227(2) 0.99884(13) 0.0199(4) Uani 1 1 d . . . . .
H9 H 0.8230 0.3907 1.0342 0.024 Uiso 1 1 calc R . . . .
C10 C 0.64078(18) 0.4016(2) 1.02416(13) 0.0206(4) Uani 1 1 d . . . . .
H10 H 0.6311 0.3562 1.0766 0.025 Uiso 1 1 calc R . . . .
C11 C 0.53998(18) 0.4474(2) 0.97199(14) 0.0236(5) Uani 1 1 d . . . . .
H11 H 0.4631 0.4338 0.9897 0.028 Uiso 1 1 calc R . . . .
C12 C 0.55412(18) 0.5134(3) 0.89327(13) 0.0266(5) Uani 1 1 d . . . . .
H12 H 0.4866 0.5422 0.8574 0.032 Uiso 1 1 calc R . . . .
C13 C 0.66905(18) 0.5366(3) 0.86810(13) 0.0224(4) Uani 1 1 d . . . . .
H13 H 0.6780 0.5825 0.8157 0.027 Uiso 1 1 calc R . . . .
O1 O 1.08080(13) 0.65159(17) 0.81241(9) 0.0240(3) Uani 1 1 d . . . . .
O2 O 1.25791(13) 0.39312(16) 0.87831(9) 0.0221(3) Uani 1 1 d . . . . .
O3 O 1.23877(12) 0.52682(17) 0.99914(9) 0.0220(3) Uani 1 1 d . . . . .
C14 C 0.76062(18) 0.6395(2) 0.62303(13) 0.0198(4) Uani 1 1 d . . . . .
C15 C 0.63193(19) 0.5878(3) 0.59621(14) 0.0243(5) Uani 1 1 d . . . . .
H15 H 0.5731 0.6551 0.6185 0.029 Uiso 1 1 calc R . . . .
C16 C 0.6559(2) 0.3434(3) 0.56494(14) 0.0272(5) Uani 1 1 d . . . . .
H16A H 0.5911 0.2749 0.5473 0.033 Uiso 1 1 calc R . . . .
H16B H 0.7273 0.2876 0.5857 0.033 Uiso 1 1 calc R . . . .
C17 C 0.6822(2) 0.4449(3) 0.49068(14) 0.0272(5) Uani 1 1 d . . . . .
H17 H 0.6539 0.3999 0.4353 0.033 Uiso 1 1 calc R . . . .
C18 C 0.81398(19) 0.4926(3) 0.49109(13) 0.0260(5) Uani 1 1 d . . . . .
H18A H 0.8646 0.4054 0.4899 0.031 Uiso 1 1 calc R . . . .
H18B H 0.8238 0.5497 0.4395 0.031 Uiso 1 1 calc R . . . .
C19 C 0.85533(18) 0.5847(2) 0.56958(12) 0.0184(4) Uani 1 1 d . . . . .
C20 C 0.97058(18) 0.6179(2) 0.59764(12) 0.0190(4) Uani 1 1 d . . . . .
H20 H 0.9797 0.6778 0.6463 0.023 Uiso 1 1 calc R . . . .
C21 C 1.08377(18) 0.5742(2) 0.56317(12) 0.0185(4) Uani 1 1 d . . . . .
C22 C 1.09443(18) 0.5346(2) 0.47734(13) 0.0211(4) Uani 1 1 d . . . . .
H22 H 1.0268 0.5373 0.4375 0.025 Uiso 1 1 calc R . . . .
C23 C 1.20497(19) 0.4913(2) 0.45141(13) 0.0245(5) Uani 1 1 d . . . . .
H23 H 1.2111 0.4664 0.3941 0.029 Uiso 1 1 calc R . . . .
C24 C 1.30678(19) 0.4848(3) 0.50995(14) 0.0253(5) Uani 1 1 d . . . . .
H24 H 1.3803 0.4530 0.4925 0.030 Uiso 1 1 calc R . . . .
C25 C 1.29784(18) 0.5261(3) 0.59469(14) 0.0252(5) Uani 1 1 d . . . . .
H25 H 1.3659 0.5229 0.6341 0.030 Uiso 1 1 calc R . . . .
C26 C 1.18834(18) 0.5721(2) 0.62112(13) 0.0214(4) Uani 1 1 d . . . . .
H26 H 1.1840 0.6019 0.6778 0.026 Uiso 1 1 calc R . . . .
O4 O 0.77986(13) 0.71461(17) 0.68791(9) 0.0244(3) Uani 1 1 d . . . . .
O5 O 0.62057(14) 0.44377(17) 0.63042(9) 0.0276(4) Uani 1 1 d . . . . .
O6 O 0.61079(13) 0.57438(19) 0.50645(10) 0.0292(4) Uani 1 1 d . . . . .
C27 C 0.57295(18) 0.3891(2) 0.25473(12) 0.0208(4) Uani 1 1 d . . . . .
C28 C 0.44016(18) 0.4327(2) 0.24824(13) 0.0225(5) Uani 1 1 d . . . . .
H28 H 0.3903 0.3501 0.2652 0.027 Uiso 1 1 calc R . . . .
C29 C 0.43141(19) 0.6303(2) 0.15679(13) 0.0217(4) Uani 1 1 d . . . . .
H29A H 0.3587 0.6845 0.1370 0.026 Uiso 1 1 calc R . . . .
H29B H 0.4930 0.6500 0.1180 0.026 Uiso 1 1 calc R . . . .
C30 C 0.47572(18) 0.6733(3) 0.24940(13) 0.0220(4) Uani 1 1 d . . . . .
H30 H 0.4447 0.7708 0.2638 0.026 Uiso 1 1 calc R . . . .
C31 C 0.61249(18) 0.6670(2) 0.26872(13) 0.0199(4) Uani 1 1 d . . . . .
H31A H 0.6496 0.7332 0.2298 0.024 Uiso 1 1 calc R . . . .
H31B H 0.6339 0.7015 0.3271 0.024 Uiso 1 1 calc R . . . .
C32 C 0.66240(17) 0.5128(2) 0.25928(12) 0.0176(4) Uani 1 1 d . . . . .
C33 C 0.77856(18) 0.4747(2) 0.25427(12) 0.0193(4) Uani 1 1 d . . . . .
H33 H 0.7913 0.3736 0.2489 0.023 Uiso 1 1 calc R . . . .
C34 C 0.88882(17) 0.5645(2) 0.25584(11) 0.0177(4) Uani 1 1 d . . . . .
C35 C 0.89779(18) 0.7145(2) 0.27878(13) 0.0207(4) Uani 1 1 d . . . . .
H35 H 0.8307 0.7635 0.2964 0.025 Uiso 1 1 calc R . . . .
C36 C 1.00568(19) 0.7899(2) 0.27540(13) 0.0237(5) Uani 1 1 d . . . . .
H36 H 1.0100 0.8896 0.2899 0.028 Uiso 1 1 calc R . . . .
C37 C 1.10754(19) 0.7184(3) 0.25058(13) 0.0245(5) Uani 1 1 d . . . . .
H37 H 1.1793 0.7704 0.2477 0.029 Uiso 1 1 calc R . . . .
C38 C 1.10157(19) 0.5696(3) 0.23020(13) 0.0244(5) Uani 1 1 d . . . . .
H38 H 1.1699 0.5206 0.2146 0.029 Uiso 1 1 calc R . . . .
C39 C 0.99376(18) 0.4934(2) 0.23304(12) 0.0214(4) Uani 1 1 d . . . . .
H39 H 0.9908 0.3932 0.2196 0.026 Uiso 1 1 calc R . . . .
O7 O 0.59994(14) 0.25794(18) 0.25280(11) 0.0321(4) Uani 1 1 d . . . . .
O8 O 0.40709(13) 0.47378(17) 0.16137(9) 0.0225(3) Uani 1 1 d . . . . .
O9 O 0.42249(13) 0.55824(19) 0.29863(9) 0.0265(3) Uani 1 1 d . . . . .


_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 1.516(3) . ?
C1 C6 1.490(3) . ?
C1 O1 1.221(2) . ?
C2 H2 0.9800 . ?
C2 O2 1.417(3) . ?
C2 O3 1.405(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.530(3) . ?
C3 O2 1.446(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.522(3) . ?
C4 O3 1.447(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.515(3) . ?
C6 C7 1.344(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.468(3) . ?
C8 C9 1.400(3) . ?
C8 C13 1.401(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.525(3) . ?
C14 C19 1.486(3) . ?
C14 O4 1.220(3) . ?
C15 H15 0.9800 . ?
C15 O5 1.417(3) . ?
C15 O6 1.402(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.527(3) . ?
C16 O5 1.447(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.526(3) . ?
C17 O6 1.448(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.516(3) . ?
C19 C20 1.348(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.467(3) . ?
C21 C22 1.401(3) . ?
C21 C26 1.404(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.384(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.521(3) . ?
C27 C32 1.493(3) . ?
C27 O7 1.224(3) . ?
C28 H28 0.9800 . ?
C28 O8 1.419(2) . ?
C28 O9 1.405(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.532(3) . ?
C29 O8 1.444(3) . ?
C30 H30 0.9800 . ?
C30 C31 1.523(3) . ?
C30 O9 1.451(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.513(3) . ?
C32 C33 1.345(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.468(3) . ?
C34 C35 1.403(3) . ?
C34 C39 1.406(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.384(3) . ?
C36 H36 0.9300 . ?
C36 C37 1.389(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.383(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.386(3) . ?
C39 H39 0.9300 . ?

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
C6 C1 C2 116.37(17) . . ?
O1 C1 C2 119.50(17) . . ?
O1 C1 C6 124.13(18) . . ?
C1 C2 H2 110.5 . . ?
O2 C2 C1 108.44(16) . . ?
O2 C2 H2 110.5 . . ?
O3 C2 C1 109.96(15) . . ?
O3 C2 H2 110.5 . . ?
O3 C2 O2 106.75(16) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
O2 C3 H3A 110.9 . . ?
O2 C3 H3B 110.9 . . ?
O2 C3 C4 104.08(16) . . ?
C3 C4 H4 110.7 . . ?
C5 C4 C3 113.61(17) . . ?
C5 C4 H4 110.7 . . ?
O3 C4 C3 102.15(15) . . ?
O3 C4 H4 110.7 . . ?
O3 C4 C5 108.72(17) . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.50(16) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C1 C6 C5 117.17(16) . . ?
C7 C6 C1 115.81(17) . . ?
C7 C6 C5 127.01(17) . . ?
C6 C7 H7 114.2 . . ?
C6 C7 C8 131.66(19) . . ?
C8 C7 H7 114.2 . . ?
C9 C8 C7 125.34(18) . . ?
C9 C8 C13 118.31(17) . . ?
C13 C8 C7 116.24(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.32(19) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.61(19) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.78(18) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.08(19) . . ?
C12 C13 H13 119.5 . . ?
C2 O2 C3 105.84(15) . . ?
C2 O3 C4 101.49(15) . . ?
C19 C14 C15 116.00(18) . . ?
O4 C14 C15 119.05(18) . . ?
O4 C14 C19 124.83(19) . . ?
C14 C15 H15 110.6 . . ?
O5 C15 C14 107.00(17) . . ?
O5 C15 H15 110.6 . . ?
O6 C15 C14 111.48(16) . . ?
O6 C15 H15 110.6 . . ?
O6 C15 O5 106.45(17) . . ?
H16A C16 H16B 109.0 . . ?
C17 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
O5 C16 H16A 111.0 . . ?
O5 C16 H16B 111.0 . . ?
O5 C16 C17 103.93(18) . . ?
C16 C17 H17 110.5 . . ?
C18 C17 C16 114.68(19) . . ?
C18 C17 H17 110.5 . . ?
O6 C17 C16 102.21(16) . . ?
O6 C17 H17 110.5 . . ?
O6 C17 C18 108.15(19) . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 C17 112.19(17) . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C14 C19 C18 117.27(17) . . ?
C20 C19 C14 116.37(18) . . ?
C20 C19 C18 126.31(18) . . ?
C19 C20 H20 115.0 . . ?
C19 C20 C21 129.93(19) . . ?
C21 C20 H20 115.0 . . ?
C22 C21 C20 124.75(18) . . ?
C22 C21 C26 118.22(17) . . ?
C26 C21 C20 117.03(17) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.45(19) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.76(19) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.32(19) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.70(19) . . ?
C25 C26 H26 119.6 . . ?
C15 O5 C16 105.77(15) . . ?
C15 O6 C17 101.28(16) . . ?
C32 C27 C28 116.52(18) . . ?
O7 C27 C28 119.16(19) . . ?
O7 C27 C32 124.27(19) . . ?
C27 C28 H28 110.7 . . ?
O8 C28 C27 107.17(16) . . ?
O8 C28 H28 110.7 . . ?
O9 C28 C27 110.91(17) . . ?
O9 C28 H28 110.7 . . ?
O9 C28 O8 106.53(17) . . ?
H29A C29 H29B 108.9 . . ?
C30 C29 H29A 110.9 . . ?
C30 C29 H29B 110.9 . . ?
O8 C29 H29A 110.9 . . ?
O8 C29 H29B 110.9 . . ?
O8 C29 C30 104.34(16) . . ?
C29 C30 H30 110.8 . . ?
C31 C30 C29 113.88(17) . . ?
C31 C30 H30 110.8 . . ?
O9 C30 C29 101.84(16) . . ?
O9 C30 H30 110.8 . . ?
O9 C30 C31 108.47(17) . . ?
C30 C31 H31A 109.1 . . ?
C30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C32 C31 C30 112.53(17) . . ?
C32 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C27 C32 C31 116.52(17) . . ?
C33 C32 C27 116.33(19) . . ?
C33 C32 C31 127.15(19) . . ?
C32 C33 H33 114.3 . . ?
C32 C33 C34 131.4(2) . . ?
C34 C33 H33 114.3 . . ?
C35 C34 C33 125.32(18) . . ?
C35 C34 C39 117.74(18) . . ?
C39 C34 C33 116.94(19) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.50(19) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 119.6 . . ?
C35 C36 C37 120.8(2) . . ?
C37 C36 H36 119.6 . . ?
C36 C37 H37 120.2 . . ?
C38 C37 C36 119.6(2) . . ?
C38 C37 H37 120.2 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.0(2) . . ?
C39 C38 H38 120.0 . . ?
C34 C39 H39 119.3 . . ?
C38 C39 C34 121.3(2) . . ?
C38 C39 H39 119.3 . . ?
C28 O8 C29 105.71(16) . . ?
C28 O9 C30 101.49(14) . . ?

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
C1 C2 O2 C3 -89.89(18) . . . . ?
C1 C2 O3 C4 73.24(19) . . . . ?
C1 C6 C7 C8 -175.9(2) . . . . ?
C2 C1 C6 C5 3.6(3) . . . . ?
C2 C1 C6 C7 -177.43(18) . . . . ?
C3 C4 C5 C6 -66.9(2) . . . . ?
C3 C4 O3 C2 40.83(18) . . . . ?
C4 C3 O2 C2 -1.79(19) . . . . ?
C4 C5 C6 C1 -8.6(3) . . . . ?
C4 C5 C6 C7 172.5(2) . . . . ?
C5 C4 O3 C2 -79.53(18) . . . . ?
C5 C6 C7 C8 2.9(4) . . . . ?
C6 C1 C2 O2 79.7(2) . . . . ?
C6 C1 C2 O3 -36.7(2) . . . . ?
C6 C7 C8 C9 5.8(4) . . . . ?
C6 C7 C8 C13 -178.2(2) . . . . ?
C7 C8 C9 C10 174.86(19) . . . . ?
C7 C8 C13 C12 -176.1(2) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C13 C8 C9 C10 -1.1(3) . . . . ?
O1 C1 C2 O2 -100.0(2) . . . . ?
O1 C1 C2 O3 143.61(19) . . . . ?
O1 C1 C6 C5 -176.7(2) . . . . ?
O1 C1 C6 C7 2.2(3) . . . . ?
O2 C2 O3 C4 -44.20(17) . . . . ?
O2 C3 C4 C5 92.8(2) . . . . ?
O2 C3 C4 O3 -24.11(19) . . . . ?
O3 C2 O2 C3 28.54(18) . . . . ?
O3 C4 C5 C6 46.1(2) . . . . ?
C14 C15 O5 C16 -89.9(2) . . . . ?
C14 C15 O6 C17 71.4(2) . . . . ?
C14 C19 C20 C21 176.2(2) . . . . ?
C15 C14 C19 C18 4.1(3) . . . . ?
C15 C14 C19 C20 -173.76(18) . . . . ?
C16 C17 C18 C19 -63.6(3) . . . . ?
C16 C17 O6 C15 41.36(19) . . . . ?
C17 C16 O5 C15 -2.4(2) . . . . ?
C17 C18 C19 C14 -11.9(3) . . . . ?
C17 C18 C19 C20 165.7(2) . . . . ?
C18 C17 O6 C15 -80.01(19) . . . . ?
C18 C19 C20 C21 -1.4(4) . . . . ?
C19 C14 C15 O5 81.2(2) . . . . ?
C19 C14 C15 O6 -34.8(3) . . . . ?
C19 C20 C21 C22 25.0(4) . . . . ?
C19 C20 C21 C26 -154.9(2) . . . . ?
C20 C21 C22 C23 -178.4(2) . . . . ?
C20 C21 C26 C25 177.2(2) . . . . ?
C21 C22 C23 C24 0.8(3) . . . . ?
C22 C21 C26 C25 -2.6(3) . . . . ?
C22 C23 C24 C25 -1.8(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C24 C25 C26 C21 1.6(3) . . . . ?
C26 C21 C22 C23 1.4(3) . . . . ?
O4 C14 C15 O5 -95.0(2) . . . . ?
O4 C14 C15 O6 149.03(19) . . . . ?
O4 C14 C19 C18 180.0(2) . . . . ?
O4 C14 C19 C20 2.1(3) . . . . ?
O5 C15 O6 C17 -44.99(19) . . . . ?
O5 C16 C17 C18 92.7(2) . . . . ?
O5 C16 C17 O6 -24.0(2) . . . . ?
O6 C15 O5 C16 29.5(2) . . . . ?
O6 C17 C18 C19 49.7(2) . . . . ?
C27 C28 O8 C29 -89.52(19) . . . . ?
C27 C28 O9 C30 71.50(18) . . . . ?
C27 C32 C33 C34 179.51(18) . . . . ?
C28 C27 C32 C31 7.7(2) . . . . ?
C28 C27 C32 C33 -172.06(17) . . . . ?
C29 C30 C31 C32 -62.3(2) . . . . ?
C29 C30 O9 C28 41.02(18) . . . . ?
C30 C29 O8 C28 -2.3(2) . . . . ?
C30 C31 C32 C27 -14.5(2) . . . . ?
C30 C31 C32 C33 165.31(19) . . . . ?
C31 C30 O9 C28 -79.38(18) . . . . ?
C31 C32 C33 C34 -0.3(3) . . . . ?
C32 C27 C28 O8 78.5(2) . . . . ?
C32 C27 C28 O9 -37.4(2) . . . . ?
C32 C33 C34 C35 12.2(3) . . . . ?
C32 C33 C34 C39 -168.4(2) . . . . ?
C33 C34 C35 C36 -177.96(18) . . . . ?
C33 C34 C39 C38 178.18(17) . . . . ?
C34 C35 C36 C37 -1.0(3) . . . . ?
C35 C34 C39 C38 -2.3(3) . . . . ?
C35 C36 C37 C38 -1.0(3) . . . . ?
C36 C37 C38 C39 1.2(3) . . . . ?
C37 C38 C39 C34 0.4(3) . . . . ?
C39 C34 C35 C36 2.6(3) . . . . ?
O7 C27 C28 O8 -98.9(2) . . . . ?
O7 C27 C28 O9 145.22(19) . . . . ?
O7 C27 C32 C31 -174.99(19) . . . . ?
O7 C27 C32 C33 5.2(3) . . . . ?
O8 C28 O9 C30 -44.79(18) . . . . ?
O8 C29 C30 C31 92.7(2) . . . . ?
O8 C29 C30 O9 -23.87(19) . . . . ?
O9 C28 O8 C29 29.24(19) . . . . ?
O9 C30 C31 C32 50.3(2) . . . . ?

_olex2_date_sample_data_collection 2017-04-04
_olex2_date_sample_submission    2017-04-04
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id lmh51
_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 1.148
_oxdiff_exptl_absorpt_empirical_full_min 0.854
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
