# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_amhwlb
_database_code_depnum_ccdc_archive 'CCDC 1045000'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_nottingham_internal_coll_name   AMHWLB
_nottingham_internal_coll_number 13644
_nottingham_internal_coll_client AM/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '3.0000, 2.0000'
_nottingham_internal_coll_frame_width 2.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   28/05/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 28/05/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 28/5/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 28/5/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 28/5/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 28/5/2014
_refine_special_details          
;
 ?
;
_audit_creation_date             2014-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H17 Cl O3'
_chemical_formula_sum            'C17 H17 Cl O3'
_chemical_formula_weight         304.76
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H17 O3 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      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                   6.2836(3)
_cell_length_b                   12.6214(7)
_cell_length_c                   37.0026(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2934.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10588
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3450
_cell_measurement_theta_min      3.5050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.369
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.4467
_exptl_crystal_size_mid          0.3345
_exptl_crystal_size_min          0.2333
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            21694
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         3.700
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2437810000
_diffrn_orient_matrix_UB_12      0.0087422000
_diffrn_orient_matrix_UB_13      -0.0033096000
_diffrn_orient_matrix_UB_21      0.0211456000
_diffrn_orient_matrix_UB_22      0.1192819000
_diffrn_orient_matrix_UB_23      -0.0080357000
_diffrn_orient_matrix_UB_31      0.0157101000
_diffrn_orient_matrix_UB_32      -0.0242747000
_diffrn_orient_matrix_UB_33      -0.0407196000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5804
_reflns_number_total             5961
_reflns_odcompleteness_completeness 99.64
_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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 2396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5961
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.056
_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)+(0.0414P)²+0.3964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0716
_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:
 C4(H4), C6(H6), C35(H35), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C33(H33A,H33B),
 C38(H38A,H38B), C39(H39A,H39B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C20(H20), C47(H47), C48(H48), C50(H50), C51(H51)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C40(H40A,H40B,H40C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 1.0199(3) 0.07270(15) 0.30280(5) 0.0230(4) Uani 1 1 d . . . . .
C2 C 1.1021(3) 0.17450(15) 0.28577(5) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.9716(3) 0.26748(15) 0.29954(5) 0.0222(4) Uani 1 1 d . . . . .
H3A H 0.8954 0.3025 0.2794 0.027 Uiso 1 1 calc R . . . .
H3B H 1.0642 0.3202 0.3116 0.027 Uiso 1 1 calc R . . . .
C4 C 0.8135(3) 0.21936(14) 0.32655(4) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.6729 0.2565 0.3263 0.024 Uiso 1 1 calc R . . . .
C5 C 0.7967(3) 0.10480(14) 0.31389(5) 0.0206(4) Uani 1 1 d . . . . .
C6 C 0.9090(3) 0.21175(15) 0.36523(5) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.8146 0.1649 0.3800 0.027 Uiso 1 1 calc R . . . .
C7 C 1.1298(3) 0.16017(16) 0.36343(5) 0.0275(4) Uani 1 1 d . . . . .
H7A H 1.2324 0.2118 0.3533 0.033 Uiso 1 1 calc R . . . .
H7B H 1.1768 0.1423 0.3882 0.033 Uiso 1 1 calc R . . . .
C8 C 1.1325(3) 0.05985(16) 0.34031(5) 0.0271(4) Uani 1 1 d . . . . .
H8A H 1.0617 0.0021 0.3538 0.033 Uiso 1 1 calc R . . . .
H8B H 1.2821 0.0385 0.3362 0.033 Uiso 1 1 calc R . . . .
C9 C 1.0410(4) -0.02630(17) 0.28001(6) 0.0331(5) Uani 1 1 d . . . . .
H9A H 1.1888 -0.0510 0.2806 0.050 Uiso 1 1 calc GR . . . .
H9B H 1.0002 -0.0104 0.2550 0.050 Uiso 1 1 calc GR . . . .
H9C H 0.9475 -0.0817 0.2897 0.050 Uiso 1 1 calc GR . . . .
O10 O 1.2451(2) 0.17972(13) 0.26413(4) 0.0327(3) Uani 1 1 d . . . . .
O11 O 0.6431(2) 0.04736(11) 0.31590(4) 0.0278(3) Uani 1 1 d . . . . .
C12 C 0.9206(3) 0.31949(16) 0.38385(5) 0.0253(4) Uani 1 1 d . . . . .
H12A H 1.0232 0.3150 0.4041 0.030 Uiso 1 1 calc R . . . .
H12B H 0.9760 0.3722 0.3664 0.030 Uiso 1 1 calc R . . . .
C13 C 0.7101(3) 0.35814(16) 0.39829(5) 0.0264(4) Uani 1 1 d . . . . .
O14 O 0.5473(3) 0.30770(14) 0.39488(4) 0.0398(4) Uani 1 1 d . . . . .
C15 C 0.7055(3) 0.46218(15) 0.41807(4) 0.0236(4) Uani 1 1 d . . . . .
C16 C 0.8767(3) 0.53270(16) 0.41796(5) 0.0267(4) Uani 1 1 d . . . . .
H16 H 1.0034 0.5147 0.4054 0.032 Uiso 1 1 calc R . . . .
C17 C 0.8635(3) 0.62906(16) 0.43613(5) 0.0285(4) Uani 1 1 d . . . . .
H17 H 0.9790 0.6776 0.4358 0.034 Uiso 1 1 calc R . . . .
C18 C 0.6783(3) 0.65253(16) 0.45473(5) 0.0266(4) Uani 1 1 d . . . . .
C19 C 0.5069(3) 0.58347(16) 0.45572(5) 0.0272(4) Uani 1 1 d . . . . .
H19 H 0.3820 0.6008 0.4689 0.033 Uiso 1 1 calc R . . . .
C20 C 0.5216(3) 0.48853(16) 0.43702(5) 0.0254(4) Uani 1 1 d . . . . .
H20 H 0.4046 0.4408 0.4371 0.031 Uiso 1 1 calc R . . . .
Cl21 Cl 0.65767(9) 0.77308(4) 0.47698(2) 0.03652(13) Uani 1 1 d . . . . .
C31 C -0.0177(3) 0.93602(16) 0.69637(5) 0.0233(4) Uani 1 1 d . . . . .
C32 C 0.2119(3) 0.91902(16) 0.68480(5) 0.0228(4) Uani 1 1 d . . . . .
C33 C 0.2575(3) 0.80087(15) 0.68225(5) 0.0229(4) Uani 1 1 d . . . . .
H33A H 0.3620 0.7789 0.7008 0.028 Uiso 1 1 calc R . . . .
H33B H 0.3137 0.7823 0.6581 0.028 Uiso 1 1 calc R . . . .
C35 C 0.0404(3) 0.74777(15) 0.68883(5) 0.0228(4) Uani 1 1 d . . . . .
H35 H 0.0545 0.6780 0.7014 0.027 Uiso 1 1 calc R . . . .
C36 C -0.0790(3) 0.82880(16) 0.71148(5) 0.0235(4) Uani 1 1 d . . . . .
C37 C -0.0938(3) 0.73937(15) 0.65372(5) 0.0231(4) Uani 1 1 d . . . . .
H37 H -0.2423 0.7194 0.6606 0.028 Uiso 1 1 calc R . . . .
C38 C -0.1018(3) 0.84807(15) 0.63487(5) 0.0237(4) Uani 1 1 d . . . . .
H38A H 0.0365 0.8610 0.6228 0.028 Uiso 1 1 calc R . . . .
H38B H -0.2128 0.8460 0.6159 0.028 Uiso 1 1 calc R . . . .
C39 C -0.1489(3) 0.94078(15) 0.66044(5) 0.0251(4) Uani 1 1 d . . . . .
H39A H -0.3026 0.9407 0.6664 0.030 Uiso 1 1 calc R . . . .
H39B H -0.1166 1.0081 0.6478 0.030 Uiso 1 1 calc R . . . .
C40 C -0.0558(3) 1.03166(17) 0.72014(6) 0.0311(4) Uani 1 1 d . . . . .
H40A H -0.2091 1.0447 0.7221 0.047 Uiso 1 1 calc GR . . . .
H40B H 0.0136 1.0937 0.7095 0.047 Uiso 1 1 calc GR . . . .
H40C H 0.0034 1.0185 0.7442 0.047 Uiso 1 1 calc GR . . . .
O41 O 0.3358(2) 0.98921(12) 0.67754(4) 0.0316(3) Uani 1 1 d . . . . .
O42 O -0.2144(2) 0.81152(13) 0.73394(4) 0.0313(3) Uani 1 1 d . . . . .
C43 C -0.0079(3) 0.65421(15) 0.62852(5) 0.0250(4) Uani 1 1 d . . . . .
H43A H 0.1232 0.6810 0.6168 0.030 Uiso 1 1 calc R . . . .
H43B H 0.0315 0.5914 0.6431 0.030 Uiso 1 1 calc R . . . .
C44 C -0.1624(3) 0.62031(15) 0.59943(5) 0.0265(4) Uani 1 1 d . . . . .
O45 O -0.3427(3) 0.65582(12) 0.59779(4) 0.0341(3) Uani 1 1 d . . . . .
C46 C -0.0891(3) 0.53981(15) 0.57228(5) 0.0265(4) Uani 1 1 d . . . . .
C47 C 0.1113(4) 0.49309(17) 0.57369(5) 0.0320(4) Uani 1 1 d . . . . .
H47 H 0.2046 0.5099 0.5931 0.038 Uiso 1 1 calc R . . . .
C48 C 0.1770(4) 0.42229(17) 0.54725(6) 0.0341(5) Uani 1 1 d . . . . .
H48 H 0.3137 0.3904 0.5483 0.041 Uiso 1 1 calc R . . . .
C49 C 0.0383(4) 0.39935(16) 0.51927(5) 0.0311(4) Uani 1 1 d . . . . .
C50 C -0.1625(4) 0.44361(17) 0.51735(5) 0.0329(4) Uani 1 1 d . . . . .
H50 H -0.2558 0.4259 0.4981 0.040 Uiso 1 1 calc R . . . .
C51 C -0.2256(4) 0.51409(17) 0.54392(5) 0.0300(4) Uani 1 1 d . . . . .
H51 H -0.3631 0.5452 0.5428 0.036 Uiso 1 1 calc R . . . .
Cl52 Cl 0.12055(10) 0.31337(4) 0.48521(2) 0.03960(13) 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 1.521(3) . ?
C1 C5 1.516(3) . ?
C1 C8 1.566(3) . ?
C1 C9 1.513(3) . ?
C2 C3 1.520(3) . ?
C2 O10 1.205(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.534(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.524(2) . ?
C4 C6 1.555(2) . ?
C5 O11 1.210(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.534(3) . ?
C6 C12 1.526(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.528(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.508(3) . ?
C13 O14 1.211(3) . ?
C13 C15 1.504(3) . ?
C15 C16 1.396(3) . ?
C15 C20 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 C19 1.386(3) . ?
C18 Cl21 1.735(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9500 . ?
C31 C32 1.520(3) . ?
C31 C36 1.514(3) . ?
C31 C39 1.566(2) . ?
C31 C40 1.513(3) . ?
C32 C33 1.521(3) . ?
C32 O41 1.210(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C35 1.539(3) . ?
C35 H35 1.0000 . ?
C35 C36 1.520(3) . ?
C35 C37 1.553(2) . ?
C36 O42 1.209(2) . ?
C37 H37 1.0000 . ?
C37 C38 1.540(2) . ?
C37 C43 1.522(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.533(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.511(3) . ?
C44 O45 1.219(3) . ?
C44 C46 1.501(3) . ?
C46 C47 1.391(3) . ?
C46 C51 1.394(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.388(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.384(3) . ?
C49 C50 1.381(3) . ?
C49 Cl52 1.742(2) . ?
C50 H50 0.9500 . ?
C50 C51 1.384(3) . ?
C51 H51 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
C2 C1 C8 107.54(15) . . ?
C5 C1 C2 101.55(15) . . ?
C5 C1 C8 101.86(14) . . ?
C9 C1 C2 115.90(16) . . ?
C9 C1 C5 116.88(16) . . ?
C9 C1 C8 111.66(16) . . ?
C3 C2 C1 109.28(15) . . ?
O10 C2 C1 125.05(18) . . ?
O10 C2 C3 125.64(18) . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C2 C3 C4 105.19(15) . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C3 C4 H4 112.3 . . ?
C3 C4 C6 111.95(15) . . ?
C5 C4 C3 102.72(14) . . ?
C5 C4 H4 112.3 . . ?
C5 C4 C6 104.54(14) . . ?
C6 C4 H4 112.3 . . ?
C1 C5 C4 105.83(15) . . ?
O11 C5 C1 126.49(17) . . ?
O11 C5 C4 127.23(17) . . ?
C4 C6 H6 108.0 . . ?
C7 C6 C4 109.59(14) . . ?
C7 C6 H6 108.0 . . ?
C12 C6 C4 112.26(14) . . ?
C12 C6 H6 108.0 . . ?
C12 C6 C7 110.78(16) . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.71(16) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C1 C8 H8A 108.8 . . ?
C1 C8 H8B 108.8 . . ?
C7 C8 C1 113.91(15) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C12 H12A 108.8 . . ?
C6 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C6 113.98(16) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
O14 C13 C12 122.27(18) . . ?
O14 C13 C15 119.57(19) . . ?
C15 C13 C12 118.16(17) . . ?
C16 C15 C13 122.72(17) . . ?
C20 C15 C13 118.03(18) . . ?
C20 C15 C16 119.26(18) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.64(19) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.50(19) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C19 122.14(18) . . ?
C17 C18 Cl21 119.11(16) . . ?
C19 C18 Cl21 118.74(16) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.57(19) . . ?
C20 C19 H19 120.7 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.88(19) . . ?
C19 C20 H20 119.6 . . ?
C32 C31 C39 105.43(14) . . ?
C36 C31 C32 102.67(16) . . ?
C36 C31 C39 102.35(15) . . ?
C40 C31 C32 115.26(17) . . ?
C40 C31 C36 117.28(15) . . ?
C40 C31 C39 112.32(16) . . ?
C31 C32 C33 109.56(16) . . ?
O41 C32 C31 124.75(18) . . ?
O41 C32 C33 125.64(18) . . ?
C32 C33 H33A 110.9 . . ?
C32 C33 H33B 110.9 . . ?
C32 C33 C35 104.47(15) . . ?
H33A C33 H33B 108.9 . . ?
C35 C33 H33A 110.9 . . ?
C35 C33 H33B 110.9 . . ?
C33 C35 H35 112.2 . . ?
C33 C35 C37 112.25(14) . . ?
C36 C35 C33 103.40(15) . . ?
C36 C35 H35 112.2 . . ?
C36 C35 C37 103.84(15) . . ?
C37 C35 H35 112.2 . . ?
C31 C36 C35 105.79(15) . . ?
O42 C36 C31 126.45(18) . . ?
O42 C36 C35 127.22(19) . . ?
C35 C37 H37 108.0 . . ?
C38 C37 C35 109.63(15) . . ?
C38 C37 H37 108.0 . . ?
C43 C37 C35 111.63(16) . . ?
C43 C37 H37 108.0 . . ?
C43 C37 C38 111.31(15) . . ?
C37 C38 H38A 108.7 . . ?
C37 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
C39 C38 C37 114.01(14) . . ?
C39 C38 H38A 108.7 . . ?
C39 C38 H38B 108.7 . . ?
C31 C39 H39A 109.0 . . ?
C31 C39 H39B 109.0 . . ?
C38 C39 C31 113.13(15) . . ?
C38 C39 H39A 109.0 . . ?
C38 C39 H39B 109.0 . . ?
H39A C39 H39B 107.8 . . ?
C31 C40 H40A 109.5 . . ?
C31 C40 H40B 109.5 . . ?
C31 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C37 C43 H43A 108.7 . . ?
C37 C43 H43B 108.7 . . ?
H43A C43 H43B 107.6 . . ?
C44 C43 C37 114.12(17) . . ?
C44 C43 H43A 108.7 . . ?
C44 C43 H43B 108.7 . . ?
O45 C44 C43 121.87(18) . . ?
O45 C44 C46 120.03(18) . . ?
C46 C44 C43 118.09(18) . . ?
C47 C46 C44 122.65(18) . . ?
C47 C46 C51 119.1(2) . . ?
C51 C46 C44 118.21(19) . . ?
C46 C47 H47 119.5 . . ?
C48 C47 C46 121.03(19) . . ?
C48 C47 H47 119.5 . . ?
C47 C48 H48 120.8 . . ?
C49 C48 C47 118.4(2) . . ?
C49 C48 H48 120.8 . . ?
C48 C49 Cl52 119.00(18) . . ?
C50 C49 C48 121.9(2) . . ?
C50 C49 Cl52 119.06(16) . . ?
C49 C50 H50 120.5 . . ?
C49 C50 C51 119.01(19) . . ?
C51 C50 H50 120.5 . . ?
C46 C51 H51 119.7 . . ?
C50 C51 C46 120.6(2) . . ?
C50 C51 H51 119.7 . . ?

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 2.09(19) . . . . ?
C2 C1 C5 C4 -37.06(17) . . . . ?
C2 C1 C5 O11 150.19(18) . . . . ?
C2 C1 C8 C7 47.7(2) . . . . ?
C2 C3 C4 C5 -24.52(17) . . . . ?
C2 C3 C4 C6 87.11(17) . . . . ?
C3 C4 C5 C1 39.00(17) . . . . ?
C3 C4 C5 O11 -148.33(18) . . . . ?
C3 C4 C6 C7 -49.2(2) . . . . ?
C3 C4 C6 C12 74.37(19) . . . . ?
C4 C6 C7 C8 -47.3(2) . . . . ?
C4 C6 C12 C13 77.26(19) . . . . ?
C5 C1 C2 C3 21.21(18) . . . . ?
C5 C1 C2 O10 -157.23(18) . . . . ?
C5 C1 C8 C7 -58.6(2) . . . . ?
C5 C4 C6 C7 61.31(18) . . . . ?
C5 C4 C6 C12 -175.15(15) . . . . ?
C6 C4 C5 C1 -78.03(16) . . . . ?
C6 C4 C5 O11 94.6(2) . . . . ?
C6 C7 C8 C1 47.5(2) . . . . ?
C6 C12 C13 O14 -0.7(3) . . . . ?
C6 C12 C13 C15 178.29(14) . . . . ?
C7 C6 C12 C13 -159.87(15) . . . . ?
C8 C1 C2 C3 -85.33(18) . . . . ?
C8 C1 C2 O10 96.2(2) . . . . ?
C8 C1 C5 C4 73.87(16) . . . . ?
C8 C1 C5 O11 -98.9(2) . . . . ?
C9 C1 C2 C3 148.95(16) . . . . ?
C9 C1 C2 O10 -29.5(3) . . . . ?
C9 C1 C5 C4 -164.17(16) . . . . ?
C9 C1 C5 O11 23.1(3) . . . . ?
C9 C1 C8 C7 175.93(17) . . . . ?
O10 C2 C3 C4 -179.48(18) . . . . ?
C12 C6 C7 C8 -171.73(15) . . . . ?
C12 C13 C15 C16 11.9(3) . . . . ?
C12 C13 C15 C20 -168.41(17) . . . . ?
C13 C15 C16 C17 178.79(17) . . . . ?
C13 C15 C20 C19 -179.79(16) . . . . ?
O14 C13 C15 C16 -169.10(19) . . . . ?
O14 C13 C15 C20 10.6(3) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C16 C17 C18 Cl21 -179.08(14) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C18 C19 C20 C15 0.9(3) . . . . ?
C20 C15 C16 C17 -0.9(3) . . . . ?
Cl21 C18 C19 C20 178.12(14) . . . . ?
C31 C32 C33 C35 5.74(19) . . . . ?
C32 C31 C36 C35 -33.99(17) . . . . ?
C32 C31 C36 O42 154.05(18) . . . . ?
C32 C31 C39 C38 50.0(2) . . . . ?
C32 C33 C35 C36 -26.29(17) . . . . ?
C32 C33 C35 C37 85.00(18) . . . . ?
C33 C35 C36 C31 38.14(17) . . . . ?
C33 C35 C36 O42 -149.99(18) . . . . ?
C33 C35 C37 C38 -50.2(2) . . . . ?
C33 C35 C37 C43 73.6(2) . . . . ?
C35 C37 C38 C39 -45.8(2) . . . . ?
C35 C37 C43 C44 163.52(15) . . . . ?
C36 C31 C32 C33 17.14(18) . . . . ?
C36 C31 C32 O41 -165.31(18) . . . . ?
C36 C31 C39 C38 -57.01(19) . . . . ?
C36 C35 C37 C38 60.79(18) . . . . ?
C36 C35 C37 C43 -175.40(15) . . . . ?
C37 C35 C36 C31 -79.21(17) . . . . ?
C37 C35 C36 O42 92.7(2) . . . . ?
C37 C38 C39 C31 44.8(2) . . . . ?
C37 C43 C44 O45 -3.0(3) . . . . ?
C37 C43 C44 C46 177.54(16) . . . . ?
C38 C37 C43 C44 -73.6(2) . . . . ?
C39 C31 C32 C33 -89.69(17) . . . . ?
C39 C31 C32 O41 87.9(2) . . . . ?
C39 C31 C36 C35 75.18(17) . . . . ?
C39 C31 C36 O42 -96.8(2) . . . . ?
C40 C31 C32 C33 145.85(16) . . . . ?
C40 C31 C32 O41 -36.6(3) . . . . ?
C40 C31 C36 C35 -161.44(17) . . . . ?
C40 C31 C36 O42 26.6(3) . . . . ?
C40 C31 C39 C38 176.34(16) . . . . ?
O41 C32 C33 C35 -171.79(18) . . . . ?
C43 C37 C38 C39 -169.77(16) . . . . ?
C43 C44 C46 C47 2.3(3) . . . . ?
C43 C44 C46 C51 -175.44(17) . . . . ?
C44 C46 C47 C48 -177.24(19) . . . . ?
C44 C46 C51 C50 177.36(18) . . . . ?
O45 C44 C46 C47 -177.15(19) . . . . ?
O45 C44 C46 C51 5.1(3) . . . . ?
C46 C47 C48 C49 0.2(3) . . . . ?
C47 C46 C51 C50 -0.5(3) . . . . ?
C47 C48 C49 C50 -0.9(3) . . . . ?
C47 C48 C49 Cl52 178.34(17) . . . . ?
C48 C49 C50 C51 0.9(3) . . . . ?
C49 C50 C51 C46 -0.2(3) . . . . ?
C51 C46 C47 C48 0.5(3) . . . . ?
Cl52 C49 C50 C51 -178.32(16) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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 0 -1 0.0847 -0.0001 0.0000 -0.9995 0.0033 0.0080 0.0407
0 0 1 0.1487 0.0001 -0.0000 0.9995 -0.0033 -0.0080 -0.0407
0 -1 1 0.1484 0.0005 -0.9998 0.9985 -0.0122 -0.1273 -0.0164
2 -1 1 0.2180 1.9992 -0.9997 0.9986 -0.4994 -0.0850 0.0150
0 2 -5 0.1200 -0.0012 1.9997 -4.9955 0.0343 0.2786 0.1549
1 5 -2 0.1508 0.9973 4.9990 -1.9941 -0.1928 0.6334 -0.0245
0 3 5 0.1242 -0.0008 2.9992 5.0003 0.0099 0.3176 -0.2764
0 1 5 0.1410 -0.0000 0.9997 4.9984 -0.0078 0.0791 -0.2278
-4 -1 -2 0.1971 -3.9972 -0.9999 -2.0002 0.9723 -0.1877 0.0429
2 5 -11 0.1589 1.9960 4.9993 -10.9894 -0.4065 0.7268 0.3575
3 6 -1 0.1514 2.9957 5.9988 -0.9935 -0.6746 0.7869 -0.0581
-3 0 -19 0.1657 -2.9995 0.0003 -18.9904 0.7941 0.0892 0.7261

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'

####################################################################### 
# 
# 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_amhwla
_database_code_depnum_ccdc_archive 'CCDC 1045001'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_nottingham_internal_coll_name   AMHWLA
_nottingham_internal_coll_number 13643
_nottingham_internal_coll_client AM/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '5.0000, 20.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   28/05/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 29/05/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 29/5/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 29/5/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 29/5/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 29/5/2014
_refine_special_details          
;
The crystal was determined to be a 2-component twin using PLATON TWINROTMATR, 
which was then used to generate an HKLF5-style file against which subsequent 
refinements were performed.
;
_vrf_PLAT340_amhwla              
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0112 Ang
RESPONSE: This is an indicator of relatively low structure quality, 
which is probably due to the twinning present.
;
_audit_creation_date             2014-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H18 O3'
_chemical_formula_sum            'C17 H18 O3'
_chemical_formula_weight         270.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H17 O3'
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                   12.1037(2)
_cell_length_b                   6.87725(12)
_cell_length_c                   16.6432(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.6683(16)
_cell_angle_gamma                90
_cell_volume                     1383.89(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20296
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3250
_cell_measurement_theta_min      2.6350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.4756
_exptl_crystal_size_mid          0.1437
_exptl_crystal_size_min          0.0722
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            5607
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.264
_diffrn_reflns_theta_min         2.658
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1110409000
_diffrn_orient_matrix_UB_12      0.0899435000
_diffrn_orient_matrix_UB_13      -0.0298412000
_diffrn_orient_matrix_UB_21      -0.0270717000
_diffrn_orient_matrix_UB_22      -0.1851661000
_diffrn_orient_matrix_UB_23      -0.0491348000
_diffrn_orient_matrix_UB_31      -0.0563424000
_diffrn_orient_matrix_UB_32      -0.0883690000
_diffrn_orient_matrix_UB_33      0.0726650000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                5548
_reflns_number_total             5607
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details 
;
 Flack x determined using 2497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5607
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0823
_refine_ls_restrained_S_all      1.078
_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)+(0.0639P)²+5.7027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2479
_refine_ls_wR_factor_ref         0.2481
_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:
 C4(H4), C6(H6), C24(H24), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C23(H23A,H23B),
 C27(H27A,H27B), C28(H28A,H28B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C36(H36), C37(H37),
 C38(H38), C39(H39), C40(H40)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 1.0740(6) 0.3556(12) 0.1162(5) 0.0222(16) Uani 1 1 d . . . . .
C2 C 0.9800(7) 0.3461(11) 0.0523(5) 0.0213(16) Uani 1 1 d . . . . .
C3 C 0.8745(6) 0.4173(12) 0.0883(4) 0.0229(17) Uani 1 1 d . . . . .
H3A H 0.8156 0.3178 0.0822 0.027 Uiso 1 1 calc R . . . .
H3B H 0.8483 0.5384 0.0615 0.027 Uiso 1 1 calc R . . . .
C4 C 0.9044(6) 0.4549(12) 0.1777(4) 0.0198(15) Uani 1 1 d . . . . .
H4 H 0.8617 0.5644 0.2007 0.024 Uiso 1 1 calc R . . . .
C5 C 1.0271(6) 0.4952(10) 0.1758(4) 0.0180(15) Uani 1 1 d . . . . .
C6 C 0.8942(7) 0.2578(12) 0.2261(5) 0.0231(17) Uani 1 1 d . . . . .
H6 H 0.8144 0.2195 0.2239 0.028 Uiso 1 1 calc R . . . .
C7 C 0.9581(7) 0.0995(13) 0.1840(5) 0.0261(17) Uani 1 1 d . . . . .
H7A H 0.9630 -0.0161 0.2195 0.031 Uiso 1 1 calc R . . . .
H7B H 0.9155 0.0615 0.1343 0.031 Uiso 1 1 calc R . . . .
C8 C 1.0741(7) 0.1559(12) 0.1622(5) 0.0239(17) Uani 1 1 d . . . . .
H8A H 1.1047 0.0536 0.1278 0.029 Uiso 1 1 calc R . . . .
H8B H 1.1222 0.1659 0.2118 0.029 Uiso 1 1 calc R . . . .
C9 C 1.1854(7) 0.4077(14) 0.0846(5) 0.0302(19) Uani 1 1 d . . . . .
H9A H 1.1808 0.5351 0.0583 0.045 Uiso 1 1 calc GR . . . .
H9B H 1.2068 0.3093 0.0457 0.045 Uiso 1 1 calc GR . . . .
H9C H 1.2409 0.4124 0.1294 0.045 Uiso 1 1 calc GR . . . .
O10 O 0.9875(6) 0.2891(9) -0.0163(3) 0.0326(14) Uani 1 1 d . . . . .
O11 O 1.0790(5) 0.6190(9) 0.2157(4) 0.0316(14) Uani 1 1 d . . . . .
C12 C 0.9313(6) 0.2836(12) 0.3151(5) 0.0217(15) Uani 1 1 d . . . . .
H12A H 0.9496 0.1545 0.3384 0.026 Uiso 1 1 calc R . . . .
H12B H 0.9994 0.3635 0.3185 0.026 Uiso 1 1 calc R . . . .
C13 C 0.8455(6) 0.3783(13) 0.3641(5) 0.0225(16) Uani 1 1 d . . . . .
O14 O 0.7605(5) 0.4468(10) 0.3320(4) 0.0344(15) Uani 1 1 d . . . . .
C15 C 0.8612(6) 0.3805(11) 0.4542(4) 0.0187(14) Uani 1 1 d . . . . .
C16 C 0.9551(8) 0.3088(12) 0.4945(5) 0.0269(17) Uani 1 1 d . . . . .
H16 H 1.0141 0.2592 0.4648 0.032 Uiso 1 1 calc R . . . .
C17 C 0.9638(7) 0.3089(12) 0.5775(5) 0.0253(17) Uani 1 1 d . . . . .
H17 H 1.0296 0.2632 0.6045 0.030 Uiso 1 1 calc R . . . .
C18 C 0.8774(7) 0.3748(12) 0.6215(5) 0.0271(17) Uani 1 1 d . . . . .
H18 H 0.8821 0.3685 0.6786 0.032 Uiso 1 1 calc R . . . .
C19 C 0.7832(7) 0.4508(12) 0.5815(5) 0.0263(17) Uani 1 1 d . . . . .
H19 H 0.7248 0.5026 0.6112 0.032 Uiso 1 1 calc R . . . .
C20 C 0.7755(7) 0.4501(12) 0.4983(5) 0.0234(16) Uani 1 1 d . . . . .
H20 H 0.7104 0.4982 0.4711 0.028 Uiso 1 1 calc R . . . .
C21 C 0.5484(6) 0.3839(12) 0.8790(4) 0.0200(15) Uani 1 1 d . . . . .
C22 C 0.4585(6) 0.3945(12) 0.9388(4) 0.0222(16) Uani 1 1 d . . . . .
C23 C 0.3591(7) 0.2751(14) 0.9067(4) 0.0258(17) Uani 1 1 d . . . . .
H23A H 0.2909 0.3549 0.9046 0.031 Uiso 1 1 calc R . . . .
H23B H 0.3476 0.1602 0.9411 0.031 Uiso 1 1 calc R . . . .
C24 C 0.3891(6) 0.2129(11) 0.8219(4) 0.0178(15) Uani 1 1 d . . . . .
H24 H 0.3564 0.0840 0.8065 0.021 Uiso 1 1 calc R . . . .
C25 C 0.5152(6) 0.2055(11) 0.8304(4) 0.0158(14) Uani 1 1 d . . . . .
C26 C 0.3596(6) 0.3714(12) 0.7590(4) 0.0213(15) Uani 1 1 d . . . . .
H26 H 0.2772 0.3833 0.7551 0.026 Uiso 1 1 calc R . . . .
C27 C 0.4065(7) 0.5688(12) 0.7877(5) 0.0245(17) Uani 1 1 d . . . . .
H27A H 0.3998 0.6630 0.7427 0.029 Uiso 1 1 calc R . . . .
H27B H 0.3618 0.6183 0.8316 0.029 Uiso 1 1 calc R . . . .
C28 C 0.5280(7) 0.5561(12) 0.8178(5) 0.0256(18) Uani 1 1 d . . . . .
H28A H 0.5499 0.6801 0.8442 0.031 Uiso 1 1 calc R . . . .
H28B H 0.5750 0.5373 0.7713 0.031 Uiso 1 1 calc R . . . .
C29 C 0.6661(6) 0.3814(13) 0.9143(5) 0.0255(17) Uani 1 1 d . . . . .
H29A H 0.6727 0.2837 0.9572 0.038 Uiso 1 1 calc GR . . . .
H29B H 0.6848 0.5098 0.9365 0.038 Uiso 1 1 calc GR . . . .
H29C H 0.7168 0.3490 0.8721 0.038 Uiso 1 1 calc GR . . . .
O30 O 0.4632(5) 0.4837(10) 1.0014(3) 0.0322(14) Uani 1 1 d . . . . .
O31 O 0.5765(5) 0.0842(9) 0.8046(4) 0.0287(13) Uani 1 1 d . . . . .
C32 C 0.3976(7) 0.3182(12) 0.6750(4) 0.0213(16) Uani 1 1 d . . . . .
H32A H 0.4737 0.3674 0.6691 0.026 Uiso 1 1 calc R . . . .
H32B H 0.3994 0.1749 0.6697 0.026 Uiso 1 1 calc R . . . .
C33 C 0.3226(6) 0.4018(11) 0.6085(5) 0.0220(16) Uani 1 1 d . . . . .
O34 O 0.2336(5) 0.4705(10) 0.6217(3) 0.0335(15) Uani 1 1 d . . . . .
C35 C 0.3584(6) 0.3874(12) 0.5230(4) 0.0209(15) Uani 1 1 d . . . . .
C36 C 0.4613(7) 0.3116(12) 0.5030(5) 0.0262(17) Uani 1 1 d . . . . .
H36 H 0.5116 0.2649 0.5441 0.031 Uiso 1 1 calc R . . . .
C37 C 0.4894(8) 0.3049(12) 0.4235(5) 0.0285(18) Uani 1 1 d . . . . .
H37 H 0.5580 0.2496 0.4101 0.034 Uiso 1 1 calc R . . . .
C38 C 0.4184(7) 0.3779(12) 0.3635(4) 0.0245(16) Uani 1 1 d . . . . .
H38 H 0.4392 0.3762 0.3092 0.029 Uiso 1 1 calc R . . . .
C39 C 0.3158(8) 0.4545(14) 0.3827(5) 0.0298(19) Uani 1 1 d . . . . .
H39 H 0.2663 0.5024 0.3414 0.036 Uiso 1 1 calc R . . . .
C40 C 0.2869(7) 0.4603(12) 0.4615(5) 0.0238(16) Uani 1 1 d . . . . .
H40 H 0.2177 0.5142 0.4745 0.029 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.522(11) . ?
C1 C5 1.510(11) . ?
C1 C8 1.571(11) . ?
C1 C9 1.514(11) . ?
C2 C3 1.516(11) . ?
C2 O10 1.215(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.536(10) . ?
C4 H4 1.0000 . ?
C4 C5 1.513(10) . ?
C4 C6 1.585(11) . ?
C5 O11 1.233(9) . ?
C6 H6 1.0000 . ?
C6 C7 1.525(12) . ?
C6 C12 1.538(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.518(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.498(10) . ?
C13 O14 1.232(9) . ?
C13 C15 1.502(10) . ?
C15 C16 1.383(11) . ?
C15 C20 1.384(11) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(12) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(11) . ?
C20 H20 0.9500 . ?
C21 C22 1.510(10) . ?
C21 C25 1.514(10) . ?
C21 C28 1.575(11) . ?
C21 C29 1.515(10) . ?
C22 C23 1.532(11) . ?
C22 O30 1.208(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.534(10) . ?
C24 H24 1.0000 . ?
C24 C25 1.526(10) . ?
C24 C26 1.543(10) . ?
C25 O31 1.208(9) . ?
C26 H26 1.0000 . ?
C26 C27 1.539(12) . ?
C26 C32 1.536(10) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.534(12) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.512(10) . ?
C33 O34 1.206(9) . ?
C33 C35 1.510(10) . ?
C35 C36 1.404(11) . ?
C35 C40 1.402(11) . ?
C36 H36 0.9500 . ?
C36 C37 1.381(11) . ?
C37 H37 0.9500 . ?
C37 C38 1.381(12) . ?
C38 H38 0.9500 . ?
C38 C39 1.400(12) . ?
C39 H39 0.9500 . ?
C39 C40 1.374(11) . ?
C40 H40 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
C2 C1 C8 106.6(6) . . ?
C5 C1 C2 101.2(6) . . ?
C5 C1 C8 103.2(6) . . ?
C5 C1 C9 116.5(7) . . ?
C9 C1 C2 114.6(7) . . ?
C9 C1 C8 113.3(7) . . ?
C3 C2 C1 109.0(6) . . ?
O10 C2 C1 125.7(8) . . ?
O10 C2 C3 125.2(7) . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C2 C3 C4 105.8(6) . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C3 C4 H4 113.3 . . ?
C3 C4 C6 109.2(6) . . ?
C5 C4 C3 101.4(6) . . ?
C5 C4 H4 113.3 . . ?
C5 C4 C6 105.5(6) . . ?
C6 C4 H4 113.3 . . ?
C1 C5 C4 107.2(6) . . ?
O11 C5 C1 126.5(7) . . ?
O11 C5 C4 126.3(7) . . ?
C4 C6 H6 107.7 . . ?
C7 C6 C4 108.9(6) . . ?
C7 C6 H6 107.7 . . ?
C7 C6 C12 113.2(7) . . ?
C12 C6 C4 111.4(7) . . ?
C12 C6 H6 107.7 . . ?
C6 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 C6 115.0(7) . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C1 C8 H8A 109.4 . . ?
C1 C8 H8B 109.4 . . ?
C7 C8 C1 111.1(7) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C12 H12A 108.9 . . ?
C6 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C6 113.3(6) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C12 C13 C15 119.3(6) . . ?
O14 C13 C12 121.1(7) . . ?
O14 C13 C15 119.6(7) . . ?
C16 C15 C13 122.9(7) . . ?
C16 C15 C20 119.0(7) . . ?
C20 C15 C13 118.1(7) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(8) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(8) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.5(7) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(8) . . ?
C20 C19 H19 120.3 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 121.0(8) . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C25 102.1(6) . . ?
C22 C21 C28 107.1(6) . . ?
C22 C21 C29 116.0(6) . . ?
C25 C21 C28 103.5(6) . . ?
C25 C21 C29 114.8(7) . . ?
C29 C21 C28 112.1(7) . . ?
C21 C22 C23 108.8(6) . . ?
O30 C22 C21 125.9(7) . . ?
O30 C22 C23 125.3(7) . . ?
C22 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
C22 C23 C24 104.7(6) . . ?
H23A C23 H23B 108.9 . . ?
C24 C23 H23A 110.8 . . ?
C24 C23 H23B 110.8 . . ?
C23 C24 H24 112.1 . . ?
C23 C24 C26 111.7(7) . . ?
C25 C24 C23 101.7(6) . . ?
C25 C24 H24 112.1 . . ?
C25 C24 C26 106.6(6) . . ?
C26 C24 H24 112.1 . . ?
C21 C25 C24 105.2(6) . . ?
O31 C25 C21 126.6(7) . . ?
O31 C25 C24 128.2(7) . . ?
C24 C26 H26 107.5 . . ?
C27 C26 C24 110.0(6) . . ?
C27 C26 H26 107.5 . . ?
C32 C26 C24 112.3(6) . . ?
C32 C26 H26 107.5 . . ?
C32 C26 C27 111.8(6) . . ?
C26 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C28 C27 C26 112.7(7) . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
C21 C28 H28A 109.2 . . ?
C21 C28 H28B 109.2 . . ?
C27 C28 C21 111.9(7) . . ?
C27 C28 H28A 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C21 C29 H29A 109.5 . . ?
C21 C29 H29B 109.5 . . ?
C21 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C32 H32A 109.1 . . ?
C26 C32 H32B 109.1 . . ?
H32A C32 H32B 107.9 . . ?
C33 C32 C26 112.3(6) . . ?
C33 C32 H32A 109.1 . . ?
C33 C32 H32B 109.1 . . ?
O34 C33 C32 121.8(7) . . ?
O34 C33 C35 119.7(7) . . ?
C35 C33 C32 118.4(6) . . ?
C36 C35 C33 123.0(7) . . ?
C40 C35 C33 118.0(7) . . ?
C40 C35 C36 118.9(7) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 120.0(8) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.5(8) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.0(7) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 120.1 . . ?
C40 C39 C38 119.8(7) . . ?
C40 C39 H39 120.1 . . ?
C35 C40 H40 119.7 . . ?
C39 C40 C35 120.7(8) . . ?
C39 C40 H40 119.7 . . ?

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 -4.5(8) . . . . ?
C2 C1 C5 C4 36.4(7) . . . . ?
C2 C1 C5 O11 -143.7(8) . . . . ?
C2 C1 C8 C7 -46.4(8) . . . . ?
C2 C3 C4 C5 25.9(8) . . . . ?
C2 C3 C4 C6 -85.1(7) . . . . ?
C3 C4 C5 C1 -39.5(8) . . . . ?
C3 C4 C5 O11 140.6(8) . . . . ?
C3 C4 C6 C7 50.4(8) . . . . ?
C3 C4 C6 C12 175.9(6) . . . . ?
C4 C6 C7 C8 48.1(9) . . . . ?
C4 C6 C12 C13 78.8(8) . . . . ?
C5 C1 C2 C3 -18.9(8) . . . . ?
C5 C1 C2 O10 161.7(8) . . . . ?
C5 C1 C8 C7 59.8(8) . . . . ?
C5 C4 C6 C7 -57.9(8) . . . . ?
C5 C4 C6 C12 67.6(8) . . . . ?
C6 C4 C5 C1 74.4(7) . . . . ?
C6 C4 C5 O11 -105.5(9) . . . . ?
C6 C7 C8 C1 -50.2(9) . . . . ?
C6 C12 C13 O14 -8.0(12) . . . . ?
C6 C12 C13 C15 169.0(7) . . . . ?
C7 C6 C12 C13 -158.2(7) . . . . ?
C8 C1 C2 C3 88.6(7) . . . . ?
C8 C1 C2 O10 -90.7(9) . . . . ?
C8 C1 C5 C4 -73.8(7) . . . . ?
C8 C1 C5 O11 106.1(9) . . . . ?
C9 C1 C2 C3 -145.1(7) . . . . ?
C9 C1 C2 O10 35.5(11) . . . . ?
C9 C1 C5 C4 161.4(7) . . . . ?
C9 C1 C5 O11 -18.7(12) . . . . ?
C9 C1 C8 C7 -173.4(7) . . . . ?
O10 C2 C3 C4 174.9(7) . . . . ?
C12 C6 C7 C8 -76.3(9) . . . . ?
C12 C13 C15 C16 4.0(12) . . . . ?
C12 C13 C15 C20 -173.3(7) . . . . ?
C13 C15 C16 C17 -178.0(8) . . . . ?
C13 C15 C20 C19 178.1(7) . . . . ?
O14 C13 C15 C16 -179.0(8) . . . . ?
O14 C13 C15 C20 3.7(12) . . . . ?
C15 C16 C17 C18 2.0(12) . . . . ?
C16 C15 C20 C19 0.7(12) . . . . ?
C16 C17 C18 C19 -3.2(13) . . . . ?
C17 C18 C19 C20 3.1(13) . . . . ?
C18 C19 C20 C15 -1.9(13) . . . . ?
C20 C15 C16 C17 -0.8(12) . . . . ?
C21 C22 C23 C24 -6.0(9) . . . . ?
C22 C21 C25 C24 38.0(7) . . . . ?
C22 C21 C25 O31 -141.7(8) . . . . ?
C22 C21 C28 C27 -46.8(8) . . . . ?
C22 C23 C24 C25 28.6(8) . . . . ?
C22 C23 C24 C26 -84.7(8) . . . . ?
C23 C24 C25 C21 -42.0(7) . . . . ?
C23 C24 C25 O31 137.7(8) . . . . ?
C23 C24 C26 C27 50.2(8) . . . . ?
C23 C24 C26 C32 175.4(6) . . . . ?
C24 C26 C27 C28 47.8(9) . . . . ?
C24 C26 C32 C33 149.1(7) . . . . ?
C25 C21 C22 C23 -19.3(8) . . . . ?
C25 C21 C22 O30 161.3(8) . . . . ?
C25 C21 C28 C27 60.6(8) . . . . ?
C25 C24 C26 C27 -60.1(8) . . . . ?
C25 C24 C26 C32 65.1(8) . . . . ?
C26 C24 C25 C21 75.2(7) . . . . ?
C26 C24 C25 O31 -105.2(9) . . . . ?
C26 C27 C28 C21 -49.0(9) . . . . ?
C26 C32 C33 O34 -12.5(11) . . . . ?
C26 C32 C33 C35 171.0(7) . . . . ?
C27 C26 C32 C33 -86.7(8) . . . . ?
C28 C21 C22 C23 89.1(7) . . . . ?
C28 C21 C22 O30 -90.3(10) . . . . ?
C28 C21 C25 C24 -73.2(7) . . . . ?
C28 C21 C25 O31 107.2(8) . . . . ?
C29 C21 C22 C23 -144.9(7) . . . . ?
C29 C21 C22 O30 35.7(12) . . . . ?
C29 C21 C25 C24 164.4(6) . . . . ?
C29 C21 C25 O31 -15.3(11) . . . . ?
C29 C21 C28 C27 -175.1(7) . . . . ?
O30 C22 C23 C24 173.3(8) . . . . ?
C32 C26 C27 C28 -77.7(8) . . . . ?
C32 C33 C35 C36 -4.3(12) . . . . ?
C32 C33 C35 C40 178.2(7) . . . . ?
C33 C35 C36 C37 -179.2(8) . . . . ?
C33 C35 C40 C39 178.8(8) . . . . ?
O34 C33 C35 C36 179.2(8) . . . . ?
O34 C33 C35 C40 1.6(12) . . . . ?
C35 C36 C37 C38 2.0(13) . . . . ?
C36 C35 C40 C39 1.2(12) . . . . ?
C36 C37 C38 C39 -1.8(13) . . . . ?
C37 C38 C39 C40 1.3(14) . . . . ?
C38 C39 C40 C35 -1.0(13) . . . . ?
C40 C35 C36 C37 -1.7(12) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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 0 -1 0.0361 0.0005 0.0002 -0.9997 0.0298 0.0491 -0.0727
0 0 1 0.0361 -0.0005 -0.0002 0.9997 -0.0298 -0.0491 0.0727
3 0 -5 0.0586 3.0009 0.0011 -4.9995 -0.1839 0.1642 -0.5325
-3 0 5 0.0406 -3.0009 -0.0011 4.9995 0.1839 -0.1642 0.5325
2 -4 5 0.2197 1.9902 -4.0008 4.9974 -0.7300 0.4414 0.6045
-1 -2 5 0.1633 -1.0051 -2.0009 4.9986 -0.2175 0.1521 0.5967
-1 3 -5 0.1647 -0.9923 3.0009 -4.9979 0.5292 -0.2832 -0.5724
-5 0 -4 0.0705 -4.9960 0.0009 -3.9976 0.6741 0.3315 -0.0091
-5 -1 2 0.1172 -5.0003 -1.0003 2.0006 0.4056 0.2223 0.5155
5 0 3 0.0527 4.9964 -0.0006 2.9979 -0.6443 -0.2824 -0.0636
-4 -4 -3 0.1892 -4.0035 -3.9991 -2.9989 0.1743 0.9962 0.3610
2 2 5 0.1574 2.0001 1.9988 4.9986 -0.1915 -0.6699 0.0739

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'

####################################################################### 
# 
# 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_arbhla
_database_code_depnum_ccdc_archive 'CCDC 1045002'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_nottingham_internal_coll_name   ARBHLA
_nottingham_internal_coll_number 13607
_nottingham_internal_coll_client ARB/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time 2.0000
_nottingham_internal_coll_frame_width 2.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   14/05/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 14/05/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 14/5/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 14/5/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 28/5/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 28/5/2014
_refine_special_details          
;
 ?
;
_audit_creation_date             2014-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H19 Cl O3'
_chemical_formula_sum            'C18 H19 Cl O3'
_chemical_formula_weight         318.78
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H19 O3 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                   7.0438(5)
_cell_length_b                   11.6921(7)
_cell_length_c                   9.8846(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.470(8)
_cell_angle_gamma                90
_cell_volume                     772.12(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4347
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.4430
_cell_measurement_theta_min      4.7290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.275
_exptl_absorpt_correction_T_max  0.829
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.7503
_exptl_crystal_size_mid          0.4512
_exptl_crystal_size_min          0.0875
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6983
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.365
_diffrn_reflns_theta_min         4.717
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1465832000
_diffrn_orient_matrix_UB_12      -0.1005605000
_diffrn_orient_matrix_UB_13      -0.0147363000
_diffrn_orient_matrix_UB_21      0.0831378000
_diffrn_orient_matrix_UB_22      -0.0208174000
_diffrn_orient_matrix_UB_23      0.1620564000
_diffrn_orient_matrix_UB_31      -0.1576635000
_diffrn_orient_matrix_UB_32      0.0824053000
_diffrn_orient_matrix_UB_33      0.0229174000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                3075
_reflns_number_total             3148
_reflns_odcompleteness_completeness 99.59
_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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.062
_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)+(0.0526P)²+0.1594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0893
_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:
 C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C9(H9A,H9B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.8842(4) 0.6719(2) 0.5600(3) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.9427(4) 0.5447(2) 0.5789(2) 0.0201(5) Uani 1 1 d . . . . .
C3 C 0.8212(4) 0.4722(2) 0.6469(3) 0.0234(5) Uani 1 1 d . . . . .
H3A H 0.8453 0.4971 0.7466 0.028 Uiso 1 1 calc R . . . .
H3B H 0.8626 0.3912 0.6481 0.028 Uiso 1 1 calc R . . . .
C4 C 0.5973(4) 0.4837(2) 0.5624(3) 0.0228(5) Uani 1 1 d . . . . .
H4A H 0.5178 0.4490 0.6183 0.027 Uiso 1 1 calc R . . . .
H4B H 0.5688 0.4404 0.4721 0.027 Uiso 1 1 calc R . . . .
C5 C 0.5292(4) 0.6099(2) 0.5274(3) 0.0209(5) Uani 1 1 d . . . . .
H5 H 0.4128 0.6252 0.5621 0.025 Uiso 1 1 calc R . . . .
C6 C 0.6964(4) 0.6915(2) 0.6011(2) 0.0193(5) Uani 1 1 d . . . . .
C7 C 0.4678(4) 0.6396(2) 0.3662(3) 0.0212(5) Uani 1 1 d . . . . .
H7 H 0.4234 0.7212 0.3560 0.025 Uiso 1 1 calc R . . . .
C8 C 0.6464(4) 0.6312(2) 0.3105(3) 0.0229(5) Uani 1 1 d . . . . .
H8A H 0.6872 0.5501 0.3114 0.027 Uiso 1 1 calc R . . . .
H8B H 0.6056 0.6582 0.2104 0.027 Uiso 1 1 calc R . . . .
C9 C 0.8242(4) 0.7013(2) 0.3989(3) 0.0218(5) Uani 1 1 d . . . . .
H9A H 0.7904 0.7836 0.3855 0.026 Uiso 1 1 calc R . . . .
H9B H 0.9397 0.6871 0.3645 0.026 Uiso 1 1 calc R . . . .
C10 C 1.0606(4) 0.7441(2) 0.6480(3) 0.0258(5) Uani 1 1 d . . . . .
H10A H 1.0257 0.8253 0.6341 0.039 Uiso 1 1 calc GR . . . .
H10B H 1.1774 0.7286 0.6172 0.039 Uiso 1 1 calc GR . . . .
H10C H 1.0921 0.7246 0.7492 0.039 Uiso 1 1 calc GR . . . .
O11 O 1.0766(3) 0.50763(16) 0.5391(2) 0.0265(4) Uani 1 1 d . . . . .
O12 O 0.6799(3) 0.76980(16) 0.67712(18) 0.0245(4) Uani 1 1 d . . . . .
C13 C 0.2888(4) 0.5677(2) 0.2792(3) 0.0234(5) Uani 1 1 d . . . . .
H13A H 0.3390 0.4956 0.2503 0.028 Uiso 1 1 calc R . . . .
H13B H 0.2069 0.5474 0.3407 0.028 Uiso 1 1 calc R . . . .
C14 C 0.1568(4) 0.6275(2) 0.1470(3) 0.0290(6) Uani 1 1 d . . . . .
O15 O 0.2098(4) 0.7146(2) 0.1028(3) 0.0552(8) Uani 1 1 d . . . . .
C16 C -0.0460(4) 0.5792(2) 0.0748(3) 0.0219(5) Uani 1 1 d . . . . .
C17 C -0.0959(4) 0.4671(2) 0.0983(3) 0.0230(5) Uani 1 1 d . . . . .
H17 H 0.0039 0.4174 0.1560 0.028 Uiso 1 1 calc R . . . .
C18 C -0.2899(4) 0.4278(2) 0.0383(3) 0.0246(5) Uani 1 1 d . . . . .
H18 H -0.3233 0.3512 0.0536 0.030 Uiso 1 1 calc R . . . .
C19 C -0.4346(4) 0.5012(2) -0.0441(3) 0.0255(5) Uani 1 1 d . . . . .
C20 C -0.3885(4) 0.6115(3) -0.0733(3) 0.0266(5) Uani 1 1 d . . . . .
H20 H -0.4884 0.6599 -0.1332 0.032 Uiso 1 1 calc R . . . .
C21 C -0.1941(4) 0.6501(2) -0.0137(3) 0.0248(5) Uani 1 1 d . . . . .
H21 H -0.1606 0.7257 -0.0330 0.030 Uiso 1 1 calc R . . . .
Cl22 Cl -0.68018(9) 0.45282(7) -0.11215(7) 0.0384(2) 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 1.540(3) . ?
C1 C6 1.518(3) . ?
C1 C9 1.552(3) . ?
C1 C10 1.525(3) . ?
C2 C3 1.505(3) . ?
C2 O11 1.211(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.539(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.556(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.511(3) . ?
C5 C7 1.552(3) . ?
C6 O12 1.213(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.528(3) . ?
C7 C13 1.532(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.520(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.514(4) . ?
C14 O15 1.212(4) . ?
C14 C16 1.491(4) . ?
C16 C17 1.396(4) . ?
C16 C21 1.401(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C19 C20 1.383(4) . ?
C19 Cl22 1.740(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(4) . ?
C21 H21 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
C2 C1 C9 108.28(19) . . ?
C6 C1 C2 109.64(19) . . ?
C6 C1 C9 105.29(19) . . ?
C6 C1 C10 112.7(2) . . ?
C10 C1 C2 109.1(2) . . ?
C10 C1 C9 111.7(2) . . ?
C3 C2 C1 115.4(2) . . ?
O11 C2 C1 120.8(2) . . ?
O11 C2 C3 123.7(2) . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C2 C3 C4 109.8(2) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.2(2) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C4 C5 H5 108.7 . . ?
C6 C5 C4 110.7(2) . . ?
C6 C5 H5 108.7 . . ?
C6 C5 C7 105.99(19) . . ?
C7 C5 C4 113.9(2) . . ?
C7 C5 H5 108.7 . . ?
C5 C6 C1 112.8(2) . . ?
O12 C6 C1 122.8(2) . . ?
O12 C6 C5 124.2(2) . . ?
C5 C7 H7 107.0 . . ?
C8 C7 C5 111.2(2) . . ?
C8 C7 H7 107.0 . . ?
C8 C7 C13 112.8(2) . . ?
C13 C7 C5 111.46(19) . . ?
C13 C7 H7 107.0 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 112.4(2) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C1 C9 H9A 109.2 . . ?
C1 C9 H9B 109.2 . . ?
C8 C9 C1 112.17(19) . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C13 H13A 108.8 . . ?
C7 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C7 113.7(2) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
O15 C14 C13 121.6(3) . . ?
O15 C14 C16 120.2(2) . . ?
C16 C14 C13 118.1(2) . . ?
C17 C16 C14 122.0(2) . . ?
C17 C16 C21 118.9(2) . . ?
C21 C16 C14 119.0(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.3(2) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 Cl22 118.9(2) . . ?
C20 C19 C18 121.6(3) . . ?
C20 C19 Cl22 119.5(2) . . ?
C19 C20 H20 120.6 . . ?
C19 C20 C21 118.8(2) . . ?
C21 C20 H20 120.6 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 120.9(3) . . ?
C20 C21 H21 119.5 . . ?

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 55.2(3) . . . . ?
C2 C1 C6 C5 -51.2(2) . . . . ?
C2 C1 C6 O12 133.7(2) . . . . ?
C2 C1 C9 C8 60.7(3) . . . . ?
C2 C3 C4 C5 -47.2(3) . . . . ?
C3 C4 C5 C6 -6.8(3) . . . . ?
C3 C4 C5 C7 112.5(2) . . . . ?
C4 C5 C6 C1 58.3(2) . . . . ?
C4 C5 C6 O12 -126.7(2) . . . . ?
C4 C5 C7 C8 -65.1(3) . . . . ?
C4 C5 C7 C13 61.7(3) . . . . ?
C5 C7 C8 C9 -53.0(3) . . . . ?
C5 C7 C13 C14 149.9(2) . . . . ?
C6 C1 C2 C3 -6.5(3) . . . . ?
C6 C1 C2 O11 172.7(2) . . . . ?
C6 C1 C9 C8 -56.5(3) . . . . ?
C6 C5 C7 C8 56.8(3) . . . . ?
C6 C5 C7 C13 -176.3(2) . . . . ?
C7 C5 C6 C1 -65.7(2) . . . . ?
C7 C5 C6 O12 109.3(3) . . . . ?
C7 C8 C9 C1 53.3(3) . . . . ?
C7 C13 C14 O15 12.4(4) . . . . ?
C7 C13 C14 C16 -165.0(2) . . . . ?
C8 C7 C13 C14 -84.1(3) . . . . ?
C9 C1 C2 C3 -120.9(2) . . . . ?
C9 C1 C2 O11 58.3(3) . . . . ?
C9 C1 C6 C5 65.1(2) . . . . ?
C9 C1 C6 O12 -110.0(2) . . . . ?
C10 C1 C2 C3 117.3(2) . . . . ?
C10 C1 C2 O11 -63.5(3) . . . . ?
C10 C1 C6 C5 -172.9(2) . . . . ?
C10 C1 C6 O12 12.0(3) . . . . ?
C10 C1 C9 C8 -179.1(2) . . . . ?
O11 C2 C3 C4 -124.0(3) . . . . ?
C13 C7 C8 C9 -179.1(2) . . . . ?
C13 C14 C16 C17 -18.4(4) . . . . ?
C13 C14 C16 C21 158.2(2) . . . . ?
C14 C16 C17 C18 174.9(2) . . . . ?
C14 C16 C21 C20 -174.6(2) . . . . ?
O15 C14 C16 C17 164.1(3) . . . . ?
O15 C14 C16 C21 -19.3(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C16 C21 C20 2.1(4) . . . . ?
C17 C18 C19 C20 2.9(4) . . . . ?
C17 C18 C19 Cl22 -177.04(19) . . . . ?
C18 C19 C20 C21 -2.5(4) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?
C21 C16 C17 C18 -1.7(4) . . . . ?
Cl22 C19 C20 C21 177.4(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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 -1 0 0.1475 -0.0000 -0.9989 0.0019 0.1004 0.0211 -0.0823
2 2 -1 0.3047 1.9981 1.9896 -0.9929 -0.4783 -0.0362 -0.1738
-3 5 2 0.3464 -2.9972 5.0106 1.9741 -0.0936 -0.0336 0.9307
-5 -1 3 0.2504 -4.9953 -0.9748 2.9746 0.7864 0.0870 0.7754
4 -2 -3 0.3941 3.9965 -2.0216 -2.9740 -0.3387 -0.1076 -0.8648
0 0 1 0.0512 -0.0005 0.0073 0.9993 -0.0154 0.1618 0.0236
0 0 -1 0.0362 0.0005 -0.0073 -0.9993 0.0154 -0.1618 -0.0236
-1 2 -5 0.1487 -0.9964 1.9618 -5.0056 0.0225 -0.9349 0.2040
1 5 -5 0.1730 1.0012 4.9577 -5.0010 -0.5716 -0.8304 0.1361
3 3 -6 0.2120 2.9992 2.9516 -5.9865 -0.6482 -0.7822 -0.3668
1 5 4 0.1493 0.9970 5.0234 3.9931 -0.7101 0.6254 0.3483
0 -6 4 0.1272 -0.0020 -5.9644 4.0086 0.5410 0.7736 -0.3993
-3 -1 6 0.1805 -2.9992 -0.9538 5.9827 0.4474 0.7401 0.5314

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'

####################################################################### 
# 
# 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_arbhlb
_database_code_depnum_ccdc_archive 'CCDC 1045003'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_nottingham_internal_coll_name   ARBHLB
_nottingham_internal_coll_number 13608
_nottingham_internal_coll_client ARB/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '5.0000, 20.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   14/05/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 15/05/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 15/5/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 15/5/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 28/5/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 28/5/2014
_refine_special_details          
;
 ?
;
_audit_creation_date             2014-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H19 N O5'
_chemical_formula_sum            'C18 H19 N O5'
_chemical_formula_weight         329.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H19 N O5'
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      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                   6.71816(7)
_cell_length_b                   13.19234(16)
_cell_length_c                   17.8880(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1585.38(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23060
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.5900
_cell_measurement_theta_min      3.3470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2936
_exptl_crystal_size_mid          0.0869
_exptl_crystal_size_min          0.0636
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33630
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.576
_diffrn_reflns_theta_min         4.164
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1934501000
_diffrn_orient_matrix_UB_12      -0.0611193000
_diffrn_orient_matrix_UB_13      0.0102778000
_diffrn_orient_matrix_UB_21      -0.1230905000
_diffrn_orient_matrix_UB_22      -0.0958597000
_diffrn_orient_matrix_UB_23      0.0167782000
_diffrn_orient_matrix_UB_31      -0.0010957000
_diffrn_orient_matrix_UB_32      -0.0267949000
_diffrn_orient_matrix_UB_33      -0.0838342000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3207
_reflns_number_total             3243
_reflns_odcompleteness_completeness 99.94
_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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.054
_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)+(0.0454P)²+0.3469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0789
_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:
 C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C9(H9A,H9B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.3825(3) 0.11073(13) 0.29710(9) 0.0243(3) Uani 1 1 d . . . . .
C2 C 0.2103(3) 0.04098(14) 0.31922(11) 0.0314(4) Uani 1 1 d . . . . .
C3 C 0.0550(3) 0.08043(16) 0.37156(16) 0.0438(5) Uani 1 1 d . . . . .
H3A H 0.0027 0.0225 0.4008 0.053 Uiso 1 1 calc R . . . .
H3B H -0.0564 0.1073 0.3413 0.053 Uiso 1 1 calc R . . . .
C4 C 0.1188(4) 0.16263(16) 0.42637(12) 0.0402(5) Uani 1 1 d . . . . .
H4A H 0.1658 0.1295 0.4728 0.048 Uiso 1 1 calc R . . . .
H4B H 0.0002 0.2035 0.4395 0.048 Uiso 1 1 calc R . . . .
C5 C 0.2832(3) 0.23503(13) 0.39868(9) 0.0251(3) Uani 1 1 d . . . . .
H5 H 0.3385 0.2717 0.4430 0.030 Uiso 1 1 calc R . . . .
C6 C 0.4472(3) 0.17190(13) 0.36516(10) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.2195(3) 0.31490(12) 0.33999(9) 0.0229(3) Uani 1 1 d . . . . .
H7 H 0.3410 0.3554 0.3276 0.027 Uiso 1 1 calc R . . . .
C8 C 0.1509(3) 0.26525(14) 0.26745(9) 0.0307(4) Uani 1 1 d . . . . .
H8A H 0.1287 0.3182 0.2291 0.037 Uiso 1 1 calc R . . . .
H8B H 0.0229 0.2300 0.2761 0.037 Uiso 1 1 calc R . . . .
C9 C 0.3045(3) 0.18937(15) 0.23867(10) 0.0343(4) Uani 1 1 d . . . . .
H9A H 0.4198 0.2277 0.2190 0.041 Uiso 1 1 calc R . . . .
H9B H 0.2451 0.1517 0.1963 0.041 Uiso 1 1 calc R . . . .
C10 C 0.5546(4) 0.05066(16) 0.26332(12) 0.0395(5) Uani 1 1 d . . . . .
H10A H 0.6622 0.0972 0.2495 0.059 Uiso 1 1 calc GR . . . .
H10B H 0.5082 0.0146 0.2187 0.059 Uiso 1 1 calc GR . . . .
H10C H 0.6039 0.0016 0.3001 0.059 Uiso 1 1 calc GR . . . .
O11 O 0.1987(3) -0.04329(11) 0.29214(10) 0.0507(4) Uani 1 1 d . . . . .
O12 O 0.6151(2) 0.17059(12) 0.38970(11) 0.0479(4) Uani 1 1 d . . . . .
C13 C 0.0652(2) 0.38931(13) 0.37021(10) 0.0242(3) Uani 1 1 d . . . . .
H13A H 0.0097 0.4289 0.3280 0.029 Uiso 1 1 calc R . . . .
H13B H -0.0453 0.3506 0.3931 0.029 Uiso 1 1 calc R . . . .
C14 C 0.1491(3) 0.46161(13) 0.42748(9) 0.0230(3) Uani 1 1 d . . . . .
O15 O 0.32666(19) 0.46730(11) 0.43977(8) 0.0326(3) Uani 1 1 d . . . . .
C16 C 0.0086(2) 0.52940(12) 0.46983(9) 0.0207(3) Uani 1 1 d . . . . .
C17 C -0.1917(2) 0.54047(12) 0.45036(9) 0.0213(3) Uani 1 1 d . . . . .
H17 H -0.2448 0.5032 0.4095 0.026 Uiso 1 1 calc R . . . .
C18 C -0.3132(2) 0.60581(12) 0.49048(9) 0.0216(3) Uani 1 1 d . . . . .
H18 H -0.4493 0.6141 0.4774 0.026 Uiso 1 1 calc R . . . .
C19 C -0.2319(2) 0.65856(12) 0.54981(9) 0.0201(3) Uani 1 1 d . . . . .
C20 C -0.0335(3) 0.64948(13) 0.57042(9) 0.0229(3) Uani 1 1 d . . . . .
H20 H 0.0189 0.6873 0.6111 0.028 Uiso 1 1 calc R . . . .
C21 C 0.0854(2) 0.58395(13) 0.53015(10) 0.0237(3) Uani 1 1 d . . . . .
H21 H 0.2213 0.5759 0.5436 0.028 Uiso 1 1 calc R . . . .
N22 N -0.3600(2) 0.72636(11) 0.59386(8) 0.0230(3) Uani 1 1 d . . . . .
O23 O -0.54107(18) 0.71670(10) 0.58769(7) 0.0280(3) Uani 1 1 d . . . . .
O24 O -0.2804(2) 0.78964(10) 0.63406(7) 0.0335(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 1.530(3) . ?
C1 C6 1.524(2) . ?
C1 C9 1.563(2) . ?
C1 C10 1.526(2) . ?
C2 C3 1.495(3) . ?
C2 O11 1.215(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.523(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.542(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.506(2) . ?
C5 C7 1.548(2) . ?
C6 O12 1.210(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.525(2) . ?
C7 C13 1.527(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.527(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.509(2) . ?
C14 O15 1.215(2) . ?
C14 C16 1.505(2) . ?
C16 C17 1.397(2) . ?
C16 C21 1.396(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C19 C20 1.388(2) . ?
C19 N22 1.470(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(2) . ?
C21 H21 0.9500 . ?
N22 O23 1.228(2) . ?
N22 O24 1.2247(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 108.58(15) . . ?
C6 C1 C2 109.11(14) . . ?
C6 C1 C9 106.16(14) . . ?
C6 C1 C10 112.04(16) . . ?
C10 C1 C2 111.27(16) . . ?
C10 C1 C9 109.51(14) . . ?
C3 C2 C1 118.69(16) . . ?
O11 C2 C1 119.7(2) . . ?
O11 C2 C3 121.5(2) . . ?
C2 C3 H3A 108.0 . . ?
C2 C3 H3B 108.0 . . ?
C2 C3 C4 117.04(17) . . ?
H3A C3 H3B 107.3 . . ?
C4 C3 H3A 108.0 . . ?
C4 C3 H3B 108.0 . . ?
C3 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C3 C4 C5 115.82(16) . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C4 C5 H5 108.1 . . ?
C4 C5 C7 116.21(15) . . ?
C6 C5 C4 108.03(14) . . ?
C6 C5 H5 108.1 . . ?
C6 C5 C7 107.97(14) . . ?
C7 C5 H5 108.1 . . ?
C5 C6 C1 113.72(14) . . ?
O12 C6 C1 123.22(16) . . ?
O12 C6 C5 123.05(17) . . ?
C5 C7 H7 106.8 . . ?
C8 C7 C5 111.61(13) . . ?
C8 C7 H7 106.8 . . ?
C8 C7 C13 111.85(14) . . ?
C13 C7 C5 112.65(13) . . ?
C13 C7 H7 106.8 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 C9 111.36(16) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C1 C9 H9A 108.3 . . ?
C1 C9 H9B 108.3 . . ?
C8 C9 C1 115.87(14) . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C13 H13A 109.0 . . ?
C7 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C7 113.14(14) . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
O15 C14 C13 121.91(16) . . ?
O15 C14 C16 119.21(16) . . ?
C16 C14 C13 118.87(14) . . ?
C17 C16 C14 122.73(15) . . ?
C21 C16 C14 117.60(14) . . ?
C21 C16 C17 119.67(15) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.17(15) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.54(15) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C20 122.68(15) . . ?
C18 C19 N22 119.13(15) . . ?
C20 C19 N22 118.18(14) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 C19 118.13(15) . . ?
C21 C20 H20 120.9 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.80(15) . . ?
C20 C21 H21 119.6 . . ?
O23 N22 C19 117.94(14) . . ?
O24 N22 C19 118.28(14) . . ?
O24 N22 O23 123.77(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 -27.6(3) . . . . ?
C2 C1 C6 C5 -58.24(19) . . . . ?
C2 C1 C6 O12 122.3(2) . . . . ?
C2 C1 C9 C8 66.3(2) . . . . ?
C2 C3 C4 C5 31.5(3) . . . . ?
C3 C4 C5 C6 -47.4(2) . . . . ?
C3 C4 C5 C7 74.0(2) . . . . ?
C4 C5 C6 C1 62.63(19) . . . . ?
C4 C5 C6 O12 -117.9(2) . . . . ?
C4 C5 C7 C8 -63.5(2) . . . . ?
C4 C5 C7 C13 63.29(19) . . . . ?
C5 C7 C8 C9 -51.5(2) . . . . ?
C5 C7 C13 C14 70.40(19) . . . . ?
C6 C1 C2 C3 39.2(2) . . . . ?
C6 C1 C2 O11 -143.43(18) . . . . ?
C6 C1 C9 C8 -50.9(2) . . . . ?
C6 C5 C7 C8 57.98(19) . . . . ?
C6 C5 C7 C13 -175.22(14) . . . . ?
C7 C5 C6 C1 -63.80(18) . . . . ?
C7 C5 C6 O12 115.6(2) . . . . ?
C7 C8 C9 C1 49.5(2) . . . . ?
C7 C13 C14 O15 9.2(2) . . . . ?
C7 C13 C14 C16 -171.59(14) . . . . ?
C8 C7 C13 C14 -162.93(15) . . . . ?
C9 C1 C2 C3 -76.1(2) . . . . ?
C9 C1 C2 O11 101.3(2) . . . . ?
C9 C1 C6 C5 58.59(19) . . . . ?
C9 C1 C6 O12 -120.8(2) . . . . ?
C10 C1 C2 C3 163.28(18) . . . . ?
C10 C1 C2 O11 -19.3(2) . . . . ?
C10 C1 C6 C5 178.09(15) . . . . ?
C10 C1 C6 O12 -1.3(3) . . . . ?
C10 C1 C9 C8 -172.02(18) . . . . ?
O11 C2 C3 C4 155.03(19) . . . . ?
C13 C7 C8 C9 -178.78(15) . . . . ?
C13 C14 C16 C17 -10.7(2) . . . . ?
C13 C14 C16 C21 170.35(15) . . . . ?
C14 C16 C17 C18 -178.57(15) . . . . ?
C14 C16 C21 C20 178.40(15) . . . . ?
O15 C14 C16 C17 168.61(17) . . . . ?
O15 C14 C16 C21 -10.4(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C16 C21 C20 -0.6(2) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C17 C18 C19 N22 -178.66(14) . . . . ?
C18 C19 C20 C21 -0.8(2) . . . . ?
C18 C19 N22 O23 16.3(2) . . . . ?
C18 C19 N22 O24 -163.17(15) . . . . ?
C19 C20 C21 C16 0.8(2) . . . . ?
C20 C19 N22 O23 -163.02(15) . . . . ?
C20 C19 N22 O24 17.6(2) . . . . ?
C21 C16 C17 C18 0.4(2) . . . . ?
N22 C19 C20 C21 178.46(14) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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 -3 -5 0.0352 0.0002 -2.9976 -5.0034 0.1318 0.2034 0.4998
0 3 5 0.0442 -0.0002 2.9976 5.0034 -0.1318 -0.2034 -0.4998
0 3 -5 0.0318 0.0012 2.9964 -5.0046 -0.2343 -0.3713 0.3393
0 -3 5 0.0318 -0.0012 -2.9964 5.0046 0.2343 0.3713 -0.3393
-4 0 -3 0.1504 -3.9988 -0.0009 -3.0039 -0.8044 0.4419 0.2562
4 0 3 0.1182 3.9988 0.0009 3.0039 0.8044 -0.4419 -0.2562
0 9 1 0.0446 0.0014 8.9911 0.9990 -0.5390 -0.8453 -0.3247
0 0 12 0.0350 -0.0016 0.0014 12.0097 0.1230 0.2016 -1.0069
0 -8 3 0.0377 -0.0018 -7.9916 3.0040 0.5190 0.8167 -0.0377
-3 3 -8 0.1105 -2.9978 2.9957 -8.0082 -0.8453 -0.0525 0.5944
2 -4 -9 0.0734 2.0001 -3.9968 -9.0057 0.5386 -0.0142 0.8599
-3 5 2 0.1385 -2.9988 4.9948 1.9995 -0.8649 -0.0761 -0.2982
1 4 -10 0.0394 1.0018 3.9949 -10.0085 -0.1532 -0.6742 0.7309
1 6 8 0.0405 0.9998 5.9950 8.0057 -0.0907 -0.5634 -0.8329
-3 -6 0 0.1099 -3.0004 -5.9944 0.0000 -0.2141 0.9439 0.1639
0 -2 -11 0.0361 0.0011 -1.9993 -11.0085 0.0093 0.0068 0.9765

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'

